WO2004056331A1 - Composition pour teindre des fibres de keratine, qui renferme au moins un compose de radicaux libres du type nitroxyle et au moins un alcool primaire ou secondaire - Google Patents

Composition pour teindre des fibres de keratine, qui renferme au moins un compose de radicaux libres du type nitroxyle et au moins un alcool primaire ou secondaire Download PDF

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Publication number
WO2004056331A1
WO2004056331A1 PCT/EP2003/015039 EP0315039W WO2004056331A1 WO 2004056331 A1 WO2004056331 A1 WO 2004056331A1 EP 0315039 W EP0315039 W EP 0315039W WO 2004056331 A1 WO2004056331 A1 WO 2004056331A1
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Prior art keywords
composition
group
oxylpiperidine
tetramethyl
dyeing
Prior art date
Application number
PCT/EP2003/015039
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English (en)
Inventor
Grégory Plos
Original Assignee
L'oreal
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from FR0216534A external-priority patent/FR2848836B1/fr
Application filed by L'oreal filed Critical L'oreal
Priority to AU2003294974A priority Critical patent/AU2003294974A1/en
Priority to DE10393955T priority patent/DE10393955T5/de
Publication of WO2004056331A1 publication Critical patent/WO2004056331A1/fr

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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
    • A61Q5/10—Preparations for permanently dyeing the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • A61K8/66—Enzymes

Definitions

  • the present invention relates to a dye composition for dyeing keratin fibres, in particular human keratin fibres such as the hair, comprising at least one free-radical compound of nitroxyl type, at least one primary or secondary alcohol, optionally a nucleophilic agent, and optionally an oxidation catalyst .
  • - direct dyeing or semi -permanent dyeing consists in introducing the colour via a coloured molecule, which is adsorbed onto the surface of the keratin fibres and/or penetrates by diffusion into the surface layers of these fibres.
  • One of the advantages of this type of dyeing is that mixing is not necessary at the time of application. The leave-in times are generally fairly short and the mild dyeing conditions preserve the integrity of the keratin fibres, but the colorations obtained by this mode of dyeing show poor wash fastness and fade out after shampooing only 4 or 5 times.
  • oxidation dyeing or permanent dyeing uses the oxidative condensation of colourless or weakly coloured molecules, known as oxidation bases, such as ortho- or para-phenylenediamines, ortho- or para-aminophenols or heterocyclic compounds in the presence of an oxidizing agent.
  • oxidation bases such as ortho- or para-phenylenediamines, ortho- or para-aminophenols or heterocyclic compounds
  • This reaction leads to the formation of insoluble coloured polymer compounds which are trapped in the keratin fibres.
  • the main advantage of oxidation dyeing lies in the longevity of the colorations obtained, in particular in the fastness to washing and to external agents such as light, bad weather, permanent waving, perspiration and rubbing, and also in the production of a wide range of shades.
  • this type of dyeing entails mixing the oxidizing agent, generally aqueous hydrogen peroxide, with oxidation bases at the time of use. Furthermore, the chemical dyeing conditions, such as the pH and an oxidizing medium, result in degradation of the keratin fibres. Moreover, this mode of dyeing requires relatively long leave-in times.
  • patents FR 2 787 708, FR 2 787 707, FR 2 787 705 and FR 2 787 706 describe the combination of an aldehyde or a ketone with, respectively, an activated methylene, a cationic derivative, an aliphatic cationic amine and a heterocyclic cationic amine .
  • the aim of the present invention is to provide a novel system for dyeing keratin fibres that does not require the mixing of an aldehyde or a ketone with a nucleophile at the time of application, that has good fastness properties, in particular with respect to repeated washing, and that does not degrade hair fibres.
  • a dye composition for the oxidation dyeing of keratin fibres comprising, in a medium that is suitable for dyeing:
  • a 2 which may be identical or different, represent an aliphatic chain of 2 to 50 carbon atoms optionally comprising one or more hetero atoms chosen from nitrogen, sulphur, oxygen and phosphorus;
  • a and A 2 together form: - an unsaturated, aromatic or non-aromatic, fused or non-fused monocarbocyclic or polycarbocyclic group containing from 6 to 50 carbon atoms;
  • - Ri represents a hydrogen atom; a Cx-Cj alkyl grou ;
  • R 2 represents a hydrogen atom; a halo group; a C ⁇ -C 4 alkyl group optionally substituted with one or more hydroxyl, C 1 -C4 alkoxy, carboxyl, hydrogenocarbonyl or C!-C 4 alkylcarbonyl groups; a hydroxyl group; a C 1 -C 4 alkoxy group; a C 1 -C 4 monoalkylamino or dialkylamino group; a C 1 -C 4 alkoxycarbonyl group; a C1-C 4 hydrogenocarbonyl- alkylcarbonyl group; a group of -CHR3-OH type in which R 3 may be a hydrogen atom or a C1-C 4 alkyl group .
  • a subject of the present invention is also a process for dyeing keratin fibres, in particular human keratin fibres such as the hair, using the above composition, and also a device for performing this process.
  • a subject of the present invention is also the use of the composition of the invention for the oxidation dyeing of keratin fibres.
  • alk means a linear or branched radical, for example methyl, ethyl, n-propyl, isopropyl or butyl.
  • An alkoxy radical is a radical alk-O-
  • an alkylcarbonyl radical is a radical alk-CO-
  • an alkoxycarbonyl radical is a radical alk-O-CO-
  • a hydrogenocarbonylalkyl- carbonyl radical is a radical H-CO-alk-CO- with the alkyl radical having the definition given above.
  • a sulphonato radical is an -S0 3 " radical .
  • a trialkylammonio radical is a radical (alk) 3 N + - with the alkyl radical having the definition given above.
  • the imidazolio, pyridinio and benzothiazolio radicals are the cationic radicals corresponding to the imidazolium, pyridinium and benzothiazolium cations.
  • a halo group denotes a halogen atom chosen from chlorine, bromine, iodine and fluorine.
  • a fused or non-fused, aromatic or non- aromatic monocarbocyclic or polycarbocyclic group containing from 6 to 50 carbon atoms may be, for example, a benzene, naphthalene, anthracene or cyclohexane ring system.
  • a 5- to 30-membered aromatic or non-aromatic, fused or non-fused, monoheterocyclic or polyheterocyclic group containing one or more hetero atoms may be, for example, a thiophene, benzofuran, benzothiophene, indole, bispyridine, benzopyran, quinoline, pyrazole, pyridine, pyrrole, furan, imidazole or benzimidazole ring system.
  • the polyheterocycle may be fused or substituted with one or more carbocycles .
  • the primary or secondary alcohol is chosen such that the radicals Ai and A 2 together form a benzene nucleus .
  • the primary or secondary alcohol is chosen from benzyl alcohol, 2-methylbenzyl alcohol, 2-aminobenzyl alcohol, 3-aminobenzyl alcohol, 4- aminobenzyl alcohol, 2-hydroxybenzyl alcohol, 1,2- di (hydroxymethyl) benzene, 1, 3-di (hydroxymethyl) benzene and 1 , 4-di (hydroxymethyl) benzene .
  • the free-radical compound of nitroxyl type is a 2,2' , 6, 6' -tetramethyl-N-oxylpiperidine derivative of formula (IV) and / or one of the addition salts thereof :
  • R 3 and R 4 independently of each other, represent a monovalent group chosen from a hydrogen atom; a C ⁇ -C 4 alkyl group; a hydroxyl group; a C ⁇ -C 4 alkoxy group; a carboxyl group; a Cx- j alkoxycarbonyl group; a hydrogenocarbonyl group; an amino group; a C 1 -C 4 acylamino group; a C 1 -C4 haloacylamino group; an isothiocyanato group; a maleimido group; a phosphonyloxy group; a Ci- j alkoxyhalophosphonyloxy group; a 4-nitrobenzoyloxy group; or R 3 and R 4 form, with the carbon atom to which they are attached, a carbonyl group.
  • Examples that may be mentioned include 2 , 2 ' , 6 , 6 ' -tetramethyl-N-oxylpiperidine, 4-hydroxy- 2,2' , 6, 6' -tetramethyl-N-oxylpiperidine, 4-amino- 2,2' ,6,6' -tetramethyl-N-oxylpiperidine, 4-acetamido- 2,2' ,6,6' -tetramethyl-N-oxylpiperidine, 4- (2- bromoacetamido) -2,2' ,6,6' -tetramethyl-N-oxylpiperidine, 4- (2-iodoacetamido) -2,2' ,6,6' -tetramethyl-N- oxylpiperidine, 4-ethoxyfluorophosphonyloxy-2 , 2 ' ,6,6'- tetramethyl-N-oxylpiperidine, 4-isothiocyanato- 2,2' , 6, 6' -te
  • the free-radical compound of nitroxyl type is N,N-diphenylnitroxyl of formula (V) :
  • the free-radical compound of nitroxyl type is N,N-di-tert-butylnitroxyl of formula (VI) :
  • the free-radical compound of nitroxyl type is 3-carbamoylproxylene of formula (VII) :
  • the free-radical compound of nitroxyl type is in the form of a polymer containing at least one of the units of formula (VIII) or (IX) below:
  • the addition salts that may be used in the context of the invention are chosen especially from the addition salts with an acid, such as the hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates, tosylates, benzene- sulphonates, phosphates and acetates, and the addition salts with a base, such as sodium hydroxide, potassium hydroxide, ammonia, amines or alkanolamines .
  • the concentration of primary or secondary alcohol is generally between 0.01% and 30% by weight and preferably between 0.05% and 20% by weight relative to the total weight of the composition.
  • the concentration of free-radical compound of nitroxyl type is generally between 0.01% and 30% by weight and preferably between 0.05% and 20% by weight relative to the total weight of the composition.
  • the dye composition of the invention may also comprise a nucleophilic agent.
  • the nucleophilic agent contains at least one amine, alcohol or activated methylene function.
  • This nucleophilic agent is preferably an aromatic compound substituted with an amine, alcohol or activated methylene function.
  • the nucleophilic agent is preferably chosen from para-phenylenediamines, para-aminophenols, ortho- phenylenediamines, ortho-aminophenols, meta-phenylene- diamines, meta-aminophenols, aminonaphthalenes, aminohydroxynaphthalenes, triaminobenzenes, tetraamino- benzenes, diaminophenols, triaminophenols, nitro-para- phenylenediamines, nitro-ortho-phenylenediamines, nitro-meta-phenylenediamines, nitroaminophenols, aminopyridines, aminohydroxypyridines, nitroanilines, diaminodiphenylamines, amino
  • composition comprises a nucleophilic agent
  • it is present in an amount generally of between 0.01% and 30% by weight and preferably between 0.05% and 20% by weight relative to the total weight of the composition.
  • the composition of the invention may furthermore contain at least one oxidation catalyst .
  • This catalyst is preferably an oxidase enzyme, preferably a laccase or a peroxidase .
  • the oxidase enzymes are obtained by extraction or via biotechnology.
  • laccases that may be used according to the invention, mention may be made of laccases that may be obtained from plants: Anacardiacea plants, Podocarpacea plants, Rosmarinus off. , Solanum tuberosum, Iris sp. , Coffea sp. , Daucus carrota, Vinca minor, Persea Americana, Catharenthus roseus, Musa sp. , Malus pumila, Gingko biloba, Monotropa hypopithys , Aesculus sp.
  • Acer pseudoplatanus Prunus persica, Pistacia palaestina and rom microorganisms : Polyporus versicolor, Rhizoctoniapraticola, Rhus vernicifera, Scytalidium, Polyporus pinsitus, Myceliophtora thermophila, Rhizoctonia solani, Pyricularia orizae, Trametes versicolor, Fomes fomentarius , Chaetomium thermophile, Neurospora crassa, Colorius versicol, Botrytis cinerea, Rigidoporus lignosus , Phellinus noxius, Pleurotus ostreatus, Aspergillus nidulans, Podospora anserina, Agaricus bisporus, Ganoderma lucidum, Glomerella cingulata, Lactarius piperatus, Russula delica, Heterobasidion annosum
  • peroxidases that may be used according to the invention, mention may be made of peroxidases that may be obtained from microorganisms : Aspergillus oryzae, Caldariomyces fumago, Inonotus weudi, Aspergillus flavus, Trametes versicolor, Aspergillus ochraceus, Phanerochaete chrysosporium, Geotrichum candidum, Aspergillus parasiticus,
  • Cochiliobolus heterostrophus Phellinus pini, Phellinus chrysoloma, Phellinus weudi, Phytophthora palmivora, Merulius tremellosus, Phanerochaete flavido-alba, Phlebia radiata, Ceriporiopsis subvermispora, Junghuhnia separabilima, Phanerochaete sordida, Pleurotus eryngii, Bjerkandera sp.
  • Phlebia ochraceofulva Nematoloma frowardii, Dichomitus squalens, Phanerochaete chrysosporium, Pycnoporus cinnabarinus , Bjerkandera adusta, Trametes hirsuta, Arthromyces ramosus, and variants thereof, and from plants: horseradish, Arachis hypogea (peanut), Raphanus sativus (Japanese radish) , Sphagnum magellani, Nicotiana tabacum.
  • composition comprises an oxidation catalyst
  • it is present in an amount generally of between 0.01% and 30% by weight and preferably between 0.05% and 20% by weight relative to the total weight of the composition.
  • the dye composition in accordance with the invention may also contain one or more direct dyes that may be chosen especially from nitrobenzene dyes, azo direct dyes and methine direct dyes. These direct dyes may be of nonionic, anionic or cationic nature.
  • composition of the present invention may also comprise one or more oxidation bases conventionally used in oxidation dyeing.
  • composition of the present invention may further comprise one or more couplers conventionally used in oxidation dyeing.
  • the medium that is suitable for dyeing also known as the dye support, generally consists of water or a mixture of water and at least one organic solvent to dissolve the compounds which would not be sufficiently soluble in water.
  • the alcohols which are useful in the invention may serve as solvents .
  • the composition may however contain other alcohols as organic solvent. Mention may be made, for example, of C 1 -C 4 lower alkanols, such as ethanol and isopropanol; polyols and polyol ethers such as 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether and monomethyl ether, and mixtures thereof .
  • the solvents are present in proportions preferably of between 1% and 40% by weight approximately relative to the total weight of the dye composition, and even more preferably between 5% and 30% by weight approximately.
  • composition in accordance with the invention can also contain various adjuvants conventionally used in compositions for dyeing the hair, such as anionic, cationic, nonionic, amphoteric or zwitterionic surfactants or mixtures thereof, anionic, cationic, nonionic, amphoteric or zwitterionic polymers or mixtures thereof, inorganic or organic thickeners, and in particular anionic, cationic, nonionic or amphoteric associative polymeric thickeners, antioxidants, penetration agents, sequestering agents, fragrances, buffers, dispersing agents, packaging agents such as, for example, silicones, which may or may not be volatile or modified or unmodified, film-forming agents, ceramides, preserving agents and opacifiers.
  • adjuvants conventionally used in compositions for dyeing the hair
  • anionic, cationic, nonionic, amphoteric or zwitterionic surfactants or mixtures thereof anionic, cationic, nonionic, amphoteric or
  • the above adjuvants are generally present in an amount for each of them of between 0.01% and 20% by weight relative to the weight of the composition.
  • the pH of the dye composition in accordance with the invention is generally between about 3 and 11 and preferably between about 4 and 10. It may be adjusted to the desired value using acidifying or basifying agents usually used in the dyeing of keratin fibres, or alternatively using standard buffer systems.
  • acidifying agents which may be mentioned, for example, are inorganic or organic acids such as hydrochloric acid, orthophosphoric acid, sulphuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid and lactic acid, and sulphonic acids .
  • basifying agents which may be mentioned, for example, are aqueous ammonia, alkaline carbonates, alkanolamines such as mono-, di- and triethanolamine and derivatives thereof, sodium hydroxide, potassium hydroxide and the compounds of formula (X) below:
  • W is a propylene residue which is optionally substituted with a hydroxyl group or a C ⁇ -C 4 alkyl radical
  • R a , Rb, Rc and R d which may be identical or different, represent a hydrogen atom, a C 1 -C4 alkyl radical or a C ⁇ .-C4 hydroxyalkyl radical.
  • the dye composition according to the invention may be in various forms, such as in the form of liquids, creams or gels, or in any other form that is suitable for dyeing keratin fibres, and especially human hair.
  • the process for dyeing keratin fibres of the present invention consists in applying to the keratin fibres a composition comprising, in a medium that is suitable for dyeing, at least one free-radical compound of nitroxyl type, at least one primary or secondary alcohol, optionally a nucleophilic agent, and optionally an oxidation catalyst, and in developing the colour using an oxidizing agent .
  • the oxidizing agent is present in an oxidizing composition that is applied simultaneously or sequentially to the keratin fibres.
  • the oxidizing agent is added to the dye composition just at the time of its application.
  • the process of the invention consists in applying to the keratin fibres, sequentially and in any order, a first composition comprising, in a medium that is suitable for dyeing, at least one free-radical compound of nitroxyl type and at least one primary or secondary alcohol and a second composition comprising, in a medium that is suitable for dyeing, at least one nucleophilic agent, one of the two compositions or both of them optionally comprising an oxidation catalyst, and then in applying an oxidizing composition comprising, in a medium that is suitable for dyeing, at least one oxidizing agent.
  • each of the compositions may optionally be followed by a rinsing operation.
  • the action time for each of the compositions is generally between 5 minutes and 1 hour and preferably between 5 minutes and 30 minutes.
  • the application temperature is generally set at between room temperature and 80°C and preferably between room temperature and 60°C.
  • the oxidizing agents used in the present invention are, for example, hydrogen peroxide, urea peroxide, persalts such as percarbonates, persulphates, perborates, 3-chloroperbenzoates and metal salts such as copper or iron salts, for instance copper II chloride .
  • this composition may also contain various adjuvants conventionally used in hair dye compositions and as defined above, and its pH may be between 3 and 12 and preferably between 5 and 11.
  • the oxidizing agent concentration is generally such that when the oxidizing composition is mixed with the other compositions, the oxidizing agent concentration in the composition obtained is between 0.01% and 30% by weight and preferably between 0.05% and 20% by weight relative to the total weight of the composition.
  • compositions applied to the keratin fibres may be in various forms, such as in the form of liquids, creams or gels, or in any other form that is suitable for dyeing keratin fibres, and especially human hair.
  • the oxidizing agent may also be atmospheric oxygen.
  • the composition is stored in an anaerobic medium and is placed in contact with air at the time of use for dyeing keratin fibres.
  • the invention then has an additional advantage, which is that of not requiring mixing at the time of application.
  • a subject of the present invention is also a multi-compartment device for performing the process for dyeing keratin fibres described above .
  • the multi-compartment device of the invention contains, in a first compartment, a composition comprising, in a medium that is suitable for dyeing, at least one free-radical compound of nitroxyl type, at least one primary or secondary alcohol, optionally a nucleophilic agent and optionally an oxidation catalyst, and, in a second compartment, a composition comprising, in a medium that is suitable for dyeing, at least one oxidizing agent.
  • the device contains, in a first compartment, a composition comprising, in a medium that is suitable for dyeing, at least one free-radical compound of nitroxyl type and at least one primary or secondary alcohol, in a second compartment, a composition comprising, in a medium that is suitable for dyeing, at least one oxidizing agent, and, in a third compartment, a composition comprising, in a medium that is suitable for dyeing, at least one nucleophilic agent.
  • one of the compositions present in the first and the third compartment or both comprises an oxidation catalyst .
  • the device contains, in a first compartment, a composition comprising, in a medium that is suitable for dyeing, at least one free-radical compound of nitroxyl type, at least one primary or secondary alcohol and at least one nucleophilic agent, in a second compartment, a composition comprising, in a medium that is suitable for dyeing, at least one oxidizing agent, and, in a third compartment, a composition comprising, in a medium that is suitable for dyeing, at least one oxidation catalyst.
  • the device contains, in a first compartment, a composition comprising, in a medium that is suitable for dyeing, at least one free-radical compound of nitroxyl type and at least one primary or secondary alcohol, in a second compartment, a composition comprising, in a medium that is suitable for dyeing, at least one oxidizing agent, in a third compartment, a composition comprising, in a medium that is suitable for dyeing, at least one nucleophilic agent, and, in a fourth compartment, a composition comprising, in a medium that is suitable for dyeing, at least one oxidation catalyst.
  • a subject of the present invention is also an anaerobically packaged aerosol containing a composition comprising, in a medium that is suitable for dyeing, at least one free-radical compound of nitroxyl type, at least one primary or secondary alcohol, optionally a nucleophilic agent and optionally an oxidation catalyst .
  • the primary or secondary alcohol does not react with the nucleophilic compound and may be stored in the same container as the said compound.
  • a subject of the present invention is also the use for dyeing keratin fibres of a composition
  • a composition comprising, in a medium that is suitable for dyeing, at least one free-radical compound of nitroxyl type, at least one primary or secondary alcohol, optionally a nucleophilic agent, optionally an oxidation catalyst and optionally an oxidizing agent.
  • Compositions .1 and 2 are applied to white hair with a leave-in time of 30 minutes, to dewhiten them.

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  • Life Sciences & Earth Sciences (AREA)
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Abstract

L'invention concerne une composition de teinture servant à teindre des fibres de kératine, en particulier des fibres de kératine humaine telles que les cheveux, qui comprend au moins un composé de radicaux libres du type nitroxyle, au moins un alcool primaire ou secondaire, éventuellement un agent nucléophile, et éventuellement un catalyseur d'oxydation. L'invention concerne également l'utilisation de cette composition pour teindre des fibres de kératine, et un procédé de teinture de fibres de kératine utilisant ladite composition.
PCT/EP2003/015039 2002-12-23 2003-12-19 Composition pour teindre des fibres de keratine, qui renferme au moins un compose de radicaux libres du type nitroxyle et au moins un alcool primaire ou secondaire WO2004056331A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU2003294974A AU2003294974A1 (en) 2002-12-23 2003-12-19 Composition for dyeing keratin fibres, comprising at least one free-radical compound of nitroxyl type and at least one primary or secondary alcohol
DE10393955T DE10393955T5 (de) 2002-12-23 2003-12-19 Zusammensetzung zum Färben von Keratinfasern, die mindestens eine freiradikalische Verbindung vom Nitroxyl-Typ und mindestens einen primären oder sekundären Alkohol enthält

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
FR0216534A FR2848836B1 (fr) 2002-12-23 2002-12-23 Composition pour la coloration des fibres keratiniques comprenant au moins un compose radicalaire de type nitroxyl et au moins un alcool primaire ou secondaire
FR02/16534 2002-12-23
US45623503P 2003-03-21 2003-03-21
US60/456,235 2003-03-21

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WO2004056331A1 true WO2004056331A1 (fr) 2004-07-08

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008000996A2 (fr) * 2006-06-29 2008-01-03 Arkema France Composition tinctoriale comprenant un polynitroxyde triazinique
US20150094267A1 (en) * 2012-04-03 2015-04-02 Kim D. Vandegriff Succinimide-activated nitroxyl compounds and methods for the use thereof for nitroxylation of proteins

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003053375A1 (fr) * 2001-12-21 2003-07-03 Henkel Kommanditgesellschaft Auf Aktien Restructuration et appretage de fibres keratiniques
EP1378544A2 (fr) * 2002-07-05 2004-01-07 L'oreal Composés tétraazapentaméthiniques et leur application pour la teinture des fibres kératiniques

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003053375A1 (fr) * 2001-12-21 2003-07-03 Henkel Kommanditgesellschaft Auf Aktien Restructuration et appretage de fibres keratiniques
EP1378544A2 (fr) * 2002-07-05 2004-01-07 L'oreal Composés tétraazapentaméthiniques et leur application pour la teinture des fibres kératiniques

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008000996A2 (fr) * 2006-06-29 2008-01-03 Arkema France Composition tinctoriale comprenant un polynitroxyde triazinique
FR2902997A1 (fr) * 2006-06-29 2008-01-04 Arkema France Composition tinctoriale comprenant un polynitroxyde triazinique
WO2008000996A3 (fr) * 2006-06-29 2008-02-28 Arkema France Composition tinctoriale comprenant un polynitroxyde triazinique
US20150094267A1 (en) * 2012-04-03 2015-04-02 Kim D. Vandegriff Succinimide-activated nitroxyl compounds and methods for the use thereof for nitroxylation of proteins
US11359004B2 (en) 2012-04-03 2022-06-14 William Schindler Succinimide-activated nitroxyl compounds and methods for the use thereof for nitroxylation of proteins

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