Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
  • A61Q1/02—Preparations containing skin colorants, e.g. pigments
  • A61Q1/10—Preparations containing skin colorants, e.g. pigments for eyes, e.g. eyeliner, mascara
• • 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
  • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
  • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
  • A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
• • 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
  • A61K8/85—Polyesters
• • 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
• • 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 aqueous dispersion comprising at least one polymeric dye
• the subject of the invention is new compositions for making up the eyes, the skin, the nails and the lips, comprising at least one polymeric sulfopolyester dye, as well as a method for making up the eyes, the skin, the nails, the lips. .
• Is usually used as coloring material in cosmetic compositions either inorganic or organic pigments or lacquers, which are generally insoluble in aqueous and organic media, or dyes dissolved 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 solubiated dyes show too much bleeding, which in particular has the effect of staining the ocular lenses in the case of eyeliners or mascaras.
• these mineral pigments are dull and bland in color, so it is necessary to introduce a large amount of them in the formulas of nail polish mascara and eyeliner to obtain a sufficiently saturated line.
• This high percentage of mineral particles strongly affects the gloss of the makeup film.
• the shiny compositions In the case of lipsticks, the problem is the same, the shiny compositions must be formulated with small amounts of pigments. In the field of make-up, therefore, coverage and saturation of color are often associated with dullness of the film.
• a pigment paste generally comprises a pigment, a surfactant or a dispersant and a wetting agent, such as glycerine or propylene glycol.
• aqueous-based nail varnishes from aqueous dispersions of polymers, having a hard, shiny, water-resistant film, but the problem of adhesion of the varnish to the nail is often encountered. .
• the film can then film easily. It is therefore sometimes necessary to use adhesion promoters.
• adhesion promoters have the disadvantage of harming other properties of the varnish film, such as gloss or hardness.
• the use of dyes dissolved in 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 skin defects that one seeks to obtain by makeup.
• These solubiated dyes often have the drawback of leaving spots on the skin and nails after makeup removal, with which they have a great affinity.
• the solubiated dyes have a very high coloring power, which leads to using them in infinitesimal quantities. Consequently, their dosage in a cosmetic formula under reproducible conditions is an extremely delicate operation. Also, it is with astonishment that the applicant has discovered new cosmetic compositions, comprising at least one polymeric sulfopolyester 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 coloration associated with a shiny effect if desired, with good lightfastness, including when the composition also comprises photoreactive pigments.
• compositions do not release dye on the skin, which avoids the appearance of streaks on the made-up skin or spots after makeup removal. They thus allow non-permanent coloring of the skin, nails, lips or eyelashes: after removing makeup, the skin, nails, lips or eyelashes are not colored. This gives a clean makeup removal. It is said that the compositions "do not scratch”.
• compositions are prepared from quantities of polymeric dye low enough not to destabilize the formulas, but in quantities large enough to be easily dosed in a reproducible manner.
• the subject of the invention is a cosmetic composition in the form of an aqueous dispersion, characterized in that it comprises at least one polymeric sulfopolyester dye and at least one film-forming polymer.
• the subject of the invention is also the use of a sulfopolyester polymeric dye, in a makeup composition for the eyes, the skin, the nails, the lips in the form of an aqueous dispersion, to form a colored film on the skin, eyelashes, eyelids, nails, lips.
• Another subject of the invention is the use of a sulfopolyester polymeric dye in a makeup composition for the eyes, the skin, the nails, the lips in the form of an aqueous dispersion, which does not color the eyelashes, eyes, nails, lips after makeup removal.
• the subject of the invention is also a method for making up the eyes, the skin, the nails, the lips, characterized in that a composition is applied to the eyelashes, the eyelids, the skin, the nails, the lips. as defined above.
• polymeric dye is meant a copolymer based on at least two distinct monomers, at least one of which is a monomeric organic dye.
• Sulfopolyester polymeric dyes can result from the polymerization of several monomers including:
• the dicarboxylic acid residues carrying a sulfonic group can be chosen from cycloaliphatic diacids such as the sulfo diacid 1,4-cyclohexane carboxylic acid, or alternatively from aromatic diacids such as sulfophthalic acids, 4-sulfonaphthalene-2,7- acid. dicarboxylic.
• 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.
• the coloring sulfopolyester may contain dicarboxylic acid residues free of sulfonic group; such residues can be of aliphatic, alicyclic or aromatic type, such as, for example, terephthalic, isophthalic acids, 1,4-cyclohexane dicarboxylic, 1,3-cyclohexane dicarboxylic, succinic, glutaric, adipic, sebacic, 1,2 dodecanedioic, 2,6-naphthalene dicarboxylic, etc.
• the organic dye monomers according to the invention must contain at least two substituents capable of reacting with at least one of the other monomers used for the preparation of the polymeric dye and must be stable at the temperature and under the conditions for preparing said polymer.
• the chemical nature of the coloring monomers does not matter for the implementation of the invention.
• These can, for example, be chosen from anthraquinones, methines, bis-methines, aza-methines, arylidenes, 3H-dibenzo [7, ij] isoquinolines, 2,5-diarylaminoterephthalic acids and their esters, phthaloyiphenothiazines, phthaloylphenoxazines, phthaloylacridone, anthrapyrimidines, anthrapyrazoles, phthalocyanines, quinophthalones, indophenols, perinones, nitroarylamines, benzodifuran, 2 H-1-benzopyran-2-one, quinophthalenes, quinophthalones quinacridones, triphenodioxazines, fluoridines, 4-amino-1, 8-naphthalimides, thioxanthrones,
• the substituents carried by the coloring monomer and capable of reacting with the other monomers can for example be chosen from the following groups: hydroxy, carboxy, ester,; amino, alkyli amino:
• R represents a group chosen from alkyls, aryls.
• R is chosen from C1-C8 alkyl groups and phenyl. Even more preferably, R is chosen from methyl, ethyl and phenyl 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%.
• a water-dispersible coloring polymer having linking groups comprising at least about 20 mol% of carbonyloxy and up to about 80 mol% of carbonylamido, said polymer containing sulfonate groups "solubility in water and having from about 0.01 to about 40 mol%, based on the total of all the equivalents of hydroxyl, carboxyl or amino reagents, of dye comprising one or more heat stable organic compounds initially having at least one condensable group, which has been reacted on or in the polymeric backbone.
• the above-mentioned equivalents include their various condensable derivatives, including carbalkoxy, carbaryloxy, N-alkylcarbamyloxy, acyloxy, chlorocarbonyl, carbamyloxy, N- (alkyl) 2 carbamyloxy, alkylamino, N- phenylcarbamyloxy, cyclohexanoyloxy and carbocyclohexyloxy.
• the coloring polymer contains carbonyloxy linking groups in the linear molecular structure, where up to 80% of said linking groups can be carbonylamido linking groups, the polymer having an inherent viscosity of about 0.1 to about 1.0, measured in a solution of 60-40 parts by weight of phenol / tetrachloroethane, at 25 ° C and at a concentration of 0.25 grams of polymer in 100 ml of the solvent, the polymer containing essentially equimolar proportions of acid equivalents (100 mole percent) relative to hydroxy and amino equivalents (100 mole percent), the polymer comprising the reaction residues of the reactants (a), ( b), (c), (d) and (e) or of their ester-generating derivatives or esteramide-generating derivatives:
• H- (OCH 2 -CH 2 ) n -OH n being an integer from 2 to about 20 or (2) from about 0.1 to less than about 15 mole percent, based on the total percentage in moles of hydroxy or hydroxy equivalents and d 'amino, are a polyethylene glycol of structural formula:
• n being an integer between 2 and about 500, and provided that the mole percentage of said polyethylene glycol in said range is inversely proportional to the value of n in said range;
• each R in reactants (c) or (d) is an H atom or an alkyl group having from 1 to 4 carbon atoms;
• the water-dispersible coloring polymer comprises:
• glycol monomer comprising from 45 to 60 mol% of diethylene glycol and from 55 to 40 mol% of 1, 4-cyclohexanedimethanol or of ethylene glycol or their mixture, (c) from 0.5 to 10 mol% of monomer dye
• sulfopolyester polymeric dyes are described in US Pat. No. 4,804,719.
• sulfopolyester polymeric dyes can be of the crystalline, semi-crystalline or amorphous type.
• the sulfopolyester polymeric dyes have an intrinsic viscosity of at least 0.20 (measured according to the method described in US Patent 4804719).
• the polymeric dye which can be used in the present invention may be in the form of a dispersible or soluble powder or of a solution or of a dispersion in an aqueous medium.
• a dispersion in an aqueous medium of a water-insoluble polymeric dye can be prepared in a known manner from water, of crude polymeric dye as described in documents US Pat. No. 5,032,670; US-4,999,418; US-5, 106.942; US-5,030,708; US-5,102,980; US-5,043,376, US-5,194,463.
• the sulfopolyester polymeric dye in the form of a powder or granule, and at least one ionic surfactant, preferably an anionic or amphoteric surfactant.
• the anionic 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 sulfopolyester 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:
• 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 is used for the implementation of this process, 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 powder of a polymeric dye composition dispersible in other media.
• an aqueous dispersion comprising at least one polymeric dye as described above and at least one film-forming polymer dispersible in water, insoluble in water.
• this polymeric dye can be incorporated in the form of an aqueous solution or dispersion or as it is, in the form of a dispersible powder or of crude powder.
• the polyester polymeric dye can be incorporated in the form of an aqueous dispersion or in the form of a water-dispersible powder.
• the polymeric dyes which can be used in the compositions according to the invention can be introduced in amounts ranging from 0.1 to 20%.
• 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 emulsions 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.
• the pigment particles are easily dissolved or dispersed in the medium, without the need for special additives. No sedimentation is observed, even after a long period of storage.
• the adhesion of the varnish film on the nail is improved by the incorporation of polymeric dyes, so there is no need to use adhesion promoters.
• aqueous compositions of nail polish which are both hard, shiny and non-peelable.
• the dispersions according to the invention comprise, in an aqueous phase, at least one sulfopolyester polymeric dye according to the invention and at least one film-forming polymer dispersible in water insoluble in water.
• composition according to the invention therefore comprises particles of film-forming polymer dispersed in an aqueous medium.
• polyurethanes for example anionics, polyester-polyurethanes, polyether-polyurethanes, radical polymers in particular of acrylic, styrene and / or vinyl type , polyesters, alkyd resins, alone or as a mixture.
• compositions can also comprise at least one water-soluble film-forming polymer or copolymer.
• film-forming polymers in water solution include water-soluble copolymers, and water-dispersible polycondensates with sulfonate functions. Such polymers are described in particular in patent application FR-A-2722404.
• water-soluble copolymers mention may, for example, be made of vinyl copolymers (vinyl alcohols, vinyl acetates, vinyl pyrrolidone, etc.), acrylics, acrylamides.
• hydrodispersible polycondensates containing sulfonate functions are known products, they are described in particular in documents US Pat. No. 3,779,993
• water-dispersible polycondensates containing sulfonate functions is preferably meant copolyesters or copolyesteramides.
• the copolyesters are obtained by polycondensation of at least one dicarboxylic acid or an ester thereof, of at least one diol and at least one difunctional compound sulfoaryldicarboxylique substituted on the aromatic ring by -S0 3 M wherein M represents a hydrogen atom or a metal ion such as Na + , Li + or K + .
• M represents a hydrogen atom or a metal ion such as Na + , Li + or K + .
• the polyesteramides are obtained in the same way as the polyesters, but the polycondensation also involves a diamine and / or an amino alcohol.
• the film-forming polymer is not colored, that is to say that it does not contain a coloring monomer.
• the dispersion may also comprise an associative polymer of the polyurethane type or a natural gum such as xanthan gum.
• the dispersion preferably has an active material content of 5 to 70% by weight.
• compositions according to the invention comprise at least one film-forming polymer.
• this polymer when this polymer has a glass transition temperature below room temperature, a increased hardness and gloss of the film.
• the film-forming polymer is not in the form of an aqueous dispersion containing a sulfopolyester and a copolymer containing vinyl acetate and a fumarate or maleate dialkyl and for which the copolymer is polymerized in the aqueous dispersion of sulfopolyester.
• 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 cosolvents, spreading agents, wetting agents, dispersing agents, defoamers, preservatives, UV filters, dyes, pigments, such as for example titanium dioxide, 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, hydrating agents.
• additives such as cosolvents, spreading agents, wetting agents, dispersing agents, defoamers, preservatives, UV filters, dyes, pigments, such as for example titanium dioxide, nacres, active ingredients such as N-butylformal, D-panthenol, phytant
• composition according to the invention can be prepared by the expert on "basic general knowledge and according to the state of the art.
• composition according to the invention may 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, in the form of a product to be applied to eyelashes, such as a mascara, of a product to be applied to the skin such as a foundation, cheek, eyeshadow, eyeliner, product to apply on the lips such as lipstick, lip lacquer, lip gloss.
• a product to be applied to the nails such as a varnish, a base for nails or a care base for nails
• eyelashes such as a mascara
• a product to be applied to the skin such as a foundation, cheek, eyeshadow, eyeliner
• product to apply on the lips such as lipstick, lip lacquer, lip gloss.
• the gloss measurements are carried out using a Micro Tri Gloss gloss meter sold by the company BYK GARDNER at an angle of 60 °.
• the hardness measurements are made according to standard NFT-30-016. This measurement is made on a film dried at 30 ° C under 50% relative humidity.
• Example 1 Composition of eyeliner
• coloring polyester comprising 10% of blue coloring monomer, prepared in accordance with Example 4 of US Pat. No. 4,804,719 put in aqueous solution with 21.6% of active material.
• composition obtained by dispersion of all the components in water is stable over time, in particular no sedimentation is observed after several weeks of storage.
• This composition is liquid and easy to apply, it gives a saturated, covering and shiny makeup.
• the varnish obtained is slightly colored, pink, and translucent, it does not color the nail after makeup removal.
• the varnish film is shiny, hard and water resistant, it is only moderately peelable.
• the varnish obtained is very colorful, burgundy and translucent, it does not color the nail after removing make-up.
• the varnish film is shiny, hard, water resistant and non-peelable. No sedimentation is observed over time.
• the varnish obtained does not color the nail after removing makeup.
• the varnish film is shiny, hard and water resistant.
• the gloss of the varnish film is measured according to Example 4, it is 94.0.

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• 1996
  • 1996-12-16 FR FR9615454A patent/FR2757048B1/fr not_active Expired - Fee Related
• 1997
  • 1997-12-15 EP EP97952063A patent/EP0944379A1/de not_active Ceased
  • 1997-12-15 WO PCT/FR1997/002304 patent/WO1998026753A1/fr not_active Application Discontinuation
  • 1997-12-15 JP JP10527391A patent/JP2000513004A/ja active Pending
  • 1997-12-15 CA CA002274939A patent/CA2274939A1/fr not_active Abandoned

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