Patent GB-1012793-A (GB)
Title: Improvements in or relating to the dyeing of hair and other keratinous material
Inventor: FROHNSDORFF RAYMOND STANLEY MA
IPC: C09B51/00
Filed: 1961-12-28
Abstract: The invention comprises (a) compounds of the formula <FORM:1012793/C2/1> where R1 is a C1-3 alkyl, or a hydroxyl- or amino-substituted C1-3 alkyl group, A is a hydroxyl or methoxy group when B is an amino group or A is an amino group when B is a hydroxyl or methoxy group, and X, which is in the 5- or 6-position, is a hydrogen or halogen atom, or a C1-3 alkyl, hydroxyl- or amino-substituted C1-3 alkyl, amino or hydroxyl group, and acid addition salts thereof, (b) compounds of the formula: <FORM:1012793/C2/2> where A1 is a methoxy group when B1 is an amino group and A1 is an amino group when B1 is a methoxy group and X1, which may be substituted in the 5- or 6-position, is a halogen atom or a C1-3 alkyl, hydroxyl- or amino-substituted C1-3 alkyl, amino or hydroxyl group, and acid addition salts thereof, and (c) compounds of the formula: <FORM:1012793/C2/3> where A is an amino group when B is a hydroxyl or methoxy group and A is a hydroxyl or methoxy group when B is an amino group and X1, which may be substituted in the 5- or 6-position, is a halogen atom or a C1-3 alkyl or hydroxyl- or amino-substituted C1-3 alkyl group, and acid additions salts thereof. The compounds are prepared by standard procedures from readily available starting materials.  Thus, compounds of Formula (III) can be obtained from the corresponding X1-substituted phenol by nitration and reduction to give the corresponding ortho- or para-aminophenol which is then acetylated, nitrated, reduced and hydrolysed to give the diamino-phenol.  Compounds of Formula (II) where X1 = alkyl, hydroxyalkyl, aminoalkyl or halogen can be prepared by O-methylation of the corresponding compound (III) if the other groups are protected by acylation. Alternatively they can be obtained from the corresponding X1-substituted anisole by the sequence described above for the diaminophenol of Formula (III).  Compounds of Formula (II), where X1 is hydroxy can be obtained by stepwise O-acetylation, nitration, ester hydrolysis, reduction, N-acetylation, nitration, amide hydrolysis and reduction of the corresponding methoxyphenol. Compounds of Formula (II) where X1 is amino may be prepared by N-acetylation followed by nitration, hydrolysis and reduction of the appropriate diaminoanisole.  The compounds of Formula (I) can be obtained from the corresponding nitroaminophenol or nitroaminoanisole by N-alkylation with an alkyl halide hydroxyalkyl halide, epoxyalkane, alkeneimine or aminoalkyl halide or from the appropriate X1-substituted nitrochlorophenol or anisole by reaction with a primary alkylamine or hydroxyalkylamine. The resulting R1-substituted nitroaminophenols or nitroaminoanisoles can then be reduced to the compounds of Formula (I). Some of the halogeno diaminophenols and diaminoanisoles can also be prepared by direct nuclear halogenation of the appropriate compound or its aryl derivative.ALSO:Preparations for use in dyeing hair and other keratinous material comprise an aqueous solution of one or more compounds of the formula: <FORM:1012793/D1-D2/1> where R is a hydrogen atom or a C1-3 alkyl or a hydroxyl- or amino-substituted C1-3 alkyl group, A is a hydroxyl or methoxy group when B is an amino group or A is an amino group when B is a hydroxyl or methoxy group, and X, which may be in the 5- or 6- position, is a hydrogen or halogen atom, or a C1-3 alkyl, hydroxyl- or amino-substituted C1-3 alkyl, amino or hydroxyl group, or the acid addition salts thereof, and one or more of the following: a surface active agent, a thickner, a solvent, a perfume, a preservative, an antioxidant, and a pH stabilizer.  Suitable surface active agents are triethanolamine lauryl sulphate, diethanolamide of cocoanut fatty acids, stearyl dimethyl benzene ammonium chloride, and sodium lauryl sulphate; a suitable thickener is the ethylene oxide derivative of higher fatty alcohols; suitable preservatives sodium sulphite and sodium borate.  The preparations can also include dyestuffs of other classes.