Cosmetic or dermatological composition comprising a water-soluble organic UV-screening agent and a thiopyridinone compound

Abstract

The present invention relates to a composition, in particular a cosmetic or dermatological composition, comprising at least one aqueous phase, at least one water-soluble organic UV-screening agent and at least one thiopyridinone compound of given formula, and / or the optical isomers or geometric isomers thereof and also the organic or mineral acid or base salts thereof, and / or solvates thereof, such as hydrates.

Description

Cosmetic or dermatological composition comprising a water-soluble organic UV-screening agent and a thiopyridinone compound

[0001] The present invention relates to a composition, in particular a cosmetic or dermatological composition, comprising at least one aqueous phase, at least one water-soluble organic UV-screening agent and at least one compound of formula (I) or (I’), as described below, and / or the optical isomers or geometric isomers thereof and also the organic or mineral acid or base salts thereof, and / or solvates thereof, such as hydrates.

[0002] A depigmenting or bleaching agent which is a thiopyridinone compound is known from patent applications WO2012 / 080075 and WO2017 / 102349. The thiopyridinone compound has depigmenting or bleaching properties which are particularly effective in reducing melanin production.

[0003] However, the stability of this compound, and in particular its stability when it is exposed to light, in particular to UV radiation, is not optimal. Thus, there remains a need to improve the photostability of this compound, notably when it is present in a composition comprising at least one aqueous phase.

[0004] The applicant has discovered, surprisingly, that by using at least one water-soluble organic UV-screening agent, it was possible to substantially improve the photostability of such a thiopyridinone compound. This discovery forms the basis of the present invention.

[0005] Thus, in accordance with one of the subjects of the present invention, a composition, and in particular a cosmetic or dermatological composition, is now proposed comprising at least one water-soluble organic UV-screening agent and at least one compound of formula (I) or (I’), as described below, and / or the optical isomers or geometric isomers thereof and also the organic or mineral acid or base salts thereof, and / or solvates thereof, such as hydrates.

[0006] The photostability of the thiopyridinone compound is improved, even in the presence of additional UV-screening agents other than the water-soluble UV-screening agent(s).

[0007] Specifically, it may be particularly advantageous to insert UV-screening agents into a cosmetic composition comprising a thiopyridinone compound in order to obtain compositions having good activity on pigmentation induced by UV and visible radiation, a high level of sun protection, and also a good physicochemical stability, and good cosmetic quality, in particular they are non-greasy and non-tacky.

[0008] Thus, in accordance with another subject of the present invention, a composition, and in particular a cosmetic or dermatological composition, is proposed comprising at least one water-soluble organic UV-screening agent, at least one additional UV-screening agent and at least one compound of formula (I) or (I’), as described below, and / or the optical isomers or geometric isomers thereof and also the organic or mineral acid or base salts thereof, and / or solvates thereof, such as hydrates.

[0009] The applicant has discovered that the use of at least one water-soluble organic UV-screening agent makes it possible to increase the photostability of a thiopyridinone compound, and / or an optical isomer, geometric isomer, and also an organic or mineral acid or base salt, and / or a solvate such as a hydrate, in particular when it is dissolved in a composition comprising at least one aqueous phase, even in the presence of additional UV-screening agents.Disclosure of the invention

[0010] Thus, one subject of the present invention is a composition, in particular a cosmetic or dermatological composition, comprising:

[0011] (a) at least one aqueous phase;

[0012] (b) at least one water-soluble organic UV-screening agent; and

[0013] (c) at least one compound selected from the compounds of formula (I), tautomers of formula (I’), salts thereof, solvates thereof, such as hydrates thereof, optical isomers thereof, racemates thereof, and mixtures thereof:

[0014] wherein:

[0015] - R1denotes a radical chosen from a) a hydrogen atom, and b) a saturated, linear C1-C10or branched C3-C10alkyl group optionally substituted with one or more groups, which may be identical or different, chosen from i) -O-R3, and ii) -S-R3, and

[0016] - R2denotes a radical chosen from a) a hydrogen atom, b) a saturated, linear C1-C12or branched C3-C12or cyclic C3-C8hydrocarbon group optionally substituted with one or more groups, which may be identical or different, chosen from i) -O-R3, ii) -S-R3, iii) -C(O)-O-R3, and iv) a C5-C12aryl group, optionally substituted with one or more hydroxyls and / or with one or more C1-C8alkoxy radicals, and c) a C5-C12aryl group, optionally substituted with one or more hydroxyls and / or with one or more C1-C8alkoxy radicals, and

[0017] - R3denotes a radical chosen from a) a hydrogen atom, and b) a saturated, linear C1-C10or branched C3-C10alkyl group.

[0018] This composition may optionally comprise at least one additional UV-screening agent.

[0019] The present invention makes it possible to obtain cosmetic or dermatological compositions which are purely aqueous or are in the form of emulsions, in which the thiopyridinone compound is stable over time, in particular during exposure to UV radiation.

[0020] The compositions in accordance with the invention also exhibit good activity on pigmentation induced by UV and visible radiation, a strong photoprotective power, a good physicochemical stability and a good cosmetic quality, in particular they are non-greasy and non-tacky.

[0021] The present invention also relates to a non-therapeutic 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 according to the invention as defined above.

[0022] The invention also relates to a non-therapeutic cosmetic process for limiting the darkening of the skin and / or improving the color and / or uniformity of the complexion, comprising the application, to the surface of the keratin material, of at least one composition as defined previously.

[0023] The invention also relates to a non-therapeutic cosmetic process for preventing and / or treating the signs of aging of a keratin material, comprising the application, to the surface of the keratin material, of at least one composition as defined previously.

[0024] The present invention also relates to the use of at least one water-soluble organic UV-screening agent for photostabilizing the thiopyridinone compound(s) as defined above, and / or the optical isomers or geometric isomers thereof and also organic or mineral acid or base salts and / or solvates such as a hydrate.

[0025] Other features, aspects and advantages of the invention will become apparent on reading the detailed description that follows.

[0026] The composition according to the invention is intended for topical application and thus contains a physiologically acceptable medium. The term “physiologically acceptable medium” means here a medium that is compatible with keratin materials.

[0027] In the context of the present invention, the term “keratin material” notably means the skin, the scalp, keratin fibers such as the eyelashes, the eyebrows, head hair and body hair, the nails, and mucous membranes such as the lips, and more particularly the skin and mucous membranes (of the body, face, area around the eyes, eyelids or lips, preferably of the body, face and lips).

[0028] In the text hereinbelow, unless otherwise indicated, the limits of a range of values are included in that range, notably in the expressions “between” and “ranging from ... to ...”.

[0029] Moreover, the expressions “at least one” and “at least” used in the present description are equivalent to the expressions “one or more” and “greater than or equal to”, respectively.

[0030] According to the invention, the term “preventing” or “prevention” means reducing the risk of occurrence or slowing down the occurrence of a given phenomenon, namely, according to the present invention, the signs of aging of a keratin material.

[0031] For the purposes of the invention, a “hydrophilic organic UV-screening agent” is understood to mean the organic UV-screening agents chosen from water-soluble organic UV-screening agents and water-dispersible organic UV-screening agents.

[0032] A “water-soluble organic UV-screening agent” means any organic screening agent capable of being completely dissolved in molecular form in a liquid aqueous phase.

[0033] A “water-dispersible organic UV-screening agent” means any organic screening agent capable of forming, in a liquid aqueous phase, a homogeneous suspension of particles with a volume-mean size of less than 100 microns. The volume-mean size is determined by laser diffraction particle size analysis.

[0034] A “lipophilic organic UV-screening agent” means any organic screening agent capable of being completely dissolved in molecular form in a liquid fatty phase or else capable of being dissolved in colloidal form (for example in micellar form) in a liquid fatty phase.

[0035] An “organic UVA-screening agent” means any organic chemical molecule capable of absorbing at least UVA radiation in the wavelength range between 320 and 400 nm; said molecule may also additionally absorb UVB radiation in the wavelength range between 280 and 320 nm.

[0036] An “organic UVB screening agent” means any organic chemical molecule capable of absorbing mainly UVB radiation in the wavelength range between 280 and 320 nm.Detailed description of the inventionWater-soluble organic UV-screening agents

[0037] The composition in accordance with the invention comprises at least one water-soluble organic UV-screening agent.

[0038] Mention may be made, among the water-soluble organic screening agents capable of absorbing UVA rays, of:

[0039] - the compound with the INCI name Terephthalylidene Dicamphor Sulfonic Acid manufactured under the name Mexoryl SX by Noveal;

[0040] - the bis-benzazolyl derivatives as described in EP 669 323 and US 2 463 264 and more particularly the compound with the INCI name Disodium Phenyl Dibenzimidazole Tetrasulfonate sold under the trade name Neo Heliopan AP by Symrise.

[0041] The water-soluble organic screening agent may also be a mixed water-soluble screening agent capable of absorbing UVA and UVB rays. Preferably, such a mixed screening agent is a benzophenone derivative comprising at least one sulfonic radical, such as in particular:

[0042] benzophenone-4, sold under the trade name Uvinul® MS40 by BASF,

[0043] benzophenone-5, and

[0044] benzophenone-9.

[0045] According to one particular embodiment of the invention, the water-soluble organic screening agent(s) capable of absorbing UVA rays are chosen from terephthalylidene dicamphor sulfonic acid, bis-benzazolyl derivatives, in particular disodium phenyl dibenzimidazole tetrasulfonate, benzophenone-4, benzophenone-5, benzophenone-9 and mixtures thereof.

[0046] Preferably, the water-soluble organic screening agent(s) capable of absorbing UVA rays are chosen from terephthalylidene dicamphor sulfonic acid, disodium phenyl dibenzimidazole tetrasulfonate, benzophenone-4, benzophenone-5, benzophenone-9 and mixtures thereof.

[0047] Even more preferentially, the water-soluble organic screening agent(s) capable of absorbing UVA rays are chosen from terephthalylidene dicamphor sulfonic acid, bis-benzazolyl derivatives, in particular disodium phenyl dibenzimidazole tetrasulfonate, and mixtures thereof.

[0048] Preferably, the water-soluble organic screening agent(s) capable of absorbing UVA rays are chosen from terephthalylidene dicamphor sulfonic acid, disodium phenyl dibenzimidazole tetrasulfonate, and mixtures thereof.

[0049] According to a first preferred embodiment, the water-soluble organic screening agent capable of absorbing UVA rays is terephthalylidene dicamphor sulfonic acid (also known as ecamsule).

[0050] According to a second preferred embodiment, the water-soluble organic screening agent capable of absorbing UVA rays is disodium phenyl dibenzimidazole tetrasulfonate (also known as bisdisulizole disodium).

[0051] The water-soluble organic UVB-screening agent(s) that can be used according to the present invention may be chosen from water-soluble cinnamic derivatives, such as ferulic acid or 3-methoxy-4-hydroxycinnamic acid; water-soluble benzylidene camphor compounds; water-soluble phenylbenzimidazole compounds; water-soluble p-aminobenzoic (PABA) compounds, glyceryl PABA or PEG-25 PABA sold under the name Uvinul® P25 by BASF; water-soluble salicylic compounds, benzylidene camphor sulfonic acid manufactured under the name Mexoryl SL by Noveal, camphor benzalkonium methosulfate manufactured under the name Mexoryl SO by Noveal, and mixtures thereof.

[0052] As preferred examples of water-soluble organic UVB-screening agents, mention may be made of phenylbenzimidazole compounds, such as 2-phenyl-1H-benzimidazole-5-sulfonic acid (INCI name: phenylbenzimidazole sulfonic acid) notably sold under the trade name Eusolex 232®by Merck.

[0053] According to a preferred embodiment, the water-soluble organic screening agent capable of absorbing UVB rays is phenylbenzimidazole sulfonic acid (also known as ensulizole).

[0054] According to a particular embodiment, the water-soluble organic screening agent(s) are present in a total amount of active material of between 0.1% and 25% by weight, preferably between 0.1% and 20% by weight, preferably between 1% and 15% by weight, and even more preferentially between 1% and 5% by weight relative to the total weight of the composition.Thiopyridinone compounds

[0055] The composition according to the present invention comprises at least one thiopyridinone compound. Two or more distinct thiopyridinone compounds of formula (I) or (I’) may be used in combination. Thus, a single thiopyridinone compound of formula (I) or (I’) or a combination of different thiopyridinone compounds of formula (I) or (I’) may be used.

[0056] The thiopyridinone compound(s) are selected from the compounds of formula (I) below, tautomers of formula (I’) below, salts thereof, solvates thereof, such as hydrates thereof, optical isomers thereof, racemates thereof, and mixtures thereof:

[0057] wherein:

[0058] R1denotes a radical chosen from a) a hydrogen atom, and b) a saturated, linear C1-C10or branched C3-C10alkyl group optionally substituted with one or more groups, which may be identical or different, chosen from i) -O-R3, and ii) -S-R3, and

[0059] R2denotes a radical chosen from a) a hydrogen atom, b) a saturated, linear C1-C12or branched C3-C12or cyclic C3-C8hydrocarbon group, optionally substituted with one or more groups, which may be identical or different, chosen from i) -O-R3, ii) -S-R3, iii) -C(O)-O-R3, and iv) a C5-C12aryl group, optionally substituted with one or more hydroxyls and / or with one or more C1-C8alkoxy radicals, and c) a C5-C12aryl group, optionally substituted with one or more hydroxyls and / or with one or more C1-C8alkoxy radicals, and

[0060] R3denotes a radical chosen from a) a hydrogen atom, and b) a saturated, linear C1-C10or branched C3-C10alkyl group.

[0061] Below, for the purposes of the present invention and unless otherwise indicated:

[0062] - a "saturated, linear C1-C12or branched C3-C12" hydrocarbon group is equivalent to a "linear (C1-C12) or branched (C3-C12) alkyl group" which corresponds to a saturated, linear C1-C12or branched C3-C12hydrocarbon group, preferably a linear C1-C10or branched C3-C10hydrocarbon group, and more preferably a linear C1-C6or branched C3-C6hydrocarbon group; preferentially, the linear or branched groups may be chosen from methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl and decyl groups; more preferentially, the saturated, linear or branched alkyl groups may be chosen from methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl, pentyl, hexyl, heptyl and octyl groups, such as methyl, ethyl, n-pentyl, n-nonyl and isobutyl groups;

[0063] - a saturated "cyclic C3-C8" hydrocarbon group is amonocyclic or bicyclic cycloalkyl group containing from 3 to 8 carbon atoms. and in particular is a monocyclic C5to C7cycloalkyl group such as a cyclohexyl group,

[0064] - an "alkoxy radical" is an alkyl-oxy radical for which the alkyl radical is a linear or branched C1-C16hydrocarbon radical, and preferentially a C1-C8hydrocarbon radical;

[0065] - when the alkoxy group is optionally substituted, this implies that the alkyl group is optionally substituted as defined above;

[0066] - an "aryl" group represents a monocyclic or fused or non-fused bicyclic carbon-based group comprising from 5 to 12 carbon atoms, preferably from 6 to 10 carbon atoms, and wherein at least one ring is aromatic; preferentially, the aryl radical is a phenyl, biphenyl or naphthyl group, more preferably a phenyl group;

[0067] - the expression "at least one" is equivalent to the expression "one or more"; and

[0068] - the term "inclusive" for a concentration range means that the limits of that range are within the defined range.

[0069] The salts of the compounds of formula (I), (I’), (II) or (II’) as defined below comprise the conventional non-toxic salts of said compounds, such as those formed from an organic or inorganic acid or from an organic or inorganic base.

[0070] As salts of the compounds of formula (I), (I’), (II) or (II’), mention may be made of:

[0071] the salts obtained by addition of the compound of formula (I) or (II) to:

[0072] a mineral base, such as sodium hydroxide, potassium hydroxide, calcium hydroxide, ammonium hydroxide, magnesium hydroxide, lithium hydroxide, or sodium, potassium or calcium carbonate or hydrogen carbonate, for example; or

[0073] an organic base such as a primary, secondary or tertiary alkylamine, for example triethylamine or butylamine. This primary, secondary or tertiary alkylamine may comprise one or more nitrogen and / or oxygen atoms and may thus comprise, for example, one or more alcohol functions. Mention may be made in particular of 2-amino-2-methylpropanol, ethanolamine, triethanolamine, 2-dimethylaminopropanol, 2-amino-2-(hydroxymethyl)-1,3-propanediol and 3-(dimethylamino)propylamine.

[0074] Mention may also be made of the salts of amino acids, for example lysine, arginine, guanidine, glutamic acid and aspartic acid. Advantageously, the salts of the compounds of formula (I) or (II) (when they comprise a carboxyl group) may be chosen from alkali metal or alkaline-earth metal salts such as sodium, potassium, calcium or magnesium salts and ammonium salts.

[0075] An "organic or inorganic acid salt" is more particularly chosen from salts chosen from among 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 methanesulfonic acid and ethanesulfonic acid; v) arylsulfonic acids: Ar-S(O)2OH such as benzenesulfonic acid and toluenesulfonic acid; vi) citric acid; vii) succinic acid; viii) tartaric acid; ix) lactic acid; x) alkoxysulfinic acids: Alk-O-S(O)OH, such as methoxysulfinic acid and ethoxysulfinic acid; xi) aryloxysulfinic acids, such as tolueneoxysulfinic acid and phenoxysulfinic acid; xii) phosphoric acid H3PO4; xiii) acetic acid CH3C(O)OH; xiv) triflic acid CF3SO3H; and xv) tetrafluoroboric acid HBF4.

[0076] The acceptable solvates of the compounds described in the specification comprise conventional solvates such as those formed during the preparation of said compounds owing to the presence of solvents. Examples that may be mentioned include solvates due to the presence of water or of linear or branched alcohols, such as ethanol or isopropanol.

[0077] The optical isomers are in particular enantiomers and diastereoisomers.

[0078] Compound (I’) is the tautomeric form of compound (I) when a tautomeric equilibrium exists according to the following scheme:

[0079] According to one embodiment of the present invention, R1represents a hydrogen atom.

[0080] According to one embodiment of the present invention, R1of formulae (I) and (I’) represents a linear (C1-C10) or branched (C3-C10) alkyl group, in particular a linear (C1-C6) or branched (C3-C6) alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably ethyl. In particular, said alkyl group of R1is not substituted.

[0081] According to one embodiment of the present invention, R2represents a hydrogen atom.

[0082] According to one embodiment of the present invention, R2represents a linear (C1-C10) or branched (C3-C10) alkyl group, in particular a linear (C1-C6) or branched (C3-C6) alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably methyl or ethyl; said alkyl group of R2not being substituted.

[0083] According to one embodiment of the present invention, R2of formulae (I) and (I’) represents a linear (C1-C10) or branched (C3-C10) alkyl group, in particular a linear (C1-C6) or branched (C3-C6) alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably methyl or ethyl; said alkyl group being substituted with one or more groups selected from i), ii), iii) and iv) as defined above. Preferably, said alkyl group is substituted with one or two groups selected from i), ii) and iii), more preferably with one or two groups chosen from i) and iii), better still substituted with one group iii) such as carboxy.

[0084] Another variant for the radical R2is that said alkyl group is substituted with a group iv), in particular substituted with a phenyl group.

[0085] According to another embodiment of the present invention, R2represents a (C3-C8) cycloalkyl group, preferably a (C5-C7) cycloalkyl group such as cyclohexyl.

[0086] According to another embodiment of the present invention, R2represents a C5-C12aryl group optionally substituted with one or more hydroxyls and / or with one or more C1-C8alkoxy radicals, preferably a phenyl group, in particular which is not substituted.

[0087] According to one embodiment, R3represents a hydrogen atom.

[0088] According to another embodiment, R3represents a saturated, linear C1-C10or branched C3-C10alkyl group; in particular a linear (C1-C6) or branched (C3-C6) alkyl group, preferably a (C1-C4) alkyl group such as the methyl group.

[0089] Preferably, the compounds of formula (I) and the tautomer (I’) or salts thereof, optical isomers, racemates and / or solvates thereof, such as hydrates thereof and derivatives thereof, alone or as a mixture, have the following meanings:

[0090] R1denotes a radical chosen from a) a hydrogen atom, and b) a saturated, linear C1-C6or branched C3-C6alkyl group optionally substituted with one or more groups, which may be identical or different, chosen from i) -O-R3, and ii) -S-R3, preferably optionally substituted with one or more groups i);

[0091] R2denotes a radical chosen from a) a hydrogen atom; b) a saturated, linear C1-C10or branched C3-C10or cyclic C3-C8, such as C5-C6, hydrocarbon group optionally substituted with one or more groups, which may be identical or different, chosen from: i) -O-R3, ii) -S-R3, iii) -C(O)-O-R3, and iv) a phenyl group, optionally substituted with one or more hydroxyls and / or with one or more C1-C4alkoxy radicals such as methoxy, preferably substituted with one or more groups selected from i) and iii), preferably iii) such as carboxy; and

[0092] R3denotes a radical chosen from a) a hydrogen atom, and b) a saturated, linear C1-C6or branched C3-C6alkyl group.

[0093] Preferentially, the compounds of formula (I) and the tautomer (I’) or salts thereof, optical isomers and racemates thereof and / or solvates thereof, such as hydrates thereof, alone or as a mixture, have the following meanings:

[0094] R1denotes a radical chosen from a) a hydrogen atom, and b) a saturated, linear C1-C4or branched C3-C4alkyl group optionally substituted with one or more groups, which may be identical or different, chosen from i) -OR3, more preferably not being substituted;

[0095] R2denotes a radical chosen from a) a hydrogen atom, and b) a saturated, linear C1-C10or branched C3-C10or cyclic C3-C8, for instance C5-C6, hydrocarbon group, optionally substituted with one or more groups, which may be identical or different, chosen from i) -O-R3, iii) -C(O)-O-R3, and iv) a C5-C12aryl group, optionally substituted with one or more hydroxyls and / or with one or more C1-C4alkoxy radicals; and

[0096] R3denotes a radical chosen from a) a hydrogen atom, and b) a saturated, linear C1-C4or branched C3-C4alkyl group, such as methyl or ethyl.

[0097] Preferentially, the compounds of formula (I) and the tautomer (I’) or salts thereof, optical isomers, racemates and / or solvates thereof, such as hydrates and derivatives thereof, alone or as a mixture, have the following meanings:

[0098] R1is a hydrogen atom; and

[0099] R2denotes a radical chosen from a) a hydrogen atom, and b) a saturated, linear C1-C5or branched C3-C5or cyclic C3-C8, for instance C5-C6, hydrocarbon group, optionally substituted with one or more groups, which may be identical or different, chosen from iii) -C(O)-O-R3, preferably substituted with a group iii) -C(O)-O-R3; R2is more preferably still a saturated, linear C1-C4or branched C3-C4hydrocarbon group substituted with a group iii) -C(O)-OR3; and

[0100] R3denotes a radical chosen from a) a hydrogen atom, and b) a saturated, linear C1-C4or branched C3-C4alkyl group, such as methyl or ethyl.

[0101] According to another preferred embodiment, the compounds of formula (I) and the tautomer (I’) are selected from the compounds of formula (II) below and also the tautomers thereof of formula (II’) below, the salts thereof, the solvates thereof and the optical isomers thereof, and the racemates thereof, alone or as a mixture: (II)(II’)

[0102] In formulae (II) and (II’), R1and R3have the same meaning as R1and R3for the compounds of formulae (I) and (I’), and X denotes an alkylene radical -(CH2)n- with n being an integer ranging inclusively from 1 to 10, preferably ranging from 1 to 6, more preferably ranging from 1 to 4, such as 1, preferably R3represents a hydrogen atom.

[0103] Among the compounds of formula (I), the following compounds are preferably used, and the tautomer (I') thereof or salts thereof, optical isomers, racemates, and / or solvates thereof, such as hydrates and derivatives thereof, alone or as a mixture:No.StructureChemical nameCAS No.1 N-ethyl-2-thioxo-1,2-dihydropyridine-3-carboxamide91859-75-52 N-methyl-2-thioxo-1,2-dihydropyridine-3-carboxamide91859-74-43 N-octyl-2-thioxo-1,2-dihydropyridine-3-carboxamide91859-77-74 N-benzyl-2-thioxo-1,2-dihydropyridine-3-carboxamide91859-79-95 N-phenyl-2-thioxo-1,2-dihydropyridine-3-carboxamide104857-16-16 N-cyclohexyl-2-thioxo-1,2-dihydropyridine-3-carboxamide91859-78-87 N-[2-(4-methoxyphenyl)ethyl]-2-thioxo-1,2-dihydropyridine-3-carboxamide923682-88-68 N-(2-methylpropyl)-2-thioxo-1,2-dihydropyridine-3-carboxamide1100027-79-99 N-pentyl-2-thioxo-1,2-dihydropyridine-3-carboxamide330667-57-710 N-nonyl-2-thioxo-1,2-dihydropyridine-3-carboxamide1031149-44-611 N-(2-hydroxyethyl)-2-thioxo-1,2-dihydropyridine-3-carboxamide12 N,N-diethyl-2-mercaptonicotinamide13 N-ethyl-N-(2-hydroxyethyl)-2-thioxo-1,2-dihydropyridine-3-carboxamide14 N-(2,3-dihydroxypropyl)-2-thioxo-1,2-dihydropyridine-3-carboxamide15 N-(1,3-dihydroxypropan-2-yl)-2-thioxo-1,2-dihydropyridine-3-carboxamide16 ethyl N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]alaninate17 ethyl N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]phenylalaninate18 ethyl N-methyl-N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycinate19 ethyl N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycinate20 N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycine21 N-methyl-N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycine22 N,N-bis(2-hydroxyethyl)-2-thioxo-1,2-dihydropyridine-3-carboxamide23 N-(3-methoxypropyl)-2-thioxo-1,2-dihydropyridine-3-carboxamide24 N-butyl-2-thioxo-1,2-dihydropyridine-3-carboxamide

[0104] Among these compounds, the following compounds are more particularly preferred:No.StructureChemical nameCAS No.1 N-ethyl-2-thioxo-1,2-dihydropyridine-3-carboxamide91859-75-52 N-methyl-2-thioxo-1,2-dihydropyridine-3-carboxamide91859-74-44 N-benzyl-2-thioxo-1,2-dihydropyridine-3-carboxamide91859-79-96 N-cyclohexyl-2-thioxo-1,2-dihydropyridine-3-carboxamide91859-78-87 N-[2-(4-methoxyphenyl)ethyl]-2-thioxo-1,2-dihydropyridine-3-carboxamide923682-88-69 N-pentyl-2-thioxo-1,2-dihydropyridine-3-carboxamide330667-57-711 N-(2-hydroxyethyl)-2-thioxo-1,2-dihydropyridine-3-carboxamide12 N,N-diethyl-2-mercaptonicotinamide14 N-(2,3-dihydroxypropyl)-2-thioxo-1,2-dihydropyridine-3-carboxamide15 N-(1,3-dihydroxypropan-2-yl)-2-thioxo-1,2-dihydropyridine-3-carboxamide16 ethyl N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]alaninate17 ethyl N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]phenylalaninate18 ethyl N-methyl-N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycinate19 ethyl N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycinate20 N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycine21 N-methyl-N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycine

[0105] More preferably, among these compounds, the following compounds are more particularly preferred:No.StructureChemical nameCAS No.1 N-ethyl-2-thioxo-1,2-dihydropyridine-3-carboxamide91859-75-59 N-pentyl-2-thioxo-1,2-dihydropyridine-3-carboxamide330667-57-716 ethyl N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]alaninate18 ethyl N-methyl-N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycinate19 ethyl N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycinate20 N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycine21 N-methyl-N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycine

[0106] Even more preferably, among these compounds, the following compounds are more particularly preferred:No.StructureChemical nameCAS No.18 ethyl N-methyl-N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycinate19 ethyl N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycinate20 N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycine21 N-methyl-N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycine

[0107] In the most preferred embodiment, the compound according to the present invention is the following:20 N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycine(INCI name: 2-mercaptonicotinoyl glycine)

[0108] All the above compounds can be obtained by a chemical process known to a person skilled in the art, from commercially available reagents.

[0109] The thiopyridinone compound (1) may be prepared in accordance with the process described, for example, in document EP-A-3390363 or WO 2017 / 102349, which is incorporated by reference.

[0110] The thiopyridinone compound (1) may be an active ingredient or an active compound in cosmetic or dermatological products. The term "active" ingredient or compound used herein denotes an ingredient or a compound which has an active cosmetic or dermatological property, such as antioxidant, whitening, UV-screening and antibacterial effects. The thiopyridinone compound (1) used in the present invention can function as a depigmenting, decolorizing or whitening agent, and thus the composition according to the present invention can be used as a whitening product or as a cosmetic composition for whitening a keratin material.

[0111] The thiopyridinone compound (1) can be used as an agent for depigmenting, decolorizing or whitening the skin, body hair, eyelashes or hair, and also the lips and / or nails, and preferably the skin, in particular to remove pigmentation spots or age spots, and / or as an anti-tanning agent.

[0112] The amount of thiopyridinone compound(s) (1) in the composition according to the present invention may be 0.01% by weight or more, preferably 0.05% by weight or more, and more preferably 0.1% by weight or more, relative to the total weight of the composition.

[0113] Furthermore, the amount of thiopyridinone compound(s) (1) in the composition according to the present invention may be 10% by weight or less, preferably 5% by weight or less, and more preferably 3% by weight or less, relative to the total weight of the composition.

[0114] The amount of thiopyridinone compound(s) (1) in the composition according to the present invention may range from 0.01% to 10% by weight, preferably from 0.05% to 5% by weight, more preferably from 0.1% to 3% by weight, relative to the total weight of the composition.

[0115] According to a particular embodiment of the invention, the weight ratio of the amount of compounds chosen from the compounds of formula (I), the tautomers of formula (I’), salts thereof, solvates thereof, optical isomers thereof and racemates thereof, to the amount of water-soluble organic UV-screening agents is between 1 / 25 and 1 / 0.5, preferably between 1 / 10 and 1 / 0.5, and more preferentially between 1 / 10 and 1.Additional UV-screening agents

[0116] The composition according to the invention may also comprise at least one additional UV-screening agent other than water-soluble organic UV-screening agents.

[0117] According to one particular embodiment, the composition in accordance with the invention comprises at least one organic UV-screening agent other than water-soluble organic UV-screening agents, notably chosen from water-dispersible organic UV-screening agents, and lipophilic organic UV-screening agents.Water-dispersible organic UV-screening agents

[0118] The water-dispersible organic UV-screening agent(s) may be chosen from the following compounds.

[0119] Methylenebis(hydroxyphenylbenzotriazole) compounds:

[0120] Methylenebis(benzotriazolyl)tetramethylbutylphenol in the form of an aqueous dispersion of micronized particles with a volume-average particle size which ranges from 0.01 to 5 µm, and more preferentially from 0.01 to 2 µm and more particularly from 0.020 to 2 µm, with at least one alkyl polyglycoside surfactant having the structure CnH2n+1O(C6H10O5)xH, in which n is an integer from 8 to 16 and x is the mean degree of polymerization of the (C6H10O5) unit and ranges from 1.4 to 1.6 such as the aqueous dispersions described in patent GB-A-2 303 549, in particular the product sold under the trade name Tinosorb® M by BASF, or in the form of an aqueous dispersion of micronized particles with a volume-average particle size which ranges from 0.02 to 2 µm, and more preferentially from 0.01 to 1.5 µm and more particularly from 0.02 to 1 µm, in the presence of at least one polyglyceryl mono(C8-C20)alkyl ester with a degree of glycerol polymerization of at least 5, such as the aqueous dispersions described in patent application WO 2009 / 063392, in particular the product sold under the name Tinosorb WPGL by BASF.Triazine compounds:

[0121] - 3,3'-(1,4-phenylene)bis(5,6-diphenyl-1,2,4-triazine), having the INCI name Phenylene Bis-Diphenyltriazine, notably sold under the name Triasorb by Pierre Fabre;

[0122] - bis(ethylhexyloxyphenol)methoxyphenyl triazine in its water-dispersible form, having the INCI name Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine (and) Acrylates / C12-22 Alkyl Methacrylate Copolymer, under the trade name Tinosorb® S LiteAqua by the company BASF,

[0123] - symmetrical triazine screening agents substituted with naphthalenyl groups or polyphenyl groups used in micronized form (mean particle size of 0.02 to 3 µm) which may be obtained, for example, via the micronization process described in patent applications GB-A-2 303 549 and EP-A-893119, and notably in aqueous dispersion form, notably 2,4,6-tris(biphenyl)triazine and 2,4,6-tris(terphenyl)triazine sold under the name Tinosorb® A2B by the company BASF and included in patent applications WO 06 / 035000, WO 06 / 034982, WO 06 / 034991, WO 06 / 035007, WO 2006 / 034992 and WO 2006 / 034985.

[0124] Among the water-dispersible organic UV-screening agents, mention may also be made of the following screening agents:Benzophenone compounds:

[0125] 1,1’-(1,4-Piperazinediyl)bis[1-[2-[4-(diethylamino)-2-hydroxybenzoyl]phenyl]methanone] (CAS 919803-06-8), as described in patent application WO 2007 / 071584; this compound advantageously being used in micronized form (volume-mean size of 0.02 to 2 µm), which may be obtained, for example, according to the micronization process described in patent applications GB-A-2 303 549 and EP-A-893119, and notably in the form of an aqueous dispersion.Benzoxazole compounds:

[0126] 2-[4-(1,3-Benzoxazol-2-yl)phenyl]-1,3-benzoxazole, having the CAS No. 904-39-2.Lipophilic organic UV-screening agents

[0127] The lipophilic organic screening agent(s) may be chosen from cinnamic compounds; anthranilate compounds; salicylic compounds, dibenzoylmethane compounds, benzylidene camphor compounds; benzophenone compounds; β,β-diphenylacrylate compounds; triazine compounds; benzotriazole compounds; benzalmalonate compounds, notably those cited in patent US 5 624 663; benzimidazole derivatives; imidazoline compounds; bis-benzazolyl compounds, as described in patents EP 669 323 and US 2 463 264; methylenebis(hydroxyphenylbenzotriazole) compounds, as described in patent applications US 5 237 071, US 5 166 355, GB 2 303 549, DE 197 26 184 and EP 893 119; benzoxazole compounds, as described in patent applications EP 0 832 642, EP 1 027 883, EP 1 300 137 and DE 101 62 844; screening polymers and screening silicones, such as those described notably in patent application WO 93 / 04665; dimeric α-alkylstyrene derivatives, such as those described in patent application DE 198 55 649; 4,4-diarylbutadiene compounds, as described in patent applications EP 0 967 200, DE 197 46 654, DE 197 55 649, EP-A-1 008 586, EP 1 133 980 and EP 133 981, and mixtures thereof.

[0128] Preferably, the lipophilic organic screening agent(s) are chosen from salicylic compounds, dibenzoylmethane compounds, benzylidene camphor compounds; benzophenone compounds; triazine compounds; benzotriazole compounds; and mixtures thereof.

[0129] As examples of lipophilic organic photoprotective agents, mention may be made of those denoted hereinbelow under their INCI name and / or their chemical name.Cinnamic compounds:

[0130] Ethylhexyl methoxycinnamate notably sold under the trade name Parsol® MCX by the company DSM Nutritional Products;

[0131] Isoamyl p-methoxycinnamate, sold under the trade name Neo Heliopan E 1000® by the company Symrise.Dibenzoylmethane compounds:

[0132] Butylmethoxydibenzoylmethane (or avobenzone) notably sold under the trade name Parsol® 1789 by the company DSM Nutritional Products.Salicylic compounds:

[0133] Homosalate sold under the name Parsol® HMS by the company DSM Nutritional Products;

[0134] Ethylhexyl salicylate sold under the name Neo Heliopan® OS by the company Symrise.β,β-Diphenylacrylate compounds:

[0135] Octocrylene, notably sold under the trade name Uvinul® N 539 T by the company BASF.Benzophenone compounds:

[0136] Benzophenone-3 or Oxybenzone, sold under the trade name Uvinul® M 40 by the company BASF,

[0137] Hexyl (diethylamino-hydroxybenzoyl)benzoate, sold under the trade name Uvinul® A Plus or, as a mixture with ethylhexyl methoxycinnamate, under the trade name Uvinul® A Plus B by the company BASF.Benzylidene camphor compounds:

[0138] 4-Methylbenzylidene camphor, sold under the name Eusolex® 6300 by the company Merck.Phenylbenzotriazole compounds:

[0139] Drometrizole trisiloxane manufactured under the name Mexoryl® XL by the company Noveal.

[0140] Methylenebis(hydroxyphenylbenzotriazole) compounds:

[0141] Methylenebis(benzotriazolyl)tetramethylbutylphenol notably in solid form, such as the product sold under the trade name Mixxim BB / 100® by the company Fairmount Chemical.Triazine compounds:

[0142] - bis-Ethylhexyloxyphenol methoxyphenyl triazine sold under the trade name Tinosorb® S by the company BASF,

[0143] - Ethylhexyl triazone, notably sold under the trade name Uvinul® T 150 by the company BASF,

[0144] - Diethylhexyl butamido triazone sold under the trade name Uvasorb® HEB by the company 3V Sigma,

[0145] - the symmetrical triazine screening agents substituted with naphthalenyl groups or polyphenyl groups, described in patent US 6 225 467, patent application WO 2004 / 085412 (see compounds 6 and 9) or the document “Symmetrical Triazine Derivatives” IP.COM IPCOM000031257 Journal, INC West Henrietta, NY, US (September 20, 2004).Anthranilic compounds:

[0146] Menthyl anthranilate sold under the trade name Neo Heliopan® MA by the company Symrise.Benzalmalonate compounds:

[0147] Polyorganosiloxane bearing benzalmalonate functions, for instance Polysilicone-15, sold under the trade name Parsol SLX® by the company DSM Nutritional Products.

[0148] According to a preferred embodiment, the additional UV-screening agent(s) are chosen from lipophilic organic UV-screening agents, preferably chosen from diethylamino hydroxybenzoyl hexyl benzoate (sold especially under the trade name Uvinul® A Plus or as a mixture with ethylhexyl methoxycinnamate under the trade name Uvinul® A Plus B by the company BASF), drometrizole trisiloxane (manufactured especially under the name Mexoryl® XL by the company Noveal), bis-ethylhexyloxyphenol methoxyphenyl triazine (sold especially under the trade name Tinosorb® S by the company BASF), ethylhexyl triazone (sold especially under the trade name Uvinul® T 150 by the company BASF) and butyl methoxydibenzoylmethane (sold especially under the trade name Parsol 1789 ® by the company DSM Nutritional Products).

[0149] The additional UV-screening agent(s) may be present in an amount of between 0.2% and 30% by weight, preferably between 0.5% and 25% by weight, preferentially between 1% and 20% by weight and even more preferentially between 2% and 18% by weight relative to the total weight of the composition.

[0150] According to another embodiment, the additional UV-screening agent(s) are present in an amount of less than 15% by weight, preferably less than 10% by weight, even more preferentially less than 5% by weight, better still less than 3% by weight and even better still less than 1% by weight relative to the total weight of the composition.Aqueous phase

[0151] The composition in accordance with the invention comprises at least one aqueous phase.

[0152] According to a particular embodiment, the composition in accordance with the invention comprises at least one aqueous phase comprising at least water.

[0153] The aqueous phase may also comprise at least one other organic solvent that is soluble in water, at 25°C, chosen, for example, from:

[0154] - C1-C4monoalkanols. The term "C1-C4monoalkanol" means any linear or branched saturated alkane compound containing from 1 to 4 carbon atoms and only one hydroxyl (OH) function. The C1-C4monoalkanol(s) present in the compositions of the invention may be chosen from methanol, ethanol, propanol, isopropanol and butanol, or mixtures thereof. Ethanol will be chosen more particularly;

[0155] - polyols notably containing from 2 to 20 carbon atoms, preferably from 2 to 6 carbon atoms, for instance glycerol, diglycerol, propylene glycol, isoprene glycol, dipropylene glycol, butylene glycol, hexylene glycol, 1,2-propanediol, 1,3-propanediol, pentylene glycol, caprylyl glycol, simple sugars, water-soluble polyalkylene glycols; and

[0156] - mixtures thereof.

[0157] The monoalkanol(s) may be present in concentrations ranging from 0.2% to 90% by weight, more preferentially from 0.5% to 50% by weight, and preferably from 1% to 10% by weight relative to the total weight of the composition.

[0158] According to a particular embodiment, the composition according to the invention comprises at least one polyol, notably as described above. The presence of at least one polyol makes it possible notably to improve the cosmetic properties, such as glidance on application, and reduces the tackiness. Preferably, it comprises at least 0.5% by weight of polyols relative to the total weight of the composition, preferably at least 1% by weight of polyols relative to the total weight of the composition, preferably at least 3% by weight of polyols relative to the total weight of the composition, preferably at least 5% by weight of polyols relative to the total weight of the composition, preferably from 10% to 50% by weight, preferably from 15% to 40% by weight, preferably from 18% to 35% by weight and even more preferentially from 20% to 30% by weight.

[0159] Preferably, the composition according to the invention comprises a polyol, preferably glycerol, butylene glycol, propylene glycol, 1,2-propanediol, caprylyl glycol, pentylene glycol or dipropylene glycol, and mixtures thereof.

[0160] According to one particular embodiment, the cosmetic composition according to the invention may comprise an acid and / or a base.

[0161] Among the acidifying agents, examples that may be mentioned include mineral or organic acids, such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids, such as acetic acid, tartaric acid, citric acid or lactic acid, and sulfonic acids.

[0162] Among the basifying agents, examples that may be mentioned include aqueous ammonia, alkali metal carbonates, alkanolamines, such as mono-, di- and triethanolamines and derivatives thereof, sodium hydroxide or potassium hydroxide.

[0163] Preferably, the cosmetic composition comprises one or more basifying agents chosen from alkanolamines, in particular triethanolamine, and sodium hydroxide.

[0164] According to one particular embodiment, the composition according to the invention has a pH of between 4 and 10, preferably between 5 and 8.5, and preferentially between 5.5 and 8.

[0165] The pH of the composition in accordance with the invention can be measured using a Mettler Toledo MPC227, SevenEasy pH or SevenGo SG2 pH meter at room temperature (25°C) and atmospheric pressure.

[0166] According to a particular embodiment of the invention, the overall aqueous phase, including all the hydrophilic substances of the composition that are capable of being dissolved or dispersed in this same phase, including hydrophilic screening agents such as water-soluble screening agents and water-dispersible screening agents, and also the thiopyridinone compound(s) as defined previously, represents from 5% to 100% by weight, preferably from 20% to 100% by weight, and preferentially from 30% to 99% by weight, and even more preferentially from 30% to 90% by weight, relative to the total weight of the composition.

[0167] The composition preferably comprises at least 5% by weight of water relative to the total weight of the composition, preferably from 10% to 99% by weight, even more preferentially from 20% to 90% by weight, better still from 30% to 80% by weight, and even better still from 40% to 70% by weight, relative to the total weight of the composition.Fatty phase

[0168] According to a particular embodiment, the composition in accordance with the invention comprises at least one fatty phase.

[0169] The fatty phase may be constituted of all the fatty substances conventionally used in the cosmetic or dermatological fields. It may notably comprise at least one oil. The fatty phase also comprises the lipophilic screening agent(s) present in the composition.

[0170] The term “oil” means any fatty substance that is in liquid form at room temperature (20-25°C) and atmospheric pressure (760 mmHg). These oils may be volatile or non-volatile.

[0171] For the purposes of the invention, the term “volatile oil” means an oil that is capable of evaporating on contact with the skin or the keratin fiber in less than one hour, at room temperature and atmospheric pressure. The volatile oil(s) of the invention are volatile cosmetic oils, which are liquid at room temperature, having a non-zero vapor pressure, at room temperature and atmospheric pressure, ranging in particular 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).

[0172] The term “non-volatile oil” means an oil that remains on the skin or the keratin fiber at room temperature and atmospheric pressure for at least several hours, and that notably has a vapor pressure of less than 10-3mmHg (0.13 Pa).

[0173] For the purposes of the present invention, the term “hydrocarbon-based oil” means any oil predominantly comprising carbon and hydrogen atoms, and optionally one or more heteroatoms, in particular nitrogen and oxygen. Thus, these oils may notably contain one or more ester, ether, fluoro, carboxylic acid and / or alcohol groups.

[0174] The term “silicone oil” means an oil comprising at least one silicon atom and notably at least one Si-O group.

[0175] As non-volatile hydrocarbon-based oils that can be used according to the invention, mention may notably be made of:

[0176] (i) hydrocarbon-based 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 C4to C24, these chains possibly being linear or branched, and saturated or unsaturated; these oils are notably wheatgerm oil, sunflower oil, grapeseed oil, sesame seed 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, marrow oil, blackcurrant oil, evening primrose oil, millet oil, barley oil, quinoa oil, rye oil, safflower oil, candlenut oil, passion flower oil and musk rose oil; or alternatively 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;

[0177] (ii) synthetic ethers containing from 10 to 40 carbon atoms;

[0178] (iii) linear or branched hydrocarbons of mineral or synthetic origin, such as petroleum jelly, polydecenes, hydrogenated polyisobutene, such as Parleam, squalane and mixtures thereof;

[0179] (iv) synthetic esters, such as the oils of formula RCOOR’ in which R represents the residue of a linear or branched fatty acid comprising from 1 to 40 carbon atoms and R’ represents a hydrocarbon chain that is notably branched, containing from 1 to 40 carbon atoms, with the proviso that R + R’ ≥ 10, for instance purcellin oil (cetostearyl octanoate), isopropyl myristate, isopropyl palmitate, C12-C15 alkyl benzoate, 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 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 Stéarinerie Dubois, alcohol or polyalcohol octanoates, decanoates or ricinoleates, such as propylene glycol dioctanoate; hydroxylated esters, such as isostearyl lactate, diisostearyl malate; and pentaerythritol esters; citrates or tartrates, such as linear C12-C13 dialkyl tartrates, such as those sold under the name Cosmacol ETI® by the company Enichem Augusta Industriale, and also linear C14-C15 dialkyl tartrates such as those sold under the name Cosmacol ETL® by the same company; acetates;

[0180] (v) fatty alcohols that are liquid at room temperature, bearing 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 or 2-undecylpentadecanol;

[0181] (vi) higher C12-C22 fatty acids such as oleic acid, linoleic acid or linolenic acid;

[0182] (vii) carbonates, such as dicaprylyl carbonate, such as the product sold under the name Cetiol CC® by the company Cognis;

[0183] and mixtures thereof.

[0184] Among the non-volatile hydrocarbon-based oils which can be used according to the invention, preference will be given more particularly to glyceride triesters and in particular to caprylic / capric acid triglycerides, synthetic esters and in particular diisopropyl adipate, diisopropyl sebacate, isopropyl palmitate, dicaprylyl carbonate, isononyl isononanoate, oleyl erucate, C12-C15 alkyl benzoate, 2-ethylphenyl benzoate and fatty alcohols, in particular octyldodecanol. Preferably, the non-volatile hydrocarbon-based oils are chosen from diisopropyl adipate, diisopropyl sebacate, isopropyl palmitate and dicaprylyl carbonate.

[0185] As volatile hydrocarbon-based oils that may be used according to the invention, mention may notably be made of hydrocarbon-based oils containing from 8 to 16 carbon atoms and notably branched C8-C16 alkanes, such as C8-C16 isoalkanes of petroleum origin (also known as isoparaffins), such as isododecane (also known as 2,2,4,4,6-pentamethylheptane), isodecane or isohexadecane, the oils sold under the Isopar or Permethyl trade names, branched C8-C16 esters, isohexyl neopentanoate, and mixtures thereof.

[0186] Mention may also be made of the alkanes described in the Cognis patent applications WO 2007 / 068371 or WO 2008 / 155059 (mixtures of different alkanes differing by at least one carbon). These alkanes are obtained from fatty alcohols, which are themselves obtained from coconut oil or palm oil. Mention may be made of 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. Mention may also be made of 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.

[0187] Other volatile hydrocarbon-based oils, such as petroleum distillates, in particular those sold under the name Shell Solt® by Shell, can also be used. According to one embodiment, the volatile solvent is chosen from volatile hydrocarbon-based oils containing from 8 to 16 carbon atoms, and mixtures thereof.

[0188] The non-volatile silicone oils may be notably chosen from non-volatile polydimethylsiloxanes (PDMSs), polydimethylsiloxanes including alkyl or alkoxy groups which are pendent and / or at the end of the silicone chain, these groups each containing from 2 to 24 carbon atoms, or phenyl silicones, such as phenyl trimethicones, phenyl dimethicones, phenyltrimethylsiloxydiphenylsiloxanes, diphenyl dimethicones, diphenylmethyldiphenyltrisiloxanes or 2-phenylethyl trimethylsiloxysilicates.

[0189] Volatile silicone oils that may be mentioned, for example, include volatile linear or cyclic silicone oils, notably those with a viscosity ≤ 8 centistokes (8×10-6m2 / s) and notably containing from 2 to 7 silicon atoms, these silicones optionally including alkyl or alkoxy groups containing from 1 to 10 carbon atoms. As volatile silicone oils that may be used in the invention, mention may notably be made of octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, heptamethylhexyltrisiloxane, heptamethyloctyltrisiloxane, hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane and dodecamethylpentasiloxane, and mixtures thereof.

[0190] Mention may also be made of the volatile linear alkyltrisiloxane oils such as:

[0191] 3-butyl-1,1,1,3,5,5,5-heptamethyltrisiloxane,

[0192] 3-propyl-1,1,1,3,5,5,5-heptamethyltrisiloxane, and

[0193] 3-ethyl-1,1,1,3,5,5,5-heptamethyltrisiloxane.

[0194] Use may also be made of volatile fluoro oils, such as nonafluoromethoxybutane, nonafluoromethoxybutane, decafluoropentane, tetradecafluorohexane, dodecafluoropentane, and mixtures thereof.

[0195] The fatty phase according to the invention may also comprise other fatty substances, mixed with or dissolved in the oil.

[0196] Another fatty substance that may be present in the oily phase may be, for example:

[0197] - a fatty acid chosen from fatty acids including from 8 to 30 carbon atoms, different from the fatty-chain amino acids as defined previously, such as stearic acid, lauric acid, palmitic acid and oleic acid;

[0198] - a gum chosen from silicone gums (dimethiconol);

[0199] - a pasty compound, such as polymeric or non-polymeric silicone compounds, esters of an oligomeric glycerol, arachidyl propionate, fatty acid triglycerides and derivatives thereof;

[0200] - and mixtures thereof.

[0201] According to a particular embodiment of the invention, the overall fatty phase, including all the lipophilic substances of the composition which are capable of being dissolved in this same phase, including lipophilic screening agents, represents from 0% to 90% by weight and preferentially from 10% to 70% by weight, and even more preferentially from 20% to 40% by weight relative to the total weight of the composition.Cosmetic active ingredients

[0202] The composition of the present invention may comprise at least one cosmetic active agent.

[0203] Examples of cosmetic active agents that may be mentioned include moisturizers; natural extracts; vitamins and derivatives thereof; alpha-hydroxy acids; retinoids; extracts of algae, fungi, plants, yeasts and bacteria; enzymes; tautening agents; agents acting on the microcirculation, and mixtures thereof.

[0204] A person skilled in the art can readily adjust the amount of cosmetic active principle according to the end use of the composition according to the present invention.Additional adjuvants or additives

[0205] The composition of the present invention may also comprise conventional cosmetic adjuvants or additives, for example fragrances, chelating agents, preserving agents and bactericides, additional thickeners, pH regulators, additional fillers, and mixtures thereof.

[0206] A person skilled in the art can select the amount of additional adjuvants or additives so as not to adversely affect the end use of the composition according to the present invention.Presentation forms

[0207] According to one particular embodiment, the compositions according to the invention have a viscosity of at least 0.10 Pa.s, measured at 25°C and under atmospheric pressure with a Rheomat RM100® viscometer from Lamy Rheology after 10 minutes of stirring. Preferably, the viscosity is between 0.10 and 20 Pa.s, more preferentially between 0.10 and 10 Pa.s, and better still between 0.10 and 5 Pa.s.

[0208] Such a viscosity typically allows the compositions to have a gelled texture.

[0209] The compositions according to the invention may be prepared according to techniques that are well known to those skilled in the art.

[0210] The compositions according to the invention may be in aqueous form, for example in the form of an aqueous gel or aqueous-alcoholic composition, but also in the form of an emulsion, notably an oil-in-water or water-in-oil, or two-phase, emulsion.

[0211] According to one particular embodiment, the composition of the invention does not comprise an oily phase. Preferably, the compositions according to the invention are oil-free. For the purposes of the invention, the term "oil-free" denotes a composition comprising only one liquid phase, which is an aqueous phase (a liquid phase comprising water). The term "oil" does not cover, for example, water-soluble active ingredients, water-soluble or water-dispersible UV-screening agents and water-soluble glycols.

[0212] In another particular embodiment, the composition according to the invention is in the form of an emulsion. When the composition according to the invention is in the form of an oil-in-water emulsion, it comprises an oily phase dispersed in an aqueous phase. When the composition according to the invention is in the form of a water-in-oil emulsion, it comprises an aqueous phase dispersed in an oily phase.

[0213] In the case of compositions in the form of oil-in-water or water-in-oil emulsions, the emulsification processes that may be used are of the paddle or impeller, rotor-stator and HPH type.

[0214] It is also possible, via HPH (between 50 and 800 bar), to obtain stable dispersions with drop sizes that may be as low as 100 nm.

[0215] The emulsions may generally contain at least one emulsifier chosen from amphoteric, anionic, cationic or nonionic emulsifiers, used alone or as a mixture. The emulsifiers are appropriately chosen according to the emulsion to be obtained (W / O or O / W).

[0216] Examples of W / O nonionic emulsifying surfactants that may be mentioned include alkyl esters or ethers of sorbitan, of glycerol, of polyol or of sugars; silicone surfactants, for instance dimethicone copolyols, such as the mixture of cyclomethicone and of dimethicone copolyol, sold under the name DC 5225 C® by Dow Corning, and alkyldimethicone copolyols such as laurylmethicone copolyol sold under the name Dow Corning 5200 Formulation Aid by Dow Corning; cetyldimethicone copolyol, such as the product sold under the name Abil EM 90R® by Goldschmidt, and the mixture of cetyldimethicone copolyol, of polyglyceryl isostearate (4 mol) and of hexyl laurate, sold under the name Abil WE O9® by Goldschmidt. One or more coemulsifiers, which may be chosen advantageously from the group comprising polyol alkyl esters, may also be added thereto.

[0217] Mention may also be made of non-silicone emulsifying surfactants, notably alkyl esters or ethers of sorbitan, of glycerol, of polyol or of sugars.

[0218] Polyol alkyl esters that may notably be mentioned include polyethylene glycol esters, for instance PEG-30 dipolyhydroxystearate, such as the product sold under the name Arlacel P135® by the company Croda.

[0219] Examples of glycerol and / or sorbitan esters that may be mentioned include polyglyceryl isostearate, such as the product sold under the name Isolan GI 34® by the company Goldschmidt; sorbitan isostearate, such as the product sold under the name Arlacel 987® by the company Croda; sorbitan glyceryl isostearate, such as the product sold under the name Arlacel 986® by the company Croda, and mixtures thereof.

[0220] For the O / W emulsions, examples of nonionic emulsifying surfactants that may be mentioned include polyoxyalkylenated (more particularly polyoxyethylenated and / or polyoxypropylenated) esters of fatty acids and of glycerol, such as the polyethylene glycol stearic acid ester having the INCI name PEG-100 Stearate sold under the name Myrj S100-PA-(SG) by the company Croda; oxyalkylenated esters of fatty acids and of sorbitan; polyoxyalkylenated (in particular polyoxyethylenated and / or polyoxypropylenated) esters of fatty acids, optionally in combination with an ester of fatty acid and of glycerol, such as the PEG-100 stearate / glyceryl stearate mixture sold, for example, by the company Croda under the name Arlacel 165; oxyalkylenated (oxyethylenated and / or oxypropylenated) ethers of fatty alcohols; esters of sugars, such as sucrose stearate; or ethers of fatty alcohol and of sugar, notably alkyl polyglucosides (APGs), such as decyl glucoside and lauryl glucoside, sold, for example, by the company Henkel under the respective names Plantaren 2000® and Plantaren 1200®, cetostearyl glucoside, optionally as a mixture with cetostearyl alcohol, sold, for example, under the name Montanov 68® by the company SEPPIC, under the name Tegocare CG90® by the company Goldschmidt and under the name Emulgade KE3302® by the company Henkel, and arachidyl glucoside, for example in the form of the mixture of arachidyl and behenyl alcohols and of arachidyl glucoside sold under the name Montanov 202® by the company SEPPIC. According to a particular embodiment of the invention, the mixture of the alkyl polyglucoside as defined above with the corresponding fatty alcohol may be in the form of a self-emulsifying composition, for example as described in WO-A-92 / 06778.

[0221] As anionic surfactants for producing O / W emulsions, mention may be made of surfactants chosen from amino acids modified with at least one C8-C30, preferably C8-C24, hydrocarbon chain, and salts thereof, in particular acyl glutamic acids (INCI name: acyl glutamic acid) or a salt thereof (acyl glutamates), such as stearoyl glutamic acid or a salt thereof, notably sodium stearoyl glutamate (INCI name).

[0222] Such compounds are sold under the name Amisoft by the company Ajinomoto and notably under the references Amisoft CA, Amisoft LA, Amisoft HS 11 PF, Amisoft MK-11, Amisoft LK-11, Amisoft CK-11, or even under the name Eumulgin SG by the company Cognis.

[0223] As anionic surfactants for producing O / W emulsions, mention may also be made of hydrophobically modified polysaccharides, in particular inulins modified with hydrophobic chains such as alkyl carbamate groups, in particular C8-C18alkyl carbamate groups, and more particularly lauryl carbamate groups.

[0224] Examples of these compounds that may notably be mentioned include the product sold under the name Inutec SL1 by the company Creachem.

[0225] The compositions according to the invention find their application in a large number of treatments, notably cosmetic treatments, for the skin, the lips and the hair, including the scalp, notably for protecting and / or caring for the skin, the lips and / or the hair, and / or for making up the skin and / or the lips.

[0226] Another subject of the present invention consists of the use of the compositions according to the invention as defined above for the manufacture of products for the cosmetic treatment of the skin, the lips, the nails, the hair, the eyelashes, the eyebrows and / or the scalp, notably care products, antisun products and makeup products.EXAMPLES

[0227] The present invention will now be described more specifically by means of examples, which do not in any way limit the scope of the invention. However, the examples make it possible to support specific features, variants and preferred embodiments of the invention.

[0228] A - Example of the synthesis of thiopyridinone compounds of formula (I) or (I')

[0229] Step 1: Synthesis of ethyl N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycinate

[0230] Route 1: via 2-mercaptonicotinic acid

[0231] Introduced into a round-bottomed flask are thionicotinic acid in acetonitrile, followed by carbonyldiimidazole (CDI). The resulting mixture is refluxed for one hour and is then left at ambient temperature.

[0232] After returning to ambient temperature, ethyl glycinate hydrochloride is added and then the resulting mixture is heated again to a temperature of 60°C for 3 hours. The mixture is then left at ambient temperature overnight.

[0233] After the overnight period, the reaction medium is evaporated. The residue is taken up in dichloromethane and washed twice with 2N HCl.

[0234] The organic phase is dried over anhydrous sodium sulfate and then evaporated and purified over silica, dichloromethane 97 / methanol 3.

[0235] The fractions are evaporated.

[0236] A light yellow powder is obtained.

[0237] Route 2: via 2-chloronicotinic acid

[0238] In a three-necked flask, 2-chloronicotinic acid (250.0 g, 1.587 mol) is introduced into ethyl acetate (500 ml) and then SOCl2(210.0 g, 1.761 mol) is added dropwise to the mixture.

[0239] The combined mixture is refluxed until complete conversion. Once the reaction is complete, the mixture is cooled to ambient temperature and diluted with ethyl acetate (375 ml).

[0240] A solution of ethyl glycinate hydrochloride (265.8 g, 1.904 mol) diluted in water (400 ml) and of triethylamine (393.5 g, 3.88 mol) is then added to the mixture.

[0241] The combined mixture is stirred for a period ranging from 3 to 4 hours and then the ethyl acetate is removed under vacuum.

[0242] The aqueous solution thus obtained is then diluted with water (1250 ml) and then acidified with 3N HCl (25 ml).

[0243] Sodium thiosulfate (1379 g, 5.555 mol) is then added and the combined mixture is then refluxed for 6 hours. After cooling to 10°C, the yellow solid is filtered off and washed with water (3 × 750 ml).

[0244] The crude product is then treated with carbon black in a 75 / 25 ethanol / water mixture.

[0245] The carbon black is then filtered off hot and the ethanol is evaporated off. The combined mixture is cooled to ambient temperature, then the product is filtered off and dried under vacuum.

[0246] A light yellow powder is thus obtained.

[0247] The 1H NMR and mass spectra are in accordance with the structure.

[0248] Melting point: 151°C (capillary tube).

[0249] Step 2: Synthesis of the compound N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycine from the compound obtained in step 1

[0250] Ethyl N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycinate (48 g, 0.317 mol) and a 95% EtOH solution (48 ml) are introduced into a three-necked flask.

[0251] The resulting mixture is cooled to 10°C.

[0252] A solution of NaOH (16 g) in 144 ml of water is added dropwise to the mixture.

[0253] The organic solvent is evaporated off and the pH of the mixture is then adjusted to a value of 3-4. The mixture is then cooled to a temperature of between 0 and 10°C and is then filtered.

[0254] The product thus obtained is washed with water and dried under vacuum.

[0255] A light yellow powder is obtained.

[0256] The 1H NMR and mass spectra are in accordance with the structure.

[0257] Melting point: 241.0-241.8°C (capillary tube).

[0258] Example 2: Synthesis of compounds I-1 and I-2:

[0259] Compound I-1

[0260] The (2-mercaptonicotinoyl)glycine obtained in example 1 (20.000 g, 1 eq, 94.242 mmol) and DMF (100 ml) are introduced into a 250 ml round-bottomed flask.

[0261] The combined mixture is stirred until a clear solution is obtained and carbonyldiimidazole (16.809 g, 1.1 eq, 103.67 mmol) is then added in portions.

[0262] The resulting suspension is stirred at a temperature of 20°C until there is no bubbling (typically for one hour).

[0263] Ethyl glycinate hydrochloride (14.470 g, 1.1 eq, 103.67 mmol) is then added and the combined mixture is then stirred for one hour at a temperature of 20°C.

[0264] The reaction medium is then added slowly to a 10% aqueous NaHCO3solution with stirring.

[0265] The suspension obtained is filtered through a frit to afford a solid which is rinsed with distilled water. The solid is dried at a temperature of 50°C under vacuum to obtain ethyl (2-mercaptonicotinoyl)glycylglycinate (compound I-1) in the form of a yellow powder.

[0266] The spectroscopic analyses are in accordance with the structure shown.

[0267] Compound I-2

[0268] Compound I-1, as obtained above, (ethyl (2-mercaptonicotinoyl)glycylglycinate) (13.440 g, 1 eq, 45.202 mmol) and distilled water (70 ml) are introduced into a 250 ml round-bottomed flask.

[0269] With stirring, a 50% sodium hydroxide solution is added until a pH value of around 12-13 is reached while maintaining the temperature below 25°C. The resulting mixture is stirred for one hour at a temperature of 25°C and then the pH is adjusted to a value of 2 with 37% hydrochloric acid.

[0270] The suspension obtained is filtered through a frit and then the resulting solid is rinsed with distilled water.

[0271] The solid is dried at 50°C under vacuum to obtain compound I-2 (2-mercaptonicotinoyl)glycylglycine in the form of a yellow powder.

[0272] B - Examples of photostability of compound I-2 in the presence of water-soluble organic UV-screening agents

[0273] The following solutions were prepared at room temperature with various water-soluble organic UV-screening agents, by mixing the ingredients that appear in the table below. The numerical values for the amounts of the ingredients are all based on “% by weight” of active materials.

[0274] SolutionINCI name1*2*3*4*5POLYSORBATE 201.001.001.001.001.00AQUAqs 100qs 100qs 100qs 100qs 100PHENYLBENZIMIDAZOLE SULFONIC ACID8.00--8.00-TEREPHTHALYLIDENE DICAMPHOR SULFONIC ACID-10.00-5.00-DISODIUM PHENYL DIBENZIMIDAZOLE TETRASULFONATE--10.0010.00-CAPRYLYL GLYCOL0.300.300.300.300.30PROPANEDIOL3.003.003.003.003.002-MERCAPTONICOTINOYL GLYCINE(Compound I-2 of example A)1.001.001.001.001.00

[0275] * = composition according to the invention

[0276] Evaluation of the photostability of compound I-2 (INCI name: 2-MERCAPTONICOTINOYL GLYCINE)Exposure conditions

[0277] The formulations are spread on polymethyl methacrylate (PMMA) plates without anti-UV additive, with an etched face having a particle size of from 5 to 6.5 µm. A thin film of 2 to 2.1 mg of formulation per cm² of plate is deposited.

[0278] For each formulation, deposits on 8 plates are prepared:

[0279] 4 plates are exposed to specific UV doses in a Suntest unit (CPS from Hereaus (Atlas / Ametek)) which simulates solar radiation (exposed test plates). A dose of 16 J / cm² is applied, representative of realistic sun exposure.

[0280] 4 plates are not exposed to UV radiation and will be used as reference samples (reference plates). They are stored in an oven at 40°C for the same duration as the UV exposure time of the other 4 plates.

[0281] All the samples are then quantified using the following UPLC-UV method.

[0282] Quantification of compound I-2 and evaluation of the photostability

[0283] Removal of the formulation on the plates is carried out with a mixture of H3PO4(0.1%) / methanol (90:10 (v / v)) assisted by sonication.

[0284] All the samples are then quantified using the following UPLC-UV method:

[0285] - System: Waters ACQUITY UPLC I-Class or equivalent;

[0286] - Column: ACQUITY UPLC BEH Shield RP18 (Waters), 1.7 µm, 2.1×100 mm or equivalent;

[0287] - Mobile phase: 12-minute gradient of a mixture of eluent A (0.1% aqueous solution of phosphoric acid) & eluent B (methanol);

[0288] - Flow rate: 0.4 ml / min;

[0289] - Detection wavelength: 296 nm.

[0290] The standards for compound I-2 are prepared by dissolution / dilution in a mixture of H3PO4(0.1%) / methanol (90:10 (v / v)) so as to correspond to the linearity of the method.

[0291] Results expressed as residual fraction (RF):

[0292] Results

[0293] The results obtained are summarized in the table below:Photostability as a percentage of compound I-2RF (%)1* after exposure82% residual2* after exposure71% residual3* after exposure74% residual4* after exposure86% residual5 after exposure63% residual

[0294] These results show that in compositions 1 to 4 according to the invention, which comprise at least one water-soluble organic UV-screening agent, compound I-2 has a significantly improved photostability than in comparative composition 5 which does not contain any water-soluble organic UV-screening agent. Specifically, the content of residual compound I-2 after exposure to UV radiation is markedly higher in compositions 1 to 4 than in composition 5.D - Illustrative example

[0295] In this example, the amounts of the ingredients present in the compositions are given as weight percentages of starting materials, relative to the total weight of the composition.

[0296] The following composition was prepared.PhaseINCI nameComposition out of 100 gA1STEARIC ACID2A1GLYCERYL STEARATE (and) PEG-100 STEARATE1.5A1ISOPROPYL LAUROYL SARCOSINATE6A1ETHYLHEXYL TRIAZONE2A1CETYL ALCOHOL0.7A1BIS-ETHYLHEXYLOXYPHENOL METHOXYPHENYL TRIAZINE2.7A1DROMETRIZOLE TRISILOXANE0.5A1BUTYL METHOXYDIBENZOYLMETHANE1.7A1TRIETHANOLAMINE0.3A1ISOPROPYL MYRISTATE8A1ETHYLHEXYL SALICYLATE4.5A1CAPRYLYL GLYCOL0.3A2TOCOPHEROL0.5B1AQUA20B1TRIETHANOLAMINE0.57B1TRISODIUM ETHYLENEDIAMINE DISUCCINATE0.155B1GLYCEROL9.15B12-MERCAPTONICOTINOYL GLYCINE(compound I-2)0.5B1PROPYLENE GLYCOL4B1HYDROXYACETOPHENONE0.3B2TEREPHTHALYLIDENE DICAMPHOR SULFONIC ACID in aqueous solution containing 32% AM1DISOPROPYL LAUROYL SARCOSINATE3DCARBOMER0.4DAMMONIUM POLYACRYLOYLDIMETHYL TAURATE0.4EAQUA16.305EPHENYLBENZIMIDAZOLE SULFONIC ACID3.6ETRIETHANOLAMINE1.92JALCOHOL DENAT.7Procedure

[0297] In a beaker, mix the ingredients of phase A1 and bring to 80°C until the mixture is liquid and clear. Cool to 65°C, then add phase A2. Phase A is obtained.

[0298] In a beaker, mix the ingredients of phase B1 and then of phase B2 and bring to 65°C. Phase B is obtained.

[0299] Gradually pour phase A into phase B while maintaining vigorous impeller stirring for 10 minutes at 65°C. Turn off the heating and maintain continuous stirring with blades until the end of production.

[0300] Mix the ingredients of phase D and add to the mixture of phases A+B, stir for 5 minutes with an impeller, and then add the premixed ingredients of phase E. Stir for 5 minutes with an impeller.

[0301] Once the mixture has returned to room temperature, add phase J, and stir for 5 minutes with an impeller.

Claims

A composition, and in particular a cosmetic or dermatological composition, comprising:a) at least one aqueous phase;b) at least one water-soluble organic UV-screening agent; andc) at least one compound selected from the compounds of formula (I), tautomers of formula (I’), salts thereof, solvates thereof, such as hydrates thereof, optical isomers thereof, racemates thereof, and mixtures thereof:wherein:- R1denotes a radical chosen from a) a hydrogen atom, and b) a saturated, linear C1-C10or branched C3-C10alkyl group optionally substituted with one or more groups, which may be identical or different, chosen from i) -O-R3, and ii) -S-R3, and- R2denotes a radical chosen from a) a hydrogen atom, b) a saturated, linear C1-C12or branched C3-C12or cyclic C3-C8hydrocarbon group optionally substituted with one or more groups, which may be identical or different, chosen from i) -O-R3, ii) -S-R3, iii) -C(O)-O-R3, and iv) a C5-C12aryl group, optionally substituted with one or more hydroxyls and / or with one or more C1-C8alkoxy radicals, and c) a C5-C12aryl group, optionally substituted with one or more hydroxyls and / or with one or more C1-C8alkoxy radicals, and- R3denotes a radical chosen from a) a hydrogen atom, and b) a saturated, linear C1-C10or branched C3-C10alkyl group.The composition as claimed in claim 1, wherein the water-soluble organic UV-screening agent(s) are chosen from water-soluble organic UV-screening agents capable of absorbing UVA rays, water-soluble organic UV-screening agents capable of absorbing UVA and UVB rays, water-soluble organic UV-screening agents capable of absorbing UVB rays, and mixtures thereof.The composition as claimed in either one of claims 1 and 2, comprising at least one water-soluble organic UV-screening agent capable of absorbing UVA rays and at least one water-soluble organic UV-screening agent capable of absorbing UVB rays.The composition as claimed in either one of claims 2 and 3, wherein the water-soluble organic screening agent(s) capable of absorbing UVA rays are chosen from:- terephthalylidene dicamphor sulfonic acid;- bis-benzazolyl derivatives, and more particularly the compound disodium phenyl dibenzimidazole tetrasulfonate.The composition as claimed in any one of claims 2 to 4, wherein the water-soluble organic UV-screening agent(s) capable of absorbing UVA and UVB rays are chosen from benzophenone derivatives comprising at least one sulfonic radical, such as benzophenone-4, benzophenone-5, and benzophenone-9.The composition as claimed in any one of claims 2 to 5, wherein the water-soluble screening agent(s) capable of absorbing UVB rays are chosen from water-soluble cinnamic derivatives, such as ferulic acid or 3-methoxy-4-hydroxycinnamic acid; water-soluble benzylidene camphor compounds; water-soluble phenylbenzimidazole compounds; water-soluble p-aminobenzoic (PABA) compounds, glyceryl PABA or PEG-25 PABA; water-soluble salicylic compounds, benzylidene camphor sulfonic acid, camphor benzalkonium methosulfate, and mixtures thereof.The composition as claimed in claim 6, wherein the water-soluble UV-screening agent(s) capable of absorbing UVB rays are chosen from phenylbenzimidazole compounds, such as 2-phenyl-1H-benzimidazole-5-sulfonic acid.The composition as claimed in any one of claims 1 to 7, wherein the water-soluble organic screening agent(s) are present in a total amount of active material of between 0.1% and 25% by weight, preferably between 0.1% and 20% by weight, preferably between 1% and 15% by weight, and even more preferentially between 1% and 5% by weight relative to the total weight of the composition.The composition as claimed in any one of claims 1 to 8, wherein R1of formulae (I) and (I’) represents a hydrogen atom; a linear (C1-C10) alkyl group or a branched (C3-C10) alkyl group, in particular a linear (C1-C6) alkyl group or a branched (C3-C6) alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably ethyl; in particular said alkyl group of R1is not substituted.The composition as claimed in any one of claims 1 to 9, wherein R2of formulae (I) and (I’) represents a hydrogen atom; a linear (C1-C10) or branched (C3-C10) alkyl group, in particular a linear (C1-C6) or branched (C3-C6) alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably methyl or ethyl; said alkyl group of R2not being substituted.The composition as claimed in any one of claims 1 to 10, wherein R3of formulae (I) and (I’) represents a hydrogen atom; a saturated, linear C1-C10or branched C3-C10alkyl group; in particular a linear (C1-C6) alkyl group or a branched (C3-C6) alkyl group, preferably a (C1-C4) alkyl group such as the methyl group.The composition as claimed in any one of claims 1 to 11, wherein R2of formulae (I) and (I’) represents a linear (C1-C10) alkyl group or a branched (C3-C10) alkyl group, in particular a linear (C1-C6) alkyl group or a branched (C3-C6) alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably methyl or ethyl; said alkyl group being substituted with one or more groups selected from i), ii), iii) and iv) as defined in claim 1, preferably said alkyl group being substituted with one or two groups selected from i), ii) and iii), more preferably with one or two groups chosen from i) and iii), better still substituted with a group iii) such as carboxy.The composition as claimed in any one of claims 1 to 12, wherein R2of formulae (I) and (I’) represents a (C3-C8) cycloalkyl group, preferably a (C5-C7) cycloalkyl group such as cyclohexyl; a C5-C12aryl group optionally substituted with one or more hydroxyls and / or with one or more C1-C8alkoxy radicals, preferably a phenyl group, in particular not being substituted.The composition as claimed in any one of claims 1 to 13, wherein R3of formulae (I) and (I’) represents a hydrogen atom; a saturated, linear C1-C10or branched C3-C10alkyl group; in particular a linear (C1-C6) alkyl group or a branched (C3-C6) alkyl group, preferably a (C1-C4) alkyl group such as a methyl group.The composition as claimed in any one of claims 1 to 14, wherein:- R1of formulae (I) and (I’) represents a radical chosen from a) a hydrogen atom, and b) a saturated, linear C1-C6or branched C3-C6alkyl group optionally substituted with one or more groups, which may be identical or different, chosen from i) -O-R3, and ii) -S-R3, preferably optionally substituted with one or more groups i);- R2of formulae (I) and (I’) represents a radical chosen from a) a hydrogen atom, and b) a saturated, linear C1-C10or branched C3-C10or cyclic C3-C8, such as C5-C6, hydrocarbon group, optionally substituted with one or more groups, which may be identical or different, chosen from i) -O-R3, ii) -S-R3, iii) -C(O)-O-R3, and iv) a phenyl group, optionally substituted with one or more hydroxyls and / or with one or more C1-C4alkoxy radicals such as methoxy, preferably substituted with one or more groups selected from i) and iii), preferably iii) such as carboxy; and- R3of formulae (I) and (I’) represents a radical chosen from a) a hydrogen atom, and b) a saturated, linear C1-C6or branched C3-C6alkyl group.The composition as claimed in any one of claims 1 to 15, wherein:- R1of formulae (I) and (I’) represents a radical chosen from a) a hydrogen atom, and b) a saturated, linear C1-C4or branched C3-C4alkyl group optionally substituted with one or more groups, which may be identical or different, chosen from i) -OR3, more preferably not being substituted;- R2of formulae (I) and (I’) represents a radical chosen from a) a hydrogen atom, and b) a saturated, linear C1-C10or branched C3-C10or cyclic C3-C8, for instance C5-C6, hydrocarbon group, optionally substituted with one or more groups, which may be identical or different, chosen from i) -O-R3, iii) -C(O)-O-R3, and iv) a C5-C12aryl group, optionally substituted with one or more hydroxyls and / or with one or more C1-C4alkoxy radicals; and- R3of formulae (I) and (I’) represents a radical chosen from a) a hydrogen atom; b) a saturated, linear C1-C4or branched C3-C4alkyl group such as methyl or ethyl.The composition as claimed in any one of claims 1 to 16, wherein the compound of formula (I) is selected from compounds 1 to 24 below, tautomers thereof, salts thereof, solvates thereof, such as hydrates thereof, optical isomers thereof, racemates thereof, and mixtures thereof, preferably compounds 1, 2, 4, 6, 7, 9, 11, 12, 14, 15, 16, 17, 18, 19, 20 or 21, more preferentially 1, 9, 16, 18, 19, 20 or 21, even more preferentially 18, 19, 20 or 21, and even better still 20:No.StructureChemical name1N-ethyl-2-thioxo-1,2-dihydropyridine-3-carboxamide2N-methyl-2-thioxo-1,2-dihydropyridine-3-carboxamide3N-octyl-2-thioxo-1,2-dihydropyridine-3-carboxamide4N-benzyl-2-thioxo-1,2-dihydropyridine-3-carboxamide5N-phenyl-2-thioxo-1,2-dihydropyridine-3-carboxamide6N-cyclohexyl-2-thioxo-1,2-dihydropyridine-3-carboxamide7N-[2-(4-methoxyphenyl)ethyl]-2-thioxo-1,2-dihydropyridine-3-carboxamide8N-(2-methylpropyl)-2-thioxo-1,2-dihydropyridine-3-carboxamide9N-pentyl-2-thioxo-1,2-dihydropyridine-3-carboxamide10N-nonyl-2-thioxo-1,2-dihydropyridine-3-carboxamide11N-(2-hydroxyethyl)-2-thioxo-1,2-dihydropyridine-3-carboxamide12N,N-diethyl-2-mercaptonicotinamide13N-ethyl-N-(2-hydroxyethyl)-2-thioxo-1,2-dihydropyridine-3-carboxamide14N-(2,3-dihydroxypropyl)-2-thioxo-1,2-dihydropyridine-3-carboxamide15N-(1,3-dihydroxypropan-2-yl)-2-thioxo-1,2-dihydropyridine-3-carboxamide16ethyl N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]alaninate17ethyl N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]phenylalaninate18ethyl N-methyl-N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycinate19ethyl N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycinate20N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycine21N-methyl-N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycine22N,N-bis(2-hydroxyethyl)-2-thioxo-1,2-dihydropyridine-3-carboxamide23N-(3-methoxypropyl)-2-thioxo-1,2-dihydropyridine-3-carboxamide24N-butyl-2-thioxo-1,2-dihydropyridine-3-carboxamideThe composition as claimed in any one of claims 1 to 17, wherein said compound of formula (I) or (I’) is present in the composition in a content ranging from 0.01% to 10% by weight, preferably from 0.05% to 5% by weight, more preferably from 0.1% to 3% by weight, relative to the total weight of the composition.The composition as claimed in any one of claims 1 to 18, wherein the weight ratio of the amount of compounds chosen from the compounds of formula (I), the tautomers of formula (I’), salts thereof, solvates thereof, optical isomers thereof and racemates thereof, to the amount of water-soluble organic UV-screening agents is between 1 / 25 and 1 / 0.5, preferably between 1 / 10 and 1 / 0.5, and more preferentially between 1 / 10 and 1.The composition as claimed in any one of claims 1 to 19, wherein the overall aqueous phase, including all the hydrophilic substances of the composition that are capable of being dissolved or dispersed in this same phase, including hydrophilic screening agents such as water-soluble screening agents and water-dispersible screening agents, and also the thiopyridinone compound(s) as defined previously, represents from 5% to 100% by weight, preferably from 20% to 100% by weight, and preferentially from 30% to 99% by weight, and even more preferentially from 30% to 90% by weight, relative to the total weight of the composition.The composition as claimed in any one of claims 1 to 20, further comprising one or more additional UV-screening agents, notably one or more additional organic UV-screening agents.The use of at least one water-soluble organic UV-screening agent for photostabilizing at least one compound selected from the compounds of formula (I), the tautomers of formula (I’), the salts thereof, the solvates thereof such as hydrates thereof, the optical isomers thereof and the racemates thereof as defined in any one of claims 1 and 9 to 17, in particular when it is dissolved in a composition comprising at least one aqueous phase, even in the presence of additional UV-screening agents.

Images