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
  • A61K8/89—Polysiloxanes
  • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
  • A61K8/894—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by a polyoxyalkylene group, e.g. cetyl dimethicone copolyol
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
  • A61K8/8135—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid; Compositions of derivatives of such polymers, e.g. vinyl esters (polyvinylacetate)
• • 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
  • A61K8/91—Graft copolymers
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/10—Preparations for permanently dyeing the hair
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
  • A61K2800/42—Colour properties
  • A61K2800/43—Pigments; Dyes
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
  • A61K2800/81—Preparation or application process involves irradiation

Definitions

• Cosmetic composition and method for the treatment of keratin materials comprising a photodimerizable compound.
• the present invention relates in general to a cosmetic composition
• a cosmetic composition comprising at least one cosmetic active agent and at least one photodimerizable material allowing the production of a deposit of material on keratin materials, and in particular on the hair, which is persistent in washing , whose location is precisely controlled, capable of providing lasting cosmetic properties to keratin materials, and can be removed at any time.
• the resistance of a deposit of material to washing can be provided by a low solubility of the deposit in aqueous detergent media.
• photocrosslinking makes it possible to selectively crosslink a deposit, in particular on specific zones of keratin materials previously coated with the photocrosslinkable composition, and thus to create a lasting deposit on certain zones and not others.
• the non-irradiated parts of the deposit for example covered with a mask
• the non-irradiated parts of the deposit remain soluble. They can then be easily removed during rinsing or shampooing after irradiation. It thus becomes possible, for example, to create patterns on keratin materials and images using “stencils” and various masks with a photocrosslinkable composition, for example colored, or even to treat only specific sensitized areas, such as the tips in the case of hair, with a conditioning composition or the like.
• photocrosslinkable materials such as materials derived from vinyl monomers, and in particular (meth) acrylate monomers.
• US Patent 5,300,285 describes a process for waving the hair and a composition for it. implementation of this process, and in particular a neutralizing composition based on silicone, comprising a silicone with vinyl function, a phonitoinitiator with free radicals and a solvent.
• This composition acts as a substitute for neutralizing solutions based on hydrogen peroxide when applied to the hair after a process of permanent deformation of the hair and photocrosslinking of the composition.
• This composition has the advantage of functioning simultaneously as a crosslinking agent for keratin, while conferring advantages on the hair such as conditioning and
• the photocrosslinking of the composition is triggered by the photoinitiator (generally a derivative of acetophenone), which releases a radical under irradiation in the UVA domain (350-385 nm).
• the photoinitiator generally a derivative of acetophenone
• compositions are also sought which are resistant to various attacks, such as water or mechanical shock, as well as compositions providing shine and long-lasting.
• compositions containing these materials derived from vinyl monomers are known to be unstable, in particular because of their sensitivity to oxygen and to humidity.
• photocrosslinking is sometimes obtained with prolonged irradiation, hence the risks of hair degradation under the action of UV.
• Japanese patent JP 09249812 describes interpenetrating networks containing molecules forming chelates and their uses, and more particularly compositions containing polymers of polyvinyl acetate type partially saponified with stilbazolium groups, crosslinked and containing chelating agents. This previously crosslinked material can then be used as it is in medical or cosmetic applications.
• this patent JP 09249812
• applying a composition containing non-crosslinked polymers to the hair or the skin before irradiation is no mention in this patent (JP 09249812) of applying a composition containing non-crosslinked polymers to the hair or the skin before irradiation.
• the object of the present invention is therefore to provide a cosmetic composition which, after application to keratin materials, in particular to keratin fibers such as the hair, is photocrosslinked in a possibly reversible manner, and results in a crosslinked deposit which does not dissolve , is persistent in washing and does not degrade the keratinous fiber, thus guaranteeing the durability of the cosmetic effects provided by this deposit.
• reversible photocrosslinking of a material or a composition is meant, within the meaning of the present application, a crosslinking by action of light of the material or composition, resulting in a deposit which can be removed at any time and easily removed from the hair.
• irradiation in the UVB domain leads to the reformation of the original double bonds and to the disappearance of the crosslinking.
• the subject of the present invention is a cosmetic composition for the treatment of keratin materials comprising at least one cosmetic active agent, characterized in that it additionally comprises at least one compound comprising at least one photodimerizable group, this compound having a molecular weight greater than 500g / mol;
• the compound comprising at least one photodimerizable group has a molecular mass greater than 700 g / mol, more advantageously greater than 850 g / mol, and even more preferably greater than 1000 g / mol.
• cosmetic active is meant, within the meaning of the present invention, any active compound having cosmetic or dermatological activity.
• photodimerizable group is meant, within the meaning of the present invention, a chemical group leading to photodimerization reactions under irradiation.
• photodimerization is meant, within the meaning of the present invention, a chemical reaction between two double bonds (of type 2 + 2) or two pairs of double bonds (of type 4 + 4).
• Materials having photodimerizable groups according to the invention have the advantage of being stable with respect to oxygen, humidity, and heat, and leading to reversible crosslinking.
• the photodimerizable groups according to the invention are very photosensitive. Consequently, even low energy irradiation leads to rapid and effective crosslinking of the material, which, in the case of a cosmetic application, induces a short duration and low energy irradiation which does not lead to degradation of the keratin materials. This is especially advantageous for a hair or nail polish application.
• - Y and 2 independently of one another denote a carbon or nitrogen atom
• - A is a divalent linking group chosen from alkylene radicals, cycloaromatic radicals, heterocyclic radicals, carbonyl radicals, alkenylene radicals and their combinations
• - B is a monovalent group chosen from alkyl radicals, cycloaromatic radicals, heterocyclic radicals, carbonyl radicals, alkenyl radicals and combinations thereof
• - X is a divalent group chosen from alkylene radicals, cycloaromatic radicals, heterocyclic radicals, carbonyl radicals, alkenylene radicals and their combinations, and each of the groups mentioned may optionally be substituted by one or more groups chosen from alkyl, hydroxy, amino, mono or dialkylamino, halogens, aryies, carboxy groups, alkoxy, alkoxycarbonyls, hydrogen carbonyls, sulfonato, amide, and acyls.
• the dimerizable groups according to the invention are in particular those cited in patents US-2,811,510, EP 0 313 220, EP 0 313 221, E 092 901, GB 2 030 575 and GB 2 076 826, as well as in the articles "Chemical review Vol 83.5 1983, p 507 "” Polym, Paint color Journal 1988, 178, p 209 “and” Current Trends in Polymer Photochemistry, Ellis Morwood Edition, NY, 1995 ".
• photodimerizable groups chosen from monovalent radicals of the following compounds:
• R represents the hydrogen atom, an alkyl or hydroxyalkyl group
• R - R ' represents the hydrogen atom or an alkyl, styrylazolium group of formula:
• A denotes a sulfur atom, an oxygen atom, or a group NR 'or C (R') 2 , R and R 'being as defined above,
• Such chemical groups have activated double bonds, so that the photodimerization of these double bonds is triggered spontaneously in the UVA domain, without requiring a photoinitiator.
• the compound comprising at least one photodimerizable group is a polymer. Even more advantageously, it is in the form of particles, in particular dispersed particles.
• photoinitiator is meant, within the meaning of the present invention, a compound which initiates the photodimerization reaction and releases a radical under irradiation, in particular in the UV field.
• composition according to the invention comprises a compound comprising at least one photodimerizable group chosen from the photodimerizable groups previously mentioned, it is preferably free of photoinitiator.
• the compounds with photodimerizable group (s) according to the invention are preferably not dyes.
• the photodimerizable groups according to the invention can be easily grafted onto any type of support compound.
• the support compound is a filler forming a particle.
• Particles include mineral particles and organic particles.
• the mineral particles can consist of oxides, dihydrate oxides, hydroxides, carbonates, sulfides, silicates, phosphates of silicon, calcium, magnesium, zinc, aluminum, titanium, zirconium, of cerium, nacres, micas, particles consisting of native metals, that is to say alkali metals, alkaline earth metals, transition metals, rare earth metals, coated or not and their alloys.
• the metals aluminum, copper, silver, gold, indium, iron, platinum, nickel, molybdenum, silicon, titanium, tungsten, antimony are preferred.
• the organic particles can consist of latexes, polystyrene, polystyrene derivatives, silicones, fluoropolymers, polypropylene, polyethylene, poly (meth) acrylic acid, polymethacrylate, polyurethane, polyamide, polycarbonate, polyvinyl chloride, polyvinyl acetate, fluoropolymers, polyethylenes, polypropylene, polysobutylene, poly (1 -butylene), the copolymers and mixtures of the polymers mentioned, alkyl cellulose, hydroxyalkyl cellulose, cellulose ethers, cellulose esters, hydroxypropylcellulose, hydroxypropyldextran, hydroxypropylmethyl cellulose, cellulose acetate, carboxyethylcellulose, cellulose sulfate,
• the polystyrene particles are commercially available from Polyscience Inc (Warrington, PA) or Duke Scientific Corporation (Palo Alto, CA). These organic particles can be crosslinked using crosslinkers such as, for example, divinylbenzene, glutaraldehyde, 1, 4- bis (acryloyl) piperazine, carbodiimides, N-hydroxysuccinimide and derivatives, divinylsufone, dithiobis (succinimidyl) propionate, N-succinimidyl-3- (2-pyridyldithio) propionate.
• crosslinkers such as, for example, divinylbenzene, glutaraldehyde, 1, 4- bis (acryloyl) piperazine, carbodiimides, N-hydroxysuccinimide and derivatives, divinylsufone, dithiobis (succinimidyl) propionate, N-succinimidyl-3- (2-pyridyldithi
• the support compound is chosen from polymers, and even more preferably from poly (vinyl) polymers and polydiorganosiloxanes.
• polyvinyl polymers polyvinyl acetate, preferably partially saponified, are particularly preferred.
• the compound (s) comprising at least one photodimerizable group according to the invention are advantageously, thus a polymer soluble or dispersed in the composition, or, more advantageously still, a polymer adsorbed on polymer particles, themselves dispersed in the composition.
• the polymer particles are very preferably particles of vinyl polymers, and better still particles of polyvinyl acetate.
• the invention relates very particularly, as compound (s) comprising at least one photodimerizable group,. aqueous dispersions of a partially saponified polyvinylacetate type polymer carrying stilbazolium groups, brought into contact, in particular mixed, with polyvinylacetate particles.
• the photodimerizable material can also form all or part of a material of the core / shell type as defined in application FR 2 838 052, filed by the Applicant.
• the compound (s) comprising at least one photodimerizable group according to the invention preferably represent (s) 0.01 to 25%, better still 0.1 to 20%, and better still 1 to 15% of the total weight of composition.
• the cosmetic composition according to the invention may, in addition, comprise an effective amount of at least one photosensitizer.
• photosensitizer is meant within the meaning of the present invention, an ingredient which modifies the wavelength of the irradiation, thus triggering the photodimerization reaction.
• the photodimerization of dimethylmaleimide groups is triggered by irradiation centered on the wavelength range ranging from 270 to 300 nm.
• a photosensitizer such as thioxanthone
• photodimerization becomes effective with irradiation centered on the wavelength range from 360 to 430 nm.
• photosensitizers which can be used according to the invention, there may be mentioned in particular thioxanthone, bengal rose, phloxin, eosin, erythrosin, fluorescein, acriflavin, thionin, riboflavin, proflavin, chlorophylls , hematoporphyrin, methylene blue and mixtures thereof.
• the photosensitizer which can be used according to the invention represents 0.00001% to 5% by total weight of the composition.
• the cosmetic active ingredient (s) according to the invention is (are) chosen from:
• coloring matters and in particular hair dyes
• the saccharide, oligosaccharide or polysaccharide type compounds, hydrolyzed or not, modified or not, which can be used in the present invention are chosen from those which are especially described in "Encyclopedia of Chemical Technology, Kirk-Othmer, Third Edition , 1982, volume 3, pp. 896-900, and volume 15, pp 439-458 ", in” Polymers in Nature, by EA MacGREGOR and CT GREENWOOD, Editions John Wiley & Sons, Chapter 6, pp 240-328, 1980 "and in the Industrial Gums - Polysaccharides and their Derivatives, Edited by Roy L. WHISTLER, Second Edition, Edition Académie Press Inc.”, the content of these three works being fully included in this request for reference.
• saccharides, oligosaccharides, polysaccharides hydrolyzed or not, modified or not, which can be used in the invention mention may be made especially of glucans, starches modified or not (such as those obtained, for example, from cereals such as wheat, corn or rice, vegetables like light peas, tubers like potatoes or cassava) and different from starch betainate as described above, amylose, amylopectin, glycogen dextrans, ⁇ -glucans, celluloses and their derivatives (methylcelluloses, hydroxyalkylcelluloses, ethylhydroxyethylcelluloses, carboxymethyl-celluloses), fructosans, inulin, levane, mannans, xylans, lignins, arabans, galactans, galacturonans, chitin, glucoronoxylans, arabinoxylans, xyloglucans, galactomannans, glucomannans, pectic acids and pe
• amino acids there may be mentioned, for example, cysteine, lysine, alanine, N-phenylalanine, arginine, glycine, leucine, and mixtures thereof.
• oligopeptides, peptides, proteins hydrolyzed or not, modified or not which can be used according to the invention, mention may in particular be made of hydrolysates of wool or silk proteins, modified or not, proteins vegetables such as wheat proteins.
• enzymes which can be used, mention may be made of laccases, peroxidases, lipases, proteases, glycosidases, dextranases, uricases, alkaline phosphatase.
• branched fatty acids or not suitable in the present invention, mention may in particular be made of Cs-C-30 carboxylic acids, such as palmitic acid, oleic acid, linoleic acid, myristic acid, stearic acid, lauric acid, and mixtures thereof.
• the fatty alcohols which can be used in the present invention include in particular the C8-C30 alcohols such as, for example, palmityl, oleyl, linoleyl, myristylic, stearyl and lauryl alcohols.
• a wax within the meaning of the present invention, is a lipophilic compound, solid at room temperature (about 25 ° C), with reversible solid / liquid state change, having a melting temperature above about 40 ° C and which can range up to 200 ° C, and having an anisotropic crystalline organization in the solid state.
• the size of the crystals of the wax is such that the crystals diffract and / or scatter light, giving the composition which comprises them a more or less opaque cloudy appearance.
• animal origin such as beeswax, spermaceti, lanolin wax and lanolin derivatives
• vegetable waxes such as Camauba, Candellila, Ouricury, Japanese wax, cocoa butter or cork fiber or sugar cane waxes
• mineral waxes by example, paraffin, petrolatum, lignite or microcrystalline waxes or ozokerites.
• ceramides mention may be made in particular of the ceramides of classes I, II, III and V according to the classification of DAWNING, and more particularly N-oleyldehydrosphingosine.
• the hydroxylated organic acids are chosen from those well known and used in the art. Mention may in particular be made of citric acid, lactic acid, tartaric acid, malic acid.
• the active UV-A and / or UV-B sun filters that can be used according to the invention are those well known to those skilled in the art. Mention may in particular be made of dibenzoylmethane derivatives such as 4-methyldibenzoylmethane, 4-isopropyldibenzoylmethane, 4-tert-butyldibenzoylmethane, 2,4-dimethyldibenzoylmethane, 4-tert-buty 4'-diisopropyldibhane p-amino benzoic acid and its esters such as 2-ethylhexyl p-dimethylaminobenzoate and N-propoxylated ethyl p-aminobenzoate, salicylates such as triethanolamine saltcylate, cinnamic acid esters such as 4- 2-ethylhexyl methoxy-cinnamate, methyl diisopropylcinnamate, menthy
• antioxidants and anti-free radical agents which can be used in the present invention, there may be mentioned, for example, ascorbic acid, ascorbylated compounds such as ascorbyl dipalmitate, t-butylhydroquinone, polyphenols such than phloroglucinol, sodium sulfite, erythorbic acid, flavonoids.
• the chelators can be chosen in particular from EDTA (ethylenediaminetetraacetic acid) and its salts such as disodium EDTA and dipotassium EDTA, phosphate compounds such as sodium metaphosphate, sodium hexametaphosphate, tetrapotassium pyrophosphate, phosphonic acids and their salts such as the salts of ethylenediaminetetramethylenephosphonic acid.
• EDTA ethylenediaminetetraacetic acid
• phosphate compounds such as sodium metaphosphate, sodium hexametaphosphate, tetrapotassium pyrophosphate
• phosphonic acids such as the salts of ethylenediaminetetramethylenephosphonic acid.
• the anti-dandruff agents are chosen, for example, from: - benzethonium chloride, benzalkonium chloride, chlorhexidine, chloramine T, chloramine B, 1, 3-dibromo-5,5-dimethylhydantoin, 1,3-dichloro 5,5-dimethylhydantoin, 3- bromo-chloro 5,5-dimethylhydantoin, N-chlorosuccinimide; - 1-hydroxy-2-pyridone derivatives such as, for example, 1-hydroxy-4-methyl-2-pyridone, 1-hydroxy-6-methyl-2-pyridone and 1-hydroxy-4, 6-dimethyl-2-pyridone;
• - triclosan - azole compounds such as climbazole, ketoconazole, clotrinazole, econazole, isoconazole and miconazole b;
• the anti-dandruff agents mentioned above can also optionally be used in the form of their physiologically acceptable organic or inorganic base addition salts.
• organic bases are in particular low molecular weight alkanolamines such as ethanolamine, diethanolamine, N-ethylethanolamine, triethanolamine, diethylaminoethanol, 2-amino-2-methylpropanedione; non-volatile bases such as ethylenediamine, hexamethylenediamine, cyclohexylamine, benzylamine, N-methylpiperazine; quaternary ammonium hydroxides, for example, trimethylbenzyl hydroxide; guanidine and its derivatives, and in particular its alkyl derivatives.
• inorganic bases are in particular the salts of alkali metals, such as sodium or potassium; ammonium salts, alkaline earth metal salts, such as magnesium, calcium; the cationic di, tri or tetravalent metal salts, such as zinc, aluminum and zirconium.
• alkali metals such as sodium or potassium
• ammonium salts such as sodium, potassium
• alkaline earth metal salts such as magnesium, calcium
• the cationic di, tri or tetravalent metal salts such as zinc, aluminum and zirconium.
• Alkanolamines, ethylenediamine and inorganic bases such as the alkali metal salts are preferred.
• the seborrhea regulating agents are, for example, succinylchitosan and poly- ⁇ -alanine.
• Soothing agents are, for example, azulene and glycyrrhetinic acid.
• the cationic surfactants are those well known per se, such as the salts of primary, secondary or tertiary fatty amines, optionally polyoxyalkylenated; quaternary ammonium salts such as chlorides or bromides of tetraalkylammonium, alkylamidoalkyl-trialkylammonium, trialkylbenzylammonium, trialkylhydroxy-alkylammonium or alkylpyridinium; imidazoline derivatives.
• cationic polymer is meant any polymer containing cationic groups and / or groups which can be ionized into cationic groups.
• the cationic polymers which can be used in accordance with the present invention can be chosen from all those already known per se as improving the cosmetic properties of hair treated with detergent compositions, namely in particular those described in patent application EP-A-0 337 354 and in French patent applications FR-A- 2 270 846, 2 383 660, 2 598 611, 2 470 596 and 2 519 863.
• the preferred cationic polymers are chosen from those which contain units comprising primary, secondary, tertiary and / or quaternary amine groups which can either be part of the main polymer chain, or be carried by a lateral substituent directly linked thereto.
• the cationic polymers used generally have a number average molecular mass of between 500 and 5.10 6 approximately, and preferably between 10 3 and 3.10 6 approximately.
• cationic polymers mention may be made more particularly of polymers of the polyamine, polyaminoamide and polyquaternary ammonium type. These are known products.
• polymers of the polyamine, polyaminoamide, and quaternary polyammonium type which can be used in the composition of the present invention are those described in French patents Nos . 2,505,348 and 2,542,997. Among these polymers, mention may be made of:
• cationic polysaccharides described more particularly in US patents 3,589,578 and 4,031,307 such as guar gums containing cationic trialkylammonium groups; (5) polymers consisting of piperazinyl units and divalent alkylene or hydroxyalkylene groups with straight or branched chains, optionally interrupted by oxygen, sulfur, nitrogen atoms or by aromatic or heterocyclic rings, as well as the products of oxidation and / or quaternization of these polymers. Such polymers are described in particular in French patents 2,162,025 and 2,280,361;
• polyaminoamide derivatives for example, adipic acid / diakylaminohydroxyalkyldialkylene-triamine polymers in which the alkyl group contains from 1 to 4 carbon atoms and preferably denotes a ' methyl group, ethyl, propyl, and the alkylene group contains from 1 to 4 carbon atoms, and preferably denotes the ethylene group.
• adipic acid / diakylaminohydroxyalkyldialkylene-triamine polymers in which the alkyl group contains from 1 to 4 carbon atoms and preferably denotes a methyl group, ethyl, propyl, and the alkylene group contains from 1 to 4 carbon atoms, and preferably denotes the ethylene group.
• the molar ratio between the polyalkylene polylamine and the dicarboxylic acid being between 0.8: 1 and 1.4: 1; the resulting polyaminoamide being reacted with epichlorohydrin in a molar ratio of epichlorohydrin relative to the secondary amine group of the polyaminoamide of between 0.5: 1 and 1.8: 1.
• alkyldiallylamine or dialkyldiallylammonium cyclopolymers such as the homopolymer of dimethyldiallyl ammonium chloride and copolymers of diallyldimethylammonium chloride and acrylamide;
• cationic polymers which can be used in the context of the invention are cationic proteins or hydrolysates of cationic proteins, polyalkyleneimines, in particular polyethyleneimines, polymers containing vinylpyridine or vinylpyridinium units, condensates of polyamines and epichlorohydrin, quaternary polyureylenes and chitin derivatives.
• amphoteric polymers which can be used in accordance with the invention can be chosen from polymers comprising units B and C distributed statistically in the polymer chain where B denotes a unit derived from a monomer comprising at least one basic nitrogen atom and C denotes a unit deriving from an acidic monomer comprising one or more carboxylic or sulphonic groups or else B and C can denote groups deriving from zwitterionic monomers of carboxybétaines or sulphobetaines; B and C can also denote a cationic polymer chain comprising primary, secondary, tertiary or quaternary amine groups, in which at least one of the amine groups carries a carboxylic or sulphonic group linked via a hydrocarbon group, or although B and C form part of a chain of a polymer with an ethylene-dicarboxylic unit, one of the carboxylic groups of which has been caused to react with a polyamine comprising one or more primary or secondary amine groups.
• a monomer derived from a vinyl compound carrying a carboxyl group such as more particularly acrylic acid, methacrylic acid, maleic acid, alpha-chloroacrylic acid
• a basic monomer derived from a substituted vinyl compound containing at least one basic atom such as more particularly the dialkylaminoalkyimethacrylate and acrylate, the dialkylaminoalkyl-methacrylamide and acrylamide.
• Such compounds are described in US Pat. No. 3,836,537. Mention may also be made
• the vinyl compound can also be a dialkyldiallylammonium salt such as diethyldiallylammonium chloride.
• copolymers of acrylic acid and the latter monomer are offered under the names Merquat ® 280, Merquat 295 and Merquat ® ® Plus 3330 by Calgon.
• (2) polymers comprising units derived from: a) at least one monomer chosen from acrylamides or methacrylamides substituted on nitrogen with an alkyl group, b) from at least one acidic comonomer containing one or more carboxylic groups reactants, and c) at least one basic comonomer such as esters with primary, secondary, tertiary and quaternary amine substituents of acrylic and methacrylic acids, and the product of quaternization of dimethylaminoethyl methacrylate with dimethyl or diethyl sulfate.
• N-substituted acrylamides or methacrylamides which are more particularly preferred according to the invention are groups whose alkyl groups contain from 2 to 12 carbon atoms and more particularly N-ethylacrylamide, N-tertiobutylacrylamide, N-tertiooctylacrylamide, N- octyl. N-decylacrylamide, N-dodecylacrylamide and the corresponding methacrylamides.
• the acid comonomers are chosen more particularly from acrylic, methacrylic, crotonic, itaconic, maleic, fumaric acids as well as alkyl monoesters having 1 to 4 carbon atoms of maleic or fumaric acids or anhydrides.
• the preferred basic comonomers are aminoethyl, butylaminoethyl, N, N'-dimethylaminoethyl, N-tert-butylaminoethyl methacrylates.
• Rio represents a divalent group derived from a saturated dicarboxylic acid, from an aliphatic mono or dicarboxylic acid having an ethylenic double bond, from an ester of a lower alkanol having 1 to 6 carbon atoms of these acids or a group deriving from the addition of any one of said acids with a primary bis or secondary derivative bis amine
• Z denotes a group of a bis-primary, mono or bis-secondary polyalkylene polyamine and preferably represents: a ) in the proportions of 60 to 100% by moles, the group
• the saturated carboxylic acids are preferably chosen from acids having 6 to 10 carbon atoms such as adipic, 2,2,4-trimethyladipic and 2,4,4-trimethyladipic, terephthalic acids, acids with ethylenic double bonds such as, for example, acrylic, methacrylic, itaconic acids.
• the alkane-sultones used in the alkylation are preferably propane- or butane-sultone, the salts of the alkylating agents are preferably the sodium or potassium salts.
• Ru denotes a polymerizable unsaturated group such as an acrylate, methacrylate, acrylamide or methacrylamide group
• y and z each represent an integer from 1 to 3
• R ⁇ 2 and R 13 represent a hydrogen atom, a methyl group, ethyl or propyl
• R and R 15 represent a hydrogen atom or an alkyl group such that the sum of the carbon atoms in R 4 and R 15 does not exceed 10.
• the polymers comprising such units can also comprise units derived from non-zwitterionic monomers such as acrylate or methacrylate of dimethyl- or diethylaminoethyl, or alkyl acrylates or methacrylates, acrylamides or methacrylamides, or vinyl acetate .
• Examples include methyl methacrylate copolymer and dimethylcarboxymethylammonioethyl methacrylate methyl such as the product sold under the name Diaformer® ® Z301 by Sandoz.
• R 2 0 represents a hydrogen atom, a CH3O group, CH 3 CH 2 O, phenyl, R 2 ⁇ denotes hydrogen or a lower alkyl group such as methyl, ethyl, R 22 denotes hydrogen or a lower alkyl group such as methyl, ethyl, R 2 3 denotes a lower alkyl group such as methyl, ethyl or a group corresponding to the formula: -R 2 4-N (R 2 2) 2, R24 representing a group -CH 2 -CH 2 -, -CH 2 -CH 2 -CH 2 -, -CH 2 -CH (CH 3 ) -, R22 having the meanings mentioned above, as well as the higher homologs of these groups and containing up to 6 carbon atoms.
• Amphoteric polymers of the -DXDX- type chosen from: a) the polymers obtained by the action of chloracetic acid or sodium chloroacetate on the compounds comprising at least one
• X denotes the symbol E or E ', E or E', identical or different, denote a bivalent group which is a straight or branched chain alkylene group containing up to 7 " carbon atoms in the main chain unsubstituted or substituted by hydroxyl groups, and which may also contain oxygen, nitrogen, sulfur atoms, 1 to 3 aromatic and / or heterocyclic rings; the oxygen, nitrogen and sulfur atoms being present in the form of ether, thioether, sulfoxide, sulfone, sulfonium, alkylamine, alkenylamine, hydroxyl groups, benzylamine, amine oxide, quaternary ammonium, amide, imide, alcohol, ester and or urethane.
• E denotes the symbol E or E 'and at least once E';
• E having the meaning given above and E 'is a bivalent group which is a straight or branched chain alkylene group having up to 7 carbon atoms in the main chain, whether or not substituted by one or more hydroxyl groups and comprising a or more nitrogen atoms, the nitrogen atom being substituted by an alkyl chain optionally interrupted by an oxygen atom and necessarily having one or more carboxyl functions or one or more hydroxyl functions and betaiized by reaction with chloracetic acid or sodium chloracetate.
• the silicones which can be used in accordance with the invention may be soluble or insoluble in water, and they may in particular be polyorganosiloxanes insoluble in water; they can be in the form of oils, waxes, resins or gums.
• the silicones are more particularly chosen from those having a boiling point of between 60 ° C. and
• This is, for example, octamethylcyclotetra-siloxane marketed in particular under the name of "VOLATILE SILICONE 7207" by UNION CARBIDE or "SILBIONE 70045 V 2" by RHODIA, decamethylcyclopentasiloxane marketed under the name "VOLATILE SILICONE 7158" by UNION CARBIDE, "SILBIONE 70045 V 5" by RHODIA.
• non-volatile silicones mention may especially be made of polyalkylsiloxanes, polyarylsiloxanes, polyalkylaryisiloxanes, gums and silicone resins, polyorganosiloxanes modified with; organofunctional groups.
• organomodified silicones which can be used in accordance with the invention are silicones as defined above and comprising in their structure one or more organofunctional groups attached via a hydrocarbon group.
• organomodified silicones mention may be made of polyorganosiloxanes comprising: - polyethyleneoxy and / or polypropyleneoxy groups optionally comprising alkyl groups, C 6 -C 2 4 as the products known as dimethicone copolyol sold by the company Dow Corning under the name DC 1248 or the oils Silwet ® L 722, L 7500, L 77, L 711 from the company UNION CARBIDE and the alkyl (C ⁇ 2 ) -methicone-copolyol sold by the company DOW CORNING under the name Q2 5200;
• substituted or unsubstituted amino groups such as the products sold under the name GP 4 Silicone Fluid and GP 7100 by the company GENESEE or the products sold under the names Q2 8220 and DOW CORNING 929 or 939 by the company DOW CORNING.
• the substituted amino groups are in particular C1-C4 aminoalkyl groups;
• oils of vegetable origin of sweet almond oil, avocado oil, castor oil, olive oil, jojoba, sunflower oil, wheat germ oil, sesame oil, peanut oil, grape seed oil, soybean oil, rapeseed oil, l safflower oil, coconut oil, corn oil, hazelnut oil, shea butter, palm oil, apricot kernel oil, calophyllum oil; as oil of animal origin, perhydrosqualene; as oils of mineral origin, paraffin oil and petrolatum oil.
• polyisobutenes and poly ( ⁇ -olefins) are chosen from those well known in the art.
• esters examples include fatty acid esters such as isopropyl myristate, isopropyl palmitate, 2-ethylhexyl palmitate, Purcellin oil (stearyl octanoate), l 'isononyl or isostearyl isononanoate, isopropyl lanolate, and mixtures thereof.
• fatty acid esters such as isopropyl myristate, isopropyl palmitate, 2-ethylhexyl palmitate, Purcellin oil (stearyl octanoate), l 'isononyl or isostearyl isononanoate, isopropyl lanolate, and mixtures thereof.
• the anionic polymers generally used in the present invention are polymers comprising groups derived from carboxylic, sulphonic or phosphoric acids, and having a molecular weight by weight of between 500 and 5,000,000.
• the carboxylic groups are provided by monoacid or unsaturated dicarboxylic acid monomers such as those corresponding to the formula:
• n is an integer from 0 to 10
• A denotes a methylene group, optionally linked to the carbon atom of the unsaturated group or to the neighboring methylene group when n is greater than 1, via a heteroatom such as oxygen or sulfur
• Ri denotes a hydrogen atom, a phenyl or benzyl group
• R 2 denotes a hydrogen atom, a lower alkyl or carboxyl group
• R3 denotes a hydrogen atom, a lower alkyl group, a group -CH 2 -COOH, phenyl or benzyl.
• a lower alkyl group preferably contains from 1 to 4 carbon atoms and denotes in particular the methyl and ethyl groups.
• the anionic polymers with carboxylic groups preferred according to the invention are:
• C) copolymers derived from -crotonic acid such as those comprising vinyl acetate or propionate units in their chain, and optionally other monomers such as the allyl or methallyl ester, vinyl ether or vinyl ester of a saturated carboxyic acid , linear or branched, with a long hydrocarbon chain, such as those containing at least 5 carbon atoms, these polymers possibly being grafted and crosslinked, or else a vinyl, allyl or methallyl ester of an ⁇ or ⁇ -cyclic carboxyic acid.
• Such polymers are described inter alia in French patents numbers 1 222 944, 1 580 545, 2265 782, 2 265 781, 1 564 110 and 2 439 798.
• Polymers also belonging to this class are the copolymers of maleic, citraconic, itaconic anhydrides and an allylic or methallylic ester optionally comprising an acrylamide, methacrylamide group, an ⁇ -olefin, acrylic or methacrylic esters, acrylic or methacrylic acids or vinylpyrrolidone in their chain, the anhydride functions are monoesterified or monoamidified.
• these polymers are for example described in French patents 2,350,384 and 2,357,241 of the applicant.
• polyacrylamides containing carboxylate groups are polymers comprising vinylsulfonic, styrene-sulfonic, naphthalene-sulfonic or acrylamido-alkylsulfonic units. These polymers can in particular be chosen from:
• salts of polyvinylsulfonic acid having a molecular mass of between approximately 1,000 and 100,000 as well as the copolymers with an unsaturated comonomer such as acrylic or methacrylic acids, and their esters, as well as acrylamide or its derivatives, vinyl ethers and vinylpyrrolidone;
• the anionic polymers are preferably chosen from acrylic acid copolymers such as the acid terpolymer acrylic / ethyl acrylate / N-tertiobutylacrylamide sold under the name ULTRAHOLD STRONG® by the company BASF,.
• copolymers derived from crotonic acid such as vinyl acetate / vinyl tert-butyl benzoate / crotonic acid terpolymers and acid terpolymers crotonic / vinyl acetate / vinyl neododecanoate sold under the name Resin 28-29-30 by the company NATIONAL STARCH
• polymers derived from maleic, fumaric, itaconic acids or anhydrides with vinyl esters, vinyl ethers, vinyl halides, phenylvinyl derivatives, acrylic acid and its esters such as the methyl vinyl ether / monoesterified maleic anhydride sold under the name Gantrez ® ES 425 by the company ISP copolymers of methacrylic acid and of methyl methacrylate sold under the name EUDRAGIT® L by the company ROHM PHARMA, the copolymer of methacrylic acid and eth acrylate yl sold under the name LUVIMER® MAEX by
• nonionic polymers which can be used according to the present invention: - vinylpyrrolidone homopolymers;
• polyalkyloxazolines such as polyethyloxazolines by Dow Chemical under the names PEOX® 50,000, Peox ® 200 000 ® and Peox 500,000
• - vinyl acetate homopolymers such as the product offered under the name of APPRETAN ® EM by the company HOECHST or the product offered under the name of RHODOPAS ® A 012 by the company RHONE POULENC
• - vinyl acetate copolymers and acrylic ester such as the product sold under the name Rhodopas AD 310 ® from Rhône-Poulenc;
• - acrylic ester copolymers such as, for example, copolymers of alkyl acrylates and alkyl methacrylates such as the products sold by the company Rohm & Haas under the names Primal AC-261 K ® and EUDRAGIT ® NE 30 D, by the company BASF under the names Acronal ® 601, Luhydran ® LR 8833 or 8845, by the company Hoechst under the names APPRETAN® N 9213 or N 921 2; - copolymers of acrylonitrile and of a nonionic monomer chosen, for example, from butadiene and alkyl (meth) acrylates; include the products provided under the names Nipol ® LX 531 8 by Nippon Zeon or those provided under the name CJ 0601 8 by the company Rohm &Haas; - polyurethanes, such as the products provided under the names Acrysol ® RM 1020 and RM 2020 ACRYSOL® by Rohm &
• Nonionic unmodified guar gums are, for example, products sold under the name VIDOGUM ® GH 175 by the company
• modified nonionic guar gums which can be used according to the invention are preferably modified with C 1 -C 6 hydroxyalkyl groups. Mention may be made, by way of example, of the hydroxymethyl, hydroxyethyl, hydroxypropyl and hydroxybutyl groups.
• guar gums are well known in the art and can, for example, be prepared by reacting corresponding alkene oxides, such as, for example, propylene oxides, with guar gum so to obtain a guar gum modified with hydroxypropyl groups.
• Such gums guar nonionic optionally modified with hydroxyalkyl groups are, for example, sold under the trade names Jaguar ® HP8, HP60 and JAGUAR® Jaguar® HP120, Jaguar DC 293 ® and JAGUAR® HP 105 by the company Meyhall, or under the name GALACTASOL ® 4H4FD2 by the company AQUALON.
• the alkyl groups of the nonionic polymers preferably contain from 1 to 6 carbon atoms.
• the reducing agents can be chosen from thioacids and their salts (thioglycolic or thiolactic acid, cysteine or cysteamine), sulphites of alkali or alkaline earth metals, reducing sugars such as glucose, vitamin C and its derivatives, derivatives of sulfinic acid, phosphines.
• the amounts of these various cosmetic active agents are those conventionally used in the fields under consideration, for example from 0.001 to 30% by weight relative to the total weight of the composition.
• composition according to the invention can also comprise a solvent or a mixture of cosmetically acceptable solvents.
• cosmetically acceptable is meant within the meaning of the invention physiologically acceptable solvents, non-toxic and capable of being applied to the skin or hair of human beings.
• the solvent (s) generally represent 0.1% to 99% of the total weight of the composition.
• the pH of the compositions according to the invention is preferably between 2 and 12, and even more preferably between 3 and 11.
• composition of the invention may also contain conventional adjuvants such as perfumes, fillers, pH adjusters (acidic or basic), and preservatives.
• adjuvants such as perfumes, fillers, pH adjusters (acidic or basic), and preservatives.
• the amounts of these various adjuvants of the composition according to the invention are those conventionally used in cosmetics.
• the present invention also relates to a process for treating keratin materials comprising the application to said keratin materials of a composition as defined above, and the irradiation of this composition to obtain a crosslinked deposit.
• the present invention relates to a process for treating keratin materials comprising the following steps: a) application to the keratin materials of a cosmetic composition according to the invention as defined above, and b) irradiation of said composition on keratin materials to crosslink the composition.
• the composition can be applied to wet or dry keratin materials, clean or not.
• the keratin materials are dried after application of the composition and before irradiation. It is also possible to include in the process, before or after step b) of irradiation, a pause at ambient temperature, or under heat, or under red light.
• the process can comprise, prior to step b) of irradiation, a step of partial masking of keratin materials, and, after step b) of irradiation, a rinsing step, or when keratin materials are hair, a shampooing or styling step.
• the method comprises, in the case of the production of such patterns, a drying step prior to the step of partially masking said keratin materials and after the step of applying the composition.
• a drying step prior to the step of partially masking said keratin materials and after the step of applying the composition.
• it is dried after application of the composition, then a part of the substrate is masked, for example with aluminum foil, and the whole area is irradiated. A rinse is then carried out.
• this rinsing can be followed by a shampoo.
• This masking technique makes it possible in particular to obtain localized cosmetic effects by subsequent action of cosmetic active agents (for example dyes) having a selective affinity for the areas treated by the irradiation.
• cosmetic active agents for example dyes
• the irradiation is preferably irradiation with radiation in the UVA or in the visible region, and even more preferably radiation in the UVA.
• irradiation in the visible range is meant in the sense of the present invention, either an irradiation carried out with an appropriate device (laser or lamps), or the simple action of sunlight.
• the method according to the invention can comprise, before or after step b) of irradiation, a step of shaping the hair, for example using tweezers, or curlers ...
• thermodimerizable (s) When the compound (s) comprising at least one photodimerizable group according to the invention is (are) also thermodimerizable (s), the various methods described above can be implemented by replacing the irradiation step by a heating step between 40 and 200 ° C.
• the keratin materials are hair or nails.
• the following example illustrates the invention without however limiting its scope. The quantities are given, unless otherwise indicated, in mass percentages.
• An aqueous dispersion D is used of a polymer of the partially saponified polyvinylacetate type and carrying stilbazolium groups, adsorbed on polyvinylacetate particles.
• This dispersion contains a dry extract of 40%.
• the lock is kneaded, combed and dried with a hair dryer.
• the lock was irradiated at 360 nm for 10 s for a total energy of 50 mJ / cm 2 , or placed in daylight for 15 minutes.

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• 2003
  • 2003-12-12 WO PCT/FR2003/003698 patent/WO2004054527A1/fr active Application Filing
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