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WO2024130622A1 - Composition pour le soin et/ou le maquillage de matières kératiniques - Google Patents

Composition pour le soin et/ou le maquillage de matières kératiniques Download PDF

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Publication number
WO2024130622A1
WO2024130622A1 PCT/CN2022/140920 CN2022140920W WO2024130622A1 WO 2024130622 A1 WO2024130622 A1 WO 2024130622A1 CN 2022140920 W CN2022140920 W CN 2022140920W WO 2024130622 A1 WO2024130622 A1 WO 2024130622A1
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WO
WIPO (PCT)
Prior art keywords
acid
hydroxypropane
composition
fatty
composition according
Prior art date
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Ceased
Application number
PCT/CN2022/140920
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English (en)
Inventor
Feixue TENG
Xinrong LIN
Xiaomin WENG
Qingsheng Tao
Su YUAN
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LOreal SA
Original Assignee
LOreal SA
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Filing date
Publication date
Application filed by LOreal SA filed Critical LOreal SA
Priority to CN202280101791.XA priority Critical patent/CN120569182A/zh
Priority to PCT/CN2022/140920 priority patent/WO2024130622A1/fr
Priority to FR2300572A priority patent/FR3143984A1/fr
Publication of WO2024130622A1 publication Critical patent/WO2024130622A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/602—Glycosides, e.g. rutin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A61K8/062—Oil-in-water emulsions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • 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
    • A61K8/34—Alcohols
    • A61K8/342—Alcohols having more than seven atoms in an unbroken chain
    • 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
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
    • 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
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8158—Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations

Definitions

  • the present invention relates to a cosmetic composition.
  • the present invention relates to a composition for caring for and/or making up keratin materials.
  • the present invention also relates to a non-therapeutic method for caring for and/or making up keratin materials.
  • the skin is the protective barrier for the human body. It protects the interior of the body from physical injury (such as trauma) and biological injury (such as bacteria, viruses or fungi) .
  • High potency can be provided by high dosage of anti-aging agents such as hydroxypropyl tetrahydropyrantriol, and luxury sensory includes high consistency, easy spreading quick penetration, and non-sticky finish, and can be provided bylamellar structure.
  • anti-aging agents such as hydroxypropyl tetrahydropyrantriol
  • luxury sensory includes high consistency, easy spreading quick penetration, and non-sticky finish, and can be provided bylamellar structure.
  • liquid leakage would happen at room temperature and 37°C.
  • the product is stable at room temperature (for example, 25°C) and 37°C.
  • compositions for caring for and/or making up the skin comprising at least one anti-aging agent such as hydroxypropyl tetrahydropyrantriol, which is stable at both room temperature (for example, 25°C) and 37°C for a relatively longer period.
  • at least one anti-aging agent such as hydroxypropyl tetrahydropyrantriol
  • compositions being stable at both room temperature (for example, 25°C) and 37°C for a relatively longer period.
  • the present invention provides a composition in the form of an oil-in-water emulsion for caring for and/or making up keratin materials, comprising:
  • At least one surfactant selected from fatty alcohols, alkylglucosides, and combinations thereof;
  • polymer derived from a monomer of 2-acrylamido-2-methylpropanesulfonic acid (abbreviated as “polymer” hereafter) ;
  • R represents a saturated C 1 to C 10 , in particular C 1 to C 4 , alkyl radical which can optionally be substituted by at least one radical selected from OH, COOH or COOR” 2 , with R” 2 being a saturated C 1 -C 4 alkyl radical,
  • - S represents a monosaccharide or a polysaccharide comprising up to 20 sugar units, in particular up to 6 sugar units, in pyranose and/or furanose form and of the L and/or D series, it being possible for the said monosaccharide or polysaccharide to be substituted by a hydroxyl group which is necessarily free and optionally one or more optionally protected amine functional group (s) , and
  • - X represents a radical selected from the–CO-, -CH (OH) -, -CH (NH 2 ) -, -CH (NHCH 2 CH 2 CH 2 OH) -, -CH (NHPh) -and–CH (CH 3 ) -groups and in particular a–CO-, -CH (OH) -or–CH (NH 2 ) -radical and more particularly a–CH (OH) -radical,
  • the S-CH 2 -X bond represents a bond of C-anomeric nature, which can be ⁇ or ⁇ ,
  • composition of the present invention is in the form of an oil-in-water emulsion.
  • said composition comprises a continuous aqueous phase and a dispersed fatty phase.
  • the present invention provides a non-therapeutic method for caring for and/or making up keratin materials, comprising applying the composition according to the first aspect of the present invention to the keratin materials.
  • keratin materials is intended to cover human skin, mucous membranes such as the lips. Facial skin is most particularly considered according to the present invention.
  • the present invention provides a composition in the form of an oil-in-water emulsion for caring for and/or making up keratin materials, comprising:
  • At least one surfactant selected from fatty alcohol, alkylglucoside, and combinations thereof;
  • the composition of the present invention comprises at least one structuring agent selected from saturated C12-C22 fatty acids.
  • saturated C12-C22 fatty acid mention can be made of myristic acid, pentadecanoic acid, palmitic acid, heptadecanoic acid, stearic acid, cetearylic acid, arachidic acid, behenic acid, and a combination thereof.
  • the structuring agent is selected from saturated C14-C18 fatty acids.
  • the structuring agent is selected from linear and saturated C14-C18 fatty acids.
  • the structuring agent is selected from myristic acid, palmitic acid, stearic acid, and a combination thereof.
  • the structuring agent is present in an amount ranging from 0.5 wt. %to 30 wt. %, preferably from 1 wt. %to 20 wt. %, more preferably from 1.5 wt. %to 7 wt. %, relative to the total weight of the composition.
  • Surfactants selected from fatty acid esters
  • the composition of the present invention comprises at least one surfactant selected from fatty acid esters.
  • the surfactant is selected from:
  • polyglyceryl esters of (a) fatty acid (s) mention be made of the product containing 2 to 10 glycerol units, such as polyglyceryl monolaurate, oleate, myristate, caprylate, or stearate comprising 2 to 10 glycerol units, polyglyceryl mono (iso) stearate comprising 2 to 10 glycerol units, polyglyceryl dioleate comprising 2 to 10 glycerol units, polyglyceryl dilaurate comprising 2 to 10 glycerol units, polyglyceryl dimyristate comprising 2 to 10 glycerol units, polyglyceryl trimyristate comprising 2 to 10 glycerol units, polyglyceryl trioleate comprising 2 to 10 glycerol units, and polyglyceryl tricaprylate comprising 2 to 10 glycerol units.
  • Polyglyceryl esters include, polyglyceryl esters of C16-C22 saturated, unsaturated and branched chain fatty acids, such as polyglyceryl-4 isostearate, polyglyceryl-3 oleate, polyglyceryl-2 oleate, polyglyceryl-2 sesquioleate, triglyceryl diisostearate, diglyceryl monooleate, tetraglyceryl monooleate, or mixtures thereof.
  • polyglyceryl esters of C16-C22 saturated, unsaturated and branched chain fatty acids such as polyglyceryl-4 isostearate, polyglyceryl-3 oleate, polyglyceryl-2 oleate, polyglyceryl-2 sesquioleate, triglyceryl diisostearate, diglyceryl monooleate, tetraglyceryl monooleate, or mixtures thereof.
  • Monoglyceryl esters include, but are not limited to, glyceryl monoesters, preferably glyceryl monoesters of C16-C22 saturated, unsaturated and branched chain fatty acids such as glyceryl oleate, glyceryl monostearate, glyceryl monoisostearate, glyceryl monopalmitate, glyceryl monobehenate, or mixtures thereof.
  • glyceryl stearate glyceryl mono-, di-and/or tristearate
  • CTFA name glyceryl stearate
  • glyceryl ricinoleate or mixtures thereof can be cited, or as polyoxyalkylenated derivatives thereof, mono-, di-or triester of fatty acids with a polyoxyalkylenated glycerol (mono-, di-or triester of fatty acids with a polyalkylene glycol ether of glycerol) , preferably polyoxyethylenated glyceryl stearate (mono-, di-and/or tristearate) , such as PEG-20 glyceryl stearate (mono-, di-, tristearate and/or triisostearate) can be cited.
  • the polyoxyalkylenated derivative of mono glyceryl ester of fatty acids includes 10 to
  • the sorbitol esters of C8-C24 fatty acids and polyoxyalkylenated derivatives thereof can be selected from sorbitan palmitate, sorbitan isostearate, sorbitan trioleate and esters of fatty acids and alkoxylated sorbitan containing for example from 20 to 100 EO, such as for example sorbitan monostearate (CTFA name: sorbitan stearate) , sold by the company ICI under the name Span 60, sorbitan monopalmitate (CTFA name: sorbitan palmitate) , sold by the company ICI under the name Span 40, or sorbitan tristearate 20 EO (CTFA name: polysorbate 65) , sold by the company ICI under the name Tween 65, polyethylene sorbitan trioleate (polysorbate 85) or the compounds marketed under the trade names Tween 20 or Tween 60 by Uniqema.
  • CTFA name sorbitan monostearate
  • ethoxylated ethers of fatty acids and glucose or alkylglucose ethoxylated ethers of fatty acids and methylglucose, and in particular the polyethylene glycol ether of the diester of methylglucose and stearic acid with about 20 moles of ethylene oxide (CTFA name: PEG-20 methyl glucose distearate) such as the product marketed under the name Glucam E-20 distearate by AMERCHOL, the polyethylene glycol ether of the mixture of monoester and diester of methyl-glucose and stearic acid with about 20 moles of ethylene oxide (CTFA name: PEG-20 methyl glucose sesquistearate) and in particular the product marketed under the name Glucamate SSE-20 by AMERCHOL and that marketed under the name Grillocose PSE-20 by GOLDSCHMIDT, or mixtures thereof, can for example be cited.
  • sucrose esters saccharose palmito-stearate, saccharose stearate and saccharose monolaurate can for example be cited.
  • the fatty acid ester of polyalkylene glycol is an ester of polyethylene glycol comprising from 1 to 200 oxyethylene groups and of a saturated or unsaturated fatty acid comprising from 12 to 30 carbon atoms, more preferably, the fatty acid ester of polyalkylene glycol is selected from polyethylene glycol 2 OE monostearate or polyethylene glycol 100 monostearate (PEG-100 stearate) .
  • the surfactant is selected from mono-and polyglyceryl esters of a fatty acid, fatty acid esters of polyalkylene glycol, and mixtures thereof.
  • the surfactant is selected from mono glyceryl esters or poly glyceryl esters of a C8-C24, preferably C12-C22, fatty acid and polyoxyalkylenated derivatives thereof, preferably containing from 10 to 200, or more preferably from 10 to 100 oxyalkylene units; sorbitol esters of a C8-C24, preferably C12-C22, fatty acid or polyoxyalkylenated derivatives thereof, preferably containing from 10 to 200, or more preferably from 10 to 100 oxyalkylene units; sugar (sucrose, maltose, glucose, fructose, and/or alkylglycose) esters of a C8-C24, preferably C12-C22, fatty acid or polyoxyalkylenated derivatives thereof, preferably containing from 10 to 200, or more preferably from 10 to 100 oxyalkylene units; or mixtures thereof.
  • the surfactant is selected from glyceryl stearate, PEG-100 stearate, and mixtures thereof.
  • Mixtures of the surfactant selected from mono-and polyglyceryl esters of a fatty acid are for example the product containing glyceryl stearate and PEG-100 stearate, marketed under the name ARLACEL 165 by CRODA, and the product containing glyceryl stearate (glyceryl mono-and distearate) and potassium stearate marketed under the name TEGIN by Goldschmidt (CTFA name: glyceryl stearate SE) , can also be used.
  • the surfactant selected from fatty acid esters is present in an amount ranging from 0.2 wt. %to 20 wt. %, preferably from 0.4 wt. %to 15 wt. %, more preferably from 0.8 wt. %to 12 wt. %, relative to the total weight of the composition.
  • Surfactants selected from fatty alcohols, alkylglucosides, and combinations thereof
  • the composition of the present invention comprises at least one surfactant selected from fatty alcohols, alkylglucosides, and combinations thereof.
  • the surfactant is selected from:
  • alkylpolyglucosides can be used, and for example, ethers of a sugar and of C 8 -C 24 fatty alcohols including decylglucoside such as the product marketed under the name MYDOL 10 by Kao Chemicals, the product marketed under the name PLANTAREN 2000 by Henkel, and the product marketed under the name ORAMIX NS 10 by Seppic, caprylyl/capryl glucoside such as the product marketed under the name ORAMIX CG 110 by Seppic or under the name LUTENSOL GD 70 by BASF, laurylglucoside such as the products marketed under the names PLANTAREN 1200 N and PLANTACARE 1200 by Henkel, coco-glucoside such as the product marketed under the name PLANTACARE 818/UP by Henkel, cetostearyl glucoside possibly mixed with cetostearyl alcohol, marketed for example under the name MONTANOV 68 by Seppic, under the name TEGO-
  • C14-C24 fatty alcohols mention can be made of oleyl alcohol, stearyl alcohol, cetyl alcohol, behenyl alcohol, arachidyl alcohol, lignocerylic alcohol and mixtures thereof.
  • the surfactant is selected from ethers of glucoside and a C12-C22 fatty alcohol; C14-C22 fatty alcohols; or combinations thereof.
  • the surfactant is selected from ethers of glucoside and a C12-C22 fatty alcohol; C16-C22 fatty alcohols; or combinations thereof.
  • the surfactant is selected from arachidyl alcohol, behenyl alcohol, oleyl alcohol, arachidyl glucoside, and mixtures thereof.
  • the surfactant is selected from arachidyl alcohol, behenyl alcohol, and arachidyl glucoside.
  • the surfactant selected from fatty alcohols, alkylglucosides, and combinations thereof is present in an amount ranging from 0.2 wt. %to 12 wt. %, preferably from 0.4 wt. %to 8 wt. %, more preferably from 0.6 wt. %to 3.5 wt. %, relative to the total weight of the composition.
  • the weight ratio of the structuring agent selected from saturated C12-C22 fatty acids to the surfactant selected from fatty alcohols, alkylglucosides, and combinations thereof is less than 2.5, preferably less than 1.8.
  • the composition of the present invention comprises at least one polymer derived from at least one monomer being acrylamido-2-methylpropanesulfonic acid (or polymer) .
  • the polymers in accordance with the invention are crosslinked or non-crosslinked homopolymers or copolymers comprising at least the acrylamido-2-methylpropanesulfonic acid monomer, in a form partially or totally neutralized with a mineral base other than ammonia, such as sodium hydroxide or potassium hydroxide.
  • They are preferably totally neutralized or virtually totally neutralized, i.e. at least 90%neutralized.
  • These polymers according to the invention may be crosslinked or non-crosslinked.
  • the crosslinking agents may be chosen from the polyolefinically unsaturated compounds commonly used for the crosslinking of polymers obtained by free-radical polymerization.
  • crosslinking agents examples include divinylbenzene, diallyl ether, dipropylene glycol diallyl ether, polyglycol diallyl ethers, triethylene glycol divinyl ether, hydroquinone diallyl ether, ethylene glycol or tetraethylene glycol di (meth) acrylate, trimethylolpropane triacrylate, methylenebisacrylamide, methylenebismethacrylamide, triallylamine, triallyl cyanurate, diallyl maleate, tetraallylethylenediamine, tetraallyloxyethane, trimethylolpropane diallyl ether, allyl (meth) acrylate, allylic ethers of alcohols of the sugar series, or other allylic or vinyl ethers of polyfunctional alcohols, and also allylic esters of phosphoric and/or vinylphosphonic acid derivatives, or mixtures of these compounds.
  • the crosslinking agent is chosen from methylenebis-acrylamide, allyl methacrylate and trimethylolpropane triacrylate (TMPTA) .
  • TMPTA trimethylolpropane triacrylate
  • the degree of crosslinking generally ranges from 0.01 mol%to 10 mol%and more particularly from 0.2 mol%to 2 mol%relative to the polymer.
  • the polymers in accordance with the invention are water-soluble or water-dispersible. In this case they are:
  • copolymers obtained from and from one or more hydrophilic or hydrophobic ethylenically unsaturated monomers and, if they are crosslinked, one or more crosslinking agents such as those defined above.
  • these copolymers comprise hydrophobic ethylenically unsaturated monomers, these monomers do not comprise a fatty chain and are preferably present in small amounts.
  • fatty chain means any hydrocarbon-based chain containing at least 7 carbon atoms.
  • water-soluble or water-dispersible means polymers which, when introduced into an aqueous phase at 25°C, to a mass concentration equal to 1%, make it possible to obtain a macroscopically homogeneous and transparent solution, i.e. asolution that has a maximum light transmittance value, at a wavelength equal to 500 nm, through a sample 1 cm thick, of at least 60%and preferably of at least 70%.
  • the "homopolymers” according to the invention are preferably crosslinked and neutralized, and they may be obtained according to the preparation process comprising the following steps:
  • the solution or dispersion of monomer obtained in (a) is neutralized with one or more mineral or organic bases, preferably ammonia NH 3 , in an amount making it possible to obtain a degree of neutralization of the sulfonic acid functions of the polymer ranging from 90%to 100%;
  • astandard free-radical polymerization is performed in the presence of free-radical initiators at a temperature ranging from 10 to 150°C; the polymer precipitates in the solution or dispersion based on tert-butanol.
  • the homopolymers according to the invention are preferably optionally crosslinked and/or neutralized 2-acrylamido-2-methylpropanesulfonic acid homopolymers, for instance the poly (2-acrylamido-2-methylpropanesulfonic acid) sold by the company Clariant under the name Hostacerin (CTFA name: ammonium polyacryldimethyltauramide) .
  • CTFA name ammonium polyacryldimethyltauramide
  • the water-soluble or water-dispersible AMPS copolymers according to the invention contain preferably water-soluble ethylenically unsaturated monomers, hydrophobic monomers or mixtures thereof.
  • the water-soluble comonomers may be ionic or nonionic.
  • ionic water-soluble comonomers examples that may be mentioned include the following compounds and the salts thereof:
  • - R 1 is chosen from H, -CH 3 , -C 2 H 5 and-C 3 H 7
  • R 2 is a linear or branched, saturated or unsaturated hydrocarbon-based radical containing from 1 to 6 carbon atoms, substituted with at least one sulfonic (-SO 3 -) and/or sulfate (-SO 4 -) and/or phosphate (-PO 4 H 2 -) group.
  • nonionic water-soluble comonomers examples that may be mentioned include:
  • N-vinyllactams comprising a cyclic alkyl group containing 4 to 9 carbon atoms, such as n-vinylpyrrolidone, N-butyrolactam and N-vinylcaprolactam,
  • - R 15 is chosen from H, -CH 3 , -C 2 H 5 and-C 3 H 7
  • R 16 is a linear or branched, saturated or unsaturated hydrocarbon-based radical containing from 1 to 6 carbons, optionally substituted with a halogen atom (iodine, bromine, chlorine or fluorine) ; ahydroxyl group (-OH) ; ether.
  • fatty-chain-free hydrophobic comonomers examples that may be mentioned include:
  • silicone derivatives which lead to silicone polymers after polymerization, such as methacryloxypropyltris (trimethylsiloxy) silane and silicone methacrylamides,
  • - R 23 is chosen from H, -CH 3 , -C 2 H 5 and-C 3 H 7
  • R 24 is a linear or branched, saturated or unsaturated hydrocarbon-based radical containing from 1 to 6 carbon atoms.
  • the water-soluble or water-dispersible polymers of the invention preferably have a molar mass ranging from 50 000 g/mol to 10 000 000 g/mol, preferably from 80 000 g/mol to 8 000 000 g/mol and even more preferably from 100 000 g/mol to 7 000 000 g/mol.
  • water-soluble or water-dispersible AMPS homopolymers in accordance with the invention include crosslinked or non-crosslinked polymers of sodium acrylamido-2-methylpropanesulfonate, such as the polymer used in the commercial product Simulgel TM 800 (CTFA name: Sodium Polyacryloyldimethyltaurate) .
  • water-soluble or water-dispersible AMPS copolymers examples include:
  • AMPS/sodium acrylate copolymer such as the copolymer used in the commercial product sold under the name Simulgel TM EG by the company SEPPIC (CTFA name: Acrylamide/Sodium Acryloyldimethyltaurate/Isohexadecane/Polysorbate-80) ;
  • AMPS/hydroxyethyl acrylate copolymer such as the copolymer used in the commercial product sold under the name Simulgel TM NS by the company SEPPIC (CTFA name: Hydroxyethyl acrylate/Sodium Acryloyldimethyltaurate copolymer (and) Squalane (and) Polysorbate-60) .
  • the preferred polymers are more particularly sodium acrylamido-2-methylpropanesulfonate homopolymers, such as the homopolymer used in the commercial product Sepigel TM 800, and acrylate copolymers, such as the copolymer used in the commercial product sold under the name Simulgel NS.
  • the polymer or copolymer will be used in powder form.
  • the polymers derived from AMPS may further be those comprising:
  • X + is a proton, an alkali metal cation, an alkaline-earth metal cation or an ammonium ion
  • n and p independently of each other, denote a number of moles and ranges from 0 to 30 and preferably from 1 to 20, with the proviso that n+p is less than or equal to 30, preferably less than 25 and better still less than 20;
  • R 1 denotes a hydrogen atom or a linear or branched C 1 -C 6 alkyl radical (preferably methyl) and
  • R 2 denotes a linear or branched alkyl comprising m carbon atoms, with m ranging from 6 to 30 and preferably from 10 to 25.
  • the polymers are obtained especially by free-radical polymerization in tert-butanol medium from which they precipitate. Using polymerization in tert-butanol, it is possible to obtain a size distribution of the polymer particles that is particularly favorable for its uses.
  • the polymerization reaction may be performed at a temperature of between 0 and 150°C, preferably between 20 and 100°C, either at atmospheric pressure or under reduced pressure. It may also be performed under inert atmosphere, and preferably under nitrogen.
  • the polymer is a copolymer of and of a C 16 -C 18 alcohol methacrylate comprising from 6 to 25 mol of oxyethylene groups, obtained from methacrylic acid or a methacrylic acid salt and from a C 16 -C 18 alcohol oxyethylenated with 6 to 25 mol of ethylene oxide.
  • the crosslinked copolymer obtained from 96.45 mol%of and 3.55 mol%of a C 16 -C 18 alcohol methacrylate comprising 25 oxyethylene groups (Genapol )
  • the crosslinking agent is trimethylolpropane triacrylate
  • the acrylamide/sodium 2-methyl-2- [ (1-oxo-2-propenyl) amino] -1-propanesulfonate copolymer such as Simulgel in the form of an emulsion containing polysorbate 80 as surfactant and containing isohexadecane as fatty phase, sold by the company SEPPIC, or alternatively Simulgel Simulgel and Simulgel sold by the same company.
  • the preferred polymers derived from is a crosslinked and/or neutralized 2-acrylamido-2-methylpropanesulfonic acid homopolymers, for instance the poly (2-acrylamido-2-methylpropanesulfonic acid) sold by the company Clariant under the name Hostacerin (CTFA name: ammonium polyacryldimethyltauramide) .
  • CTFA name ammonium polyacryldimethyltauramide
  • the polymer derived from at least one monomer of 2-acrylamido-2-methylpropanesulfonic acid is present in the composition according to the present invention in an amount ranging from 0.05 wt. %to 10 wt. %, preferably from 0.08 wt. %to 8 wt. %, more preferably from 0.1 wt. %to 2 wt. %, relative to the total weight of the composition.
  • composition of the present invention comprises at least one C-glycoside selected from compounds of formula (I) :
  • R represents a saturated C 1 to C 10 , in particular C 1 to C 4 , alkyl radical which can optionally be substituted by at least one radical selected from OH, COOH or COOR” 2 , with R” 2 being a saturated C 1 -C 4 alkyl radical,
  • - S represents a monosaccharide or a polysaccharide comprising up to 20 sugar units, in particular up to 6 sugar units, in pyranose and/or furanose form and of the L and/or D series, it being possible for the said monosaccharide or polysaccharide to be substituted by a hydroxyl group which is necessarily free and optionally one or more optionally protected amine functional group (s) , and
  • - X represents a radical selected from the–CO-, -CH (OH) -, -CH (NH 2 ) -, -CH (NHCH 2 CH 2 CH 2 OH) -, -CH (NHPh) -and–CH (CH 3 ) -groups and in particular a–CO-, -CH (OH) -or–CH (NH 2 ) -radical and more particularly a–CH (OH) -radical,
  • the S-CH 2 -X bond represents a bond of C-anomeric nature, which can be ⁇ or ⁇ ,
  • the C-glycoside of use for the implementation of the invention are in particular those for which R denotes a saturated linear C 1 to C 6 , in particular C 1 to C 4 , preferentially C 1 to C 2 , alkyl radical and more preferably a methyl radical.
  • amonosaccharide of the invention can be selected from D-glucose, D-galactose, D-mannose, D-xylose, D-lyxose or L-fucose, L-arabinose, L-rhamnose, D-glucuronic acid, D-galacturonic acid, D-iduronic acid, N-acetyl-D-glucosamine or N-acetyl-D-galactosamine and advantageously denotes D-glucose, D-xylose, N-acetyl-D-glucosamine or L-fucose and in particular D-xylose.
  • apolysaccharide of the invention comprising up to 6 sugar units can be selected from D-maltose, D-lactose, D-cellobiose, D-maltotriose, adisaccharide combining a uronic acid selected from D-iduronic acid or D-glucuronic acid with a hexosamine selected from D-galactosamine, D-glucosamine, N-acetyl-D-galactosamine or N-acetyl-D-glucosamine, an oligosaccharide comprising at least one xylose which can advantageously be selected from xylobiose, methyl- ⁇ -xylobioside, xylotriose, xylotetraose, xylopentaose and xylohexaose and in particular xylobiose, which is composed of two xylose molecules linked via a 1-4 bond.
  • Scan represent a monosaccharide selected from D-glucose, D-xylose, L-fucose, D-galactose or D-maltose and in particular D-xylose.
  • - R denotes an unsubstituted linear C 1 -C 4 , in particular C 1 -C 2 , alkyl radical, especially a methyl radical;
  • - S represents a monosaccharide as described above and selected in particular from D-glucose, D-xylose, N-acetyl-D-glucosamine or L-fucose, and in particular D-xylose;
  • - X represents a group selected from-CO-, -CH (OH) -or-CH (NH 2 ) -and preferably a-CH (OH) -group.
  • the acceptable salts of the compounds described in the present invention comprise conventional non-toxic salts of the said compounds, such as those formed from organic or inorganic acids. Mention may be made, by way of example, of the salts of inorganic acids, such as sulfuric acid, hydrochloric acid. Mention may also be made of the salts of organic acids, which can comprise one or more carboxylic, sulfonic or phosphonic acid groups. Mention may in particular be made of propionic acid, acetic acid, terephthalic acid, citric acid and tartaric acid.
  • neutralization of the acid group (s) can be carried out with an inorganic base, such as LiOH, NaOH, KOH, Ca (OH) 2 , NH 4 OH, Mg (OH) 2 or Zn (OH) 2 , or with an organic base, such as a primary, secondary or tertiary alkylamine, for example triethylamine or butylamine.
  • an inorganic base such as LiOH, NaOH, KOH, Ca (OH) 2 , NH 4 OH, Mg (OH) 2 or Zn (OH) 2
  • organic base such as a primary, secondary or tertiary alkylamine, for example triethylamine or butylamine.
  • This primary, secondary or tertiary alkylamine can comprise one or more nitrogen and/or oxygen atoms and can thus comprise, for example, one or more alcohol functional groups; mention may in particular be made of 2-amino-2-methylpropanol, triethanolamine, 2- (dimethylamino) propanol or 2-amino-2- (hydroxymethyl) -1, 3-propanediol. Mention may also be made of lysine or 3- (dimethylamino) propylamine.
  • solvates which are acceptable for the compounds described in the present invention comprise conventional solvates, such as those formed during the final stage of preparation of the said compounds due to the presence of solvents. Mention may be made, by way of example, of the solvates due to the presence of water or of linear or branched alcohols, such as ethanol or isopropanol.
  • aC-glycoside corresponding to the formula (I) can be used alone or as a mixture with other C-glycoside and in any proportion.
  • a C-glycoside which is suitable for the invention can in particular be obtained by the synthetic method described in the document WO 02/051828.
  • C- ⁇ -D-xylopyranoside-2-hydroxypropane or C- ⁇ -D-xylopyranoside-2-hydroxypropane and better still C- ⁇ -D-xylopyranoside-2-hydroxypropane can advantageously be used for the preparation of a composition according to the invention.
  • the C-glycoside can be C- ⁇ -D-xylopyranoside-2-hydroxypropane (or hydroxypropyl tetrahydropyrantriol) provided in the form of a solution containing 75%by weight of active material in water and propylene glycol.
  • the C-glycoside is present in the composition in an amount ranging from 3 wt. %to 30 wt. %, preferably from 5 wt. %to 15 wt. %, relative to the total weight of the composition.
  • the cosmetic composition of the present invention comprises a continuous aqueous phase.
  • Said aqueous phase comprises water.
  • the continuous aqueous phase comprises an organic solvent miscible with water (at room temperature 25°C) such as glycerin and glycols having from 2 to 20 carbon atoms, preferably from 2 to 10 carbon atoms, and preferentially having from 2 to 6 carbon atoms, such as propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, caprylyl glycol, dipropylene glycol, diethylene glycol; and mixtures thereof.
  • an organic solvent miscible with water at room temperature 25°C
  • glycerin and glycols having from 2 to 20 carbon atoms, preferably from 2 to 10 carbon atoms, and preferentially having from 2 to 6 carbon atoms, such as propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, caprylyl glycol, dipropylene glycol, diethylene glycol; and mixtures thereof.
  • said aqueous phase is present in an amount ranging from 30 wt. %to 95 wt. %, preferably from 35 wt. %to 90 wt. %, and more preferably from 40 wt. %to 85 wt. %, relative to the total weight of the composition.
  • the composition of the present invention comprises at least one dispersed fatty phase.
  • Said fatty phase comprises at least one oil.
  • the oil can be volatile or non-volatile.
  • oil means a water-immiscible non-aqueous compound that is liquid at room temperature (25°C) and at atmospheric pressure (760 mmHg) .
  • non-volatile oil means an oil that may remain on keratin materials at room temperature and atmospheric pressure for at least several hours and that especially has a vapour pressure of less than 10 -3 mmHg (0.13 Pa) .
  • Anon-volatile oil may also be defined as having an evaporation rate such that, under the conditions defined previously, the amount evaporated after 30 minutes is less than 0.07 mg/cm 2 .
  • oils may be of plant, mineral or synthetic origin.
  • Said oil can be selected from hydrocarbonated, or silicone oils.
  • hydrocarbon-based oil means an oil formed essentially from, or even constituted by, carbon and hydrogen atoms, and optionally O and N atoms, and free of Si and F heteroatoms. Such oil can contain alcohol, ester, ether, carboxylic acid, amine and/or amide groups.
  • silicon oil means an oil containing at least one silicon atom, especially containing Si-O groups.
  • the oil is selected from hydrocarbon-based oils, such as isohexadecane, squalane, caprylic/capric triglyceride, isononyl isononanoate, pentaerythrityl tetraisostearate, , and silicone oils, such as dimethicone.
  • hydrocarbon-based oils such as isohexadecane, squalane, caprylic/capric triglyceride, isononyl isononanoate, pentaerythrityl tetraisostearate, , and silicone oils, such as dimethicone.
  • the fatty phase can also comprise a non-oil fatty substance, for example butters and waxes, such as butyrospermum parkii butter, cera alba, myristyl myristate, and beeswax, so as to build texture and deliver a suitable skin finish.
  • a non-oil fatty substance for example butters and waxes, such as butyrospermum parkii butter, cera alba, myristyl myristate, and beeswax, so as to build texture and deliver a suitable skin finish.
  • the fatty phase is present in an amount ranging from 2 wt. %to 40 wt. %, preferably from 5 wt. %to 35 wt. %, more preferably from 7 wt. %to 30 wt. %, relative to the total weight of the composition of the present invention.
  • composition according to the present invention may comprise at least one alkali metal salt of acrylic acid homopolymer.
  • the alkali metal salt of acrylic acid homopolymer suitable for use in the composition according to the invention is selected from in particular sodium polyacrylate, potassium polyacrylate, and combinations thereof.
  • Sodium polyacrylate is preferably used.
  • the acrylic acid homopolymer may be advantageously neutralized to a degree ranging from 5%to 80%.
  • sodium polyacrylate that can be used according to the invention, use may be made of those sold under the names Cosmedia by the company Cognis, or else sold by the company BASF, the product sold by the company Sensient under the trade reference Covacryl MV or else under the trade name by Cognis.
  • the alkali metal salt of acrylic acid homopolymer is present in an amount ranging from 0.1 wt. %to 10 wt. %, preferably from 0.2 wt.%to 8 wt. %, more preferably from 0.3 wt. %to 5 wt. %, most preferably from 0.3 wt.%to 2 wt. %, relative to the total weight of the composition.
  • composition of the present invention may comprise one or more other cosmetic active ingredient in addition to the C-glycoside.
  • composition of the present invention may also comprise conventional cosmetic adjuvants or additives, for instance fragrances, preserving agents and bactericides, pH regulators, and mixtures thereof.
  • the present invention provides a composition in the form of an oil-in-water emulsion for caring for and/or making up keratin materials comprising, relative to the total weight of the composition:
  • the weight ratio of the structuring agent selected from saturated C14-C22 fatty acids to the surfactant selected from fatty alcohols, alkylglucosides, and combinations thereof is less than 1.8.
  • composition of the present invention is in the form of oil-in-water emulsion.
  • composition according to the present invention has a lamellar texture.
  • lamellar means a liquid crystal structure, or a swollen or non-swollen crystalline lamellar hydrate phase with plane symmetry, comprising several amphiphilic bilayers arranged in parallel and separated by a liquid medium.
  • composition of the present invention can be, for example, cream.
  • composition of the present invention can be used for caring for and/or making up keratin materials, for example, the skin.
  • the present invention provides a non-therapeutic method for caring for and/or making up keratin materials, comprising applying the composition according to the first aspect of the present invention to the keratin materials.
  • compositions of invention example (IE. ) 1 and comparative examples (CE. ) 1-3 were prepared according to the amounts given in Table 2. The amount of each component is given in %by weight of the total weight of the composition containing it.
  • compositions of invention examples 1-2 are compositions according to the present invention.
  • compositions of comparative examples 1-3 do not comprise a polymer derived from a monomer of 2-acrylamido-2-methylpropanesulfonic acid.
  • compositions listed above were prepared as follows, taking the composition of invention example 1 as an example:
  • composition prepared above was stored in two transparent glass bottles (100mL) , one was put in a chamber at room temperature (25°C) , and the other was put in a chamber at 37°C. After 2 moths, the appearance of each composition was observed.
  • the composition If there is liquid in the gap between the composition and the bottle, the composition is considered to be unstable, otherwise it is stable.
  • compositions of invention examples 1-2 are stable at both 37°C and room temperature (25°C) for two months.

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Abstract

L'invention concerne une composition sous la forme d'une émulsion huile dans l'eau pour le soin et/ou le maquillage de matières kératiniques, comprenant : (i) au moins un agent structurant choisi parmi les acides gras saturés en C14-C22 ; (i) au moins un agent tensioactif choisi parmi les esters d'acides gras ; (ii) au moins un agent tensioactif choisi parmi les alcools gras, les alkylglucosides et leurs combinaisons ; (iv) au moins un polymère dérivé d'un monomère de l'acide 2-acrylamido-2-méthylpropanesulfonique ; et (v) au moins un C-glycoside.
PCT/CN2022/140920 2022-12-22 2022-12-22 Composition pour le soin et/ou le maquillage de matières kératiniques Ceased WO2024130622A1 (fr)

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CN202280101791.XA CN120569182A (zh) 2022-12-22 2022-12-22 用于护理和/或化妆角蛋白材料的组合物
PCT/CN2022/140920 WO2024130622A1 (fr) 2022-12-22 2022-12-22 Composition pour le soin et/ou le maquillage de matières kératiniques
FR2300572A FR3143984A1 (fr) 2022-12-22 2023-01-23 Composition de soin et/ou de maquillage de matières kératineuses

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US20090075935A1 (en) * 2006-07-03 2009-03-19 L'oreal Composition comprising at least one c-glycoside derivative and at least one hyaluronic acid and its cosmetic use
US20100168055A1 (en) * 2008-12-30 2010-07-01 L'oreal Combination of monosaccharide with c-glycoside derivative and use thereof
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FR3113836A1 (fr) * 2020-09-07 2022-03-11 L'oreal Composition cosmétique pour pénétration améliorée

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US20080008673A1 (en) * 2006-07-03 2008-01-10 Claudie Willemin Compositions comprising at least one C-glycoside derivative
JP6644875B2 (ja) * 2015-09-03 2020-02-12 ロレアル 少なくとも１つの反射剤の油性分散体を封入するマイクロカプセルを含む、ケラチン物質をケアし、および／またはメイクアップするための水中油型エマルジョン
FR3111550B1 (fr) * 2020-06-19 2022-12-16 Oreal Composition comprenant un sel d’acide gras à chaîne courte et au moins un acide gras à chaîne longue
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US20090075935A1 (en) * 2006-07-03 2009-03-19 L'oreal Composition comprising at least one c-glycoside derivative and at least one hyaluronic acid and its cosmetic use
US20100168055A1 (en) * 2008-12-30 2010-07-01 L'oreal Combination of monosaccharide with c-glycoside derivative and use thereof
CN104644532A (zh) * 2013-11-20 2015-05-27 株式会社爱茉莉太平洋 使用天然乳化剂的低粘度化妆品组合物
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