US3665036A - Dye forming nitroparaphenylenediamine sulfonyl derivatives - Google Patents

Dye forming nitroparaphenylenediamine sulfonyl derivatives Download PDF

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US3665036A
US3665036A US10040A US3665036DA US3665036A US 3665036 A US3665036 A US 3665036A US 10040 A US10040 A US 10040A US 3665036D A US3665036D A US 3665036DA US 3665036 A US3665036 A US 3665036A
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nitro
benzene
amino
solution
methylamino
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Gregoire Kalopissis
Andree Bugaut
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LOreal SA
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LOreal SA
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    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B51/00Nitro or nitroso dyes
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41Amines
    • A61K8/418Amines containing nitro groups
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/06Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065Preparations for temporary colouring the hair, e.g. direct dyes
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/125Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

Definitions

  • R, and R are H, alkyl or hydroxyalkyl and may form a heterocyclic ring with the N atom, R is H, alkyl or hydroxyalkyl, R is H or CH and n is 2-6.
  • the present invention relates to new intermediate compounds which can be used to form dye compounds which can be used to dye keratin fibers, such as live human hair and animal fibers.
  • the object of the present invention is to provide improved nitroparaphenylenediamine dye compounds selected from the croup consisting of R1 R-I I(CHz)nN in which R, R and R are selected from the group consisting of H, lower alkyl having one to six carbon atoms and lower hydroxyalkyl having one to six carbon atoms, and R and R are selected from the group consisting of H, lower alkyl having one to six carbon atoms and lower hydroxyalkyl having one to six carbon atoms, and together with the N a group piperidino, morpholino or phtalimido, n is a number from 2 to 6, and the N group is in the 2 or 3 position on the benzene ring, wherein R and R cannot both be H, and the amino group on the benzene ring situated in the ortho position to the nitro group is never tertiary, and when the N0 group is in the 2 position either R or R" must be H, and when R and R are H, R
  • Dyes having formula (I) have the advantage of having, when cold, a great affinity for keratinic fibers. Hair dyes made from these dyes can form very strong shades and the strength of the coloration and the affinity of the dye compound for keratinic fibers, permit the dyes to be used, even in very small quantities, in tinctorial solutions at room temperature. This peculiarity is very valuable because it makes the use of dyes having a relatively poor solubility possible and satisfactory.
  • dye colorations of the dyes of the present invention have a particularly good resistance to fading caused by light and washing.
  • they may be used in a pH range which is much wider than the presentlyknown range of usage for analogous types of dyes. They may in fact be used in compositions having a pH of 4 to 10. The preferable range is 6-10.
  • Dyes of the present invention also have the peculiarity of having as a substituent on one of the amino groups fixed on the benzene ring, a chain which has a terminal amino group which is quatemizable when said terminal amino group is tertiary.
  • the quaternary compounds thus obtained may also be used as hair dyes in the same way as the corresponding tertiary compounds, and the chloro compounds of formula ll.
  • tinctorial compositions of this invention do not require the addition of peroxides such as hydrogen peroxide as other hair dyes do in order to develop the color.
  • peroxides such as hydrogen peroxide
  • other ingredients commonly used in hair-dyeing treatments may be added to these tinctorial compositions, such as organic solvents, thickeners, detergents, lacs, etc.
  • dyes of the type conforming to the invention it is possible to notably vary the dye compound concentration in the tinctorial solutions, but the preferable concentration is between 0.1 and 3.5 percent.
  • the time during which the aforementioned tinctorial solutions are in contact with the hair may vary within wide limits, but preferably it should be between 5 and 30 minutes.
  • the temperature at which the tinctorial solutions are applied may also be varied, but in most cases they may be advantageously used at ordinary room temperature.
  • any of the dyes of this invention may be mixed with other dyes of the invention or with any other nitrated dyes, such as, nitroorthophenylenediamine, nitroparaphenylenediamine and alkyl or hydroxyalkyl derivatives of these compounds.
  • the new dyes of the invention may also be mixed with azo or anthraquinone dyes or other types of dyes usually used for hair-dyeing.
  • the intermediate dye forming compounds of this invention are compounds which have the formula:
  • R and R are selected from the group consisting of hydrogen, lower alkyl and lower hydroxyalkyl, and may form a heterocyclic ring with the nitrogen atom to which they are attached, R is selected from the group consisting of hydrogen, lower alkyl and lower hydroxyalkyl, R is selected from the group consisting of hydrogen, and methyl, and n is an integer between 2 and 6 inclusive, and a compound having the formu- SOQ-Rr N/ (CH1) n N in which R,, R R R and n have the meaning defined above, in which said lower alkyl and hydroxyalkyl groups have one to six carbon atoms.
  • Second step Preparation of l-N-methylamino-2-nitro-4-[N- (B-diethylamino)ethyl]amino benzene dihydrochloride.
  • the base is then isolated from this dihydrochloride in a conventional manner.
  • reaction mixture is kept at 60 C for 3 hours. After chilling, it is extracted with ethyl acetate and the ethyl acetate solution is washed first with normal sodium hydroxide, and then with water to eliminate the initial product in the form of its tosylate. The product is then extracted using iced normal hydrochloric acid, in the form of its hydrochloride.
  • Third step 0.0133 mol(6 g) of l-[N-benzenesulfonyl-N-,B- diethyl-aminoethyl ]amino-2-nitro-4-( N '-methyl-N-acetyl amino benzene in 50 cm of concentrated hydrochloric acid is heated to reflux for 2 hours. After dilution, it is chilled while adding 5 N sodium hydroxide. Drying yields 3.2 g of l-N-B- diethyl-aminoethylamino-Z-nitro-4-methylamino benzene which after recrystallization in a mixture of benzene and hexane, melts at 74 C.
  • nitro-4-amino benzene First step: Preparation of 1-N-p-toluene-sulfonylamino-2- nitro-4-acetylarnino benzene This product is prepared in the usual manner, by reacting ptoluene sulfochloride with 1-amino-2-nitro-4-acetyl-amino benzene in solution in pyridine.
  • Second step Preparation of 1-N-p-toluenesulfonyl-N-fldiethyl-aminoethyl-amino-2-nitro-4-acety1amino benzene 0.086 mols (14.8 g) of B-diethylarnino-ethylchloride hydrochloride in solution in 50 cm of water, and 60 cm of 2 N sodium hydroxide, are simultaneously added little by little, at about 60 C, to a solution of 0.0286 mols g) of l-N-ptoluene-sulfonyl-amino-2-nitro-4-acetylamino benzene in 40 cm of normal sodium hydroxide.
  • reaction mixture is kept for three hours at 60 C. After cooling, it is extracted with ethyl acetate, and the resulting ethyl acetate solution washed first with sodium hydroxide and then with water in order to eliminate the starting product in the form of the tosylate. The product is then extracted in the form of its hydrochloride, using iced normal hydrochloric acid. The resulting solution is alkalized with sodium hydroxide and 7 g of 1-(N-p-toluenesulfonyl-N-B- diethylaminoethyl)-amino-2-nitro-4-acetylamino benzene is precipitated. When dried under vacuum and recrystallized in a toluene-hexane mixture, this melts at 166 C.
  • hydrazine hydrate 0.04 mol of hydrazine hydrate is added to a solution of 0.02 mol (10.16 g) of substituted phthalimide in 80 cm of propanol, and then heated for 30 minutes in a boiling waterbath. Most of the resultant phthalhydrazide is eliminated by filtration of the hot reaction mixture. After cooling, an orange oil is isolated by decantation and dissolved in ethyl acetate. This ethyl acetate solution is extracted with a /2 N hydrochloric solution.
  • the aqueous hydrochloric phase is alkalized, and drying yields 4.5 g of 1-N-methylamino-2-nitro-4-(N'- benzenesulfonyl-N'w-aminobutyl)-amino benzene which, after recrystallization in ethyl acetate, melts at 135 C.
  • the analysis of this product is:
  • Second step Preparation of the dihydrochloride of l-N- methylamino-2-nitro-4-( N -'y-[ N B-hydroxyethyl-methyl 'y-aminopropyl )-amino benzene.
  • Second step Preparation of l-N-methylamino2-nitro-4-(N'- benzenesulfonyl-N-w-phthalimidohexyl)amino benzene.
  • 0.0268 rnol (12.6 g) of 1-N-methylamino-2-nitro-4-(N- benzenesulfonyl-N'-w-bromohexyl)-amino benzene is dissolved in 50 cm of dimethylformamidc. 0.0322 rnol (5.96 g) of potassium phthalimide is added and the reaction mixture is heated for an hour in a boiling water-bath. It is poured into 400 cm of water and drying yields 13.8 g of a crude product which, after recrystallization in ethyl acetate, melts at 149 C.
  • the propanolic mother liquor after saturation with dry hydrochloric acid, yields another 2 g of the desired product, isolated in the form of the hydrochloride.
  • reaction mixture After chilling, the reaction mixture is poured into a liter of water and drying yields a gummy product which, after three crystallizations in toluene, yields 12 g of l-N- methylamino-2-nitro-4-(N-benzenesulfonyl-N'-B- phthalimidoethyl)-amino benzene, which melts at 218 C.
  • the yield is poorer than that obtained by the preceding method.
  • Second step Preparation of l-N-methylamino-2-nitro-4-(N- benzenesulfonyl-N'-/3-aminoethyl )-amino benzene.
  • the propanolic solution is then concentrated to about 80 cm After chilling, 30 g of the desired product are obtained in the form of an oil which crystallizes slowly. After recrystallization in a mixture of ethanol and water, the product melts at 1 C. Analysis yields the following results:
  • the sodium salt of l-N-benzene-sulfonyl-amino-2-nitro-4- acetamido benzene is used as raw material.
  • This salt may be prepared in the manner indicated in Luxembourg Pat. application No. 49,213 filed 30 July 1965. It should be noted, however, that in this Luxembourg patent it is indicated that the reaction may be carried out in water. It has since been found that the yield is much higher if dimethyl-formamide is used as the solvent, and dimethyl-formamide has accordingly been used in the first step of the present example, which will now be described.
  • Second step Preparation of the dihydrobromide of l-N- B- (diethylamino)-ethylamino2-nitro4-amino benzene.
  • 0.1 mols (34 g) of l-N-'y-(diethylamino)-propylamino-2- nitro-4 amino benzene is heated for 2 hours in a boiling waterbath, with 50 g (0.4 mols) of 99.5% glycol bromohydrin added to 10 cm of water and 20 g of calcium carbonate. 200 cm of water is then added, and the solution filtered. After alkalization with sodium hydroxide, the solution is extracted with butyl-alcohol. The solvent is eliminated under vacuum and the oily residue dissolved in methanol. The methanolic solution is saturated with dry gaseous hydrochloric acid and drying yields 30.12 g of the dihydrochloride, which melts and decomposes at C.
  • diethylaminoethyl lamino-benzene 0.152 g 4-nitro-l,3-phenylenediamine 0.030 g
  • Dihydrochloride of l-N-B-(diethylamino)- ethylamino-2-nitro-4-N'-di-fi- This composition is applied to 90% white hair and left for 10 minutes, followed by rinsing and shampooing. The result is a light golden blond.
  • This composition is applied to 90% white hair. It is left to act for 10 minutes. The hair is then rinsed and shampooed. An ash blond shade results.
  • All of the compounds of this invention may be made by reacting substituted amino chloride or halide with an alkaline, such as Na, K, etc. or alkaline earth such as Ca, Mg, etc. metal salt of an aromatic or phenyl N-aryl or phenyl sulfonyl amine in the manner illustrated by Example 2.
  • an alkaline such as Na, K, etc. or alkaline earth such as Ca, Mg, etc.
  • metal salt of an aromatic or phenyl N-aryl or phenyl sulfonyl amine in the manner illustrated by Example 2.
  • R and R are selected from the group consisting of hydrogen, lower alkyl and lower hydroxyalkyl, R is selected from the group consisting of hydrogen, lower alkyl and lower hydroxyalkyl, R is selected from the group consisting of hydrogen and methyl, and n is an integer between 2 an 6 inclusive, and a compound having the formula:

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  • Health & Medical Sciences (AREA)
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  • General Health & Medical Sciences (AREA)
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US10040A 1965-07-30 1970-02-09 Dye forming nitroparaphenylenediamine sulfonyl derivatives Expired - Lifetime US3665036A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
LU49213 1965-07-30
LU49214 1965-07-30
LU50348 1966-01-27
LU51474A LU51474A1 (zh) 1965-07-30 1966-07-04

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AT (4) AT281222B (zh)
BE (2) BE684863A (zh)
CH (8) CH457491A (zh)
DE (3) DE1569816A1 (zh)
FR (2) FR1506350A (zh)
GB (2) GB1164824A (zh)
IT (1) IT1048380B (zh)
LU (4) LU49214A1 (zh)
NL (4) NL6610759A (zh)

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3925474A (en) * 1968-05-16 1975-12-09 Oreal Nitroparaphenylene diamine derivatives and methods of making them
US4058562A (en) * 1975-09-10 1977-11-15 Pfizer Inc. Antiviral substituted (phenylenedimethylene) diamines
US4727192A (en) * 1984-12-13 1988-02-23 L'oreal 2,4-dinitro- or 2-amino-4-nitro- or 2-nitro-4-amino-6-hydroxyalkylanilines, the process for preparation thereof and their use in dyeing keratinous fibers, and especially human hair
US5041143A (en) * 1984-10-09 1991-08-20 L'oreal N,N'-disubstituted nitro-para-phenylenediamines, and dyeing compositions containing the same
US20110154583A1 (en) * 2009-12-21 2011-06-30 Living Proof, Inc. Coloring agents and methods of use thereof
US8840684B2 (en) 2010-12-15 2014-09-23 L'oreal Process for dyeing keratin fibres using a direct dye bearing a disulfide/thiol/protected thiol function and water vapour
US9044412B2 (en) 2011-07-05 2015-06-02 L'oreal Dye composition using a long-chain ether of an alkoxylated fatty alcohol and a cationic polymer, processes and devices using the same
US9060944B2 (en) 2011-07-05 2015-06-23 L'oreal Cosmetic composition rich in fatty substances comprising a polyoxyalkylenated fatty alcohol ether and a direct dye and/or an oxidation dye, the dyeing method and the device
US9066890B2 (en) 2011-07-05 2015-06-30 L'oreal Dye composition comprising an alkoxylated fatty alcohol ether and a fatty alcohol
US9265705B2 (en) 2011-02-25 2016-02-23 L'oreal Composition for dyeing keratin fibres comprising a direct dye bearing a disulphide/thiol function, a nonionic surfactant, an amphoteric surfactant, an ethoxylated fatty alcohol, an alkaline agent and a reducing agent
US9271915B2 (en) 2011-02-25 2016-03-01 L'oreal Composition for dyeing keratin fibres comprising a direct dye bearing a disulphide/thiol function, a non-cellulose-based thickening polymer, an alkaline agent and a reducing agent
US9345652B2 (en) 2011-02-25 2016-05-24 L'oreal Composition for dyeing keratin fibres comprising a direct dye bearing a disulphide/thiol function, a sparingly or non-ethoxylated fatty alcohol, a cationic surfactant, an alkaline agent and a reducing agent
US9522106B2 (en) 2011-02-25 2016-12-20 L'oreal Composition for dyeing keratinous fibres comprising a direct dye having a disulphide/thiol functional group, a thickening polymer, an ethoxylated fatty alcohol and/or a nonionic surfactant, an alkaline agent and a reducing agent
US9827185B2 (en) 2012-08-02 2017-11-28 L'oreal Dyeing composition comprising at least one fatty substance, at least one oxidizing agent and at least one non-ionic, anionic and amphoteric surfactant
US10117811B2 (en) 2013-12-23 2018-11-06 L'oreal Packaging article comprising an envelope and an anhydrous dye composition comprising an oxidation dye, use of the same and process for dyeing keratin fibres
US10130829B2 (en) 2013-12-23 2018-11-20 L'oreal Packaging article comprising an envelope and an anhydrous dye composition comprising a direct dye, use of the same and process for dyeing keratin fibres
US10137063B2 (en) 2012-08-02 2018-11-27 L'oreal Dye composition comprising nonionic guar gum or a nonionic derivative thereof, process and device for the same
US10201483B2 (en) 2012-08-02 2019-02-12 L'oreal Dye composition in cream form comprising at least one oil and little or no solid fatty alcohol, dyeing process and suitable device
US10226411B2 (en) 2012-08-02 2019-03-12 L'oreal Dyeing composition comprising a fatty substance, a non-ionic guar gum, an amphoteric surfactant and a non-ionic or anionic surfactant, and an oxidizing agent, dyeing process and suitable device
US11911636B2 (en) 2013-12-23 2024-02-27 L'oreal Process for treating keratin fibers using a packaging article comprising an envelope and an anhydrous composition comprising an oxidizing agent

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3867456A (en) * 1965-07-30 1975-02-18 Oreal Mono-omega-haloalkyl amines
LU60732A1 (zh) * 1970-04-15 1972-03-02
FR2361447A1 (fr) * 1976-08-12 1978-03-10 Oreal Composes colorants constitues de polymeres cationiques hydrosolubles et compositions tinctoriales les contenant
PT73492B (fr) * 1980-08-08 1982-10-28 Oreal Compositions tinctoriales pour cheveux a base de colorants directs nitres et procede de teinture utilisant les dites compositions
LU83686A1 (fr) * 1981-10-08 1983-06-08 Oreal Composition tinctoriale pour fibres keratiniques a base de colorants nitres benzeniques
FR2519251B1 (fr) * 1982-01-05 1985-11-22 Oreal Composition tinctoriales a base de precurseurs de colorants d'oxydation et d'orthonitranilines n-substituees comprenant une alcanolamine et du bisulfite de sodium et leur utilisation en teinture des fibres keratiniques
LU85681A1 (fr) * 1984-12-13 1986-07-17 Oreal Nouvelles nitro-2,amino-4,hydroxyalkyl-6 anilines,leur procede de preparation et leur utilisation en teinture des fibres keratiniques et en particulier des cheveux humains
LU85939A1 (fr) * 1985-06-10 1987-01-13 Oreal Nouvelles metaphenylenediamines nitrees,halogenees en position 6 et leur utilisation en teinture des matieres keratiiques
LU86309A1 (fr) * 1986-02-14 1987-09-10 Oreal Composition pour fibres keratiniques et en particulier pour cheveux humains,a base de nitroanilines halogenes,procede de teinture utilisant ladite composition tinctoriale et nouvelles 2-nitroanilines halogenees utilisees
LU86308A1 (fr) * 1986-02-14 1987-09-10 Oreal Composition tinctoriale pour fibres keratiniques a base de 2-nitrometaphenylenediamines,procede de preparation de ces composes et nouvelles 2-nitro-metaphenylenediamines utilisees
FR2724560B1 (fr) 1994-09-21 1996-12-20 Oreal Procede de coloration directe des fibres keratiniques a l'aide de colorants directs cationiques et de vapeur d'eau
FR2788273B1 (fr) 1999-01-08 2001-02-16 Oreal Nitrophenylenediamines cationiques monobenzeniques, leur utilisation pour la teinture des fibres keratiniques, compositions tinctoriales les renfermant et procedes de teinture
FR2788220B1 (fr) 1999-01-08 2001-02-16 Oreal Utilisation de composes nitres di-benzeniques cationiques en teinture des fibres keratiniques, compositions tinctoriales et procedes de teinture
FR2788221B1 (fr) 1999-01-08 2003-05-30 Oreal Utilisation de nitroanilines cationiques monobenzeniques en teinture des fibres keratiniques, compositions tinctoriales et procedes de teinture

Cited By (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3925474A (en) * 1968-05-16 1975-12-09 Oreal Nitroparaphenylene diamine derivatives and methods of making them
US4058562A (en) * 1975-09-10 1977-11-15 Pfizer Inc. Antiviral substituted (phenylenedimethylene) diamines
US5041143A (en) * 1984-10-09 1991-08-20 L'oreal N,N'-disubstituted nitro-para-phenylenediamines, and dyeing compositions containing the same
US4727192A (en) * 1984-12-13 1988-02-23 L'oreal 2,4-dinitro- or 2-amino-4-nitro- or 2-nitro-4-amino-6-hydroxyalkylanilines, the process for preparation thereof and their use in dyeing keratinous fibers, and especially human hair
US4888445A (en) * 1984-12-13 1989-12-19 L'oreal New 2,4-dinitro- or 2-amino-4-nitro- or 2-nitro-4-amino-6-hydroxyalkylanilines, the process for preparation thereof and their use in dyeing keratinous fibres, and especially human hair
US8187340B2 (en) 2009-12-21 2012-05-29 Living Proof, Inc. Coloring agents and methods of use thereof
US9248086B2 (en) 2009-12-21 2016-02-02 Living Proof, Inc. Coloring agents and methods of use thereof
EP2516555A2 (en) * 2009-12-21 2012-10-31 Living Proof, Inc. Coloring agents and methods of use thereof
US8444715B2 (en) 2009-12-21 2013-05-21 Living Proof, Inc. Coloring agents and methods of use thereof
EP2516555A4 (en) * 2009-12-21 2013-05-22 Living Proof Inc COLORING AGENT AND METHOD FOR USE THEREOF
US8758451B2 (en) 2009-12-21 2014-06-24 Living Proof, Inc. Coloring agents and methods of use thereof
US8932370B2 (en) 2009-12-21 2015-01-13 Living Proof, Inc. Coloring agents and methods of use thereof
US20110154583A1 (en) * 2009-12-21 2011-06-30 Living Proof, Inc. Coloring agents and methods of use thereof
US9504637B2 (en) 2009-12-21 2016-11-29 Living Proof, Inc. Coloring agents and methods of use thereof
US8840684B2 (en) 2010-12-15 2014-09-23 L'oreal Process for dyeing keratin fibres using a direct dye bearing a disulfide/thiol/protected thiol function and water vapour
US9522106B2 (en) 2011-02-25 2016-12-20 L'oreal Composition for dyeing keratinous fibres comprising a direct dye having a disulphide/thiol functional group, a thickening polymer, an ethoxylated fatty alcohol and/or a nonionic surfactant, an alkaline agent and a reducing agent
US9265705B2 (en) 2011-02-25 2016-02-23 L'oreal Composition for dyeing keratin fibres comprising a direct dye bearing a disulphide/thiol function, a nonionic surfactant, an amphoteric surfactant, an ethoxylated fatty alcohol, an alkaline agent and a reducing agent
US9271915B2 (en) 2011-02-25 2016-03-01 L'oreal Composition for dyeing keratin fibres comprising a direct dye bearing a disulphide/thiol function, a non-cellulose-based thickening polymer, an alkaline agent and a reducing agent
US9345652B2 (en) 2011-02-25 2016-05-24 L'oreal Composition for dyeing keratin fibres comprising a direct dye bearing a disulphide/thiol function, a sparingly or non-ethoxylated fatty alcohol, a cationic surfactant, an alkaline agent and a reducing agent
US9066890B2 (en) 2011-07-05 2015-06-30 L'oreal Dye composition comprising an alkoxylated fatty alcohol ether and a fatty alcohol
US9060944B2 (en) 2011-07-05 2015-06-23 L'oreal Cosmetic composition rich in fatty substances comprising a polyoxyalkylenated fatty alcohol ether and a direct dye and/or an oxidation dye, the dyeing method and the device
US9044412B2 (en) 2011-07-05 2015-06-02 L'oreal Dye composition using a long-chain ether of an alkoxylated fatty alcohol and a cationic polymer, processes and devices using the same
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US10117811B2 (en) 2013-12-23 2018-11-06 L'oreal Packaging article comprising an envelope and an anhydrous dye composition comprising an oxidation dye, use of the same and process for dyeing keratin fibres
US10130829B2 (en) 2013-12-23 2018-11-20 L'oreal Packaging article comprising an envelope and an anhydrous dye composition comprising a direct dye, use of the same and process for dyeing keratin fibres
US11911636B2 (en) 2013-12-23 2024-02-27 L'oreal Process for treating keratin fibers using a packaging article comprising an envelope and an anhydrous composition comprising an oxidizing agent

Also Published As

Publication number Publication date
DE1617698B2 (de) 1975-09-11
CH519466A (fr) 1972-02-29
DE1617698A1 (de) 1971-04-22
DE1617699A1 (de) 1971-07-29
LU49213A1 (zh) 1967-01-30
CH510624A (fr) 1971-07-31
IT1048380B (it) 1980-11-20
LU51474A1 (zh) 1968-03-12
NL6610759A (zh) 1967-01-31
NL6610757A (zh) 1967-01-31
LU50348A1 (zh) 1967-07-27
AT277414B (de) 1969-12-29
BE684863A (zh) 1967-01-30
NL130871C (zh)
CH516507A (fr) 1971-12-15
CH518096A (fr) 1972-01-31
DE1617699B2 (de) 1975-10-30
CH457491A (fr) 1968-06-15
CH519465A (fr) 1972-02-29
CH518902A (fr) 1972-02-15
AT279053B (de) 1970-02-25
DE1569816A1 (de) 1969-11-06
DE1543810C3 (zh) 1978-12-07
GB1164824A (en) 1969-09-24
NL7006131A (en) 1970-08-25
AT278988B (de) 1970-02-25
CH524370A (fr) 1972-06-30
DE1543810A1 (de) 1970-02-26
LU49214A1 (zh) 1967-01-30
BE684859A (zh) 1967-01-30
JPS582204B1 (zh) 1983-01-14
AT281222B (de) 1970-05-25
FR1491617A (fr) 1967-08-11
FR1506350A (fr) 1967-12-22
GB1164825A (en) 1969-09-24
DE1543810B2 (zh) 1978-04-20

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