FR2847466A1 - Cosmetic composition useful as a slimming or anticellulite product and as a product for combating formation of bags and rings under the eyes comprises a coumarin derivative and a lipophilic amino acid derivative - Google Patents

Abstract

Cosmetic composition comprises a coumarin derivative and a lipophilic amino acid derivative. An Independent claim is also included for solubilizing coumarin derivatives by mixing them with amino acid esters of formula R'1(CO)N(R'2)CH(R'3)(CH2)n(CO)OR'4 (III); n = 0-2; R'1 = 5-21C alkyl or alkenyl; R'2 = H or 1-3C alkyl; R'3 = H or 1-4C alkyl; R'4 = 1-10C alkyl, 2-10C alkenyl or a sterol residue.

Description

The present invention relates to a composition, in particular a cosmetic composition,

  comprising a coumarin derivative and a lipophilic amino acid derivative, as well as its uses in the cosmetic and / or dermatological field. It also relates to a process for solubilizing a coumarin derivative with a lipophilic amino acid derivative. It is known to use active ingredients in cosmetic and / or dermatological compositions, for example for the purpose of treating or treating or bringing beneficial effects to the skin. However, the use of some of these assets is problematic in that they are in crystalline form and where they are

  hardly or not at all soluble in water.

  Thus, if they are introduced as such into the cosmetic and / or dermatological compositions, they remain in the form of crystals, which makes the use of the

  composition containing them, ineffective for the treatment of the skin.

  Generally and for some of them, it is possible to introduce them in the presence of a solvent, but the presence of this solvent is not always desirable, especially when applied to certain areas of the face, such as the contour

eyes.

  This is particularly the case of compounds such as visnadine or its derivatives. These active principles are of interest in cosmetics, in particular because of their action on the microcirculation. In order to ensure good solubilization, these compounds are formulated in general in the presence of lipophilic constituents. Among these known solubilizers, there may be mentioned triglycerides of capricylic / caprylic acids, isopropyl myristate. Similarly, these compounds can be formulated in the presence of glycols. However, visnadine tends to recrystallize easily, which limits the amount of compound used. In order to overcome this drawback, the increase in the amount of solubilizer, in particular those mentioned above, leads to a rapid degradation of the cosmetic qualities and the

stability of the compositions.

  There remains therefore the need to be able to introduce these compounds of low solubility, in sufficient quantity, in cosmetic and / or dermatological compositions, especially in the lipophilic phase of such compositions, without loss of cosmetics. It therefore remains necessary to be able to easily solubilize the coumarin derivatives in a physiologically acceptable medium which causes a minimum of discomfort

  to the application on the skin or the scalp, and which is easy to implement.

  In addition, it is necessary to solubilize a sufficient amount of these compounds for cosmetic or dermatological use, without recrystallization of these compounds or loss of stability of the composition containing them. This instability would result in a more or less significant loss of effectiveness of these compositions and / or in a modification of their appearance, which

  could distract the user from them.

  Now, the Applicant has now discovered that lipophilic amino acid derivatives make it possible to increase, unexpectedly, the solubilization of these derivatives.

coumarin.

  The subject of the present invention is therefore a composition comprising, in a physiologically acceptable medium, at least one coumarin derivative and at least one

  minus a lipophilic amino acid derivative.

  In the present application, the term "physiologically acceptable medium" means a medium compatible with the skin, including the scalp, the mucous membranes, the

eyes and / or hair.

  The main advantage of the use of lipophilic amino acid derivatives according to the invention is that they make it possible to solubilize a sufficient quantity of coumarin derivatives, for cosmetic or dermatological use, without recrystallization of said coumarin derivatives, nor loss of stability of the composition containing them, and therefore obtaining a composition cosmetically

acceptable.

  The coumarin derivatives used in the compositions according to the invention are advantageously chosen from unsubstituted coumarins and coumarins.

  monosubstituted, and disubstituted coumarins, and / or their mixtures.

  In an advantageous aspect of the invention, the coumarin derivatives will be chosen from disubstituted coumarines. In particular, these disubstituted coumarins may be selected from bicyclic coumarines and tricyclic coumarines. In a particular aspect of the invention, the bicyclic coumarines used are represented by the formula (1) R 2 R in which R represents a hydrogen atom or a linear or branched, saturated or unsaturated alkyl group containing from 1 to 20 atoms of carbons, optionally hydroxylated, one carbon atom of which may be replaced by a heteroatom selected from oxygen, nitrogen and sulfur atoms; and R1 and R2 independently represent a hydrogen atom, or a group selected from R30, -O-R31, -N-R31R32, -CO-R31 or -O-CO-R30, wherein R30 represents a group selected from linear or branched, saturated or unsaturated alkyl groups containing from 1 to 20 carbon atoms, optionally hydroxylated, and one carbon atom of which may be replaced by a heteroatom chosen from oxygen, nitrogen and sulfur atoms; cycloalkyl containing from 3 to 8 carbon atoms, optionally hydroxylated, and one carbon atom of which may be replaced by a heteroatom chosen from oxygen, nitrogen and sulfur atoms; optionally substituted aryl; mono or bicyclic heteroaryl, containing at least one aromatic ring, comprising from 5 to 11 ring members, and from 1 to 5 heteroatoms selected from nitrogen, oxygen and sulfur, optionally substituted; an arylalkyl group in which the aryl and alkyl radicals have the same meaning as above; and heteroarylalkyl wherein the heteroaryl and alkyl radicals have the same meaning as above; and a sugar residue; R31 and R32 independently represent a hydrogen atom or a

grouping R30.

  In another particular aspect of the invention, the tricyclic coumarines used are chosen from compounds of formula (II): R6

R7 <R5

  Wherein R4 and R5 independently represent an alkyl group comprising from 1 to 6 carbon atoms, and R6 and R7 independently represent a hydrogen atom, or a group selected from R60, -O-R61, -N- R61R62, -CO-R61 or -O-CO-R60, in which R60 represents a group chosen from linear or branched, saturated or unsaturated alkyl groups containing from 1 to 20 carbon atoms, optionally hydroxylated, and an atom of which carbon may be replaced by a heteroatom selected from oxygen, nitrogen and sulfur; cycloalkyl containing from 3 to 8 carbon atoms, optionally hydroxylated, and one carbon atom of which may be replaced by a heteroatom chosen from oxygen, nitrogen and sulfur atoms; optionally substituted aryl; mono or bicyclic heteroaryl, containing at least one aromatic ring, comprising from 5 to 11 ring members, and from 1 to 5 heteroatoms selected from nitrogen, oxygen and sulfur, optionally substituted; an arylalkyl group in which the aryl and alkyl radicals have the same meaning as above; and heteroarylalkyl wherein the heteroaryl and alkyl radicals have the same meaning as above; and a sugar residue; R61 and R62 independently represent a hydrogen atom or a

grouping R60.

  In the compounds of formula (1) or (II) above, among the linear or branched alkyl radicals having 1 to 30 carbon atoms, mention may advantageously be made of methyl, ethyl, propyl, isopropyl, n-butyl and isobutyl radicals. tertbutyl, 2-butyl, pentyl, isopentyl, hexyl, octyl, nonyl, 2-ethylhexyl, dodecyl, hexadecyl, behenyl, octadecyl, 2-butyloctyl. Preferably, these radicals contain from 1 to 12 carbon atoms. Even more preferably, the alkyl radical comprises from 1 to 6 carbon atoms. Mention may be made, as lower alkyl radical, of the methyl, ethyl and propyl radicals,

  isopropyl, n-butyl, isobutyl, tert-butyl, 2-butyl, pentyl, isopentyl, hexyl.

  When unsaturated, a radical having one or more

  ethylenic unsaturations, such as more particularly the allyl radical.

  When the alkyl radical is cyclic, mention may in particular be made of the radical

  cyclohexyl, cholesteryl or terbutylcyclohexyl.

  When hydroxylated, the radical preferably comprises 1 to 6 carbon atoms and 1 to 5 hydroxyl groups. Among the monohydroxyalkyl radicals, a radical preferably containing from 1 to 3 carbon atoms, especially

  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 2,3dihydroxypropyl, 2,3,4-trihydroxybutyl and 2,3,4,5tetrahydroxypentyl radicals, is preferred. , 3,4,5,6pentahydroxyhexyle. Among the aryl radicals, mention may be made, for example, of phenyl and naphthyl radicals,

and biphenyl.

  The optionally substituted expression associated with the aryl and heteroaryl groups means that these groups are unsubstituted or substituted by one or more halogen atoms or alkyl, hydroxy, alkoxy, cyano or amino groups (optionally substituted with one or two alkyl groups). , nitro, carboxy, alkoxycarbonyl, aminocarbonyl (optionally substituted with one or

  two alkyl groups), and carbamoyl.

  By sugar residue is meant a radical derived from a mono-, di-, or trisaccharide, among which mention may be made of glucose, galactose, maltose, rhamnose, glucuronic acid. In particular glucose will be referred to. The sugar residue can be attached to the coumarin nucleus by any of the oxygen atoms it

  contains, and preferably by the oxygen atom in the anomeric position.

  Advantageously in the compounds of formula (I), the group R represents a hydrogen atom or a lower alkyl group of 1 to 6

  carbon atoms as defined above.

  Advantageously, in the compounds of formula (I), the groups R 1 and R 2 independently represent a group -O-R 31 in which R 31 is advantageously chosen from a hydrogen atom, an alkyl group such as

  previously defined, and a sugar residue.

  A compound of formula (1) which is particularly suitable for the practice of the present invention is escuioside for which R 1 represents a hydroxyl group, and R 2 represents a group -O-R 31 in which R 31 is a glucose residue:

0 O OH

O OH

OH

HO O

  Another compound of formula (1) which is particularly suitable for the implementation of the present invention is methylsculetin of formula:

O O OH

O OH

O OH

HO O

  These compounds can be obtained conventionally by chemical synthesis or

well extracted from the Horse Chestnut.

  Advantageously, the compounds of formula (II) are chosen from visnadine and its derivatives, ie compounds for which the groups R4 and R5

  each represent a methyl group.

  In the preferred compounds of formula (II), the groups R 6 and R-7 independently represent a group -O-CO-R 6, as defined above, R 6 being

  preferably an alkyl group as defined above.

  A compound of formula (II) which is particularly suitable for carrying out the present invention is visnadine, for which R4 and R5 each represent a methyl group, R6 represents a group -OCO-R6, in which R61 is a group 2 -butyl, and R7 represents a group -O-CO-R61 in which R61 is a methyl group: The lipophilic derivative of amino acid is preferably an ester chosen from the amino acid esters of formula (III ): RW1 (CO) N (R'2) CH (R'3) (CH2), (CO) OR'4 (III) in which: n is an integer equal to 0, 1 or 2, R'1 represents a linear or branched C 5 to C 21 alkyl or alkenyl radical, R '2 represents a hydrogen atom or a C 1 to C 3 alkyl group, R' 3 represents a radical chosen from the group formed by a hydrogen atom, a methyl group, an ethyl group, a linear or branched C3-C4 alkyl radical, R'4 represents a linear or branched C1-C10 alkyl radical,

  or a linear or branched C 2 to C 10 alkenyl radical or a sterol residue.

  These amino acid esters, as well as their synthesis process, are described in the patent applications EP 1 044 676 and EP 0 928 608 of the company Ajinomoto Co. In the amino acid esters of formula III, the R'1 group ( CO) - is preferably an acyl group of an acid preferably selected from the group consisting of capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid , linoleic acid, linolenic acid, oleic acid, isostearic acid, 2-ethylhexanoic acid, coconut oil fatty acids, palm kernel oil fatty acids. These fatty acids may furthermore have a hydroxyl group. Even more preferably, it will be lauric acid. The part -N (R'2) CH (R'3) (CH2) n (CO) - of the amino acid ester is preferably chosen from the following amino acids: glycine, alanine, valine, leucine, isoleucine, serine Threonine Proline Hydroxyproline 13-Alanine Acid

  aminobutyric, aminoca-proic acid, sarcosine, or N-methyl-13-alanine.

  Even more preferably, it will be sarcosine.

  The part of the amino acid esters corresponding to the group OR '4 can be obtained from the alcohols chosen from the group formed by methanol, ethanol, propanol, isopropanol, butanol, tert-butanol, isobutanol, 3-methyl-1-butanol, 2-methyl 1-butanol, fusel oil, pentanol, hexanol, cyclohexanol, octanol, 2-ethylhexanol, decanol, lauryl alcohol, myristic alcohol, cetyl alcohol, cetostearyl alcohol, stearyl alcohol, oleic alcohol, behenyl alcohol, alcohol

  jojoba, 2-hexadecyl alcohol, 2-octyldodecanol alcohol and isostearyl alcohol.

  These amino acid esters can in particular be obtained from natural sources of amino acids. In this case, the amino acids come from hydrolysis of natural plant proteins (oats, wheat, soybean, palm, coconut) and then necessarily lead to mixtures of amino acids which will then be esterified and then N-acylated. The preparation of such amino acids is more particularly described in the patent application FR 2 796 550 which is

incorporated herein by reference.

  The amino acid ester more particularly preferred for use in the present invention is isopropyl N-lauroylsarcosinate of formula:

  CH3- (CH2) I0CO-N (CH3) -CH2-COO-CH2 (CH3) 2.

  The concentration of coumarin derivatives in the composition according to the present invention is between 0.001 and 30%, preferably between 0.001 and 20%, even more preferably between 0.1 and 5% by weight relative to the total weight of the composition. The amount of amino acid esters will depend on the amount of coumarin derivatives to be solubilized and may be between 0.01 and 90% by weight and preferably between 0, 1 and 30% by weight relative to the total weight of the composition. The composition according to the invention can be used as a cosmetic composition, in particular for improving microcirculation, as a slimming composition, for combating cellulite, as a composition intended to be applied to the contour of the eye, in particular for combating the formation of

  puffiness and / or dark circles under the eyes.

  The composition according to the present invention can also be used for

  manufacture of a dermatological preparation.

  The invention therefore also relates to the cosmetic use of the composition as defined above as a slimming composition, to fight against cellulite, and to fight against the formation of bags and / or dark circles under the eyes and a process cosmetic treatment for thinning, for fighting against cellulite, and for combating the formation of puffiness and / or dark circles under the eyes, which

  comprises applying to the skin a composition according to the invention.

  The compositions used according to the invention are intended for topical application to the skin and / or its integuments and therefore contain a physiologically acceptable medium, that is to say, compatible with cutaneous tissues such as the skin, the scalp, eyelashes, eyebrows, hair, nails and / or mucous membranes. This physiologically acceptable medium may more particularly consist of water and optionally of a physiologically acceptable organic solvent chosen, for example, from lower alcohols containing from 1 to 8 carbon atoms and in particular from 1 to 6 carbon atoms, such as ethanol, isopropanol, propanol, butanol; polyethylene glycols having from 6 to 80 ethylene oxide units; polyols such as propylene glycol, isoprene glycol, butylene glycol, glycerine, sorbitol, dipropylene

  glycol, pentylene glycol and hexylene glycol.

  The compositions according to the invention may be in any of the galenical forms conventionally used for topical application and especially in the form of aqueous, hydroalcoholic, oil-in-water (O / W) or water-in-oil ( E / H) or multiple (triple: W / H / E or H / E / H), aqueous gels, or dispersions of a fatty phase in an aqueous phase using spherules, these spherules being polymeric nanoparticles such as nanospheres and nanocapsules, or lipid vesicles of ionic and / or nonionic type (liposomes,

  niosomes, oleosomes). These compositions are prepared according to the usual methods.

  In addition, the compositions used according to the invention may be more or less fluid and have the appearance of a white or colored cream, an ointment, a milk, a lotion, a serum, a paste, a foam or a biphase. They may optionally be applied to the skin in the form of an aerosol. They can also be

  present in solid form, and for example in the form of a stick.

  They can also be in anhydrous form, in particular in the form of an anhydrous stick.

  The composition used according to the invention may also contain other fatty substances.

  As oils that can be used in the composition of the invention, mention may be made, for example, of: hydrocarbon-based oils of animal origin, such as perhydrosqualene; hydrocarbon-based oils of plant origin, such as liquid triglycerides of fatty acids containing from 4 to 10 carbon atoms, for example triglycerides of heptanoic or octanoic acids or, for example, sunflower, mas, 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'COOR2 and R'OR2 in which R 'represents the residue of a fatty acid containing from 8 to 29 carbon atoms, and R2 represents a hydrocarbon chain, branched or unbranched, containing from 3 to 30 carbon atoms, for example purcellin oil, isononyl isononanoate, isopropyl myristate, 2-ethylhexyl palmitate, stearic acid, octyl-2-dodecyl, 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; 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; fatty alcohols having from 8 to 26 carbon atoms, such as cetyl alcohol, stearyl alcohol and their mixture (cetylstearyl alcohol), Guerbet alcohols such as octyldodecanol and 2-hexyldecanol, 2-butyloctanol, 2-hexyldecanol, 2-n-pentadecanol, oleic alcohol or linoleic alcohol; partially fluorinated hydrocarbon oils and / or silicone oils such as those described in document JP-A-2-295912; silicone oils such as volatile or non-volatile polymethylsiloxanes (PDMS) with a linear or cyclic silicone chain, which are liquid or pasty at room temperature, in particular cyclopolydimethylsiloxanes (cyclomethicones) such as cyclohexasiloxane; polydimethylsiloxanes 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, diphenyls dimethicones, diphenylmethyldiphenyltrisiloxanes, 2-phenylethyltrimethylsiloxysilicates, and polymethylphenylsiloxanes;

- their mixtures.

  The term "hydrocarbon oil" in the list of oils mentioned above, any oil predominantly comprising carbon and hydrogen atoms, and

  optionally ester, ether, fluoro, carboxylic acid and / or alcohol groups.

  The other fatty substances that may be present in the oily phase are, for example, fatty acids containing from 8 to 30 carbon atoms, such as stearic acid, lauric acid, palmitic acid and oleic acid; waxes such as lanolin, beeswax, carnauba or candelilla wax, paraffin waxes, lignite waxes or microcrystalline waxes, ceresin or ozokerite, synthetic waxes such as polyethylene waxes, waxes Fischer-Tropsch; silicone resins such as trifluoromethyl-Cl-4-alkyldimethicone and trifluoropropyldimethicone; and silicone elastomers such as the products sold under the names "KSG" by the company Shin-Etsu, under the names "Trefil", "BY29" or "EPSX" by the company Dow Coming or under the names "Gransil" by the

company Grant Industries.

  These fatty substances may be chosen in a varied manner by those skilled in the art in order to prepare a composition having the properties, for example of consistency or

texture, desired.

  According to a particular embodiment of the invention, the composition according to the invention is a water-in-oil (W / O) or oil-in-water (O / W) emulsion. The proportion of the oily phase of the emulsion can range from 5 to 80% by weight, and preferably from 5 to 50% by weight.

  % by weight relative to the total weight of the composition.

  The emulsions generally contain at least one emulsifier chosen from amphoteric, anionic, cationic or nonionic emulsifiers, used alone or as a mixture, and optionally a coemulsifier. The emulsifiers are suitably selected according to the emulsion to be obtained (W / O or O / W). The emulsifier and the coemulsifier are generally 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 weight.

total of the composition.

  For the W / O emulsions, examples of emulsifiers that may be mentioned include dimethicone copolyols such as the mixture of cyclomethicone and dimethicone copolyol, sold under the name "DC 5225 C" by Dow Coming, and alkyl dimethicone copolyols such as Laurylmethicone copolyol sold under the name "Dow Coming 5200 Formulation Aid" by the company Dow Coming and cetyl dimethicone copolyol sold under the name Abil EM 90R by the company Goldschmidt. It is also possible to use, as surfactant of W / O emulsions, a crosslinked solid elastomeric organopolysiloxane comprising at least one oxyalkylene group, such as those obtained according to the procedure of Examples 3, 4 and 8 of US Pat. No. 5,412,004 and examples US-A-5,811,487, especially the product of Example 3 (synthetic example) of US-A-5,412,004. and as

  that marketed under the reference KSG 21 by Shin Etsu.

  For the emulsions HI / E, mention may be made, for example, as emulsifiers, nonionic emulsifiers such as oxyalkylenated fatty acid esters of sorbitan and glycerol; oxyalkylenated fatty alcohol ethers (oxyethylenated and / or oxypropylenated);

  sugar esters such as sucrose stearate; and their mixtures.

  In known manner, the cosmetic or dermatological composition of the invention may also contain adjuvants customary in the cosmetic or dermatological field, such as active agents, antioxidants, hydrophilic or lipophilic gelling agents, solvents, perfumes, fillers, UV filters, odor absorbers, dyestuffs, plant extracts, salts. The amounts of these various adjuvants are those conventionally used in the field under consideration, and for example from 0.01 to 20% of the total weight of the composition. These adjuvants, depending on their nature, can be introduced into the fatty phase, into the aqueous phase and / or into the

lipid spherules.

  As fillers which can be used in the composition of the invention, mention may be made, for example, besides the pigments, the silica powder; talcum; polyamide particles and especially those sold under the name ORGASOL by the company Atochem; polyethylene powders; micro-spheres based on acrylic copolymers, such as those in ethylene glycol dimethacrylate / lauryl methacrylate copolymer sold by Dow Coming under the name Polytrap; expanded powders such as hollow microspheres and in particular the microspheres sold under the name Expancel by the company Kemanord Plast or under the name Micropearl F 80 ED by the company Matsumoto; silicone resin microbeads such as those marketed under

  the name TOSPEARL by the company Toshiba Silicone; and their mixtures.

  It is also possible to incorporate fibers which may be fibers of synthetic or natural, mineral or organic origin. The fibers may be those used in the manufacture of textiles and especially silk fibers, cotton, wool, linen, cellulose extracted including wood, vegetables or seaweed, polyamide (nylon) especially under the Nylon names 6 = Polyamide 6; Nylon 6,6 = polyamide 6,6; Nylon 12 = polyamide 12), rayon, viscose, acetate, especially rayon acetate, cellulose acetate or silk acetate, poly-p-phenylene terephtamide including Kevlarg, acrylic, especially polymethylmethacrylate; methyl or poly-2-hydroxyethyl methacrylate, polyolefin and in particular polyethylene or polypropylene, glass, silica, aramid, carbon in particular in graphite form, Teflon), insoluble collagen, polyesters, polyvinyl chloride, vinyl or vinylidene, polyvinyl alcohol, polyacrylonitrile, chitosan, polyurethane, polyethylene phthalate, fibers formed from a mixture of polymers such as those mentioned above, such as

  polyamide / polyester fibers, and blends of these fibers.

  These fillers may be present in amounts ranging from 0 to 20% by weight and

  preferably 1 to 10% by weight relative to the total weight of the composition.

  According to a preferred embodiment, the compositions used according to the invention may further comprise at least one organic photoprotective agent and / or at least one active inorganic photoprotective agent in the UVA and / or P'UVB (absorbers), which are water-soluble. or fat-soluble or solvent-insoluble

commonly used cosmetics.

  The organic photoprotective agents are in particular chosen from anthranilates; cinnamic derivatives; dibenzoylmethane derivatives; salicylic derivatives, camphor derivatives; triazine derivatives such as those described in patent applications US 4367390, EP863145, EP517104, EP570838, EP796851, EP775698, EP878469, EP933376, EP507691, EP507692, EP790243, EP944624; benzophenone derivatives; derivatives of PP-diphenylacrylate; benzotriazole derivatives; benzalmalonate derivatives; benzimidazole derivatives; imidazolines; bis-benzoazolyl derivatives as described in patents EP669323 and US 2,463,264; p-aminobenzocene (PABA) derivatives; methylenebis (hydroxyphenylbenzotriazole) derivatives as described in US5,237,071, US5,166, 355, GB2303549, DE 197 26 184 and EP893119; filter polymers and silicone filters such as those described in particular in application WO-93/04665; dimers derived from α-alkylstyrene such as those described in patent application DE19855649; 4,4-diarylbutadienes as described in the applications EP0967200, DE19746654, DE19755649, EP-A-1008586, EP1133980 and EP133981 and their

mixtures.

  The photoprotective agents are generally present in the compositions according to the invention in proportions ranging from 0.1 to 20% by weight relative to the total weight of the composition, and preferably ranging from 0.2 to 15% by weight relative to by weight

total of the composition.

  The compositions according to the invention may optionally contain one or more thickening compound, in preferential concentrations ranging from 0.05 to 2% by weight.

  weight relative to the total weight of the composition.

  Examples of thickening compounds that can be used in the composition of the invention are: polysaccharide biopolymers such as xanthan gum, guar gum, alginates, modified celluloses; synthetic polymers such as polyacrylics such as CARBOPOL 980 marketed by GOODRICH, acrylate / acrylonitrile copolymers such as HYPAN SS201 marketed by the company

KINGSTON;

  inorganic compounds such as smectites, modified or non-modified hectorites, such as BENTONE products marketed by RHEOX, LAPONITE products marketed by SOUTHERN CLAY PRODUCTS, and VEEGUM HS product marketed by R.T.VANDERBILT;

- and their mixtures.

  The present invention also relates to a process for solubilizing at least one coumarin derivative comprising the step of mixing it with at least one amino acid ester of formula (III): R '1 (CO) N (R') 2) CH (R! 3) (CH 2) n (CO) OR '4 (III) in which n is an integer equal to 0.1 or 2, R' represents a linear or branched C 5 to C 21 radical, alkyl or alkenyl, R'2 represents a hydrogen atom or a C1-C3 alkyl group, R'3 represents a radical chosen from the group formed by a hydrogen atom, a methyl group, an ethyl group and a radical; linear or branched C3 or C4 alkyl, R'4 represents a linear or branched C1 to C10 alkyl radical, or a radical

  C2-C10 linear or branched alkenyl, or a sterol residue.

  The subject of the invention is also a cosmetic treatment method for combating cellulite, characterized in that it comprises the application on the skin of a

composition according to the invention.

  The invention also relates to a cosmetic treatment method for combating the formation of bags and / or dark circles under the eyes characterized in that it comprises

  applying to the skin a composition according to the invention.

  According to a preferred embodiment of the invention, the ratio of coumarin derivative / amino acid ester is between 0.001 / 99.999 and 30/70, and better between

0.001 / 99.999 and 25/75.

  The examples which follow illustrate the invention without limiting its scope. -. The compounds are, as the case may be, listed in chemical names or CTFA names

  (International Cosmetic Ingredient Dictionary and Handbook).

  Example 1: Solubility: Protocol: The coumarin derivatives are weighed and placed in an airtight container. The

  Amount of amino acid lipophilic derivative (solubilizer) required is added.

  The suspension is heated to 80 ° C and stirred by magnetic stirring for one hour. The dissolution or non-dissolution of the coumarin derivative, as well as its

  evolution over time are then followed.

  The non-solubility of the coumarin derivative in the solubilizer is macroscopically characterized by a precipitate or just a cloudy solution, and

  microscopically by the presence of crystals.

  Results: A test conducted with isopropyl N-lauroylsarcosinate as a lipophilic amino acid derivative, solubilized up to 20% by weight of visnadine (the rest

  of the solution being constituted by the solubilizer).

  For comparison, using the C12-Cl5 alcohol benzoate as the solubilizer, the results led to the solubilization of at most 15% visnadine. Other solvents such as water, glycerine, paraffin oil, or

  Isopropyl palmitate does not allow this coumarin derivative to be solubilized.

  Example 2: Examples of formulations:

  Several examples in different types of emulsions have been made.

  Example A: Emulsion based on sugar esters: Phase A: ammonium polyacryloyldimethyl taurate Sodium hyaluronate Glycerol Preservative Water Phase B: PEG 120 methyl glucose dioleate Polysorbate 20 isopropyl Nlauroylsarcosinate Visnadine Phase C: Ethanol 1.5% 0.1 %% 0.4% qs 100% 0.5% 0.5%% 2%% Comparative Example A ': Phase A: ammonium polyacryloyldimethyl taurate Sodium hyaluronate Glycerol Preservative Water Phase B: PEG 120 methyl glucose dioleate 1.5% 0.1%% 0, 4% qs 100% 0.5% Polysorbate 20 Triglyceride C8-C1 0 Visnadine Phase C: Ethanol 0.5%% 2%% Procedure: Aqueous phase A is prepared by mixing the various constituents and homogenization. Phase B is prepared by adding the visnadine premix and solubilizer to the surfactant mixture. Phase A is then added to phase B at a temperature of 750C. Phase C is then added to a

  temperature of 250C to the resulting mixture.

  Example B: Emulsion Gel Phase A Acrylates / C1O-30 alkyl acrylate crosspolymer 0.25% Xanthan 0.3% Glycerol 3%

PEG-8 3%

  Base 0.15% Preservative 0.1% Water qs 100% Phase B: Volatile silicone 10% Isopropyl N-lauroylsarcosinate 15% Visnadine 2% Phase C: Ethanol 15% Silicone Polymer 2% Comparative Example B ': Phase A Acrylates / C10-30 alkyl acrylate crosspolymer 0.25% Xanthan 0.3% Glycerol 3%

PEG-8 3%

  Base 0.15% Preservative 0.1% Water qs 100% Phase B Silicone volatile 10% Triglyceride C8-C1O 10% Visnadine 2% Phase C: Ethanol 15% Silicone polymer 2% Procedure: Phase A is prepared by homogenization of different constituents. The premix of visnadine and solubilizer is added to the other constituents of phase B. Phase B is added to phase A at a temperature of 750C. The sentence

  C is then added to the resulting mixture at a temperature of 250C.

  EXAMPLE C Emulsion Based on Glycerol Esters and Sorbitan Esters Phase A: Glyceryl Stearate (and) PEG-100 Stearate 2.5% Polysorbate 60 2.5% Cetyl Alcohol 1% Stearyl Alcohol 1% Paraffin 5% Preservative 0.1% isopropyl N-lauroylsarcosinate 15% Visnadine 2% Phase B: Preservative 0.2% Carbomer 0.3% Base 0.2% Water qs 100% Comparative Example C ': Phase A: Glyceryl stearate (and ) PEG-100 Stearate 2.5% Polysorbate 60 2.5% Cetyl Alcohol 1% Stearyl Alcohol Paraffin Preservative Triglyceride C8-C10 Visnadine Phase B: Preservative Carbomer Base Water 1%% 0.1%% 2% 0.2% 0 , 3% 0.2%% qsp Example D: Fluid Emulsion: Phase A: Carbomer 0.2% Preservative 0.65% Acrylates / C10-30 alkyl acrylate crosspolymer 0.2% Glycerol 3% Antioxidant 0.3% Xanthan 0 , 2% Base 0.2% Water qs 100% Phase B: Cyclohexasiloxane 5% Isopropyl Nlauroylsarcosinate 19% Visnadine 2% Phase C: Dimethicone copolyol 5% Phase D: Polyacrylamide (and) C13-C14 isoparaffin (and) Laur Eth -7 0.4% Phase E: Ethanol 5% Procedure: Phase A is prepared by homogenization of the various constituents. The visnadine and solubilizing premix is added to the other component of the oily phase B. Phase B is added to phase A at a temperature of 300C. Then

  phases C, D, and E are added successively.

  EXAMPLE E Emulsified Gel Phase A Acrylates / C10-30 Alkyl Acrylate Crosspolymer 0.25% Xanthane 0.3% Glycerol 3% Propylene Glycol 3%

PEG-8 3%

  Base 0.15% Preservative 0.1% Water qs 100% Phase B: Volatile silicone 10% isopropyl N-lauroylsarcosinate 15% Visnadine 1% Phase C: Ethanol 15% Silicone polymer 2% The procedure is identical to the one used Example F: Emulsion Phase A: Glyceryl Stearate (and) PEG-100 Stearate Polysorbate 60 Cetyl Alcohol Stearyl Alcohol Paraffin Preservative N-Lauroylsarcosinate Isopropyl Visnadine Phase B: Preservative Carbomer Base Water 2.5 % 2.5% 1% 1%% 0.1%% 1% 0.2% 0.3% 0.2% qs 100% The procedure is identical to that used for the preparation of Example C.

Example G:

  Phase A: Glyceryl Stearate (and) PEG-100 Stearate Polysorbate 60 Cetyl Alcohol Stearyl Alcohol Retinol Soybean Oil Paraffin Preservative N-Lauroylsarcosinate Isopropyl Visnadine Phase B: Preservative Carbomer Base Water 2.5% 2.5% 1% 1%

0.08%

  1%% 0.1%% 1% 0.2% 0.3% 0.2% qs 100% The procedure is identical to that used for the preparation of Example C.

Example H:

  Phase A: Glyceryl Stearate (and) PEG-100 Stearate Polysorbate 60 Cetyl Alcohol Stearyl Alcohol Paraffin Preservative N-Lauroylsarcosinate Isopropyl Esculoside Phase B: Preservative Carbomer Base 2.5% 2.5% 1% 1%% 0.1% % 1% 0.2% 0.3% 0.2% Water qs 100% The procedure is identical to that used for the preparation of Example C. Example 3: Control of stability: pH (at 250 ° C) and the viscosity (Rheomat 180 to 250 ° C., 200s-1) of the compositions of the above examples were measured, as well as the microscopic and macroscopic aspects, at T = 0, T = 24 hours, and at T = 2 months at 45 'C. The results are summarized in the following table: Example pH Viscosity Appearance at 24 h Stability after 2 months at 450 ° C. 33.8 poises Fine emulsion Stable emulsion of the same homogeneous white appearance as at T = 24 hours A '4.5 34 , 8 poises Fine emulsion White homogeneous crystals B 5.74 59 poises Fine emulsion Stable emulsion of the same homogeneous white appearance as at T = 24 hours B '5.5 59 poises Fine emulsion Crystals homogeneous white C 6.33 537 Emulsion fluid Emulsion stable same centipoise fine homogeneous appearance at T = 24 hours white C '6.49 846 Fine emulsion Centipedes crystals homogeneous white D 6.65 11.5 Fine emulsion Stable emulsion of the same centipoise homogeneous white aspect as at T = 24 hours E 5.6 41.4 poises Fine emulsion Stable emulsion of the same homogeneous white appearance as at T = 24 hours F 5.95 600 Fine emulsion Stable emulsion of the same centipoise homogeneous white appearance at T = 24 hours G 6 700 Fine emulsion Stable emulsion of the same centipoises homogeneous white appearance at T = 24 hours H 5.8 650 Fine emulsion Stable emulsion of same centipoise homogeneous white appearance as at T = 24 hours The stability tests above show that the amino acid ester used according to the invention allows an excellent solubilization of coumarin derivatives and obtaining a perfectly satisfactory cosmetic composition both at the level of

stability than cosmetic touch.

Claims (20)

  Cosmetic composition comprising, in a physiologically acceptable medium, at least one coumarin derivative and at least one lipophilic derivative amino acid.   2. Composition according to Claim 1, characterized in that the coumarin derivative is chosen from unsubstituted coumarins and coumarins.   monosubstituted, and disubstituted coumarins, and / or their mixtures.   3. Composition according to one of claims 1 or 2, characterized in that the   Coumarin derivative is selected from the bicyclic coumarins represented by the formula (I): O O <R.R   R 2 in which R represents a hydrogen atom or a linear or branched, saturated or unsaturated alkyl group containing from 1 to 20 carbon atoms, optionally hydroxylated, and one carbon atom of which may be replaced by a heteroatom chosen from the atoms oxygen, nitrogen and sulfur; and R 1 and R 2 independently represent a hydrogen atom, or a group selected from R 30, -O-R 31, -N-R 31 R 32, -CO-R 3, or -O-CO-R 30, wherein R 30 represents a chosen group from linear or branched, saturated or unsaturated alkyl groups having from 1 to 20 carbon atoms, optionally hydroxylated and one carbon atom of which may be replaced by a heteroatom selected from oxygen, nitrogen and sulfur atoms; cycloalkyl containing from 3 to 8 carbon atoms, optionally hydroxylated, and one carbon atom of which may be replaced by a heteroatom chosen from oxygen, nitrogen and sulfur atoms; optionally substituted aryl; mono or bicyclic heteroaryl, containing at least one aromatic ring, comprising from 5 to 11 ring members, and from 1 to 5 heteroatoms selected from nitrogen, oxygen and sulfur, optionally substituted; an arylalkyl group in which the aryl and alkyl radicals have the same meaning as above; and heteroarylalkyl wherein the heteroaryl and alkyl radicals have the same meaning as above; and a sugar residue; R31 and R32 independently represent a hydrogen atom or a grouping R30.   4. Composition according to Claim 3, characterized in that the R group represents a hydrogen atom, or a linear or branched alkyl group containing from 1 to 6 carbon atoms, and the groups R 1 and R 2 independently represent a group -O -R31 wherein R3 is selected from hydrogen; an alkyl group, linear or branched, saturated or unsaturated having from 1 to 20 carbon atoms, optionally hydroxylated and a carbon atom may be replaced by a heteroatom   selected from oxygen, nitrogen and sulfur atoms; and a sugar residue.   5. Composition according to one of claims 1 to 3, characterized in that the coumarin derivative is esculoside of formula O O OH xc o OH OH HO OH   6. Composition according to one of claims 1 to 3, characterized in that the coumarin derivative is methylsculetin of formula: O O OH O O OH   7. Composition according to one of claims 1 or 2, characterized in that the   coumarin derivative is chosen from tricyclic coumarines of formula (II): R 6 R7 R5   R4 wherein R4 and R5 independently represent an alkyl group having 1 to 6 carbon atoms, and R6 and R7 independently represent a hydrogen atom, or a group selected from R60, O-R61, -N-R61R62, -CO -R61 or -O-CO-R60, in which R60 represents a group chosen from linear or branched, saturated or unsaturated alkyl groups containing from 1 to 20 carbon atoms, optionally hydroxylated, and one carbon atom of which may be replaced by a heteroatom selected from oxygen, nitrogen and sulfur atoms; cycloalkyl containing from 3 to 8 carbon atoms, optionally hydroxylated, and one carbon atom of which may be replaced by a heteroatom chosen from oxygen, nitrogen and sulfur atoms; optionally substituted aryl; mono or bicyclic heteroaryl, containing at least one aromatic ring, comprising from 5 to 11 ring members, and from 1 to 5 heteroatoms selected from nitrogen, oxygen and sulfur, optionally substituted; an arylalkyl group in which the aryl and alkyl radicals have the same meaning as above; and heteroarylalkyl wherein the heteroaryl and alkyl radicals have the same meaning as above; and a sugar residue; R6 and R62 independently represent a hydrogen atom or a grouping R60.   8. Composition according to Claim 7, characterized in that the groups R4 and   R5 are each a methyl group.   9. Composition according to Claim 7, characterized in that the groups R6 and R7 independently represent a group -O-CO-R61 in which R6 represents a linear or branched, saturated or unsaturated alkyl group containing from 1 to 20 carbon atoms. carbons, optionally hydroxylated, one carbon atom of which may be replaced by a heteroatom selected from the group consisting of   oxygen, nitrogen and sulfur atoms.   10. Composition according to one of claims 7 to 9, characterized in that the   coumarin derivative is visnadine of formula: 11. Composition according to claim 1, characterized in that the lipophilic amino acid derivative is an ester chosen from the amino acid esters of formula (III) R 'I (CO) N (R' 2) CH (R '3) (CH 2), (CO) OR' 4   (III) in which: n is an integer equal to 0.1 or 2, R'1 represents a linear or branched C5 to C21 alkyl or alkenyl radical, R'2 represents a hydrogen atom or an alkyl group; C1 to C3, R'3 represents a radical chosen from the group formed by a hydrogen atom, a methyl group, an ethyl group, a linear or branched C3 or C4 alkyl radical, R'4 represents an alkyl radical in C1 to linear or branched Clo, or a   linear or branched C2 to C10 alkenyl radical, or a sterol residue.   12. Composition according to claim 11, characterized in that said amino acid ester is isopropyl N-lauroylsarcosinate:   CH3- (CH2) 10Co-N (CH3) -CH2-COO-CH2 (CH3) 2.   13. Composition according to any one of claims 1 to 12, characterized in   said coumarin derivative represents from 0.001 to 30%, preferably from 0.001 to 20%, still more preferably from 0.1 to 5% by weight relative to to the total weight of the composition.   14. Composition according to any one of claims 1 to 13, characterized in   that said lipophilic amino acid derivative represents from 0.01 to 90% by weight, and preferably from 0.1 to 30% by weight relative to the total weight of the composition.   15. Use of a composition according to one of claims 1 to 14 as   slimming composition and / or to fight against cellulite.   16. Use of a composition according to one of claims 1 to 14 to fight   against the formation of puffiness and / or dark circles under the eyes.   17. Cosmetic treatment method for combating cellulite, characterized in that it comprises applying to the skin a composition according to one of the following:   any of claims 1 to 14.   18. A cosmetic treatment method for combating the formation of bags and / or dark circles under the eyes characterized in that it comprises the application on   the skin a composition according to any one of claims 1 to 14.   19. A process for solubilizing at least one coumarin derivative comprising the step of mixing it with at least one amino acid ester of formula (III) R '1 (CO) N (R' 2) CH (R) 3) (CH 2) n (CO) OR '4 (III) in which: n is an integer of 0, 1 or 2, R' 1 represents a linear or branched C 5 -C 21 radical, alkyl or alkenyl, R'2 represents a hydrogen atom or a C1-C3 alkyl group, R'3 represents a radical chosen from the group formed by a hydrogen atom, a methyl group, an ethyl group or a linear or branched alkyl radical; at C3 or C4, R'4 represents a linear or branched C1-C10 alkyl radical, or a radical   linear or branched C2 to C10 alkenyl, or a sterol residue.   20. Process according to claim 19, characterized in that the ratio of coumarin derivative / amino acid ester is between 0.001 / 99.999 and 30/70, preferably between 0.001 / 99.999 and 25/75.