Use of a merocyanine to photostabilize resveratrol and / or a derivative thereof

Abstract

The invention therefore relates to the use of (i) one or more merocyanine(s) of formula (3) below and also the E / E or E / Z geometric isomer forms thereof, and the tautomers thereof, the salts thereof, and the solvates thereof such as hydrates, in which formula (3): A is -O- or -NH; R is a C1-C22 alkyl group, a C2-C22 alkenyl group, a C2-C22 alkynyl group, a C3-C22 cycloalkyl group or a C3-C22 cycloalkenyl group, it being possible for said groups to be interrupted by one or more O; for (photo)stabilizing (ii) resveratrol, a derivative thereof and also the geometric isomer forms thereof, the salts thereof and the solvates thereof such as hydrates, or mixtures thereof.

Description

Use of a merocyanine to photostabilize resveratrol and / or a derivative thereof

[0001] The invention relates to the use of (i) one or more merocyanine(s) of formula (3) as defined below for photostabilizing (ii) resveratrol, a derivative thereof as defined below or mixtures thereof.

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

[0003] The invention also relates to a process for treating keratin materials, in particular facial and / or bodily skin, comprising the application of said composition to said keratin materials.

[0004] Trans-resveratrol and derivatives thereof are particularly advantageous because they have good antioxidant and anti-inflammatory properties and can be used as anti-ageing active agent or depigmenting agent.

[0005] However, trans-resveratrol and derivatives thereof possess physicochemical properties making them difficult to (photo)stabilize. This type of problem has been described in particular in patent application WO2014097260 which proposes solutions for photostabilization of trans-resveratrol by introducing UVA-UVB screening systems, and in particular at high contents.

[0006] It is therefore difficult to obtain cosmetic compositions which remain physicochemically stable, and in which said resveratrol and / or a derivative thereof is (are) not degraded, in particular under the action of UV radiation.

[0007] Consequently, there remains the need to provide cosmetic compositions, comprising resveratrol or a derivative thereof which is photo(stable), which compositions have good sensory properties, such as the feel after application or little change in odour and / or colour over time, and make it possible to give the skin benefits in terms of correcting the signs of ageing.

[0008] An aim of the present invention is also the development of cosmetic compositions in accordance with the preceding requirements, which have satisfactory stability, in particular stability evaluated after 24 h 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 merocyanines corresponding to formula (3), in particular described in patent application WO2023110764, and which have very good screening properties in long UVA radiation, allow the photostabilization of resveratrol and derivatives thereof, this being with low contents of long UVA screening agents, in particular in an amount of merocyanines of formula (3) of 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 merocyanine(s) of formula (3) below and also the E / E or E / Z geometric isomer forms thereof, the tautomers thereof, the salts thereof, and the solvates thereof such as hydrates:[Chem 1] in which formula (3):A is -O- or -NH;R is a C1-C22alkyl group, a C2-C22alkenyl group, a C2-C22alkynyl group, a C3-C22cycloalkyl group or a C3-C22cycloalkenyl group, it being possible for said groups to be interrupted by one or more oxygen atoms;for (photo)stabilizing (ii) resveratrol, a derivative thereof and also the geometric isomer forms thereof, the salts thereof and the solvates thereof such as hydrates, or mixtures thereof.

[0011] The present invention also relates to a composition, notably a cosmetic composition, comprising:(i) one or more merocyanine(s) of formula (3) below and also the E / E or E / Z geometric isomer forms thereof, the tautomers thereof, the salts thereof, and the solvates thereof such as hydrates;[Chem 2] in which formula (3):A is -O- or -NH;R is a C1-C22alkyl group, a C2-C22alkenyl group, a C2-C22alkynyl group, a C3-C22cycloalkyl group or a C3-C22cycloalkenyl group, it being possible for said groups to be interrupted by one or more O;(ii) resveratrol, a derivative thereof and also the geometric isomer forms thereof and the solvates thereof such as hydrates, or mixtures thereof;(iii) one or more antioxidant(s) other than (ii).

[0012] The present invention also relates to a cosmetic, preferably non-therapeutic, process for caring for and / or making up a keratin material, comprising the application, to the surface of said keratin material, of at least one composition in accordance with 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 24 h at 25°C.

[0014] In a particular embodiment, the composition according to the invention is intended for topical application, notably to keratin materials, in particular the skin.

[0015] According to one embodiment, the composition of the invention is aqueous and comprises one or more surfactants, preferably chosen from non-ionic and / or anionic surfactants. Particularly, the composition of the invention also comprises one or more fatty substances which are preferably liquid at 20°C and at atmospheric pressure. Advantageously, the composition according to the invention is in the form of an oil-in-water or water-in-oil emulsion, preferably an oil-in-water emulsion.

[0016] The composition of the invention comprises in particular a “cosmetically acceptable” medium, also known as a “physiologically acceptable” medium, i.e. a medium that is compatible with all keratin materials, in particular the skin.

[0017] For the purposes of the present invention, the term “keratin materials” means the skin and its integuments.

[0018] The term “skin” means human skin, notably of the face and / or body, or the scalp.

[0019] The term “integuments” means human keratin fibres, notably the eyelashes, the eyebrows, the nails and the hair, in particular the eyelashes and the hair.

[0020] In that which follows and unless otherwise indicated, the limits of a range of values are included within that range, notably in the expressions “between...” and “ranging from ... to ...”.

[0021] The term "alkyl" is understood to mean a monovalent saturated hydrocarbon group of the linear or branched (Cx-Cy) type, comprising x carbon atoms and y carbon atoms, for example, a C1-C6alkyl implies a linear or branched alkyl group comprising from 1 to 6 carbon atoms. Preferably, the alkyl group is a C1-C4group such as methyl, ethyl, propyl, i-propyl, butyl, i-butyl or t-butyl.

[0022] The term "alkenyl" is understood to mean a monovalent unsaturated hydrocarbon group of the linear or branched (Cx-Cy) type, comprising x carbon atoms and y carbon atoms, comprising one or more conjugated or non-conjugated unsaturations, preferably from 1 to 3 double bonds, for example a C2-C22alkenyl implies a linear or branched alkenyl group comprising from 2 to 22 carbon atoms and comprising one or more unsaturations, preferably from 1 to 3 double bonds.

[0023] For the purposes of the present invention, the term “fatty substance” means an organic compound that is immiscible in water at ordinary temperature (20°C) and at atmospheric pressure (760 mmHg) (solubility of less than 5%, preferably less than 1% and even more preferentially less than 0.1%); in addition, the fatty substances are miscible in particular in all proportions in organic solvents under the same temperature and pressure conditions, for instance in halogenated solvents such as chloroform or dichloromethane, lower alcohols such as ethanol or aromatic solvents such as benzene or toluene.

[0024] The term “organic or mineral acid salt” more particularly means salts chosen from a salt derived from i) hydrochloric acid HCl, ii) from hydrobromic acid HBr, iii) from sulfuric acid H2SO4, iv) from 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) from succinic acid; vii) from alkoxysulfinic acids: Alk-O-S(O)OH, such as methoxysulfinic acid and ethoxysulfinic acid; viii) from aryloxysulfinic acids, such as tolueneoxysulfinic acid and phenoxysulfinic acid; ix) from phosphoric acid H3PO4; x) from (poly)(hydroxy)(C1-C6)alkylcarboxylic acid, such as acetic acid CH3C(O)OH, citric acid, tartaric acid; lactic acid; xi) from triflic acid CF3SO3H and xii) from tetrafluoroboric acid HBF4; and also salts of “acidic” amino acids such as glutamic acid and aspartic acid salts;

[0025] The term “organic or mineral base salts” means salts of bases or alkaline agents, such as alkali metal hydroxides, such as sodium hydroxide or potassium hydroxide, aqueous ammonia, amines or alkanolamines, or else salts of “basic” amino acids such as lysine or arginine.

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

[0027] According to a first aspect, a subject of the present invention is the use of (i) one or more merocyanines as defined below for (photo)stabilizing (ii) resveratrol, a derivative thereof, or a mixture thereof.(i) MEROCYANINES

[0028] According to the present invention, use will be made of (i) a family of merocyanines corresponding to formula (3) below and also the E / E- or E / Z- geometric isomer forms thereof, the tautomers thereof, the salts thereof, and the solvates thereof such as hydrates:

[0029]

[0030] in which formula (3):

[0031] A is -O- or -NH;

[0032] R is a C1-C22alkyl group, a C2-C22alkenyl group, a C2-C22alkynyl group, a C3-C22cycloalkyl group or a C3-C22cycloalkenyl group, it being possible for said groups to be interrupted by one or more oxygen atoms O.

[0033] The merocyanine compounds of the invention may be in the E / E or E / Z geometric isomer forms thereof:

[0034]

[0035] Preferably, use will be made of one or more merocyanines corresponding to formula (3) as described above and also the E / E- or E / Z- geometric isomer forms thereof, the tautomers thereof, the salts thereof, and the solvates thereof such as hydrates, in which:

[0036] A is -O-; R is a linear or branched C1-C22alkyl group, better still R is a C1-C6alkyl group which may be interrupted by one or more O.

[0037] Among the compounds of formula (3), use will more particularly be made of those chosen from the following E / Z group and also the E / E geometric isomer forms thereof, and the tautomers thereof, the salts thereof and the solvates thereof such as hydrates:

[0038] 14 ethyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-1-ylidene}ethanoate15 (2Z)-2-cyano-N-(3-methoxypropyl)-2-{3-[(3-methoxypropyl)amino]cyclohex-2-en-1-ylidene}ethanamide25 2-ethoxyethyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-1-ylidene}ethanoate27 2-methylpropyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-1-ylidene}ethanoate29 2-butoxyethyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-1-ylidene}ethanoate31 3-methoxypropyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-1-ylidene}ethanoate37 3-ethoxypropyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-1-ylidene}ethanoate

[0039] According to one more particularly preferred mode of the invention, use will be made of the compound 2-ethoxyethyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-1-ylidene}ethanoate (25) in its E / E and / or E / Z geometric configuration, and also the tautomers thereof.

[0040] The E / Z form has the following structure (formula 25):

[0041]

[0042] The E / E form has the following structure (formula 25a):

[0043]

[0044] The screening merocyanines in accordance with the invention may be present in the compositions according to the invention in an amount of greater than or equal to 0.1% and less than or equal to 15% by weight, and preferentially greater than or equal to 0.2% and less than or equal to 10% by weight and even better still greater than or equal to 0.5% and less than or equal to 5% by weight, even 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.

[0045] The compounds of formula (3), which form a carbocyclic ring containing 6 carbon atoms, may be prepared according to the protocols described in patent application WO 2007 / 071582, in IP.com Journal (2009), 9(5A), 29-30 IPCOM000182396D under the title “Process for producing 3-amino-2-cyclohexan-1-ylidene compounds” and in US-A-4,749,643 on col. 13, line 66 – col. 14, line 57, and the references cited in this regard.

[0046] In particular, the compounds of formula (3), such as the compound 2-ethoxyethyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-1-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, which is entitled “A cyclic merocyanine UV-A absorber: mechanism of formation and crystal structure”, and represented below, for the compounds of formula (3):

[0047]

[0048] and more particularly for compound 25 described in Table 1:

[0049] (ii) Resveratrol

[0050] The composition in accordance with the invention comprises resveratrol, a derivative thereof and also the geometric isomer forms thereof, the salts thereof and the solvates thereof such as hydrates, or a mixture thereof.

[0051] Resveratrol is a polyphenol that exists in acis(or Z) form and atrans(or E) form, represented below:

[0052] .

[0053] The term "resveratrol derivative" is understood to mean compounds of which the backbone is resveratrol as defined above, at least one of the 3 hydroxyl groups of which is salified and / or functionalized in particular by a sugar, in particular glycosyl or glucoside. More particularly, the product of condensation of glucose, in D form, i.e. in the form of α- or β-glucopyranose or of α- or β-furanose, or in L form, with resveratrol, preferably in L form.

[0054] Resveratrol and derivatives thereof, in particulartrans-resveratrol, are known to have many biological properties, such as antioxidant and anti-inflammatory activity.

[0055] Resveratrol exists in the natural state in its cis and trans form, but also in other derived forms, for instance a glucosylated form.

[0056] Resveratrol and derivatives thereof are present in many plants and fruits. It is found in particular in Japanese knotweed (Fallopia japonica also known as Polygonum cuspidatum or else Reynoutria japonica) or in grapes, for instance those from the grapevine species Vitis vinifera. More particularly, resveratrol and derivatives are found, for example, in blackberries, wine or peanuts.

[0057] Generally, resveratrol and derivatives thereof are found in the following plant families: Vitaceae, Myrtaceae, Dipterocarpaceae, Cyperaceae, Gnetaceae, Fabaceae, Pinaceae, Polygonaceae, Moraceae, Fagaceae, Liliaceae, etc.

[0058] Examples of resveratrol derivatives include resveratrol triphosphate of alkali metal or alkaline-earth metal salts and especially alkali metal salts, such as sodium resveratrol triphosphate having the following formula, and also the geometric isomers thereof and the solvates thereof such as hydrates:

[0059] .

[0060] Mention may also be made of polydatin, which is a resveratrol derivative, of the following formula, and also the salts thereof and the solvates thereof such as the hydrates thereof:

[0061] .

[0062] According to a preferred embodiment, the composition comprises resveratrol, the salts thereof, resveratrol triphosphate, the salts thereof, polydatin, the salts thereof, and mixtures thereof, preferably chosen from resveratrol, sodium resveratrol triphosphate and polydatin and mixtures thereof.

[0063] More preferentially, the composition comprises resveratrol. Better still, the composition comprises resveratrol in its trans form.

[0064] The resveratrol, in particular trans-resveratrol or derivatives thereof, present in the composition according to the invention may be of synthetic or natural origin or may be in the form of a plant extract containing resveratrol, in particular trans-resveratrol.

[0065] Preferably, the resveratrol, a derivative thereof and also the geometric isomer forms thereof, the salts thereof and the solvates thereof such as hydrates, or a mixture thereof, 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 preferentially greater than or equal to 0.01% and less than or equal to 5% by weight, better still greater than or equal to 0.05% and less than or equal to 2% by weight, even 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

[0066] According to another aspect, the present invention relates to a composition comprising (i) one or more merocyanines as defined above, (ii) resveratrol, a derivative thereof or mixtures thereof as defined above, (iii) one or more antioxidant(s) other than (ii).(iii) Antioxidant(s)

[0067] The composition according to the invention comprises (iii) one or more antioxidant(s) other than (ii).

[0068] For the purposes of the present invention, “antioxidant” is understood to mean an agent that slows or prevents the oxidation of other chemical substances coming into contact with it.

[0069] This antioxidant may be chosen from antioxidants known in the art.

[0070] Preferably, said oxidizing agent (iii) is chosen from vitamins, salts thereof and derivatives thereof, ascorbic acid, salts thereof and derivatives thereof, and mixtures thereof.

[0071] The ascorbic acid preferably corresponds to L-ascorbic acid, or vitamin C. It has the structure of formula (II) below:

[0072]

[0073] The expression "ascorbic acid derivative" is preferably understood to mean a compound chosen from 5,6-di-O-dimethylsilyl ascorbate (sold in particular by Exsymol under the reference PRO-AA®), the potassium salt of DL-alpha-tocopheryl-DL-ascorbyl phosphate also known as potassium ascorbyl tocopheryl phosphate (sold by SEPPIC under the reference Sepivital EPC®), magnesium ascorbyl phosphate, sodium ascorbyl phosphate (sold by the company 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 ethylated ascorbic acid.

[0074] The term"ascorbyl glucoside" is understood to mean the condensation product of glucose, in the D form, that is to say in the form of α- or β-glucopyranose or of α- or β-furanose, or in the L form, with ascorbic acid, preferably in the L form. Preferably, the ascorbyl glucoside is L-ascorbic acid 2-O-α-D-glucopyranoside, available in particular from the company Hayashibara.

[0075] For the purposes of the present invention, the expression "ascorbic acid derivatives" may be understood to mean those obtained by blocking at least one hydroxyl site, in particular by esterification or etherification with, for example, compounds that are phosphated or sulfated, esters of ascorbic acid and of carboxylic acids, in particular of (C1-C22)alkylcarboxylic and (C2-C22)alkenyl carboxylic acid, or that are ethereal from (C1-C22)alkanols, or (C2-C22)alkenols. These may notably be magnesium ascorbyl phosphate, ascorbyl palmitate and ascorbyl glucoside.

[0076] 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.

[0077] Mention may for example be made of the product Ascorbic acid L® from Reckon Organics (pure synthetic ascorbic acid) or Ascorbic acid ultrafine powder® from DSM Nutritional Products (natural extract).

[0078] According to a preferred embodiment, the composition according to the invention comprises tocopherol, a derivative thereof, a salt thereof, an optical isomer thereof, or mixtures thereof.

[0079] The tocopherol preferably corresponds to α-tocopherol, or vitamin E. It has the structure of formula (IV) below:

[0080] (IV)

[0081] The term "tocopherol derivative" is preferably understood to mean tocopherol esters and ethers, preferably C1-C24, preferably C2-C18, esters and ethers, particularly esters of tocopherol and of carboxylic acids, in particular of (C1-C22)alkylcarboxylic acid, of (C2-C22)alkenylcarboxylic acid, of (hetero)arylcarboxylic acid such as pyridine carboxylic acids or that are ethereal from (C1-C22)alkanols, or (C2-C22)alkenols such as tocopheryl acetate, tocopheryl palmitate, tocopheryl linoleate, or tocopheryl nicotinate.

[0082] Mention may be made, for example, of the product DL Alpha tocopheryl acetate® sold by the company Eisai.

[0083] Preferably, the antioxidant is tocopherol, a derivative thereof, a salt thereof, an optical isomer thereof; more preferentially, the antioxidant is tocopherol.

[0084] 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 preferentially greater than or equal to 0.7% and less than or equal to 20% by weight, relative to the total weight of the composition.

[0085] Advantageously, the composition comprises an amount of 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 preferentially greater than or equal to 0.1% and less than or equal to 5% by weight, even more preferentially 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

[0086] A composition according to the invention may comprise an aqueous phase and optionally an oily phase.

[0087] The aqueous phase comprises water and optionally a water-soluble organic solvent and is preferably single-phase.

[0088] According to a preferred embodiment, the composition according to the present invention has a water content of between 10% and 98% by weight and preferably between 25% and 90% by weight, and more preferentially between 35% and 85%, relative to the total weight of the composition.

[0089] According to the present invention, the term “water-soluble organic solvent” denotes a compound that is liquid at ambient temperature and water-miscible (miscibility with water of greater than 50% by weight at 25°C and atmospheric pressure).

[0090] The water-soluble solvents that may be used in the composition of the invention may also be volatile.

[0091] Among the water-soluble solvents that can be used in the composition according to the invention, mention may be made most particularly of lower monoalcohols containing from 1 to 5 carbon atoms, such as ethanol and isopropanol, polyols and also alkylene carbonates.

[0092] According to an embodiment variant, the aqueous phase of a composition according to the invention may comprise at least one C2-C32polyol.

[0093] Preferably, the composition according to the invention comprises from 0.01% to 30% by total weight of at least one polyol relative to the total weight of the composition; more preferentially, the composition comprises from 0.1% to 20% by weight, even more preferentially from 0.5% to 10% by weight of at least one polyol, even better still from 0.7% to 5% by weight of at least one polyol, relative to the total weight of the composition.

[0094] For the purposes of the present invention, the term “polyol” means any organic molecule including at least two free hydroxyl (OH) groups.

[0095] A polyol that is suitable for use in the invention may be a compound of alkyl type with a linear, branched or cyclic, saturated or unsaturated hydrocarbon chain, bearing at least two -OH functions on the alkyl chain. Preferably, a polyol that may be used in the composition according to the invention is a compound of the linear alkyl type bearing on the alkyl chain at least two -OH functions, preferably from 2 to 6 hydroxyl -OH groups, more preferentially 2 or 3 hydroxyl groups.

[0096] The polyol(s) that are advantageously suitable for the formulation of the cosmetic compositions according to the present invention are those notably containing from 2 to 16 carbon atoms, preferably from 3 to 10 carbon atoms and more preferentially from 3 to 8 carbon atoms.

[0097] The polyol(s) that may be used according to the present invention are chosen from linear polyols containing from 3 to 8 carbon atoms; mention may notably be made of:

[0098] - diols, such as propylene glycol, butylene glycol, pentylene glycol; and

[0099] - triols, such as glycerol (glycerin),

[0100] and mixtures thereof.

[0101] According to a very preferred embodiment, the polyol is chosen from triols such as glycerol.

[0102] The aqueous phase may also comprise any water-soluble or water-dispersible compound that is compatible with an aqueous phase, such as stabilizers, gelling agents, film-forming polymers, thickeners, surfactants, and mixtures thereof.Fatty phase

[0103] As mentioned above, a composition according to the invention may comprise at least one fatty phase.

[0104] For the purposes of the invention, the term “fatty phase” means a phase comprising at least one oil and all of the liposoluble and lipophilic ingredients and the fatty substances, which are in particular liquid at 20°C and atm pressure, used for the formulation of the compositions of the invention.

[0105] In particular, a composition according to the invention may comprise from 5% to 95% by weight and preferably from 10% to 80% by weight of fatty phase, relative to the total weight of the composition.

[0106] The fatty phase of the composition according to the invention may comprise oils, waxes, pasty compounds, and / or silicone compounds, and preferably at least one oil, notably a cosmetic oil.Oils

[0107] The term "oil" is understood to mean a water-immiscible non-aqueous compound that is liquid at ambient temperature (20°C) and at atmospheric pressure (760 mmHg).

[0108] A fatty phase that is suitable for preparing the compositions, notably cosmetic compositions, according to the invention may comprise hydrocarbon oils, silicone oils, fluoro oils or non-fluoro oils, or mixtures thereof.

[0109] The oils may be volatile or non-volatile.

[0110] The fatty phase can comprise, besides the merocyanine screening agent(s) and optionally the lipophilic additional screening agent(s), at least one volatile or non-volatile hydrocarbon oil and / or one volatile and / or non-volatile silicone oil and / or one volatile and / or non-volatile fluoro oil.

[0111] For the purposes of the present invention, the term “hydrocarbon oil” means an oil mainly containing hydrogen and carbon atoms.

[0112] The term “silicone oil” means an oil comprising at least one silicon atom and notably at least one Si-O group.

[0113] The term “fluoro oil” means an oil comprising at least one fluorine atom.

[0114] The oils may optionally comprise oxygen, nitrogen, sulfur and / or phosphorus atoms, for example in the form of hydroxyl or acid radicals.Volatile oils

[0115] For the purposes of the invention, the term “volatile oil” refers to any oil that is capable of evaporating on contact with the skin in less than one hour, at ambient temperature and atmospheric pressure. The volatile oil is a volatile cosmetic compound that is liquid at ambient temperature, particularly having a non-zero vapour pressure, at ambient temperature and atmospheric pressure, particularly having a vapour pressure ranging from 0.13 Pa to 40 000 Pa (10-3to 300 mmHg), in particular ranging from 1.3 Pa to 13 000 Pa (0.01 to 100 mmHg) and more particularly ranging from 1.3 Pa to 1300 Pa (0.01 to 10 mmHg).

[0116] The volatile oils may be hydrocarbon oils or silicone oils.

[0117] Among the volatile hydrocarbon oils containing from 8 to 16 carbon atoms, mention may particularly be made of branched C8-C16alkanes, for instance C8-C16isoalkanes (also known as isoparaffins), isododecane, isodecane, isohexadecane and, for example, the oils sold under the trade names Isopar or Permethyl, branched C8-C16esters, for instance isohexyl neopentanoate, and mixtures thereof.

[0118] Mention may also be made of volatile linear alkanes comprising from 8 to 16 carbon atoms, in particular from 10 to 15 carbon atoms, and more particularly from 11 to 13 carbon atoms, for instance n-dodecane (C12) and n-tetradecane (C14) sold by Sasol under the respective references Parafol 12-97 and Parafol 14-97, and also mixtures thereof, the undecane-tridecane mixture, mixtures of n-undecane (C11) and of n-tridecane (C13) obtained in examples 1 and 2 of patent application WO 2008 / 155059 from the company Cognis, and mixtures thereof.

[0119] Volatile silicone oils that may be mentioned include linear volatile silicone oils such as hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, tetradecamethylhexasiloxane, hexadecamethylheptasiloxane and dodecamethylpentasiloxane.

[0120] Volatile cyclic silicone oils that may be mentioned include hexamethylcyclotrisiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, cyclohexasiloxane and dodecamethylcyclohexasiloxane, in particular cyclohexasiloxane.

[0121] Use may also be made of volatile fluoro oils, such as nonafluoromethoxybutane, decafluoropentane, tetradecafluorohexane, dodecafluoropentane, and mixtures thereof.Non-volatile oils

[0122] The term “non-volatile” refers to an oil of which the vapour pressure at ambient temperature and atmospheric pressure is non-zero and is less than 10-3mmHg (0.13 Pa).

[0123] The non-volatile oils may notably be chosen from non-volatile hydrocarbon, fluoro and / or silicone oils.

[0124] Non-volatile hydrocarbon oils that may notably be mentioned include:

[0125] - linear or branched hydrocarbons of mineral or synthetic origin, such as petroleum jelly, polydecenes, hydrogenated polyisobutene such as Parleam, and squalane, and mixtures thereof,

[0126] - non-volatile alkanes, preferably with a viscosity of less than 20 mPa.s at 20°C measured with a Rheomat RM100® viscometer from Lamy Rheology. The term “non-volatile alkane” means a hydrocarbon cosmetic oil which is liquid at ambient temperature, notably having a vapour pressure at 20°C of less than 0.01 kPa, according to the definition of a Volatile Organic Compound (VOC) of article 2 of European Council Directive 1999 / 13 / EC of 11 March, 1992: “Any organic compound having, at a temperature of 293.15 K, a vapour pressure of 0.01 kPa or more”. In particular, the non-volatile alkanes comprise from 10 to 30 carbon atoms, in particular from 12 to 26 carbon atoms, and more particularly from 15 to 19 carbon atoms, and preferably a mixture of alkanes containing from 15 to 19 carbon atoms, for example the products sold under the references Emogreen L19 and Emosmart L19 from SEPPIC,

[0127] - hydrocarbon oils of plant origin, such as glyceride triesters, which are generally fatty acid triesters of glycerol, the fatty acids of which may have varied chain lengths from 4 to 24 carbon atoms, it being possible for these chains to be saturated or unsaturated and linear or branched; these oils are notably wheatgerm oil, sunflower oil, grape seed oil, sesame oil, corn oil, apricot oil, castor oil, shea oil, avocado oil, olive oil, soybean oil, sweet almond oil, palm oil, rapeseed oil, cottonseed oil, hazelnut oil, macadamia oil, jojoba oil, alfalfa oil, poppy oil, pumpkin oil, sesame oil, marrow oil, rapeseed oil, blackcurrant oil, evening primrose oil, millet oil, barley oil, quinoa oil, rye oil, safflower oil, candlenut oil, passionflower oil and musk rose oil; or else caprylic / capric acid triglycerides, such as those sold by the company Stéarinerie Dubois or those sold under the names Miglyol 810, 812 and 818 by the company Dynamit Nobel,

[0128] - synthetic ethers containing from 10 to 40 carbon atoms, such as dicapryl ether,

[0129] - synthetic esters, such as oils of formula R1COOR2in which R1represents a residue of a linear or branched fatty acid containing 1 to 40 carbon atoms, and R2represents a hydrocarbon chain, in particular branched chain, containing 1 to 40 carbon atoms provided that R1+ R2is greater than or equal to 10, for instance Purcellin oil (ketostearyl 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 Witco or "Tegosoft TN" by Evonik Goldschmidt, 2-ethylphenyl benzoate such as the commercial product sold under the name “X-tend 226” by 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 Stearinerie Dubois, octanoates, decanoates or ricinoleates of alcohols or of polyalcohols, such as propylene glycol dioctanoate; hydroxyl esters such as isostearyl lactate, diisostearyl malate; and pentaerythritol esters; citrates, such as the ester of C3-C22tricarboxylic acid and of C1-C6alcohols with the INCI name Tiethyl Citrate, for example the product sold 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 Enichem Augusta Industriale and also 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,

[0130] - fatty amides, such as isopropyl N-lauroyl sarcosinate, for example the product sold under the trade name Eldew SL205 from Ajinomoto,

[0131] - polyol esters and pentaerythritol esters, for instance dipentaerythrityl tetrahydroxystearate / tetraisostearate,

[0132] - fatty alcohols that are liquid at ambient temperature, with a branched and / or unsaturated carbon-based chain containing from 12 to 26 carbon atoms, for instance octyldodecanol, isostearyl alcohol, oleyl alcohol, 2-hexyldecanol, 2-butyloctanol, 2-undecylpentadecanol,

[0133] - C12-C22higher fatty acids, such as oleic acid, linoleic acid and linolenic acid, and mixtures thereof,

[0134] - carbonates, such as dicaprylyl carbonate, for example the product sold under the name Cetiol CC by the company Cognis,

[0135] - non-phenyl silicone oils, for instance caprylyl methicone, and

[0136] - phenyl silicone oils, for instance phenyl trimethicones, phenyl dimethicones, phenyltrimethylsiloxydiphenylsiloxanes, diphenyl dimethicones, diphenylmethyldiphenyltrisiloxanes and 2-phenylethyl trimethylsiloxysilicates, dimethicones or phenyl trimethicone with a viscosity of less than or equal to 100 cSt, trimethylpentaphenyltrisiloxane, and mixtures thereof;

[0137] and also mixtures of these various oils.Other fatty substances

[0138] A fatty phase according to the invention may also comprise other fatty substances, mixed with or dissolved in an oil.

[0139] The other fatty substances that may be present in the oily phase are, for example:

[0140] - fatty acids including from 8 to 30 carbon atoms, such as stearic acid, lauric acid, palmitic acid and oleic acid;

[0141] - waxes, other than glyceryl trihydroxystearate, such as lanolin, beeswax, carnauba or candelilla wax, paraffin waxes, lignite waxes or microcrystalline waxes, ceresin or ozokerite, or synthetic waxes, such as polyethylene waxes or Fischer-Tropsch waxes;

[0142] - silicone resins such as trifluoromethyl(C1-C4)alkyl dimethicone and trifluoropropyl dimethicone;

[0143] - silicone elastomers such as the products sold under the name KSG by the company Shin-Etsu, under the names Trefil or BY29 by the company Dow Corning or under the name Gransil by the company Grant Industries;

[0144] - a gum chosen from silicone gums (dimethiconol);

[0145] - a pasty compound, such as polymeric or non-polymeric silicone compounds, esters of an oligomeric glycerol, arachidyl propionate, fatty acid triglycerides and derivatives thereof;

[0146] - and mixtures thereof.

[0147] As fatty substances, a composition according to the invention may comprise at least one fatty alcohol wax. Such waxes may be chosen from lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, arachidyl alcohol, behenyl alcohol, lignoceryl alcohol, ceryl alcohol, montanyl alcohol, myricyl alcohol, and mixtures thereof.

[0148] As fatty substance, a composition according to the invention may in particular comprise at least one butter, in particular a plant butter.

[0149] The plant butters that are suitable for use in the invention are preferably chosen from the group comprising avocado butter, cocoa butter, shea butter, kokum butter, mango butter, murumuru butter, coconut butter, apricot kernel butter, sal butter and urukum butter, and mixtures thereof, and in particular is shea butter.

[0150] These fatty substances may be chosen in a varied manner by a person skilled in the art in order to prepare a composition having the desired properties, for example in terms of consistency or texture.

[0151] 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 chosen from linear or branched hydrocarbons of mineral or synthetic origin, non-volatile alkanes, hydrocarbon oils of plant origin, synthetic esters, fatty amides, carbonates, and also mixtures of these various oils, even better still chosen from synthetic esters, fatty amides, carbonates, and mixtures thereof.

[0152] According to a preferred embodiment, the composition according to the invention comprises a polar oil.

[0153] 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 and preferably from 2.0% to 15.0% by weight relative to the total weight of the composition.

[0154] According to a preferred embodiment, a composition according to the invention contains at least one oil chosen from squalane, mixtures of alkanes containing from 15 to 19 carbon atoms, caprylic / capric acid triglycerides, alkyl benzoates containing between 12 and 15 carbon atoms, diisopropyl adipate, 2-ethylhexyl palmitate, diisopropyl sebacate, the ester of C3-C22tricarboxylic acid and of C1-C6alcohols having the INCI name Triethyl Citrate, isopropyl N-lauroyl sarcosinate, dicaprylyl carbonate, and mixtures thereof, even better still chosen from diisopropyl sebacate, isopropyl N-lauroyl sarcosinate, dicaprylyl carbonate.

[0155] 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 preferentially is free of silicone oil(s).

[0156] Preferably, a composition according to the invention comprises a fatty phase containing at least one fatty substance.

[0157] 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 agent / thickener

[0158] The composition according to the present invention may comprise at least one gelling agent (or thickener) that is hydrophilic, i.e. that is water-soluble or water-dispersible.

[0159] Examples of hydrophilic gelling agents that may be mentioned include modified or unmodified carboxyvinyl polymers, such as the products sold under the names Carbopol (CTFA name: carbomer) and Pemulen (CTFA name: Acrylates / C10-30 alkyl acrylate crosspolymer) by the company Goodrich; polyacrylamides; optionally crosslinked and / or neutralized 2-acrylamido-2-methylpropanesulfonic acid polymers and copolymers, for instance the poly(2-acrylamido-2-methylpropanesulfonic acid) sold by the company Hoechst under the name Hostacerin AMPS (CTFA name: Ammonium polyacryldimethyltauramide); crosslinked anionic copolymers of acrylamide and of AMPS, which are in the form of a W / O emulsion, such as those sold 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 amount of gelling agents depends on the desired objective.

[0160] More preferentially, the hydrophilic gelling agent is chosen from polysaccharide biopolymers such as scleroglucan gum.

[0161] According to one embodiment, the amount 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 active agent(s)

[0162] The composition may also comprise one or more active agent(s) other than (ii) and (iii).

[0163] Active agents that may be mentioned include, for example, moisturizers, depigmenting agents, desquamating agents, anti-ageing agents other than (ii) and (iii), mattifying agents, cicatrizing agents, preserving agents such as antibacterial agents, UV-screening agents which are notably lipophilic, and mixtures thereof.

[0164] Preferably, the composition according to the invention comprises from 0.01% to 20% by total weight of at least one active agent, preferably from 0.05% to 15% by weight, and preferentially from 0.1% to 10% by weight of at least one active agent relative to the total weight of the composition.

[0165] The compositions of the invention may contain one or more adjuvants commonly used in the cosmetic and dermatological fields; emollients; sequestrants; antioxidants; fillers; free-radical scavengers; essential oils; fragrances; film-forming agents; dyes; and mixtures thereof. The total amounts of these various adjuvants are those conventionally used in the fields under consideration. In particular, these amounts vary according to the desired aim and may range, for example, from 0.01% to 20% and preferably from 0.1% to 10% by weight relative to the total weight of the composition.

[0166] Needless to say, a person skilled in the art will take care to select the optional adjuvant(s) added to the composition according to the invention such that the advantageous properties intrinsically associated with the composition in accordance with the invention are not, or are not substantially, adversely affected by the envisaged addition.

[0167] The amounts of these various active agents are those conventionally used in the fields under consideration. In particular, these amounts vary according to the desired aim and may range, for example, from 0.01% to 20% and preferably from 0.1% to 10% by weight relative to the total weight of the composition.

[0168] A subject of the composition according to the invention is also the cosmetic use of a composition according to the invention for caring for keratin materials, in particular for caring for bodily and / or facial skin.

[0169] A subject of the present invention is also a process for treating keratin materials, notably human keratin materials such as the skin, in which a composition according to the invention is applied to said keratin materials.

[0170] More particularly, the treatment process is a process for keratin materials such as the skin, in particular bodily and / or facial skin; said process is non-therapeutic, preferably a care process, in which a composition according to the invention is applied to said keratin materials.

[0171] The composition in accordance with the invention may be obtained in the usual manner by a person skilled in the art.

[0172] The examples that follow will allow the invention to be understood more clearly, but without them being limiting in nature. The starting materials are referred to by their chemical or INCI name. The amounts are indicated as weight percentages of starting materials (SM) relative to the total weight of the composition, unless otherwise mentioned.Examples

[0173] Examples of synthesis of merocyanines of formula (3)Example A1: Preparation of the compound (14)

[0174]

[0175] 122.23 g of 3-[(3-methoxypropyl)amino]-2-cyclohexen-1-one are alkylated with dimethyl sulfate or alternatively with diethyl sulfate and treated with 75.45 g of ethyl cyanoacetate in approximately equimolar proportions in the presence of a base and optionally of a solvent.

[0176] The base / solvent combinations indicated in the following table are used.

[0177] ExampleBaseSolventExample A1.1DBU (1,8-diazabicyclo[5.4.0]undec-7-ene)dimethylacetamideExample A1.2triethylamineisopropanolExample A1.33-methoxypropylamineisopropanolExample A1.43-methoxypropylaminetert-amyl alcoholExample A1.53-methoxypropylaminetolueneExample A1.63-methoxypropylaminedimethylformamideExample A1.73-methoxypropylamineno solventExample A1.8N-morpholineisopropanol

[0178] The completion of the alkylation reaction can be monitored for example by methods such as TLC, GC or HPLC.

[0179] 162.30 g of compound (14) obtained in the form of a brown oil.

[0180] After crystallization, the product is obtained in the form of yellowish crystals.

[0181] Melting point: 92.7°C.Example A2: Preparation of the compound (15)

[0182]

[0183] 101.00 g of 3-[(3-methoxypropyl)amino]-2-cyclohexen-1-one are alkylated with dimethyl sulfate or alternatively with diethyl sulfate and treated with 86.00 g of 2-cyano-N-(3-methoxypropyl)acetamide in approximately equimolar proportions in the presence of a base and optionally of a solvent.

[0184] The base / solvent combinations indicated in the following table are used.

[0185] ExampleBaseSolventExample A2.1DBU (1,8-diazabicyclo[5.4.0]undec-7-ene)dimethylacetamideExample A2.2triethylamineisopropanolExample A2.33-methoxypropylamineisopropanolExample A2.43-methoxypropylaminetert-amyl alcoholExample A2.53-methoxypropylaminetolueneExample A2.63-methoxypropylaminedimethylformamideExample A2.73-methoxypropylamineno solvent

[0186] The crude product (15) is obtained in the form of a dark brown oil.

[0187] After silica gel column chromatography (eluent: 99 / 1 toluene / methanol), 81.8 g of product are obtained in the form of yellowish crystals.

[0188] Melting point: 84.7-85.3°C.Example A3: Preparation of the compound (27)

[0189]

[0190] 13.09 g of 3-[(3-methoxypropyl)amino]-2-cyclohexen-1-one are alkylated with dimethyl sulfate or alternatively with diethyl sulfate and treated with 10.12 g of isobutyl cyanoacetate in the presence of a base and optionally of a solvent.

[0191] The base / solvent combinations indicated in the following table are used.

[0192] ExampleBaseSolventExample A3.1DBU (1,8-diazabicyclo[5.4.0]undec-7-ene)dimethylacetamideExample A3.2triethylamineisopropanolExample A3.33-methoxypropylamineisopropanolExample A3.4N-methylmorpholinetert-amyl alcoholExample A3.53-methoxypropylaminetolueneExample A3.63-methoxypropylaminedimethylformamideExample A3.73-methoxypropylamineno solvent

[0193] 15.97 g of crude product (27) are obtained in the form of a dark brown oil.

[0194] After silica gel column chromatography (eluent: toluene / acetone), 13.46 g of product are obtained in the form of yellowish crystals.

[0195] Melting point: 96.3°C.Example A4: Preparation of the compound (25)

[0196]

[0197] 148.4 g of 3-[(3-methoxypropyl)amino]-2-cyclohexen-1-one are alkylated with dimethyl sulfate or alternatively with diethyl sulfate and treated with 130.00 g of 2-ethoxyethyl cyanoacetate in the presence of an organic base and of a solvent.

[0198] The base / solvent combinations indicated in the table below are used.

[0199] ExampleBaseSolventExample A4.1DBU (1,8-diazabicyclo[5.4.0]undec-7-ene)dimethylacetamideExample A4.2triethylamineisopropanolExample A4.33-methoxypropylamineisopropanolExample A4.4N-methylmorpholinetert-amyl alcoholExample A4.53-methoxypropylaminetolueneExample A4.63-methoxypropylaminedimethylformamideExample A4.73-methoxypropylamineno solventCompositions

[0200] The compositionsA1,A2, B1andB2were prepared from the ingredients of which the contents are indicated in the table below (% active material):

[0201] In the examples that follow, all the amounts are given as mass percentages of active material (AM) relative to the total weight of the composition (unless otherwise mentioned).

[0202] INCIPhaseA1(invention)B1(comparative)A2(invention)B2(comparative)Sodium hydroxideEqs pH 6+ / -0.3qs pH 6+ / -0.3qs pH 6+ / -0.3qs pH 6+ / -0.3TocopherolD1.001.001.001.00Ascorbic acidE12.0012.0012.0012.00Dicaprylyl carbonateB--4.004.00Preserving agentB--1.001.00Preserving agentA0.700.70--FragranceD0.200.20--WaterCQS100QS100QS100QS100Diisopropyl adipateB4.004.00--GlycerolA5.005.005.005.00Sodium stearoyl glutamateA0.750.750.750.75Preserving agentB0.300.300.200.20Sucrose tristearateB2.002.002.002.00Polyglyceryl-3 methylglucose distearateB1.001.00--Diisopropyl sebacateB3.003.003.003.00AdenosineA0.100.100.100.10Isopropyl Lauroyl SarcosinateB8.008.008.008.00Stearyl AlcoholB0.400.400.401.00Trisodium EthylenediaminedisuccinateA0.500.500.500.50ResveratrolB0.250.250.250.25Preserving agentB0.500.50--PolymerB1.001.00--Methoxypropylamino Cyclohexenylidene Ethoxyethylcyanoacetate(compound 25)B1.00 -1.00-Bis(ethylhexyloxyphenol)methoxyphenyltriazineB---0.5Butyl methoxydibenzoylmethaneB---0.5Sclerotium gumC0.800.800.501.5Active agentC2.002.00--Manufacturing process

[0203] Phase A is heated to 75°C for 15 minutes in a tank, with stirring (emulsifier 1000 and blades 30 rpm).

[0204] Phase B is heated to 75°C and introduced into phase A with stirring (emulsifier 4000 rpm and blades 60 rpm) for 15 minutes.

[0205] Phase C is introduced and mixed for 10 minutes under vacuum (-0.5 bar).

[0206] The mixture is cooled to 45°C and phase D is added with stirring, then mixing is carried out for 5 minutes under vacuum (-0.5 bar).

[0207] Phase E is added and mixing is carried out for 5 minutes (vacuum -0.7 bar) then the emulsifier is removed and the blades are left at 30 rpm under vacuum (-0.5 bar) for 5 minutes.Protocol for measuring the photostability

[0208] The compositions are analyzed to evaluate the resveratrol photostability during exposure of the compositions to UV radiation.

[0209] Each of the compositions A1, A2, B1 and B2 was applied independently onto an inert support (n=4 assays for each formula tested). The supports thus covered were exposed to UV radiation of 5 J / cm2for 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.

[0210] The amount of resveratrol in each of the compositions was measured by HPLC-UV assay at t1 and t2, as indicated below:

[0211] t1: After preparation of the composition and placing in the oven (used as a reference);

[0212] t2: After exposure of the compositions to UV radiation.

[0213] The details of the HPLC-UV assays are as follows:

[0214] Instruments / Reagents:

[0215] HPLC systemUltra Performance LC (UPLC)HPLC columnRP18, 1.7, 2.1 mm x 100 mmEluent A0.1% phosphoric acidEluent BMethanol

[0216] Conditions:

[0217] UV detector296 nmColumn temperature30℃Flow rate0.4 ml / minInjection volume1 µlMobile phaseGradientA: 0.1% phosphoric acid in waterB: Methanol

[0218] The amount of resveratrol contained in the compositions A1, A2, B1 and B2 before (t1) and after exposure to UV radiation (t2) was determined by HPLC-UV and the ratio t2 / t1 x100 was calculated.

[0219] Results:

[0220] The amounts (%) of trans-resveratrol remaining after exposure of the compositions A1, A2, B1 and B2 to UV radiation are given in the table below:

[0221] CompositionAmount of trans-resveratrol remaining after exposure to UV radiationA1 (invention)80%B1 (comparative)<10%A2 (invention)78%B2 (comparative)63%

[0222] The results obtained show that trans-resveratrol remains stable under exposure to UV radiation in the composition A1 according to the invention, unlike the composition B1 which does not comprise methoxypropylamino cyclohexenylidene ethoxyethylcyanoacetate.

[0223] The photostability of resveratrol is significantly greater in composition A2 according to the invention compared to composition B2 comprising a combination of UVA and UVB screening agents.

[0224] 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 cyclohexenylidene ethoxyethylcyanoacetate.Stability of the formulas

[0225] Measurement of stability of the compositions A1 and A2:

[0226] The stability of the compositions is evaluated after storage of the formulations and under the following conditions:

[0227] A composition is prepared and then stored at different temperatures:

[0228] i) at 4°C

[0229] ii) at ambient temperature

[0230] The composition is then evaluated as follows:

[0231] - at t = 24 hours, the macroscopic and microscopic appearance, the colour and the odour of the composition, even the pH, are characterized,

[0232] - at t = 1 month, the macroscopic and microscopic appearance, the colour and the odour of the composition.

[0233] The macroscopic appearance of the composition must remain identical or even close to the initial appearance characterized at t = 24 hours. To be compliant, a composition must remain smooth, homogeneous and unchanged in appearance, i.e. with no release, no creaming, no phase separation and no change in colour or odour.

[0234] The compositions A1 and A2 according to the invention are compliant from a microscopic and macroscopic point of view after storage for 1 month at 4°C and ambient temperature.Stability of Simplex formulas A3 and B3

[0235] 2 simplex blends A3 and B3 were prepared.A3 (invention)B3 (comparative)Resveratrol1.451.45Methoxypropylamino Cyclohexenylidene Ethoxyethylcyanoacetate(compound 25)5.795.79Tocopherol5.79-Isopropyl Lauroyl SarcosinateQS100QS100

[0236] After 1 week at 25°C, the composition B3, which does not comprise any tocopherol, browns, unlike the composition A3 which comprises tocopherol. It follows from this that tocopherol makes it possible to stabilize the formula and in particular the colour.

Claims

Use of (i) one or more merocyanine(s) of formula (3) below and also the E / E or E / Z geometric isomer forms thereof, and the tautomers thereof, the salts thereof, and the solvates thereof such as hydrates:in which formula (3):A is -O- or -NH;R is a C1-C22alkyl group, a C2-C22alkenyl group, a C2-C22alkynyl group, a C3-C22cycloalkyl group or a C3-C22cycloalkenyl group, it being possible for said groups to be interrupted by one or more O;for (photo)stabilizing (ii) resveratrol, a derivative thereof and also the geometric isomer forms thereof, the salts thereof and the solvates thereof such as hydrates, or a mixture thereof.Use according to Claim 1, in which (i) the merocyanine(s) of formula (3) and also the E / E or E / Z geometric isomer forms thereof and the tautomers thereof is (are) chosen from the compounds of formula (3) and also the geometric isomer forms thereof, the tautomers thereof, the salts thereof and the solvates thereof such as hydrates, in which:A is -O-; R is a C1-C22alkyl, better still R is a C1-C6alkyl, which may be interrupted by one or more O.Use according to either one of the preceding claims, in which (i) the merocyanine(s) of formula (3) is (are) chosen from the following compounds, and also the E / E geometric isomer forms thereof, and the tautomers thereof, the salts thereof and the solvates thereof such as hydrates:14ethyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-1-ylidene}ethanoate15(2Z)-2-cyano-N-(3-methoxypropyl)-2-{3-[(3-methoxypropyl)amino]cyclohex-2-en-1-ylidene}ethanamide252-ethoxyethyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-1-ylidene}ethanoate272-methylpropyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-1-ylidene}ethanoate292-butoxyethyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-1-ylidene}ethanoate313-methoxypropyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-1-ylidene}ethanoate373-ethoxypropyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-1-ylidene}ethanoateUse according to any one of the preceding claims, in which (i) the merocyanine of formula (3) is 2-ethoxyethyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-1-ylidene}ethanoate (25) in its E / Z geometric configuration having the following structure, and also the tautomers thereof:[Formula 25]and / or in its E / E geometric configuration having the following structure:[Formula 25a]Use according to any one of the preceding claims, in which (ii) resveratrol, a derivative thereof and also the geometric isomer forms thereof, the salts thereof and the solvates thereof such as hydrates is (are) chosen from resveratrol, the salts thereof, resveratrol triphosphate, the salts thereof, polydatin, the salts thereof, and mixtures thereof, preferably chosen from resveratrol, sodium resveratrol triphosphate and polydatin and mixtures thereof.Use according to any one of the preceding claims, in which (ii) resveratrol, a derivative thereof and also the geometric isomer forms thereof, the salts thereof and the solvates thereof such as hydrates is resveratrol, preferably in its trans form.Composition, notably cosmetic composition, comprising:(i) one or more merocyanines of formula (3) as defined in any one of Claims 1 to 4;(ii) resveratrol, a derivative thereof or mixtures thereof as defined in either one of Claims 5 and 6;(iii) one or more antioxidant(s) other than (ii).Composition according to the preceding claim, in which (i) the merocyanine(s) of formula (3) and also the E / E or E / Z geometric isomer forms thereof and the tautomers thereof, the salts thereof and the solvates thereof such as hydrates are present in an amount of greater than or equal to 0.1% and less than or equal to 15% by weight, and preferentially greater than or equal to 0.2% and less than or equal to 10% by weight and even better still greater than or equal to 0.5% and less than or equal to 5% by weight, even 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.Composition according to either one of Claims 7 and 8, in which the resveratrol, a derivative thereof and also the geometric isomer forms thereof, the salts thereof and the solvates thereof such as hydrates, or a mixture thereof, is (are) present in an amount greater than or equal to 0.001% and less than or equal to 10% by weight, more preferentially greater than or equal to 0.01% and less than or equal to 5% by weight, better still greater than or equal to 0.05% and less than or equal to 2% by weight, even 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 according to any one of Claims 7 to 9, in which (iii) the antioxidant(s) other than (ii) is (are) chosen from vitamins, salts thereof and derivatives thereof, ascorbic acid, salts thereof and derivatives thereof, more preferentially chosen from tocopherol, a derivative thereof, a salt thereof, an optical isomer thereof, such that (iii) the antioxidant is tocopherol.Composition according to any one of Claims 7 to 10, in which 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 preferentially greater than or equal to 0.7% and less than or equal to 20% by weight, relative to the total weight of the composition.Composition according to any one of Claims 7 to 11, comprising one or more oil(s), preferably a non-volatile oil, more preferentially chosen from non-volatile hydrocarbon oils, in particular chosen from linear or branched hydrocarbons of mineral or synthetic origin, non-volatile alkanes, hydrocarbon oils of plant origin, synthetic esters, fatty amides, carbonates, as well as mixtures even better still chosen from synthetic esters, fatty amides, carbonates, and mixtures thereof, such as diisopropyl sebacate, isopropyl N-lauroyl sarcosinate, dicaprylyl carbonate.Composition according to any one of Claims 7 to 12, comprising one or more hydrophilic gelling agents, more preferentially chosen from modified or unmodified carboxyvinyl polymers, polyacrylamides, polymers and copolymers of 2-acrylamido 2-methylpropanesulfonic acid, which have been optionally crosslinked and / or neutralized, such as poly(2-acrylamido 2-methylpropanesulfonic acid), crosslinked anionic copolymers of acrylamide and AMPS, polysaccharide biopolymers such as xanthan gum, guar gum, scleroglucan gum, alginates, modified celluloses, and mixtures thereof; better still, the hydrophilic gelling agent is chosen from polysaccharide biopolymers such as scleroglucan gum.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 an oil-in-water emulsion.Cosmetic process for caring for and / or making up a keratin material, comprising the application, to the surface of said keratin material, of at least one composition as defined in any one of Claims 7 to 14.

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