WO2022118983A1 - Compositions pour fibres kératiniques - Google Patents

Compositions pour fibres kératiniques Download PDF

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Publication number
WO2022118983A1
WO2022118983A1 PCT/JP2021/044606 JP2021044606W WO2022118983A1 WO 2022118983 A1 WO2022118983 A1 WO 2022118983A1 JP 2021044606 W JP2021044606 W JP 2021044606W WO 2022118983 A1 WO2022118983 A1 WO 2022118983A1
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Prior art keywords
weight
dimethylamine
ester
composition
composition according
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PCT/JP2021/044606
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English (en)
Inventor
Patrick Minou
Yoshiki Shibuya
Yi-Yun TSAO
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L'oreal
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Priority claimed from FR2100180A external-priority patent/FR3118709B1/fr
Application filed by L'oreal filed Critical L'oreal
Publication of WO2022118983A1 publication Critical patent/WO2022118983A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/416—Quaternary ammonium compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners

Definitions

  • the present invention relates to a composition for treating, such as conditioning, keratin fibers such as hair.
  • hair conditioning effects are very important properties.
  • a variety of leave-on type and rinse-off type hair care cosmetic products have been used for conditioning hair.
  • WO 2000/07562 and WO 2000/07563 discloses a cosmetic composition for hair comprising cationic surfactants.
  • An objective of the present invention is to provide a composition which can provide keratin fibers such as hair with improved conditioning effects, in particular higher strength of keratin fibers.
  • composition for treating keratin fibers comprising:
  • the (a) cationic surfactant may be represented by the following general formula (V): wherein
  • Ri, R2, R3, and R4 which may be identical or different, are chosen from linear and branched aliphatic groups, preferably alkyl groups, comprising from 1 to 30 carbon atoms and optionally comprising heteroatoms such as oxygen, nitrogen, sulfur and halogens; and X' is chosen from halides, phosphates, acetates, lactates, (Ci-Ce) alkyl sulfates and alkyl- or alkylaryl-sulfonates.
  • the (a) cationic surfactant may be represented by the following general formula (IX) with a combination with acidifying agents:
  • R is a hydrocarbon radical containing at least 6 carbon atoms, preferably from 8 to 30 carbon atoms, more preferably from 12 to 24 carbon atoms;
  • R’ is a divalent hydrocarbon radical containing less than 6 carbon atoms, preferably 2 or 3 carbon atoms;
  • R is H or a hydrocarbon radical containing less than 6 carbon atoms.
  • the (a) cationic surfactant may be selected from behentrimonium chloride, cetrimonium chloride, behentrimonium methosulfate, cetrimonium methosulfate, oleamidopropyl dimethylamine, stearamidopropyl dimethylamine, isostearamidopropyl dimethylamine, stearamidoethyl dimethylamine, lauramidopropyl dimethylamine, myristamidopropyl dimethylamine, behenamidopropyl dimethylamine, dilinoleamidopropyl dimethylamine, palmitamidopropyl dimethylamine, ricinoleamindopropyl dimethylamine, soyamidopropyl dimethylamine, wheat germamidopropyl dimethylamine, sunflowerseedamidopropyl dimethylamine, almondamidopropyl dimethylamine, avocadoamidopropyl dimethylamine, babassuamidopropyl dimethylamine
  • the amount of the (a) cationic surfactant(s) in the composition according to the present invention may be from 0.1% to 15% by weight, preferably from 0.5% to 10% by weight, and more preferably from 1% to 5% by weight, relative to the total weight of the composition.
  • ester of polyol(s) and of fatty diacid dimer, or an ester thereof may be selected from the esters of the following general formula (I):
  • CORiCO represents a fatty diacid dimer residue
  • OR2O represents a fatty alcohol dimer residue
  • OR3 represents a hydrocarbon-based monoalcohol residue, and n is an integer ranging from 1 to 15, or the following general formula (II): in which: n is an integer ranging from 1 to 15,
  • COR' i CO represents a fatty diacid dimer residue
  • OR'iO represents a diglyceryl residue of the following general formula (III): in which:
  • R'3 represents H or OR'3 represents a fatty acid residue, or the following general formula (IV):
  • ORi 'O represents a diol dimer residue obtained by hydrogenation of a dimerdilinoleic acid
  • COR2"CO represents a fatty diacid dimer residue
  • h represents an integer ranging from 1 to 9.
  • the (b) ester of polyol(s) and of fatty diacid dimer, or an ester thereof may be selected from the group consisting of the esters having the following INCI nomenclature: polyglyceryl-2 isostearate/dimerdilinoleate copolymer, bis-behenyl/isostearyl/phytosteryl dimerdilinoleyl dimerdilinoleate, dimerdilinoleyl dimerdilinoleate, and mixtures thereof.
  • the amount of the (b) ester(s) of polyol(s) and of fatty diacid dimer, or ester(s) thereof, in the composition according to the present invention may be from 0.5% to 20% by weight, preferably from 0.5% to 15% by weight, more preferably from 0.5% to 10% by weight, and even more preferably from 0.5% to 5% by weight, relative to the total weight of the composition.
  • composition according to the present invention may further comprise (c) at least one aminosilicone.
  • the (c) aminosilicone may have a degree of polymerization of less than 2,000.
  • composition according to the present invention may further comprise (e) water.
  • composition according to the present invention may further comprise (f) at least one fatty alcohol.
  • composition according to the present invention may further comprise (g) at least one oligomer of a triglyceride of hydroxylated fatty acid and of a saturated diacid.
  • composition according to the present invention may be a cosmetic composition, preferably a rinse-off type cosmetic composition, and more preferably a rinse-off type hair cosmetic composition.
  • the present invention also relates to a cosmetic process for caring for or conditioning keratin fibers, preferably hair, comprising the step of: applying onto the keratin fibers the composition according to the present invention.
  • the present invention also relates to a use of
  • Figure 1 shows a schematic view of how to determine bending angles for Examples 1-5 and Comparative Example 1.
  • the present invention mainly relates to a composition for treating keratin fibers comprising:
  • the present invention can provide keratin fibers such as hair with improved conditioning effects, in particular higher strength of keratin fibers.
  • composition according to the present invention can also provide keratin fibers with improved smoothness.
  • the present invention is useful for cosmetic treatment of keratin fibers, preferably for conditioning of keratin fibers, and more preferably for providing keratin fibers with higher strength and smoothness.
  • the composition according to the present invention can also provide keratin fibers with good cosmetic effects such as improved strength, e.g., increase in bending force, smooth feeling to the touch, and easy combing.
  • the “keratin fibers” here mean fibers which include at least one keratin substance. It is preferable that at least a part of the surface of the keratin fibers be formed by keratin substances. Examples of keratin fibers include hair, eyebrows, eyelashes, and the like. It is preferable that the present invention be used for treating hair.
  • composition for treating keratin fibers, such as hair comprising:
  • composition according to the present invention comprises (a) at least one cationic surfactant. Two or more types of cationic surfactants may be used in combination.
  • 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: those of general formula (V) below: wherein
  • Ri, R2, R3, and R4 which may be identical or different, are chosen from linear and branched aliphatic groups comprising from 1 to 30 carbon atoms and optionally comprising heteroatoms such as oxygen, nitrogen, sulfur and halogens.
  • the aliphatic groups may be chosen, for example, from alkyl, alkoxy, C2-C6 polyoxyalkylene, alkylamide, (C12- C22)alkylamido(C2-C6)alkyl, (Ci2-C22)alkylacetate and hydroxyalkyl grpups; and aromatic groups such as aryl and alkylaryl; preferably alkyl groups; and
  • X' is chosen from halides, phosphates, acetates, lactates, (Ci-Ce) alkyl sulfates and alkyl- or alkylaryl-sulfonates; quaternary ammonium salts of imidazoline, for instance those of formula (VI) below: 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;
  • Re 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
  • R 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 Re 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 Rs is hydrogen.
  • R9 is chosen from aliphatic radicals comprising from 16 to 30 carbon atoms
  • Rio, R11, R12, R13, and R14 which may be identical or different, are chosen from hydrogen and alkyl radicals comprising from 1 to 4 carbon atoms;
  • X‘ is chosen from halides, acetates, phosphates, nitrates, ethyl sulfates, and methyl sulfates.
  • An example of one such diquatemary ammonium salt is propane tallow diammonium dichloride; and quaternary ammonium salts comprising at least one ester function, such as those of formula (VIII) below: wherein:
  • R22 is chosen from Ci-Ce alkyl radicals, and Ci-Ce hydroxyalkyl and dihydroxyalkyl radicals;
  • R23 is chosen from: the radical below: linear and branched, saturated and unsaturated C1-C22 hydrocarbon-based radicals R27, and hydrogen
  • R25 is chosen from: the radical below: linear and branched, saturated and unsaturated Ci-Ce hydrocarbon-based radicals R29, and hydrogen
  • 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 the 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 the 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 present invention.
  • the anion X' is chosen from chloride and methyl sulfate.
  • ammonium salts of formula (VIII) 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: methyl, ethyl, and C14-C22 hydrocarbon-based radicals, and hydrogen;
  • R25 is chosen from: the radical below: 9 and hydrogen; R-24, 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 (VIII) 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.
  • 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.
  • 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 quatemization 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 chlorohydrin.
  • 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 and diammonium salts include, for example, distearyldimethylammonium chloride, cetyltimethylammonium chloride (such as, for example, the products sold under the trade name Dehyquart A by Cognis, or Quartamin 60 W25 by Kao, or Genamin CTAC 25 by Clariant), behenyltrimethylammonium chloride (such as the products sold for example by Clariant under the trade name Genamin KDMP or Genamin BTLF, or by Evonik Goldschmidt under the name Varisoft BT 85), behentrimonium chloride, cetrimonium chloride, oleocetyldimethylhydroxyethylammonium chloride, behenoylhydroxypropyltrimethylammonium chloride (such as the product sold by Kao under the name Quartamin BTC 131 ) stearamidopropyld
  • fatty amine salt examples include, but are not limited to: those of general formula (IX) below with a combination with acidifying agents:
  • R is a hydrocarbon radical containing at least 6 carbon atoms, preferably from 8 to 30 carbon atoms, more preferably from 12 to 24 carbon atoms.
  • R can be linear or branched, acyclic or cyclic, saturated or unsaturated, aliphatic or aromatic, substituted or unsubstituted.
  • R is a linear or branched, acyclic alkyl or alkenyl group or an alkyl phenyl group; and
  • R’ is a divalent hydrocarbon radical containing less than 6 carbon atoms, preferably 2 or 3 carbon atoms, and
  • R is H or a hydrocarbon radical containing less than 6 carbon atoms.
  • R is linear or branched, acyclic or cyclic, saturated or unsaturated, substituted or unsubstituted.
  • R is a linear or branched, acyclic alkyl or alkenyl group.
  • R is H or a methyl group.
  • the cationic surfactant is selected from behentrimonium chloride, cetrimonium chloride, behentrimonium methosulfate, cetrimonium methosulfate, oleamidopropyl dimethylamine, stearamidopropyl dimethylamine, isostearamidopropyl dimethylamine, stearamidoethyl dimethylamine, lauramidopropyl dimethylamine, myristamidopropyl dimethylamine, behenamidopropyl dimethylamine, dilinoleamidopropyl dimethylamine, palmitamidopropyl dimethylamine, ricinoleamindopropyl dimethylamine, soyamidopropyl dimethylamine, wheat germamidopropyl dimethylamine, sunflowerseedamidopropyl dimethylamine, almondamidopropyl dimethylamine, avocadoamidopropyl dimethylamine, babassuamidopropyl dimethylamine
  • the amount of the (a) cationic surfactant in the composition according to the present invention may be 0.1% by weight or more, preferably 0.3% by weight or more, and more preferably 0.5% by weight or more, relative to the total weight of the composition.
  • the amount of the (a) cationic surfactant in the composition according to the present invention may be 15% by weight or less, preferably 10% by weight or less, and more preferably 5% by weight or less, relative to the total weight of the composition.
  • the amount of the (a) cationic surfactant in the composition according to the present invention may range from 0.1% to 15% by weight, preferably from 0.3% to 10% by weight, and more preferably from 0.5% to 5% by weight, relative to the total weight of the composition.
  • composition according to the present invention comprises (b) at least one ester of polyol(s) and of fatty diacid dimer, or an ester thereof. If two or more esters of polyol(s) and of fatty diacid dimer, or ester(s) thereof are used, they may be the same or different.
  • esters of polyol(s) and of fatty diacid dimer or an ester thereof'
  • the term "or an ester thereof means one of the derivatives of these esters and of polyol(s) and of fatty diacid dimer obtained either by reaction of alcohol function(s) of the polyol, not engaged in bonds of ester type with acid functions of the diacid dimer, with one or more carboxylic functions of acid molecules other than the diacid dimer, or alternatively by reaction of acid function(s) of the diacid dimer, not engaged in bonds of ester type with alcohol functions of the polyol, with alcohol functions of alcohol molecules other than the polyol.
  • esters of polyol(s) and of fatty diacid dimer, or an ester thereof, which are suitable for use in the present invention may have a viscosity, measured at about 25°C of greater than or equal to about 1 ,500 mPa.s.
  • the viscosity of an ester of polyol(s) and of fatty diacid dimer, or an ester thereof, according to the present invention may be measured according to any process known to those skilled in the art, and for example according to the conventional process described hereinbelow.
  • the viscosity may be measured using a cone/plate or parallel plate viscometer of Ares type (TA-Instrument) operating in kinetic sweep mode over a shear range of about 1-1,000 s’ 1 to induce a flow tension of about 1 ,000 Pa.
  • Ares type TA-Instrument
  • the cone/plate or parallel plates may consist of a material selected from the group consisting of stainless steel, acrylic resins or polyphenylene sulfide (PPS resin).
  • the cone/plate diameter may be 25 mm (cone angle 0.10 radians).
  • the measurement is performed at about 25°C.
  • the stability of the sample is checked by means of the dynamic sweep period test, which makes it possible to determine if the sample is stable per se.
  • the shear viscosity is determined using the ETA value in the plateau region according to the flow.
  • the dynamic sweep period is determined at a frequency of 1.0 Hz over a period of 600 seconds.
  • the measurements at constant sweep rate are performed with a rate ranging from 1.0 to 1,000 s' 1 and for example from 1.0 to 100 s’ 1 .
  • the viscosity of an ester of polyol(s) and of fatty diacid dimer, or an ester thereof, suitable for use in the present invention may range from about 1,500 mPa.s to about 150,000 mPa.s, or for example from about 2,000 mPa.s to about 150,000 mPa.s, or for example from about 15,000 mPa.s to about 100,000 mPa.s or for example from about 30,000 mPa.s to about 80,000 mPa.s.
  • a polyol that is suitable for use in the present invention may be a diol dimer.
  • esters of diol dimer and of fatty diacid dimer that may be used in the context of the present invention are commercially available or may be prepared in a conventional manner. They may be of plant origin and may be obtained by esterification of diacid dimers with diol dimers.
  • a polyol dicarboxylate In an esterification reaction with a diacid dimer, a polyol dicarboxylate is obtained, which may have a weight-average molecular weight, determined by gel permeation chromatography (GPC), ranging from 2,000 to 25,000 g/mol or for example between 2,000 and 4,000 g/mol.
  • GPC gel permeation chromatography
  • the fatty diacid dimers, or diacid dimers may be conventionally obtained by polymerization reaction, for example by intermolecular dimerization, of at least one unsaturated fatty acid.
  • They may contain at least two carboxylic acid groups.
  • carboxylic functions of the fatty diacid dimer not engaged in the ester bond with the polyol residue(s) may be engaged in other ester bonds with other alcohol functions of alcohol molecules other than the polyol(s).
  • These alcohol molecules or residues may be monoalcohols or polyols.
  • hydrocarbon-based compounds comprising a hydroxyl function and containing from 4 to 40 carbon atoms, or for example from 6 to 36 carbon atoms, or for example from 8 to 32 carbon atoms, or for example from 16 to 28 carbon atoms, or for example from 18 to 24 carbon atoms.
  • monoalcohols that are suitable for the present invention, mention may be made, in a non-limiting manner, of butanol, pentanol, propanol, hexanol, heptanol, octanol, decanol, dodecanol, hexadecanol, octadecanol, eicosadecanol, phytosterol, isostearol, stearol, cetol, behenol, etc.
  • the fatty diacid dimers may be derived for example from the dimerization of an unsaturated fatty acid, for example of Cs to C34, or for example of C12 to C22, in particular of Ci6 to C20 and for example of Cis.
  • unsaturated fatty acids mention may be made for example of undecenoic acid, linderic acid, myristoleic acid, palmitoleic acid, oleic acid, linoleic acid, elaidinic acid, gadolenoic acid, eicosapentaenoic acid, docosahexaenoic acid, erucic acid, brassidic acid and arachidonic acid, and mixtures thereof.
  • it may be the diacid dimer from which the diol dimer to be esterified may also be derived. It may be its hydrogenated form.
  • the hydrogenated form of the diacid dimer may be partial or total, and may correspond, for example, to the saturated form, which is more stable towards oxidation. According to another embodiment variant, it may be the diacid dimer derived from the dimerization of linoleic acid.
  • the diacid dimer may be a commercial product consisting of a dicarboxylic acid containing about 36 carbon atoms. This product may also contain a trimeric acid and a monomeric acid, in proportions that depend on the degree of purity of the product.
  • Diacid dimers and for example dilinoleic diacids whose stability towards oxidation has been improved by hydrogenation of the double bonds remaining after the dimerization reaction, may also be found commercially.
  • any diacid dimer that is currently commercially available may be used.
  • the average degree of esterification and the average molecular weight of the ester obtained may be adjusted by varying the ratio of the diol dimer to the diacid dimer.
  • polyol is intended to denote any hydrocarbon-based compound comprising at least two hydroxyl functions and containing from 4 to 40 carbon atoms, or for example from 6 to 36 carbon atoms, or for example from 8 to 32 carbon atoms, or for example from 16 to 28 carbon atoms and for example from 18 to 24 carbon atoms.
  • the hydrocarbon-based chains may be interrupted, where appropriate, by the presence of at least one heteroatom, and for example an oxygen atom.
  • a polyol or a polyol ester that is suitable for use in the present invention may comprise, for example, from 2 to 12 hydroxyl functions, or for example from 2 to 8 hydroxyl functions, or for example from 4 to 6 hydroxyl functions.
  • the hydroxyl functions other than those already employed in an ester bond with the diacid dimer, may also be employed, wholly or partly in other ester bonds via reaction with acid molecules other than the diacid dimer.
  • the polyol or an ester thereof that is suitable for use in the present invention may be selected from the group consisting of linear, branched, cyclic or polycyclic, saturated or unsaturated alcohols.
  • the polyol may be selected, for example, from the group consisting of a diol, a triol, a tetraol, or a pentaol, or an ester thereof.
  • the polyol may be a diol, or an ester thereof, selected for example from the group consisting of a fatty alcohol dimer, a monoglycerol or polyglycerol, a C2-C4 monoalkylene or polyalkylene glycol, 1 ,4-butanediol and pentaerythritol.
  • diols that are also suitable for use in the present invention, mention may be made, in a non-exhaustive manner, of butanediol, pentanediol, propanediol, hexanediol, hexylene glycol, heptanediol, octanediol, nonanediol, decanediol, 1 -decanediol, dodecanediol, tridecanediol, tetradecanediol, pentadecanediol, hexadecanediol, nonadecanediol, octadecanediol, cyclohexanediol, diglycerol, erythritol, pentaerythritol, xylitol, sorbitol, ethylene glycol and xylene
  • diol dimers As an example of diols that are suitable for use in the present invention, mention may be made of diol dimers.
  • diol dimer is intended to mean saturated diols derived from the hydrogenation of the corresponding diacid dimers, a diacid dimer being as defined above, and for example a diacid dimer of at least one unsaturated fatty acid.
  • the industrially manufactured diol dimer also generally contains other components, for example a triol trimer, a monoalcohol and compounds of ether type, according to the degree of purification of the acid dimer and/or of the lower alcohol ester thereof, used as starting material.
  • a triol trimer for example a triol trimer, a monoalcohol and compounds of ether type, according to the degree of purification of the acid dimer and/or of the lower alcohol ester thereof, used as starting material.
  • products whose diol dimer content is greater than 70% may be used in the present invention.
  • a diol dimer of high purity such as a compound whose diol dimer content is greater than 90%.
  • a diol dimer may be produced by hydrogenation, for example catalytic hydrogenation, of a diacid dimer, which is itself obtained by dimerization of at least one unsaturated fatty acid.
  • a suitable fatty acid may be such as those mentioned previously, and for example of Cs to C34, or for example of C12 to C22, or for example of Ci6 to C20 and more particularly of Cis.
  • the diol dimer may be derived from the hydrogenation of dilinoleic diacid.
  • a diol dimer may be, for example, dilinoleol.
  • the diol dimer may generally be in a saturated form.
  • diol dimer that is suitable for use in the present invention, mention may be made for example of diglycerol.
  • This compound is a glycerol dimer resulting from the condensation of two molecules of glycerol, with the loss of a water molecule.
  • diglycerol denotes any isomer combination that can result from such a condensation, for instance linear isomers, branched isomers and, where appropriate, cyclic isomers resulting from an intramolecular dehydration of a diglycerol molecule.
  • the diglycerol may be obtained via any process known to those skilled in the art and especially those described in patent EP 0 750 848.
  • acid molecules that can interact with one or more hydroxyl functions of the polyol, not engaged in the ester bond with the diacid dimer, mention may be made, in a nonlimiting manner, of molecules derived from isostearic acid, behenic acid, phytostearic acid, stearic acid or cetylic acid.
  • An ester that is suitable for use in the present invention may be obtained by reacting a polyol or an ester thereof with a diacid dimer, and for example a dimerdilinoleic acid, in a molar ratio of about 1.0:0.2-1.
  • An ester that may be suitable for use in the present invention may be obtained by reacting a dimerdilinoleic acid with a dilinoleol and, where appropriate, at least one additional monoalcohol selected for example from the group consisting of behenol, isostearol, phytosterol, stearol and cetol, and mixtures thereof.
  • an ester used in the context of the present invention may be used in the form of a mixture of various esters, for example.
  • An ester that is suitable for use in the present invention may be obtained, for example, by reacting a glycerol, an isostearic acid and a dimerdilinoleic acid, for example in a molar ratio of 1.0:0.2-1.0:0.5-0.9.
  • esters of dimerdilinoleic acid and of polyol(s), or an ester thereof, suitable for the present invention mention may be made of the esters described in patent applications JP- A-2003-226609, JP-A-2004-256515 and JP-A-2005-179377.
  • An ester of polyol(s) and of fatty diacid dimer, or an ester thereof, suitable for use in the present invention may have a molecular weight ranging from about 2,000 to about 25,000 g/mol, for example from about 4,000 to about 20,000 g/mol, for example from about 5,000 to about 20,000 g/mol, for example from about 7,000 to about 15,000 g/mol and for example from about 8,000 to about 10,000 g/mol.
  • an ester in accordance with the present invention may comprise an alternating sequence of diacid dimer residue(s) and of residue(s) related to the said polyol(s), and for example to the said diol(s), the said polyols or diols being, for example, as defined above.
  • each of the two ends of the said sequence may bear, respectively, a unit OR' and OR" with R' and R" representing, independently of each other, a hydrogen atom or OR' and OR" representing, independently of each other, a C2 to C36, for example Cs to C24, for example C12 to C20 and for example Ci6 to Ci8 hydrocarbon based monoalcohol residue.
  • R' and R" may both represent a hydrogen atom.
  • OR' and OR" may both represent an identical or different hydrocarbon-based monoalcohol residue.
  • hydrocarbon-based monoalcohol residues OR' and OR" that may be suitable for the present invention, mention may be made of fatty alcohol residues.
  • esters of general formula (I), (II) or (IV) described below may be selected from the group consisting of esters of general formula (I), (II) or (IV) described below, or a mixture thereof.
  • an ester of polyol(s) and of fatty diacid dimer, or an ester thereof, that may be suitable for use in the present invention may have the general formula (I) below:
  • CORiCO represents a fatty diacid dimer residue
  • OR2O represents a fatty alcohol dimer residue
  • OR3 represents a hydrocarbon-based monoalcohol residue
  • n is an integer ranging from 1 to 15, for example from 2 to 10 or for example from 5 to 7.
  • CORiCO may represent a dimerdilinoleate residue.
  • OR2O may represent a dimerdilinoleyl residue.
  • OR3 may represent a hydrocarbon-based monoalcohol residue selected, for example, from the group consisting of behenyl, isostearyl and phytosteryl residues, and mixtures thereof.
  • ester of dimerdilinoleic acid and of polyol(s) and of fatty diacid dimer, or an ester thereof, that may be suitable for use in the present invention may for example have the general formula (II) below: in which: n is an integer ranging from 1 to 15, for example from 2 to 10 and in particular from 5 to 7,
  • COR'iCO represents a fatty diacid dimer residue
  • OR2O represents a diglyceryl residue of general formula (III) below: in which:
  • R'3 represents H or OR'3 represents a fatty acid residue.
  • COR'iCO may represent a dimerdilinoleate residue.
  • the fatty acid residue featured by OR'3 may be an isostearyl residue.
  • an ester of dimerdilinoleic acid and of polyol(s) and of fatty diacid dimer, or an ester thereof, which may be suitable for use in the present invention may be of formula (IV) below:
  • ORr O represents a diol dimer residue obtained by hydrogenation of a dimerdilinoleic acid
  • COR2 n CO represents a fatty diacid dimer residue
  • h represents an integer ranging from 1 to 9, for example from 2 to 8 and for example from 4 to 6.
  • COR 2 'GO may represent a dimerdilinoleate residue.
  • esters having the following INCI nomenclature: polyglyceryl-2 isostearate dimerdilinoleate copolymer, bis-behenyl/isostearyl/phytosteryl dimerdilinoleyl dimerdilinoleate, dimerdilinoleyl dimerdilinoleate and mixtures thereof.
  • Such compounds may be obtained, for example, under the reference Hailuscent ISDA (Kokyu Alcohol) and Plandool-G, Plandool-G7, Lusplan DD-DA5, Lusplan DD-DA7, PHY/IS-DA and Lusplan DD-DAS (Nippon Fine Chemical Company Ltd).
  • Lusplan DD-DA5 and Lusplan DD-DA7 are described in patent application FR 03/02809.
  • the amount of the (b) ester(s) of polyol(s) and of fatty diacid dimer, or ester(s) thereof, in the composition according to the present invention is 0.5% by weight or more.
  • the amount of the (b) ester(s) of polyol(s) and of fatty diacid dimer, or ester(s) thereof, in the composition according to the present invention may preferably be 1.0% by weight or more, more preferably 1.5% by weight or more, and even more preferably 2.0% by weight or more, relative to the total weight of the composition.
  • the amount of the (b) ester(s) of polyol(s) and of fatty diacid dimer, or ester(s) thereof, in the composition according to the present invention may be 20% by weight or less, preferably 15% by weight or less, more preferably 10% by weight or less, and even more preferably 5% by weight or less, relative to the total weight of the composition.
  • the amount of the (b) ester(s) of polyol(s) and of fatty diacid dimer, or ester(s) thereof, in the composition according to the present invention may range from 0.5% to 20% by weight, preferably from 0.5% to 15% by weight, more preferably from 0.5% to 10% by weight, and even more preferably from 0.5% to 5% by weight, relative to the total weight of the composition.
  • composition according to the present invention may farther comprise (c) at least one aminosilicone.
  • a single type of aminosilicone may be used, or two or more different types of aminosilicones may be used in combination.
  • the (c) aminosilicone may have a degree of polymerization of less than 2,000, preferably less than 1,500, and more preferably less than 1,000.
  • the degree of polymerization is the number of repeating units which form a polymer.
  • the degree of polymerization here represents an average value of degree of polymerization, preferably a number average value of degree of polymerization.
  • any aminosilicone compound in the field of cosmetics may be used.
  • aminosilicone here means a silicone comprising at least one primary, secondary or tertiary amine group or at least one quaternary ammonium group.
  • G independently designates a hydrogen atom, or a phenyl, OH, or a Ci-Cs alkyl group, for example methyl, or a Ci-Cs alkoxy group, for example methoxy, a and a' independently denote the number 0 or an integer from 1 to 3, in particular 0; b denotes 0 or 1 , and in particular 1 ; m and n are numbers such that the ,sum (n + m) ranges, for example, from 1 to less than 2,000 and in particular from 50 to 150, it being possible for n to denote a number from 0 to less than 1,999 and in particular from 49 to 149, and for m to denote a number, for example, from 1 to less than 2,000 and in particular from 1 to 10; R' independently denotes a monovalent group having formula -CqlfrqL in which q is a number ranging from 2 to 8 and L is an optionally quatemized amino group chosen from the following groups:
  • R" independently denotes hydrogen, phenyl, benzyl, or a saturated monovalent hydrocarbon-based group, for example a C1-C20 alkyl group;
  • Q denotes a linear or branched Cd r group, r being an integer ranging from 2 to 6, preferably from 2 to 4;
  • A" represents a cosmetically acceptable ion, in particular a halide such as fluoride, chloride, bromide or iodide.
  • a group of aminosilicones corresponding to this definition (B) is represented by the silicones called "trimethylsilylamodimethicone” having formula (C): in which n and m have the meanings given above in formula B.
  • silicones having the following formula (D) or (E): in which: m and n are numbers such that the sum (n + m) can range from 1 to 1,000, in particular from 50 to 250 and more particularly from 100 to 200, it being possible for n to denote a number from 0 to 999 and in particular from 49 to 249, and more particularly from 125 to 175, and for m to denote a number from 1 to 1,000 and in particular from 1 to 10, and more particularly from 1 to 5;
  • Ri, R2, and R3 independently represent a hydroxy or a C1-C4 alkoxy group, wherein at least one of the groups Ri to R3 denotes an alkoxy group.
  • the alkoxy group is preferably a methoxy group.
  • the hydroxy/alkoxy mole ratio ranges preferably from 0.2:1 to 0.4:1 and preferably from 0.25:1 to 0.35:1 and more particularly equals 0.3:1.
  • the weight-average molecular weight (Mw) of the silicone ranges preferably from 2,000 to 1,000,000, more particularly from 3,500 to 200,000.
  • p and q are numbers such that the sum (p + q) ranges from 1 to 1,000, particularly from 50 to 350, and more particularly from 150 to 250; it being possible for p to denote a number from 0 to 999 and in particular from 49 to 349, and more particularly from 159 to 239 and for q to denote a number from 1 to 1,000, in particular from 1 to 10, and more particularly from 1 to 5;
  • Ri and R.2 independently represent a hydroxy or C1-C4 alkoxy group, where at least one of the groups Ri or R2 denotes an alkoxy group.
  • the alkoxy group is preferably a methoxy group.
  • the hydroxy/alkoxy mole ratio ranges generally from 1 :0.8 to 1 :1.1 and preferably from 1 :0.9 to 1:1 and more particularly equals 1 :0.95.
  • the weight-average molecular weight (Mw) of the silicone ranges preferably from 2,000 to 200,000, even more particularly 5,000 to 100,000 and more particularly from 10,000 to 50,000.
  • silicones having structure (D) or (E) may include in their composition one or more other aminosilicones whose structure is different from formula (D) or (E).
  • a product containing aminosilicone having structure (D) is sold by Wacker under the name BELSILADM 652.
  • a product containing aminosilicone having structure (E) is sold by Wacker under the name FLUID WR 1300®.
  • n and n are numbers such that the sum (n + m) ranges from, for example, 1 to less than 2,000 and in particular from 50 to 150, it being possible for n to denote a number from 0 to less than 1,999 and in particular from 49 to 149, and for m to denote a number, for example, from 1 to less than 2,000 and in particular from 1 to 10;
  • A denotes a linear or branched alkylene group containing from 4 to 8 carbon atoms and preferably 4 carbon atoms. This group is preferably linear.
  • the weight-average molecular weight (Mw) of these aminosilicones ranges preferably from 2,000 to 1,000,000 and even more particularly from 3,500 to 200,000.
  • a preferred silicone of formula (F) is amodimethicone sold under the trade name XIAMETER® MEM-8299 Cationic Emulsion by Dow Coming.
  • G Another group of aminosilicones corresponding to this definition is represented by the following formula (G): in which: m and n are numbers such that the sum (n + m) ranges, for example, from 1 to less than 2,000 and in particular from 50 to 150, it being possible for n to denote a number from 0 to less than 1,999 and in particular from 49 to 149, and for m to denote a number, for example, from 1 to less than 2,000 and in particular from 1 to 10;
  • A denotes a linear or branched alkylene group containing from 4 to 8 carbon atoms and preferably 4 carbon atoms. This group is preferably branched.
  • the weight-average molecular weight (Mw) of these aminosilicones ranges preferably from 500 to 1,000,000 and even more particularly from 1,000 to 200,000.
  • a silicone having this formula is for example DC2-8566 Amino Fluid by Dow Coming.
  • Rs independently represents a monovalent hydrocarbon-based group containing from 1 to 18 carbon atoms, and in particular a Ci-Cis alkyl or C2-C18 alkenyl group, for example methyl;
  • R6 represents a divalent hydrocarbon-based group, in particular a Ci-Cis alkylene group or a divalent Ci-Cis, for example Ci-Cs, alkyleneoxy group linked to Si via an SiC bond;
  • Q' is an anion such as a halide ion, in particular chloride, or an organic acid salt (for example acetate); r represents a mean statistical value from 2 to 20 and in particular from 2 to 8; s represents a mean statistical value from 20 to 200 and in particular from 20 to 50.
  • R7 independently represents a monovalent hydrocarbon-based group containing from 1 to 18 carbon atoms, and in particular a Ci-Cis alkyl group, a C2-C18 alkenyl group or a ring containing 5 or 6 carbon atoms, for example methyl;
  • Re independently represents a divalent hydrocarbon-based group, in particular a Ci- Ci8 alkylene group or a divalent Ci-Cis, for example Ci-Cs, alkyleneoxy group linked to the Si via a SiC bond;
  • Rs independently represents a hydrogen atom, a monovalent hydrocarbon-based group containing from 1 to 18 carbon atoms, and in particular a C1-C18 alkyl group, a C2-C18 alkenyl group or a -R6-NHCOR7 group;
  • X is an anion such as a halide ion, in particular chloride, or an organic acid salt (for example acetate); r represents a mean statistical value from 2 to 200 and in particular from 5 to 100;
  • Ri, R2, R3 and R 4 independently denote a C1-C4 alkyl group or a phenyl group
  • R5 denotes a C1-C4 alkyl group or a hydroxy group; m is an integer ranging from 1 to 5; n is an integer ranging from 1 to 5; and in which x is chosen such that the amine number is between 0.01 and 1 meq/g;
  • Multiblock polyoxyalkylenated aminosilicone of type (AB) n , A being a polysiloxane block and B being a polyoxyalkylenated block containing at least one amine group.
  • Said silicones are preferably constituted of repeating units having the following general formula:
  • a is an integer greater than or equal to 1 , preferably ranging from 5 to 200, more particularly ranging from 10 to 100;
  • b is an integer comprised between 0 and 200, preferably ranging from 4 to 100, more particularly between from 5 and 30;
  • x is an integer ranging from 1 to 10,000, more particularly from 10 to 5,000;
  • R" is a hydrogen atom or a methyl
  • R independently represents a divalent linear or branched C 2 -Ci 2 hydrocarbon-based group, optionally including one or more heteroatoms such as oxygen; preferably, R independently denotes an ethylene group, a linear or branched propylene group, a linear or branched butylene group, or a -CH 2 CH 2 CH 2 OCH(OH)CH 2 - group; preferentially R independently denotes a -CH 2 CH 2 CH 2 OCH(OH)CH 2 - group;
  • R' independently represent a divalent linear or branched C 2 -Ci 2 hydrocarbon-based group, optionally including one or more heteroatoms such as oxygen; preferably, R' denotes an ethylene group, a linear or branched propylene group, a linear or branched butylene group, or a -CH 2 CH 2 CH 2 OCH(OH)CH 2 - group; preferentially R' denotes - CH(CH 3 )-CH 2 -.
  • the siloxane blocks preferably represent between 50 and 95 mol% of the total weight of the silicone, more particularly from 70 to 85 mol%.
  • the amine content is preferably between 0.02 and 0.5 meq/g of copolymer in a 30% solution in dipropylene glycol, more particularly between 0.05 and 0.2.
  • the weight-average molecular weight (Mw) of the silicone is preferably between 5,000 and 1,000,000, more particularly between 10,000 and 200,000.
  • R, R' and R" independently represent a C1-C4 alkyl or hydroxy group
  • A represents a C3 alkylene group and m and n are such that the sum of m+n is', preferably less than 2,000, more preferably less than 1,500, and even more preferably less than 1 ,000 approximately; in which: x and y are numbers such that the sum of x and y ranges from, for example, 1 to less than 2,000; preferably, x ranges from 10 to less than 1,500 and especially from 100 to 1,000; preferably, y ranges from 1 to 100;
  • R1 and R2 are linear or branched, saturated or unsaturated alkyl groups, comprising 6 to 30 carbon atoms, preferably 8 to 24 carbon atoms and especially 12 to 20 carbon atoms;
  • A denotes a linear or branched alkylene group containing from 2 to 8 carbon atoms.
  • A comprises 3 to 6 carbon atoms, especially 4 carbon atoms; preferably, A is branched.
  • R1 and R2 are independently saturated linear alkyl groups comprising 6 to 30 carbon atoms, preferably 8 to 24 carbon atoms and especially 12 to 20 carbon atoms; mention may be made in particular of dodecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl and eicosyl groups; and preferentially, R1 and R2, which may be identical or different, are chosen from hexadecyl (cetyl) and octadecyl (stearyl) groups.
  • the silicone is of formula (K) with: x ranging from, for example, 10 to 2,000 and especially from 100 to 1,000; y ranging from 1 to 100;
  • A comprising 3 to 6 carbon atoms and especially 4 carbon atoms; preferably, A is branched; and more particularly A is chosen from the following divalent groups: CH2CH2CH2 and -CH 2 CH(CH 3 )CH2-; and
  • R1 and R2 being independently linear, saturated alkyl groups comprising 6 to 30 carbon atoms, preferably 8 to 24 carbon atoms and especially 12 to 20 carbon atoms; chosen in particular from dodecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl and eicosyl groups; preferentially, R1 and R2, which may be identical or different, being chosen from hexadecyl (cetyl) and octadecyl (stearyl) groups.
  • a preferred silicone of formula (K) is bis-cetearyl amodimethicone.
  • aminosilicones of the present disclosure may also be chosen from polydimethylsiloxanes comprising primary amine groups at the chain end or on side chains, for example aminopropyl end or side groups, for instance those of formula (A), (B), or (C):
  • n is preferably less than 2,000, more preferably less than 1,500, and even more preferably less than 1,000.
  • aminosilicone (A) mention may be made of those sold under the names DMS-A11, DMS-A12, DMS-A15, DMS-A21, DMS-A31, DMS-A32 and DMS-A35 by the company Gelest.
  • n and m are such that it is preferably less than 2,000, more preferably less than 1,500, and even more preferably less than 1,000.
  • silicone (B) mention may be made of those sold under the names AMS-132, AMS-152, AMS- 162, AMS- 163, AMS-191 and AMS- 1203 by the company Gelest and KF-8015 by the company Shin Etsu.
  • n is preferably less than 2,000, more preferably less than 1,500, and even more preferably less than 1,000.
  • silicone (C) mention may be made of those sold under the names MCR-A11 and MCR-A12 by the company Gelest.
  • the (c) aminosilicone according to the present invention is amodimethicone.
  • the (c) aminosilicone is bis-cetearyl amodimethicone.
  • the (c) aminosilicone is aminopropyl dimethicone.
  • Aminosilicones suitable for use according to the present invention include, but are not limited to, volatile and non-volatile, cyclic, linear, and branched aminosilicones having a viscosity ranging from 5x10" 6 to 2.5 m 2 /s at 25°C, for example, from l xlO' 5 to 1 m 2 /s.
  • the amount of the (c) aminosilicone in the composition according to the present invention may be 0.01% by weight or more, preferably 0.1% by weight or more, and more preferably 1% by weight or more, relative to the total weight of the composition.
  • the amount of the (c) aminosilicone in the composition according to the present invention may be 15% by weight or less, preferably 10% by weight or less, and more preferably 5% by weight or less, relative to the total weight of the composition.
  • the amount of the (c) aminosilicone in the composition according to the present invention may range from 0.01% to 15% by weight, preferably from 0.1% to 10% by weight, and more preferably from 1% to 5% by weight, relative to the total weight of the composition.
  • composition according to the present invention may further comprise (d) at least one silicone other than the (c) aminosilicone.
  • a single type of silicone may be used, or two or more different types of silicones may be used in combination.
  • the (d) silicone be selected from silicone oils.
  • silicone oil means a silicone compound or substance which is in the form of a liquid or a paste at room temperature (25°C) under atmospheric pressure (760 mmHg).
  • silicone oils those generally used in cosmetics may be used alone or in combination thereof.
  • Silicones or organopolysiloxanes are defined, for instance, by Walter NOLL in “Chemistry and Technology of Silicones” (1968), Academic Press. They may be volatile or non-volatile. Thus, the silicone oil(s) may be selected from volatile silicones, non-volatile silicones and mixtures thereof.
  • the silicone oil may comprise either at least one volatile silicone oil or at least one nonvolatile silicone oil, or both at least one volatile silicone oil and at least one non-volatile silicone oil.
  • the volatile or non-volatile silicone may be selected from linear, branched, or cyclic silicones, optionally modified with at least one organo-functional moiety or group.
  • the silicone oil may be selected from the group consisting of polydialkylsiloxanes such as polydimethylsiloxanes (PDMS), polyalkylarylsiloxanes such as phenyltrimethicone, polydiarylsiloxanes, and organo-modified polysiloxanes comprising at least one organo-functional moiety or group chosen from poly(oxyalkylene) moieties or groups, alkoxy or alkoxyalkyl moieties or groups, hydroxyl or hydroxylated moieties or groups, acyloxy or acyloxyalkyl moieties or groups, carboxylic acid or carboxylate moieties or groups, acrylic moieties or groups, and oxazoline moieties.
  • PDMS polydimethylsiloxanes
  • polyalkylarylsiloxanes such as phenyltrimethicone
  • polydiarylsiloxanes polydiarylsiloxanes
  • the silicone oil(s) is/are volatile, the silicone oil(s) may be chosen from those having a boiling point ranging from 60°C to 260°C, for example:
  • cyclic silicones such as polydialkylsiloxanes comprising from 3 to 7, for instance, from 4 to 5 silicon atoms.
  • siloxanes include octamethylcyclotetrasiloxane marketed, for instance, under the trade name VOLATILE SILICONE® 7207 by UNION CARBIDE and SILBIONE® 70045 V2 by RHODIA, decamethylcyclopentasiloxane marketed under the trade name VOLATILE SILICONE® 7158 by UNION CARBIDE, and SILBIONE® 70045 V5 by RHODIA, KF-995 by SHIN ETSU, as well as mixtures thereof.
  • Cyclomethicones may also be used, for example, those marketed under the references DC 244, DC 245, DC 344, DC 345, and DC 246 by DOW CORNING. Cyclocopolymers of the dimethylsiloxane/methylalkylsiloxane type may also be used, such as SILICONE VOLATILE® FZ 3109 marketed by UNION CARBIDE, of formula wherein:
  • Combinations of cyclic silicones such as polydialkylsiloxanes with silicon derived organic compounds may also be used, such as an octamethylcyclotetrasiloxane and tetratrimethylsilylpentaerythritol (50/50) mixture, and an octamethylcyclotetrasiloxane and oxy-l,r-(hexa-2,2,2',2',3,3'-trimethylsilyloxy) bisneopentane mixture; and
  • linear volatile polydialkylsiloxanes comprising from 2 to 9 silicon atoms.
  • a nonlimiting example of such a compound is decamethyltetrasiloxane marketed, for instance, under the trade name "SH-200" by TORAY SILICONE. Silicones belonging to this class are also described, for example, in Cosmetics and Toiletries, Vol. 91, Jan. 76, P. 27-32-TODD & BYERS "Volatile Silicone Fluids for Cosmetics".
  • the silicone oil(s) may be chosen from cyclic silicones.
  • the silicone oil(s) may be chosen from non-volatile silicones, such as polydialkylsiloxanes, polyalkylarylsiloxanes, polydiarylsiloxanes, and organo-modified poly siloxanes as explained above.
  • the molecular weight of the (c) silicone preferably polydimethylsiloxanes with trimethylsilyl end groups, has a weight-average molecular weight (Mw) of 300,000 or more, preferably 350,000 or more, more preferably 400,000 or more, and preferably 3,000,000 or less, more preferably 2,000,000 or less, even more preferably 1,000,000 or less.
  • Mw weight-average molecular weight
  • the (c) silicone preferably silicone oil
  • the (c) silicones that are preferred in accordance with the present invention may be the polydimethylsiloxanes with trimethylsilyl end groups, such as the oils having a viscosity at 25°C greater than 1,000,000 cSt (mm 2 /s), even more preferentially a viscosity greater than 2,000,000 cSt, and even more particularly greater than 5,000,000 cSt, better still greater than 10,000,000 cSt and preferably less than 50,000,000 cSt, better still less than 30,000,000 cSt, even better still less than 15,000,000 cSt.
  • all the polydimethylsiloxanes can be used as they are or in the form of solutions, emulsions, nanoemulsions or microemulsions.
  • Non-limiting examples of commercial products corresponding to such polydialkylsiloxanes include BY22-029 (product of Dow Coming Toray, Co., Ltd.; nonionic emulsion of dimethicone oil), BY22-060 (product of Dow Corning Toray, Co., Ltd.; cationic emulsion containing a solution obtained by diluting highly polymerized dimethicone with a low viscosity silicone), BY22-019 (product of Dow Coming Toray, Co., Ltd.; nonionic and cationic emulsion containing a solution obtained by diluting highly polymerized dimethicone with cyclic silicone), BY22-020 (product of Dow Coming Toray, Co., Ltd.; cationic emulsion containing a solution obtained by diluting a highly polymerized dimethicone with light liquid isoparaffin), KM902 (product of Shin-Etsu Chemical Co., Ltd.; nonionic emulsion of highly polymerized dim
  • Polyalkylarylsiloxanes may be chosen from polydimethyl/methylphenylsiloxanes, linear and/or branched polydimethyl/diphenyl siloxanes.
  • Non-limiting examples of such polyalkylarylsiloxanes include the products marketed under the following trade names:
  • SILBIONE® fluids of the 70 641 series from RHODIA SILBIONE® fluids of the 70 641 series from RHODIA
  • RHODORSIL® fluids of the 70 633 and 763 series from RHODIA phenyltrimethicone fluid marketed under the reference DOW CORNING 556 COSMETIC GRADE FLUID by DOW CORNING;
  • PK series silicones from BAYER for example, the PK20 product
  • PN PH series silicones from BAYER, for example, the PN1000 and PH 1000 products; and some SF series fluids from GENERAL ELECTRIC, such as SF 1023, SF 1154, SF 1250, and SF 1265.
  • Organo-modified silicones which may be used according to the present invention include, but are not limited to, silicones such as those previously defined and comprising within their structure at least one organo-functional moiety or group linked directly or by means of a hydrocarbon group.
  • Organo-modified silicones may include, for example, polyorganosiloxanes comprising: polyethyleneoxy and/or polypropyleneoxy moieties optionally comprising C6-C24 alkyl moieties, such as products called dimethicone copolyols marketed by DOW CORNING under the trade name DC 1248 and under the trade name DC Q2-5220 and SILWET® L 722, L 7500, L 77, and L 711 fluids marketed by UNION CARBIDE and (Ci2)alkyl-methicone copolyol marketed by DOW CORNING under the trade name Q2 5200; alkoxylated moieties, such as the product marketed under the trade name "SILICONE COPOLYMER F-755" by SWS SILICONES and ABIL WAX® 2428, 2434, and 2440 by GOLDSCHMIDT; hydroxylated moieties, such as hydroxyalkyl function-containing polyorganosiloxanes described, for instance, in French
  • acyloxyalkyl moieties for example, the polyorganosiloxanes described in U.S. Pat. No. 4,957,732; anionic moieties of the carboxylic acid type, for example, the products described in European Patent No.
  • Polydimethylsiloxanes with dimethylsilanol end groups may also be used, for example, those sold under the trade name dimethiconol (CTFA), such as fluids of the 48 series marketed by RHODIA.
  • CTFA dimethiconol
  • the silicone oil(s) may be chosen from polydimethylsiloxanes and organo-modified polydimethylsiloxanes.
  • the silicone oil be selected from volatile or non-volatile silicone oils, such as volatile or non-volatile polydimethylsiloxanes (PDMS) containing a linear or cyclic silicone chain, that are liquid or pasty at ambient temperature, in particular cyclopolydimethylsiloxanes (cyclomethicones) such as cyclopentasiloxane and cyclohexasiloxane; polydimethylsiloxanes containing alkyl, alkoxy, or phenyl groups that are pendent and/or at the end(s) of the silicone chain, which groups have from 2 to 24 carbon atoms; phenyl silicones such as phenyltrimethicones, phenyldimethicones, phenyltrimethylsiloxydiphenylsiloxanes, diphenyldimethicones, diphenylmethyldiphenyltrisiloxanes, 2-phenylethyltrimethyl siloxysi
  • Non-limiting examples of such combinations include a mixture of cyclopentasiloxane and dimethiconol, marketed, for instance, under the trade name Xiameter PMX-1501 Fluid by Dow Coming.
  • the degree of polymerization of the (d) silicone be less than 2,000, more preferably less than 1,500, and even more preferably less than 1,000.
  • the amount of the (d) silicone in the composition according to the present invention may be 0.1% by weight or more, preferably 0.5% by weight or more, and more preferably 1% by weight or more, relative to the total weight of the composition.
  • the amount of the (d) silicone in the composition according to the present invention may be 30% by weight or less, preferably 25% by weight or less, and more preferably 20% by weight or less, relative to the total weight of the composition.
  • the amount of the (d) silicone in the composition according to the present invention may range from 0.1% to 30% by weight, preferably from 0.5% to 25% by weight, and more preferably from 1% to 20% by weight, relative to the total weight of the composition.
  • the weight ratio of the (c) aminosilicone/the (d) silicone may be from 0.01 to 5, preferably from 0.1 to 1, and more preferably from 0.2 to 0.5.
  • composition according to the present invention may further comprise (e) water.
  • the amount of the (e) water may be 65% by weight or more, preferably 70% by weight or more, and more preferably 75% by weight or more, relative to the total weight of the composition.
  • the amount of the (e) water may be 95% by weight or less, preferably 90% by weight or less, and more preferably 85% by weight or less, relative to the total weight of the composition.
  • the amount of the (e) water may be from 65% to 95% by weight, preferably from 70% to 90% by weight, and more preferably from 75% to 85% by weight, relative to the total weight of the composition.
  • composition according to the present invention may further comprise (f) at least one fatty alcohol. Two or more types of fatty alcohols may be used in combination.
  • fatty here means the inclusion of a relatively large number of carbon atoms.
  • alcohols which have 6 or more, preferably 8 or more, and more preferably 10 or more carbon atoms are encompassed within the scope of fatty alcohols.
  • the fatty alcohols may be saturated or unsaturated.
  • the fatty alcohol may be linear or branched. Two or more types of fatty alcohols may be used in combination.
  • the fatty alcohol may have the structure R-OH wherein R is chosen from saturated and unsaturated, linear and branched radicals containing from 8 to 40 carbon atoms, for example from 8 to 30 carbon atoms. In at least one embodiment, R is chosen from C12-C24 alkyl and C12-C24 alkenyl groups. R may be or may not be substituted with at least one hydroxyl group.
  • Non-limiting examples of fatty alcohols include lauryl alcohol, cetyl alcohol, stearyl alcohol, oleyl alcohol, behenyl alcohol, linoleyl alcohol, undecylenyl alcohol, palmitoleyl alcohol, arachidonyl alcohol, erucyl alcohol, cetearyl alcohol, and mixtures thereof.
  • Suitable fatty alcohols include, but are not limited to, cetyl alcohol, cetearyl alcohol, stearyl alcohol, behenyl alcohol, oleyl alcohol, and mixtures thereof.
  • the fatty alcohol may represent a mixture of fatty alcohols, which means that several species of fatty alcohol may coexist, in the form of a mixture, in a commercial product.
  • the fatty alcohol used in the composition according to the present invention is chosen from cetyl alcohol and cetearyl alcohol.
  • the amount of the (f) fatty alcohol in the composition according to the present invention may be 0.1% by weight or more, preferably 0.3% by weight or more, and more preferably 0.5% by weight or more, relative to the total weight of the composition.
  • the amount of the (f) fatty alcohol in the composition according to the present invention may be 20% by weight or less, preferably 15% by weight or less, and more preferably 10% by weight or less, relative to the total weight of the composition.
  • the amount of the (f) fatty alcohol in the composition according to the present invention may range from 0.1% to 20% by weight, preferably from 0.3% to 15% by weight, and more preferably from 0.5% to 10% by weight, relative to the total weight of the composition.
  • composition according to the present invention may further comprise (g) at least one oligomer of a triglyceride of hydroxylated fatty acid and of a saturated diacid If two or more oligomers of a triglyceride of hydroxylated fatty acid and of a saturated diacid are used, they may be the same or different.
  • oligomer here means a polymer in which a relatively small number of monomers are bonded. It is preferable that the number of monomers in the oligomer be 100 or less, more preferably 50 or less, and even more preferably 20 or less.
  • the (g) oligomer of a triglyceride of hydroxylated fatty acid and of a saturated diacid can be obtained by the reaction of a triglyceride of a hydroxylated fatty acid (such as hydrogenated castor oil) and of a saturated diacid.
  • the reaction may be esterification.
  • the (g) oligomer of a triglyceride of hydroxylated fatty acid and of a saturated diacid may be an oligoester of a hydroxylated fatty acid and of a saturated diacid.
  • the diacid is said to be saturated when the hydrocarbonbased chain from which it is constituted does not have an unsaturated group, i.e. a carboncarbon double bond.
  • the term "diacid” here means a hydrocarbon-based compound comprising two -COOH carboxyl functions.
  • the diacid can be a single diacid or a mixture of several different diacids.
  • the oligomer can be a mixture of several different oligomers.
  • saturated diacids that can be used, mention may be made of sebacic acid (or 1,10- decanedioic acid), malonic acid, succinic acid, glutaric acid, adipic acid, azelaic acid, octadecamethylene dicarboxylic acid, and eicosadicarboxylic acid.
  • the oligomer can be an oligoester whose monomers are represented by the following formulae (A) of triglyceride and (B) of diacid: wherein
  • Ri represents a saturated or unsaturated, linear or branched alkylene group comprising, for example, from 1 to 18 carbon atoms, preferably represents the group -(CH2)1-, where “1” can vary from 1 to 20 and especially from 3 to 16, for example from 6 to 12,
  • R.2 represents a saturated or unsaturated, linear or branched alkyl group comprising, for example, from 1 to 12 carbon atoms, preferably represents the group -(CH2) m -CH3, where “m” can vary from 0 to 11 and especially from 2 to 11 , for example from 3 to 9, and wherein
  • Xi represents a linear or branched alkylene group, preferably represents the linear alkylene group -(CH2) X - where “x” is an integer from 1 to 30, and preferably from 3 to 15.
  • the group in the above formula (A) represents the alkyl residue of 12-hydroxystearic acid (the major component of hydrogenated castor oil).
  • Xi represents the linear alkylene group -(CH2)x- where “x” is 8.
  • the average degree of polymerization of the oligomer may vary between 3 and 12, preferably between 4 and 10.
  • the (g) oligomer of a triglyceride of a hydroxylated fatty acid and of a saturated diacid can be represented by the following formula (C): wherein each of Ri, R2, and Xi have the meaning as explained above, and n means an average degree of polymerization between 3 and 12, preferably between 4 and 10.
  • the (a) oligomer of a triglyceride of a hydroxylated fatty acid and of a saturated diacid be an oligoester of hydrogenated castor oil and of sebacic acid, i.e., a hydrogenated castor oil/sebacic acid copolymer formed from hydrogenated castor oil and sebacic acid.
  • the hydrogenated castor oil/sebacic acid copolymer is especially sold by the company CRODA under various names depending on the degree of polymerization.
  • the (g) oligomer(s) of a triglyceride of a hydroxylated fatty acid and of a saturated diacid may be present in the composition according to the present invention in an amount of 0.1% by weight or more, preferably 0.3% by weight or more, and more preferably 0.5% by weight or more, relative to the total weight of the composition.
  • the (g) oligomer(s) of a triglyceride of a hydroxylated fatty acid and of a saturated diacid may be present in the composition according to the present invention in an amount of 15% by weight or less, preferably 10% by weight or less, and more preferably 5% by weight or less, relative to the total weight of the composition.
  • the (g) oligomer(s) of a triglyceride of a hydroxylated fatty acid and of a saturated diacid may be present in the composition according to the present invention in an amount ranging from 0.1% to 15% by weight, preferably from 0.3% to 10% by weight, and more preferably from 0.5% to 5% by weight, relative to the total weight of the composition.
  • composition according to the present invention may further comprise, in addition to the aforementioned essential/optional components, further optional components typically employed in cosmetics, specifically, nonionic, anionic or amphoteric surfactants, oils, dyes, fillers, polyols such as glycols and glycerol, hydrophilic or lipophilic thickeners, UV filters, natural extracts derived from animals or vegetables, preservatives, and the like, within a range which does not impair the effects of the present invention.
  • cosmetics specifically, nonionic, anionic or amphoteric surfactants, oils, dyes, fillers, polyols such as glycols and glycerol, hydrophilic or lipophilic thickeners, UV filters, natural extracts derived from animals or vegetables, preservatives, and the like, within a range which does not impair the effects of the present invention.
  • composition according to the present invention may comprise the above further optional component(s) in an amount of from 0.001% to 30% by weight, preferably from 0.01% to 20% by weight, and more preferably from 0.1% to 10% by weight, relative to the total weight of the composition.
  • composition according to the present invention can be prepared by mixing the above essential and optional ingredients in accordance with any of the processes which are well known to those skilled in the art.
  • composition according to the present invention can be in the form of a fluid, preferably a liquid or a paste, and more preferably a liquid. It is preferable that the composition according to the present invention be in the form of an emulsion.
  • composition according to the present invention can be used for treating, e.g., caring for or conditioning, keratin fibers.
  • composition according to the present invention may be a cosmetic composition, preferably a rinse-off type cosmetic composition, and more preferably a rinse-off type hair cosmetic composition
  • composition according to the present invention may be used in hair care cosmetic products such as shampoos, conditioners and the like.
  • the present invention also relates to a cosmetic process for caring for or conditioning keratin fibers, preferably hair, comprising the step of: applying onto the keratin fibers the composition according to the present invention.
  • the cosmetic process according to the present invention may further comprise the step of heating the keratin fibers after the step of applying onto the keratin fibers the composition according to the present invention.
  • the present invention may also relate to a process for providing keratin fibers such as hair with a light feeling to the touch and smoothness, comprising the step of applying onto the keratin fibers the composition according to the present invention.
  • the applying step can be performed by any conventional means such as an applicator, e.g., a brush.
  • the present invention also relates to a use of
  • the enhanced or improved conditioning effects can include higher strength of keratin fibers and improved smoothness of keratin fibers which can provide a smoother feeling to the touch and easier combing.
  • ingredients (a) and (b), as well as other optional ingredients, for the composition according to the present invention can apply to ingredients (a) and (b), as well as possible optional ingredients in the composition for the above use.
  • Each of the treatment compositions for hair according to Examples 1-5 (Ex. 1 to Ex. 5) and Comparative Example 1 (Comp. Ex. 1) was prepared by mixing the ingredients shown in Table 1. The numerical values for the amounts of the ingredients are all based on “% by weight” as raw materials.
  • Two hair swatches (hair bundles) (2.7 g, 27 cm) were prepared for each experiment. Each of the hair swatches was washed with a clarifying shampoo once. After shampooing, the hair swatch was rinsed with water. 1.1 g of each of the compositions according to Examples 1 -5 and Comparative Example 1 was applied onto each hair swatch, and left for 5 minutes. The hair swatch was then rinsed off under running water, and then dried naturally under ambient conditions to obtain a treated hair swatch.
  • the root of the hair swatch was fixed on a plate.
  • the tip of the tress was held and oriented upwardly, and then, the tip of the tress was released such that the tip of the tress could be directed downwardly.
  • the angle between the plate and the root of the hair swatch (hair bundle) was measured (cf. Fig. 1). The average value was determined as the bending angle.
  • the bending angle of the hair swatch itself was 71°.
  • Three hair swatches (2.7 g, 27 cm) were prepared for each experiment. Each of the hair swatches was washed with a clarifying shampoo once. After shampooing, the hair swatch was rinsed with water. 1.1 g of each of the compositions according to Examples 3 and 5, and Comparative Example 1 was applied onto each hair swatch, and left for 5 minutes. The hair swatch was then rinsed off under running water, and then dried naturally under ambient conditions to obtain a treated hair swatch.
  • the treated hair swatch was placed on a plate, and its root side was fixed on the plate with a hair clip.
  • the smoothness of the treated hair swatch was evaluated by scanning the hair swatch from root to tip with a sensor (Handy Rub Tester (type TL701) from Trinity Lab) and measuring COF (Coefficient of Friction). The measurement was carried out 3 times for a single treated hair swatch. The same procedure was conducted with two more hair swatches to obtain 9 results in total for one composition, and the mean values were calculated for each composition. A lower score indicates that a better smoothness effect can be exerted.
  • the COF of the hair swatch itself was 0.24.
  • compositions according to Examples 1, 2 and 4 were not evaluated.
  • Three hair swatches (2.7 g, 27 cm) were prepared for each experiment. Each of the hair swatches was washed with a clarifying shampoo once. After shampooing, the hair swatch was rinsed with water. 1.1 g of each of the compositions according to Examples 3 and 5, and Comparative Example 1 was applied onto each hair swatch. The hair swatch was left for 5 minutes. The hair swatch was rinsed off under running water, and then dried naturally under ambient conditions to obtain a treated hair swatch.
  • the benchmark means the assessment result for the hair swatch itself, i.e., without the application of any composition.
  • compositions according to Examples 1, 2 and 4 were not evaluated.
  • compositions according to Examples 1- 5 each of which comprises both a cationic surfactant and an ester of polyol(s) and of fatty diacid dimer, were able to provide hair with improved conditioning effects, in particular higher strength of hair.
  • a bending angle of 74° or more is a threshold to consider to provide good strength.
  • compositions according to Examples 3 and 5 were able to improve smoothness of hair.
  • compositions according to Examples 3 and 5 were able to provide hair with better cosmetic effects such as easier combing and better strength of hair.
  • composition according to Comparative Example 1 which comprises a cationic surfactant but does not comprise an ester of polyol(s) and of fatty diacid dimer, was able to provide hair with only very limited conditioning effects, in particular only very limited improvement in strength of hair.
  • composition according to Comparative Example 1 was able to slightly improve smoothness of hair.
  • composition according to Comparative Example 1 could not provide any perceivable better cosmetic effects in terms of combing and strength of hair.

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Abstract

La présente invention concerne une composition pour le traitement des fibres kératiniques comprenant : (a) au moins un tensioactif cationique ; et (b) au moins un ester de polyol(s) et de dimère de diacide gras, ou un ester de celui-ci, la quantité d'ester(s) de polyol(s) (b) et de dimère d'acide gras, ou d'ester(s) de celui-ci, étant de 0,5 % en poids ou plus, de préférence 1,0 % en poids ou plus, plus préférablement 1,5 % en poids ou plus, et encore plus préférablement 2,0 % en poids ou plus, par rapport au poids total de la composition. La présente invention peut fournir aux fibres kératiniques telles que les cheveux des effets de conditionnement améliorés, en particulier une plus grande résistance des fibres kératiniques.
PCT/JP2021/044606 2020-12-01 2021-11-30 Compositions pour fibres kératiniques WO2022118983A1 (fr)

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JP2020-199436 2020-12-01
JP2020199436 2020-12-01
FR2100180A FR3118709B1 (fr) 2021-01-08 2021-01-08 Compositions pour fibres keratiniques
FR2100180 2021-01-08

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