Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
  • A61K8/87—Polyurethanes
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q3/00—Manicure or pedicure preparations
  • A61Q3/02—Nail coatings
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
  • C08G18/30—Low-molecular-weight compounds
  • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
  • A61K2800/42—Colour properties
  • A61K2800/43—Pigments; Dyes
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
  • A61K2800/57—Compounds covalently linked to a(n inert) carrier molecule, e.g. conjugates, pro-fragrances

Definitions

• Cosmetic composition in the form of an organic solution or dispersion comprising at least one polymeric dye
• the subject of the invention is new cosmetic compositions comprising at least one polyurethane polymer dye, in particular a composition for making up keratin materials.
• coloring material in cosmetic compositions, either inorganic or organic pigments or lacquers, which are generally insoluble in aqueous and organic media, or dyes soluble in aqueous or organic media.
• the pigments and lacquers used in the make-up field are of very diverse origin and chemical nature. Their physicochemical properties: particle size, specific surface, density etc. are therefore very different. These differences are reflected in variations in behavior: the ease of implementation, of dispersion, the stability to light, to temperature and the mechanical properties in the case of powders are specific to each coloring matter. These differences in behavior frequently require the formulator to readjust the composition of the formula when the shade of this formula is changed. They also limit the production of certain formulas in the form of monochrome. In particular, certain shades are impracticable because the pigments or lacquers which theoretically allow them to be obtained are incompatible with one another.
• Mineral oxides are preferably used for coloring cosmetic compositions, because the organic lacquers and the soluble dyes show too much bleeding, which in particular has the effect of staining the ocular lenses in the case of eye-iiners or mascaras.
• these mineral pigments are dull and bland, so it is necessary to introduce a large amount of them in the formulas of mascara, nail polish and eyeliner to obtain a sufficiently saturated line. This high percentage of mineral particles strongly affects the gloss of the makeup film. In the field of make-up, color coverage and saturation are therefore often associated with the dullness of the film.
• soluble dyes in certain makeup compositions has the effect of accentuating wrinkles or streaks of the skin and / or nails, the dye coming to be fixed, by migration, preferably in these wrinkles or streaks. This effect is contrary to that of attenuation of the defects of the skin and / or the nail which one seeks to obtain by makeup.
• These soluble dyes often have the drawback of leaving spots on the skin and nails after removing makeup, with which they have a great affinity.
• compositions comprising at least one polyurethane polymer dye, compositions which can be prepared according to invariable formulas, whatever the desired shade, with a very wide range of shades and very nuanced, with a high intensity of coloring associated with a shiny effect if desired, good coverage, with good lightfastness, including when the composition also comprises photoreactive pigments.
• These compositions are prepared from quantities of polyurethane polymer dye sufficiently low not to destabilize the formulas, but in quantities large enough to be easily dosed in a reproducible manner.
• compositions do not release dye on the skin and on the nails, which avoids the appearance of streaks on the made-up skin or of spots after makeup removal.
• the subject of the invention is therefore a cosmetic composition in the form of an organic solution or dispersion comprising at least one organic solvent and at least one film-forming polymer, characterized in that it comprises at least one polyurethane polymer dye.
• the subject of the invention is also the use of a polyurethane polymeric dye, in a composition for making up keratin materials in the form of an organic solution or dispersion comprising at least one organic solvent and at least one film-forming polymer. , to form a colored film on said keratin materials.
• Another subject of the invention is the use of a polyurethane polymeric dye in a composition for making up keratin materials in the form of an organic solution or dispersion comprising at least one organic solvent and at least one film-forming polymer, which does not color the said keratin materials.
• the subject of the invention is also a process for making up keratin materials, characterized in that a composition as defined above is applied to said keratin materials.
• the invention also relates to a process for the preparation of such a composition, characterized in that the polymeric dye is introduced into the composition in the form of a powder.
• organic dispersion is understood to mean a dispersion of solid particles.
• polymeric dye in the present description, a copolymer based on at least two distinct monomers, at least one of which is an organic dye monomer.
• these dyes have the property of not migrating, of not exuding, of not being extractable or sublimable. They are also known to be light-stable and have a strong coloring power.
• the media in which their use is envisaged in these documents are thermoplastic media, essentially for the manufacture of packaging. None suggests the astonishing properties of these polymers once they are incorporated into cosmetic compositions.
• polyurethane polymeric dyes can be of the crystalline, semi-crystalline or amorphous type.
• polyurethane polymeric dyes have an intrinsic viscosity of at least 0.20 (according to the method described in US Pat. No. 5,194,463). and can result from the polymerization of several monomers including:
• the di-isocyanate residues can be of the aliphatic, alicycic or aromatic type, such as for example 2,4-toiylene di-isocyanate, 2,6-tolylene di-isocyanate, 4,4'-biphenylene di-isocyanate, p-xylene di-isocyanate, methylene di-p-phenyl di-isocyanate, p-phenylene di-isocyanate, m-phenylene di-isocyanate, hexamethylene di-isocyanate, isophorone di-isocyanate, etc.
• the diol residues can be chosen, for example, from ethylene glycol, 1, 2-propane diol, 1, 3-propane diol, 2-methyl-1, 3-propanediol, 1, 4-butane diol, 2,2-dimethyl-1,3-propanediol, 1,6-hexanediol, 1,10-decane diol, 1,12-dodecane diol, 1,2-cyclohexane diol, 1,4-cyclohexanediol, 1,2-cyclohexane dimethanol, x, 8-bis (hydroxymethyl) -tricyclo- [5.2.1.0] decane, in which x represents 3, 4 or 5; diols comprising at least one oxygen atom in the chain such as, for example, diethylene glycol, triethylene glycol, dipropylene glycol, 1,3-bis (2-hydroxyethyl) benzene, 1,4-bis (2- hydroxyethyl) benzene
• these diols contain 2 to 18 and preferably 2 to 12 carbon atoms.
• R is a divalent radical chosen from C2-C10 alkylene, C3-C8 cycloalkylene, arylene, alkylene (C1-C4) -arylene-alkylene (C1-C4), alkylene (C1-C4) -cycioalkylene (C3- C8) -alkylene (C1-C4), alkylene (C1-C4) -1, 2,3,4,5,6,7-octahydronaphthalene-2,6-diyl-alkylene (C1-C4),
• R 1 is a divalent organic radical comprising (a) from 1 to 100 mol% of coloring organic diol in which the hydroxyl groups of said diol are linked by an alkylene unit to the rest of the coloring compound, and (b) from 0 to 99 mol% of organic diols of formula HO-R 2 -OH, in which R 2 is a divalent radical chosen from the radicals C2-C18 alkylene, C3-C8 cycloalkylene, (C1-C4) alkylene-arylene-C1-C4 alkylene radicals ), alkylene (C1-C4) -cycloalkylene (C3-C8) -alkylene (C1-C4), alkylene (C1-C4) -1, 2,3,4,5,6,7-octahydronaphthalene-2,6- diyl-alkylene (C1 -C4), alkylene (C2-C4) -0-alkylene (C2-C4), alkylene (C2-C4)
• R1 comprises from 5 to 50 mole percent of coloring diol, and n ranges from 2 to 100.
• the coloring diol monomers are selected from a variety of classes of chromophores. These classes of chrompophores can be chosen from anthraquinones, methines, bis-methines, azo-methines, arylidenes, 3H-dibenzo [7, ij] isoquinolines, phthaloylphenoxazines, phthaloylacridone, anthrapyrimidines, anthrapyrazoles, phthalocyanines, quinophthalones, indophenols, perinones, nitroarylamines, benzodifurane, 2 H-1-benzopyran-2-one, quinophthalones, triphenodioxazines, fluoridines, benzanthrones, indigo, thioindigo, xanthene, acridine, azine, oxazine, etc., These coloring monomers must bear at least two hydroxyl groups.
• the polymeric dye comprises at least 5% by weight of coloring monomer, and does not comprise more than 55% by weight.
• the percentage by weight of coloring monomer relative to the total weight of the copolymer ranges from 10 to 40%.
• the polymeric dye which can be used in the present invention can be in crude form or in the form of a dispersible powder.
• a polymeric dye is used in the form of a crude powder soluble in organic media.
• a dispersion in an aqueous medium can be prepared in a known manner from water, from crude polymer dye as described in patent US-5, 194,463.
• the polymeric dye in the form of a powder or granule, and at least one ionic surfactant, preferably an anionic or amphoteric surfactant.
• the aionic and amphoteric surfactants can be preferably chosen from alkaline salts of C12-C24 fatty acids, soy phosphatides, phospholipids, lysophospholipids.
• these ionic surfactants are introduced in amounts preferably between 0.5 and 30%, and even more preferably between 1 and 10% by weight relative to the weight of the polymeric dye.
• these dispersions further comprise at least one nonionic surfactant, which is advantageously chosen from polyoxyethylenated derivatives having a molecular weight greater than 300, preferably around 1000 to 15000 and a hydrophilic-lipophilic balance (or HLB balance) greater than or equal to 10.
• an aqueous dispersion of polymeric dye can be prepared by following the following steps: (i) preparation of an oil-in-water emulsion from water, of a solution of the polymeric dye in a volatile organic solvent in which it is soluble, in the presence of at least one ionic surfactant and optionally a nonionic surfactant; (ii) evaporation of the volatile organic solvent.
• the volatile organic solvent which can be used for the implementation of this process must be immiscible with water and capable of dissolving the polymer.
• its boiling point is less than 100 ° C. It can for example be chosen from: hydrocarbon solvents such as n-hexane, cyclohexane, cyclopentane; chlorinated solvents such as methylene chloride, chloroform; alkyl esters of carboxylic acids, such as ethyl acetate; dialkyl ethers such as diisopropyl ether.
• a mixture of solvents comprising, in addition to the solvents described above, a volatile, polar, water-miscible solvent, such as acetone or a low molecular weight alkanol.
• a volatile, polar, water-miscible solvent such as acetone or a low molecular weight alkanol.
• the water from the aqueous dispersions described above can then be evaporated, for example by atomization or by lyophilization, in order to obtain a polymeric dye powder dispersible in other media, in particular in organic media. A dispersion of the polyurethane polymer dye is thus obtained in an organic solvent medium.
• this polymeric dye can be incorporated in the form of crude powder or dispersible powder. It can also be incorporated in the form of an organic pigment paste. The preparation of such a pigment paste is known to a person skilled in the art.
• the polymeric dyes which can be used in the compositions according to the invention can be introduced in amounts ranging from 0.01 to 10% and preferably from 0.5 to 2%.
• the polymeric dyes described above have the advantage of having the same general chemical structure and the same physicochemical properties, in very different color ranges. Thus, a red pigment will have the same behavior as a yellow pigment. This homogeneity of behavior allows the manufacture of make-up compositions in the form of monochrome. When mixing monochrome to achieve a shade, there is no problem of incompatibility between the different colors.
• polymeric dyes used in the compositions according to the invention have a coloring power very close to that of organic lakes, and have a very high light stability, this even in the presence of titanium dioxide or zinc. They can therefore be used in place of organic lacquers in all makeup formulas. Their high light stability makes it possible to present the cosmetic compositions comprising them in transparent packaging. Thus, the user can choose more precisely the color of the product she is buying. In addition, they do not interfere with oils and / or active ingredients.
• compositions according to the invention comprise, in an organic phase, at least one polymeric dye according to the invention and at least one film-forming polymer.
• the composition according to the invention therefore comprises at least one film-forming polymer which can be chosen, in particular, from alkyd, acrylic and / or vinyl resins, polyurethanes and polyesters, celluloses and cellulose derivatives such as nitrocellulose, and resins resulting from the condensation of formaldehyde with an arylsuifonamide, and mixtures thereof.
• the film-forming polymer is generally in solution, for example at 5-25% by weight, in an organic solvent such as toluene, xylene, ethyl and / or butyl acetate, ketones, glycol ethers, esters and alcohols such as ethanol, isopropanol or butanol, and mixtures thereof.
• an organic solvent such as toluene, xylene, ethyl and / or butyl acetate, ketones, glycol ethers, esters and alcohols such as ethanol, isopropanol or butanol, and mixtures thereof.
• the film-forming polymer is not colored, that is to say that it does not contain a coloring monomer.
• composition can also comprise a plasticizing agent and optionally rheological agents.
• plasticizing agents mention may be made of citrates, phthalates, esters and / or camphor, generally used in an amount of 5-30% by weight relative to the weight of the composition.
• composition according to the invention can comprise colloidal silicic acid in an amount of 0.1% to 5% by weight, preferably in an amount of 1-2% by weight relative to the total weight of the composition.
• composition according to the invention can also comprise any additive known to a person skilled in the art as being capable of being incorporated into such a composition, such as spreading agents, wetting agents, dispersing agents, foams, preservatives, UV filters, dyes, pigments, nacres, active ingredients such as N-butylformal, D-panthenol, phytantriol, vitamins and their derivatives, keratin and its derivatives, melanin, collagen, cystine, chitosan and its derivatives, ceramides, biotin, trace elements, glycerin, protein hydrolysates, phospholipids, moisturizers.
• any additive known to a person skilled in the art as being capable of being incorporated into such a composition such as spreading agents, wetting agents, dispersing agents, foams, preservatives, UV filters, dyes, pigments, nacres, active ingredients such as N-butylformal, D-panthenol, phytantriol, vitamins and their derivatives, ker
• the composition preferably has an active material content of 5 to 70% by weight.
• composition according to the invention can be prepared by a person skilled in the art on the basis of his general knowledge and according to the state of the art.
• the composition according to the invention may constitute a makeup composition for keratin materials, in particular the skin, eyes, nails or lips. It can be in the form of a product to be applied to the nails, such as a varnish, a base for nails or a care base for nails, or in the form of a product to be applied to the eyelashes, such as a mascara, or in the form of a product to be applied to the lips such as a lipstick, a lip gloss, or in the form of a product to be applied to the skin such as a base of complexion, blush, eyeshadow, eyeliner.
• a makeup composition for keratin materials in particular the skin, eyes, nails or lips. It can be in the form of a product to be applied to the nails, such as a varnish, a base for nails or a care base for nails, or in the form of a product to be applied to the eyelashes, such as a mascara, or in the form of a product to be applied to the lips such as a lipstick, a lip gloss, or in the form
• Example 1 Composition of Nail Polish

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• Health & Medical Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Animal Behavior & Ethology (AREA)
• General Health & Medical Sciences (AREA)
• Public Health (AREA)
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• Birds (AREA)
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• Chemical & Material Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Organic Chemistry (AREA)
• Cosmetics (AREA)

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• 1996
  • 1996-12-16 FR FR9615455A patent/FR2757052B1/fr not_active Expired - Fee Related
• 1997
  • 1997-12-15 JP JP10527392A patent/JP2000513005A/ja active Pending
  • 1997-12-15 CA CA002274941A patent/CA2274941A1/fr not_active Abandoned
  • 1997-12-15 WO PCT/FR1997/002305 patent/WO1998026754A1/fr not_active Application Discontinuation
  • 1997-12-15 EP EP97952064A patent/EP0944380A1/de not_active Ceased

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