Naturally derived colored powders and their uses

Abstract

This invention relates to an insoluble colored powder comprising: (i) a natural colored compound or a naturally derived colored compound or a colored extract containing the thereof, and (ii) a nitrogen-containing compound of formula (I), wherein (II) represents a single or double bond, R 1 and R 3 Each of the following is independent of or selected from H, or optionally substituted C1-C 12 Aliphatic chains, wherein one or more of the aliphatic chains, preferably 1 to 4 methylene units, are optionally substituted with O, C(O), NH or N (C1-C6 alkyl), R 2 and R 4 Each is independently selected from H, oxo group, thio group, and NR. x R y Groups, halogens, or optionally substituted C1-C 12 Aliphatic chains, wherein one or more of the aliphatic chains, preferably 1 to 4 methylene units, are optionally substituted with O, C(O), NH or N (C1-C6 alkyl), R x and R y Each can be independently represented by H or C1-C6 alkyl, R 5 and R 6 Each is independently selected from H, oxo group, thio group, or optionally substituted C1-C group. 12 Aliphatic chains, wherein one or more of the aliphatic chains preferably have 1 to 4 methylene units optionally substituted with O, C(O), NH or N (C1-C6 alkyl), or R 5 and R 6 Together with the carbon atoms to which they are bonded, they form optionally substituted aryl or optionally substituted imidazole groups. The invention also relates to their use in care and / or cosmetic compositions for use with keratin materials.

Description

Technical Field

[0001] This invention relates to the field of cosmetic compositions for the care and / or makeup of keratin materials, particularly colored powders of natural origin. Background Technology

[0002] Beauty products, especially cosmetics, use synthetic pigments or dyes, but consumers’ search for more natural and environmentally friendly ingredients has driven the development of new pigments that are more natural yet equally effective and offer a wider range of colors.

[0003] However, the natural pigments currently available on the market have poor hiding power, poor light stability, and are not very vibrant.

[0004] Therefore, there is still a need to develop new pigments (also known as colored powders) based on natural colored compounds and / or plant-derived colored extracts to meet these needs.

[0005] The applicant has clearly demonstrated that combining the nitrogen-containing compound of formula (I) with a natural colored compound or a naturally derived colored compound or a colored extract containing thereof results in colored powders with improved properties in terms of light stability, pH stability, color brightness, and hiding power. These colored powders are obtained, in particular, by dissolving the nitrogen-containing compound of formula (I) such that the natural colored compound or a naturally derived colored compound or an extract containing thereof is non-covalently fixed within or on the surface of crystals formed from the compound of formula (I).

[0006] Therefore, these naturally sourced colored powders have become an interesting alternative to synthetic pigments. Summary of the Invention

[0007] The first object of the present invention is a colored powder comprising the following combination: (i) naturally colored compounds or colored compounds of natural origin or colored extracts containing them, and (ii) Nitrogen-containing compounds of formula (I) in Indicates a single bond or a double bond. R 1 and R 3 Each of the following is independent of or selected from H, or optionally substituted C1-C 12 Aliphatic chains, wherein one or more of the aliphatic chains preferably have 1 to 4 methylene units optionally substituted with O, C(O), NH or N (C1-C6 alkyl), R 2 and R4 Each is independently selected from H, oxo group, thio group, and NR. x R y Halogens, optional substituted C1-C 12 Aliphatic chains, wherein one or more of the aliphatic chains preferably have 1 to 4 methylene units optionally substituted with O, C(O), NH or N (C1-C6 alkyl), R x and R y Independently representing H or C1-C6 alkyl, R 5 and R 6 Each is independently selected from H, oxo group, thio group, or optionally substituted C1-C group. 12 Aliphatic chains, wherein one or more of the aliphatic chains preferably have 1 to 4 methylene units optionally substituted with O, C(O), NH or N (C1-C6 alkyl), or R 5 and R 6 Together with the carbon atoms they are bonded to, they form optionally substituted aryl or optionally substituted imidazolyl groups.

[0008] Preferably, the colored powder does not contain metal salts of aluminum or zinc.

[0009] In particular, the colored powder according to the present invention is insoluble.

[0010] According to the present invention, "insoluble colored powder" is understood to mean a powdered colored material (particulate form) that is insoluble in water, ethanol, and any proportion of water / ethanol mixtures at a concentration of 0.5% by weight at room temperature (25°C).

[0011] Nitrogen-containing compounds of formula (I), particularly guanine, constitute a natural support with a high refractive index (1.8). Colored compounds and / or extracts are adsorbed onto the surface and / or interior of crystals formed from guanine, thereby forming a colored pigment (also known as a colored powder according to the invention) with more vibrant colors and better hiding power compared to currently commercially available colored pigments. Furthermore, advantageously, the method for preparing the colored powder according to the invention does not involve any metal salts. Therefore, this novel colored powder is an interesting alternative to synthetic pigments, being a naturally derived (excluding animal-derived) colored powder that offers improved performance in terms of pH stability, photostability, hiding power, and vibrancy compared to currently commercially available natural pigments.

[0012] According to a particular and preferred embodiment, the colored powder according to the invention does not contain metal salts of aluminum or zinc.

[0013] According to a particular and preferred embodiment, the colored powder according to the invention comprises a magnesium salt.

[0014] The present invention also relates to a method for preparing colored powders as defined herein, comprising the following steps: i) Dissolve the nitrogen-containing compound of formula (I) in an aqueous solution, preferably an alkaline aqueous solution. ii) Dissolving one or more naturally colored compounds or naturally derived colored compounds or extracts containing them (water-soluble compounds ii) in optionally acidified water or ethanol solution (iia), or alternatively dissolving one or more naturally colored compounds or naturally derived colored compounds or extracts containing them (lipid-soluble compounds ii) in an organic solvent, especially a carbonyl solvent (iib). iii) Introduce the solution obtained in i) into the colored solution obtained in ii), optionally with an acid present in the aqueous solution, so that the nitrogen-containing compound of formula (I) co-precipitates with the natural colored compound or a naturally derived colored compound or a colored extract containing it and forms the colored powder. iv) Separate the liquid phase from the solid colored powder by filtration or centrifugation. v) Wash the colored powder obtained in iv) with ethanol, and separate the liquid phase from the solid colored powder by filtration or centrifugation. vi) Rinse the colored powder obtained in v) with water, and separate the liquid phase from the solid colored powder by filtration or centrifugation. vii) Dry the colored powder.

[0015] In particular, a solution containing water and NaOH can be used as an alkaline solution.

[0016] In particular, citric acid, lactic acid, or acetic acid can be used as acids.

[0017] In particular, drying steps can be performed through zéodratation, freeze drying, or oven drying.

[0018] Another object of the present invention is a pigment paste comprising a colored powder as defined herein and one or more oils.

[0019] The present invention also relates to a method for preparing a pigment paste as defined above, comprising the following steps: i) Grinding the colored powder as defined in this invention, and ii) Mix with one or more oils.

[0020] The present invention also relates to a cosmetic composition comprising, in a physiologically acceptable medium, a colored powder or a pigment paste as defined herein, and one or more additional ingredients selected from oils, C1-C5 monools, glycols, surfactants, fillers, gelling agents or structuring agents, film-forming agents, cosmetic active ingredients, antioxidants, preservatives, fragrances, and mixtures thereof.

[0021] Another object of the present invention is a method for cosmetic or care applications to keratin materials, comprising applying a composition as defined in the present invention to the keratin material. Detailed Implementation

[0022] Colored powder Therefore, the first object of the present invention is a colored powder comprising the following combination: (i) naturally colored compounds or colored compounds of natural origin or colored extracts containing them, and (ii) Nitrogen-containing compounds of formula (I) in Indicates a single bond or a double bond. R 1 and R 3 Each of the following is independent of or selected from H, or optionally substituted C1-C 12 Aliphatic chains, wherein one or more of the aliphatic chains preferably have 1 to 4 methylene units optionally substituted with O, C(O), NH or N (C1-C6 alkyl), R 2 and R 4 Each is independently selected from H, oxo group, thio group, and NR. x R y Halogens, optional substituted C1-C 12 Aliphatic chains, wherein one or more of the aliphatic chains preferably have 1 to 4 methylene units optionally substituted with O, C(O), NH or N (C1-C6 alkyl), R x and R y Independently representing H or C1-C6 alkyl, R 5 and R 6 Each is independently selected from H, oxo group, thio group, or optionally substituted C1-C group. 12 Aliphatic chains, wherein one or more of the aliphatic chains preferably have 1 to 4 methylene units optionally substituted with O, C(O), NH or N (C1-C6 alkyl), or R 5 and R6 Together with the carbon atoms they are bonded to, they form optionally substituted aryl or optionally substituted imidazolyl groups.

[0023] Naturally colored compounds or colored compounds of natural origin or colored extracts containing them (compound i) The compositions of the present invention comprise at least one natural colored compound or a naturally derived colored compound or a colored extract containing the same.

[0024] According to the present invention, "natural colored compound" is understood to mean a colored compound obtained directly from soil or earth or from plants or animals through one or more applicable physical processes (e.g., grinding, refining, distillation, purification or filtration).

[0025] According to the present invention, "naturally derived colored compound" is understood to mean a naturally colored compound that has undergone one or more auxiliary chemical or industrial treatments that result in a change that does not affect the essential properties of the compound and / or a compound that primarily comprises the natural components described above, whether transformed or not. Non-limiting examples of auxiliary chemical or industrial treatments that produce changes that do not affect the essential properties of the natural compound include treatments authorized by regulatory bodies such as Ecocert (Standards for Organic and Eco-Cosmetics, January 2003) or as defined in recognized manuals in the field (e.g., "Journal of Cosmetics and Toiletries", 2005, Vol. 120, 9:10).

[0026] According to the present invention, "colored extract" is understood to mean an extract containing one or more naturally colored compounds or naturally derived colored compounds as defined above.

[0027] According to the foregoing definition, such colored extracts are preferably natural or of natural origin, and more preferably of plant origin.

[0028] According to the present invention, "naturally derived colored extracts" are understood to mean extracts containing one or more colored compounds obtained from plant material or secretions of plant material. In particular, they can be derived from any part of the plant, such as roots, stems, trunks, leaves, flowers, fruits, and mixtures thereof. They can also be derived from plant secretions, especially secretions produced in response to or prevention of stress. These plant-derived colored extracts can be obtained by grinding, extraction with water or solvents, supercritical CO2 extraction, chemical or enzymatic treatment, or a combination of these methods.

[0029] In particular, Annex IV to European Parliament and Council Regulation (CE) 1223 / 2009 of 30 November 2009 on cosmetics refers to natural colored compounds or colored compounds of natural origin or extracts thereof that can be used in cosmetics.

[0030] According to a particular embodiment, the natural or naturally derived compounds that can be used in the colored powder of the present invention are selected from the following compounds: curcumin, lactoferrin (or riboferrin), β-carotene, capsanthin / capsicum red, lycopene, caramel, chlorophyll (or copper-chlorophyll complex), indigo, carmine, anthocyanins (e.g., cyanidin, delphinidin, pheophytin, or malvidin), betaine and its derivatives, violacein and deoxyviolacein, flavonoids, or natural extracts containing them, and mixtures thereof.

[0031] For example, those skilled in the art can select the type of anthocyanin according to the desired color. For instance, they can advantageously use anthocyanin for a redder pigment and delphinidin for a bluer pigment.

[0032] According to a first specific embodiment, the colored powder according to the invention comprises a water-soluble natural colored compound or a naturally derived colored compound or an extract containing the same.

[0033] Water-soluble natural colored compounds or naturally derived colored compounds particularly include curcumin, lactoferrin, caramel, chlorophyll, anthocyanins, betalains and their derivatives, violacein and deoxyviolacein, flavonoids, or natural extracts containing them, and mixtures thereof, preferably curcumin, lactoferrin, caramel, chlorophyll, anthocyanins, betalains and their derivatives, flavonoids, or natural extracts containing them, and mixtures thereof.

[0034] According to a first specific embodiment, the colored powder according to the invention comprises a fat-soluble natural colored compound or a naturally derived colored compound or an extract containing the same.

[0035] Fat-soluble natural colored compounds or naturally derived colored compounds especially include beta-carotene, capsanthin / capsicum and lycopene.

[0036] Extracts containing them, especially plant extracts, can also be used.

[0037] Colored extracts from plant sources rich in anthocyanins include, in particular, extracts from black carrots, elderberries, hibiscus, blackcurrants, purple corn, black potatoes, purple potatoes, red cabbage, red onions, black grapes, cranberries, strawberries, raspberries, black beans, cherries, carrots, raisins, blueberries, cherries, eggplants, and black rice, with carrot or hibiscus extracts being preferred.

[0038] Extracts rich in betalains and their derivatives include, in particular, beet extract.

[0039] Turmeric extract can be considered a colored extract from a plant source rich in curcumin.

[0040] Colored extracts from plant sources rich in beta-carotene include extracts from carrots, sweet potatoes, and pumpkins.

[0041] Paprika extract can be considered a colored extract from a plant source rich in capsanthin / capsicum.

[0042] Therefore, according to a specific embodiment, the natural colored compound or naturally derived colored compound is selected from water-soluble and fat-soluble natural colored compounds, particularly curcumin, lactoferrin, caramel, chlorophyll, indigo, carmine, anthocyanins, betaine and their derivatives, violacein and deoxyviolacein, flavonoids and mixtures thereof, preferably curcumin, lactoferrin, caramel, chlorophyll, anthocyanins, betaine and their derivatives, flavonoids, or natural extracts containing them, and mixtures thereof. According to a specific and preferred embodiment, a colored compound selected from anthocyanins, curcumin and mixtures thereof is used.

[0043] Preferably, the total content of the natural colored compound or the colored compound of natural origin or the colored extract containing it is 0.01% to 15% by weight relative to the total weight of the colored powder, particularly 0.1% to 10%, or even 0.5% to 8%. Those skilled in the art can adjust the content according to the colored compound.

[0044] According to a particular embodiment, anthocyanins are used in a total content of 0.5% to 10% by weight, particularly 1% to 10% by weight, relative to the total weight of the colored powder.

[0045] According to another specific embodiment, curcumin is used in a total content of 0.5% to 5% by weight relative to the total weight of the colored powder.

[0046] The colored powder according to the invention further comprises at least one nitrogen-containing compound of formula (I) as defined below.

[0047] Nitrogen-containing compounds of formula (I) (compound ii) Therefore, the composition according to the invention comprises at least one compound of formula (I). in Indicates a single bond or a double bond. R 1 and R 3 Each of the following is independent of or selected from H, or optionally substituted C1-C 12Aliphatic chains, wherein one or more of the aliphatic chains preferably have 1 to 4 methylene units optionally substituted with O, C(O), NH or N (C1-C6 alkyl), R 2 and R 4 Each is independently selected from H, oxo group, thio group, and NR. x R y Halogenated or optionally substituted C1-C 12 Aliphatic chains, wherein one or more of the aliphatic chains preferably have 1 to 4 methylene units optionally substituted with O, C(O), NH or N (C1-C6 alkyl), R x and R y Independently representing H or C1-C6 alkyl, R 5 and R 6 Each C1-C group is independently selected from H, oxo, thio, or optionally substituted. 12 Aliphatic chains, wherein one or more of the aliphatic chains preferably have 1 to 4 methylene units optionally substituted with O, C(O), NH or N (C1-C6 alkyl), or R 5 and R 6 Together with the carbon atoms they are bonded to, they form optionally substituted aryl or optionally substituted imidazolyl groups.

[0048] It should be understood that in the compounds of formula (I), This indicates a single or double bond, making each atom in the ring neutral. In other words, the oxidation state of each nitrogen atom in the ring is 3, and the oxidation state of each carbon atom in the ring is 4.

[0049] In some implementation schemes, R 1 and R 3 They are either absent or selected from H and C1-C6 alkyl groups, especially alkyl groups.

[0050] In some implementation schemes, R 2 and R 4 Each is independently selected from H, oxo group, thio group, and NR. x R y And C1-C6 alkyl groups, especially alkyl groups.

[0051] Preferably, R 2 and R 4 Each group is independently selected from H, oxo, thio, and NH2. Typically, R... 2 and R 4 At least one of them represents an oxo group or a thio group. Preferably, R 4 It indicates an oxo group or a thio group, especially an oxo group.

[0052] In some implementation schemes, R 5 and R 6 Each is independently selected from H, oxo groups and C1-C6 alkyl groups, especially methyl.

[0053] In other implementations, R 5 and R 6 Together with the carbon atoms to which they are bonded, they form optionally substituted aryl groups (especially optionally substituted phenyl groups) or optionally substituted imidazolyl groups. Preferably, the aryl group (especially phenyl group) or imidazolyl group is optionally substituted by one or more, preferably one to two, substituents selected from C1-C6 alkyl groups, OH groups, and O-C1-C6 alkyl groups (e.g., methoxy groups).

[0054] According to a particular and preferred embodiment, the composition of the present invention comprises a compound of formula (I) corresponding to formula (IA): in R 7 Selected from H, C1-C6 alkyl, oxo, OH, thio, SH and O-C1-C6 alkyl. and R 1 To R 4 As defined above, and R 8 and R 9 Each of the following is independent of or selected from H, or optionally substituted C1-C 12 Aliphatic chains, wherein one or more of the aliphatic chains, preferably 1 to 4 methylene units, are optionally substituted with O, C(O), NH or N (C1-C6 alkyl).

[0055] R 7 Especially selected from H and oxo groups.

[0056] Preferably, in (IA), R 1 and R 3 Independently does not exist or represents H, R 2 Selected from H, oxo group and NH2, R 4 It is an oxo group, and R 7 Selected from H and oxo groups.

[0057] In one particular embodiment, the compound of formula (I) is selected from: 6,7-Dimethoxyquinazoline-2,4(1H ,3 H )-Diketone According to a preferred embodiment, the composition of the present invention comprises a compound of formula (I), wherein the compound of formula (I) is selected from compounds of formula (IA): Xanthine, hypoxanthine, uric acid and guanine are preferred, xanthine, hypoxanthine and guanine are more preferred, and guanine is even more preferred.

[0058] Preferably, in the compound of formula (IA), R 1 It does not exist, R 2 R is an NH2 group. 3 For H, and R 4 It is an oxo group. In this embodiment, the compound of formula (I) corresponds to guanine of the following formula: Guanine Within the meaning of this invention, "[C x -C y "Aliphatic chain" is understood to mean a saturated straight-chain or branched monovalent hydrocarbon chain containing x to y (especially 1 to 12) carbon atoms. According to the present invention, aliphatic chain encompasses straight-chain or branched substituted or unsubstituted alkyl, alkenyl or alkynyl groups.

[0059] Within the meaning of this invention, "(C x -C y "alkyl" is understood to mean a saturated straight-chain or branched monovalent hydrocarbon chain containing x to y (preferably x to y) carbon atoms. Examples include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl.

[0060] Within the meaning of this invention, "C" x -C y "Alkenyl" is understood to mean a straight-chain or branched monovalent hydrocarbon chain containing at least one double bond and x to y carbon atoms (where x is greater than or equal to 2). Examples include vinyl, propenyl, allyl, butenyl, pentenyl, or hexenyl.

[0061] Within the meaning of this invention, "(C x -C y "Alynyl" is understood to mean a straight-chain or branched monovalent hydrocarbon chain containing at least one triple bond and x to y carbon atoms (where x is greater than or equal to 2). Examples include ethynyl, propynyl, butynyl, pentynyl, or hexynyl.

[0062] Within the meaning of this invention, "halogen atom" or "halogen" is understood to mean fluorine, chlorine, bromine, and iodine atoms.

[0063] Within the meaning of this invention, aryl is understood to refer to an aromatic hydrocarbon group, which preferably contains 6 to 10 carbon atoms and comprises one or more linked rings, such as phenyl or naphthyl. Advantageously, it is phenyl.

[0064] Within the meaning of this invention, "heteroaryl" or "heteroaromatic" is understood to mean an aromatic group comprising 5 to 10 ring atoms, wherein the ring atoms include one or more heteroatoms, advantageously 1 to 4 heteroatoms, or even more advantageously 1 or 2 heteroatoms, such as sulfur, nitrogen, or oxygen atoms, and the remaining ring atoms are carbon atoms. Examples of heteroaryl groups include furanyl, thiopheneyl, pyrroleyl, pyridinyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, oxadiazolyl, thiazolyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, or indoleyl.

[0065] Within the meaning of this invention, "optionally substituted" is understood to mean that the mentioned groups are optionally replaced by one or more, preferably one to four, especially one or two selected from halogen atoms, C1-C6 alkyl, OH, oxo, aryl, N3, CN, NO2, aralkyl, NR a R b CoR c CO2R d CONR e R f and OR g Substituents in, where R a To R g Independently representing H, C1-C6 alkyl, C1-C6 haloalkyl, or aryl, preferably H or C1-C6 alkyl. Preferably, the substituent is selected from C1-C6 alkyl, oxo, or NR. a R b .

[0066] According to one specific implementation scheme, the compound of formula (Ia) is guanine. Guanine The guanine (Cl 75170) used according to the present invention is typically in the form of a white to pale yellow powder. It can be obtained from natural crystals (e.g., fish scales) that have been subjected to specific grinding (e.g., jet milling) to form non-disturbing particles with a particle size of less than 30 µm (preferably less than 15 µm).

[0067] "Particle size" is understood to refer to its D50 or median particle size by volume, as defined as the particle size such that 50% of the particles by volume have a particle size smaller than D50. The median particle size by volume can be evaluated using a Malvern MasterSizer laser particle size analyzer by optical diffraction, with the particles to be analyzed dispersed in a liquid medium such as octyldodecyl neovalerate.

[0068] According to one particular embodiment, the guanine particles according to the invention have a particle size of 0.5 to 30 µm, particularly 1 to 15 µm.

[0069] According to another specific implementation, the compound of formula (Ia) is xanthine.

[0070] According to another specific implementation, the compound of formula (Ia) is hypoxanthine.

[0071] Specifically, according to the present invention, a colored natural compound or a naturally derived compound or an extract containing thereof (i) is adsorbed onto the surface and / or interior of a crystal formed from a nitrogen-containing compound of formula (I). This “composite” form between the colored compound and the nitrogen-containing compound of formula (I) is produced by the following steps: dissolving the nitrogen-containing compound of formula (I) such that the natural colored compound or the naturally derived colored compound or an extract containing thereof (i) can be fixed in a non-covalent manner onto the surface or interior of the crystal of the nitrogen-containing compound of formula (I).

[0072] In the colored powder of the present invention, the content of nitrogen-containing compound (preferably guanine) of formula (I) is particularly 45% to 99% by weight relative to the total weight of the colored powder, especially 50% to 99% by weight, for example 65% to 99%, especially 70% to 98% by weight.

[0073] According to certain specific embodiments, the content of the nitrogen-containing compound (preferably guanine) of formula (I) is 45% to 99% by weight relative to the total weight of the colored powder, particularly 50% to 99%.

[0074] According to a specific implementation scheme, the nitrogen-containing compound of formula (I) is preferably guanine: - Relative to the total weight of the colored powder, it is 40% to 60% by weight, or - Relative to the total weight of the colored powder, it is 50% to 70% by weight, or - Relative to the total weight of the colored powder, it accounts for 60% to 70% by weight, or - Relative to the total weight of the colored powder, it accounts for 85% to 95% by weight, or - Relative to the total weight of the colored powder, it accounts for 90% to 95% by weight, or - Relative to the total weight of the colored powder, it accounts for 90% to 97% by weight.

[0075] The powder suitable for use in this invention, based on guanine and a colored compound selected from anthocyanins and curcumin, is thus obtained by the method according to the invention and comprises: Guanine [50-99%] + anthocyanins [0.5-10%] + citric acid [0.1-5%] Guanine [50-99%] + anthocyanins [1-10%] + citric acid [0.1-5%] Guanine [90-98%] + anthocyanins [1-10%] + citric acid [0.1-5%] Guanine [85-95%] + anthocyanins [0.5-10%] + citric acid [0.1-5%] Guanine [90-95%] + Curcumin [0.5-5%] + Citric acid [0.1-5%] Guanine [60-70%] + anthocyanins [1-10%] + citric acid [0.1-5%] Guanine [40-60%] + anthocyanins [1-10%] + citric acid [0.1-5%] Guanine [50-70%] + anthocyanins [1-10%] + citric acid [0.1-5%].

[0076] Other powders having other formulas (I) can also be obtained by the method of the present invention in a similar proportion of matrix (nitrogen-containing compound of formula (I)) and natural colored compound or naturally derived colored compound.

[0077] Method for preparing colored powders Generally, according to the method for preparing colored powder according to the present invention, a nitrogen-containing compound of formula (I) (compound i) is dissolved in an aqueous solution, and then the solution is introduced into a colored aqueous or ethanolic solution containing a natural colored compound or a colored compound of natural origin or an extract thereof (compound ii), inducing the co-precipitation of the nitrogen-containing compound of formula (I) and the colored compound, thereby forming a colored powder (or colored pigment). The colored powder is then washed with ethanol and / or water and then dried.

[0078] Therefore, the present invention also relates to a method for preparing colored powders as defined herein, comprising the following steps: i) Dissolve the nitrogen-containing compound (compound i) of formula (I) in an aqueous solution, preferably an alkaline aqueous solution. ii) Dissolving one or more naturally colored compounds or naturally derived colored compounds or extracts containing them (water-soluble compounds ii) in optionally acidified water or ethanol solution (iia), or alternatively dissolving one or more naturally colored compounds or naturally derived colored compounds or extracts containing them (lipid-soluble compounds ii) in an organic solvent, especially a carbonyl solvent (iib). iii) Introduce the solution obtained in i) into the colored solution obtained in ii), optionally with an acid present in the aqueous solution, so that the nitrogen-containing compound of formula (I) co-precipitates with the natural colored compound and / or the plant-derived extract and forms the colored powder. iv) Separate the liquid phase from the solid colored powder by filtration or centrifugation. v) Wash the colored powder obtained in iv) with ethanol, and separate the liquid phase from the solid colored powder by filtration or centrifugation. vi) Rinse the colored powder obtained in v) with water, and separate the liquid phase from the solid colored powder by filtration or centrifugation. vii) Dry the colored powder.

[0079] According to a preferred embodiment, in the dissolution step (ii), the natural colored compound or a naturally derived colored compound or an extract containing it is soluble in an aqueous solution or an ethanol solution, preferably soluble in an aqueous solution.

[0080] According to the first implementation plan, the naturally colored compound is water-soluble.

[0081] For example, the colored powder according to the invention is prepared at room temperature according to the following scheme: 1. Dissolve guanine in an alkaline aqueous solution. 2. Dissolve the natural colored compound in an aqueous solution that is acidified if necessary, or in a water-miscible organic solvent (e.g., ethanol). 3. Transfer the guanine solution to the dye solution while stirring. 4. If necessary, add acid to precipitate the precipitate and allow it to come into contact for the required time. 5. Separate the liquid from the solid (by filtration or centrifugation). 6. Wash the solid with ethanol. 7. Separate the liquid from the solid again. 8. Wash the solid with water. 9. Separate the liquid from the solid again. 10. Dry the solid (preferably at a low temperature), and 11. Grinding.

[0082] According to another implementation, the naturally colored compound is fat-soluble.

[0083] For example, the colored powder according to the invention is prepared at room temperature according to the following scheme: 1. Dissolve guanine in an alkaline aqueous solution. 2. Dissolve the natural colored compound in an aqueous solution or organic solvent (e.g., acetone) that has been acidified if necessary. 3. Transfer the guanine solution to the colored compound solution while stirring. 4. If necessary, add acid to precipitate the precipitate and allow it to come into contact for the required time. 5. Separate the liquid from the solid (by filtration or centrifugation). 6. Wash the solid with ethanol. 7. Separate the liquid from the solid again. 8. Wash the solid with water. 9. Separate the liquid from the solid again. 10. Dry the solid (preferably at a low temperature), and 11. Grinding.

[0084] Pigment paste Another object of the present invention is a pigment paste comprising a colored powder as defined herein and one or more oils.

[0085] The present invention also relates to a method for preparing a pigment paste as defined above, comprising the following steps: i) Grinding the colored powder as defined in this invention, and ii) Mix with one or more oils.

[0086] Pigment pastes may contain one or more colored powders.

[0087] According to the first embodiment, the pigment paste contains a single colored powder (single pigment).

[0088] According to another embodiment, the pigment paste comprises several colored powders (pigment mixtures) according to the invention.

[0089] According to a specific implementation scheme, the colored powder is subjected to at least one dry milling step.

[0090] In various dry grinding processes, grinding mills that can achieve fine to extremely fine grinding quality (D50 < 30 µm or even < 15 µm) through friction, collision or a combination thereof can be used, such as air jet (or neutral gas) mills or shaft mills, especially air jet mills.

[0091] In particular, an air jet mill or a shaft mill can be used, with an air jet mill being more preferred.

[0092] Those skilled in the art can use the grinding mill based on the supplier's recommendations.

[0093] The drying step is carried out, in particular by heating, preferably by placing it in an oven at a temperature greater than or equal to 60°C for 1 to 8 hours and / or by contacting it with a stream of dry air.

[0094] The drying step removes moisture, thereby enhancing the covering power of the colored powder. This step can be accomplished, in particular, using an oven.

[0095] One or more oils that can be used to prepare the pigment paste according to the present invention may be selected from hydrocarbon oils, silicone oils and mixtures thereof.

[0096] "Oil" is understood to refer to fats that are insoluble in water, and are liquid at 25°C and atmospheric pressure.

[0097] According to the present invention, "hydrocarbon oil" is understood to mean oil that mainly contains hydrogen atoms and carbon atoms.

[0098] According to the present invention, "silicone oil" is understood to mean an oil containing at least one silicon atom, especially at least one Si-O group.

[0099] Hydrocarbon oil is preferred.

[0100] These include, in particular, straight-chain or branched C8-C19 alkanes, oils selected from plant-derived hydrocarbon oils, and C... 10 -C 40 Synthetic ethers, C 10 -C 40 Synthetic esters, C 12 -C 26 fatty alcohols, C 12 -C 22 Higher fatty acids and their mixtures.

[0101] According to one particular embodiment, the pigment paste according to the invention may contain at least one ester oil.

[0102] "Ester oils" (polar) especially include: - Hydroxy esters, preferably having a total carbon number of 35 to 70, such as polyglycerol-2 triisostearate, isostearyl lactate, octyl dodecyl hydroxystearate, diisostearate malate, propyl gallate; glyceryl stearate; diethylene glycol diisonononate; - Fatty acid esters, especially fatty acid esters with 4 to 22 carbon atoms, - Synthetic esters, such as oils of the formula R1COOR2, wherein R1 represents a residue of a straight-chain or branched fatty acid containing 4 to 40 carbon atoms, and R2 represents a hydrocarbon chain containing 4 to 40 carbon atoms, especially a branched hydrocarbon chain, provided that R1+R2≥16, for example, isononyl isononanoate, ethyl 2-hexyl palmitate, octyl dodecyl neopentyl ester, octyl-2-dodecyl stearate, isostearyl isostearate, octyl-2-dodecyl benzoate, isopropyl myristate, isopropyl palmitate, butyl stearate, hexyl laurate, 2-ethylhexyl palmitate, 2-hexyldecyl palmitate, 2-octyldecyl palmitate, 2-octyl dodecyl myristate, and 2-diethylhexyl succinate; - Straight-chain fatty acid esters with a total carbon number of 35 to 70; - Esters of aromatic acids and alcohols containing 4 to 22 atoms; - Esters of fatty alcohols or esters of branched C24-C28 fatty acids; - A polyester obtained by esterification of a hydroxylated carboxylic acid with at least one triglyceride of an aliphatic monocarboxylic acid and an aliphatic dicarboxylic acid, wherein the polyester is optionally unsaturated; And their mixtures.

[0103] According to one particular embodiment, the pigment paste comprises a hydrocarbon oil selected from hydroxylated esters, synthetic esters, and mixtures thereof, preferably a hydroxylated ester.

[0104] The colored powder or pigment paste according to the invention can be formulated in a cosmetic composition, which further comprises at least one additional ingredient.

[0105] cosmetic composition Therefore, the present invention also relates to a cosmetic composition comprising, in a physiologically acceptable medium, a colored powder or a pigment paste as defined herein, and one or more other ingredients selected from oils, C1-C5 monools, glycols, surfactants, fillers, gelling agents or structuring agents, film-forming agents, cosmetic active ingredients, antioxidants, preservatives, fragrances, and mixtures thereof.

[0106] According to the present invention, "cosmetic composition" is understood to mean any composition for cosmetic (i.e., aesthetic purposes) that can come into contact with the surface parts of the human body, more particularly with keratin materials, especially human skin and / or lips.

[0107] According to the present invention, "physiologically acceptable medium" is understood to mean any excipient suitable for topical application that can contact keratin materials without the risk of toxic side effects, incompatibility, instability and / or allergic reactions.

[0108] According to the present invention, "keratin material" is understood to mean skin and / or its appendages, more particularly human skin and / or lips. Specifically, this refers to the skin of the face and / or neck and / or body, as well as the lips. In the context of the present invention, keratin material is healthy, i.e., not exhibiting a condition or symptom that is a pathological condition (a "non-healthy" subject with a symptom). The terms healthy skin and / or lips or skin and / or lips will be used interchangeably throughout the rest of the specification.

[0109] The oil in the composition includes, in particular, the oil used for pigment pastes as described above.

[0110] "Filler" should be understood to mean any shape, especially flakes, spheres, or rectangles, of colorless or white, mineral or organic, natural or synthetic particles, in an insoluble form and dispersed in the medium of the composition. These fillers are used in particular to modify the rheology or texture of the composition and / or to impart a matte effect.

[0111] The filler may be coated or uncoated on the surface. In particular, it may be treated on the surface with silicone, amino acids, fluorinated derivatives or any other substance that promotes the dispersion and compatibility of the filler in the composition.

[0112] Fillers are typically selected from inorganic or organic fillers.

[0113] These include, in particular, silica, mica, kaolin, zinc oxide, and titanium oxide of natural or synthetic origin; cellulose powder; calcium carbonate, magnesium carbonate, and magnesium bicarbonate; boron nitride; bismuth oxychloride, barium sulfate, and calcium silicate; yeast-fermented lauroyl lysine powder, such as GranPowder products; lauroyl lysine; clay; zinc, magnesium, or lithium stearate, zinc laurate, and magnesium myristate; powders of synthetic polymers, such as polyethylene, polyester, and polyamides (e.g., nylon); powders of polyacrylic acid or poly(methacrylic acid) (PMMA); powders of crosslinked elastomer organopolysiloxanes coated or uncoated with silicone resins; powders of silicone resins (INCI name: polymethylsilsesquioxane); powders of organic materials of natural origin, such as crosslinked or non-crosslinked starch powders like corn starch, wheat starch, or rice starch; and powders of plant origin, such as rice powder, cotton powder, silk powder, and mixtures thereof.

[0114] Gelling agents include, in particular, mineral gelling agents such as bentonite, and polymer gelling agents such as polysaccharides or acrylic gelling agents.

[0115] Structural agents include, in particular, fats, pasty fats and mixtures thereof.

[0116] According to the present invention, "fat" is understood to mean a compound that is solid at 25°C or a compound that contains a portion that is solid at 25°C. In particular, fats, waxes, paste-like compounds and mixtures thereof may be mentioned.

[0117] "Pasty fatty substances" refer to non-crystalline fatty compounds that contain both liquid and solid portions at a temperature of 25°C.

[0118] Fatty substances or fats can be of animal, plant, mineral, or synthetic origin.

[0119] Within the meaning of this invention, "wax" is intended to refer to a compound that is solid at 25°C, has a reversible solid / liquid state change, and a melting temperature above 30°C (preferably above 45°C).

[0120] The composition may also contain additional pigments different from the colored powders according to the invention.

[0121] "Pigment" should be understood to mean white or colored inorganic (mineral) or organic particles that are insoluble in the aqueous phase from which they are dispersed, intended to color and / or opaque compositions and / or deposits produced by those compositions. References may be made to mineral pigments, organic pigments, and composite pigments (i.e., pigments based on mineral and / or organic materials). Mineral pigments include, for example, iron oxides in black, yellow, red, and brown; manganese violet; ultramarine; chromium oxides, iron blue, and carbon black, as well as mixtures thereof.

[0122] Organic pigments include, in particular, lakes obtained from dyes such as FD&C Black 2, FD&C Blue 1, FD&C Green 3, FD&C Green 5, FD&C Orange 4, FD&C Orange 5, FD&C Orange 10, FD&C Red 3, FD&C Red 6, FD&C Red 7, FD&C Red 9, FD&C Red 13, FD&C Red 19, FD&C Red 21, FD&C Red 22, FD&C Red 27, FD&C Red 28, FD&C Red 30, FD&C Red 33, FD&C Red 36, FD&C Red 40, FD&C Yellow 5, FD&C Yellow 6, FD&C Yellow 10, carbon black, and paints based on cochineal red.

[0123] Pearlescent pigments are selected, for example, from mica coated with titanium oxide, mica titanium coated with iron oxide, mica titanium coated with iron blue, mica titanium coated with chromium oxide or tin oxide, mica titanium coated with organic pigments as described above, and pigments based on bismuth oxychloride.

[0124] According to one particular embodiment, the composition of the present invention comprises organic pigments, particularly organic pigments selected from D&C dyes and cochineal-based lakes as described above.

[0125] The compositions of the present invention can be anhydrous compositions.

[0126] "Anhydrous composition" is specifically understood to mean that water is not intentionally added to the composition of the present invention, but may be present in trace amounts in the various compounds used in the composition. In particular, the composition according to the invention contains less than 4% water by weight relative to the total weight of the composition, preferably less than 3%, more preferably less than 2%, more preferably less than 1%, even more preferably less than 0.5% water, or is completely anhydrous. According to a particular embodiment, the composition is anhydrous.

[0127] According to another embodiment, the composition of the present invention may comprise an aqueous phase.

[0128] The aqueous phase of the composition comprises water and optionally a water-soluble solvent.

[0129] According to the present invention, "water-soluble solvent" is understood to mean a compound that is liquid at room temperature and miscible with water (more than 50% by weight miscible with water at 25°C and atmospheric pressure). These particularly include: - Lower C1-C5 monools, such as ethanol, isopropanol and mixtures thereof, preferably ethanol; - C2-C8 diols, such as ethylene glycol, propylene glycol, 1,3-butanediol, pentanediol, dipropylene glycol and mixtures thereof, preferably C3-C5 diols; - C2-C32 polyols, such as glycerol, polyglycerol, polyethylene glycol, and mixtures thereof. And their mixtures.

[0130] preparation According to a particular embodiment, the compositions of the present invention are compositions for the care and / or cosmetic application of keratin materials, particularly compositions for the cosmetic application and / or care of the skin and / or lips.

[0131] It can be in the form of lotion, dispersant, gel, water-in-oil emulsion, oil-in-water emulsion, multiple emulsion, anhydrous composition, cake powder, loose powder, solid composition such as rod, molded product in small container, or paste.

[0132] As a skincare composition, creams or serums for the face and / or neck may be mentioned in particular.

[0133] Lip balm is particularly noteworthy as a lip care composition.

[0134] Cosmetic compositions for use on the skin include, in particular, foundation, primer, face powder, color corrector, eyeshadow, or blush.

[0135] Cosmetic compositions for the lips include, in particular, lip gloss, lipstick, lip liner, lip tint, lip balm, or lip balm.

[0136] According to another specific embodiment, the composition is a composition for use on the skin, particularly a foundation or face powder.

[0137] According to a particular embodiment, the compositions of the present invention are compositions for the face or lips, particularly powders for the face or compositions in the form of lipsticks, lip balms, lip glosses or lip stains for the lips.

[0138] According to a particular embodiment, the composition is a composition for the lips, particularly an anhydrous composition for the lips.

[0139] According to another embodiment, the composition is a composition for nails, particularly nail polish.

[0140] According to another embodiment, the composition is used for eyelashes and / or eyebrows.

[0141] Beauty methods Another object of the present invention is a cosmetic method for treating and / or applying keratin materials, comprising applying a composition as defined in the present invention to the keratin material.

[0142] The composition used in the cosmetic method according to the present invention is as described above.

[0143] The compositions of the present invention provide color to keratin materials when applied to them. Using the colored powders of the present invention enables the colors to possess excellent vibrancy, photostability, and pH stability, facilitating the formulation of skincare and cosmetic products even under limited pH conditions, and resulting in improved color properties and hue range in the final composition.

[0144] The invention will now be described in the following non-limiting embodiments. Unless otherwise stated, percentages are expressed as % by weight of the component relative to the total weight of the composition.

[0145] Example Example 1: Preparation of colored powder on guanine support Guanine (Cl 75170) was used as the matrix.

[0146] 1.1 Methods using hydrophilic natural compounds Various natural colored compounds were used: cyanidin (anthocyanin), carrot juice (anthocyanin), beet juice, and curcumin, which yielded corresponding colored powders.

[0147] Colored powders were prepared at room temperature according to the following scheme: 1. Dissolve guanine in an alkaline aqueous solution (1N NaOH). 2. Dissolve the natural colored compound in an aqueous solution that is acidified (e.g., with acetic acid) if necessary, or in a water-miscible organic solvent (e.g., ethanol). 3. Transfer the guanine solution to the colored compound solution while stirring. 4. If necessary, add acid to precipitate the precipitate and allow it to come into contact for the required time. 5. Separate the liquid from the solid (by filtration or centrifugation). 6. Wash the solid with ethanol. 7. Separate the liquid from the solid again. 8. Wash the solid with water. 9. Separate the liquid from the solid again. 10. Dry the solid (preferably at low temperature), for example by zeodratation or freeze-drying, and 11. Grinding.

[0148] 1.2 Methods using lipophilic natural compounds Lipophilic natural colored compounds such as β-carotene or lycopene enable the production of corresponding colored powders.

[0149] Colored powders were prepared at room temperature according to the following scheme: 1. Dissolve guanine in an alkaline aqueous solution (1N NaOH). 2. Dissolve the natural colored compound in an aqueous solution or an organic solvent (e.g., acetone) that has been acidified if necessary. 3. Transfer the guanine solution to the colored compound solution while stirring. 4. If necessary, add acid to precipitate the precipitate and allow it to come into contact for the required time. 5. Separate the liquid from the solid (by filtration or centrifugation). 6. Wash the solid with ethanol. 7. Separate the liquid from the solid again. 8. Wash the solid with water. 9. Separate the liquid from the solid again. 10. Dry the solid (preferably at low temperature), for example by zeodratation or freeze-drying, and 11. Grinding.

[0150] A powder based on guanine and a colored compound selected from anthocyanins and curcumin can be obtained by the method according to the invention and comprises: Guanine [45-99%] + anthocyanins [0.5-10%] + citric acid [0.1-5%] in particular: Guanine [50-99%] + anthocyanins [0.5-10%] + citric acid [0.1-5%] Guanine [50-99%] + anthocyanins [1-10%] + citric acid [0.1-5%] Guanine [90-98%] + anthocyanins [1-10%] + citric acid [0.1-5%] Guanine [85-95%] + anthocyanins [0.5-10%] + citric acid [0.1-5%] Guanine [90-95%] + Curcumin [0.5-5%] + Citric acid [0.1-5%] Guanine [60-70%] + anthocyanins [1-10%] + citric acid [0.1-5%] Guanine [40-60%] + anthocyanins [1-10%] + citric acid [0.1-5%] Guanine [50-70%] + anthocyanins [1-10%] + citric acid [0.1-5%].

[0151] Example 2: Comparative Study with Other Methods The colored powder used in these tests was a guanine-cyanidin powder obtained according to the method described in Example 1.1, particularly a guanine-cyanidin powder containing guanine [50-99%] + cyanidin [0.5-10%] + citric acid [0.1-5%].

[0152] Various tests were conducted under the following conditions: - Contains metal (Mg) and does not contain metal (Mg). - Compared to allantoin (other nitrogen-containing compounds not of this invention), guanine - With and without a dissolving step.

[0153] In this study, the magnesium salt used was magnesium acetate tetrahydrate. Changes in reactants were made on an equimolar basis.

[0154] Then, the obtained colored powder was evaluated according to the following scheme, based on yield (expressed as a percentage), hiding power (expressed as a percentage), and photostability (ΔE between the control and the exposure test sample): The yield is calculated based on the mass of the dried pigment (colored powder) obtained and the mass of the reactants used (anthocyanins or extracts + metal salts + guanine) according to the following formula: Yield (%) = Mass of dried pigment (g) / Mass of reactants (g) × 100 Coverage force measurement : - Preparation of nail polish containing 4% ground colored powder in the nail polish base: Weigh the colored powder, nail polish base and glass beads into a 125 ml container of an E-max grinder; then seal the container and place it in the grinder (+10°C); pre-grind at 500 rpm for 5 minutes; then grind for 15 minutes at 2000 rpm; at the end of grinding, remove the glass beads from the nail polish and fill the nail polish into 120 ml dispensers; place on a barrel roller for several hours to eliminate air bubbles.

[0155] - Apply the nail polish evenly to the comparison card (e.g., Leneta 2A) (300µm), and then allow it to dry; - The dried coating was analyzed using a spectrophotometer (MA98, with a mirror angle of 45°).

[0156] In the results described in Table 1 below, hiding power is expressed as a percentage: 100% indicates no color difference between the white and black portions of the contrast card after coating; hiding power is then obtained by comparing the white and black sides.

[0157] Light stability measurement - Cut the nail polish comparison card, expose one part to sunlight (765W / m2, 10 hours using a window glass filter), and place the other part in the dark; - Measure the color of two small cards using a spectrophotometer; The color difference between two samples allows us to obtain ΔE. The lower the ΔE, the better the photostability of the color.

[0158] The results are presented in Table 1 below: [Table 1] These results particularly indicate that: - Allantoin (other nitrogen-containing compounds different from those of formula (I) as defined in this invention) cannot produce the colored powder according to the invention; and When the colored compound and carrier are dissolved, the pigment (colored powder) has a rich, vibrant color and is stable to light. This is not the case when the carrier (in this case, guanine) is not dissolved. Therefore, dissolving the reactants allows the pigment to precipitate (i.e., form a colored powder).

[0159] Therefore, these results indicate that, compared to other conditions, the colored powders according to the invention, obtained by dissolving the matrix (e.g., guanine) and forming a complex with a colored compound (e.g., cyanidin), provide the best results in terms of yield, hiding power, and photostability. The addition of magnesium salts reduces the yield but can further improve the hiding power, and therefore may still be beneficial.

[0160] These results were confirmed by another colored compound: curcumin mixed with a guanine matrix under the following two comparative conditions: - A mixture of 0.04 g curcumin and 1.96 g guanine, wherein the guanine is dissolved (this invention). A mixture of 0.04 g curcumin and 1.96 g guanine, in which the guanine was not dissolved (comparison). [Table 2] These additional results using curcumin confirm that, compared to conditions without a matrix dissolution step, the colored powder according to the invention, obtained by dissolving a matrix (e.g., guanine) and forming a complex with a colored compound (e.g., curcumin), provides optimal results in terms of hiding power and photostability.

[0161] Example 3: Performance evaluation of the colored powder of the present invention Following the scheme described in Example 1.1, various colored powders were prepared on a guanine carrier using the following natural colored compounds: cyanidin, carrot, beet juice, and curcumin. The pH stability and light and pH stability of these colored powders (also referred to in this example as "guanine-colored compound complexes") were evaluated according to the following scheme, and compared with individual natural colored compounds: Visual assessment of pH stability (tested at pH=4 and pH=8): The colors of solutions of individual compounds and corresponding colored powders at the same concentration were observed with the naked eye at different pH values.

[0162] Visual assessment of pH and photostable stability (tested at pH=4 and pH=8): Before and after exposure to natural light, at different pH values, the colors of solutions of individual compounds and corresponding colored powders at the same concentration were observed with the naked eye.

[0163] The results are presented in Table 2 below: [Table 3] *The colored powder prepared according to the scheme described in Example 1.1.

[0164] These results indicate that the colored powder (guanine-colored compound complex) according to the present invention has better pH stability and light stability compared to natural colored compounds alone.

[0165] The vibrancy of the colors of these colored powders according to the invention was also evaluated and compared with commercial pigments (natural or synthetic).

[0166] The vibrancy of a color can be assessed visually or by calculating a vibrancy index. - Color measurement can obtain L, a, b, C, h (CIE LAB color space).

[0167] The vividness index is calculated using the following formula: The "Guinein Carrot" colored powder is more vibrant than New Red 1805 pigment.

[0168] The guanine-curcumin colored powder is more vibrant than Sunpuro yellow iron oxide pigment and J1 yellow pigment.

[0169] Example 4: Preparation of colored powders on different carriers, namely guanine, xanthine, and hypoxanthine. The colored compound used is curcumin.

[0170] The substrates used are guanine, xanthine, or hypoxanthine.

[0171] Colored powder was prepared according to the scheme described in Example 1.1.

[0172] The obtained colored powders were evaluated according to different criteria, including hiding power, color (L, C, h, a, and b), coloring ability, and yield, based on the following scheme: Opacity and photostability were evaluated as described in Example 2. Vividness index was evaluated as described in Example 3. Color and tinting ability were evaluated according to the following scheme: Powder color measurement in photographs - Measure the powder color using a photograph taken under the same lighting and exposure conditions (Canon EOS 250D, 85 mm lens; manual settings f20, 1 / 15s, ISO 200).

[0173] - Measurements were performed using ImageJ analysis software.

[0174] Color measurement (coloring power) of pastes - Grind the colored powder in an oil suitable for obtaining a colored paste; - Mix the colored paste with a commercial white filler and binder medium (ground to 50% TiO2 in a suitable oil) at a ratio of 1:4; - Grind the mixture until a homogeneous paste is obtained; obtain a degraded paste; - The degraded paste was evenly spread (0.5 mm thick) on the comparison card, and the color was measured using a spectrophotometer (MA98, 45° about the mirror angle).

[0175] The results are presented in Table 3 below: [Table 4] All results indicate that the colored powder obtained according to the present invention has good hiding power (>20) and good photostability (ΔE<8). Furthermore, as described in Example 3, the vividness index calculated based on the values ​​of L, a, b, C, h (CIE LAB color space) is greater than 5, indicating significant vividness.

[0176] Example 5: Formulation If conventional pigments use the colored powder according to the present invention, they are formulated into formulations according to conventional formulation methods, typically with a pre-dispersion step in one of the solvents of the formulation to better disperse in the composition.

[0177] 5.1 Lipstick [Table 5] *Prepared according to Example 1 5.2 Lipstick [Table 6] *Prepared according to Example 1 5.3 Nail Polish [Table 7] *Prepared according to Example 1

Claims

1. A colored powder comprising the following combination: (i) Naturally colored compounds or naturally derived colored compounds or colored extracts containing them, and (ii) Nitrogen-containing compounds of formula (I) in Indicates a single bond or a double bond. R 1 and R 3 Each of the following is independent of or selected from H, or optionally substituted C1-C 12 Aliphatic chains, wherein one or more of the aliphatic chains preferably have 1 to 4 methylene units optionally substituted with O, C(O), NH or N (C1-C6 alkyl), R 2 and R 4 Each is independently selected from H, oxo group, thio group, and NR. x R y Halogenated or optionally substituted C1-C 12 Aliphatic chains, wherein one or more of the aliphatic chains preferably have 1 to 4 methylene units optionally substituted with O, C(O), NH or N (C1-C6 alkyl), R x and R y Independently representing H or C1-C6 alkyl, R 5 and R 6 Each is independently selected from H, oxo group, thio group, or optionally substituted C1-C group. 12 Aliphatic chains, wherein one or more of the aliphatic chains preferably have 1 to 4 methylene units optionally substituted with O, C(O), NH or N (C1-C6 alkyl), or R 5 and R 6 Together with the carbon atoms they are bonded to, they form optionally substituted aryl or optionally substituted imidazolyl groups. Its features are, The colored powder does not contain aluminum or zinc metal salts.

2. The colored powder according to claim 1, characterized in that, The colored powder is insoluble.

3. The colored powder according to claims 1 to 2, characterized in that, The natural colored compounds or naturally derived colored compounds are selected from water-soluble and fat-soluble natural colored compounds, particularly curcumin, lactoferrin, β-carotene, capsanthin / capsicum, lycopene, caramel, chlorophyll, indigo, carmine, anthocyanins, betaine and their derivatives, violacein and deoxyviolacein, flavonoids or colored extracts containing them, and mixtures thereof.

4. The colored powder according to any one of claims 1 to 3, characterized in that, The compound of formula (I) corresponds to the following formula (IA): in R 7 Selected from H, C1-C6 alkyl, oxo, OH, thio, SH, and O-C1-C6 alkyl, and and R 1 To R 4 As defined in claim 1, R 8 and R 9 Each of the following is independent of or selected from H, or optionally substituted C1-C 12 Aliphatic chains, wherein one or more of the aliphatic chains, preferably 1 to 4 methylene units, are optionally substituted with O, C(O), NH or N (C1-C6 alkyl).

5. The colored powder according to claim 4, characterized in that, In the compound (IA), R 1 and R 3 Independently does not exist or represents H, R 2 Selected from H, oxo group and NH2, R 4 It is an oxo group, and R 7 Selected from H and oxo groups.

6. The colored powder according to claim 4 or claim 5, characterized in that, The compound (IA) is selected from the following compounds: Xanthine, hypoxanthine, uric acid, and guanine are preferred, with guanine being more preferred.

7. The colored powder according to any one of claims 1 to 6, characterized in that, The natural colored compound or a naturally derived colored compound or an extract containing it is adsorbed on the surface and / or inside of a crystal formed from a compound of formula (I).

8. The colored powder according to any one of claims 1 to 7, characterized in that, The colored powder contains magnesium salts.

9. The colored powder according to any one of claims 1 to 8, characterized in that, The total content of the natural colored compound or the colored compound of natural origin or the colored extract containing it is 0.01% to 15% by weight, particularly 0.1% to 10%, or even 0.5% to 8%, relative to the total weight of the colored powder.

10. The colored powder according to any one of claims 1 to 9, characterized in that, The content of the nitrogen-containing compound of formula (I) or (Ia) is 45% to 99% by weight relative to the total weight of the colored powder, particularly 50% to 99% by weight, for example 65% to 99%, particularly 70% to 98% by weight, and the nitrogen-containing compound is preferably guanine.

11. A method for preparing a colored powder as defined in any one of claims 1 to 10, comprising the following steps: i) Dissolve the nitrogen-containing compound of formula (I) in an aqueous solution, preferably an alkaline aqueous solution. ii) Dissolving one or more naturally colored compounds or naturally derived colored compounds or extracts containing them (water-soluble compounds ii) in optionally acidified water or ethanol solution (iia), or alternatively dissolving one or more naturally colored compounds or naturally derived colored compounds or extracts containing them (lipid-soluble compounds ii) in an organic solvent, especially a carbonyl solvent (iib). iii) Introduce the solution obtained in i) into the colored solution obtained in ii), optionally with an acid present in the aqueous solution, so that the nitrogen-containing compound of formula (I) co-precipitates with the natural colored compound or a naturally derived colored compound or a colored extract containing it and forms the colored powder. iv) Separate the liquid phase from the solid colored powder by filtration or centrifugation. v) Wash the colored powder obtained in iv) with ethanol, and separate the liquid phase from the solid colored powder by filtration or centrifugation. vi) Rinse the colored powder obtained in v) with water, and separate the liquid phase from the solid colored powder by filtration or centrifugation. vii) Dry the colored powder.

12. The method for preparing colored powder according to claim 11, characterized in that, In the dissolution step (ii), the natural colored compound or a naturally derived colored compound or a colored extract containing it is soluble in an aqueous solution or an ethanol solution, preferably soluble in an aqueous solution.

13. A pigment paste comprising a colored powder as defined in any one of claims 1 to 10 or a colored powder prepared by the method according to claim 11 or 12, and one or more oils.

14. A method for preparing a pigment paste as defined in claim 13, comprising the following steps: i) Grinding the colored powder as defined in any one of claims 1 to 10 or the colored powder prepared according to the method of claim 11 or 12, and ii) Mix with one or more oils.

15. A cosmetic composition comprising, in a physiologically acceptable medium, a colored powder as defined in any one of claims 1 to 10, or a colored powder prepared according to the method of claim 11 or 12, or a pigment paste as defined in claim 13, and one or more additional ingredients selected from oils, C1-C5 monools, glycols, surfactants, fillers, gelling agents or structuring agents, film-forming agents, cosmetic active ingredients, antioxidants, preservatives, fragrances, and mixtures thereof.

16. The composition according to claim 15, characterized in that, The composition is a skin and / or lip care composition or cosmetic composition, particularly for the lips.

17. A cosmetic method for treating and / or applying a keratin material, comprising applying a composition as defined in claim 15 or claim 16 to the keratin material.

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