FR3152398A3 - ANHYDROUS CARE AND/OR MAKE-UP COMPOSITION OF KERATINOUS MATERIALS - Google Patents

Abstract

ANHYDROUS COMPOSITION FOR CARE AND/OR MAKE-UP OF KERATINOUS MATERIALS The present invention relates to a composition for care and/or makeup of keratinous materials, comprising, a) at least one C-glycoside; b) at least one hydrophilic moisturizer chosen from polyhydric alcohols, which is different from the at least one C-glycoside; c) at least one non-ionic surfactant chosen from fatty acid glyceryl monoesters and fatty acid polyglyceryl esters; and d) at least one wax. The present invention also relates to a cosmetic process for care and/or makeup of keratinous materials, comprising the application to the keratinous materials of the composition according to the present invention. Figure for abstract: none

Description

ANHYDROUS CARE AND/OR MAKE-UP COMPOSITION OF KERATINOUS MATERIALS

The present invention relates to a composition for caring for and/or making up keratinous materials. More particularly, the present invention relates to an anhydrous composition for caring for and/or making up keratinous materials. The present invention also relates to a cosmetic process for caring for and making up keratinous materials.

STATE OF THE ART

Lipsticks have been used for many years to accentuate the positive aspects of the wearer's lips. Lipsticks can alter the wearer's apparent facial features. In addition to altering the shape of the lips, lipsticks can be made in a wide variety of colors and shades to achieve a desired effect or express the wearer's mood.

To date, certain prior art documents relating to solid cosmetic compositions for makeup and/or skin and/or lip care have been published.

• de 5 à 30 % en poids d’une huile apolaire non volatile, ou d’un mélange de celle-ci, par rapport au poids total de la composition,
• de 43 à 90 % en poids de la teneur totale en une huile de silicone non volatile par rapport au poids total de la composition, dans laquelle au moins une desdites huiles de silicone non volatiles est une huile de silicone phénylée non volatile, et
• de 3 à 30 % en poids d’une cire, ou d’un mélange de celle-ci, par rapport au poids total de la composition.

For example, WO 2013/191300 discloses a solid cosmetic composition for makeup and/or care of the skin and/or lips, comprising, in a physiologically acceptable medium, at least one fatty phase comprising:

• from 5 to 30% by weight of a non-volatile apolar oil, or a mixture thereof, relative to the total weight of the composition,
• from 43 to 90% by weight of the total content of a non-volatile silicone oil relative to the total weight of the composition, wherein at least one of said non-volatile silicone oils is a non-volatile phenylated silicone oil, and
• from 3 to 30% by weight of a wax, or a mixture thereof, relative to the total weight of the composition.

Some lipsticks have the disadvantage of not providing enough moisture or hydration. Dry lips often cause fine lines. Throughout the day, the feeling of dry, tight lips can make them uncomfortable to use, especially with matte lipsticks. Much effort has been made to improve this problem.

One solution is to incorporate humectants into some lipsticks.

Some lipsticks may have stability issues (e.g., oil exudation or macroscopic crystallization on the surface of lipsticks) after temperature and/or humidity fluctuation, especially when certain humectants are added into lipsticks, which is considered a quality issue by consumers.

Therefore, there is a need to develop a moisturizing lipstick, which exhibits good stability (i.e., there is no oil exudation or macroscopic crystallization on the surface of the lipsticks).

An object of the present invention is therefore to develop a moisturizing lipstick, which has good stability (i.e. there is no oil exudation or macroscopic crystallization on the surface of the lipsticks).

Another object of the present invention is to propose a cosmetic process for caring for and/or making up keratinous materials, which will provide a moisturizing effect.

1. au moins un C-glycoside ;
2. au moins un hydratant hydrophile choisi parmi les alcools polyhydriques, qui est différent de l’au moins un C-glycoside ;
3. au moins un tensioactif non ionique choisi parmi les monoesters de glycéryle d’acide gras, les esters de polyglycéryle d’acide gras et un mélange de ceux-ci ; et
4. au moins une cire.

Thus, according to a first aspect, the present invention provides a composition for caring for and/or making up keratinous materials, comprising:

1. at least one C-glycoside;
2. at least one hydrophilic moisturizer selected from polyhydric alcohols, which is different from the at least one C-glycoside;
3. at least one non-ionic surfactant selected from fatty acid glyceryl monoesters, fatty acid polyglyceryl esters and a mixture thereof; and
4. at least one wax.

According to a second aspect, the present invention provides a cosmetic process for caring for and/or making up keratinous materials comprising the application of the composition as described above to the keratinous materials.

According to a third aspect, the present invention proposes the use of an anhydrous composition comprising at least one non-ionic surfactant chosen from fatty acid glyceryl monoesters, fatty acid polyglyceryl esters and a mixture thereof, to improve the penetration of a C-glycoside, in particular hydroxypropyl tetrahydropyrantriol, into keratinous materials, in particular the lips.

The inventors have discovered that with the combination of at least one C-glycoside, at least one hydrophilic moisturizer selected from polyhydric alcohols, which is different from the at least one C-glycoside, at least one nonionic surfactant selected from fatty acid glyceryl monoesters, fatty acid polyglyceryl esters and a mixture thereof, and at least one wax, the anhydrous composition according to the present invention can deliver a moisturizing effect and does not have a stability problem for at least 2 months at 4°C, 25°C, 37°C or 45°C.

Other subjects and characteristics, aspects and advantages of the invention will appear even more clearly on reading the description and examples which follow.

DETAILED DESCRIPTION OF THE INVENTION

Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by a person skilled in the art in the field to which the present invention relates. Where the definition of a term in the present invention conflicts with the meaning commonly understood by a person skilled in the art in the field to which the present invention relates, the definition described in the present invention shall apply.

In the following and unless otherwise indicated, the limits of a range of values are included in this range, in particular in the expressions "between...and..." and "from...to...".

Furthermore, the expression "at least one" used in this description is equivalent to the expression "one or more".

Throughout this application, the term "comprising" should be interpreted to encompass all specifically mentioned features as well as optional, additional, and unspecified features. As used herein, the use of the term "comprising" also discloses the embodiment in which no features other than the specifically mentioned features are present (i.e., "consisting of").

In the present invention, all percentages refer, unless otherwise specified, to a percentage by weight.

For the purposes of the present invention, the term "anhydrous" means that the composition according to the present invention contains less than 2% by weight and preferably less than 1% by weight of water relative to the total weight of the composition. Where appropriate, these small amounts of water may be provided by ingredients of the composition which contain them in residual quantity but are not deliberately provided.

As used herein, the term “keratinous material” refers to the skin and lips. “Skin” means all skin of the body, including the scalp. Preferably, the keratinous material is the lips.

Advantageously, the anhydrous composition according to the present invention is solid.

The term "solid" as used herein means that the hardness of the composition at 20°C and atmospheric pressure (760 mmHg) is greater than or equal to 30 Nm ^-1 when measured according to the protocol described below.

The composition whose hardness is to be determined is stored at 20°C for 24 hours before measuring the hardness.

Hardness can be measured at 20°C by the 'cheese wire' method, which involves cross-cutting a rod of product, preferably a circular cylinder, using a rigid tungsten wire 250 µm in diameter, moving the wire relative to the rod at a speed of 100 mm/minute.

The hardness of the samples of compositions of the present invention, expressed in Nm ^-1 , is measured using a DFGS2 tensile testing machine from the company Indelco-Chatillon.

The measurement is repeated three times and then averaged. The average of the three shear values read using the tensile testing machine mentioned above, denoted Y, is given in grams. This average is converted to Newtons and then divided by L, which represents the longest distance traversed by the wire. In the case of a cylindrical rod, L is equal to the diameter (in meters).

Hardness is converted to Nm ^-1 by the equation below:

(Y × 10 ^-3 × 9.8)/L

For measurement at a different temperature, the composition is stored for 24 hours at this new temperature before measurement.

According to this measuring method, the composition according to the present invention preferably has a hardness at 20°C and at atmospheric pressure greater than or equal to 40 Nm ^-1 . Thus, these compositions can be formulated in a standard packaging which does not require any composition support means.

Preferably, the composition according to the present invention has in particular a hardness at 20°C of less than 200 Nm ^-1 , and preferably of less than 160 Nm ^-1 .

1. au moins un C-glycoside ;
2. au moins un hydratant hydrophile choisi parmi les alcools polyhydriques, qui est différent de l’au moins un C-glycoside ;
3. au moins un tensioactif non ionique choisi parmi les monoesters de glycéryle d’acide gras, les esters de polyglycéryle d’acide gras et un mélange de ceux-ci ; et
4. au moins une cire.

The anhydrous composition according to the present invention comprises:

1. at least one C-glycoside;
2. at least one hydrophilic moisturizer selected from polyhydric alcohols, which is different from the at least one C-glycoside;
3. at least one non-ionic surfactant selected from fatty acid glyceryl monoesters, fatty acid polyglyceryl esters and a mixture thereof; and
4. at least one wax.

C-glycoside

According to the first aspect, the composition of the present invention comprises at least one C-glycoside.

Preferably, the C-glycoside is chosen from the compounds of formula (I):
(I)

• R représente un radical alkyle saturé en C₁à C₁₀, en particulier en C₁à C₄qui peut facultativement être substitué par au moins un radical choisi parmi OH, COOH ou COOR''₂, R''₂étant un radical alkyle saturé en C₁-C₄,
• S représente un monosaccharide ou un polysaccharide comprenant jusqu’à 20 motifs sucre, en particulier jusqu’à 6 motifs sucre, sous forme de pyranose et/ou de furanose et des séries L et/ou D, ledit monosaccharide ou polysaccharide pouvant être substitué par un groupe hydroxyle qui est nécessairement libre et facultativement un ou plusieurs groupes fonctionnels amine facultativement protégés, et
• X représente un radical choisi dans les groupes -CO-, -CH(OH)-, -CH(NH₂)-, -CH(NHCH₂CH₂CH₂OH)-, -CH(NHPh)- et –CH(CH₃)- et en particulier un radical –CO-, -CH(OH)- ou –CH(NH₂)- et plus particulièrement un radical –CH(OH)-,

in which:

• R represents a saturated C ₁ to C ₁₀ alkyl radical, in particular C ₁ to C ₄ which may optionally be substituted by at least one radical chosen from OH, COOH or COOR'' ₂ , R'' ₂ being a saturated C ₁ -C ₄ alkyl radical,
• S represents a monosaccharide or polysaccharide comprising up to 20 sugar units, in particular up to 6 sugar units, in the form of pyranose and/or furanose and of the L and/or D series, said monosaccharide or polysaccharide possibly being substituted by a hydroxyl group which is necessarily free and optionally one or more optionally protected amine functional groups, and
• X represents a radical chosen from the groups -CO-, -CH(OH)-, -CH(NH ₂ )-, -CH(NHCH ₂ CH ₂ CH ₂ OH)-, -CH(NHPh)- and –CH(CH ₃ )- and in particular a radical –CO-, -CH(OH)- or –CH(NH ₂ )- and more particularly a radical –CH(OH)-,

the S-CH ₂ -X bond represents a C-anomeric bond, which can be α or β,

as well as their physiologically acceptable salts, their solvates, such as hydrates and their geometric isomers; and one of their mixtures.

The C-glycosides used for implementing the invention are in particular those for which R denotes a saturated linear alkyl radical of C ₁ to C ₆ , in particular of C ₁ to C ₄ , preferentially of C ₁ to C ₂ and more preferentially, a methyl radical.

Among the alkyl groups suitable for implementing the invention, mention may be made in particular of methyl, ethyl, isopropyl, n-propyl, n-butyl groups,
t-butyl, isobutyl, sec-butyl, pentyl, n-hexyl, cyclopropyl, cyclopentyl or cyclohexyl.

According to one embodiment of the invention, it is possible to use a C-glycoside corresponding to formula (I) for which S can represent a monosaccharide or a polysaccharide comprising up to 6 sugar units, in the form of pyranose and/or furanose and of L and/or D series, said monosaccharide or polysaccharide having at least one free hydroxyl functional group and/or optionally one or more necessarily protected amine functional groups, X and R moreover retaining all the definitions above.

Advantageously, a monosaccharide of the invention may be chosen from the following elements: D-glucose, D-galactose, D-mannose, D-xylose, D-lyxose or L-fucose, L-arabinose, L-rhamnose, D-glucuronic acid, D-galacturonic acid, D-iduronic acid, N-acetyl-D-glucosamine or N-acetyl-D-galactosamine and advantageously designates the following elements: D-glucose, D-xylose, N-acetyl-D-glucosamine or L-fucose and in particular D-xylose.

More particularly, a polysaccharide of the invention comprising up to 6 sugar units may be 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 or N-acetyl-D-glucosamine, an oligosaccharide comprising at least one xylose which may advantageously be chosen from xylobiose, methyl-β-xylobioside, xylotriose, xylotetraose, xylopentaose and xylohexaose, and in particular xylobiose, which is composed of two xylose molecules linked via a 1-4 bond.

More particularly, S may represent a monosaccharide chosen from D-glucose, D-xylose, L-fucose, D-galactose or D-maltose and in particular D-xylose.

• R désigne un radical alkyle linéaire non substitué en C₁-C₄, en particulier en C₁-C₂, notamment un radical méthyle ;
• S représente un monosaccharide tel que décrit ci-dessus et choisi en particulier parmi D-glucose, D-xylose, N-acétyl-D-glucosamine ou L-fucose, et en particulier D-xylose ;
• X représente un groupe choisi parmi -CO-, -CH(OH)- ou -CH(NH₂) et, préférentiellement un groupe -CH(OH)-.

Preferably, a C-glycoside of formula (I) is used for which:

• R denotes an unsubstituted linear _C1 - _C4 , in particular _C1 - _C2 , alkyl radical, in particular a methyl radical;
• S represents a monosaccharide as described above and chosen in particular 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)- or -CH(NH ₂ ) and, preferably a -CH(OH)- group.

Acceptable salts of the compounds described herein include conventional non-toxic salts of said compounds, such as those formed from organic or inorganic acids. Examples include salts of inorganic acids such as sulfuric acid, hydrochloric acid. Also suitable are salts of organic acids, which may comprise one or more carboxylic, sulfonic or phosphonic acid groups. Particular examples include propionic acid, acetic acid, terephthalic acid, citric acid and tartaric acid.

When the compound of formula (I) comprises an acid group, the neutralization of the acid group(s) may be carried out with an inorganic base, such as LiOH, NaOH, KOH, Ca(OH) ₂ , NH ₄ OH, Mg(OH) ₂ or Zn(OH) ₂ , or with an organic base, such as a primary, secondary or tertiary alkylamine, for example triethylamine or butylamine. This primary, secondary or tertiary alkylamine may comprise one or more nitrogen and/or oxygen atoms and may thus comprise, for example, one or more alcohol functional groups; in particular, 2-amino-2-methylpropanol, triethanolamine, 2-(dimethylamino)propanol or 2-amino-2-(hydroxymethyl)-1,3-propanediol may be mentioned. Mention may also be made of lysine or 3-(dimethylamino)propylamine.

Solvates that are acceptable for the compounds described herein include conventional solvates, such as those formed during the final stage of preparation of said compounds due to the presence of solvents. Examples include solvates due to the presence of water or linear or branched alcohols, such as ethanol or isopropanol.

Of course, according to the invention, a C-glycoside corresponding to formula (I) can be used alone or in a mixture with other C-glycosides and in any proportion.

A C-glycoside which is suitable for the invention can in particular be obtained by the synthetic method described in WO 02/051828.

In particular, mention may be made, by way of non-limiting illustration of the C-glycoside compounds which are particularly suitable for the invention, of the following compounds:

- C-β-D-xylopyranoside-n-propane-2-one,

- C-α-D-xylopyranoside-n-propane-2-one,

- C-β-D-xylopyranoside-2-hydroxypropane,

- C-α- D-xylopyranoside-2-hydroxypropane,

- 1-(C-β-D-fucopyranoside)propane-2-one,

- 1-(C-α-D-fucopyranoside)propane-2-one,

- 1-(C-β-L-fucopyranoside)propane-2-one,

- 1-(C-α-L-fucopyranoside)propane-2-one,

- 1-(C-β-D-fucopyranoside)-2-hydroxypropane,

- 1-(C-α-D-fucopyranoside)-2-hydroxypropane,

- 1-(C-β-L-fucopyranoside)-2-hydroxypropane,

- 1-(C-α-L-fucopyranoside)-2-hydroxypropane,

- 1-(C-β-D-glucopyranosyl)-2-hydroxypropane,

- 1-(C-α-D-glucopyranosyl)-2-hydroxypropane,

- 1-(C-β-D-galactopyranosyl)-2-hydroxypropane,

- 1-(C-α-D-galactopyranosyl)-2-hydroxypropane,

- 1-(C-β-D-fucofuranosyl)propane-2-one,

- 1-(C-α-D-fucofuranosyl)propane-2-one,

- 1-(C-β-L-fucofuranosyl)propane-2-one,

- 1-(C-α-L-fucofuranosyl)propane-2-one,

- C-β-D-maltopyranoside-n-propane-2-one,

- C-α-D-maltopyranoside-n-propane-2-one,

- C-β-D-maltopyranoside-2-hydroxypropane,

- C-α-D-maltopyranoside-2-hydroxypropane, their isomers and their mixtures.

According to one embodiment, C-β-D-xylopyranoside-2-hydroxypropane or C-α-D-xylopyranoside-2-hydroxypropane and better still C-β-D-xylopyranoside-2-hydroxypropane can advantageously be used for the preparation of a composition according to the invention.

In a specific embodiment, the C-glycoside may be C-β-D-xylopyranoside-2-hydroxypropane (or hydroxypropyl tetrahydropyrantriol) provided as a solution containing 70% by weight of active material in water and propylene glycol.

Advantageously, the C-glycoside is present in the composition of the present invention in an amount ranging from 1% to 10% by weight, preferably from 1.5% to 8% by weight, more preferably from 2% to 5% by weight, relative to the total weight of the composition.

Polyhydric alcohols

According to the first aspect, the composition of the present invention comprises at least one hydrophilic moisturizer chosen from polyhydric alcohols, which is different from the at least one C-glycoside.

As used herein, the term "polyhydric alcohol" refers to an alcohol comprising more than one hydroxyl. Preferably, the polyhydric alcohol is selected from the group consisting of glycerin, panthenol, hexylene glycol, polyethylene glycol, polypropylene glycol, propylene glycol, sorbitol, and mixtures thereof.

Preferably, the hydrophilic moisturizer is glycerin.

Advantageously, the hydrophilic moisturizer is present in the composition of the present invention in an amount ranging from 2% by weight to 20% by weight, preferably from 4% by weight to 15% by weight, more preferably from 5% by weight to 10% by weight, relative to the total weight of the composition.

Glyceryl monoesters of fatty acids and polyglyceryl esters of fatty acids

According to the first aspect, the composition of the present invention comprises at least one non-ionic surfactant chosen from fatty acid glyceryl monoesters, fatty acid polyglyceryl esters and a mixture thereof.

Glyceryl monoesters of fatty acids suitable for the present invention include, but are not limited to, glyceryl monoesters of one or more saturated or unsaturated, linear or branched fatty acids, including 16-22 carbon atoms.

Preferably, the fatty acid glyceryl monoester is chosen from glyceryl monooleate, glyceryl monostearate (or glyceryl stearate), glyceryl monoisostearate, glyceryl monopalmitate, glyceryl monobehenate and mixtures thereof.

More preferably, the fatty acid glyceryl monoester used in the composition of the present invention is glyceryl monostearate (or glyceryl stearate).

Polyglyceryl fatty acid esters suitable for the present invention include, but are not limited to, polyglyceryl fatty acid esters with a polyglyceryl moiety derived from 2 to 10 glycerol units.

Preferably, the fatty acid polyglyceryl ester is selected from esters of one or more saturated or unsaturated, linear or branched fatty acids including 8 to 22, preferably 16 to 22 carbon atoms and polyglycerin with a polyglyceryl moiety derived from 2 to 10 glycerol units.

More preferably, the fatty acid polyglycerol ester is selected from polyglyceryl-4 caprate, polyglyceryl-4 caprylate, polyglyceryl-6 caprylate, polyglyceryl-6 caprate, polyglyceryl-4 caprylate/caprate, polyglyceryl-6 caprylate/caprate, polyglyceryl-6 caprylate/caprate, polyglyceryl-3 cocoate, polyglyceryl-4 cocoate, polyglyceryl-10 decalinoleate, polyglyceryl-10 decaoleate, polyglyceryl-10 decastearate, polyglyceryl-3 dicaprate, polyglyceryl-3 dicocoate, polyglyceryl-10 didecanoate, polyglyceryl-2 diisostearate, polyglyceryl-3 diisostearate, polyglyceryl-4 dioleate, polyglyceryl-10 diisostearate, polyglyceryl-10 dioleate ... polyglyceryl-4, polyglycerin-2 dioleate, polyglyceryl-3 dioleate, polyglyceryl-6 dioleate, polyglyceryl-10 dioleate, polyglyceryl-6 dipalmitate, polyglyceryl-10 dipalmitate, polyglyceryl-2 dipolyhydroxystearate, polyglyceryl-2 distearate, polyglyceryl-3 distearate, polyglyceryl-6 distearate, polyglyceryl-10 distearate, polyglyceryl-10 heptaoleate, polyglyceryl-10 heptastearate, polyglyceryl-6 hexaoleate, polyglyceryl-10 hexaoleate, polyglyceryl-2 isopalmitate, polyglyceryl-2 isostearate, polyglyceryl-4 isostearate, polyglyceryl-4 diisostearate/polyhydroxystearate/sebacate, isostearate polyglyceryl-5, polyglyceryl-6 isostearate, polyglyceryl-6 isostearate, polyglyceryl-10 isostearate, polyglyceryl-2 laurate, polyglyceryl-3 laurate, polyglyceryl-4 laurate, polyglyceryl-4 laurate/sebacate, polyglyceryl-4 laurate/succinate, polyglyceryl-5 laurate, polyglyceryl-6 laurate, polyglyceryl-10 laurate, polyglyceryl-3 myristate, polyglyceryl-10 myristate, polyglyceryl-2 oleate, polyglyceryl-3 oleate, polyglyceryl-4 oleate, polyglyceryl-5 oleate, polyglyceryl-6 oleate, polyglyceryl-8 oleate, polyglyceryl-10 oleate, polyglyceryl-3 palmitate, polyglyceryl-6 palmitate, polyglyceryl-10 pentalaurate, polyglyceryl-10 pentalinoleate, polyglyceryl-4 pentaoleate, polyglyceryl-10 pentaoleate, polyglyceryl-3 pentaricinoleate, polyglyceryl-6 pentaricinoleate, polyglyceryl-10 pentaricinoleate, polyglyceryl-4 pentastearate, polyglyceryl-6 pentastearate, polyglyceryl-10 pentastearate, polyglyceryl-3 polyricinoleate, polyglyceryl-6 polyricinoleate, polyglyceryl-3 ricinoleate, polyglyceryl-3 stearate, polyglyceryl-2 stearate, polyglyceryl-4 stearate, polyglyceryl-8 stearate, polyglyceryl-10 stearate, polyglyceryl-2 tetraisostearate, polyglyceryl-6 tetraoleate, tetraoleate polyglyceryl-10, polyglyceryl-2 tetrastearate, polyglyceryl-2 triisostearate, polyglyceryl-3 triisostearate, polyglyceryl-10 trioleate, polyglyceryl-4 tristearate, polyglyceryl-10 tristearate, and mixtures thereof.

Most preferably, the fatty acid polyglyceryl ester used in the composition of the present invention is selected from polyglyceryl-2 isostearate, polyglyceryl-4 isostearate, polyglyceryl-4 diisostearate/polyhydroxystearate/sebacate, polyglyceryl-2 diisostearate, polyglyceryl-3 diisostearate, polyglyceryl-4 diisostearate, polyglyceryl-2 tetraisostearate, polyglyceryl-2 triisostearate, polyglyceryl-3 triisostearate, and mixtures thereof.

Even more preferably, the fatty acid polyglyceryl ester used in the anhydrous composition of the present invention is polyglyceryl-4 diisostearate/polyhydroxystearate/sebacate. Polyglyceryl-4 diisostearate/polyhydroxystearate/sebacate can promote the penetration of C-glycoside into the anhydrous composition, more preferably, promote the penetration of C-β-D-xylopyranoside-2-hydroxypropane (or hydroxypropyl tetrahydropyrantriol).

In some preferred embodiments, the nonionic surfactant used is selected from glyceryl monooleate, glyceryl monostearate, glyceryl monoisostearate, glyceryl monopalmitate, glyceryl monobehenate, polyglyceryl-3 pentaricinoleate, polyglyceryl-6 pentaricinoleate, polyglyceryl-10 pentaricinoleate, polyglyceryl-3 polyricinoleate, polyglyceryl-2 isostearate, polyglyceryl-4 isostearate, polyglyceryl-5 isostearate, polyglyceryl-6 isostearate, polyglyceryl-10 isostearate, polyglyceryl-2 diisostearate, polyglyceryl-3 diisostearate, polyglyceryl-4 diisostearate, Polyglyceryl-4 diisostearate/polyhydroxystearate/sebacate, polyglyceryl-10 diisostearate, polyglyceryl-2 tetastearate, polyglyceryl-2 triisostearate, polyglyceryl-3 triisostearate and mixtures thereof.

In some more preferred embodiments, the nonionic surfactant used is selected from glyceryl monostearate, polyglyceryl-2 isostearate, polyglyceryl-4 isostearate, polyglyceryl-4 diisostearate/polyhydroxystearate/sebacate, polyglyceryl-2 diisostearate, polyglyceryl-3 diisostearate, polyglyceryl-4 diisostearate, polyglyceryl-2 tetraisostearate, polyglyceryl-2 triisostearate, polyglyceryl-3 triisostearate and mixtures thereof.

Even more preferably, the non-ionic surfactant used in the anhydrous composition of the present invention is polyglyceryl-4 diisostearate/polyhydroxystearate/sebacate.

Advantageously, the non-ionic surfactant chosen from fatty acid glyceryl monoesters, fatty acid polyglyceryl esters and a mixture thereof is present in the composition of the present invention in an amount ranging from 0.1% by weight to 20% by weight, preferably from 0.5% by weight to 15% by weight, more preferably from 1% by weight to 8% by weight, relative to the total weight of the composition.

Waxes

According to the first aspect, the composition of the present invention comprises at least one wax.

The term "wax" refers to a lipophilic compound which is solid at room temperature (25°C), with a reversible solid/liquid state change, having a melting point greater than or equal to 30°C, which can go up to 200°C and in particular up to 120°C.

Preferably, the wax is selected from polyethylene wax, paraffin, microcrystalline wax, synthetic wax, a C20-40 alkyl stearate and combinations thereof.

Preferably, the polyethylene wax may have a weight average molecular weight of 300 to 5000, preferably 400 to 3000.

Advantageously, the wax is present in the composition of the present invention in an amount ranging from 1% by weight to 30% by weight, preferably from 3% by weight to 20% by weight, more preferably from 5% by weight to 15% by weight, relative to the total weight of the composition.

Advantageously, the polyethylene wax is present in the composition according to the present invention in an amount ranging from 1% by weight to 20% by weight, preferably from 1.5% by weight to 10% by weight, relative to the total weight of the composition.

Oils)

Preferably, the anhydrous composition according to the present invention comprises at least one oil.

Here, the term "oil" is understood to mean a fatty compound or substance that is in the form of a liquid or paste (not solid) at room temperature (25 °C) under atmospheric pressure (760 mmHg). As oils, those generally used in cosmetics can be used alone or in combination. These oils can be volatile or non-volatile.

The oil may be a non-polar oil such as a hydrocarbon oil, a silicone oil or the like; a polar oil such as an ester oil or a fatty alcohol; or a mixture thereof.

The oil can be vegetable oils or synthetic oils.

Examples of vegetable oils include, for example, canola oil, linseed oil, camellia oil, macadamia nut oil, corn oil, mink oil, olive oil, avocado oil, sasanqua oil, castor oil, safflower oil, jojoba oil, sunflower oil, almond oil, rapeseed oil, sesame oil, soybean oil, peanut oil and mixtures thereof.

Examples of synthetic oils include ester oils, silicone oils, hydrocarbon oils, fatty alcohols and mixtures thereof.

The ester oils are preferably liquid esters of saturated or unsaturated, linear or branched C ₁ -C ₂₆ aliphatic monoacids or polyacids and of saturated or unsaturated, linear or branched C ₁ -C ₂₆ aliphatic monoalcohols or polyalcohols, the total number of carbon atoms of the esters being greater than or equal to 10.

Among the monoesters of monoacids and monoalcohols, mention may be made of ethyl palmitate, ethylhexyl palmitate, isopropyl palmitate, dicaprylyl carbonate, alkyl myristates such as isopropyl myristate or ethyl myristate, isocetyl stearate, 2-ethylhexyl isonanoate, isononyl isonanoate, isodecyl neopentanoate and isostearyl neopentanoate.

Esters of C ₄ -C ₂₂ dicarboxylic or tricarboxylic acids and C ₁ -C ₂₂ alcohols, and esters of monocarboxylic, dicarboxylic or tricarboxylic acids and C ₄ -C ₂₆ non-sugar dihydroxy, trihydroxy, tetrahydroxy or pentahydroxy alcohols may also be used.

Examples include: diethyl sebacate; isopropyl lauroyl sarcosinate; diisopropyl sebacate; bis(2-ethylhexyl) sebacate; diisopropyl adipate; di-n-propyl adipate; dioctyl adipate; bis(2-ethylhexyl) adipate; diisostearyl adipate; bis(2-ethylhexyl) maleate; triisopropyl citrate; triisocetyl citrate; triisostearyl citrate; glyceryl trilactate; glyceryl trioctanoate; trioctyldodecyl citrate; trioleyl citrate; neopentyl glycol diheptanoate; diethylene glycol diisononanoate and mixtures thereof.

The esters according to this variant may also be selected from monoesters, diesters, triesters, tetraesters and polyesters, and mixtures thereof.

These esters may be, for example, oleates, laurates, palmitates, myristates, behenates, cocoates, stearates, linoleates, linolenates, caprates and arachidonates, or mixtures thereof such as, in particular, mixed esters of oleopalmitate, oleostearate and palmitostearate, as well as pentaerythrityl tetraethyl hexanoate, pentaerythrityl tetraisostearate and mixtures thereof.

Examples of preferable ester oils include, for example, diisopropyl adipate, dioctyl adipate, 2-ethylhexyl hexanoate, ethyl laurate, cetyl octanoate, octyldodecyl octanoate, isodecyl neopentanoate, myristyl propionate, 2-ethylhexyl 2-ethylhexanoate, 2-ethylhexyl octanate, 2-ethylhexyl caprylate/caprate, methyl palmitate, ethyl palmitate, isopropyl palmitate, dicaprylyl carbonate, isopropyl lauroyl sarcosinate, isononyl isonanoate, ethylhexyl palmitate, laurate isohexyl, hexyl laurate, isocetyl stearate, isopropyl isostearate, isopropyl myristate, isodecyl oleate, glyceryl tri(2-ethylhexanoate), pentaerythrityl tetra(2-ethylhexanoate), pentaerythrityl tetraisosterate, 2-ethylhexyl succinate, diethyl sebacate and mixtures thereof.

Examples of ester oils also include triglycerides, for example, capryl caprylyl glycerides, glyceryl trimyristate, glyceryl tripalmitate, glyceryl trilinolenate, glyceryl trilaurate, glyceryl tricaprate, glyceryl tricaprylate, glyceryl tri(caprate/caprylate) (or caprylic/capric triglyceride), and glyceryl tri(caprate/caprylate/linolenate).

Examples of silicone oils include, for example, linear organopolysiloxanes optionally comprising alkyl or alkoxy groups containing from 1 to 10 carbon atoms such as dimethylpolysiloxane, methylphenylpolysiloxane, methylhydrogenpolysiloxane and the like; cyclic organopolysiloxanes such as cyclohexasiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane and the like; and mixtures thereof.

Preferably, the silicone oil is chosen from liquid polydialkylsiloxanes, in particular liquid polydimethylsiloxanes (PDMS) and liquid polyorganosiloxanes comprising at least one aryl group. They may be volatile or non-volatile.

1. les polydialkylsiloxanes cycliques comprenant de 3 à 7 et de préférence de 4 à 5 atomes de silicium ; et
2. les polydialkylsiloxanes volatils linéaires contenant 2 à 9 atomes de silicium et ayant une viscosité inférieure ou égale à 5 × 10^-6m²/s à 25 °C.

When they are volatile, silicones are more particularly chosen from those having a boiling point between 60°C and 260°C, and even more particularly from:

1. cyclic polydialkylsiloxanes comprising from 3 to 7 and preferably from 4 to 5 silicon atoms; and
2. linear volatile polydialkylsiloxanes containing 2 to 9 silicon atoms and having a viscosity less than or equal to 5 × 10 ^-6 m ² /s at 25 °C.

Non-volatile polydialkylsiloxanes can also be used. These non-volatile silicones are more particularly chosen from polydialkylsiloxanes, among which we can mainly mention polydimethylsiloxanes containing trimethylsilyl end groups.

Also of interest are polydimethylsiloxanes containing dimethylsilanol end groups known as dimethiconol (CTFA), such as the oils in the 48 range from Rhodia.

Among the silicones containing aryl groups, mention may be made of polydiarylsiloxanes, in particular polydiphenylsiloxanes and polyalkylarylsiloxanes such as phenyl silicone oil.

• des alcanes inférieurs linéaires ou ramifiés, éventuellement cycliques, en C₆- C_16.Les exemples qui peuvent être mentionnés incluent hexane, undécane, dodécane, tridécane et isoparaffines, par exemple isohexadécane, isododécane et isodécane ; et
• les hydrocarbures linéaires ou ramifiés contenant plus de 16 atomes de carbone, tels que paraffines liquides, gelée de pétrole liquide, polydécènes et polyisobutènes hydrogénés tels que Parleam et squalane.

Hydrocarbon oils can be chosen from:

• linear or branched, optionally cyclic, lower alkanes of C ₆ - C _16. Examples that may be mentioned include hexane, undecane, dodecane, tridecane and isoparaffins, for example isohexadecane, isododecane and isodecane; and
• linear or branched hydrocarbons containing more than 16 carbon atoms, such as liquid paraffins, liquid petroleum jelly, hydrogenated polydecenes and polyisobutenes such as Parleam and squalane.

Preferred examples of hydrocarbon oils include, for example, linear or branched hydrocarbons such as isohexadecane, isododecane, squalane, mineral oil (e.g., liquid paraffin), paraffin, petrolatum or vaseline, naphthalenes, and the like; hydrogenated polyisobutene, isoeicosane, and decene/butene copolymer; and mixtures thereof.

In certain preferred embodiments, the composition of the present invention further comprises at least one oil selected from silicone oils, preferably selected from organopolysiloxanes optionally comprising alkyl or alkoxy groups containing from 1 to 10 carbon atoms such as methylpolysiloxane, caprylyl methylpolysiloxane and dimethylpolysiloxane, triglycerides and mixtures thereof.

If present, advantageously, the oil is present in the composition of the present invention in an amount ranging from 5% by weight to 80% by weight, preferably from 10% by weight to 70% by weight, relative to the total weight of the composition.

In certain preferred embodiments, the composition of the present invention further comprises at least one oil selected from organopolysiloxanes optionally comprising alkyl or alkoxy groups containing from 1 to 10 carbon atoms, triglycerides and mixtures thereof in an amount ranging from 10% by weight to 70% by weight, relative to the total weight of the composition.

SILICONE ELASTOMER

Preferably, the composition of the present invention comprises a silicone elastomer.

It can be chosen from optionally polyoxyalkylenated silicone elastomers.

Polyoxyalkylene silicone elastomer is a crosslinked organopolysiloxane which can be obtained by crosslinking addition reaction of diorganopolysiloxane containing at least one silicon-bonded hydrogen and a polyoxyalkylene containing at least two ethylenically unsaturated groups.

Preferably, the polyoxyalkylene crosslinked organopolysiloxane is obtained by a crosslinking addition reaction (A1) of diorganopolysiloxane containing at least two hydrogens each bonded to a silicon, and (B1) of polyoxyalkylene containing at least two ethylenically unsaturated groups, in particular in the presence (C1) of a platinum catalyst, as described, for example, in US patents 5,236,986 and US 5,412,004.

In particular, the organopolysiloxane can be obtained by reaction of polyoxyalkylene (in particular polyoxyethylene and/or polyoxypropylene) terminated with dimethylvinylsiloxy and methylhydropolysiloxane terminated with trimethylsiloxy, in the presence of a platinum catalyst.

Advantageously, the polyoxyalkylenated silicone elastomers can be formed from divinyl compounds, in particular polyoxyalkylenes containing at least two vinyl groups, reacting with the Si-H bonds of a polysiloxane.

The polyoxyalkylenated silicone elastomer according to the present disclosure is preferably blended with at least one hydrocarbon oil and/or a silicone oil to form a gel. In these gels, the polyoxyalkylenated elastomer may take the form of non-spherical particles.

Polyoxyalkylene elastomers are described in particular in US patents 5,236,986, US 5,412,004, US 5,837,793, and US 5,811,487.

As silicone elastomers, those with the following INCI names can be used:

Dimethicone/PEG-10/15-Crosspolymer,

PEG-15/Lauryl Dimethicone Crosspolymer,

PEG-10/Lauryl Dimethicone Crosspolymer,

PEG-12 Dimethicone Crosspolymer,

PEG-10 Dimethicone Crosspolymer,

PEG-10 Dimethicone/Vinyl Dimethicone Crosspolymer,

PEG-12 Dimethicone/PPG-20 Crosspolymer,

Dimethicone/Vinyl Dimethicone Crosspolymer;

and mixtures thereof.

If present, advantageously, the oily phase is present in the composition of the present invention in an amount ranging from 3% by weight to 20% by weight, preferably from 5% by weight to 15% by weight, relative to the total weight of the composition.

In certain preferred embodiments, the composition of the present invention further comprises an optionally polyoxyalkylenated silicone crosslinked polymer selected from Dimethicone/PEG-10/15 crosslinked polymer, PEG-15/Lauryl Dimethicone crosslinked polymer, PEG-10/Lauryl Dimethicone crosslinked polymer, PEG-12 Dimethicone crosslinked polymer, PEG-10 Dimethicone crosslinked polymer, PEG-12 Dimethicone/PPG-20 crosslinked polymer, Dimethicone/Vinyl Dimethicone crosslinked polymer; and mixtures thereof, in an amount ranging from 5% by weight to 15% by weight, based on the total weight of the composition.

Colorant(s)

The compositions according to the present invention may optionally comprise at least one colorant.

For the purposes of the present invention, the term “colorant” designates a compound capable of producing a colored optical effect when formulated in sufficient quantity in a suitable cosmetic medium.

The dye considered in the context of the present invention may be chosen from water-soluble or water-insoluble, fat-soluble or non-fat-soluble, organic or inorganic dyes, and materials with an optical effect, and mixtures thereof.

If present, advantageously, the colorant is present in the composition according to the present invention in an amount ranging from 0.01% by weight to 35% by weight, preferably from 1% by weight to 20% by weight, more preferably from 5% by weight to 15% by weight, relative to the total weight of the composition.

Other ingredients

The composition according to the present invention may further comprise other ingredients generally used in the field considered.

For example, the composition according to the present invention may further comprise other ingredients selected from polymers for improving wear, fillers, antioxidants, preservatives, perfumes, neutralizers, antiseptics, additional cosmetic active agents, such as vitamins, collagen protective agents and mixtures thereof.

It is routine for a person skilled in the art to adjust the nature and quantity of the other ingredients present in the compositions in accordance with the present invention so that the advantageous properties of the composition used according to the present invention are not, or are not substantially, negatively affected by the intended addition.

1. de 1 % en poids à 10 % en poids d'au moins un C-glycoside ;
2. de 2 % en poids à 20 % en poids d’au moins un hydratant hydrophile choisi parmi les alcools polyhydriques, qui est différent de l’au moins un C-glycoside ;
3. de 0,1 % en poids à 20 % en poids d’au moins un tensioactif non ionique choisi parmi les monoesters de glycéryle d’acide gras, les esters de polyglycéryle d’acide gras et un mélange de ceux-ci ; et
4. de 1 % en poids à 30 % en poids d’au moins une cire.

According to one embodiment, the present invention provides an anhydrous composition, comprising, relative to the total weight of the composition:

1. from 1% by weight to 10% by weight of at least one C-glycoside;
2. from 2% by weight to 20% by weight of at least one hydrophilic moisturizer selected from polyhydric alcohols, which is different from the at least one C-glycoside;
3. from 0.1% by weight to 20% by weight of at least one non-ionic surfactant selected from fatty acid glyceryl monoesters, fatty acid polyglyceryl esters and a mixture thereof; and
4. from 1% by weight to 30% by weight of at least one wax.

1. de 2 % en poids à 5 % en poids d’hydroxypropyl tétrahydropyrantriol ;
2. de 4 % en poids à 10 % en poids de glycérine ;
3. de 1 % en poids à 8 % en poids d’au moins un tensioactif non ionique choisi parmi le monostéarate de glycéryle, le polyricinoléate de polyglycéryle-6, le diisostéarate/polyhydroxystéarate/sébacatede polyglycéryle-4, l’isostéarate de polyglycéryle-4 et leur mélange ; et
4. de 1,5 % en poids à 10 % en poids de cire de polyéthylène.

According to a preferred embodiment, the present invention provides an anhydrous composition, comprising, relative to the total weight of the composition:

1. from 2% by weight to 5% by weight of hydroxypropyl tetrahydropyrantriol;
2. from 4% by weight to 10% by weight of glycerin;
3. from 1% by weight to 8% by weight of at least one non-ionic surfactant chosen from glyceryl monostearate, polyglyceryl-6 polyricinoleate, polyglyceryl-4 diisostearate/polyhydroxystearate/sebacate, polyglyceryl-4 isostearate and their mixture; and
4. from 1.5% by weight to 10% by weight of polyethylene wax.

Dosage form

The anhydrous composition of the present invention is suitable for use as a skin care and/or makeup product. More particularly, the composition of the present invention is in the form of a lipstick and the like.

The composition according to the present invention can be prepared in a conventional manner.

According to the second aspect, the present invention provides a cosmetic process for caring for/making up keratinous materials comprising the application of the composition as described above to the keratinous materials.

Keratinous material is the skin, especially the lips.

According to a third aspect, the present invention proposes the use of an anhydrous composition comprising at least one non-ionic surfactant chosen from fatty acid glyceryl monoesters, fatty acid polyglyceryl esters and a mixture thereof, to improve the penetration of a C-glycoside, in particular hydroxypropyl tetrahydropyrantriol, into keratinous materials, in particular the lips.

Examples

The following examples are given as non-limiting illustrations of the present invention.

The main raw materials used, trade names and their suppliers are listed in Table 1.

INCI name Trade name Supplier Polyglyceryl-4 diisostearate/polyhydroxystearate/sebacate ISOLAN® GPS EVONIK GOLDSCHMIDT Glycerin BP GLYCERIN ORGANIC CHEMICAL CORPORATION Polyethylene PERFORMALENE ^TM 500-L POLYETHYLENE NUCERA SOLUTIONS C20-40 alkyl stearate KESTER WAX K 82 H KOSTER KEUNEN Paraffin (and) microcrystalline wax (and) synthetic wax PARACERA® 30540 PARAMELT Dimethicone (and) dimethicone/
vinyl dimethicone crosspolymer X-25-7034H SHIN ETSU Dimethicone (and) dimethicone/
PEG-10/15 crosspolymer KSG 210 SHIN ETSU PEG-12 dimethicone/PPG-20 crosspolymer DOWSIL ^TM EL-7040 HYDRO ELASTOMER BLEND DOW

Inventive Examples 1-3 and Comparative Examples 1-4

Lipsticks according to the present invention (EI.) 1-3 and comparative lipsticks (EC) 1-4 were prepared with the ingredients listed in Table 2 (the contents are expressed as weight percentages of each material, unless otherwise indicated):

Components EI.1 EI. 2 EI.3 EC.1 EC. 2 EC. 3 EC.4 % by weight % by weight % by weight % by weight % by weight % by weight % by weight Diisostearate/polyhydroxystearate/
polyglyceryl-4 sebacate 4 4 4 - - 4 4 Glycerin 8 8 8 8 8 - - Hydroxypropyl tetrahydropyrantriol 3.15 3.15 3.15 3.15 - - 3.15 Polyethylene 2.5 2.5 2.5 2.5 2.5 2.5 2.5 C20-40 alkyl stearate 7.5 - 7.5 7.5 7.5 7.5 7.5 Paraffin (and) microcrystalline wax (and) synthetic wax - 7.5 - - - - - Dimethicone 8.54 8.54 - 19.06 19.06 19.06 19.06 Dimethicone crosslinked polymer/
vinyl dimethicone 3.66 3.66 1.8 1.8 1.8 1.8 1.8 Dimethicone/PEG-10/15 crosslinked polymer - - 5 5 5 5 5 Caprylyl methicone 16.04 16.04 - - - - - PEG-12 dimethicone/PPG-20 crosslinked polymer 3.76 3.76 - - - - - Caprylic/capric triglyceride Up to 100 Up to 100 Up to 100 Up to 100 Up to 100 Up to 100 Up to 100

The compositions of inventive examples 1 to 3 are compositions according to the present invention.

The composition of Comparative Example 1 does not include a non-ionic surfactant selected from fatty acid glyceryl monoesters and fatty acid polyglyceryl esters.

The composition of Comparative Example 2 does not include C-glycoside and non-ionic surfactant selected from fatty acid glyceryl monoesters and fatty acid polyglyceryl esters.

The composition of Comparative Example 3 does not include a C-glycoside and a hydrophilic moisturizer selected from polyhydric alcohols, which is different from the at least one C-glycoside.

The composition of Comparative Example 4 does not include a hydrophilic moisturizer selected from polyhydric alcohols, which is different from the at least one C-glycoside.

Preparation procedure :

1. pesée de triglycéride caprylique/caprique, de polyéthylène, de stéarate d’alkyle en C20-40 (si présent), de paraffine (et) la cire microcristalline (et) cire synthétique (si présents), du diisostéarate/polyhydroxystéarate/ sébacate de polyglycéryle-4 (si présent), et du diméthicone (et) du polymère réticulé diméthicone/vinyl diméthicone ont été pesés dans un récipient principal et chauffage du récipient à environ 95°C avec agitation jusqu’à ce qu’un mélange homogène ait été obtenu ;
2. ajout de polymère réticulé PEG-12 diméthicone/PPG-20 (si présent), du polymère réticulé diméthicone (et) diméthicone/PEG-10/15 (si présent) à 95 °C avec agitation jusqu’à ce qu’un mélange homogène ait été obtenu ;
3. ajout d’un pré-mélange glycérine/hydroxypropyl tétrahydropyrantriol
   (si présent) dans le récipient principal et homogénéisation de la masse avec agitation jusqu’à ce qu’un mélange homogène ait été obtenu ;
4. versement du mélange homogène obtenu à l’étape 3) dans un moule de rouge à lèvres préchauffé à 42±2 °C, fait de laisser le mélange homogène dans le moule à moins de 25 °C jusqu’à solidification ; puis solidification plus avant à moins de -20 °C jusqu’à ce que la température du vrac ait atteint 4±2 °C ; et
5. Démoulage des rouges à lèvres de leur moule.

The detailed procedure for preparing the above lipsticks is as follows:

1. weighing of caprylic/capric triglyceride, polyethylene, C20-40 alkyl stearate (if present), paraffin (and) microcrystalline wax (and) synthetic wax (if present), polyglyceryl-4 diisostearate/polyhydroxystearate/sebacate (if present), and dimethicone (and) dimethicone/vinyl dimethicone crosslinked polymer were weighed into a primary container and heating the container to about 95°C with stirring until a homogeneous mixture was obtained;
2. adding PEG-12 dimethicone/PPG-20 crosslinked polymer (if present), dimethicone (and) dimethicone/PEG-10/15 crosslinked polymer (if present) at 95°C with stirring until a homogeneous mixture has been obtained;
3. addition of a glycerin/hydroxypropyl tetrahydropyrantriol premix
   (if present) in the main container and homogenization of the mass with stirring until a homogeneous mixture has been obtained;
4. pouring the homogeneous mixture obtained in step 3) into a lipstick mold preheated to 42±2°C, leaving the homogeneous mixture in the mold at less than 25°C until solidification; then further solidification at less than -20°C until the temperature of the bulk has reached 4±2°C; and
5. Removing the lipsticks from their mold.

Lipstick Reviews :

Hardness

The hardness of the lipsticks prepared above was measured at 20°C via the “cheese wire” method, which is between 40 Nm^-1And 160 Nm^-1.

Stability

The stability of the lipsticks obtained above was evaluated as follows.

First, the lipsticks were placed in the oven at a constant temperature of 20°C. After 24 hours, the lipsticks were placed in 5 test ovens:

a HUM oven: set at 37°C and 80% RH (relative humidity); and

4 ovens: set respectively at 4°C, 25°C, 37°C and 45°C without humidity control under 45-55% RH.

Generally, 2 samples of each lipstick (one upright and one upside down) were placed in each oven at the same time, except in the HUM oven where one sample is upright without a cap and one sample is upright with a cap). At each checkpoint (first day, one month later, two months later), lipsticks were taken out, checked for appearance, recorded data, and put back in place.

If there is no macroscopic crystallization (appearance of crystals, grains, clumps, impurities or surface discoloration) and no oil exudation (a number of droplets) on the surface of all samples in the 5 ovens tested for the same lipstick, then the stability of the lipstick will be assessed as “Pass”.

In case of macroscopic crystallization (appearance of crystals, grains, clumps, impurities or surface discoloration) and/or oil exudation (a number of droplets) on the surface of any sample in the 5 ovens tested for the same lipstick, the stability of the lipstick will be assessed as “Fail”.

The stability results of the lipsticks were summarized in Table 3.

Properties EI.1 EI. 2 EI.3 EC.1 EC. 2 EC. 3 EC.4 Stability Success Success Success Failure Failure Success Success

Hydration

Hydration was tested as follows.

30 women aged 22 to 65 were invited as models.

Lip hydration was assessed on each model using a SEI-M-0034-COMB-02 corneometer, wiping the corneometer probe between each measurement. These measurements were taken at T0 (just before application of the test lipstick), and after 15 minutes (T15min). A single standardized application of the sample was performed by a skin expert on the lips of each model.

The rounded averages of the values read on the corneometer are given in Table 4.

T0 T15min Difference (T15-T0) EI.3 38 53 15 EC.1 Stability test failed, unable to perform hydration test EC.2 Stability test failed, unable to perform hydration test EC.3 38 43 5 EC.4 36 46 10

It can be seen that compared to the baseline (T0), lip hydration was significantly improved after applying the lipsticks of inventive examples 3 after 15 minutes.

In summary, the anhydrous composition according to the present invention is stable for at least 2 months. In addition, the anhydrous composition according to the present invention can provide a good moisturizing effect.

Penetration of hydroxypropyl tetrahydropyrantriol

• Peau humaine pleine épaisseur issue d’une chirurgie plastique abdominale ;
• 5 mg/cm²pour chaque composition (aire d’application : 2 cm²) ;
• 16 heures (temps d’application en vie réelle) d’application à 32^oC ;
• Lavage après la durée d’application ;
• 1-2 applications par cellule (10 cellules par traitement) ;
• Liquide récepteur (NaCl à 0,9 % dans l’eau) ;
• Le décapage a été effectué avec des disques Dsquame® ;
• Quantification LC-MS/MS en lavage, stratum corneum (SC), peau (épiderme + derme) et fluide récepteur (RF).

The penetration of hydroxypropyl tetrahydropyrantriol into the composition of inventive example 1 was carried out, using an ex vivo protocol as follows:

• Full-thickness human skin from abdominal plastic surgery;
• 5 mg/cm ² for each composition (application area: 2 cm ² );
• 16 hours (real life application time) of application at 32 ^o C;
• Wash after application time;
• 1-2 applications per cell (10 cells per treatment);
• Receiving liquid (0.9% NaCl in water);
• Stripping was carried out with Dsquame® discs;
• LC-MS/MS quantification in wash, stratum corneum (SC), skin (epidermis + dermis) and receptor fluid (RF).

The penetration results of hydroxypropyl tetrahydropyrantriol are listed in Table 5.

In epidermis + dermis + receptor fluid (μg/cm ² , median) In the epidermis
(μM, median) EI.1 4.22 1882

It can be seen that the at least one C-glycoside in the composition of the present invention can penetrate strongly into the skin.

Claims (10)

Anhydrous composition for care and/or makeup of keratinous materials comprising:
a) at least one C-glycoside;
b) at least one hydrophilic moisturizer selected from polyhydric alcohols, which is different from the at least one C-glycoside;
(c) at least one non-ionic surfactant selected from fatty acid glyceryl monoesters, fatty acid polyglyceryl esters and a mixture thereof; and
d) at least one wax. Composition according to claim 1, in which the C-glycoside is chosen from compounds of formula (I):
(I)
in which:
– R represents a saturated C ₁ to C ₁₀ alkyl radical, in particular C ₁ to C ₄ which may optionally be substituted by at least one radical chosen from OH, COOH or COOR'' ₂ , R'' ₂ being a saturated C ₁ -C ₄ alkyl radical,
– S represents a monosaccharide or polysaccharide comprising up to 20 sugar units, in particular up to 6 sugar units, in the form of pyranose and/or furanose and of the L and/or D series, said monosaccharide or polysaccharide possibly being substituted by a hydroxyl group which is necessarily free and optionally one or more optionally protected amine functional groups, and
– X represents a radical chosen from the groups -CO-, -CH(OH)-, -CH(NH ₂ )-, -CH(NHCH ₂ CH ₂ CH ₂ OH)-, -CH(NHPh)- and –CH(CH ₃ )- and in particular a radical –CO-, -CH(OH)- or –CH(NH ₂ )- and more particularly a radical –CH(OH)-,
the S-CH ₂ -X bond represents a C-anomeric bond, which can be α or β,
as well as their physiologically acceptable salts, their solvates, such as hydrates, their optical isomers and their mixtures. Composition according to claim 1 or 2, in which the C-glycoside is chosen from
- C-β-D-xylopyranoside-n-propane-2-one,
- C-α-D-xylopyranoside-n-propane-2-one,
- C-β-D-xylopyranoside-2-hydroxypropane,
- C-α- D-xylopyranoside-2-hydroxypropane,
- 1-(C-β-D-fucopyranoside)propane-2-one,
- 1-(C-α-D-fucopyranoside)propane-2-one,
- 1-(C-β-L-fucopyranoside)propane-2-one,
- 1-(C-α-L-fucopyranoside)propane-2-one,
- 1-(C-β-D-fucopyranoside)-2-hydroxypropane,
- 1-(C-α-D-fucopyranoside)-2-hydroxypropane,
- 1-(C-β-L-fucopyranoside)-2-hydroxypropane,
- 1-(C-α-L-fucopyranoside)-2-hydroxypropane,
- 1-(C-β-D-glucopyranosyl)-2-hydroxypropane,
- 1-(C-α-D-glucopyranosyl)-2-hydroxypropane,
- 1-(C-β-D-galactopyranosyl)-2-hydroxypropane,
- 1-(C-α-D-galactopyranosyl)-2-hydroxypropane,
- 1-(C-β-D-fucofuranosyl)propane-2-one,
- 1-(C-α-D-fucofuranosyl)propane-2-one,
- 1-(C-β-L-fucofuranosyl)propane-2-one,
- 1-(C-α-L-fucofuranosyl)propane-2-one,
- C-β-D-maltopyranoside-n-propane-2-one,
- C-α-D-maltopyranoside-n-propane-2-one,
- C-β-D-maltopyranoside-2-hydroxypropane,
- C-α-D-maltopyranoside-2-hydroxypropane,
their isomers and their mixtures. Composition according to any one of claims 1 to 3, in which the polyhydric alcohol is chosen from glycerin, panthenol, hexylene glycol, polyethylene glycol, polypropylene glycol, propylene glycol, sorbitol and mixtures thereof. Composition according to any one of claims 1 to 4, in which the non-ionic surfactant is chosen from glyceryl monoesters of one or more saturated or unsaturated, linear or branched fatty acids including 16 to 22 carbon atoms, and esters of saturated or unsaturated, linear or branched fatty acids, including 8 to 22, preferably 16 to 22 carbon atoms and polyglycerin with a polyglyceryl moiety derived from 2 to 10 glycerol units. A composition according to any one of claims 1 to 5, wherein the non-ionic surfactant is selected from glyceryl monooleate, glyceryl monostearate, glyceryl monoisostearate, glyceryl monopalmitate, glyceryl monobehenate, polyglyceryl-3 pentaricinoleate, polyglyceryl-6 pentaricinoleate, polyglyceryl-10 pentaricinoleate, polyglyceryl-3 polyricinoleate, polyglyceryl-6 ricinoleate, polyglyceryl-3 isostearate, polyglyceryl-2 isostearate, polyglyceryl-4 isostearate, polyglyceryl-4 diisostearate/polyhydroxystearate/sebacate, polyglyceryl-5 isostearate, polyglyceryl-6 isostearate, polyglyceryl-10 isostearate, polyglyceryl-2 diisostearate, polyglyceryl-3 diisostearate, polyglyceryl-4 diisostearate, polyglyceryl-10 diisostearate, polyglyceryl-2 tetraisostearate, polyglyceryl-2 triisostearate, polyglyceryl-3 triisostearate, and mixtures thereof; preferentially chosen from polyglyceryl-2 isostearate, polyglyceryl-4 isostearate, polyglyceryl-4 diisostearate/polyhydroxystearate/sebacate, polyglyceryl-2 diisostearate, polyglyceryl-3 diisostearate, polyglyceryl-4 diisostearate, polyglyceryl-2 tetraisostearate, polyglyceryl-2 triisostearate, polyglyceryl-3 triisostearate. A composition according to any one of claims 1 to 6, wherein the wax is selected from polyethylene, paraffin, microcrystalline wax, synthetic wax, a C20-40 alkyl stearate and combinations thereof. A composition according to any one of claims 1 to 7, further comprising an optionally polyoxyalkylenated silicone elastomer selected from Dimethicone/PEG-10/15 crosslinked polymer, PEG-15/Lauryl Dimethicone crosslinked polymer, PEG-10/Lauryl Dimethicone crosslinked polymer, PEG-12 Dimethicone crosslinked polymer, PEG-10 Dimethicone crosslinked polymer, PEG-10 Dimethicone/Vinyl Dimethicone crosslinked polymer, PEG-12 Dimethicone/PPG-20 crosslinked polymer, dimethicone/vinyl dimethicone crosslinked polymer, and mixtures thereof, in an amount ranging from 5% by weight to 15% by weight, relative to the total weight of the composition. Cosmetic process for the care and/or makeup of keratinous materials comprising the application of the composition as defined in any one of claims 1 to 8 to the keratinous materials, preferably to the lips. Use of an anhydrous composition comprising at least one non-ionic surfactant chosen from fatty acid glyceryl monoesters, fatty acid polyglyceryl esters and a mixture thereof, to improve the penetration of a C-glycoside, in particular hydroxypropyl tetrahydropyrantriol, into keratinous materials, in particular the lips.