Makeup process involving the application of a composition comprising a polyphenol, a polyglycerol compound, and a coloring agent, followed by the application of an anhydrous composition.

A makeup process using polyphenols and polyglycerol esters forms a durable coating on skin and lips, addressing the challenge of balancing performance, natural ingredients, and comfort in cosmetic products.

FR3134981B1Active Publication Date: 2025-04-18LOREAL SA
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Patent Information

Application Number
FR2022004041
Authority / Receiving Office
FR · FR
Patent Type
Patents
Current Assignee / Owner
Filing Date
2022-04-28
Publication Date
2025-04-18
Estimated Expiration
2042-04-28

AI Technical Summary

Technical Problem

Existing cosmetic products for long-lasting makeup on skin and lips struggle to balance high performance with natural ingredients, environmental impact, and comfort while maintaining resistance to external factors like water, sebum, and mechanical friction.

Method used

A makeup process using polyphenols with multiple phenol groups and polyglycerol esters forming a coating in situ, combined with an anhydrous composition, to create a hydrogen bond interaction for enhanced durability and comfort.

Benefits of technology

The process achieves long-lasting makeup that is resistant to mechanical friction, meals, water, sweat, and sebum, while maintaining comfort and using natural ingredients.

✦ Generated by Eureka AI based on patent content.
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Abstract

Title: Makeup process with the application of a composition comprising a polyphenol and a polyglycerol compound, and a coloring material followed by the application of an anhydrous composition. The invention relates to a makeup process for the skin and / or lips, consisting of carrying out the following steps: 1) a coating agent formed in situ or previously by hydrogen bonding interaction of at least one polyphenol X comprising at least two different phenol groups with at least one compound Y chosen from polyglycerol esters comprising 2 to 20 glycerol motifs is applied to the skin and / or lips; this step taking place in the presence of at least one coloring material; 2) an anhydrous composition (M) is applied to the skin and / or lips thus treated.
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Description

Title of the invention: Make-up process with the application of a composition comprising a polyphenol and a polyglycerolated compound, and a coloring material then application of an anhydrous composition

[0001] The subject of the present invention is a process for making up the skin and / or the lips, in several stages, in which a coating agent formed in situ or previously is used, by interaction by hydrogen bond(s) of at least one polyphenol X comprising at least two different phenol groups with at least one compound Y chosen from polyglycerol esters comprising 2 to 20 glycerol units, in the presence of at least one coloring matter, followed by the application of an anhydrous composition.

[0002] Today on the skin and / or lip care and / or makeup market, many products claim to last all day, resistant to external factors such as water, sebum, food, mechanical friction, etc. These "long-lasting" products for the lips, or for the face, which can be used at home, are mainly based on synthetic coating polymers in the presence of organic solvents, most of the time volatile oils. For example, compositions are known comprising a silicone resin as a coating agent, such as for example trimethylsiloxysilicate resins (INCI name) or polypropylsilses-quioxane (INCI name) or even comprising silicone polymers such as silicone acrylate dendrimer copolymers (acrylates / polytrimethylsiloxy-methacrylate copolymer - INCI name).

[0003] For several years now, consumers have become increasingly demanding about the composition of their cosmetic products and are particularly seeking to use products containing an increasingly high content of natural or naturally derived ingredients, ingredients with a minimized environmental impact and / or ingredients that are compatible with numerous packaging options.

[0004] The difficulty remains, however, in reconciling these latest trends with the fact that consumers do not want to give up the very high performance to which they have become accustomed with the products they already use.

[0005] The aim of the present invention is to propose compositions allowing excellent hold of the expected cosmetic effects, in particular the color of the makeup of the skin, the lips, which are resistant to mechanical friction, meals, water, sweat and perspiration, sebum, oil, or even cleaning products, in particular makeup removal products, such as certain micellar waters, makeup remover wipes. bowling pins, for example.

[0006] Furthermore, the present invention aims to provide compositions and application methods providing hold to expected cosmetic effects, in particular the color of the makeup, associated with an acceptable level of comfort.

[0007] These and other objectives are achieved by implementing the process for making up the skin and / or lips, preferably the lips, consisting of implementing the following steps 1) a coating agent formed in situ or previously by interaction via hydrogen bonds of at least one polyphenol X comprising at least two different phenol groups with at least one compound Y chosen from polyglycerol esters comprising 2 to 20 glycerol units is applied to the skin and / or the lips; this step taking place in the presence of at least one coloring matter; 2) an anhydrous composition (M) is applied to the skin and / or lips thus treated.

[0008] Other aspects and advantages of the present invention will appear more clearly on reading the description and examples which follow.

[0009] In the context of the present invention, it is indicated that the skin designates the skin of the face (cheeks, eyelids, eye contour), the body, the hands.

[0010] The makeup and / or skin and / or lip care compositions according to the invention are cosmetic compositions. This implies that they advantageously comprise a physiologically acceptable medium. By "physiologically acceptable" is meant compatible with the skin and / or lips, which has a pleasant color, odor and feel and which does not generate unacceptable discomfort (tingling, tightness), likely to deter the consumer from using this composition.

[0011] For the purposes of the invention, the term "hydrogen bond interaction" means an interaction involving a hydrogen atom of one of the two reactants and an electronegative heteroatom of the other reactant such as oxygen, nitrogen, sulfur and fluorine. In the context of the invention, the hydrogen bond(s) is(are) made between the hydroxyl function(s) (OH) of the reactive phenol group(s) of the polyphenol X and the hydroxyl group(s) of the compounds Y capable of reacting by hydrogen bond(s) with the polyphenol X.

[0012] By “room temperature” we mean 25°C.

[0013] By “atmospheric pressure” we mean 760 mm of Hg or 1,013.105 Pascals.

[0014] POLYPHENOL X

[0015] The polyphenols X which can be used according to the present invention comprise at least two different phenol groups in their structure.

[0016] By "polyphenol" is meant any compound having in its chemical structure at least at least two benzene compounds, in free or condensed form, each benzene compound comprising at least one hydroxyl group (OH), preferably at least 2 hydroxyl groups, or even 3 hydroxyl groups.

[0017] By “different phenol groups” is meant chemically different phenol groups.

[0018] The polyphenols X that can be used according to the invention can be synthetic or natural. They can be in the isolated state or contained in a mixture, in particular contained in a plant extract. The polyphenols are phenols comprising at least two phenolic groups differently substituted on the aromatic cycle.

[0019] The two classes of polyphenols are flavonoids and non-flavonoids.

[0020] Examples of flavonoids include chalcones such as phloretin, phloridzin, aspalathin or neohesperidin; flavanols such as catechin, fisetin, kaempferol, myricetin, quercetin, rutin, procyanidins, proanthocyanidins, pyroanthocyanidins, theaflavins or thearubigins (or thearubrins); dihydroflavonols such as astilbin, dihydroquercetin (taxifolin), or silibinin; flavanones such as hesperidin, neohesperidin, hesperetin, naringenin, naringin; anthocyanins such as cyanidin, delphinidin, malvidin, peonidin or petunidin; catechin tannins such as tannic acid; isoflavonoids such as daidzein, or genistein; neo-flavanoids; lignans such as pyroresorcinol; and mixtures thereof.

[0021] Among the natural polyphenols X that can be used according to the invention, mention may also be made of lignins.

[0022] Examples of non-flavonoids include curcuminoids such as curcumin or tetrahydrocurcumin; stilbenoids such as astringin, resveratrol or rhaponticin; aurones such as aureusidin; and mixtures thereof.

[0023] As polyphenols X which can be used according to the invention, mention may also be made of chlorogenic acid, verbascoside; coumarins substituted by phenols.

[0024] According to a particular embodiment of the invention, the polyphenol will be chosen from catechic tannins such as gallotannins chosen from tannic acid; ellagitannins such as epigallocatechin, epigallocatechin gallate, castalagin, vescalagin, vescaline, castaline, casuarictin, castanopsins, excoecarianins, grandinin, gradinin, roburines, pterocarinin, acutissimin, tellima-grandins, sanguiin, potentillin, pedunculagin, geraniin, chebulagic acid, diffusisinic acid, ascorgeraniin, stachyurin, casuarinin, casuariin, punicacortein, coriariin, cameliatannin, isodehydrodigalloyl, dehydrodigalloyl, hellinoyl, punicalagin, rhoipteleanins.

[0025] According to a particular embodiment of the invention, the polyphenol X is epigallocatechin, in particular a green tea extract with the INCI name GREEN TEA EXTRACT, in particular comprising at least 45% epigallocatechin relative to the total weight of said extract such as the commercial product sold under the name DERMOFEEL PHENON 90 MC® sold by the company Evonik Nutrition & Care or the commercial product sold under the name TEA POLYPHENOLS GREEN TEA EXTRACT® by the company Tayo Green Power.

[0026] According to a particular embodiment of the invention, polyphenol X is a procyanidin or a mixture of procyanidins, in particular an extract of maritime pine bark with the INCI name PINUS PINASTER BARK / BUD EXTRACT, in particular comprising at least 65% by weight of procyanidins relative to the total weight of said extract such as the commercial product sold under the name PYCNOGENOL® sold by the company BIOLANDES AROMES.

[0027] Tannic acid will be used more particularly as polyphenol X. This compound is notably marketed under the name Brewtan F by the company AJINOMOTO OMNICHEM Nv.

[0028] Y COMPOUNDS

[0029] Compound Y is a compound capable of forming at least two hydrogen bonds with said phenol groups of the aforementioned polyphenol X. Compound Y is chosen from polyglycerol esters comprising 2 to 20 glycerol units.

[0030] According to a particular embodiment, the compound(s) Y, in the medium of the composition, do not comprise an anionic group in their chemical structure, and in particular are non-ionic.

[0031] In a preferred embodiment, the composition comprises compounds Y whose molar mass is greater than 200 g / mol, or even greater than 350 g / mol.

[0032] More particularly, the compounds Y are chosen from polyglycerol esters comprising 2 to 20 glycerol units and carboxylic acid(s) or polymer(s) of carboxylic acid(s), saturated or unsaturated, comprising 6 to 40 carbon atoms, preferably 8 to 30 carbon atoms, or polyglycerol esters comprising 2 to 20 glycerol units and derived from vegetable oils, as well as mixtures thereof. Preferably, the compounds Y are chosen from polyglycerol esters comprising 2 to 20 glycerol units and carboxylic acid(s), saturated or unsaturated, comprising 6 to 40 carbon atoms, preferably 8 to 30 carbon atoms, or derived from vegetable oils, and mixtures thereof. The carboxylic acids may also comprise 1 to 3 carboxylic groups, and are preferably monocarboxylic acids. The polyglycerolated compounds are more particularly mono-, di- or triesters.

[0033] The composition comprises at least one compound Y, advantageously it comprises at least two, or even three compounds Y.

[0034] As examples of compounds Y, the following compounds may be mentioned, designated by their INCI name: Polyglyceryl-2 Stearate, Polyglyceryl-2 IsostearatCi Polyglyceryl-2 Diisostearate, Polyglyceryl-3 Diisostearate, Polyglyceryl-3 Dicitrate / Stearate, Poly-glyceryl-4 Diisostearate, Polyglyceryl-4 Caprate, Polyglyceryl-4 Laurate^ Poly-glyceryl-5 Laurate, Poylglyceryl-5 oleate, Polyglyceryl-6 Caprylate, Polyglyceryl-6 dicaprate, Polyglyceryl-6 Distearate, Polyglyceryl-6 Caprylate / Caprate, Polyglyceryl-6 Dioleate, Polyglyceryl-6 trilaurate, Polyglyceryl-10 Laurate, Polyglyceryl-10 Dioleate, polyglycerol esters of apricot kernel oil (Apricot Kernel Oil) including 3 to 10 patterns glycerol, as well as mixtures thereof.

[0035] COMPOSITION (A) COMPRISING POLYPHENOL(S) X

[0036] More particularly, the composition (A) has a content of polyphenol(s) X of at least 2% by weight, relative to the weight of the composition (A). Preferably the content of polyphenol(s) X is between 2 and 50% by weight, preferably between 5 and 30% by weight relative to the total weight of the composition (A).

[0037] According to a first embodiment of the invention, the composition (A) comprises water. It may be, for example, demineralized water, or a floral water such as cornflower water and / or a mineral water such as VITTEL water, LUCAS water or LA ROCHE POSAY water and / or a thermal water. More particularly, the water content is greater than or equal to 25% by weight, or even greater than 30% by weight, and more preferably ranging from 35 to 85% relative to the total weight of the composition (A).

[0038] Composition (A) may also comprise at least one C2-C8 monoalcohol, preferably C2-C5. Examples that may be mentioned are ethanol, isopropanol, butanol, and preferably ethanol, isopropanol and even more preferably ethanol.

[0039] Preferably, the content of C2-C8 monoalcohol, preferably C2-C5, and more particularly ethanol, is greater than 25% by weight, or even greater than 30% by weight, and more preferably ranging from 35 to 85% relative to the total weight of composition (A).

[0040] The pH of composition (A) is preferably less than 8.0, more preferably less than 7.0, and more particularly varies from 2 to 6.

[0041] Composition (A) may optionally comprise other ingredients or solvents soluble or miscible in water (miscibility in water greater than 50% by weight at 25°C) such as polyols having from 3 to 8 carbon atoms such as propylene glycol, 1,3-butylene glycol, caprylyl glycol, pentylene glycol, glycerin, di-propylene glycol; C3-C4 ketones, C2-C4 aldehydes.

[0042] According to another particular embodiment of the invention, composition (A) is anhydrous.

[0043] The term “anhydrous composition” means any composition comprising less than 5% by weight of water, or even less than 2% by weight, or even less than 1% by weight; relative to the total weight of the composition, or even free of water. Preferably, water is not deliberately added to the composition but may be present in small quantities, or even in trace amounts, in the various products used.

[0044] According to another particular embodiment of the invention, the composition (A) comprises an oily phase.

[0045] The term “oily phase” means a liquid phase at room temperature and atmospheric pressure comprising at least one fatty substance, different from the Y compounds, such as oils, waxes, pasty substances as well as possibly all organic solvents and ingredients which are soluble or miscible in said phase.

[0046] Oils

[0047] The oil or oils may be chosen from volatile or non-volatile, polar or apolar hydrocarbon oils, silicone oils, and mixtures thereof.

[0048] By "oil" is meant a fatty substance that is liquid at room temperature (25°C) and atmospheric pressure (760 mm Hg or 1,013.105 Pa). The oil may be volatile or non-volatile.

[0049] For the purposes of the present invention, the term “silicone oil” means an oil comprising at least one silicon atom, and in particular at least one Si-O group, and more particularly an organopolysiloxane.

[0050] The term "hydrocarbon oil" means an oil containing mainly hydrogen and carbon atoms and optionally one or more functions chosen from hydroxyl, ester, ether, carboxylic functions. These oils are therefore distinct from silicone oils.

[0051] For the purposes of the invention, the term "volatile oil" means any oil capable of evaporating on contact with the skin in less than one hour, at room temperature and atmospheric pressure. Volatile oil is a volatile cosmetic compound, liquid at room temperature, having in particular a non-zero vapor pressure, at room temperature and atmospheric pressure, in particular having a vapor pressure ranging from 2.66 Pa to 40,000 Pa, in particular ranging from 2.66 Pa to 13,000 Pa, and more particularly ranging from 2.66 Pa to 1,300 Pa.

[0052] By "non-volatile oil" is meant an oil remaining on the skin at room temperature and atmospheric pressure for at least several hours and having in particular a vapor pressure of less than 2.66 Pa, preferably less than 0.13 Pa. For example, the vapor pressure can be measured using the static method or by the isothermal thermogravimetry effusion method, according to the vapor pressure (OECD standard 104).

[0053] Volatile hydrocarbon oils

[0054] Among the volatile hydrocarbon oils, mention may be made more particularly of those chosen from hydrocarbon oils of the hydrocarbon type (therefore hydro oils apolar carbonaceous oils, consisting solely of carbon and hydrogen) as well as ester type oils. In particular, they can be chosen from volatile hydrocarbon oils having from 8 to 16 carbon atoms and mixtures thereof, and in particular: - branched C8-Ci6 alkanes such as isoalkanes (also called isoparaffins), isododecane, isodecane, isohexadecane, and mixtures thereof, and for example oils sold under the trade names Isopars or Permetyls, - linear alkanes, for example Cn-Ci5, alone or in mixtures, - branched C8-Ci6 esters, for example isohexyl neopentanoate, - mixtures thereof.

[0055] Other volatile hydrocarbon oils such as petroleum distillates, in particular those sold under the name Shell or by the company SHELL, can also be used; volatile linear alkanes such as those described in the patent application of the company Cognis DE10 2008 012 457.

[0056] Volatile silicone oils

[0057] Among the volatile silicone oils, mention may be made, inter alia, of linear, branched or cyclic silicone oils such as polydimethylsiloxanes (PDMS) having from 3 to 7 silicon atoms, preferably linear or branched polydimethylsiloxanes having from 3 to 7 silicon atoms; as well as their mixtures.

[0058] As examples of such oils, mention may be made of octyltrimethicone, hexyltrimethicone, methyl trimethicone, decamethylcyclopentasiloxane, octamethylcyclotetrasiloxane, dodecamethylcyclohexasiloxane, decamethyltetrasiloxane, polydimethylsiloxanes such as those marketed under the reference DC 200 (1.5 cSt), DC 200 (3 cSt) by Dow Corning, or KF 96 A from Shin Etsu; alone or in mixtures.

[0059] Polar non-volatile hydrocarbon oils

[0060] By "polar hydrocarbon oil" is meant an oil containing mainly hydrogen and carbon atoms and also comprising at least one oxygen atom. More particularly, such an oil comprises one or more functions chosen from hydroxyl, ester, ether, carboxylic functions, and preferably hydroxyl, ester, ether.

[0061] As an example of non-volatile hydrocarbon oil that can be used in the invention, mention may be made of: - triglycerides consisting of esters of fatty acids and glycerol, in particular the fatty acids of which may have chain lengths varying from C4 to C36, and in particular from C18 to C36, these oils being able to be linear or branched, saturated or unsaturated; these oils may in particular be heptanoic or octanoic triglycerides, wheat germ, sunflower, grape seed, sesame, corn, apricot, castor, shea, avocado, olive, soybean, sweet almond, palm oils, rapeseed, cotton, hazelnut, macadamia, jojoba, alfalfa, poppy, pumpkin, squash, blackcurrant, evening primrose, millet, barley, quinoa, rye, safflower, candlenut, passionflower, musk rose; shea oil; or caprylic / capric acid triglycerides such as those sold by the company Stéa-rineries Dubois or those sold under the names Miglyol 810®, 812® and 818® by the company Dynamit Nobel; - linear aliphatic hydrocarbon esters of formula RCOOR' in which RCOO represents a carboxylic acid residue containing from 2 to 40 carbon atoms, and R' represents a hydrocarbon chain containing from 1 to 40 carbon atoms, with at least one such as cetostearyl octanoate, esters of isopropyl alcohol such as isopropyl myristate, isopropyl palmitate, ethyl palmitate, 2-ethylhexyl palmitate, isopropyl stearate or isostearate, isostearyl isostearate, octyl stearate, heptanoates, and in particular isostearyl heptanoate, octanoates, decanoates or ricinoleates of alcohols or polyalcohols such as dioctanoate of propylene glycol, cetyl octanoate, tridecyl octanoate, 2-ethylhexyl palmitate, alkyl benzoate, hexyl laurate, neopentanoic acid esters such as isodecyl neopentanoate, isotridecyl neopentanoate, isostearyl neopentanoate,octyl-2-docecyl neopentanoate, isononanoic acid esters such as isononyl isononanoate, isotridecyl isononanoate, octyl isononanoate, oleyl erucate; isocetyl stearate, isodecyl neopentanoate, isostearyl behenate; , - polyesters obtained by condensation of dimer and / or trimer of unsaturated fatty acid and diol such as those described in patent application FR 0 853 634, such as in particular dilinoleic acid and 1,4-butanediol. In this respect, mention may in particular be made of the polymer marketed by Biosynthis under the name Viscoplast 14436H® (INCI name: Dilinoleic Acid / Butane diol Copolymer), or copolymers of polyols and diacid dimers, and their esters, such as Hailuscent ISDA®; - esters and polyesters of linear fatty acids having a total carbon number ranging from 35 to 80 such as pentaerythrityl tetrapelargonate, pentaerythrityl tetraisostearate; - aromatic esters and polyesters such as tridecyl trimellitate, C12-C15 alcohol benzoate, 2-phenyl ethyl ester of benzoic acid, butyl octyl salicylate; - esters and polyesters of dimer diol and mono- or dicarboxylic acid, such as esters of dimer diol and fatty acid and esters of dimer diols and dimer dicarboxylic acid, for example with INCI name: Dimer Dilinoleyl Dimer Dilinoleate, such as Lusplan DD-DA5® and Lusplan DD-DA7® marketed by the company NIPPON FINE CHEMICAL and described in application US 2004-175338, the content of which is incorporated into this application by reference; - fatty alcohols having 12 to 26 carbon atoms such as octyldodecanol, 2-butyloctanol, 2-hexyl decanol, 2-undecyl pentadecanol, oleyl alcohol; - synthetic ethers having 10 to 40 carbon atoms such as dicaprylyl ether; - di-alkyl carbonates, the 2 alkyl chains being able to be identical or different, such as dicaprylyl carbonate marketed under the name Cetiol CC®, by Cognis; - and their mixtures.

[0062] Non-volatile apolar hydrocarbon oils

[0063] The oil may also be chosen from non-volatile, linear or branched, saturated or unsaturated, and preferably saturated, apolar hydrocarbon oils.

[0064] The non-volatile, linear or branched, apolar hydrocarbon oil(s) are more particularly compounds comprising only carbon and hydrogen atoms (in other words, non-volatile hydrocarbon-type oils).

[0065] Said apolar, linear or branched oils can be of mineral or synthetic origin such as for example: - paraffin oil, - squalane, - isoeicosane, - mixtures of linear, saturated hydrocarbons, more particularly in C15-C2s, such as mixtures whose INCI names are for example the following: C15-19 Alkane (INCI name), C18-21 Alkane (INCI name), C21-28 Alkane (INCI name), such as for example the products Gemseal 40, Gemseal 60, Gemseal 120 marketed by Total, Emogreen L19 marketed by SEPPIC, - polybutenes, hydrogenated or not, such as, for example, products from the Indopol range marketed by the company INEOS Oligomers, - polyisobutenes, hydrogenated or not, such as for example the non-volatile compounds of the Parléam® range marketed by the company NIPPON OIL FATS, - polydecenes, hydrogenated or not, such as, for example, non-volatile compounds from the PURESYN® range marketed by the company Exxonmobil), - and their mixtures.

[0066] Non-volatile silicone oils

[0067] The non-volatile oil may also be chosen from phenylated or non-phenylated non-volatile silicone oils. More particularly, said silicone oils are free of (poly)alkoxylated groups such as in particular (poly)ethoxylated or (poly)propoxylated groups, or of (poly)glycerolated groups.

[0068] For the purposes of the invention, the term “silicone oil” means an oil comprising at least one silicon atom, and in particular at least one Si-O group.

[0069] More particularly, the non-volatile silicone oil, phenylated or non-phenylated, is chosen from dimethicones, trimethyl pentaphenyl trisiloxane, tetramethyl tetraphenyl trisiloxane, diphenyl dimethicone, trimethylsiloxyphenyl di-methicone, phenyltrimethicone, diphenylsiloxy phenyl trimethicone, as well as mixtures thereof.

[0070] These products are notably marketed under the names PH-1555 HRI Cosmetic Fluid (Trimethyl Pentaphenyl Trisiloxane), Dow Corning 556 Cosmetic Grade Fluid (Phenyltrimethicone) by Dow Corning; Diphenyl Dimethicone such as the products KF-54, KF54HV, KF-50-300CS, KF-53 d, KF-50-100CS or Diphenylsiloxy Phenyl Trimethicone KF56 A marketed by Shin Etsu, marketed by Shin Etsu; the products Belsil PDM 1000, Belsil PDM 20 marketed by Wacker Chemie (Trimethylsiloxy Phenyl Dimethicone), alone or in mixtures. The values ​​in parentheses represent the viscosities at 25°C (ASTM D-445 standard).

[0071] When composition (A) is anhydrous, preferably, the oily phase comprises at least one volatile hydrocarbon oil, more preferably chosen from C8-C16 isoalkanes of petroleum origin such as isodecane, isododecane, isohexadecane, and more particularly isododecane.

[0072] Waxes

[0073] The composition may optionally comprise at least one wax.

[0074] For the purposes of the present invention, the term "wax" means a lipophilic compound, solid at 25°C, with a reversible solid / liquid state change, having a melting point greater than or equal to 40°C and up to 120°C.

[0075] For the purposes of the invention, the melting temperature corresponds to the temperature of the most endothermic peak observed in thermal analysis (DSC) as described in the ISO 11357-3; 1999 standard. The melting temperature of the wax can be measured using a differential scanning calorimeter (DSC), for example the calorimeter sold under the name "DSC Q2000" by the company TA Instruments.

[0076] The measurement protocol is as follows: A wax sample of approximately 5 mg is placed in a crucible "hermetic aluminum capsule. The sample is subjected to a first temperature rise from -20°C to 120°C, at a heating rate of 10°C / minute, then is cooled from 120°C to -20°C at a cooling rate of 10°C / minute and finally subjected to a second temperature rise from -20°C to 120°C at a heating rate of 5°C / minute. During the second temperature rise, the melting temperature value of the solid fatty substance is measured, which corresponds to the value of the top of the most endothermic peak of the melting curve observed, representing the variation of the difference in absorbed power as a function of temperature.

[0077] The waxes can be hydrocarbon, silicone, and be of vegetable, mineral, animal and / or synthetic origin.

[0078] More particularly, the waxes are chosen from apolar hydrocarbon waxes, polar hydrocarbon waxes, preferably esters, as well as their mixtures.

[0079] Among the apolar hydrocarbon waxes (i.e. comprising only carbon and hydrogen atoms in their structure), mention may in particular be made of polyethylene waxes, microcrystalline waxes, paraffin waxes, ozokerite, polymethylene waxes, waxes obtained by Fischer-Tropsch synthesis, microwaxes, in particular of polyethylene, as well as their mixtures.

[0080] Among the polar hydrocarbon waxes (therefore comprising carbon, hydrogen and oxygen atoms), waxes advantageously comprising at least one alcohol, ester and / or ether group are suitable.

[0081] In particular, hydrocarbon waxes such as beeswax, lanolin wax; sunflower wax, rice wax, carnauba wax, candelilla wax, ouricury wax, japan wax, berry wax, shellac wax and sumac wax; montane wax, as well as mixtures thereof, may be used as wax.

[0082] Mention may also be made of waxes obtained by catalytic hydrogenation of animal or vegetable oils having linear or branched fatty chains, in C8-C32. Among these, mention may in particular be made of hydrogenated jojoba oil, hydrogenated palm oil, hydrogenated sunflower oil, hydrogenated castor oil, hydrogenated coconut oil and hydrogenated lanolin oil, di-(trimethyloi-1,1,1 propane) tetrastearate sold under the name "HEST 2T-4S®" by the company HETERENE, di-(trimethyloi-1,1,1 propane) tetrabehenate sold under the name HEST 2T-4B® by the company HETERENE.

[0083] Also suitable are waxes of the C2o-C4o alkyl (hydroxystearyloxy)stearate type, alone or as a mixture, or a C2o-C4O alkyl stearate. Such waxes are sold in particular under the names “Kester Wax K 82 P®”, “Hydroxypolyester K 82 P®”, “Kester Wax K 80 P®”, or “KESTER WAX K82H” by the company KOSTER KEUNEN.

[0084] As alcohol wax, mention may be made of mixtures of linear, saturated C30-C50 alcohols such as, for example, Performacol 550-L Alcohol wax from New Phase Technologie, stearic alcohol and cetyl alcohol.

[0085] Pasty compounds

[0086] For the purposes of the present invention, the term "pasty compound" means a lipophilic fatty compound with a reversible solid / liquid state change, and comprising at a temperature of 20°C a liquid fraction and a solid fraction. Thus, a pasty compound may have an initial melting temperature of less than 20°C. Furthermore, the A pasty compound may have an anisotropic crystalline organization in the solid state. The melting point of the pasty fatty substance is determined according to the same principle as that detailed previously for waxes.

[0087] In the case of a pasty compound, the measurement protocol is however as follows: A sample of 5 mg of pasty fatty substance placed in a crucible is subjected to a first temperature rise ranging from -20°C to 100°C, at a heating rate of 10°C / minute, then is cooled from 100°C to -20°C at a cooling rate of 10°C / minute and finally subjected to a second temperature rise ranging from -20°C to 100°C at a heating rate of 5°C / minute. The melting point of the pasty fat is the temperature value corresponding to the top of the peak of the curve representing the variation of the difference in absorbed power as a function of temperature. It should be noted that the liquid fraction by weight of the pasty fatty substance at room temperature is equal to the ratio of the enthalpy of fusion consumed at room temperature to the enthalpy of fusion of the pasty fatty substance. The heat of fusion of a pasty fat is the heat consumed by the fat to change from a solid to a liquid state. A pasty fat is said to be in a solid state when its entire mass is in crystalline solid form. A pasty fat is said to be in a liquid state when its entire mass is in liquid form. The enthalpy of fusion of the pasty fat is the amount of energy required to transform the pasty fat from the solid state to the liquid state. It is expressed in J / g. The enthalpy of fusion of the pasty fat is equal to the value under the curve of the thermogram obtained.

[0088] Preferably, this or these pasty hydrocarbon compounds are chosen from:

[0089] - vegetable butters, such as for example mango butter, such as that com marketed under the reference Lipex® 203 by the company AARHUSKARLSHAMN, shea butter, in particular that whose INCI name is Butyrospermum Parkii ButteR, such as that marketed under the reference Sheasoft® by the company AARHUSKARLSHAMN, cupuacu butter (Rain forest RF3410 from the company Beraca Sabara), murumuru butter (RAIN FOREST RF3710 from the company Beraca Sabara), cocoa butter, babassu butter such as that marketed under the name Cropure® Babassu by Croda, as well as orange wax such as, for example, that marketed under the reference Orange Peel Wax by the company Koster Keunen,

[0090] - partially hydrogenated vegetable oils, such as soybean oil hydrogenated, hydrogenated coconut oil, hydrogenated rapeseed oil, mixtures of hydrogenated vegetable oils such as the mixture of hydrogenated vegetable oil of soybean, copra, palm and rapeseed, for example the mixture marketed under the reference Akogel® by the company AARHUSKARLSHAMN (INCI name Hydrogenated Vegetable Oil), partially hydrogenated trans isomerized jojoba oil manufactured or marketed by the company Desert Whale under the commercial reference Iso-Jojoba-50®, partially hydrogenated olive oil such as, for example, the compound marketed under the reference Beurrolive by the company Soliance,

[0091] - esters of hydrogenated castor oil and C16-C22 fatty acids, in particular isostearic acid such as the compound with the INCI name Hydrogenated Castor Oil Isostearate, for example SALACOS HCIS (VL) sold by the company NISSHIN OIL,

[0092] - triglycerides of fatty acids, saturated or not, linear or branched, optionally mono or poly-hydroxylated, preferably C12-C18, optionally hydrogenated (totally or partially); such as for example the glycerides of saturated fatty acids C12-C18 marketed under the name Softisan 100® by the company Cremer Oleo (INCI name: Hydrogenated Coco-Glycerides),

[0093] - polyesters resulting from the condensation of a linear or branched dicarboxylic acid in C6-C10 and of diglycerol ester and monocarboxylic acids, optionally hydroxylated, linear or branched, in C6-C20, such as in particular the ester obtained by condensation of adipic acid and a mixture of diglycerol esters with a mixture of C6-C20 fatty acids such as caprylic acid, capric acid, stearic acid, isostearic acid and 12-hydroxystearic acid, and of INCI name Bis-Diglyceryl Polyacyladipate-2. This type of compound is notably marketed under the reference Softisan® 649 by the company Cremer Oleo.

[0094] - polyesters obtained from an acid dimer, said acid being unsaturated and comprising from 16 to 24 carbon atoms, and at least one alcohol or polyol, such as for example: * esters of dimer diol (e.g. dilinoleic alcohol) and dilinoleic acid whose hydroxyl groups are esterified by a mixture of phytosterols, behenyl alcohol and isostearyl alcohol, for example the ester sold under the name Plandool G by the company Nippon Fine Chemical (INCI name: Bis-Behenyl / Isostearyl / Phytosteryl Dimer Dilinoleyl Dimer Dilinoleate); * esters of dilinoleic acid and a mixture of phytosterols, isostearyl alcohol, cetyl alcohol, stearyl alcohol and behenyl alcohol, for example the ester sold under the name Plandool H or Plandool S by the company Nippon Fine Chemical (INCI name: Phytosteryl / Isostearyl / Cetyl / Stearyl / Behenyl Dimer Dilinoleate); * esters of hydrogenated castor oil and dilinoleic acid, such as those sold under the names RISOCAST-DA-L or RISOCASTDA-H by the company KOKYU ALCOHOL KOGYO (INCI name: Hydrogenated Castor Oil Dimer Di- linoleate).

[0095] Preferably, if the composition comprises them, the pasty hydrocarbon compound(s) are chosen from vegetable butters, partially hydrogenated vegetable oils, compounds with the INCI name Phytosteryl / Isostearyl / Cetyl / Stearyl / Behenyl Dimer Dilinoleate, Hydrogenated Coco-Glycerides, Bis-Diglyceryl Polyacyladipate-2 and mixtures thereof.

[0096] When composition (A) is anhydrous, the concentration in oily phase of said composition is preferably greater than or equal to 5% by weight, more particularly greater than 10% by weight, and more particularly varies from 20 to 85% by weight relative to the total weight of the composition relative to the total weight of composition (A).

[0097] Preferably, if the composition (A) comprises an oily phase, the latter comprises at least one non-volatile polar hydrocarbon oil. It preferably does not contain any silicone oil, volatile or non-volatile.

[0098] COMPOSITION (B) COMPRISING THE Y COMPOUNDS

[0099] Preferably, the content of compounds Y represents at least 1% by weight, more particularly from 1 to 75% by weight, preferably from 2 to 50% by weight relative to the total weight of the composition (B).

[0100] According to a first embodiment of the invention, the composition (B) comprising the compound(s) Y comprises at least water. It may be, for example, demineralized water, or else floral water such as cornflower water and / or mineral water such as VITTEL water, LUCAS water or LA ROCHE POSAY water and / or thermal water.

[0101] The quantity of water is preferably greater than or equal to 25% by weight, or even greater than 30% by weight, and more preferably ranging from 35 to 85% by weight, relative to the total weight of composition (B).

[0102] Composition (B) may also comprise at least one C2-C8 monoalcohol, preferably C2-C5. Examples that may be mentioned include ethanol, isopropanol, butanol, and preferably ethanol, isopropanol, preferably ethanol.

[0103] Preferably, the content of C2-C8 monoalcohol, preferably C2-C5, and more particularly ethanol, is greater than 25% by weight, or even greater than 30% by weight, and more preferably ranging from 35 to 85% relative to the total weight of composition (B).

[0104] The pH of composition (B) is preferably less than 8.0, more preferably less than 7.0, and more particularly varies from 2 to 6.

[0105] Composition (B) may optionally comprise other ingredients or solvents soluble or miscible in water (miscibility in water greater than 50% by weight at 25°C) such as polyols having from 3 to 8 carbon atoms such as propylene glycol, 1,3-butylene glycol, caprylyl glycol, pentylene glycol, glycerin, dipropylene glycol; C3-C4 ketones, C2-C4 aldehydes.

[0106] According to another embodiment of the invention, composition (B) is anhydrous.

[0107] According to another embodiment, composition (B) may comprise at least an oily phase as defined previously.

[0108] When composition (B) is anhydrous, preferably, the oily phase comprises at least one volatile hydrocarbon oil, more preferably chosen from C8-C16 isoalkanes of petroleum origin (also called isoparaffins) such as isodecane, isohexadecane, isododecane and more particularly isododecane.

[0109] When composition (B) is anhydrous, the concentration in oily phase of the composition of the invention is preferably greater than or equal to 5% by weight, more particularly greater than 10% by weight, and more particularly varies from 20 to 85% by weight relative to the total weight of composition (B).

[0110] Preferably, if composition (B) comprises an oily phase, the latter comprises at least one non-volatile polar hydrocarbon oil. It preferably does not contain any silicone oil, volatile or non-volatile.

[0111] Of course, those skilled in the art will take care to choose the compositions (A) and (B) so that they are compatible and can be mixed and the quantities make it possible to obtain in the mixture obtained, the formation of a coating agent by interaction by hydrogen bonds of the polyphenol X with the compounds Y as defined.

[0112] COMPOSITION (C)

[0113] The present invention also relates to a composition (C) comprising, in particular in a physiologically acceptable medium, at least one coating agent previously formed by interaction by hydrogen bonds of at least one polyphenol X with at least two compounds Y, as defined previously.

[0114] Pre-formed coating agent

[0115] The coating agent present in the compositions of the invention is obtained by reacting by interaction via hydrogen bonds, at room temperature and atmospheric pressure, at least one polyphenol X comprising at least two different phenol groups with at least two compounds Y chosen from polyglycerol esters, preferably non-ionic, comprising 2 to 20 glycerol units; both previously described; these compounds being as described previously.

[0116] Advantageously, the content of pre-formed coating agent varies from 1 to 60% by weight, more preferably ranging from 2 to 40% by weight, preferably ranging from 10 to 40% by weight relative to the total weight of the composition (C).

[0117] Process for preparing the coating agent

[0118] The reaction medium may be aqueous, hydrophilic or anhydrous. Ideally the solvent in which the preparation of the coating agent is carried out is easily removable, in particular by evaporation. Thus, the coating agent can advantageously be synthesized in water or in a volatile oil such as those indicated above, preferably isododecane.

[0119] The polyphenol X and the compounds Y are preferably introduced into the reaction medium with a ratio of the mass of polyphenol X, expressed as active material, to the mass of the compounds Y, expressed as active material, varying between 0.25 and 3, preferably between 0.5 and 2.

[0120] The order of introduction does not matter. The contact time can be very rapid or it can be left to incubate with shaking (a few hours).

[0121] The precipitate obtained corresponding to the coating agent is recovered either by filtration of the solvent or centrifugation or by evaporation of the solvent.

[0122] The precipitate is then washed several times so as to remove the initial reagents which were not involved in the formation of the precipitate. The washing solvent is more particularly chosen from the solvents of polyphenol X and / or the associated compounds Y. Ideally, the washing solvent is water.

[0123] The number of washes can be determined by measuring the polyphenol X recovered in the wash water. When the level is low, it can be considered that the excess reagents have been eliminated. The quantity of solvent present in the precipitate is more particularly less than 40% by weight relative to the weight of the precipitate, or even less than 35% by weight relative to the weight of the precipitate.

[0124] The precipitate can then be dried, in particular in the open air, under a heated atmosphere, under vacuum or freeze-dried.

[0125] According to a particular embodiment of the invention, composition (C) comprises at least water. This may in particular be demineralized water, or else floral water such as cornflower water and / or mineral water such as VITTEL water, LUCAS water or LA ROCHE POSA Y water and / or thermal water.

[0126] Depending on the nature of the aqueous composition (C), the quantity of water is preferably greater than 30% by weight, or even greater than 40% by weight, and more preferably ranging from 30 to 75% by weight relative to the total weight of the composition (C).

[0127] The composition comprises at least one coloring material which will be described later.

[0128] According to another particular embodiment, the composition (C) may comprise at least one oily phase as defined previously.

[0129] According to a particular embodiment of the invention, composition (C) is anhydrous.

[0130] According to another particular embodiment, the composition (C) may be in a multiphase form, for example in the form of an oil-in-water emulsion (continuous aqueous phase in which an oily phase is dispersed in the form of droplets so as to obtain a macroscopically homogeneous mixture), in the form of an emulsion water-in-oil (continuous oil phase in which an aqueous phase is dispersed in the form of droplets so as to obtain a macroscopically homogeneous mixture).

[0131] When composition (C) contains water, the pH of the aqueous phase is preferably less than 8.0, more preferably less than 7.0, and more particularly varies from 2 to 6.

[0132] When composition (C) comprises an oily phase, the latter comprises at least one oil

[0133] When the composition (C) comprises an oily phase, the concentration of oily phase is preferably greater than 10% by weight, or even greater than 20% by weight, and more preferably varies from 30 to 75% relative to the total weight of the composition (C).

[0134] Preferably, if the composition (C) comprises an oily phase, the latter comprises at least one non-volatile polar hydrocarbon oil. It preferably does not contain any silicone oil, volatile or non-volatile.

[0135] When composition (C) is an emulsion, it may comprise one or more emulsifying surfactants.

[0136] For the purposes of the present invention, the term “emulsifying surfactant” means an amphiphilic surfactant compound, i.e. one having two parts of different polarity. In general, one is lipophilic (soluble or dispersible in an oily phase. The other is hydrophilic (soluble or dispersible in water). Emulsifying surfactants are characterized by their HLB (Hydrophilic Lipophilic balance) value, HLB being the ratio of the hydrophilic part to the lipophilic part in the molecule. The term HLB is well known to those skilled in the art and is described for example in “The HLB System. A time-saving guide to Emulsifier Selection” (published by ICI Americas Inc.; 1984). For emulsifying surfactants, HLB generally ranges from 3 to 8 for the preparation of water-in-oil (W / O) emulsions. HLB is greater than 8 for the preparation of O / W emulsions.The HLB of the surfactant(s) used according to the invention can be determined by the GRIFFIN method or the DA VIES method.

[0137] According to a preferred form of the invention, when the composition (C) is anhydrous, the oily phase of the composition (C) comprises at least one volatile hydrocarbon oil, preferably chosen from hydrocarbon oils having from 8 to 16 carbon atoms, and in particular C8-C16 isoalkanes of petroleum origin (also called isoparaffins) such as isododecane, isodecane, isohexadecane, and particularly isododecane.

[0138] The quantity of volatile hydrocarbon oil(s) may preferably range from 20% to 80% by weight, and even more preferably from 30% to 70% by weight, relative to the total weight of said composition (C).

[0139] According to a preferred embodiment of the invention, in order to improve the dispersibility of the coating agent homogeneously in the composition (C), a thickening system (polymers, waxes or pasty bodies), a suspending agent or an emulsifying system, in particular of the lamellar phase type, can be added.

[0140] COMPOSITION (D)

[0141] Another subject of the invention relates to a composition (D) comprising, in particular in a physiologically acceptable medium, a) at least one polyphenol X as defined above, b) at least two compounds Y as defined above, and c) at least one mono-alcohol comprising from 2 to 8 carbon atoms, more particularly comprising from 2 to 5 carbon atoms, and preferably ethanol, isopropanol, even more preferably ethanol, (d) at least one coloring matter.

[0142] In this composition, the coating agent is in a latent state and only appears completely in situ, that is to say once the composition (D) has been applied to the skin and / or the lips. In other words, in the composition (D), before its application, the conditions (ingredients, contents) are such that they do not promote the interaction of the polyphenol(s) X and compound(s) Y with each other. Preferably, these compounds do not precipitate in the composition before its application.

[0143] Preferably, the content of polyphenol X in composition (D) is at least 2% by weight, preferably between 2 and 30% by weight, and even more particularly from 3 to 25% by weight, relative to the total weight of said composition (D).

[0144] Preferably, the content of compounds Y in composition (D) represents at least 1% by weight, more particularly at least 2% by weight, preferably from 2 to 40% and even more preferably from 3 to 35% by weight relative to the total weight of said composition.

[0145] More particularly, the ratio of the mass of polyphenol(s) X, expressed as active material, to the mass of compounds Y, expressed as active material, varies between 0.25 and 3, preferably between 0.5 and 2.

[0146] Advantageously, the content of C2-C8 mono-alcohol, more particularly C2-C5, in particular ethanol, is such that compounds X and Y do not react in composition (D) before its application. Said mono-alcohol can thus be considered as a hydrogen bond inhibitor. By "hydrogen bond inhibiting agent" is meant any compound capable of preventing the interaction by hydrogen bonds between polyphenol X and compounds Y and / or of dissociating the complex formed by said interaction by breaking the hydrogen bonds. More particularly, the content of C2-C8 mono-alcohol is at least 25% by weight, in particular comprised between 25 and 98% by weight, more particularly between 30 and 85% by weight and even more particularly between 35 and 80% by weight, relative to the total weight of said composition (D).

[0147] According to a first embodiment of the invention, composition (D) comprises water. Here again, it may be demineralized water, or floral water such as cornflower water and / or mineral water such as VITTEL water, LUCAS water or LA ROCHE POSA Y water and / or thermal water.

[0148] More particularly, the composition (D) comprises a water content of less than or equal to 10% by weight, more particularly less than or equal to 5% by weight, relative to the total weight of said composition. According to a particularly advantageous embodiment of the invention, the water content of the composition (D) is between 0 and 5% by weight, limits included, relative to the total weight of said composition.

[0149] If the composition comprises water, then the pH of the aqueous phase is advantageously less than 8.0, more preferably less than 7.0, and more particularly varies from 2 to 6.

[0150] The composition may optionally comprise other ingredients or solvents soluble or miscible in water (miscibility in water greater than 50% by weight at 25°C) such as polyols having from 3 to 8 carbon atoms such as propylene glycol, 1,3-butylene glycol, caprylyl glycol, pentylene glycol, glycerin, di-propylene glycol; C3-C4 ketones, C2-C4 aldehydes.

[0151] According to a particular embodiment of the invention, the composition (D) comprises an oily phase.

[0152] Reference may be made to the definition of the oily phase detailed previously during the description of composition (A).

[0153] More particularly, when composition (D) comprises it, the oily phase content is between 1 and 30% by weight, preferably between 1 and 25% by weight, relative to the total weight of said composition.

[0154] According to a first variant of the invention, if the oily phase is present in the composition, then it comprises at least one non-volatile oil.

[0155] Preferably, according to this variant, the oil(s) are chosen from non-volatile polar hydrocarbon oils. Preferably, the non-volatile oil is not chosen from non-volatile silicone oils.

[0156] According to another embodiment of the invention, the oily phase is present and comprises at least one volatile oil, preferably hydrocarbon-based. More particularly, the content of volatile oil, preferably hydrocarbon-based, is less than or equal to 20% by weight, advantageously less than or equal to 10% by weight, more particularly less than or equal to 9% by weight, preferably less than or equal to 8% by weight and even more precisely less than or equal to 5% by weight, relative to the total weight of the composition. Advantageously, composition (D) does not comprise volatile silicone oil.

[0157] Composition (D) is advantageously in a liquid form.

[0158] Composition (D) may also comprise at least one wax. Reference may be made to the list indicated previously in the description of composition (A). The content of wax(es), if composition (D) comprises any, generally varies between 0.1 and 5% by weight, more particularly from 0.5 to 5% by weight, relative to the total weight of said composition.

[0159] Composition (D) may optionally contain at least one pasty compound, as described previously in the description of composition (A). If composition (D) comprises any, the content of pasty compound(s) is more particularly less than or equal to 20% by weight, preferably between 0.5 and 10% by weight, relative to the total weight of the composition.

[0160] COLOURING MATTER

[0161] According to a particular embodiment of the invention, the composition (A), (B), (C) and / or (D) comprises at least one coloring matter, in particular chosen from synthetic, natural or naturally derived coloring matters.

[0162] The coloring matter may be chosen from coated or uncoated pigments, water-soluble dyes, fat-soluble dyes, and mixtures thereof.

[0163] Pigments

[0164] The term “pigments” means white or colored particles, mineral or organic, insoluble in the medium of the composition, intended to color and / or opacify the composition and / or the resulting deposit.

[0165] According to a first particular embodiment, the pigments used are chosen from mineral pigments.

[0166] By "mineral pigment" is meant any pigment that meets the definition of the Ullmann encyclopedia in the inorganic pigment chapter. Among the mineral pigments useful in the present invention, mention may be made of zirconium or cerium oxides, as well as zinc, iron (black, yellow or red) or chromium oxides, manganese violet, ultramarine blue, chromium hydrate and ferric blue, titanium dioxide, metal powders such as aluminum powder and copper powder. The following mineral pigments may also be used: Ta2O5, Ti3O5, Ti2O3, TiO, ZrO2 in mixture with TiO2, ZrO2, Nb2O5, CeO2, ZnS.

[0167] The size of the pigment useful in the context of the present invention is generally greater than 100 nm and can range up to 10 qm, preferably from 200 nm to 5 qm, and more preferably from 300 nm to 1 qm.

[0168] According to a particular form of the invention, the pigments have a size ca characterized by a D

[50] greater than 100 nm and up to 10 qm, preferably from 200 nm to 5 qm, and more preferably from 300 nm to 1 pm.

[0169] The sizes are measured by static light scattering using a commercial granulometer of the MasterSizer 3000® type from Malvem, making it possible to understand the particle size distribution of all the particles over a wide range from 0.01 pm to 1000 pm. The data are processed on the basis of the classical Mie scattering theory. This theory is the most suitable for size distributions ranging from submicron to multi-micron, it makes it possible to determine an “effective” particle diameter. This theory is notably described in the work of Van de Hulst, HC, “Light Scattering by Small Particles”, Chapters 9 and 10, Wiley, New York, 1957.

[0170] D

[50] represents the maximum size that 50% by volume of the particles has.

[0171] In the context of the present invention, the mineral pigments are more particularly iron oxide and / or titanium dioxide. By way of example, mention may be made more particularly of titanium dioxides and iron oxides, coated with aluminum stearoyl glutamate, for example marketed under the reference NAI® by the company MIYOSHI KASEI.

[0172] As mineral pigments which can be used in the invention, mention may also be made of nacres.

[0173] By “mother-of-pearl” is meant colored particles of any shape, iridescent or not, in particular, produced by certain molluscs in their shell or synthesized and which present a color effect by optical interference.

[0174] The nacres may be chosen from pearlescent pigments, such as titanium mica coated with iron oxide, titanium mica coated with bismuth oxychloride, titanium mica coated with chromium oxide, titanium mica coated with an organic dye, as well as pearlescent pigments based on bismuth oxychloride. They may also be mica particles on the surface of which are superimposed at least two successive layers of metal oxides and / or organic coloring materials.

[0175] Examples of mother-of-pearls that may also be mentioned include natural mica coated with titanium oxide, iron oxide, natural pigment or bismuth oxychloride.

[0176] The mother-of-pearls can more particularly have a yellow, pink, red, bronze, orange, brown, gold and / or coppery color or reflection.

[0177] Among the pigments that can be used according to the invention, mention may also be made of those with an optical effect different from a simple conventional tint effect, that is to say unified and stabilized as produced by conventional coloring materials, such as, for example, monochromatic pigments. For the purposes of the invention, "stabilized" means devoid of any effect of variability of the color with the angle of observation or in response to a change in temperature.

[0178] For example, this material may be chosen from metallic sheen particles, goniochromatic coloring agents, diffracting pigments, thermochromic agents, optical brightening agents, as well as fibers, in particular interference fibers. Of course, these different materials may be combined so as to provide the simultaneous manifestation of two effects, or even a new effect in accordance with the invention.

[0179] According to a particular embodiment, the composition ((A), (B), (C) and / or (D) according to the invention comprises at least one uncoated pigment.

[0180] According to another particular embodiment, the composition (A), (B), (C) and / or (D) according to the invention comprises at least one pigment coated with at least one lipophilic or hydrophobic compound.

[0181] This type of pigment is particularly advantageous. To the extent that they are treated with a hydrophobic compound, they exhibit a predominant affinity for an oily phase which can then carry them.

[0182] The coating may also comprise at least one additional non-lipophilic compound.

[0183] For the purposes of the invention, “coating” a pigment according to the invention generally designates the total or partial surface treatment of the pigment with a surface agent, absorbed, adsorbed or grafted onto said pigment.

[0184] The surface-treated pigments may be prepared according to surface treatment techniques of a chemical, electronic, mechanochemical or mechanical nature well known to those skilled in the art. Commercial products may also be used.

[0185] The surfactant can be absorbed, adsorbed or grafted onto the pigments by solvent evaporation, chemical reaction and creation of a covalent bond.

[0186] According to one variant, the surface treatment consists of a coating of the pigments.

[0187] The coating may represent from 0.1% to 20% by weight, and in particular from 0.5% to 5% by weight of the total weight of the coated pigment.

[0188] The coating can be carried out for example by adsorption of a liquid surfactant on the surface of the solid particles by simple mixing with stirring of the particles and said surfactant, optionally hot, prior to the incorporation of the particles into the other ingredients of the makeup or care composition.

[0189] The coating can be carried out for example by chemical reaction of a surfactant with the surface of the solid pigment particles and creation of a covalent bond between the surfactant and the particles. This method is notably described in US patent 4,578,266.

[0190] The chemical surface treatment may consist of diluting the surfactant in a volatile solvent, dispersing the pigments in this mixture, and then slowly evaporating the volatile solvent, so that the surfactant is deposited on the surface of the pigments.

[0191] When the pigment comprises a lipophilic or hydrophobic coating, the latter is preferably present in the fatty phase of the composition according to the invention.

[0192] According to a particular embodiment of the invention, the pigments may be coated according to the invention with at least one compound chosen from silicone surfactants; fluorinated surfactants; fluoro-silicone surfactants; metallic soaps; N-acylated amino acids or their salts; lecithin and its derivatives; isopropyl trisostearyl titanate; isostearyl sebacate; natural plant or animal waxes; polar synthetic waxes; fatty esters; phospholipids; and mixtures thereof.

[0193] According to a particular embodiment of the invention, the pigments can be coated with a hydrophilic compound.

[0194] According to another particular embodiment, the coloring matter is an organic, synthetic, natural or naturally occurring pigment.

[0195] By "organic pigment" is meant any pigment which meets the definition of the Ullmann encyclopedia in the organic pigment chapter. The organic pigment may in particular be chosen from nitroso, nitro, azo, xanthene, quinoline, anthraquinone, phthalocyanine, metal complex type compounds, isoindolinone, isoindoline, quinacridone, perinone, perylene, diketopyrrolopyrrole, thioindigo, dioxazine, triphenylmethane, quinophthalone.

[0196] The organic pigment(s) may be chosen, for example, from carmine, carbon black, aniline black, melanin, azo yellow, quinacridone, phthalocyanine blue, sorghum red, the blue pigments codified in the Color Index under the references CI 42090, 69800, 69825, 73000, 74100, 74160, the yellow pigments codified in the Color Index under the references CI 11680, 11710, 15985, 19140, 20040, 21100, 21108, 47000, 47005, the green pigments codified in the Color Index under the references CI 61565, 61570, 74260, the orange pigments codified in the Color Index under the references CI 11725, 15510, 45370, 71105, the red pigments codified in the Color Index under the references CI 12085, 12120, 12370, 12420, 12490, 14700, 15525, 15580, 15620, 15630, 15800, 15850, 15865, 15880, 17200, 26100, 45380, 45410, 58000, 73360, 73915, 75470, and the pigments obtained by oxidative polymerization of indole derivatives,phenolics as described in patent FR 2 679 771.,

[0197] The pigments may also be in the form of composite pigments as described in patent EP 1 184 426. These composite pigments may be composed in particular of particles comprising an inorganic core covered at least partially with an organic pigment and at least one binder ensuring the fixing of the organic pigments on the core.

[0198] The pigment may also be a lake. By lake is meant insolubilized dyes adsorbed on insoluble particles, the whole thus obtained remaining insoluble during use.

[0199] The inorganic substrates on which the dyes are adsorbed are, for example, alumina, silica, calcium and sodium borosilicate or calcium and aluminum borosilicate, and aluminum.

[0200] Among the organic dyes, we can cite cochineal carmine. Other products known under the following names include: D&C Red 21 (CI 45 380), D&C Orange 5 (CI 45 370), D&C Red 27 (CI 45 410), D&C Orange 10 (CI 45 425), D&C Red 3 (CI 45 430), D&C Red 4 (CI 15 510), D&C Red 33 (CI 17 200), D&C Yellow 5 (CI 19 140), D&C Yellow 6 (CI 15 985), D&C Green (CI 61 570), D&C Yellow 1 O (CI 77 002), D&C Green 3 (CI 42 053), D&C Blue 1 (CI 42 090).

[0201] Examples of lacquers include the product known under the name D&C Red 7 (CI 15850:1).

[0202] The pigment(s) are preferably present in the composition ((A), (B), (C) and / or (D) at contents of at least 0.01% by weight, more particularly at least 1% by weight, and even more particularly at least 2% by weight, relative to the weight of the composition concerned. More particularly, the coloring matter content is less than 50% by weight, and more particularly between 0.05 and 30% by weight, and even better still from 0.1 to 25% by weight relative to the total weight of the composition concerned (A), (B), (C) and / or (D).

[0203] Water-soluble or fat-soluble dyes

[0204] According to another particular embodiment of the invention, the coloring material is a water-soluble dye or a liposoluble dye.

[0205] For the purposes of the invention, the term "water-soluble coloring matter" means any generally organic, natural or synthetic compound, soluble in an aqueous phase or water-miscible solvents and capable of coloring.

[0206] For the purposes of the invention, the term “liposoluble coloring matter” means any generally organic, natural or synthetic compound, soluble in an oily phase or solvents miscible with the oily phase and capable of coloring.

[0207] As water-soluble dyes suitable for the invention, mention may in particular be made of synthetic or natural water-soluble dyes such as, for example, FDC Red 4, DC Red 6, DC Red 22, DC Red 28, DC Red 30, DC Red 33, DC Orange 4, DC Yellow 5, DC Yellow 6, DC Yellow 8, FDC Green 3, DC Green 5, FDC Blue 1.

[0208] Among the natural water-soluble colorants, we can cite anthocyanins.

[0209] As liposoluble dyes suitable for the invention, mention may in particular be made of liposoluble dyes such as, for example, DC Red 17, DC Red 21, DC Red 27, DC Green 6, DC Yellow 11, DC Violet 2, DC Orange 5, Sudan red, Sudan brown.

[0210] As an illustration of natural fat-soluble colorants, we can particularly mention carotenes such as [3-carotene, α-carotene, lycopene; quinoline yellow; xanthophylls such as astaxanthin, antheraxanthin, citranaxanthin, cryp-toxanthin, canthaxanthin, diatomoxanthin, flavoxanthin, fucoxanthin, lutein, rhodoxanthin, rubixanthin, siphonaxanthin, violaxanthin, zeaxanthin; annatto; curcumin; quinizarin (Ceres Green BB, D&C Green No. 6, CI 61565, 1,4-Di-p-Toluidinoanthraquinone, Green No. 202, Quinzaine Green SS) and chlorophylls.

[0211] The water-soluble or fat-soluble colorant(s) are preferably present in the composition (A), (B), (C) and / or (D) at contents of less than 4% by weight, or even less than 2% by weight, more preferably ranging from 0.01 to 2% by weight, and even better from 0.02 to 1.5% by weight relative to the total weight of the composition (A), (B), (C) or (D).

[0212] COSMETIC ADDITIVES

[0213] The compositions (A), (B), (C) and / or (D) of the invention may contain additives customary in cosmetics. Mention may in particular be made of antioxidants, preservatives, neutralizers, gelling agents or thickeners, surfactants, cosmetic active agents such as, for example, emollients, moisturizers, vitamins, and mixtures thereof.

[0214] Antioxidants

[0215] In particular, antioxidant agents are used to prevent the oxidation of polyphenol X. They can be chosen from ascorbic acid and its derivatives, erythorbic acid, citric acid, sulfites and meta bisulfite, thiol-type reducers, in particular cysteine. Mention may also be made of carotenes and lycopenes, which also act as fat-soluble colorants.

[0216] These additives may be present in compositions (A), (B), (C) and / or (D) in a content ranging from 0.01 to 15.0%, of the total weight of the composition.

[0217] Of course, those skilled in the art will take care to choose any additional additives and / or their quantity in such a way that the advantageous properties of the compositions (A), (B), (C) and / or (D) according to the invention are not, or not substantially, altered by the envisaged addition.

[0218] Compositions (A), (B), (C) and / or (D) can be manufactured by known methods, generally used in the cosmetic field.

[0219] COMPOSITION (M)

[0220] The process according to the invention is carried out in the presence of an anhydrous composition (M).

[0221] The composition (M) comprises at least one oil and optionally at least one coloring matter chosen from those defined previously.

[0222] The composition (M) in accordance with the invention may be a product, in particular a makeup or care product, or even a hybrid product (in other words with a makeup and care action).

[0223] Composition (M) is more particularly a product intended to be applied to the lips, in particular a lipstick, lip gloss and lip balm.

[0224] The compositions (M) for the lips can advantageously be presented in a fluid (gloss) to solid (stick) form.

[0225] By “fluid” (or liquid) we mean in particular a composition which is not solid at 25°C, and of which it is possible to measure a viscosity.

[0226] By “solid” we mean in particular a composition whose hardness can be measured according to the so-called “butter wire” method at 20°C.

[0227] Between these two extremes, there are intermediate textures whose viscosity and hardness cannot be measured using the methods detailed below. Such compositions are then described as pasty.

[0228] Preferably, the composition (M) is solid.

[0229] Protocol for viscosity measurement

[0230] The viscosity measurement is generally carried out at 25°C, using a RHEOMAT RM 180 viscosimeter equipped with a spindle No. 2, No. 3 or a spindle No. 4, according to the usage recommendations, the measurement being carried out after 10 minutes of rotation of the spindle within the composition at a speed of 200 rpm.

[0231] By way of example, the composition may have a viscosity of between 0.1 and 25 Pa.s at 25°C.

[0232] Hardness measurement protocol

[0233] The composition in stick form is stored at 20°C for 24 hours before measuring the hardness.

[0234] The measurement is carried out at 20°C and consists of transversely cutting a stick of product, preferably cylindrical in revolution, using a rigid tungsten wire with a diameter of 250 μm, moving the wire relative to the stick at a speed of 100 mm / min.

[0235] The hardness of the samples of compositions of the invention, expressed in Nm-1, is measured using a DFGS2 dynamometer marketed by the company INDELCO-CHATILLON.

[0236] The measurement is repeated three times and then averaged. The average of the three values ​​read using the dynamometer mentioned above, denoted Y, is given in grams. This average is converted into Newtons and then divided by L which represents the dimension the highest through which the wire passes. In the case of a cylindrical stick, L is equal to the diameter (in meters).

[0237] Hardness is converted to Nm 1 by the equation: (Y x 103 x 9.8) / L.

[0238] For example, the composition may have a hardness of between 20 and 200 NmA.

[0239] More particularly, the composition (M) comprises at least one oil.

[0240] Among the oils, one can refer to the lists indicated previously.

[0241] Preferably, the composition (M) comprises at least one non-volatile oil, preferably hydrocarbon-based. Even more particularly, the composition (M) comprises at least one polar hydrocarbon-based non-volatile oil, of ester type.

[0242] As particular examples, mention may be made of fatty acid triglycerides, in particular caprylic acid or capric acid triglycerides and mixtures thereof, vegetable oils; polyesters obtained by condensation of dimer and / or trimer of unsaturated fatty acid and diol; esters and polyesters of dimer diol and mono- or dicarboxylic acid, as well as mixtures thereof.

[0243] Depending on the galenic of the composition, the oil content may vary in particular from 10 to 80% by weight, in particular from 20 to 75% by weight, relative to the weight of the composition.

[0244] The composition (M) may optionally comprise at least one wax. Here again, reference may be made to the detailed description above.

[0245] The content of this type of ingredient varies according to the galenic of the composition (M). For example, the content of wax(es), if this type of ingredient is present in said composition, varies from 0.01 to 25% by weight, more particularly from 0.5 to 25% by weight, relative to the weight of the composition.

[0246] The composition (M) may also comprise at least one pasty compound as described previously.

[0247] If the composition (M) comprises at least one pasty compound, their content varies from 0.5 to 35% by weight, preferably from 0.5 to 25% by weight, relative to the total weight of the composition.

[0248] The composition (M) may also contain one or more ingredients commonly used in this type of product such as organic solvents; thickening agents; film-forming polymers, silicone or non-silicone; fillers; cosmetic active ingredients such as vitamins, solar UV filters, moisturizing agents, antioxidant agents.

[0249] MAKE-UP AND / OR CARE METHODS

[0250] From compositions (A) and (B)

[0251] According to a particular embodiment, the invention relates to a method for making up the skin and / or the lips, preferably the lips, consisting of implementing the steps following: 1) a) at least one composition (A) comprising, in particular in a physiologically acceptable medium, at least one polyphenol X as defined above is applied to the skin and / or the lips, preferably to the lips; and 1) b) at least one composition (B) comprising, in particular in a physiologically acceptable medium, at least one compound Y as defined previously; said compositions (A) and (B) being applied to the skin and / or the lips, i) simultaneously; or ii) in the form of an extemporaneous mixture at the time of use; or iii) successively, regardless of the order of application; one and / or the other of compositions (A) and (B) comprising at least one coloring material, preferably composition (A); 2) an anhydrous composition (M) is applied to the skin and / or lips thus treated.

[0252] Advantageously, the composition (M) is applied to the composition obtained from the end of the first step, without mixing. It is also preferably applied after at least partial drying of the composition deposited during the first step. As an indication, the second step is carried out a few minutes after the first.

[0253] First step

[0254] The first step can be carried out by applying composition (A) first, then composition (B).

[0255] According to another variant, composition (B) is applied first, then composition (A) over the first.

[0256] More particularly, the ratio of the mass of polyphenol(s) X, expressed as active material to the mass of compound(s) Y, expressed as active material, varies between 0.25 and 3, preferably between 0.5 and 2.

[0257] This operation preferably takes place without mixing the two layers together, more particularly the second layer is applied over the first, once the latter has dried.

[0258] Either of compositions (A) and (B) may be aqueous or anhydrous.

[0259] Alternatively, one of the two compositions is aqueous, while the other is anhydrous.

[0260] According to a characteristic of the process according to the invention, this first step is carried out in the presence of at least one coloring material, as defined previously.

[0261] The coloring matter(s) may be found in composition (A), in composition (B), or even in both compositions at the same time.

[0262] Preferably, the coloring matter(s) is / are in the first composition which is applied.

[0263] According to a particularly preferred embodiment, the following are successively applied to the skin and / or the lips: a) a first layer of makeup (base coat) with an anhydrous composition (B) as defined previously comprising at least one coloring matter, preferably a pigment, then b) on the skin and / or lips thus colored, a second post-treatment layer (top coat) with an aqueous composition (A) as defined previously.

[0264] From composition (C)

[0265] Another cosmetic process for making up the skin and / or the lips, preferably the lips, according to the invention, consists of implementing the following steps: 1) at least one composition (C) comprising, in particular in a physiologically acceptable medium, at least one coating agent previously formed by interaction by hydrogen bonds of at least one polyphenol X with at least one compound Y as defined previously is applied to the skin and / or the lips, preferably to the lips; the composition (C) comprising at least one coloring matter; 2) an anhydrous composition (M) is applied to the skin and / or lips thus treated.

[0266] Advantageously, the composition (M) is applied to the composition obtained at the end of the first step, without mixing. It is also preferably applied after at least partial drying of the composition deposited during the first step. As an indication, the second step is carried out a few minutes after the first.

[0267] From composition (D)

[0268] Another cosmetic process for making up the skin and / or the lips, preferably the lips, according to the invention, consists of implementing the following steps: 1) at least one composition (D) comprising, in particular in a physiologically acceptable medium, is applied to the skin and / or the lips, preferably to the lips, (a) at least one polyphenol X as defined above, (b) at least one compound Y as defined above, (c) at least one mono-alcohol containing from 2 to 8 carbon atoms, and more particularly ethanol and (d) at least one coloring matter, 2) an anhydrous composition (M) is applied to the skin and / or lips thus treated.

[0269] Advantageously, the composition (M) is applied to the composition obtained at the end of the first step, without mixing. It is also preferably applied after at least partial drying of the composition deposited during the first step. As an indication, the second step is carried out a few minutes after the first.

[0270] PACKAGING AND APPLICATORS

[0271] The compositions (A), (B) (C), (D) and / or (M) according to the invention may be condi- each given in a container delimiting at least one compartment which comprises said composition, said container being closed by a closing element.

[0272] The container may be in any suitable form. It may in particular be in the form of a bottle, a tube, a pot, a case.

[0273] The closure element may be in the form of a removable stopper, a lid, a cover, in particular of the type comprising a body fixed to the container and a cap hinged to the body. It may also be in the form of an element ensuring the selective closure of the container, in particular a pump, a valve, or a flap.

[0274] The container may be associated with an applicator, for example in the form of a brush (as described for example in patent FR 2 722 380), in the form of an element, deformable or not, made of foam or elastomer, flocked or not. The applicator may also be free (sponge) or integral with a rod carried by the closure element, as described for example in patent US 5 492 426. The applicator may be integral with the container, as described for example in patent FR 2 761 959.

[0275] The product may be contained directly in the container, or indirectly.

[0276] The closure element may be coupled to the container by screwing. Alternatively, the coupling between the closure element and the container is achieved by means other than screwing, in particular via a bayonet mechanism, by snap-fastening, or by tightening. By "snap-fastening" is meant in particular any system involving the crossing of a bead or cord of material by elastic deformation of a portion, in particular of the closure element, then by return to the non-elastically stressed position of said portion after crossing the bead or cord.

[0277] The container may be at least partly made of thermoplastic material. Examples of thermoplastic materials include polypropylene or polyethylene.

[0278] The container may have rigid walls or deformable walls, in particular in the form of a tube or a tube bottle.

[0279] The container may comprise means for causing or facilitating the dispensing of the composition. For example, the container may have deformable walls so as to cause the composition to exit in response to an overpressure inside the container, which overpressure is caused by elastic (or non-elastic) crushing of the walls of the container.

[0280] The container may be equipped with a wiper arranged in the vicinity of the opening of the container. Such a wiper makes it possible to wipe the applicator and possibly the rod to which it may be attached. Such a wiper is described for example in patent FR 2 792 618.

[0281] Throughout the description, including the claims, the expression "comprising "one" should be understood as being synonymous with "comprising at least one", unless otherwise specified.

[0282] The expressions “between... and...” and “ranging from... to...” must be understood inclusively, unless otherwise specified.

[0283] Furthermore, the sum of the quantities of the ingredients of the composition represents 100% by weight of the composition.

[0284] The invention is illustrated in more detail by the examples presented below.

[0285] Unless otherwise indicated, the quantities indicated are expressed as a mass percentage.

[0286] The following examples are presented for illustrative and non-limiting purposes of the invention. Examples

[0287] Example 1

[0288] The following composition (D) was prepared:

[0289] [Tables 1] Ingredients (INCI name or chemical name) % weight Tannic acid (Brewtan F - Ajinomoto Omnichem Nv) 15 Polyglyceryl-6 Dicaprate (SunSoft Q-102H-C - Taiyo Kagaku) ​​5 Polyglyceryl-4 Caprate (Tegosoft PC 41 - EVONIK Goldschmidt) 5 Polyglyceryl-5 Laurate (SunSoft A-121E-C - Taiyo Kagaku) ​​5 Red 7 (Unipure Red LC 3079 OR - Sensient) 10 Ethanol Qsp 100

[0290] Preparation process When cold, mix Rayneri, tannic acid and ethanol while stirring. Then, introduce the polyglycerolated compounds once the tannic acid has dissolved. Sprinkle the Red 7 pigment and let it stir for 15 minutes.

[0291] The mixture obtained is not stable over time: it separates phases but by simple manual stirring, the pigments are redispersed and the formula remains homogeneous for the duration of the makeup.

[0292] Composition (Ml

[0293] The following composition (M) was prepared

[0294] [Tables2] Ingredients (INCI name or chemical name) % weight Butyrospermum parkii (shea) butter (Lipex sheasoft- Aarhuskarlshamn) 3.7 Macadamia integrifolia seed oil (Refined Macadamia Oil BCE1010 - Biocosmethic) 32 Glyceryl dibehenate (and) tribehenin (and) glyceryl behenate (Compritol 888 CG ATO MB - Gattefossé) 17.5 Helianthus Annuus Seed Oil Qsp 100 Glyceryl stearate 5 Tocopherol qs

[0295] Method of preparation Except for the tocopherol, mix all the ingredients under a rayneri at 98°C for 20 minutes until the mixture is melted and homogeneous. Add the tocopherol and pour it into a lipstick mold. When the composition is solid, remove it from the mold and package it.

[0296] Application and evaluation

[0297] For lip makeup, composition (D) is very easy to apply with a dip applicator, allowing a very thin film to be obtained on the lips, with an intense, even color.

[0298] Once the composition has dried, composition (M) is applied over it.

[0299] A non-sticky, very comfortable deposit is obtained.

[0300] The whole thing does not transfer (e.g. kiss on the hand test).

[0301] The resulting deposit was evaluated in a test of resistance to mechanical and chemical attacks: dry friction, water and oil.

[0302] Performance evaluation protocol

[0303] L Test preparation:

[0304] Support: Supplale beige (2.5 x 5 cm) (marketed by Soudotique).

[0305] Spread the composition (D) over the entire surface 3 times in a row to obtain a homogeneous deposit. Repeat the operation on two other strips. Leave the deposit to dry on a plate heated to 34°C for 30 minutes. Apply composition (M) over the entire surface 3 times in a row to obtain a uniform coating. Do the same on the other two strips. Let the deposit dry again on a plate heated to 34°C for 30 minutes. If necessary, take a photo of each support with the deposit (made up) beforehand. the solicitation.

[0306] 2, Requests:

[0307] Preparation of a tissue for each request: Fold each tissue twice along the long edge and then twice in the other direction to form a square.

[0308] Dry resistance:

[0309] Rub once with the handkerchief folded lengthwise one of the three made-up surfaces; the force applied is that normally exerted when removing make-up from the skin or lips. Observe the condition of the rubbed support as well as the used surface of the handkerchief, in particular the remaining coloring, the transferred coloring. Possibly take a photo.

[0310] In the case where several passes are carried out, they would then be carried out with the same force and always in the same direction (i.e.: after each pass, the handkerchief is lifted to be repositioned at the “start” of the strip in order to be reapplied to the deposit in the same way as in the previous pass). Possibly take a photo between each step or only at the end of the evaluation. This type of process can be implemented to evaluate the overall resistance of the deposit.

[0311] Water resistance:

[0312] Insert the second coated support without folding it into a centrifuge tube. Add 10 grams of demineralized water. Centrifuge for 10 minutes at 450g. Optionally take a photo of the support after mixing, immediately after the operation. Rub once with a tissue along the length of the support, without waiting, with the same force as that applied for dry resistance. Observe the condition of the rubbed support as well as the used surface of the handkerchief, in particular the remaining coloring, the transferred coloring. Possibly take a photo.

[0313] The protocol for multiple passes is the same as that detailed previously for dry resistance.

[0314] Oil resistance:

[0315] Implement the same protocol as for water resistance, on the third made-up support, replacing the water with the same quantity of olive oil (Refined Olive Oil - Aarhuskarlshamn).

[0316] Rating:

[0317] For each request, note the result according to the table below:

[0318] [Tables3] Note State of the deposit Surface of the fabric in contact with the deposit - - Total or partial removal of the deposit on the rubbed area; the surface of the support appears in places Very intense coloration - very significant to total transfer of the color - Partial removal resulting in a significantly and visibly less intense coloration of the deposit. Intense coloration - significant transfer of the color + Reduction in the intensity of the color of the deposit perceptible but which does not reveal the support Medium coloration - average transfer of the color ++ No substantial variation in the color of the deposit Slight coloration - little transfer of the color +++ No variation in the color of the deposit No coloration or barely visible coloration - no to very little transfer of the color

[0319] It should be noted that to facilitate the evaluation of the resistance of the deposit, the latter comprises at least one coloring material whose coloring is sufficiently intense (for example a red coloring material, such as Red 7 in particular).

[0320] When comparing several compositions, the latter have the same shade (same quantity and same coloring matter).

[0321] It should be noted that the resistance of the deposit, as well as other properties (homogeneity, comfort, etc.) can also be evaluated by a Sensory Panel (group of trained experts allowing a description of technical characteristics to be obtained - standards ISO 8586, ISO 11132, ISO 13299).

[0322] Results:

[0323] [Tables4] Dry resistance Water resistance Oil resistance +++ + +++

Claims

Claims

1. Method for making up the skin and / or the lips, preferably the lips, consisting of carrying out the following steps: 1) applying to the skin and / or the lips a coating agent formed in situ by interaction via hydrogen bonds of at least one polyphenol X comprising at least two different phenol groups with at least one compound Y chosen from polyglycerol esters comprising 2 to 20 glycerol units; this step taking place in the presence of at least one coloring matter; 2) applying to the skin and / or the lips thus treated, an anhydrous composition (M).

2. Method according to claim 1, characterized in that the polyphenol X is chosen from catechol tannins, in particular chosen from gallotannins and ellagitannins.

3. Process according to any one of claims 1 or 2, characterized in that the polyphenol X is epigallocatechin, in particular a green tea extract, in particular comprising at least 45% by weight of epigallocatechin relative to the weight of said extract.

4. Method according to claim 1, characterized in that the polyphenol X is a procyanidin or a mixture of procyanidins, in particular an extract of maritime pine bark, in particular comprising at least 65% by weight of procyanidins relative to the total weight of said extract.

5. Process according to any one of claims 1 or 2, characterized in that the polyphenol X is tannic acid.

6. Process according to any one of the preceding claims, characterized in that the compounds Y have a molar mass greater than 200 g / mol, more particularly greater than 350 g / mol.

7. Process according to any one of the preceding claims, characterized in that the compound Y is chosen from esters, preferably non-ionic, of polyglycerol comprising 2 to 20 glycerol units and of carboxylic acid(s) or of polymer(s) of carboxylic acid(s), saturated or unsaturated, comprising 6 to 40 carbon atoms, preferably 8 to 30 carbon atoms, or derivatives of vegetable oils; and mixtures thereof.

8. Method for making up the skin and / or the lips, preferably the lips, according to any one of the preceding claims, characterized in that the compound Y is chosen from the following compounds, désignés par leur nom INCI : Polyglycéryl-2 Stéarate, Polyglyceryl-2 Isostearate, Polyglyceryl-2 Diisostéarate, Polyglyceryl-3 Diisostearate, Polyglyceryl-3 Dicitrate / Stearate, Polyglycéryl-4 Diisostearate, Poly-glyceryl-4 Caprate, Polyglyceryl-4 Laurate^ Polyglyceryl-5 Laurate, Poylglyceryl-5 oleate, Polyglyceryl-6 Caprylate, Polyglyceryl-6 dicaprate, Polyglyceryl-6 Distearate, Polyglyceryl-6 Caprylate / Caprate, Polyglyceryl-10 Laurate, Polyglyceryl-10 Dioleate, ainsi que leurs mélanges.

9. Method for making up the skin and / or the lips, preferably the lips, according to any one of claims 1 to 8, consisting of carrying out the following steps: l)a) applying to the skin and / or the lips, preferably to the lips, at least one composition (A) comprising, in particular in a physiologically acceptable medium, at least one polyphenol X as defined according to any one of claims 1 to 5; and l)b) at least one composition (B) comprising, in particular in a physiologically acceptable medium, at least one compound Y as defined according to any one of claims 1 or 6 to 8; said compositions (A) and (B) being applied to the skin and / or the lips, i) simultaneously; or ii) in the form of an extemporaneous mixture at the time of use; or iii) successively, regardless of the order of application;one and / or the other of compositions (A) and (B) comprising at least one coloring matter, preferably composition (A); 2) an anhydrous composition (M) is applied to the skin and / or lips thus treated.;

10. Process according to claim 9, characterized in that the content of polyphenol(s) X represents at least 2% by weight, more particularly from 2 to 50% by weight, preferably from 5 to 30% by weight relative to the total weight of the composition (A).

11. Process according to any one of claims 9 or 10, characterized in that the content of compound(s) Y represents at least 1% by weight, more particularly from 1 to 75% by weight, preferably from 2 to 50% by weight relative to the total weight of the composition (B).

12. Method according to any one of claims 9 to 11, characterized in that the composition (A) and / or the composition (B) comprises water more particularly at a content greater than or equal to 25% by weight, or even greater than or equal to 30% by weight, and more preferably ranging from 35 to 85% relative to the total weight of composition (A) or (B).

13. Process according to any one of claims 9 to 12, characterized in that the composition (A) and / or the composition (B) comprises at least one C2-C8 monoalcohol, more particularly C2-C5, preferably ethanol, more particularly at a content greater than or equal to 25% by weight, or even greater than or equal to 30% by weight, and more preferably ranging from 35 to 85% relative to the total weight of the composition (A) or (B).

14. Process according to any one of claims 9 to 13, characterized in that the composition (A) and / or (B) comprises at least one oily phase, more particularly at a content greater than or equal to 5% by weight, or even greater than or equal to 10% by weight, and more preferably ranging from 20 to 85% by weight, relative to the total weight of the composition (A) or (B).

15. Method for making up the skin and / or the lips, preferably the lips, according to any one of claims 1 to 8, consisting of carrying out the following steps: 1) applying to the skin and / or the lips, preferably to the lips, at least one composition (D) comprising, in particular in a physiologically acceptable medium, a) at least one polyphenol X as defined according to any one of claims 1 to 5 and b) at least one compound Y as defined according to any one of claims 1, 6 to 8 and c) at least one mono-alcohol comprising from 2 to 8 carbon atoms, more particularly comprising from 2 to 5 carbon atoms, and more particularly ethanol, the content of liquid C2-C8 mono-alcohol being greater than or equal to 25% by weight, relative to the total weight of the composition (D), d) at least one coloring matter; 2) an anhydrous composition (M) is applied to the skin and / or lips thus treated.

16. Process according to claim 15, characterized in that the content of polyphenol X is at least 2% by weight, preferably between 2 and 30% by weight, and even more particularly from 3 to 25% by weight, relative to the total weight of the composition (D).

17. Process according to any one of claims 15 or 16, characterized in that the content of compound Y represents at least 1% by weight, more particularly at least 2% by weight, preferably between 2 and 40% by weight, and even more particularly between 3 and 35% by weight, relative to the total weight of the composition (D).

18. Process according to any one of claims 15 to 17, characterized in that the ratio of the mass of polyphenol(s) X, expressed as active material, to the mass of compound(s) Y, expressed as active material, varies between 0.25 and 3, preferably between 0.5 and 2.

19. Process according to any one of claims 15 to 18, characterized in that the content of liquid C2-C8 monoalcohol ranges from 25 to 98% by weight, and even more particularly from 30 to 90% by weight, and preferably from 35 to 85% by weight, relative to the total weight of the composition (D).

20. Method according to any one of claims 15 to 19, characterized in that the composition (D) comprises at least water, more particularly in a content less than or equal to less than or equal to 10% by weight, less than or equal to 5% by weight, relative to the total weight of the composition (D).

21. Method according to any one of claims 15 to 20, characterized in that the composition (D) comprises an oily phase, more particularly at a content of between 1 and 30% by weight, preferably between 1 and 20% by weight, relative to the total weight of said composition (D).

22. Process according to any one of claims 15 to 21, characterized in that the composition (D) comprises an oily phase comprising at least one volatile hydrocarbon oil, at a content less than or equal to 20% by weight, preferably less than or equal to 10% by weight, preferably less than or equal to 8% by weight and even more precisely less than or equal to 5% by weight, relative to the total weight of the composition (D).

23. Method according to any one of the preceding claims, characterized in that the coloring matter comprises at least one synthetic, natural or naturally occurring coloring matter; in particular chosen from coated or uncoated pigments, water-soluble dyes, fat-soluble dyes, and mixtures thereof.

24. Method according to any one of the preceding claims, characterized in that the content of coloring matter(s) in the composition (A) and / or (B), of composition (D) is at least 0.01% by weight, more particularly between 0.05 and 30% by weight, in particular between 0.1 and 25% by weight, relative to the total weight of the composition concerned.

25. Method according to any one of the preceding claims, characterized in that the composition (M) comprises at least one non-volatile, hydrocarbon-based oil, preferably polar, in particular chosen from esters.

26. Method according to any one of the preceding claims, characterized in that the composition (M) comprises at least one wax or at least one pasty compound, as well as their mixtures.

27. ​​Method according to any one of the preceding claims, characterized in that the composition (M) is in a solid form.