Cosmetic or dermatological composition comprising a 2-hydroxybenzophenone compound and a thiopyridinone compound

Abstract

The present invention relates to a composition, in particular a cosmetic or dermatological composition, comprising at least one amino-substituted 2-hydroxybenzophenone compound, and at least one compound of formula (I) or (I'), as described hereinbelow, and / or optical isomers thereof, geometrical isomers thereof, and also organic or mineral acid or base salts thereof, and / or solvates thereof such as hydrates.

Description

Cosmetic or dermatological composition comprising a 2-hydroxybenzophenone compound and a thiopyridinone compound

[0001] The present invention relates to a composition, in particular a cosmetic or dermatological composition, comprising at least one amino-substituted 2-hydroxybenzophenone compound, and at least one compound of formula (I) or (I’), as described hereinbelow, and / or optical isomers thereof, geometrical isomers thereof, and also organic or mineral acid or base salts thereof, and / or solvates thereof such as hydrates.

[0002] Patent applications WO 2012 / 080075 and WO 2017 / 102349 disclose a depigmenting or lightening agent that is a thiopyridinone compound. The thiopyridinone compound has depigmenting or lightening properties that are particularly effective in reducing melanin production.

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

[0004] The Applicant has discovered, surprisingly, that by using at least one amino-substituted 2-hydroxybenzophenone compound, it is 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 objectives of the present invention, a composition and in particular a cosmetic or dermatological composition is now proposed, comprising at least one amino-substituted 2-hydroxybenzophenone compound, and at least one compound of formula (I) or (I'), as described hereinbelow, and / or optical isomers thereof, geometrical 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 amino-substituted 2-hydroxybenzophenone compound(s).

[0007] Specifically, it may be particularly advantageous to incorporate UV-screening agents into a cosmetic composition comprising a thiopyridinone compound so as to obtain compositions which have good activity on pigmentation induced by UV and visible radiation, a high level of solar protection, and also good physicochemical stability and good cosmetic qualities, notably being neither greasy nor tacky.

[0008] Thus, in accordance with another objective of the present invention, a composition and in particular a cosmetic or dermatological composition is proposed, comprising at least one amino-substituted 2-hydroxybenzophenone compound, at least one additional UV-screening agent, and at least one compound of formula (I) or (I'), as described hereinbelow, and / or optical isomers thereof, geometrical 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 amino-substituted 2-hydroxybenzophenone compound allowed an increase in the photostability of a thiopyridinone compound, and / or an optical isomer or geometrical 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 an aqueous phase, even in the presence of additional UV-screening agents.Disclosure of the invention

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

[0011] a) at least one amino-substituted 2-hydroxybenzophenone compound; and

[0012] b) at least one compound selected from the compounds of formula (I), the tautomers of formula (I'), salts thereof, solvates thereof such as hydrates thereof, optical isomers thereof, racemates thereof, and mixtures thereof:

[0013] in which:

[0014] - 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

[0015] - R2denotes a radical chosen from a) a hydrogen atom, b) a saturated, linear C1-C12or branched C3-C12or cyclic C3-C8hydrocarbon-based 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

[0016] - R3denotes a radical chosen from a) a hydrogen atom, and b) a saturated, linear C1-C10or branched C3-C10alkyl group.

[0017] This composition may optionally comprise at least one additional UV-screening agent.

[0018] The present invention affords cosmetic or dermatological compositions in which the thiopyridinone compound is stable over time, notably when exposed to UV radiation.

[0019] The compositions in accordance with the invention moreover have good activity on pigmentation induced by UV and visible radiation, high photoprotective power, good physicochemical stability, and good cosmetic qualities, notably being non-greasy and non-tacky.

[0020] 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.

[0021] The invention also relates to a non-therapeutic cosmetic process for limiting the darkening of the skin and / or improving the colour and / or uniformity of the complexion, comprising the application, to the surface of the keratin material, of at least one composition as defined previously.

[0022] The invention also relates to a non-therapeutic cosmetic process for preventing and / or treating the signs of ageing of a keratin material, comprising the application, to the surface of the keratin material, of at least one composition as defined previously.

[0023] The present invention also relates to the use of at least one amino-substituted 2-hydroxybenzophenone compound for photostabilizing the thiopyridinone compound(s) as defined previously, and / or optical isomers thereof or geometrical isomers thereof, and also the organic or mineral acid or base salts thereof, and / or solvates such as a hydrate.

[0024] Other features, aspects and advantages of the invention will become apparent on reading the detailed description that follows.

[0025] 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.

[0026] In the context of the present invention, the term “keratin material” notably means the skin, scalp, keratin fibres, such as the eyelashes, eyebrows, head hair and bodily hair, nails, mucous membranes, such as the lips, and more particularly the skin and mucous membranes (body, face, area around the eyes, eyelids, lips, preferably body, face and lips).

[0027] 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 ...”.

[0028] 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.

[0029] 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 ageing of a keratin material.

[0030] For the purposes of the invention, the term “hydrophilic organic UV-screening agent” means organic UV-screening agents chosen from water-soluble organic UV-screening agents and water-dispersible organic UV-screening agents.

[0031] The term “water-soluble organic screening agent” means any organic screening agent that can be totally dissolved in molecular form in a liquid aqueous phase.

[0032] The term “water-dispersible organic screening agent” means any organic screening agent that is 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 granulometry.

[0033] The term “lipophilic organic screening agent” means any organic screening agent that can be fully dissolved in molecular form in a liquid fatty phase or that can be dissolved in colloidal form (for example in micellar form) in a liquid fatty phase.

[0034] The term “organic UVA-screening agent” refers to any organic chemical molecule that is 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.

[0035] The term “organic UVB-screening agent” refers to any organic chemical molecule that is capable of absorbing mainly UVB radiation in the wavelength range between 280 and 320 nm.Detailed description of the inventionAmino-substituted 2-hydroxybenzophenone compounds

[0036] The amino-substituted 2-hydroxybenzophenone compound(s) that may be used in the context of the invention may be chosen from the compounds corresponding to formula (I) below:

[0037] in which:

[0038] R1and R2, which may be identical or different, denote a C1-C20alkyl radical, a C2-C20alkenyl radical, a C3-C10cycloalkyl radical, a C3-C10cycloalkenyl radical, or form a 5- or 6-membered ring with the nitrogen atom to which they are attached;

[0039] n is a number ranging from 1 to 4;

[0040] when n = 1, R3denotes a C1-C20alkyl radical, a C1-C20alkenyl radical, a C1-C5hydroxyalkyl radical, a C6-C12cyclohexyl radical, a phenyl which may be substituted with O, N or S, an aminocarbonyl radical or a C1-C5alkylcarbonyl radical;

[0041] when n = 2, R3denotes an alkyl diradical, a cycloalkyl diradical, an alkenyl diradical or an aryl diradical, or R3together with E form a diradical of formula (II):

[0042] where m is a number ranging from 1 to 3;

[0043] when n = 3, R3is an alkyl triradical;

[0044] when n = 4, R3is an alkyl tetraradical;

[0045] E is –O-, or –N(R4)- or N;

[0046] R4is hydrogen, or a C1-C5alkyl or C1-C5hydroxyalkyl radical.

[0047] As C1-C20alkyl radicals, mention may be made, for example, of methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl or n-eicosyl.

[0048] As C3-C10cycloalkyl radicals, mention may be made, for example, of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, 1-methylcyclopropyl, 1-ethylcyclopropyl, 1-propylcyclopropyl, 1-butylcyclopropyl, 1-pentylcyclopropyl, 1-methyl-1-butylcyclopropyl, 1,2-dimethylcyclopropyl, 1-methyl-2-ethylcyclopropyl, cyclooctyl, cyclononyl or cyclodecyl.

[0049] As C3-C10cycloalkenyl radicals containing one or more double bonds, mention may be made of: cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, 1,3-cyclohexadienyl, 1,4-cyclohexadienyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, 1,5-cyclooctadienyl, cyclooctatetraenyl, cyclononenyl or cyclodecenyl.

[0050] As examples of 5- or 6-membered rings formed by the radicals R1 and R2 with the nitrogen atom, mention may be made in particular of pyrrolidine or piperidine.

[0051] A most particularly preferred compound of formula (I) with n = 1 is n-hexyl 2-(4-diethylamino-2-hydroxybenzoyl)benzoate of formula (a):

[0052] having the INCI name Diethylamino hydroxybenzoyl hexyl benzoate, such as the product sold under the trade name Uvinul A Plus® by the company BASF or in admixture with ethylhexyl methoxycinnamate under the trade name Uvinul® A Plus B by the company BASF.

[0053] A most particularly preferred compound of formula (I) with n = 2 is the derivative (2-{4-[2-(4-diethylamino-2-hydroxybenzoyl)benzoyl]piperazine-1-carbonyl}phenyl)(4-diethylamino-2-hydroxyphenyl)methanone (CAS 919803-06-8) of formula (b):

[0054] which is described in patent application WO 2007 / 071 584. This compound is advantageously used in micronized form (mean size of 0.02 to 2 µm) which can be obtained, for example, according to the micronization process described in patent applications GB-A-2 303 549 and EP-A-893 119 and more particularly in the form of an aqueous dispersion.

[0055] The compounds of formula (I) as defined above are knownper seand their structures and syntheses are described in patent applications EP-A-1 046 391, EP 1 133 980, DE 100 12 408 and WO 2007 / 071 584.

[0056] According to a particular embodiment of the invention, the composition comprises n-hexyl 2-(4-diethylamino-2-hydroxybenzoyl)benzoate of formula (a):

[0057] such as the product sold under the trade name Uvinul A Plus® by the company BASF.

[0058] The amino-substituted 2-hydroxybenzophenone compound(s) are present in the compositions in accordance with the invention in contents which generally range from 0.01% to 20% by weight, preferably from 0.1% to 10% by weight and even more preferentially from 0.5% to 5% by weight, relative to the total weight of the composition.Thiopyridinone compounds

[0059] The composition according to the present invention comprises at least one thiopyridinone compound. Two or more different 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.

[0060] The thiopyridinone compound(s) are selected from the compounds of formula (I) below, the tautomers of formula (I’) below, salts thereof, solvates thereof such as hydrates thereof, optical isomers thereof, racemates thereof, and mixtures thereof:

[0061] in which:

[0062] 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

[0063] R2denotes a radical chosen from a) a hydrogen atom, b) a saturated, linear C1-C12or branched C3-C12or cyclic C3-C8hydrocarbon-based 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

[0064] R3denotes a radical chosen from a) a hydrogen atom, and b) a saturated, linear C1-C10or branched C3-C10alkyl group.

[0065] Hereinbelow, for the purposes of the present invention and unless otherwise indicated:

[0066] - a “saturated, linear C1-C12or branched C3-C12hydrocarbon-based 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-based group, preferably a linear C1-C10or branched C3-C10hydrocarbon-based group, and more preferably a linear C1-C6or branched C3-C6hydrocarbon-based 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;

[0067] - a saturated “cyclic C3-C8” hydrocarbon-based group is amonocyclic or bicyclic cycloalkyl group containing from 3 to 8 carbon atoms, and notably is a monocyclic C5to C7cycloalkyl group such as a cyclohexyl group,

[0068] - an “alkoxy radical” is an alkyl-oxy radical for which the alkyl radical is a linear or branched C1-C16hydrocarbon-based radical, and preferentially a C1-C8hydrocarbon-based radical;

[0069] - when the alkoxy group is optionally substituted, this implies that the alkyl group is optionally substituted as defined above;

[0070] - an “aryl” group represents a monocyclic or bicyclic, fused or non-fused, carbon-based group comprising from 5 to 12 carbon atoms, preferably from 6 to 10 carbon atoms, and in which at least one ring is aromatic; preferentially, the aryl radical is a phenyl, biphenyl, or naphthyl group, more preferentially a phenyl group;

[0071] - the term “at least one” is equivalent to the term “one or more”; and

[0072] - the term “inclusive” for a range of concentrations means that the limits of that range are included in the defined range.

[0073] 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 an organic or inorganic base.

[0074] As salts of the compounds of formula (I), (I'), (II) or (II'), mention may be made of:

[0075] the salts obtained by adding the compound of formula (I) or (II) to:

[0076] a mineral base, such as sodium hydroxide, potassium hydroxide, calcium hydroxide, ammonium hydroxide, magnesium hydroxide, lithium hydroxide, and sodium, potassium or calcium carbonate or hydrogen carbonate, for example; or

[0077] 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. In particular, mention may be made of 2-amino-2-methylpropanol, ethanolamine, triethanolamine, 2-dimethylaminopropanol, 2-amino-2-(hydroxymethyl)-1,3-propanediol, and 3-(dimethylamino)propylamine.

[0078] Amino acid salts, such as lysine, arginine, guanidine, glutamic acid and aspartic acid, may also be mentioned. 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.

[0079] An “organic or inorganic acid salt” is more particularly chosen from salts chosen from a salt derived from i) hydrochloric acid HCl, ii) hydrobromic acid HBr, iii) sulfuric acid H2SO4, iv) alkylsulfonic acids: Alk-S(O)2OH such as 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.

[0080] The acceptable solvates of the compounds described in the present specification comprise conventional solvates such as those formed during the preparation of said compounds due 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.

[0081] The optical isomers are in particular enantiomers and diastereoisomers.

[0082] Compound (I’) is the tautomeric form of compound (I) when a tautomeric equilibrium exists according to the following scheme:

[0083] According to one embodiment of the present invention, R1represents a hydrogen atom.

[0084] According to one embodiment of the present invention, R1of formulae (I) and (I’) represents a linear (C1-C10) or branched (C3-C10) alkyl group, notably a linear (C1-C6) or branched (C3-C6) alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl or isobutyl, more preferably ethyl. In particular, said alkyl group of R1is not substituted.

[0085] According to one embodiment of the present invention, R2represents a hydrogen atom.

[0086] According to one embodiment of the present invention, R2represents a linear (C1-C10) or branched (C3-C10) alkyl group, notably a linear (C1-C6) or branched (C3-C6) alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl or isobutyl, more preferably methyl or ethyl; said alkyl group of R2not being substituted.

[0087] According to one embodiment of the present invention, R2of formulae (I) and (I’) represents a linear (C1-C10) or branched (C3-C10) alkyl group, notably a linear (C1-C6) or branched (C3-C6) alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl or 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.

[0088] Another variant for the radical R2is that said alkyl group is substituted with a group iv), notably substituted with a phenyl group.

[0089] According to another embodiment of the present invention, R2represents a (C3-C8) cycloalkyl group, preferably a (C5-C7) cycloalkyl group such as cyclohexyl.

[0090] 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.

[0091] According to one embodiment, R3represents a hydrogen atom.

[0092] 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.

[0093] 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:

[0094] 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);

[0095] 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-based 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

[0096] R3denotes a radical chosen from a) a hydrogen atom, and b) a saturated, linear C1-C6or branched C3-C6alkyl group.

[0097] 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:

[0098] 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, which is more preferably unsubstituted;

[0099] 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-based 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

[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] 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:

[0102] R1is a hydrogen atom; and

[0103] R2denotes a radical chosen from a) a hydrogen atom, and b) a saturated, linear C1-C5or branched C3-C5or cyclic C3-C8, such as C5-C6, hydrocarbon-based group optionally substituted with one or more groups, which may be identical or different, chosen from v) -C(O)-O-R3, preferably substituted with a group iii) -C(O)-O-R3; R2is even more preferably a saturated, linear C1-C4or branched C3-C4hydrocarbon-based group substituted with a group iii) -C(O)-OR3; and

[0104] 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.

[0105] 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’)

[0106] 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.

[0107] Among the compounds of formula (I), use is preferably made of the following compounds, 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: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

[0108] 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

[0109] 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

[0110] 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

[0111] 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)

[0112] All the above compounds can be obtained via a chemical process known to those skilled in the art, from commercially available reagents.

[0113] The thiopyridinone compound (1) may be prepared in accordance with the process described, for example, in EP-A-3390363 or WO 2017 / 102349, which is incorporated by reference.

[0114] The thiopyridinone compound (1) may be an active principle or an active compound in cosmetic or dermatological products. The term “active” principle or compound used herein denotes an ingredient or compound that has an active cosmetic or dermatological property, such as antioxidant, lightening, UV-screening and antibacterial effects. The thiopyridinone compound (1) used in the present invention can function as a depigmenting, bleaching, or lightening agent, and thus the composition according to the present invention can be used as a bleaching product or as a cosmetic composition for bleaching a keratin material.

[0115] The thiopyridinone compound (1) can be used as an agent for depigmenting, bleaching or lightening the skin, bodily hair, the eyelashes or head hair, and also the lips and / or the nails, and preferably the skin, in particular for removing pigmentation spots or age spots, and / or as an anti-tanning agent.

[0116] The amount of the 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.

[0117] Moreover, the amount of the 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.

[0118] The amount of the thiopyridinone compound(s) (1) in the composition according to the present invention may be 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.Additional UV-screening agents

[0119] The composition according to the invention may also comprise at least one additional UV-screening agent other than the amino-substituted 2-hydroxybenzophenone compounds as described previously.

[0120] According to a particular embodiment of the invention, the additional UV-screening agent(s) other than the amino-substituted 2-hydroxybenzophenone compounds as described previously are chosen from organic UV-screening agents.

[0121] The additional UV-screening agent(s) may notably be chosen from hydrophilic organic UV-screening agents such as water-soluble organic UV-screening agents and water-dispersible organic UV-screening agents, and lipophilic organic UV-screening agents.Water-soluble organic UV-screening agents

[0122] The composition in accordance with the invention may comprise at least one water-soluble organic UV-screening agent.

[0123] Among the water-soluble organic screening agents that are capable of absorbing UVA rays, mention may be made of:

[0124] - the compound having the INCI name Terephthalylidenedicamphorsulfonic acid, manufactured under the name Mexoryl SX by Noveal;

[0125] - bis-benzazolyl derivatives as described in patents EP 669 323 and US 2 463 264, and more particularly the compound having the INCI name disodium phenyldibenzimidazole tetrasulfonate sold under the trade name Neo Heliopan AP by Symrise.

[0126] The water-soluble organic screening agent may also be a mixed water-soluble screening agent that is capable of absorbing UVA and UVB rays. Preferably, such a mixed screening agent is a benzophenone derivative including at least one sulfonic radical, notably such as:

[0127] Benzophenone-4, sold under the trade name Uvinul® MS40 by BASF,

[0128] Benzophenone-5, and

[0129] Benzophenone-9.

[0130] According to a particular embodiment of the invention, the water-soluble organic screening agent(s) that are capable of absorbing UVA rays are chosen from terephthalylidenedicamphorsulfonic acid, bis-benzazolyl derivatives, in particular disodium phenyldibenzimidazole tetrasulfonate, benzophenone-4, benzophenone-5, benzophenone-9, and mixtures thereof.

[0131] Preferably, the water-soluble organic screening agent(s) that are capable of absorbing UVA rays are chosen from terephthalylidenedicamphorsulfonic acid, disodium phenyldibenzimidazole tetrasulfonate, benzophenone-4, benzophenone-5, benzophenone-9, and mixtures thereof.

[0132] Even more preferentially, the water-soluble organic screening agent(s) that are capable of absorbing UVA rays are chosen from terephthalylidenedicamphorsulfonic acid, bis-benzazolyl derivatives, in particular disodium phenyldibenzimidazole tetrasulfonate, and mixtures thereof.

[0133] Preferably, the water-soluble organic screening agent(s) that are capable of absorbing UVA rays are chosen from terephthalylidenedicamphorsulfonic acid, disodium phenyldibenzimidazole tetrasulfonate, and mixtures thereof.

[0134] According to a first preferential embodiment, the water-soluble organic screening agent that is capable of absorbing UVA rays is terephthalylidenedicamphorsulfonic acid (also known as Ecamsule).

[0135] According to a second preferential embodiment, the water-soluble organic screening agent that is capable of absorbing UVA rays is disodium phenyldibenzimidazole tetrasulfonate (also known as Bisdisulizole Disodium).

[0136] The water-soluble organic UVB screening agent(s) that may 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 benzylidenecamphor compounds; water-soluble phenylbenzimidazole compounds; water-soluble p-aminobenzoic acid (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.

[0137] 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: phenylbenzimidazolesulfonic acid) sold notably under the trade name EUSOLEX 232®by Merck.

[0138] According to a preferential embodiment, the water-soluble organic screening agent that is capable of absorbing UVB rays is phenylbenzimidazolesulfonic acid (also called Ensulizole).Water-dispersible organic UV-screening agents

[0139] The water-dispersible organic UV-screening agent(s) may be chosen from the following compounds.

[0140] Methylenebis(hydroxyphenylbenzotriazole) compounds:

[0141] Methylenebis(benzotriazolyl)tetramethylbutylphenol in the form of an aqueous dispersion of micronized particles with a volume-mean particle size which ranges from 0.01 to 5 µm, 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, notably the product sold under the trade name Tinosorb® M by the company BASF, or in the form of an aqueous dispersion of micronized particles with a volume-mean particle size which ranges from 0.02 to 2 µm, 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, notably the product sold under the name Tinosorb WPGL by the company BASF.Triazine compounds:

[0142] - 3,3’-(1,4-Phenylene)bis(5,6-diphenyl-1,2,4-triazine), having the INCI name Phenylene Bis-Diphenyl triazine, notably sold under the name Triasorb by Pierre Fabre;

[0143] - 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,

[0144] - 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.

[0145] Among the water-dispersible organic UV-screening agents, mention may also be made of benzoxazole compounds such as 2-[4-(1,3-benzoxazol-2-yl)phenyl]-1,3-benzoxazole, having the CAS No. 904-39-2.Lipophilic organic UV-screening agents

[0146] The lipophilic organic screening agent(s) may be chosen from cinnamic compounds; anthranilate compounds; salicylic compounds; dibenzoylmethane compounds; benzylidene camphor compounds; benzophenone compounds other than the amino-substituted 2-hydroxybenzophenone compounds as described previously; 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; methylene bis(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.

[0147] Preferably, the lipophilic organic screening agent(s) are chosen from salicylic compounds; dibenzoylmethane compounds; benzylidenecamphor compounds; benzophenone compounds other than the amino-substituted 2-hydroxybenzophenone compounds as described previously; triazine compounds; benzotriazole compounds; and mixtures thereof.

[0148] 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:

[0149] Ethylhexyl methoxycinnamate notably sold under the trade name Parsol® MCX by the company DSM Nutritional Products,

[0150] Isoamyl p-methoxycinnamate, sold under the trade name Neo Heliopan E 1000® by the company Symrise,Dibenzoylmethane compounds:

[0151] Butylmethoxydibenzoylmethane (or avobenzone) notably sold under the trade name Parsol® 1789 by the company DSM Nutritional Products,Salicylic compounds:

[0152] Homosalate sold under the name Parsol® HMS by the company DSM Nutritional Products,

[0153] Ethylhexyl salicylate sold under the name Neo Heliopan® OS by the company Symrise,β,β-Diphenylacrylate compounds:

[0154] Octocrylene, notably sold under the trade name Uvinul® N 539 T by the company BASF,Benzophenone compounds:

[0155] Benzophenone-3 or Oxybenzone, sold under the trade name Uvinul® M 40 by the company BASF,Benzylidenecamphor compounds:

[0156] 4-Methylbenzylidenecamphor, sold under the name Eusolex® 6300 by the company Merck,Phenylbenzotriazole compounds:

[0157] Drometrizole trisiloxane manufactured under the name Mexoryl® XL by the company Noveal,

[0158] Methylenebis(hydroxyphenylbenzotriazole) compounds:

[0159] 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:

[0160] - bis-Ethylhexyloxyphenol methoxyphenyl triazine sold under the trade name Tinosorb® S by the company BASF,

[0161] - Ethylhexyl triazone, notably sold under the trade name Uvinul® T150 by the company BASF,

[0162] - Diethylhexylbutamidotriazone sold under the trade name Uvasorb® HEB by the company 3V Sigma,

[0163] - the symmetrical triazine screening agents substituted with naphthalenyl groups or polyphenyl groups, described in patent US 6 225 467, patent application WO 2004 / 085 412 (see compounds 6 and 9) or the document “Symmetrical Triazine Derivatives” IP.COM IPCOM000031257 Journal, INC West Henrietta, NY, US (20 September 2004),Anthranilic compounds:

[0164] Menthyl anthranilate sold under the trade name Neo Heliopan® MA by the company Symrise,Benzalmalonate compounds:

[0165] Polyorganosiloxane containing benzalmalonate functions, for instance Polysilicone-15, sold under the trade name Parsol SLX® by the company DSM Nutritional Products.

[0166] According to a particular embodiment of the invention, the additional UV-screening agent(s) are chosen from organic UV-screening agents other than the amino-substituted 2-hydroxybenzophenone compounds as described previously.

[0167] According to a first preferred embodiment of the invention, the organic UV-screening agent(s) are chosen from hydrophilic organic UV-screening agents such as water-soluble organic UV-screening agents and water-dispersible organic UV-screening agents, preferably water-soluble organic UV-screening agents.

[0168] According to a second preferred embodiment of the invention, the additional UV-screening agent(s) are chosen from lipophilic organic UV-screening agents other than the amino-substituted 2-hydroxybenzophenone compounds as described previously, preferably chosen from drometrizole trisiloxane (notably manufactured under the name Mexoryl® XL by the company Noveal), bis(ethylhexyloxyphenol)methoxyphenyltriazine (notably sold under the trade name Tinosorb® S by the company BASF), ethylhexyl triazone (notably sold under the trade name Uvinul® T 150 by the company BASF) and butylmethoxydibenzoylmethane (notably sold under the trade name Parsol 1789® by the company DSM Nutritional Products).

[0169] The additional UV-screening agent(s) other than the amino-substituted 2-hydroxybenzophenone compounds as described previously may be present in an amount of between 0.2% and 30% by weight, preferably between 0.5% and 20% by weight, preferably between 1% and 20% by weight, and even more preferentially between 1.5% and 15% by weight relative to the total weight of the composition.

[0170] 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

[0171] The composition in accordance with the invention may comprise at least one aqueous phase.

[0172] According to a particular embodiment, the composition according to the invention comprises at least one aqueous phase comprising at least water.

[0173] The aqueous phase may also comprise at least one other organic solvent that is soluble in water, at 25°C, chosen, for example, from:

[0174] - C1-C4 monoalkanols. 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;

[0175] - 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

[0176] - mixtures thereof.

[0177] 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.

[0178] 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 the 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.

[0179] 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.

[0180] According to a particular embodiment, the cosmetic composition according to the invention may comprise an acid and / or a base.

[0181] Among the acidifying agents, examples that may be mentioned include mineral or organic acids, for instance hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids, for instance acetic acid, tartaric acid, citric acid or lactic acid, and sulfonic acids.

[0182] 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.

[0183] Preferably, the cosmetic composition comprises one or more basifying agents selected from alkanolamines, in particular triethanolamine, and sodium hydroxide.

[0184] According to a 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, so as to optimize the dissolution and stability of the thiopyridinone compound.

[0185] The pH of the composition in accordance with the invention may be measured using an MPC227, SevenEasy pH, or SevenGo SG2 pH meter from Mettler Toledo, at room temperature (25°C) and atmospheric pressure.

[0186] According to a particular embodiment of the invention, the overall aqueous phase, including all the hydrophilic substances in the composition that can be solubilized or dispersed in this same phase, including the hydrophilic screening agents such as the water-soluble screening agents and the water-dispersible screening agents, and also the thiopyridinone compound(s) as defined previously, represents from 5% to 100% by weight, and preferentially from 30% to 100% by weight, relative to the total weight of the composition.

[0187] 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

[0188] According to a particular embodiment, the composition in accordance with the invention comprises at least one fatty phase.

[0189] 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.

[0190] 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.

[0191] 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 fibre 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 vapour 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).

[0192] The term “non-volatile oil” means an oil that remains on the skin or the keratin fibre at room temperature and atmospheric pressure for at least several hours, and that notably has a vapour pressure of less than 10-3mmHg (0.13 Pa).

[0193] For the purposes of the present invention, the term “hydrocarbon-based oil” means any oil predominantly including carbon and hydrogen atoms, and possibly 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.

[0194] The term “silicone oil” means an oil comprising at least one silicon atom and notably at least one Si-O group.

[0195] As non-volatile hydrocarbon-based oils that may be used according to the invention, mention may notably be made of:

[0196] (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, sesame seed oil, marrow oil, rapeseed 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;

[0197] (ii) synthetic ethers containing from 10 to 40 carbon atoms;

[0198] (iii) linear or branched hydrocarbons of mineral or synthetic origin, such as petroleum jelly, polydecenes, hydrogenated polyisobutene, such as Parleam, squalane and mixtures thereof;

[0199] (iv) synthetic esters, such as the oils of formula RCOOR’ in which R represents a linear or branched fatty acid residue including from 1 to 40 carbon atoms and R’ represents a hydrocarbon-based 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;

[0200] (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;

[0201] (vi) higher C12-C22 fatty acids such as oleic acid, linoleic acid or linolenic acid;

[0202] (vii) carbonates, such as dicaprylyl carbonate, such as the product sold under the name Cetiol CC® by the company Cognis;

[0203] and mixtures thereof.

[0204] Among the non-volatile hydrocarbon-based oils that may be used according to the invention, preference will be given more particularly to glyceride triesters and notably to caprylic / capric acid triglycerides, synthetic esters and notably diisopropyl adipate, diisopropyl sebacate, isopropyl palmitate, dicaprylyl carbonate, isononyl isononanoate, oleyl erucate, C12-C15 alkyl benzoate, 2-ethylphenyl benzoate and fatty alcohols, notably octyldodecanol. Preferably, the non-volatile hydrocarbon-based oils are chosen from diisopropyl adipate, diisopropyl sebacate, isopropyl palmitate and dicaprylyl carbonate.

[0205] 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.

[0206] Mention may also be made of the alkanes described in the Cognis patent applications WO 2007 / 068 371 or WO 2008 / 155 059 (mixtures of different alkanes differing by at least one carbon). These alkanes are obtained from fatty alcohols, which are themselves obtained from coconut kernel 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.

[0207] Other volatile hydrocarbon-based oils, for instance petroleum distillates, notably those sold under the name Shell Solt® by the company Shell, may 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.

[0208] 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.

[0209] 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.

[0210] Mention may also be made of linear volatile alkyltrisiloxane oils such as:

[0211] 3-butyl-1,1,1,3,5,5,5-heptamethyltrisiloxane,

[0212] 3-propyl-1,1,1,3,5,5,5-heptamethyltrisiloxane, and

[0213] 3-ethyl-1,1,1,3,5,5,5-heptamethyltrisiloxane.

[0214] Use may also be made of volatile fluoro oils, such as nonafluoromethoxybutane, nonafluoromethoxybutane, decafluoropentane, tetradecafluorohexane, dodecafluoropentane, and mixtures thereof.

[0215] The fatty phase according to the invention may also comprise other fatty substances, mixed with or dissolved in the oil.

[0216] Another fatty substance that may be present in the oily phase may be, for example:

[0217] - a fatty acid chosen from fatty acids comprising from 8 to 30 carbon atoms, other than the fatty-chain amino acids as defined previously, such as stearic acid, lauric acid, palmitic acid and oleic acid;

[0218] - a gum chosen from silicone gums (dimethiconol);

[0219] - a pasty compound, such as polymeric or non-polymeric silicone compounds, esters of an oligomeric glycerol, arachidyl propionate, fatty acid triglycerides and derivatives thereof;

[0220] - and mixtures thereof.

[0221] 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, 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

[0222] The composition of the present invention may comprise at least one cosmetic active agent.

[0223] 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.

[0224] 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

[0225] 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.

[0226] 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

[0227] According to a particular embodiment, the compositions according to the invention have a viscosity of at least 0.10 Pa.s, measured at 25°C and at atmospheric pressure with a Lamy Rheology Rheomat RM100® viscometer after 10 minutes of stirring. Preferably, it 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.

[0228] Such a viscosity typically allows the compositions to have a gel-like texture.

[0229] The compositions according to the invention may be prepared according to techniques that are well known to those skilled in the art.

[0230] The compositions according to the invention may be in aqueous form, for example in the form of an aqueous gel or an aqueous-alcoholic composition, but also in the form of an emulsion, notably an oil-in-water or water-in-oil emulsion, or a two-phase composition.

[0231] According to a 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.

[0232] 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.

[0233] It is also possible, via HPH (between 50 and 800 bar), to obtain stable dispersions with drop sizes that may be as small as 100 nm.

[0234] 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).

[0235] 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 the company Dow Corning, and alkyldimethicone copolyols such as laurylmethicone copolyol sold under the name Dow Corning 5200 Formulation Aid by the company Dow Corning; cetyldimethicone copolyol, such as the product sold under the name Abil EM 90R® by the company Goldschmidt, and the mixture of cetyldimethicone copolyol, of polyglyceryl isostearate (4 mol) and of hexyl laurate, sold under the name Abil WE O9® by the company Goldschmidt. One or more coemulsifiers, which may be chosen advantageously from the group comprising polyol alkyl esters, may also be added thereto.

[0236] Mention may also be made of non-silicone emulsifying surfactants, notably alkyl esters or ethers of sorbitan, of glycerol, of polyol or of sugars.

[0237] 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.

[0238] 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.

[0239] 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 alkylpolyglucoside 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.

[0240] As anionic surfactants making it possible to produce O / W emulsions, mention may be made of surfactants chosen from amino acids modified with at least one C8-C30, preferably C8-C24, hydrocarbon-based 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).

[0241] 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.

[0242] As anionic surfactants making it possible to produce 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-C18 alkyl carbamate groups, and more particularly lauryl carbamate groups.

[0243] Examples of these compounds that may notably be mentioned include the product sold under the name Inutec SL1 by the company Creachem.

[0244] 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.

[0245] 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

[0246] 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.

[0247] A- Example of synthesis of thiopyridinone compounds of formula (I) or (I’)

[0248] Step 1: Synthesis of ethyl N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycinate

[0249] Route 1: via 2-mercaptonicotinic acid

[0250] Thionicotinic acid is added to acetonitrile in a round-bottomed flask, and carbonyldiimidazole (CDI) is then added. The resulting mixture is heated at reflux for one hour and then left at room temperature.

[0251] After returning to room temperature, ethyl glycinate hydrochloride is added and the resulting mixture is then reheated at a temperature of 60°C for 3 hours. The mixture is then left at room temperature overnight.

[0252] The next day, the reaction medium is evaporated. The residue is recovered in dichloromethane and washed twice with 2 N HCl.

[0253] The organic phase is dried over anhydrous sodium sulfate, and then evaporated and purified on silica dichloromethane 97 / methanol 3.

[0254] The fractions are evaporated.

[0255] A pale yellow powder is obtained.

[0256] Route 2: via 2-chloronicotinic acid

[0257] 2-Chloronicotinic acid (250.0 g, 1.587 mol) is introduced into ethyl acetate (500 ml) in a three-necked flask, and SOCl2(210.0 g, 1.761 mol) is then added dropwise to the mixture.

[0258] The mixture is heated at reflux until conversion is complete. Once the reaction is complete, the mixture is cooled to room temperature and diluted with ethyl acetate (375 ml).

[0259] A solution of ethyl glycinate hydrochloride (265.8 g, 1.904 mol) diluted in water (400 ml) and triethylamine (393.5 g, 3.88 mol) is then added to the mixture.

[0260] The mixture is stirred for a duration ranging from 3 to 4 hours, and the ethyl acetate is then removed under vacuum.

[0261] The aqueous solution thus obtained is then diluted with water (1250 ml) and acidified with 3N HCl (25 ml).

[0262] Sodium thiosulfate (1379 g, 5.555 mol) is then added and the mixture is heated at reflux for 6 hours. After cooling to 10°C, the yellow solid is filtered off and washed with water (three times 750 ml).

[0263] The crude product is then treated with carbon black in a 75 / 25 ethanol / water mixture.

[0264] The carbon black is then filtered off while hot and the ethanol is evaporated off. The mixture is cooled to room temperature and the product is then filtered off and dried under vacuum.

[0265] A pale yellow powder is thus obtained.

[0266] The 1H NMR spectra and mass spectra are in accordance with the structure.

[0267] Melting point: 151°C (capillary tube).

[0268] Step 2: Synthesis of the compound N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycine from the compound obtained in step 1

[0269] Ethyl N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycinate (48 g, 0.317 mol) and 95% EtOH solution (48 mL) are placed into a three-necked flask.

[0270] The resulting mixture is cooled to 10°C.

[0271] A solution of NaOH (16 g) in 144 mL of water is added dropwise to the mixture.

[0272] 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 then filtered.

[0273] The product thus obtained is washed with water and dried under vacuum.

[0274] A pale yellow powder is obtained.

[0275] The 1H NMR spectra and mass spectra are in accordance with the structure.

[0276] Melting point: 241.0-241.8°C (capillary tube)

[0277] Example 2: Synthesis of compounds I-1 and I-2

[0278] The (2-mercaptonicotinoyl)glycine obtained in Example 1 (20.000 g, 1 eq, 94.242 mmol) and DMF (100 mL) are placed in a 250 mL round-bottomed flask.

[0279] The mixture is stirred until a clear solution is obtained, and carbonyldiimidazole (16.809 g, 1.1 eq, 103.67 mmol) is then added portionwise.

[0280] The resulting suspension is stirred at a temperature of 20°C until no more bubbling occurs (typically for one hour).

[0281] Ethyl glycinate hydrochloride (14.470 g, 1.1 eq, 103.67 mmol) is then added, and the mixture is stirred for one hour at a temperature of 20°C.

[0282] The reaction medium is then slowly added to 10% aqueous NaHCO3solution with stirring.

[0283] The suspension obtained is filtered through a sinter to yield 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.

[0284] The spectroscopic analyses are in accordance with the indicated structure.

[0285] Compound I-1, as obtained previously, (ethyl (2-mercaptonicotinoyl)glycylglycinate) (13.440 g, 1 eq, 45.202 mmol) and distilled water (70 mL) are placed into a 250 mL round-bottomed flask.

[0286] With stirring, a 50% sodium hydroxide solution is added until a pH value of about 12-13 is reached, while keeping the temperature below 25°C. The resulting mixture is stirred for one hour at a temperature of 25°C, and the pH is then adjusted to a value of 2 with 37% hydrochloric acid.

[0287] The suspension obtained is filtered through a sinter, and the resulting solid is then rinsed with distilled water.

[0288] The solid is dried at 50°C under vacuum to obtain compound I-2 (2-mercaptonicotinoyl)glycylglycine in the form of a yellow powder.

[0289] B- Examples of photostability of compound I-2 in the presence of amino-substituted 2-hydroxybenzophenone compounds

[0290] The following compositions were prepared at room temperature by mixing the ingredients listed in the table below. The numerical values for the amounts of the ingredients are all based on weight percentages as active materials.CompositionPhase12*WaterA73.4373.43Hydrophilic polymer(s)A0.50.52-Mercaptonicotinoyl glycine(Compound I-2 of Example A)A0.50.5Surfactant(s)A0.50.5Base(s)A0.070.07Ester oil(s)B23.5013.50Diethylamino hydroxybenzoyl hexyl benzoateB-10.00Lipophilic polymer(s)B1.51.5

[0291] * = composition according to the inventionProcedure

[0292] Preparation of the aqueous phase A:

[0293] The aqueous phase made up of water is heated to 70°C with continuous stirring. The hydrophilic polymer(s) are added to the aqueous phase with stirring over 10 minutes. This incorporation time is intended to ensure good dispersion of the polymer(s). After complete incorporation of the hydrophilic polymer(s), compound I-2 is added, still with vigorous stirring, over 10 minutes. This step allows homogenization of the aqueous phase and ensures the dissolution of compound I-2. The pH of the aqueous phase is adjusted.

[0294] Preparation of the oily phase B:

[0295] The oily phase, made up of diisopropyl sebacate and Intelimer H4, is heated to 72°C with continuous stirring.

[0296] Emulsification:

[0297] Phase B is poured into phase A with vigorous continuous stirring. The order of incorporation allows the formation of an oil-in-water (O / W) emulsion.

[0298] Stirring is maintained for 15 minutes after the oily phase has been completely added. This emulsification time allows small oil droplets to form and helps to stabilize the emulsion.

[0299] The emulsion is cooled to room temperature with moderate stirring. Slow, controlled cooling prevents phase separation and allows the stability of the emulsion to be maintained.

[0300] Evaluation of the photostability of compound I-2 (INCI name: 2-Mercaptonicotinoyl Glycine)Exposure conditions

[0301] The formulas are spread on polymethyl methacrylate (PMMA) plates without UV stabilizer additive, with a frosted side having a particle size of 5 to 6.5 µm. A thin film of 2 to 2.1 mg of formula per cm² of plate is deposited.

[0302] For each formula, deposits on eight plates are prepared:

[0303] Four plates are exposed to specific UV doses in a Suntest (CPS from Heraeus (Atlas / Ametek)) that simulates solar radiation (exposed test plates). A dose of 16 J / cm² is applied, representative of realistic sun exposure.

[0304] Four plates are not exposed to UV and will serve as reference samples (reference plates). They are kept in an oven at 40°C for the same duration as the UV exposure time of the other four plates.

[0305] Quantification is then performed on all samples using the following UPLC-UV method.

[0306] Quantification of compound I-2 and evaluation of photostability

[0307] Extraction of the formula from the plates is performed with a mixture of H3PO4 (0.1%) / methanol (90:10 (v / v)), assisted by sonication.

[0308] Quantification is then performed on all samples by using the following UPLC-UV method:

[0309] - System: Waters Acquity UPLC I-Class or equivalent;

[0310] - Column: Waters Acquity UPLC BEH shield RP18, 1.7 µm, 2.1X100 mm or equivalent;

[0311] - Mobile phase: 12-minute gradient of a mixture of eluent A (0.1% phosphoric acid in aqueous solution) & B (methanol);

[0312] - Flow rate: 0.4 mL / min;

[0313] - Detection wavelength: 296 nm.

[0314] 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.

[0315] Results expressed as residual fractions (RF):

[0316] Results

[0317] The results obtained are collated in the table below.Photostability as a percentage of compound I-2RF (%)1 after exposure90% residual2* after exposure97% residual

[0318] These results show that in composition 2 according to the invention, which comprises at least one amino-substituted 2-hydroxybenzophenone compound (diethylamino hydroxybenzoyl hexyl benzoate), compound I-2 has significantly improved photostability compared to the comparative composition 1, which does not contain any amino-substituted 2-hydroxybenzophenone compound. Specifically, the level of residual compound I-2 after exposure to UV radiation is markedly higher in composition 2 than in composition 1.

Claims

Composition, in particular a cosmetic or dermatological composition, comprising:a) at least one amino-substituted 2-hydroxybenzophenone compound; andb) at least one compound selected from the compounds of formula (I), the tautomers of formula (I'), salts thereof, solvates thereof such as hydrates thereof, optical isomers thereof, racemates thereof, and mixtures thereof:in which:- 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-based 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.Composition according to Claim 1, in which the amino-substituted 2-hydroxybenzophenone compound(s) are chosen from compounds corresponding to formula (I) below:in which:R1and R2, which may be identical or different, denote a C1-C20alkyl radical, a C2-C20alkenyl radical, a C3-C10cycloalkyl radical, a C3-C10cycloalkenyl radical, or form a 5- or 6-membered ring with the nitrogen atom to which they are attached;n is a number ranging from 1 to 4;when n = 1, R3denotes a C1-C20alkyl radical, a C1-C20alkenyl radical, a C1-C5hydroxyalkyl radical, a C6-C12cyclohexyl radical, a phenyl which may be substituted with O, N or S, an aminocarbonyl radical or a C1-C5alkylcarbonyl radical;when n = 2, R3denotes an alkyl diradical, a cycloalkyl diradical, an alkenyl diradical or an aryl diradical, or R3together with E form a diradical of formula (II):where m is a number ranging from 1 to 3;when n = 3, R3is an alkyl triradical;when n = 4, R3is an alkyl tetraradical;E is –O-, or –N(R4)- or N;R4is hydrogen, or a C1-C5alkyl or C1-C5hydroxyalkyl radical.Composition according to either of Claims 1 and 2, in which the amino-substituted 2-hydroxybenzophenone compound is n-hexyl 2-(4-diethylamino-2-hydroxybenzoyl)benzoate of formula (a):Composition according to any one of Claims 1 to 3, in which the amino-substituted 2-hydroxybenzophenone compound(s) are present in contents ranging from 0.01% to 20% by weight, preferably from 0.1% to 10% by weight and more preferentially from 0.5% to 5% by weight relative to the total weight of the composition.Composition according to any one of Claims 1 to 4, in which R1of formulae (I) and (I’) represents a hydrogen atom; a linear (C1-C10) alkyl group or a branched (C3-C10) alkyl group, notably a linear (C1-C6) alkyl group or a branched (C3-C6) alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl or isobutyl, more preferably ethyl; in particular, said alkyl group of R1is unsubstituted.Composition according to any one of Claims 1 to 5, in which R2of formulae (I) and (I’) represents a hydrogen atom; a linear (C1-C10) or branched (C3-C10) alkyl group, notably a linear (C1-C6) or branched (C3-C6) alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl or isobutyl, more preferably methyl or ethyl; said alkyl group of R2not being substituted.Composition according to any one of Claims 1 to 6, in which R3of formulae (I) and (I’) represents a hydrogen atom; a linear C1-C10or branched C3-C10saturated alkyl 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.Composition according to any one of Claims 1 to 7, in which R2of formulae (I) and (I’) represents a linear (C1-C10) alkyl group or a branched (C3-C10) alkyl group, notably a linear (C1-C6) alkyl group or a branched (C3-C6) alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl or 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 according to 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.Composition according to any one of Claims 1 to 8, in which 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, which is in particular unsubstituted.Composition according to any one of Claims 1 to 9, in which 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.Composition according to any one of Claims 1 to 10, in which:- 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, for instance C5-C6, hydrocarbon-based 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.Composition according to any one of Claims 1 to 11, in which:- 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, which is more preferably unsubstituted;- 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-based 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.Composition according to any one of Claims 1 to 12, in which 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 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-carboxamideComposition according to any one of Claims 1 to 13, in which 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.Composition according to any one of Claims 1 to 14, also containing one or more additional UV-screening agents.Composition according to any one of Claims 1 to 15, in which the pH is between 4 and 10, preferably between 5 and 8.5 and preferentially between 5.5 and 8.Use of at least one amino-substituted 2-hydroxybenzophenone compound as defined in any one of Claims 1 to 3, for photostabilizing at least one compound selected from the compounds of formula (I), the tautomers of formula (I'), salts thereof, solvates thereof such as hydrates thereof, optical isomers thereof, and racemates thereof, as defined in any one of Claims 1 and 5 to 13, in particular when it is dissolved in a composition comprising at least an aqueous phase, even in the presence of additional UV-screening agents.

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