EP3897858A1 - Composition comprenant un polymere photodimerisable modifie et un agent alcalin et/ou un derive amine d'alcoxysilane et procede de traitement mettant en ?uvre la composition - Google Patents
Composition comprenant un polymere photodimerisable modifie et un agent alcalin et/ou un derive amine d'alcoxysilane et procede de traitement mettant en ?uvre la compositionInfo
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- EP3897858A1 EP3897858A1 EP19820775.5A EP19820775A EP3897858A1 EP 3897858 A1 EP3897858 A1 EP 3897858A1 EP 19820775 A EP19820775 A EP 19820775A EP 3897858 A1 EP3897858 A1 EP 3897858A1
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- 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
- A61K8/8129—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 alcohol, ether, aldehydo, ketonic, acetal or ketal radical; Compositions of hydrolysed polymers or esters of unsaturated alcohols with saturated carboxylic acids; Compositions of derivatives of such polymers, e.g. polyvinylmethylether
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- 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
- A61K8/8105—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- A61K8/8117—Homopolymers or copolymers of aromatic olefines, e.g. polystyrene; Compositions of derivatives of such polymers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/31—Hydrocarbons
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
- A61K8/585—Organosilicon compounds
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- 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
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- 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
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- 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
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- 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
- A61K2800/95—Involves in-situ formation or cross-linking of polymers
Definitions
- TITLE COMPOSITION COMPRISING A MODIFIED SAND PHOTODIMERI POLYMER AND AN ALKALINE AGENT AND / OR AN AMINE DERIVATIVE
- the present invention relates to a composition, in particular a cosmetic composition, in particular a hair composition, comprising at least one modified photocrosslinkable polymer and an alkaline agent and / or an amino derivative of alkoxysilane in a particular content.
- a composition makes it possible to obtain a sheathing resistant to washing, the performance of which is stable over time. It is known to those skilled in the art to use photocrosslinkable materials such as materials from
- vinyl monomers and in particular (meth) acrylate monomers.
- document US Pat. No. 5,300,285 describes a process for waving the hair and a composition for implementing this process, and in particular a neutralizing composition based on silicone, comprising a silicone with vinyl function, a photoinitiator 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 working simultaneously as a keratin crosslinking agent, while giving the hair advantages such as conditioning and a soft feel.
- 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).
- Document EP1572139 describes a photodimerizable composition making it possible to deposit on keratin materials, in particular the hair. This document teaches that such deposits make it possible to obtain a residual deposit which provides lasting cosmetic properties over time and which can be easily removed.
- the deposits obtained from the crosslinkable compounds described in this document however exhibit limited persistence. Furthermore, the deposition of these compounds on the hair is not uniform and very dependent largely from the level of damage to the hair. Thus, the result is not uniform between the tip and the hairline.
- the present invention therefore aims to provide a composition comprising a photocrosslinkable polymer which does not have the drawbacks of the compositions of the state of the art.
- the objective of the invention is to develop photodimerizable compositions stable over time, which allow a cladding of keratin materials, and in particular of the hair, effective, homogeneous, reproducible and durable resistant to washing.
- one of the objects of the present invention is a composition comprising:
- alkaline agent (s) and / or amino derivative (s) of alkoxysilane being present (s) ) in the composition in a content ranging from 0.01 to 10% by weight relative to the total weight of the composition, the pH of the composition being greater than or equal to 7.
- Another object of the invention is a method for treating keratin materials comprising the application of said composition and a step
- compositions which are stable over time and which make it possible to obtain a uniform sheathing of the hair which is persistent after washing.
- an “alkylene chain” represents a divalent C1-C20 acyclic hydrocarbon chain; particularly in C1-C6, more particularly in C1-
- aryl or heteroaryl or the aryl or heteroaryl part of a radical may be substituted by at least one substituent on a carbon atom selected from:
- a C1-C16 preferably C Cs, alkyl radical optionally substituted by one or more radicals chosen from hydroxyl, C1-C2 alkoxy, (poly) hydroxy-C2-C4, acylamino, amino radicals substituted by two radicals C1-C4 alkyl, identical or different, optionally carrying at least one hydroxyl group or, the two radicals being able to form, with the nitrogen atom to which they are attached, a heterocycle comprising from 5 to 7 members, preferably of 5 or 6 members, saturated or unsaturated optionally substituted optionally comprising another heteroatom identical or different from nitrogen;
- a 5- or 6-membered heterocycloalkyl radical an optionally cationic 5 or 6-membered heteroaryl radical, preferably imidazolium, and optionally substituted by an (C 1 -C 4 ) alkyl radical, preferably methyl;
- a 5 or 6-membered heteroaryl radical optionally cationic, preferably imidazolium, and optionally substituted by a (C 1 -C 4 ) alkyl radical, preferably methyl;
- acylamino radical (-NR-C (O) -R ') in which the radical R is a hydrogen atom, a C 1 -C 4 alkyl radical optionally carrying at least one hydroxyl group and the radical R 'is a C 1 -C 2 alkyl radical;
- R a carbamoyl radical ((R) 2 NC (0) -) in which the radicals R, which may or may not be identical, represent a hydrogen atom, a C1-C4 alkyl radical optionally carrying at least one hydroxyl group;
- an alkylsulfonylamino radical (R'-S (0) 2 -N (R) -) in which the radical R represents a hydrogen atom, a C 1 -C 4 alkyl radical optionally carrying at least one hydroxyl group and the radical R 'represents a C 1 -C 4 alkyl radical, a phenyl radical; an aminosulfonyl radical ((R) 2 NS (0) 2 -) in which the radicals R, which may or may not be identical, represent a hydrogen atom, a C 1 -C 4 alkyl radical optionally carrying at least one hydroxyl group , a carboxylic radical in acid or salified form (preferably with an alkali metal or ammonium, substituted or not);
- a polyhaloalkyl group preferably trifluoromethyl
- cyclic, cycloalkyl or heterocyclic part of a non-aromatic radical can be substituted by at least one substituent chosen from groups:
- alkylcarbonylamino (RC (O) -N (R ') -) in which the radical R' is a hydrogen atom, a C1-C4 alkyl radical optionally carrying at least one hydroxyl group and the radical R is a radical C1-C2 alkyl, amino optionally substituted by one or two identical or different C1-C4 alkyl groups themselves optionally bearing at least one hydroxyl group, said alkyl radicals being able to form with the nitrogen atom to which they are attached, a heterocycle comprising from 5 to 7 members, saturated or unsaturated optionally substituted optionally comprising at least one other heteroatom different or not from nitrogen;
- alkylcarbonyloxy (RC (O) -O-) in which the radical R is a C1-C4 alkyl radical, amino group optionally substituted by one or two identical or different C1-C4 alkyl groups themselves optionally bearing at least a hydroxyl group, said alkyl radicals being able to form, with the nitrogen atom to which they are attached, a heterocycle comprising from 5 to 7 members, saturated or unsaturated optionally substituted optionally comprising at least one other heteroatom different or not from nitrogen;
- alkoxycarbonyl (RGC (O) -) in which the radical R is a C1-C4 alkoxy radical, G is an oxygen atom, or an amino group optionally substituted by a C1-C4 alkyl group itself optionally bearing '' at least one group hydroxyl, said alkyl radical possibly forming with the nitrogen atom to which they are attached, a heterocycle comprising from 5 to 7 members, saturated or unsaturated optionally substituted optionally comprising at least one other heteroatom different or not from nitrogen;
- aromatic of an aryl or heteroaryl radical can also be substituted by one or more oxo groups
- a cycloalkyl radical is a mono or bicyclic, hydrocarbon radical comprising from 3 to 10 carbon atoms, preferably from 4 to 7 carbon atoms such as cyclopentyl, or cyclohexyl;
- hydrocarbon chain is unsaturated when it has one or more double bonds and / or one or more triple bonds;
- an “aryl” radical represents a mono carbon group
- heteroaryl radical represents a mono or polycyclic group, condensed or not, optionally cationic, comprising from 5 to 22 links, from 1 to 6 heteroatoms chosen from the nitrogen, oxygen, sulfur and selenium atom, and of which at least one cycle is aromatic;
- heteroaryl is selected from acridinyl, benzimidazolyl, benzobistriazolyl, benzopyrazolyl, benzopyridazinyle, benzoquinolyl, benzothiazolyl, benzotriazolyl, benzoxazolyl, pyridinyl, tetrazolyl, dihydrothiazolyl, imidazopyridinyl, imidazolyl, indolyl, isoquinolyl, naphthoimidazolyle, naphthooxazolyle, naphthopyrazolyle, oxadiazolyl, oxazolyl, oxazolopyridyl , phenazinyl, phenooxazolyl, pyrazinyl, pyrazolyl, pyrilyl, pyrazoyltriazyle, pyridyle, pyridinoimidazolyle, pyrrolyle, quinolyle, t
- heterocyclic radical is a radical which may contain one or two unsaturations but not aromatic, mono or polycyclic, condensed or not, containing from 5 to 22 links, comprising from 1 to 6 heteroatoms chosen from the nitrogen, oxygen, sulfur and selenium atom;
- heterocycloalkyl radical is a heterocyclic radical comprising at least one saturated ring
- cationic heteroaryl radical is a heteroaryl group as defined above which comprises a quaternized cationic group endocyclic or exocyclic,
- R and R ' being a heterorayl substituent as defined above and particularly a (hydroxy) (Ci-C 8 ) alkyl group such as methyl;
- ammonium phosphonium such as trimethylammonium, found outside of the heteroaryl such as pyridinyl, indolyl, imidazolyl, or naphthalimidyl in question:
- R a R b R c N + - (Ci-C 6 ) alkylamino with R a , R b and R c identical or different represent a hydrogen atom or a group (Ci-Cs) alkyl such as methyl;
- a “cationic aryl with an exocyclic charge” means an aryl ring in which the quaternized cationic group is found outside of said cycle, it is in particular a substituent R + ammonium, or
- phosphonium such as trimethylammonium, found outside the aryl such as phenyl, or naphthyl:
- an “alkyl radical” is a linear or branched C1-C20 hydrocarbon radical, preferably C Cs;
- the expression “optionally substituted” attributed to the alkyl radical implies that the said alkyl radical may be substituted by one or more radicals chosen from the radicals i) hydroxyl, ii) C1-C4 alkoxy, iii) acylamino, iv) amino optionally substituted by one or two identical or different C1-C4 alkyl radicals, said alkyl radicals being able to form, with the nitrogen atom carrying them, a heterocyle comprising from 5 to 7 members, optionally comprising another heteroatom different from or not from nitrogen; v) or a quaternary ammonium group -N + R'R "R '", M for which R', R ", R '", identical or different, represent a hydrogen atom, or a C1-C4 alkyl group, or -N + R'R ”R '” forms a heteroaryl such as imidazolium optionally substituted by a C1-C4 alkyl group, and M
- alkoxy radical is an alkyl-oxy radical for which the alkyl radical is a hydrocarbon radical, linear or branched, preferably C1 to C16; when the alkoxy group is optionally substituted, this implies that the alkyl group is optionally substituted as defined above;
- organic or inorganic acid salt is meant more particularly the salts chosen from a salt derived from i) hydrochloric acid HCl, ii) acid hydrobromic HBr, iii) sulfuric acid H2SO4, iv) alkylsulfonic acids: Alk-S (O) 2 0H such as methylsulfonic acid and ethylsulfonic acid; v) arylsulfonic acids: Ar-S (0) 2 0H such as benzene sulfonic acid and toluene sulfonic acid; vi) citric acid; vii) succinic acid; viii) tartaric acid; ix) lactic acid, x) alkoxysulfinic acids: Alk-0-S (0) 0H such as methoxysulfinic acid and ethoxysulfinic acid; xi) aryloxysulfinic acids such as tolueneoxysulfinic acid and phen
- anionic counterion is meant an anion or a group
- anionic derived from organic or mineral acid salt counterbalancing the cationic charge of the dye is chosen from i) halides such as chloride, bromide; ii) nitrates; iii) sulfonates including C1-C6 alkylsulfonates: Alk-S (O) 20 such as methylsulfonate or mesylate and ethylsulfonate; iv) arylsulfonates: Ar-S (0) 2 0 such as benzenesulfonate and toluenesulfonate or tosylate; v) citrate; vi) succinate; vii) tartrate; viii) lactate; ix) alkyl sulphates: Alk-0-S (0) 0 such as methysulphate and ethyl sulphate; x) arylsulfates: Ar-0-S (0) 0 such as benzene
- photodimerizable group is meant, within the meaning of the present invention, a chemical group leading to photodimerization reactions under irradiation.
- photodimerization is a chemical reaction between two double bonds (of type 2 + 2) or two pairs of double bonds (of type 4 + 4), and more particularly between two double bonds (of type 2 +2).
- the double bond when it is photo-stimulated, generally when it is subjected to UV radiation, is capable of reacting with another double bond by cyclization.
- the double bond is said to be activated, that is to say that it is spontaneously photodimerizable without requiring the presence of a photoinitiator or of a chemical initiator.
- the activation of this double bond is generally induced by the presence of an electron-withdrawing substituent in the alpha position of this photodimerizable double bond.
- electron-withdrawing substituents mention may be made of aromatic rings, such as the phenyl group optionally substituted by one or more halogen atoms, or electron-withdrawing groups such as NO2, CN, R'- YC (Y ') -, R'-C (Y') - Y-, R'-YC (Y ') - Y-, R'-YS (0) 2 -, -S (0) 2 -Y- R ', with R' representing a hydrogen atom or a (CrC4) alkyl group optionally substituted by one or more halogen atoms, Y, and Y ', identical or different representing an oxygen, sulfur or NR atom ”With R” representing a hydrogen atom or a (Ci-Ce) alkyl group.
- the method according to the invention comprises a step a) of applying a composition comprising a polymer comprising at least one group during photodimerisable.
- the photodimerizable pendant groups which can be used according to the invention are chosen from monovalent radicals of formulas (I) and (II) below:
- - Y and Z independently denote each other a nitrogen atom or a C (R) group with R representing a hydrogen atom or a (CrC4) alkyl group such as methyl;
- A represents a bond or a divalent group chosen from the radicals (CrC 8 ) alkylene, arylene, heteroarylene, cycloalkylene,
- heterocycloalkylene (thio) carbonyls, (C2-C8) alkenylenes and combinations thereof;
- B represents a monovalent group chosen from alkyl (Cr Cs) radicals, aryl radicals, optionally cationic heteroaryl, cycloalkyl, optionally cationic heterocycloalkyl,
- C 8 alkylene, arylene, heteroarylene, cycloalkylene, heterocycloalkylene, (thio) carbonyls, (C2-C8) alkenylenes and combinations thereof;
- p represents an integer inclusive between 1 and 5, in particular between 1 and 3, preferably p is 1; represents the bond which connects the part of the monovalent radical to the rest of the molecule;
- (Ci-Ce) alkyl hydroxy, amino, (di) (Ci-C 6 ) alkylamino, phenyl, carboxy, (Ci-Ce) alkoxy, (Ci-C 6 ) alkoxy (thio) carbonyls, hydrogen (thio) groups - carbonyls, sulfonato R-0-S (0) 2 - or RS (0) 2 -0-, amide RR'NC (O) - or R- C (0) -N (R ') - or acyl RC ( O) -, ammonium RR'R ”N + - with R, R ', and R”, identical or different, representing a hydrogen atom or a group
- the pendant groups which can be dimerized according to the invention are in particular those cited in patents US-2,811, 510, EP 0 313 220, ER 0 313 221, EP 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 pendant groups chosen from monovalent radicals of the following compounds:
- R 1 and R 3 identical or different, represent a halogen atom or a (C1-C6) alkyl group; or then two contiguous R 1 or R 3 groups form together with the carbon atoms which carry it a benzo group;
- R 2 represents the hydrogen atom, a (Ci-Ce) alkyl group optionally substituted by one or more halogen atoms such as chlorine or hydroxy, preferably R 2 represents a (Cr C 6 ) alkyl group such as methyl, ethyl, propyl;
- q and r represent an integer inclusive between 0 and 4; and Q, represents an anionic counter ion preferably chosen from halide ions such as chlorides, bromides, iodides, perchlorates, tetrafluoroborates, methylsulfate, phosphates, sulfates, methanesulfonates, p-toluenesulfonate;
- halide ions such as chlorides, bromides, iodides, perchlorates, tetrafluoroborates, methylsulfate, phosphates, sulfates, methanesulfonates, p-toluenesulfonate
- the bond is on the phenyl in the para position of the styryl group on Ai or linked to the rest of the molecule via R 2 on A 2 ;
- styryl group of Ai and ⁇ 2 is found in para of the pyridinium group; - styrylazolium of formula and their geometric isomers:
- A represents a sulfur atom, an oxygen atom, or an NR 2 or C (R 2 ) 2 group ; and , Q, r, q, R 1 , R 2 , and R 3 being as defined above, preferably the bond is on the phenyl in the para position of the stryryl group, styrylpyrazine,
- the pendant or photodimerizable groups are chosen from:
- R represents a hydrogen atom, a C1-C4 alkyl or C1-C4 hydroxyalkyl group
- R ’ represents a hydrogen atom or a C1- alkyl group
- X- denotes an anionic counter ion preferably chosen from halide ions such as chlorides, bromides, iodides, perchlorates,
- tetrafluoroborates methylsulfate, phosphates, sulfates, methanesulfonates, p-toluenesulfonate; preferably the group styryre is in para of the group
- R denotes a divalent alkylene radical having from 2 to 8 carbon atoms
- R ’ represents a hydrogen atom or a C 1-6 alkyl group
- the styryre group is found in para of the pyridinium group; or b) the photodimerizable groups carrying a styrylazolium function of formula (IIa):
- R denotes a hydrogen atom, an alkyl group in C 1 -C 4 hydroxyalkyl or C 1 -C 4 alkyl;
- A denotes a sulfur atom, an oxygen atom, or an N R 'or C (R') 2 , R 'group; with R 'representing the hydrogen atom or a C 1 -C 4 alkyl group, R' preferably representing the hydrogen atom; and - X having the same meaning as that described for the preceding formula (la);
- the styryre group is on the phenyl in para.
- Such pendant photodimerizable groups have activated double bonds, so that the photodimerization of these double bonds is triggered spontaneously in the UVA domain, without requiring any
- 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.
- the composition of the invention is free of photoinitiator.
- the polymer can comprise one or more hydrophobic pendant groups.
- alkenyl groups such as phenyl, pyridyl, furyl, Indoyl, benzofuryl. thiophenyl, imizadoyl, oxazoyl, thiazoyl, pyrazinyl, pyrimidinyl;
- fluorinated groups such as fluorinated carbon groups, such as -CF3, - CHF 2 , -OCFS, -SCF 3 , CF 3 C (0) -,
- - silicone groups such as -SiR a R b R c such as -Si (CH 3 ) 3 ,
- PDMS a w dihydroxyalkyl
- PDMS a w dicarboxyalkyl
- R a , R b and R c identical or different, representing a (Ci-Cs) alkyl group optionally interrupted and / or terminated by one or more non-contiguous heteroatoms such as O, or S; and R representing a (Ci-Ce) alkyl group.
- hydrophobic pendant group (s) are chosen from a (C2-C22) alkyl group, more preferably from a (C 3 - C1 6 ) alkyl and in particular propyl group.
- the polymer backbone can be varied in nature.
- This polymer backbone can be natural or synthetic. Mention may be made, as skeletons of natural polymers, of polysaccharides.
- poly (vinyl) polymers mention may be made of poly (vinyl acetate), partially or completely hydrolyzed and polyvinyl alcohol (PVA).
- photodimerizable carrying a stylbazolium function they are obtained by reaction of the polymer considered with a chemical entity comprising a group of formula (la) or (Ib).
- the chemical entity comprising a group (la) carries a reactive group W of aldehyde or acetal type.
- the quaternary pyridinium salts can be chlorides, bromides, iodides, perchlorates, tetrafluoroborates, methosulfates, phosphates, sulfates, methanesulfonates, p-toluenesulfonates salts.
- Such chemical entities are described in GB-A-2030575.
- n-methyl-4- (4-formylstyryl) pyridinium is used
- R represents a hydrogen atom, or a (Ci-Cio) alkyl group, optionally substituted and / or interrupted by one or more heteroatoms, preferably R represents a hydrogen atom or a group (Cr C4 ) alkyl such as methyl, ethyl, or propyl, more preferably R represents a hydrogen atom;
- R 1 represents a hydrogen atom, or a (Ci-Cio) alkyl group, optionally substituted and / or interrupted by one or more heteroatoms, preferably R 1 represents a hydrogen atom or a (CrC4) alkyl group; R 2 represents a (CrC 3 o) alkyl group, saturated or unsaturated, optionally substituted and / or interrupted by one or more heteroatoms, an alkenyl group, an aryl group such as phenyl, pyridyl, furyl, Indoyl, benzofuryl.
- A represents a group derived from photodimerizable compound preferably styrylpyridinium such as (I), (II), (Ai), (A 2 ), (la), (Ib) or (lia) as defined
- X represents an oxygen atom or a sulfur, preferably oxygen
- X 'and X represent an oxygen or sulfur atom or an N (R 3 ) group with R 3 represents a hydrogen atom or a (CrC 4 ) alkyl group, preferably X' and X” represent an oxygen atom;
- these chemical entities react with a polymer of polyvinyl alcohol or polyvinyl acetal type as described in the documents cited above and also such as the polymer (III) described in the above diagram for which X, X 'and X ”represent an atom of oxygen, R and R 1 being as described above.
- a polyvinyl alcohol graft polymer comprising units of the following structure, A representing a group (I), (Ai) or (la):
- the polymers can be obtained by reacting polyvinyl alcohol or polyvinylacetate partially hydrolyzed with styrylpyridinium salts with formyl or acetal group as described in GB-A-2030575, WO 96/29312, US 5061603, GB-A-2076826, EP -A-092901.
- the chemical entity comprising a group (Ai) or (la) carries a reactive group which is a halogen atom such as chlorine.
- the photocrosslinkable polymer comprising the groups (Ib) is for example obtained by reaction of the above entity with the polysaccharide chosen from those defined above.
- the polymers having photodimerizable groups carrying a styrylazolium function are obtained by reaction of the polymer with a chemical entity comprising a group of formula (IIa).
- the chemical entity comprising a group (11a) carries a reactive group W of aldehyde or acetal type.
- Polyvinyl alcohol polymers grafted with a styrylazolium group are especially described in EP-A-313220.
- these polymers can be obtained by reacting polyvinyl alcohol or partially hydrolyzed polyvinylacetate with styrylazolium salts containing an aldehyde or acetal group.
- the polymer carrying the photodimerizable group (s) is in the form of particles, in particular dispersed particles.
- the polymer particles are more particularly polyvinyl alcohol particles.
- the polymer carrying the photodimerizable group (s) of the invention is soluble in the cosmetic medium.
- the polymer is a polyvinylacetate (PVA) type polymer partially functionalized by one or more function (s). hydroxyl (s) and one or more function (s) of formula (IX):
- PVA polyvinylacetate
- the degree of polymerization of the PVA can be between 100 and 5000 and the substitution rate, in% of functions of formula (I) as defined above, can be between 0.1 and 25.
- the following diagram represents a variant where the polymer is the polymer (III) as defined above carrying functions grafted by stylbazolium entities such as those of formula (A1) as defined above, which is capable of crosslinking under the effect of light, as shown below.
- the following diagram represents the polymer which is PVA-SbQ (polymer of PVA acetate type carrying some hydrolysed functions and some functions grafted by stylbazoliums entities), which is capable of crosslinking under the effect of light, as illustrated below. after.
- PVA-SbQ polymer of PVA acetate type carrying some hydrolysed functions and some functions grafted by stylbazoliums entities
- the photocrosslinkable polymer is represented by a natural polymer which is functionalized by photodimerizable groups.
- It can in particular be a polysaccharide which can in particular be chosen from chondroitin sulfate, keratan, keratan sulfate, heparin, heparin sulfate, xanthan, carrageenan, hyaluronic acid, chitosan, cellulose and its derivatives, alginate, starch, dextran, pullulan, galactomannan and their biologically acceptable salts.
- the degree of functionalization is of course adjusted in order to be able to confer the degree of crosslinking required during activation.
- the degree of functionalization in a photodimerizable pattern is at least 0.1%, or even at least 0.5%, or even at least 2%.
- the photodimerizable groups are carried by a polymer of the polyvinylacetate or polysaccharide type.
- the crosslinkable polymer can be carried in an aqueous medium.
- composition may contain a single polymer carrying pendant photodimerizable groups of different or different nature.
- the activated double bonds can react with another double bond of the same chemical nature or react with another double bond with a different chemical nature.
- PVA-SbQ-propional As an example of a polymer useful in the invention, mention may be made of the PVA polymer comprising pendant groups below called PVA-SbQ-propional in which preferably the amount of SbQ unit is between, limits included, 0, 5 and 5 mol%, preferably between 2 and 4 mol%, for example of the order of 2 mol%, the amount of propional group is between, limits included, 2 and 20 mol%, preferably between 5 and 15 mol%, for example of the order of 10 mol%, the amount of hydroxyl group is between, limits inclusive, 50 and 97.5 mol%, preferably between 60 and 97.5 mol%, for example around 86% molar:
- the molecular weight Mw of the PVA is between 10,000 and 100,000 g / mol, preferably between 25,000 and 80,000 g / mol.
- the molecular weight Mw is of the order of 27,000 g / mol.
- the polymer (s) comprising at least one group
- photodimerizable represents (s) preferably 0.01 to 25%, better 0.1 to 20%, and better still 1 to 15% of the total weight of the composition.
- composition according to the invention can, in addition, comprise an effective amount of at least one photosensitizer.
- photosensitizer in the sense 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 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.
- composition according to the invention also comprises one or more alkaline agent (s) and / or one or more amino derivative (s) of alkoxysilane.
- the alkaline agent (s) can be chosen from:
- alkali or alkaline earth metals preferably lithium, magnesium, calcium, sodium, potassium buffered with one or more amino acids such as glycine, - carbonates, bicarbonates or hydrogen carbonates, carbonates buffered with bicarbonate to obtain a pH ⁇ 12.0,
- alkali or alkaline earth metals such as lithium, calcium, sodium or potassium
- alkanolamines such as mono-, di- and triethanolamines, mono-, di- and tri- (hydroxymethyl) aminomethane as well as their derivatives,
- alkaline polyamino acids or alkaline polyamino acids, such as polylysines, polyarginines,
- polyethyleneimines PEI
- polyvinylamines the compounds of formula (A) below:
- R x , R y , R z and R t identical or different, represent an atom
- alkanolamine an organic amine comprising a primary, secondary or tertiary amine function, and one or more alkyl groups, linear or branched, C Cs bearing one or more hydroxyl radicals.
- organic amines chosen from alkanolamines such as mono-, di- or tri-alkanolamines, comprising one to three hydroxyalkyl radicals, which may or may not be C1-C4.
- MAA monoethanolamine
- diethanolamine diethanolamine
- triethanolamine monoisopropanolamine
- diisopropanolamine N, N-dimethylethanolamine, aminopropanol, 1-amino-propanol, 2-amino-2-methyl-1-propanol, triisopropanol-amine, 2-amino-2-methyl-1, 3 -propanediol, 3-amino-1, 2-propanediol, 3-dimethylamino-1, 2- propanediol, tris-hydroxymethylamino-methane, aminobutanol, aminopentanol, aminohexanol, preferably 2-amino-2-methyl-1-propanol.
- amino acids which can be used are of natural or synthetic origin, in their L, D or racemic form and comprise at least one acid function chosen more particularly from the acid functions
- Such basic amino acids are preferably chosen from those corresponding to the following formula (B), as well as their salts
- R represents a group chosen from: imidazolyl, preferably 5-imidazolyl; - (CH 2 ) 3 -NH 2 ; - (CH 2 ) 2 -NH 2 ; - (CH 2 ) 2 N (H) -C (O) -NH 2 ; and - (CH 2 ) 2 -N (H) -C (NH) -NH 2 .
- the compounds corresponding to formula (B) are histidine, lysine, arginine, ornithine, citrulline.
- the organic amine can also be chosen from organic amines of heterocyclic type. Mention may in particular be made, in addition to the histidine already mentioned in the amino acids, pyridine, piperidine, imidazole, triazole, tetrazole, benzimidazole.
- poly amines or “poly” amino acids is meant alkaline agents comprising at least two amino or amino acid groups linked to the same molecule, in particular these are polymers whose backbone comprises or is substituted by one or more than one amino group or amino acid group.
- the organic amine can also be chosen from the amino acid dipeptides.
- amino acid dipeptides which can be used in the present invention, mention may in particular be made of carnosine, anserine and whale.
- the organic amine can also be chosen from compounds comprising a guanidine function.
- amines of this type which can be used in the present invention, there may be mentioned in addition to the arginine already mentioned as amino acid, creatine, creatinine, 1, 1-dimethylguanidine, 1, 1 -diethylguanidine, glycocyamine, metformin, agmatine, n-amidinoalanine, 3-guanidino- acid propionic acid, 4-guanidinobutyric acid and 2 - ([[amino (imino) methyl] amino)] ethane-1-sulfonic acid.
- the alkaline agent (s) are chosen from water-soluble inorganic alkaline agents, alkanolamines, basic amino acids, organic amines, preferably organic amines.
- the alkaline agent (s) are chosen from the hydroxides of alkali or alkaline earth metals, preferably lithium, magnesium, calcium, sodium, potassium buffered with one or more amino acids such as glycine, carbonates, bicarbonates or hydrogen carbonates, carbonates buffered with bicarbonate to obtain a pH ⁇ 12.0, phosphates of alkali or alkaline earth metals such as lithium, calcium, sodium or potassium, monoethanolamine (MEA), l aminopropanol, 1-amino-propanol, 2-amino-2-methyl-1-propanol, 2-amino-2-methyl-1, 3-propanediol, aminobutanol, aminopentanol, aminohexanol, arginine and guanidine.
- amino acids such as glycine, carbonates, bicarbonates or hydrogen carbonates, carbonates buffered with bicarbonate to obtain a pH ⁇ 12.0
- phosphates of alkali or alkaline earth metals such
- the amino derivative (s) of alkoxysilane can be chosen from the compounds corresponding to formula (C) below and / or their oligomers and / or their hydrolysis products:
- Ri is a linear or branched C1-C6 hydrocarbon chain
- R alkyl Ci-C 2 o, in particular C1-C6 alkyl optionally substituted by a radical containing a silicon atom, C3-C40 or aromatic C6-C30),
- Ri can be interrupted by a heteroatom (O, S, NH) or a carbonyl group (CO).
- R 2 and R 3 which are identical or different, represent an alkyl group, linear or branched, comprising from 1 to 6 carbon atoms,
- x denotes an integer ranging from 0 to 2
- oligomer means the polymerization products of the compounds of formula (C) comprising from 2 to 10 silicon atoms.
- R 2 represents an alkyl group comprising from 1 to 4 carbon atoms, better still a linear alkyl group comprising from 1 to 4 carbon atoms, and preferably the ethyl group.
- R 3 represents an alkyl group comprising from 1 to 4 carbon atoms, better still a linear alkyl group comprising from 1 to 4 carbon atoms, and preferably methyl or ethyl groups.
- Ri is an acyclic chain.
- the compound of formula (C) only has one silicon atom in its structure.
- Ri represents an alkyl group, and even more
- a linear alkyl group comprising from 1 to 6 carbon atoms or a C 1 -C 6 aminoalkyl group.
- z varies from 1 to 3. Even more preferably z is equal to 3.
- the first composition comprises at least one compound of formula (C) chosen from 3-aminopropyltriethoxysilane (APTES), 3-aminoethyltriethoxysilane (AETES), 3-aminopropylmethyldiethoxysilane, N- (2-aminoethyl) -3- aminopropyltriethoxysilane, 3- (m-aminophenoxy) propyltrimethoxysilane, p-aminophenyltrimethoxysilane, N- (2-aminoethylaminomethyl) phenethyltrimethoxysilane, better among 3-aminopropyltriethoxysilane (APTES), 3-aminoethylmethyl N- (2-aminoethyl) -3-aminopropyltriethoxysilane or their oligomers and / or their hydrolysis products.
- the composition comprises 3-aminopropyltriethoxysilane (AP
- the alkaline agent (s) and / or the amino derivative (s) of alkoxysilane used (s) is (are) in the composition in a content ranging from 0.01 and 10% by weight, preferably between 0.02 and 5%, by weight relative to the total weight of the composition.
- the pH of the composition according to the invention is greater than or equal to 7.
- the composition of the invention has a pH ranging from 7.0 to 12.0, preferably from 7.5 to 11, better still 8 to 10, even more preferably from 8 to 9.
- the pH of the composition is stable, that is to say that it remains basic, namely greater than or equal to 7, over time.
- the pH of the composition remains basic for a storage period of at least 4 weeks, or even 8 weeks.
- composition can comprise a cosmetically acceptable medium.
- the cosmetically acceptable medium which can be used in the compositions of the invention may comprise a solvent chosen from water, the solvents
- the organic solvents can be chosen from alcohols, polyols, polyol ethers and their mixtures, the alcohols being preferably chosen from lower C1-C6 alkanols, and preferably chosen from ethanol, propanol and isopropanol , the polyols preferably being chosen from propylene glycol, hexylene glycol, glycerin, and pentanediol.
- the solvent (s) represent (s) 0.1% to 99% of the total weight of the composition.
- the composition is aqueous.
- the amount of water can vary from 5 to 98% by weight, better from 15% by weight to 95% by weight, better still from 25 to 90% by weight and even more preferably from 30 to 90% by weight. weight relative to the total weight of the composition.
- composition according to the invention may also contain additives usually used in cosmetics, such as anionic, cationic, amphoteric or nonionic surfactants, thickening agents, bodies grease, fixing or conditioning polymers, preserving agents, perfumes, dyes, pigments, oxidizing agents, agents
- additives can be present in the composition according to the invention in an amount ranging from 0 to 20% by weight relative to the total weight of the
- the process of the invention comprises, after step a) of applying the composition, a step b) of irradiating the composition on the keratin materials to crosslink the polymer.
- This irradiation may consist of illumination with ambient light or with an artificial light source, of the composition applied to keratin materials.
- Ambient or artificial light can emit visible and / or UV radiation. Preferably, it emits at least a proportion of radiation in the UV, for example a proportion of UV of at least 2% of the total irradiance of ambient light.
- the exposure comprises, or even consists of, illumination in ambient light of the surface of said layer, in particular for a period of at least 1 minute.
- the duration of exposure to ambient light can range more particularly from 10 seconds to 30 minutes, in particular from 2 to 15 minutes.
- the exposure comprises, or even consists of, illumination with an artificial light source from the surface of said layer.
- the duration of exposure to said artificial light can range from 1 second to 20 minutes, in particular from 1 second to 1 minute.
- the crosslinking can be done in natural or artificial light, for example using lighting with a lamp, a flash, a laser, LEDs, for example in the form of an array of LEDs.
- the artificial light source can emit radiation in the visible range and / or radiation in the UV.
- the light emitted may or may not be monochromatic.
- the wavelength of the emitted light is preferably centered on 365 nm, in particular between 100 nm and 500 nm, and better still between 200 nm and 420 nm.
- the crosslinking is initiated by simple illumination without requiring a photoinitiator.
- it will be an artificial light source emitting an energy of between 0.5 and 5W / cm 2 , the exposure times being adapted accordingly.
- Crosslinking can occur with a reduced light intensity
- the lighting system can produce this light intensity of, for example, between 500 mJ / cm 2 and 10 J / cm 2 .
- the dual characteristic of the absence of photoinitiator and of relatively low light intensity is particularly advantageous since it makes it possible to limit the harmful effects of aggressive initiators or of prolonged exposure to intense light, in particular in the UV wavelengths. .
- the composition is applied to keratin fibers such as the hair.
- the composition can be applied to wet or dry keratin fibers, clean or not.
- the keratin fibers are preferably dried after application of the composition and before irradiation.
- step b) of irradiation pause at room temperature, or under heat, or under red light.
- compositions were produced from the ingredients, the contents of which are indicated in the table below (% in g of active material).
- compositions which have a stable pH over time, which allows the stability of the polymer.
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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FR1873911A FR3090364B1 (fr) | 2018-12-21 | 2018-12-21 | Composition comprenant un polymere photodimerisable modifie et un agent alcalin et/ou un derive amine d’alcoxysilane et procede de traitement mettant en œuvre la composition |
PCT/EP2019/085605 WO2020127230A1 (fr) | 2018-12-21 | 2019-12-17 | Composition comprenant un polymere photodimerisable modifie et un agent alcalin et/ou un derive amine d'alcoxysilane et procede de traitement mettant en œuvre la composition |
Publications (1)
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EP3897858A1 true EP3897858A1 (fr) | 2021-10-27 |
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EP19820775.5A Pending EP3897858A1 (fr) | 2018-12-21 | 2019-12-17 | Composition comprenant un polymere photodimerisable modifie et un agent alcalin et/ou un derive amine d'alcoxysilane et procede de traitement mettant en ?uvre la composition |
Country Status (8)
Country | Link |
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US (1) | US20220087920A1 (fr) |
EP (1) | EP3897858A1 (fr) |
JP (1) | JP7350861B2 (fr) |
KR (1) | KR20210104811A (fr) |
CN (1) | CN113195058A (fr) |
BR (1) | BR112021011873A2 (fr) |
FR (1) | FR3090364B1 (fr) |
WO (1) | WO2020127230A1 (fr) |
Families Citing this family (3)
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CN112574428B (zh) * | 2020-12-16 | 2022-04-12 | 济南大学 | 一种超支化型含氟硅耐高温脱模剂及其应用 |
FR3131200A1 (fr) * | 2021-12-23 | 2023-06-30 | L'oreal | Composition comprenant un polymère photoréticulable et un agent colorant |
FR3131201A1 (fr) | 2021-12-23 | 2023-06-30 | L'oreal | Procédé pour démaquiller des fibres kératiniques ayant été préalablement traitées par une composition comprenant un polymère photoréticulable |
Family Cites Families (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2811510A (en) | 1955-09-15 | 1957-10-29 | Eastman Kodak Co | Light-sensitive polymeric stilbazoles and quaternary salts thereof |
US4272620A (en) | 1978-08-09 | 1981-06-09 | Agency Of Industrial Science And Technology | Polyvinyl alcohol-styrylpyridinium photosensitive resins and method for manufacture thereof |
JPS56147804A (en) | 1980-04-17 | 1981-11-17 | Agency Of Ind Science & Technol | Photosensitive resin material for forming fluorescent surface of cathode ray tube |
DE3374088D1 (en) | 1982-04-23 | 1987-11-19 | Autotype Int Ltd | Photopolymers |
JPS61153655A (ja) * | 1984-12-27 | 1986-07-12 | Fuji Photo Film Co Ltd | 湿し水不要感光性平版印刷版 |
EP0313220B1 (fr) | 1987-10-17 | 1994-05-11 | Autotype International Limited | Photopolymères |
EP0313221B1 (fr) | 1987-10-17 | 1994-05-04 | Autotype International Limited | Photostencil pour l'impression sérigraphique |
GB2226564B (en) | 1988-12-16 | 1993-03-17 | Sericol Group Ltd | Photopolymerisable polyvinyl alcohols and compositions containing them |
JPH0527449A (ja) * | 1991-07-23 | 1993-02-05 | Konica Corp | 湿し水不要感光性平版印刷版の処理方法 |
US5300285A (en) | 1992-10-13 | 1994-04-05 | Dow Corning Corporation | Permanent waving with silicones |
WO1996029312A1 (fr) | 1995-03-20 | 1996-09-26 | Orion Electric Co., Ltd. | Sel de stilbazolium, sa preparation et son utilisation |
AU2003296830A1 (en) * | 2002-12-13 | 2004-07-09 | L'oreal | Cosmetic composition and method for treating keratinous materials, comprising a photodimerizable compound |
GB0318115D0 (en) | 2003-08-01 | 2003-09-03 | Sericol Ltd | A printing ink |
WO2013190466A2 (fr) * | 2012-06-19 | 2013-12-27 | L'oreal | Procédé cosmétique de maquillage des yeux |
US9636293B2 (en) * | 2014-10-13 | 2017-05-02 | L'oréal | Latex nail compositions having low amounts of photo-initiator |
TWI693470B (zh) | 2015-06-30 | 2020-05-11 | 日商富士軟片股份有限公司 | 感光性樹脂組成物、硬化膜的製造方法、硬化膜及液晶顯示裝置 |
FR3046072B1 (fr) | 2015-12-23 | 2018-05-25 | L'oreal | Procede de traitement des matieres keratiniques au moyen d'une composition comprenant un polymere photodimerisable modifie |
FR3060341B1 (fr) * | 2016-12-21 | 2020-01-24 | L'oreal | Procede de traitement des matieres keratiniques mettant en œuvre une composition comprenant un compose de type thiolactone et une composition comprenant un agent alcalin et/ou un derive amine d’alcoxysilane |
-
2018
- 2018-12-21 FR FR1873911A patent/FR3090364B1/fr active Active
-
2019
- 2019-12-17 US US17/312,646 patent/US20220087920A1/en active Pending
- 2019-12-17 KR KR1020217022263A patent/KR20210104811A/ko not_active Application Discontinuation
- 2019-12-17 JP JP2021535925A patent/JP7350861B2/ja active Active
- 2019-12-17 EP EP19820775.5A patent/EP3897858A1/fr active Pending
- 2019-12-17 WO PCT/EP2019/085605 patent/WO2020127230A1/fr unknown
- 2019-12-17 CN CN201980084834.6A patent/CN113195058A/zh active Pending
- 2019-12-17 BR BR112021011873-0A patent/BR112021011873A2/pt not_active Application Discontinuation
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Publication number | Publication date |
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JP2022514899A (ja) | 2022-02-16 |
WO2020127230A1 (fr) | 2020-06-25 |
BR112021011873A2 (pt) | 2021-09-08 |
FR3090364B1 (fr) | 2021-06-18 |
CN113195058A (zh) | 2021-07-30 |
KR20210104811A (ko) | 2021-08-25 |
FR3090364A1 (fr) | 2020-06-26 |
US20220087920A1 (en) | 2022-03-24 |
JP7350861B2 (ja) | 2023-09-26 |
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