WO2012136564A2 - Composition cosmétique comprenant un composé acide cucurbique et un polymère semi-cristallin acrylique - Google Patents
Composition cosmétique comprenant un composé acide cucurbique et un polymère semi-cristallin acrylique Download PDFInfo
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- WO2012136564A2 WO2012136564A2 PCT/EP2012/055653 EP2012055653W WO2012136564A2 WO 2012136564 A2 WO2012136564 A2 WO 2012136564A2 EP 2012055653 W EP2012055653 W EP 2012055653W WO 2012136564 A2 WO2012136564 A2 WO 2012136564A2
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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
- A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
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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
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/06—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
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/06—Emulsions
- A61K8/062—Oil-in-water emulsions
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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
- A61K8/72—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
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
Definitions
- Cosmetic composition comprising a cucurbic acid compound and an acrylic semicrystalline polymer
- the present invention relates to a cosmetic composition in oil-in-water emulsion form comprising a cucurbic acid compound and a semicrystalline acrylic polymer, and also to the use of this composition in a process for treating human keratin materials.
- composition of the invention is intended for caring for and/or making up keratin materials.
- the term "keratin materials” is intended to denote, for example, the skin, mucous membranes, the lips, the scalp, the eyelashes, the eyebrows and the hair.
- Patent application EP-A-1 333 021 discloses hydrogenated cucurbic acid compounds such as 3-hydroxy-2-pentylcyclopentaneacetic acid for promoting desquamation of the skin and stimulating epidermal renewal, combating the signs of ageing of the skin, improving the radiance of the complexion and/or making facial skin smooth.
- these compounds are also described for their use as depigmenting agents.
- the aim of the present invention is thus to provide an oil-in-water emulsion comprising the hydrogenated cucurbic acid compound that is stable and homogeneous, especially after storage for one month, or even two months at 45°C.
- the inventor has discovered that such a stable emulsion can be obtained by using a particular semicrystalline acrylic polymer.
- the present invention relates to a composition in the form of an oil-in-water emulsion, comprising a cucurbic acid compound of formula (I) as described below, an oily phase comprising a semicrystalline polymer chosen from Cio-C 30 alkyl (meth)acrylate homopolymers, and an aqueous phase.
- the composition according to the invention is in particular a cosmetic composition.
- the present invention relates to a non- therapeutic treatment process for caring for or making up keratin materials, comprising the application to the said keratin materials of a composition in accordance with the invention.
- the process is in particular intended for care or makeup treatment of the skin.
- the cucurbic acid-based compound is a compound chosen from those corresponding to formula (I) below:
- Ri represents a radical COOR 3 , R 3 denoting a hydrogen atom or a Ci-C 4 alkyl radical, optionally substituted with one or more hydroxyl groups;
- R 2 represents a saturated or unsaturated linear hydrocarbon-based radical containing from 1 to 18 carbon atoms or a saturated or unsaturated branched or cyclic hydrocarbon-based radical containing from 3 to 18 carbon atoms; and also the optical isomers thereof, and the corresponding salts.
- Ri denotes a radical chosen from -COOH, -COOMe, -COO-CH 2 - CH 3 , -COO-CH 2 -CH(OH)-CH 2 OH, -COOCH 2 -CH 2 -CH 2 OH and -COOCH 2 - CH(OH)-CH 3 .
- Ri denotes a radical -COOH.
- R 2 denotes a linear, saturated or unsaturated hydrocarbon- based radical, preferably containing from 2 to 7 carbon atoms.
- R 2 may be a pentyl, pentenyl, hexyl or heptyl radical.
- the compound of formula (I) is chosen from 3- hydroxy-2-[(2Z)-2-pentenyl]cyclopentaneacetic acid and 3-hydroxy-2- pentylcyclopentaneacetic acid.
- compound (I) is 3-hydroxy-2- pentylcyclopentaneacetic acid; this compound may especially be in the form of the sodium salt.
- the salts of the compounds that may be used according to the invention are chosen in particular from salts of alkali metals, for example sodium or potassium; salts of alkaline-earth metals, for example calcium, magnesium or strontium; metal salts, for example zinc aluminium, manganese or copper; ammonium salts of formula NH 4 + ; quaternary ammonium salts; salts of organic amines, for instance salts of methylamine, dimethylamine, trimethylamine, triethylamine, ethylamine, 2-hydroxyethylamine, bis(2-hydroxyethyl)amine or tris(2-hydroxyethyl)amine; lysine or arginine salts.
- alkali metals for example sodium or potassium
- salts of alkaline-earth metals for example calcium, magnesium or strontium
- metal salts for example zinc aluminium, manganese or copper
- ammonium salts of formula NH 4 + quaternary ammonium salts
- Salts chosen from sodium, potassium, magnesium, strontium, copper, manganese and zinc salts are preferably used.
- the sodium salt is preferentially used.
- the compound of formula (I) defined previously may be present in the composition according to the invention in a content ranging from 1 % to 10% by weight, and preferably from 1 ,5% to 5% by weight, relative to the total weight of the composition.
- composition according to the invention comprises a semicrystalline polymer chosen from Ci 0 -C 30 alkyl (meth)acrylate homopolymers.
- polymers means compounds comprising at least two repeating units, preferably at least three repeating units and more especially at least ten repeating units.
- the term "semicrystalline polymer” means polymers comprising at least one crystallizable side chain with a first-order reversible change of phase temperature, in particular of melting (solid-liquid transition).
- crystallizable chain means a chain comprising at least 10 carbon atoms and which, if it were alone, would change from the amorphous state to the crystalline state reversibly, depending on whether one is above or below the melting point.
- a “chain” is a group of atoms, which are pendent or lateral relative to the polymer backbone.
- a semicrystalline polymer that is suitable for use in the invention may in particular have a melting point higher than the temperature of the skin.
- a semicrystalline polymer with crystallizable side chains may have a melting point of less than or equal to 80°C, in particular in a range from 30°C to 70°C, in particular from 40°C to 65°C, more particularly from 42°C to 60°C, or better still from 44°C to 56°C, or even from 44°C to 54°C, and more particularly less than 50°C.
- This melting point (Tm) may be measured by any known method and in particular using a differential scanning calorimeter (DSC).
- DSC differential scanning calorimeter
- the polymer may be chosen from homopolymers resulting from the polymerization of a monomer with a crystallizable side chain chosen from saturated Ci 0 to C 30 alkyl (meth)acrylates, which may be represented by formula (II) below:
- R represents a Ci 0 to C 30 alkyl group and X represents 0.
- the polymer is derived from the polymerization of monomers with a crystallizable chain chosen from saturated Ci 0 to C 30 alkyl (meth)acrylates, and more particularly homopolymers resulting from the polymerization of a monomer with a crystallizable chain chosen from Ci 4 -C 24 alkyl acrylates and Ci 4 -C 24 alkyl methacrylates.
- semicrystalline polymers that are suitable for the compositions according to the present invention, mention may also be made of the stearyl acrylate homopolymer, such as the product sold under the name Intelimer ® IPA 13-1 from the company Landec or from the company Air Products and Chemicals, or the behenyl acrylate homopolymer (such as Intelimer ® IPA-13.6) (INCI name: Poly C10-30 alkyl acrylate).
- Intelimer ® IPA 13-1 from the company Landec or from the company Air Products and Chemicals
- behenyl acrylate homopolymer such as Intelimer ® IPA-13.6
- the semicrystalline polymer may be present in the composition according to the invention in an amount ranging from 0, 1 % to 3% by weight, relative to the total weight of the composition.
- the content of the said polymer may range from 0, 1 % to 2,5% by weight relative to the total weight of the composition.
- the content of the said polymer may range from 0,2% to 2% by weight relative to the total weight of the composition.
- the cucurbic acid compound of formula (I) (referred to as A) and the semicrystalline polymer (referred to as B) described previously may be present in the composition according to the invention in an A/B weight ratio ranging from 0,5 to 2.
- this A/B weight ratio may range from 0,7 to 1 ,5.
- the cosmetic composition according to the invention comprises a physiologically acceptable medium, i.e. a medium that is compatible with human keratin materials and/or fibres, for instance, in a non-limiting manner, the skin, mucous membranes, the nails, the scalp and/or the hair.
- a physiologically acceptable medium i.e. a medium that is compatible with human keratin materials and/or fibres, for instance, in a non-limiting manner, the skin, mucous membranes, the nails, the scalp and/or the hair.
- the composition comprises an aqueous phase.
- the composition may comprise water in a content ranging from 20% to 95% by weight, preferably ranging from 30% to 90% by weight and preferentially ranging from 40% to 70% by weight, relative to the total weight of the composition.
- the water may be a floral water, for instance cornflower water and/or a mineral water, for instance Vittel water, Lucas water or La Roche Posay water and/or a spring water.
- a floral water for instance cornflower water and/or a mineral water, for instance Vittel water, Lucas water or La Roche Posay water and/or a spring water.
- composition may also comprise an organic solvent that is water-miscible at room temperature (25°C), chosen especially from monoalcohols containing from 2 to 6 carbon atoms, such as ethanol or isopropanol;
- polyols especially containing from 2 to 20 carbon atoms, preferably containing from 2 to 10 carbon atoms and preferentially containing from 2 to 6 carbon atoms, such as glycerol, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, dipropylene glycol or diethylene glycol;
- glycol ethers (especially containing from 3 to 16 carbon atoms) such as mono-, di- or tripropylene glycol (Ci-C 4 )alkyl ethers, and mono-, di- or triethylene glycol (Ci-C 4 )alkyl ethers;
- composition according to the invention may comprise a solvent that is miscible with water at room temperature, in a content ranging from 1 % to 20% by weight and preferably ranging from 3% to 15% by weight relative to the total weight of the composition.
- the composition according to the invention has a pH ranging from 5,5 to 7,5.
- the emulsion according to the invention also comprises an oily phase.
- oils that may be used in the composition of the invention, examples that may be mentioned include: - hydrocarbon-based oils of plant origin, such as liquid triglycerides of fatty acids containing from 4 to 10 carbon atoms, for instance heptanoic or octanoic acid triglycerides, or alternatively, for example, sunflower oil, corn oil, soybean oil, marrow oil, grapeseed oil, sesame seed oil, hazelnut oil, apricot oil, macadamia oil, arara oil, castor oil, avocado oil, caprylic/capric acid triglycerides, for instance those sold by the company Stearineries Dubois or those sold under the names Miglyol 810, 812 and 818 by the company Dynamit Nobel, jojoba oil and shea butter oil;
- esters and ethers especially of fatty acids, for instance the oils of formulae R 1 COOR 2 and RiOR 2 in which Ri represents a fatty acid residue containing from 8 to 29 carbon atoms and R 2 represents a branched or unbranched hydrocarbon-based chain containing from 3 to 30 carbon atoms, for instance Purcellin oil, isononyl isononanoate, isopropyl myristate, 2- ethylhexyl palmitate, 2-octyldodecyl stearate, 2-octyldodecyl erucate or isostearyl isostearate; hydroxylated esters, for instance isostearyl lactate, octyl hydroxystearate, octyldodecyl hydroxystearate, diisostearyl malate or triisocetyl citrate; fatty alcohol heptanoates, octanoates or decanoates;
- hydrocarbons of mineral or synthetic origin such as volatile or non-volatile liquid paraffins, and derivatives thereof, petroleum jelly, polydecenes, and hydrogenated polyisobutene such as Parleam oil;
- - fatty alcohols containing from 8 to 26 carbon atoms for instance cetyl alcohol, stearyl alcohol and a mixture thereof (cetylstearyl alcohol), octyldodecanol, 2- butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol, oleyl alcohol or linoleyl alcohol;
- silicone oils for instance volatile or non-volatile polymethylsiloxanes (PDMS) with a linear or cyclic silicone chain, which are liquid or pasty at room temperature, especially cyclopolydimethylsiloxanes (cyclomethicones) such as cyclohexasiloxane; polydimethylsiloxanes comprising alkyl, alkoxy or phenyl groups, which are pendent or at the end of a silicone chain, these groups containing from 2 to 24 carbon atoms; phenylsilicones, for instance phenyl trimethicones, phenyl dimethicones, phenyltrimethylsiloxydiphenylsiloxanes, diphenyl dimethicones, diphenylmethyldiphenyltrisiloxanes or 2-phenylethyl trimethylsiloxy silicates, and polymethylphenylsiloxanes;
- PDMS volatile or non-volatile polymethylsiloxanes
- hydrocarbon-based oil means any oil mainly comprising carbon and hydrogen atoms, and possibly ester, ether, fluoro, carboxylic acid and/or alcohol groups.
- the other fatty substances that may be present in the oily phase are, for example, fatty acids containing from 8 to 30 carbon atoms, for instance stearic acid, lauric acid, palmitic acid and oleic acid; waxes, for instance lanolin wax, beeswax, carnauba wax or candelilla wax, paraffin wax, lignite wax or microcrystalline waxes, ceresin or ozokerite, and synthetic waxes, for instance polyethylene waxes and Fischer-Tropsch waxes; silicone resins such as trifluoromethyl-Ci- 4 -alkyl dimethicone and trifluoropropyl dimethicone; and silicone elastomers, for instance the products sold under the name KSG by the company Shin-Etsu, under the name Trefil, BY29 or EPSX by the company Dow Corning, or under the name Gransil by the company Grant Industries.
- the proportion of the oily phase of the emulsion may range from 5%
- composition according to the invention may comprise an elastomer.
- emulsifiers examples include: oxyalkylenated (more particularly polyoxyethylenated) fatty acid esters of glycerol; oxyalkylenated (more particularly polyoxyethylenated) fatty acid esters of sorbitan; oxyalkylenated (oxyethylenated and/or oxypropylenated) fatty acid esters; oxyalkylenated (oxyethylenated and/or oxypropylenated) fatty alcohol ethers; sugar esters such as sucrose stearate; and mixtures thereof, such as the mixture of glyceryl stearate and PEG-40 stearate (polyethylene glycol containing 40 ethylene oxide units);
- the emulsifier may be a fatty acid ester of polyethylene glycol.
- the fatty acid ester of polyethylene glycol is preferably a C16-C22 fatty acid ester comprising from 8 to 100 ethylene oxide units.
- the fatty chain of the esters or ethers described previously may be a C12-C22 chain; it may be chosen especially from stearyl, behenyl, arachidyl, palmityl and cetyl chains and mixtures thereof such as cetearyl.
- the fatty chain is a stearyl chain.
- the number of ethylene oxide or propylene oxide units may range from 8 to 100, preferably from 10 to 80, better still from 10 to 50. According to one particular embodiment of the invention, this number may range from 20 to 40.
- fatty acid esters of polyethylene glycol mention may be made of stearic acid esters respectively comprising 20, 30, 40, 50 and 100 ethylene oxide units, such as the products respectively sold under the names Myrj 49 P (polyethylene glycol 20 EO stearate; CTFA name: PEG-20 stearate), Myrj 51 , Myrj 52 P (polyethylene glycol 40 EO stearate; CTFA name: PEG-40 stearate), Myrj 53 and Myrj 59 P by Croda.
- Myrj 49 P polyethylene glycol 20 EO stearate
- CTFA name PEG-20 stearate
- Myrj 51 , Myrj 52 P polyethylene glycol 40 EO stearate; CTFA name: PEG-40 stearate
- Myrj 53 and Myrj 59 P by Croda.
- the fatty acid esters of glycerol may be obtained especially from an acid comprising a saturated linear alkyl chain containing from 16 to 22 carbon atoms.
- Fatty acid esters of glycerol that may especially be mentioned include glyceryl stearate (glyceryl mono-, di- and/or tristearate) (CTFA name: Glyceryl stearate), glyceryl ricinoleate, and their mixtures.
- the fatty acid ester of glycerol used is chosen from glyceryl stearates.
- the composition according to the invention may comprise a mixture of a fatty acid ester of polyethylene glycol and a fatty acid ester of glycerol as described previously.
- the composition of the invention may especially comprise a mixture of glyceryl stearate and of polyethylene glycol 100 EO monostearate and in particular that comprising a 50/50 mixture sold under the name Arlacel 165 by the company Croda.
- the emulsifier may be present in a composition of the invention in a proportion ranging from 0, 1 % to 30% by weight and in particular from 0,5% to 20% by weight relative to the total weight of the composition.
- composition according to the invention may comprise a hydrophilic gelling agent for thickening the aqueous phase of the composition (different from semicristalline polymer according to the invention).
- the hydrophilic gelling agent may be chosen, for example, from:
- carboxyvinyl polymers for instance optionally crosslinked acrylic acid polymers
- Carbopol INCCI name: Carbomer
- sodium polyacrylate (ii) polyacrylamides and 2-acrylamido-2-methylpropanesulfonic acid polymers and copolymers, optionally crosslinked and/or neutralized, for instance the poly(2-acrylamido-2-methylpropanesulfonic acid) sold by the company Hoechst under the name Hostacerin AMPS (INCI name: ammonium polyacryloyldimethyltaurate); crosslinked anionic copolymers of acrylamide and of AMPS, which are in the form of an emulsion, such as those sold under the name Sepigel 305 (CTFA name : Polyacrylamide/Ci 3- i 4 lsoparaffin/Laureth-7) and under the name Simulgel 600 (CTFA name: : Acrylamide/sodium acryloyldimethyl
- polysaccharides such as xanthan gums, guar gums, alginates, and cellulose polymers, for instance hydroxyethylcellulose, hydroxypropylcellulose and carboxymethylcellulose;
- inorganic compounds such as modified or unmodified smectites and hectorites, such as the Bentone products sold by the company Rheox, the Laponite products sold by the company Southern Clay Products, and the product Veegum HS sold by the company R.T. Vanderbilt.
- hydrophilic gelling agents the polysaccharides described previously will be chosen more particularly, and in particular xanthan gum.
- the hydrophilic gelling agent may be present in the composition according to the invention in a content ranging from 0,01 % to 10% by weight, preferably ranging from 0, 1 % to 5% by weight and preferentially ranging from 0, 1 % to 3% by weight relative to the total weight of the composition.
- composition according to the invention may also contain adjuvants that are common in the field under consideration, such as emulsifiers, lipophilic gelling agents, waxes, hydrophilic or lipophilic additives, preserving agents, antioxidants, solvents, fragrances, fillers, UVA and/or UVB screening agents (organic or mineral, soluble or insoluble), pigments, fibres, chelating agents, odour absorbers, dyestuffs and other cosmetic active agents.
- adjuvants that are common in the field under consideration, such as emulsifiers, lipophilic gelling agents, waxes, hydrophilic or lipophilic additives, preserving agents, antioxidants, solvents, fragrances, fillers, UVA and/or UVB screening agents (organic or mineral, soluble or insoluble), pigments, fibres, chelating agents, odour absorbers, dyestuffs and other cosmetic active agents.
- the amounts of these various adjuvants are those conventionally used in the cosmetics field, and may range, for example, from 0,01 % to 30% of the total weight of the composition. In general, the amounts are adjusted as a function of the formulation prepared.
- the composition according to the invention may comprise a silicone elastomer.
- silicone elastomers are described in patent application WO-A-2009/080 958.
- a composition according to the invention may be in the form of a care product, an antisun or after-sun product, a daily photoprotective care product, a body product, a foundation to be applied to the face or the neck, a concealer product, a complexion corrector, a tinted cream or a makeup base for making up the face, or a body makeup composition.
- Examples 1 and 2 A composition (facial care cream) according to the invention (Ex. 1 ) containing the sodium salt of 3-hydroxy-2-pentylcyclopentaneacetic acid and the semicrystalline polymer of polystearyl acrylate homopolymer (Intelimer ® IPA 13- 1 from the company Air Products and Chemicals) was prepared, as was a similar composition not forming part of the invention: (without the semicrystalline polymer (Ex. 2)).
- Example 1 (invention) 2 (outside the invention)
- Ex. 2 containing the sodium salt of 3-hydroxy-2-pentylcyclopentaneacetic acid and not containing any semicrystalline polymer according to the invention is unstable.
- the semicrystalline polymer thus makes it possible to obtain a stable composition containing the acidic active agent.
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Abstract
L'invention concerne une composition cosmétique sous forme d'émulsion huile-dans-eau comprenant un composé acide cucurbique de la Formule (I), dans laquelle R1 représente un radical COOR3, R3 désignant H ou un radical alkyle en C1-C4, facultativement substitué par un ou plusieurs groupes hydroxyle ; R2 représente un radical à base d'hydrocarbure contenant de 1 à 18 atomes de carbone ; une phase huileuse comprenant un polymère semi-cristallin choisi parmi les homopolymères de (méth)acrylate d'alkyle en C10-C30 et une phase aqueuse. L'invention concerne également une utilisation pour prendre soin et conditionner des matières kératiniques.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
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FR1152902 | 2011-04-05 | ||
FR1152902A FR2973691B1 (fr) | 2011-04-05 | 2011-04-05 | Composition cosmetique comprenant un compose d'acide cucurbique et un polymere acrylique semicristallin |
US201161473893P | 2011-04-11 | 2011-04-11 | |
US61/473,893 | 2011-04-11 |
Publications (2)
Publication Number | Publication Date |
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WO2012136564A2 true WO2012136564A2 (fr) | 2012-10-11 |
WO2012136564A3 WO2012136564A3 (fr) | 2014-02-06 |
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Application Number | Title | Priority Date | Filing Date |
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PCT/EP2012/055653 WO2012136564A2 (fr) | 2011-04-05 | 2012-03-29 | Composition cosmétique comprenant un composé acide cucurbique et un polymère semi-cristallin acrylique |
Country Status (2)
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FR (1) | FR2973691B1 (fr) |
WO (1) | WO2012136564A2 (fr) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014147513A1 (fr) * | 2013-03-22 | 2014-09-25 | L'oreal | Compositions de mascara comportant un polymère semi-cristallin, un élastomère de silicone, et un agent gélifiant hydrophile |
WO2015007567A1 (fr) * | 2013-07-18 | 2015-01-22 | L'oreal | Composition cosmétique comprenant un composé d'acide cucurbique et un tensioactif anionique à base d'acide aminé |
US9034833B1 (en) | 2013-12-20 | 2015-05-19 | L'oreal | Anti-aging composition containing high levels of a jasmonic acid derivative |
US9237998B2 (en) | 2013-12-20 | 2016-01-19 | L'oreal | Carrier system for water-soluble active ingredients |
US9539198B2 (en) | 2013-12-20 | 2017-01-10 | L'oreal | Photoprotection composition containing high levels of water-soluble UV filters |
US9545373B2 (en) | 2013-12-20 | 2017-01-17 | L'oreal | Translucent cosmetic composition in the form of a water-in-oil emulsion |
US9943477B2 (en) | 2013-12-20 | 2018-04-17 | L'oreal | Emulsion compositions containing a novel preservative system |
CN108295306A (zh) * | 2017-12-22 | 2018-07-20 | 香港大学深圳医院 | 一种含介孔纳米磷酸钙颗粒填料的三维打印水凝胶材料及其制备方法 |
WO2020132855A1 (fr) * | 2018-12-25 | 2020-07-02 | L'oreal | Composition pour éclaircir ou blanchir des matières kératiniques |
WO2020132860A1 (fr) * | 2018-12-25 | 2020-07-02 | L'oreal | Composition pour éclaircir ou blanchir des matières kératiniques |
WO2020132856A1 (fr) * | 2018-12-25 | 2020-07-02 | L'oreal | Composition pour éclaircir ou blanchir des matières kératiniques |
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EP1333021A2 (fr) | 2002-02-04 | 2003-08-06 | L'oreal | Compositions comprenant des dérivés de l'acide jasmonique, et utilisation de ces dérivés pour favoriser la desquamation |
FR2921255A1 (fr) | 2007-09-21 | 2009-03-27 | Oreal | Utilisation d'un derive d'acide jasmonique a titre d'agent depigmentant |
WO2009080958A2 (fr) | 2007-12-05 | 2009-07-02 | L'oreal | Procédé cosmétique de maquillage et/ou de soin utilisant une résine de siloxane et un élastomère d'organopolysiloxane |
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US4552755A (en) * | 1984-05-18 | 1985-11-12 | Minnesota Mining And Manufacturing Company | Substantive moisturizing compositions |
FR2902000B1 (fr) * | 2006-06-09 | 2008-11-14 | Oreal | Composition h/e contenant un polymere hydrophile et un polymere semi-cristallin |
FR2921262B1 (fr) * | 2007-09-24 | 2009-11-13 | Oreal | Emulsion cosmetique de type huile dans eau |
FR2940609B1 (fr) * | 2008-12-30 | 2011-05-06 | Oreal | Association de monosaccharides et d'agents desquamants et son utilisation en cosmetique |
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JPH02295912A (ja) | 1989-05-10 | 1990-12-06 | Shiseido Co Ltd | 肌用化粧料 |
EP1333021A2 (fr) | 2002-02-04 | 2003-08-06 | L'oreal | Compositions comprenant des dérivés de l'acide jasmonique, et utilisation de ces dérivés pour favoriser la desquamation |
FR2921255A1 (fr) | 2007-09-21 | 2009-03-27 | Oreal | Utilisation d'un derive d'acide jasmonique a titre d'agent depigmentant |
WO2009080958A2 (fr) | 2007-12-05 | 2009-07-02 | L'oreal | Procédé cosmétique de maquillage et/ou de soin utilisant une résine de siloxane et un élastomère d'organopolysiloxane |
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WO2014147513A1 (fr) * | 2013-03-22 | 2014-09-25 | L'oreal | Compositions de mascara comportant un polymère semi-cristallin, un élastomère de silicone, et un agent gélifiant hydrophile |
WO2015007567A1 (fr) * | 2013-07-18 | 2015-01-22 | L'oreal | Composition cosmétique comprenant un composé d'acide cucurbique et un tensioactif anionique à base d'acide aminé |
FR3008611A1 (fr) * | 2013-07-18 | 2015-01-23 | Oreal | Composition cosmetique comprenant un compose d'acide cucurbique et un tensioactif anionique derive d'acide amine |
US9545373B2 (en) | 2013-12-20 | 2017-01-17 | L'oreal | Translucent cosmetic composition in the form of a water-in-oil emulsion |
US9237998B2 (en) | 2013-12-20 | 2016-01-19 | L'oreal | Carrier system for water-soluble active ingredients |
US9539198B2 (en) | 2013-12-20 | 2017-01-10 | L'oreal | Photoprotection composition containing high levels of water-soluble UV filters |
US9034833B1 (en) | 2013-12-20 | 2015-05-19 | L'oreal | Anti-aging composition containing high levels of a jasmonic acid derivative |
US9943477B2 (en) | 2013-12-20 | 2018-04-17 | L'oreal | Emulsion compositions containing a novel preservative system |
CN108295306A (zh) * | 2017-12-22 | 2018-07-20 | 香港大学深圳医院 | 一种含介孔纳米磷酸钙颗粒填料的三维打印水凝胶材料及其制备方法 |
CN108295306B (zh) * | 2017-12-22 | 2020-12-25 | 香港大学深圳医院 | 一种含介孔纳米磷酸钙颗粒填料的三维打印水凝胶材料及其制备方法 |
WO2020132855A1 (fr) * | 2018-12-25 | 2020-07-02 | L'oreal | Composition pour éclaircir ou blanchir des matières kératiniques |
WO2020132860A1 (fr) * | 2018-12-25 | 2020-07-02 | L'oreal | Composition pour éclaircir ou blanchir des matières kératiniques |
WO2020132856A1 (fr) * | 2018-12-25 | 2020-07-02 | L'oreal | Composition pour éclaircir ou blanchir des matières kératiniques |
CN113226253A (zh) * | 2018-12-25 | 2021-08-06 | 莱雅公司 | 用于增亮或增白角蛋白材料的组合物 |
Also Published As
Publication number | Publication date |
---|---|
FR2973691B1 (fr) | 2013-03-29 |
WO2012136564A3 (fr) | 2014-02-06 |
FR2973691A1 (fr) | 2012-10-12 |
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