FR2939311A1 - Use of pyrrolidinone diester derivative in a composition comprising liquid fatty phase and lipophilic active agent in a medium, as solvent and/or as agent that improves the solubility of the active agent in the fatty phase - Google Patents

Abstract

Use of at least one pyrrolidinone diester derivative (I) in a composition comprising at least one liquid fatty phase and at least one lipophilic active agent in a medium, as solvent, which is active in the liquid fatty phase and/or as agent that improves the solubility of the active agent in the fatty phase, is claimed. Use of at least one pyrrolidinone diester derivative of formula (I) in a composition comprising at least one liquid fatty phase and at least one lipophilic active agent in a medium, as solvent , which is active in the liquid fatty phase and/or as agent that improves the solubility of the active agent in the fatty phase, is claimed. R 1>1-20C alkyl; R 2>1-5C alkyl biradical; and R 3>1-8C alkyl. An independent claim is included for the composition comprising at least one liquid fatty phase containing (I) and at least one lipophilic active agent. [Image].

Description

USE OF A PYRROLIDINONE-CARBOXY DIESTER DERIVATIVE AS A SOLVENT IN COSMETIC COMPOSITIONS; The present invention relates to the use of at least one pyrrolidinone diester derivative of formula (I), the definition of which will be given below, in a composition comprising, in a cosmetically acceptable medium, at least one fatty phase. liquid and at least one lipophilic active agent, as a solvent for said active ingredient in said liquid fatty phase and / or as an agent improving the solubility of said active ingredient in the solid fatty phase.

The present invention relates in particular to a composition comprising in a cosmetically acceptable medium at least one liquid fatty phase characterized in that it contains at least one pyrrolidinone diester derivative of formula (I) and at least one lipophilic active agent.

Many cosmetic or dermatological products are in various galenic forms comprising a liquid fatty phase such as dispersions, oily lotions, oil / water, water / oil or multiple emulsions, cream gels. Certain cosmetic or dermatological active agents of particular interest, such as lipophilic organic filters, which are hardly soluble in the oily phase of these formulations and which tend during storage to form crystals or to precipitate in particular in emulsions. Such phenomena are undesirable from the point of view of stability of the formulation and / or consumer comfort in that they may destabilize the composition and / or affect the aesthetic appearance of the product and / or cause cosmetic discomfort to the application on the skin and / or the hair or to limit the concentration of active ingredients in these formulas which does not make it possible to obtain sufficiently effective products.

This is particularly the case with care formulations containing lipophilic active agents of low solubility, such as the active agents chosen from aminophenol derivatives, salicylic acid derivatives and 2-amino-4-alkylaminopyrimidine-3-oxide derivatives in particular. 2-amino 4-dodecylaminopyrimidine 3-oxide, DHEA (dehydroepiandrosterone), its derivatives and its precursors chemicals such as 7-hydroxy or 7-keto-DHEA, or 3R-acetoxy-7-keto-DHEA, cholesterol and its esters, plant sterols such as phytosterols and sitosterols and their esters, pentacyclic triterpene acids, 40 hydroxystilbenes, flavonoids, lipophilic organic UV filters in antisolar formulations, retinol and its derivatives, carotenoids such as lycopene, and also perfumes, essential oils, hormones, vitamins, in particular vitamin E, ceramides or mixtures thereof.

In particular, the sunscreen compositions are often in the form of an oil-in-water or water-in-oil emulsion, gels or anhydrous products which contain, in various concentrations, one or more filters. organic and / or inorganic, insoluble and / or soluble, lipophilic and / or hydrophilic, capable of selectively absorbing harmful UV radiation. These filters and their quantities are selected according to the desired protection index. Depending on their lipophilic or hydrophilic nature, these filters may be distributed, respectively, either in the fatty phase or in the aqueous phase, of the final composition.

Lipophilic filters are commonly used in solar formulations. However, for a certain number of them, their photoprotective power in formulation is rather limited in the usual cosmetic carriers containing oils such as oxyethylenated or oxypropylene (mono / poly) fatty alcohols ("CETIOL HE" from Henkel or "WITCONOL"). APM "from Witco) or fatty esters such as the benzoate of C12-C15 alcohols (" FINSOLV TN "from Finetex), triglycerides of fatty acids, for example Miglyol 812 sold by the company DYNAMIT NOBEL the amino acid derivatives ("Eldew SL205" from Ajinomoto), because of a solubility of these filters in these oils commonly used in formulation not completely satisfactory. This has the consequence: either the appearance over time, crystallization in the formulas that hinder the good quality, stability and effectiveness of solar products; or to limit the concentration of filters in the formulas which does not allow to obtain sufficiently effective products.

There is therefore the need to find new solvents for effectively dissolving lipophilic active agents and in particular lipophilic filters to improve their solubility in oils and in carriers of cosmetic or dermatological formulations containing them without the disadvantages listed above.

It is known that the pyrrolidinone derivatives are known as an agent for penetrating active ingredients such as oleocanthal in the application WO2008 / 01240 or as the alkyl esters of asprotadil in the patent US6,673,841.

However, the Applicant has now discovered, surprisingly, a new family of effective solvents consisting of pyrrolidinone diester derivatives of formula (I) which will be given the following definition, to achieve this goal. These compounds can be incorporated into many cosmetic products.

This discovery is the basis of the present invention.

The present invention relates to the use of at least one pyrrolidinone diester derivative of formula (I), the definition of which will be given below, in a composition comprising, in a cosmetically acceptable medium, at least one liquid fatty phase and at least one a lipophilic active agent, as a solvent for said active agent in said liquid fatty phase and / or as an agent improving the solubility of said active agent in said fatty phase.

The present invention relates in particular to a composition comprising in a cosmetically acceptable medium at least one liquid fatty phase characterized in that it contains at least one pyrrolidinone diester derivative of formula (I) and at least one lipophilic active. also relates to the use of at least one pyrrolidinone diester derivative of formula (I) in a composition comprising, in a cosmetically acceptable medium, at least one liquid fatty phase and at least one lipophilic active ingredient for the purpose of improving the efficacy of said active agent and / or the cosmetic qualities and / or the stability of said composition.

The present invention also relates to the use of at least one pyrrolidinone diester derivative of formula (I) in a composition comprising in a cosmetically acceptable medium at least one liquid fatty phase and at least one lipophilic organic UV filter for the purpose to improve the sun protection factor.

Other features, aspects and advantages of the invention will appear on reading the detailed description which follows.

By "cosmetically acceptable" is meant compatible with the skin and / or its integuments, which has a pleasant color, odor and feel and which does not generate unacceptable discomfort (tingling, tightness, redness), which can divert the consumer to use this composition.

For the purposes of the present patent application, the term "liquid fatty phase" means a liquid fatty phase at room temperature (25 ° C.) and atmospheric pressure (760 mmHg), composed of one or more liquid fatty substances at ambient temperature. also called oils, compatible with each other.

By "lipophilic active agent" is meant any organic cosmetic or dermatological active agent that can be completely dissolved in the molecular state in a liquid fatty phase or can be solubilized in colloidal form (for example in micellar form) in a liquid fatty phase. . Lipophilic active agent of low solubility is understood to mean any cosmetic or dermatological organic active agent having a solubility in water of less than 0.5% by weight and a solubility of less than 10% by weight in most organic solvents such as paraffin oil, benzoates of fatty alcohols and triglycerides of fatty acids, for example Miglyol 812 sold by the company DYNAMIT NOBEL. This solubility, performed at 70 ° C is defined as the amount of product in solution in the equilibrium solvent with an excess of suspended solid after return to room temperature. It can easily be evaluated in the laboratory. The pyrrolidinone diester derivatives according to the invention are chosen from those corresponding to the following general formula (I): ## STR1 ## in which: R 1 denotes a linear or branched C 1 -C 20 alkyl radical; ; R2 denotes a linear or branched C1-05 alkyl biradical; R3 denotes a linear or branched C1-C8 alkyl radical.

In formula (I), among the alkyl groups, mention may especially be made of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-octyl, 2-ethylhexyl and dodecyl groups. , hexadecyl, cyclohexyl or methylcyclohexyl.

Among the compounds of formula (I), the compounds of the following formulas (a) to (e) will be used more particularly: RN = 121564-86-1 (a) (b)

## STR2 ## (e) The derivatives of Examples (b), (d) and (e) will be used more particularly.

The derivatives of formula (I), the syntheses of which are described in the following articles: J. Med. Chem., 33 (10), pp. 2690-7 (1990); Chem. Comm., 24, pp. 1618-9 (1988); Helvetica Chem. Acta, 37, pp. 1266-72 (1954); Chem. Ber., 86, pp. 404-12 (1953); and in US 5405853 (1987) and US 6911461 (2000) can be easily obtained by the condensation of a diester of itaconic acid of formula (II) with an amino acid of formula (III), with or without solvent such as ethanol or methanol at a temperature between 20 ° C and the reflux temperature of the solvent or between 20 ° C and 150 ° C in the case of the non-use of solvent and according to the following scheme: o

According to one particular form of the invention, the derivative (s) of formula (I) according to the invention are present in a sufficient quantity to solubilize on its own or on its own. by themselves (without the need to use another solvent) the total amount of lipophilic active agent (s) present in the composition.

According to another particular form of the invention, the derivative (s) of formula (I) according to the invention constitute the sole solvent of the lipophilic active agent (s). In this case, the liquid fatty phase may consist of the derivative (s) of formula (I) and the lipophilic active agent (s) dissolved in said phase.

Among the lipophilic active agents that can be used in accordance with the invention, lipophilic organic filters will be used. They may be chosen from para-aminobenzoic acid derivatives, salicylic derivatives, cinnamic derivatives, benzophenones and aminobenzophenones, anthranilic derivatives, dibenzoylmethane derivatives, 3,3-diphenylacrylate derivatives and benzylidene derivatives. camphor, phenyl benzimidazole derivatives, benzotriazole derivatives, triazine derivatives, bis-resorcinyl triazines, imidazoline derivatives, benzalmalonate derivatives, 4,4-diarylbutadiene derivatives, benzoxazole derivatives, merocyanines , malonate or malonitrile diphenyl butadiene derivatives, chalcones and mixtures thereof.

Among the lipophilic UVA filters capable of absorbing UV from 320 to 400 nm, mention may be made of the dibenzoylmethane derivatives: 4-isopropyl-dibenzoylmethane, sold under the name "Eusolex 8020" by the company Merck, and answering with the following formula: 1- (4-methoxy-1-benzofuran-5-yl) -3-phenylpropane-1,3-dione, offered for sale by QUEST under the name of Pongamol of formula: - 1- (4-tert-butylphenyl) -3- (2-hydroxyphenyl) propane-1,3-dione of formula: butyl methoxydibenzoylmethane sold in particular under the trade name PARSOL 1789 by HOFFMANN LA ROCHE,

The aminobenzophenones n-hexyl 2- (4-diethylamino-2-hydroxybenzoyl) benzoate sold under the trade name UVINUL A +

The anthranilic derivatives: Menthyl anthranilate sold under the trade name NEO HELIOPAN MA by HAARMANN and REIMER, The 4,4-diarylbutadiene derivatives: 1,1-dicarboxy (2,2'-dimethylpropyl) -4,4-diphenylbutadiene preferential are:

Among the lipophilic UVB filters capable of absorbing UV from 280 to 320 nm, mention may be made of

Para-aminobenzoates: Ethyl PABA Ethyl Dihydroxypropyl PABA Ethylhexyl Dimethyl PABA (ESCALOL 507 from ISP)

Salicylic derivatives: Homosalate sold under the name Eusolex HMS by Rona / EM Industries, Ethylhexyl salicylate sold under the name NEO HELIOPAN OS by HAARMANN and REIMER, Dipropylene glycol salicylate sold under the name DIPSAL by SCHER, TEA Salicylate, sold under the name NEO HELIOPAN TS by Haarmann and REIMER,

The cinnamates Ethylhexyl Methoxycinnamate sold in particular under the trade name Parsol MCX by Hoffmann La Roche, Isopropyl Methoxy Cinnamate, Isoamyl Methoxy Cinnamate sold under the trade name NEO HELIOPAN E 1000 by HAARMANN and REIMER, Diisopropyl Methylcinnamate, Cinoxate, Glyceryl Ethylhexanoate Dimethoxycinnamate Derivatives of 13j3'-diphenylacrylate: Octocrylene, sold in particular under the trade name UVINUL N539 by BASF, Etocrylene, sold in particular under the trade name UVINUL N35 by BASF,

Benzylidenecamphor derivatives: 3-Benzylidene camphor manufactured under the name MEXORYL SD by CHIMEX, Methylbenzylidene camphor sold under the name EUSOLEX 6300 by MERCK, Polyacrylamidomethyl Benzylidene Camphor manufactured under the name MEXORYL SW by CHIMEX, Triazine derivatives: Ethylhexyl triazone sold in particular under the trade name UVINUL T150 by BASF, Diethylhexyl Butamido Triazone sold under the trade name UVASORB 35 HEB by SIGMA 3V, 2,4,6-tris (4'-amino benzalmalonate dineopentyl) -s-triazine 2, 4,6-tris- (4'-amino benzalmalonate diisobutyl) -s-triazine, 2,4-bis (4'-amino benzalmalonate dineopentyl) -6- (4'-aminobenzoate n-butyl) -s-triazine, 2,4-bis (n-butyl 4'-amino benzoate) -6- (aminopropyltrisiloxane) -s-triazine,

Imidazoline derivatives: Ethylhexyl Dimethoxybenzylidene Dioxoimidazoline Propionate,

Benzalmalonate derivatives: Benzalmalonate-functional polyorganosiloxanes such as Polysilicone-15 sold under the trade name PARSOL SLX by Hoffmann La Roche Di-neopentyl 4'-methoxybenzalmalonate, 50 Merocyanine derivatives Octyl-5-N, N-diethylamino -2-phenysulfonyl-2,4-pentadienoate Among the broad-spectrum lipophilic filters capable of absorbing UVA and UVB, mention may be made of

Benzophenone derivatives Benzophenone-1 sold under the trade name UVINUL 400 by BASF, Benzophenone-2 sold under the trade name UVINUL D50 by BASF Benzophenone-3 or Oxybenzone, sold under the trade name UVINUL M40 by BASF, Benzophenone-5, Benzophenone -6 sold under the trade name Helisorb 11 by Norquay Benzophenone-8 sold under the trade name Spectra-Sorb UV-24 by American Cyanamid Benzophenone-10, Benzophenone-11, Benzophenone-12, Derivatives of benzotriazole: Drometrizole Trisiloxane sold under the name Silatrizole by RHODIA CHIMIE Bumetrizole sold under the name TINOGUARD AS by CIBA-GEIGY The bis-resorcinyl triazine derivatives Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine sold under the trade name TINOSORB S by CIBA GEIGY,

The benzoxazole derivatives: 2,4-bis- [5-1 (dimethylpropyl) benzoxazol-2-yl- (4-phenyl) imino] -6- (2-ethylhexyl) imino-1,3,5-triazine sold under the name of Uvasorb K2A by Sigma 3V The derivatives of the malonate or malonitrile diphenylbutadiene family are the derivatives of general formula (IV): in which R3 represents a C1-C2alkyl group, a C1-C2alkoxy group or a C1-C2alkoxy group; C2 and n is 0, 1 or 2; R4 and R5, which are identical or different, represent -COOR6, - (C = O) NHR6, - (C = O) R6, -CN in which R6 represents an alkyl group containing from 1 to 12 carbon atoms, linear or branched, and which may contain silanic, siloxane or polysiloxane groups. R5 (1v) Among the derivatives of diphenyl butadiene malonates or malonitriles, there may be mentioned, without limitation: - dimethyl 2- (3,3-diphenylprop-2-enylidene) malonate - diisobutyl 2- (3,3-diphenylprop -2-enylidene) malonate s-bis (1,3-dimethylbutyl) 2- (3,3-diphenylprop-2-enylidene) malonate-dineopentyl 2- (3,3-diphenylprop-2-enylidene) malonate-methyl (2Z 2-cyano-5,5-diphenylpenta-2,4-dienoate-ethyl (trimethylsilyl) methyl (2Z) -2- (3,3-diphenylprop-2-enylidene) malonate - (2E) -2-cyano- 5,5-Diphenyl-N- (3- {1,3,3,3-tetramethyl-1 - [(trimethylsilyl) oxy] disiloxanyl} propyl) penta-2,4-dienamide-ethyl-2-methyl-3-yl {1,3,3,3-tetramethyl-1 - [(trimethylsilyl) oxy] disiloxanyl} propyl (2E) -2- (3,3-diphenylprop-2-enylidene) malonate-ethyl (2Z) -5.5- diphenyl-2 - {[(3- {1,3,3,3-tetramethyl-1 - [(trimethylsilyl) oxy] disiloxanyl} propyl) amino] carbonyl} penta-2,4-dienoate Among the derivatives of diphenyl butadienes mentioned above, particular use will be made of dineopentyl 2- (3,3-diphenyl lprop-2-enylidene) malonate corresponding to the following formula: It is known to use these derivatives of diphenyl butadienes in solar compositions, the patent EP 0916335 describes the carbon derivatives and its methods of obtaining and EP 1535947 and EP 1535925 disclose siloxane and silanic derivatives, respectively. The derivatives of the chalcone family are the derivatives of the following general formula (V): (R7 (v) in which the radicals R6 and R7 each independently denote a hydrogen atom, the hydroxyl radical, an alkyl group or C1-C12 alkenyl, linear or branched, a linear or branched C1-C12 alkoxy group or a linear or branched C2-C20 acyloxy group;

Among the chalcone derivatives, there may be mentioned, in a nonlimiting manner: 2-hydroxy-chalcone 4-hydroxy chalcone 4-methoxy chalcone 2-hydroxy-4-methoxy chalcone 2-hydroxy-hexyloxy 4 chalcone - 2-hydroxy-4-methyl-chalcone - 2-hydroxy-3-hexyloxy-2-chalcone-2-hydroxy-4-hexyloxy-4-methyl chalcone-2-hydroxy-4-hexanoyloxy-4-methoxy-chalcone-2-trihydroxy ', 4', 4 diallyl-3,3 'chalcone (known as Kazonol) - trihydroxy-2', 4 ', 4 (methyl-3-but-2-ene) -5' chalcone (known as Broussochalcone B) - 2'-pentahydroxy, 3 ', 4', 6 ', 4 chalcone (known as Carthamin) Among the chalcone derivatives mentioned above, 4-hydroxy will be used in particular. chalcone corresponding to the following formula (Va): or else pentahydroxy-2 ', 3', 4 ', 6', 4 chalcone (known under the name of Carthamin) corresponding to the following formula (Vb):

It is known to use these chalcone derivatives in sunscreen compositions, in particular in patents FR 2555167, FR 2602228 and FR 2608150.

The lipophilic filters are generally present in the compositions according to the invention in proportions ranging from 0.01% to 20% by weight relative to the total weight of the composition, and preferably ranging from 0.1% to 10% by weight relative to to the total weight of the composition.

Among lipophilic filters which are difficult to lipophilic, mention may be made, for example, of dibenzoylmethane derivatives, triazines, merocyanines, benzotriazoles, chalcones, benzophenones or aminobenzophenones, derivatives of the family of malonated or malonitrile diphenyl butadienes.

By lipophilic filter of low solubility is meant any cosmetic or dermatological organic active agent having a solubility in water of less than 0.5% by weight and a solubility of less than 10% by weight in most organic solvents, such as paraffin oil, benzoates of fatty alcohols and triglycerides of fatty acids, for example Miglyol 812 sold by the company DYNAMIT NOBEL. This solubility, performed at 70 ° C., is defined as the amount of product in solution in the equilibrium solvent with an excess of suspended solid after returning to ambient temperature. It can easily be evaluated in the laboratory.

The lipophilic active agents of low solubility in accordance with the invention may also be chosen from aminophenol derivatives, salicylic acid derivatives, N, N'-di (arylmethylene) ethylenediaminetriacetates derivatives, 2-amino-4- derivatives. alkylaminopyrimidine 3-oxide, flavonoids, retinol and its derivatives, carotenoids such as lycopene, and also perfumes, essential oils, hormones, vitamins especially vitamin E, ceramides or mixtures thereof.

The aminophenol derivatives used are more particularly the derivatives of formula (1) below: in which R 'is a radical chosen from the group formed by the following radicals (a), (b) and (c): (a) CO -NR 1 R 2 (b) -CO-O-R 3 (c) -SO 2 R 3 where R 1 represents a hydrogen atom or a linear or branched, saturated or unsaturated, optionally hydroxylated C 1 to C 6 alkyl radical, R 2 represents an atom hydrogen or a radical chosen from saturated or unsaturated, linear, cyclic or branched C12 to C20 alkyl radicals, optionally hydroxylated, and R3 represents a radical chosen from saturated or unsaturated C12 to C30 alkyl radicals, linear, cyclic or branched, including condensed polycyclic, and optionally hydroxylated.

In the formula (1), among linear or branched alkyl radicals R2 or R3 having from 1 to 30 carbon atoms, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, hexyl, octyl and nonyl radicals may be advantageously mentioned. , 2-ethylhexyl, dodecyl, hexadecyl, behenyl and octadecyl, 2-butyloctyl. Preferably, these radicals have from 1 to 12 carbon atoms. Even more preferably, the alkyl radical generally comprises from 1 to 6 carbon atoms. Mention may be made, as lower alkyl radical, of the methyl, ethyl, propyl, isopropyl, tert-butyl and hexyl radicals.

When unsaturated, a radical having one or more ethylenic unsaturations, such as more particularly the allyl radical, is preferred.

When the alkyl radical is cyclic, mention may in particular be made of the cyclohexyl, cholesteryl or terbutylcyclohexyl radical.

When hydroxylated, the radical preferably comprises 1 to 6 carbon atoms and 1 to 5 hydroxyl groups. Among the monohydroxyalkyl radicals, HO (1) is preferably a radical preferably containing 1 or 3 carbon atoms, especially the hydroxymethyl, 2-hydroxyethyl, 2 or 3-hydroxypropyl radicals.

Among the polyhydroxyalkyl radicals, a radical having from 3 to 6 carbon atoms and from 2 to 5 hydroxyl groups, such as the 2,3-dihydroxypropyl, 2,3,4-trihydroxybutyl and 2,3,4,5 radicals, is preferred. tetrahydroxypentyl and 2,3,4,5,6-pentahydroxyhexyl.

The alkoxylated radicals are alkyl radicals, such as in particular described above, preceded by an oxygen atom.

Preferably, the aminophenol derivatives used in the present application are those for which at least one and preferably all the conditions below are met: the function on the phenyl radical is in the ortho position or advantageously in para position, - R 'is selected from a radical of formulas (a) or (b).

Among the linear or branched alkyl radicals R ', mention may be made of methyl, ethyl, propyl, isopropyl, tert-butyl and hexyl radicals.

The aminophenol derivative preferably used in said composition is a para-aminophenol derivative, even more preferably it will be N-ethoxycarbonyl-4-para-aminophenol of formula (Ia):

## STR5 ## or N-cholesteryloxycarbonyl-4-para-aminophenol of formula (1b): ## STR2 ## These aminophenol derivatives, as well as their process of preparation, are described in US Pat. patent applications WO 99/10318 and WO 99/32077.

These derivatives have a hydrocarbon chain longer or shorter, preferably alkoxycarbonyl, linked to the nitrogen atom. They have the disadvantage of being little or not at all soluble in water or in the fatty phase of the type used in the present application. Their introduction into cosmetic compositions requires, for the short-chain hydrocarbon compounds, an aqueous-alcoholic dissolution, which is not always desirable when the composition is intended, for example, to be applied to the contour of the eye. On the other hand, long chain hydrocarbon compounds are insoluble in oils because of their steric bulk and tend to recrystallize in water. The compositions according to the present invention comprising such an aminophenol derivative may be used as a depigmenting or whitening agent in a cosmetic and / or dermatological composition.

The salicylic acid derivatives are the derivatives of formula (2): (2) in which R "1 represents a hydroxyl radical or an ester of formula -O-CO-R" 4

in which R "4 is a saturated or unsaturated aliphatic radical comprising from 1 to 26 carbon atoms, and preferably from 1 to 18 carbon atoms, an amine or thiol functional group optionally substituted by an alkyl radical comprising from 1 to 18 carbon atoms, and preferably 1 to 12 carbon atoms, R "2 and R" 3 independently of one another are in the 3, 4, 5 or 6 position on the benzene ring and independently represent one of the other a hydrogen atom or a radical: - (O) n- (CO) m -R "5 wherein n and m, independently of each other, are each an integer of 0 or 1, with the proviso that R "2 and R" 3 are not simultaneously hydrogen atoms, and R "5 represents hydrogen, a saturated aliphatic radical comprising from 1 to 18 carbon atoms, linear, branched or cyclized an unsaturated radical comprising from 3 to 18 carbon atoms, bearing one to nine conjugated or non-conjugated double bonds, the radicals being be substituted by at least one substituent chosen from halogen atoms (fluorine, chlorine, bromine, iodine), trifluoromethyl radicals, hydroxyl in free form or esterified with an acid comprising from 1 to 6 carbon atoms, or free carboxyl or esterified with a lower alcohol having 1 to 6 carbon atoms, an aromatic radical comprising 6 to 10 carbon atoms. Preferably, the salicylic acid derivative is such that R "5 represents a saturated aliphatic radical comprising from 3 to 15 carbon atoms.

Preferably, the salicylic acid derivative is such that R "1 is a hydroxyl radical Preferably, the salicylic acid derivative is such that R" 5 is at the 5-position of the benzene ring and R "2 is a hydrogen atom.

According to a preferred embodiment of the invention, these are the derivatives of n-octanoyl-5-salicylic acid, n-decanoyl-5-salicylic acid, n-dodecanoyl-5-salicylic acid, n-octyl-5- salicylic, n-heptyloxy-5-salicylic, n-heptyloxy-4-salicylic, 5-tertoctylsalicylic, 3-tert-butyl-5-methylsalicylic, 3-tert-butyl-6-methylsalicylic, 3,5-diisopropylsalicylic, 5- butoxysalicylic, 5-octyloxysalicylic, 5-propanoyl-salicylic, n-hexadecanoyl-5-salicylic, n-oleoyl-5-salicylic acid, benzoyl-5-salicylic acid, their monovalent and divalent salts and mixtures thereof.

It is particularly preferred to use the 2-hydroxy-5-octanoylbenzoic acid proposed for sale under the trade name "Mexoryl SAB" by the company CHIMEX; It has the following formula: It is known to use salicylic acid derivatives in topical compositions, for example, as a keratolytic agent for treating acne or as an anti-aging agent, FR-US patent applications. A-2,581,542 and EP-A-378,936 describe such derivatives.

The salicylic acid derivatives are of great interest, in particular to prevent or repair the main manifestations of skin aging such as fine lines and wrinkles, the disorganization of the "grain" of the skin, the modification of the complexion of the skin and the loss of firmness and tone of the skin. However, the use of these derivatives is a problem in that, when introduced as such into the topical compositions, they do not solubilize and remain in the form of crystals, which makes the use of the composition containing them, ineffective for the treatment of the skin.

Generally, these derivatives are dissolved in lower alcohols such as ethanol or isopropanol or solvents such as octyldodecanol, certain glycols, short chain (lower than C12) fatty alcohols. However, these lower alcohols have the drawback of drying out and irritating the skin; we therefore prefer to avoid using them in body care products and / or face. In addition, these solubilizers can only be introduced in small quantities, otherwise the cosmetic qualities (drying of the skin) and the stability of the compositions containing them will be impaired. The concentration of salicylic acid derivatives of the composition according to the present invention is preferably from 0.001 to 15% by weight, more preferably from 0.1 to 5% by weight relative to the total weight of the composition. The amount of amino acid esters will depend on the amount of salicylic acid derivatives to be solubilized. It may be from 0.01 to 90% by weight, and preferably from 0.1 to 60% by weight relative to the total weight of the composition.

The composition according to the invention comprising at least one salicylic derivative may be used as a cosmetic or dermatological composition, and in particular for the care, protection, cleaning and / or makeup of keratinous substances of human beings (skin, lips, keratinous fibers such as hair and eyelashes), and in particular to fight against the signs of skin aging and / or to smooth the skin of the face and / or the body and / or to treat the wrinkles and fine lines of the skin and / or to stimulate the skin. epidermal renewal process and / or to depigment and whiten the skin and / or to treat acne and / or to treat skin disorders.

These derivatives and the process for their preparation are described in patent WO 94/11338. The derivatives of the family of 2-amino-4-alkylamino pyrimidine 3-oxides are the derivatives of general formula (3): ## STR3 ## wherein R 4 represents an alkyl group comprising from 1 to 20 carbon atoms and Z 'represents a hydrogen atom or an OR5 radical in which R5 represents an alkyl group containing from 1 to 12 carbon atoms, as well as its acylated forms or its acid addition salt.

Preferably, R4 is selected from the group consisting of hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl.

Preferably, R 5 is selected from the group consisting of ethyl, propyl, butyl, pentyl, hexyl.

More preferably, it is 2-amino, 4-dodecylamino-pyrimidine 3-oxide. The derivatives of the family of 2-amino-4-alkylamino pyrimidine 3-oxides can in particular be used in or for the preparation of a cosmetic or dermatological composition according to the present invention for preventing and treating problems related to sensitive skin and the skin. skin disturbances 40 such as cutaneous discomfort, skin tightness, itchy skin, skin swelling, redness of the skin and sensation of cutaneous warmth.

Another family of molecules that falls within the definition of low water solubility molecules is DHEA, its derivatives and its chemical or metabolic precursors.

DHEA or dehydroepiandrosterone, also known as 3-betahydroxyandrost-5-en-17-one, or dehydroisoandro-sterone, but also transdhehydro androsterone or prasterone, has the formula: DHEA precursors concerned by the invention are understood to mean biological precursors which are likely to be converted into DHEA during metabolism, as well as its precursor chemicals which can be converted into DHEA by an exogenous chemical reaction. Examples of biological precursors are A5-pregnenolone, 17-hydroxy pregnenolone and 17a-hydroxy pregnenolone sulfate, without this list being limiting.

By chemical precursors of DHEA is meant in particular saponins and their derivatives such as hecogenin (3 beta, 5 alpha, 23r) -3-hydroxyspirostan-12-one) and hecogenin acetate, diosgenin (5 -spirosten-3-beta-ol), smilagenin and sarsapogenin, as well as natural extracts containing them, in particular fenugreek and extracts of Dioscoreas such as wild yam root or Wild Yam, without this list be limiting.

Derivatives of DHEA include both its metabolic derivatives and its chemical derivatives. As metabolic derivatives, there may be mentioned in particular A5-androstene-3,17-diol and especially 5-androstene 3R, 17R-diol, A4-androstene-3,17-dione, 7-hydroxy-DHEA (7a-hydroxy DHEA or 713-hydroxy-DHEA) and 7-keto-DHEA which is itself a metabolite of 7R-hydroxy DHEA, without this list being limiting. 7a-Hydroxy-DHEA is, along with 5-androstene-3, 17β-diol, a major metabolite of DHEA, obtained by the action of 7α-hydroxylase on DHEA. 7R-hydroxy DHEA is a minor metabolite of DHEA, obtained by the action of 7R-hydroxylase on DHEA. The 7-hydroxy DHEA preferably used in the compositions according to the present invention is 7a-hydroxy DHEA. A process for preparing this compound is described in patent applications FR 2 771 105 and WO 94 08588. As chemical derivatives of DHEA, mention may also be made of DHEA salts and in particular water-soluble salts. such as DHEA sulfate; DHEA esters such as esters of hydrocarboxylic acids and of DHEA, in particular those described in US Pat. No. 5,736,537, or else DHEA salicylate, DHEA acetate, DHEA valerate (or n-heptanoate), and DHEA enanthate. Mention may also be made of DHEA carbamates, DHEA 2-hydroxy malonate esters and DHEA amino acid esters. Finally, mention may be made of 3R-acetoxy-7-oxo-DHEA, which may especially be prepared as described in US Pat. Nos. 5,869,709 and 6,111,118. This list is obviously not limiting.

The concentration of DHEA-based compound in the composition according to the present invention may advantageously range from 0.001 to 30% by weight, preferably from 0.01 to 20%, and still more preferably from 0.01 to 10% by weight. % by weight relative to the total weight of the composition. These compounds will be in solubilized form between 20 ° C and 90 ° C.

According to one particular form of the invention, the derivative (s) of formula (I) according to the invention are used as sole solvent for said lipophilic active agent (s).

The compositions in accordance with the invention may comprise, in addition to other UVA and / or UVB organic UV filters which are water-soluble or insoluble in the cosmetic solvents commonly used.

Among the water-soluble UVA filters capable of absorbing UV from 320 to 400 nm, mention may be made of 30-Terephthalylidene Dicamphre Acid Sulfonic Acid manufactured under the name "MEXORYL SX" by CHIMEX - the bis-benzoazolyl derivatives as described in EP Patents 669,323, and US 2,463,264 and more particularly the compound Disodium Phenyl Dibenzimidazole Tetrasulfonate sold under the commercial name "NEO HELIOPAN AP" by Haarmann and REIMER,

Among the water-soluble UVB filters capable of absorbing UV from 280 to 320 nm, mention may be made of p-aminobenzoic (PABA) derivatives such as PABA, 40 Glyceryl PABA, and PEG-25 PABA sold under the name "UVINUL P25" by BASF Phenylbenzimidazole Sulfonic Acid sold in particular under the trade name "Eusolex 232" by Merck, Ferulic acid 45 Salicylic acid DEA methoxycinnamate Benzylidene Camphor Sulfonic acid manufactured under the name "MEXORYL SL" by CHIMEX, Camphor Benzalkonium Methosulfate manufactured under the name "MEXORYL SO" Among the water-soluble UVA and UVB filters, mention may be made of Benzophenone-4 sold under the trade name "UVINUL MS40" by BASF, Benzophenone-5, and Benzophenone-9.

Among the insoluble filters, mention may be made of methylene bis-benzotriazolyl tetramethylbutylphenol, sold in solid form under the trade name MIXXIM BB / 100 by FAIRMOUNT CHEMICAL or in micronized form in aqueous dispersion under the trade name TINOSORB M by CIBA SPECIALTY CHEMICALS, symmetrical triazine filters described in US Patent 6,225,467, WO 2004/085412 (see Compounds 6 and 9) or Symetrical Triazine Derivatives IP.COM Journal, IP.COM INC. WEST HENRIETTA, NY, US (September 20, 2004) 2,4,6-tris (biphenyl) -1,3,5-triazines (especially 2,4,6-tris (biphenyl-4-yl-1,3,5-triazine) and 2 , 4,6-tris (terphenyl) -1,3,5-triazine which is incorporated in the applications of BEIERSDORF WO 06/035000, WO 06/034982, WO 06/034991, WO 06/035007, WO 2006/034992, WO 2006/034985 Of course, those skilled in the art will take care to choose the optional additional filters and / or their quantities in such a way that the p Advantageous properties intrinsically attached to the compositions according to the invention are not, or not substantially, impaired by the addition or additions envisaged.

The compositions according to the invention may also contain agents for artificial tanning and / or browning of the skin (self-tanning agents), and more particularly dihydroxyacetone (DHA). They are present preferably in amounts ranging from 0.1 to 10% by weight relative to the total weight of the composition.

The aqueous compositions in accordance with the present invention may furthermore comprise conventional cosmetic adjuvants, chosen especially from fatty substances, organic solvents, ionic or nonionic thickeners, hydrophilic or lipophilic thickeners, softeners, humectants, opacifiers and stabilizers. , emollients, silicones, anti-foam agents, perfumes, preservatives, anionic, cationic, nonionic, zwitterionic or amphoteric surfactants, active agents, fillers, polymers, propellants, basifying agents or acidifying agents or any other ingredient usually used in the cosmetic and / or dermatological field. The fatty substances may consist of an oil or a wax other than the apolar waxes as defined above or mixtures thereof. By oil is meant a liquid compound at room temperature. By wax is meant a compound that is solid or substantially solid at room temperature and whose melting point is generally greater than 35 ° C.

As oils, mention may be made of mineral oils (paraffin); vegetable (sweet almond oil, macadamia oil, blackcurrant seed oil, jojoba oil); 50 such as perhydrosqualene, alcohols, fatty amides (such as isopropyl lauroyl sarcosinate sold under the name Eldew SL-205 by the company Ajinomoto), fatty acids or esters such as benzoate C12-alcohols. C15 sold under the trade name Finsolv TN or Witconol TN by the company WITCO, 2-ethylphenyl benzoate as the commercial product sold under the name X-TEND 226 by the company ISP, octyl palmitate, isopropyl lanolate triglycerides, including those of capric / caprylic acids, dicaprylyl carbonate sold under the name Cetiol CC by Cognis), oxyethylenated or oxypropylenated esters and fatty ethers; silicone oils (cyclomethicone, polydimethylsiloxane or PDMS) or fluorinated oils, polyalkylenes.

As waxy compounds, mention may be made of carnauba wax, beeswax, hydrogenated castor oil, polyethylene waxes and polymethylene waxes, such as that sold under the name Cirebelle 303 by the company SASOL.

Among the organic solvents, mention may be made of lower alcohols and polyols. These can be selected from glycols and glycol ethers such as ethylene glycol, propylene glycol, butylene glycol, dipropylene glycol or diethylene glycol.

As hydrophilic thickeners, mention may be made of carboxyvinyl polymers such as Carbopols (Carbomers) and Pemulen (acrylate / C10-C30-alkylacrylate copolymer); polyacrylamides, for example crosslinked copolymers sold under the names Sepigel 305 (CTFA name: polyacrylamide / C13-14 isoparaffin / Laureth 7) or Simulgel 600 (CTFA name: acrylamide / sodium acryloyldimethyltaurate copolymer / isohexadecane / polysorbate 80) by the company Seppic ; polymers and copolymers of 2-acrylamido-2-methylpropanesulphonic acid, optionally cross-linked and / or neutralized, such as poly (2-acrylamido-2-methylpropanesulphonic acid) marketed by Hoechst under the trademark Hostacerin AMPS (CTFA name: ammonium polyacryloyldimethyl taurate or SIMULGEL 800 sold by the company SEPPIC (CTFA name: sodium polyacryolyldimethyl taurate / polysorbate 80 / sorbitan oleate); copolymers of 2-acrylamido-2-methylpropanesulphonic acid and hydroxyethyl acrylate such as SIMULGEL NS and SEPINOV EMT 10 sold by the company SEPPIC, cellulosic derivatives such as hydroxyethylcellulose, polysaccharides and in particular gums such as Xanthan gum, and mixtures thereof.

As lipophilic thickeners, mention may be made of synthetic polymers such as poly C 10 -C 30 alkyl acrylates sold under the name INTELIMER IPA 13-1 and INTELIMER IPA 13-6 by the company Landec, or modified clays such as hectorite and its derivatives. derivatives, such as the products marketed under the names of Bentone.

Among the active ingredients, mention may be made of: vitamins (C, K, PP) and their derivatives or precursors, alone or in mixtures, anti-pollution agents and / or anti-radical agents; depigmenting agents and / or pro-pigmenting agents; anti-glycation agents; the soothing agents; the NO-synthase inhibitors; agents stimulating the synthesis of dermal or epidermal macromolecules and / or preventing their degradation; agents stimulating the proliferation of fibroblasts; agents stimulating the proliferation of keratinocytes; - muscle relaxants; tensing agents, matting agents, keratolytic agents, desquamating agents; the moisturizing agents; Anti-inflammatory agents; agents acting on the energetic metabolism of cells; insect repellents; antagonists of substances P or CRGP. anti-hair loss and / or hair regrowth agents anti-wrinkle agents.

Of course, those skilled in the art will take care to choose the optional additional compound or compounds mentioned above and / or their amounts in such a way that the advantageous properties intrinsically attached to the compositions according to the invention are not, or substantially not, altered by the addition or additions envisaged.

The compositions according to the invention can be prepared according to the techniques well known to those skilled in the art. They may be in particular in the form of emulsions, simple or complex (O / W, W / O, O / W / H or W / O / W) such as cream, milk or gel. cream; in the form of an aqueous gel; in the form of a lotion. They may optionally be packaged in aerosol and be in the form of foam or spray.

Preferably, the compositions according to the invention are in the form of an oil-in-water or water-in-oil emulsion.

The emulsions generally contain at least one emulsifier chosen from amphoteric, anionic, cationic or nonionic emulsifiers, used alone or as a mixture. The emulsifiers are suitably selected according to the emulsion to be obtained (W / O or O / W). The emulsions may also contain other types of stabilizers, for example fillers, gelling or thickening polymers.

Exemplary emulsifying surfactants for the preparation of W / O emulsions include, for example, alkyl esters or ethers of sorbitan, glycerol or sugars; silicone surfactants such as dimethicone copolyols such as the mixture of cyclomethicone and dimethicone copolyol, sold under the name DC 5225 C by Dow Corning, and 50 alkyl dimethicone copolyols such as Laurylmethicone copolyol sold under the name "Dow Corning" 5200 Formulation Aid "by Dow Corning; cetyl dimethicone copolyol such as the product sold under the name Abil EM 90R by Goldschmidt and the mixture of cetyl dimethicone copolyol, polyglycerol isostearate (4 moles) and hexyl laurate sold under the name ABIL WE 09 by the company Goldschmidt. One or more coemulsifiers may also be added, which advantageously may be selected from the group consisting of alkylated polyol esters.

Polyol alkyl esters that may be mentioned include polyethylene glycol esters such as PEG-30 dipolyhydroxystearate, such as the product sold under the name Arlacel P135 by the company ICI.

Examples of glycerol and / or sorbitan esters that may be mentioned are polyglycerol isostearate, such as the product sold under the name Isolan GI 34 by the company Goldschmidt; sorbitan isostearate, such as the product sold under the name Arlacel 987 by the company ICI; sorbitan isostearate and glycerol, such as the product sold under the name Arlacel 986 by the company ICI, and mixtures thereof.

Examples of O / W emulsions which may be mentioned as emulsifiers are nonionic emulsifiers such as oxyalkylenated (more particularly polyoxyethylenated) fatty acid esters of glycerol; oxyalkylenated fatty acid and sorbitan esters; oxyalkylenated fatty acid esters (oxyethylenated and / or oxypropylenated) such as PEG-100 Stearate / Glyceryl Stearate sold, for example, by the company ICI under the name Arlacel 165; oxyalkylenated fatty alcohol ethers (oxyethylenated and / or oxypropylenated); sugar esters such as sucrose stearate; fatty alcohol and sugar ethers, especially alkylpolyglucosides (APG) such as decylglucoside and laurylglucoside sold, for example, by Henkel under the respective names Plantaren 2000 and Plantaren 1200, cetostearylglucoside optionally in admixture with alcohol; cetostearyl, marketed for example under the name Montanov 68 by the company Seppic, under the name Tegocare CG90 by the company Goldschmidt and under the name Emulgade KE3302 by Henkel, as well as arachidyl glucoside, for example in the form of the mixture of arachidic and behenic alcohols and arachidylglucoside sold under the name Montanov 202 by the company Seppic. According to a particular embodiment of the invention, the mixture of the alkylpolyglucoside as defined above with the corresponding fatty alcohol may be in the form of a self-emulsifying composition, as described for example in the document WO -A-92/06778.

Among the other emulsion stabilizers, the polymers of isophthalic acid or sulphoisophthalic acid, and in particular the phthalate / sulphoisophthalate / glycol copolymers, for example the diethylene glycol / phthalate / isophthalate / 1,4 copolymer, will be used more particularly. cyclohexane dimethanol (INCI name: Polyester-5) sold under the names "Eastman AQ polymer" (AQ35S, AQ38S, AQ55S, AQ48 Ultra) by the company Eastman Chemical.

In the case of an emulsion, the aqueous phase thereof may comprise a nonionic vesicle dispersion prepared according to known methods (Bangham, Standish and Watkins, J. Mol Biot 13, 238 (1965)). FR 2 315 991 and FR2416008).

The compositions according to the invention find their application in a large number of treatments, in particular cosmetics, of the skin, lips and hair, including the scalp, in particular for the protection and / or care of the skin, lips and / or hair, and / or for makeup of the skin and / or lips.

Another object of the present invention is the use of the compositions according to the invention as defined above for the manufacture of products for the cosmetic treatment of the skin, lips, nails, hair, eyelashes. , eyebrows and / or scalp, including skincare products, sunscreen products and make-up products.

The cosmetic compositions according to the invention may for example be used as a makeup product. The cosmetic compositions according to the invention may for example be used as a care product and / or sun protection for the face and / or body of liquid to semi-liquid consistency, such as milks, more or less smooth creams. , gel-creams, pasta. They may optionally be packaged in aerosol and be in the form of foam or spray.

The compositions according to the invention in the form of vaporizable fluid lotions according to the invention are applied to the skin or the hair in the form of fine particles by means of pressurizing devices. The devices according to the invention are well known to those skilled in the art and include non-aerosol pumps or "atomizers", aerosol containers comprising a propellant and aerosol pumps using compressed air as a propellant. These are described in US Patents 4,077,441 and US 4,850,517.

The aerosol-conditioned compositions according to the invention generally contain conventional propellants such as, for example, hydrofluorinated compounds, dichlorodifluoromethane, difluoroethane, dimethyl ether, isobutane, n-butane, propane and trichlorofluoromethane. They are present preferably in amounts ranging from 15 to 50% by weight relative to the total weight of the composition.

Concrete but non-limiting examples illustrating the invention will now be given.

SOLUBILITIES COMPRISING LIPOPHILIC ASSETS BETWEEN SOLVENTS OF THE PRIOR ART AND THE SOLVENTS OF THE INVENTION 5o Filters Tested 5 15 Fi11: Isobutyl 2,4-bis (4'-aminobenzalmalonate) -6 - [(3- {1,3,3,3-tetramethyl-1 - [(trimethylsilyl) oxy] disiloxanyl} propyl) amino] -1,3,5-triazine as described in example 5 of patent EP 0841341: F112: octyl ( 2Z, 4E) -5- (diethylamino) -2- (phenylsulfonyl) penta-2,4-dienoate (known as CKK-92 from FujiFilm): F113: 5 - [(2-ethylhexyl) oxy] -2- [4- {4 - [(2-ethylhexyl) oxy] -2-hydroxyphenyl} -6- (4-methoxyphenyl) -1,3,5-triazin-2-yl] phenol (known as Tinosorb S from Ciba): 'O OHN NN HO d OC \

F114: 2-ethylhexyl 4 - ({4,6-bis [(4 - {[(2-ethylhexyl) oxy] carbonyl} phenyl) amino] -1,3,5-triazin-2-yl} amino) benzoate ( known as Uvinul T150 from BASF): F115: 1- (4-tert-butylphenyl) -3- (4-methoxyphenyl) propane-1,3-dione (known as DSM Parsol 1789): F116 butyl 4 - ({4 - {[4- (butoxycarbonyl) phenyl] amino} -6 - [(3- {1,3,3,3-tetramethyl-1 - [(trimethylsilyl) oxy] disiloxanyl} propyl) amino ] -1,3,5-triazin-2-yl} amino) benzoate 0 sb si / \ 9 ~ -Si ~~ NI, NYN NYN 10 Comparative oil 1: Finsolv TN: C12-C15 alkylbenzoate

Comparative Oil 2: Miglyol 812: Caprylic-Capric Acid Triglycerides Procedure:

X mg of product are introduced into Y mg of oil; with a slight heating (<60 ° C) and the use of a sonicator for 1 minute, the resulting solution is left at laboratory temperature for 1 month; the state of this solution is observed; if no crystals or oily deposits are visible, the solubility of the product is considered to be greater than Xx100 / (X + Y) in weight / weight; when crystals or an oily deposit appear, the test is repeated with 5% less product.

Table 1 Tested oil C12-C15 alkyl 11-diol 8% Triglycerides 6% caprylic-capric acids Compound (b) 28% The invention N io Table 2 Test oil FiI2 C12-C15 alkylbenzoate 20% Triglycerides 16% caprylic acid-capric acid Compound (c) 32% the invention Table 3 Test oil FiI3 C12-C15 alkylbenzoate 8% Triglycerides 6% caprylic-capric acids Compound (d) 21% the invention Compound (e) ) 18% the invention Table 4 Tested oil FiI4 Alkylbenzoate 5% C12-C15 Compound (b) 28% the invention Table 5 Tested oil FiI5 Alkylbenzoate 15% C12-C15 Compound (d) 40% Table 6 Test oil FiI6 C12-C15 alkylbenzoate 31% Triglycerides 28% caprylic-capric acid Compound 44% (e) the invention EXAMPLES OF FORMULATION 1-4 Composition Ex1 Ex2 Ex3 Ex4 Phase A Poly Dimethylsiloxane 0, 5 0.5 0.5 0.5 PreservativesConservatives 1 1 1 1 Stearic acid 1.5 1.5 1.5 1.5 Mixture mono-stearate glyceryl / stearate 1 1 1 1 PEG100 Mixture of cetylstearyl glucoside and alcohols 2 2 2 2 cetyl, stearyl Cetyl alcohol 0.5 0.5 0.5 0.5 Butyl 1-butyl-5-oxopyrrolidine-3-carboxylate 20 - (compound (c)) 1- (4-methoxy-1-benzofuran-5-yl) -3-phenylpropane-1,3-dione Dineopentyl 2- (3,3-diphenylprop-2-enylidene) malonate Phase B Deionized water qsp qsp qsp qsp 100 100 100 100 Glycerol 5 5 5 5 Xanthan gum 0.2 0.2 0.2 0.2 Phenyl ketyl phosphate 1 1 1 1 Phase C Isohexadecane 1 1 1 1 Copolymer acrylic acid 0.2 0.2 0.2 0.2 stearyl methacrylate Triethanolamine qs qs qs qs qsp pH pH pH H The above formulations were prepared, the amounts are expressed as percentages by weight relative to the total weight of the composition .

Procedure: The aqueous phase (Phase B) containing all of its ingredients is heated at 80 ° C. in a water bath. The fatty phase (Phase A) containing all of its ingredients is heated to 80 ° C. in a water bath. A is emulsified in B with rotor-stator type stirring (apparatus of the Moritz company). Phase C is incorporated and allowed to warm to room temperature with gentle stirring. The triethanolamine is introduced so as to adjust the pH to the desired value at the end of manufacture. The resulting sunscreen emulsions are storage stable and do not show crystals or precipitates.

Claims (15)

REVENDICATIONS1. in which: RI denotes an alkyl radical in Claims 1. in which: RI denotes a linear or branched C1-C20 alkyl radical; R2 denotes a linear or branched C1-05 alkyl biradical; R3 denotes a linear or branched C1-C8 alkyl radical in a composition comprising, in a cosmetically acceptable medium, at least one liquid fatty phase and at least one lipophilic active agent, as a solvent for said active agent in said liquid fatty phase and / or as agent improving the solubility of said active in said fatty phase. 2. Use according to claim 1, wherein the compounds of formula (I) are selected from the following compounds (a) to (c): o (a) (b) (c) 3. Use according to claim 1 or 2, wherein the derivative (s) of formula (I) according to the invention constitutes (s) the sole solvent of the lipophilic active (s). 1. Use of at least one pyrrolidinone diester derivative of formula (I): O R2 O R1 (I) 4. Use according to any one of claims 1 to 3, wherein the lipophilic active is selected from lipophilic organic UV filters. 5. Use according to any one of claims 1 to 3, wherein the lipophilic filter is selected from para-aminobenzoic acid derivatives, salicylic derivatives, cinnamic derivatives, benzophenones and aminobenzophenones, anthranilic derivatives, derivatives thereof. dibenzoylmethane derivatives, 13,13-diphenylacrylate derivatives, benzylidene camphor derivatives, phenyl benzimidazole derivatives, benzotriazole derivatives, triazine derivatives, bis-resorcinyl triazines, imidazoline derivatives, benzalmalonate derivatives 4,4-diarylbutadiene derivatives, benzoxazole derivatives, merocyanines, malonate or malonitrile diphenylbutadiene derivatives, chalcones and mixtures thereof. 15 6. Use according to claim 5, wherein the organic lipophilic UV filters are chosen from dibenzoylmethane derivatives, triazines, merocyanines, benzotriazoles, chalcones, benzophenones or aminobenzophenones, derivatives of the malonate or malonitrile diphenyl butadiene family. 20 7. Use according to any one of claims 1 to 3, wherein the lipophilic active agent is chosen from aminophenol derivatives, salicylic acid derivatives, N, N'-di (arylmethylene) ethylenediaminetriacetates derivatives, 2-amino-4-alkylaminopyrimidine 3-oxide derivatives, flavonoids, retinol and its derivatives, carotenoids, in particular lycopene, perfumes, essential oils, hormones, vitamins, in particular vitamin E, ceramides or their mixtures . 8. Composition comprising in a cosmetically acceptable medium at least one liquid fatty phase characterized in that it contains at least one pyrrolidinone diester derivative of formula (I) as defined in any one of claims 1 and 2 and at least one lipophilic active agent. 9. The composition of claim 7 wherein the lipophilic active agent is selected from lipophilic organic UV filters. 10. Composition according to claim 9, wherein the lipophilic filter is chosen from para-aminobenzoic acid derivatives, salicylic derivatives, cinnamic derivatives, benzophenones and aminobenzophenones, anthranilic derivatives, dibenzoylmethane derivatives, R, R-diphenylacrylate derivatives, benzylidene camphor derivatives, phenyl benzimidazole derivatives, benzotriazole derivatives, triazine derivatives, bisresorcinyl triazines, imidazoline derivatives, benzalmalonate derivatives, 4,4-derivatives. diarylbutadiene, benzoxazole derivatives, merocyanines, malonate or malonitrile diphenylbutadiene derivatives, chalcones and mixtures thereof. 11. A composition according to claim 10, wherein the lipophilic organic UV filter is chosen from dibenzoylmethane derivatives, triazines, merocyanines, benzotriazoles, chalcones, benzophenones oraminobenzophenones, derivatives of the malonate or malonitrile diphenylbutadiene family. 12. A composition according to claim 8, wherein the lipophilic active agent is chosen from aminophenol derivatives, salicylic acid derivatives, N, N'-di (arylmethylene) ethylenediaminetriacetates derivatives, 2-amino-4- derivatives. alkylaminopyrimidine 3-oxide, flavonoids, retinol and its derivatives, carotenoids, in particular lycopene, perfumes, essential oils, hormones, vitamins, in particular vitamin E, ceramides or their mixtures. 13. Composition according to any one of claims 8 to 12, wherein the derivative (s) of formula (I) according to the invention are preferably present in the compositions of the invention at levels ranging from 1 to 30% by weight. and more preferably from 3 to 20% by weight based on the total weight of the composition. 14. Use of at least one derivative of formula (I) as defined in any one of claims 1 and 2 in a composition comprising in a cosmetically acceptable medium at least one liquid fatty phase and at least one lipophilic active agent in the aim of improving the efficacy of said active ingredient and / or the cosmetic qualities and / or the stability of said composition. 15. Use of at least one derivative of formula (I) as defined in any one of claims 1 and 2 in a composition comprising in a cosmetically acceptable medium at least one liquid fatty phase and at least one organic UV filter. lipophilic in order to improve the sun protection factor. 30