Classifications

• • 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
  • A61Q5/04—Preparations for permanent waving or straightening the hair
• • 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
  • A61Q19/00—Preparations for care of the skin
  • A61Q19/007—Preparations for dry skin
• • 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
  • A61Q19/10—Washing or bathing preparations
• • 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
  • A61Q5/12—Preparations containing hair conditioners

Definitions

• the present invention relates to the use in cosmetic compositions, in particular capillaries, of grafted polyamino acid type polymers, as well as cosmetic compositions comprising said polymers, and their use in particular in hair compositions.
• the hair is sensitized, that is to say damaged and / or fragile, to varying degrees by the action of atmospheric agents, including light, and by the repeated action of different mechanical or chemical treatments, such as perms, straightening, coloring and discoloration.
• mechanical or chemical treatments such as perms, straightening, coloring and discoloration.
• These aggressions altering the hair fiber they can reduce the mechanical properties such as tensile strength, tensile strength and elasticity.
• fiber degradations have been observed after these treatments: the hair becomes more hydrophilic, may lose part of the scales, which results in great difficulty in disentangling and styling the hair, as well as a lack of sweetness.
• certain grafted polyamino acid-type polymers can make it possible to protect and repair keratin materials, especially damaged keratinous materials, which will result, in the case of hair, by improving disentangling properties, on dry and wet hair and / or improving anti-breakage properties.
• the subject of the present invention is therefore a cosmetic treatment process intended to improve the mechanical strength and / or the disentanglement of keratinous fibers, in particular the hair, comprising the application to said fibers of a cosmetic composition comprising, in a cosmetically acceptable medium.
• a cosmetic composition comprising, in a cosmetically acceptable medium.
• at least one polymer comprising a polymeric backbone comprising cationic-functional amino acid monomer units, and having hydrophilic grafts covalently bound to said backbone, on all or part of said backbone, said hydrophilic grafts comprising repetition of minus two hydrophilic monomeric units, having a log p value of less than or equal to 2.
• the method is intended to prevent hair breakage. It may especially be intended to repair and / or strengthen the hair, especially sensitized hair, and in particular damaged or weakened hair.
• the invention also relates to a cosmetic composition comprising some of these polymers and a cosmetically acceptable medium.
• polymers whose architecture comprises a polymer backbone comprising polymerized amino acid units resulting from the polymerization of at least one or more amino acids, a skeleton on which hydrophilic grafts are grafted, make it possible to obtain after application to keratin materials, the desired properties; in particular, these polymers may advantageously be applied to the hair, and more particularly to sensitized hair, in particular damaged or weakened hair.
• the cosmetic treatment of the keratin materials with the composition according to the invention thus makes it possible to provide repair properties, which can result in improved disentangling and / or reduced breakage (hair breakage), as well as an improvement in the softness to the touch, in the case of hair.
• compositions according to the invention can impart gloss to keratin materials, in particular the hair.
• compositions according to the invention may also make it possible to reinforce the keratin materials, and in particular to improve their resistance to tensile mechanical forces applied to them, for example during combing, in particular on weakened or sensitized hair. To image, we speak of anti-breakage effect.
• keratinous material includes in particular the skin, the lips, the nails, the hair, the eyelashes, the eyebrows, the hairs.
• polymers based on poly (amino acids) with hydrophilic grafts such as polylysine with polyethylene oxide (or PEG) grafts, for example used in the biomedical field to reduce the immunological recognition between cells / tissues, are known. as described in US5462990; or to improve the analytical recognition, including the selectivity and sensitivity of diagnostic apparatus, as described in WO00 / 65352. It is also known from US2002 / 0016304, poly (amino acid) polymers with hydrophilic grafts, including polylysine with dextran grafts, for stabilizing nucleic acids such as DNA.
• the polymers according to the invention therefore have a polymeric backbone of the poly (cationic amino acid) type, that is to say mainly comprising a repetition cationic amino acid monomer units.
• the polymeric backbone may be linear, branched, in particular star-shaped or hyperbranched, dendrimeric, or cross-linked; preferably, it is linear.
• cationic amino acids any compound having an amino acid unit, and furthermore at least one cationic function, that is to say primary, secondary, tertiary or quaternary amine, capable of being protonated at a pH between 3 and 12.
• the polymeric backbone therefore has at least one function capable of possessing a cationic charge in a pH range of between 3 and 12.
• guanidino and amidino groups of formula:
• R, R' and R representing, independently of one another, either (i) a hydrogen atom or ( ii) a linear, branched or cyclic, saturated or unsaturated, optionally aromatic, alkyl group comprising from 1 to 18 carbon atoms, which can comprise 1 to 10 heteroatoms chosen from O, N, S, F, Si and P; or (iii) R and R 'form with the nitrogen atom, a first ring, saturated or unsaturated, optionally aromatic, comprising in total 5, 6, 7 or 8 atoms, and in particular 4, 5 or 6 carbon atoms; and / or 2 to 4 heteroatoms selected from O, S and N; said first cycle being fusible with one or more other rings, saturated or unsaturated, optionally aromatic, each comprising 5, 6 or 7 atoms, and especially 4, 5, 6 or 7 carbon atoms and / or 2 to 4 heteroatoms selected from O, S and N; - the group of formula -NRR 'or -N + RR 1 R ", with R
• R1 and R2 may be, independently of one another, selected from hydrogen; a linear, branched or cyclic, saturated or unsaturated, optionally aromatic, alkyl radical comprising from 1 to 18 carbon atoms, which can comprise 1 to 10 heteroatoms chosen from O, N, S, F, Si and P; or R1 and R2 may together form a saturated or unsaturated ring, optionally aromatic, comprising in total 5, 6, 7 or 8 atoms, in particular 5 or 6 carbon atoms and / or 2 to 4 heteroatoms chosen from O, S and NOT;
• the cationic function can be chosen from NH 2 groups, guanidine dino, as well as
• the cationic amino acid monomers are preferably chosen from lysine, ornithine, arginine, histidine, glutamine and tryptophan, as well as their mixture.
• the polymeric backbone according to the invention may be a homopolymer, in particular of the polylysine type, in particular poly ( ⁇ -lysine), poly ( ⁇ -lysine), poly (L-lysine), poly (D-lysine), poly (D-lysine) , L-lysine); or of polyornithine type, especially poly (L-ornithine), poly (D-ornithine), poly (D, L-ornithine); or of polyarginine type, in particular poly (L-arginine), poly (D-arginine), poly (D, L-arginine); or of the polyhistidine type, especially poly (L-histidine), poly (D-histidine), poly (D, L-histidine); or of polyglutamine type, especially poly (L-glutamine), poly (D-glutamine), poly (D, L-glutamine); or of polytryptophan type, especially poly (L-tryptophan), poly (D-trypto
• the polymeric backbone may also be a copolymer, which may consist solely of cationic amino acid monomers, or cationic amino acid monomers in admixture with additional monomers.
• the polymer backbone can be a copolymer prepared from a mixture of cationic amino acids, for example of the poly (lysine-co-ornithine) type.
• non-cationic amino acid monomers such as alanine, in particular the D and L isomers; leucine or isoleucine, especially L-leucine, L-isoleucine, D-isoleucine; serine, especially isomers D and L; threonine, especially L-threonine; cysteine, especially the D and L isomers; aspartic acid, especially the D and L isomers; glycine, especially the D and L isomers; valine, especially the D and L isomers; asparagine, especially the D and L isomers; phenylalanine, especially the D and L isomers; tyrosine, especially the D and L isomers; glutamic acid, especially the D and L isomers; proline, especially the D and L isomers.
• non-cationic amino acid monomers such as alanine, in particular the D and L isomers
• leucine or isoleucine especially L-leucine, L-isoleu
• Polymeric backbones include poly (ornithine-costerine), poly (lysine-co-tyrosine), poly (lysine-co-alanine) and poly (leucine-co-lysine).
• the polymer backbone may be a random, alternating or block copolymer.
• the polymer backbone is preferably a block copolymer.
• the polymeric backbone can therefore comprise additional monomers or polymers of the polyalkylene glycol type, and in particular polyethylene glycol (PEG).
• Poly (lysine) -b-PEG block copolymers, poly (ornithine) -b-PEG block copolymers, poly (ornithine-co-serine) -b-PEG block copolymers may thus be mentioned.
• These polymers can be synthesized by known methods of polymerization.
• the polymerization of carbobenzoxysilyl-N-carboxylic acid anhydrides and benzyl-serine-N-carboxylic acid, in the presence of a PEG carrying an NH 2 terminal function (MW 200 to 250000 g). / mol) leads to a poly (lysine-co-serine) -b-PEG block copolymer.
• the polymeric backbone may also include vinyl monomers, especially (meth) acrylic and / or (meth) acrylamides, and / or saccharide monomers, esters, ethers, carbonates, urethanes, ureas, and mixtures thereof.
• the polymer backbone may comprise one or more blocks of poly (amino acids), for example polylysine, and one or more polyvinyl blocks, polysaccharide blocks, polyesters, polyethers, polyurethanes and / or polyureas.
• Polymeric backbones of poly-lysine-b-polyester or polylysine-b-polyurethane copolymers may be mentioned in particular.
• the polymeric backbone may also be of the poly (lactic acid-co-lysine) or poly (lysine-co-poly (N-hydroxypropylaminoethyl-D, L-aspartamide) type).
• polymers forming the polymer backbone may be prepared by any means known to those skilled in the art.
• a general method of polymerization comprises initiating, via an initiator, monomers of the alpha-amino acid type NCA (N-carboxyanhydrides), in particular of L-lysine NCA type. , L-ornithine NCA, glutamic acid NCA and its ⁇ -amide, tyrosine-NCA, serine NCA, L-threonine NCA, L-phenylalanine NCA, L-valine NCA, L-leucine NCA, L-isoleucine NCA, L-alanine NCAn, followed by polymerization.
• monomers of the alpha-amino acid type NCA N-carboxyanhydrides
• L-lysine NCA type N-carboxyanhydrides
• L-ornithine NCA glutamic acid NCA and its ⁇ -amide
• tyrosine-NCA serine NCA
• L-threonine NCA L-phenylalanine NCA
• initiator denotes any chemical species capable of initiating a polymerization process, especially any nucleophilic species such as a primary, secondary or tertiary C1-C12 alkylamine, a C1-C12 alkyl diamine, a primary or secondary arylamine or an acid amine having one or more free amino functions, a peptide having one or more free amino functions.
• a poly (lysine) -b-poly (arginine) block polymer can be carried out according to the method described in the article 'Linking poly-L-arginine to poly-DL-lysine using pentosidine linkages' Abstracts of Papers, 225th ACS National Meeting, New La, LA, United States, March 23-27, 2003. It is also possible to prepare a skeleton constituted by the assembly of non-cationic amino acid units, and then to transform them, in a subsequent step, in cationic units.
• the backbone further comprises additional monomers or polymers
• those skilled in the art will be able to choose, on the basis of their general knowledge, the most appropriate method according to the known rules of chemical reactivity.
• a PEG-b-poly (amino acid) type polymer backbone according to the method described in US Pat. No. 6,686,446, or in the article "Synthesis and Evaluation of Poly (Ethylene Glycol) -Polylysine Block Copolymers as Carriers for Genene". Delivery 'by Vanderkerken, Journal of Bioactive and Compatible Publishers, Vol. 15, No. 2, 115-138 (2000).
• polybutadiene-b-poly (lysine) polymers can be carried out according to the method described in 'Synthesis and characterization of pH sensitive PB-P (lys) block copolymer assembled in PMSE Preprints (2005), 93, pp. 198-199.
• the backbone further comprises vinyl monomers
• it can be synthesized by conventional methods of peptide sequence functionalization with for example a halogen, followed by the polymerization of vinyl monomers by controlled polymerization techniques, for example coupling ATRP as described by Klok in "Biological-synthetic hybrid block copolymers: combining the best from two worlds" Journal of Polymer Science Part A: Polymer Chemistry 2005, Volume 43, Issue 1, pp. 1-17.
• backbone further comprises saccharide, urea, or urea monomers
• backbone may be prepared in a manner similar to that described by Schlaad et al. in "Block copolymers with amino acid sequences: Molecular chimeras of polypeptides and synthetic polymers", The European Physical Journal E, Volume 10, No. 1, 2003, pp. 17 to 23.
• the polymer backbone consists of 100% cationic amino acid monomers.
• said additional monomers may represent 0.1 to 50% by weight, especially 1 to 45% by weight, or even 2 to 25% by weight. % by weight, of the total weight of the monomers forming the skeleton.
• the cationic amino acid monomers represent 50 to 99.9% by weight, preferably 55 to 99% by weight, or even 75 to 98% by weight of the total weight of monomers forming the backbone.
• the polymeric backbone comprises aminacid monomers joined by amide linkages; this polymeric backbone can be of natural or synthetic origin.
• the polymeric backbone is chosen from poly ( ⁇ -lysine), poly ( ⁇ -lysine), poly- (L-lysine), poly (D-lysine), poly (ornithine), poly (histidine) polymers. , poly (arginine) or poly (ornithine-co-serine).
• the polymeric backbone has a molecular weight (Mw) of between 1,000 and 5,000,000, especially between 2,000 and 1,000,000 and preferably between 3,000 and 100,000 g / mol.
• the polymer according to the invention also comprises hydrophilic grafts, covalently bonded to said polymeric backbone.
• Hydrophilic grafts are characterized by the fact that they contain the repetition of at least two hydrophilic monomeric units, that is to say having a decimal logarithm of the octanol-1 / water apparent partition coefficient, also called log p, less than or equal to 2, for example between -10 and 1, 8, preferably between -4 and 1.5, especially between -3 and 1, or even between -2.5 and 0.5.
• the graft contains the repetition of at least 5 hydrophilic units, which are identical or different.
• the log p values are known and are determined according to a standard test that determines the concentration of the monomer in octanol-1 and water.
• the values can be calculated using the Advanced Chemistry Development (ACD) software Solaris V4.67; they can also be obtained from Exploring QSAR: hydrophobic, electronic and steric constants (ACS professional reference book, 1995).
• ACD Advanced Chemistry Development
• Exploring QSAR hydrophobic, electronic and steric constants
• the hydrophilic monomeric units forming mainly the hydrophilic graft are chosen from the following units, and preferably exclusively from these units:
• hydrophilic grafts that can be used, alone or as a mixture, mention may be made of:
• polysaccharides in particular dextran, amylose, cellulose and its derivatives such as hydroxypropylcellulose or hydroxypropylmethylcellulose; glycoamino-glycans (GAGs) and especially hyaluronic acid; polyamino acids, in particular poly (glutamic acid), poly (serine) (-1,580), poly (threonine) (-1,233), poly (glutamine) (-1,674), poly (sarcosine) (-0.793) and their copolymers,
• alkylene polyoxides and especially polyethylene oxide
• the hydrophilic synthetic polymers comprising 100% by weight of hydrophilic monomers (with a log p of less than or equal to 2), chosen in particular from polyethylene (meth) acrylamide or polyvinylpyrrolidone (0.370) alone or as a mixture, polyvinyl methyl ether (0.509), polymethyloxazoline (-0.858), poly (hydroxypropylmethacrylamide) (-0.41), polyvinyl alcohol (0.263), poly (acrylic acid) (0.35).
• the hydrophilic grafts are chosen from polysaccharides; polyalkylene oxides, and most particularly from dextran, hyaluronic acid and polyethylene oxide; and poly (hydroxypropyl methacrylamide), and mixtures thereof.
• each hydrophilic graft has a number-average molecular mass (Mn) of between 500 g / mol and 100,000 g / mol, preferably between 550 g / mol and 50,000 g / mol, preferably between 1000 and 40,000 g / mol. .
• Mn number-average molecular mass
• the polymer according to the invention preferably has a degree of grafting of between 1 and 99%, especially between 2 and 50%, preferably between 3 and 45%, and even more preferably between 4 and 35%, or even between 5 and 25%. %.
• grafting rate is meant the ratio (x 100) between the number of cationic amino acid units grafted by a hydrophilic graft, and the total number of amino acid units (cationic and optionally non-cationic).
• the hydrophilic grafts can be distributed on the polymeric backbone statistic, alternating (1 graft every 2, 3 or x cationic amino acid units), even in blocks (no grafts on a part of the skeleton, then all the cationic amino acid units of a part of the grafted skeleton, for example ). Preferably, they are distributed statistically.
• the polymeric backbone has a molecular weight (Mw) of between 1,000 and 5,000,000, in particular between 2,000 and 1,000,000, and each hydrophilic graft has a number-average molecular weight (Mn) of between 500 g / mol and 100,000 g / m 2. mol, preferably between 550 g / mol and 50,000 g / mol.
• the polymer backbone has a molecular weight (Mw) of between 3,000 and 100,000 g / mol.
• each hydrophilic graft has a number-average molecular weight (Mn) of between 1,000 and 40,000 g / mol.
• the polymer according to the invention can be obtained in different ways.
• a first mode of preparation of the polymers according to the invention it is possible to initially prepare a functionalized polymeric backbone, that is to say carrying reactive chemical functions, then, in a second step, to graft the hydrophilic functionalized grafts comprising the hydrophilic repeating units, by reacting the reactive functional groups carried by the grafts with the reactive functional groups carried by the polymer backbone.
• This technique is known to those skilled in the art under the name of 'grafting to'.
• the grafting reaction can be of any chemical nature.
• the primary, secondary and / or tertiary amine reactive functions of said backbone can be used to couple the hydrophilic graft, via any organic chemistry reaction known to humans. job.
• hydrophilic grafts terminated with a function capable of reacting with the primary amines of lysine for example a carboxylic acid function;
• the reaction is carried out according to standard coupling techniques such as an activated ester function such as N-hydroxysuccinimide esters.
• It may also be a reductive amination reaction, that is to say a coupling between an aldehyde functionalized graft and a primary amine function carried by the backbone; a Schiff base is formed which can be reduced to form an amine bond.
• the backbone consists of cationic amino acid units and non-cationic amino acid units
• the hydrophilic grafts to non-cationic amino acid units.
• a copolymer comprising cationic amino acid units and serine units
• a hydrophilic graft terminated by a function reactive with the hydroxy functions for example a carboxylic acid function.
• the grafts, before polymerization on the backbone are in the form of macromonomers, that is to say of prepolymers comprising, generally located at at least one of their ends, a reactive group which allows said macromonomer to react with a function located on the polymeric backbone.
• macromonomers mention may be made mainly of (meth) acrylates of poly (ethylene glycol), or of alkylpoly (ethylene glycol), especially of methylpoly (ethylene glycol), also called (meth) acrylates of methoxy-poly (ethylene glycol) or MPEG.
• grafting via chemical reactions which are usually known in organic synthesis in intermediate steps, so as to functionalize the graft and / or the skeleton so that a coupling reaction can take place.
• a hydrophilic graft by a lactone unit, so that it can then react with an amine (primary) function of the skeleton, said lactone function possibly resulting from the lactonization of the lactone.
• a carboxylic acid function which can itself result from the oxidation of a hydroxy group (for example carried by a saccharide or dextran graft).
• the skilled person will be able to choose the reactive function carried by the graft in adequacy with the reactive function of the skeleton, on the basis of his general knowledge.
• a graft of the polysaccharide or polyalkylene glycol type may be grafted onto the backbone, thanks to the coupling between its reduced terminal function, converted into an aldehyde, and a primary amine function carried by the polymer backbone.
• a Schiff base is formed which can be reduced to form an amine bond (reductive amination).
• Another example is to oxidize in acid the terminal OH function of the graft such as dextran, using for example iodine, followed by lactonization.
• acid the terminal OH function of the graft such as dextran
• lactonization followed by lactonization.
• a subsequent reaction of the lactone function with an amine function of the backbone allows the grafting.
• the grafts may, moreover, be functionalized by a terminal function, for example, a thiol function, an aldehyde function, a succinic acid group, a biotin group, a dichlorotriazine, an anhy- maleic fluids, these functions not being used to graft said graft onto the skeleton.
• a terminal function for example, a thiol function, an aldehyde function, a succinic acid group, a biotin group, a dichlorotriazine, an anhy- maleic fluids, these functions not being used to graft said graft onto the skeleton.
• a functionalized polymeric backbone that is to say carrying reactive chemical functions, the latter being able to react with hydrophilic monomer units to obtain a graft polymer.
• This technique is known to those skilled in the art as grafting from.
• the monomeric units can then either polymerize directly via the cationic units when it is a polymeric backbone consisting solely of cationic amino acid units, or polymerize on other non-cationic amino acid units, when is copolymers comprising non-cationic amino acid units.
• polyglutamate graft polylysine preparation can be exemplified by a grafting from technique as described in Cylindrical polypeptide brushes, Macromolecular Chemistry and Physics, (2005) 206 (1), pp. .157-162.
• a polymer according to the invention can be further functionalized, for example carrying out the guanilation of a polylysine grafted dextran polymer, as described in Preparation of cationic comb-type. copolymer having guanidino moieties and its interaction with DNAs, Journal of Biomaterials Science, Polymer Edition (2004), 15 (9), pp.1099-1110.
• the polymers according to the invention therefore have a polymer backbone likely to result from the (co) polymerization of at least one functional amino acid. cationic, and comprise hydrophilic grafts covalently bound to this backbone, all or part of said backbone.
• the backbone comprises at least the incorporation of an amide unit resulting preferentially from the (co) polymerization of amino acids.
• the polymer according to the invention finds a very particular application in the cosmetic field, particularly in the hair field.
• the amount of polymer 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 0.01 and 30% by weight, preferably between 0, 1 and 20% by weight, especially between 0.5 and 10% by weight, or even between 1 and 5% by weight, relative to the weight of the final cosmetic composition.
• compositions according to the invention may be in any of the galenical forms conventionally used for topical application and especially in the form of an aqueous or alcoholic or aqueous-alcoholic solution or suspension, or of an oily solution or suspension, or of a solution.
• compositions may be packaged, especially in pump bottles or in aerosol containers, to ensure application of the composition in vaporized form or in foam form.
• compositions according to the invention may also be in the form of creams, gels, emulsions, lotions or waxes.
• composition according to the invention is packaged in the form of an aerosol in order to obtain a lacquer or a foam, it comprises at least one propellant.
• compositions according to the invention comprise, in addition to said polymers, a cosmetically acceptable medium, that is to say a medium that is compatible with keratin materials, in particular the skin of the face or of the body, the hair, the eyelashes, the eyebrows. and nails.
• a cosmetically acceptable medium that is to say a medium that is compatible with keratin materials, in particular the skin of the face or of the body, the hair, the eyelashes, the eyebrows. and nails.
• Said cosmetically acceptable medium comprises at least one cosmetic ingredient chosen from propellants; carbonaceous oils; Silicone oils; C8-C40 alcohols, C8-C40 esters, C8-C40 acids; nonionic surfactants, cationic surfactants, anionic surfactants, amphoteric surfactants, zwitterionic surfactants; solar filters; moisturizing agents; antidandruff agents; antioxidants; reducing agents; oxidation bases, couplers, oxidizing agents, direct dyes; the agents that relax the pearlescent and opacifying agents; plasticizers or coalescing agents; hydroxy acids; pigments; the charges; silicoids; thickeners.
• Said medium can of course include several cosmetic ingredients listed above.
• the propellants may be present at a concentration of between 5 and 90% by weight relative to the total weight of the composition in the aerosol device, and more particularly at a concentration of between 10 and 60% by weight.
• the propellant may be chosen from volatile hydrocarbons such as n-butane, propane, isobutane, pentane, a chlorinated and / or fluorinated hydrocarbon; carbon dioxide, nitrous oxide, dimethyl ether (DME), nitrogen, compressed air, and mixtures thereof.
• the carbonaceous oils in particular hydrocarbon oils, and / or the silicone oils may be present in a proportion of 0.01 to 20% by weight, especially 0.02 to 10% by weight relative to the total weight of the composition.
• Mention may in particular be made of vegetable, animal or mineral oils, whether or not hydrogenated, hydrocarbon, cyclic or aliphatic synthetic oils, linear or branched, saturated or unsaturated, such as, for example, polyalpha-olefins, in particular polydecenes and polyisobutenes. ; volatile or nonvolatile silicone oils, organomodified or otherwise, water-soluble or non-water-soluble; fluorinated or perfluorinated oils; their mixtures.
• Alcohols, esters and acids, having 8 to 40 carbon atoms can be present in a proportion of 0.01 to 50% by weight, especially 0.1 to 20% by weight relative to the total weight of the composition.
• coconut oil stearic acid, lauric acid, palmitic acid and oleic acid, behenic acid, and mixtures thereof; Mention may also be made of linear or branched chain C 16 -C 40 fatty esters, such as esters of polyols derived from fatty acids containing from 8 to 30 carbon atoms, and their oxyalkylenated and especially oxyethylenated derivatives, the polyols being preferentially chosen among the sugars, C2-C6-alkylene glycols, glycerol, polyglycerols, sorbitol, sorbitan, polyethylene glycols, polypropylene glycols and mixtures thereof.
• the oxyalkylenated polyol esters may contain 1 to 20 oxyalkylenated groups, in particular oxyethylenated groups.
• glycerol esters there may be mentioned monoglycerides such as glyceryl oleate, glyceryl linoleate, glyceryl laurate, and mixtures thereof.
• polyglycerol esters mention may be made of diglyceryl monoisostearate, diglyceryl oleate, triglyceryl mono-oleate, diglyceryl distearate, pentaglyceryl tristearate, and mixtures thereof.
• oxyethylenated glycerol ester mention may be made of oxyethylenated glycerol stearate, in particular comprising 20 oxyethylenated units.
• sorbitan esters there may be mentioned, for example, sorbitan stearate, sorbitan laurate; sorbitan palmitate, sorbitan tristearate, sorbitan oleate, sorbitan trioleate.
• polysorbates for example Polysorbate 21; and their mixtures.
• sugar esters mention may be made of those derived from the following sugars: sucrose, glucose, fructose, mannose, galactose, arabinose, xylose, maltose, cellibiose, lactose, trehalose, raffinose, gentianose.
• Ra-COORb in which Ra represents the residue of an acid comprising from 8 to 29 carbon atoms, and Rb represents a hydrocarbon chain, branched or unbranched, containing from 3 to 30 carbon atoms.
• carbon atoms such as, for example, Purcellin oil, isononyl isononanoate, isopropyl myristate, 2-ethylhexyl palmitate, octyl-2-dodecyl stearate, octyl-2-dodecyl erucate, isostearyl isostearate; hydroxylated esters such as isostearyl lactate, octylhydroxystearate, octyldodecyl hydroxystearate, diisostearyl malate, triisocetyl citrate, heptanoates, octanoates, decanoates of fatty alcohols.
• Purcellin oil isononyl isononanoate
• isopropyl myristate 2-ethylhexyl palmitate
• octyl-2-dodecyl stearate octyl-2-do
• the surfactants nonionic, cationic, anionic, amphoteric or zwitterionic, as well as their mixtures, can be present in a proportion of 0.01 to 50% by weight, especially 0.05 to 40% by weight, or even 0.1 to 30% by weight, relative to the total weight of the composition.
• alkaline salts in particular sodium salts, ammonium salts, amine salts, aminoalcohol salts and magnesium salts, of the following compounds: alkyl sulphates, alkyl ether sulphates, alkylamido ether sulphates, monoglyceride sulphates, alkyl glyceryl sulphonates, alkyl sulphonates, alkyl phosphates, alkyl amide sulphonates, alkyl aryl sulphonates, alpha olefin sulphonates, paraffin sulphonates, alkyl sulphosuccinates, alkyl ether sulphosuccinates, alky amide sulphosuccinates, alkylsulfosuccinamates, alkylsulfoacetates, alkyletherphosphates, acyliseth
• salts of fatty acids such as the salts of undecenylic, oleic, ricinoleic, palmitic and stearic acids, or acids of coconut oil or of hydrogenated coconut oil, or alternatively acylhydroxyacids such as acyls. -lactylates.
• weakly anionic surfactants such as alkyl D-galactoside uronic acids and their salts, or polyoxyalkylenated carboxylic ether acids and their salts.
• the alkyl or acyl radical of the various surfactants listed above preferably has from 8 to 22 carbon atoms.
• nonionic surfactants mention may be made of alcohols, alpha-diols, alkylphenols or polyethoxylated, polypropoxylated or polyglycerolated fatty acids, having a fatty chain comprising from 8 to 22 carbon atoms, the number of ethylene or propylene can range from 2 to 50 and that of glycerol in particular from 2 to 30.
• amphoteric or zwitterionic surfactants mention may be made of derivatives of aliphatic secondary or tertiary amines, in which the aliphatic radical is a linear or branched chain containing 8 to 22 carbon atoms and containing at least one water-soluble anionic group (for example: carboxylate, sulphonate, sulphate, phosphate or phosphonate) such as, for example, alkylbetaines, alkylaminocarboxylates, sulphobetaines, alkylamidoalkylbetaines, alkylamidoalkylsulphobetaines, imidazolium derivatives, especially those of amphocarboxyglycinate or of amphocarboxypropionate.
• the aliphatic radical is a linear or branched chain containing 8 to 22 carbon atoms and containing at least one water-soluble anionic group (for example: carboxylate, sulphonate, sulphate, phosphate or
• cationic surfactants mention may be made of optionally polyoxyalkylenated and / or quaternized fatty amine salts, esters of optionally polyoxyalkylenated and / or quaternized fatty acids and amino alcohols, quaternary ammonium salts such as chlorides or tetraalkyl bromides ammonium, alkylamidoalkyl trialkylammonium, trialkylbenzylammonium, trialkylhydroxyalkylammonium, dialkylamidoalkyldimethylammonium, alkylpyrrolidinium and imidazolium derivatives.
• the sunscreens may be present in a proportion of 0.01 to 20% by weight, in particular 0.5 to 10% by weight relative to the total weight of the composition; these filters may be active in 1 UVA and / or 1 1 UVB (absorbers), fat-soluble or water-soluble. They may be chosen in particular from salicylic derivatives, camphor derivatives; triazine derivatives; benzophenone derivatives; diphenylacrylate derivatives, benzimidazole derivatives, bis-benzoazolyl derivatives; p-aminobenzoic acid derivatives; filter polymers and silicone filters.
• the moisturizing agents may be present in a proportion of 0.01 to 20% by weight, especially 0.1 to 7% by weight relative to the total weight of the composition.
• polyols, sugars and proteins and in particular glycerin, sorbitol, D-panthenol, mannitol; fructose, galactose, sugar and N-acetylglucosamine.
• the anti-dandruff agents may be present in a proportion of 0.001 to 20% by weight, especially 0.01 to 10% by weight relative to the total weight of the composition, preferably 0.1 to 5% by weight. These include:
• pyridinethione salts in particular calcium, magnesium, barium, strontium, zinc, cadmium, tin and zirconium salts.
• R9 represents a C1-C17 alkyl group, a C2-C17 alkenyl group, a C5-C8 cycloalkyl group, a C7-C9 bicycloalkyl group; a cycloalkyl (-alkyl) group, an aryl group, an aralkyl group with a C 1 -C 4 alkyl, an arylalkenyl group with a C 2 -C 4 alkenyl, aryloxyalkyl or arylmercaptoalkyl with a C 1 -C 4 alkyl, a furylalkenyl group with C 2 -C 4 alkenyl or carboxy, C 1 -C 4 alkoxy group, nitro group, cyano group, or halogen atom:
• R10 represents a hydrogen atom, a C1-C4 alkyl group, a group C2-C4 alkenyl, a halogen atom, a phenyl group, a benzyl group;
• X represents an organic base, an alkali metal or alkaline earth metal ion, an ammonium ion;
• Z represents a halogen atom, especially Cl, or a C1-C4 trihaloalkyl group such as CF3;
• azole compounds such as climbazole, ketoconazole, clotrinazole, econazole, isoconazole and miconazole; antifungal polymers such as amphotericin B or nystatin; selenium sulphide; sulfur in its different forms, cadmium sulphide, allantoin; coal or wood tars and their derivatives, in particular cade oil; salicylic acid, undecyclic acid, fumaric acid; allylamines such as terbinafine.
• the antioxidants may be present in a proportion of 0.05 to 1.5% by weight, relative to the total weight of the composition. These include polyphenols, vitamin E, dehydroascorbic acid, hydroquinone, 2-methylhydroquinone, tert-butylhydroquinone and homogentisic acid.
• the reducing agents may be present in a proportion of 0.1 to 30% by weight, especially 0.5 to 20% by weight relative to the total weight of the composition.
• These include sulfites, bisulfites, alkylphosphines and thiols.
• the products used for the hair coloring can be chosen from oxidation bases, couplers, oxidizing agents, direct dyes, and mixtures thereof.
• para-phenylenediamines, bis-phenylalkylenediamines, para-aminophenols, ortho-aminophenols and heterocyclic bases may be mentioned as oxidation bases, among which mention may be made, by way of example, of pyridine derivatives and pyrimidine derivatives. and pyrazole derivatives.
• the couplers there may be mentioned meta-phenylenediamines, meta-aminophenols, meta-diphenols, naphthalenic couplers and heterocyclic couplers.
• the oxidation bases may be present in an amount of from 0.001 to 10% by weight, preferably from 0.005 to 6% by weight, of the total weight of the composition.
• the couplers may be present in an amount of from 0.001 to 10% by weight, preferably from 0.005 to 6% by weight, of the total weight of the composition.
• the oxidizing agents may be chosen from hydrogen peroxide or alkaline bromates, or alternatively from hydrogen peroxide, urea peroxide, alkali metal bromates, persalts such as perborates and persulfates, as well as enzymes among which include peroxidases, 2-electron oxidoreductases such as uricases and 4-electron oxygenases such as laccases.
• the content of oxidizing agent may be between 1 and 40% by weight, preferably between 1 and 20% by weight, relative to the weight of the composition.
• the direct dyes may be chosen from cationic or nonionic species, and in particular from nitrated benzene dyes, azo, azomethine, methine, tetraazapentamethine, azine, anthraquinone, quinone, naphthoquinone, benzoquinone, phenytiazine indigo, xanthene, and phenanthridine dyes. , phthalocyanines, triarylmethanics, indoamines, and natural dyes, alone or in mixtures.
• the direct dye content may be from 0.001 to 20% by weight, preferably from 0.01 to 10% by weight, relative to the total weight of the composition.
• the relaxing agents may be present in a proportion of 0.01 to 3.5% by weight, especially 0.05 to 1.5% by weight relative to the total weight of the composition.
• hydroxides preferably selected from alkali metal or alkaline earth metal hydroxides, transition metals or organic such as sodium hydroxide, potassium hydroxide, lithium hydroxide, rubidium hydroxide , cesium hydroxide, francium hydroxide, beryllium hydroxide, magnesium hydroxide, calcium hydroxide, strontium hydroxide, barium hydroxide, molybdenum hydroxide, manganese hydroxide, zinc hydroxide, cobalt hydroxide, cadmium hydroxide, cerium hydroxide, lanthanum hydroxide, actinium hydroxide, thorium hydroxide, aluminum hydroxide, guanidinium hydroxide and hydroxides of quaternary ammoniums.
• the pearlescent and opacifying agents may be present in a proportion of 0.01 to 3% by weight, especially 0.05 to 2.5% by weight relative to the total weight of the composition. Mention may in particular be made of sodium or potassium palmitates, sodium or potassium stearates or hydroxystearates or ethylene glycol mono- or disteate.
• the plasticizing or coalescing agents may be present in a proportion of 0.1 to 25% by weight, especially 1 to 10% by weight relative to the total weight of the composition.
• glycols and their derivatives can be mentioned alone or as a mixture; glycerol esters, such as glycerol diacetate or triacetate; propylene glycol derivatives; esters of carboxylic acids, such as citrates, phthalates, adipates, carbonates, tartrates, phosphates, sebacates; oxyethylenated derivatives such as oxyethylenated oils, especially vegetable oils such as castor oil; oxyethylenated silicone oils.
• the hydroxy acids may be present in a proportion of 1 to 10% by weight, in particular 2 to 5% by weight relative to the total weight of the composition. Mention may in particular be made of mono- or poly-carboxylic acids containing one or more hydroxyl functions; preferably the hydroxy acid is an alpha hydroxy acid. In particular, mention may be made of citric, lactic, methyllactic, phenyllactic, malic, mandelic, glycolic, tartronic, tartaric, gluconic, benzylic and 2-hydroxycaprylic acids.
• the pigments and fillers may be present in a proportion of 0.01 to 50% by weight, especially 0.02 to 30% by weight relative to the total weight of the composition. Mention may in particular be made of mineral or organic fillers of any form: platelet, spherical or oblong.
• organic carboxylic acids
• Silicones can be volatile or not; polyorganosiloxanes, which may or may not be modified, namely oils, gums and resins of polyorganosiloxanes, may be mentioned in particular, or in the form of solutions in organic solvents, or in the form of emulsions or microemulsions. In particular, it is possible to mention, alone or as a mixture:
• volatile silicones which have a boiling point between 60 ° C. and 260 ° C., and which may be among cyclic silicones containing from 3 to 7 silicon atoms and preferably from 4 to 5.
• polyalkylsiloxanes and especially polydimethylsiloxanes, in particular linear with trimethylsilyl end groups; DC 200 oils from Dow Corning; PDMS with hydroxydimethylsilyl end groups;
• polyarylsiloxanes
• polyalkylarylsiloxanes and in particular polymethylphenylsiloxanes, polydimethylmethylphenylsiloxanes and linear or branched polydimethyldiphenylsiloxanes;
• silicone gums are polydiorganosiloxanes with a molecular weight of between 200,000 and 5,000,000, which can be used alone or as a mixture in a solvent chosen from volatile silicones, polydimethylsiloxane (PDMS) oils, polyphenylmethylsiloxane (PPMS) oils, isoparaffins, methylene chloride, pentane, dodecane, tridecane, tetradecane or mixtures thereof.
• PDMS polydimethylsiloxane
• PPMS polyphenylmethylsiloxane
• polydimethylsiloxanes poly [(dimethylsiloxane) / (methylvinylsiloxane)], poly [(dimethylsiloxane) / (diphenylsiloxane)], poly [(dimethylsiloxane) / (phenylmethylsiloxane) ], poly [(dimethylsiloxane) / (diphenylsiloxane) / (methylvinylsiloxane)].
• polydimethylsiloxanes poly [(dimethylsiloxane) / (methylvinylsiloxane)]
• poly [(dimethylsiloxane) / (methylvinylsiloxane) / (diphenylsiloxane)] poly [(dimethylsiloxane) / (diphenylsiloxane) / (methylvinylsiloxane)].
• the following mixtures may also be mentioned
• mixtures of two PDMSs of different viscosity in particular a PDMS gum and a PDMS oil;
• silicone resins preferably crosslinked siloxane systems containing the units R2SiO2 / 2, RSiO3 / 2 and SiO4 / 2 in which R represents a hydrocarbon group having 1 to 6 carbon atoms or a grouping phenyl.
• organomodified polyorganosiloxanes that is to say silicones as defined above, comprising in their general structure, one or more organofunctional groups directly attached to the siloxane chain or attached via a hydrocarbon radical; mention may be made of silicones comprising:
• polyethyleneoxy and / or polypropyleneoxy groups optionally containing alkyl groups, such as dimethicone copolyols and alkyl (C12) meticone copolyol; - (per) fluorinated groups such as trifluoroalkyl groups,
• substituted or unsubstituted amino groups are in particular amino-C1-C4 or aminoalkyl (C1-C4) aminoalkyl (C1-C4) groups. More particularly, silicones called amodimethicone and trimethylsilylamodimethicone according to the CTFA name are used;
• hydroxyl groups such as polyorganosiloxanes with hydroxyalkyl function
• alkoxylated groups comprising at least 12 carbon atoms
• acyloxyalkyl groups comprising at least 12 carbon atoms
• amphoteric or betaine groups include amphoteric or betaine groups; bisulfite groups;
• grafted silicone polymers having a non-silicone organic skeleton, consisting of an organic main chain formed from organic monomers containing no silicone, on which is grafted, inside said chain as well as optionally at least one of its ends, at least one polysiloxane macromonomer;
• the grafted silicone polymers having a polysiloxane backbone grafted with non-silicone organic monomers, comprising a polysiloxane main chain on which is grafted, inside said chain as well as optionally at at least one at its ends, at least one organic macromonomer not comprising a silicone.
• the thickeners may be present in a proportion of from 0.01 to 10% by weight, in particular from 0.1 to 5% by weight relative to the total weight of the composition. They can be chosen from cellulose, cellulose derivatives, acrylic thickening polymers (Carbopol), alginates, gums such as xanthan gum, guar gum, carob or gum arabic or polyethylene glycols, bentonites and montmorillonites
• composition may comprise water, one or more C 1 -C 6 alcohols, alone or as a mixture with water, and in particular a water / ethanol, water / isopropanol or water / benzyl alcohol mixture.
• composition may also comprise polymers, especially polymers that are water-soluble or soluble in carbonaceous and / or silicone oils; they may be present in a proportion of 0.01 to 20% by weight, especially 0.1 to 10% by weight relative to the total weight of the composition.
• the composition may for example comprise a film-forming polymer, that is to say a polymer capable of forming on its own or in the presence of an auxiliary filtering agent, a continuous and adherent film on a support, in particular on the keratin materials.
• film-forming polymers that may be used in the composition of the present invention, mention may be made of synthetic polymers, of radical type or of polycondensate type, polymers of natural origin and their mixtures, in particular acrylic polymers, polyurethanes polyesters, polyamides, polyureas, cellulosic polymers such as nitrocellulose.
• the polymer may also be chosen from cationic polymers of the polyamine, polyaminoamide or quaternary polyammonium type, and in particular:
• vinylpyrrolidone-dialkylaminoalkyl acrylate or methacrylate copolymers whether or not quaternized, such as the polymers described in FR2077143 and FR2393573;
• cationic cellulose derivatives such as cellulose copolymers or cellulose derivatives grafted with a water-soluble quaternary ammonium monomer, and described especially in US4131576, such as hydroxyalkyl celluloses, such as hydroxymethyl, hydroxyethyl or hydroxypropyl; grafted celluloses, in particular with a salt of methacryloylethyltrimethylammonium, methacrylamidopropyltrimethylammonium or dimethyldiallylammonium salt.
• Polymers consisting of piperazinyl units and straight or branched chain alkylene or hydroxyalkylene divalent radicals, optionally interrupted by oxygen, sulfur, nitrogen or aromatic or heterocyclic rings, as well as oxidation and / or quaternization products of these polymers.
• Such polymers are in particular described in FR2162025 and FR2280361.
• water-soluble polyamino amides prepared in particular by polycondensation of an acidic compound with a polyamine; these polyaminoamides may be crosslinked by an epihalohydrin, a diepoxide, a dianhydride, an unsaturated dianhydride, a bis-unsaturated derivative, a bis-halohydrin, a bisazeti- tinium, a bis-haloacyldiamine, a bis-alkyl halide or else by an oligomer resulting from the reaction of a bifunctional compound reactive with a bis-halohydrin, a bis-azetidinium, a bis-haloacyldiamine, an alkyl bis-halide, a an epilhalohydrin, a diepoxide or a bis-unsaturated derivative, the crosslinking agent being used in proportions ranging from 0.025 to 0.35% by mole per amine group of the polyaminoamide; these polya
• polymers are in particular described in FR2252840 and FR2368508.
• the polyamino amide derivatives resulting from the condensation of polyalkylene polyamines with polycarboxylic acids followed by alkylation with difunctional agents Mention may be made, for example, of adipic acid-diacoylaminohydroxyalkyldialoylene triamine polymers in which the alkyl radical contains from 1 to 4 carbon atoms and preferably denotes methyl, ethyl or propyl.
• alkyl radical contains from 1 to 4 carbon atoms and preferably denotes methyl, ethyl or propyl.
• Such polymers are in particular described in FR1583363.
• polyamines such as the "POLYQUART H” sold by HENKEL, referenced under the name “POLYETHYLENEGLYCOL TALLOW POLYAMINE” in the CTFA dictionary.
• crosslinked polymers of methacryloyloxyethyltrimethylammonium salts such as the polymers obtained by homopolymerization of dimethylaminoethyl methacrylate quaternized with methyl chloride, or by copolymerization of acrylamide with dimethylaminoethyl methacrylate quaternized with methyl chloride, homo- or the copolymerization being followed by crosslinking with an olefinically unsaturated compound, in particular methylenebisacrylamide.
• a crosslinked acrylamide / methacryloyloxyethyltrimethylammonium chloride copolymer (20/80 by weight) in the form of a dispersion containing 50% by weight of said copolymer in mineral oil.
• Other cationic polymers that may be used in the context of the invention are polyalkyleneimines, in particular polyethyleneimines, polymers containing vinylpyridine or vinylpyridinium units, condensates of polyamines and of epichlorohydrin, quaternary polyureylenes and chitin derivatives. Cellulose ether derivatives containing quaternary ammonium groups, polysaccharides and in particular cationic guar gums and cyclopolymers of methyl diallyl amine or of dimethyl diallyl ammonium are preferred.
• cationic fixing film-forming polymers chosen from polymers comprising primary, secondary, tertiary and / or quaternary amine groups forming part of the polymer chain or directly connected thereto, and having a molecular weight of between 500 and about 5,000,000 and preferably between 1,000 and 3,000,000.
• polymers comprising the following units:
• R3 denotes a hydrogen atom or a CH3 radical
• - A is a divalent linear or branched alkylene group having 1 to 6 carbon atoms or a hydroxyalkylene group having 1 to 4 carbon atoms;
• R1 and R2 identical or different, represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms;
• R4, R5, R6, identical or different, represent an alkyl group having 1 to 18 carbon atoms or a benzyl radical;
• X denotes a methosulphate anion or a halide such as chloride, iodide or bromide.
• These polymers of the family (1) may also contain one or more units derived from comonomers which may be chosen from the family of acrylamides, methacrylamides, diacetones-acrylamides, acrylamides and methacrylamides substituted on the nitrogen by lower alkyl groups (C1- C4), groups derived from acrylic or methacrylic acids or their esters, vinyllactams such as vinylpyrrolidone or vinylcaprolactam, vinyl esters.
• comonomers which may be chosen from the family of acrylamides, methacrylamides, diacetones-acrylamides, acrylamides and methacrylamides substituted on the nitrogen by lower alkyl groups (C1- C4), groups derived from acrylic or methacrylic acids or their esters, vinyllactams such as vinylpyrrolidone or vinylcaprolactam, vinyl esters.
• comonomers which may be chosen from the family of acrylamides, methacrylamides, diacetones-acrylamide
• chitosans or their salts are, in particular, chitosan acetate, lactate, glutamate, gluconate or pyrrolidone carboxylate.
• chitosan having a deacetylation rate of 90.5% by weight sold under the name KYTAN BRUT STANDARD by the company ABER TECHNOLOGIES
• the chitosan pyrrolidonecarboxylate sold under the name KYTAMER® PC by the company Amerchol.
• amphoteric fixing polymers chosen from polymers comprising units B and C statistically distributed 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 derived from an acidic monomer having one or more carboxylic or sulfonic groups, or B and C may denote groups derived from zwitterionic monomers of carboxybetaines or sulfobetaines; B and C may also designate a cationic polymer chain having primary amine groups, se- tertiary or quaternary, in which at least one of the amino groups carries a carboxylic or sulfonic group connected through a hydrocarbon group, or B and C are part of a chain of a patterned polymer ethylene- ⁇ , ⁇ -dicarboxylic group in which one of the carboxylic groups has been reacted with a polyamine containing one or more primary or secondary amine groups.
• B and C may also designate a
• copolymers with acidic vinyl units and basic vinyl units such as those resulting from the copolymerization of a monomer derived from a vinyl compound carrying a carboxylic group such as, more particularly, acrylic acid, methacrylic acid, maleic acid, alpha-chloroacrylic acid, and a basic monomer derived from a substituted vinyl compound containing at least one basic atom, such as, more particularly, dialkylaminoalkyl methacrylate and acrylate, dialkylaminoalkylmethacrylamide and acrylamide.
• a monomer derived from a vinyl compound carrying a carboxylic 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, dialkylaminoalkyl methacrylate and acrylate, dialkylaminoalkylmethacrylamide and acrylamide.
• (2) polymers comprising units derived from: a) at least one monomer chosen from acrylamides or methacrylamides substituted on the nitrogen atom with an alkyl group; b) with at least one acidic comonomer containing one or more several reactive carboxylic groups, and c) at least one basic comonomer such as primary, secondary, tertiary and quaternary amine substituted esters of acrylic and methacrylic acids, and the quaternization product of dimethylaminoethyl methacrylate with dimethyl sulfate or diethyl.
• the N-substituted acrylamides or methacrylamides which are more particularly preferred are the compounds whose alkyl groups contain from 2 to 12 carbon atoms, and more particularly N-ethylacrylamide, N-tert-butylacrylamide, N-tert-octylacrylamide, N-octylacrylamide, N-decylacrylamide, N-dodecylacrylamide and the corresponding methacrylamides.
• the acid comonomers are chosen more particularly from acrylic, methacrylic, crotonic, itaconic, maleic and fumaric acids as well as alkyl monoesters having 1 to 4 carbon atoms of maleic or fumaric acids or anhydrides.
• Preferred basic comonomers are aminoethyl, butylaminoethyl, N, N'-dimethylaminoethyl, N-tert-butylaminoethyl methacrylates.
• the composition according to the invention may be in the form of a lotion, thickened or not, a cream, thickened or not, a gel, a foam or any other suitable form. It can optionally be packaged in a pump bottle or in an aerosol container. Preferably, it is in the form of a lotion, thickened or not.
• the cosmetic composition according to the invention may be in the form of a product for the care, cleaning and / or make-up of the skin of the body or the skin. lips, eyelashes, nails and hair, a suntan or self-tanning product, a personal hygiene product, a hair product, in particular care, cleaning, styling, shape, coloring of the hair. It particularly finds a particularly interesting application in the hair field, especially for maintaining the hairstyle or shaping the hair, or the care, the cosmetic treatment or the cleaning of the hair.
• the hair compositions are preferably shampoos, conditioners, styling or care gels, lotions or care creams, conditioners, styling lotions, blow-dry lotions, fixing compositions and the like.
• the lotions may be packaged in various forms, in particular in vaporizers, pump-bottles or in aerosol containers to ensure application of the composition in vaporized form or in the form of foam.
• a hair coloring product in particular oxidation dye, optionally in the form of a coloring shampoo; in the form of a composition of perm, straightening or discoloration, or in the form of a composition to be rinsed, to be applied before or after a coloration, a discoloration, a permanent or a straightening or between the two stages of a permanent or a straightening.
• the composition according to the invention may be in the form of a care composition, in particular a moisturizer, for the skin of the body or of the face, the lips and / or integuments, in particular of a care product, not colored, intended to cosmetically treat the skin and in particular to moisturize it, smooth it, depigment it, nourish it, protect it from the sun's rays, or give it a specific cosmetic treatment.
• a care composition in particular a moisturizer, for the skin of the body or of the face, the lips and / or integuments, in particular of a care product, not colored, intended to cosmetically treat the skin and in particular to moisturize it, smooth it, depigment it, nourish it, protect it from the sun's rays, or give it a specific cosmetic treatment.
• a base of care for the lips a fixing base for lipstick, a composition of sunscreen or artificial tanning, a composition of care (day, night, anti-aging, moisturizing) for the face ; a mattifying composition.
• compositions for cleaning the skin for example a makeup remover or a bath or shower gel, or a bread or cleaning soap. It may also be in the form of a personal hygiene composition, especially in the form of a deodorant product, antiperspirant, or in the form of a depilatory composition or an aftershave gel or lotion.
• a makeup product for the skin of the body or the face, lips, eyelashes, nails or hair; especially a foundation, a blush, a blush, an eyeliner, an eyeliner, a mascara, a lipstick, a lip gloss, a lip liner; nail polish, nail care; a temporary tattoo product from the skin of the body.
• the composition according to the invention finds an interesting application for the care and the cosmetic treatment, in particular the protection, of hair, in particular weakened and / or damaged hair, for example by chemical or mechanical treatments; the polymers according to the invention may in particular be used after the treatment, after a step of coloring, bleaching or straightening the hair.
• the problem of the permanent technique known to date is that their application to the hair can induce in the long term an alteration of the quality of the hair, resulting in a decrease in their cosmetic properties, such as their gloss, and a degradation of their mechanical properties, more particularly a degradation of their mechanical strength, or even an increase in their porosity.
• the weakened hair can become brittle, especially during subsequent treatments such as brushings.
• the subject of the invention is therefore a process for the cosmetic treatment, in particular of makeup, care, cleaning, coloring, shaping, keratin materials, in particular of the skin of the body or of the face, lips, nails , hair and / or eyelashes, comprising the application on said materials of a cosmetic composition comprising at least one polymer as defined above.
• it is a cosmetic treatment method for the care and / or the cleaning and / or the cosmetic treatment, and especially for the strengthening, of the hair, in particular the damaged and / or weakened hair, comprising application of such a composition; optionally followed by a rinsing step and / or optionally a heat treatment step.
• a cosmetic treatment method for the care and / or the cleaning and / or the cosmetic treatment and especially for the strengthening, of the hair, in particular the damaged and / or weakened hair, comprising application of such a composition; optionally followed by a rinsing step and / or optionally a heat treatment step.
• a heat treatment by heating at a temperature preferably of between 30 and 60 ° C., for 10 to 25 hours. minutes.
• this operation can be carried out by means of a hairdressing helmet, a hair dryer, an infrared dispenser, or any other usual heating appliance.
• a heating iron at a temperature of between 60 and 220 ° C., preferably between 120 and 200
• the weight average molar masses (Mw) and number (Mn) are determined by gel permeation liquid chromatography or GPC (solvent THF, calibration curve established with linear polystyrene standards, refractometer detector metric).
• the GPC is made with STYRAGEL HR4 / 7.8 x 300 mm columns, sold by Waters WAT044225.
• the detection is carried out with a WATERS 410 refractometer.
• the eluent is THF (tetrahydrofuran), at a flow rate of 1 ml / minute.
• the injected volume is 50 microliter at 25 ° C. Calibration is performed using polystyrene standards.
• the solution is then dialyzed (Spectra Por with a cut-off point of 12000 to 14000 g / mol) for 24 hours against a phosphate buffered saline solution PBS (pH 7.4, 0.1 ml of solution for 285 ml of buffer; % mOsm / kg H 2 O) then, for 48 hours, with deionized water.
• PBS phosphate buffered saline solution
• An aqueous solution of the polymer is obtained.
• the polymer is then lyophilized and stored at -20 ° C. under argon.
• the product is characterized by 1 H NMR (D 2 O, ppm) 1.35, 1.60, 1.68 (-CH 2 -), 2.88 (- CH 2 -N-), 3.55 (PEG), 4.20 (-N-CHR-COO- ).
• the determination of the degree of grafting is carried out by 1 H NMR by integrating the proton areas corresponding to the pendant chain of lysine with those of PEG.
• the polymer obtained is a poly (lysine) whose backbone has a molecular weight of 20,000 g / mol, and the PEG grafts have a molecular weight (Mw) of 5 kDa (5000 g / mol). It is found that 1 unit of lysine on 3.5 is grafted, which corresponds to a grafting rate of 28%.
• the product is purified via a dialysis membrane, with a cutoff threshold of 10,000 g / mol and the final product is freeze-dried.
• the desired polymer is obtained in the form of a white powder.
• the functionalized poly (N-2-hydroxypropylmethacrylamide) carboxylic acid is prepared.
• a second step 0.240 g of poly (lysine) bromohydrate of molecular weight 20000 g / mol and 0.485 g of pHPMA-COOH prepared above are dissolved in 180 ml of water.
• the pH is adjusted to 5 by adding a 0.5% HCl solution.
• a solution of 0.318 g of 1-ethyl, 3- (dimethylaminopropyl) carbodiimide chloride in 20 ml of water is added dropwise to the mixture.
• the pH is held at 5 for 2 hours and the mixture is left at room temperature (25 ° C.) overnight.
• the solution is dialyzed using a Spectra Por dialysis membrane with a cutoff of 3500, and then freeze-dried. 0.57 g of polymer is obtained in the form of a white solid.
• the determination by 1 H NMR shows that 8 mol% of the polylysine units are grafted (by comparing the respective intensity of the signals at 3.9 ppm CH of the pHPMA and at 4.3 ppm CH of the PLL).
• the polymer obtained is a PHPMA grafted polylysine, with a degree of grafting of 8% (8 lysine units out of 100 are grafted).
• a solution comprising 100 mg of poly (L-ornithine) in 60 ml of a 0.08 M sodium tetraborate buffer solution (pH 8.5) is prepared. The mixture is stirred for 3 hours and then 200 mg of methoxypolyethylene glycol p-nitrophenylcarbonate (Mw 5000 g / mol) are added in 3 portions. The mixture is stirred all night and protected from light. The mixture is then dialyzed (5 liters of water) with 6 changes over a period of 24 hours. An aqueous solution of the desired polymer is obtained.
• a panel of testers evaluated the disentangling and smoothing criteria of the locks treated with the composition according to the invention, in comparison with untreated control locks.
• the hair treatment according to the invention causes changes in the mass and surface properties of the damaged hair. Indeed the damaged hair has a rough surface texture which becomes smooth after treatment according to the invention; this effect remains residual up to 5 consecutive shampoos after treatment.
• a shampoo comprising (% by weight) is prepared: 1% MA (active ingredient) of polymer of Example 1 - 12.5% of lauryl ether sulfate.
• a foaming solution is obtained, which is applied to locks of SA hair of 1 g, at a rate of 0.3 g of solution per wick. Leave for 3 minutes and rinse with water; we untangle the hair and we find that the hair is very easily disentangled; they are dried under helmet at 40 0 C for 15 minutes. It is found that the disentangling of dry hair is very good. The hair once dried is very soft and shiny.
• a styling lotion is obtained.
• a hydroalcoholic solution comprising, in g of
• a mascara is prepared having the following composition:
• Example 1 Foaming cream for cleaning
• composition comprising (% by weight) is prepared:
• the aqueous phase consisting of water-soluble ingredients (water, preservatives,
• EDTA, PEG-8, polymer of Example 1 is brought to 80 ° C.
• the fatty phase consisting of fatty acids, glyceryl stearate and n-octanoylsalicylic acid, is heated to 80 ° C. and added with stirring to the aqueous phase.
• the cocoyl glucoside is then added and the KOH is solubilized in part of the water. Stirring is maintained for 10 minutes at 80 ° C., then the mixture is cooled with stirring.
• a composition comprising (% by weight of MA) is prepared:
• composition comprising (% by weight) is prepared:
• a moisturizing oil for dry skin is prepared using the following constituents:
• caprylic / capric triglycerides 6.5 g
• a moisturizing care cream for normal and combination skin is prepared using the following constituents:
• a moisturizing composition is prepared using the following constituents
• Phases A1 and B are brought to 65 ° C before being mixed with stirring.
• the dispersion is homogenized (between 20 ⁇ 10 6 Pa and 60 ⁇ 10 6 Pa) to obtain a dispersion whose oil globule size is less than 500 nm.
• Phase A2 is dispersed at room temperature in the first dispersion, with vigorous stirring.
• Phase C previously prepared, is then added.
• a moisturizing emulsion adapted for dry skin is obtained.
• composition comprising (% by weight) is prepared:
• An oxidizing bleaching is carried out using the commercial product PLATIFIZ from the L'OREAL company, on natural brown hair. After the discoloration, the hair is rinsed with water before being treated for 5 minutes with a composition comprising a 2% aqueous solution of the polymer of Example 1 in the presence of a preservative. The treated hair is rinsed again with plenty of water before being dried. It is found that the hair treated with the composition according to the invention are smoother, softer and easier to disentangle than control hair (discolored and untreated).
• oxidizing coloration is carried out using the product Excellence Excellence Crème Châtain 4, from L'Oréal Paris, on natural chestnut hair.
• a composition comprising an aqueous solution at 2% by weight of the polymer of Example 1 in the presence of a preservative is applied for 15 minutes, then the hair is rinsed with water and dried.
• a hair straightening composition containing tetramethylguanidine at a concentration of 0.8M in water was made as a hair straightener.
• the pH of the composition is 13.3. This composition is applied to naturally curly African hair for 15 minutes, at a temperature of 30 ° C. The hair is straightened effectively.
• the solution is applied for 15 minutes.
• the hair is then rinsed and dried. It is found that the treated relaxed hair is easy to comb and soft to the touch.

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• 2007
  • 2007-02-16 FR FR0753314A patent/FR2912650A1/fr not_active Withdrawn
• 2008
  • 2008-02-12 WO PCT/FR2008/050209 patent/WO2008104694A2/fr not_active Ceased
  • 2008-02-12 US US12/527,286 patent/US20100061953A1/en not_active Abandoned
  • 2008-02-12 JP JP2009549452A patent/JP2010519188A/ja active Pending
  • 2008-02-12 EP EP08762061A patent/EP2124875A2/de not_active Withdrawn
  • 2008-02-18 EP EP08762112A patent/EP2124876A1/de not_active Withdrawn
  • 2008-02-18 WO PCT/FR2008/050264 patent/WO2008125761A1/fr not_active Ceased
  • 2008-02-18 US US12/527,258 patent/US20100092416A1/en not_active Abandoned
  • 2008-02-18 JP JP2009549845A patent/JP2010519215A/ja active Pending

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