Composition based on robinine and hydrotropic agents

The cosmetic composition, which includes hydrotropic agents and robinine, addresses the solubility issues of robinine in water, enabling the formulation of stable cosmetic products for skin and mucous membrane care.

FR3157205A1Pending Publication Date: 2025-06-27LOREAL SA
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Patent Information

Application Number
FR2023015292
Authority / Receiving Office
FR · FR
Patent Type
Applications
Current Assignee / Owner
Filing Date
2023-12-26
Publication Date
2025-06-27

AI Technical Summary

Technical Problem

Robinine, an active ingredient in cosmetics, is not soluble in water at room temperature, making it difficult to formulate stable cosmetic compositions applicable to the skin.

Method used

A cosmetic composition comprising at least 6% by weight of a hydrotropic agent, such as caffeine and niacinamide, combined with robinine and water, which solubilizes robinine in water, enabling the formulation of stable cosmetic compositions.

Benefits of technology

The composition effectively solubilizes robinine in water, allowing for the creation of stable and applicable cosmetic products, such as lotions, gels, or emulsions, for skin and mucous membrane care.

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Abstract

Composition based on robinine and hydrotropic agents 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) at least 6% by weight relative to the total weight of the composition of at least one hydrotropic agent, and (c) water. 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
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Description

Title of the invention: Composition based on robinine and hydrotropic agents

[0001] The present invention relates to a cosmetic composition comprising: a. 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, b. at least 6% by weight relative to the total weight of the composition of at least one hydrotropic agent, and c. water.

[0002] 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.

[0003] There is always a need for new cosmetic compositions having interesting properties, particularly on the skin.

[0004] Robinine is an interesting active ingredient for this purpose. Indeed, this type of active ingredient is known in cosmetics, for example from application EP4171476.

[0005] 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.

[0006] 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).

[0007] 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.

[0008] In this context, the inventors surprisingly discovered that particular hydrotropic compounds allow the solubilization of robinine in water.

[0009] The invention therefore aims to provide a cosmetic composition responding to these problems.

[0010] Thus, the present invention relates to a cosmetic composition comprising:

[0011] (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 any of their salts or hydrates:

[0012] [Chem.l] (I)

[0013] in which:

[0014] - 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;

[0015] - 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,

[0016] it being understood that R', R”, R” ' and R” ” do not represent H at the same time,

[0017] (b) at least 6% by weight relative to the total weight of the composition of at least one hydrotropic agent, and

[0018] (c) water.

[0019] Preferably, the present invention relates to a cosmetic composition consisting of:

[0020] (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 any of its salts or hydrates,

[0021] (b) at least 6% by weight relative to the total weight of the composition of at least one hydrotropic agent, and

[0022] (c) water.

[0023] 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.

[0024] The invention also relates to the use of a composition according to the invention for the care of the skin and / or mucous membranes.

[0025] 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% relative to the total weight of the composition of a composition as described above (i.e. comprising ingredients a) to c)). This final composition corresponds in particular to the final commercialized cosmetic product.

[0026] The composition according to the invention is preferably in the form of a lotion, an emulsion or a gel.

[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 above, said monosaccharide units comprising at least 5 carbon atoms, preferably 6, particularly the mono-osidic units are linked together in 1,4 or 1,6 in anomer α (alpha) or [3 (beta), each osidic 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 of 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 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 equal to 1 NTU.

[0031] 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).

[0032] 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;

[0033] - by “skin” we mean the skin of the face and / or body, the scalp;

[0034] - by "annexes" we mean eyelashes, eyebrows, nails, and hair, in particular especially eyelashes and hair;

[0035] - 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 ...";

[0036] - moreover, the expression “at least one” used in the present description is equivalent to the expression “one or more”. Compound of formula (I)

[0037] The composition according to the invention comprises 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:

[0038] [Chem.l] (I)

[0039] in which:

[0040] - 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;

[0041] - 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,

[0042] it being understood that R', R”, R” ' and R” ” do not represent H at the same time.

[0043] 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.

[0044] 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.

[0045] 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.

[0046] 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.

[0047] Preferably, R'” and R” ” represent hydrogen.

[0048] 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.

[0049] 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.

[0050] 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.

[0051] 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.

[0052] Robinin (C33H40O19) (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-mannopyranosyl)oxy]-5-hydroxy-2-(4-hydroxyphenyl)-4h-l-benzopyran-4-one) is the compound of formula (I) below:

[0053] [Chem.2] OH 0„ A Xk Ja >! i laughed \Orl3 / s A V—f JO OH OH OH 0 O----: HC r-0 I HOa-O VH / Oh Oh Oh (II)

[0054] Robinine can exist in two forms of anomers α and [3.

[0055] The compound of formula (I) is the [3] anomer of robinine.

[0056] Robinine can also be present in salt form.

[0057] Preferably, the composition according to the invention comprises robinine or one of its salts in the form [3. 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 form [3.

[0058] 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).

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

[0060] Preferably, the composition comprises between 0.1 and 10% 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, preferably of robinine or one of its salts, relative to the total weight of the composition, preferably between 0.2 and 8% by weight, preferably between 0.3 and 5% by weight, preferably between 0.4 and 4% by weight, and more preferably between 0.4 and 1% by weight. Hydrotropic agent

[0061] The composition according to the invention comprises at least 6% by weight relative to the total weight of the composition of at least one hydrotropic agent.

[0062] Preferably, the composition according to the invention comprises at least 6% by weight relative to the total weight of the composition of at least two hydrotropic agents.

[0063] Preferably, the hydrotropic agents are cosmetically acceptable hydrotropic agents.

[0064] By "hydrotrope" or "hydrotropic agent" is meant a water-soluble compound which has an amphiphilic molecular structure and which has the capacity to considerably increase the solubility of poorly water-soluble organic molecules.

[0065] Hydrotropes are similar to surfactants, but are distinguished by their hydrophobic part, which is shorter and does not allow spontaneous self-aggregation to occur. Unlike surfactants, these compounds do not have a critical micellar concentration.

[0066] Among the hydrotropic 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 monoglycol sulfate, 4-aminobenzoic acid HCl, sodium cumene sulfonate, N,N-diethylnicotinamide, N-picolylnicotinamide, N-allylnicotinamide, 2-methacryloyloxyethyl phospho-rylcholine, resorcinol, urea, hydroxyethyl 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 isoniazid.

[0067] A list of hydrotropes is detailed in the following works: Lee J. et al, "Hy- drotropic Solubilization of Paclitaxel: Analysis of Chemical Structures for Hy-drotropic Property", Pharmaceutical Research, Vol. 20, No. 7, 2003, Lee S. et al, "Hy-drotropic Polymers: Synthesis and Characterization of Polymers Containing Picolylni-cotinamide Moieties", Macromolecules, 36, 2248-2255, 2003, and Hodgon TK, Kaler EW, "Hydrotropic Solutions", Current Opinion in Colloid and Interface Science,12, 121-128,2007.

[0068] Cosmetically acceptable hydrotropes designate hydrotropes which are compatible with a cosmetic application, i.e. an application to the skin, mucous membranes and / or appendages.

[0069] Preferably, the appropriate hydrotrope according to the invention is chosen from the following hydrotropes and their mixtures:

[0070] [Tables 1] Name Structure Niacinamide (or nicotinamide) "TT O xnh2 Caffeine HgC-^ N CT î / CH3 JL J ch3 Urea H2hT Q Sodium PCA OH c NaH î Sodium Salicylate Na HOX 0\ L >0 Hydroxyethyl urea

[0071] Preferably, the composition according to the invention comprises at least one hydrotropic agent chosen from caffeine, niacinamide and their mixtures.

[0072] Preferably, the composition according to the invention comprises a mixture of caffeine and niacinamide.

[0073] Preferably, caffeine and niacinamide are present in the composition according to the invention in a caffeine:niacinamide weight ratio of between 1:1 and 1:2.

[0074] Preferably, the amount of hydrotropic agent(s) in the composition according to the invention is between 6 and 20% by weight relative to the total weight of the com- position, preferably between 6 and 15% by weight, preferably between 6 and 10% by weight.

[0075] Preferably, the weight ratio of hydrotropic 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 12:1.

[0076] Preferably, the weight ratio of hydrotropic agent(s): robinine in the composition according to the invention is at least 12:1. Water

[0077] The composition according to the invention comprises water.

[0078] 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.

[0079] The composition preferably comprises at least 30% by weight, preferably at least 50% by weight, preferably at least 60% by weight, preferably at least 70% by weight.

[0080] The composition preferably comprises from 15% to 98% by weight of water relative to the total weight of the composition, more preferably from 30% to 95% by weight, even more preferably from 50% to 90% by weight.

[0081] 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.

[0082] 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.

[0083] 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.

[0084] The composition in accordance with the invention can be obtained in a conventional manner by a person skilled in the art.

[0085] The invention also relates to a final cosmetic composition comprising, in a cosmetically acceptable medium, at least 50% by weight relative to the total weight of the composition of a composition as described previously (i.e. comprising ingredients a), b) and c)), preferably from 60 to 99% by weight, more preferably preferably from 70 to 95% by weight. The final composition corresponds in particular to the final commercialized cosmetic product, based on robinine. By cosmetically acceptable medium, we mean a medium compatible with the skin and / or its appendages.

[0086] 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.

[0087] 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.

[0088] 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

[0089] Example 1: Preparation of compositions according to the invention and evaluation with respect to comparative compositions

[0090] Comparative compositions A, B, C and D and E, F, G and H according to the invention were prepared.

[0091] Comparative compositions A, B, C and D have a quantity of hydrotropic agents (i.e. caffeine and niacinamide) strictly less than 6% by weight relative to the total weight of the composition.

[0092] Compositions E, F, G and H according to the invention have a quantity of hydrotropic agents greater than or equal to 6% by weight relative to the total weight of the composition.

[0093] The compositions in Table 2 were prepared according to the following protocol:

[0094] - a solution of hydrotropes is made by mixing caffeine and niacinamide in the water, then

[0095] - robinine is solubilized by sprinkling in the hydrotrope solution under magnetic stirring and heated to a maximum temperature of 50°C.

[0096] The niacinamide used is Niacinalide PC® marketed by DSM NU-TRITIONAL PRODUCTS.

[0097] The caffeine used is CAFFEINE POWDER® marketed by CSPC Innovation Pharmaceutical.

[0098] [Tables2] Comparative compositions Compositions according to the invention Ingredients (% w / w) ABCDEFGH Niacinami - 1.5 2.5 2.75 3 3.5 5 4 Caffeine - 1.5 2.5 2.75 3 3.5 5 2 Robinin 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 Water Qsp 100 Qsp 100 Qsp 100 Qsp 100 Qsp 100 Qsp 100 Qsp 100 QSP 100 Appearance at 24 hours at room temperature Crystal X Crystal

[0099] The results show that robinine is soluble in water when the overall quantity of hydrotropic agents in the composition is greater than or equal to 6% by weight relative to the total weight of the composition.

[0100] On the contrary, robinine is not soluble in water when the overall quantity of hydrotropic agents in the composition is less than 6% by weight relative to the total weight of the composition.

[0101] Example 2: preparation of a composition according to the invention in gel form

[0102] The composition described in Table 3 below is prepared according to the following protocol:

[0103] - Phase A is prepared by mixing the niacinamide in a portion of the water for 2 minutes at 40°C, then adding the caffeine and mixing for another 20 minutes at 40°C,

[0104] - Robinine (B) is then solubilized in the mixture,

[0105] - The compounds of phase C are added and mixed for 3 minutes at 230 rpm,

[0106] - The compounds of phase D are added by mixing at 230 rpm and heating at 40°C for 5 min until a smooth, shiny gel is obtained.

[0107] - Water is added and mixed for 2 minutes at 500 rpm.

[0108] [Tables3] Ingredients Concentration (% w / w) Phase Niacinamide (Niacinalide PC® from DSM NUTRITIONAL PRODUCTS) 4 A Caffeine (CAFFEINE POWDER® from CSPC Innovation Pharmaceutical) 2 A Water Qsp 100 A Robinine 0.5 B Hydroxyacetophenone 0.5 C Caprylyl glycol 0.5 C Sodium polyacrylate (Cosmedia SP from BASF) 0.125 D Ammonium polyacryloyl-dimethyl taurate (HOSTACERIN AMPS from CLARIANT) 0.375 D Appearance at 24h at room temperature Translucent, slightly pale yellow gel, without crystals pH = 6.5 Viscosity at 30s = 15 poises Viscosity at 10 min = 15 poises

[0109] The viscosity is measured with a Rhéomat RM180 mobile 3, at room temperature (approximately 20°C). The viscosity value of the composition is recorded at 30 seconds and 10 minutes.

[0110] The composition obtained is a translucent gel, which is pleasant to apply to the skin, and in which the robinine has been well solubilized.

Claims

Claims

1. 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.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 function(s) 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, (b) at least 6% by weight relative to the total weight of the composition of at least one hydrotropic agent, and (c) water.

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 or 2, which comprises between 0.1 and 10% 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 8% by weight, preferably between 0.3 and 5% by weight, preferably between 0.4 and 4% by weight.

4. Composition according to one of the preceding claims, which comprises at least two hydrotropic agents.

5. Composition according to one of the preceding claims, in which the quantity of hydrotropic agent(s) is between 6 and 20% by weight relative to the total weight of the composition, preferably between 6 and 15% by weight, preferably between 6 and 10% by weight.

6. Composition according to one of the preceding claims, in which the weight ratio of hydrotropic 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 hydrotropic agent(s): robinine, is at least 12:

1.

7. Composition according to one of the preceding claims, which comprises at least one hydrotropic agent chosen from niacinamide, caffeine, urea, sodium PCA, sodium salycilate, hydroxyethyl urea and mixtures thereof.

8. Composition according to one of the preceding claims, which comprises at least one hydrotropic agent chosen from caffeine, niacinamide and their mixtures.

9. Composition according to one of the preceding claims, which comprises a mixture of caffeine and niacinamide in a caffeine:niacinamide weight ratio of between 1:1 and 1:

2.

10. Composition according to one of the preceding claims, which comprises from 15% to 98% by weight of water relative to the total weight of the composition, preferably from 30% to 95% by weight, preferably from 50% to 90% by weight.

11. Composition according to one of the preceding claims, in the form of a lotion, an emulsion or a gel.

12. 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 11.

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

14. Use of a composition according to one of claims 1 to 11 or 12 for the care of the skin and / or mucous membranes.

Citation Information

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