Antioxidant compositions comprising thiopyridone compounds

Abstract

A composition comprising: A) a thiopyridone compound and B) an antioxidant selected from ascorbic acid or a stabilized derivative thereof in an amount of from 15% to 30% by weight of the composition.

Description

Technical Field The present invention relates to antioxidant compositions comprising thiopyridone compounds which are useful for caring for keratin materials and in particular the skin.

[0002] background The ultimate goal in the cosmetics field is always to make products with skin benefits, such as hydration, moisturizing, anti-aging, brightening, cleansing, etc. Consumers are always highly interested in brightening the skin, especially those with deep or dark skin tones. Unfortunately, some people see the appearance of darker and / or more colored spots on their skin (and more especially on the hands) at various times in their lives, which brings unevenness to the skin. These spots are particularly due to the high concentration of melanin in the keratinocytes located at the surface of the skin.

[0003] It is known that certain thiopyridone compounds exhibit good depigmentation activity even at low concentrations, see, for example, WO2012080075 and WO2017 / 102349. Thiopyridone compounds can show strong depigmentation or lightening effects by reducing the production of melanin.

[0004] However, there is still a need in the art for new uses of thiopyridones. SUMMARY OF THE INVENTION The inventors have surprisingly found that a composition comprising the following components can not only achieve the desired depigmentation or lightening effect, but also promote an antioxidant effect: A) a compound of formula (I) or (I') which can be regarded as a thiopyridone compound, or a salt thereof, an optical isomer, a racemate and / or a solvate (e.g. a hydrate), and the like, alone or in a mixture; and B) an antioxidant, which comprises ascorbic acid or a stabilized derivative thereof in an amount of at least 5% by weight of the composition.

[0006] In the formula (I) and formula (I'): R 1 represents a group selected from the following: a) Hydrogen atom; b) Saturated straight chain C 1 -C 10 or branched chain C 3 -C 10 An alkyl group, which is optionally substituted by one or more groups which may be the same or different and are selected from the following: i)-OR 3 ; ii)-SR 3 ; R2 represents a group selected from the following: a) Hydrogen atom; b) Straight chain C 1 -C 12 or branched chain C 3 -C 12 or cyclic C 3 -C 8 A saturated hydrocarbon group, which is optionally substituted by one or more groups which may be the same or different and are selected from the following: i)-OR 3 ; ii)-SR 3 ; iii) -C(O)-OR 3 ; iv) C 5 -C 12 Aryl, which is optionally substituted by one or more hydroxyl groups and / or one or more C 1 -C 8 Alkoxy substitution; c)C 5 -C 12 Aryl, which is optionally substituted by one or more hydroxyl groups and / or one or more C 1 -C 8 Alkoxy substitution; R 3 represents a group selected from the following: a) Hydrogen atom; b) Saturated straight chain C 1 -C 10 or branched chain C 3 -C 10 Hydrocarbon; Compound (I') is a tautomeric form of compound (I) where a tautomeric equilibrium exists according to the following formula: According to one embodiment of the present invention, R 1 Represents a hydrogen atom.

[0007] According to another embodiment of the present invention, R 1 Represents a straight chain (C 1 -C 10 ) alkyl or branched (C 3 -C 10 ) alkyl, especially straight chain (C 1 -C 6 ) alkyl or branched (C 3 -C 6 ) alkyl, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably ethyl.1 The alkyl group is unsubstituted.

[0008] According to one embodiment of the present invention, R 2 Represents a hydrogen atom.

[0009] According to another embodiment of the present invention, R 2 Represents a straight chain (C 1 -C 10 ) alkyl or branched (C 3 -C 10 ) alkyl, especially straight chain (C 1 -C 6 ) alkyl or branched (C 3 -C 6 ) alkyl, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably methyl or ethyl; R 2 The alkyl group is unsubstituted.

[0010] According to another embodiment of the present invention, R 2 Represents a straight chain (C 1 -C 10 ) alkyl or branched (C 3 -C 10 ) alkyl, especially straight chain (C 1 -C 6 ) alkyl or branched (C 3 -C 6 )alkyl, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably methyl or ethyl; the alkyl is substituted by one or more groups selected from i), ii), iii) and iv) as defined above. The alkyl is preferably substituted by one or two groups selected from i), ii) and iii), more preferably substituted by one or two groups selected from i) and iii), more preferably substituted by one group iii) (such as carboxyl).

[0011] For group R 2 Another variant of is that the alkyl is substituted by a group iv), in particular by a phenyl.

[0012] According to another embodiment of the present invention, R 2 Representative (C 3 -C 8 ) cycloalkyl, preferably (C 5 -C 7 ) cycloalkyl, for example cyclohexyl.

[0013] According to another embodiment of the present invention, R 2 Represents C 5 -C 12Aryl, which is optionally substituted by one or more hydroxyl groups and / or one or more C 1 -C a Alkoxy substituted, preferably unsubstituted phenyl.

[0014] According to one embodiment, R 3 Represents a hydrogen atom.

[0015] According to another embodiment, R 3 Represents a saturated straight chain C 1 -C 10 or branched chain C 3 -C 10 Hydrocarbyl; especially straight chain (C 1 -C 6 ) alkyl or branched (C 3 -C 6 ) alkyl, preferably (C 1 -C 4 ) alkyl, for example methyl.

[0016] Embodiments of the invention Throughout the specification (including claims), unless otherwise mentioned, the term "comprising" should be understood as being synonymous with "comprising at least one". In addition, the expression "at least one" used in this specification is equivalent to the expression "one or more".

[0017] For the purposes of the present invention, and unless otherwise indicated: "Straight Chain C 1 -C 12 or branched chain C 3 -C 12 Saturated hydrocarbon group" is equivalent to "straight chain (C 1 -C 12 ) alkyl or branched (C 3 -C 12 ) alkyl", which corresponds to a saturated C-based 1 -C 12 Straight chain or C 3 -C 12 branched hydrocarbon radical, and preferably based on C 1 -C 10 Straight chain or C 3 -C 10 A branched hydrocarbon group, more preferably based on C 1 -C 6 Straight chain or C 3 -C 6branched hydrocarbon radical; preferably, the straight or branched radical may be selected from methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl and decyl.

[0018] More preferably, the saturated straight or branched hydrocarbon group can be selected from methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl, pentyl, hexyl, heptyl and octyl, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl.

[0019] ■ Ring C 3 -C 8 The saturated hydrocarbon group is a monocyclic cycloalkyl or bicyclic cycloalkyl group containing 3 to 8 carbon atoms, especially a monocyclic C5-C7 cycloalkyl group, such as cyclohexyl, ■ "Alkoxy" is an alkyl-oxy group, wherein the alkyl group is a straight or branched chain based on C 1 -C 16 (and preferably C 1 -C 8 ) a hydrocarbon group; ■ When alkoxy is optionally substituted, this means that alkyl is optionally substituted as defined above; ■ "Aryl" represents a fused or non-fused monocyclic or bicyclic carbon-based group containing 5 to 12 carbon atoms, preferably 6 to 10 carbon atoms, and wherein at least one ring is aromatic; preferably, aryl is phenyl, biphenyl, naphthyl, more preferably phenyl; ■ The term "at least one" is equivalent to the term "one or more"; and ■ The term "inclusive" with respect to a concentration range means that the upper and lower limits of the defined range are included in the range.

[0020] Salts of compounds of formula (I), (I'), (II) or (II') as defined hereinafter include conventional non-toxic salts of said compounds such as those formed from organic or inorganic acids or from organic or inorganic bases.

[0021] As salts of the compounds of formula (I), (I'), (II) or (II'), mention may be made of: Salts obtained by addition of a compound of formula (I) or (II) with: - inorganic bases, for example sodium hydroxide, potassium hydroxide, calcium hydroxide, ammonium hydroxide, magnesium hydroxide, lithium hydroxide and for example sodium, potassium or calcium carbonate or sodium, potassium or calcium bicarbonate; or - organic bases, for example primary, secondary or tertiary alkylamines, for example triethylamine or butylamine. The primary, secondary or tertiary alkylamines may contain one or more nitrogen atoms and / or oxygen atoms and may therefore contain, for example, one or more alcohol functions; mention may especially be made of 2-amino-2-methylpropanol, ethanolamine, triethanolamine, 2-dimethylaminopropanol, 2-amino-2-(hydroxymethyl)-1,3-propanediol and 3-(dimethylamino)propylamine.

[0022] Mention may also be made of the salts of amino acids such as lysine, arginine, guanidine, glutamic acid and aspartic acid. Advantageously, the salt of the compound of formula (I) or (II) when it comprises a carboxyl group may be chosen from alkali metal salts or alkaline earth metal salts, such as sodium, potassium, calcium or magnesium salts, and ammonium salts.

[0023] As "acid salt of organic or inorganic acid", more particularly, it is selected from the following salts: it is selected from the salts derived from the following acids: i) hydrochloric acid HCl, ii) hydrobromic acid HBr, iii) sulfuric acid H 2 SO 4 iv) Alkyl sulfonic acid: Alk-S(O) 2 OH, such as methanesulfonic acid and ethanesulfonic acid; v) arylsulfonic acid: Ar-S(O) 2 OH, such as benzenesulfonic acid and toluenesulfonic acid; vi) citric acid; vii) succinic acid; viiii) tartaric acid; ix) lactic acid; x) alkoxysulfinic acid: Alk-OS(O)OH, such as methoxysulfinic acid and ethoxysulfinic acid; xi) aryloxysulfinic acid, such as tolyloxysulfinic acid and phenoxysulfinic acid; xii) phosphoric acid H 3 PO 4 ; xiii) acetic acid CH 3 C(O)OH; xiv) trifluoromethanesulfonic acid CF 3 SO 3 H; and xv) tetrafluoroborate HBF 4 ; ■ Acceptable solvates of the compounds described in the present invention include customary solvates, such as those formed during the preparation of the compounds due to the presence of solvents. By way of example, mention may be made of solvates due to the presence of water or linear or branched alcohols such as ethanol or isopropanol.

[0024] ■ Optical isomers, especially enantiomers and diastereomers.

[0025] Preferably, the "keratin material" according to the invention is the skin. By "skin" we intend (mean) all body skin. Still preferably, the keratin material is the face or neck, in particular the face.

[0026] In the present application, the amount, content, part and percentage are expressed on a weight basis unless specifically mentioned otherwise.

[0027] In the present application, when necessary, numerical range is defined with lower limit and upper limit, for example, one or more lower limits and one or more upper limits are given, to form a range (optionally together with one or more preferred ranges). A given range can be defined by selecting the lower limit and upper limit of the boundary defining a given range. All ranges defined in this way are inclusive and combinable, that is, any lower limit can be combined with any upper limit to form a range, as long as the lower limit and upper limit are provided to limit the same object. For example, when the scope of 60-110 and 80-120 is listed for a particular object, it should be understood that scope 60-120 and 80-110 are also considered and covered. In addition, if the lower limit listed is 1 and 2, and the upper limit listed is 3, 4 and 5, then the following ranges are all predictable, and within the scope of the present disclosure: 1-3, 1-4, 1-5, 2-3, 2-4 and 2-5.

[0028] Except in the operating examples, or where otherwise indicated, all numbers expressing amounts of ingredients and / or reaction conditions are to be understood as being modified in all instances by the term "about," having the conventional meaning in the art, e.g., within 10% of the indicated value (e.g., "about 10%" means 9%-11%, and "about 2%" means 1.8%-2.2%).

[0029] The present invention provides a composition comprising the following components: A) a compound of formula (I) or (I'), and B) a specific antioxidant.

[0030] Component A) The composition according to the present invention comprises, as component A), a compound of the following formula (I) or (I') or the following tautomer (I') or a salt thereof, an optical isomer thereof, a racemate thereof and / or a solvate (eg hydrate), and the like, alone or in a mixture: In the formula (I) and formula (I'): R 1 represents a group selected from the following: a) Hydrogen atom; b) Saturated straight chain C 1 -C 10 or branched chain C 3 -C 10 A hydrocarbon group, which is optionally substituted with one or more groups which may be the same or different and are selected from: i)-OR 3 ; ii)-SR3 ; R 2 represents a group selected from the following: a) Hydrogen atom; b) Straight chain C 1 -C 12 or branched chain C 3 -C 12 or cyclic C 3 -C 8 A saturated hydrocarbon group, which is optionally substituted by one or more groups which may be the same or different and are selected from the following: i)-OR 3 ; ii)-SR 3 ; iii) -C(O)-OR 3 ; iv) C 5 -C 12 Aryl, which is optionally substituted by one or more hydroxyl groups and / or one or more C 1 -C 8 Alkoxy substitution; c)C 5 -C 12 Aryl, which is optionally substituted by one or more hydroxyl groups and / or one or more C 1 -C 8 Alkoxy substitution; R 3 represents a group selected from the following: a) Hydrogen atom; b) Saturated straight chain C 1 -C 10 or branched chain C 3 -C 10 Hydrocarbon; Compound (I') is a tautomeric form of compound (I) where a tautomeric equilibrium exists according to the following formula: According to one embodiment of the present invention, R 1 Represents a hydrogen atom.

[0031] According to another embodiment of the present invention, R 1 Represents a straight chain (C 1 -C 10 ) alkyl or branched (C 3 -C 10 ) alkyl, especially straight chain (C 1 -C 6 ) alkyl or branched (C 3 -C 6) alkyl, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably ethyl. 1 The alkyl group is unsubstituted.

[0032] According to one embodiment of the present invention, R 2 Represents a hydrogen atom.

[0033] According to another embodiment of the present invention, R 2 Represents a straight chain (C 1 -C 10 ) alkyl or branched (C 3 -C 10 ) alkyl, especially straight chain (C 1 -C 6 ) alkyl or branched (C 3 -C 6 ) alkyl, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably methyl or ethyl; R 2 The alkyl group is unsubstituted.

[0034] According to another embodiment of the present invention, R 2 Represents a straight chain (C 1 -C 10 ) alkyl or branched (C 3 -C 10 ) alkyl, especially straight chain (C 1 -C 6 ) alkyl or branched (C 3 -C 6 )alkyl, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably methyl or ethyl; the alkyl is substituted by one or more groups selected from i), ii), iii) and iv) as defined above. The alkyl is preferably substituted by one or two groups selected from i), ii) and iii), more preferably substituted by one or two groups selected from i) and iii), more preferably substituted by one group iii) (such as carboxyl).

[0035] For group R 2 Another variant of is that the alkyl is substituted by a group iv), in particular by a phenyl.

[0036] According to another embodiment of the present invention, R 2 Representative (C 3 -C 8 ) cycloalkyl, preferably (C 5 -C 7 ) cycloalkyl, for example cyclohexyl.

[0037] According to another embodiment of the present invention, R 2 Represents C 5-C 12 Aryl, which is optionally substituted by one or more hydroxyl groups and / or one or more C 1 -C 8 Alkoxy substituted, preferably unsubstituted phenyl.

[0038] According to one embodiment, R 3 Represents a hydrogen atom.

[0039] According to another embodiment, R 3 Represents a saturated straight chain C 1 -C 10 or branched chain C 3 -C 10 Hydrocarbyl; especially straight chain (C 1 -C 6 ) alkyl or branched (C 3 -C 6 ) alkyl, preferably (C 1 -C 4 ) alkyl, for example methyl.

[0040] Preferably, the compound of formula (I) and tautomer (I') or salts thereof, optical isomers, racemates and / or solvates (eg hydrates) thereof, alone or in mixture, and; Has the following meanings: R 1 represents a group selected from the following: a) Hydrogen atom; b) Saturated straight chain C 1 -C 6 or branched chain C 3 -C 6 A hydrocarbon group, which is optionally substituted with one or more groups which may be the same or different and are selected from: i)-OR 3 ; ii)-SR 3 ; Preferably, it is optionally substituted with one or more groups i); R 2 represents a group selected from the following: a) Hydrogen atom; b) Straight chain C 1 -C 10 or branched chain C 3 -C 10 or cyclic C 3 -C 8 (e.g. C5-C6) saturated hydrocarbon group, which is optionally substituted by one or more groups which may be the same or different and are selected from the following: i)-OR 3 ; ii)-SR- 3 ; iii) -C(O)-OR 3 ; iv) phenyl, which is optionally substituted by one or more hydroxyl groups and / or one or more C 1 -C 4 Alkoxy (e.g. methoxy) substitution; Preferably substituted by one or more groups selected from i) and iii), preferably iii) (eg carboxyl); R 3 represents a group selected from the following: a) Hydrogen atom; b) Saturated straight chain C 1 -C 6 or branched chain C 3 -C 6 Hydrocarbon; Preferably, the compound of formula (I) and tautomer (I') or salts thereof, optical isomers, racemates and / or solvates (eg hydrates) thereof, alone or in mixture, and; Has the following meanings: R 1 represents a group selected from the following: a) Hydrogen atom; b) Saturated straight chain C 1 -C 4 or branched chain C 3 -C 4 a hydrocarbon group, which is optionally substituted by one or more groups which may be the same or different and are selected from i) -OR 3 substituted with, more preferably unsubstituted; R 2 represents a group selected from the following: a) Hydrogen atom; b) Straight chain C 1 -C 10 or branched chain C 3 -C 10 or cyclic C 3 -C 8 (e.g. C5-C6) saturated hydrocarbon group, which is optionally substituted by one or more groups which may be the same or different and are selected from the following: i)-OR 3 ; iii) -C(O)-OR 3 ; iv) C 5 -C 12 Aryl, which is optionally substituted by one or more hydroxyl groups and / or one or more C 1 -C4 Alkoxy substitution; R 3 represents a group selected from the following: a) Hydrogen atom; b) Saturated straight chain C 1 -C 4 or branched chain C 3 -C 4 A hydrocarbon group, such as a methyl or ethyl group.

[0041] Preferably, the compound of formula (I) and tautomer (I') or salts thereof, optical isomers, racemates and / or solvates (eg hydrates) thereof, alone or in mixture, and; Has the following meanings: R 1 is a hydrogen atom; and R 2 represents a group selected from the following: a) Hydrogen atom; b) Straight chain C 1 -C 5 or branched chain C 3 -C 5 or cyclic C 3 -C 8 (such as C5-C6) saturated hydrocarbon group, which is replaced by one or more groups which may be the same or different and are selected from v) -C(O)-OR 3 substituted by a group, preferably by a group iii) -C(O)-OR 3 replace; R 2 Even more preferably, a straight chain C 1 -C 4 or branched chain C 3 -C 4 Saturated hydrocarbon group, which is replaced by a group iii) -C(O)-OR 3 replace.

[0042] According to another preferred embodiment, the compound of formula (I) and the tautomer (I') are selected from the compound of formula (II) and also its tautomers, its salts, its solvates, and its optical isomers, and its racemates, alone or in mixture: In formulae (II) and (II'), R1 and R3 have the same meanings as for the compounds of formulae (I) and (I'), and X represents an alkylene group -(CH 2 ) n -, wherein n is an integer ranging from 1 to 10, preferably ranging from 1 to 6, more preferably ranging from 1 to 4, for example 1, preferably R 3Represents a hydrogen atom.

[0043] Among the compounds of formula (I), the following compounds, and their tautomers or salts thereof, their optical isomers, racemates and / or solvates (eg hydrates), and the like are preferably used alone or in a mixture: Among these compounds, the following compounds are more particularly preferred: More preferably, among these compounds, the following compounds are more particularly preferred: Even more preferably, among these compounds, the following compounds are more particularly preferred: In a most preferred embodiment, the compound according to the invention is the following compound:

[0044] All compounds can be obtained from commercially available reagents by chemical methods known to those skilled in the art. For example, the synthesis method disclosed in European patent application EP3390363 can be used.

[0045] Compound 20, N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycine, also named 3-carboxymethylaminocarbonyl-2-thiopyridone, is a typical representative of useful thiopyridone compounds according to the present invention.

[0046] The component A) compound may be present in an amount ranging, for example, from 0.01% to 10%, preferably from 0.1% to 5% or preferably from 0.5% to 3% by weight relative to the total weight of the composition.

[0047] Component B) Antioxidant The compositions according to the invention comprise antioxidants as component B).

[0048] Without being bound by any known theory, it has surprisingly been found that for component A), vitamin C or a stabilized derivative thereof is particularly useful in component B).

[0049] Therefore, according to one embodiment of the present invention, the composition necessarily comprises vitamin C or a stabilized derivative thereof in component B).

[0050] As useful antioxidants, vitamin C and derivatives can be used, including ascorbic acid, isoascorbic acid, or derivatives thereof (particularly stabilized derivatives thereof), such as sodium ascorbate / sodium isoascorbate, and fat-soluble esters tetrahexyldecyl ascorbate / tetrahexyldecyl isoascorbate and ascorbyl palmitate, magnesium ascorbyl phosphate, ascorbyl glucoside, ascorbyl glucosamine, ascorbyl acetate, etc. In addition, it is also possible to use plants containing a large amount of vitamin C, such as extracts of Camu (Myrciaria dubia), Acerola, Emblica officinalis; and bioflavonoids from rose hips and citrus, including water-soluble bioflavonoids, such as hesperidin methyl chalcone.

[0051] Component B) may also contain an "additional antioxidant" different from vitamin C or its derivatives, which may be cinnamic acid or its derivatives, such as phenylpropanoids. Phenylpropanoids include: cinnamic acid, caffeic acid, ferulic acid, trans-ferulic acid (including its antioxidant pharmacore 2,6-dihydroxyacetophenone), 5-hydroxyferulic acid, sinapic acid, coumarin, coniferyl alcohol, sinapyl alcohol, eugenol, chavicol, baicalein, p-coumaric acid and sinapic acid. Without limiting the mode of action of the present invention, phenylpropanoids can neutralize free radicals.

[0052] In particular, useful cinnamic acid derivatives may include 2-ethylhexyl methoxycinnamate, isopropyl methoxycinnamate, isoamyl methoxycinnamate, diisopropyl methoxycinnamate, pentaerythritol tetrakis (di-tert-butyl hydroxyhydrocinnamate) (Tinogard TT), octadecyl di-tert-butyl-4-hydroxyhydrocinnamate, caffeic acid, ferulic acid. Caffeic acid and ferulic acid may be preferred, and ferulic acid may be more preferred.

[0053] According to the invention, vitamin C or its stabilized derivative may be present in the composition according to the invention in an amount of 15% to 30% by weight, or preferably 15% to 20% by weight, relative to the total weight of the composition.

[0054] According to one embodiment of the invention, the "additional antioxidant" present in the composition according to the invention may be v%-2% by weight, preferably 0%-1% by weight or preferably 0.1%-0.5% by weight relative to the total weight of the composition.

[0055] Medium / Solvent The composition according to the invention may advantageously comprise at least one medium / solvent including water and / or an organic medium / solvent.

[0056] water Compositions according to the present invention may advantageously include various amounts of water. For low-viscosity applications of the composition, such as in the form of a leave-on emulsion, relatively large amounts of water may be used. For example, relative to the gross weight of the composition, the use content of water is greater than or equal to 40 weight %. Relative to the gross weight of the low-viscosity composition according to the present invention, the water content in the composition preferably ranges from 40 weight % to 99 weight %, or preferably from 50 weight % to 90 weight % or from 60 weight % to 80 weight %.

[0057] For high viscosity applications of the composition, for example in the form of a leave-on cream, relatively small amounts of water may be used. The composition advantageously comprises water in an amount less than or equal to 40% by weight relative to the total weight of the high viscosity composition according to the invention. The water content in the composition preferably ranges from 10% to 40% by weight, or preferably from 15% to 35% by weight or from 20% to 30% by weight relative to the total weight of the high viscosity composition according to the invention.

[0058] Organic medium / solvent The composition according to the invention may also comprise one or more organic media / solvents, preferably water-soluble organic media / solvents (solubility in water at 25° C. and atmospheric pressure greater than or equal to 5%).

[0059] Examples of organic media / solvents that may be mentioned include the following, alone or in mixtures: linear or branched, and preferably saturated, mono- or diols containing 2 to 10 carbon atoms, such as ethanol, (iso)propanol, butanol, hexanediol (2-methyl-2,4-pentanediol), neopentyl glycol and 3-methyl-1,5-pentanediol, butanediol, dipropylene glycol and propylene glycol; aromatic alcohols, such as phenylethyl alcohol; polyols containing more than two hydroxyl functions, especially C3-C6 polyols, such as glycerol; polyol ethers, such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether and ethylene glycol monobutyl ether, propylene glycol or its ethers, such as propylene glycol monomethyl ether; and also diethylene glycol alkyl ethers (especially C3-C6 polyols). 1 -C 4 alkyl ethers), such as diethylene glycol monoethyl ether or diethylene glycol monobutyl ether.

[0060] When an organic medium / solvent is present, it is present in an amount ranging from 0.1% to 40% by weight, preferably from 1% to 30% by weight or from 5% to 20% by weight relative to the total weight of the composition according to the invention.

[0061] The composition according to the invention can be used for various purposes, including direct application on keratin materials or for formulating other cosmetic products, such as body creams and especially various facial masks.

[0062] Thus, depending on the particular use, various additional components may be incorporated into the composition, or used with the composition according to the present invention.

[0063] Other active agents In the case of a mask, it is also possible to use active agents for improving the condition of the skin, such as moisturizers or agents for improving the natural lipid barrier. It is also possible to use enzymes that are active on the skin.

[0064] As other examples of active agents that may be suitable for practicing the present invention, there are agents used in medicines, peptides, proteins, detectable markers, imaging agents, analgesics, anesthetics, antibacterial agents, antiyeast agents, antifungal agents, antiviral agents, antidermatitis agents, antipruritic agents, antiemetic agents, vascular protectants, anti-motion sickness agents, anti-irritants, anti-inflammatory agents, immunomodulators, anti-hyperkeratotic agents, agents for treating dry skin, antiperspirants, antipsoriatic agents, antidandruff agents, anti-aging agents, anti-asthmatic agents and bronchodilators, sunscreens, antihistamines, healing agents, corticosteroids, tanning agents, and mixtures thereof.

[0065] The content of other active agents in the composition according to the invention may be adjusted as the intended purpose of the kit varies.

[0066] preservative For the use according to the invention, the composition according to the invention may comprise at least one preservative. The preservative useful according to the invention may be any one conventionally used in cosmetics, in particular for facial masks.

[0067] Preferably, the content of the preservative is 0.01 wt%-5 wt%, preferably 0.01 wt%-3 wt%, preferably 0.01 wt%-1 wt%, based on the weight of the composition.

[0068] pH Adjusters The composition according to the invention may optionally comprise at least one pH adjusting agent.

[0069] Examples of pH adjusters include, but are not limited to, aminomethyl propanol, aminomethyl propylene glycol, triethanolamine, triethylamine, citric acid, sodium hydroxide, acetic acid, potassium hydroxide, lactic acid, and any combination thereof.

[0070] The amount of the pH adjusting agent in the composition according to the present invention can be adjusted and determined by a technician according to the desired pH, as long as its amount does not bring other substantial harmful effects. For example, relative to the total weight of the composition, the pH adjusting agent can be present in an amount of 1 wt%-20 wt%, such as 5 wt%-15 wt%.

[0071] Adjuvants In a known manner, depending on the end use and / or the specific product form, the composition according to the invention may also contain adjuvants customary in the cosmetic, pharmaceutical and / or dermatological fields, such as hydrophilic or lipophilic gelling agents, emulsifiers, hydrophilic or lipophilic active agents, fragrances, fillers, odor absorbers and dyes. The amounts of these various adjuvants are those conventionally used in the field under consideration and are, for example, from 0.01% to 20% by weight, based on the total weight of the composition.

[0072] These adjuvants and their concentrations must be such that they do not alter the desired properties of the compositions of the present invention.

[0073] The composition according to the invention can be manufactured by known methods generally used in the cosmetic or dermatological fields.

[0074] The composition according to the invention finds its application in a large number of cosmetic treatments for keratin materials such as the skin, scalp or mucous membranes (lips), and more particularly the skin, in particular in facial care, to lighten the skin. For example, the composition according to the invention may be particularly useful in mask products.

[0075] A subject of the invention is also a cosmetic method for caring for or making up keratin materials, which comprises applying to the keratin materials a composition as defined above.

[0076] A subject of the present invention is also a non-therapeutic cosmetic method for caring for or making up keratin materials, which comprises applying to the keratin materials a composition as defined above.

[0077] The invention also relates to the cosmetic use of a composition as defined above for caring for or making up keratin materials.

[0078] More particularly, a subject of the present invention is the cosmetic use of a composition as defined above for caring for the skin, preferably for lightening the skin, and / or for reducing or lightening darker and / or more pigmented spots on the skin.

[0079] In a particular embodiment, the composition is suitable for treating darker and / or more pigmented spots on the skin. Example The following examples of compositions according to the invention are given by way of illustration and not limitation. The compounds are indicated by chemical name or INCI name.

[0081] Compound 20 was synthesized as disclosed in Example 2 of patent EP3390363.

[0082] Unless otherwise indicated, the amounts / concentrations of ingredients in the compositions / formulations described below are expressed in weight % relative to the total weight of the respective composition / formulation.

[0083] Example A The inventive compositions of Ex.1-Ex.2 and the comparative compositions of CE.1-CE.4 were prepared from the ingredients specified in Table 1 below (wherein the contents are specified in weight % of the material relative to the total weight of the composition): Table 1 INCI Ex.1 Ex.2 CE.1 CE.2 CE.3 CE.4 ascorbic acid 15.00 15.00 20.00 0.00 13.00 13.00 Compound 20 0.75 0.25 0.75 Ferulic acid 1.90 glycerin 0.80 0.80 0.80 0.80 0.80 0.80 Chlorphenesin 0.20 0.20 0.20 0.20 0.20 0.20 Potassium hydroxide 9.72 9.30 12.59 0.20 8.23 8.16 water Appropriate amount up to 100 Appropriate amount up to 100 Appropriate amount up to 100 Appropriate amount up to 100 Appropriate amount up to 100 Appropriate amount up to 100 Taking Ex.1 as an example, the composition is prepared by the following steps: 1). Preparing an aqueous solution of compound 20 (or ferulic acid); 2). Heat the solution at 60°C for 20 minutes and then cool to room temperature; 3). Adding ascorbic acid and chlorphenesin; and 4). Add potassium hydroxide to adjust the pH.

[0084] Example B The antioxidant properties of the inventive compositions of Ex.1-Ex.2 and the comparative compositions of CE.1-CE.4 prepared in Example A were evaluated by a thin layer squalene oxidation test comprising the following steps: 1. Apply the artificial essence on the squalene solution; 2. Prepare a smoke solution, which is known in the art as an acetonitrile aqueous solution imbibed with smoke; 3. Apply the inventive compositions of Ex.1-Ex.2 and the comparative compositions of CE.1-CE.4, and apply the smoke solution (5 plates / composition), and apply the compositions and the smoke solution to a 2.5 cm*2 cm slide in sequence; 4. Simulated sunlight (5J / cm 2 , 17 minutes); 5. Let the reaction stand overnight; 6. Cut the glass into pieces, extract with 5 ml MeOH, and shake for 1 hour; 7. Filter all extracts; and 8. The response of SQOOH & SQ was detected by LCMS.

[0085] The detection of the response of SQOOH & SQ is a test well known in the art to measure antioxidant performance. The smaller the value of SQOOH / SQ, the better the antioxidant performance.

[0086] The results are given in Table 2 below.

[0087] Table 2 nature Ex.1 Ex.2 CE.1 CE.2 CE.3 CE.4 SQOOH / SQ 9 10.2 10.8 15.9 13 16

Claims

1. A composition comprising the following components: A) at least one compound selected from the group consisting of compounds of formula (I) and tautomers of formula (I') hereinafter, alone or in mixture; and salts, optical isomers, racemates and / or solvates such as hydrates thereof: In the formula (I) and formula (I'): -R1 represents a group selected from the following: a) Hydrogen atom; b) Saturated straight chain C1-C 10 or branched C3-C 10 A hydrocarbon group, which is optionally substituted with one or more groups which may be the same or different and are selected from: i) -O-R3; ii) -S-R3; -R2 represents a group selected from the following: a) Hydrogen atom; b) Straight chain C1-C 12 or branched C3-C 12 or a cyclic C3-C8 saturated hydrocarbon group, which is optionally substituted by one or more groups which may be the same or different and are selected from the following: i) -O-R3; ii) -S-R3; iii) -C(O)-O-R3; iv) C5-C 12 Aryl, which is optionally substituted with one or more hydroxyl groups and / or one or more C1-C8 alkoxy groups; c) C5-C 12 Aryl, which is optionally substituted with one or more hydroxyl groups and / or one or more C1-C8 alkoxy groups; -R3 represents a group selected from the following: a) Hydrogen atom; b) Saturated straight chain C1-C 10 or branched C3-C 10 Hydrocarbon; B) an antioxidant comprising vitamin C or a stabilized derivative thereof selected from the group consisting of ascorbic acid, erythorbic acid, sodium ascorbate / sodium isoascorbate, tetrahexyldecyl ascorbate / tetrahexyldecyl isoascorbate, ascorbyl palmitate, magnesium ascorbyl phosphate, ascorbyl glucoside, ascorbyl glucosamine and ascorbyl acetate in an amount of 15% to 30% by weight of the composition.

2. The composition according to claim 1, wherein: - R1 in formula (I) and formula (I') represents a hydrogen atom, or - R1 in formula (I) and formula (I') represents a straight chain (C1-C 10 ) alkyl or branched (C3-C 10 )alkyl, especially linear (C1-C6)alkyl or branched (C3-C6)alkyl, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably ethyl, especially the alkyl group of R1 is unsubstituted.

3. A composition according to any one of the preceding claims, wherein: - R2 in formula (I) and formula (I') represents a hydrogen atom; or - R2 in formula (I) and formula (I') represents a straight chain (C1-C 10 ) alkyl or branched (C3-C 10 )alkyl, especially linear (C1-C6)alkyl or branched (C3-C6)alkyl, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably methyl or ethyl; the alkyl of R2 is unsubstituted.

4. The composition according to claim 1 or 2, wherein: - R2 in formula (I) and formula (I') represents a straight chain (C1-C 10 ) alkyl or branched (C3-C 10 )alkyl, in particular straight-chain (C1-C6)alkyl or branched (C3-C6)alkyl, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably methyl or ethyl; the alkyl is substituted by one or more groups selected from i), ii), iii) and iv) as defined in claim 1, the alkyl is preferably substituted by one or two groups selected from i), ii) and iii), more preferably substituted by one or two groups selected from i) and iii), more preferably substituted by a group iii) such as carboxyl.

5. The composition according to claim 1 or 2, wherein - R2 in formula (I) and formula (I') represents a (C3-C8) cycloalkyl group, preferably a (C5-C7) cycloalkyl group, such as a cyclohexyl group; or - R2 in formula (I) and formula (I') represents C5-C 12 Aryl, which is optionally substituted by one or more hydroxyl groups and / or one or more C1-C8alkoxy groups, is preferably in particular unsubstituted phenyl.

6. A composition according to any one of the preceding claims, wherein - R3 in formula (I) and formula (I') represents a hydrogen atom; or - R3 in formula (I) and formula (I') represents a saturated straight chain C1-C 10 or branched C3-C 10 Hydrocarbyl; in particular straight-chain (C1-C6) alkyl or branched (C3-C6) alkyl, preferably (C1-C4) alkyl, such as methyl.

7. A composition according to any one of the preceding claims, wherein: - R1 in formula (I) and formula (I') represents a group selected from the following: a) Hydrogen atom; b) a saturated straight-chain C1-C6 or branched C3-C6 hydrocarbon group, which is optionally substituted by one or more groups which may be the same or different and are selected from the following: i) -O-R3; ii) -S-R3; Preferably, it is optionally substituted with one or more groups i); - R2 in formula (I) and formula (I') represents a group selected from the following: -a) Hydrogen atom; -b) Straight chain C1-C 10 Saturated hydrocarbon groups, or branched C3-C 10 A saturated hydrocarbon group or a cyclic C3-C8 saturated hydrocarbon group such as a cyclic C5-C6 saturated hydrocarbon group, which is optionally substituted with one or more groups which may be the same or different and are selected from the following: -i)-O-R3; -ii)-SR-3; -iii)-C(O)-O-R3; -iv) phenyl, which is optionally substituted by one or more hydroxyl groups and / or one or more C1-C4 alkoxy groups such as methoxy; - preferably substituted by one or more groups selected from i) and iii), preferably iii) such as carboxyl; - R3 in formula (I) and formula (I') represents a group selected from the following: -a) Hydrogen atom; -b) a saturated straight-chain C1-C6 or branched C3-C6 hydrocarbon group; - preferably, compounds of formula (I) and tautomers (I') or salts thereof, optical isomers, racemates and / or solvates such as hydrates thereof, and the like, alone or in mixture; - has the following meanings: - R1 in formula (I) and formula (I') represents a group selected from the following: -a) Hydrogen atom; -b) a saturated linear C1-C4 or branched C3-C4 hydrocarbon group, which is optionally substituted by one or more groups which may be the same or different and are selected from i) -OR3, more preferably, which is unsubstituted; - R2 in formula (I) and formula (I') represents a group selected from the following: -a) Hydrogen atom; -b) Straight chain C1-C 10 Saturated hydrocarbon groups, or branched C3-C 10 a saturated hydrocarbon group or a cyclic C3-C8 saturated hydrocarbon group such as a cyclic C5-C6 saturated hydrocarbon group, which is optionally substituted by one or more groups which may be the same or different and are selected from the following: -i) -O-R3; -iii)-C(O)-O-R3; -iv)C5-C 12 Aryl, which is optionally substituted with one or more hydroxyl groups and / or one or more C1-C4 alkoxy groups; - R3 in formula (I) and formula (I') represents a group selected from the following: -a) Hydrogen atom; -b) a saturated straight-chain C1-C4 or branched C3-C4 hydrocarbon group, such as methyl or ethyl.

8. A composition according to any one of the preceding claims, wherein The compound of formula (I) is selected from the following compounds 1 to 24, and their tautomers or salts thereof, optical isomers, racemates and / or solvates such as hydrates, either alone or in mixture, and is particularly selected from compound 1, compound 2, compound 4, compound 6, compound 7, compound 9, compound 11, compound 12, compound 14, compound 15, compound 16, compound 17, compound 18, compound 19, compound 20 or compound 21, more particularly selected from compound 1, compound 9, compound 16, compound 18, compound 19, compound 20 or compound 21, preferably compound 18, compound 19, compound 20 or compound 21, and more preferably compound 20:

9. A composition according to any one of the preceding claims, wherein the compound of formula (I) or (I') is present in an amount ranging from 0.01% to 20% by weight, preferably from 0.05% to 10% by weight, or preferably from 0.1% to 5% by weight, relative to the total weight of the composition.

10. A composition according to any one of the preceding claims, wherein the vitamin C or stabilized derivative thereof is present in the composition in an amount of 15% to 20% by weight relative to the total weight of the composition.

11. The composition according to any one of the preceding claims, wherein the component B) further comprises an additional antioxidant selected from cinnamic acid or its derivatives; and The additional antioxidant is present in the composition in an amount of 0% to 2% by weight, preferably 0% to 1% by weight or preferably 0.1% to 0.5% by weight relative to the total weight of the composition.

12. Use of ascorbic acid or a stabilized derivative thereof for stabilizing compounds of formula (I) and tautomers of formula (I') as defined in any one of claims 1 to 8, for example for stabilizing compound 20, wherein the ascorbic acid or a stabilized derivative thereof is selected from ascorbic acid, isoascorbic acid, sodium ascorbate / sodium isoascorbate, tetrahexyldecyl ascorbate / tetrahexyldecyl isoascorbate, ascorbyl palmitate, magnesium ascorbyl phosphate, ascorbyl glucoside, ascorbyl glucosamine and ascorbyl acetate, in an amount of at least 5% by weight relative to the final composition to be applied to keratin materials.

13. A non-therapeutic cosmetic method for depigmenting, lightening and / or bleaching keratinous material, preferably skin, comprising the steps of: A composition according to any one of claims 1 to 11 is applied to a keratinous material.

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