WO2025091239A1

WO2025091239A1 - Composition in the form of oil-in-water emulsion

Info

Publication number: WO2025091239A1
Application number: PCT/CN2023/128447
Authority: WO
Inventors: Feixue TENG; Xiaomin WENG
Original assignee: LOreal SA
Current assignee: LOreal SA
Priority date: 2023-10-31
Filing date: 2023-10-31
Publication date: 2025-05-08
Anticipated expiration: 2026-04-30
Also published as: FR3154610B3; FR3154610A3

Abstract

Provided is a composition in the form of oil-in-water emulsion, comprising: (i) at least one saturated C14-C22 fatty acid; (ii) at least one nonionic surfactant selected from glyceryl C14-C22 fatty acid ester, polyoxyethylenated C14-C22 fatty acid ester, and mixtures thereof; (iii) at least 8wt.% of at least one C-glycoside, relative to the total weight of the composition; and (iv) at least 2wt.% of niacinamide and/or a derivative thereof, relative to the total weight of the composition. A non-therapeutic method for caring for and/or making up keratin materials is also provided.

Description

COMPOSITION IN THE FORM OF OIL-IN-WATER EMULSION

TECHNICAL FIELD

The present invention relates to a cosmetic composition. In particular, the present invention relates to a composition in the form of oil-in-water emulsion. In addition, the present invention also relates to a non-therapeutic method for caring for and/or making up keratin materials.

BACKGROUND ART

The development of cosmetic products dedicated to caring for and/or making up the skin and/or lips, is permanent.

Different cosmetic products will comprise different cosmetic active ingredients due to the desired use.

Hydroxypropyl tetrahydropyrantriol is a sugarprotein hybrid derived from xylose, a natural sugar found abundantly in beech trees. It can promote the production of collagen and skin’s natural moisturizers, such as hyaluronic acid. Hence, it can help slow down skin aging and give a plump appearance.

Niacinamide, also called VB3, can protect and sooth the skin.

In order to achieve high cosmetic efficacy, it is desirable to have high content of cosmetic active ingredients in the cosmetic products.

However, it was found that when high dosage of hydroxypropyl tetrahydropyrantriol and niacinamide are added into a cream formula, the formula obtained is not stable.

It is therefore desirable to provide stable compositions, preferably caring for and/or making up of keratin materials, which comprises a relatively high content of hydroxypropyl tetrahydropyrantriol and/or a similar compound and a relatively high content of niacinamide and/or a derivative thereof.

SUMMARY OF THE INVENTION

It is an object of the present invention to develop stable compositions comprising a relatively high content of hydroxypropyl tetrahydropyrantriol and/or a similar compound and a relatively high content of niacinamide and/or a derivative thereof, which are stable.

It is another object of the present invention to provide a non-therapeutic method for caring for and/or making up keratin materials with above compositions.

The inventors have now discovered that it is possible to formulate such compositions comprising a relatively high content of hydroxypropyl tetrahydropyrantriol and/or a similar compound and a relatively high content of niacinamide and/or a derivative thereof, which are stable.

Accordingly, in a first aspect, the present invention relates to a composition in the form of oil-in-water emulsion, preferably for caring for and/or making up keratin materials, comprising:

(i) at least one saturated C14-C22 fatty acid;

(ii) at least one nonionic surfactant selected from glyceryl C14-C22 fatty acid ester, polyoxyethylenated C14-C22 fatty acid ester, and mixtures thereof;

(iii) at least 8 wt. %of at least one C-glycoside, relative to the total weight of the composition; and

(iv) at least 2 wt. %of niacinamide and/or a derivative thereof, relative to the total weight of the composition.

The composition of the present invention is in the form of an oil-in-water emulsion. Thus, said composition comprises a continuous aqueous phase and a dispersed oily phase.

The composition of the present invention is stable, i.e. there is no phase separation after having been rotated at 4000 rpm/min for 4 hours at 45℃.

In a second aspect, the present invention relates to a non-therapeutic method for caring for and/or making up keratin materials, comprising applying the composition according to the present invention to the keratin materials.

Other characteristics and advantages of the invention will emerge more clearly on reading the description and the examples that follow.

DETAILED DESCRIPTION OF THE INVENTION

Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the art the present invention belongs to. When the definition of a term in the present description conflicts with the meaning as commonly understood by those skilled in the art the present invention belongs to, the definition described herein shall apply.

In that which follows and unless otherwise indicated, the limits of a range of values are included within this range, in particular in the expressions "between... and…" and "from... to... ".

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

The expression "and/or" used in the present description is equivalent to the expression "one or both" of indicated elements.

Throughout the instant application, the term “comprising” is to be interpreted as encompassing all specifically mentioned features as well optional, additional, unspecified ones. As used herein, the use of the term “comprising” also discloses the embodiment wherein no features other than the specifically mentioned features are present (i.e. “consisting of” ) .

Unless otherwise specified, all numerical values expressing amount of ingredients and the like which are used in the description and claims are to be understood as being modified by the term “about” . Accordingly, unless indicated to the contrary, the numerical values and parameters described herein are approximate values which are capable of being changed according to the desired purpose as required.

As used herein, the term “keratin materials” refer to the skin and the lips. By “skin” , we intend to mean all the body skin, including the scalp. Preferably, the keratin material is the facial skin.

All percentages in the present invention refer to weight percentage, unless otherwise specified.

The composition according to the present invention comprises:

(i) at least one saturated C14-C22 fatty acid;

Saturated C14-C22 fatty acids

According to the first aspect, the composition of the present invention comprises at least one saturated C14-C22 fatty acid.

As examples of saturated C14-C22 fatty acid, mention can be made of myristic acid, pentadecanoic acid, palmitic acid, heptadecanoic acid, stearic acid, cetearylic acid, arachidic acid, behenic acid, and combinations thereof.

Preferably, the fatty acid is selected from saturated C14-C18 fatty acids.

More preferably, the fatty acid is selected from linear and saturated C14-C18 fatty acids.

Particularly preferably, the fatty acid is selected from myristic acid, palmitic acid, stearic acid, and combinations thereof.

Advantageously, the saturated C14-C22 fatty acid is present in an amount ranging from 0.5 wt. %to 30 wt. %, preferably from 0.8 wt. %to 10 wt. %, more preferably from 1 wt. %to 7 wt. %, relative to the total weight of the composition.

Nonionic surfactants

According to the first aspect, the composition of the present invention comprises at least one nonionic surfactant selected from glyceryl C14-C22 fatty acid ester, polyoxyethylenated C14-C22 fatty acid ester, and mixtures thereof.

As used herein, glyceryl C14-C22 fatty acid ester means an ester of glycerol and a C14-C22 fatty acid.

For glyceryl C14-C22 fatty acid esters, the C14-C22 fatty acid can be an unsaturated or saturated, linear or branched acid, for example, stearic acid, isostearic acid, oleic acid, palmitic acid, and/or myristic acid.

As examples of glyceryl C14-C22 fatty acid ester, mention can be made of glyceryl oleate, glyceryl stearate, glyceryl isostearate, glyceryl palmitate, glyceryl myristate, glyceryl arachidate, glyceryl behenate, and mixtures thereof.

As used herein, polyoxyethylenated C14-C22 fatty acid ester is an ester of polyethylene glycol and a C14-C22 fatty acid.

For polyoxyethylenated C14-C22 fatty acid esters, the C14-C24 fatty acid can be an unsaturated or saturated, linear or branched acid, for example, stearic acid, isostearic acid, oleic acid, palmitic acid, and/or myristic acid.

Preferably, the polyethylene glycol comprises from 1 to 200 oxyethylene groups. More preferably, the polyethylene glycol comprises from 10 to 150 oxyethylene groups. Most preferably, the polyethylene glycol comprises from 20 to 100 oxyethylene groups.

More preferably, the nonionic surfactant is selected from glyceryl esters of a saturated C14-C22 fatty acid, esters of polyethylene glycol comprising from 10 to 150 oxyethylene groups and a saturated C14-C22 fatty acid, and combinations thereof.

Even more preferably, the nonionic surfactant is selected from glyceryl stearate, glyceryl isostearate, glyceryl palmitate, glyceryl myristate, esters of polyethylene glycol comprising from 20 to 100 oxyethylene groups and a C14-C22 fatty acid selected from myristic acid, palmitic acid, stearic acid and isostearic acid, and combinations thereof.

Even more preferably, the surfactant is selected from glyceryl stearate, PEG-100 stearate, and a mixture thereof.

Preferably, the nonionic surfactant is a mixture of glyceryl stearate, glyceryl isostearate, glyceryl palmitate, glyceryl myristate, and esters of polyethylene glycol comprising from 20 to 100 oxyethylene groups and a C14-C22 fatty acid selected from myristic acid, palmitic acid, stearic acid and isostearic acid.

More preferably, the nonionic surfactant is a mixture of glyceryl stearate and PEG-100 stearate.

Advantageously, the nonionic surfactant is present in the composition according to the present invention in an amount ranging from 0.2 wt. %to 20 wt. %, preferably from 0.4 wt. %to 15 wt. %, more preferably from 0.8 wt. %to 12 wt. %, relative to the total weight of the composition.

It was found with the combination of at least one saturated C14-C22 fatty acids and at least one nonionic surfactant selected from glyceryl C14-C22 fatty acid ester, polyoxyethylenated C14-C22 fatty acid ester, and mixtures thereof, the composition according to the present invention can have a lamellar structure, the structure can help build up the viscosity of the composition and increase the stablity of the composition.

Preferably, the weight ratio of the at least one saturated C14-C22 fatty acids to the at least one nonionic surfactant selected from glyceryl C14-C22 fatty acid ester, polyoxyethylenated C14-C22 fatty acid ester, and mixtures thereof, is less than 2.5, preferably less than 1.8.

C-glycosides

According to the first aspect, the composition of the present invention comprises at least 8 wt. %of at least one C-glycoside, relative to the total weight of the composition.

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

in which:

- R represents a saturated C₁ to C₁₀, in particular C₁ to C₄, alkyl radical which can optionally be substituted by at least one radical selected from OH, COOH or COOR”₂, with R”₂ being a saturated C₁-C₄ alkyl radical,

- S represents a monosaccharide or a polysaccharide comprising up to 20 sugar units, in particular up to 6 sugar units, in pyranose and/or furanose form and of the L and/or D series, it being possible for the said monosaccharide or polysaccharide to be substituted by a hydroxyl group which is necessarily free and optionally one or more optionally protected amine functional group (s) , and

-X represents a radical selected from the–CO-, -CH (OH) -, -CH (NH₂) -, -CH (NHCH₂CH₂CH₂OH) -, -CH (NHPh) -and–CH (CH₃) -groups and in particular a–CO-, -CH (OH) -or–CH (NH₂) -radical and more particularly a–CH (OH) -radical,

the S-CH₂-X bond represents a bond of C-anomeric nature, which can beαorβ,

and also their physiologically acceptable salts, their solvates, such as the hydrates, and their optical and geometrical isomers.

The C-glycoside of use for the implementation of the invention are in particular those for which R denotes a saturated linear C₁ to C₆, in particular C₁ to C₄, preferentially C₁ to C₂, alkyl radical and more preferably a methyl radical.

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

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

Advantageously, amonosaccharide of the invention can be selected from 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 denotes D-glucose, D-xylose, N-acetyl-D-glucosamine or L-fucose and in particular D-xylose.

More particularly, apolysaccharide of the invention comprising up to 6 sugar units can be selected from D-maltose, D-lactose, D-cellobiose, D-maltotriose, adisaccharide combining a uronic acid selected from D-iduronic acid or D-glucuronic acid with a hexosamine selected from D-galactosamine, D-glucosamine, N-acetyl-D-galactosamine or N-acetyl-D-glucosamine, an oligosaccharide comprising at least one xylose which can advantageously be selected 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, Scan represent a monosaccharide selected from D-glucose, D-xylose, L-fucose, D-galactose or D-maltose and in particular D-xylose.

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

- R denotes an unsubstituted linear C₁-C₄, in particular C₁-C₂, alkyl radical, especially a methyl radical;

- S represents a monosaccharide as described above and selected in particular from D-glucose, D-xylose, N-acetyl-D-glucosamine or L-fucose, and in particular D-xylose;

- X represents a group selected from-CO-, -CH (OH) -or-CH (NH₂) -and preferably a-CH (OH) -group.

The acceptable salts of the compounds described in the present invention comprise conventional non-toxic salts of the said compounds, such as those formed from organic or inorganic acids. Mention may be made, by way of example, of the salts of inorganic acids, such as sulfuric acid, hydrochloric acid. Mention may also be made of the salts of organic acids, which can comprise one or more carboxylic, sulfonic or phosphonic acid groups. Mention may in particular be made of propionic acid, acetic acid, terephthalic acid, citric acid and tartaric acid.

When the compound of formula (I) comprises an acid group, neutralization of the acid group (s) can be carried out with an inorganic base, such as LiOH, NaOH, KOH, Ca (OH) ₂, NH₄OH, 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 can comprise one or more nitrogen and/or oxygen atoms and can thus comprise, for example, one or more alcohol functional groups; mention may in particular be made of 2-amino-2-methylpropanol, triethanolamine, 2- (dimethylamino) propanol or 2-amino-2- (hydroxymethyl) -1, 3-propanediol. Mention may also be made of lysine or 3- (dimethylamino) propylamine.

The solvates which are acceptable for the compounds described in the present invention comprise conventional solvates, such as those formed during the final stage of preparation of the said compounds due to the presence of solvents. Mention may be made, by way of example, of the solvates due to the presence of water or of linear or branched alcohols, such as ethanol or isopropanol.

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

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

Mention may in particular 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-propan-2-one,
-C-β-D-xylopyranoside-2-hydroxypropane,
-C-α-D-xylopyranoside-2-hydroxypropane,
-1- (C-β-D-fucopyranoside) propan-2-one,
-1- (C-α-D-fucopyranoside) propan-2-one,
-1- (C-β-L-fucopyranoside) propan-2-one,
-1- (C-α-L-fucopyranoside) propan-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) propan-2-one,
-1- (C-α-D-fucofuranosyl) propan-2-one,
-1- (C-β-L-fucofuranosyl) propan-2-one,
-1- (C-α-L-fucofuranosyl) propan-2-one,
-C-β-D-maltopyranoside-n-propane-2-one,
-C-α-D-maltopyranoside-n-propan-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.

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

Advantageously, the C-glycoside is present in the composition in an amount ranging from 8 wt. %to 30%, preferably from 9 wt. %to 20 wt. %, more preferably from 9.5 wt. %to 15 wt. %, relative to the total weight of the composition.

Niacinamide and/or derivatives thereof

According to the first aspect, the composition of the present invention comprises at least 2 wt. %of niacinamide and/or a derivative thereof, relative to the total weight of the composition.

Niacinamide, also called Vitamin B3, is a compound of the following formula:

Niacinamide derivatives that may be mentioned include, for example, nicotinic acid, nicotinyl alcohol, nicotinuric acid, niconityl hydroxamic acid, nicotinic acid esters such as tocopherol nicotinate, amides derived from niacinamide by substitution of the hydrogen of-CONH₂, products from reaction with carboxylic acids and amino acids, esters of nicotinyl alcohol and of carboxylic acids such as acetic acid, salicyclic acid, glycolid acid or palmitic acid.

Mention may also be made of the following derivatives: 2-chloronicotinamide, 6-methylnicotinamide, 6-aminonicotinamide, N-methylnicotinamide, N, N-dimethylnicotinamide, N- (hydroxymethyl) nicotinamide, quinolinic acid imide, nicotinanilide, N-benzylnicotinamide, N-ethylnicotinamide, nifenazone, nicotinaldehyde, isonicotinic acid, methylisonicotinic acid, thionicotinamide, nialamide, 2-mercaptonicotinic acid, nicomol and niaprazine, methyl nicotinate and sodium nicotinate.

Advantageously, niacinamide and/or a derivative thereof is present in the composition of the present invention in an amount ranging from 2 wt. %to 20 wt. %, preferably from 3 wt. %to 15 wt. %, and more preferably from 4 wt. %to 10 wt. %, relative to the total weight of the composition.

Aqueous phase

As an oil-in-water emulsion, the composition of the present invention comprises a continuous aqueous phase.

Said aqueous phase is preferably present in an amount ranging from 10 wt. %to 85 wt. %, more preferably from 20 wt. %to 85 wt. %, relative to the total weight of the composition.

The continuous aqueous phase comprises water.

Water is preferably present in the composition of the present invention in an amount ranging from 10 wt. %to 85 wt. %, preferably from 20 wt. %to 80 wt. %, relative to the total weight of the composition.

Optionally, the continuous hydrophilic phase comprises at least one organic solvent miscible with water (at room temperature 25℃) such as for example monoalcohols having from 2 to 6 carbon atoms such as ethanol, isopropanol; polyols having from 2 to 20 carbon atoms, preferably from 2 to 10 carbon atoms, and preferentially having from 2 to 6 carbon atoms, such as glycerin, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, caprylyl glycol, dipropylene glycol, diethylene glycol; glycol ethers (notably having from 3 to 16 carbon atoms) such as mono-, di-or tri-propylene glycol (C₁-C₄) alkyl ethers, mono-, di-or tri-ethylene glycol (C₁-C₄) alkyl ethers and mixtures thereof.

If presents, the organic solvent is preferably present in the composition of the present invention in an amount ranging from 1 wt. %to 30 wt. %, preferably from 1 wt. %to 25 wt. %, more preferably from 5 wt. %to 20 wt. %, relative to the total weight of the composition.

Oily phase

As an oil-in-water emulsion, the composition of the present invention further comprises a dispersed oily phase.

The oily phase contains at least one oil, notably a cosmetic oil. It may also contain other fatty substances such as waxes, for example beeswax.

The term “oil” means a water-immiscible non-aqueous compound that is liquid at room temperature (20℃) and at atmospheric pressure (760 mmHg) .

The oils may be volatile or non-volatile.

The term “non-volatile” refers to an oil whose vapor pressure at room temperature and atmospheric pressure is non-zero and is less than 10^-3 mmHg (0.13 Pa) .

The term "volatile oil" means any oil that is capable of evaporating in contact with the skin in less than one hour, at room temperature and atmospheric pressure.

The oily phase may comprise hydrocarbon-based oils, silicone oils such as dimethicone, or mixtures thereof.

They may be of animal, plant, mineral or synthetic origin.

The term "hydrocarbon-based oil" means an oil mainly containing hydrogen and carbon atoms.

The term “silicone oil” means an oil comprising at least one silicon atom, and notably at least one Si-O group.

The oils may optionally comprise oxygen, nitrogen, sulfur and/or phosphorus atoms, for example in the form of hydroxyl or acid radicals.

Preferably, the oil is a hydrocarbon-based oil, more preferably is isononyl isononanoate.

Advantageously, the oily phase is present in the composition of the present invention in an amount ranging from 1 wt. %to 30 wt. %, preferably from 5 wt. %to 20 wt. %, relative to the total weight of the composition of the present invention.

Cosmetic active ingredients

As a composition for caring for keratin materials, the composition of the present invention may comprise an additional cosmetic active ingredient.

As examples of additional cosmetic active ingredients, mention can be made of moisturizing agents; brightening agents; tightening agents; peeling agents; repairing and soothing agents; agents acting on the microcirculation, and mixtures thereof.

It is easy for the skilled person in the art to adjust the amount of the cosmetic active ingredient based on the final use of the composition according to the present invention.

Additional adjuvants or additives

The cosmetic composition of the present invention may also contain conventional cosmetic adjuvants or additives, for instance fragrances, chelating agents, preserving agents and bactericides, additional surfactants (for example, nonionic surfactant such as C12-C22 fatty alcohol, C12-C22 alkyl glucoside) , thickeners such as sodium polyacrylate, carbomer, ammonium polyacryloyldimethyltaurate, xanthan gum, fillers, pH regulators, saponifiers (such as potassium hydroxide) , and mixtures thereof.

The skilled person in the art can adjust the amount of the additional adjuvants or additive so as not to adversely impact the final use of the composition according to the present invention.

According to a particularly preferred embodiment, the present invention provides a composition in the form of an oil-in-water emulsion, preferably for caring for and/or making up keratin materials, comprising, relative to the total weight of the composition:

(i) from 1 wt. %to 7 wt. %of at least one saturated C14-C22 fatty acid selected from myristic acid, palmitic acid, stearic acid, and a combination thereof;

(ii) from 0.8 wt. %to 12 wt. %of at least one nonionic surfactant selected from glyceryl laurate, glyceryl stearate, glyceryl isostearate, glyceryl palmitate, glyceryl myristate, esters of polyethylene glycol comprising from 20 to 100 oxyethylene groups and a C14-C22 fatty acid selected from lauric acid, myristic acid, palmitic acid and stearic acid, and combinations thereof;

(iii) from 8 wt. %to 15 wt. %of hydroxypropyl tetrahydropyrantriol; and

(iv) from 4 wt. %to 10 wt. %of niacinamide.

Method and use

The composition of the present invention can be used for caring for and/or making up keratin materials.

According to the second aspect, the present invention relates to a non-therapeutic method for caring for and/or making up keratin materials, comprising applying the composition according to the present invention to the keratin materials.

In particular, the keratin material can be the skin, for example the facial skin.

EXAMPLES

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

Main raw materials used, trade names and supplier thereof are listed in Table 1.

Table 1

Invention Example 1 and comparative examples 1-3

Compositions of invention example (IE) 1 and comparative examples (CE) 1-3 were prepared based on the amounts given in Table 2. The amounts are given in%by weight of active ingredient relative to the total weight of the composition.

Table 2

Composition of invention example 1 represents a composition according to the present invention.

Composition of comparative example 1 does not comprise at least one nonionic surfactant selected from glyceryl C14-C22 fatty acid ester, polyoxyethylenated C14-C22 fatty acid ester, and mixtures thereof.

Composition of comparative example 2 does not comprise at least one saturated C14-C22 fatty acid.

Composition of comparative example 3 does not comprise at least one saturated C14-C22 fatty acid and at least one nonionic surfactant selected from glyceryl C14-C22 fatty acid ester, polyoxyethylenated C14-C22 fatty acid ester, and mixtures thereof.

Preparation process:

The compositions listed above were prepared as follows, taking the composition of invention example 1 as an example:

1. heating stearic acid, palmitic acid, myristic acid, glyceryl stearate (and) PEG-100 stearate, arachidyl alcohol (and) behenyl alcohol (and) arachidyl glucoside, dimethicone, isononyl isononanoate, and beeswax to 75-80℃ to obtain mixture A;

2. heating water to 75-80℃;

3. adding the mixture A into water at 75-80℃ with stirring;

4. adding sodium potassium at 75-80℃ with stirring;

5. adding sodium polyacrylate at 75-80℃ with strring;

6. adding hydroxypropyl tetrahydropyrantriol and niacinamide at 75-80℃ with stirring;

7. cooling down the composition obtained.

Evaluation of compositions

The stability of each composition prepared was evaluated.

Amachine was used to predict long-term stability under extreme condition. In the test, the composition to be evaluated was contained in a sample tube and put into themachine. The machine ran under pre-set protocol, which are 4000 rpm/min, 4 hours, and at 45℃.

After the test is finished, stability can be judged based on sample separation condition.

If there is no separation between the aqueous phase and the oily phase of the composition evaluated, then the composition passes in the stability test.

If there is separation between the aqueous phase and the oily phase of the composition evaluated, then the composition fails in the stability test.

The results of the stability of compositions of invention example 1 and comparative examples 1-3 were summarized below.

Table 3

It can be seen that the composition of invention example 1 is stable.

Claims

A composition in the form of oil-in-water emulsion, preferably for caring for and/or making up keratin materials, comprising:

(i) at least one saturated C14-C22 fatty acid;

(ii) at least one nonionic surfactant selected from glyceryl C14-C22 fatty acid ester, polyoxyethylenated C14-C22 fatty acid ester, and mixtures thereof;

(iii) at least 8 wt. %of at least one C-glycoside, relative to the total weight of the composition; and

(iv) at least 2 wt. %of niacinamide and/or a derivative thereof, relative to the total weight of the composition.
Composition according to claim 1, wherein the fatty acid is selected from linear and saturated C14-C18 fatty acids, preferably, the fatty acid is selected from myristic acid, palmitic acid, stearic acid, and a combination thereof.
Composition according to claim 1 or 2, wherein the saturated C14-C22 fatty acid is present in an amount ranging from 0.5 wt. %to 30 wt. %, preferably from 0.8 wt. %to 10 wt. %, more preferably from 1 wt. %to 7 wt. %, relative to the total weight of the composition.
Composition according to any of claims 1 to 3, wherein the nonionic surfactant is selected from glyceryl esters of a saturated C14-C22 fatty acid, esters of polyethylene glycol comprising from 10 to 150 oxyethylene groups and a saturated C14-C22 fatty acid, and combinations thereof, preferably selected from glyceryl stearate, glyceryl isostearate, glyceryl palmitate, glyceryl myristate, esters of polyethylene glycol comprising from 20 to 100 oxyethylene groups and a saturated C14-C22 fatty acid selected from myristic acid, palmitic acid, stearic acid and isostearic acid, and combinations thereof.
Composition according to any of claims 1 to 4, wherein the nonionic surfactant is present in an amount ranging from 0.2 wt. %to 20 wt. %, preferably from 0.4 wt. %to 15 wt. %, more preferably from 0.8 wt. %to 12 wt. %, relative to the total weight of the composition.
Composition according to any of claims 1 to 5, wherein the weight ratio of the at least one saturated C14-C22 fatty acid to the at least one nonionic surfactant selected from glyceryl C14-C22 fatty acid ester, polyoxyethylenated C14-C22 fatty acid ester, and mixtures thereof, is less than 2.5, preferably less than 1.8.
Composition according to any of claims 1 to 6, wherein the C-glycoside is selected from compounds of formula (I) :

in which:

- R represents a saturated C₁ to C₁₀, in particular C₁ to C₄, alkyl radical which can optionally be substituted by at least one radical selected from OH, COOH or COOR”₂, with R”₂ being a saturated C₁-C₄ alkyl radical,

- S represents a monosaccharide or a polysaccharide comprising up to 20 sugar units, in particular up to 6 sugar units, in pyranose and/or furanose form and of the L and/or D series, it being possible for the said monosaccharide or polysaccharide to be substituted by a hydroxyl group which is necessarily free and optionally one or more optionally protected amine functional group (s) , and

- X represents a radical selected from the–CO-, -CH (OH) -, -CH (NH₂) -, -CH (NHCH₂CH₂CH₂OH) -, -CH (NHPh) -and–CH (CH₃) -groups and in particular a–CO-, -CH (OH) -or–CH (NH₂) -radical and more particularly a–CH (OH) -radical,

the S-CH₂-X bond represents a bond of C-anomeric nature, which can be α or β,

and also their physiologically acceptable salts, their solvates, such as the hydrates, and their optical and geometrical isomers.
Composition according to any of claims 1 to 7, wherein the C-glycoside is selected from

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

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

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

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

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

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

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

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

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

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

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

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

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

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

- C-α-D-maltopyranoside-2-hydroxypropane,

their isomers and their mixtures.
Composition according to any of claims 1 to 8, wherein the C-glycoside is present in the composition in an amount ranging from 8 wt. %to 30%, preferably from 9 wt. %to 20 wt. %, more preferably from 9.5 wt. %to 15 wt. %, relative to the total weight of the composition.
Composition according to any of claims 1 to 9, wherein the niacinamide derivative is selected from 2-chloronicotinamide, 6-methylnicotinamide, 6- aminonicotinamide, N-methylnicotinamide, N, N-dimethylnicotinamide, N- (hydroxymethyl) nicotinamide, quinolinic acid imide, nicotinanilide, N-benzylnicotinamide, N-ethylnicotinamide, nifenazone, nicotinaldehyde, isonicotinic acid, methylisonicotinic acid, thionicotinamide, nialamide, 2-mercaptonicotinic acid, nicomol, niaprazine, methyl nicotinate, sodium nicotinate, and a mixture thereof.
Composition according to any of claims 1 to 10, wherein niacinamide and/or a derivative thereof is present in an amount ranging from 2 wt. %to 20 wt. %, preferably from 3 wt. %to 15 wt. %, and more preferably from 4 wt. %to 10 wt. %, relative to the total weight of the composition.
Composition according to any of claims 1 to 11, wherein the composition comprises an aqueous phase in an amount ranging from 10 wt. %to 85 wt. %, more preferably from 20 wt. %to 85 wt. %, relative to the total weight of the composition.
Composition according to any of claims 1 to 12, wherein the composition comprises an oily phase in an amount ranging from 1 wt. %to 30 wt. %, preferably from 5 wt. %to 20 wt. %, relative to the total weight of the composition.
Composition according to claim 1, comprising, relative to the total weight of the composition:

(i) from 1 wt. %to 7 wt. %of at least one saturated C14-C22 fatty acid selected from myristic acid, palmitic acid, stearic acid, and combinations thereof;

(ii) from 0.8 wt. %to 12 wt. %of at least one nonionic surfactant selected from glyceryl stearate, glyceryl isostearate, glyceryl palmitate, glyceryl myristate, and esters of polyethylene glycol comprising from 20 to 100 oxyethylene groups and a C14-C22 fatty acid selected from myristic acid, palmitic acid, stearic acid and isostearic acid, and combinations thereof;

(iii) from 8 wt. %to 15 wt. %of hydroxypropyl tetrahydropyrantriol; and

(iv) from 4 wt. %to 10 wt. %of niacinamide.
A non-therapeutic method for caring for and/or making up keratin materials, comprising applying the composition according to any of claims 1 to 14 to the keratin materials.