公开(公告)号：DE1967172B1

公开(公告)日：1979-03-29

申请号：DE1967172

申请日：1969-07-31

Applicant: OREAL

Inventor： KALOPISSIS GREGOIRE ,  ARMANCEY BUGAUT GEB ,  GASTON-BRETON HUBERT

IPC: A61K20060101 ,  C07C103/38 ,  C07C103/183 ,  A61K7/13

Abstract: 1,229,517. Substituted aminophenols. L'OREAL. 14 Aug., 1969 [14 Aug., 1968], No. 40713/69. Heading C2C. [Also in Division D1] The invention comprises the compounds of formula in which R represents hydrogen, a lower alkyl or hydroxyalkyl or acyl radical, or a N-alkylated or unsubstituted amino lower alkyl or carbamylmethyl group, the "alkyl" groups of these radicals having 1-6 carbon atoms. The N-acyl compounds may be prepared by reacting the corresponding acid anhydride with 3-amino-2,6- dimethyl phenol while the compounds of the above formula in which R represents an alkyl, hydroxyalkyl, amino-alkyl, or carbamyl-methyl radical may be obtained by reacting a suitably selected halogenated derivative with 3-amino- 2,6-dimethyl phenol. 3-Amino-2,6-dimethylphenol may be obtained by reducing the corresponding nitro compound. The following compounds are prepared in the examples: 3-amino- 2,6 - dimethylphenol; 3 - acetylamino - 2,6 - dimethylphenol; 3 - propionylamino - 2,6 - dimethylphenol, and 3-carbamylmethylamino- 2,6-dimethylphenol.

公开(公告)号：GB1272329A

公开(公告)日：1972-04-26

申请号：GB4438069

申请日：1969-09-08

Applicant: OREAL

Inventor： KALOPISSIS GREGOIRE ,  GASCON JEAN ,  BUGAUT ANDREE ,  GALLIEN JACQUELINE ,  GASTON-BRETON HUBERT

IPC: C07C275/14

Abstract: 1,272,329. Hair dyeing compositions. L'OREAL. 8 Sept., 1969 [9 Sept., 1968; 16 Jan., 1969], No. 44380/69. Heading D1B. [Also in Division C2] Oxidation bases, used in hair dyeing compositions, have the general formula 5 wherein R 1 and R 2 are each H, halogen, alkyl or alkoxy; 2 is oxygen or sulphur and n is an integer from 2 to 4. Their acid addition salts may be used. The compositions which may be in the form of an aqueous solution, cream, gel or aerosol are preferably alkaline at pH 8 to 10 and comprise an oxidation base, preferably 0.1 to 10% by weight, a carrier and at least one coupler, e.g. m - aminophenol, 3 - N - carbamylmethylamino - phenol, resorcinol, m - phenylene diamine, 2,4 - diamionanisole sulphate or 3 - hydroxyphenylurea. The molar ratio base : coupler is preferably 1:1 to 1:4. Other conventional adjuvants include dyestuffs, wetting, dispersing or penetrating agents and the compositions are applied together with an oxidising agent, e.g. hydrogen peroxide by contacting the hair for 5 to 30 minutes followed by rinsing, shampooing and drying.

公开(公告)号：GB1199641A

公开(公告)日：1970-07-22

申请号：GB3419067

申请日：1967-07-25

Applicant: OREAL

Inventor： KALOPISSIS GREGOIRE ,  BUGAUT ANDREE ,  GASTON-BRETON HUBERT

IPC: A61K8/35 ,  A61K8/41 ,  A61Q5/06 ,  C09B1/20 ,  C09B1/28 ,  C09B51/00 ,  C09B69/00 ,  D06P1/42 ,  D06P3/14

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 11 wherein Z 11 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 11 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 111 is the same as, or is a radical capable of being converted during the course of the reaction into Z and when Z 111 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 1 - dibenzenesulphonyl - N - [(3 - nitro - 4 - methylamino) - phenyl] - N 1 - [4 1 - nitrophenyl] ethylenediamine; N,N 1 - dibenzenesulphonyl - N - [(2 - nitro - 4 - acetamino)- phenyl] - N 1 - [4 - nitrophenyl] - ethylenediamine and N - [(2 - nitro - 4 - amino) phenyl]- N 1 - [41 - nitrophenyl] ethylenediamine; N - [(3 - nitro - 4 - methylamino) phenyl - N - methyl - N 1 - benzenesulphonyl - N 1 - [(3 1 - nitro - 4 1 - methylamino) phenylethylenediamine; N - [(2 - nitro - 4 - benzenesulphonylamino) phenyl] - N 1 - [41 - nitrophenyl] ethylenediamine, N - [(2 - nitro - 4 - (benzenesulphonyl, # - diethylaminoethyl) amino) phenyl] - N 1 - [41 - nitrophenyl]- ethylene diamine and N-[(2-nitro-4-#-diethylaminoethylamino) phenyl] - N 1 - [4 - nitrophenyl] ethylenediamine; N - benzenesulphonyl - N - [(3 - nitro - 4 - methylamino) phenyl] - N 1 - [(2 1 - nitro - 41 - methoxy) phenyl] ethylenediamine; 2 - nitro - 4 - N - benzenesulphonyl - N - # - bromoethylamino - chlorobenzene, N,N 1 - dibenzenesulphonyl - N - [(3 - nitro - 4 - chloro)- phenyl] - N 1 - [4 1 - nitrophenyl] ethylenediamine, N,N 1 - dibenzenesulphonyl - N - [(3 - nitro - 4 - # - acetaminoethylamino) phenyl] - N 1 - [4 1 - nitrophenyl] ethylenediamine and N- [(3 - nitro - 4 - # - acetaminoethylamino) phenyl]- N 1 - [4 1 - 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 1 - benzenesulphonyl - N 1 - [(31 - nitro - 4 1 - methylamino) - phenyl] ethylenediamine; 1 - benzenesulphonylamino - 2 - nitro - 4 - acetaminobenzene and N,N 1 - dibenzenesulphonyl - N,N 1 - bis [(2 - nitro - 4 - acetamino) phenyl] tetramethylenediamine; 1 - (N - benzenesulphonyl - N - # - bromoethyl) amino - 2 - nitro - 4 - acetaminobenzene and N,N 1 - dibenzenesulphonyl - N,N 1 - bis [(2 - nitro - 4 - acetamino) phenyl] ethylenediamine; N,N 1 - di - benzenesulphonyl - N,N 1 - bis [(3 - nitro - 4 - methylamino) phenyl] tetramethylenediamine; N,N 1 - di - benzenesulphonyl - N,N 1 - bis [(3- nitro - 4 - chloro)- phenyl] tetramethylenediamine and N,N 1 -dibenzenesulphonyl - N,N 1 - bis [(3 - nitro - 4 - # - aminoethylamino) phenyl] tetramethylenediamine; and N,N 1 -di-benzenesulphonyl-N,N 1 -[(3- nitro - 4 - # - hydroxyethylamino) phenyl] tetramethylenediamine.