WO2014131871A2 - Cosmetic composition in the form of an oil-in-water nanoemulsion for the oxidation dyeing of keratin fibres, and process for the same - Google Patents

Cosmetic composition in the form of an oil-in-water nanoemulsion for the oxidation dyeing of keratin fibres, and process for the same Download PDF

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Publication number
WO2014131871A2
WO2014131871A2 PCT/EP2014/053910 EP2014053910W WO2014131871A2 WO 2014131871 A2 WO2014131871 A2 WO 2014131871A2 EP 2014053910 W EP2014053910 W EP 2014053910W WO 2014131871 A2 WO2014131871 A2 WO 2014131871A2
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composition
chosen
weight
fatty
alkyl
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PCT/EP2014/053910
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French (fr)
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WO2014131871A3 (en
Inventor
Delphine Charrier
Géraldine Fack
Aurélie CAMBLONG
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L'oreal
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Priority claimed from FR1351772A external-priority patent/FR3002441B1/en
Priority claimed from FR1351774A external-priority patent/FR3002439B1/en
Application filed by L'oreal filed Critical L'oreal
Publication of WO2014131871A2 publication Critical patent/WO2014131871A2/en
Publication of WO2014131871A3 publication Critical patent/WO2014131871A3/en

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A61K8/062—Oil-in-water emulsions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/21—Emulsions characterized by droplet sizes below 1 micron

Definitions

  • Cosmetic composition in the form of an oil-in-water nanoemulsion for the oxidation dyeing of keratin fibres and process for the same
  • the present invention relates to a cosmetic composition in the form o f an oil-in-water nanoemulsion for the oxidation dyeing o f keratin fibres, in particular human keratin fibres such as the hair.
  • a subj ect of the present invention is a dying cosmetic composition (A) in the form o f an oil-in-water nanoemulsion comprising one or more oxidation dyes, one or more surfactants, one or more fatty substances and water in a content of greater than or equal to 40% by weight relative to the total weight of the composition; the number-average size of the oil droplets in the said nanoemulsion being less than or equal to 100 nm.
  • the present invention also relates to the use of the composition according to the invention for dyeing keratin fibres.
  • the present invention also relates to a process for dyeing keratin fibres, in particular human keratin fibres such as the hair, using composition (A) according to the invention.
  • this process also uses an oxidizing composition (B) .
  • the present invention relates to a kit for the oxidation dyeing o f keratin fibres, which is suitable for performing such a process.
  • oxidation dyeing methods also known as oxidation dyeing, which use dye compositions containing oxidation dye precursors, generally referred to as oxidation bases, such as ortho- or para- phenylenediamines, ortho- or para-aminopheno ls and heterocyclic compounds, have been developed for dyeing human keratin fibres in a long-lasting manner.
  • oxidation bases are co lourless or weakly co loured compounds, which, when combined with oxidizing products, may give rise to coloured compounds via a process of oxidative condensation.
  • couplers or coloration modifiers the latter being chosen especially from aromatic meta- diaminobenzenes, meta-aminophenols, meta-diphenols and certain heterocyclic compounds such as indole compounds.
  • the prior art compositions are not entirely satisfactory, and their performance qualities can be improved in particular, firstly, as regards the working qualities after mixing with an oxidizing composition, especially in terms of texture, ease o f application and ease o f spreading on the ends, and, secondly, as regards the dyeing qualities obtained with these mixtures, especially in terms o f intensity, homogeneity and selectivity o f the dyeing obtained.
  • One subj ect of the present invention is thus a cosmetic composition (A) in the form o f an oil-in-water nanoemulsion comprising one or more oxidation dyes, one or more surfactants, one or more fatty substances and at least 40% by weight of water, relative to the total weight of the composition; the number-average size o f the oil droplets in the said nanoemulsion being less than or equal to 100 nm.
  • composition according to the invention has very good working qualities, and especially a particularly pleasant texture.
  • composition according to the invention has superior dyeing quality, especially in terms of intensity, homogeneity and selectivity o f the dyeing obtained.
  • This dye composition (A) may be used in a process for dyeing keratin fibres using this composition in combination with an oxidizing composition (B) .
  • a subj ect of the invention is thus also a process for dyeing keratin fibres, which consists in applying to the keratin fibres a composition (A) according to the invention, the said composition being applied sequentially to or simultaneously with an oxidizing composition (B) comprising one or more oxidizing agents.
  • the oxidizing composition (B) is also in the form o f a nanoemulsion and comprises one or more oxidizing agents, one or more surfactants, one or more fatty substances and water; the number-average size of the oil droplets in the said nanoemulsion being less than or equal to 100 nm.
  • composition (A) according to the invention is in the form o f an oil-in-water nanoemulsion.
  • the oxidizing composition (B) is also in the form o f an oil-in-water nanoemulsion.
  • oil-in-water nanoemulsion denotes a true emulsion, i. e. a thermodynamically unstable dispersion of oil droplets in a continuous aqueous phase.
  • Nanoemulsions are to be distinguished from microemulsions, which are thermo dynamically stable dispersions in the form o f micelles of oil-swo llen surfactants, and which form spontaneously by simple mixing o f the constituents, without substantial input of energy.
  • the number-average size of the oil droplets in the nanoemulsions according to the invention is less than or equal to 100 nm.
  • the number-average size o f the oil droplets of the nanoemulsion(s) according to the invention ranges from 10 to 90 nm, better still from 20 to 80 nm and more preferentially from 40 to 60 nm.
  • the number-average size of the particles may be determined in particular according to the known method of quasi-elastic light scattering.
  • a machine that may be used for this determination mention may be made of the Brookhaven brand machine equipped with an SX 200 optical bed (with a 532 nm laser) and a BI 9000 correlator. This machine gives a measurement of the mean diameter by photon correlation spectroscopy (PCS), which makes it possible to determine the number-average diameter from the polydispersity factor, which is also measured by the machine.
  • PCS photon correlation spectroscopy
  • the nanoemulsion may also be characterized by measuring its turbidity according to the NTU method using a 21 OOP mo del turbidimeter from the company Hach, at room temperature.
  • the turbidity o f the nanoemulsions o f the invention is generally less than 400 NTU units and preferably between 50 and 250 NTU units.
  • a nanoemulsion generally has a transparent to blueish or translucent appearance, in the absence of opacifying or nacreous additional compound(s).
  • the reduction in the size of the oil globules makes it possible especially to promote the penetration of the active ingredients into the keratin materials, for example through the surface layers of the hair (vehicle effect) .
  • the cosmetic composition (A) according to the invention comprises one or more oxidation dyes .
  • the oxidizing composition (B) does not comprise any oxidation dyes .
  • oxidation dyes that may be used in the present invention are generally chosen from oxidation bases, optionally combined with one or more couplers .
  • the oxidation dye(s) comprise one or more oxidation bases.
  • the oxidation bases may be chosen especially from para- phenylene diamines, bis (phenyl) alky lene diamines, para-aminophenols, ortho-aminopheno ls and heterocyclic bases, and the addition salts thereo f.
  • para-phenylenediamines examples that may be mentioned include para-phenylenediamine, para-tolylenediamine, 2- chloro-para-pheny lene diamine, 2,3 -dimethyl-para-phenylenediamine, 2, 6 -dimethyl-para-pheny lene diamine, 2,6-diethyl-para- phenylenediamine, 2,5 -dimethyl-para-phenylenediamine, N,N- dimethyl-para-pheny lene diamine, ⁇ , ⁇ -diethyl-para-phenylenedi amine, ⁇ , ⁇ -dipropyl-para-pheny lene diamine, 4 -amino -N,N- diethyl- 3 - methylaniline, N,N-bis( -hydroxy ethyl) -para-phenylenediamine, 4- N,N-bis( -hydroxy ethyl) amino -2 -met hylaniline,
  • para-phenylenediamine para-tolylenediamine, 2-isopropyl-para- phenylenediamine, 2- -hydroxyethyl-para-phenylenediamine, 2- ⁇ - hydroxyethyloxy-para-phenylenediamine, 2, 6 -dimethyl-par a- phenylene diamine, 2, 6- diet hyl-para-phenylene diamine, 2, 3 -dimethyl- par a-phenylenediamine, N, N-bis( - hydroxy ethyl) -par a- phenylenediamine, 2-chloro-para-phenylenediamine and 2- ⁇ - acetylaminoethyloxy-para-phenylenediamine, and the addition salts thereo f with an acid, are particularly preferred.
  • the bis(phenyl)alkylenediamines examples include N,N'-bis( -hydroxyethyl)-N,N'-bis(4'- aminophenyl)- l ,3 -diaminopropanol, N,N'-bis( -hydroxyethyl)-N,N'- bis (4 '-aminophenyl) ethylene diamine, N,N'-bis(4- aminophenyl)tetramethylenediamine, N, N'-bis( -hydroxy ethyl) -N,N '- bis(4- amino phenyl)tetramethylenediamine, N,N'-bis(4- methylaminophenyl)tetramethylenediamine, N,N'-bis(ethyl)-N,N'- bis(4'-amino-3 '-methylphenyl)ethylenediamine, 1 , 8 -bis (2,5 - diamin
  • para-aminophenols examples that may be mentioned include para-aminophenol, 4-amino-3 -methylpheno l, 4- amino-3 -fluoropheno l, 4-amino-3 -chlorophenol, 4-amino-3 - hydroxymethylpheno l, 4-amino-2-methylpheno l, 4-amino-2- hydroxymethylpheno l, 4-amino-2-methoxymethylpheno l, 4-amino-2- aminomethylpheno l, 4-amino-2-( -hydroxyethyl-aminomethyl)pheno l and 4-amino-2-fluorophenol, and the addition salts thereof with an acid.
  • ortho-aminopheno ls examples that may be mentioned include 2-aminophenol, 2-amino-5 -methylpheno l, 2-amino- 6-methylpheno l and 5 -acetamido-2-aminopheno l, and the addition salts thereo f.
  • heterocyclic bases examples that may be mentioned include pyridine derivatives, pyrimidine derivatives and pyrazole derivatives.
  • pyridine derivatives that may be mentioned are the compounds described, for example, in patents GB 1 026978 and GB 1 153 196, for instance 2,5-diaminopyridine, 2-(4- methoxyphenyl)amino-3-aminopyridine and 3,4-diaminopyridine, and the addition salts thereof.
  • pyridine oxidation bases that are useful in the present invention are the 3-aminopyrazolo[ 1 ,5-a]pyridine oxidation bases or the addition salts thereof described, for example, in patent application FR 2 801 308.
  • Examples that may be mentioned include pyrazolo[l ,5- a]pyrid-3-ylamine, 2-(acetylamino)pyrazolo[ 1 ,5-a]pyrid-3-ylamine, 2- (morpholin-4-yl)pyrazolo[ 1 ,5-a]pyrid-3-ylamine, 3- aminopyrazolo[ 1 ,5-a]pyridine-2-carboxylic acid, 2- methoxypyrazolo[ 1 ,5-a]pyrid-3-ylamine, (3-aminopyrazolo[ 1 ,5- a]pyrid-7-yl)methanol, 2-(3-aminopyrazolo[ 1 ,5-a]pyrid-5-yl
  • pyrimidine derivatives that may be mentioned are the compounds described, for example, in the patents DE 2359399; JP 88-169571; JP 05-63124; EP 0770375 or patent application WO 96/15765, such as 2,4,5,6-tetraaminopyrimidine, 4-hydroxy-2,5,6- triaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 2,4- dihydroxy-5,6-diaminopyrimidine, 2,5,6-triaminopyrimidine and the addition salts thereof and the tautomeric forms thereof, when a tautomeric equilibrium exists.
  • pyrazole derivatives that may be mentioned are the compounds described in patents DE 3843892 and DE 4133957 and patent applications WO 94/08969, WO 94/08970, FR-A-2733 749 and DE 195 43 988, for instance 4,5-diamino- 1 -methylpyrazole, 4,5- diamino- 1 -( -hydroxyethyl)pyrazole, 3,4-diaminopyrazole, 4,5- diamino- 1 -(4 '-chlorobenzyl)pyrazole, 4,5-diamino - 1 ,3- dimethylpyrazole, 4,5-diamino-3-methyl- 1 -phenylpyrazole, 4,5- diamino- 1 -methyl-3-phenylpyrazole, 4-amino- 1 ,3-dimethyl-5- hydrazinopyrazole, 1 -benzyl-4,5-diamino-3-
  • a 4,5-diaminopyrazole will preferably be used, and even more preferentially 4,5-diamino- 1 -( -hydroxyethyl)pyrazole and/or a salt thereof.
  • Pyrazole derivatives that may also be mentioned include diamino-N,N-dihydropyrazolopyrazolones and especially those described in patent application FR-A-2886 136, such as the following compounds and the addition salts thereof: 2,3-diamino-6,7-dihydro- lH,5H-pyrazolo[ 1 ,2-a]pyrazol- 1 -one, 2-amino-3-ethylamino-6,7- dihydro- lH,5H-pyrazolo[ 1 ,2-a]pyrazol- 1 - one, 2-amino-3- isopropylamino-6,7-dihydro-lH,5H-pyrazolo[ 1 ,2-a]pyrazol- 1 -one, 2- amino-3-(pyrrolidin-l-yl)-6,7-dihydro-lH,5H-pyrazolo[ 1 ,2-a]pyrazol- 1-one, 4,5-d
  • Use will preferably be made of 2,3-diamino-6,7-dihydro- lH,5H-pyrazolo[l,2-a]pyrazol-l-one and/or one of its salts.
  • Heterocyclic bases that will preferentially be used include 4,5- diamino-l -( -hydroxyethyl)pyrazole and/or 2,3-diamino-6,7-dihydro- lH,5H-pyrazolo[l,2-a]pyrazol-l-one and/or a salt thereof.
  • the oxidation dye(s) may also comprise one or more couplers, which may be chosen from those conventionally used for the dyeing of keratin fibres.
  • couplers mention may be made especially of meta-phenylenediamines, meta-aminophenols, meta-diphenols, naphthalene-based couplers and heterocyclic couplers, and also the addition salts thereof.
  • Examples that may be mentioned include 1,3- dihydroxybenzene, 1 ,3-dihydroxy-2-methylbenzene, 4-chloro- 1 ,3- dihydroxybenzene, 2,4-diamino- 1 -( -hydroxyethyloxy)benzene, 2- amino -4 -( ⁇ - hydroxy ethy lamino) - 1 -methoxybenzene, 1,3- diaminobenzene, 1 ,3-bis(2,4-diaminophenoxy)propane, 3- ureidoaniline, 3-ureido- 1 -dimethylaminobenzene, sesamol, 1- ⁇ - hydroxyethylamino-3,4-methylenedioxybenzene, cc-naphthol, 2- methyl- 1 -naphthol, 6-hydroxyindole, 4-hydroxyindole, 4-hydroxy-N- methylindole, 2-amino-3-hydroxypyridine, 6-
  • addition salts o f the oxidation bases and couplers that may be used within the context of the invention are especially chosen from the addition salts with an acid such as the hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates .
  • the oxidation base(s) may advantageously represent from 0.0001 % to 10% by weight relative to the total weight of the composition containing them, preferably from 0.005 % to 5 % by weight and better still from 0. 1 % to 2% by weight relative to the total weight of this composition.
  • the coupler(s), if they are present, may advantageously represent from 0.0001 % to 1 0% by weight relative to the total weight of the composition containing them, and preferably from 0.005 % to 5 % by weight relative to the total weight of this composition.
  • Composition (A) according to the invention comprises one or more surfactants .
  • the oxidizing composition (B) also comprises one or more surfactants .
  • They may be chosen especially from nonionic, cationic, anionic and amphoteric or zwitterionic surfactants .
  • the said surfactant(s) according to the invention preferably comprise one or more nonionic surfactants .
  • nonionic surfactant(s) that may be used in the compositions are described, for example, in the Handbook of Surfactants by M .R. Porter, published by Blackie & Son (Glasgow and London), 1991 , pp . 1 16- 178.
  • nonionic surfactants examples include the fo llowing nonionic surfactants :
  • (C8-C3o)alkyl(poly)glucosides (C8-C3o)alkenyl(poly) glucosides, which are optionally oxyalkylenated (0 to 10 oxyalkylene units) and comprising from 1 to 15 glucose units, (C8-C3o)alkyl (poly)glucoside esters;
  • the oxyalkylene units are more particularly oxyethylene or oxypropylene units, or a combination thereof, preferably oxyethylene units.
  • the number of moles of ethylene oxide and/or propylene oxide preferably ranges from 1 to 250, more particularly from 2 to 100 and better still from 2 to 50; the number of moles of glycerol ranges especially from 1 to 50 and better still from 1 to 10.
  • nonionic surfactants according to the invention do not comprise any oxypropylene units.
  • glycerolated nonionic surfactants use is preferably made of monoglycerolated or polyglycerolated C8-C40 alcohols, comprising from 1 to 50 mol of glycerol and preferably from 1 to 10 mol of glycerol.
  • lauryl alcohol containing 4 mol of glycerol (INCI name: Polyglyceryl-4 Lauryl Ether), lauryl alcohol containing 1.5 mol of glycerol, oleyl alcohol containing 4 mol of glycerol (INCI name: Polyglyceryl-4 Oleyl Ether), oleyl alcohol containing 2 mol of glycerol (INCI name: Polyglyceryl-2 Oleyl Ether), cetearyl alcohol containing 2 mol of glycerol, cetearyl alcohol containing 6 mol of glycerol, oleyl/cetyl alcohol containing 6 mol of glycerol, and octadecanol containing 6 mol of glycerol.
  • the glycerolated alcohols it is more particularly preferred to use the Cs/Cio alcohol containing 1 mol of glycerol, the C10 C12 alcohol containing 1 mol of glycerol and the C12 alcohol containing 1.5 mol of glycerol.
  • the nonionic surfactant(s) according to the invention are preferentially chosen from:
  • - oxyethylenated C8-C40 alcohols comprising from 1 to 100 mol of ethylene oxide, preferably from 2 to 50 and more particularly from 2 to 40 mol of ethylene oxide and comprising one or two fatty chains;
  • saturated or unsaturated oxyethylenated plant oils comprising from 1 to 100 and preferably from 2 to 50 mol of ethylene oxide;
  • - monoglycerolated or polyglycerolated C8-C40 alcohols comprising from 1 to 50 mol of glycerol and preferably from 1 to 10 mol of glycerol.
  • nonionic surfactant(s) are chosen from:
  • Composition (A) according to the invention and the oxidizing composition (B) may comprise one or more cationic surfactants .
  • cationic surfactant means a surfactant that is positively charged when it is contained in the composition according to the invention. This surfactant may bear one or more positive permanent charges or may contain one or more cationizable functions in the compositions .
  • the cationic surfactant(s) are preferably chosen fro m optionally po lyoxyalkylenated, primary, secondary or tertiary fatty amines, or salts thereof, and quaternary ammonium salts, and mixtures thereo f.
  • the fatty amines generally comprise at least one C 8 - C30 hydrocarbon-based chain.
  • the groups Rs to Rn which may be identical or different, represent a linear or branched aliphatic group comprising from 1 to 30 carbon atoms, or an aromatic group such as aryl or alkylaryl, at least one of the groups Rs to Rn denoting a group comprising from 8 to 30 carbon atoms and preferably from 12 to 24 carbon atoms.
  • the aliphatic groups may comprise heteroatoms especially such as oxygen, nitrogen, sulfur and halogens .
  • the aliphatic groups are chosen, for example, from C 1 - C30 alkyl, C 1 - C30 alkoxy, polyoxy(C2- Ce)alkylene, C 1 - C30 alkylamide, (C i 2-C22)alkylamido(C2- C 6 )alkyl, (C i 2 -C 22 )alkyl acetate and C 1 - C 30 hydroxyalkyl groups;
  • X " is an anion chosen from the group of halides, phosphates, acetates, lactates, (C i -C 4 )alkyl sulfates, and (C i -C 4 )alkyl- or (C i - C 4 )alkylarylsulfonates.
  • quaternary ammonium salts of formula (I) those that are preferred are, on the one hand, tetraalkylammonium salts, for instance dialkyldimethylammonium or alkyltrimethylammonium salts in which the alkyl group contains approximately from 12 to 22 carbon atoms, in particular behenyltrimethylammonium, distearyldimethylammonium, cetyltrimethylammonium or benzyldimethylstearylammonium salts, or, on the other hand, the palmitylamidopropyltrimethylammonium salt, the stearamidopropyltrimethylammonium salt, the stearamidopropyldimethylcetearylammonium salt, or the stearamidopropyldimethyl(myristyl acetate)ammonium salt sold under the name Ceraphyl® 70 by the company Van Dyk. It is particularly preferred to use the chloride salts of these compounds .
  • Ri 2 represents an alkenyl or alkyl group containing from 8 to 30 carbon atoms, derived for example from tallow fatty acids
  • Ri 3 represents a hydrogen atom, a C 1 -C 4 alkyl group or an alkenyl or alkyl group containing from 8 to 30 carbon atoms
  • R14 represents a C 1 -C 4 alkyl group
  • R15 represents a hydrogen atom or a C 1 -C 4 alkyl group
  • X " is an anion chosen from the group consisting of halides, phosphates, acetates, lactates, alkyl sulfates, alkylsulfonates or alkylarylsulfonates in which the alkyl and aryl groups respectively preferably comprise from 1 to 20 carbon atoms and from 6 to 30 carbon atoms.
  • Ri 2 and R13 preferably denote a mixture of alkenyl or alkyl groups containing from 12 to 21 carbon atoms, derived for example from tallow fatty acids, R14 preferably denotes a methyl group, and R15 preferably denotes a hydrogen atom.
  • R14 preferably denotes a methyl group
  • R15 preferably denotes a hydrogen atom.
  • Rewoquat ® W 75 by the company Rewo;
  • Ri 6 denotes an alkyl radical comprising approximately from 16 to 30 carbon atoms which is optionally hydroxylated and/or interrupted by one or more oxygen atoms
  • R17 is chosen from hydrogen or an alkyl radical comprising from 1 to 4 carbon atoms or an
  • R 21 which may be identical or different, are chosen from hydrogen or an alkyl radical comprising from 1 to 4 carbon atoms and X " is an anion chosen from the group of the halides, acetates, phosphates, nitrates and methyl sulfates.
  • Such compounds are, for example, Finquat CT-P, available from the company Finetex (Quaternium 89), and Finquat CT, available from the company Finetex (Quaternium 75).
  • - quaternary ammonium salts containing at least one ester function such as those of formula (IV) below:
  • R22 is chosen from Ci-C 6 alkyl groups and Ci-C 6 hydroxyalkyl or dihydroxyalkyl groups;
  • R23 is chosen from:
  • R27 which are linear or branched, saturated unsaturated C1-C22 hydrocarbon-based groups
  • R25 is chosen from:
  • R24, R26 and R28 which may be identical or different, are chosen from linear or branched, saturated or unsaturated C7-C21 hydrocarbon-based groups;
  • r, s and t which may be identical or different, are integers ranging from 2 to 6;
  • y is an integer ranging from 1 to 10;
  • x and z which may be identical or different, are integers ranging from 0 to 10;
  • X " is a simple or complex, organic or mineral anion
  • the alkyl groups R22 may be linear or branched, and more particularly linear.
  • R22 denotes a methyl, ethyl, hydroxyethyl or dihydroxypropyl group , and more particularly a methyl or ethyl group .
  • the sum x + y + z is from 1 to 10.
  • R23 is an R 27 hydrocarbon-based group, it may be long and may contain from 12 to 22 carbon atoms, or may be short and may contain from 1 to 3 carbon atoms.
  • R25 is an R2 hydrocarbon-based group , it preferably contains 1 to 3 carbon atoms .
  • R24 , R26 and R28 which may be identical or different, are chosen from linear or branched, saturated or unsaturated C 1 1 -C 2 1 hydrocarbon-based groups, and more particularly from linear or branched, saturated or unsaturated C n -C 2 1 alkyl and alkenyl groups .
  • x and z which may be identical or different, are equal to 0 or 1 .
  • y is equal to 1 .
  • r, s and t which may be identical or different, are equal to 2 or 3 , and even more particularly are equal to 2.
  • the anion X " is preferably a halide (chloride, bromide or iodide) or an alkyl sulfate, more particularly methyl sulfate .
  • a halide chloride, bromide or iodide
  • an alkyl sulfate more particularly methyl sulfate .
  • use may be made o f methanesulfonate, phosphate, nitrate, tosylate, an anion derived from an organic acid, such as acetate or lactate, or any other anion compatible with the ammonium containing an ester function.
  • the anion X " is even more particularly chloride or methyl sulfate.
  • R22 denotes a methyl or ethyl group
  • x and y are equal to 1 ;
  • z is equal to 0 or 1 ;
  • r, s and t are equal to 2;
  • R23 is chosen from: - the group
  • R25 is chosen from:
  • R24, R26 and R28 which may be identical or different, are chosen from linear or branched, saturated or unsaturated C 13 -C 17 hydrocarbon-based groups, and preferably from linear or branched, saturated or unsaturated C 13 -C 17 alkyl and alkenyl groups.
  • hydrocarbon-based groups are advantageously linear.
  • acyl groups preferably contain 14 to 18 carbon atoms and are obtained more particularly from a vegetable oil, such as palm oil or sunflower oil.
  • these groups may be identical or different.
  • These products are obtained, for example, by direct esterification of triethanolamine, triisopropanolamine, an alkyldiethanolamine or an alkyldiisopropanolamine, which are optionally oxyalkylenated, with Cio-C 3 o fatty acids or with mixtures of Cio-C 3 o fatty acids of plant or animal origin, or by transesterification of the methyl esters thereof.
  • This esterification is followed by quaternization using an alkylating agent such as an alkyl (preferably methyl or ethyl) halide, a dialkyl (preferably methyl or ethyl) sulfate, methyl methanesulfonate, methyl para-toluenesulfonate, glyco l chlorohydrin or glycerol chlorohydrin.
  • an alkylating agent such as an alkyl (preferably methyl or ethyl) halide, a dialkyl (preferably methyl or ethyl) sulfate, methyl methanesulfonate, methyl para-toluenesulfonate, glyco l chlorohydrin or glycerol chlorohydrin.
  • Such compounds are, for example, sold under the names Dehyquart ® by the company Henkel, Stepanquat ® by the company Stepan, Noxamium ® by the company Ceca or Rewoquat ® WE 1 8 by the company Rewo-Witco .
  • composition according to the invention may contain, for example, a mixture o f quaternary ammonium monoester, diester and triester salts with a weight majority o f diester salts .
  • Use may be made o f behenoylhydroxypropyltrimethylammonium chloride, provided by Kao under the name Quatarmin BTC 13 1 .
  • the ammonium salts containing at least one ester function contain two ester functions.
  • quaternary ammonium salts containing at least one ester function which can be used, it is preferred to use dipalmitoylethylhydroxyethylmethylammonium salts.
  • the cationic surfactants are preferably chosen from those of formula (I) and those of formula (IV), and even more preferentially from those o f formula (I) .
  • Composition (A) according to the invention and the oxidizing composition (B) may comprise one or more anionic surfactants .
  • anionic surfactant means a surfactant comprising, as ionic or ionizable groups, only anionic groups . These anionic groups are preferably chosen from the fo llowing groups :
  • anionic surfactants that may be used in the composition according to the invention, mention may be made o f alkyl sulfates, alkyl ether sulfates, alkylamido ether sulfates, alkylaryl polyether sulfates, monoglyceride sulfates, alkylsulfonates, alkylamidesulfonates, alkylarylsulfonates, a-olefin sulfonates, paraffin sulfonates, alkyl sulfosuccinates, alkyl ether sulfo succinates, alkylamide sulfosuccinates, alkyl sulfoacetates, acylsarcosinates, acylglutamates, alkyl sulfosuccinamates, acylisethionates and N- acyltaurates, polyglycoside polycarboxylic acid and alkyl
  • These compounds can be oxyethylenated and then preferably comprise from 1 to 50 ethylene oxide units.
  • the salts o f C 6 - C24 alkyl monoesters of polyglycoside- polycarboxylic acids may be chosen from C 6 - C24 alkyl po lyglycoside- citrates, C 6 - C24 alkyl polyglycoside-tartrates and C 6 - C24 alkyl poly glycoside-sulfo succinates .
  • anionic surfactant(s) When the anionic surfactant(s) are in salt form, they may be chosen from alkali metal salts such as the sodium or potassium salt and preferably the sodium salt, ammonium salts, amine salts and in particular amino alcohol salts, or alkaline-earth metal salts such as the magnesium salts .
  • Examples o f amino alcoho l salts that may especially be mentioned include monoethano lamine, diethanolamine and triethanolamine salts, monoisopropanolamine, diisopropanolamine or triisopropanolamine salts, 2-amino-2-methyl- 1 -propanol salts, 2- amino-2-methyl- 1 ,3 -propanediol salts and tris(hydroxymethyl)amino methane salts.
  • Alkali metal or alkaline-earth metal salts and in particular sodium or magnesium salts, are preferably used.
  • anionic surfactants use is preferably made o f (C 6 - C24)alkyl sulfates, (C 6 - C24)alkyl ether sulfates comprising from 2 to 50 ethylene oxide units, in particular in the form o f alkali metal, ammonium, amino alcohol and alkaline-earth metal salts, or a mixture of these compounds.
  • (C i 2 -C 2 o)alkyl sulfates (C 1 2 - C 2 o)alkyl ether sulfates comprising from 2 to 20 ethylene oxide units, especially in the form o f alkali metal, ammonium, amino alcoho l and alkaline-earth metal salts, or a mixture of these compounds .
  • sodium lauryl ether sulfate containing 2.2 mo l o f ethylene oxide.
  • Composition (A) according to the invention and the oxidizing composition (B) may comprise one or more amphoteric or zwitterionic surfactants .
  • amphoteric or zwitterionic surfactant(s), which are preferably non-silicone, which may be used in the present invention may especially be derivatives o f aliphatic secondary or tertiary amines, optionally quaternized in which derivatives the aliphatic group is a linear or branched chain comprising from 8 to 22 carbon atoms, the said amine derivatives containing at least one anionic group, for instance a carboxylate, sulfonate, sulfate, phosphate or phosphonate group .
  • R a represents a C 1 0 - C30 alkyl or alkenyl group derived from an acid R a COOH preferably present in hydro lysed coconut oil, or a heptyl, nonyl or undecyl group;
  • - R b represents a beta-hydroxyethyl group;
  • R c represents a carboxymethyl group
  • - M + represents a cationic counterion derived from an alkali metal or alkaline-earth metal, such as sodium, an ammonium ion or an ion derived from an organic amine, and
  • - X " represents an organic or mineral anionic counterion, such as that chosen from halides, acetates, phosphates, nitrates, (Ci- C 4 )alkyl sulfates, (Ci-C 4 )alkylsulfonates or (Ci- C 4 )alkylarylsulfonates, in particular methyl sulfate and ethyl sulfate; or alternatively M + and X " are absent;
  • - B represents the group -CH 2 CH 2 OX'
  • - X* represents the group -CH 2 COOH, -CH 2 -COOZ', -CH 2 CH 2 COOH, -CH 2 CH 2 -COOZ', or a hydrogen atom;
  • - Y* represents the group -COOH, -COOZ'
  • - Z' represents a cationic counterion derived from an alkali metal or alkaline-earth metal, such as sodium, an ammonium ion or an ion derived from an organic amine;
  • R a ' represents a Cio-C 3 o alkyl or alkenyl group of an acid R a '-COOH which is preferably present in coconut oil or in hydrolysed linseed oil, or an alkyl group, especially a C 17 group, and its iso form, or an unsaturated C 17 group.
  • - Y represents the group -COOH, -COOZ " ,
  • Rd and R e represent, independently of each other, a C 1 - C 4 alkyl or hydroxyalkyl radical
  • - Z" represents a cationic counterion derived from an alkali metal or alkaline-earth metal, such as sodium, an ammonium ion or an ion derived from an organic amine;
  • R a " represents a C i o-C 3 o alkyl or alkenyl group of an acid R a "-COOH which is preferably present in coconut oil or in hydrolysed linseed oil;
  • n denote, independently o f each other, an integer ranging from 1 to 3.
  • amphoteric or zwitterionic surfactants use is preferably made of (C 8 -C 2 o)alkylbetaines such as cocoylbetaine, (C 8 -C 2 o)alkylamido(C 3 - C 8 )alkylbetaines such as cocamidopropylbetaine, and mixtures thereof, and the compounds of formula (VII) such as the sodium salt o f diethylaminopropyl laurylamino succinamate (INCI name : sodium diethylaminopropyl cocoaspartamide).
  • composition (A) according to the invention and/or the oxidizing composition (B) comprise one or more nonionic surfactants and one or more cationic surfactants .
  • the surfactant(s) represent from 1 % to 50%, preferably from 5 % to 40% and better still from 10% to 20% by weight relative to the total weight of composition (A) .
  • these surfactants preferably represent from 1 % to 50% by weight, more preferentially from 5 % to 40% by weight and better still from 10% to 20% by weight relative to the total weight of composition (B) .
  • composition (A) according to the invention comprises one or more fatty substances .
  • the oxidizing composition (B) also comprises one or more fatty substances .
  • fatty substance means an organic compound that is inso luble in water at ordinary temperature (25 °C) and at atmospheric pressure (760 mmHg) (so lubility o f less than 5 %, preferably less than 1 % and even more preferentially less than 0. 1 %). They have in their structure at least one hydrocarbon-based chain comprising at least 6 carbon atoms or a sequence of at least two siloxane groups.
  • the fatty substances are generally soluble in organic so lvents under the same temperature and pressure conditions, for instance chloroform, dichloromethane, carbon tetrachloride, ethanol, benzene, toluene, tetrahydrofuran (THF), liquid petroleum j elly or decamethy Icy clop entasiloxane.
  • the fatty substances of the invention preferably do not contain any salified carboxylic acid groups .
  • the fatty substances o f the invention are neither oxyalkylenated nor glycerolated ethers .
  • oil means a " fatty substance” that is liquid at room temperature (25 °C) and at atmospheric pressure (760 mmHg; i. e. 1 .013 x 10 s Pa) .
  • non-silicone oil means an oil not containing any silicon atoms (Si) and the term “ silicone oil” means an oil containing at least one silicon atom.
  • the fatty substances are chosen from C 6 - C i 6 hydrocarbons, hydrocarbons containing more than 16 carbon atoms, non- silicone oils of animal origin, plant or synthetic oils o f triglyceride type, fluoro oils, fatty alcoho ls, fatty acid and/or fatty alcoho l esters other than triglycerides and plant waxes, non-silicone waxes other than fatty alcoho ls, and silicones, and mixtures thereof.
  • the fatty alcoho ls, esters and acids more particularly contain at least one saturated or unsaturated, linear or branched hydrocarbon-based group comprising 6 to 30 and better still from 8 to 30 carbon atoms, which is optionally substituted, in particular by one or more hydroxyl groups (in particular 1 to 4) . If they are unsaturated, these compounds may comprise one to three conjugated or unconjugated carbon-carbon double bonds .
  • C 6 - C i 6 hydrocarbons may be linear, branched, and optionally cyclic, and are preferably chosen from alkanes. Examples that may be mentioned include hexane, dodecane, undecane, tridecane, and isoparaffins, for instance isohexadecane, isododecane and isodecane.
  • the linear or branched hydrocarbons of mineral or synthetic origin are preferably chosen from liquid paraffins, petroleum j elly, liquid petroleum j elly, polydecenes, squalane, and hydrogenated polyisobutene such as Parleam ® .
  • a hydrocarbon-based oil o f animal origin that may be mentioned is perhydrosqualene.
  • the triglyceride oils of plant or synthetic origin are preferably chosen from liquid fatty acid triglycerides containing from 6 to 30 carbon atoms, for instance heptanoic or octanoic acid triglycerides, or alternatively, for example, sunflower oil, corn oil, soybean oil, pumpkin oil, grapeseed oil, sesame seed oil, hazelnut oil, apricot oil, macadamia oil, arara oil, sunflower oil, castor oil, avocado oil, caprylic/capric acid triglycerides, for instance those sold by the company Stearineries Dubois or those sold under the names Miglyol® 810, 812 and 818 by the company Dynamit Nobel, jojoba oil and shea butter oil.
  • Use will preferably be made of triglyceride oils of plant origin.
  • the fluoro oils may be chosen from perfluoromethylcyclopentane and perfluoro- 1 ,3-dimethylcyclohexane, sold under the names Flutec® PCI and Flutec® PC3 by the company BNFL Fluorochemicals; perfluoro- 1 ,2-dimethylcyclobutane; perfluoroalkanes such as dodecafluoropentane and tetradecafluorohexane, sold under the names PF 5050® and PF 5060® by the company 3M, or bromoperfluorooctyl sold under the name Foralkyl® by the company Atochem; nonafluoromethoxybutane and nonafluoroethoxyisobutane; perfluoromorpholine derivatives such as 4-trifluoromethyl perfluoromorpholine sold under the name PF 5052® by the company 3M.
  • the fatty alcohols that are suitable for use in the invention are more particularly chosen from linear or branched, saturated or unsaturated alcohols comprising from 6 to 30 carbon atoms and preferably from 8 to 30 carbon atoms. Examples that may be mentioned include cetyl alcohol, stearyl alcohol and the mixture thereof (cetylstearyl alcohol), octyldodecanol, 2-butyloctanol, 2- hexyldecanol, 2-undecylpentadecanol, oleyl alcohol and linoleyl alcohol.
  • esters of saturated or unsaturated, linear or branched Ci-C 26 aliphatic mono- or polyacids and of saturated or unsaturated, linear or branched Ci-C 26 aliphatic mono- or polyalcohols the total carbon number of the esters being greater than or equal to 6 and more advantageously greater than or equal to 10.
  • dihydroabietyl behenate octyldodecyl behenate; isocetyl behenate; cetyl lactate; C 12 - Ci5 alkyl lactate; isostearyl lactate; lauryl lactate; linoleyl lactate; oleyl lactate; (iso)stearyl octanoate; isocetyl octanoate; octyl octanoate; cetyl octanoate; decyl oleate; isocetyl isostearate; isocetyl laurate; iso cetyl stearate; isodecyl octanoate; isodecyl oleate; isononyl isononanoate; iso stearyl palmitate; methyl acetyl ricino leate; myristyl stea
  • esters of C4 - C22 dicarboxylic or tricarboxylic acids and of C 1 - C22 alcoho ls and esters of mono-, di- or tricarboxylic acids and of C2 - C26 di-, tri-, tetra- or pentahydroxy alcohols may also be used.
  • esters mentioned above use is preferably made o f ethyl, isopropyl, myristyl, cetyl or stearyl palmitate, 2-ethylhexyl palmitate, 2-octyldecyl palmitate, alkyl myristates, such as isopropyl, butyl, cetyl or 2-octyldodecyl myristate, hexyl stearate, butyl stearate, isobutyl stearate, dioctyl malate, hexyl laurate, 2-hexyldecyl laurate, isononyl isononanoate or cetyl octanoate.
  • alkyl myristates such as isopropyl, butyl, cetyl or 2-octyldodecyl myristate, hexyl stearate, butyl stearate, isobuty
  • compositions may also comprise, as fatty ester, sugar esters and diesters of C6 - C30 and preferably C 12 - C22 fatty acids.
  • sugar esters and diesters of C6 - C30 and preferably C 12 - C22 fatty acids.
  • sugar esters oxygen-bearing hydrocarbon- based compounds containing several alcohol functions, with or without aldehyde or ketone functions, and which comprise at least 4 carbon atoms.
  • sugars may be monosaccharides, oligosaccharides or polysaccharides .
  • sucrose or saccharose
  • glucose or galactose
  • ribose or fucose
  • maltose fructose
  • mannose mannose
  • arabinose xylose
  • lactose and derivatives thereo f, especially alkyl derivatives, such as methyl derivatives, for instance methylglucose.
  • the sugar esters of fatty acids may be chosen especially from the group comprising the esters or mixtures of esters of sugars described previously and of linear or branched, saturated or unsaturated C6 - C30 and preferably C 1 2 - C22 fatty acids . If they are unsaturated, these compounds may comprise one to three conjugated or unconjugated carbon-carbon double bonds.
  • esters according to this variant may also be chosen from monoesters, diesters, triesters, tetraesters and polyesters, and mixtures thereo f.
  • esters may be, for example, o leates, laurates, palmitates, myristates, behenates, cocoates, stearates, linoleates, linolenates, caprates and arachidonates, or mixtures thereof such as, especially, oleopalmitate, oleostearate and palmitostearate mixed esters .
  • monoesters and diesters and in particular mono- or di-o leate, -stearate, -behenate, -oleate/palmitate, -lino leate, -lino lenate or -oleate/stearate of sucrose, glucose or methylglucose.
  • esters or mixtures of esters of sugar and of fatty acid examples include :
  • Ryoto Sugar Esters for example referenced B370 and corresponding to sucrose behenate formed from 20% monoester and 80% diester-triester-polyester;
  • sucrose mono-dipalmitate/stearate sold by the company Goldschmidt under the name Tegoso ft ® PSE .
  • the non-silicone wax(es) other than fatty alcoho ls are chosen especially from carnauba wax, candelilla wax, esparto wax, paraffin wax, ozokerite, plant waxes, such as olive tree wax, rice wax, hydrogenated jojoba wax or absolute flower waxes, such as the blackcurrant blossom essential wax sold by the company Bertin (France), or animal waxes, such as beeswaxes or modified beeswaxes (cerabellina); other waxes or waxy raw materials that can be used according to the invention are in particular marine waxes, such as the product sold by the company Sophim under the reference M82, polyethylene waxes or polyolefin waxes in general.
  • the fatty substance(s) according to the invention may be chosen from silicones.
  • the silicones that can be used in accordance with the invention may be in the form o f oils, waxes, resins or gums .
  • the silicone(s) are chosen from polydialkylsiloxanes, in particular po lydimethylsiloxanes (PDMSs), and organomodified polysiloxanes comprising at least one functional group chosen from amino groups, aryl groups and alkoxy groups .
  • PDMSs po lydimethylsiloxanes
  • organomodified polysiloxanes comprising at least one functional group chosen from amino groups, aryl groups and alkoxy groups .
  • Organopolysiloxanes are defined in greater detail in Walter Noll ' s Chemistry and Technology of Silicones ( 1968), Academic Press . They may be vo latile or non-vo latile.
  • the vo latile silicones are more particularly chosen from silicones with a boiling point of between 60°C and 260°C , and even more particularly silicones chosen from:
  • cyclic po lydialkylsiloxanes comprising from 3 to 7 and preferably from 4 to 5 silicon atoms.
  • cyclic po lydialkylsiloxanes comprising from 3 to 7 and preferably from 4 to 5 silicon atoms.
  • These are, for example, octamethylcyclotetrasiloxane sold in particular under the name Volatile Silicone ® 7207 by Union Carbide or Silbione ® 70045 V2 by Rhodia, decamethylcyclopentasiloxane sold under the name Volatile Silicone ® 7158 by Union Carbide, and Silbione ® 70045 V5 by Rhodia, and mixtures thereo f.
  • non-vo latile silicones that may be used according to the invention may preferably be non-volatile po lydialkylsiloxanes, polydialkylsiloxane gums and resins, polyorganosiloxanes modified with organic functional groups chosen from amine groups, aryl groups and alkoxy groups, and also mixtures thereof.
  • organomodified silicones that may be used in accordance with the invention are silicones as defined above and comprising in their structure one or more organofunctional groups attached via a hydrocarbon-based group .
  • the organomodified silicones may be polydiarylsiloxanes, in particular polydiphenylsiloxanes, and polyalkylarylsiloxanes functionalized with the organo functional groups mentioned previously.
  • the po lyalkylarylsiloxanes are particularly chosen from linear and/or branched polydimethyl/methylphenylsiloxanes and polydimethyl/diphenylsiloxanes with a viscosity ranging from l x l O "5 to 5 x l 0 "2 m 2 /s at 25 °C .
  • oils o f the SF series from General Electric such as SF 1023 , SF 1 154, SF 1250 and SF 1265.
  • organomodified silicones of polyorganosiloxanes comprising :
  • substituted or unsubstituted amine groups such as the products sold under the names GP 4 Silicone Fluid and GP 71 00 by the company Genesee or the products sold under the names Q2 8220 and Dow Corning 929 or 939 by the company Dow Corning.
  • the substituted amine groups are, in particular, C 1 - C 4 amino alkyl groups; - alkoxylated groups, such as the product sold under the name Silicone Copolymer F-755 by SWS Silicones and Abil Wax® 2428 , 2434 and 2440 by the company Go ldschmidt.
  • the fatty substances are chosen from compounds that are liquid or pasty at room temperature (25 °C) and at atmospheric pressure.
  • the fatty substance(s) are chosen from compounds that are liquid at a temperature of 25 °C and at atmospheric pressure.
  • the fatty substances are advantageously chosen from C 6 - C i 6 alkanes, linear or branched hydrocarbons, of mineral or synthetic origin, containing more than 1 6 carbon atoms, non-silicone oils o f plant, mineral or synthetic origin, fatty alcohols, and fatty acid and/or fatty alcoho l esters, or mixtures thereof.
  • the fatty substance(s) are chosen from linear or branched liquid hydrocarbons, of mineral or synthetic origin, containing more than 16 carbon atoms, and especially liquid petroleum j elly and hydrogenated po lyisobutene, C 6 - C i 6 alkanes, liquid fatty acid and/or fatty alcoho l esters, and liquid fatty alcoho ls, or mixtures thereo f.
  • the fatty substances may represent from 1 % to 60%, preferably from 2% to 50%>, better still from 5 % to 40%> by weight, even better still from 7% to 30% by weight and very preferentially from 12% to 25 % by weight relative to the total weight of composition (A) .
  • the oxidizing composition (B) contains one or more fatty substances, they preferably represent from 1 % to 60%>, more preferentially from 2% to 50%, better still from 5 % to 40% by weight, even better still from 7% to 30% by weight and very preferentially from 12% to 25 % by weight relative to the total weight of composition (B) .
  • Composition (A) according to the invention comprises water, in a content of greater than or equal to 40% by weight relative to the total weight of composition (A) .
  • the oxidizing composition (B) also comprises water, in a content more preferentially greater than or equal to 40% by weight relative to the total weight of the oxidizing composition (B) .
  • compositions (A) and/or (B) preferably ranges from 40% to 95 % by weight, more preferentially from 40% to 80% by weight and in particular from 40% to 70% by weight, relative to the total weight of composition (A) and/or (B), respectively.
  • Composition (A) according to the invention and/or the oxidizing composition (B) may also comprise one or more water- so luble organic so lvents (so lubility o f greater than or equal to 5 % in water at 25 °C and at atmospheric pressure) .
  • Examples o f water-so luble organic solvents that may be mentioned include linear or branched and preferably saturated monoalcoho ls or dio ls, comprising 2 to 10 carbon atoms, such as ethyl alcoho l, isopropyl alcoho l, hexylene glycol (2-methyl-2,4- pentanedio l), neopentyl glyco l and 3 -methyl- 1 ,5 -pentanedio l, butylene glyco l, dipropylene glycol and propylene glycol; aromatic alcoho ls such as phenylethyl alcohol; polyols containing more than two hydroxyl functions, such as glycero l; polyo l ethers, for instance ethylene glycol monomethyl, monoethyl and monobutyl ether, propylene glyco l or ethers thereof, for instance propylene glyco l monomethyl ether;
  • the water-so luble organic solvents when they are present, generally represent between 1 % and 20% by weight relative to the total weight of the composition according to the invention, and preferably between 5 % and 10% by weight relative to the total weight of each composition containing them.
  • Composition (A) according to the invention and/or the oxidizing composition (B) may also comprise one or more alkaline agents .
  • the alkaline agent(s) are especially chosen from aqueous ammonia, alkali metal carbonates or bicarbonates, organic amines with a pKb at 25°C of less than 12, in particular less than 10 and even more advantageously less than 6; from the salts of the amines mentioned previously with acids such as carbonic acid or hydrochloric acid: it should be noted that it is the pKb corresponding to the function of highest basicity.
  • the amines are chosen from alkanolamines, in particular comprising a primary, secondary or tertiary amine function, and one or more linear or branched Ci-Cs alkyl groups bearing one or more hydroxyl radicals; from oxyethylenated and/or oxypropylenated ethylenediamines, and from amino acids and compounds having the following formula:
  • W is a Ci-C 6 alkylene residue optionally substituted with a hydroxyl group or a Ci-C 6 alkyl radical
  • Rx, Ry, Rz and Rt which may be identical or different, represent a hydrogen atom or a Ci-C 6 alkyl, Ci-C 6 hydroxyalkyl or Ci-C 6 aminoalkyl radical.
  • composition (A) according to the invention and/or the oxidizing composition (B) comprise aqueous ammonia and/or at least one alkanolamine and/or at least one basic amino acid, more advantageously aqueous ammonia and/or at least one alkanolamine, such as monoethanolamine, or mixtures thereof.
  • the content of alkaline agent(s) ranges from 0.01% to 30% by weight, preferably from 0.1% to 20% by weight and better still from 1% to 10% by weight relative to the weight of each composition containing them. It should be noted that this content is expressed as NH 3 when the alkaline agent is aqueous ammonia.
  • composition (A) of the invention preferably ranges from 1.5 to 12, better still from 6 to 11 and even better still from 8 to 11.
  • the pH of the oxidizing composition (B) preferably ranges from 1.5 to 9, better still from 1.5 to 7 and even better still from 2 to 4. It can be adjusted by adding acidifying agents, such as hydrochloric acid, (ortho)phosphoric acid, sulfuric acid, boric acid, and also carboxylic acids, for instance acetic acid, lactic acid or citric acid, or sulfonic acids . Alkaline agents such as those previously mentioned may also be used.
  • Composition (A) according to the invention and/or the oxidizing composition (B) may also comprise one or more direct dyes .
  • Examples of particularly suitable direct dyes include nitrobenzene dyes; azo direct dyes; azomethine direct dyes; methine direct dyes; azacarbocyanin direct dyes, for instance tetraazacarbocyanines (tetraazapentamethines); quinone and in particular anthraquinone, naphthoquinone or benzoquinone direct dyes; azine direct dyes; xanthene direct dyes; triarylmethane direct dyes; indoamine direct dyes; indigoid direct dyes; phthalocyanine direct dyes, porphyrin direct dyes and natural direct dyes, alone or as mixtures.
  • o f direct dyes from among : azo; methine; carbonyl; azine; nitro (hetero)aryl; tri(hetero)arylmethane; porphyrin; phthalocyanine and natural direct dyes, alone or as mixtures.
  • the direct dye(s) may represent from 0.0001 % to 10%> by weight and preferably from 0.005 % to 5 % by weight relative to the weight of composition (A) and/or (B) containing them.
  • the oxidizing composition (B) does not comprise any direct dye(s) .
  • Composition (A) according to the invention and/or the oxidizing composition (B) may also comprise one or more cosmetic adjuvants.
  • they may comprise one or more standard additives that are well known in the art, such as anionic, cationic, nonionic or amphoteric polymers or mixtures thereof, agents for preventing hair lo ss, so lid fatty substances other than those mentioned previously, vitamins and provitamins including pantheno l, sunscreens, mineral or organic pigments, sequestrants, plasticizers, solubilizers, acidifying agents, mineral or organic thickeners, especially polymeric thickeners, opacifiers, antioxidants, hydroxy acids, nacreous agents, fragrances and preserving agents .
  • standard additives that are well known in the art, such as anionic, cationic, nonionic or amphoteric polymers or mixtures thereof, agents for preventing hair lo ss, so lid fatty substances other than those mentioned previously, vitamins and provitamins including pantheno l, sunscreens, mineral or organic pigments, sequestrants, plasticizers, solubilizers, acidifying agents, mineral or organic thickeners, especially poly
  • the above adjuvants may generally be present in an amount, for each o f them, of between 0 and 20% by weight relative to the total weight of each composition containing them.
  • composition (A) according to the invention may also comprise one or more oxidizing agents.
  • the composition is then said to be "ready to use” in the sense that it does not require the use of the oxidizing composition (B) .
  • the oxidizing agent(s) used in the context of the invention are chemical oxidizing agents other than atmospheric oxygen.
  • the said oxidizing agent(s) are preferably chosen from the group formed by hydrogen peroxide, urea peroxide, alkali metal bromates or ferricyanides, peroxygenated salts, for instance persulfates, perborates, peracids and precursors thereof and alkali metal or alkaline-earth metal percarbonates, and most particularly hydrogen peroxide.
  • the oxidizing agent(s) may represent from 0.01 % to 20%, preferably from 0. 1 % to 10% and better still from 2% to 8% by weight, relative to the total weight of composition (A) .
  • the oxidizing composition (B) that may be used in the process according to the invention comprises one or more oxidizing agents .
  • the oxidizing agent(s) of the oxidizing composition (B) are as defined above.
  • the oxidizing agent(s) may represent from 0.01 % to 20%, preferably from 0. 1 % to 10% and better still from 2% to 8% by weight, relative to the total weight of the oxidizing composition (B) .
  • the oxidizing composition (B) is preferably in the form o f a nanoemulsion.
  • composition (A) and the oxidizing composition (B) are such that the mixture of these two compositions is also in the form o f a nanoemulsion.
  • compositions (A) and/or (B) according to the invention may especially be in the form o f fluid or thickened liquids, gels or creams.
  • the nanoemulsions according to the invention may be prepared by mixing water, the fatty substance(s) and the surfactant(s), with vigorous stirring, at a temperature preferably between a temperature close to 20°C and 45 °C , followed by one or more steps of homogenization at high pressure, i. e. at a pressure preferably greater than or equal to 5 x 10 7 Pa and preferably ranging from 6 x 10 7 to 1 8 x 10 7 Pa.
  • the shear will preferably be from 2 x l 0 6 s " 1 to 5 x 10 8 s " 1 , and more preferentially from l x l O 8 s " 1 to 3 x l 0 8 s " 1 .
  • nanoemulsions according to the invention several successive high-pressure homogenization steps as described above are performed.
  • nanoemulsions according to the invention may also be prepared with the aid o f a ternary phase diagram (fatty substance/surfactant/water), established beforehand, according to the fo llowing process :
  • step (ii) the addition o f the water-so luble ingredients such as the oxidation dyes, the couplers or the optional oxidizing agents takes place at the end of step (ii) or after step (iii) .
  • the temperature Tm is preferably between 20 and 100°C and better still between 20 and 85 °C . It should be noted that the particle size of the nanoemulsion is conserved during and after this cooling.
  • the invention also relates to the use of composition (A) as described above for dyeing keratin fibres, in particular the hair.
  • Another subj ect of the invention is a process for dyeing human keratin fibres, in particular the hair, using composition (A) as defined according to the invention.
  • composition (A) is "ready to use” , i. e . it already contains at least one oxidizing agent.
  • the keratin fibre dyeing process consists in applying the "ready-to-use" composition to the keratin fibres.
  • the keratin fibre dyeing process consists in applying composition (A) according to the invention to the keratin fibres, the said composition being applied sequentially to or simultaneously with the oxidizing composition (B) .
  • composition (A) according to the invention is mixed at the time o f use with the oxidizing composition (B) as described above.
  • composition (A) according to the invention is applied to the keratin fibres before or after the oxidizing composition (B) as described above.
  • the process may be repeated several times in order to obtain the desired coloration.
  • composition(s) are usually left in place on the fibres for a time generally ranging from 1 minute to 1 hour and preferably from 5 minutes to 30 minutes.
  • the temperature during the process is conventionally between 20 and 80°C and preferably between 20 and 60°C .
  • the human keratin fibres are advantageously rinsed with water. They may optionally be washed with a shampoo , followed by rinsing with water, before being dried or left to dry.
  • Another subj ect of the invention concerns a multi-compartment device, or a kit for dyeing keratin fibres, comprising at least two compartments :
  • the kit also comprises an additional compartment containing an additional composition comprising one or more treating agents.
  • compositions of the kit are packaged in separate compartments, which may be optionally accompanied by suitable identical or different application means, such as fine brushes, coarse brushes or sponges .
  • kit may also be equipped with means allowing the delivery to the hair o f the desired mixture, such as, for example, the device described in patent FR 2 586 913.
  • a cosmetic composition A in the form o f a nanoemulsion was prepared, in accordance with the invention, from the ingredients indicated in the table below (in which the contents are indicated in grams o f active material) :
  • PEG-8 isostearate 13.5
  • the nanoemulsion o f composition A above was obtained from the knowledge of the surfactants/hydrogenated polyisobutene/water ternary phase diagram.
  • the mixture of surfactants and of hydrogenated polyisobutene o f the above composition according to the invention was brought to a temperature of 60°C and the mixture was then diluted with the water of the formula at the same temperature.
  • the composition was finally cooled to room temperature (20 to 25 °C) .
  • the water-so luble compounds including the oxidation dyes and the couplers are added either after addition o f the water or after cooling to room temperature.
  • a nanoemulsion in which the size o f the oil globules, measured by quasi-elastic light scattering, is less than 100 nm is obtained.
  • This composition is stable on storage for at least 2 months at room temperature and at 45 ° C .
  • Composition A is mixed at the time of use with an oxidizing composition B in the fo llowing proportions : 10 g of composition A according to the invention and 10 g of oxidizing composition B .
  • Composition B amount (in g)
  • the mixture obtained is applied to locks at a rate of 10 g o f mixture per 1 g of hair.
  • the Applicant finds that the above composition according to the above example has very good working qualities, and especially a particularly pleasant texture.
  • the Applicant finds that the mixture derived from the composition according to the invention is easy to apply and to spread onto the locks of hair. It spreads easily from the roots to the ends .
  • composition is left in place for 30 minutes .
  • the hair is then rinsed, washed with a standard shampoo and dried.
  • the oxidizing composition C in the form o f a nanoemulsion was prepared, in accordance with the invention, from the ingredients indicated in the table below (in which the contents are indicated in grams o f active material) :
  • the oxidizing nanoemulsion C above was obtained from the knowledge of the surfactants/hydrogenated polyisobutene/water ternary phase diagram.
  • the mixture of surfactants and of hydrogenated polyisobutene o f composition C above was brought to a temperature of 60°C and the mixture was then diluted with the water of the formula at the same temperature.
  • the composition was finally cooled to room temperature (20 to 25 °C).
  • the water-soluble compounds including the oxidizing agents are added either after addition of the water or after cooling to room temperature. After this cooling to room temperature, the pH is then optionally adjusted to the desired value to obtain the desired composition.
  • a nanoemulsion in which the size o f the oil globules, measured by quasi-elastic light scattering, is less than 100 nm is obtained.
  • This composition is stable on storage for at least 2 months at room temperature and at 45 °C .
  • compositions (A) according to Example 1 and (C) as described above are mixed at the time of use in the fo llowing proportions : 1 0 g of dye composition (A) according to the invention and 10 g of oxidizing composition (C) .
  • the App licant finds that the mixture thus formed conserves the nanoemulsion form.
  • the mixture is applied to locks at a rate of 10 g of mixture per 1 g of hair.
  • composition obtained after mixing has very good working qualities, and especially a particularly pleasant texture.
  • the said composition spreads easily from the roots to the ends.
  • composition is left in place for 30 minutes.
  • the hair is then rinsed, washed with a standard shampoo and dried.
  • the said composition gives the hair a light chestnut coloration, which is judged to be visually very satisfactory.

Abstract

Cosmetic composition in the form of an oil-in-water nanoemulsion for the oxidation dyeing of keratin fibres, and process for the same The present invention relates to a cosmetic composition(A) in the form of an oil-in-water nanoemulsion comprising one or more oxidation dyes, one or more surfactants, one or more fatty substances and water in a content of greater than or equal to 40% by weight relative to the total weight of the composition; the number-average size of the oil droplets in the said nanoemulsion being less than or equal to 100 nm. The present invention also relates to a process for dyeing keratin fibres, which consists in applying to the keratin fibres composition (A) according to the invention and in particular an oxidizing composition(B), the said composition possibly being in the form of a nanoemulsion.

Description

Cosmetic composition in the form of an oil-in-water nanoemulsion for the oxidation dyeing of keratin fibres, and process for the same The present invention relates to a cosmetic composition in the form o f an oil-in-water nanoemulsion for the oxidation dyeing o f keratin fibres, in particular human keratin fibres such as the hair.
More precisely, a subj ect of the present invention is a dying cosmetic composition (A) in the form o f an oil-in-water nanoemulsion comprising one or more oxidation dyes, one or more surfactants, one or more fatty substances and water in a content of greater than or equal to 40% by weight relative to the total weight of the composition; the number-average size of the oil droplets in the said nanoemulsion being less than or equal to 100 nm.
The present invention also relates to the use of the composition according to the invention for dyeing keratin fibres.
The present invention also relates to a process for dyeing keratin fibres, in particular human keratin fibres such as the hair, using composition (A) according to the invention.
According to a preferred embo diment, this process also uses an oxidizing composition (B) .
Finally, the present invention relates to a kit for the oxidation dyeing o f keratin fibres, which is suitable for performing such a process.
Many people have for a long time sought to modify the co lour of their hair, and especially to dye it in order, for example, to mask their grey hair.
"Permanent" dyeing methods also known as oxidation dyeing, which use dye compositions containing oxidation dye precursors, generally referred to as oxidation bases, such as ortho- or para- phenylenediamines, ortho- or para-aminopheno ls and heterocyclic compounds, have been developed for dyeing human keratin fibres in a long-lasting manner. These oxidation bases are co lourless or weakly co loured compounds, which, when combined with oxidizing products, may give rise to coloured compounds via a process of oxidative condensation.
It is also known that the shades obtained with these oxidation bases can be varied by combining them with couplers or coloration modifiers, the latter being chosen especially from aromatic meta- diaminobenzenes, meta-aminophenols, meta-diphenols and certain heterocyclic compounds such as indole compounds.
One o f the difficulties encountered during the implementation of the dyeing processes of the prior art arises from the fact that they are performed under alkaline conditions and in the presence of one or more oxidizing agents .
In order to improve the performance qualities of processes for dyeing human keratin fibres, and to limit the drawbacks associated with the use of alkaline agents and oxidizing agents, it has been proposed to use in dye compositions a substantial amount of one or more fatty substances .
However, the prior art compositions are not entirely satisfactory, and their performance qualities can be improved in particular, firstly, as regards the working qualities after mixing with an oxidizing composition, especially in terms of texture, ease o f application and ease o f spreading on the ends, and, secondly, as regards the dyeing qualities obtained with these mixtures, especially in terms o f intensity, homogeneity and selectivity o f the dyeing obtained.
The Applicant has now discovered that the use of an oxidation dye in an oil-in-water nanoemulsion makes it possible to obtain a cosmetic composition, for the oxidation dyeing of keratin fibres, which can overcome the above drawbacks and which has improved properties .
One subj ect of the present invention is thus a cosmetic composition (A) in the form o f an oil-in-water nanoemulsion comprising one or more oxidation dyes, one or more surfactants, one or more fatty substances and at least 40% by weight of water, relative to the total weight of the composition; the number-average size o f the oil droplets in the said nanoemulsion being less than or equal to 100 nm.
The composition according to the invention has very good working qualities, and especially a particularly pleasant texture.
Furthermore, it is easy to apply and to spread on the locks of hair, in particular on the roots.
In addition, it does not run and remains well located at the points o f application and spreads easily from the roots to the ends .
Finally, the composition according to the invention has superior dyeing quality, especially in terms of intensity, homogeneity and selectivity o f the dyeing obtained.
This dye composition (A) may be used in a process for dyeing keratin fibres using this composition in combination with an oxidizing composition (B) .
A subj ect of the invention is thus also a process for dyeing keratin fibres, which consists in applying to the keratin fibres a composition (A) according to the invention, the said composition being applied sequentially to or simultaneously with an oxidizing composition (B) comprising one or more oxidizing agents.
According to a particularly preferred embodiment, the oxidizing composition (B) is also in the form o f a nanoemulsion and comprises one or more oxidizing agents, one or more surfactants, one or more fatty substances and water; the number-average size of the oil droplets in the said nanoemulsion being less than or equal to 100 nm.
Other characteristics and advantages of the invention will emerge more clearly on reading the description and the examples that fo llow.
According to the invention, composition (A) according to the invention is in the form o f an oil-in-water nanoemulsion.
Preferably, the oxidizing composition (B) is also in the form o f an oil-in-water nanoemulsion. According to the present invention, the term "oil-in-water nanoemulsion" denotes a true emulsion, i. e. a thermodynamically unstable dispersion of oil droplets in a continuous aqueous phase.
Nanoemulsions are to be distinguished from microemulsions, which are thermo dynamically stable dispersions in the form o f micelles of oil-swo llen surfactants, and which form spontaneously by simple mixing o f the constituents, without substantial input of energy.
The number-average size of the oil droplets in the nanoemulsions according to the invention is less than or equal to 100 nm.
In a particularly preferred manner, the number-average size o f the oil droplets of the nanoemulsion(s) according to the invention ranges from 10 to 90 nm, better still from 20 to 80 nm and more preferentially from 40 to 60 nm.
The number-average size of the particles may be determined in particular according to the known method of quasi-elastic light scattering. As a machine that may be used for this determination, mention may be made of the Brookhaven brand machine equipped with an SX 200 optical bed (with a 532 nm laser) and a BI 9000 correlator. This machine gives a measurement of the mean diameter by photon correlation spectroscopy (PCS), which makes it possible to determine the number-average diameter from the polydispersity factor, which is also measured by the machine.
The nanoemulsion may also be characterized by measuring its turbidity according to the NTU method using a 21 OOP mo del turbidimeter from the company Hach, at room temperature. The turbidity o f the nanoemulsions o f the invention is generally less than 400 NTU units and preferably between 50 and 250 NTU units.
A nanoemulsion generally has a transparent to blueish or translucent appearance, in the absence of opacifying or nacreous additional compound(s).
In the compositions according to the invention, the reduction in the size of the oil globules makes it possible especially to promote the penetration of the active ingredients into the keratin materials, for example through the surface layers of the hair (vehicle effect) .
As indicated previously, the cosmetic composition (A) according to the invention comprises one or more oxidation dyes .
Preferably, the oxidizing composition (B) does not comprise any oxidation dyes .
The oxidation dyes that may be used in the present invention are generally chosen from oxidation bases, optionally combined with one or more couplers .
Preferentially, the oxidation dye(s) comprise one or more oxidation bases.
The oxidation bases may be chosen especially from para- phenylene diamines, bis (phenyl) alky lene diamines, para-aminophenols, ortho-aminopheno ls and heterocyclic bases, and the addition salts thereo f.
Among the para-phenylenediamines, examples that may be mentioned include para-phenylenediamine, para-tolylenediamine, 2- chloro-para-pheny lene diamine, 2,3 -dimethyl-para-phenylenediamine, 2, 6 -dimethyl-para-pheny lene diamine, 2,6-diethyl-para- phenylenediamine, 2,5 -dimethyl-para-phenylenediamine, N,N- dimethyl-para-pheny lene diamine, Ν,Ν-diethyl-para-phenylenedi amine, Ν,Ν-dipropyl-para-pheny lene diamine, 4 -amino -N,N- diethyl- 3 - methylaniline, N,N-bis( -hydroxy ethyl) -para-phenylenediamine, 4- N,N-bis( -hydroxy ethyl) amino -2 -met hylaniline, 4-N,N-bis( - hy droxy ethyl) amino -2 -chloro aniline, 2- -hydroxyethyl-para- phenylenediamine, 2- fluoro -para-phenylenediamine, 2-isopropyl-para- phenylenediamine, N-( -hydroxypropyl)-para-phenylenediamine, 2- hydroxymethyl-para-phenylenediamine, N, N- dimethyl- 3 -methyl-par a- pheny lene diamine, N, N- (ethyl- β- hydroxy ethyl) -para- phenylenediamine, N-( ,y-dihydroxypropyl)-para-phenylenediamine, N- (4 '-aminophenyl) -para-phenylenediamine, N-phenyl-para- phenylenediamine, 2- -hydroxyethyloxy-para-phenylenediamine, 2-β- acetylaminoethyloxy-para-phenylenediamine, N- (β-methoxy ethyl) - para-phenylenediamine, 4-aminophenylpyrrolidine, 2-thienyl-para- phenylenediamine, 2- -hydroxyethylamino-5 -aminotoluene and 3 - hydroxy- 1 -(4'-aminophenyl)pyrrolidine, and the addition salts thereo f with an acid.
Among the para-phenylenediamines mentioned above, para- phenylenediamine, para-tolylenediamine, 2-isopropyl-para- phenylenediamine, 2- -hydroxyethyl-para-phenylenediamine, 2-β- hydroxyethyloxy-para-phenylenediamine, 2, 6 -dimethyl-par a- phenylene diamine, 2, 6- diet hyl-para-phenylene diamine, 2, 3 -dimethyl- par a-phenylenediamine, N, N-bis( - hydroxy ethyl) -par a- phenylenediamine, 2-chloro-para-phenylenediamine and 2-β- acetylaminoethyloxy-para-phenylenediamine, and the addition salts thereo f with an acid, are particularly preferred.
Among the bis(phenyl)alkylenediamines, examples that may be mentioned include N,N'-bis( -hydroxyethyl)-N,N'-bis(4'- aminophenyl)- l ,3 -diaminopropanol, N,N'-bis( -hydroxyethyl)-N,N'- bis (4 '-aminophenyl) ethylene diamine, N,N'-bis(4- aminophenyl)tetramethylenediamine, N, N'-bis( -hydroxy ethyl) -N,N '- bis(4- amino phenyl)tetramethylenediamine, N,N'-bis(4- methylaminophenyl)tetramethylenediamine, N,N'-bis(ethyl)-N,N'- bis(4'-amino-3 '-methylphenyl)ethylenediamine, 1 , 8 -bis (2,5 - diaminophenoxy)-3 ,6-dioxaoctane and the addition salts thereof.
Among the para-aminophenols, examples that may be mentioned include para-aminophenol, 4-amino-3 -methylpheno l, 4- amino-3 -fluoropheno l, 4-amino-3 -chlorophenol, 4-amino-3 - hydroxymethylpheno l, 4-amino-2-methylpheno l, 4-amino-2- hydroxymethylpheno l, 4-amino-2-methoxymethylpheno l, 4-amino-2- aminomethylpheno l, 4-amino-2-( -hydroxyethyl-aminomethyl)pheno l and 4-amino-2-fluorophenol, and the addition salts thereof with an acid.
Among the ortho-aminopheno ls, examples that may be mentioned include 2-aminophenol, 2-amino-5 -methylpheno l, 2-amino- 6-methylpheno l and 5 -acetamido-2-aminopheno l, and the addition salts thereo f. Among the heterocyclic bases, examples that may be mentioned include pyridine derivatives, pyrimidine derivatives and pyrazole derivatives.
Among the pyridine derivatives that may be mentioned are the compounds described, for example, in patents GB 1 026978 and GB 1 153 196, for instance 2,5-diaminopyridine, 2-(4- methoxyphenyl)amino-3-aminopyridine and 3,4-diaminopyridine, and the addition salts thereof.
Other pyridine oxidation bases that are useful in the present invention are the 3-aminopyrazolo[ 1 ,5-a]pyridine oxidation bases or the addition salts thereof described, for example, in patent application FR 2 801 308. Examples that may be mentioned include pyrazolo[l ,5- a]pyrid-3-ylamine, 2-(acetylamino)pyrazolo[ 1 ,5-a]pyrid-3-ylamine, 2- (morpholin-4-yl)pyrazolo[ 1 ,5-a]pyrid-3-ylamine, 3- aminopyrazolo[ 1 ,5-a]pyridine-2-carboxylic acid, 2- methoxypyrazolo[ 1 ,5-a]pyrid-3-ylamine, (3-aminopyrazolo[ 1 ,5- a]pyrid-7-yl)methanol, 2-(3-aminopyrazolo[ 1 ,5-a]pyrid-5-yl)ethanol, 2-(3-aminopyrazolo[ 1 ,5-a]pyrid-7-yl)ethanol, (3-aminopyrazolo[ 1 ,5- a]pyrid-2-yl)methanol, 3,6-diaminopyrazolo[ 1 ,5-a]pyridine, 3,4- diaminopyrazolo[ 1 ,5-a]pyridine, pyrazolo[l ,5-a]pyridine-3,7-diamine, 7-(morpholin-4-yl)pyrazolo[l ,5-a]pyrid-3-ylamine, pyrazolo[l ,5- a]pyridine-3, 5 -diamine, 5-(morpholin-4-yl)pyrazolo[l ,5-a]pyrid-3- ylamine, 2-[(3-aminopyrazolo[ 1 ,5-a]pyrid-5-yl)(2- hydroxyethyl)amino]ethanol, 2-[(3-aminopyrazolo[ 1 ,5-a]pyrid-7-yl)(2- hydroxyethyl)amino]ethanol, 3-aminopyrazolo[ 1 ,5-a]pyridin-5-ol, 3- aminopyrazolo[ 1 ,5-a]pyridin-4-ol, 3-aminopyrazolo[ 1 ,5-a]pyridin-6- ol, 3-aminopyrazolo[ 1 ,5-a]pyridin-7-ol and the addition salts thereof.
Among the pyrimidine derivatives that may be mentioned are the compounds described, for example, in the patents DE 2359399; JP 88-169571; JP 05-63124; EP 0770375 or patent application WO 96/15765, such as 2,4,5,6-tetraaminopyrimidine, 4-hydroxy-2,5,6- triaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 2,4- dihydroxy-5,6-diaminopyrimidine, 2,5,6-triaminopyrimidine and the addition salts thereof and the tautomeric forms thereof, when a tautomeric equilibrium exists.
Among the pyrazole derivatives that may be mentioned are the compounds described in patents DE 3843892 and DE 4133957 and patent applications WO 94/08969, WO 94/08970, FR-A-2733 749 and DE 195 43 988, for instance 4,5-diamino- 1 -methylpyrazole, 4,5- diamino- 1 -( -hydroxyethyl)pyrazole, 3,4-diaminopyrazole, 4,5- diamino- 1 -(4 '-chlorobenzyl)pyrazole, 4,5-diamino - 1 ,3- dimethylpyrazole, 4,5-diamino-3-methyl- 1 -phenylpyrazole, 4,5- diamino- 1 -methyl-3-phenylpyrazole, 4-amino- 1 ,3-dimethyl-5- hydrazinopyrazole, 1 -benzyl-4,5-diamino-3-methylpyrazole, 4,5- diamino-3-tert-butyl- 1 -methylpyrazole, 4,5-diamino - 1 -tert-butyl-3- methylpyrazole, 4,5-diamino - 1 - (β-hydroxy ethy l)-3 -methylpyrazole, 4,5-diamino - 1 - ethy 1-3 -methylpyrazole, 4,5-diamino - 1 - ethy 1-3 -(4 '- methoxyphenyl)pyrazole, 4,5-diamino- 1 -ethyl-3- hydroxymethylpyrazole, 4,5-diamino-3-hydroxymethyl- 1 - methylpyrazole, 4,5-diamino-3-hydroxymethyl- 1 -isopropylpyrazole, 4, 5 -diamino -3 -methyl- 1 - isopropylpyrazole, 4-amino -5 -(2 '- amino ethyl) amino - 1 ,3-dimethylpyrazole, 3 ,4,5-triaminopyrazole, 1 - methyl-3,4,5-triaminopyrazole, 3,5-diamino-l-methyl-4- methylaminopyrazole and 3,5-diamino-4-( -hydroxyethyl)amino-l- methylpyrazole, and the addition salts thereof. 4,5-Diamino- 1 -(β- methoxyethyl)pyrazole may also be used.
A 4,5-diaminopyrazole will preferably be used, and even more preferentially 4,5-diamino- 1 -( -hydroxyethyl)pyrazole and/or a salt thereof.
Pyrazole derivatives that may also be mentioned include diamino-N,N-dihydropyrazolopyrazolones and especially those described in patent application FR-A-2886 136, such as the following compounds and the addition salts thereof: 2,3-diamino-6,7-dihydro- lH,5H-pyrazolo[ 1 ,2-a]pyrazol- 1 -one, 2-amino-3-ethylamino-6,7- dihydro- lH,5H-pyrazolo[ 1 ,2-a]pyrazol- 1 - one, 2-amino-3- isopropylamino-6,7-dihydro-lH,5H-pyrazolo[ 1 ,2-a]pyrazol- 1 -one, 2- amino-3-(pyrrolidin-l-yl)-6,7-dihydro-lH,5H-pyrazolo[ 1 ,2-a]pyrazol- 1-one, 4,5-diamino-l,2-dimethyl-l,2-dihydropyrazol-3-one, 4,5- diamino-l ,2-diethyl- 1 ,2-dihydropyrazol-3-one, 4,5-diamino-l ,2-bis(2- hydroxy ethyl) - 1 ,2-dihydropyrazol-3-one, 2-amino-3-(2- hydroxyethyl)amino-6,7-dihydro-lH,5H-pyrazolo[ 1 ,2-a]pyrazol- 1 -one, 2-amino-3-dimethylamino-6,7-dihydro- lH,5H-pyrazolo[ 1 ,2-a]pyrazol- 1-one, 2,3-diamino-5,6,7,8-tetrahydro-lH,6H-pyridazino[l ,2- ajpyrazol- 1-one, 4 -amino - 1 ,2-diethyl-5-(pyrrolidin- 1 -yl)- 1 ,2- dihydropyrazol-3-one, 4-amino-5-(3-dimethylaminopyrrolidin- 1 -yl)- 1 ,2-diethyl- 1 ,2-dihydropyrazo 1-3 -one or 2,3-diamino-6-hydroxy-6,7- dihydro- lH,5H-pyrazolo[ 1 ,2-a]pyrazol- 1-one.
Use will preferably be made of 2,3-diamino-6,7-dihydro- lH,5H-pyrazolo[l,2-a]pyrazol-l-one and/or one of its salts.
Heterocyclic bases that will preferentially be used include 4,5- diamino-l -( -hydroxyethyl)pyrazole and/or 2,3-diamino-6,7-dihydro- lH,5H-pyrazolo[l,2-a]pyrazol-l-one and/or a salt thereof.
The oxidation dye(s) may also comprise one or more couplers, which may be chosen from those conventionally used for the dyeing of keratin fibres.
Among these couplers, mention may be made especially of meta-phenylenediamines, meta-aminophenols, meta-diphenols, naphthalene-based couplers and heterocyclic couplers, and also the addition salts thereof.
Examples that may be mentioned include 1,3- dihydroxybenzene, 1 ,3-dihydroxy-2-methylbenzene, 4-chloro- 1 ,3- dihydroxybenzene, 2,4-diamino- 1 -( -hydroxyethyloxy)benzene, 2- amino -4 -(β- hydroxy ethy lamino) - 1 -methoxybenzene, 1,3- diaminobenzene, 1 ,3-bis(2,4-diaminophenoxy)propane, 3- ureidoaniline, 3-ureido- 1 -dimethylaminobenzene, sesamol, 1-β- hydroxyethylamino-3,4-methylenedioxybenzene, cc-naphthol, 2- methyl- 1 -naphthol, 6-hydroxyindole, 4-hydroxyindole, 4-hydroxy-N- methylindole, 2-amino-3-hydroxypyridine, 6- hydroxybenzomorpholine, 3,5-diamino-2,6-dimethoxypyridine, 1-N- (P-hydroxyethyl)amino-3,4-methylenedioxybenzene, 2,6-bis(P- hydroxyethylamino)toluene, 6-hydroxyindoline, 2,6-dihydroxy-4- methylpyridine, 1 -H-3 -methylpyrazol-5 -one, l -phenyl-3 - methylpyrazol-5 -one, 2,6-dimethylpyrazolo [ 1 ,5 -b] - 1 ,2,4-triazole, 2,6- dimethyl[3 ,2-c] - l ,2,4-triazole and 6-methylpyrazolo [ 1 ,5 - ajbenzimidazole, the addition salts thereof with an acid, and mixtures thereo f.
In general, the addition salts o f the oxidation bases and couplers that may be used within the context of the invention are especially chosen from the addition salts with an acid such as the hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates .
The oxidation base(s) may advantageously represent from 0.0001 % to 10% by weight relative to the total weight of the composition containing them, preferably from 0.005 % to 5 % by weight and better still from 0. 1 % to 2% by weight relative to the total weight of this composition.
The coupler(s), if they are present, may advantageously represent from 0.0001 % to 1 0% by weight relative to the total weight of the composition containing them, and preferably from 0.005 % to 5 % by weight relative to the total weight of this composition.
Composition (A) according to the invention comprises one or more surfactants .
Preferably, the oxidizing composition (B) also comprises one or more surfactants .
They may be chosen especially from nonionic, cationic, anionic and amphoteric or zwitterionic surfactants .
The said surfactant(s) according to the invention preferably comprise one or more nonionic surfactants .
The nonionic surfactant(s) that may be used in the compositions are described, for example, in the Handbook of Surfactants by M .R. Porter, published by Blackie & Son (Glasgow and London), 1991 , pp . 1 16- 178.
Examples of nonionic surfactants that may be mentioned include the fo llowing nonionic surfactants :
- oxyalkylenated (Cs- C 24)alkylphenols; - saturated or unsaturated, linear or branched, oxyalkylenated or glycerolated C8-C40 alcohols, comprising one or two fatty chains;
- saturated or unsaturated, linear or branched, oxyalkylenated C8-C30 fatty acid amides;
- esters of saturated or unsaturated, linear or branched, C8-C30 acids and of polyethylene glycols;
- esters of saturated or unsaturated, linear or branched, C8-C30 acids and of sorbitol, preferably oxyethylenated;
- fatty acid esters of sucrose;
- (C8-C3o)alkyl(poly)glucosides, (C8-C3o)alkenyl(poly) glucosides, which are optionally oxyalkylenated (0 to 10 oxyalkylene units) and comprising from 1 to 15 glucose units, (C8-C3o)alkyl (poly)glucoside esters;
- saturated or unsaturated, oxyethylenated plant oils;
- condensates of ethylene oxide and/or of propylene oxide, inter alia, alone or as mixtures;
- N-(C8-C3o)alkylglucamine and N-(C8-C3o) acylmethylglucamine derivatives;
- aldobionamides;
- amine oxides;
- oxyethylenated and/or oxypropylenated silicones;
- and mixtures thereof.
The oxyalkylene units are more particularly oxyethylene or oxypropylene units, or a combination thereof, preferably oxyethylene units.
The number of moles of ethylene oxide and/or propylene oxide preferably ranges from 1 to 250, more particularly from 2 to 100 and better still from 2 to 50; the number of moles of glycerol ranges especially from 1 to 50 and better still from 1 to 10.
Advantageously, the nonionic surfactants according to the invention do not comprise any oxypropylene units.
As examples of glycerolated nonionic surfactants, use is preferably made of monoglycerolated or polyglycerolated C8-C40 alcohols, comprising from 1 to 50 mol of glycerol and preferably from 1 to 10 mol of glycerol.
As examples of compounds of this type, mention may be made of lauryl alcohol containing 4 mol of glycerol (INCI name: Polyglyceryl-4 Lauryl Ether), lauryl alcohol containing 1.5 mol of glycerol, oleyl alcohol containing 4 mol of glycerol (INCI name: Polyglyceryl-4 Oleyl Ether), oleyl alcohol containing 2 mol of glycerol (INCI name: Polyglyceryl-2 Oleyl Ether), cetearyl alcohol containing 2 mol of glycerol, cetearyl alcohol containing 6 mol of glycerol, oleyl/cetyl alcohol containing 6 mol of glycerol, and octadecanol containing 6 mol of glycerol.
Among the glycerolated alcohols, it is more particularly preferred to use the Cs/Cio alcohol containing 1 mol of glycerol, the C10 C12 alcohol containing 1 mol of glycerol and the C12 alcohol containing 1.5 mol of glycerol.
The nonionic surfactant(s) according to the invention are preferentially chosen from:
- oxyethylenated C8-C40 alcohols comprising from 1 to 100 mol of ethylene oxide, preferably from 2 to 50 and more particularly from 2 to 40 mol of ethylene oxide and comprising one or two fatty chains;
saturated or unsaturated oxyethylenated plant oils comprising from 1 to 100 and preferably from 2 to 50 mol of ethylene oxide;
- (C8-C3o)alkyl(poly)glucosides, which are optionally oxyalkylenated (0 to 10 OE) and comprising 1 to 15 glucose units;
- monoglycerolated or polyglycerolated C8-C40 alcohols, comprising from 1 to 50 mol of glycerol and preferably from 1 to 10 mol of glycerol.
- saturated or unsaturated, linear or branched, oxyalkylenated C8-C30 fatty acid amides;
- esters of saturated or unsaturated, linear or branched, C8- C30 acids and of polyethylene glycols;
- and mixtures thereof. Even more preferentially, the nonionic surfactant(s) according to the invention are chosen from:
saturated or unsaturated, linear or branched, oxyalkylenated C 8 - C40 alcoho ls, comprising one or two fatty chains, especially ceteareth-60 myristyl glyco l;
- (C 8 - C3 o)alkyl(poly)glucosides , especially caprylyl/capryl glucoside ;
- esters of saturated or unsaturated, linear or branched, C8 - C30 acids and of po lyethylene glycols and especially PEG- 8 isostearate;
- and mixtures thereof.
Composition (A) according to the invention and the oxidizing composition (B) may comprise one or more cationic surfactants .
The term " cationic surfactant" means a surfactant that is positively charged when it is contained in the composition according to the invention. This surfactant may bear one or more positive permanent charges or may contain one or more cationizable functions in the compositions .
The cationic surfactant(s) are preferably chosen fro m optionally po lyoxyalkylenated, primary, secondary or tertiary fatty amines, or salts thereof, and quaternary ammonium salts, and mixtures thereo f.
The fatty amines generally comprise at least one C 8 - C30 hydrocarbon-based chain.
Examp les of quaternary ammonium salts that may especially b e mentioned include :
- those corresponding to the general formula (I) b elow :
Figure imgf000014_0001
in which the groups Rs to Rn , which may be identical or different, represent a linear or branched aliphatic group comprising from 1 to 30 carbon atoms, or an aromatic group such as aryl or alkylaryl, at least one of the groups Rs to Rn denoting a group comprising from 8 to 30 carbon atoms and preferably from 12 to 24 carbon atoms. The aliphatic groups may comprise heteroatoms especially such as oxygen, nitrogen, sulfur and halogens . The aliphatic groups are chosen, for example, from C 1 - C30 alkyl, C 1 - C30 alkoxy, polyoxy(C2- Ce)alkylene, C 1 - C30 alkylamide, (C i 2-C22)alkylamido(C2- C6)alkyl, (C i 2-C22)alkyl acetate and C 1 - C 30 hydroxyalkyl groups; X" is an anion chosen from the group of halides, phosphates, acetates, lactates, (C i -C4)alkyl sulfates, and (C i -C4)alkyl- or (C i - C4)alkylarylsulfonates.
Among the quaternary ammonium salts of formula (I), those that are preferred are, on the one hand, tetraalkylammonium salts, for instance dialkyldimethylammonium or alkyltrimethylammonium salts in which the alkyl group contains approximately from 12 to 22 carbon atoms, in particular behenyltrimethylammonium, distearyldimethylammonium, cetyltrimethylammonium or benzyldimethylstearylammonium salts, or, on the other hand, the palmitylamidopropyltrimethylammonium salt, the stearamidopropyltrimethylammonium salt, the stearamidopropyldimethylcetearylammonium salt, or the stearamidopropyldimethyl(myristyl acetate)ammonium salt sold under the name Ceraphyl® 70 by the company Van Dyk. It is particularly preferred to use the chloride salts of these compounds .
- quaternary ammonium salts o f imidazo line, for instance those of formul (II) below:
Figure imgf000015_0001
(II) in which Ri2 represents an alkenyl or alkyl group containing from 8 to 30 carbon atoms, derived for example from tallow fatty acids, Ri3 represents a hydrogen atom, a C1-C4 alkyl group or an alkenyl or alkyl group containing from 8 to 30 carbon atoms, R14 represents a C1-C4 alkyl group, R15 represents a hydrogen atom or a C1-C4 alkyl group, X" is an anion chosen from the group consisting of halides, phosphates, acetates, lactates, alkyl sulfates, alkylsulfonates or alkylarylsulfonates in which the alkyl and aryl groups respectively preferably comprise from 1 to 20 carbon atoms and from 6 to 30 carbon atoms. Ri2 and R13 preferably denote a mixture of alkenyl or alkyl groups containing from 12 to 21 carbon atoms, derived for example from tallow fatty acids, R14 preferably denotes a methyl group, and R15 preferably denotes a hydrogen atom. Such a product is sold, for example, under the name Rewoquat® W 75 by the company Rewo;
- di- or triquaternary ammonium salts, in particular of formula
(III):
R 17 R 19
Rl6 -N-(CH2)3-N-R21 2X-
Figure imgf000016_0001
(III)
in which Ri6 denotes an alkyl radical comprising approximately from 16 to 30 carbon atoms which is optionally hydroxylated and/or interrupted by one or more oxygen atoms, R17 is chosen from hydrogen or an alkyl radical comprising from 1 to 4 carbon atoms or an
(Rl6a)(Rl7a)(Rl8a)N-(CH2)3- group, R16a, Rl7a, Rl8a, Rl8, Rl9, R20 and
R21, which may be identical or different, are chosen from hydrogen or an alkyl radical comprising from 1 to 4 carbon atoms and X" is an anion chosen from the group of the halides, acetates, phosphates, nitrates and methyl sulfates. Such compounds are, for example, Finquat CT-P, available from the company Finetex (Quaternium 89), and Finquat CT, available from the company Finetex (Quaternium 75). - quaternary ammonium salts containing at least one ester function, such as those of formula (IV) below:
Figure imgf000017_0001
in which:
R22 is chosen from Ci-C6 alkyl groups and Ci-C6 hydroxyalkyl or dihydroxyalkyl groups;
R23 is chosen from:
O
R
- the group 26
- groups R27, which are linear or branched, saturated unsaturated C1-C22 hydrocarbon-based groups,
- a hydrogen atom,
R25 is chosen from:
O
R,
- the group ' 28
- groups R29, which are linear or branched, saturated or unsaturated Ci-C6 hydrocarbon-based groups,
- a hydrogen atom,
R24, R26 and R28, which may be identical or different, are chosen from linear or branched, saturated or unsaturated C7-C21 hydrocarbon-based groups;
r, s and t, which may be identical or different, are integers ranging from 2 to 6;
y is an integer ranging from 1 to 10;
x and z, which may be identical or different, are integers ranging from 0 to 10;
X" is a simple or complex, organic or mineral anion;
with the proviso that the sum x + y + z is from 1 to 15, that when x is 0 then R23 denotes R27, and that when z is 0 then R25 denotes
R29- The alkyl groups R22 may be linear or branched, and more particularly linear.
Preferably, R22 denotes a methyl, ethyl, hydroxyethyl or dihydroxypropyl group , and more particularly a methyl or ethyl group .
Advantageously, the sum x + y + z is from 1 to 10.
When R23 is an R27 hydrocarbon-based group, it may be long and may contain from 12 to 22 carbon atoms, or may be short and may contain from 1 to 3 carbon atoms.
When R25 is an R2 hydrocarbon-based group , it preferably contains 1 to 3 carbon atoms .
Advantageously, R24 , R26 and R28 , which may be identical or different, are chosen from linear or branched, saturated or unsaturated C 1 1 -C2 1 hydrocarbon-based groups, and more particularly from linear or branched, saturated or unsaturated C n -C2 1 alkyl and alkenyl groups .
Preferably, x and z, which may be identical or different, are equal to 0 or 1 .
Advantageously, y is equal to 1 .
Preferably, r, s and t, which may be identical or different, are equal to 2 or 3 , and even more particularly are equal to 2.
The anion X" is preferably a halide (chloride, bromide or iodide) or an alkyl sulfate, more particularly methyl sulfate . However, use may be made o f methanesulfonate, phosphate, nitrate, tosylate, an anion derived from an organic acid, such as acetate or lactate, or any other anion compatible with the ammonium containing an ester function.
The anion X" is even more particularly chloride or methyl sulfate.
Use is made more particularly, in the composition according to the invention, of the ammonium salts o f formula (IV) in which:
R22 denotes a methyl or ethyl group,
x and y are equal to 1 ;
z is equal to 0 or 1 ;
r, s and t are equal to 2;
R23 is chosen from: - the group
Figure imgf000019_0001
- methyl, ethyl or C14-C22 hydrocarbon-based groups,
- a hydrogen atom;
R25 is chosen from:
O - the group ^28 ^
- a hydrogen atom;
R24, R26 and R28, which may be identical or different, are chosen from linear or branched, saturated or unsaturated C13-C17 hydrocarbon-based groups, and preferably from linear or branched, saturated or unsaturated C13-C17 alkyl and alkenyl groups.
The hydrocarbon-based groups are advantageously linear.
Mention may be made, for example, of compounds of formula (IV), such as diacyloxyethyldimethylammonium, diacyloxyethyl(hydroxyethyl)methylammonium,
monoacyloxyethyldi(hydroxyethyl)methylammonium,
triacyloxyethylmethylammonium or monoacyloxyethyl(hydroxyethyl)dimethylammonium salts (in particular chloride or methyl sulfate), and mixtures thereof. The acyl groups preferably contain 14 to 18 carbon atoms and are obtained more particularly from a vegetable oil, such as palm oil or sunflower oil.
When the compound contains several acyl groups, these groups may be identical or different.
These products are obtained, for example, by direct esterification of triethanolamine, triisopropanolamine, an alkyldiethanolamine or an alkyldiisopropanolamine, which are optionally oxyalkylenated, with Cio-C3o fatty acids or with mixtures of Cio-C3o fatty acids of plant or animal origin, or by transesterification of the methyl esters thereof. This esterification is followed by quaternization using an alkylating agent such as an alkyl (preferably methyl or ethyl) halide, a dialkyl (preferably methyl or ethyl) sulfate, methyl methanesulfonate, methyl para-toluenesulfonate, glyco l chlorohydrin or glycerol chlorohydrin.
Such compounds are, for example, sold under the names Dehyquart® by the company Henkel, Stepanquat® by the company Stepan, Noxamium® by the company Ceca or Rewoquat® WE 1 8 by the company Rewo-Witco .
The composition according to the invention may contain, for example, a mixture o f quaternary ammonium monoester, diester and triester salts with a weight majority o f diester salts .
Use may also be made o f the ammonium salts containing at least one ester function that are described in patents US-A-4 874 554 and US-A-4 137 1 80.
Use may be made o f behenoylhydroxypropyltrimethylammonium chloride, provided by Kao under the name Quatarmin BTC 13 1 .
Preferably, the ammonium salts containing at least one ester function contain two ester functions.
Among the quaternary ammonium salts containing at least one ester function, which can be used, it is preferred to use dipalmitoylethylhydroxyethylmethylammonium salts.
The cationic surfactants are preferably chosen from those of formula (I) and those of formula (IV), and even more preferentially from those o f formula (I) .
Composition (A) according to the invention and the oxidizing composition (B) may comprise one or more anionic surfactants .
The term "anionic surfactant" means a surfactant comprising, as ionic or ionizable groups, only anionic groups . These anionic groups are preferably chosen from the fo llowing groups :
-COOH, -COO", - S O3H, - S O3 ", -O S O3 H, -O S O3", -PO2H2 , -PO2H", -PO2 2 ", -P(OH)2, =P(0)OH, -P(OH)0", =P(0)0", =POH, =PO , the anionic parts comprising a cationic counterion such as an alkali metal, an alkaline-earth metal or an ammonium.
As examples of anionic surfactants that may be used in the composition according to the invention, mention may be made o f alkyl sulfates, alkyl ether sulfates, alkylamido ether sulfates, alkylaryl polyether sulfates, monoglyceride sulfates, alkylsulfonates, alkylamidesulfonates, alkylarylsulfonates, a-olefin sulfonates, paraffin sulfonates, alkyl sulfosuccinates, alkyl ether sulfo succinates, alkylamide sulfosuccinates, alkyl sulfoacetates, acylsarcosinates, acylglutamates, alkyl sulfosuccinamates, acylisethionates and N- acyltaurates, polyglycoside polycarboxylic acid and alkyl monoester salts, acyl lactylates, salts o f D-galactoside uronic acids, salts o f alkyl ether carboxylic acids, salts o f alkylaryl ether carboxylic acids, salts of alkylamido ether carboxylic acids, and the corresponding non- salified forms of all these compounds; the alkyl and acyl groups of all these compounds comprising from 6 to 40 carbon atoms and the aryl group denoting a phenyl group .
These compounds can be oxyethylenated and then preferably comprise from 1 to 50 ethylene oxide units.
The salts o f C6 - C24 alkyl monoesters of polyglycoside- polycarboxylic acids may be chosen from C6 - C24 alkyl po lyglycoside- citrates, C6 - C24 alkyl polyglycoside-tartrates and C6 - C24 alkyl poly glycoside-sulfo succinates .
When the anionic surfactant(s) are in salt form, they may be chosen from alkali metal salts such as the sodium or potassium salt and preferably the sodium salt, ammonium salts, amine salts and in particular amino alcohol salts, or alkaline-earth metal salts such as the magnesium salts .
Examples o f amino alcoho l salts that may especially be mentioned include monoethano lamine, diethanolamine and triethanolamine salts, monoisopropanolamine, diisopropanolamine or triisopropanolamine salts, 2-amino-2-methyl- 1 -propanol salts, 2- amino-2-methyl- 1 ,3 -propanediol salts and tris(hydroxymethyl)amino methane salts.
Alkali metal or alkaline-earth metal salts, and in particular sodium or magnesium salts, are preferably used.
Among the anionic surfactants mentioned, use is preferably made o f (C6 - C24)alkyl sulfates, (C6 - C24)alkyl ether sulfates comprising from 2 to 50 ethylene oxide units, in particular in the form o f alkali metal, ammonium, amino alcohol and alkaline-earth metal salts, or a mixture of these compounds.
In particular, it is preferred to use (C i 2-C2o)alkyl sulfates, (C 1 2- C2o)alkyl ether sulfates comprising from 2 to 20 ethylene oxide units, especially in the form o f alkali metal, ammonium, amino alcoho l and alkaline-earth metal salts, or a mixture of these compounds . Better still, it is preferred to use sodium lauryl ether sulfate containing 2.2 mo l o f ethylene oxide.
Composition (A) according to the invention and the oxidizing composition (B) may comprise one or more amphoteric or zwitterionic surfactants .
In particular, the amphoteric or zwitterionic surfactant(s), which are preferably non-silicone, which may be used in the present invention may especially be derivatives o f aliphatic secondary or tertiary amines, optionally quaternized in which derivatives the aliphatic group is a linear or branched chain comprising from 8 to 22 carbon atoms, the said amine derivatives containing at least one anionic group, for instance a carboxylate, sulfonate, sulfate, phosphate or phosphonate group .
Mention may be made in particular of (C8-C2o)alkylbetaines, (C8-C2o)alkylsulfobetaines, (C8-C2o)alkylamido(C3 -C8)alkylbetaines and (C8-C2o)alkylamido(C6-C8)alkylsulfobetaines.
Among the secondary or tertiary aliphatic amine derivatives optionally quaternized that may be used, as defined above, mention may also be made of the compounds having the respective structures (V) and (VI) below :
Ra-CONHCH2CH2-N+(Rb)(Rc)-CH2COCr, M+ , X" (V) in which formula:
- Ra represents a C 1 0 - C30 alkyl or alkenyl group derived from an acid RaCOOH preferably present in hydro lysed coconut oil, or a heptyl, nonyl or undecyl group; - Rb represents a beta-hydroxyethyl group; and
- Rc represents a carboxymethyl group;
- M+ represents a cationic counterion derived from an alkali metal or alkaline-earth metal, such as sodium, an ammonium ion or an ion derived from an organic amine, and
- X" represents an organic or mineral anionic counterion, such as that chosen from halides, acetates, phosphates, nitrates, (Ci- C4)alkyl sulfates, (Ci-C4)alkylsulfonates or (Ci- C4)alkylarylsulfonates, in particular methyl sulfate and ethyl sulfate; or alternatively M+ and X" are absent;
Ra'-CONHC^C ^-NtBXB') (VI) in which formula:
- B represents the group -CH2CH2OX';
- B' represents the group -(CH2)ZY', with z = 1 or 2;
- X* represents the group -CH2COOH, -CH2-COOZ', -CH2CH2COOH, -CH2CH2-COOZ', or a hydrogen atom;
- Y* represents the group -COOH, -COOZ',
-CH2CH(OH)S03H or the group -CH2CH(OH)S03Z';
- Z' represents a cationic counterion derived from an alkali metal or alkaline-earth metal, such as sodium, an ammonium ion or an ion derived from an organic amine;
- Ra' represents a Cio-C3o alkyl or alkenyl group of an acid Ra'-COOH which is preferably present in coconut oil or in hydrolysed linseed oil, or an alkyl group, especially a C17 group, and its iso form, or an unsaturated C17 group.
These compounds are classified in the CTFA dictionary, 5th edition, 1993, under the names disodium cocoamphodiacetate, disodium lauroamphodiacetate, disodium caprylamphodiacetate, disodium capryloamphodiacetate, disodium cocoamphodipropionate, disodium lauroamphodipropionate, disodium caprylamphodipropionate, disodium capryloamphodipropionate, lauroamphodipropionic acid and cocoamphodipropionic acid. By way o f example, mention may be made o f the cocoamphodiacetate sold by the company Rhodia under the trade name Mirano l® C2M Concentrate.
Use may also be made o f the compounds of formula (VII) :
Ra" -NHCH(Y " )-(CH2)nCONH(CH2)n ' -N(Rd) (Re) (VII) in which formula:
- Y" represents the group -COOH, -COOZ " ,
-CH2CH(OH)S03H or the group -CH2CH(OH)S03Z " ;
- Rd and Re represent, independently of each other, a C 1 - C 4 alkyl or hydroxyalkyl radical;
- Z" represents a cationic counterion derived from an alkali metal or alkaline-earth metal, such as sodium, an ammonium ion or an ion derived from an organic amine;
- Ra" represents a C i o-C3 o alkyl or alkenyl group of an acid Ra"-COOH which is preferably present in coconut oil or in hydrolysed linseed oil;
- n and n' denote, independently o f each other, an integer ranging from 1 to 3.
Among the compounds o f formula (VII), mention may be made of the compound classified in the CTFA dictionary under the name sodium diethylaminopropyl cocoaspartamide and sold by the company Chimex under the name Chimexane HB .
These compounds may be used alone or as mixtures.
Among the amphoteric or zwitterionic surfactants mentioned above, use is preferably made of (C 8-C2o)alkylbetaines such as cocoylbetaine, (C8-C2o)alkylamido(C3 - C8)alkylbetaines such as cocamidopropylbetaine, and mixtures thereof, and the compounds of formula (VII) such as the sodium salt o f diethylaminopropyl laurylamino succinamate (INCI name : sodium diethylaminopropyl cocoaspartamide).
Among all the surfactants mentioned, use is preferably made o f one or more nonionic surfactants . In a preferred embodiment, composition (A) according to the invention and/or the oxidizing composition (B) comprise one or more nonionic surfactants and one or more cationic surfactants .
In general, the surfactant(s) represent from 1 % to 50%, preferably from 5 % to 40% and better still from 10% to 20% by weight relative to the total weight of composition (A) .
When the oxidizing composition (B) contains one or more surfactants, these surfactants preferably represent from 1 % to 50% by weight, more preferentially from 5 % to 40% by weight and better still from 10% to 20% by weight relative to the total weight of composition (B) .
As indicated previously, composition (A) according to the invention comprises one or more fatty substances .
Preferably, the oxidizing composition (B) also comprises one or more fatty substances .
The term "fatty substance" means an organic compound that is inso luble in water at ordinary temperature (25 °C) and at atmospheric pressure (760 mmHg) (so lubility o f less than 5 %, preferably less than 1 % and even more preferentially less than 0. 1 %). They have in their structure at least one hydrocarbon-based chain comprising at least 6 carbon atoms or a sequence of at least two siloxane groups. In addition, the fatty substances are generally soluble in organic so lvents under the same temperature and pressure conditions, for instance chloroform, dichloromethane, carbon tetrachloride, ethanol, benzene, toluene, tetrahydrofuran (THF), liquid petroleum j elly or decamethy Icy clop entasiloxane.
The fatty substances of the invention preferably do not contain any salified carboxylic acid groups .
Particularly, the fatty substances o f the invention are neither oxyalkylenated nor glycerolated ethers .
The term "oil" means a " fatty substance" that is liquid at room temperature (25 °C) and at atmospheric pressure (760 mmHg; i. e. 1 .013 x 10s Pa) . The term "non-silicone oil" means an oil not containing any silicon atoms (Si) and the term " silicone oil" means an oil containing at least one silicon atom.
More particularly, the fatty substances are chosen from C6 - C i 6 hydrocarbons, hydrocarbons containing more than 16 carbon atoms, non- silicone oils of animal origin, plant or synthetic oils o f triglyceride type, fluoro oils, fatty alcoho ls, fatty acid and/or fatty alcoho l esters other than triglycerides and plant waxes, non-silicone waxes other than fatty alcoho ls, and silicones, and mixtures thereof.
It is recalled that the fatty alcoho ls, esters and acids more particularly contain at least one saturated or unsaturated, linear or branched hydrocarbon-based group comprising 6 to 30 and better still from 8 to 30 carbon atoms, which is optionally substituted, in particular by one or more hydroxyl groups (in particular 1 to 4) . If they are unsaturated, these compounds may comprise one to three conjugated or unconjugated carbon-carbon double bonds .
As regards the C6 - C i 6 hydrocarbons, they may be linear, branched, and optionally cyclic, and are preferably chosen from alkanes. Examples that may be mentioned include hexane, dodecane, undecane, tridecane, and isoparaffins, for instance isohexadecane, isododecane and isodecane.
The linear or branched hydrocarbons of mineral or synthetic origin, containing more than 16 carbon atoms, are preferably chosen from liquid paraffins, petroleum j elly, liquid petroleum j elly, polydecenes, squalane, and hydrogenated polyisobutene such as Parleam®.
A hydrocarbon-based oil o f animal origin that may be mentioned is perhydrosqualene.
The triglyceride oils of plant or synthetic origin are preferably chosen from liquid fatty acid triglycerides containing from 6 to 30 carbon atoms, for instance heptanoic or octanoic acid triglycerides, or alternatively, for example, sunflower oil, corn oil, soybean oil, pumpkin oil, grapeseed oil, sesame seed oil, hazelnut oil, apricot oil, macadamia oil, arara oil, sunflower oil, castor oil, avocado oil, caprylic/capric acid triglycerides, for instance those sold by the company Stearineries Dubois or those sold under the names Miglyol® 810, 812 and 818 by the company Dynamit Nobel, jojoba oil and shea butter oil.
Use will preferably be made of triglyceride oils of plant origin.
The fluoro oils may be chosen from perfluoromethylcyclopentane and perfluoro- 1 ,3-dimethylcyclohexane, sold under the names Flutec® PCI and Flutec® PC3 by the company BNFL Fluorochemicals; perfluoro- 1 ,2-dimethylcyclobutane; perfluoroalkanes such as dodecafluoropentane and tetradecafluorohexane, sold under the names PF 5050® and PF 5060® by the company 3M, or bromoperfluorooctyl sold under the name Foralkyl® by the company Atochem; nonafluoromethoxybutane and nonafluoroethoxyisobutane; perfluoromorpholine derivatives such as 4-trifluoromethyl perfluoromorpholine sold under the name PF 5052® by the company 3M.
The fatty alcohols that are suitable for use in the invention are more particularly chosen from linear or branched, saturated or unsaturated alcohols comprising from 6 to 30 carbon atoms and preferably from 8 to 30 carbon atoms. Examples that may be mentioned include cetyl alcohol, stearyl alcohol and the mixture thereof (cetylstearyl alcohol), octyldodecanol, 2-butyloctanol, 2- hexyldecanol, 2-undecylpentadecanol, oleyl alcohol and linoleyl alcohol.
As regards the fatty acid and/or fatty alcohol esters, which are advantageously different from the triglycerides mentioned above, mention may be made especially of esters of saturated or unsaturated, linear or branched Ci-C26 aliphatic mono- or polyacids and of saturated or unsaturated, linear or branched Ci-C26 aliphatic mono- or polyalcohols, the total carbon number of the esters being greater than or equal to 6 and more advantageously greater than or equal to 10.
Among the monoesters, mention may be made of dihydroabietyl behenate; octyldodecyl behenate; isocetyl behenate; cetyl lactate; C12- Ci5 alkyl lactate; isostearyl lactate; lauryl lactate; linoleyl lactate; oleyl lactate; (iso)stearyl octanoate; isocetyl octanoate; octyl octanoate; cetyl octanoate; decyl oleate; isocetyl isostearate; isocetyl laurate; iso cetyl stearate; isodecyl octanoate; isodecyl oleate; isononyl isononanoate; iso stearyl palmitate; methyl acetyl ricino leate; myristyl stearate; octyl isononanoate; 2-ethylhexyl isononate; octyl palmitate; octyl pelargonate; octyl stearate; octyldodecyl erucate; oleyl erucate; ethyl and isopropyl palmitates, 2-ethylhexyl palmitate, 2-octyldecyl palmitate, alkyl myristates such as isopropyl, butyl, cetyl, 2- octyldodecyl, myristyl or stearyl myristate, hexyl stearate, butyl stearate, isobutyl stearate; dio ctyl malate, hexyl laurate, 2-hexyldecyl laurate.
Still within the context of this variant, esters of C4 - C22 dicarboxylic or tricarboxylic acids and of C 1 - C22 alcoho ls and esters of mono-, di- or tricarboxylic acids and of C2 - C26 di-, tri-, tetra- or pentahydroxy alcohols may also be used.
Mention may in particular be made of: diethyl sebacate; diisopropyl sebacate; diisopropyl adipate; di(n-propyl) adipate; dioctyl adipate; diisostearyl adipate; dio ctyl maleate; glyceryl undecylenate; octyldodecyl stearoyl stearate; pentaerythrityl monoricino leate; pentaerythrityl tetraisononanoate; pentaerythrityl tetrapelargonate; pentaerythrityl tetraisostearate; pentaerythrityl tetraoctanoate; propylene glyco l dicaprylate; propylene glycol dicaprate; tridecyl erucate; triisopropyl citrate; triisostearyl citrate; glyceryl trilactate; glyceryl trioctanoate; trioctyldodecyl citrate; trio leyl citrate; propylene glyco l dioctanoate; neopentyl glyco l diheptanoate; diethylene glycol diisanonate; and polyethylene glyco l distearates.
Among the esters mentioned above, use is preferably made o f ethyl, isopropyl, myristyl, cetyl or stearyl palmitate, 2-ethylhexyl palmitate, 2-octyldecyl palmitate, alkyl myristates, such as isopropyl, butyl, cetyl or 2-octyldodecyl myristate, hexyl stearate, butyl stearate, isobutyl stearate, dioctyl malate, hexyl laurate, 2-hexyldecyl laurate, isononyl isononanoate or cetyl octanoate.
The compositions may also comprise, as fatty ester, sugar esters and diesters of C6 - C30 and preferably C 12 - C22 fatty acids. It is recalled that the term "sugar" means oxygen-bearing hydrocarbon- based compounds containing several alcohol functions, with or without aldehyde or ketone functions, and which comprise at least 4 carbon atoms. These sugars may be monosaccharides, oligosaccharides or polysaccharides .
Examples o f suitable sugars that may be mentioned include sucrose (or saccharose), glucose, galactose, ribose, fucose, maltose, fructose, mannose, arabinose, xylose and lactose, and derivatives thereo f, especially alkyl derivatives, such as methyl derivatives, for instance methylglucose.
The sugar esters of fatty acids may be chosen especially from the group comprising the esters or mixtures of esters of sugars described previously and of linear or branched, saturated or unsaturated C6 - C30 and preferably C 1 2 - C22 fatty acids . If they are unsaturated, these compounds may comprise one to three conjugated or unconjugated carbon-carbon double bonds.
The esters according to this variant may also be chosen from monoesters, diesters, triesters, tetraesters and polyesters, and mixtures thereo f.
These esters may be, for example, o leates, laurates, palmitates, myristates, behenates, cocoates, stearates, linoleates, linolenates, caprates and arachidonates, or mixtures thereof such as, especially, oleopalmitate, oleostearate and palmitostearate mixed esters .
More particularly, use is made of monoesters and diesters and in particular mono- or di-o leate, -stearate, -behenate, -oleate/palmitate, -lino leate, -lino lenate or -oleate/stearate of sucrose, glucose or methylglucose.
Mention may be made, by way o f examp le, of the product sold under the name Glucate® DO by the company Amercho l, which is a methylglucose dio leate .
Examples o f esters or mixtures of esters of sugar and of fatty acid that may also be mentioned include :
- the products sold under the names F 160, F 140, F 1 10, F90, F70 and SL40 by the company Crodesta, respectively denoting sucrose palmitate/stearates formed from 73 % monoester and 27% diester and triester, from 61 %> monoester and 39% diester, triester and tetraester, from 52% monoester and 48% diester, triester and tetraester, from 45 % monoester and 55 % diester, triester and tetraester, from 39% monoester and 6 1 % diester, triester and tetraester, and sucrose mono laurate;
- the products sold under the name Ryoto Sugar Esters, for example referenced B370 and corresponding to sucrose behenate formed from 20% monoester and 80% diester-triester-polyester;
- the sucrose mono-dipalmitate/stearate sold by the company Goldschmidt under the name Tegoso ft® PSE .
The non-silicone wax(es) other than fatty alcoho ls are chosen especially from carnauba wax, candelilla wax, esparto wax, paraffin wax, ozokerite, plant waxes, such as olive tree wax, rice wax, hydrogenated jojoba wax or absolute flower waxes, such as the blackcurrant blossom essential wax sold by the company Bertin (France), or animal waxes, such as beeswaxes or modified beeswaxes (cerabellina); other waxes or waxy raw materials that can be used according to the invention are in particular marine waxes, such as the product sold by the company Sophim under the reference M82, polyethylene waxes or polyolefin waxes in general.
The fatty substance(s) according to the invention may be chosen from silicones.
The silicones that can be used in accordance with the invention may be in the form o f oils, waxes, resins or gums .
Preferably, the silicone(s) are chosen from polydialkylsiloxanes, in particular po lydimethylsiloxanes (PDMSs), and organomodified polysiloxanes comprising at least one functional group chosen from amino groups, aryl groups and alkoxy groups .
Organopolysiloxanes are defined in greater detail in Walter Noll ' s Chemistry and Technology of Silicones ( 1968), Academic Press . They may be vo latile or non-vo latile. The vo latile silicones are more particularly chosen from silicones with a boiling point of between 60°C and 260°C , and even more particularly silicones chosen from:
(i) cyclic po lydialkylsiloxanes comprising from 3 to 7 and preferably from 4 to 5 silicon atoms. These are, for example, octamethylcyclotetrasiloxane sold in particular under the name Volatile Silicone® 7207 by Union Carbide or Silbione® 70045 V2 by Rhodia, decamethylcyclopentasiloxane sold under the name Volatile Silicone® 7158 by Union Carbide, and Silbione® 70045 V5 by Rhodia, and mixtures thereo f.
Mention may also be made o f cyclocopolymers of the dimethylsiloxane/methylalkylsiloxane type, such as Volatile Silicone® FZ 3 109 so ld by the company Union Carbide, of formula:
CH3
Figure imgf000031_0001
CH, with D" : — Si - O— with D' : - Si - O—
CH3 C8 H17
Mention may also be made o f mixtures o f cyclic polydialkylsiloxanes with organosilicon compounds, such as the mixture of octamethylcyclotetrasiloxane and tetra(trimethylsilyl)pentaerythrito l (50/50) and the mixture of octamethylcyclotetrasiloxane and oxy- 1 , 1 ' -bis(2 ,2,2 ' ,2 ' ,3 ,3 ' - hexatrimethylsilyloxy)neopentane;
(ii) linear vo latile po lydialkylsiloxanes containing 2 to 9 silicon atoms and having a viscosity o f less than or equal to 5 x 10"6 m2/s at 25 °C . An example is decamethyltetrasiloxane so ld in particular under the name SH 200 by the company Toray Silicone . Silicones belonging to this category are also described in the article published in Cosmetics and Toiletries, Vol. 91 , Jan. 76, pp . 27-32 , Todd & Byers, Volatile Silicone Fluids for Cosmetics .
The non-vo latile silicones that may be used according to the invention may preferably be non-volatile po lydialkylsiloxanes, polydialkylsiloxane gums and resins, polyorganosiloxanes modified with organic functional groups chosen from amine groups, aryl groups and alkoxy groups, and also mixtures thereof.
The organomodified silicones that may be used in accordance with the invention are silicones as defined above and comprising in their structure one or more organofunctional groups attached via a hydrocarbon-based group .
The organomodified silicones may be polydiarylsiloxanes, in particular polydiphenylsiloxanes, and polyalkylarylsiloxanes functionalized with the organo functional groups mentioned previously.
The po lyalkylarylsiloxanes are particularly chosen from linear and/or branched polydimethyl/methylphenylsiloxanes and polydimethyl/diphenylsiloxanes with a viscosity ranging from l x l O"5 to 5 x l 0"2 m2/s at 25 °C .
Among these polyalkylarylsiloxanes, examples that may be mentioned include the products sold under the following names :
- the Silbione® oils o f the 70 641 series from Rhodia;
- the oils o f the Rhodorsil® 70 633 and 763 series from Rhodia;
- the oil Dow Corning 556 Cosmetic Grade Fluid from Dow Corning;
- the silicones o f the PK series from Bayer, such as the product
PK20;
- the silicones o f the PN and PH series from Bayer, such as the products PN 1000 and PH 1 000;
- certain oils o f the SF series from General Electric, such as SF 1023 , SF 1 154, SF 1250 and SF 1265.
Mention may also be made, among the organomodified silicones, of polyorganosiloxanes comprising :
- substituted or unsubstituted amine groups, such as the products sold under the names GP 4 Silicone Fluid and GP 71 00 by the company Genesee or the products sold under the names Q2 8220 and Dow Corning 929 or 939 by the company Dow Corning. The substituted amine groups are, in particular, C 1 - C 4 amino alkyl groups; - alkoxylated groups, such as the product sold under the name Silicone Copolymer F-755 by SWS Silicones and Abil Wax® 2428 , 2434 and 2440 by the company Go ldschmidt.
More particularly, the fatty substances are chosen from compounds that are liquid or pasty at room temperature (25 °C) and at atmospheric pressure.
Preferably, the fatty substance(s) are chosen from compounds that are liquid at a temperature of 25 °C and at atmospheric pressure.
The fatty substances are advantageously chosen from C6 - C i 6 alkanes, linear or branched hydrocarbons, of mineral or synthetic origin, containing more than 1 6 carbon atoms, non-silicone oils o f plant, mineral or synthetic origin, fatty alcohols, and fatty acid and/or fatty alcoho l esters, or mixtures thereof.
Preferably, the fatty substance(s) are chosen from linear or branched liquid hydrocarbons, of mineral or synthetic origin, containing more than 16 carbon atoms, and especially liquid petroleum j elly and hydrogenated po lyisobutene, C6 - C i 6 alkanes, liquid fatty acid and/or fatty alcoho l esters, and liquid fatty alcoho ls, or mixtures thereo f.
In general, the fatty substances may represent from 1 % to 60%, preferably from 2% to 50%>, better still from 5 % to 40%> by weight, even better still from 7% to 30% by weight and very preferentially from 12% to 25 % by weight relative to the total weight of composition (A) .
When the oxidizing composition (B) contains one or more fatty substances, they preferably represent from 1 % to 60%>, more preferentially from 2% to 50%, better still from 5 % to 40% by weight, even better still from 7% to 30% by weight and very preferentially from 12% to 25 % by weight relative to the total weight of composition (B) .
Composition (A) according to the invention comprises water, in a content of greater than or equal to 40% by weight relative to the total weight of composition (A) . Preferably, the oxidizing composition (B) also comprises water, in a content more preferentially greater than or equal to 40% by weight relative to the total weight of the oxidizing composition (B) .
The water content in compositions (A) and/or (B) preferably ranges from 40% to 95 % by weight, more preferentially from 40% to 80% by weight and in particular from 40% to 70% by weight, relative to the total weight of composition (A) and/or (B), respectively.
Composition (A) according to the invention and/or the oxidizing composition (B) may also comprise one or more water- so luble organic so lvents (so lubility o f greater than or equal to 5 % in water at 25 °C and at atmospheric pressure) .
Examples o f water-so luble organic solvents that may be mentioned include linear or branched and preferably saturated monoalcoho ls or dio ls, comprising 2 to 10 carbon atoms, such as ethyl alcoho l, isopropyl alcoho l, hexylene glycol (2-methyl-2,4- pentanedio l), neopentyl glyco l and 3 -methyl- 1 ,5 -pentanedio l, butylene glyco l, dipropylene glycol and propylene glycol; aromatic alcoho ls such as phenylethyl alcohol; polyols containing more than two hydroxyl functions, such as glycero l; polyo l ethers, for instance ethylene glycol monomethyl, monoethyl and monobutyl ether, propylene glyco l or ethers thereof, for instance propylene glyco l monomethyl ether; and also diethylene glyco l alkyl ethers, especially C 1 - C 4 alkyl ethers, for instance diethylene glycol monoethyl ether or monobutyl ether, alone or as a mixture.
The water-so luble organic solvents, when they are present, generally represent between 1 % and 20% by weight relative to the total weight of the composition according to the invention, and preferably between 5 % and 10% by weight relative to the total weight of each composition containing them.
Composition (A) according to the invention and/or the oxidizing composition (B) may also comprise one or more alkaline agents .
The alkaline agent(s) are especially chosen from aqueous ammonia, alkali metal carbonates or bicarbonates, organic amines with a pKb at 25°C of less than 12, in particular less than 10 and even more advantageously less than 6; from the salts of the amines mentioned previously with acids such as carbonic acid or hydrochloric acid: it should be noted that it is the pKb corresponding to the function of highest basicity.
Preferably, the amines are chosen from alkanolamines, in particular comprising a primary, secondary or tertiary amine function, and one or more linear or branched Ci-Cs alkyl groups bearing one or more hydroxyl radicals; from oxyethylenated and/or oxypropylenated ethylenediamines, and from amino acids and compounds having the following formula:
Rx Rz
/N W-N
Ry NRt
in which W is a Ci-C6 alkylene residue optionally substituted with a hydroxyl group or a Ci-C6 alkyl radical; Rx, Ry, Rz and Rt, which may be identical or different, represent a hydrogen atom or a Ci-C6 alkyl, Ci-C6 hydroxyalkyl or Ci-C6 aminoalkyl radical.
According to one embodiment of the invention, composition (A) according to the invention and/or the oxidizing composition (B) comprise aqueous ammonia and/or at least one alkanolamine and/or at least one basic amino acid, more advantageously aqueous ammonia and/or at least one alkanolamine, such as monoethanolamine, or mixtures thereof.
Advantageously, the content of alkaline agent(s) ranges from 0.01% to 30% by weight, preferably from 0.1% to 20% by weight and better still from 1% to 10% by weight relative to the weight of each composition containing them. It should be noted that this content is expressed as NH3 when the alkaline agent is aqueous ammonia.
The pH of composition (A) of the invention preferably ranges from 1.5 to 12, better still from 6 to 11 and even better still from 8 to 11.
The pH of the oxidizing composition (B) preferably ranges from 1.5 to 9, better still from 1.5 to 7 and even better still from 2 to 4. It can be adjusted by adding acidifying agents, such as hydrochloric acid, (ortho)phosphoric acid, sulfuric acid, boric acid, and also carboxylic acids, for instance acetic acid, lactic acid or citric acid, or sulfonic acids . Alkaline agents such as those previously mentioned may also be used.
Composition (A) according to the invention and/or the oxidizing composition (B) may also comprise one or more direct dyes .
Examples of particularly suitable direct dyes that may be mentioned include nitrobenzene dyes; azo direct dyes; azomethine direct dyes; methine direct dyes; azacarbocyanin direct dyes, for instance tetraazacarbocyanines (tetraazapentamethines); quinone and in particular anthraquinone, naphthoquinone or benzoquinone direct dyes; azine direct dyes; xanthene direct dyes; triarylmethane direct dyes; indoamine direct dyes; indigoid direct dyes; phthalocyanine direct dyes, porphyrin direct dyes and natural direct dyes, alone or as mixtures. In particular, mention may be made o f direct dyes from among : azo; methine; carbonyl; azine; nitro (hetero)aryl; tri(hetero)arylmethane; porphyrin; phthalocyanine and natural direct dyes, alone or as mixtures.
The direct dye(s) may represent from 0.0001 % to 10%> by weight and preferably from 0.005 % to 5 % by weight relative to the weight of composition (A) and/or (B) containing them.
Preferably, the oxidizing composition (B) does not comprise any direct dye(s) .
Composition (A) according to the invention and/or the oxidizing composition (B) may also comprise one or more cosmetic adjuvants.
For example, they may comprise one or more standard additives that are well known in the art, such as anionic, cationic, nonionic or amphoteric polymers or mixtures thereof, agents for preventing hair lo ss, so lid fatty substances other than those mentioned previously, vitamins and provitamins including pantheno l, sunscreens, mineral or organic pigments, sequestrants, plasticizers, solubilizers, acidifying agents, mineral or organic thickeners, especially polymeric thickeners, opacifiers, antioxidants, hydroxy acids, nacreous agents, fragrances and preserving agents .
Needless to say, a person skilled in the art will take care to select this or these optional additional compound(s) such that the advantageous properties intrinsically associated with the invention are not, or are not substantially, adversely affected by the envisaged addition(s) .
The above adjuvants may generally be present in an amount, for each o f them, of between 0 and 20% by weight relative to the total weight of each composition containing them.
According to one embodiment, composition (A) according to the invention may also comprise one or more oxidizing agents. The composition is then said to be "ready to use" in the sense that it does not require the use of the oxidizing composition (B) .
Advantageously, the oxidizing agent(s) used in the context of the invention are chemical oxidizing agents other than atmospheric oxygen.
The said oxidizing agent(s) are preferably chosen from the group formed by hydrogen peroxide, urea peroxide, alkali metal bromates or ferricyanides, peroxygenated salts, for instance persulfates, perborates, peracids and precursors thereof and alkali metal or alkaline-earth metal percarbonates, and most particularly hydrogen peroxide.
The oxidizing agent(s) may represent from 0.01 % to 20%, preferably from 0. 1 % to 10% and better still from 2% to 8% by weight, relative to the total weight of composition (A) .
The oxidizing composition (B) that may be used in the process according to the invention comprises one or more oxidizing agents .
The oxidizing agent(s) of the oxidizing composition (B) are as defined above.
The oxidizing agent(s) may represent from 0.01 % to 20%, preferably from 0. 1 % to 10% and better still from 2% to 8% by weight, relative to the total weight of the oxidizing composition (B) . As outlined above, the oxidizing composition (B) is preferably in the form o f a nanoemulsion. In this case, particularly preferably, composition (A) and the oxidizing composition (B) are such that the mixture of these two compositions is also in the form o f a nanoemulsion.
Compositions (A) and/or (B) according to the invention may especially be in the form o f fluid or thickened liquids, gels or creams.
The nanoemulsions according to the invention may be prepared by mixing water, the fatty substance(s) and the surfactant(s), with vigorous stirring, at a temperature preferably between a temperature close to 20°C and 45 °C , followed by one or more steps of homogenization at high pressure, i. e. at a pressure preferably greater than or equal to 5 x 107 Pa and preferably ranging from 6 x 107 to 1 8 x 107 Pa. The shear will preferably be from 2 x l 06 s" 1 to 5 x 108 s" 1 , and more preferentially from l x l O8 s" 1 to 3 x l 08 s" 1 .
According to a preferred embodiment of the nanoemulsions according to the invention, several successive high-pressure homogenization steps as described above are performed.
The nanoemulsions according to the invention may also be prepared with the aid o f a ternary phase diagram (fatty substance/surfactant/water), established beforehand, according to the fo llowing process :
(i) mixing with stirring of one or more fatty substances and o f one or more surfactants, at a temperature Tm and at normal atmospheric pressure;
(ii) addition o f water with stirring, so as to reach the nanoemulsion zone, detected beforehand by means o f the ternary phase diagram;
(iii) cooling o f the composition to room temperature.
The addition o f the water-so luble ingredients such as the oxidation dyes, the couplers or the optional oxidizing agents takes place at the end of step (ii) or after step (iii) .
The temperature Tm is preferably between 20 and 100°C and better still between 20 and 85 °C . It should be noted that the particle size of the nanoemulsion is conserved during and after this cooling.
The invention also relates to the use of composition (A) as described above for dyeing keratin fibres, in particular the hair.
Another subj ect of the invention is a process for dyeing human keratin fibres, in particular the hair, using composition (A) as defined according to the invention.
According to a first preferred embodiment of the invention, composition (A) is "ready to use" , i. e . it already contains at least one oxidizing agent.
In this case, the keratin fibre dyeing process consists in applying the "ready-to-use" composition to the keratin fibres.
According to a second preferred embodiment, the keratin fibre dyeing process consists in applying composition (A) according to the invention to the keratin fibres, the said composition being applied sequentially to or simultaneously with the oxidizing composition (B) .
In a first variant of the second embodiment above, composition (A) according to the invention is mixed at the time o f use with the oxidizing composition (B) as described above.
In a second variant of the second embodiment above, composition (A) according to the invention is applied to the keratin fibres before or after the oxidizing composition (B) as described above.
The process may be repeated several times in order to obtain the desired coloration.
Irrespective o f the process used and the number o f compositions used, the composition(s) described previously, optionally mixed beforehand, are applied to wet or dry keratin fibres.
The composition(s) are usually left in place on the fibres for a time generally ranging from 1 minute to 1 hour and preferably from 5 minutes to 30 minutes.
The temperature during the process is conventionally between 20 and 80°C and preferably between 20 and 60°C . After the treatment, the human keratin fibres are advantageously rinsed with water. They may optionally be washed with a shampoo , followed by rinsing with water, before being dried or left to dry.
Another subj ect of the invention concerns a multi-compartment device, or a kit for dyeing keratin fibres, comprising at least two compartments :
- a first compartment containing a dye composition (A) as described above; and
- a second compartment containing an oxidizing composition (B) as described above.
According to one variant of the invention, the kit also comprises an additional compartment containing an additional composition comprising one or more treating agents.
The compositions of the kit are packaged in separate compartments, which may be optionally accompanied by suitable identical or different application means, such as fine brushes, coarse brushes or sponges .
The abovementioned kit may also be equipped with means allowing the delivery to the hair o f the desired mixture, such as, for example, the device described in patent FR 2 586 913.
The examples that follow are given purely as illustrations o f the present invention.
EXAMPLES
A cosmetic composition A in the form o f a nanoemulsion was prepared, in accordance with the invention, from the ingredients indicated in the table below (in which the contents are indicated in grams o f active material) :
Composition A amount (in g)
Resorcino l 0.67 Hydroxybenzomorpholine 0.033
m-Aminopheno l 0. 12
2,4-Diaminophenoxyethanol
0.02
hydrochloride
2,5 -Toluenediamine 0.7623
PEG-8 isostearate 13.5
Ceteareth-60 myristyl glyco l 3
Hydrogenated polyisobutene 15
PEG-8 1 .5
Ethano lamine 4
Reducing agent/antioxidants qs
Water qs 100 g
The nanoemulsion o f composition A above was obtained from the knowledge of the surfactants/hydrogenated polyisobutene/water ternary phase diagram. The mixture of surfactants and of hydrogenated polyisobutene o f the above composition according to the invention was brought to a temperature of 60°C and the mixture was then diluted with the water of the formula at the same temperature. The composition was finally cooled to room temperature (20 to 25 °C) . The water-so luble compounds including the oxidation dyes and the couplers are added either after addition o f the water or after cooling to room temperature. A nanoemulsion in which the size o f the oil globules, measured by quasi-elastic light scattering, is less than 100 nm is obtained. This composition is stable on storage for at least 2 months at room temperature and at 45 ° C .
Composition A is mixed at the time of use with an oxidizing composition B in the fo llowing proportions : 10 g of composition A according to the invention and 10 g of oxidizing composition B .
Composition B amount (in g)
Tocopherol 0. 1
Sodium stannate 0.04 Pentasodium pentetate 0.06
Polyquaternium-6 0.2
Cetearyl alcoho l 6
Hexamethrine chloride 0. 15
Glycero l 0.5
Hydrogen peroxide 6
Tetrasodium pyrophosphate 0.03
Mineral oil 20
PEG-4 rapeseed amide 1 . 19
Steareth-20 5
Phosphoric acid qs pH 2.2
Water qs l OOg
The mixture obtained is applied to locks at a rate of 10 g o f mixture per 1 g of hair.
The Applicant finds that the above composition according to the above example has very good working qualities, and especially a particularly pleasant texture. The Applicant finds that the mixture derived from the composition according to the invention is easy to apply and to spread onto the locks of hair. It spreads easily from the roots to the ends .
The composition is left in place for 30 minutes . The hair is then rinsed, washed with a standard shampoo and dried.
The said composition gives the hair a light chestnut coloration, which is judged to be visually very satisfactory. Example 2
The oxidizing composition C in the form o f a nanoemulsion was prepared, in accordance with the invention, from the ingredients indicated in the table below (in which the contents are indicated in grams o f active material) :
Oxidizing composition (C) :
Figure imgf000043_0001
ater qs g
The oxidizing nanoemulsion C above was obtained from the knowledge of the surfactants/hydrogenated polyisobutene/water ternary phase diagram. The mixture of surfactants and of hydrogenated polyisobutene o f composition C above was brought to a temperature of 60°C and the mixture was then diluted with the water of the formula at the same temperature. The composition was finally cooled to room temperature (20 to 25 °C). The water-soluble compounds including the oxidizing agents are added either after addition of the water or after cooling to room temperature. After this cooling to room temperature, the pH is then optionally adjusted to the desired value to obtain the desired composition. A nanoemulsion in which the size o f the oil globules, measured by quasi-elastic light scattering, is less than 100 nm is obtained. This composition is stable on storage for at least 2 months at room temperature and at 45 °C .
The two compositions (A) according to Example 1 and (C) as described above are mixed at the time of use in the fo llowing proportions : 1 0 g of dye composition (A) according to the invention and 10 g of oxidizing composition (C) . The App licant finds that the mixture thus formed conserves the nanoemulsion form.
The mixture is applied to locks at a rate of 10 g of mixture per 1 g of hair.
The Applicant finds that the composition obtained after mixing has very good working qualities, and especially a particularly pleasant texture.
The Applicant finds that this composition is easy to apply and to spread onto the locks of hair.
In addition, the said composition spreads easily from the roots to the ends.
The composition is left in place for 30 minutes. The hair is then rinsed, washed with a standard shampoo and dried.
The said composition gives the hair a light chestnut coloration, which is judged to be visually very satisfactory.

Claims

1 . Cosmetic composition in the form of an oil-in-water nanoemulsion comprising one or more oxidation dyes, one or more surfactants, one or more fatty substances and at least 40% by weight of water, relative to the total weight of the composition; the number- average size of the oil droplets in the said nanoemulsion being less than or equal to 100 nm.
2. Composition according to Claim 1 , characterized in that the oxidation dye(s) comprise one or more oxidation bases preferably chosen from para-phenylenediamines, bis(phenyl)alkylenediamines, para-aminophenols, ortho-aminopheno ls and heterocyclic bases, and the addition salts thereo f.
3. Composition according to the preceding claim, characterized in that the said oxidation base(s) represent from 0.0001 % to 10% by weight relative to the total weight of the composition, preferably from 0.005 % to 5 % by weight and better still from 0. 1 % to 2% by weight relative to the total weight of the composition.
4. Composition according to any one of the preceding claims, characterized in that the oxidation dye(s) comprise one or more couplers preferably chosen from meta-phenylenediamines, meta- aminopheno ls, meta-dipheno ls, naphthalene-based couplers and heterocyclic couplers, and also the addition salts thereo f.
5. Composition according to the preceding claim, characterized in that the said coupler(s) represent from 0.000 1 %) to 10%> by weight relative to the total weight of the composition, preferably from 0.005 % to 5 % by weight relative to the total weight of the composition.
6. Composition according to any one of the preceding claims, characterized in that the said surfactant(s) comprise one or more nonionic surfactants preferably chosen from:
- oxyalkylenated (Cs- C 24)alkylphenols;
- saturated or unsaturated, linear or branched, oxyalkylenated or glycerolated C 8 - C 40 alcohols, comprising one or two fatty chains; saturated or unsaturated, linear or branched, oxyalkylenated C8 - C30 fatty acid amides;
- esters of saturated or unsaturated, linear or branched, C8- C30 acids and of po lyethylene glyco ls;
- esters of saturated or unsaturated, linear or branched, C8-
C30 acids and of sorbito l, preferably oxyethylenated;
- fatty acid esters o f sucrose;
- (C8 - C3 o)alkyl(poly)glucosides, (C 8 - C3 o)alkenyl(poly) glucosides, which are optionally oxyalkylenated (0 to 1 0 oxyalkylene units) and comprising from 1 to 1 5 glucose units, (Cs- C3 o)alkyl (poly)glucoside esters;
- saturated or unsaturated, oxyethylenated plant oils;
- condensates of ethylene oxide and/or of propylene oxide, inter alia, alone or as mixtures;
- N-(C8-C3 o)alkylglucamine and N-(C8-C3 o) acylmethylglucamine derivatives;
- aldobionamides;
- amine oxides;
- oxyethylenated and/or oxypropylenated silicones; - and mixtures thereof.
7. Composition according to the preceding claim, characterized in that the said nonionic surfactant(s) are chosen from:
saturated or unsaturated, linear or branched, oxyalkylenated C8 - C40 alcoho ls, comprising one or two fatty chains;
- (C8 - C3 o)alkyl(poly)glucosides;
- esters of saturated or unsaturated, linear or branched, C8- C30 acids and of po lyethylene glyco ls;
- and mixtures thereof.
8. Composition according to any one of the preceding claims, characterized in that it contains one or more cationic surfactants, preferably chosen from those corresponding to the following formulae :
- those corresponding to the following general formula (I) :
Figure imgf000047_0001
in which the groups Rs to Rn, which may be identical or different, represent a linear or branched aliphatic group comprising from 1 to 30 carbon atoms, or an aromatic group such as aryl or alkylaryl, at least one of the groups Rs to Rn denoting a group comprising from 8 to 30 carbon atoms and preferably from 12 to 24 carbon atoms; X" is an anion chosen from the group of halides, phosphates, acetates, lactates, (Ci-C4)alkyl sulfates, and (Ci- C4)alkylsulfonates or (Ci-C4)alkylarylsulfonates;
- quaternary ammonium salts of imidazoline, for instance those of formula (II) below:
Figure imgf000047_0002
(II) in which Ri2 represents an alkenyl or alkyl group containing from 8 to 30 carbon atoms, R represents a hydrogen atom, a C1-C4 alkyl group or an alkenyl or alkyl group containing from 8 to 30 carbon atoms, R14 represents a C1-C4 alkyl group, R15 represents a hydrogen atom or a C1-C4 alkyl group; X" is an anion chosen from the group consisting of halides, phosphates, acetates, lactates, alkyl sulfates, alkylsulfonates or alkylarylsulfonates in which the alkyl and aryl groups respectively preferably comprise from 1 to 20 carbon atoms and from 6 to 30 carbon atoms; - di- or triquaternary ammonium salts, in particular rmula (III):
Figure imgf000048_0001
in which Ri6 denotes an alkyl radical comprising approximately from 16 to 30 carbon atoms which is optionally hydroxylated and/or interrupted by one or more oxygen atoms, R17 is chosen from hydrogen or an alkyl radical comprising from 1 to 4 carbon atoms or an
(Rl6a)(Rl7a)(Rl8a)N-(CH2)3 group, R16a, Rl7a, Rl8a, Rl8, Rl9, R20 and
R21, which may be identical or different, are chosen from hydrogen or an alkyl radical comprising from 1 to 4 carbon atoms and X" is an anion chosen from the group of halides, acetates, phosphates, nitrates and methyl sulfates;
- quaternary ammonium salts containing at least one ester function, such as those of formula (IV) below:
Figure imgf000048_0002
in which:
R22 is chosen from Ci-C6 alkyl groups and Ci-C6 hydroxyalkyl or dihydroxyalkyl groups;
R23 is chosen from:
- the group
Figure imgf000048_0003
- groups R27, which are linear or branched, saturated or unsaturated Ci-C22 hydrocarbon-based groups,
- a hydrogen atom,
R25 is chosen from:
R
- the group 28 - groups R29 , which are linear or branched, saturated or unsaturated C i -C6 hydrocarbon-based groups,
- a hydrogen atom,
R24 , R26 and R28 , which may be identical or different, are chosen from linear or branched, saturated or unsaturated C7 - C2 1 hydrocarbon-based groups;
r, s and t, which may be identical or different, are integers ranging from 2 to 6;
y is an integer ranging from 1 to 1 0;
x and z, which may be identical or different, are integers ranging from 0 to 1 0;
X" is a simp le or complex, organic or mineral anion;
with the proviso that the sum x + y + z is from 1 to 15 , that when x is 0 then R23 denotes R27 , and that when z is 0 then R25 denotes R29.
9. Composition according to the preceding claim, characterized in that the said cationic surfactant(s) are chosen from those o f formula (I) and those of formula (IV), preferably from those of formula (I) .
10. Composition according to any one of the preceding claims, characterized in that the said surfactant(s) represent from 1 % to 50%, preferably from 5 % to 40% and better still from 10% to 20% by weight relative to the total weight of the composition.
1 1 . Composition according to any one of the preceding claims, characterized in that the fatty substance(s) are chosen from C6 - C i 6 hydrocarbons, hydrocarbons containing more than 16 carbon atoms, non-silicone oils o f animal origin, plant or synthetic oils o f triglyceride type, fluoro oils, fatty alcoho ls, fatty acid and/or fatty alcoho l esters other than triglycerides and plant waxes, non-silicone waxes other than fatty alcoho ls, and silicones, and mixtures thereo f.
12. Composition according to any one of the preceding claims, characterized in that the fatty substance(s) are chosen from compounds that are liquid at a temperature of 25 °C and at atmospheric pressure.
13. Composition according to the preceding claim, characterized in that the fatty substance(s) are chosen from linear or branched liquid hydrocarbons, o f mineral or synthetic origin, containing more than 16 carbon atoms, and especially liquid petroleum j elly and hydrogenated po lyisobutene, C6 - C i 6 alkanes, liquid fatty acid and/or fatty alcoho l esters, and liquid fatty alcoho ls, or mixtures thereo f.
14. Composition according to any one of the preceding claims, characterized in that the said fatty substance(s) represent from 1 % to 60%, preferably from 2% to 50%, better still from 5 % to 40% by weight, even better still from 7% to 30%> by weight and very preferentially from 12% to 25 % by weight, relative to the total weight of the composition.
15 . Composition according to any one of the preceding claims, characterized in that its water content ranges from 40% to 95 % by weight, more particularly from 40% to 80% by weight and in particular from 40% to 70% by weight relative to the total weight of the composition.
16. Composition according to any one of the preceding claims, characterized in that it also comprises one or more oxidizing agents .
17. Composition according to the preceding claim, characterized in that the said oxidizing agent(s) are chosen from hydrogen peroxide, urea peroxide, alkali metal bromates or ferricyanides and peroxygenated salts, and is preferably hydrogen peroxide.
1 8. Composition according to Claim 16 or 17, characterized in that the oxidizing agent(s) represent from 0.01 % to 20%, preferably from 0. 1 % to 10% and better still from 2% to 8% by weight relative to the total weight of the composition.
19. Process for dyeing keratin fibres, which consists in applying to the keratin fibres :
- a composition (A) as defined in any one of Claims 1 6 to 1 8 ; or
- a composition (A) as defined in any one of Claims 1 to 15 , the said composition being app lied sequentially to or simultaneously with an oxidizing composition (B) comprising one or more oxidizing agents.
20. Process according to Claim 19, characterized in that composition (A) is mixed at the time of use with the oxidizing composition (B), and the resulting mixture is then applied to the keratin fibres.
21. Process according to either of Claims 19 and 20, characterized in that the oxidizing agent(s) present in the oxidizing composition (B) are as defined in either of Claims 17 and 18.
22. Process according to any one of Claims 19 to 21, characterized in that the oxidizing composition (B) is in the form of a nanoemulsion and also comprises one or more surfactants, one or more fatty substances and water; the number-average size of the oil droplets in the said nanoemulsion being less than or equal to 100 nm.
23. Process according to Claim 22, characterized in that the said surfactant(s) of the oxidizing composition (B) are as defined in any one of Claims 6 to 10.
24. Process according to either of Claims 22 and 23, characterized in that the said fatty substance(s) of the oxidizing composition (B) are as defined in any one of Claims 11 to 14.
25. Process according to any one of Claims 22 to 24, characterized in that the water content of the oxidizing composition (B) is greater than or equal to 40% by weight, preferably ranging from 40% to 95% by weight, more particularly from 40%> to 80%> by weight and in particular from 40% to 70% by weight relative to the total weight of composition (B).
26. Process according to any one of Claims 22 to 25, characterized in that composition (A) and the oxidizing composition (B) are such that the mixture of these two compositions is also in the form of a nanoemulsion.
27. Kit for the oxidation dyeing of keratin fibres, comprising at least two compartments:
- a first compartment containing a composition (A) as defined in any one of Claims 1 to 15; - a second compartment containing an oxidizing composition (B) as defined in any one o f Claims 19 to 25.
PCT/EP2014/053910 2013-02-28 2014-02-28 Cosmetic composition in the form of an oil-in-water nanoemulsion for the oxidation dyeing of keratin fibres, and process for the same WO2014131871A2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
FR1351772A FR3002441B1 (en) 2013-02-28 2013-02-28 PROCESS FOR COLORING KERATIN FIBERS USING COLORING NANOEMULSION AND OXIDIZING NANOEMULSION
FR1351774A FR3002439B1 (en) 2013-02-28 2013-02-28 COSMETIC COMPOSITION IN THE FORM OF AN OIL-IN-WATER NANOEMULSION FOR THE COLORING OF KERATIN FIBER OXIDATION
FR1351772 2013-02-28
FR1351774 2013-02-28

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WO2014131871A2 true WO2014131871A2 (en) 2014-09-04
WO2014131871A3 WO2014131871A3 (en) 2015-01-15

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US11116220B2 (en) 2017-12-22 2021-09-14 Ecolab Usa Inc. Antimicrobial compositions with enhanced efficacy
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US11540984B2 (en) 2018-05-23 2023-01-03 Conopco, Inc. Nanoemulsions and a method for making the same

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