Use of a merocyanin to photostabilize resveratrol and / or one of its derivatives

Abstract

Use of a merocyanin for photostabilizing resveratrol and / or one of its derivatives. The invention therefore relates to the use of (i) one or more merocyanins of the following formula (3) and their isomeric geometric forms E / E or E / Z, and their tautomers, salts, and solvates such as hydrates: [Formula 3] Formula 3 wherein: A is –O- or –NH; R is a C1-C22 alkyl group, a C2-C22 alkenyl group, a C2-C22 alcinyl group, a C3-C22 cycloalkyl group, or a C3-C22 cycloalkenyl group, said groups being able to be interrupted by one or more O groups, for (photo)stabilizing (ii) resveratrol, one of its derivatives, and their isomeric geometric forms, salts, and solvates such as hydrates or their mixtures.

Description

Title of the invention: Use of a merocyanin to photostabilize resveratrol and / or one of its derivatives

[0001] The invention relates to the use of (i) one or more merocyanin(s) of formula (3) as defined below for photo-stabilizing (ii) resveratrol, one of its derivatives as defined below or mixtures thereof.

[0002] The invention also relates to a composition, particularly a cosmetic one, comprising: (i) one or more merocyanins of formula (3) as defined below; (ii) resveratrol, one of its derivatives as defined below or mixtures thereof; (iii) one or more antioxidant(s) other than (ii).

[0003] The invention also relates to a method for treating keratinous materials, in particular facial and / or body skin, comprising applying said composition to said keratinous materials.

[0004] Trans-resveratrol and its derivatives are particularly interesting because they have good antioxidant and anti-inflammatory properties and can be used as an anti-aging active ingredient or depigmenting agent.

[0005] However, trans-resveratrol and its derivatives possess physicochemical properties that make them difficult to (photo)stabilize. This type of problem has been described in particular in patent application WO2014097260, which proposes solutions for the photo-stabilization of trans-resveratrol through the introduction of UVA-UVB filtering systems, especially at high concentrations.

[0006] It is therefore difficult to obtain cosmetic compositions which remain physico-chemically stable, and in which said resveratrol and / or one of its derivatives is (are) not degraded, in particular under the action of UV radiation.

[0007] Consequently, there remains a need to provide cosmetic compositions, comprising resveratrol or one of its (photostable) derivatives and which exhibit good sensory properties such as touch after application, little change in odor and / or color over time, and which allow the skin to benefit from correcting the signs of aging.

[0008] The present invention also aims at the development of cosmetic compositions conforming to the previous requirements, having satisfactory stability, in particular stability evaluated after 24 hours at 25°C, after 1 week and after two months of storage at 4°C, 25°C and 45°C.

[0009] We have found, surprisingly, that the use of merocyanins conforming to formula (3), particularly those described in the patent application WO2023110764, which exhibit very good filtration properties in long UVA radiation, allow the photo stabilization of resveratrol and its derivatives, and this with low levels of long UVA filters, in particular in quantity of merocyanins of formula (3) less than or equal to 3% by weight relative to the total weight of the composition.

[0010] The invention therefore relates to the use of (i) one or more merocyanin(s) of the following formula (3) as well as its isomeric geometric forms E / E or E / Z, their tautomers, their salts, and their solvates such as hydrates: [Chem 1] Formula 3 in which: A is -O- or -NH; R is a C1-C22 alkyl group, a C2-C22 alkenyl group, a C2-C22 alcinyl group, a C3-C22 cycloalkyl group or a C3-C22 cycloalkenyl group, said groups being able to be interrupted by one or more oxygen atoms, to (photo) stabilize (ii) resveratrol, one of its derivatives and their isomeric geometric forms, their salts and their solvates such as hydrates or mixtures thereof.

[0011] The present invention also relates to a composition, in particular a cosmetic one, comprising: (i) one or more merocyanin(s) of the following formula (3) as well as its isomeric geometric forms E / E or E / Z, their tautomers, their salts, and their solvates such as hydrates; [Chem 2] Formula 3 in which: A is -O- or -NH; R is an alkyl group C1-C22, an alkenyl group C2-C22, an alcinyl group C2-C22, a cycloalkyl group C3-C22 or a cycloalkenyl group C3-C22, said groups being able to be interrupted by one or more O groups, (ii) resveratrol, one of its derivatives, as well as their isomeric geometric forms and their solvates such as hydrates or mixtures thereof; (iii) one or more antioxidant agent(s) different from (ii).

[0012] The present invention also relates to a cosmetic treatment method, preferably non-therapeutic, for the care and / or makeup of a keratinous material comprising the application on the surface of said keratinous material of at least one composition according to the present invention.

[0013] A composition is considered to remain stable when its properties after storage, in particular two months at 4°C, 25°C and 45°C, remain close to those characterized at 24h at 25°C.

[0014] The composition according to the invention is in a particular mode intended for topical application, in particular on keratinous materials, especially the skin.

[0015] According to one embodiment, the composition of the invention is aqueous and comprises one or more surfactants, preferably selected from nonionic and / or anionic surfactants. In particular, the composition of the invention further comprises one or more fatty substances, preferably liquid at 20°C and atmospheric pressure. Advantageously, the composition according to the invention is in the form of an oil-in-water or water-in-oil emulsion, preferably oil-in-water.

[0016] The composition of the invention includes in particular a “cosmetically acceptable” medium also called a “physiologically acceptable” medium, that is to say a medium compatible with all keratinous materials, in particular the skin.

[0017] For the purposes of the present invention, "keratinous materials" means the skin and its appendages.

[0018] By “skin”, we mean human skin, in particular of the face and / or body, the scalp.

[0019] By “annexes” we mean human keratinous fibres, in particular eyelashes, eyebrows, nails, and hair, in particular eyelashes and hair.

[0020] In what follows, and unless otherwise indicated, the bounds of a range of values ​​are included in that range, in particular in the expressions "between" and "ranging from ... to ..."

[0021] By "alkyl" is meant a monovalent saturated hydrocarbon group of the type (Cx-Cy), linear or branched, comprising x to y carbon atoms, for example a C-C6 alkyl, implies an alkyl group, linear or branched, comprising from 1 to 6 carbon atoms. Preferably the alkyl group is a C1-C4 group such as methyl, ethyl, propyl, i-propyl, butyl, i-butyl, t-butyl.

[0022] By "alkenyl" is meant a monovalent unsaturated hydrocarbon group of the (Cx-Cy) type, linear or branched, comprising x carbon atoms and y atoms of carbon, comprising one or more unsaturations, conjugated or non-conjugated, preferably of 1 to 3 double bonds, for example a C2-C22 alkenyl, implies an alkenyl group, linear or branched, comprising from 2 to 22 carbon atoms, and comprising one or more unsaturations, preferably of 1 to 3 double bonds.

[0023] For the purposes of this invention, "fatty substance" means an organic compound that is not miscible in water at ordinary temperature (20 °C) and atmospheric pressure (760 mm Hg) (solubility less than 5%, and preferably 1%, even more preferably 0.1%); furthermore, fatty substances are miscible in particular in all proportions in organic solvents under the same conditions of temperature and pressure, such as halogenated solvents such as chloroform, dichloromethane, lower alcohols such as ethanol or aromatic solvents such as benzene or toluene.

[0024] By "organic or mineral acid salt" is meant more particularly salts selected from a salt derived from i) hydrochloric acid HCl, ii) hydrobromic acid HBr, iii) sulfuric acid H2SO4, iv) alkylsulfonic acids: Alk-S(O)2OH such as methylsulfonic acid and ethylsulfonic acid; v) arylsulfonic acids: Ar-S(O)2OH such as benzenesulfonic acid and toluenesulfonic acid; vi) succinic acid; vii) alkoxysulfinic acids: Alk-OS(O)OH such as methoxysulfinic acid and ethoxysulfinic acid; viii) aryloxysulfinic acids such as tolueneoxysulfinic acid and phenoxysulfinic acid; ix) phosphoric acid H3PO4; x) (poly)(hydroxy)(Ci-C6)alkylcarboxylic acid such as acetic acid CH3C(O)OH, citric acid, tartaric acid; lactic acid; xi) triflic acid CF3SO3H and xii) tetrafluoroboric acid HBF4;as well as so-called "acidic" amino acid salts such as glutamic acid salts and aspartic acid;

[0025] By "organic or mineral base salts" we mean the salts of bases or of alkali agents such as alkali metal hydroxides like soda, potash, ammonia, amines or alkanolamines or even the salts of so-called "basic" amino acids such as lysine or arginine.

[0026] Furthermore, the expression "at least one" used in this description is equivalent to the expression "one or more". USE

[0027] According to a first aspect, the present invention relates to the use of (i) one or more merocyanins as defined below to (photo) stabilize (ii) resveratrol, one of its derivatives or their mixture. (i) MEROCYANINS

[0028] According to the present invention, (i) a family of merocyanins corresponding to the following formula (3) will be used, as well as its isomeric geometric forms E / E- or E / Z- and their tautomers, salts and solvates such as hydrates:

[0029] [Chem.3] CK

[0030] Formula 3 wherein: A is -O- or -NH; R is a C1-C22 alkyl group, a C2-C22 alkenyl group, a C2-C22 alcinyl group, a C3-C22 cycloalkyl group or a C3-C22 cycloalkenyl group, said groups being able to be interrupted by one or more oxygen atoms O.

[0031] The merocyanine compounds of the invention can be in their isomeric geometric forms E / E, E / Z:

[0032] [Chem.4]

[0033] Preferably, one or more merocyanins corresponding to formula (3) as described above, as well as its isomeric geometric forms E / E- or E / Z-, their tautomers, their salts and their solvates such as hydrates, will be used, in which: A is -O-; R is an alkyl group, linear or branched, in Ci-C22, better R is an alkyl group in Ci-C6 which may be interrupted by one or more O's.

[0034] Among the compounds of formula (3), particular use will be made of those chosen from the following E / Z group, as well as their isomeric E / E geometric forms, and their tautomers, salts and solvates such as hydrates:

[0035] [Tables 1] ethyl(2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-e n-1 - y lidene} ethanoate 15 AC. S........ | HTTJ (2Z)-2-cyano-N-(3-methoxypropyl)-2-{3-[(3-methoxyprop yl)amino]cyclohex-2-en-l-ylidene}ethanamide 25 ...ov 2-ethoxyethyl(2Z)-cyano{3-[(3-methoxypropyl)amino]cycl ohex-2-en-1-ylidene} ethanoate 27 । 1 o ck 1 HT C_jr n 2-methylpropyl(2Z)-cyano{3-[(3-methoxypropyl)amino]cy clohex-2-en- 1-ylidene} ethanoate 29 A 0 1 H ] ° l J 2-butoxyethyl(2Z)-cyano{3-[(3-methoxypropyl)ammo]cycl ohex-2-en- 1-ylidene} ethanoate 31 1 Ô 0.. 3-methoxypropyl(2Z)-cyano{3-[(3-methoxypropyl)amino]c yclohex-2-en-1 -ylidene} ethanoate

[0036] According to a more particularly preferred embodiment of the invention, the compound 2-ethoxyethyl(2Z)-cyano{3-[(3-methoxypropyl)-amino]cyclohex-2-en-ly lidene]ethanoate (25) will be used in its E / E and / or E / Z geometric configuration as well as its tautomers.

[0037] The E / Z form has the following structure (formula 25):

[0038] [Chem.5]

[0039] The E / E form has the following structure (formula 25 bis):

[0040] [Chem.6]

[0041] The filtering merocyanins according to the invention may be present in the compositions according to the invention in an amount greater than or equal to 0.1% and less than or equal to 15% by weight, and preferably greater than or equal to 0.2% and less than or equal to 10% by weight and even better greater than or equal to 0.5% and less than or equal to 5% by weight, even better greater than or equal to 0.7% and less than or equal to 3% by weight relative to the total weight of the composition.

[0042] The compounds of formula (3), which form a carbocyclic ring containing 6 carbon atoms, can be prepared according to the protocols described in Pat. Appl. WO 2007 / 071582, in IP.com Journal (2009), 9(5A), 29-30 IPCOM000182396D under the heading “Process for producing 3-amino-2-cyclohexan-l-ylidene compounds” and in US-A-4,749,643 on col. 13, line 66 - col. 14, line 57 and the references cited therein.

[0043] In particular, compounds of formula (3), such as the compound 2-ethoxyethyl (2Z)-cyano{3-[(3-methoxypropyl)-amino]cyclohex-2-en-l-ylidene]ethanoate (25) can be synthesized according to the synthesis scheme described in the publication by B. Winkler et al., Tetrahedron Letters, 55 (2014) 1749-1751, entitled “A cyclic merocyanine UV-A absorber: mechanism of formation and crystal structure”, and shown below, for compounds of formula (3):

[0044] [Chem.7]

[0045] And more particularly for compound 25 described in Table 1:

[0046] [Chem. 8] (ii) Resveratrol

[0047] The composition according to the invention comprises resveratrol, one of its derivatives as well as their isomeric geometric forms, their salts and their solvates such as hydrates or their mixture.

[0048] Resveratrol is a polyphenol that exists in a cis (or Z) form and a trans (or E) form, represented below:

[0049] [Chem.9] frâfl^resvérato Œ-æSVÊfato

[0050] By "resveratrol derivative" is meant compounds whose skeleton is resveratrol as defined above, of which at least one of the three hydroxyl groups is salified and / or functionalized, in particular by a sugar, especially a glycosyl or glucoside. More particularly, the condensation product of glucose, in the D form, i.e., in the form of α- or β-glucopyranose or α- or β-furanose, or in the L form, with resveratrol, preferably in the L form

[0051] Resveratrol and its derivatives, in particular trans-resveratrol, are known to have many biological properties such as antioxidant and anti-inflammatory activity.

[0052] Resveratrol exists in nature in its cis and trans forms, but also in other derived forms such as a glucosylated form.

[0053] Resveratrol and its derivatives are present in many plants and fruits. They are found, in particular, in Japanese knotweed (Fallopia japonica, also known as Polygonum cupistadum or Reynoutria japonica) and in grapes, such as those from the grapevine species Vitis vinifera. More specifically, resveratrol and its derivatives are found, for example, in blackberries, wine, and peanuts.

[0054] Generally speaking, resveratrol and its derivatives are found in the following plant families: Vitaceae, Myrtaceae, Dipterocarpaceae, Cyperaceae, Gnetaceae, Fabaceae, Pinaceae, Polygonaceae, Moraceae, Fagaceae, Liliaceae, etc.

[0055] Examples of resveratrol derivatives include resveratrol triphosphate, alkali or alkaline earth salts, and in particular alkali salts such as sodium resveratrol triphosphate with the following formula, as well as its geometric isomers and solvates such as hydrates:

[0056] [Chem. 10]

[0057] We can also mention polydatin, which is a derivative of resveratrol, with the following formula, as well as its salts and solvates such as its hydrates:

[0058] [Chem. 11]

[0059] According to a preferred embodiment, the composition comprises resveratrol, its salts, resveratrol triphosphate, its salts, polydatin, its salts, and mixtures thereof, preferably selected from resveratrol, sodium resveratrol triphosphate, polydatin and mixtures thereof.

[0060] More preferably, the composition comprises resveratrol. Better still, the composition comprises resveratrol in its trans form.

[0061] Resveratrol, in particular trans-resveratrol or its derivatives, present in the composition according to the invention may be of synthetic origin, natural or may be in the form of a plant extract containing resveratrol, in particular trans-resveratrol.

[0062] Preferably, resveratrol, one of its derivative(s) as well as their isomeric geometric forms, their salts and their solvates such as hydrates or their mixture is / are present in the composition according to the invention in an amount greater than or equal to 0.001 and less than or equal to 10% by weight, more preferably greater than or equal to 0.01 and less than or equal to 5% by weight, better greater than or equal to 0.05 and less than or equal to 2% by weight, better still greater than or equal to 0.1% by weight and less than or equal to 1% by weight relative to the total weight of the composition. COMPOSITION

[0063] According to another aspect, the present invention relates to a composition comprising (i) one or more merocyanins as defined above, (ii) resveratrol, one of its derivatives or mixtures thereof as defined above, (iii) one or more antioxidant agent(s) different from (ii). (iii) Antioxidant agent(s)

[0064] The composition according to the invention comprises (iii) one or more antioxidant agent(s) different from (ii).

[0065] For the purposes of this invention, "antioxidant agent" means an agent that slows down or prevents the oxidation of other chemical substances in contact with it.

[0066] This antioxidant agent can be chosen from among the known antioxidant agents of art.

[0067] Preferably, said (iii) oxidizing agent is selected from vitamins, their salts and derivatives, ascorbic acid, its salts and derivatives, and mixtures thereof.

[0068] Ascorbic acid preferably corresponds to L-ascorbic acid, or vitamin C. It has the following structure (II):

[0069] [Chem. 12]

[0070] By "ascorbic acid derivative", preferably means a compound selected from 5,6-di-O-dimethylsilylascorbate (in particular sold by Exsymol under the reference PRO-AA®), potassium salt of DL-alpha-tocopheryl-DL-ascorbyl-phosphate also called Potassium Ascorbyl Tocopheryl Phosphate (sold by SEPPIC under the reference SEPIVITAL EPC®), magnesium ascorbyl phosphate, sodium ascorbyl phosphate (sold by DSM under the reference Stay-C 50®), disodium ascorbyl sulfate, sulfinyl-L-ascorbic acid, glucopyranosyl-L-ascorbic acid, ascorbyl palmitate, ascorbyl glucoside, erythorbic acid and ethyl ascorbic acid.

[0071] By "ascorbyl glucoside" is meant the condensation product of glucose, in D form, i.e. in the form of α- or β-3-glucopyranose or α- or β-3-furanose, or in L form, with ascorbic acid, preferably in L form. Preferably, Ascorbyl glucoside is L-ascorbic acid 2-OaD-glucopyranoside, notably available from the company HAYASHIBARA.

[0072] The term "ascorbic acid derivatives" within the meaning of the present invention may be understood to mean those obtained by blocking at least one hydroxyl site, in particular by esterification or etherification with, for example, phosphate compounds, sulfate compounds, esters of ascorbic acid and carboxylic acids, in particular (CrC22)alkylcarboxylic acid and (C2-C22)alkenylcarboxylic acid, or ethers from (C1-C22)alkanols, or (C2-C22)alkenols. These may include, in particular, ascorbyl magnesium phosphate, ascorbyl palmitate, and ascorbyl glucoside.

[0073] The salts of ascorbic acid or erythorbic acid may be chosen from alkali metal or alkaline earth metal salts, preferably alkali metal salts such as sodium or potassium salts

[0074] Examples include RECKON ORGANICS' Ascorbic acid L® (pure synthetic ascorbic acid) or DSM nutritional product's Ascorbic acid Ultrafine powder® (natural extract).

[0075] According to a preferred embodiment, the composition according to the invention comprises tocopherol, one of its derivatives, one of its salts, one of their optical isomers or mixtures thereof.

[0076] Tocopherol preferably corresponds to α-tocopherol, or vitamin E. Its structure is the following formula (IV):

[0077] [Chem. 13] (IV) (IV)

[0078] By "tocopherol derivative" is preferably tocopherol esters and ethers, preferably C1-C24 esters and ethers, preferably C2-C18 esters and ethers, particularly tocopherol esters and carboxylic acids, especially (C1-C22)alkylcarboxylic acid, (C2-C22)alkenylcarboxylic acid, (hetero)arylcarboxylic acid such as pyridinic carboxylic acids or ethers from (C1-C22)alkanols, or (C2-C22)alkenols such as tocopherol acetate, tocopherol palmitate, tocopherol linoleate, or tocopherol nicotinate.

[0079] One can cite, for example, the product DL Alpha Tocopheryl acetate® marketed by the company EISAI.

[0080] Preferably, the antioxidant agent is tocopherol, one of its derivatives, one of its salts, one of its optical isomers, more preferably the antioxidant agent is tocopherol.

[0081] Preferably, the amount of oxidizing agent (iii) other than (ii) in the composition is greater than or equal to 0.1% and less than or equal to 30% by weight, preferably greater than or equal to 0.5% and less than or equal to 25% by weight, more preferably greater than or equal to 0.7% and less than or equal to 20% by weight, relative to the total weight of the composition.

[0082] Advantageously, the composition comprises an amount greater than or equal to 0.01% and less than or equal to 20% by weight, preferably greater than or equal to 0.05% and less than or equal to 10% by weight, more preferably greater than or equal to 0.1% and less than or equal to 5% by weight, even more preferably greater than or equal to 0.5% and less than or equal to 2% by weight of tocopherol, relative to the total weight of the composition. Aqueous phase

[0083] A composition according to the invention may include an aqueous phase, and optionally an oily phase.

[0084] The aqueous phase comprises water and optionally a water-soluble organic solvent and is preferably monophasic.

[0085] According to a preferred embodiment, the composition according to the present invention comprises a water content of between 10% and 98% by weight, preferably between 25% and 90% by weight, and more preferably between 35% and 85%, relative to the total weight of the composition.

[0086] By "water-soluble organic solvent" according to the present invention, we mean a compound that is liquid at room temperature and miscible with water (miscibility in water greater than 50% by weight at 25 °C and atmospheric pressure).

[0087] The water-soluble solvents usable in the composition of the invention may also be volatile.

[0088] Among the water-soluble solvents that can be used in the composition according to the invention, particular mention may be made of lower monoalcohols having 1 to 5 carbon atoms such as ethanol and isopropanol, polyols and also alkylene carbonates.

[0089] According to one embodiment, the aqueous phase of a composition according to the invention may comprise at least one C2-C32 polyol.

[0090] Preferably, the composition according to the invention comprises from 0.01% to 30% by total weight of at least one polyol(s) relative to the total weight of the composition; more preferably, the composition comprises from 0.1% to 20% by weight, or even more preferably from 0.5% to 10% by weight of at least one polyol, even better from 0.7% to 5% by weight of at least one polyol relative to the total weight of the composition.

[0091] For the purposes of this invention, "polyol" means any organic molecule comprising at least two free hydroxyl groups (OH).

[0092] A polyol suitable for the invention may be an alkyl-type compound, with a linear, branched or cyclic hydrocarbon chain, saturated or unsaturated, bearing on the alkyl chain at least two -OH groups. Preferably, a polyol that can be used in the composition according to the invention is a linear alkyl-type compound bearing on the alkyl chain at least two -OH groups, preferably from 2 to 6 hydroxyl groups, more preferably 2 or 3 hydroxyl groups.

[0093] The polyol(s) advantageously suitable for the formulation of cosmetic compositions according to the present invention is / are those having in particular from 2 to 16 carbon atoms, preferably 3 to 10 carbon atoms, more preferably from 3 to 8 carbon atoms.

[0094] The polyol(s) that can be used according to the present invention is / are chosen from linear polyols having 3 to 8 carbon atoms, including, in particular: - diols, such as propylene glycol, butylene glycol, pentylene glycol; and - triols, such as glycerol (glycerin), and their mixtures.

[0095] According to a much preferred embodiment, the polyol is chosen from triols such as glycerin.

[0096] The aqueous phase may further include any water-soluble or water-dispersible compound compatible with an aqueous phase such as stabilizing agents, gelling agents, film-forming polymers, thickeners, surfactants and mixtures thereof. Fatty phase

[0097] As mentioned previously, a composition according to the invention may comprise at least one fatty phase.

[0098] For the purposes of the invention, "fat phase" means a phase comprising at least one oil and all the fat-soluble and lipophilic ingredients and fats, in particular liquid at 20 °C and atmospheric pressure, used for the formulation of the compositions of the invention.

[0099] In particular, a composition according to the invention may comprise varying from 5% to 95% by weight, preferably from 10% to 80% by weight of fat phase, relative to the total weight of the composition.

[0100] The oily phase of the composition according to the invention may comprise oils, waxes, pastes, and / or silicone compounds, and preferably at least one oil, in particular a cosmetic oil. Oils

[0101] By "oil" is meant a non-aqueous compound, immiscible with water, liquid at room temperature (20 °C) and atmospheric pressure (760 mm Hg).

[0102] A fatty phase suitable for the preparation of compositions, particularly cosmetics, according to the invention may comprise hydrocarbon, silicone, fluorinated or non-fluorinated oils, or mixtures thereof.

[0103] The oils may be volatile or non-volatile.

[0104] The oily phase may include, in addition to the merocyanin filter(s) and possibly additional lipophilic filters, at least one volatile or non-volatile hydrocarbon oil and / or a volatile and / or non-volatile silicone oil and / or a volatile and / or non-volatile fluorinated oil.

[0105] For the purposes of the present invention, "hydrocarbon oil" means an oil containing mainly hydrogen and carbon atoms.

[0106] The term “siliconized oil” means an oil comprising at least one silicon atom, and in particular at least one Si-O group.

[0107] The term “fluoridated oil” means an oil comprising at least one fluorine atom.

[0108] The oils may optionally include atoms of oxygen, nitrogen, sulfur and / or phosphorus, for example, in the form of hydroxyl or acid radicals. Volatile oils

[0109] For the purposes of this invention, "volatile oil" means any oil capable of evaporating upon contact with the skin in less than one hour, at room temperature and atmospheric pressure. The volatile oil is a volatile cosmetic compound, liquid at room temperature, having in particular a non-zero vapor pressure, at room temperature and atmospheric pressure, in particular having a vapor pressure ranging from 0.13 Pa to 40000 Pa (10-3 to 300 mm Hg), in particular ranging from 1.3 Pa to 13000 Pa (0.01 to 100 mm Hg), and more particularly ranging from 1.3 Pa to 1300 Pa (0.01 to 10 mm Hg).

[0110] Volatile oils can be hydrocarbon or silicone-based.

[0111] Among volatile hydrocarbon oils having 8 to 16 carbon atoms, we can mention in particular C8-C16 branched alkanes such as C8-C16 iso-alkanes (also called isoparaffins), isododecane, isodecane, isohexadecane and for example the oils sold under the trade names Isopars or Permetyls, C8-C16 branched esters such as isohexyl neopentanoate, and mixtures thereof.

[0112] One can also mention volatile linear alkanes comprising 8 to 16 carbon atoms, in particular 10 to 15 carbon atoms, and more particularly 11 to 13 carbon atoms, for example such as n-dodecane (C12) and n-tetradecane (Cl4) sold by Sasol respectively under the references Parafol 12-97 and Parafol 14-97, as well as their mixtures, the undecane-tridecane mixture, the mixtures of n-undecane (Cl1) and n-tridecane (Cl3) obtained in Examples 1 and 2 of application WO 2008 / 155059 of Société Cognis, and their mixtures.

[0113] Examples of volatile silicone oils include linear volatile silicone oils such as hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, tetradecamethylhexasiloxane, hexadecamethylheptasiloxane and dodecamethylpentasiloxane.

[0114] Examples of cyclic siliconized volatile oils include hexamethylcyclotrisiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, cyclohexasiloxane and dodecamethylcyclohexasiloxane, and in particular cyclohexasiloxane.

[0115] Fluorinated volatile oils, such as nonafluoromethoxybutane, decafluoropentane, tetradecafluorohexane, dodecafluoropentane and mixtures thereof, may also be used Non-volatile oils

[0116] By "non-volatile" is meant an oil whose vapor pressure at ambient temperature and atmospheric pressure is non-zero and less than 10-3 mm of Hg (0.13 Pa).

[0117] Non-volatile oils may, in particular, be chosen from hydrocarbon, fluorinated and / or non-volatile silicone oils.

[0118] Examples of non-volatile hydrocarbon oils include: - linear or branched hydrocarbons, of mineral or synthetic origin such as petroleum jelly, polydecenes, hydrogenated polyisobutene, such as paream, squalane, and mixtures thereof, - Non-volatile alkanes, preferably with a viscosity of less than 20 mPa.s at 20 °C measured with a Lamy Rheology Rhéomat RM 100® viscometer. "Non-volatile alkane" means a hydrocarbon cosmetic oil, liquid at room temperature, having in particular a vapor pressure at 20 °C of less than 0.01 kPa, according to the definition of a Volatile Organic Compound (VOC) in Article 2 of European Council Directive 1999 / 13 / EC of 11 March 1992: "Any organic compound having a vapor pressure of 0.01 kPa or more at a temperature of 293.15 K". In particular, non-volatile alkanes comprise from 10 to 30 carbon atoms, especially from 12 to 26 carbon atoms, and more particularly from 15 to 19 carbon atoms, and preferably a mixture of alkanes with 15 to 19 carbon atoms. carbon, for example the products marketed under the references Emogreen L19 and Emosmart L19 from Seppic, - hydrocarbon oils of vegetable origin, such as glyceride triesters which are generally triesters of fatty acids and glycerol whose fatty acids can have varying chain lengths from 4 to 24 carbon atoms, the latter being linear or branched, saturated or unsaturated; These oils include wheat germ oil, sunflower oil, grapeseed oil, sesame oil, corn oil, apricot kernel oil, castor oil, shea butter, avocado oil, olive oil, soybean oil, sweet almond oil, palm oil, rapeseed oil, cottonseed oil, hazelnut oil, macadamia oil, jojoba oil, alfalfa oil, poppy seed oil, pumpkin seed oil, sesame seed oil, squash oil, rapeseed oil, blackcurrant oil, evening primrose oil, millet oil, barley oil, quinoa oil, rye oil, safflower oil, candlenut oil, passionflower oil, rosehip oil; or caprylic / capric acid triglycerides such as those sold by Stéarineries Dubois or those sold under the names Miglyol 810, 812 and 818 by Dynamit Nobel. - Synthetic ethers having 10 to 40 carbon atoms, such as dicapryl ether; - Synthetic esters, such as oils with the formula RiCOOR2, in which RI represents a remnant of a linear or branched fatty acid containing 1 to 40 carbon atoms and R2 represents a hydrocarbon chain, particularly a branched one, containing 1 to 40 carbon atoms, provided that RI + R2 is greater than or equal to 10, such as Purcellin oil (cetostearyl octanoate), isopropyl myristate, isopropyl palmitate, alkyl benzoate having between 12 and 15 carbon atoms, such as the product sold under the trade name "Finsolv TN" or "Witconol TN" by the company Witco or "Tegosoft TN" by the company Evonik Goldschmidt, 2-ethylphenyl benzoate such as the product commercial product sold under the name "X-Tend 226" by the company ISP, isopropyl lanolate, hexyl laurate, diisopropyl adipate, isononyl isononanoate, oleyl erucate,2-Ethylhexyl palmitate, isostearyl isostearate, diisopropyl sebacate such as the product sold under the name "Dub Dis" by the company Stearinerie Dubois, octanoates, decanoates or ricinoleates of alcohols or polyalcohols such as propylene glycol dioctanoate; hydroxylated esters such as isostearyl lactate, di-isostearyl malate; and esters of pentaerythritol; citrates, such as the C3-C22 tricarboxylic acid and C1-C6 alcohol ester with the INCI name Tiethyl Citrate, for example that marketed under the name Citrofol AI Extra by the company Jungbunzlauer; tartrates such as linear dialkyl tartrates having 12 or 13 carbon atoms, for example those sold under the name Cosmacol ETI by the company Enichem Augusta Industriale, as well as linear dialkyl tartrates having between 14 and 15 carbon atoms, for example those sold under the name Cosmacol ETL by the same company, and acetates, , - fatty amides such as Isopropyl N-lauroyl sarcosinate, for example the product sold under the trade name "Eldew SL205" by Ajinomoto, - polyol esters and pentaerythritol esters, such as dipentaerythritol tetrahydroxystearate / tetraisostearate, - fatty alcohols that are liquid at room temperature with a branched and / or unsaturated carbon chain having 12 to 26 carbon atoms, such as octyldodecanol, isostearyl alcohol, oleic alcohol, 2-hexyldecanol, 2-butyloctanol, 2-undecylpentadecanol, - higher C12-C22 fatty acids, such as oleic acid, linoleic acid, linolenic acid, and mixtures thereof, - carbonates, such as dicaprylyl carbonate, for example the product sold under the name "Cetiol CC" by the company Cognis; - non-phenylated silicone oils, such as caprylyl methycone, and - phenylated silicone oils, such as phenyl trimethicones, phenyl dimethicones, phenyl trimethylsiloxy diphenylsiloxanes, diphenyl dimethicones, diphenyl methyldiphenyl trisiloxanes, and 2-phenylethyl trimethylsiloxysilicates, dimethicones or phenyltrimethicone with a viscosity of 100 cSt or less, trimethylpentaphenyltrisiloxane, and mixtures thereof; as well as mixtures of these different oils. Other fats

[0119] A fatty phase according to the invention may further comprise, mixed with or solubilized in an oil, other fatty substances.

[0120] Other fatty substances that may be present in the oily phase include, for example: - fatty acids with 8 to 30 carbon atoms, such as stearic acid, lauric acid, palmitic acid and oleic acid; - waxes, distinct from glyceryl trihydroxystearate, such as lanolin, beeswax, Camauba or Candelilla wax, paraffin waxes, lignite or microcrystalline waxes, ceresin or ozokerite, synthetic waxes such as polyethylene waxes, Fischer-Tropsch waxes; - silicone resins such as trifluoromethyl-Cl-C4-alkyldimethicone and trifluoropropyldimethicone; - silicone elastomers such as products marketed under the names "KSG" by the company Shin-Etsu, under the names "Trefil" or "BY29" by the company Dow Corning or under the names "Gransil" by the company Grant Industries; - a gum chosen from among the silicone gums (dimethiconol), - a pasty compound, such as polymeric or non-polymer silicone compounds, esters of an oligomeric glycerol, arachidyl propionate, fatty acid triglycerides and their derivatives, - and mixtures thereof.

[0121] As a fatty substance, a composition according to the invention may comprise at least one fatty alcohol wax. Such waxes may be selected from lauryl alcohol, myristic alcohol, cetyl alcohol, stearyl alcohol, arachidyl alcohol, behenyl alcohol, lignoceryl alcohol, ceryl alcohol, montanyyl alcohol, myricyl alcohol and mixtures thereof.

[0122] As a fat, a composition according to the invention may include in particular at least one butter, more particularly a vegetable butter.

[0123] The vegetable butter(s) suitable for the invention are preferably chosen from the group including avocado butter, cocoa butter, shea butter, kokum butter, mango butter, murumuru butter, coconut butter, apricot kernel butter, sal butter, annatto butter and mixtures thereof, and in particular is shea butter.

[0124] These fats can be chosen in a variety of ways by a person skilled in the art in order to prepare a composition having the desired properties, for example of consistency or texture.

[0125] According to a preferred embodiment, a composition according to the invention comprises at least one non-volatile oil, preferably at least one non-volatile hydrocarbon oil, in particular selected from linear or branched hydrocarbons of mineral or synthetic origin, non-volatile alkanes, hydrocarbon oils of vegetable origin, synthetic esters, fatty amides, carbonates, and mixtures of these different oils, even better selected from synthetic esters, fatty amides, carbonates and mixtures thereof.

[0126] According to a preferred embodiment, the composition according to the invention comprises a polar oil.

[0127] In particular, such non-volatile hydrocarbon oils may be present in a composition according to the invention in a content ranging from 2.0% to 20.0% by weight, preferably from 2.0% to 15.0% by weight, relative to the total weight of the composition.

[0128] According to a preferred embodiment, a composition according to the invention contains at least one oil selected from squalane, mixtures of alkanes of 15 to 19 carbon atoms, caprylic / capric acid triglycerides, alkyl benzoates having between 12 and 15 carbon atoms, diisopropyl adipate, 2-ethylhexyl palmitate, diisopropyl sebacate, C3-C22 tricarboxylic acid ester and C1-C6 alcohols with INCI name Tiethyl Citrate, Isopropyl N-lauroyl sarcosinate, dicaprylyl carbonate, and mixtures thereof, better still chosen from diisopropyl sebacate, isopropyl N-lauroyl sarcosinate, dicaprylyl carbonate.

[0129] Preferably, a composition according to the invention comprises less than 2.0% by weight of silicone oil(s), in particular less than 1.0% by weight of silicone oil(s), preferably less than 0.5% by weight of silicone oil(s), relative to the total weight of the composition, and more preferably is free of silicone oil(s).

[0130] Preferably, a composition according to the invention comprises a fatty phase containing at least one fatty substance.

[0131] According to a preferred embodiment, a composition according to the invention comprises at least one non-volatile hydrocarbon oil, and preferably at least one non-volatile ester oil. Hydrophilic Gelling / Thickening Agent

[0132] The composition according to the present invention may include at least one hydrophilic gelling (or thickening) agent, i.e. soluble or dispersible in water.

[0133] Examples of hydrophilic gelling agents include modified or unmodified carboxyvinyl polymers, such as the products marketed under the names Carbopol (CTFA name: carbomer) and Pemulen (CTFA name: Acrylates / C 10-30 akyl acrylate crosspolymer) by Goodrich, polyacrylamides, polymers and copolymers of 2-acrylamido 2-methylpropane sulfonic acid, possibly crosslinked and / or neutralized, such as poly(2-acrylamido 2-methylpropane sulfonic acid) marketed by Hoechst under the name "Hostacerin AMPS" (CTFA name: Ammonium Polyacryldimethyltauramide), crosslinked anionic copolymers of acrylamide and AMPS, in the form of a W / O emulsion,such as those marketed under the name Sepigel 305 (CTFA name: Polyacrylamide / C13-14 Isoparaffin / Laureth-7) and under the name Simulgel 600 (CTFA name: Acrylamide / Sodium acryloyldimethyltaurate copolymer / Isohexadecane / Polysorbate 80) by the company Seppic, polysaccharide biopolymers such as xanthan gum, guar gum, scleroglucan gum, alginates, modified celluloses, and mixtures thereof. The quantity of gelling agents depends on the desired purpose.

[0134] More preferably, the hydrophilic gelling agent is chosen from polysaccharide biopolymers such as scleroglucan gum.

[0135] According to one embodiment, the quantity of hydrophilic gelling agents ranges for example from 0.01 to 10% and for example from 0.05 to 5% by weight, relative to the total weight of the composition. Additional asset(s)

[0136] The composition may also include one or more active ingredients different from (ii) and (iii).

[0137] Examples of active ingredients include moisturizing agents; depigmenting agents, desquamating agents, anti-aging agents other than (ii) and (iii), mattifying agents; healing agents; preservatives such as antibacterial agents; UV filters, particularly lipophilic ones and mixtures thereof.

[0138] Preferably, the composition according to the invention comprises from 0.01% to 20% by total weight of at least one active ingredient, preferably from 0.05% to 15% by weight, and preferably from 0.1% to 10% by weight of at least one active ingredient relative to the total weight of the composition.

[0139] The compositions of the invention may contain one or more of the adjuvants commonly used in the cosmetic and dermatological fields; emollients; sequestrants; antioxidants; fillers; free radical scavengers; essential oils; perfumes; film-forming agents; colorants; and mixtures thereof. The total quantities of these various adjuvants are those conventionally used in the fields concerned. In particular, these quantities vary according to the desired purpose and may, for example, range from 0.01% to 20%, and preferably from 0.1% to 10% by weight of the total weight of the composition.

[0140] Of course, a person skilled in the art will take care to choose the possible adjuvant(s) added to the composition according to the invention such that the advantageous properties intrinsically attached to the composition according to the invention are not, or substantially not, altered by the envisaged addition.

[0141] The quantities of these different active ingredients are those classically used in the fields concerned. In particular, these quantities vary according to the intended purpose and can, for example, range from 0.01% to 20%, and preferably from 0.1% to 10% by weight of the total weight of the composition.

[0142] The composition according to the invention also relates to the cosmetic use of a composition according to the invention for the care of keratinous materials, in particular for the care of the skin of the body and / or face.

[0143] The present invention also relates to a process for treating keratinous materials, particularly human materials such as skin, in which a composition according to the invention is applied to said keratinous materials.

[0144] More particularly, the treatment process is a process for keratinous materials such as skin, in particular the skin of the body and / or face, said process is non-therapeutic, preferably for care, in which a composition according to the invention is applied to said keratinous materials.

[0145] The composition according to the invention can be obtained in a conventional manner by a person skilled in the art.

[0146] The following examples will help to better understand the invention, but are not intended to be limiting. Raw materials are named by their chemical or INCI name. Unless otherwise stated, quantities are given as a percentage by weight of raw materials relative to the total weight of the composition. Examples

[0147] Examples of synthesis of merocyanins of formula (3) Example Al: Preparation of compound (14)

[0149] 122.23 grams of 3-[(3-methoxypropyl)amino]-2-cyclohexen-l-one are alkylated with dimethyl sulfate or alternatively with diethyl sulfate and treated with 75.45 grams of ethyl cyanoacetate in approximately equimolar proportions in the presence of a base and optionally a solvent.

[0150] The base / solvent combinations indicated in the following table are used.

[0151] [Tables2] Example Base Solvent Example ALI DBU (1,8-diazabicyclo[5.4.0]undec-7-ene)dimethylacetamide Example A 1.2 Triethylamine isopropanol Example A 1.3 3-Methoxypropylamine isopropanol Example A 1.4 3-Methoxypropylamine tert-amyl alcohol Example A 1.5 3-Methoxypropylamine toluene Example A 1.6 3-Methoxypropylamine dimethylformamide Example A 1.7 Solvent-free 3-Methoxypropylamine Example A 1.8 N-Morpholine isopropanol

[0152] The completion of the alkylation reaction can be monitored, for example, by methods such as TLC, GC or HPLC.

[0153] 162.30 grams of compound (14) are obtained in the form of a brown oil.

[0154] After crystallization, the product is obtained in the form of yellowish crystals.

[0155] Melting point: 92.7 °C. Example A2: Preparation of compound (15)

[0156]

[0157] 101.00 grams of 3-[(3-methoxypropyl)amino]-2-cyclohexen-l-one are alkylated with dimethyl sulfate or alternatively with diethyl sulfate and treated with 86.00 grams of 2-cyano-N-(3-methoxy-propyl)-acetamide in approximately equimolar proportions in the presence of a base and optionally a solvent.

[0158]

[0159] The base / solvent combinations shown in the following table are used. [Tables 3] Example Solvent Base Example A2.1 DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) dimethylacetamide Example A2.2 Triethylamine isopropanol Example A2.3 3-Methoxypropylamine isopropanol Example A2.4 3-Methoxypropylamine tert-amyl alcohol Example A2.5 3-Methoxypropylamine toluene Example A2.6 3-Methoxypropylamine dimethylformamide Example A2.7 3-Methoxypropylamine solvent-free The crude product (15) is obtained in the form of a dark brown oil. After silica gel column chromatography (eluent: toluene / methanol)

[0160]

[0161]

[0162]

[0163]

[0164] 99 / 1), 81.8 grams of product are obtained in the form of yellowish crystals. Melting point: 84.7-85.3 °C. Example A3: Preparation of compound (27)

[0165]

[0166] 13.09 grams of 3-[(3-methoxypropyl)amino]-2-cyclohexen-l-one are alkylated with dimethyl sulfate or alternatively with diethyl sulfate and treated with 10.12 grams of isobutyl cyanoacetate in the presence of a base and optionally a solvent. The base / solvent combinations indicated in the following table are used. [Tables 4] Example Solvent Base Example A3.1 DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) dimethylacetamide Example A3.2 Triethylamine isopropanol Example A3.3 3-Methoxypropylamine isopropanol Example A3.4 N-Methylmorpholine tert-amyl alcohol Example A3.5 3-Methoxypropylamine toluene Example A3.6 3-Methoxypropylamine dimethylformamide Example A3.7 Solvent-free 3-Methoxypropylamine 15.97 grams of crude product (27) are obtained in the form of a dark brown oil. After silica gel column chromatography (eluent: toluene / acetone),

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173] 13.46 grams of product are obtained in the form of yellowish crystals. Melting point: 96.3 °C. Example A4: Preparation of compound (25) 148.4 grams of 3-[(3-methoxypropyl)amino]-2-cyclohexen-l-one are alkylated with dimethyl sulfate or alternatively with diethyl sulfate and treated with 130.00 grams of 2-ethoxyethyl cyanoacetate in the presence of an organic base and a solvent. The base / solvent combinations shown in the table below are used. [Tables5] Example Solvent Base Example A4.1 DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) dimethylacetamide Example A4.2 Triethylamine isopropanol Example A4.3 3-Methoxypropylamine isopropanol Example A4.4 N-Methylmorpholine tert-amyl alcohol Example A4.5 3-Methoxypropylamine toluene Example A4.6 3-Methoxypropylamine dimethylformamide Example A4.7 Solvent-free 3-Methoxypropylamine Compositions

[0174] Compositions A1, A2, B1 and B2 were prepared from the ingredients whose contents are indicated in the table below (% active ingredient):

[0175] In the following examples, all quantities are given as mass percentage of active material (AM) relative to the total weight of the composition (unless otherwise stated).

[0176] [Tableauxô] INCI Phase Al (inven tion) Bl(compar atif) A2 (invention ) B2 (comparati 0 SODIUM HYDROXIDE E QS pH 6 + / -0,3 QS pH 6 + / -0,3 QS pH 6 + / -0,3 QS pH 6 + / -0,3 TOCOPHEROL D 1,00 1,00 1,00 1,00 ASCORBIC ACID E 12,00 12,00 12,00 12.00 DICAPRYLYL CARBONATE B - - 4,00 4.00 CONSERVATEUR B - - 1 ,00 1.00 CONSERVATEUR A 0,70 0,70 - - FRAGRANCE D 0,20 0,20 - - WATER C QS100 QS100 QS100 QS100 DIISOPROPYL ADIPATE B 4,00 4,00 - - GLYCERIN A 5,00 5,00 5,00 5,00 SODIUM STEAROYL GLUTA MATE A 0,75 0,75 0,75 0,75 CONSERVATEUR B 0,30 0,30 0,20 0,20 SUCROSE TRISTEARATE B 2,00 2,00 2,00 2,00 POLYGLYCERYL-3 METHY LGLUCOSE DISTEARATE B 1,00 1,00 - - DIISOPROPYL SEBACATE B 3,00 3,00 3,00 3,00 ADENOSINE A 0,10 0,10 0,10 0,10 ISOPROPYL LAUROYL SAR COSINATE B 8,00 8,00 8,00 8,00 STEARYL ALCOHOL B 0,40 0,40 0,40 1,00 TRISODIUM ETHYLENEDIA MINE DISUCCINATE A 0,50 0,50 0,50 0,50 RESVERATROL B 0.25 0.25 0.25 0.25 PRESERVATIVE B 0.50 0.50 - - POLYMER B 1.00 1.00 - - METHOXYPROPYLAMINO CYCLOHEXENYLIDENE E THOXYETHYLCYANOACE TATE (compound 25) B 1.00 1.00 BIS-ETHYLHEXYLOXYPH NOL METHOXYPHENYL TR IAZINE B - - - 0.5 BUTYL METHOXYDIBENZO YLMETHANE B - - - 0.5 SCLEROTIUM GUM C 0.80 0.80 0.50 1.5 ACTIVE C 2.00 2.00 - - Manufacturing process

[0177] In a tank, heat phase A under agitation (emulsifier 1000 and blades 30 rpm) up to 75°C for 15 minutes.

[0178] Heat phase B to 75°C and introduce it into phase A under agitation (emulsifier 4000 rpm and blades 60 rpm) for 15 minutes.

[0179] Introduce phase C and mix for 10 minutes under vacuum (-0.5 bar).

[0180] Cool the mixture to 45°C and add phase D while stirring, then Mix for 5 minutes under vacuum (-0.5 bar).

[0181] Add phase E and mix for 5 minutes (vacuum -0.7 bar) then remove the emulsifier and leave the blades at 30 rpm under vacuum (-0.5 bar) for 5 minutes. Photostability measurement protocol

[0182] The compositions are analyzed to evaluate the photostability of resveratrol when the compositions are exposed to UV radiation.

[0183] Each of the compositions Al, A2, B1, and B2 was applied independently to an inert support (n=4 trials for each formula tested). The coated supports were exposed to UV radiation of 5 J / cm² for approximately 1 hour. The exposed compositions were then diluted in a solvent (organic solvent), and the solutions were analyzed by HPLC or UPLC chromatographic methods.

[0184] The amount of resveratrol in each of the compositions was measured by HPLC-UV assay at t1 and t2, as shown below: tl: After the preparation of the composition and putting it in the oven (serving as a reference); t2: After exposure of the compositions to UV radiation.

[0185] The details of the HPLC-UV tests are as follows:

[0186] Devices / reagents: [Paintings?] Ultra-high-performance LC (UPLC) system, RP18 HPLC column, 1.7, 2.1 mm x 100 mm. Eluent A: 0.1% phosphoric acid. Eluent B: Methanol.

[0187] Conditions: [Tables 8] UV detector 296 nm Column temperature 30°C Flow rate 0.4 mL / min Injection volume 1 pL Mobile phase Gradient A: 0.1% phosphoric acid in water B: Methanol

[0188] The amount of resveratrol contained in compositions Al, A2, B1 and B2 before (tl) and after exposure to UV radiation (t2) was determined by HPLC-UV and the ratio t2 / tl xlOO was calculated.

[0189] Results:

[0190] The quantities (%) of trans-resveratrol remaining after exposure to UV radiation of compositions Al, A2, B1 and B2 are given in the table below: [Tables 5] Composition Amount of trans-resveratrol remaining after exposure to UV radiation A1 (invention) 80% B1 (comparative) <10% A2 (invention) 78% B2 (comparative) 63%

[0191] The results obtained show that trans-resveratrol remains stable under exposure to UV radiation in composition Al according to the invention unlike composition B1 which does not include METHOXYPROPYLAMINO CYCLOHEXENYLIDENEETHOXYETHYLCYANOACETATE.

[0192] The photostability of resveratrol is significantly greater in the composition A2 according to the invention compared to composition B2 comprising a combination of UVA and UVB filters.

[0193] It follows that compositions A1 and A2 according to the invention allow significantly better photostability of resveratrol compared to compositions B1 and B2 not comprising METHOXYPROPYLAMINO CYCLOHEXENYLIDENEETHOXYETHYLCYANOACETATE. Formula stability

[0194] Stability measurement of Al and A2 compositions: The stability of the compositions is evaluated after storage of the formulas and under the following conditions: A mixture is prepared and then stored at different temperatures: i) at 4°C ii) ambient temperature The composition is then evaluated as follows: - at t = 24 hours, the macroscopic and microscopic appearance, the color and odor of the composition, and even the pH are characterized, - at t = 1 month, the macroscopic and microscopic appearance, the color and the odor of the composition.

[0195] The macroscopic appearance of the composition must remain identical or close to the initial appearance characterized at t = 24 hours. To be compliant, a composition must remain smooth, homogeneous and without any change in appearance, that is to say without release, without creaming, without phase separation and without any change in color or odor.

[0196] The Al and A2 compositions according to the invention are compliant after storage for 1 month at 4°C and room temperature from a microscopic and macroscopic point of view. Stability of Simplex A3 and B3 formulas

[0197] We made 2 simplex mixtures A3 and B3. A3 (invention) B3 (comparative) RESVERATROL 1.45 1.45 METHOXYPROPYLAMINO CYCLOHEXENYLIDENE ETHOXYE THYLCYANOACETATE 5.79 5.79 (compound 25) TOCOPHEROL 5.79 - ISOPROPYL LAUROYL SARCO SINATE QS100 QS100

[0198] After 1 week at 25°C, composition B3, which does not contain tocopherol, turns brown, unlike composition A3, which does contain tocopherol. It follows that tocopherol allows for the stabilization of the formula, and in particular its color.

Claims

1. Demands Use of (i) one or more merocyanin(s) of the following formula (3) and its isomeric geometric forms E / E or E / Z and their tautomers, salts and solvates such as hydrates:

2.

3. Formula 3 in which: A is -O- or -NH; R is an alkyl group CrC22, an alkenyl group C2-C22, an alcinyl group C2-C22, a cycloalkyl group C3-C22 or a cycloalkenyl group C3-C22, said groups being able to be interrupted by one or more O's, to (photo) stabilize (ii) resveratrol, one of its derivatives and their isomeric geometric forms, their salts and their solvates such as hydrates or mixtures thereof. Use according to claim 1 wherein (i) the merocyanin(s) of formula (3) and its isomeric geometric forms E / E or E / Z and their tautomers is / are selected from compounds of formula (3) and their isomeric geometric forms, their tautomers, their salts and their solvates such as hydrates wherein: A is -O- ; R is a Ci-C22 alkyl, better R is a Ci-C6 alkyl that can be interrupted by one or more O's. Use according to any one of the preceding claims, wherein (i) the merocyanin(s) of formula (3) is / are selected from the following compounds, as well as their isomeric E / E geometric forms, and their tautomers, salts and solvates such as hydrates: 14 ethyl (2Z)-cyano{ 3-[(3-methoxypropyl)amino]cycloh ex-2-en-1 -ylidene} ethanoate 15 (2Z)-2-cyano-N-(3-methoxypropyl)-2-{3-[(3-methox ypropyl)amino] cyclohex-2-en-1 -ylidene} ethanamide 25 2-ethoxyethyl (2Z)-cyano{3-[(3-methoxypropyl)amin o] cyclohex-2-en-1 -ylidene} ethanoate 27 1 1 O 1 H T 2-methylpropyl (2Z)-cyano{ 3-[(3-methoxypropyl)am ino]cyclohex-2-en-1 -ylidene}ethanoate 29 A 0-, . .. 1 h i ° T T 2-butoxyethyl (2Z)-cyano{3-[(3-methoxypropyl)amin o] cyclohex-2-en-1 -ylidene} ethanoate 31 A o.. Ah ] [ J 3-methoxypropyl (2Z)-cyano{ 3-[(3-methoxypropyl)a mino] cyclohex-2-en-1 -ylidene} ethanoate 37 1 H ] 1 1 T J 3-ethoxypropyl (2Z)-cyano{ 3-[(3-methoxypropyl)am ino]cyclohex-2-en-1 -ylidene}ethanoate

4. Use according to any one of the preceding claims, wherein (i) the merocyanine of formula (3) is 2-ethoxyethyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-l-ylidene}ethanoate (25) in its E / Z geometric configuration of the following structure and their tautomers: [Formula 25]HTrT and / or in its E / E geometric configuration of the following structure: [Formula 25bis]Ni11r

5. H i J ! Use according to any one of the preceding claims wherein (ii) resveratrol, one of its derivatives and their isomeric geometric forms, their salts and their solvates such as hydrates is (are) selected from resveratrol, its salts, resveratrol triphosphate, its salts, polydatin, its salts, and mixtures thereof, preferably selected from resveratrol, sodium resveratrol triphosphate, polydatin and mixtures thereof.

6. Use according to any one of the preceding claims wherein (ii) resveratrol, one of its derivatives and their isomeric geometric forms, their salts and their solvates such as hydrates, is resveratrol, preferably in its trans form.

7. Composition, in particular cosmetic, comprising: (i) one or more merocyanins of formula (3) as defined in any one of claims 1 to 4; (ii) resveratrol, one of its derivatives or mixtures thereof as defined in any one of claims 5 to 6; (iii) one or more antioxidant agent(s) other than (ii).

8. Composition according to the preceding claim wherein (i) the merocyanin(s) of formula (3) and its isomeric geometric forms E / E or E / Z and their tautomers, their salts and their solvates such as hydrates are present in an amount greater than or equal to 0.1% and less than or equal to 15% by weight, and preferably greater than or equal to 0.2% and less than or equal to 10% by weight and even better greater than or equal to 0.5% and less than or equal to 5% by weight better still greater than or equal to 0.7% and less than or equal to 3% by weight relative to the total weight of the composition.

9. Composition according to any one of claims 7 to 8 wherein resveratrol, one of its derivative(s) and their isomeric geometric forms, their salts and their solvates such as hydrates or mixtures thereof is (are) present in an amount greater than or equal to 0.001 and less than or equal to 10% by weight, more preferably greater than or equal to 0.01 and less than or equal to 5% by weight, better greater than or equal to 0.05 and less than or equal to 2% by weight, better still greater than or equal to 0.1% by weight and less than or equal to 1% by weight relative to the total weight of the composition.

10. Composition according to any one of claims 7 to 9 wherein (iii) the antioxidant agent(s) other than (ii) is / are selected from vitamins, their salts and derivatives, ascorbic acid, its salts and derivatives, more preferably selected from tocopherol, one of its derivatives, one of its salts, one of its optical isomers such that (iii) the antioxidant agent is tocopherol.

11. Composition according to any one of claims 7 to 10 wherein the amount of oxidizing agent (iii) other than (ii) is greater than or equal to 0.1% and less than or equal to 30% by weight, preferably greater than or equal to 0.5% and less than or equal to 25% by weight, more preferably greater than or equal to 0.7% and less than or equal to 20% by weight, relative to the total weight of the composition.

12. A composition according to any one of claims 7 to 11 comprising one or more oil(s), preferably a non-volatile oil, more preferably selected from non-volatile hydrocarbon oils, in particular selected from linear or branched hydrocarbons, of mineral or synthetic origin, non-volatile alkanes, vegetable hydrocarbon oils, synthetic esters, fatty amides, carbonates, and mixtures thereof better chosen from synthetic esters, fatty amides, carbonates and their mixture, such as diisopropyl sebacate, isopropyl N-lauroyl sarcosinate, dicaprylyl carbonate.

13. Composition according to any one of claims 7 to 12 comprising one or more hydrophilic gelling agents, more preferably selected from modified or unmodified carboxyvinyl polymers, polyacrylamides, 2-acrylamido-2-methylpropane sulfonic acid polymers and copolymers, optionally crosslinked and / or neutralized, such as poly(2-acrylamido-2-methylpropane sulfonic acid), crosslinked anionic copolymers of acrylamide and AMPS, polysaccharide biopolymers such as xanthan gum, guar gum, scleroglucan gum, alginates, modified celluloses, and mixtures thereof, preferably the hydrophilic gelling agent being selected from polysaccharide biopolymers such as scleroglucan gum.

14. Composition according to any one of claims 7 to 13 characterized in that it is in the form of an oil-in-water or water-in-oil emulsion, preferably oil-in-water.

15. Cosmetic method for the care and / or makeup of a keratinous material comprising the application on the surface of said keratinous material of at least one composition as defined in any one of claims 7 to 14.