FR3127399A1 - O/W emulsion with C-glycoside and specific surfactants - Google Patents

Abstract

O/W emulsion with C-glycoside and specific surfactants The present invention relates to a composition in the form of an oil-in-water (O/W) emulsion, in particular cosmetic, comprising a C-glycoside and a mixture of specific surfactants, as well as that the uses of this composition. Figure for the abstract: none

Description

O/W emulsion with C-glycoside and specific surfactants

The present invention relates to a composition in the form of an oil-in-water (O/W) emulsion, in particular cosmetic, comprising a C-glycoside and a mixture of specific surfactants, as well as the uses of this composition.

Biologically active molecules are commonly used in cosmetic products: their function is to have a biological action on the skin. In this respect, hydrophilic active agents, for example of the C-glycoside derivative type, prove to be particularly advantageous. In particular, these compounds are effective in treating the problems of skin aging.

In order to increase their effect, there is a need to increase the penetration into the skin of such active agents. In addition, there is a need for homogeneous and stable care compositions containing such active agents, chosen in particular from C-glycosides, in particular C-beta-D-xylopyranoside-2-hydroxy-propane, which have a stable viscosity. over time.

In particular, compositions comprising such active agents, chosen in particular from C-glycosides, in particular C-beta-D-xylopyranoside-2-hydroxy-propane, formulated in an emulsion based on the combination of an alkylpolyglycoside and an acylamino acid such as disodium stearoyl glutamate, generally exhibit non-optimized properties. In particular, a drop of 30 points in the viscosity is observed during the Rheomat measurements between the start of the measurement and the measurement at 10 minutes, during the measurements at room temperature and at 24 hours after manufacture.

There is therefore a need for such compositions, which are stable over time, and without a drop in viscosity observed on measurement.

Surprisingly, the applicant has discovered that the addition of a particular gemini surfactant, in an emulsion based on C-glycoside and a combination of alkylpolyglycoside and acylamino acid such as disodium stearoyl glutamate, makes it possible to reduce this drop in viscosity, both at room temperature and also at 45°C. Such an addition also increases the penetration of C-glycoside into the skin.

The subject of the present invention is therefore a composition in the form of an oil-in-water (O/W) emulsion, in particular cosmetic and/or dermatological, comprising:

• at least one C-glycoside,
• at least one C8-C30 alkyl(poly)glycoside,
• at least one acylamino acid, and
• at least one twin surfactant.

The present invention also relates to the use, in particular cosmetic use, of a composition according to the invention for the care of keratin materials.

The present invention also relates to a cosmetic process for caring for and/or making up keratin materials, comprising the topical application to the keratin materials of the composition according to the invention.

By “keratin materials”, is meant the skin and/or the lips and/or the hair.

The composition according to the invention is a W/O emulsion: it comprises an oily phase dispersed in a continuous aqueous phase.

The constituents of the composition according to the invention are now described in more detail.

C-glycoside

The composition includes at least one C-glycoside.

C-glycoside is a hydrophilic active ingredient. The term “hydrophilic active” means a water-soluble or water-dispersible active capable of forming hydrogen bonds.

Preferably, the composition according to the invention comprises from 0.1% to 15% by weight of at least one C-glycoside, preferentially from 1% to 10% by weight, and preferentially from 2% to 5% by weight of at least one C-glycoside relative to the total weight of the composition.

In particular, the C-glycoside is chosen from the C-glycoside derivatives of general formula (I) below:

(I)

in which :

• R denotes an unsubstituted linear C ₁ -C ₄ , in particular C ₁ -C ₂ , alkyl radical, in particular methyl;
• S represents a monosaccharide chosen from D-glucose, D-xylose, N-acetyl-D-glucosamine or L-fucose, and in particular D-xylose;
• X represents a group chosen from -CO-, -CH(OH)-, -CH(NH ₂ )-, and preferably a -CH(OH)- group;

as well as their cosmetically acceptable salts, their solvates such as hydrates and their optical isomers.

By way of non-limiting illustration of the C-glycosides of formula (I) more particularly suitable for the invention, mention may be made in particular of the following compounds:

• C-beta-D-xylopyranoside-n-propane-2-one;
• C-alpha-D-xylopyranoside-n-propane-2-one;
• C-beta-D-xylopyranoside-2-hydroxy-propane;
• C-alpha-D-xylopyranoside-2-hydroxy-propane;
• 1-(C-beta-D-glucopyranosyl)-2-hydroxy-propane;
• 1-(C-alpha-D-glucopyranosyl)-2-hydroxy-propane;
• 1-(C-beta-D-glucopyranosyl)-2-amino-propane;
• 1-(C-alpha-D-glucopyranosyl)-2-amino-propane;
• 3'-(acetamido-C-beta-D-glucopyranosyl)-propane-2'-one;
• 3'-(acetamido-C-alpha-D-glucopyranosyl)-propan-2'-one;
• 1-(acetamido-C-beta-D-glucopyranosyl)-2-hydroxyl-propane;
• 1-(acetamido-C-beta-D-glucopyranosyl)-2-amino-propane;
• as well as their cosmetically acceptable salts, their solvates such as hydrates and their optical isomers.

Preferably, C-beta-D-xylopyranoside-2-hydroxy-propane or C-alpha-D-xylopyranoside-2-hydroxy-propane is used, and better still C-beta-D-xylopyranoside-2-hydroxy- propane. Preferably, a C-glycoside of formula (I) suitable for the invention may advantageously be C-beta-D-xylopyranoside-2-hydroxy-propane, whose INCI name is HYDROXYPROPYL TETRAHYDROPYRANTRIOL in particular marketed under the name MEXORYL SBB® or MEXORYL SCN® by CHIMEX. Such a C-glycoside can be present in concentrated form, i.e. in a hydrophilic dispersion concentrated at 70% in active material; such a C-glycoside is marketed under the name MEXORYL SCS by NOVEAL. The salts of the C-glycosides of formula (I) suitable for the invention may comprise conventional physiologically acceptable salts of these compounds such as those formed from organic or inorganic acids. By way of example, mention may be made of the salts of mineral acids, such as sulfuric acid, hydrochloric acid, hydrobromic acid, hydriodic acid, phosphoric acid and boric acid. Mention may also be made of the salts of organic acids, which may contain one or more carboxylic, sulphonic or phosphonic acid groups. They may be linear, branched or cyclic aliphatic acids or alternatively aromatic acids. These acids may additionally comprise one or more heteroatoms chosen from O and N, for example in the form of hydroxyl groups. Mention may in particular be made of propionic acid, acetic acid, terephthalic acid, citric acid and tartaric acid.

Acceptable solvates for the compounds described above include conventional solvates such as those formed during the last stage of preparation of said compounds due to the presence of solvents. By way of example, mention may be made of the solvates due to the presence of water or of linear or branched alcohols such as ethanol or isopropanol.

C-glycosides (I) are known from document WO 02/051828.

AlkylC8-C30(poly)glycosides

The composition according to the invention also comprises at least one C8-C30 alkyl(poly)glycoside.

These surfactants can be more particularly represented by the following general formula:

R1O-(R2O)t (G)v

in which R1 represents a linear or branched alkyl and/or alkenyl radical containing approximately from 8 to 30 carbon atoms, an alkylphenyl radical in which the linear or branched alkyl radical contains from 8 to 24 carbon atoms; R2 represents an alkylene radical comprising approximately 2 to 4 carbon atoms; G represents a sugar unit comprising from 5 to 6 carbon atoms; t denotes a value ranging from 0 to 10, preferably 0 to 4, preferably 0 to 3; and v denotes a value ranging from 1 to 15, preferably from 1 to 4.

It should also be noted that each unit of the polysaccharide part of the alkylpolyglycoside can be in the α or β isomeric form, in the L or D form, and the configuration of the saccharide residue can be of the furanoside or pyranoside type.

It is of course possible to use mixtures of alkyl polysaccharides, which may differ from each other by the nature of the alkyl unit carried and/or the nature of the polysaccharide carrier chain.

According to a particular embodiment, the alkyl(poly)glycoside surfactants are compounds of formula described above in which R1 denotes more particularly a saturated or unsaturated, linear or branched alkyl radical comprising from 12 to 24 carbon atoms, t denotes a value ranging from 0 to 3 and more particularly still equal to 0, G can denote glucose, fructose, galactose, maltose, maltotriose, lactose, cellobiose, mannose, ribose, dextran, talose, allose, xylose, levoglucan , cellulose or starch, preferably glucose. The degree of polymerization, i.e. the value of v in the above formula, can range from 1 to 5, preferably from 1 to 4. The average degree of polymerization is more particularly between 1 and 2.5, preferably from 1.05 to 2.5, and more preferably from 1.1 to 2.

The glucosidic bonds between the sugar units are of the 1-6 or 1-4 and preferably 1-4 type.

It is possible in particular to use coco(poly)glucoside (for example MONTANOV 82® and MONTANOV S®), arachidyl(poly)glucoside (for example MONTANOV 202®), Myristyl(poly)glucoside (for example MONTANOV 14®), cetylstearyl(poly)glucoside (for example MONTANOV 68®), C12-C20 alkyl(poly)glucosides (for example MONTANOV L®), isostearyl(poly)glucoside (for example Montanov WO 18®) or octyldodecyl(poly)xyloside (for example FLUIDANOV 20X®).

Preference will be given to cetylstearyl(poly)glucoside (cetearylglucoside) such as the commercial product MONTANOV 68® from SEPPIC.

According to a particular embodiment of the invention, the content of alkyl(poly)glycosides varies from 0.05 to 10% by weight, preferably from 0.1 to 5% by weight, and more preferably from 0. 2 to 1% by weight relative to the total weight of the composition.

Alcohol bold including from 8 to 40 carbon atoms

According to a particular embodiment, the composition according to the invention comprises at least one C8-40 fatty alcohol.

Preferably, the C ₈ -C ₃₀ alkyl(poly)glycoside is mixed with at least one C8-40 fatty alcohol.

By C8-40 fatty alcohol is meant a long-chain aliphatic alcohol comprising from 8 to 40 carbon atoms, and comprising at least one OH hydroxyl group.

Preferably, the fatty alcohols are R-OH structures with R denoting a linear alkyl group, optionally substituted by one or more hydroxy groups, comprising from 8 to 40, better still from 10 to 30, even from 12 to 24 atoms, even better from 14 to 22 carbon atoms.

The fatty alcohols likely to be used can be chosen from, alone or as a mixture, lauryl or lauryl alcohol (1-dodecanol), myristic or myristyl alcohol (1-tetradecanol), cetyl alcohol (1-hexadecanol ), stearyl alcohol (1-octadecanol), arachidyl alcohol (1-eicosanol), behenyl alcohol (1-docosanol), lignoceryl alcohol (1-tetracosanol), ceryl alcohol (1-hexacosanol ), montanyl alcohol (1-octacosanol), and myricyl alcohol (1-triacontanol).

Preferably, the fatty alcohol is chosen from cetyl alcohol, stearyl alcohol, arachidyl alcohol, behenyl alcohol and mixtures thereof, and even more preferably from cetyl alcohol, stearyl alcohol, alcohol behenyl and mixtures thereof.

Preferably, the fatty alcohol(s) are present in concentrations ranging from 0.01% to 10% by weight, preferably from 0.1% to 5% by weight, and more preferably from 0.2% to 3% by weight. weight, relative to the total weight of the composition.

Acylamino acid

The composition according to the invention also comprises at least one acylamino acid.

As acylamino acids, mention may be made, for example, of sodium cocoylglycinate marketed by the company Ajinomoto under the name Amilite GCS-12, sodium cocoylglycinate marketed by the company Ajinomoto under the name Amilite GCK-12, disodium cocoyl glutamate marketed by the Ajinomoto under the name Amisoft ECS-22SB, sodium lauroyl glutamate marketed by Ajinomoto under the name Amisoft LS11, sodium lauroyl sarcosinate marketed by Seppic under the name ORAMIX L 30, sodium and disodium stearoyl glutamate marketed by the company Ajinomoto under the names Amisoft HS21 P and HS11 Pf and the sodium cocoyl sarcosinate marketed by the company ZSCHIMMER & SCHWARZ under the name Protelan LS 9011/C.

Mention may also be made of the sodium salt of oat lauroyl amino acids such as Proteol OAT marketed by the company Seppic or the compound bearing the INCI name sodium cocoyl amino acids such as Proteol SAV 5OS from Seppic.

The amino acid derivatives can be chosen, for example, from sarcosinates and in particular acylsarcosinates, such as sodium lauroyl sarcosinate marketed under the name SARKOSYL NL 97® by the company Ciba or marketed under the name ORAMIX L 30® by the company Seppic, myristoyl sodium sarcosinate, marketed under the name NIKKOL SARCOSINATE MN® by the company Nikkol, sodium palmitoyl sarcosinate, marketed under the name NIKKOL SARCOSINATE PN® by the company Nikkol; alaninates such as sodium N-lauroyl-N-methylamidopropionate, marketed under the name SODIUM NIKKOL ALANINATE LN 30® by the company Nikkol or marketed under the name ALANONE ALE®, by the company Kawaken, and N-lauroyl N-methylalanine triethanolamine, marketed under the name ALANONE ALTA® by the company Kawaken; aspartates such as the mixture of N-lauroylaspartate of triethanolamine and of N-myristoylaspartate of triethanolamine, marketed under the name ASPARACK® by the company Mitsubishi; the citrates.

Mention may also be made of the alkaline salts of acyl (C10-C22) glutamic acids, preferably an alkaline salt of acyl (C12-C20) glutamic acids, and for example an alkaline salt of acyl (C16-C10) glutamic acids. The alkaline salts are, for example, sodium salts, potassium salts and lithium salts, and preferably sodium salts. It may in particular be one of the alkaline salts of stearoyl glutamic acid, lauroyl glutamic acid, acyl C16 glutamic acid, myristoyl glutamic acid, cocoyl glutamic acid or glutamic hydrogenated tallow acyl acid.

Preferably, the acylamino acid is chosen from sodium stearoyl glutamate, disodium stearoyl glutamate, potassium stearoyl glutamate, sodium lauroyl glutamate, disodium lauroyl glutamate, potassium lauroyl glutamate, sodium cocoyl glutamate, sodium hydrogenated tallow acyl glutamate, and mixtures thereof, and preferably sodium stearoyl glutamate.

By way of illustration, mention may be made, for example, of the disodium steroyl glutamate marketed by the company AJINOMOTO under the reference AMISOFT HS 11 PF®.

Preferably, the acylamino acid is present in concentrations ranging from 0.01% to 15% by weight, preferably from 0.1% to 10% by weight, and more preferably from 0.2% to 1% by weight, relative to the total weight of the composition.

Geminate surfactant

The composition in accordance with the invention comprises at least one geminal surfactant.

By “geminated surfactant”, is meant a surfactant comprising at least two hydrophilic heads linked together by a spacer, and at least two hydrophobic tails, each hydrophobic tail being linked to a hydrophilic head. The spacer can be polar or apolar, flexible or rigid, short or long. The hydrophilic heads can be anionic, cationic or nonionic. In particular, the geminal surfactant comprises two hydrophilic heads linked together by a spacer, and two hydrophobic tails.

Preferably, the geminal surfactant is chosen from the compounds of the following chemical formula (A) and (B), as well as their stereoisomers:

in which :

Y' independently represents a carboxylic acid group or an alkali salt of a carboxylic acid group such as a sodium salt of a carboxylic acid group;

j1, k1, j2 and k2 represent an integer such that (j1, k1, j2, k2) = (2, 0, 2, 0), (2, 0, 0, 2), (0, 2, 2, 0 ) or (0, 2, 0, 2); And

l represents an integer ranging from 6 to 16, preferably from 8 to 14, and advantageously from 10 to 12,

And

in which :

R1 and R3 denote, independently of one another, an alkyl radical having from 1 to 25 carbon atoms;

R2 denotes a spacer consisting of a linear or branched alkylene chain having from 1 to 12 carbon atoms;

X and Y denote, independently of each other, a -(C2H4O)a-(C3H6O)bZ group where

Z denotes a hydrogen atom or a -CH2-COOM, -SO3M, -P(O)(OM)2, -C2H4-SO3M, -C3H6-SO3M or -CH2(CHOH)4CH2OH radical, where M represents H or an alkaline or alkaline-earth or ammonium or alkanolammonium ion,

a ranges from 0 to 15,

b goes from 0 to 10, and

the sum of a + b ranges from 1 to 25; And

n ranges from 1 to 10.

Preferably, the composition in accordance with the invention comprises at least one geminal surfactant of chemical formula (A), or one of its stereoisomers:

in which :

Y' independently represents a carboxylic acid group or an alkali salt of a carboxylic acid group such as a sodium salt of a carboxylic acid group;

j1, k1, j2 and k2 represent an integer such that (j1, k1, j2, k2) = (2, 0, 2, 0), (2, 0, 0, 2), (0, 2, 2, 0 ) or (0, 2, 0, 2); And

l represents an integer ranging from 6 to 16, preferably from 8 to 14, and advantageously from 10 to 12.

According to a particular embodiment of the invention, in formula (A), l represents an integer ranging from 8 to 12, j1 = j2 = 0, and k1 = k2 = 2.

Preferably, in formula (A), Y' represents -COONa, j1 = j2 = 0, k1 = k2 = 2; and l = 10.

As examples of geminal surfactants of formula (A), mention may be made of sodium lysine dilauramidoglutamide, sodium lysine dimyristoylglutamide and sodium lysine distearoylglutamide. Sodium lysine dilauramidoglutamide is particularly preferred. Sodium dilauramidoglutamide lysine is marketed by Asahi Kasei Chemicals under the names PELLICER L-30, PELLICER LB-30G and PELLICER LB-10.

The geminal surfactant(s) of formula (A) is (are) described in particular in application WO 2004/020394.

The composition in accordance with the invention may alternatively comprise at least one geminal surfactant of chemical formula (B):

in which :

R1 and R3 denote, independently of one another, an alkyl radical having from 1 to 25 carbon atoms;

R2 denotes a spacer consisting of a linear or branched alkylene chain having from 1 to 12 carbon atoms;

X and Y denote, independently of each other, a -(C2H4O)a-(C3H6O)bZ group where

Z denotes a hydrogen atom or a -CH2-COOM, -SO3M, -P(O)(OM)2, -C2H4-SO3M, -C3H6-SO3M or -CH2(CHOH)4CH2OH radical, where M represents H or an alkaline or alkaline-earth or ammonium or alkanolammonium ion,

a ranges from 0 to 15,

b goes from 0 to 10, and

the sum of a + b ranges from 1 to 25; And

n ranges from 1 to 10.

The gemini surfactant of formula (B) is preferably such that each of the R1-CO- and R3-CO- groups comprises from 8 to 20 carbon atoms, and preferably denotes a residue of coconut fatty acids (mainly comprising lauric acid and myristic acid).

In addition, this surfactant is preferably such that, for each of the radicals X and Y, the sum of a and b has an average value ranging from 10 to 20 and is preferably equal to 15. A preferred group for Z is the group -SO3M where M is preferably an alkali ion such as a sodium ion.

The spacer R2 advantageously consists of a linear C1-C3 alkylene chain, and preferably of an ethylene chain (CH2CH2).

Finally, n is advantageously equal to 1.

A surfactant of this type is in particular that identified by the INCI name Sodium dicocoylethylenediamine PEG-15 sulfate, having the following structure:

it being understood that PEG represents the group -CH2CH2O-, and cocoyl represents the fatty acid residue of coconut.

This surfactant has a molecular structure very close to that of ceramide-3.

Preferably, the gemini surfactant of formula (B) is used as a mixture with other surfactants, and in particular as a mixture with (a) a C6-C22 (preferably C14-C20) fatty acid ester such as a stearate) and glyceryl, (b) a C6-C22 fatty acid diester (preferably C14-C20 such as a stearate) and citric acid and glycerol (in particular a C6 fatty acid diester -C22 and glyceryl monocitrate), and (c) a C10-C30 fatty alcohol (preferably behenyl alcohol).

Advantageously, the composition according to the invention comprises a mixture of Sodium Dicocoylethylenediamine PEG-15 Sulfate, glyceryl stearate, glyceryl monocitrate stearate and behenyl alcohol.

More preferentially, the geminal surfactant of formula (B) represents from 10 to 20% by weight, and advantageously 15% by weight; the C6-C22 fatty acid glyceryl ester represents from 30 to 40% by weight, advantageously 35% by weight; the C6-C22 fatty acid diester of citric acid and glycerol represents from 10 to 20% by weight, advantageously 15% by weight; and the C10-C30 fatty alcohol represents from 30 to 40% by weight, advantageously 35% by weight, relative to the total weight of the mixture of surfactants containing the geminal surfactant.

Advantageously, the composition according to the invention comprises a mixture of 10 to 20% (in particular 15%) by weight of Sodium Dicocoylethylenediamine PEG-15 Sulfate, from 30 to 40% (in particular 35%) by weight of glyceryl stearate, from 10 to 20% (in particular 15%) by weight of glyceryl monocitrate stearate, from 30 to 40% (in particular 35%) by weight of behenyl alcohol, relative to the total weight of the mixture of surfactants containing the surfactant geminate.

As a variant, the gemini surfactant of formula (B) can be used mixed with an anionic surfactant such as a salt of lauric acid ester and of lactyl lactate, such as sodium lauroyl lactylate. In this case, the geminal surfactant preferably represents from 30 to 50% by weight, and the anionic surfactant represents from 50 to 70% by weight, relative to the total weight of the mixture of surfactants.

The geminal surfactant of formula (B) can be used, for example, in a mixture with other surfactants in the form of the products marketed by the company SASOL under the names CERALUTION®, and in particular the following products:

Ceralution® H: Behenyl Alcohol, Glyceryl Stearate, Glyceryl Stearate Citrate and Sodium Dicocoylethylenediamine PEG-15 Sulfate,

Ceralution® F: Sodium Lauroyl Lactylate and Sodium Dicocoylethylenediamine PEG-15 Sulfate,

Ceralution® ES: Disodium Ethylene Dicocamide PEG-15 Disulfate and Ceteareth-25, or

Ceralution® C: Aqua, Capric/Caprylic triglyceride, Glycerin, Ceteareth-25, Sodium Dicocoylethylenediamine PEG-15 Sulfate, Sodium Lauroyl Lactylate, Behenyl Alcohol, Glyceryl Stearate, Glyceryl Stearate Citrate, Gum Arabic, Xanthan Gum, Phenoxyethanol, Methylparaben, Ethylparaben, Butylparaben, Isobutylparaben (INCI names).

The geminal surfactant represents from 3 to 50% of the weight of these mixtures.

The twin surfactant(s) may be present in the composition in an amount of active ingredient ranging from 0.01 to 4% by weight, preferably from 0.05 to 1% by weight, preferably from 0.07 to 0.8 % by weight relative to the total weight of the composition.

Aqueous phase

The composition in accordance with the invention comprises at least one aqueous phase.

The aqueous phase comprises at least water. Depending on the pharmaceutical form of the composition, the amount of aqueous phase can range from 1 to 99% by weight, preferably from 5 to 98% by weight, better still from 30 to 95% by weight, and even better still from 40 to 80% by weight relative to the total weight of the composition.

The amount of water can represent all or part of the aqueous phase, and it is generally at least 30% by weight relative to the total weight of the composition, preferably at least 40% by weight, better still at least 50 % in weight.

The aqueous phase may comprise at least one organic solvent which is miscible with water at ambient temperature (25° C.) such as, for example, substantially linear or branched lower mono-alcohols having from 2 to 6 carbon atoms, such as ethanol, propanol, butanol, isopropanol, isobutanol; polyols having in particular from 2 to 20 carbon atoms, preferably from 2 to 6 carbon atoms, such as glycerin, propylene glycol, isoprene glycol, butylene glycol, pentylene glycol, hexylene glycol, propylene glycol, glycerol, sorbitol, polyethylene glycols, polypropylene glycols, and mixtures thereof.

The composition can also comprise at least one polymer, in particular hydrophilic. Such a polymer is preferably a water-soluble or water-dispersible polymer (homo- or copolymer) of AMPS®.

The water-soluble or water-dispersible AMPS® polymers preferably have a molar mass ranging from 50,000 g/mole to 10,000,000 g/mole, preferably from 80,000 g/mole to 8,000,000 g/mole, and even more more preferably from 100,000 g/mole to 7,000,000 g/mole.

As water-soluble or water-dispersible homopolymers of AMPS suitable for the invention, mention may be made, for example, of the crosslinked or non-crosslinked polymers of sodium 2-acrylamido-2-methyl propane sulfonate acid such as that used in the commercial product SIMULGEL 800 (name CTFA: Sodium Polyacryloyldimethyl Taurate), crosslinked polymers of ammonium 2-acrylamido-2-methyl propane sulfonate (INCI name: AMMONIUM POLYACRYLDIMEHYLTAURAMIDE) such as the product sold under the trade name HOSTACERIN AMPS® by the company Clariant.

As water-soluble or water-dispersible copolymers of AMPS in accordance with the invention, mention may be made, for example:

- sodium acrylamide/acrylamido-2-methyl propane sulfonate crosslinked copolymers such as that used in the commercial product SEPIGEL 305 (CTFA name: POLYACRYLAMIDE/C13-C14 ISOPARAFFIN/LAURETH-7) or that used in the commercial product sold under the name SIMULGEL 600 (CTFA name: ACRYLAMIDE/SODIUM ACRYLOYLDIMETHYLTAURATE/ISOHEXADECANE/POLYSORBATE-80) by the company SEPPIC;

- copolymers of AMPS® and vinylpyrrolidone or vinylformamide such as that used in the commercial product sold under the name ARISTOFLEX AVC® by the company CLARIANT (CTFA name: AMMONIUM ACRYLOYLDIMETHYLTAURATE/VP COPOLYMER) but neutralized with soda or potash ;

- copolymers of AMPS® and sodium acrylate, such as for example the AMPS/sodium acrylate copolymer such as that used in the commercial product sold under the name SIMULGEL EG® by the company SEPPIC or under the trade name SEPINOV EM under (CTFA name: HYDROXYETHYL ACRYLATE/SODIUM ACRYLOYLDIMETHYL TAURATE COPOLYMER);

- AMPS® and hydroxyethyl acrylate copolymers, such as for example the AMPS®/hydroxyethyl acrylate copolymer such as that used in the commercial product sold under the name SIMULGEL NS® by the company SEPPIC (CTFA name: HYDROXYETHYL ACRYLATE/SODIUM ACRYLOYLDIMETHYLTAURATE COPOLYMER (AND) SQUALANE (AND) POLYSORBATE 60) or like the product marketed under the name COPOLYMER ACRYLAMIDO-2-METHYL PROPANE SULFONATE DE SODIUM/HYDROXYETHYLACRYLATE like the commercial product SEPINOV EMT 10 (INCI name: HYDROXYETHYL ACRYLATE/SODIUM ACRYLOYLDIMETHYL TAURATE COPOLYMER );

- copolymers of AMPS® and ethoxylated cetearyl methacrylate, optionally crosslinked, such as Aristoflex® HMS, which bears the name of copolymer AMPS/ethoxylated cetearyl methacrylate (25 EO) 80/20, crosslinked by trimethylolpropane triacrylate (TMPTA ) or even Ammonium Acryloyldimethyltaurate/Steareth-25 methacrylate crosspolymer in the INCI name.

The amount of polymer can range from 0.2 to 10% by weight, preferably from 0.3 to 5% by weight, better still from 0.5 to 3% by weight relative to the total weight of the composition.

Oil phase

The composition according to the invention comprises at least one oily phase, which preferably comprises at least one oil, in particular a cosmetic oil. It may also contain other fatty substances.

As oils that can be used in the composition of the invention, mention may be made, for example:

- hydrocarbon oils of animal origin, such as perhydrosqualene;

- hydrocarbon oils of vegetable origin, such as liquid triglycerides of fatty acids comprising from 4 to 10 carbon atoms such as triglycerides of heptanoic or octanoic acids or, for example, sunflower, corn, soybean oils, pumpkin, grape seed, sesame, hazelnut, apricot, macadamia, arara, sunflower, castor, avocado, caprylic/capric acid triglycerides such as those sold by the company Stearineries Dubois or those sold under the names Miglyol 810, 812 and 818 by Dynamit Nobel, jojoba oil, shea butter oil;

- synthetic esters and ethers, in particular of fatty acids, such as the oils of formulas R1COOR2 and R1OR2 in which R1 represents the residue of a fatty acid comprising from 8 to 29 carbon atoms, and R2 represents a hydrocarbon chain, branched or not, containing from 3 to 30 carbon atoms, such as for example Purcellin's oil, isononyl isononanoate, isopropyl myristate, isopropyl isostearate, ethyl-2- palmitate hexyl, octyl-2-dodecyl stearate, octyl-2-dodecyl erucate, isostearyl isostearate; hydroxylated esters such as isostearyl lactate, octylhydroxystearate, octyldodecyl hydroxystearate, diisostearylmalate, triisocetyl citrate, heptanoates, octanoates, decanoates of fatty alcohols; polyol esters, such as propylene glycol dioctanoate, neopentyl glycol diheptanoate and diethylene glycol diisononanoate; and pentaerythritol esters such as pentaerythrityl tetraisostearate;

- linear or branched hydrocarbons, of mineral or synthetic origin, such as paraffin oils, volatile or not, and their derivatives, branched chain hydrocarbon oils containing 10 to 20 carbon atoms such as isohexadecane, isododecane, isoparaffins and mixtures thereof, petroleum jelly, polydecenes, hydrogenated polyisobutene such as Parléam® oil;

- natural or synthetic essential oils such as, for example, oils of eucalyptus, lavandin, lavender, vetiver, litsea cubeba, lemon, sandalwood, rosemary, chamomile, savory, walnut nutmeg, cinnamon, hyssop, caraway, orange, geraniol, cade and bergamot;

- fatty alcohols having 8 to 26 carbon atoms, such as cetyl alcohol, stearyl alcohol, mixture of cetyl alcohol and stearyl alcohol (cetylstearyl alcohol), octyldodecanol, 2-butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol, oleyl alcohol or linoleic alcohol;

- partially hydrocarbon and/or silicone fluorinated oils such as those described in document JP-A-2-295912;

- silicone oils such as volatile or non-volatile polymethylsiloxanes (PDMS) with a linear or cyclic silicone chain, liquid or pasty at room temperature, in particular cyclopolydimethylsiloxanes (cyclomethicones) such as cyclohexasiloxane; polydimethylsiloxanes comprising alkyl, alkoxy or phenyl groups, pendent or at the end of the silicone chain, groups having from 2 to 24 carbon atoms; phenyl silicones such as phenyltrimethicones, phenyldimethicones, phenyltrimethylsiloxydiphenylsiloxanes, diphenyl-dimethicones, diphenylmethyldiphenyl trisiloxanes, 2-phenylethyltrimethyl-siloxysilicates, and polymethylphenylsiloxanes; Or

- their mixtures.

The other fatty substances which may be present in the oily phase are, for example, fatty acids comprising from 8 to 30 carbon atoms, such as stearic acid, lauric acid, cetylic acid, palmitic acid and acid oleic; waxes such as lanolin, beeswax, carnauba or candelilla wax, paraffin or lignite waxes or microcrystalline waxes, ceresin or ozokerite, synthetic waxes such as polyethylene waxes, waxes of Fischer-Tropsch; silicone resins such as trifluoromethyl-C1-4-alkyldimethicone and trifluoropropyldimethicone; and silicone elastomers such as the products marketed under the names "KSG" by the company Shin-Etsu, under the names "Trefil", "BY29" or "EPSX" by the company Dow Corning or under the names "Gransil" by the Grant Industries company.

These fatty substances can be chosen in a variety of ways by those skilled in the art in order to prepare a composition having the properties, for example of consistency or texture, desired.

The amount of oily phase can range for example from 1 to 45%, and for example from 10 to 35% by weight relative to the total weight of composition.

According to a particular embodiment, the composition according to the invention also comprises active agents other than C-glycoside and/or cosmetically acceptable excipients.

By "cosmetically acceptable" is meant compatible with the skin and/or its appendages, which has a pleasant color, smell and touch and which does not cause unacceptable discomfort (tingling, tightness, redness), likely to divert the consumer to use this composition.

According to one embodiment, the composition according to the invention may also comprise at least one excipient chosen from preservatives, fillers, coloring materials, perfumes and mixtures thereof.

The filler can be inorganic or organic. The filler can be chosen from synthetic or natural mica; silica powder; talc; polyamide particles and in particular those sold under the name ORGASOL by the company Atochem; polyethylene powders; nylon powders; microspheres based on acrylic copolymers, such as those made of ethylene glycol dimethacrylate/lauryl methacrylate copolymer sold by the company Dow Corning under the name POLYTRAP; expanded powders such as hollow microspheres and in particular the microspheres marketed under the name EXPANCEL by the company Kemanord Plast or under the name MICROPEARL F 80 ED by the company Matsumoto; silicone resin microbeads such as those marketed under the name TOSPEARL by the company Toshiba Silicone; and their mixtures.

These fillers may be present in amounts ranging from 0.1 to 10% by weight and preferably from 0.3 to 5% by weight relative to the total weight of composition.

The invention also relates to the use, in particular cosmetic use, of a composition according to the invention for the care of keratin materials.

The invention also relates to a cosmetic process for caring for and/or making up keratin materials, comprising the topical application to the keratin materials of the composition according to the invention.

The invention also relates to a cosmetic and/or aesthetic care method comprising the topical application to keratin materials of a composition according to the invention.

Concrete, but in no way limiting, examples illustrating the invention will now be given.

In the examples, all the percentages are given by weight, unless otherwise indicated, and the temperature is that of ambient temperature (20° C.) and expressed in degrees Celsius, unless otherwise indicated, and the pressure is atmospheric pressure, unless otherwise indicated.

In the examples, the amounts of the ingredients of the compositions are given in % by weight relative to the total weight of the composition (% w/w).

Example 1: Com parison of the viscosities of a composition cosmetic position according to the invention with a comparative composition

The comparative compositions according to the invention are prepared according to the following protocol:

Formulation with 6-blade rotor with wide slot stator - Cold/hot process:

1- Solubilization at room temperature of phase A; hyaluronic acid (hydrolyzed) is predispersed in the humectant (glycerin) before its introduction into phase A,

2- Heating of phase B to 75°C, addition of fillers (phase B1) just before emulsification,

3- Emulsification at 65°C, to be able to emulsify at a speed of at least 2000 rpm, addition of ammonium polyacryloyldimethyl taurate,

4- Dilution of the formula with the addition of phase C,

5- At a temperature below 40°C, introduce aluminum starch octenylsuccinate (phase F) and hydroxypropyl tetrahydropyrantriol (phase E),

6- Add the polyacrylamide (and) C13-14 isoparaffin (and) laureth-7 (phase D1) under a deflocculator.

Viscosity

The viscosity of the compositions is measured by the following protocol, after 24 hours at room temperature (25° C.), and after 2 months at 45° C.:

The viscosity is measured using a Rhéomat 180, at 25° C., 1 atm., with a spindle 3, the speed of rotation being 200 rpm, at T0 and after 10 minutes (T10), the shear rate being 200 s ^-1 . Viscosity is read off the device in units of deviation (DU).

Phase INCI name Comparative composition
(% w/w) Composition according to the invention
(% w/w) AT Hydrolyzed hyaluronic acid 0.10 0.10 AT Chelating 0.10 0.10 AT SODIUM DILAURAMIDOGLUTAMIDE LYSINE
(Pellicer LB-30G from Asahi Kasei: mixed with butylene glycol and water) - 0.35 (*0.0955% active ingredient) AT ADENOSINE 0.10 0.10 AT Humectant 10.00 10 AT Base for pH 0.05 0.05 A1 Water Qsp 100 Qsp 100 B Stearic acid 0.75 0.75 B Conservative 0.70 0.7 B DIMETHICONE 3.00 3 B OCTYLDODECANOL 1.80 1.8 B Capryloyl salicylic acid 0.30 0.3 B ISOPROPYL ISOSTEARATE 2.70 2.7 B BEHENYL ALCOHOL 1.50 1.5 B CETEARYL ALCOHOL (and) CETEARYL GLUCOSIDE
(Montanov 68® from Seppic) 0.60 0.6 B DISODIUM STEAROYL GLUTAMATE
(Ajinomoto's Amisoft HS 11 PF®) 0.30 0.3 B ISOHEXADECANE 4.60 4.6 B PEG-100 STEARATE 0.20 0.2 B CETYL ALCOHOL 1.70 1.7 B1 NYLON-12 2.00 2 B1 POLYETHYLENE 0.50 0.5 VS Water 30.00 30 D AMMONIUM POLYACRYLOYLDIMETHYL TAURATE 1.20 1.2 D1 POLYACRYLAMIDE (and) C13-14 ISOPARAFFIN (and) LAURETH-7 0.80 0.8 E HYDROXYPROPYL TETRAHYDROPYRANTRIOL
(MEXORYL SBB® from Chimex) 9.00
(*3% in active matter) 9
(*3% in active ingredient) F Starch filler 3.00 3 Viscosity UD mobile 3, after 24 hours at room temperature (25°C) T0: 114UD
T10: 66UD T0: 130UD
T10: 100UD Viscosity UD mobile 3, after 2 months at 45°C T0: 23UD
T10: 21UD T0: 140 UD
T10: 130UD

The results clearly show that only the formula according to the invention has a stable viscosity at T0 and after 10 minutes, whether at room temperature or at 45°C.

E example 2 : Composition cosmetic position according to the invention

The composition according to the invention is prepared according to the protocol of example 1.

Phase INCI Composition according to the invention (% w/w) AT Water Qsp 100 AT CAPRYLYL GLYCOL 0.2 AT Humectant 10 AT SODIUM DILAURAMIDOGLUTAMIDE LYSINE
(Pellicer LB-30G from Asahi Kasei: mixed with butylene glycol and water) 0.35
(*0.0955% in active ingredient) AT Base for pH 0.122 AT Dyes 0.00038 AT ADENOSINE 0.1 AT SODIUM HYALURONATE 0.1 B fatty alcohol 3.2 B PEG-100 STEARATE 0.2 B ISOHEXADECANE 4.6 B DISODIUM STEAROYL GLUTAMATE
(Amisoft HS 11 PF® from Ajinomoto) 0.3 B CETEARYL ALCOHOL (and) CETEARYL GLUCOSIDE
(Montanov 68 ® of Seppic) 0.6 B Stearic acid 0.75 B ISOPROPYL ISOSTEARATE 2.7 B Capryloyl salicylic acid 0.3 B OCTYLDODECANOL 1.8 B DIMETHICONE 3 B Conservative Q's B1 LAUROYL LYSIN 0.38 B1 boron nitride 1.28 VS Water 26.05362 D AMMONIUM POLYACRYLOYLDIMETHYL TAURATE 1.3 D1 POLYACRYLAMIDE (and) C13-14 ISOPARAFFIN (and) LAURETH-7 0.8 G Scent 0.3 G RETINYL PALMITATE 0.15 E ACETYL DIPEPTIDE-1 CETYL ESTER 0.1 E HYDROXYPROPYL TETRAHYDROPYRANTRIOL
(MEXORYL SBB® from Chimex) 9
(*3% in active ingredient) F Starch filler 2.33 H Water 4 H ASCORBYL GLUCOSIDE 0.21 H SODIUM CITRATE 0.074

Claims (14)

Composition in the form of an oil-in-water emulsion, in particular cosmetic and/or dermatological, comprising:
at least one C-glycoside,
at least one C8-C30 alkyl(poly)glycoside,
at least one acylamino acid, and
at least one twin surfactant. Composition according to Claim 1, characterized in that the C-glycoside is chosen from the C-glycoside derivatives of general formula (I) below:
(I)
in which :
R denotes an unsubstituted linear C ₁ -C ₄ , in particular C ₁ -C ₂ , alkyl radical, in particular methyl;
S represents a monosaccharide chosen from D-glucose, D-xylose, N-acetyl-D-glucosamine or L-fucose, and in particular D-xylose;
X represents a group chosen from -CO-, -CH(OH)-, -CH(NH ₂ )-, and preferably a -CH(OH)- group;
as well as their cosmetically acceptable salts, their solvates such as hydrates and their optical isomers,
preferably the C-glycoside is C-beta-D-xylopyranoside-2-hydroxy-propane or C-alpha-D-xylopyranoside-2-hydroxy-propane, and better still C-beta-D-xylopyranoside-2- hydroxy-propane. Composition according to Claim 1 or 2, characterized in that it comprises from 0.1% to 15% by weight of at least one C-glycoside, preferentially from 1% to 10% by weight, and preferentially from 2% to 5% by weight of at least one C-glycoside relative to the total weight of the composition. Composition according to one of Claims 1 to 3, characterized in that the C8-C30 alkyl(poly)glycoside is represented by the following general formula:
R1O-(R2O)t (G)v
in which R1 represents a linear or branched alkyl and/or alkenyl radical containing approximately from 8 to 30 carbon atoms, an alkylphenyl radical in which the linear or branched alkyl radical contains from 8 to 24 carbon atoms; R2 represents an alkylene radical comprising approximately 2 to 4 carbon atoms; G represents a sugar unit comprising from 5 to 6 carbon atoms; t denotes a value ranging from 0 to 10, preferably 0 to 4, preferably 0 to 3; and v denotes a value ranging from 1 to 15, preferably from 1 to 4,
preferably, the C8-C30 alkyl(poly)glycoside is chosen from coco(poly)glucoside, arachidyl(poly)glucoside, Myristyl(poly)glucoside, cetylstearyl(poly)glucoside, C12-C20 alkyl(poly) ) glucosides, isostearyl (poly) glucoside and octyldodecyl (poly) xyloside, preferably the C8-C30 alkyl (poly) glycoside is cetylstearyl (poly) glucoside. Composition according to one of Claims 1 to 4, characterized in that the content of alkyl(poly)glycosides varies from 0.05% to 10% by weight, preferably from 0.1% to 5% by weight, and from more preferably from 0.2% to 1% by weight relative to the total weight of the composition. Composition according to one of Claims 1 to 5, characterized in that the acylamino acid is chosen from sodium cocoylglycinate, sodium cocoylglycinate, disodium cocoyl glutamate, sodium lauroyl glutamate, sodium lauroyl sarcosinate, sodium and disodium stearoyl glutamate, sodium cocoyl sarcosinate, sodium salt of lauroyl amino acids of oats, sodium lauroyl sarcosinate, sodium myristoyl sarcosinate, sodium palmitoyl sarcosinate, N-lauroyl-N-methylamidopropionate sodium, N-lauroyl N-methylalanine triethanolamine, the mixture of N-lauroylaspartate of triethanolamine and N-myristoylaspartate of triethanolamine, the alkaline salts of acyl (C10-C22) glutamic acids and their mixtures, preferably the acylamino acid is chosen from sodium stearoyl glutamate, disodium stearoyl glutamate, potassium stearoyl glutamate, sodium lauroyl glutamate, disodium lauroyl glutamate, potassium lauroyl glutamate, sodium cocoyl glutamate, sodium hydrogenated tallow acyl glutamate , and mixtures thereof, and preferably sodium stearoyl glutamate. Composition according to one of Claims 1 to 6, characterized in that the acylamino acid is present in concentrations ranging from 0.01% to 15% by weight, preferably from 0.1% to 10% by weight, and more preferably from 0.2% to 1% by weight, relative to the total weight of the composition. Composition according to one of Claims 1 to 7, characterized in that the geminal surfactant is chosen from the compounds of the following chemical formula (A) and (B), as well as their stereoisomers:

in which :
Y' independently represents a carboxylic acid group or an alkaline salt of a carboxylic acid group such as a sodium salt of a carboxylic acid group;
j1, k1, j2 and k2 represent an integer such that (j1, k1, j2, k2) = (2, 0, 2, 0), (2, 0, 0, 2), (0, 2, 2, 0 ) or (0, 2, 0, 2); And
l represents an integer ranging from 6 to 16, preferably from 8 to 14, and advantageously from 10 to 12,
And

in which :
R1 and R3 denote, independently of one another, an alkyl radical having from 1 to 25 carbon atoms;
R2 denotes a spacer consisting of a linear or branched alkylene chain having from 1 to 12 carbon atoms;
X and Y denote, independently of each other, a -(C2H4O)a-(C3H6O)bZ group where
Z denotes a hydrogen atom or a -CH2-COOM, -SO3M, -P(O)(OM)2, -C2H4-SO3M, -C3H6-SO3M or -CH2(CHOH)4CH2OH radical, where M represents H or an alkaline or alkaline-earth or ammonium or alkanolammonium ion,
a ranges from 0 to 15,
b goes from 0 to 10, and
the sum of a + b ranges from 1 to 25; And
n ranges from 1 to 10. Composition according to one of Claims 1 to 8, characterized in that the geminal surfactant is of formula (A), preferably chosen from sodium dilauramidoglutamide lysine, sodium dimyristoylglutamide lysine and sodium distearoylglutamide lysine, preferably is sodium lysine dilauramidoglutamide. Composition according to one of Claims 1 to 9, characterized in that the geminal surfactant is present in the composition in an amount of active ingredient ranging from 0.01% to 4% by weight, preferably from 0.05% to 1 % by weight, preferably from 0.07% to 0.8% by weight relative to the total weight of the composition. Composition according to one of Claims 1 to 10, characterized in that it comprises at least one aqueous phase comprising at least water, preferably in an amount of at least 30% by weight relative to the total weight of the composition, preferably at least 40% by weight, better still at least 50% by weight, and optionally at least one organic solvent miscible with water at ambient temperature, preferably chosen from substantially linear or branched lower mono-alcohols having 2 with 6 carbon atoms, polyols having in particular from 2 to 20 carbon atoms and mixtures thereof; preferably it also comprises at least one hydrophilic polymer. Composition according to one of Claims 1 to 11, characterized in that it comprises at least one oily phase, which preferably comprises at least one oil and optionally other fatty substances. Use, in particular cosmetic use, of a composition according to one of Claims 1 to 12 for the care of keratin materials. Cosmetic process for caring for and/or making up keratin materials, comprising the topical application to the keratin materials of the composition according to one of Claims 1 to 12.