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 between 14 and 16. It also relates to a method for skin and / or mucous membrane care 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 composition weight 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 exhibiting 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 consists 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 includes protecting the body from dehydration and aggressions, particularly external, chemical or mechanical ones.

[0005] There is always a need for new cosmetic compositions with 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 not in water at room temperature. Therefore, it does not, as such, allow for the formulation of stable cosmetic compositions applicable to the skin.

[0008] The formulator is therefore looking for compositions including robinine that are stable and applicable in particular by topical route (i.e. on the skin and / or mucous membranes).

[0009] Such compositions must also include 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 aqueous medium.

[0011] The invention therefore aims to provide a cosmetic composition that meets the requirements of all these problems.

[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 composition weight 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 selected from methyl, ethyl, propyl, isopropyl, butyl and isobutyl, preferably a methyl group, or a monosaccharide or polysaccharide comprising up to 20 sugar units, preferably up to 6 sugar units, in the form of pyranose and / or furanose and of the L and / or D series, said mono- or polysaccharide being optionally substituted by a compulsorily free hydroxyl group, and / or optionally substituted by one or more amine function(s), possibly 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 hydroxyl groups by a (Ci-C4)acyl group, preferably an acetyl group, or by a hydroxycinnamyl fragment, selected from coumaroyl, caféoyl, 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 exhibiting 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 including 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 composition weight 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 exhibiting 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 skin and / or mucous membrane care 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% 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 marketed cosmetic product.

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

[0028] - a "sugar" radical is a monosaccharide or disaccharide radical. Examples include 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 any of their salts or solvates such as hydrates;

[0030] - by "disaccharide" we mean a di-osidic sugar which is a compound made up of of two sugars linked together by O-glycosidic bonds, said compounds being composed of two monosaccharides (also called mono-glycosidics) as defined above, 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 sugar unit being able to be of L or D configuration, as well as one of its salts or solvates such as hydrates. A disaccharide is more particularly a polymer formed of two sugars (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 that represents x - 1;

[0031] - by "transparent composition", for the purposes of the present invention, means 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 equal to 1 NTU.

[0032] NTUs (nephelometric turbidity units) are the units of measurement for the turbidity of a composition. Turbidity measurement is carried out, for example, with a Hach Company model 2100P turbidimeter, 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 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 "accessories" we mean eyelashes, eyebrows, nails, and hair, in particular tinting eyelashes and hair;

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

[0037] - moreover, the expression "at least one" used in this 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) 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:

[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 selected from methyl, ethyl, propyl, isopropyl, butyl and isobutyl, preferably a methyl group, or a monosaccharide or polysaccharide comprising up to 20 sugar units, preferably up to 6 sugar units, in the form of pyranose and / or furanose and of the L and / or D series, said mono- or polysaccharide being optionally substituted by a compulsorily free hydroxyl group, and / or optionally substituted by one or more amine function(s), possibly 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 hydroxyl groups by a (Ci-C4)acyl group, preferably an acetyl group, or by a hydroxycinnamyl fragment, selected from coumaroyl, caféoyl, 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 the form of pyranose and / or furanose and of the L and / or D series, said mono- or polysaccharide having at least one obligatorily free hydroxyl function and / or optionally one or more obligatorily protected amine function(s).

[0045] Advantageously, the monosaccharide is selected 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 designates D-glucose, L-rhamnose, D-xylose, N-acetyl-D-glucosamine or L-fucose, and more preferentially L-rhamnose.

[0046] Advantageously, the polysaccharide containing up to 6 sugar units is selected from D-maltose, D-lactose, D-cellobiose, D-maltotriose, a disaccharide combining a uronic acid selected from D-iduronic acid or D-glucuronic acid with a hexosamine selected 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 can advantageously be selected 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 selected 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 a hydrogen.

[0049] The monosaccharide and / or polysaccharide of R' and / or R' ' can 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 selected 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 the 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 robine or one of its salts, is present in solubilized form in the composition. By "in solubilized form" it is understood 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-rh amnopyranosyloxy)flavone) is the compound of the following formula (II):

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

[0055] Robinine can exist in two anomer forms a and [3.

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

[0057] Robinine can also be presented 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 selected from robinine and its salts in the form [3.

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

[0060] Robinine is marketed for example 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. "Maximum content of 4% by weight" means 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) between 14 and 16.

[0064] Hydrophilic solvents are selected from organic solvents soluble in water at 25°C. The mixture of hydrophilic solvents according to the invention (b) is a mixture presenting 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, ôPet 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] Representing this equation in the Hansen frame (O, ôD, ôP ôH) yields an ellipsoid known as the "Hansen solubility sphere". Its radius, R, represents the solubility limit of compound C, whose coordinates are, of course, those of the center of the sphere.

[0072] All solvents whose coordinates lie inside the sphere will be considered good solvents, and all solvents located outside the sphere will be considered non-solvents or poor solvents. Thus, if 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 poor 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 where the Aô value is greater than the R value of each solvent may result in a mixture with an Aô value less than R, which is sufficient to solubilize robinin.

[0073] Robinine has the following Hansen solubility parameters: ΔD = 16, ΔP = 23 and ΔH = 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, 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 the alcohols in the form of Ci-Cio, more preferably in the form of Ci-C5, such as ethanol, isopropanol, propanol and butanol. Preferably, the alcohol is ethanol.

[0078] The polyol is preferably selected from polyols having from 2 to 20 carbon atoms, more preferably from 2 to 6 carbon atoms. Preferably, the polyol is selected 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 selected from PEG-6, PEG-8, and mixtures thereof.

[0079] Preferably, the hydrophilic solvent is chosen from the alcohols in the Ci-Cio range, 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 of at least three polyols, preferably of 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 includes dipropylene glycol.

[0083] Preferably, the hydrophilic solvent mixture 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 hydrophilic solvent mixture 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 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) of 42:10:5:3.

[0085] Preferably, the hydrophilic solvent mixture 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 hydrophilic solvent mixture 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 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 a mixture of at least two hydrophilic solvents, the mixture having an A0 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 include water.

[0089] The water used may be sterile demineralized water and / or a 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 totally 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, of robinine or one of its salts, and

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

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

[0096] The quantities of these different ingredients are those typically used in the field concerned, 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 oil phase and / or the aqueous phase.

[0097] Of course, a person 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 according to the invention are not, or substantially not, altered by the envisaged addition.

[0098] The composition according to 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 commercial cosmetic product based on robinine. By cosmetically acceptable medium, we mean a medium compatible with the skin and / or its appendages.

[0100] The invention also relates to a method for skin and / or mucous membrane care comprising the application of the composition according to the invention or of the final composition according to the invention on 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 help to better understand the invention, but are not intended to be limiting. Raw materials are named by their chemical or INCI name. Unless otherwise stated, quantities are expressed as a percentage by weight of raw materials relative to the total weight of the composition (% w / w). Examples

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

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

[0105] The robinine is added by sprinkling it into the water under magnetic stirring or under Rayneri, until a transparent and clear solution is obtained.

[0106] [Tables 1] Robinine solvent 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. Insoluble water, insoluble, insoluble, insoluble, insoluble, insoluble, insoluble.

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

[0108] Example 2: Preparation of compositions according to the invention and evaluation against 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 12H comparative 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 com-parative 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 a transparent and clear solution is obtained.

[0116] [Tables2] Ingredients (% w / w) 12A 12B 12C 12D 12E 12F 12G 12H* Robinine 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-propanediol 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 24 hours at room temperature Transparent Crystals

[0117] The results show that the tested solvent mixture allows robinine to be solubilized 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 against comparative compositions

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

[0120] Compositions 13A to 13G according to the invention and 13H and 131 comparative 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 solvent mixture 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 of 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 a transparent and clear solution is obtained.

[0126] [Tables3] Ingredients (% w / w) 13A 13B 13C 13D 13E 13F 13G Robinine 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 tested solvent mixture allows robinine to be solubilized up to a content of 4% by weight relative to the total weight of the composition.

Claims

Demands

1. Cosmetic composition comprising: (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: [Chem.l] (I) in which: -R' and R”, identical or different, preferably different, represent a hydrogen or a (Ci-C4)alkyl group, for example, selected from methyl, ethyl, propyl, isopropyl, butyl, and isobutyl, preferably a methyl group, or a monosaccharide or polysaccharide comprising up to 20 sugar units, preferably up to 6 sugar units, in the form of pyranose and / or furanose and of the L and / or D series, said mono- or polysaccharide being optionally substituted by a compulsorily free hydroxyl group, and / or optionally substituted by one or more amine functions, possibly protected, said monosaccharide or polysaccharide being optionally substituted at its -CH2OH group by a -C(O)-CO2H group, and said monosaccharide or polysaccharide being optionally substituted at one or more of its hydroxyl groups by a (Ci-C4)acyl group, preferably an acetyl group, or by a fragment hydroxycinnamyl, selected from coumaroyl, caffeoyl,feruloyl and sinapoyl; -R”' and R””, identical or different, represent a hydrogen or an (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 exhibiting 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.

2. 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. Composition according to claim 1, comprising 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 any one of the preceding claims, wherein the hydrophilic solvents are selected from organic solvents soluble in water at 25°C, preferably selected from alcohols, polyols and mixtures thereof.

5. Composition according to claim 4, wherein the alcohols are selected from the alcohols in the form of Ci-Cio, more preferably Ci-C5, such as ethanol, isopropanol, propanol and butanol, preferably the alcohol being ethanol; and / or the polyols are selected from the 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 any one of the preceding claims, wherein the mixture of hydrophilic solvents is a mixture of at least two polyols, preferably of at least three polyols, preferably of 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 includes dipropylene glycol.

7. A composition according to any one of the preceding claims, wherein 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 any one of the preceding claims, wherein the hydrophilic solvent mixture 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 40-45:8-12:3-7:2-4:23-26, preferably the hydrophilic solvent mixture 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 42:10:5:3:24.

5.

9. Composition according to any one of the preceding claims, which includes water.

10. Composition according to any one of the preceding claims, consisting 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 A0 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.

11. Final cosmetic composition comprising, in a cosmetically acceptable medium, at least 50% by weight, preferably 60 to 99% by weight, more preferably 70 to 95% by weight relative to the total weight of the composition of a composition according to any one of claims 1 to 10.

12. A method for the treatment of skin and / or mucous membranes comprising the application of a composition according to one of claims 1 to 10 or 11 on the skin and / or mucous membranes.

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