Composition based on robinine and hydrophilic solvents

Abstract

Composition based on robinine and hydrophilic solvents The present invention relates to a cosmetic composition comprising: a maximum content of 4% by weight relative to the total weight of the composition, of 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, and 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 of between 14 and 16. It also relates to a method for caring for the skin and / or mucous membranes comprising the application of the composition according to the invention to the skin and / or mucous membranes. Figure for the abstract: none

Description

Title of the invention: Composition based on robinine and hydrophilic solvents

[0001] The present invention relates to a cosmetic composition comprising:

[0002] (a) a maximum content (i.e. less than or equal to) of 4% by weight relative to the total weight of composition, of at least one compound of formula (I) as defined below, 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, and

[0003] (b) a mixture of at least two hydrophilic solvents, the mixture having an Aô 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 between 14 and 16.

[0004] Human skin is made up of two compartments, namely a deep compartment, the dermis, and a superficial compartment, the epidermis. The epidermis is in contact with the external environment, and its role is in particular to protect the body from dehydration and from external, chemical or mechanical attacks.

[0005] There is always a need for new cosmetic compositions having interesting properties, particularly on the skin.

[0006] Robinine is an interesting active ingredient for this purpose. Indeed, this type of active ingredient is known in cosmetics, for example from application EP4171476.

[0007] However, robinine is soluble in certain solvents such as hot alcohols (which poses flammability and therefore safety problems). Robinine is soluble in hot water, but is not soluble in water at room temperature. It therefore does not allow, as such, the formulation of stable cosmetic compositions applicable to the skin.

[0008] The formulator is therefore looking for compositions comprising robinine which are stable and applicable in particular topically (i.e. on the skin and / or mucous membranes).

[0009] Such compositions must further comprise a certain amount of water, in order to be able to formulate robinine in a wide range of cosmetic carriers including lotions, gels or emulsions.

[0010] In this context, the inventors have surprisingly discovered that particular hydrophilic solvents allow the solubilization of robinine, and are compatible with a formulation in an aqueous medium.

[0011] The invention therefore aims to provide a cosmetic composition meeting all these issues.

[0012] Thus, the present invention relates to a cosmetic composition comprising:

[0013] (a) a maximum content (i.e. less than or equal to) of 4% by weight relative to the total weight of composition, of 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:

[0014] [Chem.l] (I)

[0015] in which:

[0016] - R' and R”, identical or different, preferably different, represent a hydrogen or a (Ci-C4)alkyl group, for example chosen from methyl, ethyl, propyl, isopropyl, butyl and isobutyl, preferably a methyl, or a monosaccharide or a polysaccharide comprising 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 being optionally substituted by a hydroxyl group which must be free, 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)-CO2 H 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 coumaroyl, caffeoyl, feruloyl and sinapoyl;

[0017] - R' ” and R” ”, identical or different, represent a hydrogen or a group (Ci - C4)alkyl for example chosen from methyl, ethyl, propyl, isopropyl, butyl and isobutyl, preferably a methyl,

[0018] it being understood that R', R”, R” ' and R” ” do not represent H at the same time,

[0019] and

[0020] (b) a mixture of at least two hydrophilic solvents, the mixture having an Aô 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 included between 14 and 16.

[0021] Preferably, the present invention relates to a cosmetic composition consisting of:

[0022] (a) a maximum content (i.e. less than or equal to) of 4% by weight relative to the total weight of composition, of 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, and

[0023] (b) a mixture of at least two hydrophilic solvents, the mixture having an Aô 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 between 14 and 16.

[0024] The invention also relates to a method for caring for the skin and / or mucous membranes comprising the application of the composition according to the invention to the skin and / or mucous membranes.

[0025] The invention also relates to the use of a composition according to the invention for the care of the skin and / or mucous membranes.

[0026] 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% by weight, and more preferably from 70% to 95% relative to the total weight of the composition of a composition as described above (i.e. comprising ingredients a) and b)). This final composition corresponds in particular to the final commercialized cosmetic product.

[0027] For the purposes of the present invention, and unless otherwise indicated:

[0028] - a “sugar” radical is a monosaccharide or disaccharide radical. We can cite as sugar radical: sucrose (or saccharose), glucose, galactose, rhamnose, galactose, ribose, fucose, maltose, fructose, mannose, arabinose, xylose or lactose;

[0029] - by “monosaccharide” is meant a monosaccharide sugar comprising at least 5 carbon atoms of formula CX(H2O)X, with x being an integer greater than or equal to 5, preferably x is greater than or equal to 6, in particular x is inclusively between 5 and 7, preferably x is 6. They may be of D or L configuration, and of alpha or beta anomer, as well as one of their salts or their solvates such as hydrates;

[0030] - by "disaccharide" is meant a di-osidic sugar which is a compound consisting of two oses linked together by O-osidic bonds, said compounds being made up of two monosaccharides (also called mono-osidics) as defined previously, said monosaccharide units comprising at least 5 carbon atoms, preferably 6, particularly the monosaccharide units are linked together in 1,4 or 1,6 in anomer a (alpha) or [3 (beta), each saccharide unit being able to be of L or D configuration, as well as one of its salts or its solvates such as hydrates. A disaccharide is more particularly a polymer formed from two oses (or monosaccharides) having the 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 inclusively between 5 and 7, preferably x is 6, and y is an integer which represents x - 1;

[0031] - by “transparent composition” is meant within the meaning of the present invention a composition having a turbidity value of less than 200 NTU, preferably less than 150 NTU, preferably less than 100 NTU. Preferably, the turbidity of the compositions is at least 1 NTU.

[0032] NTU (nephelometric turbidity units) are the units of measurement for the turbidity of a composition. The measurement of turbidity is carried out, for example, with a turbidimeter model 2100P from Hach Company, the tubes used for the measurement being referenced AR397A cat 24347-06. The measurements are carried out at room temperature (from 20°C to 25°C).

[0033] Preferably, the composition is transparent and has a turbidity value of between 1 and 200 NTU, preferably between 1 and 150 NTU, preferably less than 100 NTU;

[0034] - by “skin” we mean the skin of the face and / or body, the scalp;

[0035] - by "annexes" we mean eyelashes, eyebrows, nails, and hair, in particular especially eyelashes and hair;

[0036] - in what follows, and unless otherwise indicated, the limits of a domain of values ​​are included in this domain, notably in the expressions “between” and “ranging from ... to ...";

[0037] - moreover, the expression “at least one” used in the present description is equivalent to the expression “one or more”. Compound of formula (I)

[0038] The composition according to the invention comprises a maximum content (i.e. less than or equal to) 4% by weight relative to the total weight of the composition, of at least one compound of 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:

[0039] [Chem.l] (I)

[0040] in which:

[0041] - R' and R”, identical or different, preferably different, represent a hydrogen or a (Ci-C4)alkyl group, for example chosen from methyl, ethyl, propyl, isopropyl, butyl and isobutyl, preferably a methyl, or a monosaccharide or a polysaccharide comprising 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 being optionally substituted by a hydroxyl group which must be free, 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)-CO2 H 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 coumaroyl, caffeoyl, feruloyl and sinapoyl;

[0042] - R' ” and R” ”, identical or different, represent a hydrogen or a group (Ci - C4)alkyl for example chosen from methyl, ethyl, propyl, isopropyl, butyl and isobutyl, preferably a methyl,

[0043] 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 hydroxyl function which is obligatorily free and / or optionally one or more amine functions which are obligatorily protected.

[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 combining 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 combining L-rhamnose and D-galactose, an oligosaccharide containing at least one xylose which may be advantageously chosen from xylobiose, methyl-[3-xylobioside, xylotriose, xylotetraose, xylopentaose and xylohexaose and in particular xylobiose which is composed of two xylose molecules linked by a 1-4 bond.

[0047] More preferably, R' and R' ' are different and represent a monosaccharide or a polysaccharide chosen from 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 combining L-rhamnose and D-galactose.

[0048] Preferably, R'” and R” ” represent hydrogen.

[0049] The monosaccharide and / or the 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 or 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 robinine and its salts. Preferably, the composition according to the invention comprises a maximum content of 4% (i.e. less than or equal to 4%) by weight relative to the total weight of composition, of robinine or one of its salts.

[0052] The compound of formula (I) or its optical isomer, or its cis-trans isomer (such as an alpha or beta anomer), or its tautomer, or its salt, or its hydrate, preferably robin or one of its salts, is present in solubilized form in the composition. By "in solubilized form" is meant that the compound does not form crystals visible to the naked eye in the composition.

[0053] Robinin (C33H40Oi9) (or Kaempferol-3-o-gal-rham-7-o-rham, or 3-[[6-o-(6-deoxy-al-mannopyranosyl)-[3-d-galactopyranosyl]oxy]-7-[(6-deoxy-al-ma nnopyranosyl)oxy]-5-hydroxy-2-(4-hydroxyphenyl)-4h-l-benzopyran-4-one; IUPAC name 4',5-Dihydroxy-3-[aL-rhamnopyranosyl-(1 —>6)-[3-D-galactopyranosyloxy]-7-(aL-rhamnopyranosyloxy)flavone) is the compound of the following formula (II):

[0054] [Chem.2] OH OH OH (II)

[0055] Robinine can exist in two forms of anomers α and [3.

[0056] The compound of formula (II) is the [3] anomer of robinine.

[0057] Robinine can also be present in salt form.

[0058] 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 robinine and its salts in the form [3.

[0059] Robinine is a molecule derived from kaempferol. It is a flavone that comes in the form of a yellow-orange powder. This molecule is present, for example, in the leaves and seeds of the black locust (Robinia pseudoacacia).

[0060] Robinin is for example marketed by INTERCHIM under the name NAVQU®, or by SIGMA under the name Robinin®.

[0061] The composition according to the invention comprises a maximum content of 4% by weight relative to the total weight of the composition, of at least one compound of 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. By "maximum content of 4% by weight", is meant a content less than or equal to 4% by weight.

[0062] Preferably, the composition comprises between 0.1 and 4% by weight of 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 relative to the total weight of the composition, preferably between 0.2 and 4% by weight, preferably between 0.3 and 4% by weight, preferably between 0.5 and 4% by weight. Hydrophilic solvent

[0063] The composition according to the invention also comprises a mixture of at least two hydrophilic solvents, the mixture having an Aô 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 robinine) of between 14 and 16.

[0064] The hydrophilic solvents are chosen from organic solvents soluble in water at 25°C. The mixture of hydrophilic solvents according to the invention (b) is a mixture having an Aô 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 robinine, between 14 and 16.

[0065] The principle of Hansen's solubility sphere is simple, it is based on the Hildebrand parameter:

[0066] The total solubility parameter ô is the resultant of the contribution of ôD, ôP and ôH: 8 ~ 8. “h â 8 DFM

[0067] with ô: Hildebrand solubility parameter (MPa1 / 2), and ôD, ôP and ôH: Hansen solubility parameters (MPa1 / 2).

[0068] The principle of Hansen's theory remains the same as that of Hildebrand mixtures: the closer the solubility parameters are, the more soluble the compounds are. Considering Hansen's parameters, the difference (distance in terms of solubility) between a compound C and a solvent S is expressed as follows:

[0069] [Math.l] A5 = ^(S) -5 d (C)f+ MS) -5„(C) ) 2 + (5„(5)MC) f

[0070] where Aô is the distance between C and S in terms of solubility.

[0071] By representing this equation in the Hansen reference frame (O, ôD, ôP ôH), we obtain an ellipsoid called the “Hansen solubility sphere”. The radius of this, R, represents the solubility limit of compound C, the coordinates of which are of course those of the center of the sphere.

[0072] All solvents whose coordinates are located inside the sphere will be good solvents, and all solvents that are located outside the sphere will be considered non-solvents or bad solvents. Thus, in the case where Aô is less than R, solvent S is a good solvent for compound C at a concentration less than or equal to that measured. Otherwise, solvent S is a bad solvent for compound C at a concentration equal to that measured. As a general rule, the shorter the distance, the better the affinity between the two, and therefore the greater the probability of having a good solvent. Nevertheless, a mixture of solvents whose Aô value is greater than R of each of the solvents can lead to a mixture of Aô less than R allowing solubilization of robinine.

[0073] Robinine has the following Hansen solubility parameters: ôD = 16, ôP= 23 and ôH = 19.

[0074] The mixture of hydrophilic solvents according to the invention is a mixture having an Aô 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 14 and 16.

[0075] Advantageously, the mixture of hydrophilic solvents according to the invention is a mixture having an Aô with robinine between 14 and 16.

[0076] Preferably, the hydrophilic solvent is chosen from alcohols, polyols and their mixtures.

[0077] Among the alcohols, mention may be made of C1-C10 alcohols, more preferably C1-C5 alcohols, such as ethanol, isopropanol, propanol and butanol. Preferably, the alcohol is ethanol.

[0078] The polyol is preferably chosen from polyols having from 2 to 20 carbon atoms, more preferably from 2 to 6 carbon atoms. Preferably, the polyol is chosen from glycerol, propylene glycol, butylene glycol, 1,3-propanediol, pentylene glycol and polyethylene glycols having from 2 to 10 ethylene oxide units. The polyethylene glycol having from 2 to 10 ethylene oxide units is preferably chosen from PEG-6, PEG-8 and mixtures thereof.

[0079] Preferably, the hydrophilic solvent is chosen from C 1 -C 10 alcohols, more preferably from ethanol, glycerol, propylene glycol, butylene glycol, 1,3-propanediol, pentylene glycol, PEG-6, PEG-8 and mixtures thereof.

[0080] 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.

[0081] Preferably, the mixture of hydrophilic solvents according to the invention is a mixture of at least glycerol, propylene glycol, 1,3-propanediol and pentylene glycol.

[0082] Preferably, the mixture of hydrophilic solvents according to the invention also comprises dipropylene glycol.

[0083] 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 (glycerol: propylene glycol: 1,3-propanediol: pentylene glycol) of 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 (glycerol: propylene glycol: 1,3-propanediol: pentylene glycol) of 42: 10: 5: 3.

[0084] The present invention also relates to a cosmetic composition comprising, preferably consisting of: a. a maximum content of 4% by weight relative to the total weight of the composition, of 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, and b. a mixture of glycerol, propylene glycol, 1,3-propanediol and pentylene glycol, preferably in a weight ratio (glycerol: propylene glycol: 1,3-propanediol: pentylene glycol) of 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 (glycerol: propylene glycol: 1,3-propanediol: pentylene glycol) equal to 42: 10:5:3.

[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 (glycerol: propylene glycol: 1,3-propanediol: pentylene glycol: dipropylene glycol) of 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 (glycerol: propylene glycol: 1,3-propanediol: pentylene glycol: dipropylene glycol) of between 42: 10: 5: 3: 24.5.

[0086] The present invention also relates to a cosmetic composition comprising, preferably consisting of: a. a maximum content of 4% by weight relative to the total weight of the composition, of 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, and b. a mixture of glycerol, propylene glycol, 1,3-propanediol, pentylene glycol and dipropylene glycol, preferably in a weight ratio (glycerol:propylene glycol:1,3-propanediol:pentylene glycol:dipropylene glycol) of 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 (glycerol:propylene glycol:1,3-propanediol:pentylene glycol:dipropylene glycol) of between 42:10:5:3:24.5.

[0087] According to one embodiment, the composition comprises from 96% to 99.99% by weight relative to the total weight of the composition of a mixture of at least two hydrophilic solvents, the mixture having an Aô 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 robinine, of between 14 and 16, more preferably from 96% to 99.5% by weight. Water

[0088] The composition according to the invention may comprise water.

[0089] 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 natural thermal or mineral water such as VITTEL water, LUCAS water or LA ROCHE POSAY water.

[0090] The composition preferably comprises at most 10% by weight of water relative to the total weight of the composition, preferably at most 7% by weight, preferably at most 5% by weight, preferably at most 3% by weight, preferably at most 1% by weight.

[0091] Preferably, the composition is completely free of water.

[0092] Preferably, the present invention relates to a cosmetic composition comprising:

[0093] (a) a maximum content of 4% by weight relative to the total weight of composition, robinine or one of its salts, and

[0094] (b) a mixture of at least two hydrophilic solvents, the mixture having an Aô with robinine between 14 and 16.

[0095] The composition according to the invention may also contain ingredients usual in the cosmetic field, such as preservatives, perfumes, fillers, oils, waxes, pasty fatty substances, sun protection filters or UV filters, odor absorbers, coloring materials, basic agents, acids, sequestering agents or active ingredients.

[0096] The quantities of these different ingredients are those conventionally used in the field considered, and for example from 0.01 to 20% of the total weight of the composition. These ingredients, depending on their nature, can be introduced into the fatty phase and / or into the aqueous phase.

[0097] Of course, those skilled in the art will take care to choose the possible compound(s) to be added to the composition according to the invention and their quantities in such a way that the advantageous properties intrinsically attached to the composition in accordance with the invention are not, or not substantially, altered by the envisaged addition.

[0098] The composition in accordance with the invention can be obtained in a conventional manner by a person skilled in the art.

[0099] 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% by weight, and more preferably from 70% to 95% by weight relative to the total weight of the composition of a composition as described above (i.e. comprising ingredients a) and b)). This final composition corresponds in particular to the final commercialized cosmetic product based on robinine. By cosmetically acceptable medium is meant a medium compatible with the skin and / or its appendages.

[0100] The invention also relates to a method for caring for the skin and / or mucous membranes comprising the application of the composition according to the invention or of the final composition according to the invention to the skin and / or mucous membranes.

[0101] The invention also relates to the use of a composition according to the invention or of the final composition according to the invention for the care of the skin and / or mucous membranes.

[0102] The following examples will allow a better understanding of the invention, without however being limiting in nature. The raw materials are named by their chemical or INCI name. The quantities indicated are in % by weight of raw materials relative to the total weight of the composition (% w / w), unless otherwise stated. Examples

[0103] Example 1: preparation of compositions outside the invention with a single solvent

[0104] The compositions in Table 2 were prepared according to the following protocol:

[0105] Robinine is added by sprinkling into the water under magnetic stirring or under Rayneri, until you obtain a clear and transparent solution.

[0106] [Tables 1] Solvent Robinine at 0.50% w / w Robinine at 1% w / w Robinine at 1.50% w / w Robinine at 2% w / w Robinine at 2.50% w / w Robinine at 3% w / w Water insoluble insoluble insoluble insoluble insoluble insoluble

[0107] The results show that robinine is not soluble in water, whatever the concentration tested, in particular from 0.5% to 3% by weight.

[0108] Example 2: Preparation of compositions according to the invention and evaluation with respect to comparative compositions

[0109] Compositions 12A to 12G according to the invention and comparative 12H (marked by a star) were prepared.

[0110] Compositions 12A to 12G according to the invention and comparative 12H each have a weight ratio (glycerol: propylene glycol: 1,3-propanediol: pentylene glycol) equal to 42: 10: 5: 3. [YES] The mixture of solvents of compositions 12A to 12G according to the invention and 12H comparative is a mixture having an Aô with robinine equal to 15.

[0112] The compositions in Table 3 were prepared according to the following protocol:

[0113] - the polyols are mixed,

[0114] - the mixture is heated to 50°C, then

[0115] - robinine is added by sprinkling under magnetic stirring or under Rayneri, until you obtain a clear and transparent solution.

[0116] [T ables 2] Ingredients (% w / w) 12A 12B 12C 12D 12E 12F 12G 12H* Robinin 0.5 1 1.5 2 2.5 3 4 5 Glycerol 69.65 69.30 68.95 68.60 68.25 67.90 67.20 66.50 Propylene glycol 16.58 16.50 16.42 16.33 16.25 16.17 16.00 15.83 1,3-propaned iol 8.29 8.25 8.20 8.17 8.12 8.08 8.00 7.92 Pentylene glycol 4.98 4.95 4.93 4.90 4.88 4.85 4.80 4.75 Appearance at 24h at room temperature Transparent Crystals

[0117] The results show that the mixture of solvents tested makes it possible to solubilize robinine up to a content of 4% by weight relative to the total weight of the composition.

[0118] Example 3: Preparation of compositions according to the invention and evaluation with respect to comparative compositions

[0119] Compositions 13A to 13G according to the invention and comparative compositions 13H and 131 (marked by a star) were prepared.

[0120] Compositions 13A to 13G according to the invention and comparative compositions 13H and 131 each have a weight ratio (glycerol: propylene glycol: 1,3-propanediol: pentylene glycol: dipropylene glycol) equal to 42: 10: 5: 3: 24.5.

[0121] The mixture of solvents of compositions 13A to 13G according to the invention and 13H and 131 comparative is a mixture having an Aô with robinine equal to 14,

[0122] The compositions in Tables 4 and 5 were prepared according to the following protocol:

[0123] - the polyols are mixed,

[0124] - the mixture is heated to 50°C, then

[0125] - robinine is added by sprinkling under magnetic stirring or under Rayneri, until you obtain a clear and transparent solution.

[0126] [Tables3] Ingredients (% w / w) 13A 13B 13C 13D 13E 13F 13G Robinin 0.5 1 1.5 2 2.5 3 4 Glycerol 49.46 49.21 48.96 48.71 48.46 48.22 47.72 Propylene glycol 11.78 11.72 11.66 11.60 11.54 11.48 11.36 1,3-propane diol 5.89 5.86 5.83 5.80 5.77 5.74 5.68 Pentylene glycol 3.52 3.51 3.50 3.48 3.46 3.44 3.41 Dipropylene glycol 28.85 28.70 28.55 28.41 28.27 28.12 27.83 Appearance at 24 hours at room temperature Transparent

[0127] [Tables4] Ingredients (% w / w) 13H* 131* Robinine 7 10 Glycerol 46.22 44.73 Propylene glycol 11.02 10.65 1,3-propanediol 5.50 5.33 Pentylene glycol 3.30 3.20 Dipropylene glycol 26.96 26.09 Appearance at 24h at room temperature Cloudy Opaque

[0128] The results show that the mixture of solvents tested makes it possible to solubilize robinine up to a content of 4% by weight relative to the total weight of the composition.

Claims

Claims

1. Cosmetic composition comprising: (a) a maximum content of 4% by weight relative to the total weight of the composition, of 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.l] (I) in which: -R' and R”, which may be identical or different, preferably different, represent a hydrogen or a (Ci-C4)alkyl group, for example chosen from methyl, ethyl, propyl, isopropyl, butyl and isobutyl, preferably a methyl, or a monosaccharide or a polysaccharide comprising 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 being optionally substituted by a hydroxyl group which must be free, and / or optionally substituted by one or more amine functions which may be protected, said monosaccharide or polysaccharide being optionally substituted on its -CH2OH group by a -C(O)-CO2H 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, selected from coumaroyl, caffeoyl,feruloyl and sinapoyl;, -R”' and R””, identical or different, represent a hydrogen or a (CrC4)alkyl group for example chosen from 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, and (b) a mixture of at least two hydrophilic solvents, the mixture having an Aô 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 14 and 16.

2. A 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 selected from robinine and its salts, preferably in the form [3.

3. A composition according to claim 1, which comprises between 0.1 and 4% by weight of 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 relative to the total weight of the composition, preferably between 0.2 and 4% by weight, preferably between 0.3 and 4% by weight, preferably between 0.5 and 4% by weight.

4. Composition according to one of the preceding claims, in which the hydrophilic solvents are chosen from organic solvents soluble in water at 25°C, preferably chosen from alcohols, polyols and their mixtures.

5. Composition according to claim 4, in which the alcohols are chosen from C 1 -C 10 alcohols, more preferably C 1 -C 5 alcohols, such as ethanol, isopropanol, propanol and butanol, preferably the alcohol is ethanol; and / or the polyols are chosen from polyols having from 2 to 20 carbon atoms, more preferably from 2 to 6 carbon atoms, preferably from glycerol, propylene glycol, butylene glycol, 1,3-propanediol, pentylene glycol and polyethylene glycols having from 2 to 10 ethylene oxide units.

6. Composition according to one of the preceding claims, in which 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 glycerol, propylene glycol, 1,3-propanediol and pentylene glycol and optionally also comprises dipropylene glycol.

7. Composition according to one of the preceding claims, in which the mixture of hydrophilic solvents is a mixture of glycerol, propylene glycol, 1,3-propanediol and pentylene glycol, in a weight ratio (glycerol: propylene glycol: 1,3-propanediol: pentylene glycol) 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 (glycerol: propylene glycol: 1,3-propanediol: pentylene glycol) equal to 42: 10: 5:

3.

8. Composition according to one of the preceding claims, in which the mixture of hydrophilic solvents is a mixture of glycerol, propylene glycol, 1,3-propanediol, pentylene glycol and dipropylene glycol, in a weight ratio (glycerol: propylene glycol: 1,3-propanediol: pentylene glycol: dipropylene glycol) of 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 (glycerol: propylene glycol: 1,3-propanediol: pentylene glycol: dipropylene glycol) of between 42: 10: 5: 3: 24.

5.

9. A composition according to any preceding claim, which comprises water.

10. Composition according to one of the preceding claims, which consists of: a. a maximum content of 4% by weight relative to the total weight of composition, of 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, and b. a mixture of at least two hydrophilic solvents, the mixture having an 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 of between 14 and 16.

11. 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% by weight relative to the total weight of the composition of a composition according to one of claims 1 to 10.

12. Process for caring for the skin and / or mucous membranes comprising the application of a composition according to one of claims 1 to 10 or 11 to the skin and / or the mucous membranes.

13. Use of a composition according to one of claims 1 to 10 or 11 for the care of the skin and / or mucous membranes.