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
  • 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
  • A61K8/89—Polysiloxanes
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• • 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

Definitions

• Cosmetic or pharmaceutical composition comprising a polycondensate, said polycondensate and a cosmetic treatment method
• the present invention relates to cosmetic compositions, especially makeup and in particular lipsticks, comprising very specific polycondensates.
• compositions for which gloss properties of the deposited film, after application to the keratin materials include lipsticks, nail polish or some hair products.
• esters resulting from the. condensation of a polyol with a carboxylic acid of "neo" type especially 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, esters of fatty alcohols or of C24-C28 branched fatty acids, silicone oils and / or oils of plant origin. .
• Patent Application EP0792637 describes a composition combining an aromatic ester and a polybutene or polyisobutene type polymer.
• compositions and combinations even if they improve the gloss significantly, are still considered insufficient in a long-term perspective of this brightness, over time.
• the object of the present invention is to provide novel polymers which can confer significant brightness to a particularly film-forming deposit, while maintaining a good durability over time of this gloss; this may find a particularly advantageous application in the field of lipsticks.
• polymers are also to give the composition an excellent hold over time on keratin materials, especially on the lips.
• Alkyd resins 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 by unsaturated oils, soybean oil or castor oil. for example, which make it possible to modulate their film-forming properties, in particular their drying speed, their hardness, their resistance.
• WO2006 / 004911 is also known, which describes polyester polyol polymers that can be used in cosmetics, in particular to replace castor oil; however, the polymers described herein all have a dynamic viscosity at 25 ° C of 200 to 5000 centipoise (mPa.s). However, these polymers do not give the compositions comprising them the desired properties in terms of gloss, maintaining this gloss over time, and long-lasting composition on keratin materials, including skin.
• alkyd resins do not have a suitable solubility in the oily media usually used in cosmetics, such as vegetable oils, alkanes, fatty esters, fatty alcohols, silicone oils, and the like. especially comprising isododecane, Parleam, isononyl isononanoate, octyldodecanol, phenyl trimethicone, C12-C15 alkyl benzoate and / or D5 (decamethylcyclopentasiloxane).
• the subject of the present invention is therefore a cosmetic or pharmaceutical composition
• a cosmetic or pharmaceutical composition comprising, in a cosmetically or pharmaceutically acceptable medium, at least one polycondensate obtainable by reaction of the following monomers only:
• the subject of the invention is also the polycondensate thus defined.
• the cosmetic compositions have good applicability and good coverage; good adhesion to the support, whether on the nail, hair, eyelashes, skin or lips; adequate flexibility and film strength, to avoid cracking, for example in the case of varnishes or lipsticks; as well as an excellent level of lasting shine.
• the comfort and slip properties are also very satisfying.
• These polycondensates are easily transportable in solvent or oily cosmetic media, especially oils, fatty alcohols and / or fatty esters, which facilitates their implementation in the cosmetics field, especially in lipsticks or foundations. .
• the polycondensates according to the invention can be prepared easily, in a single synthesis step, and without generating waste, this at low cost. Moreover, it is easily possible to modify the structure and / or the properties of the polycondensates according to the invention, by varying the chemical nature of the various constituents and / or their proportions.
• the polycondensates according to the invention are advantageously branched (branched); it can be thought that this makes it possible to generate a network by entanglement of the polymer chains, and thus to obtain the desired properties, in particular in terms of improved behavior, improved gloss, and in terms of solubility. It has indeed been found that the linear polycondensates did not make it possible to obtain a significant improvement in the strength of the composition, and that the dendrimer polycondensates, whose chains are regular, did not exhibit optimum solubility.
• the polycondensates according to the invention are polycondensates of alkyd type, and are therefore capable of being obtained by esterification / polycondensation, according to methods known to those skilled in the art, constituents described below.
• One of the constituents necessary for the preparation of the polycondensates according to the invention is a compound comprising 3 to 6 hydroxyl groups (polyol), 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 interposed 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 in mixture:
• triols such as 1, 2,4-butanetriol, 1, 2,6-hexanetriol, trimethylolethane, trimethylolpropane, glycerol;
• tetraols such as pentaerythritol (tetramethylolmethane), erythritol, di-glycerol or dithmethylolpropane;
• pentols such as xylitol
• hexols such as sorbitol and mannitol; or dipentaerythritol or triglycerol.
• the polyol is selected from glycerol, pentaerythritol, diglycerol, sorbitol and mixtures thereof; and even better is pentaerythritol.
• the polyol, or 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.
• Another constituent necessary for the preparation of the polycondensates according to the invention is a saturated or unsaturated, linear, branched and / or cyclic non-aromatic monocarboxylic acid comprising 6 to 32 carbon atoms, in particular 8 to 28 carbon atoms, and even better 10 to 24 or even 12 to 20 carbon atoms.
• a mixture of such nonaromatic monocarboxylic acids can be used.
• 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 11 to 19 carbon atoms.
• the radical R is saturated. Even better, said radical R is linear or branched, and preferably C5-C31, or even C11-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, 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, cyclohexanecarboxylic acid, cyclohexylacetic acid, 4-cyclohexylbut
• unsaturated but nonaromatic monocarboxylic acids such as caproleic acid, obtusilic acid, undecylenic acid, dodecylenic acid, linderic acid, myristoleic acid, physcherrique acid, tsuzuique acid , palmitoleic acid, oleic acid, petroselinic acid, vaccenic acid, elaidic acid, gondoic acid, gadoleic acid, erucic acid, cetoleic acid, nervonic acid , linoleic acid, linolenic acid, arachidonic acid.
• unsaturated but nonaromatic monocarboxylic acids such as caproleic acid, obtusilic acid, undecylenic acid, dodecylenic acid, linderic acid, myristoleic acid, physcherrique acid, tsuzuique acid , palmitoleic acid, oleic acid, petroselinic acid
• nonaromatic monocarboxylic acids having a melting temperature greater than or equal to 25 ° C. mention may be made, alone or as a mixture:
• decanoic acid capric
• lauric acid tridecanoic acid
• myristic acid palmitic acid
• stearic acid arachidic acid
• behenic acid behenic acid
• 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 a polycarboxylic acid, and / or a cyclic anhydride of such a polycarboxylic acid, and / or a lactone carrying at least one COOH group; as well as their mixtures.
• Said polycarboxylic acid may in particular be chosen from linear, branched and / or cyclic, saturated or unsaturated or even aromatic polycarboxylic acids, comprising 2 to 50, in particular 2 to 40, carbon atoms, in particular 3 to 36, or even 3 at 18, and even more preferably 4 to 12 carbon atoms, or even 5 to 10 carbon atoms; said acid comprising at least two carboxylic groups COOH, preferably from 2 to 4 COOH groups; and may comprise 1 to 10 heteroatoms, preferably 1 to 6, identical or different, selected from O, N and S; and / or may comprise at least one perfluorinated radical chosen from -CF 2 - (divalent) or -CF 3 .
• said polycarboxylic acid is saturated, linear aliphatic and comprises 2 to 36 carbon atoms, especially 3 to 18 carbon atoms, or even 4 to 12 carbon atoms; or is aromatic and comprises 8 to 12 carbon atoms. It preferably comprises 2 to 4 COOH groups.
• Said 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 in total 6 to 10 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, cyclobutanedicarboxylic acid, naphthalene-1,4-dicarboxylic acid, naphthalene-2,3-dicarboxylic acid, naphthalene-2,6-dicarboxylic acid, suberic acid, oxalic acid, malonic acid, succinic acid, phthalic acid, terephthalic acid, isophthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, pimelic acid, sebacic acid, acid azelaic acid, glutamic acid, adipic acid, fumaric acid, maleic acid, itaconic acid, dimers of fatty acids (in particular C36) such as the products sold under the names Pripol 1006 , 1009, 1013 and
• tricarboxylic acids such as cyclohexanetricarboxylic acid, trimellitic acid, 1,2,3-benzenetricarboxylic acid, 1,3,5-benzenetricarboxylic acid; aconitic acid, especially trans-aconitic acid;
• tetracarboxylic acids such as butanetetracarboxylic acid and pyromellitic acid
• cyclic anhydrides of these acids and especially phthalic anhydride, trimellitic anhydride, maleic anhydride and succinic anhydride.
• adipic acid Preferably, it is possible to use adipic acid, phthalic anhydride and / or isophthalic acid, and even better isophthalic acid alone.
• linear or branched chain saturated or unsaturated polycarboxylic acids comprising at least one heteroatom selected from O, N and / or S, in particular 1 to 10 identical or different heteroatoms, and / or comprising at least one perfluorinated radical; -CF 2 - or -CF 3 and also having at least 2 carboxyl groups COOH, especially 2 to 4 COOH groups; and / or a cyclic anhydride of such a polycarboxylic acid; and or
• heterocyclic polycarboxylic acids saturated or unsaturated, or even aromatic, comprising at least one heteroatom selected from O, N and / or S, in particular 1 to 10, or even 1 to 4, identical or different hetero atoms, and at least 2 COOH carboxylic groups, especially 2 to 4 COOH groups; and / or a cyclic anhydride of such a polycarboxylic acid; and or
• polycarboxylic acids derived from sugar obtainable in particular by oxidation of an aldose, and comprising at least 2 carboxylic groups COOH, in particular 2 or 3 COOH groups; and / or a cyclic anhydride of such a polycarboxylic acid; and or
• polycarboxylic amino acids including heterocyclic), ie linear or branched saturated or unsaturated chain polycarboxylic acids, and / or cyclic, optionally comprising at least one heteroatom selected from O, N and / or S, in particular 1 to 10 identical or different heteroatoms, and / or optionally comprising at least one perfluorinated radical -CF 2 - or -CF 3 ; and further comprising at least one primary, secondary or tertiary amine function (especially NR1 R2 with R1 and R2, independently of one another selected from H and C1-C12 alkyl), in particular 1 to 3 identical amino functions, or different, and also having at least 2 carboxylic groups COOH, especially 2 to 4 COOH groups; and / or a cyclic anhydride of such a polycarboxylic acid.
• heterocyclic ie linear or branched saturated or unsaturated chain polycarboxylic acids, and / or cyclic, optionally comprising at least one heteroatom selected from O
• dicarboxylic acids may be mentioned alone or as a mixture:
• Poly (ethylene glycol) disuccinate in particular of 250-600 mass
• Poly (ethylene glycol) bis (carboxymethyl) ether in particular of mass 250-600
• Pyrrolidinedicarboxylic acid 1-phenyl-1H-pyrrole-3,4-dicarboxylic acid, 2,4-pyrrolidinedicarboxylic acid, 5-phenyl-2,4-pyrrolidinedicarboxylic acid, 3,5-Piperidinedicarboxylic acid , 3,4-Pyrrolidinedicarboxylic acid, 1-butyl-2,5-pyrrolidinedicarboxylic acid, 1 - (phenylmethyl) -3,4-
• Pyrrolidinedicarboxylic acid N- (2-carboxyethyl) -N-phenyl- ⁇ -alanine, N- (carboxymethyl) -N-octyl-glycine, N- (1-carboxyethyl) -L-alanine, L-acid glutamic acid, L-aspartic acid, N- (2-carboxyethyl) -Aspartic acid; and their mixtures.
• 2,2'-sulfinylbisacetic acid 2,2'-[methylenebis (sulphonyl)] bis-acetic acid, N, N '- (1,3-dioxo-1,3) are particularly preferred.
• propanediyl) bisglycine 2,5-Furanedicarboxylic acid, D-Tartaric acid, DL-Tartaric acid, L-Tartaric acid, Galactaric acid, L-glutamic acid, L-aspartic acid, and mixtures thereof.
• a lactone comprising at least one carboxylic group, in particular 1, 2 or 3 COOH groups.
• the lactones comprise 5 to 14 carbon atoms, in particular 6 to 13 or even 6 to 12 carbon atoms.
• lactones can be mentioned, alone or as a mixture:
• tetrahydro-5-oxo-2,3-furandicarboxylic acid can be used, 1,3-dihydro-3-oxo-4-lsobenzofurancarboxylic acid, 1,3-dihydro-1-oxo-5-lsobenzofurancarboxylic acid, tetrahydro-5-oxo-2-phenyl-3-furanecarboxylic acid isocitric acid lactone, 5-oxo-2-tetrahydrofuranecarboxylic acid and mixtures thereof.
• Said polycarboxylic acid and / or its cyclic anhydride and / or lactone, and mixtures thereof preferably represents 1 to 40% by weight, especially 5 to 30% by weight, and more preferably 10 to 25% by weight, of the total weight of the final polycondensate.
• the polycondensate according to the invention may further comprise a hydroxyl functional silicone (OH) and / or carboxylic acid (COOH). 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. Silicones having a weight average molecular weight (Mw) of between 300 and 20000, in particular 400 and 10,000, or even 800 and 4000, are preferably used. 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, R1 to R6 are saturated or aromatic, and may especially be chosen from alkyl radicals, in particular the methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, octyl, decyl, dodecyl and octadecyl radicals, cycloalkyl radicals, in particular the cyclohexyl radical, aryl radicals, in particular phenyl radicals; and naphthyl, arylalkyl radicals, especially benzyl and phenylethyl, as well as tolyl and xylyl radicals.
• alkyl radicals in particular the methyl, ethyl, propyl, iso
• 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.
• the ⁇ , ⁇ -diol polydimethylsiloxanes having a weight-average molecular weight (Mw) of between 400 and 10,000, even between 500 and 5,000, and especially between 800 and 4000, will be used.
• Mw weight-average molecular weight
• said silicone may 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 polycondate.
• the polycondensate according to the invention does not comprise other families of monomers than those mentioned above; in particular, it does not include aromatic monocarboxylic acids.
• the fact that the polycondensate is capable of being obtained by reaction of the only monomers mentioned above does not, of course, exclude the presence, during the reaction, of catalyst, initiator, or any other usual adjuvant of the reaction reactions. esterification and polymerization.
• the polycondensate according to the invention 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 according to the invention has a weight average molecular weight (Mw) of between 1500 and 300 000, even between 2000 and 200 000, and especially between 3000 and 150 000.
• 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 under consideration.
• the polymer according to the invention has a very high viscosity, which can be characterized as follows. At 25 ° C., when this viscosity can be measured (in particular when the polymer is not in solid form), it is strictly greater than 5000 mPa.s (centipoises), especially between 5100 and 10000 mPa.s. even between 6000 and 9500 mPa.s.
• the polycondensate according to the invention has a viscosity, measured at 110 ° C., of between 100 and 4000 mPa.s, especially between 130 and 3500 mPa.s, or even between 150 and 3000 mPa.s and even better between 200 and 3000 mPa.s. and 2500 mPa.s. More preferably, the polycondensate according to the invention has a viscosity, measured at 80 0 C, of between 150 and 5000 mPa.s, in particular between 200 and 4000 mPa.s, or between 250 and 3000 mPa.s and even better between 300 and 2000 mPa.s.
• This viscosity can be measured using a BROOKFIELD CAP 1000+ cone-plane viscometer.
• the adapted cone-plane is determined by the person skilled in the art, on the basis of his knowledge; especially :
• 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 (decamethylcyclopentasiloxane).
• 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 (decamethylcyclopentasiloxane).
• 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, at least 50 % by weight, at 25 ° C.
• the polycondensate according to the invention can be prepared by the esterification / polycondensation processes usually employed by those skilled in the art.
• a general method of preparation consists of: - mixing the polyols and the nonaromatic monocarboxylic acids,
• esterification catalysts for example of the sulfonic acid type (especially at a concentration by weight of between 1 and 10%) or titanate type (in particular at a concentration by weight of between 5 and 100 ppm). It is also possible to carry out the reaction, in whole or in part, in an inert solvent such as xylene and / or under reduced pressure, to facilitate the removal of water.
• an inert solvent such as xylene and / or under reduced pressure
• Said preparation process 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, so as 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 there may be mentioned BHT, BHA, TBHQ, 1,3,5-trimethyl-2,4,6, tris (3,5-di-tertbutyl-4-hydroxybenzyl) benzene , octadecyl-3,5, di-tert-butyl-4-hydroxycinnamate, tetrakis-methylene-3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate methane, octadecyl-3- (3) 4,5-di-tert-butyl-4-hydroxyphenyl) propionate 2,5-di-tert-butyl hydroquinone, 2,2-methyl-bis- (4-methyl-6-tert-butylphenol), 2,2-methylene-bis- (4-ethyl-6-tert-butylphenol), 4,4-butylidene-bis (6-tertbutyl-m-cresol), N, N-hexamethylene bis (3,5-d
• the polycondensates according to the invention can be used very advantageously in a composition, in particular a cosmetic or pharmaceutical composition, which moreover comprises a physiologically, in particular cosmetically or pharmaceutically acceptable medium, that is to say a medium which is compatible with cutaneous tissues. like the skin of the face or body, and keratin materials such as hair, eyelashes, eyebrows and nails.
• a physiologically, in particular cosmetically or pharmaceutically acceptable medium that is to say a medium which is compatible with cutaneous tissues. like the skin of the face or body, and keratin materials such as hair, eyelashes, eyebrows and nails.
• 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 final cosmetic or pharmaceutical composition.
• composition may then comprise, according to the intended application, the usual constituents for this type of composition.
• composition according to the invention may advantageously comprise a liquid fatty phase, which may constitute a solvent medium for the polymers according to the invention, and which may comprise at least one compound chosen from oils and / or solvents of mineral, animal, vegetable or synthetic, carbonaceous, hydrocarbon, fluorinated and / or silicone, volatile or nonvolatile, alone or in mixture to the extent that they form a homogeneous and stable mixture and are compatible with the intended use.
• a liquid fatty phase which may constitute a solvent medium for the polymers according to the invention, and which may comprise at least one compound chosen from oils and / or solvents of mineral, animal, vegetable or synthetic, carbonaceous, hydrocarbon, fluorinated and / or silicone, volatile or nonvolatile, alone or in mixture to the extent that they form a homogeneous and stable mixture and are compatible with the intended use.
• volatile in the sense of the invention, any compound capable of evaporating in contact with keratin materials, or lips, in less than one hour, at room temperature (25 ° C) and atmospheric pressure (1 atm).
• this volatile compound has a non-zero vapor pressure, at ambient temperature and atmospheric pressure, in particular ranging from 0.13 Pa to 40 000 Pa (10 -3 to 300 mmHg), in particular ranging from 1.3 Pa.
• the physiologically acceptable medium of the composition according to the invention may comprise, in a liquid fatty phase, at least one oil and / or a solvent which may be chosen from, alone or as a mixture:
• ester is a C12-C15 alkyl benzoate or has the following formula: R'rCOO-R'2 where:
• R ' 1 represents a linear or branched alkyl radical of 1 to 40 carbon atoms, preferably 7 to 19 carbon atoms, optionally comprising one or more ethylenic double bonds, optionally substituted and whose hydrocarbon chain may be interrupted by one or more several heteroatoms chosen from N and O and / or one or more carbonyl functions
• R'2 represents a linear or branched alkyl radical of 1 to 40 carbon atoms, preferably of 3 to 30 carbon atoms and better still of 3 to 20 carbon atoms.
• R'1 and / or R'2 may carry one or more substituents selected, for example, from groups comprising one or more heteroatoms selected from O and / or N, such as amino, amino , alkoxy, hydroxyl.
• R ' 1 groups are those derived from the preferably higher fatty acids selected from the group consisting of acetic, propionic, butyric, caproic, caprylic, pelargonic, capric, undecanoic, lauric, myristic, palmitic, stearic, isostearic. , arachidic, behenic, oleic, linolenic, linoleic, oleostearic, arachidonic, erucic, and mixtures thereof.
• R'1 is an unsubstituted branched alkyl group of 4 to 14 carbon atoms, preferably 8 to 10 carbon atoms and R 2 is an unsubstituted branched alkyl group of 5 to 15 carbon atoms, preferably from 9 to 11 carbon atoms.
• C 4 -C 4 esters optionally incorporating into their hydrocarbon chain one or more heteroatoms of N and O and / or one or more carbonyl functions; and more particularly purcellin oil (cetostearyl octanoate), isononyl isononanoate, isopropyl myristate, isopropyl palmitate, 2-ethylhexyl palmitate, octyl-2 stearate dodecyl, octyl-2-dodecyl erucate, isostearyl isostearate, C 2 to C 5 alcohol benzoate, hexyl laurate, diisopropyl adipate; and the heptanoates, octanoates, decanoates or ricinoleates of alcohols or polyalcohols, for example of fatty alcohols such as propylene glycol dioctanoate, as well as is
• oils with a high triglyceride content consisting of esters of fatty acids and of glycerol, the fatty acids of which may have various chain lengths of C 4 to C 24 , the latter may be linear or branched, saturated or unsaturated; these oils include wheat germ, maize, sunflower, shea, castor oil, sweet almond, macadamia, apricot, soya, rapeseed, cotton, alfalfa, poppy, pumpkin, sesame, squash, avocado, hazelnut, grape seed or black currant, evening primrose, millet, barley, quinoa, olive, rye, safflower, ofnadooulier, passionflower, muscat rose, jojoba, palm, calophyllum; or triglycerides of caprylic / capric acids such as those sold by Stearinerie Dubois or those sold under the names "Miglyol 810 ®", "812 ®” and "8
• C6-C32 monoalcohols in particular C12-C26, such as oleic alcohol, linoleic alcohol, linolenic alcohol, isostearyl alcohol, 2-hexyldecanol, 2 -butyloctanol, 2-undecylpentadecanol and octyldodecanol;
• hydrocarbon oils volatile or not, of synthetic or mineral origin, which may be chosen from hydrocarbon-based oils having from 5 to 100 carbon atoms, and in particular petroleum jelly, polydecenes, hydrogenated polyisobutenes such as Parleam, squalane, perhydrosqualine and their mixtures.
• linear, branched and / or cyclic C5-C48 alkanes and preferably branched C8-C16 alkanes such as C8-C16 isoalkanes of petroleum origin (also known as isoparaffins); especially decane, heptane, dodecane, cyclohexane; as well as isododecane, isodecane, isohexadecane.
• Volatile silicone oils that may be mentioned include volatile linear or cyclic silicone oils, in particular those having a viscosity of less than 8 centistokes, and especially having from 2 to 10 silicon atoms, these silicones possibly comprising alkyl or alkoxy groups.
• octamethylcyclotetrasiloxane having from 1 to 22 carbon atoms; and in particular octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, heptamethylhexyltrisiloxane, heptamethyloctyltrisiloxane, hexamethyldisiloxane, octamethyltrisiloxane, demethyltetrasiloxane, dodecamethylpentasiloxane, methylhexyldimethylsiloxane and mixtures thereof.
• the nonvolatile silicone oils that may be used according to the invention may be polydimethylsiloxanes (PDMSs), polydimethylsiloxanes comprising alkyl or alkoxy groups, during and / or at the end of the silicone chain, groups each having from 2 to 24 carbon atoms.
• PDMSs polydimethylsiloxanes
• phenyl silicones such as phenyltrimethicones, phenyldimethicones, phenyltrimethylsiloxydiphenylsiloxanes, diphenyldimethicones, diphenylmethyldiphenyltrisiloxanes and 2-phenylethyl trimethylsiloxysilicates.
• the physiologically acceptable medium of the composition according to the invention comprises, in a liquid fatty phase, at least one oil and / or a solvent chosen from, alone or as a mixture, isododecane, Parleam, the isononanoate of isononyl, octyldodecanol, phenyl trimethicone, C12-C15 alkyl benzoates and / or D5 (decamethylcyclopentasiloxane).
• the liquid fatty phase may further comprise additional oils and / or solvents, which may be chosen from, alone or as a mixture:
• fluorinated oils such as perfluoropolyethers, perfluoroalkanes such as perfluorodecalin, perfluorodamantanes, monoesters, diesters and triesters of perfluoroalkylphosphates and fluorinated ester oils;
• propylene glycol ethers which are liquid at room temperature, such as propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate or dipropylene glycol mono-butyl ether;
• - C8-C32 fatty acids such as oleic acid, linoleic acid, linolenic acid and mixtures thereof.
• Bifunctional oils comprising two functions selected from ester and / or amide and comprising from 6 to 30 carbon atoms, in particular 8 to 28 carbon atoms, more preferably 10 to 24 carbons, and 4 heteroatoms selected from O and N; preferably the amide and ester functions being in the chain;
• ketones which are liquid at ambient temperature (25 ° C.), such as methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, isophorone, cyclohexanone and acetone;
• aldehydes that are liquid at room temperature, such as benzaldehyde, acetylene, talconvergehyde;
• the liquid fatty phase 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. .
• hydrophobic silicas such as those described in EP-A-898960, for example, under the references "Aerosil R812 ®” by Degussa, "CAB-O-SIL TS-530 ®", “CAB O-SIL TS-610 ® “,” CAB-O-SIL TS-720 ® “by the company Cabot,” AEROSIL R972 ® “,” AEROSIL R974 ® “by Degussa;
• clays such as montmorillonite, modified clays, such as benzones, stearalkonium hectorite, stearalkonium bentonite,
• polysaccharide alkyl ethers in particular in which the alkyl group contains from 1 to 24 carbon atoms, preferably from 1 to 10, better still from 1 to 6, and more particularly from 1 to 3, such as those described in EP-A); A-898958.
• the amount of thickening agent in the composition according to the invention may range from 0.05 to 40% by weight, relative to the total weight of the composition, preferably from 0.5 to 20% and better still from 1 to 15%. in weight.
• composition according to the invention may also comprise at least one wax of vegetable, animal, mineral, synthetic or even silicone origin.
• hydrocarbon waxes such as beeswax can be mentioned alone or as a mixture; Carnauba wax, Candellila wax, Ouricoury wax, Japan wax, cork fiber wax or sugar cane wax; paraffin waxes of lignite; microcrystalline waxes; lanolin wax; the wax of Montan; ozokerites; polyethylene waxes; waxes obtained by Fischer-Tropsch synthesis; hydrogenated oils, fatty esters and concrete glycerides at 25 ° C. It is also possible to use silicone waxes, among which mention may be made of alkyls, alkoxys and / or polymethylsiloxane esters.
• the amount of wax in the composition according to the invention may range from 0.1 to 70% by weight, relative to the total weight of the composition, preferably from 1 to 40% by weight, and better still from 5 to 30% by weight. weight.
• the composition according to the invention may also comprise one or more dyestuffs chosen from pulverulent compounds such as pigments, fillers, nacres and flakes, and / or fat-soluble or water-soluble dyes.
• the dyestuffs, in particular pulverulent may be present in the composition in a content of from 0.01 to 50% by weight, relative to the weight of the composition, preferably from 0.1 to 40% by weight, or even from 1 to 30% by weight.
• pigments it is necessary to understand particles of any shape, white or colored, mineral or organic, insoluble in the physiological medium, intended to color the composition.
• nacres it is necessary to understand particles of any iridescent form, in particular produced by certain molluscs in their shell or else synthesized.
• the pigments may be white or colored, inorganic and / or organic, interferential or not.
• inorganic pigments mention may be made of titanium dioxide, optionally surface-treated, zirconium or cerium oxides, as well as iron or chromium oxides, manganese violet, ultramarine blue, hydrate of chrome and ferric blue.
• organic pigments mention may be made of carbon black, D & C type pigments, and lacquers based on cochineal carmine, barium, strontium, calcium, aluminum.
• the pearlescent pigments may be chosen from white pearlescent pigments such as mica coated with titanium, or bismuth oxychloride, colored pearlescent pigments such as titanium mica with iron oxides, titanium mica with in particular ferric blue or chromium oxide, titanium mica with an organic pigment of the aforementioned type as well as pearlescent pigments based on bismuth oxychloride.
• the fillers can be mineral or organic, lamellar or spherical. Mention may be made of talc, mica, silica, kaolin, powders of nylon and polyethylene, poly- ⁇ -alanine and polyethylene, Teflon, lauroyl-lysine, starch, nitrile and the like.
• organic carboxylic acids having from 8 to 22 atoms carbon, preferably from 12 to 18 carbon atoms, for example zinc, magnesium or lithium stearate, zinc laurate, magnesium myristate.
• Liposoluble dyes are for example Sudan Red, DC Red 17, DC Green 6, ⁇ -carotene, soybean oil, Sudan Brown, DC Yellow, 11, DC Violet 2, Orange DC 5 , yellow quinoline. They may represent 0.01 to 20% of the weight of the composition and better still 0.1 to 6%.
• the water-soluble dyes are, for example, beet juice, methylene blue and may represent 0.01 to 6% of the total weight of the composition.
• the composition may further include other ingredients commonly used in cosmetic compositions.
• Such ingredients may be chosen from antioxidants, perfumes, essential oils, preservatives, cosmetic active agents, moisturizers, vitamins, ceramides, sunscreens, surfactants, spreading agents, wetting agents, dispersing agents, antifoams, neutralizers, stabilizers, polymers and especially fat-soluble film-forming polymers, and mixtures thereof.
• antioxidants perfumes, essential oils, preservatives, cosmetic active agents, moisturizers, vitamins, ceramides, sunscreens, surfactants, spreading agents, wetting agents, dispersing agents, antifoams, neutralizers, stabilizers, polymers and especially fat-soluble film-forming polymers, and mixtures thereof.
• perfumes perfumes, essential oils, preservatives, cosmetic active agents, moisturizers, vitamins, ceramides, sunscreens, surfactants, spreading agents, wetting agents, dispersing agents, antifoams, neutralizers, stabilizers, polymers and especially fat-soluble film
• compositions according to the invention may be in any form acceptable and customary for a cosmetic or pharmaceutical composition. They can therefore be in the form of a suspension, a dispersion including oil in water with vesicles; an organic or oily solution optionally thickened or even gelled; an oil-in-water, water-in-oil or multiple emulsion; a gel or a mousse; an oily or emulsified gel; a dispersion of vesicles, in particular lipids; a two-phase or multiphase lotion; a spray; a lotion, a cream, an ointment, a soft paste, an ointment, a solid cast or molded and especially stick or cup, or compacted solid.
• compositions in accordance with the invention having improved gloss and gloss strength compared with the state of the art, they can be used for the care or the makeup of keratin materials such as the hair, the skin, the skin and the skin.
• They 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.
• Example 1 Synthesis of Pentaerythrityl Isophthalate / Isostearate
• a reactor equipped with a mechanical stirrer an inlet of argon and a distillation system, 280 g of isostearic acid and 100 g of pentaerythritol are charged and then heated gradually, under a gentle stream of argon at 110-130 ° C. to obtain a homogeneous solution.
• the temperature is then gradually increased to 180 ° C. and maintained for about 2 hours.
• the temperature is again raised to 220 ° C and maintained until an acid number of less than or equal to 1 is obtained, which takes about 11 hours.
• polycondensate 430 g of polycondensate are thus obtained in the form of a very thick oil.
• the polycondensate has the following characteristics:
• polycondensate 410 g of polycondensate are thus obtained in the form of a thick oil.
• the polycondensate has the following characteristics:
• Example 4 Synthesis of sorbitol sebacate / isostearate In a reactor equipped with a mechanical stirrer, an inlet of argon and a distillation system, 305 g of isostearic acid, 105 g of sorbitol and 90 g of sebacic acid are charged and then heated up to 180 0 C and the temperature is maintained for about 30 hours.
• polycondensate 400 g of polycondensate are thus obtained in the form of a very thick oil.
• the polycondensate has the following characteristics:
• a lipstick having the following composition was prepared:
• a lipstick can be prepared similarly by replacing the polycondensate of Example 1 with that of Example 2, 3 or 4.
• polycondensate 430 g of polycondensate are thus obtained in the form of a thick oil.
• the polycondensate has the following characteristics:
• polycondensate In a reactor equipped with a mechanical stirrer, an inlet of argon and a distillation system, 270 g of isostearic acid, 90 g of glycerol, 35 g of trans-aconitic acid and 105 g of sebacic acid are charged. then heated gradually to 220 0 C and the temperature is maintained for about 8 hours. 440 g of polycondensate are thus obtained in the form of a thick oil.
• the polycondensate has the following characteristics:
• polycondensate 450 g of polycondensate are thus obtained in the form of a thick oil.
• the polycondensate has the following characteristics:
• polycondensate 450 g of polycondensate are thus obtained in the form of a thick oil.
• the polycondensate has the following characteristics:

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