Composition comprising a thiopyridinone compound, niacinamide and gluconolactone

A composition with thiopyridinone, niacinamide, and gluconolactone, along with a surfactant system and crosslinked copolymer, addresses thiopyridinone instability and achieves effective skin depigmentation.

WO2025181321A1PCT designated stage Publication Date: 2025-09-04LOREAL SA

Patent Information

Application Number
PCT/EP2025/055487
Authority / Receiving Office
WO · WO
Patent Type
Applications
Current Assignee / Owner
Priority Date
2024-02-29
Filing Date
2025-02-28
Publication Date
2025-09-04

AI Technical Summary

Technical Problem

Thiopyridinone compounds used in cosmetic compositions are prone to instability over time, particularly at high temperatures, and there is a need for a stable composition that can effectively reduce pigment spots on the skin.

Method used

A composition comprising thiopyridinone compound, niacinamide, gluconolactone, a surfactant system, and a non-associative crosslinked copolymer of acrylic acid and/or methacrylic acid, which provides stability and efficacy in reducing skin pigment spots.

Benefits of technology

The composition maintains stability over time and effectively reduces skin pigment spots, offering a stable and effective skincare solution.

✦ Generated by Eureka AI based on patent content.

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Abstract

The present invention relates to a composition, preferably cosmetic, comprising: - at least one thiopyridinone compound chosen from the compounds of formula (I), the tautomers of formula (I') below, salts thereof, solvates thereof such as hydrates, optical isomers thereof, racemates thereof, and mixtures thereof: - at least niacinamide or one of its derivatives; - at least gluconolactone; - a surfactant system comprising (i) at least one N-acyl-amino surfactant and (ii) at least one amphoteric surfactant; and - at least one non-associative crosslinked copolymer of acrylic acid and / or methacrylic acid, or one of their esters.
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Description

[0001] Composition comprising a thiopyridinone compound, niacinamide and giuconolactone

[0002] The present invention relates to a composition, preferably cosmetic, for the care of keratin materials, in particular skin care.

[0003] At various stages of their lives, some people see darker and / or more colored spots appear on their skin, and more particularly on their face and hands, which give their skin a heterogeneous appearance. These spots are particularly due to a high concentration of melanin in the keratinocytes located on the skin surface.

[0004] The use of harmless effective topical depigmenting substances is more particularly sought in order to reduce pigment spots.

[0005] For example, arbutin, niacinamide and kojic acid are known as skin depigmenting agents.

[0006] Moreover, W02012 / 080075 and WO2017 / 102349 disclose a novel depigmenting or whitening agent which is a thiopyridinone compound. This thiopyridinone compound has particularly effective depigmenting or whitening properties by reducing melanin production.

[0007] However, it has been discovered that thiopyridinone compounds tend to destabilize in a composition over time, in particular when the composition including this compound is kept for a relatively long period at a high temperature.

[0008] Thus, an objective of the present invention is that of providing a composition including a thiopyridinone compound with increased stability over time, in particular when the composition is kept for a relatively long period at a high temperature.

[0009] Another objective is that of providing a rinsed composition, typically a skin cleansing composition, in particular for the skin of the face and / or body, including a thiopyridinone compound which makes it possible to reduce pigment spots.

[0010] The present invention addresses these needs. The composition according to the invention is a stable cleansing composition, typically a face and body cleansing gel, containing a thiopyridinone compound. It makes it possible to reduce dark spots.

[0011] Thus, the present invention also relates to a composition, preferably cosmetic, comprising: - at least one thiopyridinone compound chosen from the compounds of formula (I) below, the tautomers of formula (I’) below, salts thereof, solvates thereof such as hydrates, optical isomers thereof, racemates thereof and mixtures thereof:

[0012] [Chem 1]

[0013] 0) (I1) wherein,

[0014] - Ri denotes a radical chosen from a) a hydrogen atom, and b) a linear C1-C10 or branched C3-C10 saturated alkyl group optionally substituted by one or more groups, which may be identical or different, chosen from i) -O-R3, and ii) -S-R3, and

[0015] - R2 denotes a radical chosen from a) a hydrogen atom, b) a linear C1-C12 or branched C3-C12 or cyclic C3-C8 saturated hydrocarbon group optionally substituted by one or more groups, which may be identical or different, chosen from i) -O-R3, ii) -S-R3, iii) -C(0)-0-R3, and iv) a C5-C12 aryl group, optionally substituted by one or more hydroxyls and / or by one or more Ci-Cs alkoxy radicals, and c) a C5-C12 aryl group, optionally substituted by one or more hydroxyls and / or by one or more Ci-Ce alkoxy radicals and

[0016] - R3 denotes a radical chosen from a) a hydrogen atom, and b) a linear C1-C10 or branched C3-C10 saturated alkyl group;

[0017] - at least niacinamide or one of its derivatives;

[0018] - at least gluconolactone;

[0019] - a surfactant system comprising (i) at least one N-acyl-amino surfactant and (ii) at least one amphoteric surfactant; and

[0020] - at least one non-associative crosslinked copolymer of acrylic acid and / or methacrylic acid, or one of their esters. The invention also relates to a method for cleansing the skin, preferably the skin of the face, neck or body, comprising (i) applying a composition according to the invention onto the skin, then (ii) rinsing this composition.

[0021] The term ''skin'' means all of the skin of the body, and the scalp and preferably, the skin of the face, neckline, neck, arms and forearms, hands, or even more preferably, the skin of the face (in particular the forehead, nose, cheeks, chin), neckline and neck.

[0022] The term "intended to be administered topically" means an application on the surface of the skin in question.

[0023] The composition according to the invention is now described in detail hereinafter.

[0024] Thiopyridinone compound

[0025] The composition according to the present invention comprises at least one thiopyridinone compound of formula (I) or (I’), one of their salts, one of their solvates such as hydrates, one of their optical isomers, one of their racemates and / or mixtures thereof.

[0026] Two different thiopyridinone compounds, of formula (I) or (I’), can 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’) can be used.

[0027] The thiopyridinone compound(s) are chosen from the compounds of formula (I) below, the tautomers of formula (I’) below, salts thereof, solvates thereof such as hydrates, optical isomers thereof, racemates thereof, and mixtures thereof:

[0028] [Chem 1]

[0029] (I) d’) wherein:

[0030] Ri denotes a radical chosen from: a) a hydrogen atom, and b) a linear C1-C10 or branched C3-C10 saturated alkyl group optionally substituted by one or more groups, which may be identical or different, chosen from i) -O-R3, and ii) -S-R3, and

[0031] R2 denotes a radical chosen from: a) a hydrogen atom, b) a linear Ci-Ci2or branched C3-C12 or cyclic C3-C8 saturated hydrocarbon group, optionally substituted by one or more groups, which may be identical or different, chosen from i) -O-R3, ii) -S-R3, iii) -C(0)-0-R3, and iv) a C5-C12 aryl group, optionally substituted by one or more hydroxyls and / or by one or more Ci-Ca alkoxy radicals and c) a C5-C12 aryl group, optionally substituted by one or more hydroxyls and / or by one or more Ci-Cs alkoxy radicals, and

[0032] R3 denotes a radical chosen from: a) a hydrogen atom, and b) a linear C1-C10 or branched C3-C10 saturated alkyl group.

[0033] Hereinafter, for the purposes of the present invention and unless indicated otherwise:

[0034] - a "linear C1-C12 or branched C3-C12 saturated" hydrocarbon group is equivalent to a "linear (C1-C12) or branched (C3-C12) alkyl group" which corresponds to a linear C1-C12 or branched C3-C12 saturated hydrocarbon group, preferably a linear C1-C10 or branched C3-C10 hydrocarbon group, and more preferably a linear C1-C6 or branched C3-C6 hydrocarbon group; preferably, the linear or branched groups can be chosen from methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl and decyl; more preferably, the linear or branched saturated alkyl groups can 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, isobutyl; a "cyclic C3-C8" saturated hydrocarbon group is a mono or bicyclic cycloalkyl group containing from 3 to 8 carbon atoms, and in particular is a monocyclic C5 to C7 cycloalkyl group such as a cyclohexyl group, an "alkoxy radical" is an alkyl-oxy radical for which the alkyl radical is a linear or branched C1-C16 hydrocarbon radical, and preferably a C1-C8 hydrocarbon radical; when the alkoxy group is optionally substituted, this implies that the alkyl group is optionally substituted as defined above; an "aryl" group represents a monocyclic or bicyclic carbon-based group, fused or not, comprising from 5 to 12 carbon atoms, preferably from 6 to 10 carbon atoms, and wherein at least one ring is aromatic; preferably, the aryl radical is a phenyl, biphenyl, naphthyl group, more preferably a phenyl group.

[0035] The salts of the compounds of formula (I), (I’), (II) or (II’) as defined below comprise conventional non-toxic salts of said compounds, such as those formed using an organic or inorganic acid or an organic or inorganic base.

[0036] As salts of the compounds of formula (I), (I’), (II) or (II’), mention can be made of:

[0037] - salts obtained by adding the compound of formula (I) or (II) to:

[0038] - a mineral base, such as sodium hydroxide, potassium hydroxide, calcium hydroxide, ammonium hydroxide, magnesium hydroxide, lithium hydroxide, sodium, potassium or calcium carbonate or hydrogen carbonate for example; or

[0039] - an organic base such as a primary, secondary or tertiary alkylamine, for example triethylamine or butylamine. This primary, secondary or tertiary alkylamine can comprise one or more nitrogen and / or oxygen atoms and can thus comprise, for example, one or more alcohol groups. Mention can be made in particular of 2-amino-2-methylpropanol, ethanolamine, triethanolamine, 2-dimethylaminopropanol, 2-amino-2-(hydroxymethyl)-1 ,3- propanediol and 3-(dimethylamino)propylamine.

[0040] Mention can also be made of amino acid salts, for example lysine, arginine, guanidine, glutamic acid and aspartic acid. Advantageously, the salts of the compounds of formula (I) or (II) (when they comprise a carboxy group) can be chosen from alkali or alkaline earth metal salts such as sodium, potassium, calcium or magnesium salts and ammonium salts. An "organic or mineral acid salt" is more particularly chosen from salts chosen from a salt derived from i) hydrochloric acid HCI, ii) hydrobromic acid HBr, iii) sulfuric acid H2SO4, iv) alkylsulfonic acids: Alk-S(O)zOH such as methylsulfonic acid and ethylsulfonic 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.

[0041] The acceptable solvates of the compounds described comprise conventional solvates such as those formed during the preparation of said compounds due to the presence of solvents. Mention can be made, for example, of solvates due to the presence of water or linear or branched alcohols, such as ethanol or isopropanol.

[0042] The optical isomers are in particular enantiomers and diastereoisomers.

[0043] The compound (!’) is the tautomeric form of the compound (I) when there is a tautomeric equilibrium according to the following diagram:

[0044] According to one embodiment of the present invention, Ri represents a hydrogen atom. According to one embodiment of the present invention, Ri of formula (I) and (I’) represents a linear (C1-C10) or branched (C3-C10) alkyl group, in particular a linear (C1-C6) or branched (C3-C6) alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably, ethyl. In particular, said Ri alkyl group is not substituted.

[0045] According to one embodiment of the present invention, R2 represents a hydrogen atom.

[0046] According to one embodiment of the present invention, R2 represents a linear (C1-C10) or branched (C3-C10) alkyl group, in particular a linear (C1-C6) or branched (C3-C6) alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably methyl or ethyl; said alkyl group of R2 not being substituted.

[0047] According to one embodiment of the present invention, R2 of formula (I) and (I’) represents a linear (C1-C10) or branched (C3-C10) alkyl group, in particular a linear (C1-C6) or branched (C3-C6) alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably methyl or ethyl; said alkyl group being substituted by one or more groups selected from i), ii), iii) and iv) as defined above. Preferably, said alkyl group being substituted by one or two groups selected from i), ii) and iii), more preferably by one or two groups selected from i) and iii), more preferably substituted by a group iii) such as carboxy.

[0048] Another variant for the radical R2 is that said alkyl group is substituted by a group iv) in particular substituted by a phenyl group.

[0049] According to another embodiment of the present invention, R2represents a (C3-C8) cycloalkyl group, preferably a (C5-C7) cycloalkyl group such as cyclohexyl. cording to another embodiment of the present invention, R2represents a C5-C12 aryl group optionally substituted by one or more hydroxyls and / or by one or more CrCs alkoxy radicals, preferably phenyl group, in particular unsubstituted.

[0050] According to one embodiment, R3 represents a hydrogen atom.

[0051] According to another embodiment, R3 represents a linear C1-C10 or branched C3-C10 saturated alkyl group; in particular a linear (C1-C6) or branched (C3-C6) alkyl group, preferably a (C1-C4) alkyl group such as the methyl group.

[0052] Preferably, 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 in a mixture, have the following meanings:

[0053] R1 denotes a radical chosen from: a) a hydrogen atom, and b) a linear (C1-C6or branched C3-C6 saturated alkyl group optionally substituted by one or more groups, which may be identical or different, chosen from: i) -O-R3, and ii) -S-R3, preferably optionally substituted by one or more groups i);

[0054] R2denotes a radical chosen from: a) a hydrogen atom; b) a linear C1-C10 or branched C3-C10 or cyclic C3-C8 saturated hydrocarbon group such as C5-C6 optionally substituted by one or more groups, which may be identical or different, chosen from: i) -O-R3, ii) -S-R3, iii) -C(0)-0-R3, and iv) a phenyl group optionally substituted by one or more hydroxyls and / or by one or more C1-C4 alkoxy radicals such as methoxy, preferably substituted by one or more groups selected from i) and iii), preferably iii) such as carboxy; and

[0055] R3 denotes a radical chosen from: a) a hydrogen atom, and b) a linear C1-C6 or branched C3-C6 saturated alkyl group. Preferably, the compounds of formula (I) and the tautomer (I’) or salts thereof, optical isomers, racemates, and / or solvates thereof such as hydrates, alone or in a mixture, have the following meanings:

[0056] Ri denotes a radical chosen from: a) a hydrogen atom, and b) a linear C1-C4 or branched C3-C4 saturated alkyl group optionally substituted by one or more groups, which may be identical or different, chosen from i) -OR3, more preferably unsubstituted;

[0057] R2 denotes a radical chosen from: a) a hydrogen atom; and b) a linear C1-C10 or branched C3-C10 or cyclic C3-C8 such as Cs-Ce saturated hydrocarbon group, optionally substituted by one or more groups, which may be identical or different, chosen from: i) -O-R3, iii) -C(O)-O-R3, iv) a C5-C12 aryl group, optionally substituted by one or more hydroxyls and / or by one or more C1-C4 alkoxy radicals; and

[0058] R3denotes a radical chosen from: a) a hydrogen atom, and b) a linear C1-C4 or branched C3-C4 saturated alkyl group such as methyl or ethyl.

[0059] Preferably, 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 in a mixture, have the following meanings:

[0060] R1 is a hydrogen atom; and

[0061] R2 denotes a radical chosen from: a) a hydrogen atom, and b) a linear C1-C5 or branched C3-C5 or cyclic C3-Ce such as C5-C6 saturated hydrocarbon group may be identical or different, chosen from v) -C(O)-O-R3, preferably substituted by a group iii) -C(O)-O-R3; R2 is even more preferably a linear C1-C4 or branched C3-C4 saturated hydrocarbon group substituted by a group iii) -C(O)-OR3; and

[0062] R3denotes a radical chosen from: a) a hydrogen atom, and b) a linear C1-C4 or branched C3-C4 saturated alkyl group such as methyl or ethyl. According to another preferred embodiment, the compounds of formula (I) and the tautomer (I’) are selected from compounds of formula (II) below and also their tautomers of formula (II’) below, salts thereof, solvates and optical isomers thereof, and racemates thereof, alone or in a mixture: [Table 1]

[0063] In formula (II) and (II’), Ri and R3 have the same meaning as R1 and R3 for the compounds of formula (I) and (I’), and X denotes an alkylene radical -(CH2 )n- where n is an integer ranging from 1 to 10 inclusive, preferably ranging from 1 to 6, more preferably ranging from 1 to 4, such as 1 ; preferably, R3 represents a hydrogen atom.

[0064] Among the compounds of formula (I), the following compounds are preferably used, and their tautomer (I’) or salts thereof, optical isomers, racemates, and / or solvates thereof such as hydrates and derivatives thereof, alone or in a mixture: [Table 2]

[0065] Among these compounds, the following compounds are more particularly preferred: [Table 3]

[0066] More preferably, among these compounds, the following compounds are more particularly preferred:

[0067] [Table 4] Even more preferably, among these compounds, the following compounds are more particularly preferred:

[0068] [Table 5] In one most preferred embodiment, the compound according to the present invention is the following: All of the above compounds can be obtained with a chemical process known to those skilled in the art, from commercially available reagents.

[0069] The thiopyridinone compound can be prepared according to the method described, for example, in EP-A-3390363 or WO 2017 / 102349, which is incorporated herein by way of reference.

[0070] The thiopyridinone compound can be an active substance or an active compound in cosmetic or dermatological products. The term "active" substance or compound used here means an ingredient or compound which has an active cosmetic or dermatological property.

[0071] Preferably, the quantity of the thiopyridinone compound(s) of formula (I) or (I’) in the composition according to the present invention is at least 0.01% by weight, preferably at least 0.03% by weight, and more preferably at least 0.04% by weight relative to the total weight of the composition.

[0072] Preferably, the quantity of the thiopyridinone compound(s) of formula (I) or (I’) in the composition according to the present invention is less than 5% by weight, preferably less than 3% by weight, and more preferably less than 1% by weight relative to the total weight of the composition.

[0073] Preferably, the quantity of the thiopyridinone compound(s) of formula (I) or (I’) in the composition according to the present invention is between 0.01% and 1% by weight, preferably between 0.03% and 0.8% by weight, more preferably between 0.04% and 0.3% by weight relative to the total weight of the composition.

[0074] Niacinamide and derivatives thereof

[0075] The composition according to the invention comprises niacinamide or one of its derivatives. For the purposes of the invention, niacinamide has a structure according to the following formula:

[0076] [Chem 2]

[0077] The term "niacinamide derivative" preferably denotes a compound wherein the amide group of the niacinamide is secondary or tertiary, preferably substituted by one or two alkyl groups independently chosen from C1-C4 alkyl groups and / or wherein at least one hydrogen atom of the pyridine group is replaced by a C1-C4 alkyl group.

[0078] Preferably, the compound chosen from niacinamide and derivatives thereof is niacinamide. Mention can be made for example of the product Niacinamide PC® marketed by DSM NUTRITIONAL PRODUCTS.

[0079] Preferably, the composition comprises from 0.1% to 2.5% by weight of the compound chosen from niacinamide and derivatives thereof relative to the total weight of the composition, preferably from 0.2% to 2% by weight, preferably from 0.3% to 1.5%, more preferably from 0.4% to 1% by weight.

[0080] Preferably, the weight ratio of the quantity of compound chosen from niacinamide and derivatives thereof to the quantity of thiopyridinone compound, in the composition according to the present invention, is at least equal to 1 .6, preferably at least equal to 5, and more preferably at least equal to 8.

[0081] Preferably, the weight ratio of the quantity of compound chosen from niacinamide and derivatives thereof to the quantity of thiopyridinone compound, in the composition according to the present invention, is between 1.6 and 20, preferably between 5 and 15, and more preferably between 9 and 12.

[0082] Gluconolactone

[0083] Gluconolactone is a polyhydroxy acid (or PHA).

[0084] Preferably, the gluconolactone is delta-gluconolactone (or glucono-delta-lactone), of the following formula:

[0085] [Chem 3]

[0086] Mention can be made, for example, of the product Glucono-delta-lactone F5010 Personal Care marketed by Jungbunzlauer.

[0087] Preferably, the composition comprises from 0.1% to 5% by weight of gluconolactone relative to the total weight of the composition, preferably from 0.3% to 2% by weight, preferably from 0.6% to 1 .5% by weight, more preferably from 0.9% to 1.1% by weight.

[0088] Surfactant system The composition according to the invention contains a surfactant system that gives the composition its foaming property. Said surfactant system comprises (i) at least one N-acyl- amino surfactant and (ii) at least one amphoteric surfactant.

[0089] Preferably, the surfactant system is present in the composition in a quantity ranging from 1% to 30% by weight, preferably from 5% to 25% by weight, preferably from 7% to 20% by weight relative to the total weight of the composition.

[0090] Foaming surfactants are detergents and differ from emulsifiers by the values of their HLB (Hydrophilic-Lipophilic Balance), the HLB being the ratio between the hydrophilic part and the lipophilic part of the molecule. The term "HLB" is well known to those skilled in the art and is described for example in "The HLB system. A time-saving guide to Emulsifier Selection" (published by ICI Americas Inc; 1984). For emulsifiers, the HLB generally varies from 3 to 8 for the preparation of W / O emulsions and from 8 to 18 for the preparation of O / W emulsions, whereas foaming surfactants generally have an HLB greater than 20.

[0091] N-acyl amino surfactant

[0092] The N-acyl amino surfactant is preferably chosen from glycine derivatives (glycinates).

[0093] The N-acyl amino surfactant is preferably sodium N-cocoyl glycinate, such as that marketed underthe name Amilite GCS-12K®, or potassium N-cocoyl glycinate, such as that marketed under the name Amilite GCK 12H® by Ajinomoto.

[0094] Preferably, the N-acyl amino surfactant is sodium N-cocoyl glycinate.

[0095] The N-acyl amino surfactant is preferably present in the composition in a quantity ranging from 0.8 to 15% by weight, in particular from 1 to 10% by weight, and more particularly from 1.5 to 5% by weight relative to the total weight of the composition.

[0096] Amphoteric surfactant

[0097] The amphoteric surfactant is preferably chosen from betaines, alkyl betaines, N- alkylamidobetaines and derivatives thereof.

[0098] As betaines, mention can in particular be made of alkylbetaines for example such as coco betaine, such as the product sold under the name Dehyton AB-30® by Cognis, lauryl betaine, such as the product sold under the trade name Genagen KB® by Clariant, oxyethylenated lauryl betaine (10 OE), such as the product sold under the trade name Lauryl ether (10 OE) Betaine® by Shin Nihon Rica, oxyethylenated stearyl betaine (10 OE), such as the product sold under the trade name Stearyl Ether (10 OE) Betaine® by Shin Nihon Rica.

[0099] Among the N-alkylamidobetaines and derivatives thereof, mention can be made of cocamidopropyl betaine, such as that marketed under the trade name Lebon 2000 HG® by Sanyo or under the trade name Empigen BB® by Albright & Wilson, or lauramidopropyl betaine, such as that marketed under the trade name Rewoteric AMB12P® by Witco.

[0100] Preferably, the amphoteric surfactant is chosen from coco betaine, lauryl betaine, oxyethylenated lauryl betaine (10 OE), oxyethylenated stearyl betaine (10 OE), cocamidopropyl betaine and mixtures thereof, and more preferably is chosen from lauryl betaine, coco betaine and mixtures thereof, and, even more preferably, coco betaine.

[0101] The amphoteric surfactant is preferably present in the composition according to the present invention in a quantity ranging from 1% to 20% by weight, in particular from 2% to 15% by weight, and more particularly from 3 to 10% by weight relative to the total weight of the composition.

[0102] According to a particular embodiment, the weight ratio between the N-acyl amino surfactant and the amphoteric surfactant varies from 1 :2 to 2:1 and preferably between 0.5 and 1.7.

[0103] Non-associative crosslinked copolymer of acrylic acid and / or methacrylic acid

[0104] The composition according to the invention comprises at least one non-associative crosslinked copolymer of acrylic acid and / or methacrylic acid, or one of their esters.

[0105] For the purposes of the present invention, the term "non-associative polymer" means that the polymer does not have the behavior of an associative polymer, i.e. a hydrophilic polymer comprising more particularly at least one hydrophilic region and at least one hydrophobic region, which is capable, in an aqueous medium, of associating together or with other molecules.

[0106] According to a particular embodiment, said non-associative crosslinked copolymer of acrylic acid and / or methacrylic acid is capable of forming a microgel.

[0107] According to the present invention, a microgel is a gel wherein at least 90%, preferably 95%, more preferably all of the gel is in particle form. According to one embodiment, the crosslinked copolymer can be in the form of a dispersion in water. The average copolymer particle size number in the dispersion is generally between 10 and 500 nm, for example from 20 to 200 nm and more preferably for example from 50 to 150 nm.

[0108] The non-associative crosslinked copolymer of acrylic acid and / or methacrylic acid, and optionally one of their esters, acts as a thickening polymer and also contributes to the ability of the composition to deposit additional ingredients when present, even after rinsing.

[0109] The copolymers are partially or fully crosslinked with at least one standard crosslinking agent. The crosslinking agent can be chosen for example from polyunsaturated compounds, such as polyethylenically unsaturated compounds. For example, these compounds can be chosen from polyalkenyl ethers of sucrose, polyakenyl ethers of polyols, diallyl phthalates, divinylbenzene, allyl (meth)acrylate, ethyleneglycol di(meth)acrylate, methylene bis-acrylamide, trimethylolpropane tri(meth)acrylate, diallyl itaconate, diallyl fumarate, diallyl maleate, zinc (meth)acrylate, castor oil derivatives and polyol derivatives manufactured from unsaturated carboxylic acids.

[0110] For the purposes of the present invention, the non-associative crosslinked copolymer of acrylic acid and / or methacrylic acid means that the copolymer comprises at least one acrylic acid unit or one methacylic acid unit or a mixture thereof. The copolymer can comprise other units such as units formed by an ester of acrylic acid or methacrylic acid, preferably acrylic, comprising less than 6 carbon atoms, i.e. a C1-C4 alkyl acrylate group chosen from methyl acrylate, ethyl acrylate and butyl acrylate, hereinafter referred to as "simple ester".

[0111] According to a particular embodiment, a non-associative crosslinked copolymer according to the present invention comprises at least one acrylic acid unit.

[0112] According to another embodiment, a non-associative crosslinked copolymer according to the present invention comprises at least one methacrylic acid unit.

[0113] According to another embodiment, a non-associative crosslinked copolymer according to the present invention comprises at least one acrylic acid unit and at least one methacrylic acid unit.

[0114] Mention can be made of the crosslinked copolymers of vinyl neodecanoate and one or more monomers of acrylic acid, methacrylic acid or one of their simple esters crosslinked with a trimethylolpropane or pentaerythritol allyl ether such as the product sold under the trade name ACULYN 38® (INCI name: ACRYLATES / VINYL NEODECANOATE CROSSPOLYMER) sold by THE DOW CHEMICAL COMPANY. As other examples of such non-associative crosslinked copolymers of acrylic acid and / or methacrylic acid, mention can be made of:

[0115] (1 ) homopolymers of acrylic acid crosslinked with a pentaerythritol allyl ether, a sucrose allyl ether or a propylene allyl ether such as the carbomer sold under the trade name CARBOPOL® by LUBRIZOL,

[0116] (2) non-associative crosslinked copolymers of acrylic acid and / or methacrylic acid and esters thereof. As examples of such non-associative crosslinked copolymers of acrylic acid and / or methacrylic acid and esters thereof, mention can be made of: i) Crosslinked copolymers of acrylic acid and / or methacrylic acid comprising less than 6 carbon atoms and more particularly in the form of a 30% aqueous copolymer dispersion sold under the trade name ACULYN 33® by DOW CHEMICAL COMPANY and having the INCI name: ACRYLATES COPOLYMER, ii) Crosslinked copolymers including at least one methacrylic acid unit and at least one C1- C4 alkyl acrylate unit. These copolymers are described for example in patent application WO 01 / 76552. As used here, the crosslinked copolymer comprising at least one methacrylic acid unit and at least one C1-C4 alkyl acrylate unit means a crosslinked copolymer comprising at least one methacrylic acid unit and at least one alkyl acrylate unit, wherein the alkyl acrylate unit is chosen from C1-C4 alkyl acrylates.

[0117] In the crosslinked copolymers described here, the methacrylic acid unit can be present for example in a quantity ranging from 20% to 80% by weight, such as from 25 to 70% by weight, and more preferably from 35 to 60% by weight relative to the total weight of the copolymer.

[0118] In the crosslinked copolymer described here, the alkyl acrylate unit can be present for example in a quantity ranging from 15% to 80% by weight, preferably from 25% to 75% by weight and more preferably from 40% to 65% by weight relative to the total weight of the copolymer. The alkyl acrylate unit can be chosen for example from methyl acrylate, ethyl acrylate, and butyl acrylate. In one embodiment, the alkyl acrylate unit is ethyl acrylate.

[0119] For example, the crosslinked copolymers comprising at least one methacrylic acid unit and at least one ethyl acrylate unit can be used, for example in the form of a 30% aqueous dispersion manufactured and sold under the trade name CARBOPOL AQUA SF-1® by NOVEON.

[0120] As other examples of such non-associative crosslinked copolymers of acrylic acid and / or methacrylic acid, mention can be made of: (3) anionic associative crosslinked polymers of acrylic acid and / or methacrylic acid and / or esters thereof and more particularly those consisting of 95 to 60% by weight of acrylic acid (hydrophilic unit), 4 to 40% by weight of C10-C30 alkyl acrylate (hydrophobic unit), and 0 to 6% by weight of crosslinking polymerizable monomer, or alternatively those consisting of 98 to 96% by weight of acrylic acid (hydrophilic unit), 1 to 4% by weight of C10-C30 alkyl acrylate (hydrophobic unit) and 0.1 to 0.6% by weight of crosslinking polymerizable monomer such as those described above.

[0121] Among the above polymers, mention can be made of the products marketed by GOODRICH under the trade names PEMULEN TR1®, PEMULEN TR2®, CARBOPOL 1382®, and even more preferably PEMULEN TR1®, and the product marketed by S.E.P.P.LC. under the trade name COATEX SX®, and bearing the INCI name: ACRYLATES / C10-C30 ALKYL ACRYLATE CROSSPOLYMER.

[0122] Mention can also be made of copolymers comprising among their monomers an a,0- monoethylene unsaturated carboxylic acid and an a,p-monoethylene unsaturated carboxylic acid ester and an oxyalkylenated faty alcohol. Preferably, these compounds also comprise, as a monomer, an ester of caboxylic acid with a,p-monoethylene unsaturation and a C1-C4 alcohol. As an example of this type of compound, mention can be made of ACULYN 22® marketed by THE DOW CHEMICAL COMPANY which is an oxyalkylenated stearyl methacrylate / ethyl acrylate / methacrylic acid terpolymer bearing the INCI name ACRYLATES / STEARETH-20 METHACRYLATE COPOLYMER.

[0123] Mention can also be made of crosslinked copolymers of acrylic acid / vinyl isodecanoate such as those sold under the trade name STABYLEN 30 ® (INCI name: ACRYLATES / VINYL ISODECANOATE CROSSPOLYMER) marketed by SIGMA 3V.

[0124] Preferably, the non-associative crosslinked copolymer of acrylic acid and / or methacrylic acid, and optionally one of their esters, is chosen from:

[0125] - a crosslinked copolymer of acrylic acid and / or methacrylic acid and an ester thereof comprising less than 6 carbon atoms,

[0126] - a crosslinked copolymer comprising at least one methacrylic unit and at least one C1-C4 alkyl acrylate unit, for example an ethyl acrylate unit,

[0127] - a crosslinked copolymer of vinyl neodecanoate and one or more monomers of acrylic acid, methacrylic acid or one of their simple esters crosslinked with an allyl ether of trimethylolpropane or pentaerythritol, and

[0128] - mixtures thereof. The non-associative crosslinked copolymer of acrylic acid and / or methacrylic acid, and optionally esters thereof, is preferably present in the composition according to the present invention in an active substance content greater than or equal to 0.3% by weight, more particularly greater than or equal to 0.5% by weight relative to the total weight of the composition, for example in a content ranging from 0.3% to 8% by weight, preferably from 0.5% to 5% by weight, preferably from 0.7% to 3% by weight relative to the total weight of the composition.

[0129] Additional surfactant

[0130] The composition according to the invention can comprise, in addition to the surfactant system comprising (i) at least one N-acyl-amino surfactant, and (ii) at least one amphoteric surfactant, an additional surfactant.

[0131] This additional surfactant can be chosen from anionic, amphoteric (or zwitterionic), nonionic and cationic surfactants.

[0132] Preferably, the additional surfactant is nonionic, preferably chosen from alkylpolyglucosides (APGs), oxyalkylenated glycerol esters, oxyalkylenated sugar esters, and mixtures thereof. As APGs, those containing an alkyl group comprising from 6 to 30 carbon atoms, preferably from 8 to 16 carbon atoms, and containing a glucoside group comprising preferably from 1.2 to 3 glucoside units, are preferably used. The APGs can be chosen for example from decylglucosides (alkyl-C9 / C11 -polyglucoside (1.4)), such as the product sold under the trade name Mydol 10® by Kao Chemicals or the product sold under the trade name Plantacare 2000 UP® by Cognis; caprylyl / capryl glucoside, such as the product sold under the trade name Plantacare KE 3711® by Cognis; laurylglucoside, such as the product sold under the trade name Plantacare 1200 UP® by Cognis; cocoglucoside, such as the product sold under the trade name Plantacare 818 UP® by Cognis; caprylylglucoside, such as the product sold under the trade name Plantacare 810 UP® by Cognis; and mixtures thereof. The oxyalkylenated glycerol esters are in particular the polyoxyethylenated derivatives of glycerol and fatty acid esters and hydrogenated derivatives thereof.

[0133] These oxyalkylenated glycerol esters can be chosen for example from hydrogenated and oxyethylenated glycerol and fatty acid esters such as PEG-200 hydrogenated glyceryl palmate, sold under the trade name Rewoderm Ll-S 80 by Goldschmidt; oxyethylenated glycerol cocoates, such as PEG-7 glyceryl cocoate, sold under the trade name Tegosoft GC by Goldschmidt, or PEG-30 glyceryl cocoate sold under the trade name Rewoderm LI- 63 by Goldschmidt; and mixtures thereof. The oxyalkylenated sugar esters used in the invention are in particular polyethylene glycol ethers of fatty acids and sugars. These oxyalkylenated sugar esters can be chosen, for example, from oxyethylenated glucose esters, such as PEG-120 methyl glucose dioleate, sold under the name Glucamate DOE 120 by Amerchol.

[0134] According to a preferred embodiment of the invention, the additional surfactant is an oxyalkylenated sugar ester which can be chosen in particular from oxyethylenated glucose esters, such as PEG-120 methyl glucose dioleate.

[0135] Antioxidant reducing agent

[0136] Preferably, the composition according to the invention also comprises at least one antioxidant reducing agent.

[0137] Preferably, the antioxidant reducing agent is chosen from sodium thiosulfate, sodium metabisulfite, thioglycolic acid, thiolactic acid, cysteine, cysteamine, homocysteine and mixtures thereof.

[0138] Preferably, the antioxidant reducing agent is sodium thiosulfate.

[0139] Preferably, the composition comprises from 0.01% to 3% by weight of antioxidant reducing agent relative to the total weight of the composition, preferably from 0.05% to 1 % by weight, more preferably from 0.08% to 0.3% by weight.

[0140] Vitamin E and derivatives thereof

[0141] Preferably, the composition according to the invention also comprises vitamin E or one of its derivatives.

[0142] Vitamin E is a fat-soluble vitamin which covers eight organic molecules, i.e. four tocopherols (alpha-tocopherol, beta-tocopherol, gamma-tocopherol and delta-tocopherol) and four tocotrienols (a-tocotrienol, p-tocotrienol y-tocotrienol and 6-tocotrienol).

[0143] Preferably, the composition according to the invention comprises a vitamin E derivative, preferably tocopheryl acetate.

[0144] Preferably, the composition comprises from 0.01% to 3% by weight of vitamin E or one of its derivatives relative to the total weight of the composition, preferably from 0.05% to 1% by weight, more preferably from 0.08% to 0.5% by weight. Preferably, the composition according to the invention comprises a mixture of sodium thiosulfate and tocopheryl acetate.

[0145] Physiologically acceptable medium

[0146] In addition to the compounds indicated above, the composition according to the invention comprises a physiologically acceptable medium.

[0147] The term "physiologically acceptable medium" means a medium that is particularly suitable for the application of a composition of the invention onto keratin materials, in particular the skin.

[0148] The physiologically acceptable medium is generally adapted to the nature of the substrate onto which the composition is to be applied, and also to the aspect in which the composition is to be packaged.

[0149] The cosmetic compositions of the invention can be in the form of a gel, in particular aqueous, or in the form of an O / W emulsion.

[0150] The physiologically acceptable medium can comprise water and optionally one or more water-miscible solvent(s).

[0151] According to a preferred embodiment, the compositions according to the invention comprise at least 20% by weight of water, particularly at least 40% by weight of water relative to the total weight of said composition.

[0152] Preferably, the composition according to the invention has a water content ranging from 20% to 95% by weight, more preferably from 40% to 90% by weight relative to the total weight of the composition.

[0153] A water suitable for the invention can be a floral water such as cornflower water and / or a mineral water such as VITTEL water, VICHY water or LA ROCHE POSAY water and / or a spring water.

[0154] Among the water-miscible organic solvents (at ambient temperature, i.e. 25°C), mention can be made of one or more cosmetically acceptable organic solvents, which can be alcohols, in particular monovalent alcohols such as ethanol, isopropyl alcohol, benzyl alcohol and phenylethyl alcohol; diols such as ethylene glycol, propylene glycol, propane- 1 ,3-diol, butylene glycol and pentylene glycol; and ethers such as monomethyl, monoethyl and monobutyl ethers of ethylene glycol, monomethyl, monoethyl and monobutyl ether of propylene glycol, and monomethyl, monoethyl and monobutyl ethers of butylene glycol, and glycerin. The water-miscible organic solvent(s) can be present at a concentration of 0.01% to 30% by weight, preferably from 0.1% to 20% by weight and more preferably from 1% to 15% by weight, relative to the total weight of the composition.

[0155] The composition according to the invention can also comprise at least one fatty substance such as one or more oil(s).

[0156] According to one embodiment, the composition can comprise from 0.1% to 50% by weight of faty substance, preferably oil(s), and preferably from 0.5% to 40% of faty substance, preferably oil(s), by weight relative to the total weight of said composition.

[0157] The term "oil" means any fatty substance in liquid form at ambient temperature (20-25°C) and at atmospheric pressure. These oils may be of plant, mineral or synthetic origin.

[0158] As oils suitable for use in the composition of the invention, mention can be made for example of: hydrocarbon oils of animal origin; hydrocarbon oils of plant origin;

[0159] - synthetic esters and ethers, in particular of fatty acids, such as the oils of formulas R1COOR2 and R1OR2 wherein R1 represents the residue of a faty acid including 8 to 29 carbon atoms, and R2 represents a hydrocarbon chain, branched or not, containing 3 to 30 carbon atoms; linear or branched hydrocarbons, of mineral or synthetic origin;

[0160] - faty alcohols having from 8 to 26 carbon atoms; partially hydrocarbon and / or silicone fluorinated oils;

[0161] - silicone oils; mixtures thereof.

[0162] The term hydrocarbon oil in the list of oils cited above denotes any oil comprising mostly carbon and hydrogen atoms, and optionally ester, ether, fluorinated, carboxylic acid and / or alcohol groups.

[0163] The composition according to the invention may comprise at least one sequestrant.

[0164] Among the preferred sequestrants, mention can be made of ethylenediamine disuccinic acid salts, EDTA and its salts, and mixtures thereof.

[0165] The ethylenediamine disuccinic acid is a compound of formula (III):

[0166] [Chem 4]

[0167] Preferably, the ethylene diamine disuccinic acid salt is selected from alkali metal salts, such as potassium and sodium salts, ammonium salts, and amine salts. The alkali metal salts of ethylenediamine disuccinic acid are more specifically preferred.

[0168] Preferably, the ethylene diamine disuccinic acid salt used according to the invention is trisodium ethylene diamine disuccinate.

[0169] For example, such a compound is that marketed under the trade name Natrlquest® E30 by Innospec Active Chemicals, or that marketed under the trade name Octaquest E30® by Octel Performance Chemicals.

[0170] According to a particular alternative embodiment, the ethylenediamine disuccinic acid salt can be introduced in the composition dissolved in water, in particular at a concentration ranging from 25% to 50% by weight, preferably from 35% to 40% by weight in water.

[0171] For example, such a compound is marketed under the trade name Natrlquest® E30 by Innospec Active Chemicals, at 37% by weight in water.

[0172] Preferably, the composition comprises an EDTA salt, preferably disodium EDTA.

[0173] Preferably, the composition comprises trisodium ethylene diamine disuccinate and disodium EDTA.

[0174] The composition according to the invention can comprise at least one glycol, preferably caprylyl glycol.

[0175] Preferably, the composition according to the invention comprises from 0.1% to 2% by weight, preferably from 0.2% to 1.5% by weight of glycol(s) relative to the total weight of the composition.

[0176] In a particular embodiment of the invention, the composition according to the present invention can also comprise at least one pH correction agent (pH corrector).

[0177] Two or more pH correction agents can be used in combination. Thus, a single type of pH correction agent or a combination of different types of pH correction agents can be used.

[0178] As a pH correction agent, at least one acidifying agent and / or at least one alkalizing agent (alkaline agent) can be used.

[0179] The acidifying agent can be a monovalent or polyvalent, such as divalent, acid. The acidifying agents can be, for example, mineral (inorganic) acids such as hydrochloric acid, sulfuric acid, phosphoric acid, or organic acids such as carboxylic acids, for example tartaric acid, citric acid, and lactic acid, and sulfonic acids.

[0180] The alkalizing agent can be a monovalent or polyvalent, such as divalent, base.

[0181] The alkalizing agents can be mineral (inorganic) or organic, or hybrid.

[0182] The alkalizing agent can be an organic or mineral base, for example sodium hydroxide.

[0183] Preferably, the composition according to the present invention has a pH at least equal to 4.5, preferably at least equal to 5. Preferably, the composition according to the present invention has a pH less than or equal to 7.0, preferably less than or equal to 6.5. Preferably, the composition according to the present invention has a pH ranging from 4.5 to 6.5, and more preferably from 5.4 to 6.0.

[0184] The pH of the composition means the pH of the aqueous phase of the composition according to the present invention.

[0185] It may be preferable that at least one buffer or buffer agent be also used, as the pH correction agent, in combination with the acidifying agent and / or the alkalizing agent, in order to stabilize the pH of the composition according to the present invention.

[0186] As a buffer, any commonly known buffer can be used. For example, acid or base salts, preferably weak acid or weak base salts, can be used. For example, sodium citrate or sodium lactate can be used as a buffer, if citric acid or lactic acid is used as an acidifying agent.

[0187] A cosmetic composition according to the invention can also further comprise any additive usually used in the field in question, for example chosen from gums, resins, dispersing agents, polymers, antioxidants, essential oils, preservatives, perfumes, antiseptic agents, UV filters, cosmetic active agents and mixtures thereof.

[0188] A person skilled in the art can adjust the type and quantity of additives present in the compositions according to the invention by means of routine operations, so that the cosmetic properties and the stability properties sought for these compositions are not affected by the additives.

[0189] The composition according to the invention can be in any dosage forms normally used in the cosmetic field.

[0190] It can in particular be in the form of an aqueous, hydroalcoholic solution, optionally gelled, an optionally biphasic lotion type dispersion, an oil-in-water or water-in-oil or multiple emulsion, an aqueous gel, a dispersion of oils in an aqueous phase, in particular using spherules, these spherules being capable of being polymeric particles or preferably, ionic and / or nonionic type lipid vesicles, or in the form of a powder, a serum, a paste or a soft stick or a stick. It can be of solid, pasty, or more or less fluid liquid consistency. It could possibly be applied on the skin in the form of a spray. It may also be in solid form, and for example in stick form.

[0191] The composition according to the invention is typically suitable for topical application. Thus, the composition can comprise all the constituents usually used in the envisaged topical application and administration.

[0192] The composition according to the invention can advantageously be in the form of an emulsion, in particular obtained by dispersing an aqueous phase in a fatty phase (O / W) or a fatty phase in an aqueous phase (W / O), of liquid or semi-liquid consistency of the milk type, or of soft, semi-solid or solid consistency of the cream or gel type, or multiple emulsion (W / O / W or O / W / O). These compositions are prepared using routine methods.

[0193] Preferably, the composition according to the invention is in the form of a gel, preferably an aqueous gel, preferably a cleansing gel.

[0194] The compositions according to the invention can be applied directly onto the skin or, alternatively, onto occlusive or non-occlusive cosmetic substrates, intended to be applied locally onto the skin. As non-limiting examples of cosmetic substrates, mention can be made in particular of a patch, a wipe, a roll-on or a pen.

[0195] Preferably, the composition is rinsed after being applied onto the skin.

[0196] Thus, the invention also relates to a method for cleansing the skin, preferably the skin of the face, neck or body, comprising (i) applying a composition according to the invention onto the skin, then (ii) rinsing this composition.

[0197] The invention is now illustrated by the following examples. Unless specified otherwise, the quantities are given as a percentage by weight relative to the total weight of the composition (% w / w).

[0198] Example 1 : Composition according to the invention

[0199] The composition according to the following invention was prepared by mixing the different ingredients:

[0200] [Table 7] a.s. = active substance

[0201] This composition is stored for two months at 4°C or at 45°C, then niacinamide is assayed and the presence of niacin is tested. After two months of storage at 4°C or at 45°C, the niacinamide contents are conforming and stable (0.5% assayed for each case), and the niacin contents are below the limit of quantification (<10ppm).

[0202] Moreover, the 2-mercaptonicotinoyl glycine assays obtained after two months at 45°C are conforming with the theoretical levels (i.e. within the limit of a maximum loss of 10%), and no degradation product is detected.

[0203] In conclusion, the composition according to the invention is stable at ambient temperature, and after two months at 4°C and at 45°C.

[0204] Example 2: Clinical study of a composition according to the invention

[0205] The composition according to the following invention was prepared by mixing the different ingredients:

[0206] [Table 8] a.s. = active substance

[0207] This composition was assessed for reducing pigment spots as follows:

[0208] 49 Caucasian women aged from 40 to 65 years and of phototype l-IV participated in the study in South Africa. They had pigmented spots on their face (actinic lentigo, senile lentigo and / or sun spots) with at least a defined and homogeneous size greater than or equal to 3 mm in diameter.

[0209] These women applied the composition twice daily (morning and evening) for 8 weeks, followed by one week of retention (9thweek without application). The assessment is performed using at TO, T5weeks, T8weeks and T9weeks:

[0210] -clinical scoring by a dermatologist, using a 10-point scale (0=NAD to 9=severe);

[0211] -clinical scoring by a dermatologist, using the Skin Aging Atlas (Skin Aging Atlas, vol. 2 Asian type (R. BAZIN, F. FLAMENT).

[0212] The results show that after 5 weeks and 8 weeks of application of the composition, with clinical scoring by a dermatologist on a 10-point scale, a statistically significant improvement is observed in:

[0213] - "liver spot visibility" with -23.1% and -36.3% variation respectively; and

[0214] - "isolated pigment spot contrast" with -21 .6% and -27.1% variation respectively.

[0215] Retention assessment a- At the D63 time interval, after one week of non-application of the composition (i.e. end of the 9thweek), the results show a statistically significant improvement compared to the baseline level in:

[0216] - "liver spot visibility" with -37.1% variation; and - "isolated pigment spot contrast" with -27.1 % variation. b- No change was observed between 63 days (end of 9thweek) and 56 days (end of 8thweek).

[0217] All of these results show that the efficacy of the product on "liver spot visibility" and on "isolated pigment spot contrast" lasts one week after the last application, and is maintained at a comparable level of efficacy to that after 56 days of application.

Claims

CLAIMS1. Composition, preferably cosmetic, comprising:- at least one thiopyridinone compound chosen from the compounds of formula (I) below, the tautomers of formula (I’) below, salts thereof, solvates thereof such as hydrates, optical isomers thereof, racemates thereof and mixtures thereof:[Chem 1]0) (I1) wherein:- Ri denotes a radical chosen from a) a hydrogen atom, and b) a linear C1-C10 or branched C3-C10 saturated alkyl group optionally substituted by one or more groups, which may be identical or different, chosen from i) -O-R3, and ii) -S-R3, and- R2 denotes a radical chosen from a) a hydrogen atom, b) a linear C1-C12 or branched C3-C12 or cyclic C3-C8 saturated hydrocarbon group optionally substituted by one or more groups, which may be identical or different, chosen from i) -O-R3, ii) -S-R3, Hi) -C(0)-0-R3, and iv) a C5-C12 aryl group, optionally substituted by one or more hydroxyls and / or by one or more Ci-Ca alkoxy radicals, and c) a C5-C12 aryl group, optionally substituted by one or more hydroxyls and / or by one or more CrCs alkoxy radicals and- R3 denotes a radical chosen from a) a hydrogen atom, and b) a linear C1-C10 or branched C3-C10 saturated alkyl group;- at least niacinamide or one of its derivatives;- at least gluconolactone;- a surfactant system comprising (i) at least one N-acyl-amino surfactant and (ii) at least one amphoteric surfactant; and- at least one non-associative crosslinked copolymer of acrylic acid and / or methacrylic acid, or one of their esters.

2. Composition according to claim 1 , wherein the compounds of formula (I) and the tautomer (I’) or salts thereof, optical isomers, racemates, and / or solvates thereofsuch as hydrates and derivatives thereof, alone or in a mixture, have the following meanings:R1 is a hydrogen atom; andR2 denotes a radical chosen from: a) a hydrogen atom, and b) a linear C1-C5 or branched C3-C5 or cyclic C3-C8 such as C5-C6 saturated hydrocarbon group may be identical or different, chosen from v) -C(0)-0-R3, preferably substituted by a group iii) -C(0)-0-R3; R2 is even more preferably a linear C1-C4 or branched C3-C4 saturated hydrocarbon group substituted by a group iii) -C(O)-OR3: and R3 denotes a radical chosen from: a) a hydrogen atom, and b) a linear C1-C4 or branched C3-C4 saturated alkyl group such as methyl or ethyl.

3. Composition according to claim 1 or 2, wherein the C-glycoside is chosen from:[Table 2]4. Composition according to one of the preceding claims, wherein the thiopyridone compound is as follows:

5. Composition according to one of the preceding claims, wherein the thiopyridinone compound is present in an quantity of at least 0.01 % by weight, preferably at least 0.03% by weight, and more preferably at least 0.04% by weight relative to the total weight of the composition; and / or in an quantity of less than 5% by weight, preferably less than 3% by weight, and more preferably less than 1% by weight relative to the total weight of the composition; and / or in a quantity between 0.01% and 1% by weight, preferably between 0.03% and 0.8% by weight, more preferably between 0.04% and 0.3% by weight relative to the total weight of the composition.

6. Composition according to one of the preceding claims, characterized in that it comprises from 0.1% to 2.5% by weight of compound chosen from niacinamide and derivatives thereof relative to the total weight of composition, preferably from 0.2% to 2% by weight, more preferably from 0.3% to 1.5%, even more preferably from 0.4% to 1% by weight.

7. Composition according to one of the preceding claims, wherein the weight ratio of the quantity of compound chosen from niacinamide and derivatives thereof to the quantity of thiopyridinone compound is at least equal to 1.6, preferably at least equal to 5, and more preferably at least equal to 8, preferably between 1 .6 and 20, preferably between 5 and 15, and more preferably between 9 and 12.

8. Composition according to one of the preceding claims, which comprises from 0.1% to 5% by weight of gluconolactone relative to the total weight of composition,preferably from 0.3% to 2% by weight, preferably from 0.6% to 1.5% by weight, more preferably from 0.9% to 1.1% by weight.

9. Cosmetic composition according to one of the preceding claims, which comprises the surfactant system in a quantity ranging from 1% to 30% by weight, preferably from 5% to 25% by weight, preferably from 7% to 20% by weight relative to the total weight of the composition.

10. Composition according to one of the preceding claims, wherein the N-acyl amino surfactant is chosen from glycine derivatives, preferably from sodium N-cocoyl glycinate and potassium N-cocoyl glycinate, preferably the N-acyl amino surfactant is sodium N-cocoyl glycinate.

11. Composition according to one of the preceding claims, wherein the N-acyl amino surfactant is present in a quantity ranging from 0.8 to 15% by weight, in particular from 1 to 10% by weight, and more particularly from 1.5 to 5% by weight relative to the total weight of the composition.

12. Composition according to one of the preceding claims, wherein the amphoteric surfactant is chosen from betaines, alkyl betaines, N-alkylamidobetaines and derivatives thereof; preferably chosen from coco betaine, lauryl betaine, oxyethylenated lauryl betaine (10 OE), oxyethylenated stearyl betaine (10 OE), cocamidopropyl betaine and lauramidopropyl betaine; preferably chosen from lauryl betaine, coco betaine and mixtures thereof; even more preferably, it is coco betaine.

13. Composition according to one of the preceding claims, wherein the amphoteric surfactant is present in a quantity ranging from 1 % to 20% by weight, in particular from 2% to 15% by weight, and more particularly from 3 to 10% by weight relative to the total weight of the composition.

14. Composition according to one of the preceding claims, wherein the weight ratio between the N-acyl amino surfactant and the amphoteric surfactant ranges from 1 :2 to 2:1 and preferably between 0.5 and 1.7.

15. Composition according to one of the preceding claims, wherein the non- associative crosslinked copolymer of acrylic acid and / or methacrylic acid, and optionally one of their esters, is chosen from:- a crosslinked copolymer of acrylic acid and / or methacrylic acid and an ester thereof comprising less than 6 carbon atoms,- a crosslinked copolymer comprising at least one methacrylic unit and at least one C1-C4 alkyl acrylate unit, for example an ethyl acrylate unit,- a crosslinked copolymer of vinyl neodecanoate and one or more monomers of acrylic acid, methacrylic acid or one of their simple esters crosslinked with an allyl ether of trimethylolpropane or pentaerythritol, and- mixtures thereof.

16. Composition according to one of the preceding claims, wherein the non- associative crosslinked copolymer of acrylic acid and / or methacrylic acid, and optionally esters thereof, is present in an active substance content greater than or equal to 0.3% by weight, more particularly greater than or equal to 0.5% by weight relative to the total weight of the composition, for example in a content ranging from 0.3% to 8% by weight, preferably from 0.5% to 5% by weight, preferably from 0.7% to 3% by weight relative to the total weight of the composition.

17. Composition according to one of the preceding claims, which comprises, in addition to the surfactant system comprising (i) at least one N-acyl-amino surfactant and (ii) at least one amphoteric surfactant, an additional surfactant; preferably the additional surfactant is nonionic, preferably chosen from alkylpolyglucosides (APGs), oxyalkylenated glycerol esters, oxyalkylenated sugar esters, and mixtures thereof; preferably the additional surfactant is an oxyalkylenated sugar ester which can be chosen in particular from oxyethylenated glucose esters, such as PEG-120 methyl glucose dioleate.

18. Composition according to one of the preceding claims, which also comprises at least one antioxidant reducing agent, preferably chosen from sodium thiosulfate, sodium metabisulfite, thioglycolic acid, thiolactic acid, cysteine, cysteamine, homocysteine and mixtures thereof.

19. Composition according to claim 18, which comprises from 0.01% to 3% by weight of antioxidant reducing agent relative to the total weight of the composition, preferably from 0.05% to 1% by weight, preferably from 0.08% to 0.3% by weight.

20. Composition according to one of the preceding claims, which also comprises vitamin E or one of its derivatives, preferably tocopheryl acetate, preferably the composition comprises tocopheryl acetate and sodium thiosulfate.

21. Composition according to claim 20, which comprises from 0.01% to 3% by weight of vitamin E or one of its derivatives relative to the total weight of the composition, preferably from 0.05% to 1% by weight, preferably from 0.08% to 0.5% by weight.

22. Composition according to one of the preceding claims, which is in the form of a gel, preferably an aqueous gel, preferably a cleansing gel, or an emulsion, in particular obtained by dispersing an aqueous phase in a fatty phase (W / O) or of a fatty phase in an aqueous phase (O / W).

23. Method for cleansing the skin, preferably the skin of the face, neck or body, comprising (i) applying a composition according to one of the preceding claims onto the skin, then (ii) rinsing this composition.

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