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WO2024000388A1 - 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
WO2024000388A1
WO2024000388A1 PCT/CN2022/102784 CN2022102784W WO2024000388A1 WO 2024000388 A1 WO2024000388 A1 WO 2024000388A1 CN 2022102784 W CN2022102784 W CN 2022102784W WO 2024000388 A1 WO2024000388 A1 WO 2024000388A1
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Prior art keywords
composition
hydroxypropane
acid
composition according
saturated
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PCT/CN2022/102784
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English (en)
Inventor
Hongling Xu
Yangdong CHEN
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LOreal SA
Original Assignee
LOreal SA
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Priority to CN202280096446.1A priority Critical patent/CN119255780A/zh
Priority to PCT/CN2022/102784 priority patent/WO2024000388A1/fr
Priority to FR2207736A priority patent/FR3138308B1/fr
Publication of WO2024000388A1 publication Critical patent/WO2024000388A1/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
    • A61K8/33—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
    • A61K8/60—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
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/732—Starch; Amylose; Amylopectin; Derivatives 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/735—Mucopolysaccharides, e.g. hyaluronic acid; Derivatives 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
    • A61K8/72—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
    • A61K8/8147—Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; 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
    • A61K8/8152—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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin

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) .
  • compositions in the form of creams or emulsions.
  • the product is stable at room temperature and even at a high temperature for example above 55°C.
  • moisturizing agents which are in particular hygroscopic substances that cause rehydration of the skin by capturing atmospheric water and by retention of water in the skin.
  • Hyaluronic acid (HA) and salts thereof are commonly used as moisturizing agents in cosmetic products.
  • phase separation is easy to occur and there will be water leakage or oil leakage.
  • compositions for caring for and/or making up the skin comprising at least one moisturizing agent, which is stable at room temperature (for example, 25°C) immediately after it was prepared and at a relatively high temperature for example 55°C.
  • compositions being stable at room temperature (for example, 25°C) immediately after it was prepared and at a relatively high temperature for example 55°C for at least one week.
  • 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 moisturizing agent selected from optionally acetylated hyaluronic acid and salts thereof;
  • 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.
  • composition of the present invention has a lamellar texture and is stable at room temperature (for example, 25°C) immediately after it was prepared and at a relatively high temperature for example 55°C for at least one week.
  • 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.
  • Fig. 1 shows polarized light microscopy image of the composition obtained in invention example 1.
  • 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 moisturizing agent selected from optionally acetylated hyaluronic acid and salts thereof;
  • the composition of the present invention comprises at least one structuring agent selected from saturated C14-C22 fatty acids.
  • saturated C14-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 1.3 wt. %to 10 wt. %, most preferably from 1.3 wt. %to 4 wt. %, relative to the total weight of the composition.
  • the composition according to the present invention comprises at least one hydrophilic gelling agent.
  • the hydrophilic gelling agent is capable of swelling in water to form a microgel in the form of particles with a particle size of 50-400 ⁇ m.
  • the hydrophilic gelling agent is selected from alkali metal salts of acrylic acid homopolymers, modified starches, and mixtures thereof.
  • the homopolymer suitable for use in the composition according to the invention is chosen in particular from sodium polyacrylates and potassium polyacrylates.
  • 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 EM 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.
  • modified starches suitable for use in the composition according to the invention is chosen in particular from those derived from maize starch, rice starch, cassava starch, potato starch, wheat starch, sorghum starch, pea starch, and mixtures thereof.
  • modified starches mention may be made of precooked starches, hydrolysed starches, crosslinked starches, for example crosslinked with a methylolurea derivative or with octenylsuccinic anhydride or else with epichlorohydrin, esterified starches, etherified starches, oxidized starches, refined starches, starches roasted in the presence of an acid, or else grafted starches, for example grafted with sodium polyacrylates, coated starches, for example coated with amino acids, and/or mixtures thereof.
  • modified starches that are particularly suitable for the invention, mention may be made of:
  • the hydrophilic gelling agent is selected from sodium polyacrylates, potassium polyacrylates, sodium polyacrylate starch, sodium polyacrylate starch, and mixtures thereof.
  • the hydrophilic gelling agent 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.
  • the composition of the present invention comprises at least one surfactant different from saturated C14-C22 fatty acids.
  • the surfactant is selected from:
  • sarcosinates such as sodium lauroyl sarcosinate
  • 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 surfactant may be selected from esters of polyols with fatty acids with a saturated or unsaturated chain containing for example from 8 to 24 carbon atoms, preferably 12 to 22 carbon atoms, or polyoxyalkylenated derivatives thereof, preferably containing from 10 to 200, or more preferably from 10 to 100 oxyalkylene units, such as 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 alkylglycos
  • surfactants such as 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 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
  • esters of fatty acids and glucose or alkylglucose glucose palmitate, alkylglucose sesquistearates such as methylglucose sesquistearate, alkylglucose palmitates such as methylglucose or ethylglucose palmitate, methylglucoside fatty esters, the diester of methylglucoside and oleic acid (CTFA name: Methyl glucose dioleate) , the mixed ester of methylglucoside and the mixture of oleic acid/hydroxystearic acid (CTFA name: Methyl glucose dioleate/hydroxystearate) , the ester of methylglucoside and isostearic acid (CTFA name: Methyl glucose isostearate) , the ester of methylglucoside and lauric acid (CTFA name: Methyl glucose laurate) , the mixture of monoester and diester of methylglucoside and isostearic acid (CT
  • 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.
  • 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 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, ethers of a sugar and of C8-C24 fatty alcohols, fatty acid esters of polyalkylene glycol, C14-C24 fatty alcohols, and mixtures thereof.
  • the surfactant is selected from glyceryl stearate, PEG-100 stearate, arachidyl alcohol, behenyl alcohol, oleyl alcohol, arachidyl glucoside, and mixtures thereof.
  • the surfactant 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.
  • the composition of the present invention comprises at least one moisturizing agent selected from optionally acetylated hyaluronic acid and salts thereof.
  • Hyaluronic acid is a non-sulfated linear glycosaminoglycan composed of repeating units of D-glucuronic acid and N-acetyl-D-glucosamine.
  • the acetylated hyaluronic acid in the present invention denotes to a derivative in which the hydroxyl groups of hyaluronic acid has been at least partially acetylated.
  • Acetylated hyaluronic acid can be manufactured by any method known to persons skilled in the art, e.g., referring to JPH 0853501; or is commercially available, e.g., under the name of HymagicTM from Bloomage Biotechnology Corporation Limited.
  • the optionally acetylated hyaluronic acid salts may be chosen from alkali salts such as sodium and potassium salts or other salts, e.g., zinc salts, silver salts, and mixtures thereof.
  • the composition according to the present invention comprises at least one moisturizing agent selected from optionally acetylated hyaluronic acid, sodium, potassium, zinc and silver salts thereof.
  • the moisturizing agent selected from optionally acetylated hyaluronic acid or salts thereof is one or more of high molecular weight (HMW) or low molecular weight (LMW) optionally acetylated hyaluronic acid or salts thereof.
  • HMW high molecular weight
  • LMW low molecular weight
  • LMW optionally acetylated hyaluronic acid or salts thereof means a optionally acetylated hyaluronic acid or salts thereof having a weight average molecular weight of less than or equal to 60,000 Daltons.
  • the LMW optionally acetylated hyaluronic acid or salts thereof has a weight average molecular weight of less than or equal to 60,000 Daltons, preferably less than or equal to 50,000 Daltons, for example from 10,000 Daltons to 60,000 Daltons, preferably 15,000 Daltons to 50,000 Daltons, more particularly 20,000 Daltons to 50,000 Daltons.
  • the composition according to the invention comprises sodium hyaluronate, such as sold by GIVAUDA under the trade name of RENOVHYAL.
  • HMW optionally acetylated hyaluronic acid has a weight average molecular weight of from 80,000 Daltons to 1,500,000 Daltons, or from 100,000 Daltons to 1,000,000 Daltons.
  • the composition according to the invention comprises sodium hyaluronate, such as sold by BLOOMAGE FREDA BIOPHARM under the trade name of SODIUM HYALURONATE (HA-T) .
  • H-T SODIUM HYALURONATE
  • the useful acetylated hyaluronic acid or salts thereof has an average molecular weight of is from 10,000 to 1,000,000 Daltons, preferably 20,000 to 50,000 Daltons, or preferably 30,000 to 50,000 Daltons.
  • the acetylated hyaluronic acid or a salt thereof has an acetyl group substitution number is 2.5 to 4.0.
  • acetylated hyaluronic acid or a salt thereof is used in combination with hyaluronic acid or a salt thereof.
  • the optionally acetylated hyaluronic acid and/or a salt thereof is introduced into an aqueous phase in the composition.
  • the moisturizing agent is present in an amount ranging from 0.001 wt. %to 10 wt. %, preferably from 0.001 wt. %to 5 wt. %, more preferably, 0.001 wt. %to 1 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 ⁇ , and also their physiologically acceptable salts, their solvates, such as the hydrates, and their optical and geometrical isomers.
  • 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.
  • a monosaccharide 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.
  • a polysaccharide 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.
  • S can 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.
  • a C-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 11 wt. %to 20%, preferably from 12 wt. %to 15 wt. %, relative to the total weight of the composition.
  • the composition of the present invention comprises at least one saponifier.
  • the saponifier can be used to react with a saturated C14-C22 fatty acid to produce a salt.
  • the saponifier can be, for example, inorganic bases, such as alkali metal hydroxides (for example, sodium hydroxide and potassium hydroxide) , alkaline earth metal hydroxides (for example, magnesium hydroxide) or ammonium hydroxide, or organic bases, for example, monoethanolamine (MEA) , diethanolamine, triethanolamine, tromethamine, N-methylglucamine, arginine, lysine and arginine.
  • inorganic bases such as alkali metal hydroxides (for example, sodium hydroxide and potassium hydroxide) , alkaline earth metal hydroxides (for example, magnesium hydroxide) or ammonium hydroxide
  • organic bases for example, monoethanolamine (MEA) , diethanolamine, triethanolamine, tromethamine, N-methylglucamine, arginine, lysine and arginine.
  • the saponifier is selected from sodium hydroxide, potassium hydroxide, magnesium hydroxide, ammonium hydroxide, monoethanolamine, diethanolamine, triethanolamine, tromethamine, N-methylglucamine, arginine, lysine, arginine, and a combination thereof.
  • the molar ratio of the saponifier to the structuring agent selected from saturated C14-C22 fatty acids is from 15%to 50%
  • 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 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.
  • 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) .
  • a non-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, silicone or fluorinated 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.
  • fluorinated oil means an oil containing at least one fluorine atom.
  • the oil is selected from hydrocarbon-based oils, such as isohexadecane, squalane, caprylic/capric triglyceride, isononyl isononanoate, pentaerythrityl tetraisostearate, myristyl myristate, and silicone oils, such as dimethicone.
  • hydrocarbon-based oils such as isohexadecane, squalane, caprylic/capric triglyceride, isononyl isononanoate, pentaerythrityl tetraisostearate, myristyl myristate, 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, 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, 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 of the present invention may comprise one or more cosmetic active ingredient.
  • cosmetic active ingredient examples include natural extracts; vitamins such as vitamin A (retinol) , vitamin E (tocopherol) , vitamin C (ascorbic acid) , vitamin B5 (panthenol) , vitamin B3 (niacinamide) , and derivatives of said vitamins (in particular esters) and mixtures thereof; urea; caffeine; salicylic acid and derivatives thereof; alpha-hydroxyacids such as lactic acid or glycolic acid and derivatives thereof; sunscreens; extracts from algae, fungi, plants, yeasts and bacteria; enzymes; other moisturing agents such as hydroxyethyl urea, agents acting on the microcirculation, and mixtures thereof.
  • vitamins such as vitamin A (retinol) , vitamin E (tocopherol) , vitamin C (ascorbic acid) , vitamin B5 (panthenol) , vitamin B3 (niacinamide)
  • urea caffeine
  • salicylic acid and derivatives thereof alpha-hydroxyacids
  • composition of the present invention may also comprise conventional cosmetic adjuvants or additives, for instance fragrances, preserving agents (for example, chlorphenesin and phenoxyethanol) and bactericides, pH regulators (for example citric acid) , thickeners such as xanthan gum, and mixtures thereof.
  • fragrances for instance, fragrances, preserving agents (for example, chlorphenesin and phenoxyethanol) and bactericides, pH regulators (for example citric acid) , thickeners such as xanthan gum, and mixtures thereof.
  • preserving agents for example, chlorphenesin and phenoxyethanol
  • bactericides for example, bactericides
  • pH regulators for example citric acid
  • thickeners such as xanthan gum
  • 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:
  • hydrophilic gelling agent selected from alkali metal salts of acrylic acid homopolymers, modified starches, and mixtures thereof;
  • surfactant selected from mono-and polyglyceryl esters of a fatty acid, ethers of a sugar and of C8-C24 fatty alcohols, fatty acid esters of polyalkylene glycol, C14-C24 fatty alcohols, and mixtures thereof;
  • 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, it can be used as foundation cream, hand cream, body cream, and so on.
  • 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 examples (IE. ) 1-4 and comparative examples (CE. ) 1-4 were prepared according to the amounts given in Tables 2 and 3. The amount of each component is given in%by weight of the total weight of the composition containing it.
  • GLYCERYL STEARATE (and) PEG-100 STEARATE 1) : comprising 50 wt. %of GLYCERYL STEARATE and 50 wt. %of PEG-100 STEARATE.
  • ARACHIDYL ALCOHOL (and) BEHENYL ALCOHOL (and) ARACHIDYL GLUCOSIDE 2) : comprising 55 wt. %of ARACHIDYL ALCOHOL, 30 wt. %of BEHENYLALCOHOL and 15 wt. %of ARACHIDYL GLUCOSIDE.
  • HYDROXYPROPYL TETRAHYDROPYRANTRIOL 3 is hydroxypropyl tetrahydropyrantriol in water and propylene glycol at a content of 70 wt. %, relative to the total weight of hydroxypropyl tetrahydropyrantriol and water and propylene glycol.
  • compositions of invention examples 1-4 are compositions according to the present invention.
  • compositions of comparative examples 1-3 do not comprise C-glycoside.
  • Composition of comparative example 4 comprises less than 12 wt. %C-glycoside, relative to the total weight of the composition.
  • compositions listed above were prepared as follows, taking the composition of invention example 3 as an example:
  • Phase B premix at 85°C, then adding it to the yellowish transparent liquid at 75°C under a stirring rate of 1500 rpm and mixing for 10 minutes to obtain a white emulsion;
  • compositions was observed using a Leica DLMB microscope under 90° cross polarized light, and microscopic pictures were taken.
  • Fig. 1 shows polarized light microscopy image of the composition obtained in invention example 1.
  • compositions of invention examples 2-4 (IE. 2-4) .
  • composition If there is water leakage at room temperature (25°C) immediately after a composition was prepared, then the composition is not stable. If there is oil leakage upon storage at 55°C for 1 week, then the composition is not stable, and if there is only little oil leakage, then the composition has an acceptable stability.
  • compositions of invention examples 1-4 have a lamellar texture and are stable.

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Abstract

L'invention concerne une composition sous la forme d'une émulsion huile-dans-eau pour le soin et/ou le maquillage de matières kératiniques, comprenant : (i) au moins un agent structurant choisi parmi les acides gras C14-C22 saturés; (ii) au moins un agent gélifiant hydrophile; (iii) au moins un tensioactif différent des acides gras C14-C22 saturés; (iv) au moins un agent hydratant choisi parmi l'acide hyaluronique éventuellement acétylé et ses sels; et (v) par rapport au poids total, au moins 12 % en poids d'au moins un C-glycoside. La présente divulgation concerne également un procédé non thérapeutique de soin et/ou de maquillage des matières kératiniques, comprenant l'application de ladite composition sur les matières kératiniques.
PCT/CN2022/102784 2022-06-30 2022-06-30 Composition pour le soin et/ou le maquillage de matières kératiniques Ceased WO2024000388A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
CN202280096446.1A CN119255780A (zh) 2022-06-30 2022-06-30 用于护理和/或化妆角蛋白材料的组合物
PCT/CN2022/102784 WO2024000388A1 (fr) 2022-06-30 2022-06-30 Composition pour le soin et/ou le maquillage de matières kératiniques
FR2207736A FR3138308B1 (fr) 2022-06-30 2022-07-27 Composition pour le soin et/ou le maquillage de matières kératiniques

Applications Claiming Priority (1)

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PCT/CN2022/102784 WO2024000388A1 (fr) 2022-06-30 2022-06-30 Composition pour le soin et/ou le maquillage de matières kératiniques

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WO2024000388A1 true WO2024000388A1 (fr) 2024-01-04

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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3007974A1 (fr) * 2013-07-04 2015-01-09 Oreal Composition comprenant un derive c-glycoside ou un derive d'acide cucurbique, un corps gras pateux et un derive non ionique de cellulose modifie hydrophobe
WO2020087273A1 (fr) * 2018-10-30 2020-05-07 L'oreal Composition cosmétique pour soin de la peau
WO2020128005A1 (fr) * 2018-12-20 2020-06-25 L'oreal Composition comprenant un polysaccharide, un polyol et un ester spécifique
US20210015719A1 (en) * 2017-06-05 2021-01-21 L'oreal Stable emulsified gel composition having a high concentration of active components
US20210401715A1 (en) * 2020-06-30 2021-12-30 L'oreal Cosmetic composition for improved penetration
WO2022006047A1 (fr) * 2020-06-30 2022-01-06 L'oreal Composition cosmétique pour pénétration améliorée
WO2022129469A1 (fr) * 2020-12-18 2022-06-23 L'oreal Composition comprenant des agents gélifiants aqueux, un tensioactif et de l'acide ascorbique
WO2022129477A1 (fr) * 2020-12-18 2022-06-23 L'oreal Composition comprenant des gélifiants aqueux, un tensioactif, des huiles, des charges et de l'acide ascorbique

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2818547B1 (fr) 2000-12-22 2006-11-17 Oreal Nouveaux derives c-glycosides et utilisation
FR3029106B1 (fr) * 2014-12-02 2018-09-14 L'oreal Emulsion comprenant un tensioactif gemine ayant deux groupements amide gras et un derive c-glycoside ou un derive d'acide tetrahydrojasmonique

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3007974A1 (fr) * 2013-07-04 2015-01-09 Oreal Composition comprenant un derive c-glycoside ou un derive d'acide cucurbique, un corps gras pateux et un derive non ionique de cellulose modifie hydrophobe
US20210015719A1 (en) * 2017-06-05 2021-01-21 L'oreal Stable emulsified gel composition having a high concentration of active components
WO2020087273A1 (fr) * 2018-10-30 2020-05-07 L'oreal Composition cosmétique pour soin de la peau
WO2020128005A1 (fr) * 2018-12-20 2020-06-25 L'oreal Composition comprenant un polysaccharide, un polyol et un ester spécifique
US20210401715A1 (en) * 2020-06-30 2021-12-30 L'oreal Cosmetic composition for improved penetration
WO2022006047A1 (fr) * 2020-06-30 2022-01-06 L'oreal Composition cosmétique pour pénétration améliorée
WO2022129469A1 (fr) * 2020-12-18 2022-06-23 L'oreal Composition comprenant des agents gélifiants aqueux, un tensioactif et de l'acide ascorbique
WO2022129477A1 (fr) * 2020-12-18 2022-06-23 L'oreal Composition comprenant des gélifiants aqueux, un tensioactif, des huiles, des charges et de l'acide ascorbique

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FR3138308B1 (fr) 2025-06-20
CN119255780A (zh) 2025-01-03

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