WO2024065606A1

WO2024065606A1 - Composition for caring for keratin materials

Info

Publication number: WO2024065606A1
Application number: PCT/CN2022/123071
Authority: WO
Inventors: Xinxin Chen; Shanshan ZANG; Yao GU
Original assignee: LOreal SA
Current assignee: LOreal SA
Priority date: 2022-09-30
Filing date: 2022-09-30
Publication date: 2024-04-04
Anticipated expiration: 2025-03-30
Also published as: FR3141855A1; FR3141855B1; CN119968193A

Abstract

A composition for caring for keratin materials comprises: (i) carageenan; (ii) at least one alkoxylated silicone phosphate; and (iii) at least one C-glycoside. A non-therapeutic method for keratin materials comprises applying the composition to the keratin materials.

Description

COMPOSITION FOR CARING FOR KERATIN MATERIALS

TECHNICAL FIELD

The present invention relates to a cosmetic composition. In particular, the present invention relates to a composition for caring for keratin materials. The present invention also relates to a non-therapeutic method for caring for keratin materials.

BACKGROUND ART

The skin is the protective barrier for the human body. It protects the interior of the body from physical injury (such as trauma) and biological injury (such as bacteria, viruses or fungi) .

The development of formulations dedicated to caring for the skin and/or lips, is permanent.

In cosmetic industry, hydroxypropyl tetrahydropyrantriol is a well-known ingredient which can immediately improve skin quality, result in good moisturizing and rejuvenate skin after long-term usage.

For example, WO2013034855A2 discloses a combination of carrageenan and c-glycoside and uses thereof. The combination can be used for improving the barrier function or the biomechanical properties of the skin.

Recently, consumers have become increasingly demanding on skin quality improvement.

In order to meet the higher demand, higher concentration of hydroxypropyl tetrahydropyrantriol is added into some cosmetic products to result in stronger anti-aging efficacy, but it will bring unpleasant skin sensory during application.

It is desired to have cosmetic products, which are effective in anti-aging while can deliver a good skin sensory during application.

SUMMARY OF THE INVENTION

The inventors have now discovered that it is possible to formulate compositions effective in anti-aging while can deliver a good skin sensory during application.

Accordingly, in a first aspect, the present invention provides a composition for caring for keratin materials, comprising:

(i) carrageenan;

(ii) at least one alkoxylated silicone phosphate; and

(iii) at least one C-glycoside selected from compounds of formula (I) :

in which:

- R represents a saturated C ₁ to C ₁₀, in particular C ₁ to C ₄, 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 C ₁-C ₄ 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 (NH ₂) -, -CH (NHCH ₂CH ₂CH ₂OH) -, -CH (NHPh) -and–CH (CH ₃) -groups and in particular a–CO-, -CH (OH) -or–CH (NH ₂) -radical and more particularly a–CH (OH) -radical,

the S-CH ₂-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.

The inventors found that the composition of the present invention is effective in anti-aging while can deliver a good skin sensory during application.

In a second aspect, the present invention provides a non-therapeutic method for caring for keratin materials, comprising applying the composition according to the first aspect of the present invention to the keratin materials.

Other advantages of the present 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" .

Throughout the instant application, the term “comprising” is to be interpreted as encompassing all specifically mentioned features as well as 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.

For the purposes of the present invention, the term “keratin materials” is intended to cover human skin, mucous membranes such as the lips. Facial skin is most particularly considered according to the present invention.

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

According to the first aspect, the present invention provides a composition for caring for keratin materials, comprising:

(i) carrageenan;

(ii) at least one alkoxylated silicone phosphate; and

(iii) at least one C-glycoside.

Carrageenan

According to the first aspect, the composition of the present invention comprises carrageenan.

Carrageenans are sulfated polysaccharides which constitute the cell walls of various red algae, from which they may be obtained. Among these red algae mention may be made in a nonlimiting manner of Kappaphycus alvarezii, Eucheuma denticulatum, Eucheuma spinosum, Chondrus crispus, Betaphycus gelatinum, Gigartina skottsbergii, Gigartina canaliculata, Sarcothalia crispata, Mazzaella laminaroides, Hypnea musciformis, Mastocarpus stellatus and Iridaea cordata.

Carrageenans comprise long galactan chains formed by disaccharide units. These polysaccharides are composed of an alternation of (1→3) β-D-galactopyranose (G unit) and (1→4) α-galactopyranose (D unit) or 3, 6-anhydro-a-galactopyranose (AnGal unit) . Each sugar unit may be sulfated one or more times in position 2, 3, 4 or 6. Methyl and pyruvic acid groups may also be found, along with other sugar units grafted onto the base structures described previously. Carrageenans were initially subdivided into subfamilies as a function of their solubility in KCI and then accordingto the number and position of the sulfate groups and the presence of 3', 6'-anhydro bridges on the galactopyranosyl residues. At least 15 carrageenans are listed, the structure of which depends on the alga of origin and on the extraction method. Amongthe most common, mention may be made of the following carrageenans: μ-carrageenan ( (1→3) β-D-galactopyranose-4-sulfate- (1→4) -α-D-galactopyranose-6-sulfate) , κ-carrageenan ( (1→3) β-D-galactopyranose-4-sulfate- (1→4) 3, 6-anhydro-α-D-galactopyranose) , v-carrageenan ( (1→3) β-D-galactopyranose-4-sulfate- (1→4) -α-D-galactopyranose-2, 6-disulfate) , τ-carrageenan ( (1→3) β-D-galactopyranose-4-sulfate- (1→4) 3, 6-anhydro-α-D-galactopyranose-2-sulfatesulfate) ) , λ-carrageenan ( (1→3) β-D-galactopyranose-2-sulfate- (1→4) -α-D-galactopyranose-2, 6-disulfate) , θ-carrageenan ( (1→3) β-D-galactopyranose-2-sulfate- (1→4) 3, 6-anhydro-α-D-galactopyranose-2-sulfate.

These carrageenans may be obtained in the form of mixtures of different structures such as, in a non-limiting manner, mixtures of the κβ, κι and κμ forms.

Carrageenans that may be used may be selected especially from carrageenans of the μ, κ, v, ι or λ type, and mixtures thereof in all proportions, preferably λ type.

Carrageenans that are particularly suitable for use in the invention are carrageenans of lambda, kappa or iota form, hybrids thereof, and mixtures thereof in all proportions. Use will be made especially of carrageenans of λ form, of K form and/or of ιform, or mixtures thereof.

The carrageenans of the present invention may be used in acid form or in salified form. Acceptable salts that may be mentioned in a non-limiting manner include lithium, sodium, potassium, calcium, zinc and ammonium salts or the salts obtained with an organic base counterion, such as a primary, secondary or tertiary (C1-C6) alkylamine, especially 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 functions; mention may be made especially of amino-2-methyl-2-propanol, triethanolamine and dimethylamino-2-propanol. Mention may also be made of lysine or 3- (dimethylamino) propylamine. These sulfated polysaccharides may also comprise a mixture of counterions among those defined above in a non-limiting manner.

The molecular weight of the carrageenans that are useful for the present invention is between 300 and 100 x 10 ⁶daltons. Their molecular weight is preferentially between 10x 10 ³ Da and 10x10 ⁶ Da.

The sulfur content of the carrageenans is preferentially between 5%and 25% (calculated on a weight basis relative to the total weight of the carrageenan) and more preferentially between 7%and 20%. Carrageenans may especially have a sulfur content from about 15%to 20%.

Preferably, carrageenans used in the invention predominantly comprise lambda (λ) forms, or are in lambda (λ) form. The term "predominantly" means that the percentage of this type of chain in the composition of the product is greater than or equal to 50%, this proportion possibly being greater than or equal to 80%in certain embodiments. Such carrageenans may be that sold under the names SATIAGUM ^TM VPC 410 by the company Cargill.

Preferably, the carrageenan is present in the composition accordingto the present invention in an amount rangingfrom 0.05 wt. %to 15 wt. %, preferablyfrom 0.1 wt. %to 10 wt. %, and more preferably from 0.1 wt. %to 5 wt. %, relative to the total weight of the composition.

Alkoxylated silicone phosphates

According to the first aspect, the composition of the present invention comprises at least one alkoxylated silicone phosphate.

Suitable alkoxylated silicone phosphates for use in the composition of the present invention are selected from silicone compounds comprising at least one phosphate group and at least one alkoxylated chain. Such silicone phosphates may be selected from those which are water soluble, oil soluble, water-dispersible and/or soluble in organic solvents.

The at least one phosphate group in the alkoxylated silicone phosphates of the present invention may be selected from terminal phosphate groups and pendant phosphate groups.

Further, the at least one phosphate group may be selected from groups of formula -O-P (O) (OH) ₂, groups of formula-OP (O) (OH) (OR) , and groups of formula-O-P (O) (OR) ₂, wherein R may be selected from H, inorganic cations, and organic cations. Non-limiting examples of inorganic cations include alkali metals, such as, potassium, lithium, and sodium. A non-limiting example of organic cation is at least one additional silicone compound which may be identical to or different from the at least one silicone compound bonded to the other oxygen of the phosphate group.

Preferably, the alkoxylated silicone phosphate is selected from silicone compounds of formula (A) and salts thereof:

wherein:

a is an integer ranging from 0 to 200;

b is an integer ranging from 2 to 500;

R is selected from-OH, and alkyl groups containing 1 to 9 carbon atoms;

R' is represented by formula (B) :

-R"- (EO) _c- (PO) _d- (EO) _e-R"' (B)

wherein

R" is selected from alkylene groups containing 1 to 10 carbon atoms;

c, d, and e, which may be identical or different, are each integers ranging from 0 to 20 with the proviso that the sum c+d+e is at least 1;

R"' is a phosphate group selected from groups of formula-OP (O) (OH) ₂, groups of formula-O-P (O) (OH) (OR1) , and groups of formula-O-P (O) (OR1) ₂, wherein R1 is selected from hydrogen, inorganic cations, and organic cations.

More preferably, the alkoxylated silicone acid is selected from dimethicone PEG-8 phosphate, dimethicone PEG-7 phosphate and combinations thereof.

Non-limiting examples of suitable alkoxylated silicone phosphates include those commercially available from the company Phoenix Chemical, Inc. of New Jersey under the name of

such as

PS-100,

PS-112,

PS-150,

PS-200,

WDS-100,

WDS-200,

PS-100 B, and

PS-100 K, those commercially available from the company LUBRIZOL under the name of SILSENSE PE-200L SILICONE, and those commercially available from the company Siltech under the name Silphos A-100 and Silphos A-150. Other non-limiting examples of suitable alkoxylated silicone phosphates include those described in U.S. Patent Nos. 5,070,171, 5,093,452, and 5,149,765 the disclosures of which are incorporated herein by reference.

Advantageously, the alkoxylated silicone phosphate is present in the composition according to the present invention in an amount ranging from 0.1 wt. %to 20 wt. %, preferably from 0.5 wt. %to 10 wt. %, more preferably from 1 wt. %to 5 wt. %, relative to the total weight of the composition.

C-glycosides

According to the first aspect, the composition of the present invention comprises at least one C-glycoside selected from compounds of formula (I) :

in which:

the S-CH ₂-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.

The C-glycoside of use for the implementation of the invention are in particular those for which R denotes a saturated linear C ₁ to C ₆, in particular C ₁ to C ₄, preferentially C ₁ to C ₂, 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, S can 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 C ₁-C ₄, in particular C ₁-C ₂, 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 (NH ₂) -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, NH ₄OH, 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 according to the present invention in an amount ranging from 0.1 wt. %to 40%, preferably from 0.5 wt. %to 25 wt. %, and more preferably from 1 wt. %to 15 wt. %, relative to the total weight of the composition.

Unexpectedly, the inventors have found that carrageenan and alkoxylated silicone phosphate, especially, dimethicone PEG-7 phosphate work together to boost the anti-aging efficacy of C-glycoside, especially, hydroxypropyl tetrahydropyrantriol, so as to provide better anti-aging efficacy, meanwhile this combination can further provide better skin sensory during application.

Anti-redness active ingredients

Preferably, the composition according to the present invention comprises an anti-redness active ingredient.

As examples of anti-redness active ingredients, mention can be made to madecassoside, saccharide isomerate, palmitoyl tripeptide-8, panthenol, olea europaea (olive) leaf extract, mentha piperita (peppermint) extract, leontopodium alpinum extract, dipotassium glycyrrhizate, acetyl dipeptide-1 cetyl ester, acetyl tetrapeptide-15, boswellia serrata extract, sodium palmitoyl proline (and) nymphaea alba flower extract.

In some embodiments, the composition of the present invention comprises at least one anti-redness active ingredient selected from madecassoside, saccharide isomerate, palmitoyl tripeptide-8, panthenol, olea europaea (olive) leaf extract, Mentha piperita (peppermint) extract, leontopodium alpinum extract, dipotassium glycyrrhizate, acetyl dipeptide-1 cetyl ester, acetyl tetrapeptide-15, boswellia serrata extract, sodium palmitoyl proline (and) nymphaea alba flower extract, and a combination thereof.

In some embodiments, the composition of the present invention comprises leontopodium alpinum extract, in particular, leontopodium alpinum callus culture extract, as anti-redness active ingredient.

If presents, advantageously, the anti-redness active ingredient is present in the composition according to the present invention in an amount ranging from 0.01 wt. %to 20%, preferably from 0.1 wt. %to 10 wt. %, and more preferably from 0.5 wt. %to 5 wt. %, relative to the total weight of the composition.

Truffle extracts

Preferably, the composition of the present invention comprises a truffle extract.

Truffle is the common name given to the edible fruiting body of an ectomycorrhizal ascomyscetes fungus which takes a more or less globular form. The fungus may produce several truffles.

The truffle (s) which may be used within the context of the invention are preferentially truffles of the genus Tuber, of the Tuberaceae family, in the Pezizales order. There are more than a hundred species thereof. Among the latter, mention may especially be made of black (Périgord) truffle (Tuber melanosporum) , white (Piedmont) truffle (Tuber magnatum) , white (summer) truffle (Tuber aestivum) , winter truffle (Tuber Brumale) , bianchetto truffle (Tuber borchii) , or else Chinese truffles (Tuber sinensis and Tuber indicum) .

According to one particular embodiment, the truffle (s) used within the context of the invention are selected from white truffles and black truffles. According to a preferred embodiment, the truffle (s) used within the context of the invention are black (Périgord) truffle (Tuber melanosporum) , white (summer) truffle (Tuber aestivum) , or a mixture of the two.

Within the context of the invention, the truffle extract (s) may especially be obtained from an extraction solvent by using an extraction technique selected from the extraction techniques well known from the prior art.

Generally, the extraction solvent is chosen from water, water-soluble or water-miscible solvents (hydrophilic solvents) , and mixtures thereof.

Among the hydrophilic solvents, mention may especially be made of substantially linear or branched lower monoalcohols having from 1 to 8 carbon atoms, such as ethanol, propanol, butanol, isopropanol or isobutanol; polyols, such as propylene glycol, isoprene glycol, butylene glycol, propylene glycol, glycerol, sorbitol, polyethylene glycols and derivatives thereof; and mixtures thereof.

When the extraction solvent is water, the truffle extract is said to be aqueous.

When the extraction solvent is a substantially linear or branched lower monoalcohol having from 1 to 8 carbon atoms, the truffle extract is said to be alcoholic.

When the extraction solvent is a polyol, the truffle extract is said to be glycolic.

When the extraction solvent is a mixture of water and of one or more substantially linear or branched lower monoalcohols having from 1 to 8 carbon atoms, the extract is said to be aqueous-alcoholic.

When the extraction solvent is a mixture of water and of one or more polyols, the extract is said to be aqueous-glycolic.

Within the context of the invention, the truffle extract (s) are obtained from an extraction solvent comprising water. The truffle extract (s) are then aqueous, aqueous-alcoholic or aqueous-glycolic. Preferably, the truffle extract (s) are aqueous or aqueous-glycolic.

If presents, advantageously, the truffle extract is present in the composition according to the present invention in an amount ranging from 0.01 wt. %to 15%, preferably from 0.05 wt. %to 10 wt. %, and more preferably from 0.05 wt. %to 5 wt. %, relative to the total weight of the composition.

Aqueous phase

The composition of the present invention may comprise an aqueous phase.

Said aqueous phase comprises water.

Preferably, the aqueous phase comprises an organic solvent miscible with water (at room temperature 25℃) selected from ethanol, glycols and 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; and mixtures thereof, so as to provide a hydration effect.

If presents, advantageously, the organic solvent miscible with water selected from ethanol, glycols and polyols is present in the composition in an amount ranging from 0.5 wt. %to 20 wt. %, preferably from 1 wt. %to 10 wt. %, relative to the total weight of the composition.

Preferably, the aqueous phase of the composition of the present invention comprises water, ethanol, and glycerin.

If presents, advantageously, aqueous phase is present in the composition of the present invention in an amount ranging from 50 wt. %to 95 wt. %, preferably from 70 wt. %to 90 wt. %, relative to the total weight of the composition.

Oily phase

The composition of the present invention may comprise an oily phase.

Said oily phase comprises an oil.

The oil can be volatile or non-volatile.

The term “oil” means a water-immiscible non-aqueous compound that is liquid at room temperature (25℃) and at atmospheric pressure (760 mmHg) . The term “non-volatile oil” means an oil that may remain on keratin materials at room temperature and atmospheric pressure for at least several hours and that especially has a vapour pressure of less than 10 ^-3 mmHg (0.13 Pa) . A non-volatile oil may also be defined as having an evaporation rate such that, under the conditions defined previously, the amount evaporated after 30 minutes is less than 0.07 mg/cm ².

The oils may be of plant, mineral or synthetic origin.

Said oil can be selected from hydrocarbonated, silicone or fluorinated oils.

The term “hydrocarbon-based oil” means an oil formed essentially from, or even constituted by, carbon and hydrogen atoms, and optionally O and N atoms, and free of Si and F heteroatoms. Such oil can contain alcohol, ester, ether, carboxylic acid, amine and/or amide groups.

The term “silicone oil” means an oil containing at least one silicon atom, especially containing Si-O groups.

The term “fluorinated oil” means an oil containing at least one fluorine atom.

Preferably, the oil is selected from hydrocarbon-based oils, and silicone oils, such as dimethicone.

If presents, advantageously, the oily phase is present in the composition of the present invention in an amount ranging from 1 wt. %to 20 wt. %, preferably from 2 wt. %to 10 wt. %, relative to the total weight of the composition of the present invention.

Additional cosmetic active ingredients

The composition of the present invention may comprise one or more additional cosmetic active ingredient different from C-glycoside, anti-redness active ingredients and truffle extract.

As examples of cosmetic active ingredient, mention can be made of vitamins such as vitamin A (retinol) , vitamin E (tocopherol) , vitamin C (ascorbic acid) , vitamin B5 (panthenol) , vitamin B3 (niacinamide) , and derivatives of said vitamins (in particular esters) and mixtures thereof; urea; caffeine; salicylic acid and derivatives thereof; alpha-hydroxyacids such as lactic acid or glycolic acid and derivatives thereof; sunscreens; extracts from algae, fungi, plants, yeasts and bacteria; enzymes; other moisturing agents such as hydroxyethyl urea, agents acting on the microcirculation, and mixtures thereof.

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

Additional adjuvants or additives

The composition of the present invention may also comprise conventional cosmetic adjuvants or additives, for instance, surfactants, fragrances, preserving agents (for example, chlorphenesin and phenoxyethanol) and bactericides, pH regulators (for example citric acid) , thickeners (such as xanthan gum and carbomer) , and mixtures thereof.

The skilled in the art can select 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 for caring for keratin materials comprising, relative to the total weight of the composition:

(i) from 0.1 wt. %to 5 wt. %of carrageenan;

(ii) from 1 wt. %to 5 wt. %of at least one alkoxylated silicone phosphate selected from dimethicone PEG-8 phosphate, dimethicone PEG-7 phosphate and combinations thereof;

(iii) from 1 wt. %to 15 wt. %of at least one C-glycoside selected from C-β-D-xylopyranoside-2-hydroxypropane or C-α-D-xylopyranoside-2-hydroxypropane, and combinations thereof;

(iv) from 0.5 wt. %to 5 wt. %of leontopodium alpinum callus culture extract; and

(iv) from 0.05 wt. %to 5 wt. %of tuber aestivum extract.

Galenic form and method

The composition of the present invention may be in the form of emulsion, such as gel, cream, or lotion.

The composition of the present invention can be used for caring for keratin materials.

According to the second aspect, the present invention provides a non-therapeutic method for caring for keratin materials, comprising applying the composition according to the first aspect of the present invention to the keratin materials.

The following examples serve to illustrate the present invention without, however, being limiting in nature.

EXAMPLES

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

Table 1

Invention example 1 and comparative examples 1-2

Compositions of invention example (IE. ) 1 and comparative examples (CE. ) 1-2 were prepared according to the amounts given in Table 2. The amount of each component is given in%by weight of the total weight of the composition containing it.

Table 2

Composition of invention example 1 is composition according to the present invention.

Composition of comparative example 1 does not comprise carrageenan.

Composition of comparative example 2 does not comprise an alkoxylated silicone phosphate.

Preparation process:

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

1) . adding water, glycerin, phenoxyethanol, carbomer, and carrageenan into a main vessel and heating up to 75℃ with stirring to obtain an uniform mixture;

2) . cooling the uniform mixture to around 60℃ in the main vessel;

3) . premixing dimethicone and squalane in another container with stirring to obain an uniform oil phase; and transferring the oil phase into the main vessel when the temperature of the uniform mixture in the main vessel is around 60℃, stirring for 10 minutes to obtain an uniform combination;

4) . cooling the uniform combination from 60℃ to 30℃;

5) . adding triethanolamine into the main vessel when the temperature in the main vessel is 40℃;

6) . adding hydroxypropyl tetrahydropyrantriol, dimethicone PEG-7 phosphate, leontopodium alpinum callus culture extract, tuber aestivum extract into the vessel below 40℃ with stirring,

7) . adding ethanol below 30℃ with stirring to obtain the composition of invention example 1.

Evaluation

Viscosity

The viscosity of a composition was measured at 25℃ upon preparation using a Rheomat 100 Plus viscometer equipped with a spindle M2, the measurement being performed after 10 minutes of rotation of the spindle in a composition (after which time stabilization of the viscosity and of the spin speed of the spindle are observed) , at a shear rate of 200 rpm.

Stability

The stability was evaluated as follows:

1) filling 40 mL of the sample into a 60 mL glass bottle and preparing 7 bottles for each composition to be tested;

2) putting one bottle under UV light (for UV-test) , one bottle at room temperature, one bottle into a refrigerator at 4℃, one bottle into an oven at 37℃, one bottle into an oven at 45℃, and one bottle into an oven at 55℃ (for stability tests at different temperatures) , and one bottle into an oven with the temperature cycling from-20℃ to 20℃ (for cycle stability) ; and

3) observing the samples’ appearance after 24 hours for the UV stability test, 2 months for stability tests at room temperature, 4℃, 37℃, and 45℃, 1 week for stability test at 55℃, or 10 days for cycle stability test.

The stability of a composition will be evaluated as stable if its appearance, color, and odor do not show visible change, and its viscosity and pH as well as particle sizes of emulsified droplets do not change more than 7%after all of the stability tests mentioned above, otherwise, it will be evaluated as unstable.

The results on viscosity and stability of each composition prepared above were summarized in Table 3.

Table 3

Properties	IE. 1	CE. 1	CE. 2
Viscosity (UD)	40	40	40
Stability	Stable	Stable	Stable

Cosmetic Performance (Anti-aging Efficacy and Skin Sensory)

10 female consumers were invited to use the composition to be evaluated once in the morning and once at night for one day and evaluated the composition in terms of anti-aging efficay (including radiant skin, firming skin, and skin feels softer) and skin sensory (including better penetration and better skin affinity) , then gave the scores (1-10) based on the following standard. The scores were averaged.

The results of cosmetic performance were summarized in Table 4 below.

Table 4

It can be seen from Table 3 that during application, composition of invention example 1 performed better on penetration and skin affinity, as compared with compositions of comparative examples 1 and 2.

It can be also seen from Table 3 that after usage, composition of invention example 1 performed better on anti-aging efficacy in terms of more radiant/firming/soft skin, as compared with compositions of comparative examples 1 and 2.

Claims

A composition for caring for keratin materials, comprising:

(i) carrageenan;

(ii) at least one alkoxylated silicone phosphate; and

(iii) at least one C-glycoside selected from compounds of formula (I) :

in which:

- R represents a saturated C ₁ to C ₁₀, in particular C ₁ to C ₄, 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 C ₁-C ₄ 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 (NH ₂) -, -CH (NHCH ₂CH ₂CH ₂OH) -, -CH (NHPh) -and–CH (CH ₃) -groups and in particular a–CO-, -CH (OH) -or–CH (NH ₂) -radical and more particularly a –CH (OH) -radical,

the S-CH ₂-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 claim 1, wherein the carrageenan is selected from carrageenans of the μ, κ, v, i or λ type, and mixtures thereof in all proportions, preferably carrageenans of λ type.
Composition according to claim 1 or 2, wherein the carrageenan is present in an amount ranging from 0.05 wt. %to 15 wt. %, preferably from 0.1 wt. %to 10 wt. %, and more preferably 0.1 wt. %to 5 wt. %, relative to the total weight of the composition.
Composition according to any of claims 1 to 3, wherein the alkoxylated silicone phosphate is selected from silicone compounds of formula (A) and salts thereof:

wherein:

a is an integer ranging from 0 to 200;

b is an integer ranging from 2 to 500;

R is selected from -OH, and alkyl groups containing 1 to 9 carbon atoms;

R' is represented by formula (B) :

-R"- (EO) _c- (PO) _d- (EO) _e-R"' (B)

wherein

R" is selected from alkylene groups containing 1 to 10 carbon atoms;

c, d, and e, which may be identical or different, are each integers ranging from

0 to 20 with the proviso that the sum c+d+e is at least 1;

R"' is a phosphate group selected from groups of formula -OP (O) (OH) ₂, groups of formula -O-P (O) (OH) (OR1) , and groups of formula -O-P (O) (OR1) ₂, wherein R1 is selected from hydrogen, inorganic cations, and organic cations.
Composition according to any of claims 1 to 3, wherein the alkoxylated silicone acid is selected from dimethicone PEG-8 phosphate, dimethicone PEG-7 phosphate and combinations thereof.
Composition according to any of claims 1 to 5, wherein the alkoxylated silicone phosphate is present in an amount ranging from 0.1 wt. %to 20 wt. %, preferably from 0.5 wt. %to 10 wt. %, more preferably from 1 wt. %to 5 wt. %, relative to the total weight of the composition.
Composition according to any of claims 1 to 6, 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 7, wherein the C-glycoside is present in an amount ranging from 0.1 wt. %to 40%, preferably from 0.5 wt. %to 25 wt. %, and more preferably from 1 wt. %to 15 wt. %, relative to the total weight of the composition.
Composition according to any of claims 1 to 7, further comprising an anti-redness active ingredient selected from madecassoside, saccharide isomerate, palmitoyl tripeptide-8, panthenol, olea europaea (olive) leaf extract, mentha piperita (peppermint) extract, leontopodium alpinum extract, dipotassium glycyrrhizate, acetyl dipeptide-1 cetyl ester, acetyl tetrapeptide-15, boswellia serrata extract, sodium palmitoyl proline (and) nymphaea alba flower extract, leontopodium alpinum callus culture extract and a combination thereof.
Composition according to claim 9, wherein the anti-redness active ingredient is present in an amount ranging from 0.01 wt. %to 20%, preferably from 0.1 wt. %to 10 wt. %, and more preferably from 0.5 wt. %to 5 wt. %, relative to the total weight of the composition.
Composition according to any of claims 1 to 10, further comprising a truffle extract, wherein the truffle is selected from white truffles and black truffles such as black (Périgord) truffle (Tuber melanosporum) , white (summer) truffle (Tuberaestivum) and mixtures thereof.
Composition according to claim 11, wherein the truffle extract is present in an amount ranging from 0.01 wt. %to 15 wt. %, preferably from 0.05 wt. %to 10 wt. %, and more preferably from 0.05 wt. %to 5 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 0.1 wt. %to 5 wt. %of carrageenan;

(ii) from 1 wt. %to 5 wt. %of at least one alkoxylated silicone phosphate selected from dimethicone PEG-8 phosphate, dimethicone PEG-7 phosphate and combinations thereof;

(iii) from 1 wt. %to 15 wt. %of at least one C-glycoside selected from C-β-D-xylopyranoside-2-hydroxypropane or C-α-D-xylopyranoside-2-hydroxypropane, and combinations thereof;

(iv) from 0.5 wt. %to 5 wt. %of leontopodium alpinum callus culture extract; and

(iv) from 0.05 wt. %to 5 wt. %of tuber aestivum extract.
A non-therapeutic method for caring for keratin materials, comprising applying the composition according to any of claims 1 to 13 to the keratin materials.