SE327254B - - Google Patents

Info

Publication number
SE327254B
SE327254B SE10801/67*A SE1080167A SE327254B SE 327254 B SE327254 B SE 327254B SE 1080167 A SE1080167 A SE 1080167A SE 327254 B SE327254 B SE 327254B
Authority
SE
Sweden
Prior art keywords
nitro
phenyl
ethylenediamine
formula
benzenesulphonyl
Prior art date
Application number
SE10801/67*A
Inventor
G Kalopissis
A Bugaut
H Gaston-Breton
Original Assignee
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
Application filed by Oreal filed Critical Oreal
Publication of SE327254B publication Critical patent/SE327254B/xx

Links

Classifications

    • 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
    • C09B69/00Dyes not provided for by a single group of this subclass
    • 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
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35Ketones, e.g. benzophenone
    • A61K8/355Quinones
    • 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
    • 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
    • C09B1/00Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16Amino-anthraquinones
    • C09B1/20Preparation from starting materials already containing the anthracene nucleus
    • C09B1/207Dyes with amino groups and with onium groups
    • 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
    • C09B1/00Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16Amino-anthraquinones
    • C09B1/20Preparation from starting materials already containing the anthracene nucleus
    • C09B1/26Dyes with amino groups substituted by hydrocarbon radicals
    • C09B1/28Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups
    • C09B1/285Dyes with no other substituents than the amino groups
    • 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

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1,199,641. Nitrobenzene compounds and intermediates therefor. L'OREAL. 25 July, 1967 [25 July, 1966; 6 July, 1967; 7 July, 1967], No. 34190/67. Heading C2C. [Also in Divisions C4 and D1] The invention comprises (1) compounds of the formula wherein each of the Z radicals represents a nitrobenzene radical, at least one of which Z radicals being substituted by an amino group which is unsubstituted or substituted by one or two alkyl, hydroxyalkyl, aminoalkyl,mono- or dialkylaminoalkyl radicals, the alkyl radicals in the said substituents containing 1 to 4 C atoms or by a C 1 -C 4 alkyl or alkoxy radical; E represents H or OH; m is 0, 1, 2, 3 or 4; and each of the R radicals represents H, C 1 -C 4 alkyl or hydroxyalkyl radical or a radical of the formula wherein n is 2, 3, 4, 5 or 6; and each of R 6 and R 7 represents H or a C 1 -C 4 alkyl radical subject to the proviso that at least one of R 6 and R 7 is alkyl or R 6 and R, together with the N atom form a heterocyclic ring; subject to the proviso that when E represents OH, m is not 2, and acid addition salts and quaternary ammonium salts thereof and (2) compounds of the formulµ and acid addition salts and quaternary ammonium salts thereof, and where X represents a halogen atom. These compounds including those in which E represents OH and m is 2 may be obtained by condensing a compound of the formula wherein Y represents a halogen atom, an alkali metal or alkaline earth metal atom, or a primary, secondary or tertiary amine group, Q represents H or a halogen atom, V is the same as R or represents the radical SO 2 -Z<SP>11</SP> wherein Z<SP>11</SP> represents phenyl or tolyl radical; with (i) a compound of the formula if Y represents a halogen atom; (ii) a compound of the formula wherein Q 1 represents a mobile group, such as NO 2 or a halogen atom, which is readily substituted by an amino group if Y represents a primary amino group; (iii) a compound of the formula if Y represents a secondary or tertiary amino group; (iv) a compound of the formula or of the formula if Y represents an alkali metal or alkaline earth metal and n in Formula IV is 0 and hydrolysing the SO 2 -Z<SP>11</SP> group; and optionally reacting the resulting compound so as to replace Q by a radical of the formula where R 5 represents H, C 1 -C 4 alkyl, hydroxy (C 1 -C 4 ) alkyl or (C 1 -C 4 ) alkoxy-(C 1 -C 4 ) alkyl or a radical of the formula where R 8 and R 9 represent H, C 1 -C 4 alkyl or hydroxyalkyl, acetyl or together with the N atom to which they are attached form a heterocyclic ring; in which Z<SP>111</SP> is the same as, or is a radical capable of being converted during the course of the reaction into Z and when Z<SP>111</SP> is not the same as Z converting it thereto, X represents a halogen atom, M represents an alkali metal or alkaline earth metal atom and n is an integer from 2 to 6, except where indicated otherwise, and, optionally, hydrolysing the product. Further embodiments describe the preparation of restricted classes of compounds falling within the scope of the general Formulµ I, II and III above and methods of modifying the compounds obtained by the said processes. Examples are given for the preparation of the compounds. They are useful as hair dyes. The following intermediates are also prepared:-N,N<SP>1</SP> - dibenzenesulphonyl - N - [(3 - nitro - 4 - methylamino) - phenyl] - N<SP>1</SP> - [4<SP>1</SP> - nitrophenyl] ethylenediamine; N,N<SP>1</SP> - dibenzenesulphonyl - N - [(2 - nitro - 4 - acetamino)- phenyl] - N<SP>1</SP> - [4 - nitrophenyl] - ethylenediamine and N - [(2 - nitro - 4 - amino) phenyl]- N<SP>1</SP> - [41 - nitrophenyl] ethylenediamine; N - [(3 - nitro - 4 - methylamino) phenyl - N - methyl - N<SP>1</SP> - benzenesulphonyl - N<SP>1</SP> - [(3<SP>1</SP> - nitro - 4<SP>1</SP> - methylamino) phenylethylenediamine; N - [(2 - nitro - 4 - benzenesulphonylamino) phenyl] - N<SP>1</SP> - [41 - nitrophenyl] ethylenediamine, N - [(2 - nitro - 4 - (benzenesulphonyl, # - diethylaminoethyl) amino) phenyl] - N<SP>1</SP> - [41 - nitrophenyl]- ethylene diamine and N-[(2-nitro-4-#-diethylaminoethylamino) phenyl] - N<SP>1</SP> - [4 - nitrophenyl] ethylenediamine; N - benzenesulphonyl - N - [(3 - nitro - 4 - methylamino) phenyl] - N<SP>1</SP> - [(2<SP>1</SP> - nitro - 41 - methoxy) phenyl] ethylenediamine; 2 - nitro - 4 - N - benzenesulphonyl - N - # - bromoethylamino - chlorobenzene, N,N<SP>1</SP>- dibenzenesulphonyl - N - [(3 - nitro - 4 - chloro)- phenyl] - N<SP>1</SP> - [4<SP>1</SP> - nitrophenyl] ethylenediamine, N,N<SP>1</SP> - dibenzenesulphonyl - N - [(3 - nitro - 4 - # - acetaminoethylamino) phenyl] - N<SP>1</SP> - [4<SP>1</SP> - nitrophenyl] ethylenediamine and N- [(3 - nitro - 4 - # - acetaminoethylamino) phenyl]- N<SP>1</SP> - [4<SP>1</SP> - nitrophenyl] ethylenediamine; 1 - N - benzenesulphonylamino - 3 - dimethylamino - 4 - nitrobenzene, 1 - N - benzenesulphonyl - N - # - bromoethylamino - 3 - dimethylamino - 4 - nitrobenzene, 1 - N - # - bromoethylamino - 3 - dimethylamino - 4 - nitrobenzene and N - [(4 - nitro - 3 - dimethylamino) phenyl] - N<SP>1</SP> - benzenesulphonyl - N<SP>1</SP> - [(31 - nitro - 4<SP>1</SP> - methylamino) - phenyl] ethylenediamine; 1 - benzenesulphonylamino - 2 - nitro - 4 - acetaminobenzene and N,N<SP>1</SP> - dibenzenesulphonyl - N,N<SP>1</SP> - bis [(2 - nitro - 4 - acetamino) phenyl] tetramethylenediamine; 1 - (N - benzenesulphonyl - N - # - bromoethyl) amino - 2 - nitro - 4 - acetaminobenzene and N,N<SP>1</SP> - dibenzenesulphonyl - N,N<SP>1</SP> - bis [(2 - nitro - 4 - acetamino) phenyl] ethylenediamine; N,N<SP>1</SP> - di - benzenesulphonyl - N,N<SP>1</SP> - bis [(3 - nitro - 4 - methylamino) phenyl] tetramethylenediamine; N,N<SP>1</SP> - di - benzenesulphonyl - N,N<SP>1</SP> - bis [(3- nitro - 4 - chloro)- phenyl] tetramethylenediamine and N,N<SP>1</SP>-dibenzenesulphonyl - N,N<SP>1</SP> - bis [(3 - nitro - 4 - # - aminoethylamino) phenyl] tetramethylenediamine; and N,N<SP>1</SP>-di-benzenesulphonyl-N,N<SP>1</SP>-[(3- nitro - 4 - # - hydroxyethylamino) phenyl] tetramethylenediamine.
SE10801/67*A 1966-07-25 1967-07-24 SE327254B (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
LU51630A LU51630A1 (en) 1966-07-25 1966-07-25
LU54037 1967-07-06
LU54049 1967-07-07

Publications (1)

Publication Number Publication Date
SE327254B true SE327254B (en) 1970-08-17

Family

ID=27350604

Family Applications (1)

Application Number Title Priority Date Filing Date
SE10801/67*A SE327254B (en) 1966-07-25 1967-07-24

Country Status (7)

Country Link
AT (3) AT277413B (en)
BE (2) BE701744A (en)
DE (2) DE1569820C3 (en)
GB (1) GB1199641A (en)
LU (3) LU51630A1 (en)
NL (4) NL6710232A (en)
SE (1) SE327254B (en)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2456764A2 (en) * 1979-05-18 1980-12-12 Oreal Poly:quat. ammonium polymeric dyes - or dye precursors, for keratin fibres, esp. human hair
FR2788221B1 (en) 1999-01-08 2003-05-30 Oreal USE OF CATIONIC MONOBENZENIC NITROANILINS FOR DYEING KERATINIC FIBERS, DYE COMPOSITIONS AND DYEING METHODS
FR2788220B1 (en) * 1999-01-08 2001-02-16 Oreal USE OF CATIONIC DI-BENZENIC NITERS IN DYING KERATINIC FIBERS, TINCTORIAL COMPOSITIONS AND DYING METHODS
FR2788273B1 (en) 1999-01-08 2001-02-16 Oreal CATIONIC MONOBENZENIC NITROPHENYLENEDIAMINES, THEIR USE FOR DYEING KERATINIC FIBERS, TINCTORIAL COMPOSITIONS CONTAINING THEM AND DYEING METHODS
DE19930927A1 (en) * 1999-07-06 2001-01-11 Henkel Kgaa New dyes and dyes
US7241319B2 (en) 2002-12-23 2007-07-10 L'oreal S.A. Dye composition comprising at least one polycationic direct dye, dyeing processes, uses, and multi-compartment devices
FR2848837B1 (en) * 2002-12-23 2005-07-08 Oreal TINCTORIAL COMPOSITION COMPRISING A PARTICULAR POLYCATIONIC DIRECT COLORANT, METHOD FOR DYING, USE AND DEVICES WITH SEVERAL COMPARTMENTS.
US7303591B2 (en) 2004-02-27 2007-12-04 L'oreal S.A. Composition comprising at least one mixed dye comprising at least two chromophores of (hetero) aromatic nitro or cyclic azine type, dyeing process, and mixed dyes
FR2879927A1 (en) * 2004-02-27 2006-06-30 Oreal Tinctorial composition, useful for the dyeing of keratinous fibers in human, comprises a mixed dye comprising two different chromophores
FR2866808A1 (en) * 2004-02-27 2005-09-02 Oreal New mixed dyes, useful for dyeing keratin fibers, especially human hair, comprising at least two chromophores, including at least one of nitrated (hetero)aromatic type, connected by linking arm
FR2866803B1 (en) * 2004-02-27 2007-06-29 Oreal COMPOSITION COMPRISING A MIXED COLOR BASED ON AT LEAST ONE CYCLIC AROMATIC OR CYCLIC AZINE CHROMOPHORIDE (HETERO), COLORING PROCESS AND MIXED COLORANTS
FR2889954B1 (en) * 2005-08-26 2007-10-19 Oreal CATIONIC MIXED DYES COMPRISING ANTHRAQUINONE CHROMOPHORE AND THEIR USE IN CAPILLARY COLOR

Also Published As

Publication number Publication date
NL6710234A (en) 1968-01-26
AT279054B (en) 1970-02-25
BE701744A (en) 1968-01-24
DE1569819A1 (en) 1970-10-01
NL131593C (en)
DE1569820C3 (en) 1973-11-22
BE701743A (en) 1968-01-24
GB1199641A (en) 1970-07-22
LU54037A1 (en) 1969-03-24
AT279055B (en) 1970-02-25
AT277413B (en) 1969-12-29
DE1569820A1 (en) 1970-11-05
LU54049A1 (en) 1969-03-24
DE1569820B2 (en) 1973-04-26
DE1569819B2 (en) 1975-03-06
LU51630A1 (en) 1968-03-14
NL6710232A (en) 1968-01-26
NL131592C (en)
DE1569819C3 (en) 1975-11-06

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