WO2014170591A1

WO2014170591A1 - Cosmetic composition comprising a cucurbic acid compound and a (poly)oxyalkylenated polar oil

Info

Publication number: WO2014170591A1
Application number: PCT/FR2014/050901
Authority: WO
Inventors: Sonia EYRAUD; Virginie DESVENAIN; Céline SAHEB; Vincent Grandjon
Original assignee: L'oreal
Priority date: 2013-04-17
Filing date: 2014-04-14
Publication date: 2014-10-23
Also published as: FR3004641B1; FR3004641A1

Abstract

The invention relates to a composition especially in the form of an emulsion, particularly a water-in-oil emulsion, comprising a cucurbic acid compound and a (poly)oxyalkylenated (C3-C4) polar oil. The invention is applicable to the care and make-up of keratinic materials.

Description

Cosmetic composition comprising a cucurbic acid compound and a polar (poly) oxyalkylenated oil

The present invention relates to especially cosmetic and / or dermatological compositions comprising a cucurbic acid compound and a (poly) oxyalkylenated (C 3 -C 4) polar oil, as well as the use of these compositions in a method of non-therapeutic treatment of keratin materials especially human beings.

More particularly, the compositions of the invention are intended for caring for and / or making up keratin materials.

For the purposes of the invention, the term "keratin materials" is intended to mean, for example, the skin, the mucous membranes, the lips, the scalp, the keratinous fibers such as eyelashes, eyebrows and hair.

It is known in the application EP-A-1333021 cucurbic acid compounds such as 3-hydroxy-2-pentyl-cyclopentane acetic acid to promote desquamation of the skin and stimulate epidermal renewal, fight against the signs of aging skin, improve the radiance of the complexion and / or smooth the skin of the face. In the application FR-A62921255 these compounds are also described for their use as a depigmenting agent.

However, the introduction of these compounds mentioned above into cosmetic formulations in the form of an emulsion, in particular of an oil-in-water emulsion, can greatly impair the stability of the compositions comprising them, which can result, for example, in a decrease negligible viscosity and / or phase shift of the composition.

However, the compositions containing derivatives of cucurbic acid have insufficient cosmetic properties, especially a touch sticky, rough effect, which gives compositions that are not pleasant to apply by a consumer.

Moreover, the derivatives of cucurbic acid also have the disadvantage of being poorly soluble, It follows a recrystallization of these derivatives which causes instability of the formulations. The derivatives of cucurbic acid are then no longer available to act on the skin.

It is known to use in cosmetics containing cucurbic acid or its derivatives oils and emollients whose role is to soften, soften, moisturize and improve the comfort of the skin. However, these oils do not make it possible to maintain the stability of the cucurbic acid derivatives while having good cosmetic properties.

Thus, there is a need for compositions comprising cucurbic acid compounds, which are stable and which have good cosmetic properties, especially a touch whose texture is non-greasy, non-sticky. Moreover, the compositions have a smooth and shiny appearance.

Surprisingly, the inventors have observed that the use of a cucurbic acid compound in combination with a particular polar oil makes it possible to achieve such objectives.

More specifically, the present invention relates to a composition comprising in a physiologically acceptable medium:

at least one cucurbic acid compound, in particular of formula (I) below:

in which : R 1 represents a COOR 3 radical, R 3 denoting a hydrogen atom or a C 1 -C 4 alkyl radical, optionally substituted by one or more hydroxyl groups;

R2 represents a hydrocarbon radical, saturated or unsaturated, linear having from 1 to 18 carbon atoms, or branched or cyclic having from 3 to

18 carbon atoms; as well as their optical isomers, and corresponding salts and

at least one (poly) oxyalkylenated (poly) C 3 -C 4 polar oil of formula (II) below.

The compositions obtained have good stability over time, a pleasant appearance, and during their application, good sensory properties.

"Stable composition" means a composition which, after 24 hours of storage at all temperatures between 4 ° C and 50 ° C, shows little or no macroscopic change in color, odor or viscosity, in particular wherein the cucurbic acid compound does not recrystallize over time and / or as a function of temperature. According to yet another of its objects, the present invention relates to a method of non-therapeutic treatment care or makeup of keratin materials comprising the application on said keratin materials of a composition according to the invention. Cucurbic acid compound.

The compound derived from cucurbic acid is a compound chosen from those corresponding to the following formula (I):

in which :

R 1 represents a COOR 3 radical, R 3 denoting a hydrogen atom or a C 1 -C 4 alkyl radical, optionally substituted by one or more hydroxyl groups;

R2 represents a hydrocarbon radical, saturated or unsaturated, linear having 1 to 18 carbon atoms, or branched or cyclic having 3 to 18 carbon atoms; as well as their optical isomers, and corresponding salts.

Preferably, R 1 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, - COOCH ₂ -CH (OH) -CH3. Preferably, R 1 denotes a -COOH radical.

Preferentially, R ₂ denotes a hydrocarbon radical, linear, saturated or unsaturated, and preferably having from 2 to 7 carbon atoms. In particular, R ₂ 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] -cyclopentane acetic acid or 3-hydroxy-2-pentyl-cyclopentane acid. acetic acid or their salts. Preferably, the compound (I) is 3-hydroxy-2-pentylcyclopentane acetic acid or its salts; this compound may especially be in the form of sodium salt. The salts of the compounds that may be used according to the invention are in particular chosen from alkali metal salts, for example sodium and potassium; alkaline earth metal salts, for example calcium, magnesium, strontium, metal salts, for example zinc, aluminum, manganese, copper; ammonium salts of formula NH ₄ ⁺ ; quaternary ammonium salts; organic amine salts, such as for example the salts of methylamine, dimethylamine, trimethylamine, triethylamine, ethylamine, 2-hydroxyethylamine, bis- (2-hydroxyethyl) amine, tri- (2- hydroxyethyl) amine; lysine salts, arginine. Salts chosen from among the sodium, potassium, magnesium, strontium, copper, manganese and zinc salts are preferably used. Preferably, the sodium salt is used.

The cucurbic acid derivative compound of formula (I) defined above may be present in the composition according to the invention in a content ranging from 0.01 to 15% by weight, relative to the total weight of the composition, preferably from 0.1 to 10% by weight and more preferably 0.5 to 5% by weight.

C3-C4 oxyalkylenated polar oil (polv) Polar oil within the meaning of the present invention means an oil whose surface tension corresponds to the force per unit length, expressed in mN / m, is greater than 20 mN / m at temperature. ambient temperature (25 ° C) and at atmospheric pressure. These oils can be of different chemical natures such as: esters, ethers, alkanes, alcohols, alkenes, vegetable oils, of natural or synthetic origin, hydrocarbon or silicone, linear or branched, polymerized or not. According to the invention, the (poly) oxyalkylenated C 3 -C 4 oils generally do not comprise oxyethylenated groups. The polar oil according to the invention according to the invention has a surface tension greater than 15 mN / m, better still greater than 20 mN / M and preferably greater than 25 mN / m and more particularly ranging from 25 to 40 mN / m.

Surface Voltage Measurement Method

tensiometry

The surface tension is measured according to conventional methods, in particular according to the method of the hanging drop and more particularly according to the method of the Du Nouy ring.

The technique of the Du Nouy ring consists of immersing a platinum ring in the liquid whose surface tension is to be measured and then pulling the ring towards the liquid / air interface at room temperature. The monitor will search for the maximum force at this interface and measure it (Figure k). This force is written Pm and can not be obtained directly; it undergoes a correction according to the geometry of the ring. The device will first calculate gs ^* called measured surface tension. It is obtained by the relation: gs ^* = Pm / [2TT (Ri + Ro)]; with Ri and Ro respectively the inner and outer rays of the ring. Then he will deduce gs from the relation: gs = gs ^* .F; where F is the correction factor depending on the density of the liquid as well as the ratio of the diameters of the ring.

The manipulation is carried out with a Kruss K12 tensiometer, the liquid is placed in a perfectly cleaned crystallizer (crystallizer 46mm in diameter ref GL5 Kruss) and the ring is in platinum iridium (ref RI01 Kruss). The device gives the surface tension directly in mN / m.

The polar oil according to the invention is a (poly) oxyalkene compound of formula (II):

RO (AO) _n H (II)

in which

R represents a linear or branched, saturated or unsaturated C 1 -C 22, preferably C 3 -C 18, alkyl or acyl radical; AO represents an oxyalkylene group comprising from 3 to 4 carbon atoms, and preferably 3,

n represents the average number of moles of AO units and n ranges from 1 to 100, preferably from 3 to 50 and more particularly from 5 to 20.

Preferably, R is an alkyl radical, preferably C 1 -C 22, better still C 3 -C 18.

The polar (poly) oxyalkylenated oil of formula (II) according to the invention is preferably chosen from PPG-2 butyl ether; PPG-3 butyl ether; PPG-4 Butyl

Ether; PPG-5 butyl ether; PPG-9 butyl ether; PPG-12 butyl ether; PPG-14

Butyl Ether, PPG-15 Butyl Ether, PPG-16 Butyl Ether; PPG-17 Butyl Ether;

PPG-18 Butyl Ether; PPG-20 butyl ether; PPG-22 Butyl Ether; PPG-24 Butyl

Ether; PPG-26 Butyl Ether; PPG-30 Butyl Ether; PPG-33 Butyl Ether; PPG-Butyl Ether; PPG-52 Butyl Ether; PPG-53 Butyl Ether; PPG-3 Caprylyl

Ether; PPG-4 Caprylyl Ether; PPG-5 Caprylyl Ether; PPG-6 Caprylyl Ether;

PPG-10 Caprylyl Ether; PPG-10 Cetyl Ether, PPG-20 Cetyl Ether; PPG-28

Cetyl ether; PPG-30 Cetyl Ether; PPG-50 Cetyl Ether; PPG-4 Lauryl Ether;

PPG-7 Lauryl Ether; PPG-10 Lauryl Ether, PPG-2 Methyl Ether, PPG-3 Methyl Ether; PPG-4 Methyl Ether PPG-3 Myristyl Ether; PPG-4 Myristyl Ether; PPG-

Oleyl Ether, PPG-20 Oleyl Ether, PPG-23 Oleyl Ether; PPG-30 Oleyl Ether;

PPG-37 Oleyl Ether; PPG-50 Oleyl Ether; PPG-1 1 Stearyl Ether; PPG-15

Stearyl Ether and their mixtures.

(PPG stands for PolyPropylene Glycol)

Preferably, the (poly) oxyalkylenated (polar) polar oil according to the invention is PPG-Stearyl ether, PPG-3 Myristyl ether, PPG-12 butyl ether, PPG-10 caprylyl ether; PPG-10 Cetyl Ether, PPG-20 Cetyl Ether, PPG-10 Oleyl Ether, PPG-20 Oleyl Ether, PPG-23 Oleyl Ether and more particularly PPG-15 Stearyl Ether and PPG-3 Myristyl Ether, even better PPG -15 Stearyl Ether. The (poly) oxyalkylenated C 3 -C 4 polar oil according to the invention is generally present in the compositions according to the invention in a content ranging from 0.1% to 20% by weight, relative to the total weight of the composition. and preferably from 0.5% to 10% by weight, and more preferably from 1 to 5% by weight relative to the total weight of the composition.

The compositions used according to the invention comprise a physiologically acceptable medium, that is to say compatible with the keratin materials of human beings such as the skin, the scalp, the hair, the nails.

The compositions according to the invention can be in the form of aqueous solutions, hydroalcoholic solutions, oil-in-water (O / W) or water-in-oil (W / O) or multiple (triple: E / W) emulsions. H / E or H / E / H), aqueous gels. The compositions can also be anhydrous. These compositions are prepared according to the usual methods.

The physiologically acceptable medium may comprise water, organic solvents such as a C ₁ -C ₈ alcohol, in particular ethanol, isopropanol, tert-butanol, n-butanol; a polyol such as glycerine; a glycol such as butylene glycol, isoprene glycol, propylene glycol, polyethylene glycols such as PEG-8; polyol ethers. When the composition is an emulsion, the proportion of the fatty phase 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 oils, the waxes, the emulsifiers and the coemulsifiers used in the composition in emulsion form are chosen from those conventionally used in the cosmetics field. The emulsifier and the coemulsifier are present in the composition in a proportion ranging from 0.3% to 30% by weight, and preferably from 0.5 to 20% by weight relative to the total weight of the composition. The emulsion may further contain lipid vesicles.

When the composition is a solution or an oily gel, the fatty phase may represent more than 90% of the total weight of the composition.

The composition according to the invention may comprise an amount of aqueous phase which may range, for example, from 30 to 97% by weight, preferably from 40 to 95% by weight and better still from 50 to 90% by weight relative to the total weight of the composition.

The aqueous phase comprises water and any other water-soluble compound that may be present, such as, in particular, water-soluble solvents and additives (for example hydrophilic and active surfactants). As water-soluble solvents, mention may be made in particular of lower alcohols and polyols. The term "lower alcohol" is understood to mean alcohols containing from 1 to 8 and more particularly from 1 to 6 carbon atoms, such as ethanol. Examples of polyols that may be mentioned include glycerin, propylene glycol, butylene glycol and polyethylene glycols (for example PEG-8). These alcohols and / or polyols may be present in the composition in an amount ranging preferably from 0.1 to 25% and from 1 to 15% of the total weight of the composition.

The composition comprises a fatty phase which comprises at least the polar oil according to the invention.

The fatty phase consists of oils and all the other fatty substances and lipophilic constituents that may be present in the composition of the invention. All cosmetically acceptable oils can be used. The term "oil" means a fatty substance that is liquid at ambient temperature (25 ° C.) and atmospheric pressure.

As oil, for example:

hydrocarbon oils of animal origin, such as perhydrosqualene and squalane;

hydrocarbon-based oils of plant origin, such as liquid triglycerides of fatty acids containing from 4 to 10 carbon atoms, for instance triglycerides of heptanoic or octanoic acids or, for example, sunflower, corn or soybean oils, squash, grape seed, sesame, hazelnut, apricot, macadamia, arara, sunflower, castor oil, avocado, triglycerides of caprylic / capric acids such as those sold by Stearineries Dubois or those sold under the names Miglyol 810, 812 and 818 by the company Dynamit Nobel, jojoba oil, shea butter oil;

esters and synthetic ethers, in particular of fatty acids, such as the oils of formulas R ¹ COOR ² and R ¹ OR ² in which R ¹ represents the residue of a fatty acid comprising from 8 to 29 carbon atoms, and R ² represents a hydrocarbon chain, branched or unbranched, containing from 3 to 30 carbon atoms, for example Purcellin oil, isononyl isononanoate, isopropyl myristate or 2-ethyl palmitate; hexyl, octyl-2-dodecyl stearate, octyl-2-dodecyl erucate, isostearyl isostearate; hydroxylated esters such as isostearyl lactate, octyl hydroxystearate, octyldodecyl hydroxystearate, diisostearyl malate, triisocetyl citrate, heptanoates, octanoates, decanoates of fatty alcohols; polyol esters, such as propylene glycol dioctanoate, neopentyl glycol diheptanoate and diethylene glycol diisononanoate; and pentaerythritol esters such as pentaerythrityl tetraisostearate (Prisorine 3631);

linear or branched hydrocarbons of mineral or synthetic origin, such as paraffin oils, volatile or not, and their derivatives, petroleum jelly, polydecenes, hydrogenated polyisobutene such as Parleam oil; volatile linear alkanes, advantageously of plant origin, comprising from 7 to 17 carbon atoms, in particular from 9 to 15 carbon atoms, and more particularly from 1 to 13 carbon atoms. As examples of volatile linear alkanes that are suitable for the invention, mention may be made of those described in the patent application of Cognis WO 2007/068371. By way of example of a volatile linear alkane which is suitable for the invention, mention may be made of n-nonane (C ₉ ), n-decane (d ₀ ), n-undecane (C n), n-dodecane ( Ci ₂ ), n-tridecane (Ci ₃ ), n-tetradecane (C ₄ ), n-pentadecane (C ₅ ), n-hexadecane (de) and n-heptadecane (C ₇ ) and mixtures thereof . According to one embodiment, use will be made of a mixture of undecane (Cn) and tridecane (Ci ₃ ) as obtained in Examples 1 and 2 of Application WO2008 / 155059 from Cognis. Mention may also be made of n-dodecane (C12) and n-tetradecane (C14), such as those sold by Sasol respectively under the references PARAFOL 12-97 and PARAFOL 14-97, as well as their mixtures.

silicone oils, for example volatile or non-volatile polymethylsiloxanes (PDMSs) with a linear or cyclic silicone chain, which are liquid or pasty at room temperature, in particular cyclopolydimethylsiloxanes (cyclomethicones) such as cyclohexasiloxane and cyclopentasiloxane; polydimethylsiloxanes (or dimethicones) comprising alkyl, alkoxy or phenyl groups, during or at the end of the silicone chain, groups having from 2 to 24 carbon atoms; phenyl silicones such as phenyltrimethicones, phenyldimethicones, phenyltrimethylsiloxydiphenylsiloxanes, diphenyl-dimethicones, diphenylmethyldiphenyltrisiloxanes, 2-phenylethyltrimethylsiloxysilicates, and polymethylphenylsiloxanes;

fatty alcohols having from 8 to 26 carbon atoms, such as cetyl alcohol, stearyl alcohol and their mixture (cetylstearyl alcohol);

partially fluorinated hydrocarbon oils and / or silicone oils such as those described in document JP-A-2-295912;

- and their mixtures. Mention may also be made of the oils chosen from:

the esters resulting from the reaction of at least one fatty acid comprising at least 6 carbon atoms, preferably from 6 to 26 carbon atoms and better still from 6 to 20 carbon atoms, more preferably from 6 to 16 carbon atoms; and at least one alcohol comprising 1 to 17 carbon atoms and more preferably 3 to 15 carbon atoms; mention may be made in particular of isopropyl myristate, isopropyl palmitate, ethyl 2-hexyl caprate / caprylate (or octyl caprate / caprylate), 2-ethylhexyl palmitate, isostearyl neopentanoate, isononyl isononanoate, hexyl laurate, esters of lactic acid and of fatty alcohols comprising 12 or 13 carbon atoms, dicaprylyl carbonate, such as that marketed under the name CETIOL CC by the company Cognis,

fatty acid ethers comprising from 6 to 20 carbon atoms, such as dicaprylyl ether (Cetiol OE from Cognis),

glycerol ethers comprising from 6 to 12 carbon atoms, such as glycerol 2-ethyl hexyl ether (INCI name: ethylhexylglyce n), such as Sensiva SC 50 from Schulke & Mayr GmbH,

The fatty phase may be present in the composition according to the invention in an amount ranging from 5 to 60%, better still from 5 to 50% and preferably from 10 to 40% by weight relative to the total weight of the composition. This amount does not include the polyhydroxy fatty acid ester and polyalkylene glycol ester emulsifier.

In particular, the composition according to the invention may comprise from 5 to 40% and preferably from 10 to 30% by weight of oils relative to the total weight of the composition.

In addition to the oils mentioned above, the composition of the invention may contain other fatty substances in the fatty phase, such as fatty acids having from 8 to 30 carbon atoms, such as stearic acid; silicone resins such as trifluoromethyl-C1-4-alkyldimethicone and the trifluoropropyldimethicone; silicone gums (dimethiconol), non-emulsifying silicone elastomers, such as the products sold under the names "KSG 6" or "KSG 16" by the company Shin-Etsu, under the names "Trefil", "BY29" or " EPSX "by Dow Corning or under the names" Gransil "by Grant Industries; waxes, for example mineral waxes, waxes of animal origin, such as beeswax, waxes of plant origin, hydrogenated oils which are concretes at 25 ° C., fatty esters and concrete glycerides at 25 ° C. synthetic waxes, silicone waxes; pasty fatty substances as and also butters such as shea butter, cocoa butter, shorea butter, muru muru butter, cupuac butter, and mixtures thereof.

emulsifiers

According to one embodiment, the composition according to the invention may comprise one or more emulsifier (or surfactant).

The emulsifier may be chosen for example from nonionic emulsifiers derived from fatty acid and polyol, succinic-terminated polyolefins, and mixtures thereof.

As succinically terminated polyolefins, mention may be made in particular of esterified succinic-terminated polyisobutylenes and their salts, in particular the diethanolamine salts, such as the products sold under the names Lubrizol 2724, Lubrizol 2722 and Lubrizol 5603 by the company Lubrizol.

Preferably, the emulsifier is chosen from fatty acid esters and polyols. By fatty acid esters of polyols' according to the invention is understood to mean fatty acid esters of polyols, wherein the fatty acid comprises an alkyl chain C ₆ -C ₂ 2, preferably C ₆ -C ₂ o, and the polyol is selected from glycerol, a polyglycerol, sorbitan, and mixtures thereof. The fatty acid may also be in a polymeric form, as is the case of polyhydroxystearic acid (12-hydroxystearic acid polymer).

In a particular embodiment, the fatty acid and polyol ester is a C ₆ -C ₂₀ fatty acid ester and glycerol and / or sorbitan, and mixtures thereof.

Examples of linear or branched C ₆ -C ₂₀ fatty acids include stearic acid, isostearic acid, lauric acid, myristic acid, palmitic acid. An example of a C16-C20 fatty acid polymer is poly12-hydroxystearic acid.

Preferably, stearic acid, isostearic acid, poly (1-hydroxystearic acid) and mixtures thereof are used.

By polyglycerols is meant compounds of formula

in which the degree of condensation n ranges from 1 to 1 1, preferably from 2 to 6 and even more preferably from 3 to 6.

According to one particular embodiment, the fatty acid and polyol ester contains 2 to 10 moles (units) of polyols, preferably 2 to 4 moles of polyols, in particular 2 to 4 units of glycerol or a mixture of polyglycerols (glycerol). , di-, tri-, tetra-25, penta-, oligoglycerols).

Even more preferably, the fatty acid and polyol ester contains 4 moles or units) of polyol, in particular 4 moles (or units) of glycerol. According to a preferred embodiment, said fatty acid and polyol ester is, in addition, a fatty acid ester of a dicarboxylic acid having 2 to 16 carbon atoms, preferably 8 to 14 carbon atoms, such as azelaic acid, sebacic acid, dodecanedioic acid, and preferably sebacic acid (d ₀ ), and polyol.

As examples of fatty acid and polyol esters that may be used in the composition of the invention, mention may be made of isostearic acid and polyol esters and their mixtures, in particular esters of isostearic acid and of glycerol and / or sorbitan, such as for example polyglycerol isostearate (4 mol) (INCI name: Polyglyceryl-4 isostearate) sold under the name Isolan ^® GI34 by Goldschmidt, the diisostearate polyglycerolated (3 mol) sold under the Lameform TGI ^® denomination by Cognis; distearate polyglycerolated (2 mol) sold under the name Emalex PGSA ^® by Nihon emulsion society; polyglycerol monoisostearate (10 moles) sold under the name Nikkol decaglyn 1 -IS by the company Nihon Surfactant (INCI name: Polyglyceryl-10 isostearate); the polyglyceryl-4 diisostearate polyhydroxystearate sebacate sold under the name ISOLAN GPS by Goldschmidt; the mixture of sorbitan isostearate and glycerol isostearate, such as the product sold under the name Arlacel 986 by the company ICI, the mixture of isostearate of sorbitan and polyglyceryl isostearate (3 moles) marketed under the name Arlacel 1690 by Uniqema, mixture of sorbitan isostearate and polyglyceryl isostearate (3 moles) sold under the name Arlacel ^® 1690 by Uniqema, and mixtures thereof.

Mention may also be made of silicone surfactants such as dimethicone copolyols and alkyl dimethicone copolyols such as the mixture of cyclomethicone and dimethicone copolyol, sold under the name "DC 5225 C" by Dow Corning, and Laurylmethicone copolyol sold under the name " Dow Corning 5200 Formulation Aid "by Dow Corning and cetyl dimethicone copolyol sold under the name Abil EM 90 ^R by the company Goldschmidt.

Preferably, the emulsifier is chosen from fatty acid esters, preferably C ₆ -C ₂ o, in particular stearic acid or isostearic acid, and polyol chosen from glycerol and / or sorbitan .

The emulsifier may be present in a content (of solids) ranging from 0.05 to 5% by weight relative to the total weight of the composition, preferably from 0.1 to 3% by weight relative to the total weight of the composition. composition.

additives

In known manner, the composition for topical application of the invention may also contain one or more adjuvants usual in the cosmetic or dermatological field. As adjuvants, mention may be made of thickeners, active agents, preservatives, antioxidants, perfumes, solvents, salts, fillers, sunscreens (= UV filters), inorganic or organic, dyestuffs, basic agents. (triethanolamine, diethanolamine, sodium hydroxide) or acids (citric acid), and mixtures thereof. These adjuvants are used in the usual proportions in the cosmetic field, and for example from 0.01 to 30% of the total weight of the composition, and they are, according to their nature, introduced into the aqueous phase of the composition or into the phase oily, or in vesicles or any other type of vector. These adjuvants and their concentrations must be such that they do not modify the properties desired for the composition of the invention.

Depending on the viscosity desired for the composition according to the invention, one or more hydrophilic thickeners may be incorporated therein. For example, modified or unmodified carboxyvinyl polymers, such as the products sold under the names Carbopol Noveon company; polyacrylamides; polymers and copolymers of 2-acrylamido-2-methylpropanesulphonic acid, optionally crosslinked and / or neutralized, such as poly (2-acrylamido-2-methylpropanesulphonic acid) marketed by the company Clariant under the name "Hostacerin AMPS" (INCI name) ammonium polyacryldimethyltauramide); crosslinked anionic copolymers of acrylamide and of AMPS, in the form of an W / O emulsion, such as those marketed under the name SEPIGEL 305 (CTFA name: Polyacrylamide / C13-14 Isoparaffin / Laureth-7) and under the name SIMULGEL 600 (CTFA name Acrylamide / Sodium acryloyldimethyltaurate copolymer / Isohexadecane / Polysorbate 80) by the company SEPPIC; polysaccharide biopolymers such as xanthan gum, guar gum, alginates, modified or unmodified celluloses; and their mixtures. When they are present, these gelling agents must be introduced in such a quantity that they do not modify the properties of the composition according to the invention. As lipophilic gelling agents, mention may be made in particular of modified clays, such as modified magnesium silicate (RHEOX bentonite gel VS38), and hectorite modified with distearyl dimethyl ammonium chloride (INCI name: Disteardimonium hectorite) marketed under the name "bentone". 38 EC "by the company RHEOX.

As active agents that may be used in the composition of the invention, mention may be made, for example, of moisturizing agents such as protein hydrolysates; sodium hyaluronate; polyols such as glycerin, glycols such as polyethylene glycols, and sugar derivatives; anti-inflammatories; procyannidol oligomers; vitamins such as vitamin A (retinol), vitamin E (tocopherol), vitamin K, vitamin C (ascorbic acid), vitamin B5 (panthenol), vitamin B3 or PP (niacinamide), derivatives of these vitamins (especially esters) and mixtures thereof; keratolytic and / or desquamating agents such as salicylic acid and its derivatives, alpha-hydroxy acids such as lactic acid and glycolic acid and their derivatives, ascorbic acid and its derivatives; urea; caffeine; depigmenting agents such kojic acid, hydroquinone and caffeic acid; salicylic acid and its derivatives; retinoids such as carotenoids and vitamin A derivatives; hydrocortisone; melatonin; self-tanning agents such as DHA, extracts of algae, fungi, plants, yeasts, bacteria; steroids; anti-bacterial active agents such as 2,4,4'-trichloro-2'-hydroxy diphenyl ether (or triclosan), 3,4,4'-trichlorocarbanilide (or triclocarban) and the acids indicated above and in particular the salicylic acid and its derivatives; enzymes; flavonoids; tensing agents such as synthetic polymers, plant proteins, polysaccharides of vegetable origin, starches, wax dispersions, mixed silicates and colloidal particles of inorganic fillers; ceramides; anti-inflammatory agents; soothing agents; mattifying agents; agents for preventing and / or regrowing hair; anti-wrinkle agents; essential oils ; and their mixtures; and any suitable asset for the ultimate purpose of the composition.

A composition of the invention may be in any conceivable galenic form.

In particular, the composition may have the form of aqueous, alcoholic, hydroalcoholic or oily solution; dispersion of the lotion or serum type; water-in-oil, oil-in-water or multiple emulsion; suspension; microcapsules or microparticles; vesicular dispersions of ionic and / or nonionic type; aqueous, oily or serum lotion; capsules, granules, syrups, tablets; foam, solid preparation; aerosol composition composition also comprising a propellant under pressure.

A composition according to the invention may be in the form of a composition for hair care, in particular a shampoo, a setting lotion, a treatment lotion, a cream or a styling gel, a dyeing composition, in particular oxidation, restructuring lotions for hair, a composition of permanent (including a composition for the first time of a perm), a lotion or a fall protection gel, a pest control shampoo. It may also be in the form of a composition for cleaning, protecting, treating or caring for the face, the hands, the feet, the large anatomical folds or the body (for example, day creams). , night cream, make-up remover, sunscreen composition, body protection or care milk, after-sun milks, lotion, gel or mousse for skin care, such as cleaning lotion, artificial tanning composition); a makeup composition for the body or the face such as a foundation; a bath composition; a deodorant composition comprising, for example, a bactericidal agent; aftershave composition; an epilatory composition; a composition against insect bites; an anti-pain composition; a dermatological or pharmaceutical composition for treating certain skin diseases such as eczema, rosacea, psoriasis, lichens, severe pruritus.

When a composition according to the invention is intended for use as a peel, it may also be in any of the galenical forms mentioned above, provided that it is easily removed by rinsing, and in particular in the form of an aqueous gel. of aqueous or hydroalcoholic solution.

A composition according to the invention may be applied by any means allowing a uniform distribution and especially using a cotton, a rod, a brush, a gauze, a spatula or a buffer, or by spraying, and may be removed by rinsing with water or a mild detergent. A composition according to the invention may be in a fluid form of liquid type vaporizable or not, in the form of paste, gel or support impregnated, in solid form, in particular compact, pulverulent or cast or in a stick form.

A composition according to the invention may also be in the form of a care product, a solar product or after sun, a daily photoprotective care product, a product for the body, d a foundation to be applied to the face or neck, a concealer, a concealer, a tinted cream or makeup base for face makeup or a makeup composition for the body.

A composition according to the invention may be used for the purpose of improving the general condition of an epidermis, in particular of the skin, and in particular for maintaining or restoring its physiological functions and / or its aesthetic appearance.

Thus, a composition according to the invention can be advantageously used in order to fight against aging of the epidermis, maintain and / or stimulate hydration and / or fight against drying of the skin, improve the tone of the skin maintain or restore the suppleness and elasticity of the skin, improve the mineralization of the epidermis, improve the vitality of the epidermis, facilitate inter-cellular exchanges, and fight against cracking and the cracked appearance of the skin .

A composition according to the invention may be intended for a cosmetic and / or dermatological application.

Other characteristics and advantages of the invention will emerge more clearly from the examples which follow, given by way of illustration and not limitation. In what follows or what precedes, the proportions are given in percentage by weight, unless otherwise indicated. Examples 1 to 5

An O / W emulsion (exemplel) comprising a polar oil according to the invention and 3 comparative emulsions (Examples 2 to 4) comprising oils outside the invention, and the stability of these compositions was observed.

Phase 1 2 3 4 5

A1 Cetyl alcohol 1.7 1.7 1.7 1.7 1.7

Behenyl alcohol 1.5 1.5 1.5 1.5 1.5

Stearic acid 1,1 1,1 1,1 1,1 1,1

Mixture of C ₄ -C ₂ alcohols 2

and Ci ₄ -C ₂ o alkylglucoside

0.6 0.6 0.6 0.6 0.6 (80/20) ( 68 MONTANOV ^® of

SEPPIC)

POLOXAMER 338

(Synperonic PE / F 108 0.4 0.4 0.4 0.4 0.4 CRODA)

PEG-100 STEARATE

0.2 0.2 0.2 0.2 0.2 (Myrj S100-PA from CRODA)

A2 PPG-15 STEARYL ETHER

3

(Arlamol® PS15E from CRODA)

PENTAERYTHRITYL TETRAETHYLH EXANOATE

3

(DUB PTO from STEARINERIE

DUBOIS)

C12-15 ALKYL BENZOATE

(DUB B1215de 3

STEARINERIE DUBOIS)

CAPRYLIC / CAPRIC

3

TRIGLYCERIDES (DUB MCT 7030 from

STEARINERIE DUBOIS)

PPG-3 MYRISTYL ETHER

(TEGOSOFT APM of 3 EVONIK GOLDSCHMIDT)

A3 ISOPROPYL ISOSTEARATE 2,6

DIMETHICONE 350 CST

(BELSIL DM 350 of 0.5 WACKER)

Octyldodecanol 3

CAPRYLOYL SALICYLIC

0.3 ACID

Conservatives 0.9

Adenosine 0909 from CHENG

0.1 Yl PHARMACEUTICAL)

B Water 25

Glycerin 8

DISODIUM EDTA 0.1

C Water QSP 100%

D Sodium salt of 3-hydroxy-2-pentyl-cyclopentanic acid

30% acetic acid in a 6.7% (2% MA) water / dipropylene mixture

glycol (70/30).

E DIMETHICONE 6 CST

(Xiameter PMX-200 Silicone

6,6 Fluid 5CS from DOW

CORNING)

CARBOMER (Carbopol Ultrez

0.5 10 Polymer of LUBRIZOL) Homopolymer of acid

acrylamidomethyl propane

Crosslinked sulfonic acid 0.8 (HOSTACERIN AMPS® from

Clariant)

SODIUM HYALURONATE

0.1

(Hyal Crystal from SOLIANCE)

F Sodium hydroxide in

30% aqueous solution of qs pH 6 active ingredient

G Blend (50/50 by weight) of

Polytetrafluoro wax

Ethylene (Fluoropure 103 C

2 of SHAMROCK

TECHNOLOGY and

Polyethylene (Micropoly 220 L

from MICRO POWDERS)

Operating mode:

- Weigh all the MPs of A together and heat to 75 ° C-80 ° C under Rayneri

- Solubilize B at room temperature with magnetic stirring

- Emulsify B in A with strong stirring

- Add the dilution phase C

- Add D

- Add E (soften gelling agents in silicone under Rayneri) - Add F

- Add G (invention) (invention)

Voltage 30m N / m 28,9mN / 32mN / m 29m N / m 30m N / m superficial

phase

A2

Stability 1 Stable Recrystalli Recristallis Recristalli Stable month 45 ° C Fine sation of the sation of Fine and 4 ° C dispersion derivative derived derivative homogeneous dispersion of acid acid of acid acid cucurbic cucurbic cucurbic

e at 4 ° C to 4 ° C to 4 ° C

The compositions according to the invention (ex 1 and 5) containing the sodium salt of 3-hydroxy-2-pentylcyclopentane acetic acid and polar (poly) oxypropylenated oil are stable and homogeneous for at least 1 month at 4. ° C and at 45 ° C, while the compositions comprising an oil outside the invention containing oxyalkylenated groups are not stable or homogeneous.

The compositions 1 and 5 are homogeneous, smooth, shiny and spread easily on the skin, without feeling sticky or greasy, and without linting.

Compositions 2, 3 and 4 are dull and are not homogeneous.

Example 6: A solar milk is prepared having the following composition:

PPG-15 STEARYL ETHER (ARLAMOL® PS15E from CRODA) 4%

Glycerin 5%

Sodium salt of 3-hydroxy-2-pentyl-cyclopentane acetic acid 30% in water / dipropylene glycol (70/30) 2% MA

Conservatives 0.3%

C12-15 alkyl benzoate (Tegosoft TN from Evonik / Goldschmidt) 10% PEG-100 stearate / glyceryl stearate (Arlacel 165 from

of Croda) 5%

Xanthan Gum 0.5% Octocrylene (UVINUL N539 from BASF) 10%

Butyl methoxydibenzoylmethane

(PARSOL 1789 by the company Hoffmann La Roche) 3%

Ethylhexyl methoxycinnamate

(PARSOL MCX from Hoffmann La Roche) 7% Water qs 100%

Example 7 Mattifying Moisturizing Emulsion

The following composition is prepared:

PPG-15 STEARYL ETHER (ARLAMOL® PS15E from CRODA) 4% PEG-30 dipolyhydroxystearate

(CITHROL DPHS-SO- (MV) from Croda) 3%

Polyglyceryl-4 isostearate (Isolan ^® GI34 Goldschmidt) 1%

Dicaprylyl carbonate 6%

Polydimethylsiloxane 10 cSt

(DOW CORNING SH 200 C FLUID 10 CS Dow Corning) 2% Vaseline 3%

Silica 3%

Disteardimonium hectorite 0.4%

Glycerin 5%

Sodium salt of 3-hydroxy-2-pentyl-cyclopentane

30% acetic acid in water / dipropylene glycol mixture (70/30) 1, 5% MA Conservatives 0.3%

Demineralized water qs 100%

Example 8: Moisturizing Body Milk

The following composition is prepared:

PPG-15 STEARYL ETHER (ARLAMOL® PS15E from CRODA) 1, 5% Sodium salt of 3-hydroxy-2-pentyl-cyclopentane

30% acetic acid in water / dipropylene glycol mixture (70/30) 1% MA

Conservatives 0.3%

Glycerin 10% PEG-100 Stearate / Glyceryl Stearate (Arlacel 165

of Croda) 2%

Dicaprylyl carbonate 10%

Octyldodecanol 8%

Demineralized water qs 100%

Example 9: Foundation

A foundation composition is prepared:

PPG-15 STEARYL ETHER (ARLAMOL® PS15E from CRODA)

Sodium salt of 3-hydroxy-2-pentyl-cyclopentane

30% acetic acid in water / dipropylene glycol mixture (70/30) 2.4% MA Preservatives 0.3%

Glycerin 10%

POLYGLYCERYL-4 ISOSTEARATE (and) CETYL PEG / PPG-10/1 DIMETH ICON (and) HEXYL LAURATE (ABIL WE 09 from Evonik /

Goldschmidt) 10%

Dicaprylyl carbonate 10%

Coated Yellow Iron Oxide 1 .6%

Coated brown iron oxide 0.4%

Coated black iron oxide 0.25%

10% coated titanium oxide

Demineralized water qs 100% The compositions of Examples 6 to 9 above are stable.

The compositions applied to the skin spread easily without feeling of stickiness or fat.

Claims

Composition comprising in a physiologically acceptable medium:

at least one cucurbic acid compound, especially of formula (I) below:

in which :

R2 represents a hydrocarbon radical, saturated or unsaturated, linear having 1 to 18 carbon atoms, or branched or cyclic having 3 to 18 carbon atoms; as well as their optical isomers, and corresponding salts and

at least one (poly) oxyalkylenated (C 3 -C 4) polar oil of formula (II):

RO (AO) _n H (II)

in which

R represents a linear or branched, saturated or unsaturated C 1 -C 22, preferably C 3 -C 18, alkyl or acyl radical;

AO represents an oxyalkylene group comprising from 3 to 4 carbon atoms, and preferably 3,

n represents the average number of moles of AO units and n ranges from 1 to 100, preferably from 3 to 50 and more particularly from 5 to 20. Composition according to Claim 1, characterized in that the compound (I) is such that R 1 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,

-COOCH ₂ -CH (OH) -CH 3; R ₂ denotes a hydrocarbon radical, linear, saturated or unsaturated, having from 2 to 7 carbon atoms.

Composition according to one of Claims 1 or 2, characterized in that, in the compound of formula (I), R1 denotes a -COOH radical.

Composition according to any one of the preceding claims, characterized in that, in the compound of formula (I), R ₂ denotes a hydrocarbon radical, linear, saturated or unsaturated, and preferably having from 2 to 7 carbon atoms.

Composition according to any one of the preceding claims, characterized in that R2 is a pentyl, pentenyl, hexyl or heptyl radical.

Composition according to one of the preceding claims, characterized in that the compound (I) is 3-hydroxy-2-pentylcyclopentane acetic acid or a salt thereof.

Composition according to any one of the preceding claims, characterized in that the compound of formula (I) is present in a content ranging from 0.01 to 15% by weight, relative to the total weight of the composition, preferably from 0 to 1 to 10% by weight and more preferably 0.5 to 5% by weight.

Composition according to any one of the preceding claims, characterized in that said polar oil of formula (II) has a tension superficial greater than 15mN / nn, better than 20mN / m and preferentially greater than 25mN / m.

9. Composition according to any one of the preceding claims, characterized in that the (poly) oxyalkylenated polar oil of formula (II) is chosen from PPG-2 butyl ether; PPG-3 butyl ether; PPG-4 butyl ether; PPG-5 butyl ether; PPG-9 butyl ether; PPG-12 butyl ether; PPG-14 Butyl Ether, PPG-15 Butyl Ether, PPG-16 Butyl Ether; PPG-17 Butyl Ether; PPG-18 Butyl Ether; PPG-20 butyl ether; PPG-22 Butyl

Ether; PPG-24 Butyl Ether; PPG-26 Butyl Ether; PPG-30 Butyl Ether; PPG-33 Butyl Ether; PPG-40 butyl ether; PPG-52 Butyl Ether; PPG-53 Butyl Ether; PPG-3 Caprylyl Ether; PPG-4 Caprylyl Ether; PPG-5 Caprylyl Ether; PPG-6 Caprylyl Ether; PPG-10 Caprylyl Ether; PPG-10 Cetyl Ether, PPG-20 Cetyl Ether; PPG-28 Cetyl Ether; PPG-30 Cetyl

Ether; PPG-50 Cetyl Ether; PPG-4 Lauryl Ether; PPG-7 Lauryl Ether; PPG-10 Lauryl Ether, PPG-2 Methyl Ether, PPG-3 Methyl Ether; PPG-4 Methyl Ether PPG-3 Myristyl Ether; PPG-4 Myristyl Ether, PPG-10 Oleyl Ether, PPG-20 Oleyl Ether, PPG-23 Oleyl Ether; PPG-30 Oleyl Ether; PPG-37 Oleyl Ether; PPG-50 Oleyl Ether; PPG-1 1 Stearyl Ether; PPG

Stearyl Ether.

10. Composition according to any one of the preceding claims, characterized in that the (poly) oxyalkylenated (C3-C4) polar oil of formula (II) is present in a content ranging from 0.1% to 20% by weight. weight, relative to the total weight of the composition, preferably from 0.5% to 10% by weight, and better still from 1 to 5% by weight relative to the total weight of the composition.

1 1. Composition according to any one of the preceding claims, characterized in that it is in the form of an emulsion, in particular of a water-in-oil emulsion. 12. A method of non-therapeutic treatment of keratin materials comprising applying to said keratin materials a composition according to any one of claims 1 to 1 1.