FR3029410A1 - USE OF 1,3-BUTANEDIOL ESTERS AND N-ACYL DERIVATIVES OF AMINO ACIDS AS A BROWNING AND / OR TANNING AGENT OF HUMAN SKIN - Google Patents

Abstract

Use of a compound of formula (I): in which R 'and R "represent either a hydrogen atom or a monovalent radical of formula (II): or a composition (C1) comprising 99% to 20% by mass of at least one compound of formula (Ia) and from 1% to 80% by weight of at least one compound of formula (Ib): formulas (Ia) and (Ib) in which R 'and R represent a monovalent radical of formula (II): formula (II) in which the group R1-C (= O) - represents the octanoyl radical or the hexadecanoyl radical, for browning and / or tanning the human skin in a cosmetic composition. and medicine.

Description

The present invention relates to the use of esters of N-acyl derivatives of amino acids and 1,3-butanediol as a dyeing agent for the skin of the human body, as well as treatment methods for tan and / or brown the skin of the human body implementing them.

Human skin is the first image offered in the eyes of others, and therefore, the improvement of its appearance is a subject of constant concern for human beings. The skin is a reflection of a state of well-being, often associated with youth, and "a contrario" of a state of fatigue and / or aging. Thus, a tanned complexion and tanned skin are signs of good health and people are attaching more and more importance to this appearance of "good looks". The color of the skin results from the combination of two biological components: the vascularization and the pigmentation of the skin; said pigmentation of the skin being the resultant of the quantities of melanins and carotenes present in human skin. Melanins are produced by specific epidermal cells: melanocytes. These are found at the level of the basal layer of the epidermis or in the hair follicles. Melanins are large cells with many long extensions called dendrites. These dendrites come into contact with the surrounding keratinocytes, which may be up to two superior cell bases, to transmit the melanin grouped in melanosomes.

Epidermal Unit of Melanization (EMU), the group of melanocytes and keratinocytes, interacting together to give color to the skin. An EMU comprises in particular a melanocyte and forty keratinocytes. The process of melanogenesis itself includes melanin synthesis by melanocytes, their transfer and distribution to neighboring keratinocytes.

The synthesis of melanins occurs in melanocytes, and more particularly in specialized organelles, melanosomes. This synthesis is made from tyrosine and involves several enzymes, including tyrosinase which is the first enzyme to intervene in the reaction chain. There are two main groups of melanins: eumelanins (brown or black) and phaeomelanines (yellow-orange). The maturation of melanosomes goes through four stages in order to be mature and able to be transferred to keratinocytes. During their maturation, melanosomes migrate to the end of the dendrites through a system of microtubules and microfilaments. The transfer between melanocytes and keratinocytes is by a more or less detailed system of phagocytosis / endocytosis / pinocytosis, in particular via a PAR-2 membrane receptor. The pigmentation of the skin can either be constitutive or induced. The constitutive pigmentation is based on the genetic heritage of the individual, hormonal factors and age. Induced pigmentation results mainly from ultraviolet radiation exposures. It appears between 48 hours and 72 hours after exposure of the skin to ultraviolet radiation and disappears quickly after the exposure has stopped. This induction of pigmentation results in particular from an activation of tyrosinase, an increase in the size and number of melanocytes and an increase in the transfer of melanosomes to keratinocytes.

An indirect action on keratinocytes also comes into play to promote the process of melanogenesis by the secretion of soluble factors. An increase in the synthesis and / or activity of melanogenic enzymes allowing an increase in the amount of melanins produced by melanocytes, and more generally in the biogenesis of melanosomes, their transport and transfer to keratinocytes, will lead to their visible manifestation, namely the coloration and / or natural browning of human skin. Natural tanning is not always recommended because it requires prolonged exposures to sunlight, and more particularly to ultraviolet radiation from the sun, and more particularly to UV-A and UV-B radiation from the sun that causes browning. human skin, but also cause unwanted reactions and alteration of human skin, especially for sensitive skin. Among these reactions and alterations, mention may be made of erythema, burning, external signs of aging of the skin, for example alteration or loss of elasticity, lack of tone, lack of firmness, appearance or digging wrinkles or fine lines of human skin. The Ministry of Health and Social Protection, in collaboration with INPES and the Health Insurance, under the cancer plan, recently drafted recommendations on these exposures in order to limit the risk of developing skin cancers. To combine tanned skin and unaltered skin, there are products for tanning and / or artificial browning of the skin, for example carbonyl-containing chemicals which, by interaction with the amino acids of human skin, allow the formation of colored products on the surface of the skin. Mention may be made, for example, of mono- or polycarbonyl compounds such as dihydroxyacetone (DHA), erythrulose, mesotartaric aldehyde, glutaraldehyde, glyceraldehyde, alloxane and ninhydrin.

DHA is the self-tanning agent most commonly used for the preparation of cosmetic compositions intended to brown and / or artificially tan human skin because it makes it possible to obtain an external effect of tanning or browning of the skin. human skin similar to that which may result from exposure to sunlight. However, DHA has disadvantages: its effectiveness is not universal, the coloration generated by its application to the skin depends on the type of skin, and the consumer may encounter problems of unevenness in the coloring obtained on the skin. DHA has the disadvantage of degrading over time, depending on the cosmetic medium in which it is formulated, partially oxidizing during storage, which is manifested by the appearance of a long term yellowish or even orange coloring of the cosmetic composition comprising it. To overcome the disadvantages of DHA as a self-tanning agent for human skin, the cosmetic industry has deployed over the last twenty years many solutions, including combining DHA with other cosmetically acceptable ingredients.

European Patent Publication No. EP 0 425 324 B1 discloses the combination of DHA with an indole derivative for coloring human skin in an intense and rapid manner over time. In addition, academic studies have highlighted the possibility of long-term genotoxicity of DHA (1). To reach a tanned skin, there are also specific ultraviolet radiation exposure technologies, such as cabins called "UV cabins", which are enclosed spaces in which the subject is subjected for a variable duration to UV radiation. -A (320-400 nm). Their regular use is, however, harmful to human health. There are also chemical substances and compositions, more particularly extracts of plants or bacteria, which are disclosed as a coloring agent for human skin. There may be mentioned the French patent application published under the number FR 2 973 697 A1 which discloses the use of a hydroglycolic extract of "Tribulus terrestris" and of chaulmoogra oil in cosmetic compositions for pigmenting the skin. The use of plant extracts and bacteria, however, has the disadvantage of showing unreliable and non-repetitive performances over time due to the variability of the content of the raw materials used to obtain them. There are also active synthetic ingredients, for example peptides and polypeptides, which are described as coloring agents for human skin. The French patent application published under the number FR 2 970 968 A1 discloses the increase of the amount of melanin in biopsies of human skin, treated with peptide compounds. The French patent published under the number FR 2 913 685 B1 discloses the use, as agents for treating disorders of skin pigmentation, of unsaturated fatty amino acid derivatives of formula (A): NH 2 - CH2- [CH (Rn)] n-CH2 = CH (R1) -COOR (A) wherein R represents a hydrogen atom or a linear or branched alkyl group having from 1 to 6 carbon atoms, optionally substituted by a halogen, more particularly fluorine; R1 represents a hydrogen, fluorine, chlorine or bromine atom or a -CF3 group or a linear or branched alkyl group containing from 1 to 6 carbon atoms; R represents a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms, optionally substituted by halogen, in particular fluorine; n represents an integer between 2 and 14. The French patent application published under the number FR 2 827 511 A1 discloses self-tanning compositions comprising self-tanning agents and N-acylated esters of amino acids of general formula (B): R'1- (C = O) -N (R'2) -CH (R'3) (CH2) (C = O) OR'4 (B) wherein n represents an integer equal to at 0, 1 or 2; R'1 represents a linear or branched alkyl or alkenyl radical containing from 5 to 21 carbon atoms; R'2 represents the hydrogen atom or an alkyl group having from 1 to 3 carbon atoms; R '3 represents a radical chosen from the group consisting of a hydrogen atom, the methyl group, the ethyl group, a linear or branched alkyl radical comprising 3 or 4 carbon atoms; R'4 represents a linear or branched alkyl radical containing from 1 to 10 carbon atoms, or a linear or branched alkenyl radical containing from 2 to 10 carbon atoms or a sterol residue. The French patent application published under the number FR 2 827 511 A1 specifically discloses self-tanning compositions comprising self-tanning agents and isopropyl N-lauroyl sarcosinate, and the use of the compounds of formula (B) for to improve the stability and the coloration of the compositions comprising a self-tanning agent. Japanese Patent Application No. 2000-229121 discloses the use of N-acylamino acid ester polyols as high performance surfactants. The international application published under the number WO 2010/034917 describes the mono-esters and di-esters of polyols of N- (β-undecylenoyl) phenylalanine, and more particularly the mono-esters and diesters resulting from the reaction. glycerol and N- (w-undecylenoyl) phenylalanine, and their uses as lightening agents in human skin. The international application published under the number WO 2013/060964 A1 describes mono-esters and diesters resulting from the esterification reaction between 1,3-butanediol and N-acyl derivatives of amino acids. , their use as a cosmetic active agent, for preventing and / or limiting the unsightly effects generated by the hypoxia of the endothelial cells of the human body, and more particularly for preventing and / or limiting the unsightly effects generated by the dark circles, the periosteal sacs. eyepieces and / or heavy legs.

In the context of their search for new active agents intended to color and / or brown the skin of the human body, the inventors have endeavored to develop a new technical solution consisting of the use of products resulting from the esterification reaction between 1,3-butanediol and N-acylated amino acid derivatives for staining and / or browning the skin of the human body, and a cosmetic method for tanning and / or browning the skin of the human body by application to said skin of a topical cosmetic formulation comprising said products resulting from the esterification reaction between 1,3-butanediol and N-acyl derivatives of amino acids. This is why, according to a first aspect, the subject of the invention is the use of a compound of formula (I): ## STR3 ## in which formula (I) in which R 'and R ", which may be identical or different, represent either a hydrogen atom or a monovalent radical of formula (II): ## STR2 ## in which the group R 1 -C (= O) - represents the octanoyl radical or the hexadecanoyl radical, it being understood that at least one of the radicals R 'or R "does not represent a hydrogen atom and that when none of the radicals radicals R 'and R "represents a hydrogen atom, R' and R" are identical, or a mixture of compounds of formula (I), said use being for the purpose of browning and / or tanning the human skin and said use being in a cosmetic composition.

According to a first particular aspect, the subject of the invention is the use as defined above of a composition (C1) comprising for 100% of its mass: from 99% by weight to 20% by weight of at least one compound of formula (Ia) wherein R 'represents a monovalent radical of formula (II): ## STR2 ## wherein R' represents a monovalent radical of formula (II): ## STR2 ## Embedded image in which the group R 1 -C (= O) - represents the octanoyl radical or the hexadecanoyl radical, - from 1% by mass to 80% by weight of at least one compound of formula (Ib): Embedded image in which R is a monovalent radical of formula (II): ## STR5 ## wherein formula (II) in which the group R 1 -C (= O) - represents the octanoyl radical or the hexadecanoyl radical. By "browning and / or tanning of human skin" is meant, in the sense of the invention, a modification of the external appearance of the skin resulting in the appearance and development of a brown color, more or less intense, from the surface of the human skin. According to another particular aspect, the subject of the invention is the use as described above for which in the monovalent radical (II) compounds of formulas (I), (Ia) and (Ib), the group R1-C ( = O) - represents the octanoyl radical. According to another particular aspect, the subject of the invention is the use as described above for which, in the monovalent radical (II), compounds of formulas (I), (Ia) and (Ib), the group R1-C (= O) - represents the hexadecanoyl radical.

Examples of compounds of formula (I) or mixtures of compounds of formula (I) used in the context of the present invention are 3-hydroxybutyl N-octanoyl valinate or N-octanoyl valinate. hexadecanoyl 3-hydroxy butyl valinate. Examples of compositions (C1) used in the context of the present invention are those in which the compound of formula (Ia) is 3-hydroxybutyl N-octanoyl valinate and the compound of formula (Ib) 1,3-butanediyl bis (N-octanoyl valinate); or that in which the compound of formula (Ia) is 3-hydroxybutyl N-hexadecanoyl valinate and the compound of formula (1b), 1,3-butanediyl bis (N-hexadecanoyl valinate). The compound of formula (I) as defined above may be prepared according to a preparation method comprising: - a step a) of esterification of a compound of formula (III): ## STR2 ## 1,3-butanediol of formula (IV): CH 3 HO -CHFCHCH (OH), to obtain either the compound of formula (Ia) or the compound of formula (Ib) or a mixture (M) of the compound of formula (Ia) and the compound of formula (Ib); and if necessary or if desired, - a step b) of separating the compounds of formula (Ia) and formula (Ib), from said mixture (M) obtained in step (a). The compounds of formulas (III) are known or are synthesizable by N-acylation of the corresponding α-amino acids, according to methods known to those skilled in the art. In the process as defined above, the molar ratio of compound of formula (III) to 1,3-butanediol of formula (IV) is generally between 3/1 and 1/5, more particularly between 1/1 and 1 / 5, and even more particularly between 1/1 and 1/3. In the process as defined above, step b) of separating compounds of formula (Ia) and formula (Ib) is carried out by conventional separation methods known to those skilled in the art. The compound of formula (I) as defined above may also be prepared according to a preparation method comprising: an esterification step a1) or a compound of formula (III): CH3 / CH3O HC R1 NH 0 with an alcohol of formula (V): R5-OH (V), in which R5 represents a linear aliphatic radical having 1 to 4 carbon atoms, to form a compound of formula (VI): CH CH3 Wherein R 1 -C (= O) - and R 5 are as previously defined; A step a2) of trans-esterification of the compound of formula (VI) obtained in step a1), by reaction with 1,3-butanediol of formula (IV), to obtain either the compound of formula (la ), or the compound of formula (Ib), or a mixture (M) of the compound of formula (Ia) and the compound of formula (Ib); and if necessary or if desired, - The implementation of step b). In the process as described above, step a1) is generally carried out at a temperature of about 60 ° C to 120 ° C, under an inert gas, and in the presence of an acidic catalyst system. By acidic catalytic system are meant strong acids such as sulfuric acid, hydrochloric acid, phosphoric acid, nitric acid, hypophosphorous acid, methanesulfonic acid, para-toluene sulfonic acid, trifluoromethanesulfonic acid, or acidic ion exchange resins.

In step a1) of the process as described above, the molar ratio of compound of formula (III) to alcohol of formula (V) is generally between 1/1 and 1/10, more particularly between 1/1 and 1/8, and even more particularly between 1/2 and 1/8. In the process as described above, step a2) of transesterification of the ester of formula (VI) obtained in step a1) is generally carried out at a temperature of about 25 between 80 ° C. and 180 ° C, more particularly between 100 ° C and 150 ° C, even more particularly between 120 ° C and 150 ° C, under inert gas, and in the presence of an acid catalytic system such as previously described and with vacuum distillation of the alcohol of formula (V) formed in situ. In step a2) of the process as described above, the molar ratio of compound of formula (VI) to 1,3-butanediol of formula (IV) is between 3/1 and 1/5, more particularly between 1/1 and 1/5, and even more particularly between 1/1 and 1/3. The composition (C1) as defined above can be prepared by various routes. A first route of preparation of the composition (C1), used in the object of the invention, consists in mixing, in the desired mass proportions, the compound of formula (Ia) as defined above, with the compound of formula (Ib) as defined above. A second route of preparation of the composition (C1), used in the object of the invention, consists in carrying out the process for preparing the compound of formula (I) as described above, by reacting in the desired proportions, 1,3-butanediol of formula (IV) with the compound of formula (III).

A third route for preparing the composition (C1), used in the object of the invention, consists in implementing the variant of the process for the preparation of the compound of formula (I) as described above, in reacting in the desired proportions, the compound of formula (III) with the alcohol of formula (V), then 1,3-butanediol of formula (IV).

The invention also relates to a method for the purpose of browning and / or tanning human skin comprising at least one step A of application to said human skin of a cosmetic formulation for topical use comprising at least one excipient cosmetically acceptable and an effective amount of at least one compound of formula (I) or one of a composition (C1), as defined above.

The expression "for topical use" used in the definition of the cosmetic formulation used in step A) of the cosmetic process which is the subject of the present invention means that said formulation is applied by application to the skin, which it is a direct application in the case of a cosmetic formulation or an indirect application when the cosmetic formulation according to the invention is impregnated on a support intended to be placed in contact with the skin (paper, wipe, textile, transdermal device, etc ...). The expression "cosmetically acceptable" used in the definition of the cosmetic formulation for topical use, used in step A) of the cosmetic process that is the subject of the present invention, means according to the directive of the Council of the European Economic Community No. 76/768 / EEC of 27 July 1976 as amended by Directive 93/35 / EEC of 14 June 3029410 10 S1 0075 1993, that said formulation for topical use includes any substance or preparation intended to be put in contact with the various parts the human body (epidermis, hair and hair system, nails, lips and genitals) or with oral teeth and mucous membranes with a view, exclusively and principally, to cleanse, perfume, and change their appearance 5 and / or to correct body odors and / or protect them or keep them in good condition. By effective amount of the compound of formula (I) or of a composition (C1) as defined previously present in the cosmetic formulation for topical use implemented in step A) of the cosmetic process that is the subject of the present invention, is meant for 100% of the mass of said cosmetic formulation for topical use, the amount of between 0.1% and 5% by weight, more particularly between 0.1% and 3% by weight, and even more particularly between 0.5% and 2% by weight of compound of formula (I) or composition (C1). In a particular embodiment, the method as defined above further comprises a step B of exposure to sunlight or ultraviolet radiation generated by an artificial light device, said human skin having undergone said step A.

Among the artificial light devices capable of generating ultraviolet radiation and capable of being used in step B) of the cosmetic tanning or browning process of the human skin which is the subject of the present invention, mention may be made for example ultraviolet lamps, consisting of one or more fluorescent lamps emitting ultraviolet radiation, 95% of which consists of ultraviolet-A radiation (wavelength 400 to 315 nanometers) and 5% consisting of by ultraviolet-B radiation (wavelength 315 to 280 nanometers) (with a margin of error of ± 3%). Advantageously, the cosmetic tanning or browning process of human skin, comprising steps A) and B) as described above, makes it possible to obtain a tanning or browning of the treated skin after short duration, characterized by greater color intensity and prolonged duration of persistence after completion of step B). The cosmetic formulations for topical use used in stage A) of the cosmetic process which is the subject of the present invention are generally in the form of aqueous or hydro-alcoholic or hydro-glycolic solutions, in the form of a suspension. emulsion, microemulsion or nanoemulsion, whether of the water-in-oil, oil-in-water, water-in-oil-in-water or oil-in-water type. in-oil, or in the form of a powder. The topical cosmetic formulations used in the cosmetic process which is the subject of the present invention may be packaged in a bottle, in a pump-type device, in pressurized form in an aerosol device, in a device provided with a perforated wall such as a grid or in a device provided with a ball applicator (called "roll-on"). In general, the compound of formula (I) or the composition (Cl), present in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention, is associated with chemical additives usually in the field of formulations for topical use, such as foaming and / or detergent surfactants, thickening and / or gelling surfactants, thickening and / or gelling agents, stabilizing agents, film-forming compounds, solvents and co-solvents, hydrotropic agents, thermal or mineral waters, plasticizers, emulsifiers and co-emulsifiers, opacifying agents, pearlescent agents, superfatting agents, sequestering agents, chelating agents, oils, waxes, antioxidants , perfumes, essential oils, preservatives, conditioners, deodorants, bleaching agents s intended for the bleaching of the 15 hairs and the skin, the active principles intended to provide a treating and / or protective action with respect to the skin or the hair, the sunscreens, the mineral fillers or the pigments, the particles providing a visual effect or intended for the encapsulation of active ingredients, exfoliating particles, texture agents, optical brighteners, repellents for insects. As examples of foaming and / or detergent surfactants which can be combined with the compound of formula (I) or with the composition (Cl) in topical cosmetic formulations used in the cosmetic process which is the subject of the present invention, mention may be made foaming surfactants and / or anionic, cationic, amphoteric or nonionic detergents. Among the foaming and / or detergent anionic surfactants which can be combined with the compound of formula (I) or with the composition (Cl) in the topical cosmetic formulations used in the cosmetic process which is the subject of the present invention, mention may be made of the alkali metal, alkaline earth metal, ammonium, amine or alkylalcohol salts of alkyl ether sulfates, alkyl sulphates, alkylamidoether sulphates, alkylaryl polyether sulphates, monoglyceride sulphates, alpha-olefinsulfonates, paraffin sulfonates, alkyl phosphates, alkyl ether phosphates, alkyl sulfonates, alkyl amide sulfonates, alkylaryl sulfonates, alkyl carboxylates, alkyl sulfosuccinates, alkyl ether sulfosuccinates, alkylamidesulfosuccinates, alkylsulfoacetates, alkyl sarcosinates, acylisethionates, N-acyltaurates, acyl lactylates, N-acyl derivatives of amino acids, N-acyl derivatives of peptides, N-acylated proteins, N-acyl derivatives of fatty acids. Among the foaming and / or detergent amphoteric surfactants that can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention, mention may be made of alkyl betaines, alkyl amidobetaines, sultaines, alkylamidoalkylsulfobetaines, imidazoline derivatives, phosphobetaines, amphopolyacetates and amphopropionates. Among the foaming and / or detergent cationic surfactants that can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention, mention may be made especially of quaternary ammonium derivatives. Among the foaming and / or detergent nonionic surfactants that can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention. mention may be made more particularly of alkyl polyglycosides comprising a linear or branched, saturated or unsaturated aliphatic radical containing from 8 to 16 carbon atoms, such as octyl polyglucoside, decyl polyglucoside, undecylenyl polyglucoside and dodecyl polyglucoside; tetradecyl polyglucoside, hexadecyl polyglucoside, 1,12-dodecanediyl polyglucoside; ethoxylated hydrogenated castor oil derivatives such as the product sold under the INCI name "Peg-40 hydrogenated castor oil"; polysorbates such as Polysorbate 20, Polysorbate 40, Polysorbate 60, Polysorbate 70, Polysorbate 80, Polysorbate 85; coconut amides; N-alkylamines. As examples of thickening and / or gelling surfactants which can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process which is the subject of the present invention, mention may be made of optionally alkoxylated alkyl polyglycoside fatty esters, such as ethoxylated methyl polyglucoside esters such as PEG 120 methyl glucose trioleate and PEG 120 methyl glucose dioleate, sold respectively under the names GLUCAMATETM LT and GLUMATETM DOE 120; alkoxylated fatty esters such as PEG 150 pentaerythrityl tetrastearate sold under the name CROTHIX ™ DS53, PEG 55 propylene glycol oleate sold under the name ANTIL ™ 141; fatty chain polyalkylene glycol carbamates such as PPG-14 laureth isophoryl dicarbamate marketed under the name ELFACOSTM T211, PPG-14 palmeth-60 hexyl dicarbamate sold under the name ELFACOSTM GT2125. Examples of thickening and / or gelling agents that can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process which is the subject of the present invention mention may be made of linear or branched or crosslinked polyelectrolytic polymers, such as the homopolymer of partially or totally salified acrylic acid, the homopolymer of partially or totally salified methacrylic acid, the homopolymer of the acid, Partially or completely salified 2-methyl [(1-oxo-2-propenyl) amino] -1-propanesulfonic acid (AMPS), copolymers of acrylic acid and APS, copolymers of acrylamide and AMPS, copolymers of vinylpyrrolidone and AMPS, copolymers of AMPS and (2-hydroxyethyl acrylate), copolymers of AMPS and (2-hydroxyethyl methacrylate), copolymers of APSH and hydroxyethylacryl amide, copolymers of AMPS and N, N-dimethyl acrylamide, copolymers of AMPS and tris (hydroxymethyl) acrylamido methane (THAM), copolymers of acrylic or methacrylic acid and acrylate (2-hydroxyethyl), copolymers of acrylic or methacrylic acid and (2-hydroxyethyl) methacrylate, copolymers of acrylic or methacrylic acid and hydroxyethylacrylamide, copolymers of acrylic acid or methacrylic and THAM, copolymers of acrylic or methacrylic acid and N, N-dimethyl acrylamide, terpolymers of acrylic or methacrylic acid, APSA and (2-hydroxyethyl) acrylate ), terpolymers of acrylic or methacrylic acid, AMPS and (2-hydroxyethyl) methacrylate, terpolymers of acrylic or methacrylic acid, AMPS and THAM, terpolymers of acrylic acid or methacrylic acid, AMPS and N, N-dimethyl acrylamide, erpolymers of acrylic or methacrylic acid, AMPS and acrylamide, copolymers of acrylic acid or methacrylic acid and alkyl acrylates having a carbon chain of between four and thirty atoms of carbon and more particularly between ten and thirty carbon atoms, the copolymers of AMPS and of alkyl acrylates whose carbon chain comprises between four and thirty carbon atoms and more particularly between ten and thirty carbon atoms, the linear, branched or crosslinked terpolymer of at least one monomer having a strong, free, partially salified or fully salified acidic function, with at least one neutral monomer, and at least one monomer of formula (VIII): CH 2 = C (R 6 ) -C (= O) - [CH 2 -CH 2 -O], - R 7 (VIII) in which R 6 represents a hydrogen atom or a methyl radical, R 7 represents a linear or branched alkyl radical containing from eight at thirty carbon atoms and n represents a number greater than or equal to one and less than or equal to fifty. Polymers of polyelectrolytic type, linear or branched or crosslinked that can be associated with the compound of formula (I) or with the composition (C1) in topical cosmetic formulations used in the cosmetic process that is the subject of the present invention. The invention may be in the form of a solution, an aqueous suspension, a water-in-oil emulsion, an oil-in-water emulsion, a powder. Polyelectrolytes, linear or branched or crosslinked polymers that can be combined with the compound of formula (I) or composition (C1) in topical cosmetic formulations used in the cosmetic process object of this The invention can be selected from the products sold under the names SIMULGELTM EG, SIMULGELTMEPG, SEPIGEL Tm 305, SIMULGELTM 600, SIMULGELTM NS, SIMULGELTM INS 100, SIMULGELTM FL, SIMULGELTM A, SIMULGELTM SMS 88, SEPINOVTMEMT 10, SEPIPLUSTM400, 15 SEPIPLUSTM265, SEPIPLUSTMS , SEPIMAXTMZen, ARISTOFLEXTMAVC, ARISTOFLEXTMAVS, NOVEMERTMEC-1, NOVEMERTMEC 2, ARISTOFLEXTMHMB, COSMEDIATMSP, FLOCARETMET 25, FLOCARETMET 75, FLOCARETMET 26, FLOCARETMET 30, FLOCARETMET 58, FLOCARETMPSD 30, VISCOLAMTMAT 64, VISCOLAMTMAT 100. Examples of thickeners and / or or gelling agents which can be combined with the compound of formula (I) or with the composition (C1) in cosmetic formulations with topical use used in the cosmetic process that is the subject of the present invention, mention may be made of polysaccharides consisting solely of monosaccharides, such as glucans or homopolymers of glucose, glucomannoglucans, xyloglycans and galactomannans whose degree of substitution (DS) D-galactose units on the main D-mannose chain are between 0 and 1, and more particularly between 1 and 0.25, such as galactomannans derived from cassia gum (DS = 1/5), locust bean gum (DS = 1/4), tara gum (DS = 1/3), guar gum (DS = 1/2), fenugreek gum (DS = 1). Examples of thickening and / or gelling agents that can be combined with the compound of formula (I) or with the composition (C1) in cosmetic formulations for topical use used in the cosmetic process that is the subject of the present invention mention may be made of polysaccharides consisting of monosaccharides, such as sulphated galactans and more particularly carrageenans and agar, uronans and more particularly alginines, alginates and pectins, heteropolymers of oses and acids. uronic and more particularly xanthan gum, gellan gum, exudates of gum arabic and karaya gum, glucosaminoglycans. Examples of thickening and / or gelling agents that can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process which is the subject of the present invention there may be mentioned cellulose, cellulose derivatives such as methyl cellulose, ethyl cellulose, hydroxypropyl cellulose, silicates, starch, hydrophilic derivatives of starch, polyurethanes. As examples of stabilizing agents that can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention, mention may be made of microcrystalline waxes, and more particularly ozokerite, mineral salts such as sodium chloride or magnesium chloride, silicone polymers such as polysiloxane polyalkyl polyether copolymers.

As examples of solvents which can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process which is the subject of the present invention, mention may be made of water, organic solvents such as glycerol, diglycerol, oligomers of glycerol, ethylene glycol, propylene glycol, butylene glycol, 1,3-propanediol, 1,2-propanediol, hexylene glycol, diethylene glycol , xylitol, erythritol, sorbitol, water-soluble alcohols such as ethanol, isopropanol or butanol, water mixtures and said organic solvents. As examples of thermal or mineral waters which can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process which is the subject of the present invention, it is possible to mention thermal or mineral waters having a mineralization of at least 300 mg / l, in particular Avene water, Vittel water, Vichy basin water, Uriage water, the water of La Roche Posay, the water of the Bourboule, the water of Enghien-les-Bains, the water of Saint-Gervais-les Bains, the water of Nérisles-baths, the water of Allevard- the baths, the water of Digne, the water of the Maizieres, the water of Neyrac-lesbains, the water of Lons le Saunier, the water of Rochefort, the water of Saint Christau, the water of the Fumades 30 and the water of Tercis-les-bains. As examples of hydrotropic agents that can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process which is the subject of the present invention, mention may be made of the xylene sulphonates, cumene sulphonates, hexyl polyglucoside, (2-ethylhexyl) polyglucoside, n-heptyl polyglucoside. As examples of emulsifying surfactants which can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process which is the subject of the present invention, it is possible to mention nonionic surfactants, anionic surfactants, cationic surfactants. As examples of emulsifying nonionic surfactants that can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process which is the subject of the present invention, it is possible to Mention esters of fatty acids and sorbitol, such as the products marketed under the names MONTANET ™ 40, MONTANET ™ 60, MONTANET ™ 70, MONTANET ™ 80 and MONTANET ™ 85; compositions comprising glycerol stearate and ethoxylated stearic acid between 5 moles and 150 moles of ethylene oxide, such as the composition comprising stearic acid ethoxylated with 135 moles of ethylene oxide and glycerol stearate. Sold under the name SIMULSOL ™ 165; mannitan esters; ethoxylated mannitan esters; sucrose esters; methyl glucoside esters; alkyl polyglycosides comprising a linear or branched, saturated or unsaturated aliphatic radical containing from 14 to 36 carbon atoms, such as tetradecyl polyglucoside, hexadecyl polyglucoside, octadecyl polyglucoside, hexadecyl polyxyloside or octadecyl polyxyloside; Eicosyl polyglucoside, dodecosyl polyglucoside, 2-octyldodecyl polyxyloside, 12-hydroxystearyl polyglucoside; linear or branched fatty alcohol compositions, saturated or unsaturated, and containing from 14 to 36 carbon atoms, and alkylpolyglycosides as described above, for example the compositions sold under the brand name MONTANOVTM68, MONTANOVTM82, MONTANOVTm14, MONTANOVTm202 , MONTANOVTMS, 25 MONTANOVTMWO 18, FLUIDANOVTm2OX and EASYNOVTM. As examples of anionic surfactants that can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention, mention may be made of glyceryl stearate citrate, cetearyl sulphate, soaps such as sodium stearate or triethanolammonium stearate, N-acyl derivatives of salified amino acids such as stearoyl glutamate. As examples of emulsifying cationic surfactants that can be combined with the compound of formula (I) or with the composition (C1) in the cosmetic formulations for topical use used in the cosmetic process that is the subject of the present invention, it is possible to use the same composition. Mention may be made of aminoxides, quaternium-82 and the surfactants described in the international application published under the number WO 96/00719 and mainly those whose fatty chain comprises at least 16 carbon atoms. Examples of opacifying and / or nacrating agents that can be combined with the compound of formula (I) or with the composition (C1) in topical cosmetic formulations used in the cosmetic process that is the subject of the present invention mention may be made of sodium palmitate, sodium stearate, sodium hydroxystearate, magnesium palmitate, magnesium stearate, magnesium hydroxystearate, ethylene glycol monostearate and ethylene glycol distearate, polyethylene glycol monostearate, polyethylene glycol distearate, and fatty alcohols having from 12 to 22 carbon atoms. As examples of texture agents that can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention, mention may be made of N-acylated derivatives of amino acids, such as lauroyl lysine marketed under the name AMINOHOPETMLL, octenyl starch succinate sold under the name DRYFLOTM, myristyl polyglucoside sold under the name MONTANOVTM 14, cellulose fibers, cotton fibers, chitosan fibers, talc, sericite, mica. As examples of deodorant agents that can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention, mention may be made of alkali silicates, zinc salts such as zinc sulphate, zinc gluconate, zinc chloride, zinc lactate; quaternary ammonium salts such as cetyltrimethylammonium salts, cetylpyridinium salts; glycerol derivatives such as glycerol caprate, glycerol caprylate, polyglycerol caprate; 1,2 decanediol; 1,3 propanediol; salicylic acid; sodium bicarbonate; cyclodextrins; metallic zeolites; TRICLOSANTM; aluminum bromohydrate, aluminum chlorohydrates, aluminum chloride, aluminum sulphate, aluminum and zirconium hydrochlorides, aluminum and zirconium trihydrochloride, aluminum zirconium tetrachlorohydrate , aluminum and zirconium pentachlorohydrate, aluminum and zirconium octochlorohydrate, aluminum sulphate, sodium aluminum lactate, aluminum and glycol hydrochloride complexes, as the complex propylene glycol aluminum dihydrochloride complex, aluminum and propylene glycol sesquichlorohydrate complex, aluminum 0075 complex of aluminum dihydrochloride and polyethylene glycol, the complex of aluminum sesquichlorohydrate and polyethylene glycol. As examples of oils which can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process which is the subject of the present invention, mention may be made of the mineral oils such as paraffin oil, liquid petrolatum, isoparaffins or mineral white oils; oils of animal origin, such as squalene or squalane, vegetable oils, such as phytosqualane, sweet almond oil, coconut oil, castor oil, jojoba oil, olive oil, rapeseed oil, peanut oil, sunflower oil, wheat germ oil, corn germ oil, soybean oil, cottonseed oil, alfalfa oil, poppy oil, pumpkin oil, evening primrose oil, millet oil, barley oil, rye oil, l safflower oil, bancoulin oil, passionflower oil, hazelnut oil, palm oil, shea butter, apricot kernel oil, calophyllum oil, l sysymbrium oil, avocado oil, calendula oil, oils derived from flowers or vegetables, ethoxylated vegetable oils; synthetic oils such as fatty acid esters such as butyl myristate, propyl myristate, isopropyl myristate, cetyl myristate, isopropyl palmitate, octyl palmitate, butyl stearate, hexadecyl stearate, isopropyl stearate, octyl stearate, isocetyl stearate, dodecyl oleate, hexyl laurate, propylene glycol dicaprylate, lanolic acid derived esters, such as isopropyl lanolate, isocetyl lanolate, monoglycerides, diglycerides and triglycerides of fatty acids such as glycerol triheptanoate, alkylbenzoates, hydrogenated oils, poly (alpha-olefin), polyolefins such as poly ( isobutane), synthetic isoalkanes such as isohexadecane, isododecane, perfluorinated oils; silicone oils such as dimethylpolysiloxanes, methylphenyl polysiloxanes, amine-modified silicones, fatty acid-modified silicones, alcohol-modified silicones, alcohol-modified silicones and fatty acids, modified silicones by polyether groups, modified epoxy silicones, silicones modified with fluorinated groups, cyclic silicones and silicones modified with alkyl groups. By "oils" is meant herein the compounds and / or the mixtures of water-insoluble compounds having a liquid appearance at a temperature of 25 ° C. As examples of waxes that can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention, mention may be made of bee, carnauba wax, candelilla wax, ouricoury wax, japanese wax, cork fiber wax, sugar cane wax, paraffin waxes, waxes lignite, microcrystalline waxes, lanolin wax; ozokerite; polyethylene wax; silicone waxes; vegetable waxes; fatty alcohols and solid fatty acids at room temperature; glycerides solid at room temperature. By "waxes" is meant in this application compounds and / or mixtures of water-insoluble compounds having a solid appearance at a temperature of 45 ° C or higher. As examples of active principles that can be associated with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention, mention may be made of vitamins and their derivatives, especially their esters, such as retinol (vitamin A) and its esters (retinyl palmitate for example), ascorbic acid (vitamin C) and its esters, ascorbic acid sugar derivatives ( as ascorbyl glucoside), tocopherol (vitamin E) and its esters (such as tocopherol acetate), vitamins B3 or B10 (niacinamide and its derivatives); compounds showing a lightening or depigmenting action on the skin, such as the w-undecelynoyl phenylalanine sold under the name SEPIWHITETMMSH, SEPICALMTMVG, the mono ester and / or the glycerol diester of the w-undecylenoyl phenylalanine, the w-undecelynoyl dipeptides, arbutin, kojic acid, hydroquinone; the compounds showing a soothing action including SEPICALM ™ S, allantoin and bisabolol; anti-inflammatory agents; compounds showing a moisturizing action such as urea, hydroxyureas, glycerol, polyglycerols, glycerol glucoside, diglycerol glucoside, polyglyceryl glucosides, xylityl glucoside; plant extracts rich in polyphenols such as grape extracts, pine extracts, wine extracts, olive extracts; compounds showing a slimming or lipolytic action such as caffeine or its derivatives, ADIPOSLIM ™, ADIPOLES ™, fucoxanthin; N-acylated proteins; N-acyl peptides such as MATRIXIL ™; N-acyl amino acids; partial hydrolysates of N-acylated proteins; amino acids; peptides; total hydrolysts of protein; soy extracts, for example Raffermine TM; wheat extracts, for example TENSINETM or GLIADINETM; plant extracts, such as tannin-rich plant extracts, plant extracts rich in isoflavones or plant extracts rich in terpenes; seaweed or freshwater algae extracts; marine plant extracts; marine extracts in general such as corals; essential waxes; bacterial extracts; ceramides; phospholipids; compounds showing antimicrobial action or purifying action, such as LIPACIDETM C8G, LIPACIDETM UG, SEPICONTROLTM A5; OCTOPIROXTm or SENSIVATM SC50; compounds showing an energizing or stimulating property, such as the panthenol and its derivatives such as SEPICAP ™ PM; anti-aging actives such as SEPILIFTTM DPHP, LIPACIDETM PVB, SEPIVINOLTM, SEPIVITALTM, MANOLIVATM, PHYTO-AGETM, TIMECODETM; SURVICODETM; anti-aging photo active ingredients; the active ingredients protecting the integrity of the dermal-epidermal junction; actives enhancing the synthesis of extracellular matrix components such as collagen, elastins, glycosaminoglycans; assets acting favorably on chemical cellular communication such as cytokines or physical ones such as integrins; the active ingredients creating a sensation of "heating" on the skin, such as the activators of cutaneous microcirculation (such as derivatives of nicotinic acid) or products creating a sensation of "freshness" on the skin (such as menthol and derivatives ); the active agents improving cutaneous microcirculation, for example the venotonic ones; draining assets; decongestant active ingredients such as extracts of ginko biloba, ivy, horse chestnut, bamboo, ruscus, holly, centalla asiatica, fucus, rosemary, willow; tanning agents or skin browning agents, for example dihydroxyacetone (DHA), erythrulose, mesotartaric aldehyde, glutaraldehyde, glyceraldehyde, alloxane, ninhydrin, plant extracts, for example wood extracts red Pterocarpus and Baphia genus such as Pteropcarpus santalinus, Pterocarpus osun, Pterocarpus soyauxii, Pterocarpus erinaceus, Pterocarpus indicus or Baphia nitida such as those described in European Patent Application EP 0 971 683; agents known for their action of facilitating and / or of accelerating the tanning and / or browning of human skin, and / or for their action of coloring human skin, for example caratenoids (and more particularly beta carotene and gamma carotene), the product marketed under the tradename "Carrot oil" (INCI name: Daucus Carota, helianthus annuus sunflower oil) by Provital, which contains carotenoids, vitamin E and vitamin K ; tyrosine and / or its derivatives, known for their effect on the tanning acceleration of human skin in association with exposure to ultraviolet radiation, for example the product marketed under the brand name "SunTan AcceleratorTM" by the Provital company which contains tyrosine and riboflavins (vitamin B), the tyrosine tyrosinase complex marketed under the brand name "Zymo Tan Complex" by Zymo Line, the product sold under the trade name MelanoBronzeTM ( INCI name: Acetyl Tyrosine, Monk's pepper extract (Vitex Agnus-castus)) by the company Mibelle which contains acetyl tyrosine, product sold under the brand name Unipertan VEG-24/242/2002 (INCI name: butylene glycol and Acetyl Tyrosine and Hydrolyzed Vegetable Protein and Adenosine Triphosphate) by the company UNIPEX, the product marketed under the trademark "Try-ExcellTm" (INCI name: Oleoyl Tyrosine 3029410 21 S1 0075 and Luffa Cylindrica (Seed) Oil and Oleic Acid) by Sederma Company which contains extracts of pumpkin seed (or Loofah oil), the product sold under the trade name "Actibronze TM" (INCI name: hydrolyzed wheat protein and acetyl tyrosine and copper gluconate) by the company Alban Muller, the product sold under the brand name Tyrostan TM (INCI name 5: potassium caproyl tyrosine) by the company Synerga, the product sold under the trade name Tyrosinol (INCI name: Sorbitan Isostearate, Glyceryl Oleate, Caproyl Tyrosine) by Synerga, the product sold under the brand name InstaBronzeTM (INCI name: Dihydroxyacetone and Acetyl Tyrosine and Copper Gluconate) marketed by Alban Muller, the product sold under the trade name Tyrosilane (INCI name: methylsilanol 10 and acetyl tyrosine) by Exymol; peptides known for their effect of activating melanogenesis, for example the product marketed under the brand name Bronzing SF Peptide powder (INCI name: Dextran and Octapeptide-5) by the company Infinitec Activos, the product sold under the brand name Melitane (INCI name: Glycerin and Aqua and Dextran and Acetyl hexapeptide-1) comprising acetyl hexapeptide-1 known for its alpha-MSH agonist action, the product marketed under the brand name Melatimes SolutionsTM (INCI name: Butylene glycol, Palmitoyl Tripeptide-40) by LIPOTEC, sugars and sugar derivatives, for example the product marketed under the brand name TanositolTM (INCI name: inositol) by the company Provital, the product marketed under the brand name Thalitan TM (or PhycosaccharideTM AG) by the company CODIF International (INCI name: 20 Aqua and hydrolyzed algin (Laminaria Digitata) and magnesium sulfate and manganese sulfate) containing an olig marine origin osaccharide (guluronic acid and mannuronic acid chelated with magnesium and manganese ions), the product sold under the brand name MelactivaTM (INCI name: Maltodextrin, Mucuna Pruriens Seed extract) by the company Alban Muller, the compounds rich in flavonoids for example the product marketed under the brand name "Biotanning" (INCI name: Hydrolyzed citrus Aurantium dulcis fruit extract) by the company Silab and known to be rich in flavonoids of lemon (hesperidin type). As examples of antioxidants that can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention, mention may be made of EDTA and its salts, citric acid, tartaric acid, oxalic acid, BHA (butylhydroxyanisole), BHT (butylhydroxytoluene), tocopherol derivatives such as tocopherol acetate, mixtures of compounds antioxidants such as DISSOLVINETM GL 47S marketed by Akzo Nobel under the name INCI: Tetrasodium Glutamate Diacetate.

As examples of sunscreens that can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process which is the subject of the present invention, it is possible to may include all those listed in the Cosmetic Directive 76/768 / EEC amended Annex VII. Among the solar organic filters which can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process which is the subject of the present invention, mention may be made of family of benzoic acid derivatives such as para-aminobenzoic acids (PABA), in particular the monoglycerol esters of PABA, the ethyl esters of N, N-propoxy PABA, the ethyl esters of N, N-diethoxy PABA, the ethyl esters N, N-dimethyl PABA, N, N-dimethyl PABA methyl esters, N, N-dimethyl PABA butyl esters; the family of anthranilic acid derivatives such as homomenthyl-N-acetyl anthranilate; the family of salicylic acid derivatives such as amyl salicylate, homomenthyl salicylate, ethylhexyl salicylate, phenyl salicylate, benzyl salicylate, p-isopropanolphenyl salicylate; the family of cinnamic acid derivatives such as ethylhexyl cinnamate, ethyl-4-isopropyl cinnamate, methyl-2,5-diisopropyl cinnamate, p-methoxypropyl cinnamate, pmethoxyisopropyl cinnamate, p-methoxyisoamyl cinnamate, p-methoxyoctyl cinnamate (p-methoxy 2-ethylhexyl cinnamate), p-methoxy 2-ethoxyethyl cinnamate, p-methoxycyclohexyl cinnamate, ethyl-a-cinnamate cyano-6-phenyl, (2-ethylhexyl) -α-cyano-6-phenyl cinnamate, diparamethoxy mono-2-ethylhexanoyl glyceryl cinnamate; the family of benzophenone derivatives such as 2,4-dihydroxybenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2 ', 4,4'-tetrahydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonate, 4-phenylbenzophenone, 2-ethylhexyl-4'-phenylbenzophenone-2-carboxylate, 2-hydroxy -4-n-octyloxybenzophenone, 4-hydroxy-3-carboxybenzophenone; 3- (4'-methylbenzylidene) -d, 1-camphor, 3- (benzylidene) -d, 1-camphor, benzalkonium methosulfate camphor; urocanic acid, ethyl urocanate; the family of sulfonic acid derivatives such as sulfonic acid 2-phenylbenzimidazole-5 and its salts; the family of triazine derivatives such as hydroxyphenyl triazine, ethylhexyloxyhydroxyphenyl-4-methoxyphenyltriazine, 2,4,6-trianillino- (p-carbo-2'-ethylhexyl-t-oxy) -1,3, 5-Triazine, 4,4 - ((6 - (((1,1-dimethylethyl) amino) carbonyl) phenyl) amino) -1,3,5-triazine-2,4-diyl diimino) bis- (2-triazine) benzoic acid ester, 2-phenyl-5-methylbenzoxazole, 2,2'-hydroxy-5-methylphenylbenzotriazole, 2- (2'-hydroxy-5'-toctylphenyl) benzotriazole, 2- (2'-hydroxy-5'-methylphenyl) benzotriazole; dibenzazine; Sodium dibutylmethane, 4-methoxy-4 "-t-butylbenzoylmethane, 5- (3,3-dimethyl-2-norbornylidene) -3-pentan-2-one, the family of diphenylacrylate derivatives such as 2-ethylhexyl-2-cyano-3,3-diphenyl-2-propenoate, ethyl-2-cyano-3,3-diphenyl-2-propenoate, the family of polysiloxanes such as benzylidene malonate siloxane.

Among the inorganic solar filters, also called "inorganic screens", which can be combined with the compound of formula (I) or with the composition (C1) in cosmetic formulations for topical use implemented in the cosmetic process object of the present invention can be made of titanium oxides, zinc oxides, cerium oxide, zirconium oxide, iron oxides yellow, red or black, chromium oxides. These inorganic screens may or may not be micronized, may or may not have undergone surface treatments and may optionally be presented in the form of aqueous or oily pre-dispersions. The subject of the invention is also a compound of formula (I) or a composition (C1) as defined above, for their use in a therapeutic treatment method intended to stimulate the production of melanins for preventing and / or treating human skin. The following examples illustrate the invention without limiting it. EXAMPLE 1 Preparation of a Composition (C18) According to the Invention 400.1 grams of valine is introduced, ie one molar equivalent in a mixture of hydroalcoholic consisting of 1439.7 grams of water and 160.1 grams isopropanol at a temperature of 20 ° C. The pH of the medium is adjusted to 10 by addition of a 30% sodium hydroxide solution. 444.8 grams of octanoyl chloride, ie 0.8 molar equivalents, are then gradually added to the mixture maintained between 20 ° C. and 40 ° C., and at a pH of between 10 and 10.5. The reaction medium is then stirred for two hours and then heated to reach 80 ° C., then 1113.2 grams of a 75% phosphoric acid solution are added to progressively reach a pH value of about 2.0. The aqueous phase of the medium is decanted and withdrawn and the organic phase remaining in the reactor is washed several times with 10% brine at 80 ° C. with stirring. After washing and then drying the remaining water by vacuum distillation, the organic phase comprising 636.9 grams of desired N-octanoyl valine is obtained. 45.8 grams of 1,3-butanediol, ie one molar equivalent, are introduced into the reactor comprising 125.2 grams of the dried reaction medium obtained in the preceding step. The temperature is raised to 120 ° C. 0.39 grams of 98% sulfuric acid and 0.39 grams of 50% hypophosphorous acid are then added and the resulting mixture is heated to 125 ° C. under partial vacuum with bubbling. nitrogen. The reaction mixture is then maintained for 23 hours with stirring at this temperature, then neutralized by addition of a 30% sodium hydroxide solution so as to obtain a pH of the composition (C1A), diluted to 5% in water, between 3.0 and 6.0.

The analytical characteristics of the composition (C1A) obtained are as follows: acid number (according to NFT 60-204) = 55.7 pH of the composition (C1A) at 5% in water (according to the method NFT 73-206 ) = 4.2 Hydroxyl number (according to US Pharmacopeia XXI NF XVI 01/011985) = 194.6 Ester number (calculated as the difference between the saponification number measured according to the method NFT 60-110 and acid number measured according to the method NFT 60-204) = 128.2 Saponification number (according to NFT 60-206) = 183.9 mg KOH / g Exem the 2nd ation of a Cl composition according to l The procedure of the process described in Example 1 is carried out by replacing the 0.8 molar equivalent of octanoyl chloride with 0.8 molar equivalents of hexadecanoyl chloride to give the composition (C1B). whose analytical characteristics are as follows: Acid value (according to NFT 60-204) = 36.5 pH of the composition (C1B) at 5% in water (according to the NFT 73-206 method) = 7.1 Hydroxyl number (according to US Pharmacopeia XXI NF XVI 01/011985) = 135.5 Ester number (calculated by the difference between the saponification number measured according to the NFT 60-110 method and the acid number measured according to the method NFT 60-204) = 100.8 Saponification number (according to NFT 60-206) = 137.3 mg KOH / g Example 3: Preparation of a Composition (A) according to US Pat. STATE OF THE ART The procedure of the process described in Example 1 is carried out by replacing the 0.8 molar equivalent of octanoyl chloride with 0.8 molar equivalents of (wundecylenoyl) chloride in order to obtain the composition. (A), whose analytical characteristics are as follows: Acid number (according to NFT 60-204) = 50.0 pH of Composition (A) at 5% in water (according to method NFT 73-206) = 5 , 3 Hydroxyl number (according to US Pharmacopeia XXI NF XVI 01/011985) = 149.9 Ester number (calculated by the difference between the saponification number measured according to the NFT method 60-110 and the acid number measured according to the method NFT 60-204) = 114.0 S0 0075 Saponification number (according to NFT 60-206) = 164.0 mg KOH / g Example 4: preparation of a Composition (B) according to the state of the art The procedure of the method described in Example 1 is carried out by replacing the molar equivalent of valine one molar equivalent of isoleucine, to obtain the Composition (B) whose analytical characteristics are as follows: Acid value (according to NFT 60-204) = 60.0 pH of the Composition (B) at 5% in water (according to the NFT 73-206 method) = 4.6 Index d Hydroxyl (according to US Pharmacopeia XXI NF XVI 01/011985) = 212.2 Ester number (calculated as the difference between the saponification number measured according to the method NFT 60-110 and the acid number measured according to the method NFT 60-204) = 132.8 Saponification number (according to NFT 60-206) = 192.8 mg KOH / g Example 5: Preparation of a Composition (D) according to the state of the art.

The procedure of the process described in Example 1 is carried out by replacing the molar equivalent of valine with a molar equivalent of alanine, to obtain Composition (D), the analytical characteristics of which are as follows: NFT 60-204) = 21.9 pH of Composition (D) at 5% in water (according to method NFT 73-206) = 4.6 20 Hydroxyl Index (according to US Pharmacopeia XXI NF XVI 01 / 011985) = 221.5 Ester number (calculated as the difference between the saponification number measured according to the NFT method 60-110 and the acid number measured according to the NFT 60-204 method) = 176.8 Index saponification (according to NFT 60-206) = 198.7 mg KOH / g.

Demonstration of the human skin staining activity of the compounds and compositions according to the invention by a study of the production of melanin on a line of murine melanocytes B16 / F1 The demonstration of the activity of staining was performed by the implementation of a study model of the production of melanin on a line of murine melanocytes B16 / F1.

This test is commonly used in the cosmetics and pharmaceutical sector. Protocol: B16F1 murine melanocytes were amplified in T75 culture flask, then seeded at 5000 cells / well in 96-well culture plates in a specific culture medium, at 37 ° C. in a humid atmosphere containing 5% CO 2.

After 24 hours of plaque amplification, the cells were treated with the compositions according to the invention, or culture medium alone (control) and then incubated for 72 hours at 37 ° C. under 5% CO 2. Each condition has been realized in triplicate.

Evaluation of the effects: After the incubation, the supernatants were recovered and the melanin secreted by the cells in the (extracellular) culture medium was quantified by spectrophotometric measurement at 450 nm of these culture supernatants, against a standard range of melanin. The results were expressed in μg of melanin / ml of culture medium.

The cell mats were lysed in PBS using a sonication rod and 2 evaluations were performed on them: Evaluation of the amount of melanin by spectrophotometric measurement at 450 nm of the lysates against a melanin standard range; Evaluation of the amount of protein by assay according to the method of Bradford.

The results of melanin production by cells (intracellular) were expressed relative to the amount of protein present in the carpets. Thus the final result is given as pg melanin per mg protein. Statistical analysis using the Student's test was performed to compare each condition with the control condition.

A first series of tests was conducted with compositions (C1A) and (C1B) according to the invention, compared to the culture control and to Composition (A). The results obtained are recorded in the following Table 1. Table 1 Products tested Intracellular melanin (μg / mg protein) Culture control 91 ± 3 Composition (C1A) (50 μg / ml) 115 ± 2 Composition (C1B) (50 μg / ml) 128 ± 5 Composition (A) ( 50 μg / ml). Observed toxicity A second series of tests was conducted with comparative compositions (B) and (D) compared to the culture control. The results obtained are recorded in the following Table 2.

TABLE 2 Products Tested Intracellular Melanin (μg / mg Protein) Culture Control 93 ± 8 Composition (B) (50 μg / ml) Toxicity Observed Composition (D) (50 μg / ml) 66 ± 4 Relative to control, the use of the compositions (C1A) and (C1B), induce an increase in the production of intracellular melanin at the dose of 50 μg / ml, whereas the use of the composition (D) does not induce increased production of intracellular melanin at a dose of 50 μg / ml, but a decrease. Moreover, the compositions (A) and (B) were cytotoxic when tested under the same conditions and at the same dose.

Bibliography (1): Petersen et al., "Dihydroxyacetone, the active browning ingredient in sunless tanning lotions, DNA damage digests, cell-cycle block and apoptosis in cultured HaCaT keratinocytes", 2004, Mutat Res, Jun 13; 560 (2). ): 173-86.

Examples of cosmetic formulations In the following examples, the proportions are expressed as weight percentages. Non-greasy tanning machine for face and body LANOLTM 2681: 3.0% 20 SEPIMAXTmZen: 2.5% Water: q.s. 100% Composition (C1B): 1.0% Perfume: 0.2% SEPICIDETM HB: 0.8% 25 Soda: q.s. pH = 5 Bronzing emulsion without sun LANOLTM 99: 15% MONTANOVTM 68: 5.0% PARSOLTM MCX: 3.0% 3029410 28 S1 0075 Water: qsp100 ° / 0 Composition (CIA) 3.0% Monosodium phosphate: 0, 2% SEPIMAXTM Zen: 0.5% 5 Perfume: 0.3% SEPICIDETM HB: 0.8% Soda: qs pH = 5. Pressed powder Earth of sun SIMULGELTmEG: 2.00% 10 LANOLTM 99: 12,00% Composition (C1B): 1,00% Talc: 33,00% MICROPEARLTM M310: 3,00% Iron oxide yellow: 0,80% 15 Iron oxide red: 0.30% Iron oxide black: 0.05% Mica: qs 100% self-tanning gel SIMULGELTmEG: 5.0% Ethanol: 30% Composition (CIA) 5% Menthol: 0.1% Caffeine: 2.5% Ivry extract: 2% 25 SEPICIDETM HB: 1% Water: q.s. 100% Sunblock and self-tanning gel MONTANOVTM S: 3.0% Glyceryl triheptanoate: 10.0% LIPACIDETM PVB: 1.05% SIMULGELTmEG: 2.2% Water: q.s. 100% Composition (C1B): 5% Fragrance: 0.1% 3029410 29 S1 0075 SEPICIDETM HB: 0.3% SEPICIDETM CI: 0.1% PARSOLTM MCX: 4.0% Self-bronzing cream with 5-hydroxy acids MONTANOVTM 68 : 5.0% LIPACIDETM PVB: 1.05% LANOLTM 99: 10.0% Water: qs 100% Gluconic acid: 1.5% 10 Composition (C1B): 3% Triethanolamine: 0.9% SEPIMAXTmZen: 1.5% Fragrance: 0.4% SEPICIDETM HB: 0.2% 15 SEPICIDETM CI: 0.4% Self-tanning cream with a-hydroxy acids for sensitive skin Mixture of N-lauroyl amino acids: 0.1% to 5% Magnesium and potassium aspartate: 0.002% to 0.5% MONTANOVTM 68: 5.0% 20 LANOLTM 99: 2 , 0% Water: qs 100% Lactic Acid: 1.5% Composition (C1B): 3.5% Triethanolamine: 0.9% SIMULGELTMINS 100: 1.5% Fragrance: 0.4% SEPICIDETM HB: 0.3% SEPICIDETM Cl: 0, 2% Satin self-tanning moisturizing emulsion 30 SIMULSOLTM 165: 5.0% LANOLTM 1688: 8.5% Galam butter: 2% Liquid paraffin: 6.5% LANOLTM 14M: 3% 3029410 30 S1 0075 LANOLTM S: Water: Composition (C1B): MICROPEARLTM M100: 5 SIMULGELTmNS: AQUAXYL TM Vitamin E acetate: Sodium pyrolidinonecarboxylate: Fragrance: 10 SEPICIDETM HB: SEPICIDETM CI: Satin self-tanning moisturizing emulsion A Disodium water EDTA Sodium Benzoate Soda (12%) 0, 6% 66.2% 3% 5% 3% 5% 0.20% 0.20% 0.2% 0.5% 0.3% Up to 100% 0.10% 0.30% 0.07% B MONTANOVTM L 1.00% SIMULSOLTM 165 2.00% LANOLTM P 2.00% Caprylic / Capric Triglyceride 5.00% Neopentyl Glycol 8.00% Dimethicone 1.00% Composition (C1B) 1.00% C SEPIMAXTM ZEN 1.50% SOLAGUMTM AX 0.50% D Phenoxyethanol and Ethylhexylglycerin 1.00% Suncare Lotion - SPF15 Up to 100% A Aqua / Water SOLAGUMTM AX 0.50% Triethanolamine (99%) 0.40% B SENSANOVTM VVR 3.00% MONTANOVTM S 1.00% 3029410 31 S1 0075 C12-15 Alkyl Benzoate 10.00% Ethylhexylmethoxycinnamate and BHT 5.00% Butylmethoxydibenzoylmethane 2.50% C Cyclopentasiloxane and cyclohexasiloxane 2.50% D AQUAXYLTM 3.00% Phenoxyethanol and Ethylhexylglycerin 1.00% Composition (C1B) 1.00% Perfume / Fragrance 0.10% Lactic Acid (25%) 0.09% Activator cream gel with DHA A Aqua / Water Qs 100% B SIMULGELTM SMS 88 3.00% C12-15 Alkyl Benzoate 10.00% Dimethicone 5.00 % C Glycerin 3.00% Monopropylene Glycol 2.00% Phenoxyethanol and Ethylhexylglycerin 1.00% Tocopherol 0.05% D Aqua / Water 40.00% Dihydroxyacetone 3.00% E Composition (C1B) 1.00% Fragrance / Fragrance 0.10% Citric Acid Qs pH Body Lotion after Solar A Water Up to 100 ° A SEPIMAXTM ZEN 0.50% B AQUAXYLTM 2.00% SEPICALMTM S WP 1.00% 3029410 32 S1 0075 C Butylene Glycol 3.00% SEPICLEARTM G7 1.30% Fragrance / Fragrance 0.03% Phenoxyethanol and Ethylhexyl Glycerin 0.80% Compositio n (C1B) 1.00% The commercial products used in the examples are defined as follows: - LANOLTM 2681 is a caprylate mixture, coconut caprate, marketed by the company SEPPIC - SEPIMAXTMZen (INCI name polyacrylate crosspolymer-6) is a thickening agent Emulsifier and stabilizer; LANOLTM 99 is isononyl isononanoate marketed by the company SEPPIC; MONTANOV-68 (cetearyl glucoside), is a self-emulsifiable composition as described in WO 92/06778, sold by the company SEPPIC; SEPICIDETM HB (INCI name: Phenoxyethanol / Methylparaben / Ethylparaben / Propylparaben 10 / Butylparaben) is a preserving agent marketed by the company SEPPIC; PARSOL ™ MCX is octyl para-methoxy cinnamate; marketed by GIVAUDAN; MICROPEARL ™ M310 is an ultra-fine powder with a very soft feel and mattifying action marketed by MATSUMO; SIMULGELTMEG (INCI name: sodium acryloyldimethyltaurate / sodium acrylate, and isohexadecane and polysorbate 80) is a thickening, emulsifying and stabilizing agent marketed by the company SEPPIC; - MONTANOVTM S is a pearlescent agent, marketed by the company SEPPIC, based on a mixture of alkyl polyglucosides such as those described in WO 95/13863; LIPACIDETM PVB is an acyl wheat protein hydrolyzate marketed by the company SEPPIC; SEPICIDETM C1, imidazolidine urea, is a preserving agent marketed by the company SEPPIC; SIMULGELTMINS 100 (INCI name: sodium acryloyldimethyltaurate / hydroxy ethyl acrylate, and isohexadecane and polysorbate 60) is a thickening, emulsifying and stabilizing agent marketed by the company SEPPIC; SIMULSOL ™ 165 is self-emulsifiable glycerol stearate marketed by the company SEPPIC; - LANOLTM 1688 is an emollient non-fat ester sold by the company SEPPIC 3029410 33 S1 0075 - LANOLTM 14M and LANOLTM S are consistency factors marketed by the company SEPPIC; SIMULGELTMNS (INCI name: sodium acryloyldimethyltaurate / hydroxy ethyl acrylate, and squalane and polysorbate 60) is a thickening, emulsifying and stabilizing agent marketed by the company SEPPIC; AQUAXYLTM (INCI name: Xylitylglucoside and Anhydroxylitol and Xylitol): moisturizing composition marketed by the company SEPPIC; - MONTANOVTM L (INCI name: C14-22 Alkyl Alcohol C12-20 Alkyl Glucoside) is an emulsifying composition marketed by the company SEPPIC; LANOL ™ P is an emollient ester of palmitic acid and ethylene glycol; SOLAGUMTM AX is a mixture of acacia gum and xanthan gum used as an emulsifier; SENSANOVTM WR (INCI name: C20-22 Alkyl phosphate & C20-22 Alcohols) is an anionic surfactant mixture sold by the company SEPPIC; SIMULGEL ™ SMS 88 (INCI name: Sodium acrylate / Acryloyldimethyl taurate / Dimethylacrylamide crosspolymer & Isohexadecane & Polysorbate 60) is a thickening and emulsifying agent marketed by the company SEPPIC; SEPICALMTM S WP (INCI name: Sodium Cocoyl Amino Acids & Sarcosine & Potassium Aspartate. & Magnesium) is a soothing agent marketed by the company SEPPIC; SEPICLEARTM G7 (INCI name: heptyl glucoside) is a solubilizing agent marketed by the company SEPPIC.

Claims (6)

REVENDICATIONS1. Use of a compound of formula (I): ## STR5 ## wherein R 'and R ", which may be identical or different, represent either a hydrogen atom, ie a monovalent radical of formula (II): ## STR2 ## in which the group R 1 -C (= O) represents the octanoyl radical; or the hexadecanoyl radical, it being understood that at least one of the radicals R 'or R "does not represent a hydrogen atom and that when none of the radicals R' and R" represents a hydrogen atom, R 'and R "are identical, or a mixture of compounds of formula (I), said use being for the purpose of browning and / or tanning the human skin and said use being in a cosmetic composition. 2. Use as defined in claim 1, of a composition (C1) comprising for 100% of its mass - from 99% by weight to 20% by weight of at least one compound of formula (la) F-O-CHFCHFC1 Wherein R 'represents a monovalent radical of formula (II): ## STR2 ## wherein R1-C (= O) - represents the octanoyl radical or the hexadecanoyl radical; - 1% by weight to 80% by weight of at least one compound of formula (Ib): ## STR2 ## ), wherein R is a monovalent radical of formula (II): wherein R1-C (= O) - represents the octanoyl radical or the hexadecanoyl radical. 3. A process for the purpose of browning and / or tanning human skin comprising at least one application step A on said human skin of a topical cosmetic formulation comprising at least one cosmetically acceptable excipient and an effective amount of at least one compound of formula (I): ## STR5 ## wherein R 'and R ", which may be identical or different, represent either a hydrogen atom or or a monovalent radical of formula (II): ## STR1 ## in which formula (II) in which the group R 1 -C (= O) - represents the octanoyl radical or the hexadecanoyl radical, it being understood that at least one of the radicals R 'or R "does not represent a hydrogen atom and that when none of the radicals R' and R" represents a hydrogen atom, R 'and R "are identical. 20 4. A process for the purpose of browning and / or tanning human skin comprising at least one step A of application to said human skin of a topical cosmetic formulation comprising at least one cosmetically acceptable excipient and an effective amount of a composition (C1) comprising for 100% of its mass: from 99% by weight to 20% by weight of at least one compound of formula (Ia) CH 3 F -O-CHFCHFCH-OH (Ia), Wherein R 'represents a monovalent radical of formula (II): ## STR2 ## wherein formula (II) in which R1-C (= O) - represents the octanoyl radical or the hexadecanoyl radical, - from 1 wt.% to 80 wt.% of at least one compound of formula (lb): ## STR5 ## wherein the radical R, represents a monovalent radical of formula (II): ## STR3 ## in which the group R 1 -C (= O) represents the octanoyl radical or the radical adical hexadecanoyl. 15 5. Compound of formula (I): ## STR3 ## in which R 'and R ", which may be identical or different, represent either a hydrogen atom or a monovalent radical; of formula (II): embedded image wherein R 1 -C (= O) represents the octanoyl radical or the hexadecanoyl radical, it being understood that at least one of the radicals R 'or R "does not represent a hydrogen atom and when none of the radicals R' and R" is hydrogen, R 'and R "are identical, for its use in a therapeutic treatment method for stimulating the production of melanins to prevent and / or treat diseases of human skin. 6. Composition (C1) comprising for 100% of its mass: 10 - from 99% by mass to 20% by weight of at least one compound of formula (Ia) CH3 F -O-CHFCHFCH-OH (la), formula (la in which R 'represents a monovalent radical of formula (II): wherein R1-C (= O) - represents the octanoyl radical or the hexadecanoyl radical, From 1 wt.% To 80 wt.% Of at least one compound of formula (Ib): ## STR5 ## wherein R is a monovalent radical of formula II): ## STR5 ## wherein R 1 -C (= O) - represents the octanoyl radical or the hexadecanoyl radical, for example its use in a therapeutic treatment method for stimulating the production of melanins to prevent and / or treat diseases of human skin.