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
• • 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
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/34—Alcohols
• • 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
  • A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
• • 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
  • A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
  • A61Q1/06—Lipsticks
• • 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
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
• • 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
  • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
  • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
  • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
• • 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
  • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
  • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
  • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
  • C08G63/16—Dicarboxylic acids and dihydroxy compounds
  • C08G63/20—Polyesters having been prepared in the presence of compounds having one reactive group or more than two reactive groups

Definitions

• Solid cosmetic composition comprising a polyester
• the present invention relates to cosmetic compositions comprising polymers of the family of polyesters, and to their use in particular in lipsticks.
• compositions according to the invention can be applied to supports such as the skin of the face or of the body, the lips and the keratin materials such as the hair, the eyelashes, the eyebrows and the nails.
• esters resulting from the condensation of a polyol with a carboxylic acid of "neo" type in particular in FR2838049.
• EP1457201 which describes a composition combining a polyester of triglycerides of hydroxylated carboxylic acids and a low molecular weight oil chosen from polybutylenes, hydrogenated polyisobutylenes, hydrogenated or non-hydrogenated polydecenes, copolymers of vinylpyrrolidones, Linear fatty acids, hydroxylated esters, C24-C28 branched fatty alcohol or fatty acid esters, silicone oils and / or vegetable oils.
• a low molecular weight oil chosen from polybutylenes, hydrogenated polyisobutylenes, hydrogenated or non-hydrogenated polydecenes, copolymers of vinylpyrrolidones, Linear fatty acids, hydroxylated esters, C24-C28 branched fatty alcohol or fatty acid esters, silicone oils and / or vegetable oils.
• compositions and combinations when in the form of a stick or poured pot, have a relatively low gloss compared to liquid or pasty compositions.
• the polymers used in the context of the present invention are preferably alkyd resins, which constitute a particular class of polyesters by being the reaction product of polyols and polycarboxylic acids, generally modified with unsaturated fatty acids, such as oleic acid, or unsaturated oils, eg soybean oil or castor oil.
• compositions comprising polyesters have been described in the prior art.
• JP58023614 is also known which describes the use of a modified polyester obtained by condensation of pentaerythritol with cis-4-cyclohexene-1,2-dicarboxylic acid and castor oil fatty acids and then reaction with a dioxirane compound.
• epoxy resin type or JP54011244 which describes the use of a modified polyester obtained by condensation of dipentaerythritol with cyclohexane-1,2-dicarboxylic acid and castor oil fatty acids and then reaction with an epoxy resin-type dioxirane compound.
• polyesters used in the context of the present invention have a different structure from known polyesters.
• they when they are formulated in combination with particular ingredients, they make it possible to achieve cosmetic properties equal to or better than the performance already obtained with the known polyesters.
• the object of the present invention is to provide cast cosmetic compositions whose gloss level reaches for the first time that of a cosmetic composition in the form of a paste or a liquid such as a gloss.
• polyesters lead to solid cosmetic compositions, cast or in the form of a stick, having once applied a gloss as high as the gloss obtained in the prior art with liquid compositions.
• a stick does not allow equal tint to obtain a gloss as gloss pasty.
• the subject of the present invention is therefore a solid cosmetic composition, especially a cast composition, comprising at least one polyester that can be obtained by reaction:
• At least one polyol comprising 3 to 6 hydroxyl groups; at least one nonaromatic monocarboxylic acid;
• At least one polycarboxylic acid comprising at least 2 carboxyl groups COOH and / or a cyclic anhydride of such a polycarboxylic acid
• the present invention also relates to a cast cosmetic composition containing a benzoic acid / isophthalic acid / isostearic acid / pentaerythritol polymer, a benzoic acid / isophthalic acid / stearic acid / pentaerythritol polymer, or a mixture thereof.
• hydrocarbon is meant a radical or a compound formed essentially or even consisting of carbon atoms and hydrogen, and optionally oxygen, nitrogen, sulfur, phosphorus, and not containing no silicon atom or fluorine. It may contain alcohol, ether, carboxylic acid, amine and / or amide groups.
• hydrocarbon refers to a radical or compound consisting solely of carbon and hydrogen atoms, and oxygen.
• branched is meant a compound comprising at least one branch containing at least two carbon atoms.
• the polyisobutenes are not branched within the meaning of the present invention. More generally, the number of branches of a molecule corresponds to the number of side groups containing at least one carbon atom and connected to the main chain of the molecule, the main chain corresponding to the longest carbon chain of the molecule. molecule (see Organic Chemistry, SH Pine, 5 th Edition, McGraw-Hill, chapter 3).
• composition of the invention may be in the form of a paste, a solid or a cream more or less viscous. It can be an oil-in-water or water-in-oil emulsion, a rigid or flexible anhydrous gel. In particular, it is in cast form in a stick or cup and more particularly in the form of an anhydrous rigid gel including anhydrous stick.
• the hardness of the composition may be between 30 to 300 g, especially between 50 to 250 g, preferably from 70 to 230 g, for example from 100 to 200 g, in particular from 150 to 175 g.
• the hardness of a stick can be measured by the so-called "butter cutter” method, which consists of cutting a 12.7 mm lipstick and measuring the hardness at 20 ° C, using a DFGHS 2 dynamometer from the Indelco-Chatillon company moving at a speed of 100 mm / minute. It is expressed as the shear force (expressed in grams) needed to cut a stick under these conditions.
• the hardness of a composition according to the invention ranges from 50 to 300 g, preferably from 100 to 250 g and for example from 150 to 230 g.
• the hardness of the composition according to the invention can also be measured by means of a textuometer which makes it possible to obtain the variation of the resistance to the deformation of the composition as a function of the movement of a moving part in a sample. of said composition.
• the texturometer measures the resistance strength to the deformation of the composition as soon as the mobile comes into contact with the sample. After reaching a programmed maximum depth LO in the sample, the mobile returns to the initial point.
• the hardness (expressed in gram or in Newton) is equal to the strength value of the composition when the mobile is at the end of the stroke, and the elasticity (expressed as a percentage) is equal to the ratio of i) the distance L at which the contact break between the mobile and the sample occurs during the removal of the mobile and ii) the distance LO.
• the contact rupture results in the cancellation of the resistance force of the composition on the mobile.
• the texturometer used can be a texturometer Stable Micro System TAX-T2i ® equipped with the operating software Texture Expert Exceed ® equipped with a plastic hemispherical mobile P / 0.5 HS Rheo's.
• the parameters applied are advantageously the following: speed before contact: 0.1 mm.s-1, speed of displacement in the sample: 0.1 mm.s-1, withdrawal speed: 0.1 mm.s-1 , - maximum depth LO: 1 mm.
• composition samples are prepared by hot casting a sufficient quantity of the test composition, for example in a petri dish 100 x 15 mm previously tared, to obtain a sample of about 1 cm thick.
• the interest of the choice of this conditioning is its width sufficient to overcome any edge effects.
• Two petri dishes are thus prepared, which are allowed to stand for at least 24 hours at 20 ° C. before characterization.
• At least three measurements are made on each sample: one, in the center and others, on points located equidistant from the center and the edge thereof.
• the hardness is equal to the average of the measurements made, at least six. More particularly, the hardness of the composition measured according to this method may vary from 30 g to 200 g, in particular from 50 g to 190 g, or even from 70 to 175 g and more particularly from 100 g to 150 g.
• the wet gloss index of a film of composition according to the invention may be measured according to an evaluation method comprising the steps of, the film being illuminated by at least one light source: applying a film of composition on the lips measure a first index representative of the intensity of the non-diffuse brightness of at least part of the film, determine a second index representative of a heterogeneity of gloss of the film, that is to say the level of fragmentation observable brightness areas - calculating a perceived brightness index from the first and second indices at least.
• the measurement of the perceived brightness comprises the steps of: acquire by polarimetric imaging two images of keratin materials, in particular lips, made up with a cosmetic product, one (C) in crossed polarized configuration and the other (P) in parallel polarized configuration, to make the difference of the two images to obtain a resultant image representative of the light non-diffusely reflected by the film surface, defining on the resulting image (PC) a region of interest to be analyzed, including a rectangle encompassing the lips, generating a histogram of levels of on the region of interest, calculate a first index representative of the average gray level of the lightest pixels, in particular the last 0.5% of the histogram, evaluate a second index representative of the brightness heterogeneity in school. visually image the resulting image (PC) using an atlas or by image analysis by segmenting on the region of interest of the gloss areas, determine a brightness index perceived from the first and second indices, in particular by adding at least the first and second indices.
• the image processing may include the detection of high-area spots, by definition of area greater than 100 pixels, and the corresponding total area Ab may be measured.
• the processing may also include detecting small area patches, by surface definition less than 20 pixels, and the corresponding total area As may be measured.
• the wet gloss index may for example be defined by the formula 40 log [(1 + Ab) / (1 + As)].
• the representative image of the non-diffuse brightness can be generated other than by difference of the P-C images, for example by the operation (P-C) / (P + C) carried out pixel by pixel.
• the representative image of the non-diffused gloss can be obtained by color or spectral polarimetric imaging.
• the chromatic or spectral characteristics of the image and in particular the brightness areas may be taken into account in calculating the different indices.
• high gloss that is to say when the brightness areas are sufficiently contrasted with the diffuse background, it is possible to calculate the wet gloss index on non-polarized images generated under visible, ultraviolet light or infrared.
• the wet gloss index of the compositions according to the invention is advantageously greater than or equal to 20, preferably greater than or equal to 30, more preferably greater than or equal to 40.
• the wet gloss index is less than 150, in particular less than 100, or even less than 80.
• the polyester (hereinafter also referred to as polycondensate) is advantageously obtained by reacting a polyol, a polycarboxylic acid, a nonaromatic monocarboxylic acid, and an aromatic monocarboxylic acid.
• the nonaromatic monocarboxylic acid content is between 5 and 80% by weight, preferably between 20 and 70% by weight, for example from 25 to 65% by weight relative to the total weight of the polycondensate.
• the polyesters are advantageously obtained from the reaction of a polyol, a polycarboxylic acid and at least one nonaromatic monocarboxylic acid, said monocarboxylic acid being in a significant amount.
• the polycondensates are capable of being obtained by esterification / polycondensation, according to the methods known to those skilled in the art, of the constituents described below.
• One of the constituents necessary for the preparation of the polycondensates according to the invention is a polyol, preferably comprising 3 to 6 hydroxyl groups, in particular 3 to 4 hydroxyl groups. It is of course possible to use a mixture of such polyols.
• Said polyol may especially be a hydrocarbon compound, in particular linear, branched and / or cyclic, saturated or unsaturated, comprising 3 to 18 carbon atoms, especially 3 to 12 or even 4 to 10 carbon atoms, and 3 to 6 groups.
• hydroxy (OH) and may further comprise one or more oxygen atoms intercalated in the chain (ether function).
• Said polyol is preferably a saturated hydrocarbon compound, linear or branched, comprising 3 to 18 carbon atoms, especially 3 to 12 or even 4 to 10 carbon atoms, and 3 to 6 hydroxyl groups (OH). It can be chosen from, alone or as a mixture:
• triols such as 1,2,4-butanetriol, 1,2,6-hexanetriol, trimethylolethane, trimer, thylolpropane, glycerol;
• tetraols such as pentaerythritol (tetramethylolmethane), erythritol, diglycerol or ditrimethylolpropane;
• pentols such as xylitol; hexols such as sorbitol and mannitol; or dipentaerythritol or triglycerol.
• the polyol is chosen from glycerol, pentaerythritol, diglycerol, sorbitol and their mixtures; and most preferably the polyol is a tetraol such as pentaerythritol.
• the polyol, or the polyol mixture preferably represents 10 to 30% by weight, especially 12 to 25% by weight, and more preferably 14 to 22% by weight, of the total weight of the final polycondensate.
• the nonaromatic monocarboxylic acid may be saturated or unsaturated, linear, branched and / or cyclic, comprising 6 to 32 carbon atoms, especially 8 to 28 carbon atoms, and still more preferably 10 to 24 or even 12 to 20 carbon atoms. . It is of course possible to use a mixture of such nonaromatic monocarboxylic acids.
• non-aromatic monocarboxylic acid is meant a compound of formula RCOOH, in which R is a linear, branched and / or cyclic saturated or unsaturated hydrocarbon radical comprising 5 to 31 carbon atoms, especially 7 to 27 carbon atoms, and still more preferably 9 to 23 carbon atoms, or even 1 to 19 carbon atoms.
• R is saturated.
• said radical R is linear or branched, and preferably C5-C31, or even C1-C21.
• the nonaromatic monocarboxylic acid has a melting point greater than or equal to 25 ° C, especially greater than or equal to 28 ° C, or even 30 ° C; it has indeed been found that when such an acid is used, in particular in large quantities, it is possible, on the one hand, to obtain a good gloss and the holding of said gloss, and on the other hand to reduce the amount of waxes usually present in the composition envisaged.
• nonaromatic monocarboxylic acids that may be used, mention may be made, alone or as a mixture, of: saturated monocarboxylic acids such as caproic acid, caprylic acid, isoheptanoic acid, 4-ethylpentanoic acid, 2-ethylhexanoic acid, 4,5-dimethylhexanoic acid, 2- heptylheptanoic acid, 3,5,5-trimethylhexanoic acid, octanoic acid, isooctanoic acid, nonanoic acid, decanoic acid, isononanoic acid, lauric acid, tridecanoic acid, myristic acid, palmitic acid, stearic acid, isostearic acid, arachidic acid, behenic acid, cerotic acid (hexacosanoic acid); cyclopentanecarboxylic acid, cyclopentaneacetic acid, 3-cyclopentylpropionic acid,
• nonaromatic monocarboxylic acids having a melting temperature greater than or equal to 25 ° C.
• decanoic acid capric
• lauric acid tridecanoic acid
• myristic acid palmitic acid
• stearic acid arachidic acid
• acid behenic cerotic acid (hexacosanoic)
• 2-ethylhexanoic acid isooctanoic acid, lauric acid, myristic acid, isoheptanoic acid, isononanoic acid, nonanoic acid, palmitic acid, isostearic acid, stearic acid, behenic acid and mixtures thereof, and even better isostearic acid alone or stearic acid alone.
• Said nonaromatic monocarboxylic acid, or the mixture of said acids is preferably 30 to 80% by weight, especially 40 to 75% by weight, or even 45 to 70% by weight, and more preferably 50 to 65% by weight, of the total weight. of the final polycondensate.
• Another constituent necessary for the preparation of the polycondensates according to the invention is an aromatic monocarboxylic acid.
• This acid can comprise 7 to 11 atoms carbon, optionally further substituted with 1 to 3 alkyl radicals, saturated or unsaturated, linear, branched and / or cyclic, which comprise 1 to 32 carbon atoms, especially 2 to 12, or even 3 to 8 carbon atoms.
• aromatic monocarboxylic acid is meant a compound of formula R'COOH, in which R 'is an aromatic hydrocarbon radical containing 6 to 10 carbon atoms, and in particular the benzoic and naphthoic radicals.
• Said radical R ' can also be substituted with 1 to 3 saturated or unsaturated, linear, branched and / or cyclic alkyl radicals comprising 1 to 32 carbon atoms, in particular 2 to 12 or even 3 to 8 carbon atoms.
• benzoic acid 4-tert-butylbenzoic acid, o-toluic acid, m-toluic acid, 1-naphthoic acid can be used alone or in mixtures; and even better, benzoic acid alone.
• Said aromatic monocarboxylic acid, or the mixture of said acids is preferably 0.1 to 10% by weight, especially 0.5 to 9.95% by weight, more preferably 1 to 9.5% by weight, or even 1, 5 to 8% by weight, of the total weight of the final polycondensate.
• the polyester may be obtained from a linear, branched and / or cyclic, saturated or unsaturated, nonaromatic monocarboxylic acid comprising 10 to 32 carbon atoms, in particular 12 to 28 carbon atoms and more preferably 12 to 24 carbon atoms. carbon; and having a melting point greater than or equal to 25 ° C, especially greater than or equal to 28 ° C, or even 30 ° C. It is of course possible to use a mixture of such nonaromatic monocarboxylic acids.
• nonaromatic monocarboxylic acid is meant a compound of formula RCOOH, in which R is a saturated or unsaturated hydrocarbon radical, linear, branched and / or cy- and preferably comprises from 9 to 31 carbon atoms, especially from 11 to 27 carbon atoms, and most preferably from 11 to 23 carbon atoms.
• the radical R is saturated. Even better, said radical R is linear or branched, and preferably C11-C21.
• nonaromatic monocarboxylic acids having a melting temperature greater than or equal to 25 ° C. which can be used, mention may be made, alone or as a mixture:
• decanoic acid capric
• lauric acid tridecanoic acid
• myristic acid palmitic acid
• stearic acid arachidic acid
• acid behenic cerotic acid (hexacosanoic)
• unsaturated but nonaromatic monocarboxylic acids petroselinic acid, vaccenic acid, elaidic acid, gondoic acid, gadoleic acid, erucic acid, nervonic acid.
• lauric acid, palmitic acid, stearic acid, behenic acid and mixtures thereof may be used, and even more preferably stearic acid or behenic acid alone.
• Said nonaromatic monocarboxylic acid having a melting point greater than or equal to 25 ° C., or a mixture of said acids is preferably 22 to 80% by weight, especially 25 to 75% by weight, or even 27 to 70% by weight, and better 28 to 65% by weight, of the total weight of the final polycondensate.
• the polyester may be obtained from a saturated or unsaturated, linear, branched and / or cyclic, nonaromatic monocarboxylic acid comprising 6 to 32 carbon atoms, in particular 8 to 28 carbon atoms and more preferably 10 to 20, or even 12 to 18 carbon atoms; and having a melting temperature strictly below 25 ° C, especially below 20 ° C, or even 15 ° C. It is of course possible to use a mixture of such nonaromatic monocarboxylic acids.
• nonaromatic monocarboxylic acid is meant a compound of formula RCOOH, in which R is a linear, branched and / or cyclic saturated or unsaturated hydrocarbon radical comprising 5 to 31 carbon atoms, especially 7 to 27 carbon atoms. and still more preferably 9 to 19 carbon atoms, or even 1 to 17 carbon atoms.
• the radical R is saturated.
• said radical R is linear or branched, and preferably C5-C31.
• nonaromatic monocarboxylic acids having a melting temperature of less than 25 ° C. which may be used, mention may be made, alone or as a mixture:
• octanoic acid isooctanoic acid, nonanoic acid, isononanoic acid, isostearic acid; - Among the unsaturated but nonaromatic monocarboxylic acids: caproleic acid, obtusilic acid, undecylenic acid, dodecylenic acid, linderic acid, myristoleic acid, physeteric acid, acid tsuzuic, palmitoleic acid, oleic acid, linoleic acid, linolenic acid, arachidonic acid.
• Said nonaromatic monocarboxylic acid with a melting temperature below 25 ° C., or a mixture of said acids preferably represents 0.1 to 35% by weight, in particular 0.5 to 32% by weight, or even 1 to 30% by weight. and more preferably 2 to 28% by weight, of the total weight of the final polycondensate.
• the polyester is obtained from a nonaromatic monocarboxylic acid, having a melting temperature greater than or equal to 25 ° C, and at 30 ° C and from a non-aromatic monocarboxylic acid, having a melting point below 25 ° C.
• the total amount of nonaromatic monocarboxylic acids, to have those having a melting point greater than 25 ° C. and those having a melting temperature below 25 ° C. is advantageously between 30 ° C. and 80% by weight, in particular between 40 and 70% by weight, or even between 45 and 65% by weight, and better still between 50 and 60% by weight, of the total weight of the final polycondensate.
• Another constituent necessary for the preparation of the polycondensates according to the invention is a polycarboxylic acid, saturated or unsaturated, or even aromatic, linear, branched and / or cyclic, comprising at least 2 carboxylic groups COOH, especially 2 to 4 COOH groups; and / or a cyclic anhydride of such a polycarboxylic acid. It is of course possible to use a mixture of such polycarboxylic acids and / or anhydrides.
• Said polycarboxylic acid may in particular be chosen from linear, branched and / or cyclic, saturated or unsaturated or even aromatic polycarboxylic acids, comprising 3 to 50, especially 3 to 40, carbon atoms, in particular 3 to 36 or even 3 to 18 carbon atoms. and still more preferably 4 to 12 carbon atoms, or even 4 to 10 carbon atoms;
• Said acid comprises at least two carboxylic groups COOH, preferably from 2 to 4 COOH groups.
• said polycarboxylic acid is aliphatic and comprises 3 to 36 carbon atoms, especially 3 to 18 carbon atoms, or even 4 to 12 carbon atoms; or said polycarboxylic acid is aromatic and comprises 8 to 12 carbon atoms. It preferably comprises 2 to 4 COOH groups.
• the cyclic anhydride of such a polycarboxylic acid may in particular correspond to one of the following formulas:
• a and B represent a hydrogen atom or together form an aromatic ring comprising a total of 6 carbon atoms.
• polycarboxylic acids or their anhydrides that may be used, mention may be made, alone or as a mixture:
• dicarboxylic acids such as decanedioic acid, dodecanedioic acid, cyclopropanedicarboxylic acid, cyclohexanedicarboxylic acid, cyclobutane dicarboxylic acid, naphthalene-1,4-dicarboxylic acid and naphthalene-2 acid; , 3-dicarboxylic acid, naphthalene-2,6-dicarboxylic acid, suberic acid, oxalic acid, malonic acid, succinic acid, phthalic acid, terephthalic acid, isophic acid talic acid, tetrahydrophthalic acid, hexahydrophthalic acid, pimelic acid, sebacic acid, azelaic acid, glutaric acid, adipic acid, fumaric acid, maleic acid, itaconic acid, dimers of fatty acids (in particular C36) such as the products marketed under the names Pripol 1006, 1009,
• tetracarboxylic acids such as butanetetracarboxylic acid and pyromelic acid; cyclic anhydrides of these acids and especially phthalic anhydride, trimellitic anhydride, maleic anhydride and succinic anhydride.
• adipic acid, phthalic anhydride and / or isophthalic acid, and more preferably isophthalic acid alone, may be used.
• Said polycarboxylic acid and / or its cyclic anhydride is preferably 5 to 40% by weight, especially 10 to 30% by weight, and more preferably 14 to 25% by weight, of the total weight of the final polycondensate.
• the polycondensate may further comprise hydroxyl (OH) and / or carboxylic (COOH) functional silicone.
• It can comprise 1 to 3 hydroxyl and / or carboxylic functions, and preferably comprises two hydroxyl functions or two carboxylic functions. These functions can be located at the end of the chain or in the chain, but advantageously at the end of the chain.
• This silicone may be of formula:
• W W
• p and q are, independently of one another, equal to 0 or 1,
• R1 to R6 are, independently of one another, a linear carbon radical, branched and / or cyclic, saturated or unsaturated or aromatic; comprising 1 to 20 carbon atoms, especially 2 to 12 carbon atoms; preferably, R 1 to R 6 are saturated or aromatic, and may especially be chosen from alkyl radicals, in particular the methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, octyl, decyl, decadyl and octadecyl radicals, cycloalkyl radicals, in particular the cyclohexyl radical, aryl radicals, especially phenyl and naphthyl radicals, arylalkyl radicals, in particular benzyl and phenylethyl radicals, as well as tolyl and xylyl radicals.
• alkyl radicals in particular the methyl, ethyl, propyl, is
• m and n are, independently of each other, integers between 1 and 140, and are such that the weight average molecular weight (Mw) of the silicone is between 300 and 20,000, in particular between 400 and and 10,000 or even between 800 and 4000.
• Mw weight average molecular weight
• Particularly exemplary are the ⁇ , ⁇ -diol or ⁇ , ⁇ -dicarboxylic polyalkylsiloxanes, and in particular the ⁇ , ⁇ -diol polydimethylsiloxanes and the ⁇ , ⁇ -dicarboxylic polydimethylsiloxanes; ⁇ , ⁇ -diol or ⁇ , ⁇ -dicarboxylic polyarylsiloxanes, and in particular ⁇ , ⁇ -diol or ⁇ , ⁇ -dicarboxylic polyphenylsiloxanes; silanol-functional polyarylsiloxanes such as polyphenylsiloxane; silanol-functional poly
• the ⁇ , ⁇ -diol polydimethylsiloxanes having a weight-average molecular weight (Mw) of between 400 and 10,000, or even between 500 and 5,000, and especially between 800 and 4000, will be used. preferably represent 0.1 to 15% by weight, especially 1 to 10% by weight, or even 2 to 8% by weight, of the weight of the polycondensate.
• the aromatic monocarboxylic acid is present in a molar amount less than or equal to that of the nonaromatic monocarboxylic acid; in particular the ratio between the number of moles of aromatic monocarboxylic acid and the number of moles of nonaromatic monocarboxylic acid is preferably between 0.08 and 0.70, in particular between 0.10 and 0.60, in particular between 0.12 and 0.40. It has been found that this makes it possible in particular to obtain a polymer that is advantageously soluble in the oily media generally used to formulate cosmetic compositions such as lipsticks or foundation; Moreover, the film obtained It has adequate stiffness and flexibility for use in this type of formulation, while having the gloss and shine as desired.
• the polyester is obtainable by reaction:
• At least one polyol comprising 3 to 6 hydroxyl groups
• At least one non-aromatic monocarboxylic acid comprising 6 to 32 carbon atoms
• At least one aromatic monocarboxylic acid comprising 7 to 11 carbon atoms
• At least one polycarboxylic acid comprising at least 2 carboxyl groups COOH and / or a cyclic anhydride of such a polycarboxylic acid
• the polyester is selected from benzoic acid / isophthalic acid / isostearic acid / pentaerythritol polymers, benzoic acid / isophthalic acid / stearic acid / pentaerythritol polymers, and mixtures thereof.
• the nonaromatic monocarboxylic acid does not comprise a free OH group.
• the polycondensate can be obtained by reaction:
• said polycondensate can be obtained by reaction:
• polycarboxylic acid from 10 to 25% by weight, relative to the total weight of the polycondensate, of at least one polycarboxylic acid, saturated or unsaturated, or even aromatic, linear, branched and / or cyclic, comprising at least 2 carboxylic groups COOH, in particular 2 at 4 COOH groups; and / or a cyclic anhydride of such a polycarboxylic acid.
• the composition comprises a polycondensate as defined above, such that the ratio between the number of moles of aromatic monocarboxylic acid and the number of moles of nonaromatic monocarboxylic acid is between 0.08 and 0. 70.
• the composition comprises a polycondensate as defined above, provided that when the polycondensate comprises 10% by weight of at least one aromatic monocarboxylic acid comprising 7 to 11 carbon atoms, optionally further substituted with 1 to 3 saturated or unsaturated, linear, branched and / or cyclic alkyl radicals which comprise 1 to 32 carbon atoms; then the ratio between the number of moles of aromatic monocarboxylic acid and the number of moles of non-aromatic monocarboxylic acid is between 0.08 and 0.70.
• the polycondensate is obtainable by reaction:
• At least one polyol chosen from, alone or as a mixture, 1,2,6-hexanetriol, trimethylol ethane, trimethylolpropane and glycerol; pentaerythritol, erythritol, diglycerol, ditrimethylolpropane; xylitol, sorbitol, mannitol, dipentaerythritol and / or triglycerol; preferably present in an amount of 10 to 30% by weight, especially 12 to 25% by weight, and more preferably 14 to 22% by weight, relative to the total weight of the final polycondensate; at least one nonaromatic monocarboxylic acid chosen from, alone or as a mixture, caproic acid, caprylic acid, isoheptanoic acid, 4-ethylpentanoic acid, 2-ethylhexanoic acid, 4,5-dimethylhexanoic acid, 2-heptylheptanoic
• At least one aromatic monocarboxylic acid chosen from, alone or as a mixture, benzoic acid, o-toluic acid, m-toluic acid, p-toluic acid, 1-naphthoic acid, 2-naphthoic acid, 4-tert-butylbenzoic acid, 1-methyl-2-naphthoic acid, 2-isopropyl-1-naphthoic acid; preferably present in an amount of 0.1 to 10% by weight, in particular 1 to 9.5% by weight, or even 1.5 to 8% by weight, relative to the total weight of the final polycondensate; and
• the polycondensate can be obtained by reacting: from 10 to 30% by weight, relative to the total weight of the polycondensate, of at least one polyol comprising 3 to 6 hydroxyl groups; from 22 to 80% by weight, relative to the total weight of the polycondensate, of at least one saturated or unsaturated, linear, branched and / or cyclic, nonaromatic monocarboxylic acid comprising 10 to 32 carbon atoms, and having a melting temperature greater than or equal to 25 ° C; from 0.1 to 35% by weight, relative to the total weight of the polycondensate, of at least one linear, branched and / or cyclic, saturated or unsaturated, non-aromatic monocarboxylic acid comprising 6 to 32 carbon atoms, and having a melting temperature strictly below 25 ° C;
• polycarboxylic acid from 5 to 40% by weight, relative to the total weight of the polycondensate, of at least one polycarboxylic acid, saturated or unsaturated, or even aromatic, linear, branched and / or cyclic, comprising at least 2 carboxylic groups COOH, in particular 2 at 4 COOH groups; and / or a cyclic anhydride of such a polycarboxylic acid.
• the polycondensate is obtainable by reaction of: at least one polyol chosen from, alone or as a mixture, glycerol, pentaerythritol, sorbitol and their mixtures, and even better pentaerythritol alone; present in an amount of 10 to 30% by weight, especially 12 to 25% by weight, and more preferably 14 to 22% by weight, relative to the total weight of the final polycondensate; at least one nonaromatic monocarboxylic acid chosen from, alone or in a mixture, 2-ethylhexanoic acid, isooctanoic acid, lauric acid, palmitic acid, isostearic acid, isononanoic acid, stearic acid, behenic acid and mixtures thereof, and even better isostearic acid alone or stearic acid alone; present in an amount of 30 to 80% by weight, especially 40 to 75% by weight, and more preferably 45 to 70% by weight, relative to the total weight of
• the polycondensate has: an acid number, expressed as mg of potassium hydroxide per g of polycondensate, greater than or equal to 1; in particular between 2 and 30, and even better between 2.5 and 15; and or
• a hydroxyl number expressed in mg of potassium hydroxide per g of polycondensate greater than or equal to 40; in particular between 40 and 120, and even better between 45 and 80.
• the polycondensate has a weight average molecular weight (Mw) of between 1500 and 300 000, even between 2000 and 200 000, and especially between 3000 and 100,000.
• Mw weight average molecular weight
• the average molecular weight can be determined by gel permeation chromatography or by light scattering, depending on the solubility of the polymer in question.
• the polycondensate has a viscosity, measured at 110 ° C, of between 20 and 4000 mPa.s, especially between 30 and 3500 mPa.s, or between 40 and 3000 mPa.s and even better between 50 and 2500 mPa. s. This viscosity is measured as described before the examples.
• the polycondensate is advantageously soluble in the oily cosmetic media usually employed, and in particular in vegetable oils, alkanes, fatty esters, fatty alcohols, silicone oils, and more particularly in media comprising isododecane, Parleam, isononyl isononanoate, octyldodecanol, phenyl trimethicone, C12-C15 alkyl benzoate and / or D5 (decamethylcyclopentosiloxane).
• oily cosmetic media usually employed, and in particular in vegetable oils, alkanes, fatty esters, fatty alcohols, silicone oils, and more particularly in media comprising isododecane, Parleam, isononyl isononanoate, octyldodecanol, phenyl trimethicone, C12-C15 alkyl benzoate and / or D5 (decamethylcyclopentosiloxane).
• Soluble means that the polymer forms a clear solution in at least one solvent chosen from isododecane, Parleam, isononyl isononanoate, octyldodecanol and C12-C15 alkyl benzoate, at least 50% by weight at 70 ° C. Some compounds even have a particularly advantageous solubility in certain fields of application, namely a solubility in at least one of the solvents mentioned above. above, at least 50% by weight, at 25 ° C.
• the polycondensate may be prepared by the esterification / polycondensation processes usually employed by those skilled in the art.
• a general method of preparation consists of:
• Said method of preparation may further comprise a step of adding at least one antioxidant agent to the reaction medium, in particular at a concentration by weight of between 0.01 and 1%, relative to the total weight of monomers, of in order to limit any damage caused by prolonged heating.
• the antioxidant may be of primary or secondary type, and may be selected from hindered phenols, aromatic secondary amines, organophosphorus compounds, sulfur compounds, lactones, acrylated bisphenols; and their mixtures.
• antioxidants mention may be made especially of BHT, BHA, TBHQ, 1,3,5-trimethyl-2,4,6, tris (3,5-di-tert-butyl-4-hydroxybenzyl) -benzene, 3,5-roctadecyl, di-tert-butyl-4-hydroxycinnamate , tetrakis-methylene-3- (3,5-di-tert-butyl-4-hydroxy-phenyl) propionate methane, octadecyl-3- (3,5-di-tertbutyl-4-hydroxyphenyl) propionate 2,5- di-tert-butyl hydroquinone, 2,2-methyl-bis- (4-methyl-6-tertbutyl phenol), 2,2-methylene-bis- (4-ethyl-6-tertbutyl phenol), butylidene-bis (6-tertbutyl-m-cresol), N, N-hexamethylene bis (3,5-di-
• the amount of polycondensate present in the compositions depends, of course, on the type of composition and the desired properties and can vary within a very wide range, generally between 0.1 and 70% by weight, preferably between 1 and 50% by weight, especially between 10 and 45% by weight, or even between 20 and 40% by weight, and better still between 25 and 35% by weight, relative to the weight of the cosmetic composition. According to one mode of implementation, the amount of polycondensate present in the compositions is between 10 and 20% by weight relative to the weight of the cosmetic composition.
• the non-volatile oil may represent 1 to 90% by weight of the composition, in particular from 5 to 75% by weight, in particular from 10 to 60% by weight, or even 25 to 55% by weight, of the total weight of the composition. composition.
• the non-volatile oil can represent from 35 to 60% by weight.
• non-volatile oil means an oil having a vapor pressure of less than 0.13 Pa.
• the non-volatile oils may be hydrocarbon oils, silicone oils, fluorinated oils, or their mixtures.
• silicon oil means an oil comprising at least one silicon atom, and in particular at least one Si-O group.
• hydrocarbon-based oil means an oil containing mainly hydrogen and carbon atoms and optionally oxygen, nitrogen, sulfur and / or phosphorus atoms.
• hydrocarbon is meant an oil containing only hydrogen and carbon atoms.
• the non-volatile oils may in particular be chosen from fluorinated hydrocarbon oils which may be fluorinated and / or non-volatile silicone oils.
• Non-volatile hydrocarbon oils that may especially be mentioned include: hydrocarbon oils of plant origin such as phyto-stearyl esters, such as phytostearyl oleate, phytostearyl isostearate and lauroyl / octyldodecyl glutamate / phytostearyl (AJINOMOTO, ELDEW PS203), triglycerides consisting of esters of fatty acids and of glycerol, the fatty acids of which can have various chain lengths of C 4 to C 24 , the latter possibly being linear or branched, saturated or unsaturated; these oils are, in particular, heptanoic or octanoic triglycerides, wheat germ, sunflower, grape seed and sesame oils, maize, apricot, castor oil, shea butter, avocado, olive, soy
• esters may in particular be chosen from esters, in particular of fatty acids such as, for example, cetostearyl octanoate, esters of isopropyl alcohol, such as isopropyl myristate, isopropyl palmitate or palmitate.
• esters in particular of fatty acids such as, for example, cetostearyl octanoate, esters of isopropyl alcohol, such as isopropyl myristate, isopropyl palmitate or palmitate.
• the non-volatile silicone oils that may be used in the composition may be non-volatile poly-dimethylsiloxanes (PDMS), polydimethylsiloxanes containing pendant alkyl or alkoxy groups and / or silicone chain ends, groups each having from 2 to 24 carbon atoms.
• PDMS poly-dimethylsiloxanes
• polydimethylsiloxanes containing pendant alkyl or alkoxy groups and / or silicone chain ends groups each having from 2 to 24 carbon atoms.
• phenyl silicones such as phenyl trimethicones, phenyl dimethicones, phenyl trimethylsiloxy diphenylsiloxanes, diphenyl dimethicones, diphenyl methyldiphenyl trisiloxanes, and 2-phenylethyl trimethylsiloxysilicates, dimethicones or phenyltrimethicones with viscosities less than or equal to 100 cSt, and their mixtures.
• the silicone oil corresponds to the formula R R R R
• R groups independently of one another are methyl or phenyl.
• said organopolysiloxane comprises at least three phenyl groups, for example at least four or at least five. Mixtures of the phenyl organopolysiloxanes described above can be used.
• the silicone oil corresponds to the formula Ph Ph Ph
• Ph phenyl
• phenyl silicone is especially manufactured by Dow Corning under the reference Dow Corning 555 Cosmetic Fluid (INCI name: trimethyl pentaphenyl trisiloxane).
• Dow Corning 554 Cosmetic Fluid can also be used.
• the non-volatile oil is preferably apolar, in the sense that its delta solubility parameter a is equal to 0. WAX
• the composition may contain a wax.
• wax means a lipophilic compound, solid at room temperature (25 ° C.), with a reversible solid / liquid state change, having a melting point of greater than or equal to 30 ° C. at 120 ° C.
• the melting point of the wax can be measured using a differential scanning calorimeter (D.S.C.), for example the calorimeter sold under the name DSC 30 by the METTLER Company.
• D.S.C. differential scanning calorimeter
• the waxes may be hydrocarbon-based, fluorinated and / or silicone-based and may be of vegetable, mineral, animal and / or synthetic origin.
• the waxes have a melting temperature above 25 ° C and more preferably above 45 ° C.
• linear hydrocarbon waxes may be mentioned. Their melting point is advantageously greater than 35 ° C., for example greater than 55 ° C., preferably greater than 80 ° C.
• the linear hydrocarbon waxes are advantageously chosen from substituted linear alkanes, unsubstituted linear alkanes, unsubstituted linear alkenes, substituted linear alkenes, and an unsubstituted compound consisting solely of carbon and hydrogen.
• the substituents mentioned above do not contain carbon atoms.
• the linear hydrocarbon waxes include polymers and copolymers of ethylene, with a molecular weight of between 400 and 800, for example Polywax 500 or Polywax 400 marketed by New Phase Technologies.
• Linear hydrocarbon waxes include linear paraffin waxes, such as S & P 206, S & P 173 and Strahl & Pitsch S & P 434 paraffins.
• Linear hydrocarbon waxes include long-chain linear alcohols, such as products comprising a blend of polyethylene and alcohols having 20 to 50 carbon atoms, including Performacol 425 or Performacol 550 (20/80 blend) marketed by New Phase Technologies. Examples of silicone waxes are, for example
• the amount of wax in the composition according to the invention may range from 5 to 70% by weight, relative to the total weight of the composition, preferably from 5 to 40% by weight, and more preferably from 10 to 30% by weight.
• composition according to the invention may contain a dyestuff, in a proportion of 0.5 to 50% dyestuff, preferably from 2 to 40% and better still from 5 to 30%, relative to the total weight of the composition.
• the dyestuff may be any inorganic and / or organic compound, having an absorption between 350 and 700 nm, or capable of generating an optical effect such as the reflection of incident light or interferences for example.
• the dyestuffs useful in the present invention are chosen from all the organic and / or inorganic pigments known in the art, in particular those described in Kirk-Othmer's encyclopaedia of chemical technology and in the encyclopedia of industrial chemistry. from Ullmann.
• mineral dyestuffs examples include titanium dioxide, surface treated or untreated, zinc oxide, zirconium or cerium oxides, iron or chromium oxides, manganese, ultramarine blue, chromium hydrate and ferric blue.
• inorganic pigments can be used: Ta 2 O 5 , Ti 3 O 5 , Ti 2 O 3 , TiO, ZrO 2 mixed with TiO 2 , ZrO 2 , Nb 2 O 5 , CeO 2 , ZnS.
• organic dyestuffs examples include nitroso, nitro, azo, xanthene, quinoline, anthraquinone, phthalocyanine, metal complex, isoindolinone, isoindoline, quinacridone, perinone, perylene, diketopyrrolopyrrole, thioindigo, dioxazine, triphenylmethane, quinophthalone.
• the dyestuffs may be chosen from carmine, carbon black, aniline black, azo yellow, quinacridone, phthalocyanine blue, sorghum red, blue pigments codified in the Color Index under the references Cl 42090, 69800, 69825, 73000, 74100, 74160, the yellow pigments coded in the Color Index under the references Cl 11680, 11710, 15985, 19140, 20040, 21100, 21108, 47000, 47005, the green pigments codified in the Color Index under the references Cl 61565, 61570, 74260, the orange pigments coded in the Color Index under the references Cl 1 1725, 15510, 45370, 71105, the red pigments codified in the Color Index under the references Cl 12085, 12120 , 12370, 12420, 12490, 14700, 15525, 15580, 15620, 15630, 15800, 15850, 15865, 15880, 17200, 26100, 45380, 45410,
• the pigments according to the invention may also be in the form of composite pigments as described in patent EP 1 184 426.
• These composite pigments may be composed in particular of particles comprising an inorganic core. at least one binder for fixing the organic pigments on the core, and at least one organic pigment at least partially covering the core.
• the dyestuffs may be chosen from dyes, lacquers or pigments.
• the dyes are, for example, fat-soluble dyes, although water-soluble dyes can be used.
• Liposoluble dyes are, for example, Sondan red, D & C Red 17, D & C Green 6, ⁇ -carotene, soya bean oil, Sudan brown, D & C Yellow 1 1, D & C Violet 2, D & C orange 5, yellow quinoline, annatto. They may represent from 0 to 20% of the weight of the composition and better still from 0.1 to 6%.
• the water-soluble dyes are in particular beet juice, methylene blue and may represent from 0.1 to 6% by weight of the composition (if present).
• lacquer is meant dyes adsorbed on insoluble particles, the assembly thus obtained remaining insoluble during use.
• the inorganic substrates on which the dyes are adsorbed are, for example, alumina, silica, calcium and sodium borosilicate or calcium and aluminum borosilicate, and aluminum.
• Organic dyes include cochineal carmine.
• lacquers As examples of lacquers, mention may be made of the products known under the following names: D & C Red 21 (Cl 45 380), D & C Orange 5 (Cl 45 370), D & C Red 27 (Cl 45 410). ), D & C Orange 10 (Cl 45,425), D & C Red 3 (Cl 45,430), D & C Red 7 (Cl 15,850: 1), D & C Red 4 (Cl 15,510), D & C Red.
• pigments should be understood to mean white or colored, inorganic or organic particles intended to color and / or opacify the composition.
• the pigments according to the invention may for example be chosen from white or colored pigments, special effect pigments such as pearlescent agents, reflective pigments or interference pigments.
• pigments which can be used in the invention mention may be made of titanium, zirconium or cerium oxides as well as zinc, iron or chromium oxides and ferric blue.
• organic pigments mention may be made of carbon black, and lacquers of barium, strontium, calcium (D & C Red No. 7), aluminum.
• the nacres may be present in the composition in a proportion of 0.001 to 20% of the total weight of the composition, preferably at a rate of the order of 1 to 15%.
• the pigments may be present in the composition in a proportion of 0.05 to 30% by weight of the final composition, and preferably in a proportion of 2 to 20%.
• Special effect pigments are pigments which generally create a colored appearance (characterized by a certain nuance, a certain vivacity and a certain clarity) which is non-uniform and changeable according to the conditions of observation (light, temperature , observation angles ). They are therefore opposed to white or colored pigments that provide a uniform opaque, semi-transparent or conventional transparent tint.
• white pearlescent pigments such as mica coated with titanium, or bismuth oxychloride
• colored pearlescent pigments such as mica coated with titanium and with iron oxides.
• mica coated with titanium and in particular ferric blue or chromium oxide mica coated with titanium and an organic pigment as defined above
• pearlescent pigments based on bismuth oxychloride mention may be made of Cellini nacres marketed by Engelhard (Mica-TiO2-lacquer), Prestige marketed by Eckart (Mica-TiO2), Colorona marketed by Merck (Mica-TiO2-Fe2O3).
• Non-fixed interference-effect pigments may also be mentioned, such as liquid crystals (Wacker's Helicones HC) and interferential holographic flakes (Spectratek's Geometry Pigments or Spectra f / x).
• Special effect pigments also include fluorescent pigments, whether they are daylight fluorescent or ultraviolet fluorescent, phosphorescent pigments, photochromic pigments, and thermochromic pigments.
• composition advantageously contains goniochromatic pigments, for example interferential multilayer pigments, and / or reflective pigments. These two types of pigments are described in the application FR0209246 whose contents are incorporated by reference in the present application.
• the composition may contain reflecting pigments, which may or may not be goniochromatic, whether or not they are interferential.
• the reflective particles will preferably have a size of at least 10 ⁇ m, for example between about 20 ⁇ m and about 50 ⁇ m.
• dimension is meant the dimension given by the statistical size distribution at half of the population, called D50.
• the size of the reflective particles may depend on their surface state. The more reflective this is, the smaller the dimension can be, a priori, and vice versa.
• Reflective particles that can be used in the invention, with a metallic or white sheen can for example reflect light in all visible components without significantly absorbing one or more wavelengths.
• the spectral reflectance of these reflective particles may for example be greater than 70% in the range 400-700 nm, and more preferably at least 80%, even 90% or 95%.
• the reflective particles, whatever their shape, may have a multilayer structure or not and, in the case of a multilayer structure, for example at least one layer of uniform thickness, especially a reflective material, which coats a substrate.
• the substrate may be chosen from glasses, ceramics, graphite, metal oxides, aluminas, silicas, silicates, in particular aluminosilicates and borosilicates and synthetic mica, this list not being limiting.
• the reflective material may include a layer of metal or a metal compound.
• the layer of metal or metal compound may or may not completely coat the substrate and the metal layer may be at least partially covered by a layer of another material, for example a transparent material. It may be preferable that the metal or metal compound layer coats all, directly or indirectly, that is to say with the interposition of at least one intermediate layer, metallic or otherwise, the substrate.
• the metal may be chosen for example from Ag, Au, Cu, Al, Ni, Sn, Mg, Cr, Mo, Ti, Pt, Va, Rb, W, Zn, Ge, Te, Se and their alloys.
• Ag, Au, Al, Zn, Ni, Mo, Cr, Cu and their alloys (eg, bronzes and brasses) are preferred metals.
• the metal layer may be present at a content representing for example from 0.1 to 50% of the total weight of the particles, or even between 1 and 20%.
• Particles of glass coated with a metal layer are described in particular in JP-A-09188830, JP-A-10158450, JP-A-10158541, JP-A-07258460 and JP-A-05017710.
• Platelet-coated silver-coated glass substrate particles are sold under the name MICROGLASS METASHINE REFSX 2025 PS by the company TOYAL.
• Particles with a glass substrate coated with a nickel / chromium / molybdenum alloy are sold under the name CRYSTAL STAR GF 550, GF 2525 by the same company.
• the reflective particles may also be chosen from particles with a synthetic substrate at least partially coated with at least one layer of at least one metal compound, in particular a metal oxide chosen, for example, from titanium oxides.
• TiO 2 especially TiO 2 , iron in particular Fe 2 O 3 , tin, chromium, barium sulfate and the following compounds: MgF 2 , CrF 3 , ZnS, ZnSe, SiO 2 , Al 2 O 3 , MgO, Y 2 O 3 , SeO 3 , SiO, HfO 2 , ZrO 2 , CeO 2 , Nb 2 O 5 , Ta 2 O 5 , MoS 2 and mixtures or alloys thereof.
• particles comprising a synthetic mica substrate coated with titanium dioxide, or glass particles coated with either brown iron oxide or titanium oxide, tin oxide or a mixture thereof such as those sold under the trade name REFLECKS ® by ENGELHARD.
• pigments of the METASHINE 1080R range marketed by NIPPON SHEET GLASS CO. LTD are C-GLASS glass flakes comprising 65 to 72% of SiO 2 , covered with a layer of titanium oxide of rutile type (TiO 2 ). These glass flakes have an average thickness of 1 micron and an average size of 80 microns is a ratio average size / average thickness of 80. They have blue, green, yellow or silver-tone reflections depending on the thickness of the layer of TiO 2 .
• particles having a size of between 80 and 100 ⁇ m comprising a synthetic mica substrate (fluorophlogopite) coated with titanium dioxide representing 12% of the total weight of the particle, sold under the name PROMINENCE by the company NIHON KOKEN.
• the reflective particles may also be chosen from particles formed from a stack of at least two layers with different refractive indices. These layers may be polymeric or metallic in nature and in particular include at least one polymeric layer. Such particles are described in particular in WO 99/36477, US Pat. No. 6,299,979 and US Pat. No. 6,387,498.
• the composition may contain one or more goniochromatic pigments.
• the goniochromatic coloring agent may be chosen, for example, from interferential multilayer structures and liquid crystal coloring agents.
• this may comprise for example at least two layers, each layer, independently or not of the other layer (s) being made for example from at least one material selected from the group consisting of the following materials: MgF 2 , CeF 3 , ZnS, ZnSe, Si, SiO 2 , Ge, Te, Fe 2 O 3 , Pt, Va, Al 2 O 3 , MgO, Y 2 O 3 , S 2 O 3 , SiO, HfO 2 , ZrO 2 , CeO 2 , Nb 2 O 5 , Ta 2 O 5 , TiO 2 , Ag, Al, Au, Cu, Rb, Ti, Ta, W, Zn , MoS 2 , cryolite, alloys, polymers and their combinations.
• the multilayer structure may or may not have, with respect to a central layer, a symmetry at the chemical nature of the stacked layers.
• Examples of symmetrical interferential multilayer structures that can be used in are, for example, the following structures: Al / SiO 2 / Al / SiO 2 / Al, pigments having this structure being marketed by DuPont de Nemours; Cr / MgF 2 / AI / MgF 2 / Cr, pigments having this structure being marketed under the name CHROMAFLAIR by the company FLEX; MoS 2 / SiO 2 / Al / SiO 2 / MoS 2 ; Fe 2 O 3 / SiO 2 / Al / SiO 2 / Fe 2 O 3, and Fe 2 O 3 / SiO 2 / Fe 2 O 3 / SiO 2 / Fe 2 O 3 , pigments having these structures being marketed under the name SICOPEARL by BASF; MoS 2 / SiO 2 / mica-oxide / SiO 2 / MoS 2 ; Fe 2 O 3 / SiO 2 / mica-oxide / SiO 2 / Fe 2 O 3 ; TiO
• pigments having these structures being marketed under the name XIRONA by the company Merck (Darmstadt).
• these pigments may be the pigments of silica / titania / tin oxide structure sold under the name Xirona Magic by the company Merck, the silica / brown iron oxide structural pigments marketed under the name XIRONA.
• goniochromatic coloring agents having a multilayer structure comprising an alternation of polymeric layers, for example of the polyethylene naphthalate and polyethylene terephthalate type.
• Such agents are described in particular in WO-A-96/19347 and WO-A-99/36478.
• liquid crystal coloring agents comprise, for example, silicones or cellulose ethers onto which mesomorphic groups are grafted.
• liquid crystal goniochromatic particles that may be used include those sold by the company Chenix well as those sold under the name Helicone® ® HC by Wacker.
• the composition may further comprise dispersed goniochromatic fibers.
• Such fibers may, for example, have a size of between 200 ⁇ m and 700 ⁇ m, for example about 300 ⁇ m.
• interferential fibers with a multilayer structure can be used.
• Fibers with a multilayer structure of polymers are described in particular in documents EP-A-921217, EP-A-686858 and US-A-5472798.
• the multilayer structure may comprise at least two layers, each layer, independently or not of the other layer (s), being made of at least one synthetic polymer.
• the polymers present in the fibers may have a refractive index ranging from 1.30 to 1.82 and more preferably from 1.35 to 1.75.
• Preferred polymers for forming the fibers are polyesters such as polyethylene terephthalate, polyethylene naphthalate, polycarbonate; acrylic polymers such as polymethylmethacrylate; polyamides.
• Goniochromatic fibers with a polyethylene terephthalate / nylon-6 bilayer structure are marketed by TEIJIN under the name MORPHOTEX
• compositions according to the invention may be in any acceptable and customary form for a cosmetic composition.
• compositions according to the invention can be used for the care or makeup of keratin materials such as the hair, the skin, the eyelashes, the eyebrows, the nails, the lips, the scalp and more particularly for lip makeup.
• eyelashes and / or face can therefore be in the form of a care product and / or makeup of the skin of the body or face, lips, eyelashes, eyebrows, hair, leather hair or nails; a suntan or self-tanning product; a hair product including coloring, conditioning and / or hair care; they are advantageously in the form of mascara, lipstick, lip gloss (gloss), blush or eyelid, foundation.
• the subject of the invention is also a process for the cosmetic treatment of keratin materials, in particular the skin of the body or of the face, the lips, the nails, the hair and / or the eyelashes, comprising the application on the said materials of a cosmetic composition as defined above.
• This method according to the invention allows in particular the care or makeup of the lips, by applying a composition of lipstick or lip gloss (gloss) according to the invention.
• the invention also relates to the use of a polycondensate and a non-volatile oil, especially in the proportions and the chemical constitution described above for the makeup of the lips in order to improve the gloss behavior in the time.
• the present invention also relates to a cosmetic assembly comprising:
• a container delimiting at least one compartment, said container being closed by a closing element
• composition as described previously disposed inside said compartment.
• the container can be in any suitable form. It may especially be in the form of a pot, a case, a box, or a case.
• the closure member may be in the form of a removable cap, a lid, a lid, in particular of the type comprising a body attached to the container and a cap hinged to the body.
• the applicator may be in the form of a block of foam or elastomer, a felt, or a spatula.
• the applicator may be free (puff or sponge) or integral with a rod carried by the closure member, as described for example in US Patent 5,492,426.
• the applicator may be integral with the container, as described for example the patent FR 2 761 959.
• the closure member may be coupled to the container by screwing.
• the coupling between the closure element and the container is other than by screwing, in particular via a bayonet mechanism, snap-fastening, clamping, welding, gluing, or magnetic attraction.
• “snapping” is meant in particular any system involving the crossing of a bead or a bead of material by elastic deformation of a portion, in particular of the closure element, then by return to the position not elastically constrained of said portion after crossing the bead or the bead.
• the container may be at least partly made of thermoplastic material.
• thermoplastic materials include polypropylene or polyethylene.
• the container is made of non-thermoplastic material, in particular glass or metal (or alloy).
• the container may have rigid walls or deformable walls, in particular in the form of a tube or a tube flask.
• the container may include means for causing or facilitating the dispensing of the composition.
• the container can be driven by a piston mechanism.
• the container may comprise a mechanism, including rack, or with a threaded rod, or with a helical ramp, and able to move a stick towards said opening.
• a mechanism is described, for example, in patent FR 2 806 273 or in patent FR 2 775 566.
• Such a mechanism for a liquid product is described in patent FR 2 727 609. The invention is illustrated in more detail in the following examples.
• the viscosity at 80 ° C. or at 110 ° C. of the polymer is measured using a planar cone viscometer of the BROOKFIELD CAP 1000+ type.
• the adapted cone-plane is determined by the person skilled in the art on the basis of his knowledge; especially :
• a lipstick was prepared having the following composition: polycondensate of Example 2 30 g
• pentaerythrityl benzoate / isophthalate / isostearate / stearate polycondensate are thus obtained in the form of a very thick oil.
• the polycondensate has the following characteristics:
• the mixture is cooled to a temperature of between 100 and 130 ° C., then 90 g of isophthalic acid and 50 g of Shin-Etsu ⁇ , ⁇ diol X22-160AS silicone are introduced, and the mixture is heated again gradually to 220 ° C. for about 11 hours.
• 510 g of pentaerythrityl benzoate / isophthalate / laurate / PDMS polycondensate are thus obtained in the form of a thick oil which solidifies at room temperature.
• phase B is melted at 95-100 ° C.
• Phase D is then milled in phase A.
• Phase C is then added to melted phase B under Rayneri, and then phase E is added after homogenization.
• the paste obtained is cast at 95 ° C in a mold at 42 ° C. the sticks are cooled to -4 ° C before being demolded.
• the wet gloss and hardness are measured as previously described.

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• 2006
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• 2007
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