Composition with robinin, hydrophilic solvents and hydrotrope agents

Abstract

The present invention relates to a cosmetic composition comprising: (a) at least one compound of formula (I), or one of its optical isomers, its cis-trans isomers (such as an alpha or beta anomer), tautomers, or one of its salts or hydrates, (b) a mixture of at least two hydrophilic solvents, the mixture having a ∆δ with the compound of formula (I) or one of its optical isomers, its cis-trans isomers (such as an alpha or beta anomer), tautomers, or one of its salts or hydrates comprised between 13 and 16, (c) at least one hydrotrope agent, and (d) water. It also relates to a method for care of the skin and / or mucosa comprising application of the composition according to the invention on the skin and / or mucosa.

Description

[0001] Composition with robinin, hydrophilic solvents and hydrotrope agents

[0002] The present invention relates to a cosmetic composition comprising:

[0003] (a) at least one compound of formula (I) as defined hereinafter, or one of its optical isomers, its cis-trans isomers (such as an alpha or beta anomer), tautomers, or one of its salts or hydrates,

[0004] (b) a mixture of at least two hydrophilic solvents, the mixture having a A6 with the compound of formula (I) or one of its optical isomers, its cis-trans isomers (such as an alpha or beta anomer), tautomers, or one of its salts or hydrates comprised between 13 and 16,

[0005] (c) at least one hydrotrope agent, and

[0006] (d) water.

[0007] Human skin is composed of two compartments, namely a deep compartment (the dermis) and a surface compartment (the epidermis). The epidermis is in contact with the external environment, and it particularly has the role of protecting the body from dehydration and stress in particular external, chemical or mechanical stress.

[0008] There is still a need for novel cosmetic compositions having advantageous properties, in particular on the skin.

[0009] Robinin may be an advantageous active agent in this aim. Indeed, this type of active agent is known in cosmetics, for example from application EP4171476.

[0010] However, robinin is soluble in some solvents like hot alcohols, but is not soluble in water at room temperature. Therefore, it does not allow, per se, the formulation of cosmetic compositions that are stable and applicable on the skin.

[0011] Therefore, the formulator seeks compositions comprising robinin which are stable and applicable in particular topically (i.e. on the skin and / or mucosa).

[0012] Such compositions must furthermore comprise a certain quantity of water, in order to be able to formulate robinin in a wide range of cosmetic substrates including lotions, gels or emulsions.

[0013] In this context, the inventors have surprisingly discovered that particular hydrophilic solvents and particular hydrotrope compounds allow dissolving robinin, while being used in acceptable amounts in terms of skin tolerance, and while being compatible with a formulation in an aqueous medium. Therefore, the aim of the invention is that of providing a cosmetic composition addressing all these issues.

[0014] Thus, the present invention relates to a cosmetic composition comprising:

[0015] (a) at least one compound of formula (I), or one of its optical isomers, its cis-trans isomers (such as an alpha or beta anomer), tautomers, or one of its salts or hydrates:

[0016] [Chem 1] wherein:

[0017] - R’ and R”, identical or different, preferably different, represent a hydrogen or a (Ci- C4)alkyl group for example chosen from among methyl, ethyl, propyl, isopropyl, butyl and isobutyl, preferably a methyl, or a monosaccharide or a polysaccharide including up to 20 sugar units, preferably up to 6 sugar units, in pyranose and / or furanose form and of L and / or D series, said mono- or polysaccharide optionally being substituted by an obligatorily free hydroxyl group, and / or optionally substituted by one or more optionally protected amine function(s), said monosaccharide or polysaccharide being optionally substituted on its - CH2OH group by a -C(O)-CC>2H group, and said monosaccharide or polysaccharide being optionally substituted on one or more of its hydroxy groups by a (Ci-C4)acyl group, preferably an acetyl group, or by a hydroxycinnamyl fragment, chosen from among coumaroyl, cafeoyl, feruloyl and sinapoyl;

[0018] - R’” and R””, identical or different, represent a hydrogen or a (Ci-C4)alkyl group for example chosen from among methyl, ethyl, propyl, isopropyl, butyl and isobutyl, preferably a methyl, it being understood that R’, R”, R’” and R”” do not represent H at the same time,

[0019] (b) a mixture of at least two hydrophilic solvents, the mixture having a Ab with the compound of formula (I) or one of its optical isomers, its cis-trans isomers (such as an alpha or beta anomer), tautomers, or one of its salts or hydrates comprised between 13 and 16,

[0020] (c) at least one hydrotrope agent, and

[0021] (d) water. Preferably, the present invention relates to a cosmetic composition consisting of:

[0022] (a) at least one compound of formula (I) as defined above, or one of its optical isomers, its cis-trans isomers (such as an alpha or beta anomer), tautomers, or one of its salts or hydrates,

[0023] (b) a mixture of at least two hydrophilic solvents, the mixture having a Ab with the compound of formula (I) or one of its optical isomers, its cis-trans isomers (such as an alpha or beta anomer), tautomers, or one of its salts or hydrates comprised between 13 and 16,

[0024] (c) at least one hydrotrope agent, and

[0025] (d) water.

[0026] The invention also relates to a method for care of the skin and / or mucosa comprising application of the composition according to the invention on the skin and / or mucosa.

[0027] The invention also relates to the use of a composition according to the invention for care of the skin and / or mucosa.

[0028] The invention also relates to a final cosmetic composition comprising, in a cosmetically-acceptable medium, from 0.01% to 5% by weight with respect to the total weight of the composition of a composition as described before (i.e. comprising the ingredients a), b), c) and d)). This final composition corresponds in particular to the marketed final cosmetic product.

[0029] The invention also relates to a final cosmetic composition comprising, in a cosmetically-acceptable medium, at least 50% by weight, preferably from 60% to 99%, and more preferably from 70% to 95% by weight with respect to the total weight of the composition of a composition as described before (i.e. comprising the ingredients a), b), c) and d)). This final composition corresponds in particular to the marketed final cosmetic product.

[0030] Preferably, the composition according to the invention is in the form of an emulsion or a gel.

[0031] According to the present invention, and unless indicated otherwise:

[0032] - a "sugar1' radical is a monosaccharide or disaccharide radical. As sugar radical, mention may be made of: sucrose (or saccharose), glucose, galactose, rhamnose, galactose, ribose, fucose, maltose, fructose, mannose, arabinose, xylose or lactose; - "monosaccharide" means a mono-glycoside sugar comprising at least 5 carbon atoms of formula CX(H2O)X, where x is an integer greater than or equal to 5, preferably x is greater than or equal to 6, in particular x is between 5 and 7 inclusive, preferably x is 6. They may be D or L series, and of alpha or beta anomer, as well as one of their salts or their solvates such as hydrates;

[0033] - "disaccharide" means a di-glycoside sugar which is a compound consisting of two glycosides bonded together by O-glycosidic bonds, said compounds consisting of two monosaccharides (also referred to as mono-glycosides) as defined above, said monosaccharide units comprising at least 5 carbon atoms, preferably 6, particularly the mono-glycoside units are bonded together at 1 ,4 or 1 ,6 in a (alpha) or p (beta) anomer, each glycoside unit being capable of being L or D series, as well as one of its salts or its solvates such as hydrates. More particularly, a disaccharide is a polymer formed by two glycosides (or monosaccharides) having as a general formula: -[Cx(H2O)y)]2- or -[(CH2O)X]2-, with x being an integer greater than or equal to 5, preferably x is greater than or equal to 6, in particular x is comprised inclusively between 5 and 7, preferably x is 6, and y is an integer which represents x - 1 ;

[0034] - by "transparent composition", it should be understood, in the context of the present invention, a composition having a turbidity value lower than 200 NTU, preferably lower than 150 NTU, preferably lower than 100 NTU. Preferably, the turbidity of the compositions is equal to at least 1 NTU.

[0035] NTUs (nephelometric turbidity units) are units for measurement of the turbidity of a composition. The turbidity measurement is made, for example, with a model 2100P turbidity meter from Hach Company, the tubes used for the measurement being referenced AR397A cat 24347-06. The measurements are made at ambient temperature (from 20°C to 25°C). Preferably, the composition is transparent and has a turbidity value between 1 and 200 NTU, preferably between 1 and 150 NTU, and preferably less than 100 NTU;

[0036] - "skin" means facial skin and / or body skin, and the scalp;

[0037] - "appendages" means eyelashes, eyebrows, nails and hair, and particularly eyelashes and hair;

[0038] - hereinafter, and unless indicated otherwise, the ranges of values are inclusive, in particular in the expressions "between and" and "ranging from ... to ...";

[0039] - moreover, the expression "at least one" used in the present description is equivalent to the expression "one or more".

[0040] Compound of formula (I) The compound according to the invention comprises at least one compound according to the following formula (I), or one of its optical isomers, its cis-trans isomers (such as an alpha or beta anomer), tautomers, or one of its salts or hydrates:

[0041] [Chem 1] wherein:

[0042] - R’ and R”, identical or different, preferably different, represent a hydrogen or a (Ci- C4)alkyl group for example chosen from among methyl, ethyl, propyl, isopropyl, butyl and isobutyl, preferably a methyl, or a monosaccharide or a polysaccharide including up to 20 sugar units, preferably up to 6 sugar units, in pyranose and / or furanose form and of L and / or D series, said mono- or polysaccharide optionally being substituted by an obligatorily free hydroxyl group, and / or optionally substituted by one or more optionally protected amine function(s), said monosaccharide or polysaccharide being optionally substituted on its - CH2OH group by a -C(O)-CC>2H group, and said monosaccharide or polysaccharide being optionally substituted on one or more of its hydroxy groups by a (Ci-C4)acyl group, preferably an acetyl group, or by a hydroxycinnamyl fragment, chosen from among coumaroyl, cafeoyl, feruloyl and sinapoyl;

[0043] - R’” and R””, identical or different, represent a hydrogen or a (Ci-C4)alkyl group for example chosen from among methyl, ethyl, propyl, isopropyl, butyl and isobutyl, preferably a methyl, it being understood that R’. R”, R’” and R”” do not represent H at the same time.

[0044] Advantageously, R’ and R”, identical or different, preferably different, represent a monosaccharide or a polysaccharide containing up to 6 sugar units, in pyranose and / or furanose form and of L and / or D series, said mono- or polysaccharide having at least one necessarily free hydroxyl function and / or optionally one or more necessarily protected amine function(s).

[0045] Advantageously, the monosaccharide is chosen from D-glucose, D-allose, D- galactose, D-mannose, D-xylose, D-lyxose, L-fucose, L-arabinose, L-rhamnose, D- glucuronic acid, D-galacturonic acid, D-iduronic acid, N-acetyl-D-glucosamine, N-acetyl-D- galactosamine and advantageously denotes D-glucose, L-rhamnose, D-xylose, N-acetyl-D- glucosamine or L-fucose, and more preferably L-rhamnose.

[0046] Advantageously, the polysaccharide containing up to 6 sugar units is chosen from D-maltose, D-lactose, D-cellobiose, D-maltotriose, a disaccharide associating a uronic acid chosen from D-iduronic acid or D-glucuronic acid with a hexosamine chosen from D- galactosamine, D-glucosamine, N-acetyl-D-galactosamine, N-acetyl-D-glucosamine, a disaccharide associating L-rhamnose and D-galactose, an oligosaccharide containing at least one xylose which may be advantageously chosen from xylobiose, methyl-p- xylobioside, xylotriose, xylotetraose, xylopentaose and xylohexaose and in particular xylobiose which is composed to xylose molecules bonded by a 1-4 bond.

[0047] More preferably, R’ and R” are different and represent a monosaccharide or a polysaccharide selected from among D-glucose, D-allose, D-xylose, L-fucose, L-rhamnose, D-galactose, and D-maltose, preferably L-rhamnose and D-galactose in monosaccharide or disaccharide form. More preferably R’ represents a monosaccharide such as L- Rhamnose and R” represents a disaccharide such as a disaccharide associating L- Rhamnose and D-galactose.

[0048] Preferably, R’” and R”” represent a hydrogen.

[0049] The monosaccharide and / or polysaccharide of R’ and / or R” may be substituted on one or more hydroxymethyl residue(s) by a -C(O)-COOH group.

[0050] The salt of the compound of formula (I) may be an alkali metal salt or an alkaline- earth metal salt, preferably a calcium, magnesium, sodium or potassium salt.

[0051] Preferably, the compound of formula (I) or one of its optical isomers, its cis-trans isomers (such as an alpha or beta anomer), tautomers, or one of its salts or hydrates is chosen from robinin and its salts.

[0052] The compound of formula (I) or one of its optical isomers, or its cis-trans isomer (such as an alpha or beta anomer), or its tautomer, or its salt, or its hydrate, preferably robinin or one of its salts, is present in solubilized form in the composition. "In solubilized form" means that the compound does not form crystals visible to the naked eye in the composition. Robinin (C33H40O19) (or Kaempferol-3-o-gal-rham-7-o-rham, or 3-[[6-o-(6-deoxy-a-l- mannopyranosyl)-p-d-galactopyranosyl]oxy]-7-[(6-deoxy-a-l-mannopyranosyl)oxy]-5- hydroxy-2-(4-hydroxyphenyl)-4h-1-benzopyran-4-one; IIIPAC name 4',5-Dihydroxy-3-[a-L- rhamnopyranosyl-(1— >6)-p-D-galactopyranosyloxy]-7-(a-L-rhamnopyranosyloxy)flavone) is the compound with the following formula (II):

[0053] [Chem 2]

[0054] Robinin can exist in two a and p anomer forms.

[0055] The compound of formula (I) is the p anomer of robinin.

[0056] Robinin may also be presented in salt form.

[0057] Preferably, the composition according to the invention comprises robinin or one of its salts in p form. Preferably, the compound of formula (I) or one of its optical isomers, its cis-trans isomers (such as an alpha or beta anomer), tautomers, or one of its salts or hydrates is chosen from robinin and its salts in p form.

[0058] Robinin is a molecule derived from kaempferol. It is a flavone presented in the form of an orange-yellow powder. This molecule is for example present in the leaves and seeds of black locust (Robinia pseudoacacia).

[0059] Robinin is for example marketed by INTERCHIM under the name NAVQll®, or by SIGMA under the name Robinin®.

[0060] Preferably, the composition comprises between 0.1 and 5% by weight of the compound of formula (I) or one of its optical isomers, its cis-trans isomers (such as an alpha or beta anomer), tautomers, or one of its salts or hydrates, preferably robinin or one of its salts, with respect to the total weight of the composition, preferably between 0.1 and 4% by weight, preferably between 0.15 and 3% by weight, preferably between 0.2 and 2% by weight, preferably between 0.3 and 1.5% by weight, and more preferably between 0.4 and 1% by weight.

[0061] Hydrophilic solvent

[0062] The composition according to the invention also comprises a mixture of at least two hydrophilic solvents, the mixture having a Ab with the compound of formula (I) or one of its optical isomers, its cis-trans isomers (such as an alpha or beta anomer), tautomers, or one of its salts or hydrates (preferably with robinin) comprised between 13 and 16, preferably between 13.5 and 15.

[0063] By “hydrophilic solvent”, it is meant an organic solvent that is soluble in water at 25°C and that is liquid or viscous liquid at 25°C (i.e. that does flow under its own weight at 25°C). The hydrophilic solvents are selected from among organic solvents soluble in water at 25°C. The mixture of hydrophilic solvents according to the invention (b) is a mixture having a Ab with the compound of formula (I) or one of its optical isomers, its cis-trans isomers (such as an alpha or beta anomer), tautomers, or one of its salts or hydrates (preferably with robinin) comprised between 13 and 16, preferably between 13.5 and 15.

[0064] The principle of the Hansen solubility sphere is simple, it is based on the Hildebrand parameter:

[0065] The total solubility parameter b is the resultant of the contribution of bo, bp and bn: with b: Hildebrand solubility parameter (MPa1 / 2), and bo, bp and bn: Hansen solubility parameters (MPa1 / 2).

[0066] The principle of Hansen theory remains the same as that of Hildebrand mixtures: the more the solubility parameters are close and the more the compounds are soluble. When considering Hansen parameters, the difference (distance in terms of solubility) between a compound C and a solvent S is expressed as follows:

[0067] [Math 1] where Ab is the distance between C and S in terms of solubility.

[0068] By representing this equation in the Hansen reference frame (O, bo, bp, bn), we obtain a so-called "Hansen solubility sphere" ellipsoid. The radius of the latter, R, represents the limit of solubility of the compound C whose coordinates are of course those of the center of the sphere.

[0069] All of the solvents whose coordinates will be located inside the sphere will be good solvents, and all of the solvents that will be located outside the sphere will be considered as non-solvents or poor solvents. Thus, in the case where Ab < R, the solvent S is a good solvent of the compound C at a concentration lower than or equal to the measured one. Otherwise, the solvent S is a poor solvent of the compound C at the concentration equal to the measured one. As a general rule, the shorter the distance, the best the affinity between the two will be, and therefore the higher the probability of having a good solvent will be. Nevertheless, a mixture of solvents whose Ab value is higher than the R of each of the solvents could lead to a mixture with a Ab lower than the R allowing solubilizing robinin.

[0070] Robinin has the following Hansen solubility parameters: bo = 16, bp = 23 and bn = 19.

[0071] The mixture of hydrophilic solvents according to the invention is a mixture having a Ab with the compound of formula (I) or one of its optical isomers, its cis-trans isomers (such as an alpha or beta anomer), tautomers, or one of its salts or hydrates, comprised between 13 and 16, preferably between 13.5 and 15.

[0072] Advantageously, the mixture of hydrophilic solvents according to the invention is a mixture having a Ab with robinin comprised between 13 and 16, preferably between 13.5 and 15.

[0073] Preferably, the hydrophilic solvent is selected from among alcohols, polyols and mixtures thereof.

[0074] Among the alcohols, mention may be made of C1-C10, more preferably C1-C5, alcohols, such as ethanol, isopropanol, propanol and butanol. Preferably, the alcohol is ethanol.

[0075] Preferably, the polyol is selected from among polyols having from 2 to 20 carbon atoms, more preferably from 2 to 6 carbon atoms. Preferably, the polyol is selected from among glycerol, propylene glycol, butylene glycol, 1 ,3-propanediol, pentylene glycol and polyethylene glycols having from 2 to 10 ethylene oxide units. Preferably, polyethylene glycol having from 2 to 10 ethylene oxide units is selected from among PEG-6, PEG-8 and mixtures thereof. Preferably, the hydrophilic solvent is selected from among C1-C10 alcohols, more preferably from among ethanol, glycerol, propylene glycol, butylene glycol, 1 ,3-propanediol, pentylene glycol, PEG-6, PEG-8 and mixtures thereof.

[0076] Preferably, the mixture of hydrophilic solvents according to the invention is a mixture of at least two polyols, preferably at least three polyols, preferably at least four polyols.

[0077] Preferably, the mixture of hydrophilic solvents according to the invention is a mixture at least of propylene glycol, 1 ,3-propanediol and pentylene glycol.

[0078] Preferably, the mixture of hydrophilic solvents according to the invention also comprises glycerol and / or dipropylene glycol and / or PEG-6.

[0079] Preferably, the mixture of hydrophilic solvents according to the invention is a mixture of glycerol, propylene glycol, 1 ,3-propanediol and pentylene glycol, in a weight ratio (glycerokpropylene glycol: 1 ,3-propanediol:pentylene glycol) comprised between 40-45: 8- 12: 3-7: 2-4. Preferably, the mixture of hydrophilic solvents according to the invention is a mixture of glycerol, propylene glycol, 1 ,3-propanediol and pentylene glycol, in a weight ratio (glycerokpropylene glycol: 1 ,3-propanediokpentylene glycol) equal to 42: 10: 5: 3.

[0080] The present invention also relates to a cosmetic composition comprising, preferably consisting of:

[0081] (a) at least one compound of formula (I), or one of its optical isomers, its cis-trans isomers (such as an alpha or beta anomer), tautomers, or one of its salts or hydrates,

[0082] (b) a mixture of glycerol, propylene glycol, 1 ,3-propanediol and pentylene glycol, preferably in a weight ratio (glycerokpropylene glycol: 1 ,3-propanediokpentylene glycol) comprised between 40-45: 8-12: 3-7: 2-4. Preferably, the mixture of hydrophilic solvents is a mixture of glycerol, propylene glycol, 1 ,3-propanediol and pentylene glycol, in a weight ratio (glycerokpropylene glycol: 1 ,3-propanediokpentylene glycol) equal to 42: 10: 5: 3,

[0083] (c) at least one hydrotrope agent, preferably in an amount of at least 3% by weight with respect to the total weight of the composition, and

[0084] (d) water.

[0085] Preferably, the mixture of hydrophilic solvents according to the invention is a mixture of glycerol, propylene glycol, 1 ,3-propanediol, pentylene glycol and dipropylene glycol, in a weight ratio (glycerokpropylene glycol: 1 ,3-propanediol:pentylene glycokdipropylene glycol) comprised between 40-45: 8-12: 3-7: 2-4: 23-26. Preferably, the mixture of hydrophilic solvents according to the invention is a mixture of glycerol, propylene glycol, 1 ,3- propanediol, pentylene glycol and dipropylene glycol, in a weight ratio (glycerokpropylene glycol: 1 ,3-propanediokpentylene glycokdipropylene glycol) equal to 42: 10: 5: 3: 24.5.

[0086] The present invention also relates to a cosmetic composition comprising, preferably consisting of:

[0087] (a) at least one compound of formula (I), or one of its optical isomers, its cis-trans isomers (such as an alpha or beta anomer), tautomers, or one of its salts or hydrates,

[0088] (b) a mixture of glycerol, propylene glycol, 1 ,3-propanediol, pentylene glycol and dipropylene glycol, preferably in a weight ratio (glycerokpropylene glycol: 1 ,3- propanediokpentylene glycokdipropylene glycol) comprised between 40-45: 8-12: 3-7: 2-4: 23-26. Preferably, the mixture of hydrophilic solvents is a mixture of glycerol, propylene glycol, 1 ,3-propanediol, pentylene glycol and dipropylene glycol, in a weight ratio (glycerokpropylene glycol: 1 ,3-propanediokpentylene glycokdipropylene glycol) equal to 42: 10: 5: 3: 24.5,

[0089] (c) at least one hydrotrope agent, preferably in an amount of at least 3% by weight with respect to the total weight of the composition, and

[0090] (d) water.

[0091] Preferably, the mixture of hydrophilic solvents according to the invention is a mixture of propylene glycol, 1 ,3-propanediol, pentylene glycol and dipropylene glycol, in a weight ratio (propylene glycol: 1 ,3-propanediokpentylene glycokdipropylene glycol) comprised between 8-12: 3-7: 2-4: 23-26. Preferably, the mixture of hydrophilic solvents is a mixture of propylene glycol, 1 ,3-propanediol, pentylene glycol and dipropylene glycol, in a weight ratio (propylene glycol: 1 ,3-propanediokpentylene glycokdipropylene glycol) equal to 10: 5: 3: 24.5.

[0092] The present invention also relates to a cosmetic composition comprising, preferably consisting of:

[0093] (a) at least one compound of formula (I), or one of its optical isomers, its cis-trans isomers (such as an alpha or beta anomer), tautomers, or one of its salts or hydrates,

[0094] (b) a mixture of propylene glycol, 1 ,3-propanediol, pentylene glycol and dipropylene glycol, in a weight ratio (propylene glycol: 1 ,3-propanediokpentylene glycokdipropylene glycol) comprised between 8-12: 3-7: 2-4: 23-26. Preferably, the mixture of hydrophilic solvents is a mixture of propylene glycol, 1 ,3-propanediol, pentylene glycol and dipropylene glycol, in a weight ratio (propylene glycol: 1 ,3-propanediol:pentylene glycokdipropylene glycol) equal to 10: 5: 3: 24.5,

[0095] (c) at least one hydrotrope agent, preferably in an amount of at least 3% by weight with respect to the total weight of the composition, and

[0096] (d) water.

[0097] Preferably, the mixture of hydrophilic solvents according to the invention is a mixture of propylene glycol, 1 ,3-propanediol, pentylene glycol, dipropylene glycol and PEG-6, in a weight ratio (propylene glycol: 1 ,3-propanediol:pentylene glycokdipropylene glycol: PEG-6) comprised between 3-12: 3-12: 1-6: 18-26: 2-10. Preferably, the mixture of hydrophilic solvents is a mixture of propylene glycol, 1 ,3-propanediol, pentylene glycol, dipropylene glycol and PEG-6, in a weight ratio (propylene glycol: 1 ,3-propanediokpentylene glycokdipropylene glycol: PEG-6) equal to 5: 10: 1.75: 24.5 or 25: 10, respectively. Preferably, the mixture of hydrophilic solvents is a mixture of propylene glycol, 1 ,3- propanediol, pentylene glycol, dipropylene glycol and PEG-6, in a weight ratio (propylene glycol: 1 ,3-propanediokpentylene glycokdipropylene glycol: PEG-6) equal to 5: 5: 3.5: 25: 10, respectively. Preferably, the mixture of hydrophilic solvents is a mixture of propylene glycol, 1 ,3-propanediol, pentylene glycol, dipropylene glycol and PEG-6, in a weight ratio (propylene glycol: 1 ,3-propanediokpentylene glycokdipropylene glycol: PEG-6) equal to 10: 7.5: 5.25: 18.65: 2.5.

[0098] The present invention also relates to a cosmetic composition comprising, preferably consisting of:

[0099] (a) at least one compound of formula (I), or one of its optical isomers, its cis-trans isomers (such as an alpha or beta anomer), tautomers, or one of its salts or hydrates,

[0100] (b) a mixture of propylene glycol, 1 ,3-propanediol, pentylene glycol, dipropylene glycol and PEG-6, in a weight ratio (propylene glycol: 1 ,3-propanediokpentylene glycokdipropylene glycol: PEG-6) comprised between 3-12: 3-12: 1-6: 18-26: 2-10. Preferably, the mixture of hydrophilic solvents is a mixture of propylene glycol, 1 ,3- propanediol, pentylene glycol, dipropylene glycol and PEG-6, (i) in a weight ratio (propylene glycol: 1 ,3-propanediokpentylene glycokdipropylene glycol: PEG-6) equal to 5: 10: 1.75: 24.5 or 25: 10; or (ii) in a weight ratio (propylene glycol: 1 ,3-propanediokpentylene glycokdipropylene glycol: PEG-6) equal to 5: 5: 3.5: 25: 10; or (iii) in a weight ratio (propylene glycol: 1 ,3-propanediokpentylene glycokdipropylene glycol: PEG-6) equal to 10: 7.5: 5.25: 18.65: 2.5, (c) at least one hydrotrope agent, preferably in an amount of at least 3% by weight with respect to the total weight of the composition, and

[0101] (d) water.

[0102] Preferably, the composition comprises, with respect to the total of the composition, from 30 to 42% by weight glycerol and / or from 4 to 10% by weight propylene glycol and / or from 2 to 5% by weight 1 ,3-propanediol and / or from 1 to 3% by weight pentylene glycol and / or from 16 to 24.5% dipropylene glycol and / or from 8 to 12% by weight butylene glycol and / or from 2 to 10% by weight PEG-6.

[0103] According to one embodiment, the composition comprises a mixture of at least two hydrophilic solvents, said mixture being present in an amount greater than 30% by weight with respect to the total weight of the composition, preferably greater than 35% by weight, preferably greater than 40% by weight, the mixture having a Ab with the compound of formula (I) or one of its optical isomers, its cis-trans isomers (such as an alpha or beta anomer), tautomers, or one of its salts or hydrates, preferably with robinin, comprised between 13 and 16, preferably between 13.5 and 15.

[0104] Hydrotrope agent

[0105] The composition according to the invention comprises at least one hydrotrope agent.

[0106] Preferably, the hydrotrope agents are cosmetically-acceptable hydrotrope agents.

[0107] "Hydrotrope" or "hydrotrope agent" means a water-soluble compound which has an amphiphilic molecular structure and which is capable of considerably increasing the solubility of organic molecules slightly soluble in water. A hydrotrope is different from a polymer (i.e. chemical compound constituted of repetitions of a structural unit and having a molar mass greater than 10 000 g / mol). A hydrotrope is a small molecule; typically it presents a molar mass comprised between 1 and 600 g / mol.

[0108] Hydrotropes are like surfactants, but are distinguished by their hydrophobic part which is shorter and does not make it possible to induce spontaneous autoagreggation. Unlike surfactants, these compounds do not have a critical micellar concentration.

[0109] Among the hydrotrope agents known from the prior art, mention may be made of sodium 1 ,3-benzenedisulfonate, sodium benzoate, sodium 4-pyridinecarboxylate (sodium PCA), sodium salicylate, sodium benzene sulfonate, caffeine, sodium p-toluene sulfonate, sodium butyl monoglycolsulfate, 4-aminobenzoic acid and its HCI salt, sodium cumene sulfonate, N,N-diethylnicotinamide, N-picolylnicotinamide, N-allylnicotinamide, 2- methacryloyloxyethyl phosphorylcholine, resorcinol, urea, hydroxyethyl urea, N,N-dimethyl urea, pyrogallol, N-picolylacetamide 3.5, procaine hydrochloride, proline hydrochloride, niacinamide (or nicotinamide), pyridine, 3-picolylamine, ibuprofen sodium, sodium xylene sulfonate, ethyl carbamate, pyridoxal hydrochloride, sodium benzoate, 2-pyrrolidone, ethylurea, N,N-dimethylacetamide, N-methylacetamide or isoniazide.

[0110] A list of hydrotropes is detailed in the following publications: Lee J. et al, "Hydrotropic Solubilization of Paclitaxel: Analysis of Chemical Structures for Hydrotropic Property", Pharmaceutical Research, Vol. 20, No. 7, 2003, Lee S. et al., "Hydrotropic Polymers: Synthesis and Characterization of Polymers Containing Picolylnicotinamide Moieties", Macromolecules, 36, 2248-2255, 2003, and Hodgon T.K., Kaier E.W., "Hydrotropic Solutions", Current Opinion in Colloid and Interface Science, 12, 121-128, 2007. Cosmetically-acceptable hydrotropes denote hydrotropes which are compatible with a cosmetic application, i.e. application on the skin, mucosa and / or skin appendages.

[0111] Preferably, the suitable hydrotrope according to the invention is chosen from the following hydrotropes and mixtures thereof:

[0112] [Table 1]

[0113] Preferably, the composition according to the invention comprises at least one hydrotrope agent chosen from caffeine, niacinamide and mixtures thereof.

[0114] Preferably, the composition according to the invention comprises a mixture of caffeine and niacinamide.

[0115] Preferably, caffeine and niacinamide are present in the composition according to the invention in a weight ratio caffeinemiacinamide comprised between 2:1 and 1 :2, preferably about 1 :1.

[0116] Preferably, the amount of hydrotrope agents in the composition according to the invention is at least 3% by weight with respect to the total weight of the composition, preferably between 3 and 15% by weight, preferably between 3 and 10% by weight, preferably between 3 and 6% by weight.

[0117] Preferably, the weight ratio of hydrotrope agent(s): compound of formula (I) or one of its optical isomers, its cis-trans isomers (such as an alpha or beta anomer), tautomers, or one of its salts or hydrates, in the composition according to the invention is at least 6:1.

[0118] Preferably, the weight ratio hydrotrope agent(s):robinin in the composition according to the invention is at least 6:1.

[0119] Water

[0120] The composition according to the invention comprises water. The water used may be sterile demineralized water and / or floral water such as rose water, cornflower water, chamomile water or linden water, and / or a spring or natural mineral water, such as VITTEL water, LUCAS water or LA ROCHE POSAY water.

[0121] Preferably, the composition comprises at least 10% by weight water with respect to the total weight of the composition, preferably at least 20% by weight, preferably at least 30% by weight.

[0122] Preferably, the composition comprises at most 60% by weight water with respect to the total weight of the composition, preferably at most 55% by weight, preferably at most 54% by weight.

[0123] Preferably, the composition is completely free of water.

[0124] The composition according to the invention may also contain ingredients that are common in the cosmetics industry, such as preservatives, perfumes, charges, oils, waxes, pasty fats, solar protection filters or UV filters, odor absorbers, colorants, basic agents, acids, sequestrants or active ingredients.

[0125] The quantities of these various ingredients are conventionally the quantities used in the field considered, for example from 0.01 to 20% of the total weight of the composition. These ingredients, depending on their nature, may be introduced into the oily phase and / or into the aqueous phase.

[0126] Obviously, those skilled in the art will take care to choose the optional compound(s) to add to the composition according to the invention and their quantities in such a way that the advantageous properties intrinsically associated with the composition according to the invention are not altered, or are not substantially altered, by the envisaged addition.

[0127] The composition according to the invention may be obtained conventionally by those skilled in the art.

[0128] The invention also relates to a final cosmetic composition comprising, in a cosmetically-acceptable medium, at least 50% by weight, preferably from 60% to 99%, and more preferably from 70% to 95% by weight with respect to the total weight of the composition of a composition as described before (i.e. comprising the ingredients a), b), c) and d)). In particular, this final composition corresponds to the robinin-based commercialized final cosmetic product. Cosmetically-acceptable medium means a medium compatible with the skin and / or its appendages.

[0129] The invention also relates to a method for care of the skin and / or mucosa comprising application of the composition according to the invention or the final composition according to the invention on the skin and / or mucosa.

[0130] The invention also relates to the use of a composition according to the invention or the final composition according to the invention for care of the skin and / or mucosa.

[0131] The following examples make it possible to understand the invention better, without being in any way limitative. The raw materials are referred to with the chemical or INCI name thereof. The quantities indicated are as a % by weight of raw materials with respect to the total weight of the composition (% w / w), unless specified otherwise.

[0132] Examples

[0133] Example 1 : preparation of compositions not covered by the invention with water

[0134] The compositions in Table 2 were prepared according to the following protocol:

[0135] Robinin is added by sprinkling in water under magnetic stirring or under Rayneri stirring, until obtaining a transparent and limpid solution.

[0136] [Table 2]

[0137] The results show that water does not allow solubilizing robinin, irrespective of the tested concentration. to the invention and assessment relative to a com com Each of the compositions 7B to 7H according to the invention comprises (i) a mixture of solvents according to the invention, and (ii) a caffeinemiacinamide mixture in a weight ratio of 1 :1. The comparative composition 7A* comprises (i) a mixture of solvents according to the invention but does not comprise a caffeinemiacinamide mixture.

[0138] The compositions of the tables 3 and 4 have been prepared according to the following protocol:

[0139] - Prepare the solution of hydrotropes by firstly dissolving Niacinamide in the water of the composition. Homogenizing and heating at 40°C to promote the dissolution of the raw material. Then add Caffeine and homogenize by heating at 40°C for 20 minutes,

[0140] - Weigh the glycols (Propylene glycol, 1 ,3-propanediol, Pentylene glycol, Dipropylene glycol and / or PEG-6) in the preparation beaker,

[0141] - Add the solution of hydrotropes prepared beforehand,

[0142] - Sprinkle robinin,

[0143] - Mix with a magnetic stir bar or a saw tooth propeller and heat at 50°C for 1 hour at most,

[0144] - Complete with the water QS at the end to compensate for water losses over the process.

[0145] [Table 3]

[0146] [Table 4]

[0147] The results show that, in the presence of water (and in the absence of a hydrotropic compounds), the mixture of the solvent according to the invention alone does not allow solubilizing robinin, even in an amount of only 0.5% by weight. On the other hand, the results show that the addition of at least 3% by weight of hydrotropic compounds such as caffeine and niacinamide again allows solubilizing robinin in a composition comprising a great amount of water.

Claims

CLAIMS1. A cosmetic composition comprising:(a) at least one compound of formula (I), or one of its optical isomers, its cis-trans isomers (such as an alpha or beta anomer), tautomers, or one of its salts or hydrates:[Chem 1]wherein:- R’ and R”, identical or different, preferably different, represent a hydrogen or a (Ci- C4)alkyl group for example chosen from among methyl, ethyl, propyl, isopropyl, butyl and isobutyl, preferably a methyl, or a monosaccharide or a polysaccharide including up to 20 sugar units, preferably up to 6 sugar units, in pyranose and / or furanose form and of L and / or D series, said mono- or polysaccharide optionally being substituted by an obligatorily free hydroxyl group, and / or optionally substituted by one or more optionally protected amine function(s), said monosaccharide or polysaccharide being optionally substituted on its - CH2OH group by a -C(O)-CC>2H group, and said monosaccharide or polysaccharide being optionally substituted on one or more of its hydroxy groups by a (Ci-C4)acyl group, preferably an acetyl group, or by a hydroxycinnamyl fragment, chosen from among coumaroyl, cafeoyl, feruloyl and sinapoyl;- R’” and R””, identical or different, represent a hydrogen or a (Ci-C4)alkyl group for example chosen from among methyl, ethyl, propyl, isopropyl, butyl and isobutyl, preferably a methyl, it being understood that R’, R”, R’” and R”” do not represent H at the same time,(b) a mixture of at least two hydrophilic solvents, the mixture having a Ab with the compound of formula (I) or one of its optical isomers, its cis-trans isomers (such as an alpha or beta anomer), tautomers, or one of its salts or hydrates comprised between 13 and 16,(c) at least one hydrotrope agent, and(d) water.

2. The composition according to claim 1 , wherein the compound of formula (I) or one of its optical isomers, its cis-trans isomers (such as an alpha or beta anomer), tautomers, or one of its salts or hydrates is chosen from robinin and its salts, preferably in P form.

3. The composition according to claim 1 or 2, which comprises between 0.1 and 5% by weight of the compound of formula (I), or one of its optical isomers, its cis-trans isomers (such as an alpha or beta anomer), tautomers, or one of its salts or hydrates with respect to the total weight of the composition, preferably between 0.1 and 4% by weight, preferably between 0.15 and 3% by weight, preferably between 0.2 and 2% by weight, preferably between 0.3 and 1.5% by weight, preferably between 0.4 and 1 % by weight.

4. The composition according to one of the preceding claims, wherein the mixture of at least two hydrophilic solvents is present in an amount greater than 30% by weight with respect to the total weight of the composition, preferably greater than 35% by weight, preferably greater than 40% by weight.

5. The composition according to one of the preceding claims, wherein the hydrophilic solvents are selected from among organic solvents soluble in water at 25°C, preferably selected from among alcohols, polyols and mixtures thereof.

6. The composition according to claim 5, wherein the alcohols are selected from among C1-C10 alcohols, more preferably C1-C5 alcohols, such as ethanol, isopropanol, propanol and butanol, preferably the alcohol is ethanol; and / or the polyols are selected from among polyols having from 2 to 20 carbon atoms, more preferably from 2 to 6 carbon atoms, preferably from among glycerol, propylene glycol, butylene glycol, 1 ,3-propanediol, pentylene glycol and polyethylene glycols having from 2 to 10 ethylene oxide units.

7. The composition according to one of the preceding claims, wherein the mixture of hydrophilic solvents is a mixture of at least two polyols, preferably at least three polyols, preferably at least four polyols, preferably the mixture of hydrophilic solvents is a mixture of at least one propylene glycol, 1 ,3-propanediol and pentylene glycol and could also comprise glycerol and / or dipropylene glycol and / or PEG-6.

8. The composition according to one of the preceding claims, wherein the amount of hydrotrope agent(s) is at least 3% by weight with respect to the total weight ofthe composition, preferably between 3 and 15% by weight, preferably between 3 and 10% by weight, preferably between 3 and 6% by weight.

9. The composition according to one of the preceding claims, wherein the weight ratio of hydrotrope agent(s): compound of formula (I), or one of its optical isomers, its cis-trans isomers (such as an alpha or beta anomer), tautomers, or one of its salts or hydrates, preferably the weight ratio of hydrotrope agent(s):robinin, is at least 6:1.

10. The composition according to one of the preceding claims, which comprises at least one hydrotrope agent selected from among niacinamide, caffeine, urea, PCA sodium, sodium salicylate, hydroxyethyl urea and mixtures thereof, preferably selected from among caffeine, niacinamide and mixtures thereof.

11. The composition according to one of the preceding claims, which comprises a mixture of caffeine and niacinamide in a caffeinemiacinamide weight ratio comprised between 2:1 and 1 :2, preferably about 1 :1.

12. The composition according to one of claims 1 to 11 , wherein the mixture of hydrophilic solvents is a mixture of glycerol, propylene glycol, 1 ,3-propanediol and pentylene glycol, in a weight ratio (glycerokpropylene glycol: 1 ,3-propanediol:pentylene glycol) comprised between 40-45: 8-12: 3-7: 2-4, preferably the mixture of hydrophilic solvents is a mixture of glycerol, propylene glycol, 1 ,3-propanediol and pentylene glycol, in a weight ratio (glycerokpropylene glycol: 1 ,3-propanediokpentylene glycol) equal to 42: 10: 5: 3.

13. The composition according to one of claims 1 to 11 , wherein the mixture of hydrophilic solvents is a mixture of glycerol, propylene glycol, 1 ,3-propanediol, pentylene glycol and dipropylene glycol, in a weight ratio (glycerokpropylene glycol: 1 ,3- propanediokpentylene glycokdipropylene glycol) comprised between 40-45: 8-12: 3-7: 2-4: 23-26, preferably the mixture of hydrophilic solvents is a mixture of glycerol, propylene glycol, 1 ,3-propanediol, pentylene glycol and dipropylene glycol, in a weight ratio (glycerokpropylene glycol: 1 ,3-propanediokpentylene glycokdipropylene glycol) equal to 42: 10: 5: 3: 24.5.

14. The composition according to one of claims 1 to 11 , wherein the mixture of hydrophilic solvents is a mixture of propylene glycol, 1 ,3-propanediol, pentylene glycol and dipropylene glycol, in a weight ratio (propylene glycol: 1 ,3-propanediokpentylene glycokdipropylene glycol) comprised between 8-12: 3-7: 2-4: 23-26, preferably the mixtureof hydrophilic solvents is a mixture of propylene glycol, 1 ,3-propanediol, pentylene glycol and dipropylene glycol, in a weight ratio (propylene glycol: 1 ,3-propanediol:pentylene glycokdipropylene glycol) equal to 10: 5: 3: 24.5.

15. The composition according to one of the preceding claims, which comprises, with respect to the total weight of the composition, from 30 to 42% by weight glycerol and / or from 4 to 10% by weight propylene glycol and / or from 2 to 5% by weight 1 ,3- propanediol and / or from 1 to 3% by weight pentylene glycol and / or from 16 to 24.5% de dipropylene glycol and / or from 8 to 12% by weight butylene glycol and / or from 2 to 10% by weight PEG-6.

16. The composition according to one of the preceding claims, which comprises water in an amount lower than or equal to 60% by weight with respect to the total weight of the composition, preferably lower than or equal to 55% by weight, preferably lower than or equal to 54% by weight; and / or at least 10% by weight water with respect to the total weight of the composition, preferably at least 20% by weight, preferably at least 30% by weight.

17. A final cosmetic composition comprising, in a cosmetically-acceptable medium, at least 50% by weight, preferably from 60% to 99% by weight, more preferably from 70% to 95% with respect to the total weight of the composition of a composition according to claims 1 to 16.

18. Method for skin and / or mucosa care comprising the application of a composition according to one of claims 1 to 16 or 17 on the skin and / or the mucosa.

19. Use of a composition according to one of claims 1 to 16 or 17 for skin and / or mucosa care.

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