WO2015003968A1 - Glycine-betaine amide and ester derivatives as deodorising active substances, and cosmetic compositions containing same - Google Patents

Glycine-betaine amide and ester derivatives as deodorising active substances, and cosmetic compositions containing same Download PDF

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Publication number
WO2015003968A1
WO2015003968A1 PCT/EP2014/064047 EP2014064047W WO2015003968A1 WO 2015003968 A1 WO2015003968 A1 WO 2015003968A1 EP 2014064047 W EP2014064047 W EP 2014064047W WO 2015003968 A1 WO2015003968 A1 WO 2015003968A1
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Prior art keywords
compound
composition
branched
linear
formula
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PCT/EP2014/064047
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French (fr)
Inventor
Maria Dalko
Julien Hitce
Xavier Schultze
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L'oreal
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Publication of WO2015003968A1 publication Critical patent/WO2015003968A1/en

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/06Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
    • C07C229/10Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
    • C07C229/12Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of acyclic carbon skeletons
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00Anti-perspirants or body deodorants
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/04Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C237/06Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms

Definitions

  • the present invention relates to glycine-betaine esters and amide derivatives as deodorant active agents, cosmetic compositions comprising them, as well as their uses in cosmetics.
  • the present invention relates to a combination of glycine-betaine ester and amide derivatives with one or more deodorant active agents and / or one or more antiperspirant active agents.
  • Deodorant substances usually destroy the resident bacterial flora.
  • Triclosan (2,4,4'-trichloro-2'-hydroxydiphenyl ether) and farnesol which have the disadvantage of significantly modifying the ecology of skin flora.
  • transition metal chelating agents such as EDTA or DPTA. These materials deprive the medium of metals necessary for the growth of bacteria.
  • Cipropriate patent application CN86106630 discloses compositions comprising surfactants which would have deodorizing and sterilizing activity, but would be mainly used for the deodorization of toilets, farm pens, poultry houses, animal rearing rooms, and to eliminate bad odors produced by rotten food, the smell of fish and meat in the refrigerator, kitchen, food processing workshops, grocery stores and sewerage (abbreviated).
  • the teaching of this application does not solve the problems posed by the the present invention, these applications being very different from the treatment of odors or perspiration in a human being.
  • Escherichia coli Escherichia coli, Shigella sp., Salmonella sp. and Listeria monocytogenes or antifungal on different fungi.
  • French application FR 2 869 913 describes surfactants comprising an ester or amide of glycine betaine for their detergent, emulsifying or foaming properties.
  • This application describes in particular compositions of liquid soap, bubble bath, shower gel or shampoo.
  • glycine-betaine ester and amide derivatives of formula (I) detailed below have good deodorant efficacy and can be easily formulated as a product intended to reduce body odor, alone, in particular. combination, or in combination with conventional antiperspirants or deodorant actives.
  • the invention relates to the use of a compound of formula (I), which will be given later in detail, as a deodorant agent in particular in a composition comprising a physiologically acceptable carrier.
  • the subject of the present invention is also a composition, in particular a cosmetic composition, comprising in a physiologically acceptable medium at least one compound of formula (I) in combination with at least one antiperspirant active agent and / or at least one deodorant active agent.
  • the subject of the present invention is also a cosmetic method for treating body odors, in particular axillary odors, consisting in applying to the surface of the skin a composition comprising in a physiologically acceptable medium at least one compound of formula (I) or a composition containing it .
  • the present invention is particularly intended for the treatment of body odors of a human being.
  • the present invention is intended for the treatment of axillary odors.
  • glycine-betaine derivatives according to the invention are chosen from those corresponding to the following formula (I) and their optical isomers:
  • X denotes an organic or inorganic anion
  • Y denotes O (oxygen atom, forming ester derivatives) or NR '(forming amide derivatives);
  • an aralkyl radical in which the alkyl is C1-C22, linear or branched, saturated or unsaturated, in particular an aralkyl radical, the aryl part of which is a phenyl radical, optionally substituted with 1 to 4 linear C1-C4 alkyl radicals; or branched;
  • aryl radical in particular a phenyl radical optionally substituted with 1 to 4 linear or branched C1-C4 alkyl radicals;
  • an aralkyl radical in which the linear or branched, saturated or unsaturated C1-C22 alkyl, in particular an aralkyl radical, the aryl part of which is a phenyl radical, optionally substituted with 1 to 4 linear or branched C1-C4 alkyl radicals; ;
  • aryl radical in particular a phenyl radical, optionally substituted with 1 to 4 linear or branched C1-C4 alkyl radicals.
  • X " refers for example, without this list is exhaustive: halide (such as for example chloride or bromide, preferably chloride), sulfate, methanesulfonate, citrate, lactate, acetate and any combination thereof.
  • Aryl refers to a monocyclic or polycyclic aromatic hydrocarbon radical comprising from 5 to 22 carbon atoms such as, phenyl or naphthyl, and may optionally include one or more heteroatoms.
  • the aryl radical may comprise one or more substituents, and in particular 1 to 4 linear or branched C1-C4 alkyl radicals.
  • Alkyl denotes an alkyl radical in which a hydrogen atom is substituted with an aryl radical, and in particular with a phenyl radical, optionally substituted with 1 to 4 linear or branched C1-C4 alkyl radicals.
  • the aralkyl radical is bonded to Y by the alkyl radical.
  • R denotes a linear or branched, saturated or unsaturated C 2 -C 22 alkyl radical
  • Y represents O or NR '
  • R and / or R 'de notes a C2-C22 alkyl, linear or branched, saturated or unsaturated.
  • - R denotes a linear or branched, saturated or unsaturated C 2 -C 22 alkyl radical and / or
  • Y represents O or NH.
  • the invention also relates to compounds of formula (I), their optical isomers.
  • the invention relates to compounds which have not been described hitherto in the prior art.
  • the invention relates to a compound below or one of their optical isomers:
  • chloride representing an inorganic organic anion with the exception of chloride, and preferably selected from bromide, sulfate, methanesulfonate, citrate, lactate, acetate, and any combination thereof.
  • the invention relates to the following compounds:
  • the invention relates to the following compound, and in particular its methanesulphonate salt:
  • the invention also relates to combinations of several compounds of formula (I).
  • a compound is considered to possess deodorant properties on resident bacterial flora.
  • the activity of such a compound can be tested on Corynebacterium xerosis strains.
  • a compound is considered active when it reduces the number of revivable bacteria germs by several log, preferably at least 3 log relative to a reference sample in which the test compounds are not present.
  • the present invention also relates to the preparation of compounds defined according to the invention.
  • glycine-betaine ester derivatives (I) which are the subject of the present invention can be obtained for example in two steps from glycine betaine (A):
  • glycine-betaine amide derivatives (I) which are the subject of the present invention can be obtained for example in three steps from glycine betaine (A):
  • the invention also relates to compositions, especially cosmetic, in particular deodorant and possibly antiperspirant, comprising a physiologically acceptable medium.
  • the invention relates in particular to a composition, in particular a cosmetic composition
  • a composition in particular a cosmetic composition
  • a physiologically acceptable medium comprising, in a physiologically acceptable medium, at least one compound of formula (I) according to the invention, in combination with at least one antiperspirant active agent and / or at least one other deodorant active agent.
  • physiologically acceptable medium means a medium suitable for the administration of a composition topically.
  • a physiologically acceptable medium is preferably a cosmetically or dermatologically acceptable medium, that is to say without odor, or unpleasant appearance, and which is perfectly compatible with the topical route of administration.
  • composition is intended to be administered topically, that is to say by surface application of the keratin material in question, such a medium is in particular considered physiologically acceptable when it does not generate tingling, tugging or redness unacceptable to the user.
  • composition according to the invention comprises one or more other deodorant active agents and / or one or more antiperspirant active agents.
  • the term "deodorant active agent” is intended to mean any active ingredient which, by itself, has the effect of masking, absorbing, improving and / or reducing the unpleasant odor resulting from the decomposition of human sweat.
  • An active agent and a deodorant agent have an equivalent meaning according to the present invention.
  • antiperspirant active we mean any substance which, by itself, has the effect of reducing the flow of sweat, of reducing the sensation on the skin of moisture linked to human sweat, of masking human sweat.
  • An antiperspirant active and an anti-perspirant agent have an equivalent meaning according to the present invention.
  • composition according to the invention may contain one or more additional deodorant active agents other than the compounds according to the invention, for example:
  • Bacteriostatic agents or other bactericidal agents such as 2,4,4'-trichloro-2'-hydroxydiphenyl ether (Triclosan), 2,4-dichloro-2'-hydroxydiphenyl ether, 3 ', 4', 5 ' -trichlorosalicylanilide, 1 - (- 3 ', 4'-dichlorophenyl) -3- (4'-chlorophenyl) urea (Triclocarban) or 3,7,1 1 -trimethyldodeca-2,5,10-trienol (Farnesol); quaternary ammonium salts such as cetyltrimethylammonium salts, cetylpyridinium salts; chlorhexidine and salts; diglycerol monocaprate, diglycerol monolaurate, glycerol monolaurate; polyhexamethylene biguanide salts; zinc salts such as zinc salicylate, zinc phenolsulfonate, zinc pyrrol
  • odor absorbers such as zeolites, cyclodextrins, metal oxide silicates such as those described in the application US2005 / 063928; transition metal-modified metal oxide particles as described in US2005084464 and US2005084474, aluminosilicates such as those described in EP1658863, particles of chitosan derivatives such as those described in US6916465;
  • substances blocking the enzymatic reactions responsible for the formation of odorous compounds such as the inhibitors of arylsulfatase, 5-lipoxygenase, aminocyclase, ⁇ -glucoronidase;
  • the deodorant active agents may be present in the composition according to the invention in a proportion of from 0.01% to 20% by weight relative to the total weight of the composition, and preferably at a level of from , 1 to 10% by weight.
  • composition according to the invention may contain one or more antiperspirant active agents.
  • the antiperspirant active agents are preferably chosen from aluminum and / or zirconium salts; complexes of zirconium hydroxychloride and of aluminum hydroxychloride with an amino acid such as those described in patent US-3792068.
  • Such complexes are generally known by the name ZAG (when the amino acid is Glycine).
  • the ZAG complexes usually have an Al / Zr quotient ranging from about 1.67 to 12.5 and a Metal / Cl quotient ranging from about 0.73 to 1.93.
  • aluminum salts mention may be made of aluminum chlorohydrate, aluminum chlorohydrex, aluminum chlorohydrex PEG, aluminum chlorohydrex PG, aluminum dichlorohydrate, aluminum dichlorohydrex PEG, aluminum dichlorohydrex PG, aluminum sesquichlorohydrate, aluminum sesquichlorohydrex PEG, aluminum sesquichlorohydrex PG, alum salts, aluminum sulfate, aluminum zirconium octachlorohydrate, aluminum zirconium pentachlorohydrate, aluminum zirconium tetrachlorohydrate, aluminum zirconium trichlorohydrate and more particularly the aluminum hydroxychloride marketed by the company REHEIS under the name REACH 301® or by the company Guilini Chemie under the name ALOXICOLL PF 40®. Examples of aluminum and zirconium salts are those marketed by REHEIS under the name REACH AZP-908-SUF®.
  • Aluminum chlorohydrate in activated or non-activated form will be used more particularly.
  • the antiperspirant active agents may be present in the composition according to the invention in a proportion of 0.001 to 30% by weight relative to the total weight of the composition and preferably in a proportion of 0.5 to 25% by weight.
  • composition according to the invention may be in any of the galenical forms conventionally used for topical application and especially in the form of aqueous gels, aqueous or aqueous-alcoholic solutions. They can also, by addition of a fatty or oily phase, be in the form of lotion-type dispersions, emulsions of liquid or semi-liquid consistency of the milk type, obtained by dispersion of a fatty phase in an aqueous phase.
  • compositions are prepared according to the usual methods.
  • compositions may in particular be packaged in pressurized form in an aerosol device or in a pump bottle; packaged in a device provided with a perforated wall including a grid; packaged in a device equipped with a roll-on applicator, packaged in the form of sticks (sticks), in the form of loose or compacted powder, in this respect they contain the ingredients generally used in this type of product and well known to those skilled in the art.
  • compositions according to the invention can be anhydrous.
  • anhydrous composition is meant a composition containing less than 2% by weight of water, or even less than 0.5% of water, and especially free of water, the water not being added during the preparation of the composition but corresponding to the residual water provided by the mixed ingredients.
  • compositions according to the invention can be solid, in particular in the form of a stick or a stick.
  • solid composition it is meant that the measurement of the maximum force measured in texturometry during the insertion of a probe into the sample of formula must be at least 0.25 Newton, in particular at least equal to 0.30 Newton, especially at least 0.35 Newton, appreciated under precise measurement conditions as follows.
  • the formulas are poured hot in pots 4 cm in diameter and 3 cm deep. Cooling is done at room temperature. The hardness of the formulas is measured after 24 hours of waiting.
  • the pots containing the samples are characterized in texturometry using a texturometer such as that marketed by Rhéo TA-XT2, according to the following protocol: a ball-type stainless steel probe of diameter 5 mm is brought into contact with the sample at a speed of 1 mm / s.
  • the measurement system detects the interface with the sample with a detection threshold equal to 0.005 newtons.
  • the probe sinks 0.3 mm into the sample at a rate of 0.1 mm / s.
  • the meter records the evolution of the force measured in compression over time, during the penetration phase.
  • the hardness of the sample corresponds to the average of the maximum values of the force detected during the penetration, on at least 3 measurements.
  • compositions according to the invention intended for cosmetic use may comprise at least one aqueous phase. They are in particular formulated in aqueous lotions or in water-in-oil, oil-in-water or multiple emulsion emulsions (triple oil-in-water-in-oil or water-in-oil-in-water emulsion). such emulsions are known and described for example by C. FOX in "Cosmetics and Toiletries" - november 1986 - Vol 101 - pages 101-122).
  • the aqueous phase of said compositions contains water and in general other solvents soluble or miscible in water.
  • Solvents that are soluble or miscible in water include short-chain monohydric alcohols, for example C 1 -C 4 alcohols, such as ethanol or isopropanol; diols or polyols such as ethylene glycol, 1,2-propylene glycol, 1,3-butylene glycol, hexylene glycol, diethylene glycol, dipropylene glycol, 2-ethoxyethanol, diethylene glycol monomethyl ether, triethylene glycol monomethyl ether and sorbitol. More particularly, propylene glycol and glycerol, propane 1,3 diol will be used.
  • composition according to the invention preferably has a pH ranging from 3 to 9 depending on the support chosen.
  • emulsifiers that may be used in oil-in-water emulsions or oil-in-water-in-oil tri-emulsions include, for example, nonionic emulsifiers such as oxyalkylenated fatty acid and glycerol esters (more particularly polyoxyethylenes); oxyalkylenated fatty acid and sorbitan esters; oxyalkylenated fatty acid esters (oxyethylenated and / or oxypropylenated); oxyalkylenated fatty alcohol ethers (oxyethylenated and / or oxypropylenated); sugar esters such as sucrose stearate; and mixtures thereof such as the mixture of glyceryl stearate and PEG-40 stearate.
  • nonionic emulsifiers such as oxyalkylenated fatty acid and glycerol esters (more particularly polyoxyethylenes); oxyalkylenated fatty acid and sorb
  • fatty alcohol / alkylpolyglycoside emulsifying mixtures as described in applications WO92 / 06778, WO95 / 13863 and WO98 / 47610, such as the commercial products sold by the company SEPPIC under the names MONTANOV®.
  • Water-in-oil emulsifiers as described in applications WO92 / 06778, WO95 / 13863 and WO98 / 47610, such as the commercial products sold by the company SEPPIC under the names MONTANOV®.
  • alkyl dimethicone copolyols such as Cetyl PEG / PPG-10/1 DIMETHICONE and more particularly the Cetyl PEG / PPG mixture.
  • -10/1 DIMETICONE and Dimethicone (INCI name) as the product sold under the trade name ABIL EM90® by GOLDSCHMIDT or the mixture (Polyglyceryl-4-stearate and Cetyl PEG / PPG-10 (and) Dimethicone (and) Hexyl Laurate) as the product sold under the trade name ABIL WE09® by the same company.
  • dimethicone copolyols such as PEG-18 / PPG-18 Dimethicone and more particularly the mixture CYCLOPENTASILOXANE (and) PEG-18 / PPG-18 Dimethicone (INCI name) such as the product sold by Dow Corning under the trade name Silicone DC 5225 C® or KF-6040® from Shin Etsu.
  • water-in-oil emulsifiers mention may also be made of nonionic emulsifiers derived from fatty acid and polyol, alkylpolyglycosides (APG), sugar esters and mixtures thereof.
  • APG alkylpolyglycosides
  • nonionic emulsifiers derived from fatty acid and polyol it is possible in particular to use the fatty acid and polyol esters, the fatty acid having in particular a C 8 -C 24 alkyl chain, and the polyols being, for example, glycerol and sorbitan.
  • fatty acid and polyol esters examples include esters of isostearic acid and of polyols, esters of stearic acid and of polyols, and mixtures thereof, in particular esters of isostearic acid and of glycerol, and / or sorbitan.
  • esters of stearic acid and of polyols mention may in particular be made of polyethylene glycol esters such as PEG-30 dipolyhydroxystearate, such as the product sold under the name Arlacel P135® by the company ICI.
  • glycerol and / or sorbitan esters examples include polyglycerol isostearate, such as the product sold under the name Isolan Gl 34® by the company Goldschmidt; sorbitan isostearate, such as the product sold under the name Arlacel 987 by the company ICI; sorbitan isostearate and glycerol, such as the product sold under the name Arlacel 986® by the company ICI, the mixture of sorbitan isostearate and polyglycerol isostearate (3 moles) sold under the name Arlacel 169® by the company Unigema, and their mixtures.
  • polyglycerol isostearate such as the product sold under the name Isolan Gl 34® by the company Goldschmidt
  • sorbitan isostearate such as the product sold under the name Arlacel 987 by the company ICI
  • sorbitan isostearate and glycerol such as the product sold under the name Arlacel 986® by the
  • the emulsifier may also be chosen from alkylpolyglycosides having an HLB of less than 7, for example those represented by the following general formula (1):
  • R'-O- (G) x (1) in which R 'represents a branched and / or unsaturated alkyl radical containing from 14 to 24 carbon atoms, G represents a reduced sugar containing from 5 to 6 carbon atoms, and x denotes a value ranging from 1 to 10 and preferably from 1 to 4, and G denotes, in particular, glucose, fructose or galactose.
  • the unsaturated alkyl radical may comprise one or more ethylenic unsaturations, and in particular one or two ethylenic unsaturations.
  • alkylpolyglycosides of this type mention may be made of alkylpolyglucosides
  • G glucose in formula (I)), and in particular the compounds of formula (I) in which R more particularly represents an oleyl radical (unsaturated C18 radical) or isostearyl radical (saturated d 8), G denotes glucose, x is a value from 1 to 2, in particular isostearyl glucoside, oleyl-glucoside and their mixtures.
  • This alkylpolyglucoside may be used in admixture with a co-emulsifier, more particularly with a fatty alcohol and in particular a fatty alcohol having the same fatty chain as that of the alkylpolyglucoside, that is to say comprising from 14 to 24 carbon atoms.
  • succinic-terminated polyolefins such as ester-terminated polyisobutylenes and their salts, especially diethanolamine salts, such as the products sold under the names Lubrizol 2724®, Lubrizol 2722® and Lubrizol 5603 by Lubrizol®. or the CHEMCINNATE 2000® commercial product.
  • the total amount of emulsifiers will preferably be in the composition according to the invention at contents of active material ranging from 1 to 8% by weight and more particularly from 2 to 6% by weight relative to the total weight of the composition.
  • compositions according to the invention may contain at least one immiscible organic liquid phase in water called the fatty phase.
  • This generally comprises one or more hydrophobic compounds which render said phase immiscible in water.
  • Said phase is liquid (in the absence of structuring agent) at room temperature (20-25 ° C).
  • the immiscible organic liquid phase in water according to the invention generally comprises at least one volatile oil and / or a non-volatile oil and optionally at least one structuring agent.
  • oil means a fatty substance that is liquid at ambient temperature (25 ° C.) and atmospheric pressure (760 mmHg, ie 1 ⁇ 05 ⁇ 10 5 Pa).
  • the oil may be volatile or non-volatile.
  • volatile oil means an oil capable of evaporating on contact with the skin or keratin fiber in less than one hour at ambient temperature and atmospheric pressure.
  • volatile oils of the invention are volatile cosmetic oils which are liquid at ambient temperature and have a non-zero vapor pressure at ambient temperature and atmospheric pressure, in particular from 0.13 Pa to 40 000 Pa (10 -3 to 300 mmHg), in particular ranging from 1.3 Pa to 13000 Pa (0.01 to 100 mmHg), and more particularly ranging from 1, 3 Pa at 1300 Pa (0.01 to 10 mm Hg).
  • non-volatile oil is meant an oil remaining on the skin or keratin fiber at room temperature and atmospheric pressure for at least several hours and having in particular a vapor pressure of less than 10 -3 mmHg (0.13 Pa). .
  • the oil may be chosen from all physiologically acceptable and in particular cosmetically acceptable oils, in particular mineral, animal, vegetable, and synthetic oils; in particular volatile and / or nonvolatile hydrocarbon and / or silicone and / or fluorinated oils and mixtures thereof.
  • hydrocarbon-based oil means an oil comprising mainly carbon and hydrogen atoms and optionally one or more functional groups chosen from hydroxyl, ester, ether and carboxylic functions.
  • the oil has a viscosity of 0.5 to 100,000 mPa.s, preferably 50 to 50,000 mPa.s and more preferably 100 to 300,000 mPa.s.
  • volatile hydrocarbon oils chosen from hydrocarbon oils having 8 to 16 carbon atoms, and especially the C 8 -C isoalkanes 6 of petroleum origin (also known as isoparaffins), for instance isododecane (also known as 2,2,4, 4,6-pentamethylheptane), isodecane, isohexadecane, and for example the oils sold under the trade names Isopars or permetyls, branched C 8 -C 18 esters, isohexyl neopentanoate, and their mixtures.
  • Other volatile hydrocarbon oils such as petroleum distillates, especially those sold under the name Shell or by Shell, may also be used; volatile linear alkanes such as those described in the patent application of Cognis DE10 2008 012 457.
  • volatile silicones for example volatile linear or cyclic silicone oils, in particular those having a viscosity ⁇ 8 centistokes (8 10 ⁇ 6 m 2 / s), and having in particular 2 to 7 silicon atoms, these silicones optionally comprising alkyl or alkoxy groups having 1 to 10 carbon atoms.
  • volatile silicone oil that can be used in the invention, there may be mentioned in particular octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, heptamethylhexyltrisiloxane, heptamethyloctyltrisiloxane, hexamethylisiloxane, octamethyltrisiloxane and decamethyl tetrasiloxane, dodecamethylpentasiloxane
  • R represents an alkyl group comprising from 2 to 4 carbon atoms and one or more hydrogen atoms of which may be substituted by a fluorine or chlorine atom.
  • non-volatile oil that may be used in the invention, mention may be made of:
  • hydrocarbon oils of animal origin such as perhydrosqualene
  • vegetable hydrocarbon oils such as liquid triglycerides of fatty acids of 4 to 24 carbon atoms such as triglycerides of heptanoic or octanoic acids or oils oils of wheat germ, olive oil, sweet almond oil , palm, colza, cotton, alfalfa, poppy, pumpkin, squash, black currant, evening primrose, millet, barley, quinoa, rye, safflower,nadooulier, passionflower , musk rose, sunflower, maize, soya, squash, grape seed, sesame, hazelnut, apricot, macadamia, castor, avocado, caprylic / capric acid triglycerides as those sold by Stearineries Dubois or those sold under the names Miglyol 810, 812 and 818 by Dynamit Nobel, jojoba oil, shea butter;
  • linear or branched hydrocarbons of mineral or synthetic origin such as liquid paraffins and derivatives thereof, petroleum jelly, polydecenes, polybutenes, hydrogenated polyisobutene such as Parleam, squalane;
  • synthetic ethers having from 10 to 40 carbon atoms; synthetic esters, in particular of fatty acids, such as the oils of formula R COOR 2 in which R represents the residue of a linear or branched higher fatty acid containing from 1 to 40 carbon atoms and R 2 represents a hydrocarbon chain, in particular a branched hydrocarbon chain, containing from 1 to 40 carbon atoms with R 1 + R 2 > 10 such as, for example, purcellin oil (cetostearyl octanoate), isononyl isononanoate, isopropyl myristate, isopropyl palmitate, benzoate of C12 to C15 alcohol, hexyl laurate, diisopropyl adipate, ethyl 2-hexyl palmitate, octyl 2-dodecyl stearate, octyl 2-dodecyl erucate, isostearyl isostearate, tridecyl trimellitate
  • branched-chain and / or unsaturated carbon-chain liquid fatty alcohols having from 12 to 26 carbon atoms, such as octyl dodecanol, isostearyl alcohol, 2-butyloctanol, 2-hexyl decanol and 2-undecyl; pentadecanol, oleic alcohol;
  • higher fatty acids such as oleic acid, linoleic acid, linolenic acid;
  • fluorinated oils that may be partially hydrocarbon-based and / or silicone-based, such as fluorosilicone oils, fluorinated polyethers or fluorinated silicones, as described in document EP-A-847752;
  • silicone oils such as non-volatile, linear or cyclic polydimethylsiloxanes (PDMS); polydimethylsiloxanes comprising alkyl, alkoxy or phenyl groups, during or at the end of the silicone chain, groups having from 2 to 24 carbon atoms; phenyl silicones such as phenyl trimethicones, phenyl dimethicones, phenyl trimethylsiloxy diphenyl siloxanes, diphenyl dimethicones, diphenyl methyldiphenyl trisiloxanes, 2-phenylethyl trimethylsiloxysilicates, and
  • the cosmetic compositions according to the invention may furthermore comprise cosmetic adjuvants chosen from softeners, antioxidants, opacifiers, stabilizers, moisturizing agents, vitamins, bactericides, preservatives, polymers, perfumes and a structuring agent.
  • cosmetic adjuvants chosen from softeners, antioxidants, opacifiers, stabilizers, moisturizing agents, vitamins, bactericides, preservatives, polymers, perfumes and a structuring agent.
  • fatty phase in particular chosen from waxes, pasty compounds, gelling agents; organic or inorganic fillers; thickeners or suspending agents, propellants or any other ingredient usually used in cosmetics for this type of application.
  • the wax is in general a lipophilic compound, solid at room temperature (25 ° C.), with reversible solid / liquid state change, having a melting point of greater than or equal to 30 ° C. and up to 200 'C and especially up to 120' C.
  • the waxes that are suitable for the invention may have a melting point greater than or equal to 45 ° C., and in particular greater than or equal to 55 ° C.
  • the melting temperature corresponds to the temperature of the most endothermic peak observed in thermal analysis (DSC) as described in the ISO 1 1357-3 standard; 1999.
  • the melting point of the wax can be measured using a differential scanning calorimeter (DSC), for example the calorimeter sold under the name "MDSC 2920®” by the company TA Instruments.
  • the measurement protocol is as follows:
  • a sample of 5 mg of wax placed in a crucible is subjected to a first temperature rise from -20 ° C. to 100 ° C., at the heating rate of 10 ° / minute, and is then cooled from 100 ° C. to 20 ° C at a cooling rate of 10 ⁇ / minute and finally subjected to a second temperature rise from -20 ° C to 100 ° C at a heating rate of 5 ° C / minute.
  • the melting point of the compound is the value of the temperature corresponding to the top of the peak of the curve representing the variation of the difference in power absorbed as a function of the temperature.
  • the waxes that may be used in the compositions according to the invention are chosen from waxes, solid, at room temperature of animal, vegetable, mineral or synthetic origin, and mixtures thereof.
  • Illustrative waxes suitable for the invention include hydrocarbon waxes such as beeswax, lanolin wax, and Chinese insect wax, rice bran wax, Carnauba wax Candellila wax, Ouricury wax, Alfa wax, berry wax, shellac wax, Japanese wax and sumac wax; montan wax, orange and lemon waxes, refined sunflower wax sold under the name SUNFLOWER WAX® by KOSTER KEUNEN, microcrystalline waxes, paraffins and ozokerite; polyethylene waxes, waxes obtained by Fisher-Tropsch synthesis and waxy copolymers and their esters.
  • hydrocarbon waxes such as beeswax, lanolin wax, and Chinese insect wax, rice bran wax, Carnauba wax Candellila wax, Ouricury wax, Alfa wax, berry wax, shellac wax, Japanese wax and sumac wax
  • montan wax, orange and lemon waxes refined sunflower wax sold under the name SUNFLOWER WAX® by KOSTER
  • isomérz jojoba oil such as trans isomerized partially hydrogenated jojoba oil manufactured or marketed by Desert Whale under the trade reference lso-Jojoba-50®, sunflower oil hydrogenated castor oil, hydrogenated coconut oil, hydrogenated lanolin oil, and di- (trimethylol-1,1,1-propane) tetrastearate sold under the name Hest 2T-4S® by the company HETERENE.
  • silicone waxes C30-45 ALKYL DIMETHICONE
  • fluorinated waxes C30-45 ALKYL DIMETHICONE
  • waxes obtained by hydrogenation of castor oil esterified with cetyl alcohol sold under the names Phytowax Ricin 16L64® and 22L73® by the company SOPHIM. Such waxes are described in application FR-A-2792190.
  • a C20-C40 alkyl (hydroxystearyloxy) stearate (the alkyl group comprising from 20 to 40 carbon atoms), alone or in admixture, can be used.
  • Such a wax is especially sold under the names "Kester Wax K 82 P®", “Hydroxypolyester K 82 P®” and “Kester Wax K 80 P®” by the company Koster Keunen.
  • micro-waxes that can be used in the compositions according to the invention, mention may be made in particular of carnauba micro-waxes such as that marketed under the name MicroCare 350® by the company MICRO POWDERS, the microwaxes of synthetic wax such as that marketed under the name MicroEase 1 14S® by the company MICRO POWDERS, the micro waxes consisting of a mixture of carnauba wax and polyethylene wax such as those sold under the names of Micro Care 300® and 310® by the company MICRO POWDERS, micro waxes consisting of a mixture of carnauba wax and synthetic wax such as that marketed under the name Micro Care 325® by the company MICRO POWDERS, polyethylene micro-waxes such as those marketed under the names Micropoly 200®, 220®, 220L® and 250S® by the company Micro Powders, the commercial products PERFOMALEN 400 POLYETHYLENE® and PERFORMALENE 500-L POLYETHYLENE®
  • the term "pasty compound” is intended to mean a lipophilic fat compound having a reversible solid / liquid state change, having in the solid state an anisotropic crystalline organization, and comprising at a temperature of 23.degree. liquid and a solid fraction.
  • the pasty compound is preferably chosen from synthetic compounds and compounds of plant origin.
  • a pasty compound can be obtained synthetically from starting materials of plant origin.
  • composition according to the invention may further contain one or more suspending agents and / or one or more gelling agents. Some of them can play both roles at once.
  • optionally modified clays in particular hydrophobic modified montmorillonite clays, such as hydrophobic modified bentonites or hectorites, such as hectorites modified with a C10 ammonium chloride.
  • C 22 such as hectorite modified by chloride distearyl di-methyl ammonium such as, for example, the product disteardimonium hectorite (CTFA name) (product of reaction of hectorite and of distearyldimonium chloride) sold under the Bentone 38 or Bentone Gel by Elementis Specialties.
  • CFA name product disteardimonium hectorite
  • CFA name reaction product of bentonite and of quaternary ammonium stearalkonium chloride
  • CTFA name reaction product of bentonite and of quaternary ammonium stearalkonium chloride
  • Tixogel MP 250® by the company Sud Chemie Rheologicals, United Catalysts Inc.
  • hydrotalcites in particular hydrophobic modified hydrotalcites, for example the products sold under the name Gilugel by the company BK Giulini.
  • fumed silica optionally treated with hydrophobic surface, the particle size of which is less than 1 ⁇ . It is indeed possible to chemically modify the surface of the silica, by chemical reaction generating a decrease in the number of silanol groups present on the surface of the silica. In particular, it is possible to substitute silanol groups with hydrophobic groups: a hydrophobic silica is then obtained.
  • the hydrophobic groups may be trimethylsiloxyl groups, which are especially obtained by treatment of fumed silica in the presence of hexamethyldisilazane. Silicas thus treated are called “Silica silylate” according to the CTFA (8th edition, 2000).
  • Silicas thus treated are called "Silica dimethyl silylate” according to the CTFA (8th edition, 2000). They are for example marketed under the references Aerosil R972®, and Aerosil R974® by the company DEGUSSA, CAB-O-SIL TS-610® and CAB-O-SIL TS-720® by CABOT.
  • the hydrophobic fumed silica has in particular a particle size that can be nanometric to micrometric, for example ranging from about 5 to 200 nm.
  • suspending agents or gelling agents may be used, in this case in hydrophilic media (aqueous and / or ethanolic).
  • hydrophilic media aqueous and / or ethanolic.
  • cellulosic derivatives which may be microcrystalline
  • xanthan xanthan
  • guar starch including modified corn starch marketed under the name Structure XL by Akzo Nobel
  • carob agar agar.
  • compositions according to the invention are those conventionally used in compositions, especially for the treatment of perspiration and / or body odor. aerosols
  • compositions according to the invention may be pressurized and packaged in an aerosol device consisting of:
  • Propellants generally used in this type of product and well known to those skilled in the art are, for example, dimethyl ether (DME); volatile hydrocarbons such as n-butane, propane, isobutane, and mixtures thereof, optionally with at least one chlorinated and / or fluorinated hydrocarbon; among these are the compounds sold by the company Dupont de Nemours under the names Freon® and Dymel®, and in particular monofluorotrichloromethane, difluorodichloromethane, tetrafluorodichloroethane and 1,1-difluoroethane sold especially under the trade name Dymel 152 A® by DUPONT.
  • DME dimethyl ether
  • volatile hydrocarbons such as n-butane, propane, isobutane, and mixtures thereof, optionally with at least one chlorinated and / or fluorinated hydrocarbon
  • Freon® and Dymel® the compounds sold by the company Dupont de Nemours under the names Fre
  • compositions containing the perlite particles as defined above and the propellant (s) may be in the same compartment or in different compartments in the aerosol container.
  • concentration of propellant generally varies from 5 to 95% by weight pressurized and more preferably from 50 to 85% by weight relative to the total weight of the pressurized composition.
  • the dispensing means which forms part of the aerosol device, is generally constituted by a dispensing valve controlled by a dispensing head, itself comprising a nozzle through which the aerosol composition is vaporized.
  • the container containing the pressurized composition may be opaque or transparent. It may be glass, polymeric material or metal, optionally covered with a layer of protective varnish.
  • the invention also relates to a package ("packaging") or information notice including, possibly among other visual information, the mention of the presence of one or more of the compounds according to the invention, and / or the presence at least one antiperspirant active agent and / or at least one other deodorant active agent.
  • the invention relates to a package or information notice comprising the list of ingredients of a composition according to the present invention.
  • the packaging or the information leaflet presents visual information concerning the treatment of odors and / or perspiration, in particular in a human being. More particularly, this packaging or information notice is intended to inform a user of the destination of the composition or device according to the invention, already packaged or which should be packed therein.
  • the invention also relates to a composition according to the invention, or a device comprising it, accompanied by a packaging or information notice, particularly as defined above.
  • the invention relates in particular to a composition, in particular a cosmetic composition, comprising in a physiologically acceptable medium at least one compound of formula (I) according to the invention, optionally in combination with at least one antiperspirant active agent and / or at least one other active ingredient.
  • deodorant in a physiologically acceptable medium said composition being accompanied by a package or information notice presenting visual information concerning the treatment of odors and / or perspiration of a human being, and / or information on the presence of at least one asset antiperspirant and / or at least one deodorant active, possibly among other visual information.
  • the temperature is that ambient (20-25 ° C)
  • the pressure is atmospheric (101 325 Pa), unless otherwise indicated.
  • the mass of ingredients is expressed as a percentage relative to the mass of the total composition considered.
  • Example 2 Preparation of Compound 2
  • a mixture of betaine (A) (24 g, 0.2 mol), 3-octanol (60 ml) and methanesulfonic acid (18 ml) is heated at 140 ° C. for 8 h under an inert atmosphere (N 2 ). After returning to ambient temperature, the excess of acid is neutralized by adding a saturated aqueous solution of betaine. This mixture is then concentrated to dryness by evaporation under reduced pressure. The residue is taken up in acetone to redissolve the product. After filtration of the betaine salts, the filtrate is concentrated by evaporation under reduced pressure. The compound thus obtained is purified by recrystallization from n-heptane. The product 2 is thus isolated in the form of a brown solid. (3g - yield 4.5%).
  • a mixture of betaine (A) (150 g, 1.28 mol), isopropanol (615 g) and methanesulfonic acid (91 ml) is heated at 130 ° C. with stirring while distilling the isopropanol continuously and with continuous addition of isopropanol. After 24 h, 100 ml of methanesulfonic acid are added. After 48 hours and follow the formation of the product by NMR 75 ml of methanesulfonic acid are added. After 72h, the reaction medium is filtered and the filtrate is concentrated by evaporation under reduced pressure. The reaction crude is purified by adding betaine in isopropanol to neutralize the residual acid. The mixture is centrifuged, the pellet is removed and the liquid phase is evaporated under reduced pressure. The product 8 is thus isolated in the form of a white solid. (107g - 33% yield).
  • reaction medium is placed at 4 ⁇ C to precipitate the residual betaine.
  • the filtrate is then concentrated and the product is precipitated in diethyl ether. It is isolated in the form of a white solid.
  • the principle of the method is as follows: the raw materials are put in contact with the bacteria in a suitable medium, and after a contact time of 24 hours, the reduction in the number of revivable germs is measured, compared to a placebo without said raw materials.

Abstract

The invention relates to the use of at least one compound of the following formula (I) or one of the optical isomers thereof, as a deodorising agent in a composition, especially a cosmetic composition. The invention also relates to compositions comprising such a compound, to devices comprising the composition, to compounds as such, and to a cosmetic method for treating body odours.

Description

Dérivés esters et amides de glycine-bétaine comme actifs déodorants, compositions cosmétiques qui les comprennent  Derivatives of glycine-betaine esters and amides as deodorant active ingredients, cosmetic compositions which comprise them
La présente invention concerne des dérivés esters et amides de glycine-bétaïne comme actifs déodorants, des compositions cosmétiques en comprenant, ainsi que leurs utilisations en cosmétique. The present invention relates to glycine-betaine esters and amide derivatives as deodorant active agents, cosmetic compositions comprising them, as well as their uses in cosmetics.
La présente invention concerne en particulier une association des dérivés esters et amides de glycine-bétaïne avec un ou plusieurs actifs déodorants et/ou un ou plusieurs actifs anti-transpirants.  In particular, the present invention relates to a combination of glycine-betaine ester and amide derivatives with one or more deodorant active agents and / or one or more antiperspirant active agents.
Dans le domaine cosmétique, il est bien connu d'utiliser en application topique, des produits déodorants contenant des substances actives de type anti-transpirant ou de type déodorant pour diminuer voire supprimer les odeurs axillaires généralement désagréables.  In the cosmetic field, it is well known to use, in topical application, deodorant products containing active substances of the antiperspirant or deodorant type to reduce or even eliminate the generally unpleasant axillary odors.
Les substances déodorantes détruisent en général la flore bactérienne résidente. Parmi ces substances, les plus employées sont le Triclosan (2,4,4'-trichloro-2'- hydroxydiphényléther) et le farnésol qui présentent l'inconvénient de modifier de façon importante l'écologie de la flore cutanée. Il existe les substances qui diminuent la croissance des bactéries. Parmi ces substances, on peut citer les chélatants de métaux de transition comme le l'EDTA ou le DPTA. Ces matériaux privent le milieu des métaux nécessaires à la croissance des bactéries.  Deodorant substances usually destroy the resident bacterial flora. Among these substances, the most used are Triclosan (2,4,4'-trichloro-2'-hydroxydiphenyl ether) and farnesol which have the disadvantage of significantly modifying the ecology of skin flora. There are substances that decrease the growth of bacteria. Among these substances, mention may be made of transition metal chelating agents such as EDTA or DPTA. These materials deprive the medium of metals necessary for the growth of bacteria.
Il subsiste cependant le besoin de trouver de nouveaux ingrédients actifs qui soient efficaces en activité déodorante, et notamment améliorant l'efficacité déodorante, tout en étant faciles à formuler comme produit destiné à diminuer la transpiration et/ou les odeurs, en particulier chez l'être humain, et plus particulièrement pour lutter contre les odeurs corporelles et plus spécifiquement les odeurs axillaires.  However, there remains the need to find new active ingredients that are effective in deodorant activity, including improving deodorant efficiency, while being easy to formulate as a product for reducing perspiration and / or odors, particularly in the be human, and more particularly to fight against body odors and more specifically axillary odors.
Certains composés de formule (I) sont connus de l'art antérieur (Par exemple Chemische Berichte, 1943, vol. 76, p. 15, 18). Cependant, leurs activités connues ne permettaient pas d'envisager de préparer des produits destinés à diminuer la transpiration et/ou les odeurs corporelles chez l'être humain.  Certain compounds of formula (I) are known from the prior art (eg Chemische Berichte, 1943, vol 76, p 15, 18). However, their known activities did not allow to consider preparing products intended to reduce perspiration and / or body odor in humans.
La demande de brevet chinois CN86106630 décrit des compositions comprenant des tensioactifs qui auraient une activité de désodorisation et de stérilisation, mais seraient principalement utilisées pour la désodorisation des toilettes, enclos de ferme, poulaillers, chambres d'élevage d'animaux, et pour éliminer les mauvaises odeurs produites par la nourriture pourrie, l'odeur de poisson et de viande dans le réfrigérateur, de cuisine, des ateliers de transformation alimentaire, épiceries et d'égouts (abrégé). L'enseignement de cette demande ne permet pas de résoudre les problèmes posés par la présente invention, ces applications étant très différentes du traitement des odeurs ou de la transpiration chez un être humain. Chinese patent application CN86106630 discloses compositions comprising surfactants which would have deodorizing and sterilizing activity, but would be mainly used for the deodorization of toilets, farm pens, poultry houses, animal rearing rooms, and to eliminate bad odors produced by rotten food, the smell of fish and meat in the refrigerator, kitchen, food processing workshops, grocery stores and sewerage (abbreviated). The teaching of this application does not solve the problems posed by the the present invention, these applications being very different from the treatment of odors or perspiration in a human being.
Il est connu également que des sels d'ammonium quaternaire présentent une activité bactéricide (voir A.E. EPSHTEIN et al.: "Bactericidal quaternary ammonium salts based on monochloroacetic acid esters", & Khim.-Farm. Zh. 1980, 14(5), 23-6). Seule l'activité sur des micro-organismes du type Escherichia coli ou Staphylococcus aureus sont décrites. Ainsi l'enseignement de ce document ne permet pas de résoudre les problèmes posés par la présente invention.  It is also known that quaternary ammonium salts exhibit bactericidal activity (see AE EPSHTEIN et al .: "Bactericidal quaternary ammonium salts based on monochloroacetic acid esters", & Khim.-Farm, 1980, 14 (5), 23-6). Only the activity on microorganisms of the Escherichia coli or Staphylococcus aureus type are described. Thus the teaching of this document does not solve the problems posed by the present invention.
La demande internationale WO 2005/044237 décrit des esters de bétaïne utilisés comme tensioactifs dans les compositions pharmaceutiques notamment pour former des vecteurs de délivrance d'ingrédients actifs.  International application WO 2005/044237 describes betaine esters used as surfactants in pharmaceutical compositions, in particular to form active ingredient delivery vectors.
Par ailleurs, des dérivés esters et amides de bétaïne sont décrits dans le brevet Furthermore, betaine esters and amide derivatives are described in the patent.
US 2 888 383, ainsi que leur synthèse. Cependant ces compositions sont particulièrement adaptées à l'hygiène bucco-dentaire. Il s'agit en particulier de dentifrices. US 2,888,383, as well as their synthesis. However, these compositions are particularly suitable for oral hygiene. These are in particular toothpastes.
La demande internationale WO 2006/105669 concernent des produits qui présenteraient une activité antimicrobienne sur Staphylococcus aureus, Bacillus cereus, International application WO 2006/105669 relates to products which would exhibit antimicrobial activity on Staphylococcus aureus, Bacillus cereus,
Escherichia coli, Shigella sp., Salmonella sp. et Listeria monocytogenes ou antifongique sur différents champignons. Escherichia coli, Shigella sp., Salmonella sp. and Listeria monocytogenes or antifungal on different fungi.
Enfin, la demande française FR 2 869 913 décrit des tensioactifs comprenant un ester ou amide de glycine bétaïne pour leurs propriétés détergentes, émulsifiantes ou moussantes. Cette demande décrit en particulier des compositions de savon liquide, bain moussant, gel douche ou shampooing.  Finally, the French application FR 2 869 913 describes surfactants comprising an ester or amide of glycine betaine for their detergent, emulsifying or foaming properties. This application describes in particular compositions of liquid soap, bubble bath, shower gel or shampoo.
Ainsi, aucun de ces documents antérieurs ne permet de résoudre les problèmes techniques que se propose de résoudre la présente invention.  Thus, none of these prior documents can solve the technical problems that the present invention proposes to solve.
Les inventeurs ont découvert d'une manière surprenante que des dérivés esters et amides de glycine-bétaine de formule (I) détaillée ci-dessous présentaient une bonne efficacité déodorante et pouvaient être facilement formulés comme produit destiné à diminuer les odeurs corporelles, seul, en combinaison, ou en association avec des anti- transpirants ou des actifs déodorants classiques.  The inventors have surprisingly discovered that glycine-betaine ester and amide derivatives of formula (I) detailed below have good deodorant efficacy and can be easily formulated as a product intended to reduce body odor, alone, in particular. combination, or in combination with conventional antiperspirants or deodorant actives.
Ainsi l'invention concerne l'utilisation d'un composé de formule (I), que l'on donnera plus loin en détail, comme agent déodorant notamment dans une composition comprenant un support physiologiquement acceptable.  Thus, the invention relates to the use of a compound of formula (I), which will be given later in detail, as a deodorant agent in particular in a composition comprising a physiologically acceptable carrier.
La présente invention a pour objet également une composition, notamment cosmétique, comprenant dans un milieu physiologiquement acceptable au moins un composé de formule (I) en association avec au moins un actif anti-transpirant et/ou au moins un actif déodorant. La présente invention a pour objet également une méthode cosmétique de traitement des odeurs corporelles en particulier axillaires, consistant à appliquer sur la surface de la peau une composition comprenant dans un milieu physiologiquement acceptable au moins un composé de formule (I) ou une composition en contenant. The subject of the present invention is also a composition, in particular a cosmetic composition, comprising in a physiologically acceptable medium at least one compound of formula (I) in combination with at least one antiperspirant active agent and / or at least one deodorant active agent. The subject of the present invention is also a cosmetic method for treating body odors, in particular axillary odors, consisting in applying to the surface of the skin a composition comprising in a physiologically acceptable medium at least one compound of formula (I) or a composition containing it .
La présente invention est en particulier destinée au traitement des odeurs corporelles d'un être humain. En particulier, la présente invention est destinée au traitement des odeurs axillaires.  The present invention is particularly intended for the treatment of body odors of a human being. In particular, the present invention is intended for the treatment of axillary odors.
L'invention est décrite ci-dessous plus en détails.  The invention is described below in more detail.
Dérivés esters et amides de qlvcine-bétaine Derivatives of esters and amides of quinoline-betaine
Les dérivés de glycine-bétaine conformes à l'invention sont choisis parmi ceux répondant à la formule (I) suivante et leurs isomères optiques :
Figure imgf000004_0001
The glycine-betaine derivatives according to the invention are chosen from those corresponding to the following formula (I) and their optical isomers:
Figure imgf000004_0001
 or
X" désigne un anion organique ou inorganique ; X " denotes an organic or inorganic anion;
Y désigne O (atome d'oxygène, formant des dérivés esters) ou NR' (formant des dérivés amides) ;  Y denotes O (oxygen atom, forming ester derivatives) or NR '(forming amide derivatives);
R désigne:  R designates:
- un radical alkyle en C2-C22, linéaire ou ramifié, saturé ou insaturé ;  a C2-C22 alkyl radical, linear or branched, saturated or unsaturated;
- un radical aralkyle, où l'alkyle est en C1 -C22, linéaire ou ramifié, saturé ou insaturé, en particulier un radical aralkyle, dont la partie aryle désigne un radical phényle, éventuellement substitué par 1 à 4 radicaux alkyles C1 -C4 linéaires ou ramifiés ;  an aralkyl radical, in which the alkyl is C1-C22, linear or branched, saturated or unsaturated, in particular an aralkyl radical, the aryl part of which is a phenyl radical, optionally substituted with 1 to 4 linear C1-C4 alkyl radicals; or branched;
- un radical aryle, en particulier un radical phényle éventuellement substitué par 1 à 4 radicaux alkyles C1 -C4 linéaires ou ramifiés ;  an aryl radical, in particular a phenyl radical optionally substituted with 1 to 4 linear or branched C1-C4 alkyl radicals;
R' désigne :  R 'designates:
o un atome d'hydrogène ;  o a hydrogen atom;
o un radical alkyle en C1 -C22, linéaire ou ramifié, saturé ou insaturé ;  o a linear or branched, saturated or unsaturated C 1 -C 22 alkyl radical;
o un radical aralkyle, où l'alkyle en C1 -C22, linéaire ou ramifié, saturé ou insaturé, en particulier un radical aralkyle dont la partie aryle désigne un radical phényle, éventuellement substitué par 1 à 4 radicaux alkyles C1 -C4 linéaires ou ramifiés ;  an aralkyl radical, in which the linear or branched, saturated or unsaturated C1-C22 alkyl, in particular an aralkyl radical, the aryl part of which is a phenyl radical, optionally substituted with 1 to 4 linear or branched C1-C4 alkyl radicals; ;
o un radical aryle, en particulier un radical phényle, éventuellement substitué par 1 à 4 radicaux alkyles C1 -C4 linéaires ou ramifiés. X" désigne par exemple, sans que cette liste soit exhaustive : halogénure (tel que par exemple chlorure ou bromure, de préférence chlorure), sulfate, méthanesulfonate, citrate, lactate, acétate et l'une quelconque de leurs combinaisons. an aryl radical, in particular a phenyl radical, optionally substituted with 1 to 4 linear or branched C1-C4 alkyl radicals. X " refers for example, without this list is exhaustive: halide (such as for example chloride or bromide, preferably chloride), sulfate, methanesulfonate, citrate, lactate, acetate and any combination thereof.
« Aryle » désigne un radical hydrocarboné aromatique monocyclique ou polycyclique comprenant de 5 à 22 atomes de carbone tels que, phényle ou naphthyle, et peut comprendre éventuellement un ou plusieurs hétéroatomes. Le radical aryle peut comprendre un ou plusieurs substituants, et en particulier 1 à 4 radicaux alkyles C1 -C4 linéaires ou ramifiés.  "Aryl" refers to a monocyclic or polycyclic aromatic hydrocarbon radical comprising from 5 to 22 carbon atoms such as, phenyl or naphthyl, and may optionally include one or more heteroatoms. The aryl radical may comprise one or more substituents, and in particular 1 to 4 linear or branched C1-C4 alkyl radicals.
"Aralkyle" désigne un radical alkyle dans lequel un atome d'hydrogène est substitué par un radical aryle, et en particulier par un radical phényle, éventuellement substitué par 1 à 4 radicaux alkyles C1 -C4 linéaires ou ramifiés. Le radical aralkyle est lié à Y par le radical alkyle.  "Aralkyl" denotes an alkyl radical in which a hydrogen atom is substituted with an aryl radical, and in particular with a phenyl radical, optionally substituted with 1 to 4 linear or branched C1-C4 alkyl radicals. The aralkyl radical is bonded to Y by the alkyl radical.
Parmi les composés de formule (I), et leurs isomères optiques on choisira de préférence les composés pour lesquels :  Among the compounds of formula (I), and their optical isomers, the compounds for which:
- R désigne un radical alkyle linéaire ou ramifié, saturé ou insaturé en C2-C22 ; - R denotes a linear or branched, saturated or unsaturated C 2 -C 22 alkyl radical;
- Y représente O ou NR' ;  Y represents O or NR ';
- R' désigne :  - R 'designates:
o un atome d'hydrogène  o a hydrogen atom
o un radical alkyle en C1 -C22, linéaire ou ramifié, saturé ou insaturé. o a linear or branched, saturated or unsaturated C 1 -C 22 alkyl radical.
De préférence, R et/ou R' désigne un C2-C22 alkyle, linéaire ou ramifié, saturé ou insaturé. Preferably, R and / or R 'denotes a C2-C22 alkyl, linear or branched, saturated or unsaturated.
Parmi les composés de formule (I), ou l'un de ses isomères optiques, on choisit de façon particulièrement préférée les composés pour lesquels :  Among the compounds of formula (I), or one of its optical isomers, compounds which are:
- R désigne un radical alkyle linéaire ou ramifié, saturé ou insaturé en C2-C22 et/ou- R denotes a linear or branched, saturated or unsaturated C 2 -C 22 alkyl radical and / or
- Y représente O ou NH. Y represents O or NH.
Parmi les composés de formule (I), on choisit encore plus particulièrement les composés suivants, ou leurs isomères optiques : Among the compounds of formula (I), the following compounds, or their optical isomers, are chosen more particularly:
Tableau 1 Table 1
Composés Structure
Figure imgf000006_0001
Figure imgf000007_0001
Figure imgf000008_0001
Structure compounds
Figure imgf000006_0001
Figure imgf000007_0001
Figure imgf000008_0001
X" ayant la même signification que précédemment. X " having the same meaning as above.
L'invention concerne également des composés de formule (I), leurs isomères optiques. En particulier, l'invention concerne des composés qui ne sont pas décrits jusqu'alors dans l'art antérieur. The invention also relates to compounds of formula (I), their optical isomers. In particular, the invention relates to compounds which have not been described hitherto in the prior art.
Plus particulièrement, l'invention concerne un composé ci-dessous ou l'un de leurs isomères optiques :  More particularly, the invention relates to a compound below or one of their optical isomers:
Figure imgf000008_0002
Figure imgf000008_0002
, X" ayant la même signification que précédemment ; X " having the same meaning as before;
Figure imgf000008_0003
représentant un anion organique inorganique à l'exception du chlorure, et de préférence choisi parmi bromure, sulfate, méthanesulfonate, citrate, lactate, acétate, et l'une quelconque de leurs combinaisons.
Figure imgf000008_0003
representing an inorganic organic anion with the exception of chloride, and preferably selected from bromide, sulfate, methanesulfonate, citrate, lactate, acetate, and any combination thereof.
En particulier, l'invention concerne les composés suivants :  In particular, the invention relates to the following compounds:
Figure imgf000008_0004
Figure imgf000008_0004
Il s'agit des sels de méthanesulfonate des composés précités.  These are the methanesulphonate salts of the aforementioned compounds.
Plus particulièrement, l'invention concerne le composé suivant, et notamment son sel de méthanesulfonate : More particularly, the invention relates to the following compound, and in particular its methanesulphonate salt:
Figure imgf000009_0001
Figure imgf000009_0001
L'invention concerne également des combinaisons de plusieurs composés de formule (I). The invention also relates to combinations of several compounds of formula (I).
Par l'expression « selon l'invention », on entend l'un quelconque des modes de réalisation ou variantes, y compris ceux généraux et ceux plus spécifiques ou préférés et leurs combinaisons, cette référence devant être interprétée au sens le plus large.  By the term "according to the invention" is meant any of the embodiments or variants, including those general and those more specific or preferred and combinations thereof, this reference to be interpreted in the broadest sense.
Un composé est considéré comme possédant des propriétés déodorantes sur la flore bactérienne résidante. On peut tester l'activité d'un tel composé sur des souches Corynebacterium xérosis. Un composé est considéré actif lorsqu'il réduit le nombre de germes de bactéries revivifiables par plusieurs log, de préférence d'au moins 3 log par rapport à un échantillon de référence dans lequel les composés testés ne sont pas présents.  A compound is considered to possess deodorant properties on resident bacterial flora. The activity of such a compound can be tested on Corynebacterium xerosis strains. A compound is considered active when it reduces the number of revivable bacteria germs by several log, preferably at least 3 log relative to a reference sample in which the test compounds are not present.
La présente invention concerne également la préparation de composés définis selon l'invention.  The present invention also relates to the preparation of compounds defined according to the invention.
Certains des composés de formule (I) étant connus de l'art antérieur, l'homme du métier peut s'appuyer sur la littérature pour la préparation de l'ensemble des composés de formule (I) de l'invention.  Since some of the compounds of formula (I) are known from the prior art, those skilled in the art can rely on the literature for the preparation of all the compounds of formula (I) of the invention.
Des schémas généraux de synthèse sont les suivants : General schemes of synthesis are as follows:
Préparation des dérivés esters (Y = O) Preparation of ester derivatives (Y = O)
Les dérivés esters de glycine-bétaine (I) faisant l'objet de la présente invention peuvent être obtenus par exemple en deux étapes à partir de la glycine bétaine (A) :  The glycine-betaine ester derivatives (I) which are the subject of the present invention can be obtained for example in two steps from glycine betaine (A):
- en utilisant l'alcool ROH comme solvant, acidification de la bétaine initialement sous forme zwitterionique par un excès d'acide HX  - using alcohol ROH as solvent, acidification of betaine initially in zwitterionic form with an excess of HX acid
- puis estérification du mélange ainsi obtenu (présence d'acide HX résiduel) par exemple avec un chauffage à 60-160 'Ό. ) - Then esterification of the mixture thus obtained (presence of residual HX acid) for example with a heating at 60-160 'Ό. )
Figure imgf000010_0001
Figure imgf000010_0001
Préparation des dérivés amides (Y = NFO Preparation of amide derivatives (Y = NFO
Les dérivés amides de glycine-bétaine (I) faisant l'objet de la présente invention peuvent être obtenus par exemple en trois étapes à partir de la glycine bétaine (A) :  The glycine-betaine amide derivatives (I) which are the subject of the present invention can be obtained for example in three steps from glycine betaine (A):
- activation de la glycine bétaine (A) sous la forme du chlorure d'acyle correspondant  activation of glycine betaine (A) in the form of the corresponding acyl chloride
- substitution du chlore par la 2-mercaptothiazoline en milieu basique (obtention de l'intermédiaire (B))  - substitution of chlorine by 2-mercaptothiazoline in basic medium (obtaining intermediate (B))
- transamidation avec l'aminé RR'NH  transamidation with amine RR'NH
Figure imgf000010_0002
Figure imgf000010_0002
R I R I
HN
Figure imgf000010_0003
HN
Figure imgf000010_0003
L'invention concerne encore des compositions, notamment cosmétiques, en particulier à pouvoir déodorant et éventuellement anti-transpirant, comprenant un milieu physiologiquement acceptable. The invention also relates to compositions, especially cosmetic, in particular deodorant and possibly antiperspirant, comprising a physiologically acceptable medium.
L'invention concerne notamment une composition, notamment composition cosmétique comprenant dans un milieu physiologiquement acceptable au moins un composé de formule (I) selon l'invention, en association avec au moins un actif anti- transpirant et/ou au moins un autre actif déodorant dans un milieu physiologiquement acceptable. Au sens de la présente invention, on entend désigner par « milieu physiologiquement acceptable », un milieu convenant à l'administration d'une composition par voie topique. The invention relates in particular to a composition, in particular a cosmetic composition comprising, in a physiologically acceptable medium, at least one compound of formula (I) according to the invention, in combination with at least one antiperspirant active agent and / or at least one other deodorant active agent. in a physiologically acceptable medium. For the purposes of the present invention, the term "physiologically acceptable medium" means a medium suitable for the administration of a composition topically.
Un milieu physiologiquement acceptable est préférentiellement un milieu cosmétiquement ou dermatologiquement acceptable, c'est-à-dire sans odeur, ou aspect désagréable, et qui est parfaitement compatible avec la voie d'administration topique.  A physiologically acceptable medium is preferably a cosmetically or dermatologically acceptable medium, that is to say without odor, or unpleasant appearance, and which is perfectly compatible with the topical route of administration.
Dans le cas présent où la composition est destinée à être administrée par voie topique, c'est à dire par application en surface de la matière kératinique considérée, un tel milieu est en particulier considéré comme physiologiquement acceptable lorsqu'il ne génère pas de picotement, tiraillement ou rougeur inacceptable pour l'utilisateur.  In the present case where the composition is intended to be administered topically, that is to say by surface application of the keratin material in question, such a medium is in particular considered physiologically acceptable when it does not generate tingling, tugging or redness unacceptable to the user.
Avantageusement la composition selon l'invention comprend un ou plusieurs autres actifs déodorants et/ou un ou plusieurs actifs anti-transpirants.  Advantageously, the composition according to the invention comprises one or more other deodorant active agents and / or one or more antiperspirant active agents.
Par « actif déodorant », on entend dans le cadre de la présente invention tout actif qui, à lui seul, a pour effet de masquer, absorber, améliorer et/ou diminuer l'odeur désagréable résultant de la décomposition de la sueur humaine. Un actif et un agent déodorant ont un sens équivalent selon la présente invention.  For the purposes of the present invention, the term "deodorant active agent" is intended to mean any active ingredient which, by itself, has the effect of masking, absorbing, improving and / or reducing the unpleasant odor resulting from the decomposition of human sweat. An active agent and a deodorant agent have an equivalent meaning according to the present invention.
Par « actif anti-transpirant » on entend toute substance qui, à elle seule, a pour effet de diminuer le flux sudoral, de diminuer la sensation sur la peau d'humidité liée à la sueur humaine, de masquer la sueur humaine. Un actif et un agent anti-transpirant ont un sens équivalent selon la présente invention.  By "antiperspirant active" we mean any substance which, by itself, has the effect of reducing the flow of sweat, of reducing the sensation on the skin of moisture linked to human sweat, of masking human sweat. An antiperspirant active and an anti-perspirant agent have an equivalent meaning according to the present invention.
Composition cosmétiques Cosmetic composition
Actifs déodorants additionnels Additional deodorant active ingredients
La composition selon l'invention peut contenir un ou plusieurs actifs déodorants additionnels autres que les composés selon de l'invention, comme par exemple : The composition according to the invention may contain one or more additional deodorant active agents other than the compounds according to the invention, for example:
- Des agents bactériostatiques ou d'autres agents bactéricides tels que 2,4,4'- trichloro-2'-hydroxydiphényléther (Triclosan), le 2,4-dichloro-2'-hydroxydiphényléther, le 3',4',5'-trichlorosalicylanilide, la 1 -(-3',4'-dichlorophenyl)-3-(4'chlorophenyl)urée (Triclocarban) ou le 3,7,1 1 -triméthyldodéca-2, 5,10-triénol (Farnesol) ; les sels d'ammonium quaternaires comme les sels de cétyltrimethylammonium, les sels de cétylpyridinium ; la chlorhexidine et les sels ; le monocaprate de diglycérol, le monolaurate de diglycérol, monolaurate de glycérol ; les sels de polyhexaméthylène biguanide ; - des sels de zinc comme le salicylate de zinc, le phénolsulfonate de zinc, le pyrrolidone carboxylate de zinc (plus communément appelé pidolate de zinc), le sulfate de zinc, le chlorure de zinc, le lactate de zinc, le gluconate de zinc, ricinoléate de zinc, glycinate de zinc, carbonate de zinc, citrate de zinc, chlorure de zinc, le laurate de zinc, l'oléate de zinc, l'orthophosphate de zinc, le stéréate de zinc, le tartrate de zinc, l'acétate de zinc ou leurs mélanges ; Bacteriostatic agents or other bactericidal agents such as 2,4,4'-trichloro-2'-hydroxydiphenyl ether (Triclosan), 2,4-dichloro-2'-hydroxydiphenyl ether, 3 ', 4', 5 ' -trichlorosalicylanilide, 1 - (- 3 ', 4'-dichlorophenyl) -3- (4'-chlorophenyl) urea (Triclocarban) or 3,7,1 1 -trimethyldodeca-2,5,10-trienol (Farnesol); quaternary ammonium salts such as cetyltrimethylammonium salts, cetylpyridinium salts; chlorhexidine and salts; diglycerol monocaprate, diglycerol monolaurate, glycerol monolaurate; polyhexamethylene biguanide salts; zinc salts such as zinc salicylate, zinc phenolsulfonate, zinc pyrrolidone carboxylate (more commonly known as zinc pidolate), zinc sulphate, zinc chloride, zinc lactate, zinc gluconate, zinc ricinoleate, zinc glycinate, zinc carbonate, zinc citrate, zinc chloride, zinc laurate, zinc oleate, zinc orthophosphate, zinc steroid, zinc tartrate, acetate zinc or mixtures thereof;
- des absorbeurs d'odeurs comme les zéolites, les cyclodextrines, les silicates d'oxyde métallique telles que celles décrite dans la demande US2005/063928 ; des particules d'oxyde métallique modifiées par un métal de transition telles que décrites dans les demandes US2005084464 et US2005084474, des aluminosilicates comme ceux décrits dans la demande EP1658863, des particules de dérivés de chitosan comme celles décrites dans le brevet US6916465 ;  odor absorbers such as zeolites, cyclodextrins, metal oxide silicates such as those described in the application US2005 / 063928; transition metal-modified metal oxide particles as described in US2005084464 and US2005084474, aluminosilicates such as those described in EP1658863, particles of chitosan derivatives such as those described in US6916465;
- des substances bloquant les réactions enzymatiques responsables de la formation de composés odorants comme les inhibeurs d'arylsulfatase, de 5- Lipoxygenase, d'aminocyclase, de β-glucoronidase ;  substances blocking the enzymatic reactions responsible for the formation of odorous compounds such as the inhibitors of arylsulfatase, 5-lipoxygenase, aminocyclase, β-glucoronidase;
et leurs mélanges.  and their mixtures.
Les actifs déodorants (y compris les composés selon l'invention) peuvent être présents dans la composition selon l'invention à raison de 0,01 à 20 % en poids par rapport au poids total de la composition, et de préférence à raison de 0,1 à 10 % en poids. The deodorant active agents (including the compounds according to the invention) may be present in the composition according to the invention in a proportion of from 0.01% to 20% by weight relative to the total weight of the composition, and preferably at a level of from , 1 to 10% by weight.
Actifs anti-transpirants Antiperspirant active ingredients
La composition selon l'invention peut contenir un ou plusieurs actifs anti- transpirants. The composition according to the invention may contain one or more antiperspirant active agents.
Les actifs anti-transpirants sont choisis de préférence parmi les sels d'aluminium et/ou de zirconium ; les complexes d'hydroxychlorure de zirconium et d'hydroxychlorure d'aluminium avec un acide aminé tels que ceux décrits dans le brevet US-3792068. De tels complexes sont généralement connus sous l'appellation ZAG (lorsque l'acide aminé est la Glycine). Les complexes ZAG présentent d'ordinaire un quotient Al/Zr allant d'environ 1 ,67 à 12,5 et un quotient Métal/Cl allant d'environ 0,73 à 1 ,93. Parmi ces produits on peut citer l'aluminium zirconium octachlorohydrex GLY, l'aluminium zirconium pentachlorohydrex GLY, l'aluminium zirconium tetrachlorohydrate GLY et l'aluminium zirconium trichlorohydrate-GLY.  The antiperspirant active agents are preferably chosen from aluminum and / or zirconium salts; complexes of zirconium hydroxychloride and of aluminum hydroxychloride with an amino acid such as those described in patent US-3792068. Such complexes are generally known by the name ZAG (when the amino acid is Glycine). The ZAG complexes usually have an Al / Zr quotient ranging from about 1.67 to 12.5 and a Metal / Cl quotient ranging from about 0.73 to 1.93. Among these products, mention may be made of aluminum zirconium octachlorohydrex GLY, aluminum zirconium pentachlorohydrex GLY, aluminum zirconium tetrachlorohydrate GLY and aluminum zirconium trichlorohydrate-GLY.
Parmi les sels d'aluminium, on peut citer le chlorhydrate d'aluminium, l'aluminium chlorohydrex, l'aluminium chlorohydrex PEG, l'aluminium chlorohydrex PG, l'aluminium dichlorohydrate, l'aluminium dichlorohydrex PEG, l'aluminium dichlorohydrex PG, l'aluminium sesquichlorohydrate, l'aluminium sesquichlorohydrex PEG, l'aluminium sesquichlorohydrex PG, les sels d'alun, l'aluminium sulfate, l'aluminium zirconium octachlorohydrate, l'aluminium zirconium pentachlorohydrate, l'aluminium zirconium tetrachlorohydrate, l'aluminium zirconium trichlorohydrate et plus particulièrement l'hydroxychlorure d'aluminium commercialisé par la société REHEIS sous la dénomination REACH 301® ou par la société GUILINI CHEMIE sous la dénomination ALOXICOLL PF 40®. Des sels d'aluminium et de zirconium sont par exemple celui commercialisé par la société REHEIS sous la dénomination REACH AZP-908-SUF®. Among the aluminum salts, mention may be made of aluminum chlorohydrate, aluminum chlorohydrex, aluminum chlorohydrex PEG, aluminum chlorohydrex PG, aluminum dichlorohydrate, aluminum dichlorohydrex PEG, aluminum dichlorohydrex PG, aluminum sesquichlorohydrate, aluminum sesquichlorohydrex PEG, aluminum sesquichlorohydrex PG, alum salts, aluminum sulfate, aluminum zirconium octachlorohydrate, aluminum zirconium pentachlorohydrate, aluminum zirconium tetrachlorohydrate, aluminum zirconium trichlorohydrate and more particularly the aluminum hydroxychloride marketed by the company REHEIS under the name REACH 301® or by the company Guilini Chemie under the name ALOXICOLL PF 40®. Examples of aluminum and zirconium salts are those marketed by REHEIS under the name REACH AZP-908-SUF®.
On utilisera plus particulièrement le chlorohydrate d'aluminium sous forme activée ou non activée.  Aluminum chlorohydrate in activated or non-activated form will be used more particularly.
Les actifs anti-transpirants peuvent être présents dans la composition selon l'invention à raison de 0,001 à 30 % en poids par rapport au poids total de la composition et de préférence à raison de 0,5 à 25 % en poids.  The antiperspirant active agents may be present in the composition according to the invention in a proportion of 0.001 to 30% by weight relative to the total weight of the composition and preferably in a proportion of 0.5 to 25% by weight.
Formes qaléniques Qalenic forms
La composition selon l'invention peut se présenter sous toutes les formes galéniques classiquement utilisées pour une application topique et notamment sous forme de gels aqueux, de solutions aqueuses ou hydroalcooliques. Elles peut aussi, par ajout d'une phase grasse ou huileuse, se présenter sous forme de dispersions du type lotion, d'émulsions de consistance liquide ou semi-liquide du type lait, obtenues par dispersion d'une phase grasse dans une phase aqueuse (H/E) ou inversement (E/H), ou de suspensions ou émulsions de consistance molle, semi-solide ou solide du type crème ou gel, ou encore d'émulsions multiples (E/H/E ou H/E/H), de microémulsions, de dispersions vésiculaires de type ionique et/ou non ionique, ou des dispersions cire/phase aqueuse. Ces compositions sont préparées selon les méthodes usuelles. The composition according to the invention may be in any of the galenical forms conventionally used for topical application and especially in the form of aqueous gels, aqueous or aqueous-alcoholic solutions. They can also, by addition of a fatty or oily phase, be in the form of lotion-type dispersions, emulsions of liquid or semi-liquid consistency of the milk type, obtained by dispersion of a fatty phase in an aqueous phase. (W / O) or conversely (W / O), or suspensions or emulsions of soft, semi-solid or solid consistency of the cream or gel type, or multiple emulsions (W / O / W or H / E / H), microemulsions, vesicular dispersions of ionic and / or nonionic type, or wax / aqueous phase dispersions. These compositions are prepared according to the usual methods.
Les compositions peuvent être notamment conditionnées sous forme pressurisée dans un dispositif aérosol ou dans un flacon pompe ; conditionnée dans un dispositif muni d'une paroi ajourée notamment une grille ; conditionnées dans un dispositif muni d'un applicateur à billes ("roll-on) ; conditionnées sous forme de bâtonnets (sticks), sous forme de poudre libre ou compactée. Elles contiennent à cet égard les ingrédients généralement utilisés dans ce type de produits et bien connus de l'homme de l'art.  The compositions may in particular be packaged in pressurized form in an aerosol device or in a pump bottle; packaged in a device provided with a perforated wall including a grid; packaged in a device equipped with a roll-on applicator, packaged in the form of sticks (sticks), in the form of loose or compacted powder, in this respect they contain the ingredients generally used in this type of product and well known to those skilled in the art.
Selon une autre forme particulière de l'invention, les compositions selon l'invention peuvent être anhydres. On entend par composition anhydre une composition contenant moins de 2 % en poids d'eau, voire moins de 0,5 % d'eau, et notamment exempte d'eau, l'eau n'étant pas ajoutée lors de la préparation de la composition mais correspondant à l'eau résiduelle apportée par les ingrédients mélangés. According to another particular form of the invention, the compositions according to the invention can be anhydrous. By anhydrous composition is meant a composition containing less than 2% by weight of water, or even less than 0.5% of water, and especially free of water, the water not being added during the preparation of the composition but corresponding to the residual water provided by the mixed ingredients.
Selon une autre forme particulière de l'invention, les compositions selon l'invention peuvent être solides en particulier sous forme de bâtonnet ou stick.  According to another particular form of the invention, the compositions according to the invention can be solid, in particular in the form of a stick or a stick.
Par «composition solide», on entend que la mesure de la force maximale mesurée en texturométrie lors de l'enfoncement d'une sonde dans l'échantillon de formule doit être au moins égale à 0,25 Newton, en particulier au moins égal à 0,30 Newton, notamment au moins égale 0,35 Newton, appréciée dans des conditions de mesure précises comme suit.  By "solid composition" it is meant that the measurement of the maximum force measured in texturometry during the insertion of a probe into the sample of formula must be at least 0.25 Newton, in particular at least equal to 0.30 Newton, especially at least 0.35 Newton, appreciated under precise measurement conditions as follows.
Les formules sont coulées à chaud dans des pots de 4 cm de diamètre et 3 cm de fond. Le refroidissement est fait à température ambiante. La dureté des formules réalisées est mesurée après 24 heures d'attente. Les pots contenant les échantillons sont caractérisés en texturométrie à l'aide d'un texturomètre tel que celui commercialisé par la société Rhéo TA-XT2, selon le protocole suivant : une sonde de type bille en inox de diamètre 5 mm est amenée au contact de l'échantillon à une vitesse de 1 mm/s. Le système de mesure détecte l'interface avec l'échantillon avec un seuil de détection égal à 0,005 newtons. La sonde s'enfonce de 0,3 mm dans l'échantillon, à une vitesse de 0,1 mm/s. L'appareil de mesure enregistre l'évolution de la force mesurée en compression au cours du temps, pendant la phase de pénétration. La dureté de l'échantillon correspond à la moyenne des valeurs maximales de la force détectée pendant la pénétration, sur au moins 3 mesures. Phase aqueuse  The formulas are poured hot in pots 4 cm in diameter and 3 cm deep. Cooling is done at room temperature. The hardness of the formulas is measured after 24 hours of waiting. The pots containing the samples are characterized in texturometry using a texturometer such as that marketed by Rhéo TA-XT2, according to the following protocol: a ball-type stainless steel probe of diameter 5 mm is brought into contact with the sample at a speed of 1 mm / s. The measurement system detects the interface with the sample with a detection threshold equal to 0.005 newtons. The probe sinks 0.3 mm into the sample at a rate of 0.1 mm / s. The meter records the evolution of the force measured in compression over time, during the penetration phase. The hardness of the sample corresponds to the average of the maximum values of the force detected during the penetration, on at least 3 measurements. Aqueous phase
Les compositions selon l'invention destinées à l'usage cosmétique peuvent comporter au moins une phase aqueuse. Elles sont notamment formulées en lotions aqueuses ou en émulsion eau-dans-huile, huile-dans-eau, ou en émulsion multiple (émulsion triple huile-dans-eau-dans-huile ou eau-dans-huile-dans-eau (de telles émulsions sont connues et décrites par exemple par C. FOX dans « Cosmetics and Toiletries » - november 1986 - Vol 101 - pages 101 -1 12). The compositions according to the invention intended for cosmetic use may comprise at least one aqueous phase. They are in particular formulated in aqueous lotions or in water-in-oil, oil-in-water or multiple emulsion emulsions (triple oil-in-water-in-oil or water-in-oil-in-water emulsion). such emulsions are known and described for example by C. FOX in "Cosmetics and Toiletries" - november 1986 - Vol 101 - pages 101-122).
La phase aqueuse des dites compositions contient de l'eau et en général d'autres solvants solubles ou miscibles dans l'eau. Les solvants solubles ou miscibles dans l'eau comprennent les mono alcools à chaîne courte par exemple en C1 -C4 comme l'éthanol, l'isopropanol ; les diols ou les polyols comme l'éthylèneglycol, le 1 ,2-propylèneglycol, le 1 ,3-butylène glycol, l'hexylèneglycol, le diéthylèneglycol, le dipropylene glycol, le 2- éthoxyéthanol, le diéthylène glycol monométhyléther, le triéthylène glycol monométhyléther et le sorbitol. On utilisera plus particulièrement le propylèneglycol et la glycérine, le propane 1 ,3 diol. The aqueous phase of said compositions contains water and in general other solvents soluble or miscible in water. Solvents that are soluble or miscible in water include short-chain monohydric alcohols, for example C 1 -C 4 alcohols, such as ethanol or isopropanol; diols or polyols such as ethylene glycol, 1,2-propylene glycol, 1,3-butylene glycol, hexylene glycol, diethylene glycol, dipropylene glycol, 2-ethoxyethanol, diethylene glycol monomethyl ether, triethylene glycol monomethyl ether and sorbitol. More particularly, propylene glycol and glycerol, propane 1,3 diol will be used.
La composition selon l'invention a de préférence un pH allant de 3 à 9 selon le support choisi.  The composition according to the invention preferably has a pH ranging from 3 to 9 depending on the support chosen.
Émulsionnants Emulsionnants huile-dans-eau Emulsifiers oil-in-water emulsifiers
Comme émulsionnants pouvant être utilisés dans les émulsions huile-dans-eau ou émulsions triples huile-dans-eau-dans-huile, on peut citer par exemple les émulsionnants non ioniques tels que les esters d'acides gras et de glycérol oxyalkylénés (plus particulièrement polyoxyéthylénés) ; les esters d'acides gras et de sorbitan oxyalkylénés ; les esters d'acides gras oxyalkylénés (oxyéthylénés et/ou oxypropylénés) ; les éthers d'alcools gras oxyalkylénés (oxyéthylénés et/ou oxypropylénés) ; les esters de sucres comme le stéarate de sucrose ; et leurs mélanges tels que le mélange de stéarate de glycéryle et de stéarate de PEG-40. Examples of emulsifiers that may be used in oil-in-water emulsions or oil-in-water-in-oil tri-emulsions include, for example, nonionic emulsifiers such as oxyalkylenated fatty acid and glycerol esters (more particularly polyoxyethylenes); oxyalkylenated fatty acid and sorbitan esters; oxyalkylenated fatty acid esters (oxyethylenated and / or oxypropylenated); oxyalkylenated fatty alcohol ethers (oxyethylenated and / or oxypropylenated); sugar esters such as sucrose stearate; and mixtures thereof such as the mixture of glyceryl stearate and PEG-40 stearate.
On peut citer également les mélanges émulsionnants alcool gras/alkylpolyglycoside tels que sont décrits dans les demandes WO92/06778, W095/13863 et WO98/47610 comme les produits commerciaux vendus par la société SEPPIC sous les appellations MONTANOV ®. Emulsionnants eau-dans-huile  Mention may also be made of the fatty alcohol / alkylpolyglycoside emulsifying mixtures as described in applications WO92 / 06778, WO95 / 13863 and WO98 / 47610, such as the commercial products sold by the company SEPPIC under the names MONTANOV®. Water-in-oil emulsifiers
Parmi les émulsionnants pouvant être utilisés dans les émulsions eau-dans-huile ou émulsions triples, on peut citer à titre d'exemple les alkyl dimethicone copolyols comme le Cetyl PEG/PPG-10/1 DIMETHICONE et plus particulièrement le mélange Cetyl PEG/PPG-10/1 DIMETICONE and Dimethicone (nom INCI) comme le produit vendu sous le nom commercial ABIL EM90® par la société GOLDSCHMIDT ou bien le mélange (Polyglyceryl-4-stearate and Cetyl PEG/PPG-10 (and) Dimethicone (and) Hexyl Laurate) comme le produit vendu sous le nom commercial ABIL WE09® par la même société. Among the emulsifiers that may be used in water-in-oil emulsions or triple emulsions, mention may be made by way of example of alkyl dimethicone copolyols such as Cetyl PEG / PPG-10/1 DIMETHICONE and more particularly the Cetyl PEG / PPG mixture. -10/1 DIMETICONE and Dimethicone (INCI name) as the product sold under the trade name ABIL EM90® by GOLDSCHMIDT or the mixture (Polyglyceryl-4-stearate and Cetyl PEG / PPG-10 (and) Dimethicone (and) Hexyl Laurate) as the product sold under the trade name ABIL WE09® by the same company.
Parmi les émulsionnants eau-dans-huile, on peut citer également les dimethicone copolyols comme le PEG-18/PPG-18 Dimethicone et plus particulièrement le mélange CYCLOPENTASILOXANE (and) PEG-18/PPG-18 Dimethicone (nom INCI) tel que le produit vendu par la société Dow Corning sous la dénomination commerciale Silicone DC 5225 C® ou KF-6040® de la société Shin Etsu. Among the water-in-oil emulsifiers, mention may also be made of dimethicone copolyols such as PEG-18 / PPG-18 Dimethicone and more particularly the mixture CYCLOPENTASILOXANE (and) PEG-18 / PPG-18 Dimethicone (INCI name) such as the product sold by Dow Corning under the trade name Silicone DC 5225 C® or KF-6040® from Shin Etsu.
Parmi les émulsionnants eau-dans-huile, on peut citer également les émulsionnants non ioniques dérivés d'acide gras et de polyol, les alkylpolyglycosides (APG), les esters de sucres et leurs mélanges.  Among the water-in-oil emulsifiers, mention may also be made of nonionic emulsifiers derived from fatty acid and polyol, alkylpolyglycosides (APG), sugar esters and mixtures thereof.
Comme émulsionnants non ioniques dérivés d'acide gras et de polyol, on peut utiliser notamment les esters d'acide gras et de polyol, l'acide gras ayant notamment une chaîne alkyle en C8-C24, et les polyols étant par exemple le glycérol et le sorbitan.  As nonionic emulsifiers derived from fatty acid and polyol, it is possible in particular to use the fatty acid and polyol esters, the fatty acid having in particular a C 8 -C 24 alkyl chain, and the polyols being, for example, glycerol and sorbitan.
Comme esters d'acide gras et de polyol, on peut citer notamment les esters d'acide isostéarique et de polyols, les esters d'acide stéarique et de polyols, et leurs mélanges, en particulier les esters d'acide isostéarique et de glycérol et/ou de sorbitan.  Examples of fatty acid and polyol esters that may be mentioned include esters of isostearic acid and of polyols, esters of stearic acid and of polyols, and mixtures thereof, in particular esters of isostearic acid and of glycerol, and / or sorbitan.
Comme esters d'acide stéarique et de polyols, on peut citer notamment les esters de polyéthylèneglycol comme le PEG-30 Dipolyhydroxystearate tel que le produit commercialisé sous le nom Arlacel P135® par la société ICI.  As esters of stearic acid and of polyols, mention may in particular be made of polyethylene glycol esters such as PEG-30 dipolyhydroxystearate, such as the product sold under the name Arlacel P135® by the company ICI.
Comme esters de glycérol et/ou de sorbitan, on peut citer par exemple l'isostéarate de polyglycérol, tel que le produit commercialisé sous la dénomination Isolan Gl 34® par la société Goldschmidt ; l'isostéarate de sorbitan, tel que le produit commercialisé sous la dénomination Arlacel 987 par la société ICI ; l'isostéarate de sorbitan et le glycérol, tel que le produit commercialisé sous la dénomination Arlacel 986® par la société ICI, le mélange d'isostéarate de sorbitan et d'isostéarate de polyglycérol (3 moles) commercialisé sous la dénomination Arlacel 169® par la société Unigema, et leurs mélanges.  Examples of glycerol and / or sorbitan esters that may be mentioned are polyglycerol isostearate, such as the product sold under the name Isolan Gl 34® by the company Goldschmidt; sorbitan isostearate, such as the product sold under the name Arlacel 987 by the company ICI; sorbitan isostearate and glycerol, such as the product sold under the name Arlacel 986® by the company ICI, the mixture of sorbitan isostearate and polyglycerol isostearate (3 moles) sold under the name Arlacel 169® by the company Unigema, and their mixtures.
L'émulsionnant peut être choisi aussi parmi les alkylpolyglycosides ayant un HLB inférieur à 7, par exemple ceux représentés par la formule générale (1 ) suivante :  The emulsifier may also be chosen from alkylpolyglycosides having an HLB of less than 7, for example those represented by the following general formula (1):
R'-0-(G)x (1 ) dans laquelle R' représente un radical alkyle ramifié et/ou insaturé, comportant de 14 à 24 atomes de carbone, G représente un sucre réduit comportant de 5 à 6 atomes de carbone, et x désigne une valeur allant de 1 à 10 et de préférence de 1 à 4, et G désigne notamment le glucose, le fructose ou le galactose. R'-O- (G) x (1) in which R 'represents a branched and / or unsaturated alkyl radical containing from 14 to 24 carbon atoms, G represents a reduced sugar containing from 5 to 6 carbon atoms, and x denotes a value ranging from 1 to 10 and preferably from 1 to 4, and G denotes, in particular, glucose, fructose or galactose.
Le radical alkyle insaturé peut comprendre une ou plusieurs insaturations éthyléniques, et en particulier une ou deux insaturations éthyléniques. The unsaturated alkyl radical may comprise one or more ethylenic unsaturations, and in particular one or two ethylenic unsaturations.
Comme alkylpolyglycosides de ce type, on peut citer les alkylpolyglucosides As alkylpolyglycosides of this type, mention may be made of alkylpolyglucosides
(G=glucose dans la formule (I)), et notamment les composés de formule (I) dans laquelle R représente plus particulièrement un radical oléyle (radical insaturé en C18) ou isostéaryle (radical saturé en d8), G désigne le glucose, x est une valeur allant de 1 à 2, notamment l'isostéaryl-glucoside, l'oléyl-glucoside et leurs mélanges. Cet alkylpolyglucoside peut être utilisé en mélange avec un co-émulsionnant, plus spécialement avec un alcool gras et notamment un alcool gras ayant la même chaîne grasse que celle de l'alkylpolyglucoside, c'est-à-dire comportant de 14 à 24 atomes de carbone et ayant une chaîne ramifiée et/ou insaturée, et par exemple l'alcool isostéarylique quand l'alkylpolyglucoside est l'isostéaryl-glucoside, et l'alcool oléylique quand l'alkylpolyglucoside est l'oleyl-glucoside, éventuellement sous forme d'une composition autoémulsionnante, comme décrit par exemple dans le document WO-A- 92/06778. (G = glucose in formula (I)), and in particular the compounds of formula (I) in which R more particularly represents an oleyl radical (unsaturated C18 radical) or isostearyl radical (saturated d 8), G denotes glucose, x is a value from 1 to 2, in particular isostearyl glucoside, oleyl-glucoside and their mixtures. This alkylpolyglucoside may be used in admixture with a co-emulsifier, more particularly with a fatty alcohol and in particular a fatty alcohol having the same fatty chain as that of the alkylpolyglucoside, that is to say comprising from 14 to 24 carbon atoms. carbon and having a branched and / or unsaturated chain, and for example isostearyl alcohol when the alkylpolyglucoside is isostearylglucoside, and oleyl alcohol when the alkylpolyglucoside is oleylglucoside, optionally in the form of a self-emulsifying composition, as described for example in WO-A-92/06778.
On peut également citer les polyoléfines à terminaison succinique, comme les polyisobutylènes à terminaison succinique estérifiée et leurs sels, notamment les sels de diéthanolamine, tels que les produits commercialisés sous les dénominations Lubrizol 2724®, Lubrizol 2722® et Lubrizol 5603 par la société Lubrizol® ou le produit commercial CHEMCINNATE 2000®.  Mention may also be made of succinic-terminated polyolefins, such as ester-terminated polyisobutylenes and their salts, especially diethanolamine salts, such as the products sold under the names Lubrizol 2724®, Lubrizol 2722® and Lubrizol 5603 by Lubrizol®. or the CHEMCINNATE 2000® commercial product.
La quantité totale en émulsionnants sera de préférence dans la composition selon l'invention à des teneurs en matière active allant de 1 à 8% en poids et plus particulièrement de 2 à 6% en poids par rapport au poids total de la composition.  The total amount of emulsifiers will preferably be in the composition according to the invention at contents of active material ranging from 1 to 8% by weight and more particularly from 2 to 6% by weight relative to the total weight of the composition.
Phase grasse Fatty phase
Les compositions selon l'invention peuvent contenir au moins une phase liquide organique non-miscible dans l'eau appelée phase grasse. Celle-ci comprend en général un ou plusieurs composés hydrophobes qui rendent ladite phase non-miscible dans l'eau. Ladite phase est liquide (en l'absence d'agent structurant) à température ambiante (20- 25°C). De manière préférentielle, la phase liquide organique non-miscible dans l'eau conforme à l'invention comprend généralement au moins une huile volatile et/ou une huile non volatile et éventuellement au moins un agent structurant.  The compositions according to the invention may contain at least one immiscible organic liquid phase in water called the fatty phase. This generally comprises one or more hydrophobic compounds which render said phase immiscible in water. Said phase is liquid (in the absence of structuring agent) at room temperature (20-25 ° C). Preferably, the immiscible organic liquid phase in water according to the invention generally comprises at least one volatile oil and / or a non-volatile oil and optionally at least one structuring agent.
Par « huile », on entend un corps gras liquide à température ambiante (25 °C) et pression atmosphérique (760mm de Hg soit 1 .05x105 Pa) L'huile peut être volatile ou non volatile. The term "oil" means a fatty substance that is liquid at ambient temperature (25 ° C.) and atmospheric pressure (760 mmHg, ie 1 × 05 × 10 5 Pa). The oil may be volatile or non-volatile.
Par « huile volatile », on entend au sens de l'invention une huile susceptible de s'évaporer au contact de la peau ou de la fibre kératinique en moins d'une heure, à température ambiante et pression atmosphérique. Les huiles volatiles de l'invention sont des huiles cosmétiques volatiles, liquides à température ambiante, ayant une pression de vapeur non nulle, à température ambiante et pression atmosphérique, allant en particulier de 0,13 Pa à 40 000 Pa (10~3 à 300 mm de Hg), en particulier allant de 1 ,3 Pa à 13 000 Pa (0,01 à 100 mm de Hg), et plus particulièrement allant de 1 ,3 Pa à 1300 Pa (0,01 à 10 mm de Hg). For the purposes of the invention, the term "volatile oil" means an oil capable of evaporating on contact with the skin or keratin fiber in less than one hour at ambient temperature and atmospheric pressure. The volatile oils of the invention are volatile cosmetic oils which are liquid at ambient temperature and have a non-zero vapor pressure at ambient temperature and atmospheric pressure, in particular from 0.13 Pa to 40 000 Pa (10 -3 to 300 mmHg), in particular ranging from 1.3 Pa to 13000 Pa (0.01 to 100 mmHg), and more particularly ranging from 1, 3 Pa at 1300 Pa (0.01 to 10 mm Hg).
Par « huile non volatile », on entend une huile restant sur la peau ou la fibre kératinique à température ambiante et pression atmosphérique au moins plusieurs heures et ayant notamment une pression de vapeur inférieure à 10~3 mm de Hg (0,13 Pa). By "non-volatile oil" is meant an oil remaining on the skin or keratin fiber at room temperature and atmospheric pressure for at least several hours and having in particular a vapor pressure of less than 10 -3 mmHg (0.13 Pa). .
L'huile peut être choisie parmi toutes les huiles physiologiquement acceptables et en particulier cosmétiquement acceptables, notamment les huiles minérales, animales, végétales, synthétiques ; en particulier les huiles hydrocarbonées et/ou siliconées et/ou fluorées volatiles ou non volatiles et leurs mélanges.  The oil may be chosen from all physiologically acceptable and in particular cosmetically acceptable oils, in particular mineral, animal, vegetable, and synthetic oils; in particular volatile and / or nonvolatile hydrocarbon and / or silicone and / or fluorinated oils and mixtures thereof.
Plus précisément, par « huile hydrocarbonée », on entend une huile comportant principalement des atomes de carbone et d'hydrogène et éventuellement une ou plusieurs fonctions choisies parmi les fonctions hydroxyle, ester, éther, carboxylique. Généralement, l'huile présente une viscosité de 0,5 à 100 000 mPa.s, de préférence de 50 à 50 000 mPa.s et de préférence encore de 100 à 300 000 mPa.s.  More precisely, the term "hydrocarbon-based oil" means an oil comprising mainly carbon and hydrogen atoms and optionally one or more functional groups chosen from hydroxyl, ester, ether and carboxylic functions. Generally, the oil has a viscosity of 0.5 to 100,000 mPa.s, preferably 50 to 50,000 mPa.s and more preferably 100 to 300,000 mPa.s.
A titre d'exemple d'huile volatile utilisable dans l'invention, on peut citer :  By way of example of volatile oil that may be used in the invention, mention may be made of:
les huiles hydrocarbonées volatiles choisies parmi les huiles hydrocarbonées ayant de 8 à 16 atomes de carbones, et notamment les isoalcanes en C8-Ci6 d'origine pétrolière (appelées aussi isoparaffines) comme l'isododécane (encore appelé 2,2,4,4,6-pentaméthylheptane), l'isodécane, l'isohexadécane, et par exemple les huiles vendues sous les noms commerciaux d'Isopars ou de Permetyls, les esters ramifiés en C8-Ci6, le néopentanoate d'iso-hexyle, et leurs mélanges. D'autres huiles hydrocarbonées volatiles comme les distillais de pétrole, notamment ceux vendus sous la dénomination Shell Soit par la société SHELL, peuvent aussi être utilisées ; les alcanes linéaires volatils comme ceux décrits dans la demande de brevet de la société Cognis DE10 2008 012 457. volatile hydrocarbon oils chosen from hydrocarbon oils having 8 to 16 carbon atoms, and especially the C 8 -C isoalkanes 6 of petroleum origin (also known as isoparaffins), for instance isododecane (also known as 2,2,4, 4,6-pentamethylheptane), isodecane, isohexadecane, and for example the oils sold under the trade names Isopars or permetyls, branched C 8 -C 18 esters, isohexyl neopentanoate, and their mixtures. Other volatile hydrocarbon oils such as petroleum distillates, especially those sold under the name Shell or by Shell, may also be used; volatile linear alkanes such as those described in the patent application of Cognis DE10 2008 012 457.
les silicones volatiles, comme par exemple les huiles de silicones linéaires ou cycliques volatiles, notamment celles ayant une viscosité < 8 centistokes (8 10~6 m2/s), et ayant notamment de 2 à 7 atomes de silicium, ces silicones comportant éventuellement des groupes alkyle ou alkoxy ayant de 1 à 10 atomes de carbone. Comme huile de silicone volatile utilisable dans l'invention, on peut citer notamment l'octaméthyl cyclotétrasiloxane, le décaméthyl cyclopentasiloxane, le dodécaméthyl cyclohexasiloxane, l'heptaméthyl hexyltrisiloxane, l'heptaméthyloctyl trisiloxane, l'hexaméthyl disiloxane, l'octaméthyl trisiloxane, le décaméthyl tétrasiloxane, le dodécaméthyl pentasiloxane volatile silicones, for example volatile linear or cyclic silicone oils, in particular those having a viscosity <8 centistokes (8 10 ~ 6 m 2 / s), and having in particular 2 to 7 silicon atoms, these silicones optionally comprising alkyl or alkoxy groups having 1 to 10 carbon atoms. As volatile silicone oil that can be used in the invention, there may be mentioned in particular octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, heptamethylhexyltrisiloxane, heptamethyloctyltrisiloxane, hexamethylisiloxane, octamethyltrisiloxane and decamethyl tetrasiloxane, dodecamethylpentasiloxane
et leurs mélanges. On peut également citer les huiles linéaires alkyltrisiloxanes volatiles de formule générale (I) : and their mixtures. It is also possible to mention volatile alkyltrisiloxane linear oils of general formula (I):
Figure imgf000019_0001
Figure imgf000019_0001
où R représente un groupe alkyle comprenant de 2 à 4 atomes de carbone et dont un ou plusieurs atomes d'hydrogène peuvent être substitués par un atome de fluor ou de chlore.  where R represents an alkyl group comprising from 2 to 4 carbon atoms and one or more hydrogen atoms of which may be substituted by a fluorine or chlorine atom.
Parmi les huiles de formule générale (I), on peut citer :  Among the oils of general formula (I), mention may be made of:
le 3-butyl 1 ,1 ,1 ,3,5,5,5-heptaméthyl trisiloxane,  3-butyl 1,1,1,5,5,5-heptamethyltrisiloxane,
le 3-propyl 1 ,1 ,1 ,3,5,5,5-heptaméthyl trisiloxane, et  3-propyl-1,1,1,5,5,5-heptamethyltrisiloxane, and
le 3-éthyl 1 ,1 ,1 ,3,5,5,5-heptaméthyl trisiloxane,  3-ethyl-1,1,1,5,5,5-heptamethyltrisiloxane,
correspondant aux huiles de formule (I) pour lesquelles R est respectivement un groupe butyle, un groupe propyle ou un groupe éthyle. A titre d'exemple d'huile non volatile utilisable dans l'invention, on peut citer :  corresponding to the oils of formula (I) for which R is respectively a butyl group, a propyl group or an ethyl group. As an example of a non-volatile oil that may be used in the invention, mention may be made of:
les huiles hydrocarbonées d'origine animale telles que le perhydrosqualène ;  hydrocarbon oils of animal origin such as perhydrosqualene;
les huiles hydrocarbonées végétales telles que les triglycérides liquides d'acides gras de 4 à 24 atomes de carbone comme les triglycérides des acides heptanoïque ou octanoïque ou encore les huiles les huiles de germe de blé, d'olive, l'huile d'amande douce, de palme, de colza, de coton, de luzerne, de pavot, de potimarron, de courge, de cassis, d'onagre, de millet, d'orge, de quinoa, de seigle, de carthame, de bancoulier, de passiflore, de rosier muscat, de tournesol, de maïs, de soja, de courge, de pépins de raisin, de sésame, de noisette, d'abricot, de macadamia, de ricin, d'avocat, les triglycérides des acides caprylique/caprique comme ceux vendus par la société Stearineries Dubois ou ceux vendus sous les dénominations Miglyol 810, 812 et 818 par la société Dynamit Nobel, l'huile de jojoba, de beurre de karité ;  vegetable hydrocarbon oils such as liquid triglycerides of fatty acids of 4 to 24 carbon atoms such as triglycerides of heptanoic or octanoic acids or oils oils of wheat germ, olive oil, sweet almond oil , palm, colza, cotton, alfalfa, poppy, pumpkin, squash, black currant, evening primrose, millet, barley, quinoa, rye, safflower, bancoulier, passionflower , musk rose, sunflower, maize, soya, squash, grape seed, sesame, hazelnut, apricot, macadamia, castor, avocado, caprylic / capric acid triglycerides as those sold by Stearineries Dubois or those sold under the names Miglyol 810, 812 and 818 by Dynamit Nobel, jojoba oil, shea butter;
les hydrocarbures linéaires ou ramifiés, d'origine minérale ou synthétique tels que les huiles de paraffine et leurs dérivés, la vaseline, les polydécènes, les polybutènes, le polyisobutène hydrogéné tel que le Parleam, le squalane ;  linear or branched hydrocarbons of mineral or synthetic origin such as liquid paraffins and derivatives thereof, petroleum jelly, polydecenes, polybutenes, hydrogenated polyisobutene such as Parleam, squalane;
les éthers de synthèse ayant de 10 à 40 atomes de carbone ; les esters de synthèse notamment d'acides gras comme les huiles de formule R COOR2 dans laquelle R représente le reste d'un acide gras supérieur linéaire ou ramifié comportant de 1 à 40 atomes de carbone et R2 représente une chaîne hydrocarbonée notamment ramifiée contenant de 1 à 40 atomes de carbone avec R1 + R2 > 10 comme par exemple l'huile de Purcellin (octanoate de cétostéaryle), l'isononanoate d'isononyle, le myristate d'isopropyle, le palmitate d'isopropyle, le benzoate d'alcool en C12 à C15, le laurate d'hexyle, l'adipate de diisopropyle, le palmitate d'éthyl 2-hexyle, le stéarate d'octyl 2-dodécyle, l'érucate d'octyl 2-dodécyle, l'isostéarate d'isostéaryle, le tridecyl trimellitate ; les octanoates, décanoates ou ricinoléates d'alcools ou de polyalcools comme le dioctanoate de propylène glycol ; les esters hydroxylés comme l'isostéaryl lactate, l'octyl hydroxy stéarate, l'hydroxy stéarate d'octyl dodécyle, le diisostéaryl malate, le citrate de triisocétyle, des heptanoates, octanoates, décanoates d'alcools gras ; des esters de polyol comme le dioctanoate de propylène glycol, le diheptanoate de néopentyl glycol, le diisononanoate de diéthylène glycol ; et les esters du pentaérythritol comme le tétra-isostéarate de pentaérythrytyle ; synthetic ethers having from 10 to 40 carbon atoms; synthetic esters, in particular of fatty acids, such as the oils of formula R COOR 2 in which R represents the residue of a linear or branched higher fatty acid containing from 1 to 40 carbon atoms and R 2 represents a hydrocarbon chain, in particular a branched hydrocarbon chain, containing from 1 to 40 carbon atoms with R 1 + R 2 > 10 such as, for example, purcellin oil (cetostearyl octanoate), isononyl isononanoate, isopropyl myristate, isopropyl palmitate, benzoate of C12 to C15 alcohol, hexyl laurate, diisopropyl adipate, ethyl 2-hexyl palmitate, octyl 2-dodecyl stearate, octyl 2-dodecyl erucate, isostearyl isostearate, tridecyl trimellitate; octanoates, decanoates or ricinoleates of alcohols or polyalcohols such as propylene glycol dioctanoate; hydroxylated esters such as isostearyl lactate, octyl hydroxy stearate, octyl dodecyl hydroxystearate, diisostearyl malate, triisocetyl citrate, heptanoates, octanoates, decanoates of fatty alcohols; polyol esters such as propylene glycol dioctanoate, neopentyl glycol diheptanoate, diethylene glycol diisononanoate; and pentaerythritol esters such as pentaerythritol tetraisostearate;
- des alcools gras liquides à température ambiante à chaîne carbonée ramifiée et/ou insaturée ayant de 12 à 26 atomes de carbone comme l'octyl dodécanol, l'alcool isostéarylique, le 2-butyloctanol, le 2-hexyl décanol, le 2-undécyl pentadécanol, l'alcool oléique ;  branched-chain and / or unsaturated carbon-chain liquid fatty alcohols having from 12 to 26 carbon atoms, such as octyl dodecanol, isostearyl alcohol, 2-butyloctanol, 2-hexyl decanol and 2-undecyl; pentadecanol, oleic alcohol;
- les acides gras supérieurs tels que l'acide oléique, l'acide linoléique, l'acide linolénique ;  higher fatty acids such as oleic acid, linoleic acid, linolenic acid;
- les carbonates ;  - carbonates;
- les acétates ;  - acetates;
- les citrates ;  - citrates;
- les huiles fluorées éventuellement partiellement hydrocarbonées et/ou siliconées comme les huiles fluorosiliconées, les polyéthers fluorés, les silicones fluorées telles que décrit dans le document EP-A-847752;  fluorinated oils that may be partially hydrocarbon-based and / or silicone-based, such as fluorosilicone oils, fluorinated polyethers or fluorinated silicones, as described in document EP-A-847752;
- les huiles siliconées comme les polydiméthylsiloxanes (PDMS) non volatiles, linéaires ou cycliques ; les polydiméthylsiloxanes comportant des groupements alkyle, alcoxy ou phényle, pendant ou en bout de chaîne siliconée, groupements ayant de 2 à 24 atomes de carbone ; les silicones phénylées comme les phényl triméthicones, les phényl diméthicones, les phényl triméthylsiloxy diphényl siloxanes, les diphényl diméthicones, les diphényl méthyldiphényl trisiloxanes, les 2-phényl éthyl triméthyl-siloxysilicates, et  silicone oils, such as non-volatile, linear or cyclic polydimethylsiloxanes (PDMS); polydimethylsiloxanes comprising alkyl, alkoxy or phenyl groups, during or at the end of the silicone chain, groups having from 2 to 24 carbon atoms; phenyl silicones such as phenyl trimethicones, phenyl dimethicones, phenyl trimethylsiloxy diphenyl siloxanes, diphenyl dimethicones, diphenyl methyldiphenyl trisiloxanes, 2-phenylethyl trimethylsiloxysilicates, and
leurs mélanges. Additifs their mixtures. additives
Les compositions cosmétiques selon l'invention peuvent comprendre en outre des adjuvants cosmétiques choisis parmi les adoucissants, les antioxydants, les opacifiants, les stabilisants, les agents hydratants, les vitamines, des bactéricides, les conservateurs, les polymères, les parfums, un agent structurant de phase grasse en particulier choisi parmi les cires, les composés pâteux, les gélifiants; les charges organiques ou inorganiques ; les agents épaississants ou de mise en suspension, des agents propulseurs ou tout autre ingrédient habituellement utilisé en cosmétique pour ce type d'application. The cosmetic compositions according to the invention may furthermore comprise cosmetic adjuvants chosen from softeners, antioxidants, opacifiers, stabilizers, moisturizing agents, vitamins, bactericides, preservatives, polymers, perfumes and a structuring agent. fatty phase in particular chosen from waxes, pasty compounds, gelling agents; organic or inorganic fillers; thickeners or suspending agents, propellants or any other ingredient usually used in cosmetics for this type of application.
Bien entendu, l'homme de métier veillera à choisir ce ou ces éventuels composés complémentaires de manière telle que les propriétés avantageuses attachées intrinsèquement à la composition cosmétique conforme à l'invention ne soient pas, ou substantiellement pas, altérées par la ou les adjonctions envisagées.  Of course, those skilled in the art will take care to choose this or these optional additional compounds in such a way that the advantageous properties intrinsically attached to the cosmetic composition in accordance with the invention are not, or not substantially, impaired by the addition or additions envisaged. .
Cire(s) Wax (es)
La cire est d'une manière générale un composé lipophile, solide à température ambiante (25 'C), à changement d'état solide/liquide réversible, ayant un point de fusion supérieur ou égal à 30 'C pouvant aller jusqu'à 200 'C et notamment jusqu'à 120 'C.  The wax is in general a lipophilic compound, solid at room temperature (25 ° C.), with reversible solid / liquid state change, having a melting point of greater than or equal to 30 ° C. and up to 200 'C and especially up to 120' C.
En particulier, les cires convenant à l'invention peuvent présenter un point de fusion supérieur ou égal à 45 'C, et en particulier supérieur ou égal à 55 'C.  In particular, the waxes that are suitable for the invention may have a melting point greater than or equal to 45 ° C., and in particular greater than or equal to 55 ° C.
Au sens de l'invention, la température de fusion correspond à la température du pic le plus endothermique observé en analyse thermique (DSC) telle que décrite dans la norme ISO 1 1357-3 ; 1999. Le point de fusion de la cire peut être mesuré à l'aide d'un calorimètre à balayage différentiel (DSC), par exemple le calorimètre vendu sous la dénomination « MDSC 2920® » par la société TA Instruments. For the purposes of the invention, the melting temperature corresponds to the temperature of the most endothermic peak observed in thermal analysis (DSC) as described in the ISO 1 1357-3 standard; 1999. The melting point of the wax can be measured using a differential scanning calorimeter (DSC), for example the calorimeter sold under the name "MDSC 2920®" by the company TA Instruments.
Le protocole de mesure est le suivant :  The measurement protocol is as follows:
Un échantillon de 5 mg de cire disposé dans un creuset est soumis à une première montée en température allant de -20 'C à 100 'C, à la vitesse de chauffe de 10 ^/minute, puis est refroidi de 100 'C à -20 °C à une vitesse de refroidissement de 10 ^/minute et enfin soumis à une deuxième montée en température allant de -20 °C à 100 'C à une vitesse de chauffe de 5 °C/minute. Pendant la deuxième montée en température, on mesure la variation de la différence de puissance absorbée par le creuset vide et par le creuset contenant l'échantillon de cire en fonction de la température. Le point de fusion du composé est la valeur de la température correspondant au sommet du pic de la courbe représentant la variation de la différence de puissance absorbée en fonction de la température. A sample of 5 mg of wax placed in a crucible is subjected to a first temperature rise from -20 ° C. to 100 ° C., at the heating rate of 10 ° / minute, and is then cooled from 100 ° C. to 20 ° C at a cooling rate of 10 ^ / minute and finally subjected to a second temperature rise from -20 ° C to 100 ° C at a heating rate of 5 ° C / minute. During the second temperature rise, the variation of the power difference absorbed by the empty crucible and the crucible containing the wax sample as a function of temperature is measured. The melting point of the compound is the value of the temperature corresponding to the top of the peak of the curve representing the variation of the difference in power absorbed as a function of the temperature.
Les cires susceptibles d'être utilisées dans les compositions selon l'invention sont choisies parmi les cires, solides, à température ambiante d'origine animale, végétale, minérale ou de synthèse et leurs mélanges.  The waxes that may be used in the compositions according to the invention are chosen from waxes, solid, at room temperature of animal, vegetable, mineral or synthetic origin, and mixtures thereof.
A titre illustratif des cires convenant à l'invention, on peut notamment citer les cires hydrocarbonées comme la cire d'abeille, la cire de lanoline, et les cires d'insectes de Chine, la cire de son de riz, la cire de Carnauba, la cire de Candellila, la cire d'Ouricury, la cire d'Alfa, la cire de berry, la cire de shellac, la cire du Japon et la cire de sumac; la cire de montan, les cires d'orange et de citron, Cire de Tournesol raffinée commercialisée sous la dénomination SUNFLOWER WAX® par KOSTER KEUNEN, les cires microcristallines, les paraffines et l'ozokérite; les cires de polyéthylène, les cires obtenues par la synthèse de Fisher-Tropsch et les copolymères cireux ainsi que leurs esters.  Illustrative waxes suitable for the invention include hydrocarbon waxes such as beeswax, lanolin wax, and Chinese insect wax, rice bran wax, Carnauba wax Candellila wax, Ouricury wax, Alfa wax, berry wax, shellac wax, Japanese wax and sumac wax; montan wax, orange and lemon waxes, refined sunflower wax sold under the name SUNFLOWER WAX® by KOSTER KEUNEN, microcrystalline waxes, paraffins and ozokerite; polyethylene waxes, waxes obtained by Fisher-Tropsch synthesis and waxy copolymers and their esters.
On peut aussi citer des cires obtenues par hydrogénation catalytique d'huiles animales ou végétales ayant des chaînes grasses, linéaires ou ramifiées, en C8-C32. Parmi celles-ci, on peut notamment citer l'huile de jojoba isomérisée telle que l'huile de jojoba partiellement hydrogénée isomérisée trans fabriquée ou commercialisée par la société Désert Whale sous la référence commerciale lso-Jojoba-50®, l'huile de tournesol hydrogénée, l'huile de ricin hydrogénée, l'huile de coprah hydrogénée, l'huile de lanoline hydrogénée, et le tétrastéarate de di-(triméthylol-1 ,1 ,1 propane) vendu sous la dénomination de Hest 2T-4S® par la société HETERENE. Can also be made of waxes obtained by catalytic hydrogenation of animal or plant oils containing fatty chains, linear or branched C 8 -C 32. Among these, there may be mentioned isomérisée jojoba oil such as trans isomerized partially hydrogenated jojoba oil manufactured or marketed by Desert Whale under the trade reference lso-Jojoba-50®, sunflower oil hydrogenated castor oil, hydrogenated coconut oil, hydrogenated lanolin oil, and di- (trimethylol-1,1,1-propane) tetrastearate sold under the name Hest 2T-4S® by the company HETERENE.
On peut encore citer les cires de silicone (C30-45 ALKYL DIMETHICONE), les cires fluorées.  Mention may also be made of silicone waxes (C30-45 ALKYL DIMETHICONE) and fluorinated waxes.
On peut également utiliser les cires obtenues par hydrogénation d'huile de ricin estérifiée avec l'alcool cétylique vendues sous les dénominations de Phytowax ricin 16L64® et 22L73® par la société SOPHIM. De telles cires sont décrites dans la demande FR-A- 2792190.  It is also possible to use the waxes obtained by hydrogenation of castor oil esterified with cetyl alcohol sold under the names Phytowax Ricin 16L64® and 22L73® by the company SOPHIM. Such waxes are described in application FR-A-2792190.
Comme cire, on peut utiliser un (hydroxystéaryloxy)stéarate d'alkyle en C20-C40 (le groupe alkyle comprenant de 20 à 40 atomes de carbone), seul ou en mélange.  As the wax, a C20-C40 alkyl (hydroxystearyloxy) stearate (the alkyl group comprising from 20 to 40 carbon atoms), alone or in admixture, can be used.
Une telle cire est notamment vendue sous les dénominations « Kester Wax K 82 P® », « Hydroxypolyester K 82 P® » et « Kester Wax K 80 P® » par la société KOSTER KEUNEN.  Such a wax is especially sold under the names "Kester Wax K 82 P®", "Hydroxypolyester K 82 P®" and "Kester Wax K 80 P®" by the company Koster Keunen.
Comme micro-cires pouvant être utilisées dans les compositions selon l'invention, on peut citer notamment les micro cires de carnauba telles que celle commercialisée sous la dénomination de MicroCare 350® par la société MICRO POWDERS, les microcires de cire synthétique telles que celle commercialisée sous la dénomination de MicroEase 1 14S® par la société MICRO POWDERS, les micro cires constituées d'un mélange de cire de carnauba et de cire de polyéthylène telles que celles commercialisées sous les dénominations de Micro Care 300® et 310® par la société MICRO POWDERS, les micro cires constituées d'un mélange de cire de carnauba et de cire synthétique telles que celle commercialisée sous la dénomination Micro Care 325® par la société MICRO POWDERS, les micro cires de polyéthylène telles que celles commercialisées sous les dénominations de Micropoly 200®, 220®, 220L® et 250S® par la société MICRO POWDERS, les produits commerciaux PERFOMALEN 400 POLYETHYLENE® et PERFORMALENE 500-L POLYETHYLENE® de NEW PHASE TECHNOLOGIES, le PERFORMALENE 655 POLYETHYLENE ou les cires de paraffine comme la cire ayant pour nom INCI , MICROCRISTALLINE WAX and SYNTHETIC WAX et vendue sous le nom commercial MICROLEASE par la Société SOCHIBO. ; les micro cires de polytétrafluoroéthylène telles que celles commercialisées sous les dénominations de Microslip 519® et 519 L® par la société MICRO POWDERS. As micro-waxes that can be used in the compositions according to the invention, mention may be made in particular of carnauba micro-waxes such as that marketed under the name MicroCare 350® by the company MICRO POWDERS, the microwaxes of synthetic wax such as that marketed under the name MicroEase 1 14S® by the company MICRO POWDERS, the micro waxes consisting of a mixture of carnauba wax and polyethylene wax such as those sold under the names of Micro Care 300® and 310® by the company MICRO POWDERS, micro waxes consisting of a mixture of carnauba wax and synthetic wax such as that marketed under the name Micro Care 325® by the company MICRO POWDERS, polyethylene micro-waxes such as those marketed under the names Micropoly 200®, 220®, 220L® and 250S® by the company Micro Powders, the commercial products PERFOMALEN 400 POLYETHYLENE® and PERFORMALENE 500-L POLYETHYLENE® from NEW PHASE TECHNOLOGIES, PERFORMALENE 655 POLYETHYLENE or paraffin waxes as the wax having the name INCI, MICROCRYSTALLINE WAX and SYNTHETIC WAX and sold under the trade name MICROLEASE by the a SOCHIBO company. ; polytetrafluoroethylene micro waxes such as those sold under the names Microslip 519® and 519 L® by the company Micro Powders.
Composés pâteux Paste compounds
Par « composé pâteux » au sens de la présente invention, on entend un composé gras lipophile à changement d'état solide/liquide réversible, présentant à l'état solide une organisation cristalline anisotrope, et comportant à la température de 23 'C une fraction liquide et une fraction solide.  For the purposes of the present invention, the term "pasty compound" is intended to mean a lipophilic fat compound having a reversible solid / liquid state change, having in the solid state an anisotropic crystalline organization, and comprising at a temperature of 23.degree. liquid and a solid fraction.
Le composé pâteux est de préférence choisi parmi les composés synthétiques et les composés d'origine végétale. Un composé pâteux peut être obtenu par synthèse à partir de produits de départ d'origine végétale.  The pasty compound is preferably chosen from synthetic compounds and compounds of plant origin. A pasty compound can be obtained synthetically from starting materials of plant origin.
Le composé pâteux peut avantageusement être choisi parmi :  The pasty compound may advantageously be chosen from:
- la lanoline et ses dérivés,  - lanolin and its derivatives,
- les composés siliconés polymères ou non,  polymeric or non-polymeric silicone compounds,
- les composés fluorés polymères ou non,  polymeric or non-polymeric fluorinated compounds,
- les polymères vinyliques, notamment :  vinyl polymers, in particular:
- les homopolymères d'oléfines,  homopolymers of olefins,
- les copolymères d'oléfines,  copolymers of olefins,
- les homopolymères et copolymères de diènes hydrogénés,  homopolymers and copolymers of hydrogenated dienes,
- les oligomères linéaires ou ramifiés, homo ou copolymères de (méth)acrylates d'alkyles ayant de préférence un groupement alkyle en C8-C30, - linear or branched oligomers, homo- or copolymers of alkyl (meth) acrylates having preferably an alkyl group in C 8 -C 30,
- les oligomères homo et copolymères d'esters vinyliques ayant des groupements alkyles en C8-C3o, et - les oligomères homo et copolymères de vinyléthers ayant des groupements alkyles en C8-C3o, - homo- and copolymeric oligomers of vinyl esters having alkyl groups of C 8 -C 3 °, and the homo- and copolymer oligomers of vinyl ethers having C 8 -C 3 alkyl groups,
- les polyéthers liposolubles résultant de la polyéthérification entre un ou plusieurs diols en C2-Ci 0o, de préférence en C2-C5o, the liposoluble polyethers resulting from the polyetherification between one or more C 2 -C 0 0 diols, preferably C 2 -C 5 o diols,
- les esters,  the esters,
- leurs mélanges.  - their mixtures.
Agents de suspension/ Gélifiants La composition selon l'invention peut en outre contenir un ou plusieurs agents de suspension et/ou un ou plusieurs gélifiants. Certains d'entre eux peuvent jouer les deux rôles à la fois. Suspension Agents / Gelling Agents The composition according to the invention may further contain one or more suspending agents and / or one or more gelling agents. Some of them can play both roles at once.
Parmi les agents pouvant être utilisés comme agent de suspension et/ou comme gélifiant lipophile, on peut citer les argiles éventuellement modifiées notamment les argiles montmorillonites modifiées hydrophobes comme les bentonites ou hectorites modifiées hydrophobes comme les hectorites modifiées par un chlorure d'ammonium en C10 à C22, comme l'hectorite modifiée par du chlorure de di-stéaryl di-méthyl ammonium telle que, par exemple, le produit Disteardimonium Hectorite (nom CTFA) (produit de réaction de l'hectorite et du chlorure de distéaryldimonium) vendu sous le nom de Bentone 38 ou Bentone Gel par la société Elementis Specialities. On peut citer par exemple le produit Stearaikonium Bentonite (nom CTFA) (produit de réaction de la bentonite et de l'ammonium quaternaire chlorure de stéaralkonium) tel que le produit commercial vendu sous le nom TIXOGEL MP 250® par la société Sud Chemie Rheologicals, United Catalysts Inc. Among the agents that can be used as suspending agent and / or as lipophilic gelling agent, there may be mentioned optionally modified clays, in particular hydrophobic modified montmorillonite clays, such as hydrophobic modified bentonites or hectorites, such as hectorites modified with a C10 ammonium chloride. C 22, such as hectorite modified by chloride distearyl di-methyl ammonium such as, for example, the product disteardimonium hectorite (CTFA name) (product of reaction of hectorite and of distearyldimonium chloride) sold under the Bentone 38 or Bentone Gel by Elementis Specialties. Mention may be made, for example, of the product Stearaikonium Bentonite (CTFA name) (reaction product of bentonite and of quaternary ammonium stearalkonium chloride), such as the commercial product sold under the name Tixogel MP 250® by the company Sud Chemie Rheologicals, United Catalysts Inc.
On peut aussi utiliser des hydrotalcites, en particulier des hydrotalcites modifiées hydrophobes comme par exemple les produits vendus sous le nom de Gilugel par la société BK Giulini.  It is also possible to use hydrotalcites, in particular hydrophobic modified hydrotalcites, for example the products sold under the name Gilugel by the company BK Giulini.
On peut également citer la silice pyrogénée éventuellement traitée hydrophobe en surface dont la taille des particules est inférieure à 1 μηι. Il est en effet possible de modifier chimiquement la surface de la silice, par réaction chimique générant une diminution du nombre de groupes silanol présents à la surface de la silice. On peut notamment substituer des groupes silanol par des groupements hydrophobes : on obtient alors une silice hydrophobe. Les groupements hydrophobes peuvent être des groupements triméthylsiloxyle, qui sont notamment obtenus par traitement de silice pyrogénée en présence de l'hexaméthyldisilazane. Des silices ainsi traitées sont dénommées « Silica silylate » selon le CTFA (8ème édition, 2000). Elles sont par exemple commercialisées sous les références Aerosil R812® par la société DEGUSSA, CAB-O- SIL TS-530® par la société CABOT, des groupements diméthylsilyloxyle ou polydiméthylsiloxane, qui sont notamment obtenus par traitement de silice pyrogénée en présence de polydiméthylsiloxane ou du diméthyldichlorosilane. Des silices ainsi traitées sont dénommées « Silica diméthyl silylate » selon le CTFA (8ème édition, 2000). Elles sont par exemple commercialisées sous les références Aerosil R972®, et Aerosil R974® par la société DEGUSSA, CAB-O-SIL TS-610® et CAB-O-SIL TS-720® par la société CABOT. It is also possible to mention fumed silica optionally treated with hydrophobic surface, the particle size of which is less than 1 μηι. It is indeed possible to chemically modify the surface of the silica, by chemical reaction generating a decrease in the number of silanol groups present on the surface of the silica. In particular, it is possible to substitute silanol groups with hydrophobic groups: a hydrophobic silica is then obtained. The hydrophobic groups may be trimethylsiloxyl groups, which are especially obtained by treatment of fumed silica in the presence of hexamethyldisilazane. Silicas thus treated are called "Silica silylate" according to the CTFA (8th edition, 2000). They are for example sold under the references Aerosil R812® by the company Degussa, Cab-O-Sil TS-530® by the company Cabot, dimethylsilyloxyl or polydimethylsiloxane groups, which are obtained in particular by treatment of fumed silica in the presence of polydimethylsiloxane or dimethyldichlorosilane. Silicas thus treated are called "Silica dimethyl silylate" according to the CTFA (8th edition, 2000). They are for example marketed under the references Aerosil R972®, and Aerosil R974® by the company DEGUSSA, CAB-O-SIL TS-610® and CAB-O-SIL TS-720® by CABOT.
La silice pyrogénée hydrophobe présente en particulier une taille de particules pouvant être nanométrique à micrométrique, par exemple allant d'environ de 5 à 200 nm.  The hydrophobic fumed silica has in particular a particle size that can be nanometric to micrometric, for example ranging from about 5 to 200 nm.
D'autres agents de suspension ou gélifiants peuvent être utilisés, en l'occurrence dans des milieux hydrophiles (aqueux et/ou éthanoliques). Il s'agit de dérivés cellulosiques (pouvant être microcristalline), de xanthane, guar amidon (dont l'amidon de maïs modifié commercialisé sous la dénomination Structure XL par AKZO NOBEL), caroube, agar agar.  Other suspending agents or gelling agents may be used, in this case in hydrophilic media (aqueous and / or ethanolic). These are cellulosic derivatives (which may be microcrystalline), xanthan, guar starch (including modified corn starch marketed under the name Structure XL by Akzo Nobel), carob, agar agar.
Les quantités de ces différents constituants pouvant être présents dans la composition selon l'invention sont celles classiquement utilisées dans des compositions, notamment pour le traitement de la transpiration et/ou des odeurs corporelles. Aérosols  The amounts of these various constituents that may be present in the composition according to the invention are those conventionally used in compositions, especially for the treatment of perspiration and / or body odor. aerosols
Les compositions selon l'invention peuvent être pressurisées et conditionnées dans un dispositif aérosol constitué par : The compositions according to the invention may be pressurized and packaged in an aerosol device consisting of:
(A) au moins un récipient comprenant une composition selon l'invention,  (A) at least one container comprising a composition according to the invention,
(B) au moins un agent propulseur et au moins un moyen de distribution de la dite composition sous forme aérosol.  (B) at least one propellant and at least one means for dispensing said composition in aerosol form.
Les propulseurs généralement utilisés dans ce type de produits et bien connus de l'homme de l'art, sont comme par exemple le diméthyléther (DME) ; les hydrocarbures volatils tels que le n-butane, le propane, l'isobutane, et leurs mélanges, éventuellement avec au moins un hydrocarbure chloré et/ou fluoré; parmi ces derniers on peut citer les composés vendus par la société Dupont de Nemours sous les dénominations Fréon® et Dymel®, et en particulier le monofluorotrichlorométhane, le difluorodichlorométhane, le tétrafluorodichloroéthane et le 1 ,1 -difluoroéthane vendu notamment sous la dénomination commerciale DYMEL 152 A® par la société DUPONT. On peut également utiliser en tant qu'agent propulseur le gaz carbonique, le protoxyde d'azote, l'azote ou l'air comprimé. Les compositions contenant les particules de perlite telles que définies précédemment et le ou les agents propulseurs peuvent se trouver dans le même compartiment ou dans des compartiments différents dans le récipient aérosol. Selon l'invention, la concentration en agent propulseur varie généralement de 5 à 95% en poids pressurisée et plus préférentiellement de 50 à 85% en poids par rapport au poids total de la composition pressurisée. Propellants generally used in this type of product and well known to those skilled in the art are, for example, dimethyl ether (DME); volatile hydrocarbons such as n-butane, propane, isobutane, and mixtures thereof, optionally with at least one chlorinated and / or fluorinated hydrocarbon; among these are the compounds sold by the company Dupont de Nemours under the names Freon® and Dymel®, and in particular monofluorotrichloromethane, difluorodichloromethane, tetrafluorodichloroethane and 1,1-difluoroethane sold especially under the trade name Dymel 152 A® by DUPONT. It is also possible to use as propellant carbon dioxide, nitrous oxide, nitrogen or compressed air. The compositions containing the perlite particles as defined above and the propellant (s) may be in the same compartment or in different compartments in the aerosol container. According to the invention, the concentration of propellant generally varies from 5 to 95% by weight pressurized and more preferably from 50 to 85% by weight relative to the total weight of the pressurized composition.
Le moyen de distribution, qui forme une partie du dispositif aérosol, est généralement constitué par une valve de distribution commandée par une tête de distribution, elle-même comprenant une buse par laquelle la composition aérosol est vaporisée. Le récipient contenant la composition pressurisée peut être opaque ou transparent. Il peut être en verre, en matériau polymérique ou en métal, recouvert éventuellement d'une couche de vernis protecteur.  The dispensing means, which forms part of the aerosol device, is generally constituted by a dispensing valve controlled by a dispensing head, itself comprising a nozzle through which the aerosol composition is vaporized. The container containing the pressurized composition may be opaque or transparent. It may be glass, polymeric material or metal, optionally covered with a layer of protective varnish.
Emballage-notice d'informations Packaging-information sheet
L'invention concerne encore un emballage (« packaging ») ou notice d'information comprenant, éventuellement parmi d'autres informations visuelles, la mention de la présence d'un ou plusieurs des composés selon l'invention, et/ou de la présence d'au moins un actif anti-transpirant et/ou au moins un autre actif déodorant. En particulier l'invention concerne un emballage ou notice d'information comprenant la liste des ingrédients d'une composition selon la présente invention. Selon une variante, l'emballage ou la notice d'information présente des informations visuelles concernant le traitement des odeurs et/ou de la transpiration, en particulier chez un être humain. Plus particulièrement, cet emballage ou notice d'information est destiné à l'information d'un utilisateur sur la destination de la composition ou du dispositif selon l'invention, déjà emballé ou qui devrait y être emballé.  The invention also relates to a package ("packaging") or information notice including, possibly among other visual information, the mention of the presence of one or more of the compounds according to the invention, and / or the presence at least one antiperspirant active agent and / or at least one other deodorant active agent. In particular the invention relates to a package or information notice comprising the list of ingredients of a composition according to the present invention. According to one variant, the packaging or the information leaflet presents visual information concerning the treatment of odors and / or perspiration, in particular in a human being. More particularly, this packaging or information notice is intended to inform a user of the destination of the composition or device according to the invention, already packaged or which should be packed therein.
L'invention concerne encore une composition selon l'invention, ou un dispositif la comprenant, accompagnée d'un emballage ou notice d'information, notamment tel que défini ci-dessus.  The invention also relates to a composition according to the invention, or a device comprising it, accompanied by a packaging or information notice, particularly as defined above.
L'invention concerne notamment une composition, notamment cosmétique, comprenant dans un milieu physiologiquement acceptable au moins un composé de formule (I) selon l'invention, éventuellement en association avec au moins un actif anti- transpirant et/ou au moins un autre actif déodorant dans un milieu physiologiquement acceptable, ladite composition étant accompagnée d'un emballage ou notice d'information présentant des informations visuelles concernant le traitement des odeurs et/ou de la transpiration d'un être humain, et/ou des informations sur la présence d'au moins un actif anti-transpirant et/ou au moins un actif déodorant, éventuellement parmi d'autres informations visuelles. The invention relates in particular to a composition, in particular a cosmetic composition, comprising in a physiologically acceptable medium at least one compound of formula (I) according to the invention, optionally in combination with at least one antiperspirant active agent and / or at least one other active ingredient. deodorant in a physiologically acceptable medium, said composition being accompanied by a package or information notice presenting visual information concerning the treatment of odors and / or perspiration of a human being, and / or information on the presence of at least one asset antiperspirant and / or at least one deodorant active, possibly among other visual information.
Les expressions « compris entre ... et ... » et « allant de ... à ... » doivent se comprendre bornes incluses, sauf si le contraire est spécifié.  Expressions "between ... and ..." and "from ... to ..." must be understood as inclusive terms unless otherwise specified.
Les exemples qui suivent illustrent la présente invention sans en limiter la portée. The following examples illustrate the present invention without limiting its scope.
Dans les exemples, la température est celle ambiante (20-25°C), la pression est celle atmosphérique (101 325 Pa), sauf indications contraires. La masse des ingrédients est exprimée en pourcentage par rapport à la masse de la composition totale considérée. In the examples, the temperature is that ambient (20-25 ° C), the pressure is atmospheric (101 325 Pa), unless otherwise indicated. The mass of ingredients is expressed as a percentage relative to the mass of the total composition considered.
Exemples Examples
Exemple 1 : préparation du composé 3
Figure imgf000027_0001
Example 1 Preparation of Compound 3
Figure imgf000027_0001
3 3
Un mélange de bétaine (A) (2g, 16,9mmol), 1 -decanol (8mL) et acide méthanesulfonique (1 ,4mL) est chauffé à 140 °C pendant 8h, sous atmosphère inerte (N2). Après retour à température ambiante, l'excès d'acide est neutralisé par addition d'une solution aqueuse saturée en bétaine. Ce mélange est ensuite concentré à sec par évaporation sous pression réduite. Le résidu est repris dans l'acétone pour redissoudre le produit. Après filtration des sels de bétaine, le filtrat est concentré par évaporation sous pression réduite. Le brut réactionnel est purifié par recristallisation dans le n-heptane. Le produit est ainsi isolé sous la forme d'un solide blanc. (2,6g - rdt 44%). A mixture of betaine (A) (2 g, 16.9 mmol), 1-decanol (8 ml) and methanesulphonic acid (1.4 ml) is heated at 140 ° C. for 8 h under an inert atmosphere (N 2 ). After returning to ambient temperature, the excess of acid is neutralized by adding a saturated aqueous solution of betaine. This mixture is then concentrated to dryness by evaporation under reduced pressure. The residue is taken up in acetone to redissolve the product. After filtration of the betaine salts, the filtrate is concentrated by evaporation under reduced pressure. The crude reaction product is purified by recrystallization from n-heptane. The product is thus isolated in the form of a white solid. (2.6g - 44% yield).
Le spectre RMN H et le spectre de masse confirment la structure du composé 3 attendu.  The 1 H NMR spectrum and the mass spectrum confirm the structure of the expected compound 3.
RMN 1 H (MeOD) : 0,85-0,94 (m, 3H); 1 ,20-1 ,48 (m, 14H); 1 ,60-1 ,80 (m, 2H); 2,69 (s, 3H); 3,33 (s, 9H); 4,25 (t, 2H); 4,38 (s, 2H) 1 H NMR (MeOD): 0.85-0.94 (m, 3H); 1, 20-1, 48 (m, 14H); 1.60-1.80 (m, 2H); 2.69 (s, 3H); 3.33 (s, 9H); 4.25 (t, 2H); 4.38 (s, 2H)
Spectrom. masse : détecté = 258 - attendu pour [Ci5H32N02]+ = 258 Spectrom. mass: detected = 258 - expected for [Ci 5 H 32 N0 2 ] + = 258
Exemple 2 : préparation du composé 2
Figure imgf000027_0002
Un mélange de bétaine (A) (24g, 0,2mol), 3-octanol (60ml_) et acide méthanesulfonique (18ml_) est chauffé à 140°C pendant 8h, sous atmosphère inerte (N2). Après retour à température ambiante, l'excès d'acide est neutralisé par addition d'une solution aqueuse saturée en bétaine. Ce mélange est ensuite concentré à sec par évaporation sous pression réduite. Le résidu est repris dans l'acétone pour redissoudre le produit. Après filtration des sels de bétaine, le filtrat est concentré par évaporation sous pression réduite. Le composé ainsi obtenu est purifié par recristallisation dans le n- heptane. Le produit 2 est ainsi isolé sous la forme d'un solide brun. (3g - rdt 4,5%).
Example 2 Preparation of Compound 2
Figure imgf000027_0002
A mixture of betaine (A) (24 g, 0.2 mol), 3-octanol (60 ml) and methanesulfonic acid (18 ml) is heated at 140 ° C. for 8 h under an inert atmosphere (N 2 ). After returning to ambient temperature, the excess of acid is neutralized by adding a saturated aqueous solution of betaine. This mixture is then concentrated to dryness by evaporation under reduced pressure. The residue is taken up in acetone to redissolve the product. After filtration of the betaine salts, the filtrate is concentrated by evaporation under reduced pressure. The compound thus obtained is purified by recrystallization from n-heptane. The product 2 is thus isolated in the form of a brown solid. (3g - yield 4.5%).
Le spectre RMN H et le spectre de masse confirment la structure du composé 2 attendu.  The 1 H NMR spectrum and the mass spectrum confirm the structure of the expected compound 2.
RMN 1H (MeOD) : 0,83-1 ,00 (m, 6H); 1 ,32 (s, 6H); 1 ,56-1 ,79 (m, 4H); 2,69 (s, 3H); 3,26-3,41 (m, 9H); 4,43 (s, 2H); 4,96-5,09 (m, 1 H). 1 H NMR (MeOD): 0.83-1.00 (m, 6H); 1, 32 (s, 6H); 1, 56-1, 79 (m, 4H); 2.69 (s, 3H); 3.26-3.41 (m, 9H); 4.43 (s, 2H); 4.96-5.09 (m, 1H).
Spectrom. masse : détecté = 230 - attendu pour [Ci3H28N02]+ = 230 Spectrom. mass: detected = 230 - expected for [Ci 3 H 28 N0 2 ] + = 230
Exemple 3 : préparation du composé 6 o Example 3 Preparation of Compound 6
II  II
H -S-O
Figure imgf000028_0001
H -SO
Figure imgf000028_0001
6  6
Un mélange de bétaine (A) (55,4g, 0,47mol), 3-méthyl-1 -butanol (210mL) et acide méthanesulfonique (36,8mL) est chauffé à 140 ^ pendant 7h, sous atmosphère inerte (N2). Le milieu réactionnel est agité à température ambiante pendant 17h, l'excès d'acide est neutralisé par addition d'une solution aqueuse saturée en bétaine. L'eau contenue est ensuite éliminée par évaporation sous pression réduite, et les sels de bétaine sont filtrés. Le filtrat est concentré à sec sous pression réduite. Le résidu est repris dans l'heptane. Le produit 6 est ainsi isolé sous la forme d'un solide blanc. (76,4g - rdt 57%) A mixture of betaine (A) (55.4 g, 0.47 mol), 3-methyl-1-butanol (210 ml) and methanesulfonic acid (36.8 ml) is heated at 140 ° C. for 7 h under an inert atmosphere (N 2 ). . The reaction medium is stirred at room temperature for 17 h, the excess acid is neutralized by addition of a saturated aqueous solution of betaine. The water contained is then removed by evaporation under reduced pressure, and the betaine salts are filtered. The filtrate is concentrated to dryness under reduced pressure. The residue is taken up in heptane. The product 6 is thus isolated in the form of a white solid. (76.4g - 57% yield)
Le spectre RMN H et le spectre de masse confirment la structure du composé 6 attendu.  The 1 H NMR spectrum and the mass spectrum confirm the structure of the expected compound 6.
RMN 1H (DMSO) : 0,82-0,94 (d, 6H); 1 ,45-1 ,56 (td, 2H); 1 ,56-1 ,72 (m, 1 H); 2,32- 2,41 (m, 3H); 3,17-3,29 (m, 9H); 4,17-4,27 (m, 2H); 4,40-4,46 (m, 2H) 1 H NMR (DMSO): 0.82-0.94 (d, 6H); 1.45-1.56 (td, 2H); 1, 56-1.72 (m, 1H); 2.32-2.41 (m, 3H); 3.17-3.29 (m, 9H); 4.17-4.27 (m, 2H); 4.40-4.46 (m, 2H)
Spectrom. masse : détecté = 188 - attendu pour [CioH22N02]+ = 188 Exemple 4 : préparation du composé 7
Figure imgf000029_0001
Spectrom. mass: detected = 188 - expected for [C10H 22 N0 2 ] + = 188 Example 4 Preparation of compound 7
Figure imgf000029_0001
7  7
Un mélange de composé 6, 10g de résine échangeuse d'ion DOWEX 1 x2-200 et 20ml_ de méthanol est agité à température ambiante pendant 24h. La résine est élimnée par filtration et le filtrat est concentré par évaporation sous pression réduite. Le produit 7 est ainsi isolé sous la forme d'un solide gris blanc. (2g - rdt 69%)  A mixture of compound 6, 10 g of DOWEX 1 x 2-200 ion exchange resin and 20 ml of methanol is stirred at room temperature for 24 hours. The resin is removed by filtration and the filtrate is concentrated by evaporation under reduced pressure. The product 7 is thus isolated in the form of a white gray solid. (2g - 69% yield)
Le spectre RMN H et le spectre de masse confirment la structure du composé 7 attendu.  The 1 H NMR spectrum and the mass spectrum confirm the structure of the expected compound 7.
RMN 1 H (MeOD) : 0,88-1 ,02 (d, 6H); 1 ,54-1 ,63 (td, 2H); 1 ,63-1 ,81 (m, 1 H); 3,27- 3,41 (m, 9H); 4,27-4,38 (t, 2H); 4,38-4,47 (m, 2H). 1 H NMR (MeOD): 0.88-1.02 (d, 6H); 1, 54-1, 63 (td, 2H); 1.63-1.81 (m, 1H); 3.27- 3.41 (m, 9H); 4.27-4.38 (t, 2H); 4.38-4.47 (m, 2H).
Spectrom. masse : détecté = 188 - attendu pour [CioH22N02]+ = 188 Spectrom. mass: detected = 188 - expected for [C10H 22 N0 2 ] + = 188
Exemple 5 : préparation du composé 4
Figure imgf000029_0002
Example 5 Preparation of compound 4
Figure imgf000029_0002
4  4
Un mélange de bétaine (A) (4g, 34,1 mmol), alcool allylique (18,6mL) et acide méthanesulfonique (2,9mL) est chauffé à δΟ 'Ό pendant 5h, sous atmosphère inerte (N2). Après retour à température ambiante, l'excès d'acide est neutralisé par addition d'une solution aqueuse saturée en bétaine. Ce mélange est ensuite concentré à sec par évaporation sous pression réduite. Le résidu est repris dans l'acétone pour redissoudre le produit. Après filtration des sels de bétaine, le filtrat est concentré par évaporation sous pression réduite. Le brut réactionnel est purifié par recristallisation dans le n-heptane. Le produit 4 est ainsi isolé sous la forme d'un solide jaune clair. (5g - rdt 58%) A mixture of betaine (A) (4g, 34.1 mmol), allyl alcohol (18.6 ml) and methanesulfonic acid (2.9 ml) is heated at δΟ'Ό for 5 h, under an inert atmosphere (N 2 ). After returning to ambient temperature, the excess of acid is neutralized by adding a saturated aqueous solution of betaine. This mixture is then concentrated to dryness by evaporation under reduced pressure. The residue is taken up in acetone to redissolve the product. After filtration of the betaine salts, the filtrate is concentrated by evaporation under reduced pressure. The crude reaction product is purified by recrystallization from n-heptane. The product 4 is thus isolated in the form of a light yellow solid. (5g - 58% reduction)
Le spectre RMN H et le spectre de masse confirment la structure du composé 4 attendu.  The 1 H NMR spectrum and the mass spectrum confirm the structure of the expected compound 4.
RMN 1H (MeOD) : 2,69 (s, 3H); 3,25-3,42 (m, 9H); 4,43 (s, 2H); 4,74-4,85 (d, 2H); 5,28-5,54 (m,2H); 5,94-6,14 (m, 1 H). 1 H NMR (MeOD): 2.69 (s, 3H); 3.25-3.42 (m, 9H); 4.43 (s, 2H); 4.74-4.85 (d, 2H); 5.28-5.54 (m, 2H); 5.94-6.14 (m, 1H).
Spectrom. masse : détecté = 158 - attendu pour [C8H16N02]+ = 158 Exemple 6 : préparation du composé 5
Figure imgf000030_0001
Spectrom. mass: detected = 158 - expected for [C 8 H 16 N0 2 ] + = 158 Example 6 Preparation of Compound 5
Figure imgf000030_0001
Un mélange de bétaine (A) (2g, 16,9mmol), n-hexanol (8ml_) et acide méthanesulfonique (1 ,4ml_) est chauffé à 140 °C pendant 8h, sous atmosphère inerte (N2). Après retour à température ambiante, l'excès d'acide est neutralisé par addition d'une solution aqueuse saturée en bétaine. Ce mélange est ensuite concentré à sec par évaporation sous pression réduite. Le résidu est repris dans l'acétone pour redissoudre le produit. Après filtration des sels de bétaine, le filtrat est concentré par évaporation sous pression réduite. Le brut réactionnel est purifié par recristallisation dans le n-heptane. Le produit est 5_ainsi isolé sous la forme d'un solide blanc. (2,6g - rdt 52%). A mixture of betaine (A) (2 g, 16.9 mmol), n-hexanol (8 ml) and methanesulfonic acid (1.4 ml) is heated at 140 ° C. for 8 h under an inert atmosphere (N 2 ). After returning to ambient temperature, the excess of acid is neutralized by adding a saturated aqueous solution of betaine. This mixture is then concentrated to dryness by evaporation under reduced pressure. The residue is taken up in acetone to redissolve the product. After filtration of the betaine salts, the filtrate is concentrated by evaporation under reduced pressure. The crude reaction product is purified by recrystallization from n-heptane. The product is isolated in the form of a white solid. (2.6g - 52% yield).
Le spectre RMN H et le spectre de masse confirment la structure du composé 5 attendu.  The 1 H NMR spectrum and the mass spectrum confirm the structure of the expected compound.
RMN 1H (MeOD) : 0,87-1 ,00 (m, 3H); 1 ,29-1 ,51 (m, 6H); 1 ,64-1 ,80 (q, 2H); 2,71 (s, 3H); 3,35 (s, 9H); 4,24-4,35 (t, 2H); 4,41 (s, 2H). 1 H NMR (MeOD): 0.87-1.00 (m, 3H); 1, 29-1, 51 (m, 6H); 1.64-1.80 (q, 2H); 2.71 (s, 3H); 3.35 (s, 9H); 4.24-4.35 (t, 2H); 4.41 (s, 2H).
Spectrom. masse : détecté = 202 - attendu pour [ΰιιΗ24Ν02]+ = 202 Spectrom. mass: Range = 202 - expected [24 ΰιιΗ Ν0 2] + = 202
Exemple 7 : préparation du composé 8 Example 7 Preparation of Compound 8
Figure imgf000030_0002
Figure imgf000030_0002
Un mélange de bétaine (A) (20g, 0,17mol), et d'alcool benzylique (277g) est chauffé à 40 °C. Après solubilisation de la bétaine dans l'alcool benzylique, l'acide méthanesulfonique (14mL) est additionné et le mélange est agité à 120°C pendant 24h. Le milieu réactionnel est ensuite distillé à 140^ sous vide pendant 4h. Le résidu est précipité dans l'éther diéthylique puis filtré. Le produit 8 est ainsi isolé après séchage sous vide à 30°C sous la forme d'un solide beige. (16,03g - rdt 31 %).  A mixture of betaine (A) (20 g, 0.17 mol), and benzyl alcohol (277 g) is heated to 40 ° C. After solubilization of betaine in benzyl alcohol, methanesulfonic acid (14 ml) is added and the mixture is stirred at 120 ° C. for 24 hours. The reaction medium is then distilled at 140 ° under vacuum for 4 hours. The residue is precipitated in diethyl ether and filtered. The product 8 is thus isolated after drying under vacuum at 30 ° C in the form of a beige solid. (16.03g - 31% yield).
Le spectre RMN H confirme la structure du composé 8 attendu.  The 1 H NMR spectrum confirms the structure of the expected compound 8.
RMN 1H (DMSO) : 2,30 (s, 3H); 3,21 (s, 9H); 4,51 (s, 2H); 5,21 (s, 2H); 7,25-7,42 (m, 5H). Exemple 8 : préparation du composé 9 1 H NMR (DMSO): 2.30 (s, 3H); 3.21 (s, 9H); 4.51 (s, 2H); 5.21 (s, 2H); 7.25-7.42 (m, 5H). Example 8 Preparation of Compound 9
Figure imgf000031_0001
Figure imgf000031_0001
Un mélange de bétaine (A) (150g, 1 ,28mol), isopropanol (615g) et acide méthanesulfonique (91 mL) est chauffé à 130°C sous agitation tout en distillant l'isopropanol en continu et avec ajout continuel d'isopropanol. Après 24h, , 100ml_ d'acide méthanesulfonique sont ajoutés. Après 48h et suivi de la formation du produit par RMN 75ml_ d'acide méthanesulfonique sont ajoutés. Après 72h, le milieu réactionnel est filtré puis le filtrat est concentré par évaporation sous pression réduite. Le brut réactionnel est purifié par ajout de bétaine dans l'isopropanol pour neutralier l'acide résiduel. Le mélange est centrifugé, le culot est éliminé et la phase liquide est évaporée sous pression réduite. Le produit 8 est ainsi isolé sous la forme d'un solide blanc. (107g - rdt 33%).  A mixture of betaine (A) (150 g, 1.28 mol), isopropanol (615 g) and methanesulfonic acid (91 ml) is heated at 130 ° C. with stirring while distilling the isopropanol continuously and with continuous addition of isopropanol. After 24 h, 100 ml of methanesulfonic acid are added. After 48 hours and follow the formation of the product by NMR 75 ml of methanesulfonic acid are added. After 72h, the reaction medium is filtered and the filtrate is concentrated by evaporation under reduced pressure. The reaction crude is purified by adding betaine in isopropanol to neutralize the residual acid. The mixture is centrifuged, the pellet is removed and the liquid phase is evaporated under reduced pressure. The product 8 is thus isolated in the form of a white solid. (107g - 33% yield).
Le spectre RMN H et le spectre de masse confirment la structure du composé 8 attendu.  The 1 H NMR spectrum and the mass spectrum confirm the structure of the expected compound 8.
RMN 1 H (DMSO) : 1 ,21 -1 ,29 (d, 6H); 3,22 (s, 9H); 4,39 (s, 2H), 5,00-5,12 (m, 1 H) Spectrom. masse : détecté = 160 - attendu pour [C8Hi8N02]+ = 160 1 H NMR (DMSO): 1.21-1.29 (d, 6H); 3.22 (s, 9H); 4.39 (s, 2H), 5.00-5.12 (m, 1H) Spectrom. mass: detected = 160 - expected for [C 8 Hi 8 N0 2 ] + = 160
Exemple 9 : préparation du composé 10 Example 9 Preparation of Compound 10
Figure imgf000031_0002
Figure imgf000031_0002
Un mélange de bétaine (A) (120g, 1 ,02mol), et d'éthanol (897mL) est chauffé à 50°C pendant 5h. L'acide méthanesulfonique (80mL) est ajouté en 45 minutes sous agitation. Le milieu réactionnel est ensuite chauffé au reflux (80°C) pendant 18h avant d'être ramené à température ambiante. Après 48h à température ambiante, la bétaine qui n'a pas réagi est filtrée. Le filtrat est concentré par évaporation sous pression réduite. Le produit 10 est ainsi isolé sous la forme d'un solide blanc.  A mixture of betaine (A) (120 g, 1.02 mol) and ethanol (897 ml) is heated at 50 ° C. for 5 hours. The methanesulfonic acid (80 ml) is added in 45 minutes with stirring. The reaction medium is then heated under reflux (80 ° C.) for 18 hours before being brought back to ambient temperature. After 48 hours at room temperature, unreacted betaine is filtered. The filtrate is concentrated by evaporation under reduced pressure. The product 10 is thus isolated in the form of a white solid.
La conversion de la bétaine en ester, estimée par RMN H, est de 96% molaire. The conversion of betaine to ester, estimated by 1 H NMR, is 96 mol%.
Le spectre RMN H confirme la structure du composé 10 attendu. The 1 H NMR spectrum confirms the structure of the expected compound.
RMN 1H (D20) : 1 ,2 (t, 3H); 2,6-2,8 (s, 3H); 3,2-3,4 (s, 9H); 4,2-4,4 (m, 4H) Exemple 10 : préparation du composé 11
Figure imgf000032_0001
1 H NMR (D 2 0): 1, 2 (t, 3H); 2.6-2.8 (s, 3H); 3.2-3.4 (s, 9H); 4.2-4.4 (m, 4H) Example 10 Preparation of compound 11
Figure imgf000032_0001
Un mélange de bétaine (A) (30g, 0,25mol), 2-méthyl-1 -butanol (300g, 4mol) est chauffé à 80 'C. Une fois que le mélange est homogène, l'acide méthanesulfonique (29.5g, 0.30mol) est ajouté. Le milieu réactionnel est chauffé à 130 ^ pendant 28h. La conversion de la bétaine en ester est de 90% molaire (suivi RMN H). A mixture of betaine (A) (30 g, 0.25 mol), 2-methyl-1-butanol (300 g, 4 mol) is heated to 80 ° C. Once the mixture is homogeneous, methanesulfonic acid (29.5g, 0.30mol) is added. The reaction medium is heated at 130 ° C. for 28 hours. The conversion of betaine to ester is 90 mol% (H NMR monitoring).
Le milieu réactionnel est placé à 4<C afin de faire précipiter la bétaine résiduelle. Le filtrat est ensuite concentré, puis le produit est précipité dans l'éther diéthylique. Il est isolé sous la forme d'un solide blanc. The reaction medium is placed at 4 <C to precipitate the residual betaine. The filtrate is then concentrated and the product is precipitated in diethyl ether. It is isolated in the form of a white solid.
Le spectre RMN H confirme la structure du composé 11 attendu.  The 1 H NMR spectrum confirms the structure of the expected compound 11.
RMN 1H (D20) : 0,8-1 (d, 6H); 1 ,8-2 (m, 1 H); 2,6-2,8 (s, 3H); 3,2-3,4 (s, 9H); 4 (dd, 2H); 4,2-4,4 (s, 2H) 1 H NMR (D 2 0): 0.8-1 (d, 6H); 1.8-2 (m, 1H); 2.6-2.8 (s, 3H); 3.2-3.4 (s, 9H); 4 (dd, 2H); 4.2-4.4 (s, 2H)
Exemple 11 : préparation du composé 12 Example 11 Preparation of compound 12
Figure imgf000032_0002
Figure imgf000032_0002
12  12
1ère étape : intermédaire (B) 1st step: intermediary (B)
Figure imgf000032_0003
Figure imgf000032_0003
(A) TEA (A) TEA
(B)  (B)
Un mélange de bétaine (A) (2g, 16,9mol), chlorure de thionyle (1 ,84mL) et acétonitrile (20mL) est chauffé à ôO'C pendant 2h, sous atmosphère inerte (Ar). Ce mélange est ensuite concentré à sec par évaporation sous pression réduite. Le résidu est mis en suspension dans le dichlorométhane puis refroidi à 0°C. Après l'addition de 2- mercaptothiazoline (2,26g), et triéthylamine (2,57mL), le milieu réactionnel est remonté à température ambiante et agité pendant 17h. Après filtration, le précipité est lavé deux fois par du dichlorométhane. L'intermédiaire (B) est ainsi isolé sous la forme d'un solide. (2,1 g - rdt 49%) A mixture of betaine (A) (2g, 16.9mol), thionyl chloride (1.84mL) and acetonitrile (20mL) is heated at 60 ° C for 2h under an inert atmosphere (Ar). This The mixture is then concentrated to dryness by evaporation under reduced pressure. The residue is suspended in dichloromethane and then cooled to 0 ° C. After the addition of 2-mercaptothiazoline (2.26 g) and triethylamine (2.57 ml), the reaction medium is brought up to room temperature and stirred for 17 h. After filtration, the precipitate is washed twice with dichloromethane. The intermediate (B) is thus isolated in the form of a solid. (2.1 g - 49% yield)
Le spectre RMN H confirme la structure de l'intermédiaire (B) attendu.  The H NMR spectrum confirms the structure of the expected intermediate (B).
RMN 1H (DMSO) : 3,26-3,30 (m, 9H); 3,47-3,55 (t, 2H); 4,55-4,63 (t, 2H); 5,22 (s, 1 H NMR (DMSO): 3.26-3.30 (m, 9H); 3.47-3.55 (t, 2H); 4.55-4.63 (t, 2H); 5.22 (s,
2H) 2H)
2ème éta e 2nd stage
Figure imgf000033_0001
Figure imgf000033_0001
(B) (12)  (B) (12)
Un mélange d'intermédiaire (B) (337mg, 1 ,32mmol), octadecylamine (250mg) et THF (20mL) est agité à température ambiante pendant 17h, sous atmosphère inerte (Ar). L'insoluble formé est filtré et le précipité est lavé au dichlorométhane. Le précipité est purifié par recristallisation dans un mélange éthanol/dichlorométhane. Le produit 12 est ainsi isolé sous la forme d'un solide floconneux beige. (248mg - rdt 69%).  A mixture of intermediate (B) (337 mg, 1, 32 mmol), octadecylamine (250 mg) and THF (20 ml) is stirred at room temperature for 17 h under an inert atmosphere (Ar). The insoluble material is filtered and the precipitate is washed with dichloromethane. The precipitate is purified by recrystallization from an ethanol / dichloromethane mixture. The product 12 is thus isolated in the form of a beige fluffy solid. (248mg - 69% yield).
Exemple 12 : Activité sur C. xerosis Example 12: Activity on C. xerosis
L'activité antimicrobienne du composé 6 à 1 % w/w a été évaluée in vitro sur Corynebacterium xerosis. The antimicrobial activity of compound 6 at 1% w / w was evaluated in vitro on Corynebacterium xerosis.
Le principe de la méthode est le suivant : les matières premières sont mises en contact avec les bactéries dans un milieu adéquat, et après un temps de contact de 24h, la réduction du nombre de germes revivifiables est mesurée, par rapport à un placébo sans lesdites matières premières.  The principle of the method is as follows: the raw materials are put in contact with the bacteria in a suitable medium, and after a contact time of 24 hours, the reduction in the number of revivable germs is measured, compared to a placebo without said raw materials.
Après 24h, la réduction en nombre de log par rapport au placebo s'élève à 3.  After 24 hours, the reduction in number of log compared to placebo is 3.
Les inventeurs considèrent que le composé 6 de formule (I) présente une activité déodorante. Exemple 13 : Formulation déodorant aérosolThe inventors consider that the compound 6 of formula (I) has a deodorant activity. Example 13 Aerosol Deodorant Formulation
Composé 6 1 %Compound 6 1%
Silicone 3%Silicone 3%
Parfum 0,75%Perfume 0,75%
Isobutane et propane 45%Isobutane and propane 45%
Alcool éthylique qsp 100% Ethyl alcohol qs 100%
Exemple 14 : Formulation anti-transpirante roll-on EXAMPLE 14 Antiperspirant Formulation Roll-On
Composé 6 1 %Compound 6 1%
Aluminium Chlorhydrate 15%Aluminum Hydrochloride 15%
PPG- 15 Stearyl Ether 2%PPG-15 Stearyl Ether 2%
Silicone 1 ,25%Silicone 1, 25%
Cetareth-33 2%Cetareth-33 2%
Parfum 0,7%Perfume 0,7%
Eau qsp 100% Water qs 100%

Claims

REVENDICATIONS
1 .- Utilisation d'au moins un composé de formule (I) suivante ou l'un de ses isomères optiques, comme agent déodorant :
Figure imgf000035_0001
1 .- Use of at least one compound of the following formula (I) or one of its optical isomers, as a deodorant agent:
Figure imgf000035_0001
 or
X" désigne un anion organique ou inorganique ; X " denotes an organic or inorganic anion;
Y désigne O ou NR' ;  Y is O or NR ';
R désigne:  R designates:
o un radical alkyle en C2-C22, linéaire ou ramifié, saturé ou insaturé ;  a C2-C22 alkyl radical, linear or branched, saturated or unsaturated;
o un radical aralkyle, où l'alkyle est en C1 -C22, linéaire ou ramifié, saturé ou insaturé, en particulier un radical aralkyle dont la partie aryle désigne un radical phényle éventuellement substitué par 1 à 4 radicaux alkyles C1 -C4 linéaires ou ramifiés ;  an aralkyl radical, in which the alkyl is C1-C22, linear or branched, saturated or unsaturated, in particular an aralkyl radical whose aryl part designates a phenyl radical optionally substituted with 1 to 4 linear or branched C1-C4 alkyl radicals; ;
o un radical aryle, en particulier un radical phényle éventuellement substitué par 1 à 4 radicaux alkyles C1 -C4 linéaires ou ramifiés ;  an aryl radical, in particular a phenyl radical optionally substituted with 1 to 4 linear or branched C1-C4 alkyl radicals;
R' désigne :  R 'designates:
o un atome d'hydrogène ;  o a hydrogen atom;
o un radical alkyle en C1 -C22, linéaire ou ramifié, saturé ou insaturé ;  o a linear or branched, saturated or unsaturated C 1 -C 22 alkyl radical;
o un radical aralkyle, où l'alkyle est en C1 -C22, linéaire ou ramifié, saturé ou insaturé, en particulier un radical aralkyle dont la partie aryle désigne un radical phényle éventuellement substitué par 1 à 4 radicaux alkyles C1 -C4 linéaires ou ramifiés ;  an aralkyl radical, in which the alkyl is C1-C22, linear or branched, saturated or unsaturated, in particular an aralkyl radical whose aryl part designates a phenyl radical optionally substituted with 1 to 4 linear or branched C1-C4 alkyl radicals; ;
o un radical aryle, en particulier un radical phényle éventuellement substitué par 1 à 4 radicaux alkyle C1 -C4 linéaires ou ramifiés.  an aryl radical, in particular a phenyl radical optionally substituted with 1 to 4 linear or branched C1-C4 alkyl radicals.
2.- Utilisation selon la revendication 1 , caractérisée en ce que le composé de formule (I) est choisi parmi les composés pour lesquels : 2. Use according to claim 1, characterized in that the compound of formula (I) is chosen from compounds for which:
- R désigne un radical alkyle linéaire ou ramifié, saturé ou insaturé en C2-C22 ; - R denotes a linear or branched, saturated or unsaturated C 2 -C 22 alkyl radical;
- Y représente O ou NR' ;  Y represents O or NR ';
- R' désigne :  - R 'designates:
o un atome d'hydrogène  o a hydrogen atom
o un radical alkyle en C1 -C22, linéaire ou ramifié, saturé ou insaturé. o a linear or branched, saturated or unsaturated C 1 -C 22 alkyl radical.
3. - Utilisation selon la revendication 1 ou 2, caractérisée en ce que le composé de formule (I) est choisi parmi les composés pour lesquels : 3. - Use according to claim 1 or 2, characterized in that the compound of formula (I) is chosen from compounds for which:
- R désigne un radical alkyle linéaire ou ramifié, saturé ou insaturé en C2-C22, et/ouR denotes a linear or branched, saturated or unsaturated C 2 -C 22 alkyl radical and / or
- Y représente O ou NH. Y represents O or NH.
4. - Utilisation selon l'une quelconque des revendications précédentes, caractérisée en ce que X" désigne : halogénure, tel que par exemple chlorure ou bromure, et de préférence chlorure ; sulfate, méthanesulfonate, citrate, lactate, acétate, et l'une quelconque de leurs combinaisons. 4. - Use according to any one of the preceding claims, characterized in that X " denotes: halide, such as for example chloride or bromide, and preferably chloride, sulphate, methanesulphonate, citrate, lactate, acetate, and one any of their combinations.
5. - Utilisation selon l'une quelconque des revendications précédentes, caractérisée en ce que le composé de formule (I) est choisi parmi les composés suivants : 5. - Use according to any one of the preceding claims, characterized in that the compound of formula (I) is chosen from the following compounds:
Figure imgf000036_0001
x-
Figure imgf000036_0002
Figure imgf000036_0001
x-
Figure imgf000036_0002
Figure imgf000036_0003
Figure imgf000036_0003
Figure imgf000036_0004
Figure imgf000036_0005
Figure imgf000036_0004
Figure imgf000036_0005
Figure imgf000037_0001
Figure imgf000037_0001
Figure imgf000037_0002
Figure imgf000037_0002
Figure imgf000037_0003
Figure imgf000037_0003
Figure imgf000037_0004
Figure imgf000037_0004
Figure imgf000037_0005
Figure imgf000037_0005
X" étant tel que défini selon la revendication 1 ou 4. X " being as defined in claim 1 or 4.
6.- Utilisation selon l'une quelconque des revendications précédentes, caractériséeue le composé de formule (I) est choisi parmi les composés suivants :
Figure imgf000037_0006
6. The use as claimed in any one of the preceding claims, characterized in that the compound of formula (I) is chosen from the following compounds:
Figure imgf000037_0006
Figure imgf000037_0007
Figure imgf000038_0001
Figure imgf000038_0002
Figure imgf000038_0003
Figure imgf000038_0004
Figure imgf000038_0005
Figure imgf000038_0006
Figure imgf000038_0007
Figure imgf000037_0007
Figure imgf000038_0001
Figure imgf000038_0002
Figure imgf000038_0003
Figure imgf000038_0004
Figure imgf000038_0005
Figure imgf000038_0006
Figure imgf000038_0007
Figure imgf000039_0001
Figure imgf000039_0001
7. Utilisation selon l'une quelconque des revendications 1 à 6, caractérisée en ce que le ou les composés de formule (I) sont présents dans une composition comprenant un milieu physiologiquement acceptable. - Composé choisi parmi les composés suivants :
Figure imgf000039_0002
, X" désignant un anion organique inorganique ;
7. Use according to any one of claims 1 to 6, characterized in that the compound or compounds of formula (I) are present in a composition comprising a physiologically acceptable medium. - compound selected from the following compounds:
Figure imgf000039_0002
X " denoting an inorganic organic anion;
Figure imgf000039_0003
, Z représentant un anion organique ou inorganique à l'exception du chlorure, et de préférence choisi parmi bromure, sulfate, méthanesulfonate, citrate, lactate, acétate ;
Figure imgf000039_0003
Z, representing an organic or inorganic anion except chloride, and preferably selected from bromide, sulfate, methanesulfonate, citrate, lactate, acetate;
ou l'un de leurs isomères optiques.  or one of their optical isomers.
9.- Composé selon la revendication 8, caractérisé en ce qu'il est choisi parmi les mposés suivants : 9. A compound according to claim 8, characterized in that it is chosen from the following formulas:
Figure imgf000039_0004
ou l'un de leurs isomères optiq
Figure imgf000039_0004
or one of their optiq isomers
10.- Composé selon la revendication 8, caractérisé en ce qu'il est représenté par la formule suivante :
Figure imgf000040_0001
, Z représentant un anion organique ou inorganique à l'exception du chlorure, et de préférence choisi parmi bromure, sulfate, méthanesulfonate, citrate, lactate, acétate, et plus préférentiellement le méthanesulfonate ;
10. A compound according to claim 8, characterized in that it is represented by the following formula:
Figure imgf000040_0001
, Z representing an organic or inorganic anion with the exception of chloride, and preferably selected from bromide, sulfate, methanesulphonate, citrate, lactate, acetate, and more preferably methanesulphonate;
ou l'un de ses isomères optiques.  or one of its optical isomers.
1 1 . - Composition, notamment composition cosmétique comprenant dans un milieu physiologiquement acceptable au moins un composé de formule (I) tel que défini selon l'une quelconque des revendications 1 à 10, en association avec au moins un actif anti- transpirant et/ou au moins un autre actif déodorant dans un milieu physiologiquement acceptable. 1 1. Composition, in particular a cosmetic composition comprising, in a physiologically acceptable medium, at least one compound of formula (I) as defined according to any one of Claims 1 to 10, in combination with at least one antiperspirant active agent and / or at least one another deodorant active agent in a physiologically acceptable medium.
12. - Composition, notamment composition cosmétique, comprenant dans un milieu physiologiquement acceptable au moins un composé de formule (I), tel que défini selon l'une quelconque des revendications 1 à 10, éventuellement en association avec au moins un actif anti-transpirant et/ou au moins un autre actif déodorant dans un milieu physiologiquement acceptable, ladite composition étant accompagnée d'un emballage ou notice d'information présentant des informations visuelles concernant le traitement des odeurs et/ou de la transpiration d'un être humain, et/ou des informations sur la présence d'au moins un actif anti-transpirant et/ou au moins un actif déodorant, éventuellement parmi d'autres informations visuelles. 12. - Composition, in particular a cosmetic composition, comprising in a physiologically acceptable medium at least one compound of formula (I), as defined according to any one of claims 1 to 10, optionally in combination with at least one antiperspirant active agent and / or at least one other deodorant active agent in a physiologically acceptable medium, said composition being accompanied by a package or information notice presenting visual information concerning the treatment of odors and / or perspiration of a human being, and / or information on the presence of at least one antiperspirant active agent and / or at least one deodorant active agent, possibly among other visual information.
13. - Dispositif aérosol constitué par : 13. - Aerosol device consisting of:
(A) au moins un récipient comprenant une composition telle que définie selon la revendication 1 1 ou 12,  (A) at least one container comprising a composition as defined according to claim 1 1 or 12,
(B) au moins un agent propulseur et au moins un moyen de distribution de la dite composition sous forme aérosol.  (B) at least one propellant and at least one means for dispensing said composition in aerosol form.
14.- Composition telle que définie selon la revendication 1 1 ou 12, ou dispositif la comprenant, accompagné(e) d'un emballage (« packaging ») ou notice d'information comprenant, éventuellement parmi d'autres informations visuelles, la mention de la présence d'un ou plusieurs des composés tels que définis selon l'une quelconque des revendications 1 à 10, éventuellement en association avec au moins un actif anti- transpirant et/ou au moins un autre actif déodorant, ledit emballage ou ladite notice d'information présentant des informations visuelles concernant le traitement des odeurs et/ou de la transpiration d'un être humain et/ou des informations sur la présence d'au moins un actif anti-transpirant et/ou au moins un actif déodorant. 15- Méthode cosmétique de traitement des odeurs corporelles, en particulier axillaires, consistant à appliquer sur la surface de la peau une composition comprenant dans un milieu physiologiquement acceptable au moins un composé de formule (I) tel que défini selon l'une quelconque des revendications 1 à 10, ou une composition telle que définie selon l'une quelconque des revendications 1 1 à 12. 14.- composition as defined in claim 1 1 or 12, or device comprising it, accompanied (e) a packaging ("packaging") or information notice including, possibly among other visual information, the mention the presence of one or more of the compounds as defined in any one of claims 1 to 10, optionally in combination with at least one antiperspirant active agent and / or at least one other deodorant active agent, said package or said notice information presenting visual information concerning the treatment of odors and / or perspiration of a human being and / or information on the presence of at least one antiperspirant active and / or at least one deodorant active. 15- A cosmetic method for treating body odors, in particular axillary, comprising applying to the surface of the skin a composition comprising, in a physiologically acceptable medium, at least one compound of formula (I) as defined according to any one of the claims 1 to 10, or a composition as defined according to any one of claims 1 1 to 12.
PCT/EP2014/064047 2013-07-10 2014-07-02 Glycine-betaine amide and ester derivatives as deodorising active substances, and cosmetic compositions containing same WO2015003968A1 (en)

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CN106588680A (en) * 2016-11-07 2017-04-26 杭州海尔希畜牧科技有限公司 Lauryl betaine preparation method
FR3088930A1 (en) * 2018-11-27 2020-05-29 Surfactgreen Process for the preparation of a surfactant composition based on a glycine ester salt of betaine and composition thus obtained
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US20220024855A1 (en) * 2018-11-27 2022-01-27 Surfactgreen Process for preparing a surfactant composition based on a glycine betaine ester salt, and composition thus obtained
FR3099058A1 (en) 2019-11-22 2021-01-29 Surfactgreen Use of a glycine betaine derivative as a hair conditioning agent
WO2021099715A1 (en) 2019-11-22 2021-05-27 Surfactgreen Use of a glycine betaine derivative as an agent for conditioning keratin fibres
FR3112946A1 (en) 2020-07-31 2022-02-04 Surfactgreen Use of a cosmetic composition containing a glycine betaine derivative for protecting the skin against external aggressions

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