WO2012136564A2 - Cosmetic composition comprising a cucurbic acid compound and an acrylic semicrystalline polymer - Google Patents
Cosmetic composition comprising a cucurbic acid compound and an acrylic semicrystalline polymer 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
-
- 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
-
- 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
Abstract
The invention relates to a cosmetic composition in oil-in-water emulsion form comprising a cucurbic acid compound of Formula (I), in which represents a radical COOR3, R3 denoting H or a C1-C4 alkyl radical, optionally substituted with one or more hydroxyl groups; R2 represents a hydrocarbon-based radical containing from 1 to 18 carbon atoms; an oily phase comprising a semicrystalline polymer chosen from C10-C30 alkyl (meth)acrylate homopolymers and an aqueous phase. Use for caring for and making up keratin materials.
Description
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.
More particularly, the composition of the invention is intended for caring for and/or making up keratin materials.
For the purposes of the invention, 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. In patent application FR-A-62921255, these compounds are also described for their use as depigmenting agents.
However, introducing these hydrogenated cucurbic acid compounds into an oil- in-water emulsion gives rise to instability of the composition, especially after storage for one month, or even two months at 45°C: the emulsion then shows phase separation of oil at the surface; the oil globules dispersed in the aqueous phase have a coarse aspect, making the emulsion non-uniform.
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. More specifically, 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-C30 alkyl (meth)acrylate homopolymers, and an aqueous phase. The composition according to the invention is in particular a cosmetic composition.
Surprisingly, the inventor has observed that the addition of a cucurbic acid compound to a composition comprising a semicrystalline polymer as described previously does not significantly affect the viscosity of the said composition and thus enables it to be formulated in a form that is suited to its handling during its application.
According to yet another of its subjects, 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:
in which:
Ri represents a radical COOR3, R3 denoting a hydrogen atom or a Ci-C4 alkyl radical, optionally substituted with one or more hydroxyl groups;
R2 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.
Preferably, Ri denotes a radical chosen from -COOH, -COOMe, -COO-CH2- CH3, -COO-CH2-CH(OH)-CH2OH, -COOCH2-CH2-CH2OH and -COOCH2- CH(OH)-CH3. Preferentially, Ri denotes a radical -COOH.
Preferentially, R2 denotes a linear, saturated or unsaturated hydrocarbon- based radical, preferably containing from 2 to 7 carbon atoms. In particular, R2 may be a pentyl, pentenyl, hexyl or heptyl radical.
According to one embodiment, the compound of formula (I) is chosen from 3- hydroxy-2-[(2Z)-2-pentenyl]cyclopentaneacetic acid and 3-hydroxy-2- pentylcyclopentaneacetic acid. Preferably, 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 NH4 +; 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. 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.
The composition according to the invention comprises a semicrystalline polymer chosen from Ci0-C30 alkyl (meth)acrylate homopolymers.
For the purposes of the invention, the term "polymers" means compounds comprising at least two repeating units, preferably at least three repeating units and more especially at least ten repeating units.
For the purposes of the invention, 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).
For the purposes of the invention, the expression "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. For the purposes of the invention, 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.
According to one particular embodiment, a semicrystalline polymer with crystallizable side chains that is suitable for use in the invention 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).
According to one particular embodiment of the invention, the polymer may be chosen from homopolymers resulting from the polymerization of a monomer with a crystallizable side chain chosen from saturated Ci0 to C30 alkyl (meth)acrylates, which may be represented by formula (II) below:
in which is H or CH3, R represents a Ci0 to C30 alkyl group and X represents 0.
According to a more particular embodiment of the invention, the polymer is derived from the polymerization of monomers with a crystallizable chain chosen from saturated Ci0 to C30 alkyl (meth)acrylates, and more particularly homopolymers resulting from the polymerization of a monomer with a crystallizable chain chosen from Ci4-C24 alkyl acrylates and Ci4-C24 alkyl methacrylates.
As a particular example of a semicrystalline polymer that may be used in a composition according to the invention, mention may be made of the Intelimer™ products from the company Landec described in the brochure "Intelimer™ Polymers", Landec IP22. These polymers are in solid form at room temperature. They bear crystallizable side chains and correspond to saturated Ci4-C24 alkyl acrylate or methacrylate homopolymers.
As 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).
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. Preferably, the content of the said polymer may range from 0, 1 % to 2,5% by weight relative to the total weight of the composition.
Preferentially, the content of the said polymer may range from 0,2% to 2% by weight relative to the total weight of the composition.
Advantageously, 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.
Preferably, 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.
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.
The 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-C4)alkyl ethers, and mono-, di- or triethylene glycol (Ci-C4)alkyl ethers;
and mixtures thereof. The 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. Advantageously, 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. As 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;
- synthetic esters and ethers, especially of fatty acids, for instance the oils of formulae R1COOR2 and RiOR2 in which Ri represents a fatty acid residue containing from 8 to 29 carbon atoms and R2 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; polyol esters, for instance propylene glycol dioctanoate, neopentyl glycol diheptanoate and diethylene glycol diisononanoate; and pentaerythritol esters, for instance pentaerythrityl tetraisostearate;
- linear or branched 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;
- partially hydrocarbon-based and/or silicone-based fluoro oils, for instance those described in document JP-A-2-295 912;
- 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;
- mixtures thereof. In the list of oils mentioned above, the term "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% to 80% by weight and preferably from 5% to 50% by weight relative to the total weight of the composition.
The composition according to the invention may comprise an elastomer.
Examples of emulsifiers that may be mentioned 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);
fatty acid esters of polyethylene glycol;
C16-C22 fatty acid esters of glycerol;
C16-C22 fatty acids.
According to one embodiment of the invention, 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. Preferably, 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.
As examples of 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.
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. Preferably, the fatty acid ester of glycerol used is chosen from glyceryl stearates.
In particular, 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.
The 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:
(i) carboxyvinyl polymers (for instance optionally crosslinked acrylic acid polymers), such as the products sold under the names Carbopol (INCI name: Carbomer) by the company Goodrich; 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/Ci3-i4 lsoparaffin/Laureth-7) and under the name Simulgel 600 (CTFA name: : Acrylamide/sodium acryloyldimethyltaurate copolymer/isohexadecane/polysorbate 80) by the company SEPPIC; crosslinked anionic copolymers of acrylic acid and of AMPS, which are in the form of an emulsion, such as those sold under the name Simulgel EG (CTFA name: Sodium acrylate/sodium acryloyldimethyltaurate copolymer/isohexadecane/polysorbate 80); 2-acrylamido-2- methylpropanesulfonic acid/ethoxylated C12-C14 alkyl methacrylate copolymers (Aristoflex LNC from Clariant), 2-acrylamido-2- methylpropanesulfonic acid/ethoxylated stearyl methacrylate copolymers (Aristoflex HMS and Aristoflex SNC from Clariant);
(iii) polysaccharides such as xanthan gums, guar gums, alginates, and cellulose polymers, for instance hydroxyethylcellulose, hydroxypropylcellulose and carboxymethylcellulose;
(iv) 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.
Among these 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.
The 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.
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.
Advantageously, the composition according to the invention may comprise a silicone elastomer. Examples of 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.
Other characteristics and advantages of the invention will emerge more clearly from the examples that follow, which are given as non-limiting illustrations. In the text hereinbelow or hereinabove, the proportions are given as weight percentages, unless otherwise indicated.
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)).
For each composition, the following were performed:
centrifugation for 1 hour at 25°C and 900 χ g;
a microscopic evaluation of the composition.
The following results were obtained:
Example 1 (invention) 2 (outside the invention)
Sodium salt of 3-hydroxy-2- 6,67%, i.e. 6,67%, i.e. 2% pentylcyclopentaneacetic acid 2% AM AM at 30% in a water/dipropylene
glycol mixture (70/30 by
weight)
Water qs 100 % qs 100 %
Disodium salt of 0,3 0,3 ethylenediaminetetraacetic acid
Adenosine 0, 1 0, 1
Beeswax 2 2
Shea butter 5 5
2-Ethylhexyl salicylate 5 5
2-Ethylhexyl cyano-3,3- 7 7 diphenylacrylate
Homomenthyl salicylate 6 6
Xanthan gum (Rhodicare XC 0,2 0,2 from Rhodia)
Acrylic acid/C10-C30 alkyl 0,3 0,3 methacrylate crosslinked
copolymer (Pemulen TR-2
Polymer from Lubrizol)
Sodium polyacrylate (Cosmedia 0,5 0,5 SP from Cognis)
Polystearyl acrylate (Intelimer 2 0 IPA 13-1 from Landec)
Silica microspheres (Sunsphere 1 1
H 51 from AGC Sl-Tech)
Dimethicone 10 cSt 3,5 3,5
Mixture of cross I inked 3 3
polydimethylsiloxane and of
polydimethylsiloxane (6 cSt)
(24/76) (KSG16 from Shin-Etsu)
Glycerol 5 5
Sodium hyaluronate (Cristalhyal 0, 1 0, 1
from Soliance)
Caprylyl glycol 0,3 0,3
Stearic acid 1 ,2 1 ,2
Mixture of glyceryl stearate and 2 2
PEG-100 stearate (Arlacel® 165
FL from Uniqema)
Preserving agent qs qs
centrifugation HomoNon- geneous homogeneous
Microscopic appearance HomoHeterogeneous geneous
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 formula according to the invention (Ex. 1 ) containing the sodium salt of 3- hydroxy-2-pentylcyclopentaneacetic acid and the semicrystalline polymer is stable and homogeneous.
The semicrystalline polymer thus makes it possible to obtain a stable composition containing the acidic active agent.
Claims
1 . Cosmetic composition in the form of an oil-in-water emulsion comprising a compound of formula (I) below:
in which:
Ri represents a radical COOR3, R3 denoting a hydrogen atom or a Ci-C4 alkyl radical, optionally substituted with one or more hydroxyl groups; R2 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;
an oily phase comprising a semicrystalline polymer chosen from Ci0-C30 alkyl (meth)acrylate homopolymers,
and an aqueous phase.
2. Composition according to Claim 1 , characterized in that compound (I) is such that Ri denotes a radical chosen from -COOH, -COOMe, -COO-CH2-CH3, -
COO-CH2-CH(OH)-CH2OH, -COOCH2-CH2-CH2OH and -COOCH2-CH(OH)- CH3;
R2 denotes a linear, saturated or unsaturated hydrocarbon-based radical containing from 2 to 6 carbon atoms.
3. Composition according to Claim 1 or 2, characterized in that compound (I) is 3-hydroxy-2-pentylcyclopentaneacetic acid.
4. Composition according to any one of the preceding claims, characterized in that the compound of formula (I) is present in a content ranging from 1 % to 10% by weight and preferably ranging from 1 .5% to 5% by weight relative to the total weight of the composition.
5. Composition according to any one of the preceding claims, characterized in that the semicrystalline acrylic polymer is chosen from stearyl acrylate homopolymers and behenyl acrylate homopolymers.
6. Composition according to any one of the preceding claims, characterized in that the semicrystalline acrylic polymer is chosen from stearyl acrylate homopolymers.
7. Composition according to any one of the preceding claims, characterized in that the semicrystalline acrylic polymer is present in a content ranging from 0.1 % to 3% by weight, preferably ranging from 0.1 % to 2,5% by weight and preferentially ranging from 0.2% to 2% by weight relative to the total weight of the composition.
8. Composition according to any one of the preceding claims, characterized in that it comprises an emulsifier.
9. Composition according to any one of the preceding claims, characterized in that it comprises an emulsifier chosen from:
oxyalkylenated fatty acid esters of glycerol; oxyalkylenated fatty acid esters of sorbitan; oxyalkylenated fatty acid esters; oxyalkylenated fatty alkyl ethers; sugar esters such as sucrose stearate; and mixtures thereof;
fatty acid esters of polyethylene glycol;
C16-C22 fatty acid esters of glycerol;
C16-C22 fatty acids.
10. Composition according to any one of the preceding claims, characterized in that it comprises a hydrophilic gelling agent.
1 1 . Non-therapeutic process for treating keratin materials, comprising the application to the said keratin materials of a cosmetic composition as defined according to one of the preceding claims.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR1152902 | 2011-04-05 | ||
FR1152902A FR2973691B1 (en) | 2011-04-05 | 2011-04-05 | COSMETIC COMPOSITION COMPRISING A CUCURBIC ACID COMPOUND AND A SEMICRYSTALLINE ACRYLIC POLYMER |
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 (en) | 2012-10-11 |
WO2012136564A3 WO2012136564A3 (en) | 2014-02-06 |
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Cited By (11)
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WO2014147513A1 (en) * | 2013-03-22 | 2014-09-25 | L'oreal | Mascara compositions comprising a semicrystalline polymer, a silicone elastomer, and a hydrophilic gelling agent |
WO2015007567A1 (en) * | 2013-07-18 | 2015-01-22 | L'oreal | Cosmetic composition comprising a cucurbic acid compound and an amino acid-based anionic surfactant |
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 (en) * | 2017-12-22 | 2018-07-20 | 香港大学深圳医院 | A kind of 3 D-printing hydrogel material of containing mesopore nano-calcium phosphate granular filler and preparation method thereof |
WO2020132856A1 (en) * | 2018-12-25 | 2020-07-02 | L'oreal | Composition for brightening or whitening keratin materials |
WO2020132855A1 (en) * | 2018-12-25 | 2020-07-02 | L'oreal | Composition for brightening or whitening keratin materials |
WO2020132860A1 (en) * | 2018-12-25 | 2020-07-02 | L'oreal | Composition for brightening or whitening keratin materials |
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JPH02295912A (en) | 1989-05-10 | 1990-12-06 | Shiseido Co Ltd | Cosmetic |
EP1333021A2 (en) | 2002-02-04 | 2003-08-06 | L'oreal | Compositions containing derivatives of jasmonic acid and their use for stimulating skin peeling |
FR2921255A1 (en) | 2007-09-21 | 2009-03-27 | Oreal | Cosmetic use of jasmonic acid derivative, to prepare a composition for depigmenting and bleaching of the skin, to reduce or eliminate the pigmentation, and/or to reduce the size of lentigo |
WO2009080958A2 (en) | 2007-12-05 | 2009-07-02 | L'oreal | Cosmetic make-up and/or care method using a siloxane resin and an organopolysiloxane elastomer |
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FR2902000B1 (en) * | 2006-06-09 | 2008-11-14 | Oreal | O / W COMPOSITION CONTAINING HYDROPHILIC POLYMER AND SEMI-CRYSTALLINE POLYMER |
FR2921262B1 (en) * | 2007-09-24 | 2009-11-13 | Oreal | COSMETIC EMULSION OF OIL TYPE IN WATER |
FR2940609B1 (en) * | 2008-12-30 | 2011-05-06 | Oreal | ASSOCIATION OF MONOSACCHARIDES AND DESQUAMANT AGENTS AND USE THEREOF IN COSMETICS |
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JPH02295912A (en) | 1989-05-10 | 1990-12-06 | Shiseido Co Ltd | Cosmetic |
EP1333021A2 (en) | 2002-02-04 | 2003-08-06 | L'oreal | Compositions containing derivatives of jasmonic acid and their use for stimulating skin peeling |
FR2921255A1 (en) | 2007-09-21 | 2009-03-27 | Oreal | Cosmetic use of jasmonic acid derivative, to prepare a composition for depigmenting and bleaching of the skin, to reduce or eliminate the pigmentation, and/or to reduce the size of lentigo |
WO2009080958A2 (en) | 2007-12-05 | 2009-07-02 | L'oreal | Cosmetic make-up and/or care method using a siloxane resin and an organopolysiloxane elastomer |
Cited By (14)
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WO2014147513A1 (en) * | 2013-03-22 | 2014-09-25 | L'oreal | Mascara compositions comprising a semicrystalline polymer, a silicone elastomer, and a hydrophilic gelling agent |
WO2015007567A1 (en) * | 2013-07-18 | 2015-01-22 | L'oreal | Cosmetic composition comprising a cucurbic acid compound and an amino acid-based anionic surfactant |
FR3008611A1 (en) * | 2013-07-18 | 2015-01-23 | Oreal | COSMETIC COMPOSITION COMPRISING A CUCURBIC ACID COMPOUND AND ANIONIC SURFACTANT DERIVED FROM AMINO ACID |
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 (en) * | 2017-12-22 | 2018-07-20 | 香港大学深圳医院 | A kind of 3 D-printing hydrogel material of containing mesopore nano-calcium phosphate granular filler and preparation method thereof |
CN108295306B (en) * | 2017-12-22 | 2020-12-25 | 香港大学深圳医院 | Three-dimensional printing hydrogel material containing mesoporous nano calcium phosphate particle filler and preparation method thereof |
WO2020132856A1 (en) * | 2018-12-25 | 2020-07-02 | L'oreal | Composition for brightening or whitening keratin materials |
WO2020132855A1 (en) * | 2018-12-25 | 2020-07-02 | L'oreal | Composition for brightening or whitening keratin materials |
WO2020132860A1 (en) * | 2018-12-25 | 2020-07-02 | L'oreal | Composition for brightening or whitening keratin materials |
CN113226253A (en) * | 2018-12-25 | 2021-08-06 | 莱雅公司 | Composition for lightening or whitening keratin materials |
Also Published As
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WO2012136564A3 (en) | 2014-02-06 |
FR2973691A1 (en) | 2012-10-12 |
FR2973691B1 (en) | 2013-03-29 |
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