WO2013136535A1 - A composition for cleansing keratin fibres - Google Patents

A composition for cleansing keratin fibres Download PDF

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Publication number
WO2013136535A1
WO2013136535A1 PCT/JP2012/057655 JP2012057655W WO2013136535A1 WO 2013136535 A1 WO2013136535 A1 WO 2013136535A1 JP 2012057655 W JP2012057655 W JP 2012057655W WO 2013136535 A1 WO2013136535 A1 WO 2013136535A1
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WO
WIPO (PCT)
Prior art keywords
composition
pentaerythritol
fatty
alkyl
iii
Prior art date
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PCT/JP2012/057655
Other languages
French (fr)
Inventor
Shinichi Yamada
Maxime De Boni
Original Assignee
L'oreal
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Publication date
Application filed by L'oreal filed Critical L'oreal
Priority to JP2014539180A priority Critical patent/JP2015515444A/en
Priority to CN201280070920.XA priority patent/CN104135991A/en
Priority to PCT/JP2012/057655 priority patent/WO2013136535A1/en
Publication of WO2013136535A1 publication Critical patent/WO2013136535A1/en

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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34Alcohols
    • A61K8/342Alcohols having more than seven atoms in an unbroken chain
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37Esters of carboxylic acids
    • A61K8/375Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/02Preparations for cleaning the hair
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/12Preparations containing hair conditioners

Definitions

  • the present invention relates to a composition for cleansing keratin fibres.
  • a composition for cleansing keratin fibres such as hair, in particular the hair of a human, which comprises surfactants as an active ingredient is widely known.
  • Such a composition commonly comprises one or more surfactants selected from conventional surfactants especially of the anionic, nonionic and or amphoteric type, but more particularly of the anionic type.
  • a composition for cleansing keratin fibres is applied to wet hair and the foam generated by massaging or rubbing with the hands allows, after rinsing with water, the removal of the various types of dirt initially present on the keratin fibres such as hair.
  • a composition for cleansing keratin fibres comprising surfactants possesses good cleansing power.
  • silicones and/or silicone derivatives such as dimethicone and amodimethicone are commonly added to a composition for cleansing keratin fibres such as a shampoo.
  • a derivative of an organosilicon compound in a shampoo is also disclosed, for example, in US Patent Application Publication No. 2011/0182842 and US 6,511,671, which are incorporated into the present
  • silicones and/or silicone derivatives are known as excellent conditioning agents for a composition for cleansing keratin fibres such as shampoos in terms of cosmetic performances of the composition.
  • silicones and/or silicone derivatives is not always suitable regarding, for example, hair squeakiness and stiffness after frequent applications.
  • silicones are known as excellent conditioning agents for a composition for cleansing keratin fibres such as shampoos in terms of cosmetic performances of the composition.
  • silicones and/or silicone derivatives is not always suitable regarding, for example, hair squeakiness and stiffness after frequent applications.
  • silicones are known as excellent conditioning agents for a composition for cleansing keratin fibres such as shampoos in terms of cosmetic performances of the composition.
  • silicones and/or silicone derivatives is not always suitable regarding, for example, hair squeakiness and stiffness after frequent applications.
  • silicones are known as excellent conditioning agents for a composition for cleansing keratin fibres such as shampoos in terms of cosmetic performances of the composition.
  • non-biodegradable chemical substances Replacement of silicone with more environmental friendly materials in a composition for cleansing keratin fibres such as shampoos is desired. That is, it is desired to provide a composition for cleansing keratin fibres which comprises a reduced amount of silicones and/or silicone derivatives compared to an amount conventionally used or even contains no silicones and silicone derivatives while desired cosmetic effects such as improved disentangling property as described above are still imparted to the keratin fibers.
  • the objective of the present invention is to provide a composition for cleansing keratin fibres comprising a reduced amount of silicones and/or silicone derivatives compared to ordinary amounts thereof
  • a composition for cleansing keratin fibres which does not comprise silicones and silicone derivatives by replacing at least a part of or all of the silicones and/or silicone derivatives with more environmental friendly materials and achieving at least one of the desired effects usually imparted by using the silicones and/or silicone derivatives.
  • a use of a combination of oily substances instead of silicones and/or silicone derivatives could be an alternative method to impart desired cosmetic or conditioning effects to the keratin fibres, but it was difficult to replace silicones by other oily substances without deteriorating foam qualities and cleansing power of a composition for cleansing keratin fibres.
  • a composition of the present invention for cleansing keratin fibres is characterized by comprising, in a medium which is acceptable for a composition for cleansing keratin fibers, (i) at least one surfactant, (ii) at least one fatty alcohol selected from the group consisting of behenyl alcohol and. a mixture of fatty alcohols comprising behenyl alcohol, and (iii) at least one ester of pentaerythritol comprising at least one C 6 -C 3 o fatty chain.
  • silicone derivatives from the amounts commonly used to impart good cosmetic and conditioning effects to keratin fibres such as hair by employing components (ii) and (iii) in addition to component (i) in a composition for cleansing keratin fibres while good cosmetic and conditioning effects on keratin fibres can be achieved.
  • any type of fatty alcohol can be used in combination with behenyl alcohol
  • Such fatty alcohols may be linear or branched, saturated or unsaturated fatty alcohols.
  • linear or branched, preferably linear, and saturated fatty alcohols having 8 to 20, preferably 12 to 20, in particular 14 to 20 carbon atoms are preferably used in combination with behenyl alcohol.
  • fatty alcohols which may be used with behenyl alcohol in a mixture of fatty alcohols mention may be made of saturated linear or branched, preferably linear and saturated fatty alcohols such as octyl alcohol, decyl alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, cetostearyl alcohol, and stearyl alcohol. Any one or more of such alcohols may be used together with behenyl alcohol as the aforementioned component (ii) .
  • KALCOL® 220-80 manufactured by KAO Corporation, which comprises 80 wt% or more of C 22 saturated fatty alcohol and 7 wt% or less of Cis saturated fatty alcohol and having a melting point between 67 to 73°C as measured according to the so-called "transparent method”
  • LANETTE® 22 and 22N comprising behenyl alcohol and having a melting point of approximately 69 °C manufactured by Cognis
  • CONOL® 2265 comprising 10 to 20 wt% of C 2 o saturated fatty alcohol and 65 to 70 wt% of C 2 2 saturated fatty alcohol and having a melting point between 65 and 73°C as measured according to the so-called "transparent method”
  • CONOL® 2280 comprising 80 to 85 wt% of C 2 2 saturated fatty alcohol and having a melting point between 65 to 73 °C as measured by the so-called "temperature rise method", which are manufactured by New Japan Chemical Co. , Ltd. It is necessary
  • a preferred amount of behenyl alcohol as component (ii) is in the range 0.01 to 5 % by weight, preferably 0.03 to 1% by weight, more preferably 0.05 to 0.5% by weight relative to the total amount of the composition.
  • esters of pentaerythritol comprising at least one C 6 -C3o fatty chain should be used as component (iii) " in combination with component (i) and component (ii) as described above .
  • ester compounds which may be used as component (iii) in the present invention could be compounds of formula (I):
  • R2, R3, and R4 are identical or different, and independently represent a hydrogen atom, a Cg-C 3 o alkyl or a C6-C30 alkenyl group, where these alkyl or alkenyl groups are independently linear, branched, or cyclic, or a mixture thereof; pi and p2 ⁇
  • Rl represents a C 6 -C 3 o alkyl or a C6-C 30 alkenyl group or a Z of formula (1-2 ) :
  • R' and R" are identical or different, and independently represent a C 6 -C 3 o alkyl or a C 6 -C 30 alkenyl group; where the alkyl or alkenyl groups of Rl and Z are linear, branched, or cyclic, or a mixture thereof;, and * is the bonding point with the rest of formula (I).
  • R3 preferably represents a C5-C29 alkyl or a C5-C29 alkenyl group
  • R4 preferably represents a C5-C29 alkyl or a C5-C29 alkenyl group
  • Rl represents an alkyl or alkenyl group
  • Rl preferably represents a C5-C29 alkyl or a C5-C29 alkenyl group
  • R2 preferably represents a C5-C2 .
  • 9 alkyl or a C5-C29 alkenyl group; and, the aforementioned alkyl and alkenyl groups may be linear, branched, or cyclic, or a mixture thereof.
  • C 6 -C 3 o fatty acid esters of pentaerythritol are one embodiment of the esters of pentaerythritol comprising at least one C6-C 3 o fatty chain, which are represented by formula (I).
  • C6 ⁇ C 3 o fatty acid esters of pentaerythritol which may be used as a component (iii) for the present invention are not particularly limited.
  • Such compounds are for example pentaerythrityl
  • stearate such as CRODAMOL PMS from CRODA
  • pentaerythrityl tetraabietate such as CRODAMOL PMS from CRODA
  • pentaerythrityl tetrabehenate such as
  • tetracaprylate/tetracaprate such as Crodamol PTC from CRODA
  • pentaerythrityl tetracocoate pentaerythrityl
  • tetraethylhexanoate such as NS-408 from NIPPON CHEMICAL
  • pentaerythrityl tetraisononanoate such as Pelemol P-49 from PHOENIX
  • pentaerythrityl tetraisostearate such as Covaclear from LCW
  • pentaerythrityl tetralaurate such as Pelemol PTL from PHOENIX
  • pentaerythrityl tetramyristate such as Technol PTM from TECHNONET
  • pentaerythrityl tetraoleate such as Liponate PO-4 from LIPO
  • pentaerythrityl tetrastearate such as Liponate PS-4 from LIPO
  • pentaerythrityl trioleate such as Pelemol PTP from PHOENIX
  • di-, tri-, or tetra-C 6 -C 2 2 fatty acid esters of pentaerythritol in particular, di-C6-C 22 fatty acid esters of pentaerythritol, tetra-C6-C 2 2 fatty acid esters of pentaerythritol or a mixture thereof.
  • esters being formed from at least one of C6-C30 fatty acids and pentaerythritol and having two or more hydroxyl groups per molecule are so-called "partial esters".
  • partial esters may be prepared, for example, by means of transesterification using at least one C6-C30 fatty acid methyl ester and an excess amount of pentaerythritol in an appropriate molar ratio such that the hydroxyl groups of the resulting reaction product is two or more per molecule.
  • Such partial esters may also be used for preparing a pentaerythritol ester of formula (I) wherein Rl represents a Z group, by reacting with an ester being formed from at least one C 6 -C 30 fatty alcohol and citric acid and having one or more carboxylic acid groups per molecule are also so-called "partial esters".
  • the aforementioned esters being formed from at least one C6-C30 fatty alcohol and citric acid and having one or more carboxylic acid groups per molecule are also so-called “partial esters” .
  • the aforementioned partial ester of pentaerythritol and the aforementioned partial ester of citric acid are preferably used for preparing the aforementioned pentaerythritol ester of formula (I), wherein Rl of formula (I) represents a Z group, by means of an intermolecular esterification reaction.
  • C 6 -C 30 fatty alcohols and C 6 -C 30 fatty acids are the same as explained above for the partial fatty acid esters of pentaerythritol and the partial fatty alcohol esters of citric acid.
  • Such mixed esters can be prepared by means a method for preparing ester compounds from carboxylic acids and alcohols such as a condensation reaction by removing water from reaction mixture.
  • a transesterification reaction between a lower alkyl ester of carboxylic acid such as a carboxylic acid methyl ester and a compound having hydroxyl group (s) may be also effective to prepare mixed esters.
  • GB 962,919 discloses a method for preparing a mixed ester from pentaerythritol-di-fatty acid ester such as pentaerythritol di-coconut oil fatty acid ester and a citric acid-di-fatty alcohol ester such as citric acid di-octadecyl ester.
  • the method disclosed in GB 962,919 may be preferably used for preparing the mixed ester used for the present invention, which mixed ester is formed from pentaerythritol , at least one C 6 -C 3 o fatty alcohol, citric acid, and at least one C 6 -C 30 fatty acid.
  • Such a mixed ester used for the present invention may also be prepared by esterification between at least one ester being formed from at least one C6 ⁇ C 3 o fatty acid and pentaerythritol and having two or more hydroxyl groups per molecule and at least one ester being formed from at least one C6-C 30 fatty alcohol and citric acid and having one or more carboxylic acid groups per molecule using the method as disclosed in GB 962,919.
  • pentaerythritol or a mixture thereof may be used alone as component (iii) .
  • the molar ratio of at least one ester according to the first embodiment to at least one ester according to the second embodiment are preferably from 1:2 to 2:1, most preferably 1:1, when these two kinds of materials are used in combination as component (iii) of the present invention .
  • mixed esters formed from pentaerythritol, at least one 0 6 - ⁇ 3 ⁇ fatty alcohol, citric acid, and at least one C6-C30 fatty acid, which are represented by formula (I) where Rl represents a Z group, are most preferably used.
  • cocoyl fatty acid is most preferably used as the C 6 -C3o fatty acid and stearyl alcohol is most preferably used as the C6-C30 fatty alcohol, but not limited thereto.
  • the ester compound most preferably used as component (iii) in the composition of the present invention is the product whose INCI name is Dicocoyl Pentaerythrityl Distearyl Citrate, which is commercially available under the tradename of Cutina® Shine manufactured by Cognis. Therefore, it is preferred that component (iii) of the composition of the present invention consists of or comprises Dicocoyl Pentaerythrityl Distearyl Citrate in order to achieve good cosmetic and conditioning effects on keratin fibres.
  • Dicocoyl Pentaerythrityl Distearyl Citrate in a hair care products may have already been known. However, it was not known that the use of Dicocoyl Pentaerythrityl Distearyl Citrate in combination with behenyl alcohol or a mixture of fatty alcohol comprising behenyl alcohol in addition to a surfactant can impart good cosmetic and conditioning effects to a composition for cleansing keratin fibres even if silicones and/or silicone derivatives commonly used for hair care products are not used or the amount thereof is reduced.
  • the cosmetic and conditioning effects provided on keratin fibers by the present invention may be better than the effects of a conventional composition for cleansing keratin fibres comprising silicones such as dimethicone and/or silicone derivatives such as amodimethicone .
  • the composition of the present invention comprises at least one surfactant as a component (i) . It is possible to use one or more surfactants selected from any types of surfactants which can be used for compositions for cleansing keratin fibres . As such surfactants which may be suitably used for the present invention, mention may be made of anionic surfactants, nonionic surfactants, amphoteric or zwitterionic surfactants, and cationic surfactants, which are described in more details below.
  • anionic surfactants or to employ anionic surfactants in combination with one or more selected from the group consisting of amphoteric surfactants and nonionic surfactants as component (i) of the composition of the present invention in order to provide good cleansing power as well as desirable cosmetic and conditioning effects on keratin fibers.
  • anionic surfactant be selected from the group consisting of (C e -C 3 o) alkyl sulfates,
  • polyoxyalkylenated (C6-C30 ) alkyl ether carboxylic acid salts polyoxyalkylenated (C 6 -C 30 ) alkylaryl ether carboxylic acid salts; polyoxyalkylenated (C 6 -C 3 o) alkylamido ether carboxylic acid salts ; and corresponding acids.
  • the anionic surfactants are in the form of salts such as salts of alkali metals, for instance sodium; salts of alkaline-earth metals , for instance magnesium; ammonium salts; amine salts; and amino alcohol salts.
  • nonionic surfactants themselves are also compounds which are well known per se (in this respect see especially the "Handbook of Surfactants” by M. R. Porter, published by Blackie & Son (Glasgow and London), 1991, pp. 116-178, the disclosure of which is incorporated by reference) .
  • they can, for example, be chosen from alcohols , alpha-diols, alkylphenols and esters of fatty acids that are polyethoxylated,
  • N- (C10-C14 ) acylaminopropylmorpholine oxides and mixtures thereof.
  • the nonionic surfactants may be chosen from:
  • oxyalkylenated nonionic surfactants examples include:
  • amphoteric or zwitterionic surfactants can be, for example (nonlimiting list) , amine derivatives such as aliphatic secondary or tertiary amine, and optionally quaternized amine derivatives, in which the aliphatic radical is a linear or branched chain comprising 8 to 22 carbon atoms and containing at least one water-solubilizing anionic group (for example, carboxylate, sulphonate, sulphate, phosphate or phosphonate) .
  • amine derivatives such as aliphatic secondary or tertiary amine
  • optionally quaternized amine derivatives in which the aliphatic radical is a linear or branched chain comprising 8 to 22 carbon atoms and containing at least one water-solubilizing anionic group (for example, carboxylate, sulphonate, sulphate, phosphate or phosphonate) .
  • amphoteric surfactant may preferably be selected from the group consisting of betaines and amidoaminecarboxylated derivatives.
  • the betaine-type amphoteric surfactant is preferably selected from the group consisting of alkylbetaines , alkylamidoalkylbetaines, sulfobetaines , phosphobetaines , and alkylamidoalkylsulfobetaines , in particular,
  • amphoteric surfactants of betaine type are chosen from (C 8 -C2 4 ) alkylbetaines ,
  • Non-limiting examples that may be mentioned include the compounds classified in the CTFA dictionary, 9th edition, 2002, under the names cocobetaine, laurylbetaine, cetylbetaine , coco/oleamidopropylbetaine, cocamidopropylbetaine, palmitamidopropylbetaine, stearamidopropylbetaine,
  • laurylhydroxysultaine and cocosultaine , alone or as mixtures .
  • the betaine-type amphoteric surfactant is preferably an alkylbetaine and an alkylamidoalkylbetaine, in particular cocobetaine and cocamidopropylbetaine .
  • amidoaminecarboxylated derivatives mention may be made of the products sold under the name Miranol, as described in U.S. Pat. Nos. 2,528,378 and 2,781,354 and classified in the CTFA dictionary, 3rd edition, 1982 (the disclosures of which are incorporated herein by reference) , under the names Amphocarboxyglycinates and
  • Rl denotes an alkyl radical of an acid Rl-COOH present in hydrolysed coconut oil, a heptyl, nonyl or undecyl radical, R2 denotes a beta-hydroxyethyl group, and
  • R3 denotes a carboxymethyl group
  • X' denotes a -CH 2 CH 2 -COOH group, -CH 2 -COOZ', -CH 2 CH 2 -COOH, -CH 2 CH 2 -COOZ' or a hydrogen atom
  • Y' denotes -COOH, -COOZ', -CH 2 -CHOH-S0 3 Z' or a -CH 2 -CHOH-S0 3 H radical
  • Z' represents an ion of an alkaline or alkaline earth metal such as sodium, an ammonium ion or an ion derived from an organic amine, and
  • Rl' denotes an alkyl radical of an acid Rl'-COOH present in coconut oil or in hydrolysed linseed oil, an alkyl radical, such as a C 7 , C 9 , C or Ci 3 alkyl radical, a Cn alkyl radical and its iso form, or an unsaturated Ci 7 radical.
  • amphoteric surfactant be selected from (C 8 -C 2 ) -alkyl amphomonoacetates , (C 8 -C24) alkyl amphodiacetates, (C 8 -C 2 4 ) alkyl amphomonopropionates , and (C 8 -C 2 4 ) alkyl amphodipropionates . These compounds are classified in the CTFA dictionary, 5th edition, 1993, under the names Disodium Cocoamphodiacetate, Disodium
  • Caprylamphodipropionate Disodium Caprylamphodipropionate, Lauroamphodipropionic acid and Cocoamphodipropionic acid.
  • cocoamphodiacetate sold under the trade name Miranol® C2M concentrate by the company Rhodia Chimie.
  • the cationic surfactant may be selected from the group consisting of optionally polyoxyalkylenated, primary, secondary or tertiary fatty amine salts, quaternary ammonium salts, and mixtures thereof.
  • quaternary ammonium salts examples include, but are not limited to:
  • Rl, R2, R3, and R4 which may be identical or different, are chosen from linear and branched aliphatic radicals comprising from 1 to 30 carbon atoms and optionally comprising heteroatoms such as oxygen, nitrogen, sulfur and halogens.
  • the aliphatic radicals may be chosen, for example, from alkyl, alkoxy, C 2 -Ce polyoxyalkylene, alkylamide, ( C12 -C22 ) alkylamido (C 2 -C6) alkyl, ( C12-C22 ) alkylacetate and hydroxyalkyl radicals; and aromatic radicals such as aryl and alkylaryl; and X "" is chosen from halides, phosphates, acetates, lactates, ( C2-C6) alkyl sulfates and alkyl- or alkylaryl-sulfonates ;
  • R5 is chosen from alkenyl and alkyl radicals comprising from 8 to 30 carbon atoms, for example fatty acid derivatives of tallow or of coconut;
  • R6 is chosen from hydrogen, C1-C4 alkyl radicals, and alkenyl and alkyl radicals comprising from 8 to 30 carbon atoms;
  • R7 is chosen from C1-C4 alkyl radicals;
  • R8 is chosen from hydrogen and C1-C4 alkyl radicals
  • X ⁇ is chosen from halides , phosphates, acetates, lactates, alkyl sulfates, alkyl sulfonates, and alkylaryl sulfonates.
  • R5 and R6 are, for example, a mixture of radicals chosen from alkenyl and alkyl radicals comprising from 12 to 21 carbon atoms, such as fatty acid derivatives of tallow, R7 is methyl and R8 is hydrogen. Examples of such products include, but are not limited . to, Quaternium-27 (CTFA 1997) and
  • Quaternium-83 (CTFA 1997), which are sold under the names "Rewoquat®” W75, W90, W75PG and W75HPG by the company Witco; diquaternary ammonium salts of formula (IV):
  • R9 is chosen from aliphatic radicals comprising from 16 to 30 carbon atoms
  • RIO is chosen from hydrogen or alkyl radicals comprising from 1 to 4 carbon atoms or a group (R16a) (Rl7a) (R18a) N + (CH 2 ) 3 ; Rll, R12, R13, R14, R16a, R17a, and R18a, which may be identical or different, are chosen from hydrogen and alkyl radicals comprising from 1 to 4 carbon atoms; and
  • X " is chosen fromhalides, acetates, phosphates, nitrates, ethyl sulfates, and methyl sulfates.
  • diquaternary ammonium salt is FINQUAT CT-P of FINETEX ( Quaternium-89 ) or FINQUAT CT of FINETEX (Quaternium-75 ) ;
  • quaternary ammonium salts comprising at least one ester function, such as those of formula (V) below: wherein :
  • R22 is chosen from C1-C6 alkyl radicals and C1-C6 hydroxyalkyl and dihydroxyalkyl radicals;
  • R23 is chosen from:
  • hydrocarbon-based radicals R27, and hydrogen are hydrocarbon-based radicals R27, and hydrogen
  • R25 is chosen from:
  • R24, R26, and R28 which may be identical or different, are chosen from linear and branched, saturated and unsaturated, C 7 -C2i, hydrocarbon-based radicals;
  • r, s, and t which may be identical or different, are chosen from integers ranging from 2 to 6;
  • y is chosen from integers ranging from 1 to 10;
  • x and z which may be identical or different, are chosen from ' integers ranging from 0 to 10;
  • X ⁇ is chosen from simple and complex, organic and inorganic anions; with the proviso that the sum x+y+z ranges from 1 to 15, that when x is 0, R23 denotes R27, and that when z is 0, R25 denotes R29.
  • R22 may be chosen from linear and branched alkyl radicals. In one embodiment, R22 is chosen from linear alkyl radicals. In another embodiment, R22 is chosen from methyl, ethyl, hydroxyethyl, and dihydroxypropyl radicals , for example methyl and ethyl radicals. In one embodiment, the sum x+y+z ranges from 1 to 10.
  • R23 is a hydrocarbon-based radical R27, it may be long and comprise from 12 to 22 carbon atoms, or short and comprise from 1 to 3 carbon atoms.
  • R25 is a hydrocarbon-based radical R29, it may comprise, for example, from 1 to 3 carbon atoms.
  • R24, R26, and R28 which may be identical or different, are chosen from linear and branched, saturated and unsaturated, C11-C21 hydrocarbon-based radicals, for example from linear and branched, saturated and unsaturated C11-C21 alkyl and alkenyl radicals.
  • x and z which may be identical or different, are 0 or 1.
  • y is equal to 1.
  • r, s and t which may be identical or different, are equal to 2 or 3, for example equal to 2.
  • the anion X- may be chosen from, for example, halides, such as chloride, bromide, and iodide; and C1-C4 alkyl sulfates, such as methyl sulfate.
  • halides such as chloride, bromide, and iodide
  • C1-C4 alkyl sulfates such as methyl sulfate.
  • methanesulfonate, phosphate, nitrate, tosylate, an anion derived from an organic acid, such as acetate and lactate, and any other anion that is compatible with the ammonium comprising an ester function are other non-limiting examples of anions that may be used according to the invention.
  • the anion X- is chosen from chloride and methyl sulfate.
  • ammonium salts of formula (V) may be used, wherein:
  • R22 is chosen from methyl and ethyl radicals
  • 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 radical below:
  • R25 is chosen from:
  • R24, R26, and R28 which may be identical or different, are chosen from linear and branched, saturated and unsaturated, C13-C17 hydrocarbon-based radicals, for example from linear and branched, saturated and unsaturated, C13-C17 alkyl and alkenyl radicals .
  • the hydrocarbon-based radicals are linear .
  • Non-limiting examples of compounds of formula (V) that may be mentioned include salts, for example chloride and methyl sulfate, of diacyloxyethyl-dimethylammonium, of
  • the acyl radicals may comprise from 14 to 18 carbon atoms, and may be derived, for example, from a plant oil, for instance palm oil and sunflower oil. When the compound comprises several acyl radicals, these radicals may be identical or different.
  • alkyldiisopropanolamine onto fatty acids or onto mixtures of fatty acids of plant or animal origin, or by transesterification of the methyl esters thereof.
  • This esterification may be followed by a quaternization using an alkylating agent chosen from alkyl halides, for example methyl and ethyl halides; dialkyl sulfates, for example dimethyl and diethyl sulfates; methyl methanesulfonate; methyl para-toluenesulfonate; glycol chlorohydrin; and glycerol chlorohydrin .
  • alkylating agent chosen from alkyl halides, for example methyl and ethyl halides; dialkyl sulfates, for example dimethyl and diethyl sulfates; methyl methanesulfonate; methyl para-toluenesulfonate; glycol chlorohydrin; and glycerol chloro
  • Such compounds are sold, for example, under the names Dehyquart® by the company Cognis, Stepanquat® by the company Stepan, Noxamium® by the company Ceca, and "Rewoquat® WE 18" by the company Rewo-Goldschmidt .
  • quaternary ammonium salts mentioned above that may be used in compositions according to the invention include, but are not limited to, those corresponding to formula (II), for example tetraalkylammonium chlorides, for instance dialkyldimethylammonium and alkyltrimethylammonium chlorides in which the alkyl radical comprises from about 12 to 22 carbon atoms, such as behenyltrimethylammonium,
  • the present invention it is preferred to use one or more anionic surfactants alone or in combination with one or more nonionic surfactants and/or amphoteric surfactants as described above.
  • the amounts of the one or more surfactants contained in the composition of the present invention are not particularly limited as far as desired cleansing property of the composition is obtained.
  • the amount of the surfactants contained in the composition of the present invention is not particularly limited.
  • surfactants are commonly contained in a composition for cleansing keratin fibres of the present invention in the range from 4% to 50% by weight, preferably from 4% to 35% by weight of the total weight of the final composition.
  • anionic surfactants are contained in the composition according to the- invention in the range from 4% to 50% by weight, preferably from 4% to 35% by weight of the total weight of the composition.
  • anionic surfactants used as component (i) and the esters of pentaerythritol used as a component (iii) under the condition where the ratio of the total weight of anionic surfactants to the total weight of esters of pentaerythritol is within the range of 60:1 to 25:1; preferably of 50:1 to 30:1.
  • the ratio of the total weight of surfactants (that is, the weight of all surfactants) used as component (i) to the total weight of esters of pentaerythritol used as component (iii) of the composition of the present invention is preferably in the range of 80 : 1 to 25 : 1.
  • good cosmetic and conditioning effects on keratin fibres may be achieved by using behenyl alcohol or fatty alcohols comprising behenyl alcohol as component (ii) and pentaerythritol fatty esters used as component (iii) in combination with surfactants used as component (i) even without employing silicones and/or silicone derivatives such as dimethicones and amodimethicones commonly used for hair care products.
  • silicones and/or silicone derivatives in addition to components (ii) and (iii) .
  • the amounts of silicones and/or silicone derivatives contained in the composition of the present invention can be reduced compared to the amounts usually employed in hair care products.
  • silicones and/or silicones derivatives are present in the composition in an amount of 0.5wt% or less, relative to the total amount of the composition, most preferably are absent from the composition (0% of silicones and silicone derivatives).
  • Silicones which may be used for compositions for cleansing keratin fibres are disclosed, for example, from line 22 in columns 5 to line 14 in column 7 of US 6,511,671, which is incorporated herein by reference.
  • the use of silicones such as dimethicone is well known in the art.
  • the use of silicone derivatives such as amodimethicone for compositions for cleansing keratin fibres is also known in the art.
  • the use of silicone derivatives for compositions for cleansing keratin fibres is disclosed, for example, from line 9 on page 23 to line 3 on page 28 of the English text of JP-A-2011-132241, which is incorporated herein by reference.
  • At least one selected from silicones and silicone derivatives which are known in the art to be used in cosmetic compositions may also be employed in the composition of the present invention, if desired, in addition to the combination of aforementioned components (i) to (iii) of the present invention.
  • One or more substances commonly used in a composition for cleansing keratin fibers may also be optionally added to the composition of the present invention. Such substances are shown below, but not limited thereto.
  • compositions according to the invention have a final pH generally ranging from 3 to 10.
  • the pH ranges from 4 to 9.
  • the adjustment of the pH to the desired value may be carried out conventionally by addition of a base (organic or inorganic) to the composition, for example ammonium hydroxide, sodium hydroxide, sodium carbonate or a primary, secondary or tertiary (poly) amine, such as monoethanolamine, diethanolamine, triethanolamine, isopropanolamine or
  • compositions according to the present invention may also contain viscosity-regulating agents such as electrolytes, or thickening agents.
  • viscosity-regulating agents such as electrolytes, or thickening agents.
  • viscosity-regulating agents such as electrolytes, or thickening agents.
  • compositions according to the invention may also optionally contain other agents which have the effect of improving the cosmetic properties of keratin fibres without, however, adversely impairing the stability of the compositions .
  • agents which have the effect of improving the cosmetic properties of keratin fibres without, however, adversely impairing the stability of the compositions .
  • cationic polymers such as polyquaternium-10 , polyquaternium-6, polyquaternium-7 , polyquaternium- , polyquaternium-37 , amphoteric polymers such as polyquaternium-22 , proteins, protein hydrolysates , ceramides, pseudoceramides , fatty acids with linear or branched (Ci 6 -C 0 ) chains such as
  • compositions for cleansing keratin fibres for example, a solution, a suspension, an emulsion such as a W/O or 0/W emulsion, a gel, and the like.
  • Fatty alcohol a mixture of behenyl alcohol (72 to 80% by weight), arachidyl alcohol and stearyl alcohol: LANETTE 22 available from COGNIS, with a melting point of approximately 69°C;
  • Alkyl carboxylate Laureth-5 carboxylate: AKYPO RLM 45CA available from KAO CHEMICALS;
  • a shampoo according to the present invention was prepared, whose formulation is as shown in Table 1.
  • Example 1 Shampoo
  • the protocol for preparation of the shampoo is as follows: 1. A mixture of behenyl, arachidyl and stearyl alcohols (LANETTE 22) and dicocoyl pentaerythrityl distearyl citrate (CUTINA SHINE) were dispersed in lauryl glucoside (PLANTAREN 1200 N UP) at 75 °C, followed by cooling to room temperature.
  • LANETTE 22 behenyl, arachidyl and stearyl alcohols
  • CUTINA SHINE dicocoyl pentaerythrityl distearyl citrate
  • Glycol distearate (TEGIN BL 315) was dispersed in a part of sodium laureth sulfate (TEXAPON N 702) at 75°C, followed by cooling to room temperature.
  • Panelists after applying an appropriate amount of the shampoo to wet hair, foamed the shampoo and massaged the hair and scalp with the shampoo, followed by rinsing with water and drying.

Abstract

The objective of the present invention is to provide a composition for cleansing keratin fibres which can exhibit good cosmetic or conditioning effects in addition to good cleansing power even silicones and/or silicone derivatives are not used or the amount thereof is reduced compared to the amounts thereof conventionally used. The present invention relates to a A composition for cleansing keratin fibres, characterized by comprising (i) at least one surfactant, (ii) at least one fatty alcohol selected from the group consisting of behenyl alcohol and a mixture of fatty alcohols comprising behenyl alcohol, and (iii) at least one ester of pentaerythritol comprising at least one C6-C30 fatty chain.

Description

DESCRIPTION
[Title of Invention] A COMPOSITION FOR CLEANSING KERATIN FIBRES
[0001]
[Technical Field of Invention]
The present invention relates to a composition for cleansing keratin fibres.
[0002]
[Technical Background]
A composition for cleansing keratin fibres such as hair, in particular the hair of a human, which comprises surfactants as an active ingredient is widely known. Such a composition commonly comprises one or more surfactants selected from conventional surfactants especially of the anionic, nonionic and or amphoteric type, but more particularly of the anionic type. A composition for cleansing keratin fibres is applied to wet hair and the foam generated by massaging or rubbing with the hands allows, after rinsing with water, the removal of the various types of dirt initially present on the keratin fibres such as hair.
[0003]
A composition for cleansing keratin fibres comprising surfactants possesses good cleansing power. However, it is also desired to use some additives to impart cosmetic effects to a composition for cleansing keratin fibers. In order to impart cosmetic effects such as sheen, softness, suppleness, lightness, a natural feel and/or improved disentangling property to the keratin fibres, silicones and/or silicone derivatives such as dimethicone and amodimethicone are commonly added to a composition for cleansing keratin fibres such as a shampoo. Such a use of a derivative of an organosilicon compound in a shampoo is also disclosed, for example, in US Patent Application Publication No. 2011/0182842 and US 6,511,671, which are incorporated into the present
specification by reference.
[0004] [Problems to be Solved]
As mentioned above, silicones and/or silicone
derivatives are known as excellent conditioning agents for a composition for cleansing keratin fibres such as shampoos in terms of cosmetic performances of the composition. However, the use of silicones and/or silicone derivatives is not always suitable regarding, for example, hair squeakiness and stiffness after frequent applications. Moreover silicones are
non-biodegradable chemical substances. Replacement of silicone with more environmental friendly materials in a composition for cleansing keratin fibres such as shampoos is desired. That is, it is desired to provide a composition for cleansing keratin fibres which comprises a reduced amount of silicones and/or silicone derivatives compared to an amount conventionally used or even contains no silicones and silicone derivatives while desired cosmetic effects such as improved disentangling property as described above are still imparted to the keratin fibers. Thus, the objective of the present invention is to provide a composition for cleansing keratin fibres comprising a reduced amount of silicones and/or silicone derivatives compared to ordinary amounts thereof
conventionally used or even a composition for cleansing keratin fibres which does not comprise silicones and silicone derivatives by replacing at least a part of or all of the silicones and/or silicone derivatives with more environmental friendly materials and achieving at least one of the desired effects usually imparted by using the silicones and/or silicone derivatives. A use of a combination of oily substances instead of silicones and/or silicone derivatives could be an alternative method to impart desired cosmetic or conditioning effects to the keratin fibres, but it was difficult to replace silicones by other oily substances without deteriorating foam qualities and cleansing power of a composition for cleansing keratin fibres.
[0005]
[Means to Solve the Problems] To achieve the objective as described above, the inventors of the present invention have studied extensively and found that the use of a combination of behenyl alcohol or fatty alcohols comprising behenyl alcohol and at least one ester compound selected from particular fatty acid ester compounds derived from pentaerythritol can impart good cosmetic and conditioning effects to keratin fibres, even if the amounts of silicones and/or silicone derivatives contained in the composition for cleansing keratin fibres are reduced from an amount conventionally employed or even if silicones and silicone derivatives are not added to the composition.
[0006]
That is, a composition of the present invention for cleansing keratin fibres is characterized by comprising, in a medium which is acceptable for a composition for cleansing keratin fibers, (i) at least one surfactant, (ii) at least one fatty alcohol selected from the group consisting of behenyl alcohol and. a mixture of fatty alcohols comprising behenyl alcohol, and (iii) at least one ester of pentaerythritol comprising at least one C6-C3o fatty chain..
[0007]
By using the combination of components (i) to (iii) described above in a composition for cleansing keratin fibres, even if silicones and/or silicone derivatives are not added to the composition, or the amounts of silicones and/or silicone derivatives added to the composition are reduced from an amount conventionally employed for such a composition of the prior art, at least one, preferably two or more of the aforementioned good cosmetic and conditioning effects on keratin fibres can be achieved. In other words, it is possible to exclude silicones and/or silicone derivatives from the composition or reduce the amounts of silicones . and/or silicone derivatives from the amounts commonly used to impart good cosmetic and conditioning effects to keratin fibres such as hair by employing components (ii) and (iii) in addition to component (i) in a composition for cleansing keratin fibres while good cosmetic and conditioning effects on keratin fibres can be achieved.
[0008]
Details of each of the components which may be used for the composition of the present invention are described below.
[0009]
[Medium which may be used for the composition of the present invention]
The composition for cleansing keratin fibers of the present invention comprises the aforementioned components (i) to (iii) in a medium which is acceptable for a composition for cleansing keratin fibers. The medium acceptable for the composition for cleansing keratin fibres can be also referred to as a cosmetically acceptable aqueous medium, which is widely known in the art. As examples of the aqueous medium, mention may be made of water or a mixture of water and a cosmetically acceptable solvent such as C1-C4 alcohols, for instance, ethanol, isopropanol, tert-butanol or n-butanol; and alkylene glycols such as propylene glycol or glycol ethers. Any one or more of the solvents may be used in combination with water. It is also preferred to use water alone as a medium for the composition of the present invention.
[0010]
Preferably, the composition of the present invention comprises from 50 to 95% by weight of water relative to the total weight of the composition, but not limited thereto.
[0011]
[Fatty alcohols which may be used for the composition of the present invention]
As fatty alcohols which may be used as a component (ii) for the present invention, mention may be made of behenyl alcohol and a mixture of fatty alcohols comprising behenyl alcohol as an essential component. If a mixture of fatty alcohols comprising behenyl alcohol is used for the present invention, fatty alcohol components other than behenyl alcohol are not particularly limited. However, if a mixture of fatty alcohols is used as a component (ii), it is preferred to use a mixture of fatty alcohols comprising at least 25% by weight of behenyl alcohol. Preferably, the mixture of fatty alcohols exists in a solid state at 50°C, preferably 60°C. By using a mixture of fatty alcohols which exists in a solid state at 50°C, preferably at 60°C, in combination with the aforementioned components (i) and (iii) , good cosmetic and conditioning effects as mentioned above can be imparted to the keratin fibres such as hair. As far as a resulting mixture of fatty alcohols exists in a solid state at 50°C, preferably at 60°C, any type of fatty alcohol can be used in combination with behenyl alcohol Such fatty alcohols may be linear or branched, saturated or unsaturated fatty alcohols. However, linear or branched, preferably linear, and saturated fatty alcohols having 8 to 20, preferably 12 to 20, in particular 14 to 20 carbon atoms are preferably used in combination with behenyl alcohol. As examples of fatty alcohols which may be used with behenyl alcohol in a mixture of fatty alcohols, mention may be made of saturated linear or branched, preferably linear and saturated fatty alcohols such as octyl alcohol, decyl alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, cetostearyl alcohol, and stearyl alcohol. Any one or more of such alcohols may be used together with behenyl alcohol as the aforementioned component (ii) .
[0012]
Linear and saturated C22 fatty alcohol is referred to as behenyl alcohol. For the present invention, pure behenyl alcohol can be used as component (ii) . However, commercially available "behenyl alcohol" comprising linear and saturated C22 fatty alcohol can be also preferably used as component (ii) . As such "benehyl alcohol", the following products are commercially available: KALCOL® 220-80 manufactured by KAO Corporation, which comprises 80 wt% or more of C22 saturated fatty alcohol and 7 wt% or less of Cis saturated fatty alcohol and having a melting point between 67 to 73°C as measured according to the so-called "transparent method"; LANETTE® 22 and 22N comprising behenyl alcohol and having a melting point of approximately 69 °C manufactured by Cognis; and CONOL® 2265 comprising 10 to 20 wt% of C2o saturated fatty alcohol and 65 to 70 wt% of C22 saturated fatty alcohol and having a melting point between 65 and 73°C as measured according to the so-called "transparent method", and CONOL® 2280 comprising 80 to 85 wt% of C22 saturated fatty alcohol and having a melting point between 65 to 73 °C as measured by the so-called "temperature rise method", which are manufactured by New Japan Chemical Co. , Ltd. It is necessary that a mixture of fatty alcohols used as component (ii) of the present invention comprises linear and saturated C22 fatty alcohol whose chemical name is behenyl alcohol.
[0013]
A preferred amount of behenyl alcohol as component (ii) is in the range 0.01 to 5 % by weight, preferably 0.03 to 1% by weight, more preferably 0.05 to 0.5% by weight relative to the total amount of the composition.
[0014]
[Esters of pentaerythritol comprising at least one C6-C30 fatty chain]
For the composition of the present invention, esters of pentaerythritol comprising at least one C6-C3o fatty chain should be used as component (iii)" in combination with component (i) and component (ii) as described above . Such ester compounds which may be used as component (iii) in the present invention could be compounds of formula (I):
Figure imgf000007_0001
in which
R2, R3, and R4 are identical or different, and independently represent a hydrogen atom, a Cg-C3o alkyl or a C6-C30 alkenyl group, where these alkyl or alkenyl groups are independently linear, branched, or cyclic, or a mixture thereof; pi and p2 ι
independently equal to 0 or 1; and
Rl represents a C6-C3o alkyl or a C6-C30 alkenyl group or a Z of formula (1-2 ) :
Figure imgf000008_0001
in which R' and R" are identical or different, and independently represent a C6-C3o alkyl or a C6-C30 alkenyl group; where the alkyl or alkenyl groups of Rl and Z are linear, branched, or cyclic, or a mixture thereof;, and * is the bonding point with the rest of formula (I).
In formula (I), when pi is 1, R3 preferably represents a C5-C29 alkyl or a C5-C29 alkenyl group; when p2 is 1, R4 preferably represents a C5-C29 alkyl or a C5-C29 alkenyl group; when Rl represents an alkyl or alkenyl group, Rl preferably represents a C5-C29 alkyl or a C5-C29 alkenyl group; and R2 preferably represents a C5-C2.9 alkyl or a C5-C29 alkenyl group; and, the aforementioned alkyl and alkenyl groups may be linear, branched, or cyclic, or a mixture thereof.
[0015]
[C6-C3o fatty acid esters of pentaerythritol]
C6-C3o fatty acid esters of pentaerythritol are one embodiment of the esters of pentaerythritol comprising at least one C6-C3o fatty chain, which are represented by formula (I). C6~C3o fatty acid esters of pentaerythritol which may be used as a component (iii) for the present invention are not particularly limited.
[0016]
That is, in a first embodiment of the invention, in formula (I), Rl represents a C6-C30, preferably C5-C29 alkyl or a C6-C3o, preferably C 5-C29 alkenyl group and more particularly a C6-C22 r especially C5-C2i alkyl or a C6-C22, especially C5-C2i alkenyl group .
[0017]
Such compounds are for example pentaerythrityl
stearate (such as CRODAMOL PMS from CRODA) , pentaerythrityl tetraabietate, pentaerythrityl tetrabehenate (such as
Liponate PB4 from LIPO) , pentaerythrityl
tetracaprylate/tetracaprate (such as Crodamol PTC from CRODA) , pentaerythrityl tetracocoate, pentaerythrityl
tetraethylhexanoate (such as NS-408 from NIPPON CHEMICAL), pentaerythrityl tetraisononanoate (such as Pelemol P-49 from PHOENIX) , pentaerythrityl tetraisostearate (such as Covaclear from LCW) , pentaerythrityl tetralaurate ( such as Pelemol PTL from PHOENIX) , pentaerythrityl tetramyristate ( such as Technol PTM from TECHNONET) , pentaerythrityl tetraoleate (such as Liponate PO-4 from LIPO) , pentaerythrityl tetrastearate (such as Liponate PS-4 from LIPO), pentaerythrityl trioleate, pentaerythrityl tetrapelargonate (such as Pelemol PTP from PHOENIX) , pentaerythrityl distearate (such as Radiasurf 7175 from ATOFINA) .
[0018]
In this embodiment, it is preferred to use di-, tri-, or tetra-C6-C22 fatty acid esters of pentaerythritol , in particular, di-C6-C22 fatty acid esters of pentaerythritol, tetra-C6-C22 fatty acid esters of pentaerythritol or a mixture thereof.
[0019]
C6-C30 fatty acid esters of pentaerythritol may be prepared by means of any of the conventional synthetic methods for preparing fatty acid esters such as esterification reactions of C5-C3o, preferably C6-C22, more preferably Ci2-C22, in particular Ci4-C22 fatty acids and pentaerythritol or transesterification reactions of alkyl esters such as methyl esters of C6-C30, preferably C6-C22, more preferably Ci2-C22, in particular Ci4-C22 fatty acids and pentaerythritol. The method for preparing di-fatty acid ester of pentaerythritol as disclosed in GB 962, 919, which is incorporated into the present specification by reference, can be used for preparing C6-C3o fatty acid esters of pentaerythritol having a different average number of hydroxyl groups per molecule depending on the molar ratio of alkyl esters of fatty acids to pentaerythritol employed for the transesterification reaction.
[0020]
The aforementioned esters being formed from at least one of C6-C30 fatty acids and pentaerythritol and having two or more hydroxyl groups per molecule are so-called "partial esters". Such partial esters may be prepared, for example, by means of transesterification using at least one C6-C30 fatty acid methyl ester and an excess amount of pentaerythritol in an appropriate molar ratio such that the hydroxyl groups of the resulting reaction product is two or more per molecule.
[0021]
Such partial esters may also be used for preparing a pentaerythritol ester of formula (I) wherein Rl represents a Z group, by reacting with an ester being formed from at least one C6-C30 fatty alcohol and citric acid and having one or more carboxylic acid groups per molecule are also so-called "partial esters". The aforementioned esters being formed from at least one C6-C30 fatty alcohol and citric acid and having one or more carboxylic acid groups per molecule are also so-called "partial esters" . Such partial esters having one or more carboxylic acid groups per molecule may be prepared, for example, by means of esterification in an aqueous medium using at least one C6-C30 fatty alcohol and an excess amount of citric acid in an appropriate molar ratio such that one or more carboxyl groups remains per molecule of the resulting partial esters. Such a method for preparing partial esters of fatty alcohol and citric acid is disclosed in GB 962,919, whose disclosures are incorporated into the present specification by reference.
[0022]
As C6-C30 fatty alcohols which may be used for preparing partial esters of citric acid, mention may be made of linear or branched, saturated or unsaturated fatty alcohols, in particular linear and saturated C6-C30, preferably C^- z, more preferably C12-C22, in particular C14-C22 fatty alcohol such as octyl alcohol, decyl alcohol, lauryl alcohol, myristyl alcohol, cetanol, cetostearyl alcohol, stearyl alcohol, behenyl alcohol, and a mixture of two or more of the aforementioned alcohols.
[0023]
The aforementioned partial ester of pentaerythritol and the aforementioned partial ester of citric acid are preferably used for preparing the aforementioned pentaerythritol ester of formula (I), wherein Rl of formula (I) represents a Z group, by means of an intermolecular esterification reaction.
[0024]
In a second embodiment of the invention, as the ester of pentaerythritol comprising at least one C6-C3o fatty chain used for the present invention, mention may be made of esters of formula (I) wherein Rl represents a Z group. Such a compound is, for example, Dicocoyl Pentaerythrityl Distearyl Citrate (which is available as Cutina Shine from COGNIS) . These mixed esters are formed, for example, from pentaerythritol, at least one C6~C3o fatty alcohol, citric acid, and at least one C6~C3o fatty acid. C6-C30 fatty alcohols and C6-C30 fatty acids are the same as explained above for the partial fatty acid esters of pentaerythritol and the partial fatty alcohol esters of citric acid. Such mixed esters can be prepared by means a method for preparing ester compounds from carboxylic acids and alcohols such as a condensation reaction by removing water from reaction mixture. Alternatively, a transesterification reaction between a lower alkyl ester of carboxylic acid such as a carboxylic acid methyl ester and a compound having hydroxyl group (s) may be also effective to prepare mixed esters. GB 962,919 discloses a method for preparing a mixed ester from pentaerythritol-di-fatty acid ester such as pentaerythritol di-coconut oil fatty acid ester and a citric acid-di-fatty alcohol ester such as citric acid di-octadecyl ester. The method disclosed in GB 962,919 may be preferably used for preparing the mixed ester used for the present invention, which mixed ester is formed from pentaerythritol , at least one C6-C3o fatty alcohol, citric acid, and at least one C6-C30 fatty acid.
[0025]
Such a mixed ester used for the present invention may also be prepared by esterification between at least one ester being formed from at least one C6~C3o fatty acid and pentaerythritol and having two or more hydroxyl groups per molecule and at least one ester being formed from at least one C6-C30 fatty alcohol and citric acid and having one or more carboxylic acid groups per molecule using the method as disclosed in GB 962,919.
[0026]
The aforementioned C6-C30 fatty acid esters of
pentaerythritol or a mixture thereof may be used alone as component (iii) . However, it is also possible to use at least two esters and particularly to use at least one ester formed from at least one C6-C30 fatty acid and pentaerythritol according to the first embodiment in combination with at least one ester according to the second embodiment.
[0027]
A preferred amount of component (iii) is in the range 0.01 to 5 % by weight, preferably 0.05 to 1%, more preferably 0.08 to 0.5% relative to the total amount of the composition. The weight ratio of component (ii) to component (iii) in the composition is preferably in the range of 1:4 to 4:1, in particular 1:2 to 2:1. Using components (ii) and (iii) in this ratio in the composition, cosmetic and conditioning effects on keratin fibres achieved by using the composition can be further improved. That is, by using components (ii) and (iii) in the aforementioned ratio in the composition, good flexible and silky feeling can be imparted to keratin fibres such as the hair.
[0028]
The molar ratio of at least one ester according to the first embodiment to at least one ester according to the second embodiment are preferably from 1:2 to 2:1, most preferably 1:1, when these two kinds of materials are used in combination as component (iii) of the present invention . Using these two kinds of esters in a molar ratio as described above, very good cosmetic and high conditioning effects on keratin fibres can be achieved.
[0029]
As component (iii) of the present invention, mixed esters formed from pentaerythritol, at least one 063ο fatty alcohol, citric acid, and at least one C6-C30 fatty acid, which are represented by formula (I) where Rl represents a Z group, are most preferably used.
[0030]
In connection with the ester compounds derived from pentaerythritol as described above, cocoyl fatty acid is most preferably used as the C6-C3o fatty acid and stearyl alcohol is most preferably used as the C6-C30 fatty alcohol, but not limited thereto.
[0031]
The ester compound most preferably used as component (iii) in the composition of the present invention is the product whose INCI name is Dicocoyl Pentaerythrityl Distearyl Citrate, which is commercially available under the tradename of Cutina® Shine manufactured by Cognis. Therefore, it is preferred that component (iii) of the composition of the present invention consists of or comprises Dicocoyl Pentaerythrityl Distearyl Citrate in order to achieve good cosmetic and conditioning effects on keratin fibres.
[0032]
Using Dicocoyl Pentaerythrityl Distearyl Citrate in a hair care products may have already been known. However, it was not known that the use of Dicocoyl Pentaerythrityl Distearyl Citrate in combination with behenyl alcohol or a mixture of fatty alcohol comprising behenyl alcohol in addition to a surfactant can impart good cosmetic and conditioning effects to a composition for cleansing keratin fibres even if silicones and/or silicone derivatives commonly used for hair care products are not used or the amount thereof is reduced. The cosmetic and conditioning effects provided on keratin fibers by the present invention may be better than the effects of a conventional composition for cleansing keratin fibres comprising silicones such as dimethicone and/or silicone derivatives such as amodimethicone .
[0033]
[Surfactants]
The composition of the present invention comprises at least one surfactant as a component (i) . It is possible to use one or more surfactants selected from any types of surfactants which can be used for compositions for cleansing keratin fibres . As such surfactants which may be suitably used for the present invention, mention may be made of anionic surfactants, nonionic surfactants, amphoteric or zwitterionic surfactants, and cationic surfactants, which are described in more details below. However, it is preferable to employ anionic surfactants or to employ anionic surfactants in combination with one or more selected from the group consisting of amphoteric surfactants and nonionic surfactants as component (i) of the composition of the present invention in order to provide good cleansing power as well as desirable cosmetic and conditioning effects on keratin fibers.
[0034]
(A) Anionic Surfactant ( s )
It is preferable that the anionic surfactant be selected from the group consisting of (Ce-C3o) alkyl sulfates,
(C6-C3o) alkyl ether sulfates, (C6-C30) alkylamido ether sulfates, alkylaryl polyether sulfates, monoglyceride sulfates;
(C6-C30) alkylsulfonates, (C6-C3o) alkylamide sulfonates,
(C6-C3o) alkylaryl sulfonates, -olefin sulfonates, paraffin sulfonates; (C6-C3o) alkyl phosphates; (C6-C30) alkyl
sulfosuccinates , (C6-C3o) alkyl ether sulfosuccinates ,
(C6~C3o) alkylamide sulfosuccinates ; (C6-C30) alkyl
sulfoacetates; (C6-C24)acyl sarcosinates ; (C6-C24)acyl
glutamates; (C6-C30) alkylpolyglycoside carboxylic ethers.;
(C6-C30) alkylpolyglycoside sulfosuccinates ; (C6-C3o) alkyl sulfosuccinamates ; (Cg-C24)acyl isethionates ; N- (C6-C24) acyl taurates; C6_C3o fatty acid salts; coconut oil acid salts or hydrogenated coconut oil acid salts; (C3-C2o)acyl lactylates;
(C6-C30) alkyl-D-galactoside uronic acid salts;
polyoxyalkylenated (C6-C30 ) alkyl ether carboxylic acid salts; polyoxyalkylenated (C6-C30) alkylaryl ether carboxylic acid salts; polyoxyalkylenated (C6-C3o) alkylamido ether carboxylic acid salts ; and corresponding acids.
[0035]
It is more preferable that the anionic surfactant be selected from salts of (C3-C30) alkyl sulfate or
polyoxyalkylenated (C6-C30) alkyl ether carboxylic acid salts.
[0036]
In at least one embodiment, the anionic surfactants are in the form of salts such as salts of alkali metals, for instance sodium; salts of alkaline-earth metals , for instance magnesium; ammonium salts; amine salts; and amino alcohol salts.
[0037]
(B) Nonionic Surfactant ( s )
The nonionic surfactants themselves are also compounds which are well known per se (in this respect see especially the "Handbook of Surfactants" by M. R. Porter, published by Blackie & Son (Glasgow and London), 1991, pp. 116-178, the disclosure of which is incorporated by reference) . Thus, they can, for example, be chosen from alcohols , alpha-diols, alkylphenols and esters of fatty acids that are polyethoxylated,
polypropoxylated or polyglycerolated and have at least one fatty chain comprising, for example, from 8 to 18 carbon atoms, it being possible for the number of ethylene oxide or propylene oxide groups to range from 2 to 50, and for the number of glycerol groups to range from 2 to 30. Maltose derivatives may also be mentioned. Non-limiting mention may also be made of copolymers of ethylene oxide and/or of propylene oxide; condensates of ethylene oxide and/or of propylene oxide with fatty alcohols; polyethoxylated fatty amides comprising, for example, from 2 to 30 mol of ethylene oxide; polyglycerolated fatty amides comprising, for example, from 1 to 5 glycerol groups, such as from 1.5 to 4; ethoxylated fatty acid esters of sorbitan comprising from 2 to 30 mol of ethylene oxide; ethoxylated oils from plant origin; fatty acid esters of sucrose; fatty acid esters of polyethylene glycol; fatty acid mono or diesters of glycerol; (C6-C24) alkylpolyglycosides ;
N- (C6-C24 ) alkylglucamine derivatives, amine oxides such as (C10-C14) alkylamine oxides or
N- (C10-C14 ) acylaminopropylmorpholine oxides; and mixtures thereof.
[0038]
The nonionic surfactants may be chosen from
monooxyalkylenated or polyoxyalkylenated, monoglycerolated or polyglycerolated nonionic surfactants.. The oxyalkylene units are more particularly oxyethylene or oxypropylene units, or a combination thereof, preferably oxyethylene units.
[0039]
Examples of oxyalkylenated nonionic surfactants that may be mentioned include:
oxyalkylenated (C8-C24) alkylphenols ,
saturated or unsaturated, linear or branched, oxyalkylenated C8-C30 alcohols,
saturated or unsaturated, linear or branched, oxyalkylenated C8-C30 amides,
esters of saturated or unsaturated, linear or branched, C8-C30 acids and of polyethylene glycols,
polyoxyalkylenated esters of saturated or unsaturated, linear or branched, C8-C3o acids and of sorbitol,
saturated or unsaturated, oxyalkylenated plant oils, condensates of ethylene oxide and/or of propylene oxide, inter alia, alone or as mixtures.
[0040]
The surfactants may contain a number of moles of ethylene oxide and/or of propylene oxide of between 1 and 100 and preferably between 2 and 50. Advantageously, the nonionic surfactants do not comprise any oxypropylene units.
[0041]
In accordance with one preferred embodiment of the invention, the oxyalkylenated nonionic surfactants are chosen from oxyethylenated C8-C30 alcohols or ethoxylated fatty esters .
[0042]
It will be noted that alkylpolyglycosides constitute nonionic surfactants which are particularly well suited within the context of the present invention.
[0043]
(C) Amphoteric or Zwitterionic Surfactant ( s )
The amphoteric or zwitterionic surfactants can be, for example (nonlimiting list) , amine derivatives such as aliphatic secondary or tertiary amine, and optionally quaternized amine derivatives, in which the aliphatic radical is a linear or branched chain comprising 8 to 22 carbon atoms and containing at least one water-solubilizing anionic group (for example, carboxylate, sulphonate, sulphate, phosphate or phosphonate) .
[0044]
The amphoteric surfactant may preferably be selected from the group consisting of betaines and amidoaminecarboxylated derivatives.
[0045]
The betaine-type amphoteric surfactant is preferably selected from the group consisting of alkylbetaines , alkylamidoalkylbetaines, sulfobetaines , phosphobetaines , and alkylamidoalkylsulfobetaines , in particular,
(C8-C24 ) alkylbetaines, (C8-C24 ) alkylamido (Ci-C8) alkylbetaines, sulphobetaines , and
( C8-C24) alkylamido (C.i-Cs) alkylsulphobetaines . In one
embodiment, the amphoteric surfactants of betaine type are chosen from (C8-C24 ) alkylbetaines ,
(C8-C24 ) alkylamido (Ci-C8) alkylsulphobetaines, sulphobetaines, and phosphobetaines.
[0046]
Non-limiting examples that may be mentioned include the compounds classified in the CTFA dictionary, 9th edition, 2002, under the names cocobetaine, laurylbetaine, cetylbetaine , coco/oleamidopropylbetaine, cocamidopropylbetaine, palmitamidopropylbetaine, stearamidopropylbetaine,
cocamidoethylbetaine, cocamidopropylhydroxysultaine, oleamidopropylhydroxysultaine, cocohydroxysultaine,
laurylhydroxysultaine, and cocosultaine , alone or as mixtures .
[0047]
The betaine-type amphoteric surfactant is preferably an alkylbetaine and an alkylamidoalkylbetaine, in particular cocobetaine and cocamidopropylbetaine .
[0048]
Among the amidoaminecarboxylated derivatives, mention may be made of the products sold under the name Miranol, as described in U.S. Pat. Nos. 2,528,378 and 2,781,354 and classified in the CTFA dictionary, 3rd edition, 1982 (the disclosures of which are incorporated herein by reference) , under the names Amphocarboxyglycinates and
Amphocarboxypropionates , with the respective structures:
Rl-CONHCH2CH2-N+ (R2) (R3) (CH2COO-) in which:
Rl denotes an alkyl radical of an acid Rl-COOH present in hydrolysed coconut oil, a heptyl, nonyl or undecyl radical, R2 denotes a beta-hydroxyethyl group, and
R3 denotes a carboxymethyl group; and
Rl'-CONHCH2CH2-N(B) (C) in which:
B represents -CH2CH2OX',
C represents -(CH2)Z-Y', with z=l or 2,
X' denotes a -CH2CH2-COOH group, -CH2-COOZ', -CH2CH2-COOH, -CH2CH2-COOZ' or a hydrogen atom,
Y' denotes -COOH, -COOZ', -CH2-CHOH-S03Z' or a -CH2-CHOH-S03H radical,
Z' represents an ion of an alkaline or alkaline earth metal such as sodium, an ammonium ion or an ion derived from an organic amine, and
Rl' denotes an alkyl radical of an acid Rl'-COOH present in coconut oil or in hydrolysed linseed oil, an alkyl radical, such as a C7, C9, C or Ci3 alkyl radical, a Cn alkyl radical and its iso form, or an unsaturated Ci7 radical.
[0049]
It is preferable that the amphoteric surfactant be selected from (C8-C2 ) -alkyl amphomonoacetates , (C8-C24) alkyl amphodiacetates, (C8-C24 ) alkyl amphomonopropionates , and (C8-C24 ) alkyl amphodipropionates . These compounds are classified in the CTFA dictionary, 5th edition, 1993, under the names Disodium Cocoamphodiacetate, Disodium
Lauroamphodiacetate, Disodium Caprylamphodiace.tate, Disodium Capryloamphodiacetate, Disodium Cocoamphodipropionate, Disodium Lauroamphopropionate, Disodium
Caprylamphodipropionate, Disodium Caprylamphodipropionate, Lauroamphodipropionic acid and Cocoamphodipropionic acid.
[0050]
By way of example, mention may be made of the
cocoamphodiacetate sold under the trade name Miranol® C2M concentrate by the company Rhodia Chimie.
[0051]
(D) Cationic Surfactants
The cationic surfactant may be selected from the group consisting of optionally polyoxyalkylenated, primary, secondary or tertiary fatty amine salts, quaternary ammonium salts, and mixtures thereof.
[0052]
Examples of quaternary ammonium salts that may be mentioned include, but are not limited to:
those of general formula (II) below:
Figure imgf000020_0001
(ID
wherein
Rl, R2, R3, and R4 , which may be identical or different, are chosen from linear and branched aliphatic radicals comprising from 1 to 30 carbon atoms and optionally comprising heteroatoms such as oxygen, nitrogen, sulfur and halogens. The aliphatic radicals may be chosen, for example, from alkyl, alkoxy, C2-Ce polyoxyalkylene, alkylamide, ( C12 -C22 ) alkylamido (C2-C6) alkyl, ( C12-C22 ) alkylacetate and hydroxyalkyl radicals; and aromatic radicals such as aryl and alkylaryl; and X"" is chosen from halides, phosphates, acetates, lactates, ( C2-C6) alkyl sulfates and alkyl- or alkylaryl-sulfonates ;
quaternary ammonium salts of imidazoline, for instance those of formula (III) below:
Figure imgf000020_0002
(III)e
wherein:
R5 is chosen from alkenyl and alkyl radicals comprising from 8 to 30 carbon atoms, for example fatty acid derivatives of tallow or of coconut;
R6 is chosen from hydrogen, C1-C4 alkyl radicals, and alkenyl and alkyl radicals comprising from 8 to 30 carbon atoms; R7 is chosen from C1-C4 alkyl radicals;
R8 is chosen from hydrogen and C1-C4 alkyl radicals; and
X~ is chosen from halides , phosphates, acetates, lactates, alkyl sulfates, alkyl sulfonates, and alkylaryl sulfonates. In one embodiment, R5 and R6 are, for example, a mixture of radicals chosen from alkenyl and alkyl radicals comprising from 12 to 21 carbon atoms, such as fatty acid derivatives of tallow, R7 is methyl and R8 is hydrogen. Examples of such products include, but are not limited. to, Quaternium-27 (CTFA 1997) and
Quaternium-83 (CTFA 1997), which are sold under the names "Rewoquat®" W75, W90, W75PG and W75HPG by the company Witco; diquaternary ammonium salts of formula (IV):
Figure imgf000021_0001
(IV)
wherein :
R9 is chosen from aliphatic radicals comprising from 16 to 30 carbon atoms;
RIO is chosen from hydrogen or alkyl radicals comprising from 1 to 4 carbon atoms or a group (R16a) (Rl7a) (R18a) N+ (CH2) 3; Rll, R12, R13, R14, R16a, R17a, and R18a, which may be identical or different, are chosen from hydrogen and alkyl radicals comprising from 1 to 4 carbon atoms; and
X" is chosen fromhalides, acetates, phosphates, nitrates, ethyl sulfates, and methyl sulfates.
An example of one such diquaternary ammonium salt is FINQUAT CT-P of FINETEX ( Quaternium-89 ) or FINQUAT CT of FINETEX (Quaternium-75 ) ; and
quaternary ammonium salts comprising at least one ester function, such as those of formula (V) below:
Figure imgf000022_0001
wherein :
R22 is chosen from C1-C6 alkyl radicals and C1-C6 hydroxyalkyl and dihydroxyalkyl radicals;
R23 is chosen from:
the radical blow:
Figure imgf000022_0002
linear and branched, saturated and unsaturated C1-C22
hydrocarbon-based radicals R27, and hydrogen,
R25 is chosen from:
the radical below:
O
Figure imgf000022_0003
linear and branched, saturated and unsaturated C1-C6
hydrocarbon-based radicals R29, and hydrogen,
R24, R26, and R28, which may be identical or different, are chosen from linear and branched, saturated and unsaturated, C7-C2i, hydrocarbon-based radicals;
r, s, and t, which may be identical or different, are chosen from integers ranging from 2 to 6;
each of rl and tl, which may be identical or different, is 0 or 1, and r2+rl=2r and tl+2t=2t;
y is chosen from integers ranging from 1 to 10;
x and z, which may be identical or different, are chosen from' integers ranging from 0 to 10;
X~ is chosen from simple and complex, organic and inorganic anions; with the proviso that the sum x+y+z ranges from 1 to 15, that when x is 0, R23 denotes R27, and that when z is 0, R25 denotes R29. R22 may be chosen from linear and branched alkyl radicals. In one embodiment, R22 is chosen from linear alkyl radicals. In another embodiment, R22 is chosen from methyl, ethyl, hydroxyethyl, and dihydroxypropyl radicals , for example methyl and ethyl radicals. In one embodiment, the sum x+y+z ranges from 1 to 10. When R23 is a hydrocarbon-based radical R27, it may be long and comprise from 12 to 22 carbon atoms, or short and comprise from 1 to 3 carbon atoms. When R25 is a hydrocarbon-based radical R29, it may comprise, for example, from 1 to 3 carbon atoms. By way of a non-limiting example, in one embodiment, R24, R26, and R28, which may be identical or different, are chosen from linear and branched, saturated and unsaturated, C11-C21 hydrocarbon-based radicals, for example from linear and branched, saturated and unsaturated C11-C21 alkyl and alkenyl radicals. In another embodiment, x and z, which may be identical or different, are 0 or 1. In one embodiment, y is equal to 1. In another embodiment, r, s and t, which may be identical or different, are equal to 2 or 3, for example equal to 2. The anion X- may be chosen from, for example, halides, such as chloride, bromide, and iodide; and C1-C4 alkyl sulfates, such as methyl sulfate. However, methanesulfonate, phosphate, nitrate, tosylate, an anion derived from an organic acid, such as acetate and lactate, and any other anion that is compatible with the ammonium comprising an ester function, are other non-limiting examples of anions that may be used according to the invention. In one embodiment, the anion X- is chosen from chloride and methyl sulfate.
[0053]
In another embodiment, the ammonium salts of formula (V) may be used, wherein:
R22 is chosen from methyl and ethyl radicals,
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 radical below:
Figure imgf000024_0001
methyl, ethyl, and C14-C22 hydrocarbon-based radicals, hydrogen;
R25 is chosen from:
the radical below:
o
Figure imgf000024_0002
and hydrogen;
R24, R26, and R28, which may be identical or different, are chosen from linear and branched, saturated and unsaturated, C13-C17 hydrocarbon-based radicals, for example from linear and branched, saturated and unsaturated, C13-C17 alkyl and alkenyl radicals .
[0054]
In one embodiment, the hydrocarbon-based radicals are linear .
[0055]
Non-limiting examples of compounds of formula (V) that may be mentioned include salts, for example chloride and methyl sulfate, of diacyloxyethyl-dimethylammonium, of
diacyloxyethyl-hydroxyethyl-methylammonium, of
monoacyloxyethyl-dihydroxyethyl-methylammonium, of
triacyloxyethyl-methylammonium, of
monoacyloxyethyl-hydroxyethyl-dimethyl-ammonium, and mixtures thereof. In one embodiment, the acyl radicals may comprise from 14 to 18 carbon atoms, and may be derived, for example, from a plant oil, for instance palm oil and sunflower oil. When the compound comprises several acyl radicals, these radicals may be identical or different.
[0056]
These products may be obtained, for example, by direct esterification of optionally oxyalkylenated triethanolamine, triisopropanolamine, alkyldiethanolamine or
alkyldiisopropanolamine onto fatty acids or onto mixtures of fatty acids of plant or animal origin, or by transesterification of the methyl esters thereof. This esterification may be followed by a quaternization using an alkylating agent chosen from alkyl halides, for example methyl and ethyl halides; dialkyl sulfates, for example dimethyl and diethyl sulfates; methyl methanesulfonate; methyl para-toluenesulfonate; glycol chlorohydrin; and glycerol chlorohydrin .
[0057]
Such compounds are sold, for example, under the names Dehyquart® by the company Cognis, Stepanquat® by the company Stepan, Noxamium® by the company Ceca, and "Rewoquat® WE 18" by the company Rewo-Goldschmidt .
[0058]
Other non-limiting examples of ammonium salts that may be used in the compositions according to the invention include the ammonium salts comprising at least one ester function described in U.S. Pat. Nos . 4 , 874 , 554 and 4,137,180.
[0059]
Among the quaternary ammonium salts mentioned above that may be used in compositions according to the invention include, but are not limited to, those corresponding to formula (II), for example tetraalkylammonium chlorides, for instance dialkyldimethylammonium and alkyltrimethylammonium chlorides in which the alkyl radical comprises from about 12 to 22 carbon atoms, such as behenyltrimethylammonium,
distearyldimethylammonium, cetyltrimethylammonium and benzyldimethylstearylammonium chloride;
palmitylamidopropyltrimethylammonium chloride; and
stearamidopropyldimethyl (myristyl acetate) ammonium chloride, sold under the name "Ceraphyl® 70" by the company Van Dyk.
[0060]
According to one embodiment, the cationic surfactant that may be used in the compositions of the invention is chosen from quaternary ammonium salts, for example from behenyltrimethylammonium chloride, cetyltrimethylammonium chloride, Quaternium-83 , Quaternium-87 , Quaternium-22 , behenylamidopropyl-2 , 3-dihydroxypropyldimethylammonium chloride, palmitylamidopropyltrimethylammonium chloride, and stearamidopropyldimethylamine .
[0061]
For the present invention, it is preferred to use one or more anionic surfactants alone or in combination with one or more nonionic surfactants and/or amphoteric surfactants as described above. The amounts of the one or more surfactants contained in the composition of the present invention are not particularly limited as far as desired cleansing property of the composition is obtained.
[0062]
The amount of the surfactants contained in the composition of the present invention is not particularly limited. However, surfactants are commonly contained in a composition for cleansing keratin fibres of the present invention in the range from 4% to 50% by weight, preferably from 4% to 35% by weight of the total weight of the final composition. In a preferred embodiment anionic surfactants are contained in the composition according to the- invention in the range from 4% to 50% by weight, preferably from 4% to 35% by weight of the total weight of the composition.
[0063]
In order to avoid occurrence of sticky or waxy feeling in touch of the keratin fibres such as the hair, it is advantageous to employ anionic surfactants used as component (i) and the esters of pentaerythritol used as a component (iii) under the condition where the ratio of the total weight of anionic surfactants to the total weight of esters of pentaerythritol is within the range of 60:1 to 25:1; preferably of 50:1 to 30:1.
[0064]
The ratio of the total weight of surfactants (that is, the weight of all surfactants) used as component (i) to the total weight of esters of pentaerythritol used as component (iii) of the composition of the present invention is preferably in the range of 80 : 1 to 25 : 1. By using component (iii) in this ratio, unpleasant sticky and waxy feeling in touch of keratin fibres can be prevented.
[0065]
[Silicones and silicone derivatives which may be used for the present invention]
According to the present invention, good cosmetic and conditioning effects on keratin fibres may be achieved by using behenyl alcohol or fatty alcohols comprising behenyl alcohol as component (ii) and pentaerythritol fatty esters used as component (iii) in combination with surfactants used as component (i) even without employing silicones and/or silicone derivatives such as dimethicones and amodimethicones commonly used for hair care products. However, it is still possible to add such silicones and/or silicone derivatives in addition to components (ii) and (iii) . However, the amounts of silicones and/or silicone derivatives contained in the composition of the present invention can be reduced compared to the amounts usually employed in hair care products. Preferably, silicones and/or silicones derivatives are present in the composition in an amount of 0.5wt% or less, relative to the total amount of the composition, most preferably are absent from the composition (0% of silicones and silicone derivatives).
[0066]
Silicones which may be used for compositions for cleansing keratin fibres are disclosed, for example, from line 22 in columns 5 to line 14 in column 7 of US 6,511,671, which is incorporated herein by reference. The use of silicones such as dimethicone is well known in the art. In addition, the use of silicone derivatives such as amodimethicone for compositions for cleansing keratin fibres is also known in the art. The use of silicone derivatives for compositions for cleansing keratin fibres is disclosed, for example, from line 9 on page 23 to line 3 on page 28 of the English text of JP-A-2011-132241, which is incorporated herein by reference. At least one selected from silicones and silicone derivatives which are known in the art to be used in cosmetic compositions may also be employed in the composition of the present invention, if desired, in addition to the combination of aforementioned components (i) to (iii) of the present invention.
[0067]
[Other optional components of the composition]
One or more substances commonly used in a composition for cleansing keratin fibers may also be optionally added to the composition of the present invention. Such substances are shown below, but not limited thereto.
[0068]
The compositions according to the invention have a final pH generally ranging from 3 to 10. Preferably, the pH ranges from 4 to 9. The adjustment of the pH to the desired value may be carried out conventionally by addition of a base (organic or inorganic) to the composition, for example ammonium hydroxide, sodium hydroxide, sodium carbonate or a primary, secondary or tertiary (poly) amine, such as monoethanolamine, diethanolamine, triethanolamine, isopropanolamine or
1 , 3-propanediamine, or by addition of an inorganic or organic acid, preferably a carboxyli'c acid, such as, for example citric acid.
[0069]
The compositions according to the present invention may also contain viscosity-regulating agents such as electrolytes, or thickening agents. There may be mentioned in particular sodium chloride, sodium xylenesulphonate , scleroglucans , xanthan gums, fatty acid alkanolamides, alkyl ether carboxylic acid alkanolamides which are optionally oxyethylenated with up to 5 mol of ethylene oxide, such as the product marketed under the name AMINOL® A15 by the company CHEM Y, and natural or synthetic polymers such as cellulose derivatives (e.g hydroxyethyl cellulose) , xanthan gum or crosslinked
polyacrylic acids and crosslinked acrylic acid/ (Ci0-C3o) alkyl' acrylate copolymers. These viscosity-regulating agents are used in the compositions according to the invention in proportions which may be up to 10% by weight relative to the total weight of the composition.
[0070]
The compositions according to the invention may also contain up to 5% of pearlescent or opacifying agents which are well known in the state of the art, such as, for example, fatty chain-containing acylated derivatives, such as ethylene glycol or polyethylene glycol monostearates or distearates, fatty chain-containing ethers such as, for example, distearyl ether or 1- (hexadecyloxy) -2-octadecanol .
[0071]
The compositions according to the invention may of course further contain, in addition, all the customary adjuvants encountered in the field of compositions for cleansing keratin fibres such as shampoos, such as for example perfumes, preservatives, sequestrants , foam modifiers, colorants, moisturizing agents, antidandruff agents, antiseborrhoeic agents, sunscreens and the like.
[0072]
The compositions according to the invention may also optionally contain other agents which have the effect of improving the cosmetic properties of keratin fibres without, however, adversely impairing the stability of the compositions . There may be mentioned, in this respect, for example, cationic polymers such as polyquaternium-10 , polyquaternium-6, polyquaternium-7 , polyquaternium- , polyquaternium-37 , amphoteric polymers such as polyquaternium-22 , proteins, protein hydrolysates , ceramides, pseudoceramides , fatty acids with linear or branched (Ci6-C 0) chains such as
18-methyleicosanoic acid, hydroxy acids, vitamins, panthenol, and oil agents such as vegetable oils, synthetic oils and mixtures thereof. As other optional additives such as preservatives and antimicrobial agents, mention may be made of, for example, sodium benzoate, salicylic acid, caprylyl glycol and the like.
[0073]
[Formulation of the composition of the present invention]
The form of the composition is not limited to particular forms, and it may be in the form of any one of known forms of compositions for cleansing keratin fibres, for example, a solution, a suspension, an emulsion such as a W/O or 0/W emulsion, a gel, and the like.
[0074]
In one preferred embodiment of the composition of the present invention, fatty alcohols used as component (ii) , ester compounds used as component (iii) , and eventually oil agents are dispersed as fine particles in a aqueous medium, in particular water. Such fine particles may be formed by mixing an fatty phase containing components (ii) and (iii) and an aqueous phase at an appropriate temperature by using an apparatus such as a homo mixer which is conventionally used for dispersing fatty substances into an aqueous medium.
[0075]
The present invention is also directed to a use of a combination of components (ii) and (iii) to impart good cosmetic and conditioning effects to a composition comprising a surfactant, in particular anionic surfactant for cleansing keratin fibres, preferably where silicones such as dimethicones and/or silicone derivatives such as amodimethicones are not added to the composition or the amounts thereof are
significantly reduced compared to the amounts conventionally used .
[0076]
When the composition of the present invention is a.shampoo, it is preferably applied to wet keratin fibres such as the hair in an amount that is effective for washing them, and the lather generated by massaging or frictioning with the hands may then be removed, after an optional leave-on time, by rinsing with water, the operation possibly being repeated one or more times.
[0077] [Example]
The present invention is further described below based on a concrete example, but the present invention is not limited to the example.
Some of the raw materials used for the following concrete example are as follows:
Fatty alcohol: a mixture of behenyl alcohol (72 to 80% by weight), arachidyl alcohol and stearyl alcohol: LANETTE 22 available from COGNIS, with a melting point of approximately 69°C;
Pentaerythritol ester: dicocoyl pentaerythrityl distearyl citrate: CUTINA SHINE available from COGNIS;
Alkyl carboxylate: Laureth-5 carboxylate: AKYPO RLM 45CA available from KAO CHEMICALS;
Lauryl glucoside as an alkyl glucoside: PLANTAREN 1200 N UP available from COGNIS.
[0078]
[Example of a composition of the present invention]
A shampoo according to the present invention was prepared, whose formulation is as shown in Table 1.
[Table 1]
Example 1 : Shampoo
Figure imgf000031_0001
SALICYLIC ACID SALICYLIC ACID 0.20
JQC (HUAYIN)
PHARMACEUTICAL
GLYCOL DISTEARATE TEGIN BL 315 2.00
EVONIK GOLDSCHMIDT
SODIUM CHLORIDE TFC PUREX SODIUM 0.17
CHLORIDE MORTON SALT
FRAGRANCE 5276119 FLANELLE 0.50
MOD CC
IFF
LAURYL GLUCOSIDE PLANTAREN 1200 N UP 3.64 (2.0 AM) (a nonionic surfactant) COGNIS
BEHENYL, ARACHIDYL and LANETTE 22 0.20 (0.154 STEARYL ALCOHOL COGNIS AM behenyl (fatty alcohols) alcohol)
DICOCOYL CUTINA SHINE 0.30
PENTAERYTHRITYL COGNIS DISTEARYL CITRATE
(a pentaerythritol
ester)
CITRIC ACID CITRIC ACID An
MONOHYDRATE FINE appropriate GRANULAR amount
CITRIQUE BELGE
HEXYLENE GLYCOL HEXYLENE GLYCOL An
RHODIA appropriate amount
WATER Balance
[0079]
The protocol for preparation of the shampoo is as follows: 1. A mixture of behenyl, arachidyl and stearyl alcohols (LANETTE 22) and dicocoyl pentaerythrityl distearyl citrate (CUTINA SHINE) were dispersed in lauryl glucoside (PLANTAREN 1200 N UP) at 75 °C, followed by cooling to room temperature.
2. Glycol distearate (TEGIN BL 315) was dispersed in a part of sodium laureth sulfate (TEXAPON N 702) at 75°C, followed by cooling to room temperature.
3. The cooled mixtures prepared in steps 1 and 2 were added to a mixture of other raw materials, followed by mixing the resulting mixture to prepare a shampoo according to the present invention.
[0080]
[Evaluation of the shampoo thus prepared]
Stability of the shampoo stored for 2 months at 45°C was evaluated by visible inspection. The shampoo of the present invention was stable under the storage condition.
[0081]
[Evaluation of cosmetic and conditioning effects of the shampoo on the hair]
Panelists, after applying an appropriate amount of the shampoo to wet hair, foamed the shampoo and massaged the hair and scalp with the shampoo, followed by rinsing with water and drying.
Panelists reported that the shampoo imparted to the hair smoothness and discipline effects which are similar or better than those of a conventional shampoo comprising dimethicone instead of the combination of LANETTE 22 and CUTINA SHINE.

Claims

Claims
1. A composition for cleansing keratin fibres, characterized by comprising
(i) at least one surfactant,
(ii) at least one fatty alcohol selected from the group consisting of behenyl alcohol and a mixture of fatty alcohols comprising behenyl alcohol, and
(iii) at least one ester of pentaerythritol comprising at least one C6-C30 fatty chain.
2. The composition of Claim 1, characterized in that the ester compound (iii) is selected from the group consisting of a C6-C30 fatty acid ester of pentaerythritol; and a mixed ester formed from pentaerythritol, at least one C6~C3o fatty alcohol, citric acid, and at least one C6-C30 fatty acid.
The composition of Claim 1 or 2, characterized in that the ter compound (iii) is selected from compounds of formula (I) :
Figure imgf000034_0001
in which:
R2, R3, and R4 are identical or different, and independently represent a hydrogen atom, a C6-C30 alkyl or a C6-C30 alkenyl group, wherein these alkyl or alkenyl groups are linear, branched, cyclic or mixed groups thereof; pi and p2 are independently equal to 0 or 1; and Rl represents a.C6-C30 alkyl or a C6-C30 alkenyl group or a Z group of formula (1-2) :
Figure imgf000035_0001
in which R' and R" are identical or different, and independently represent a C6-C30 alkyl or a 063ο alkenyl group, wherein the alkyl or alkenyl groups of Rl and Z are linear, branched, cyclic or mixed and * is the contact point with the rest of formula (I) .
4. The composition of Claim 3, characterized in that the ester (iii) is a compound of formula (I) with Rl equal to Z, particularly is dicocoyl pentaerythrityl distearyl citrate.
5. The composition of Claim 3, characterized in that the esters (iii) are di-C6-C22 fatty acid ester of pentaerythritol , tetra-C6-C22 fatty acid ester of pentaerythritol or a mixture thereof.
6. The composition of any one of Claim 1 to 5, characterized in that the amount of behenyl alcohol as component (ii) is in the range 0.01 to 5 % by weight , preferably 0.03 to 1%, more preferably 0.05 to 0.5% relative to the total amount of the composition.
7. The composition of any one of Claim 1 to 6, characterized in that if a mixture of fatty alcohols is used, then behenyl alcohol represents at least 25% by weight of the total weight of the mixture.
8. The composition of any one of Claim 1 to 7, characterized in that the amount of ester components (iii) is in the range 0.01 to 5 % by weight , preferably 0.05 to 1%, more preferably 0.08 to 0.5% relative to the total weight of the composition.
9. The composition of any one of Claim 1 to 8, characterized in that the surfactants are one or more surfactants selected from anionic, non ionic, cationic or amphoteric surfactants, preferably from anionic surfactants eventually associated with one or more of amphoteric and/or nonionic surfactants.
10. The composition of any one of Claim 1 to 9, characterized in that it contains anionic surfactants in the range from 4% to 50% by weight, preferably from 4% to 35% by weight of the total weight of the final composition.
11. The composition of any one of Claim 1 to 10, characterized in that it contains anionic surfactants, and that the ratio of the total weight of the anionic surfactants to the total weight of the esters of pentaerythritol is within the range of 60:1 to 25:1.
12. The composition of any one of Claim 1 to 11, characterized in that the ratio of the total weight of the surfactants used as component (i) to the total weight of the esters of pentaerythritol used as component (iii) of the composition of the present invention is preferably in the range of 80 : 1 to 25 : 1.
13. The composition of any one of Claim 1 to 12, characterized in that the ratio of the weight of behenyl alcohol used as component (ii) to the total weight of pentaerythritol esters used as component (iii) in the composition is in the range of 1:4 to 4:1, in particular 1:2 to 2:1.
14. The composition of any one of Claims 1 to 13, characterized in that silicones and silicone derivatives are present in an amount of 0.5 wt% or less relative to the total weight of the composition .
15. The composition of any one of Claims 1 to 14, characterized by comprising at least one cationic polymer.
PCT/JP2012/057655 2012-03-16 2012-03-16 A composition for cleansing keratin fibres WO2013136535A1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2014539180A JP2015515444A (en) 2012-03-16 2012-03-16 Keratin fiber cleaning composition
CN201280070920.XA CN104135991A (en) 2012-03-16 2012-03-16 A composition for cleansing keratin fibres
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CN107708658A (en) * 2015-06-25 2018-02-16 莱雅公司 Pearly-lustre base-material and the composition for including it

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