Patent GB-760705-A (GB)
Title: Improvements in azo dyestuffs
IPC: C09B35/50
Filed: 1953-10-16
Abstract: The invention comprises polyazo dyestuffs of formula:-Z-N=N-D-N=N-Y wherein D is a 4 : 41 - diphenyl radical which possesses in one of the two ortho positions to each -N=N- a metallizeable substituent,, i.e. -OH, -OCH3, -OC2H5, -OCH2, COOH and -COOH, Y is a residue of formula:- <FORM:0760705/IV(b)/1> wherein R is hydrogen, alkyl, hydroxyalkyl, cycloalkyl, aralkyl or aryl and A may bear further substituents other than carboxylic acid groups, and wherein Z possesses the significance of Y or is of the same formula as Y or denotes the residue of any other coupling component of the benzene or naphthalene series which contains in ortho - position to the couplable carbon atom an hydroxy group, and/or the ortho - hydroxy - carboxy grouping.  The dyestuffs are prepared by coupling 1 mol of the tetrazo compound from a 4 : 41 - diamino - diphenyl compound substituted as described above with 2 mols of a compound of formula (I), or coupled at the same time or in any desired sequence with 1 mol of a compound of formula (I) and 1 mol of a different compound of formula (I) or 1 mol of a coupling component of the benzene or naphthalene series containing ortho to the couplable carbon atom an hydroxy group, and/or the ortho - hydroxy - carboxy grouping. The dyestuffs dye cotton and regenerated cellulose fibres in the single bath coppering or after-coppering processes in marine-blue, grey or black shades.  Compounds of formula (I) are obtained by acid coupling diazotized 1 - amino - 2 - hydroxybenzenes with a 2 amino - 5 - hydroxy - 7 - naphthalene - 7 - sulphonic acid which may be substituted on the amino group. Specified substituents R on the amino group are methyl, ethyl, propyl, hydroxyethyl, cyclohexyl, phenyl, 21 - or 31 - or 41 - methylphenyl, 31 - 41 - chlor phenyl, 41 - amino - or carboxy - phenyl, 31 - carboxy - 41 - hydroxyphenyl, 31 - or 41 - sulphophenyl, 411 - amino - 11 : 111 - diphenyl or benzyl. Specified 1 - amino - 2 - - hydroxybenzenes are 1 - amino - 2 - hydroxybenzene, 1 - amino - 2 - hydroxybenzene - 4 - or 5 - sulphonic acid, 1 - amino - 2 - hydroxybenzene - 5 - sulphonamide or - sulphonmethylamide or - sulphonethylamide or - sulphondiethylamide or - sulphondimethylamide or - sulphonphenylamide or - sulphonic acid - (31 - carboxy - 41 - hydroxy) - phenylamide, 1 - amino - 2 - hydroxy - 5 - chloro - or - nitro - benzene - 4 - sulphonic acid, 1- amino - 2 - hydroxy - 3 - or - 5 - chloro - or - bromo - or nitro - benzene - 3 - or - 5 - sulphonic acid, 1 - amino - 2 - hydroxy - 4 - nitrobenzene, 1 - amino - 2 - hydroxy - 4 - nitrobenzene - 5 - sulphonic acid, 1 - amino - 2 - hydroxy - 5 - nitro - or - chlorobenzene, 1 - amino - 2 - hydroxy - 3 - or - 4 - nitro - 5 - chlorobenzene, 4 : 41 - dihydroxy - 3 amino - 1 : 11 - azobenzene - 31 - sulphonic acid and 4 - hydroxy - 3 - amino - 1 : 11 - azobenzene - 31 - sulphonic acid. Specified coupling components of the benzene and naphthalene series are 1-hydroxybenzene-2 - carboxylic acid 1 - hydroxy - 4 - methylbenzene, 1 - hydroxy - 6 - methylbenzene - 2 - carboxylic acid, 1 - hydroxynaphthalene - 2 - carboxylic acid, 2 - hydroxynaphthalene - 3 - carboxylic acid, 1 - hydroxynaphthalene - 4 - sulphonic acid or - sulphonamide, 2 - hydroxynaphthalene, 2 : 4 - dihydroxynaphthalene, 2 - hydroxynaphthalene - 4 - or - 6 - or - 7 - or - 8 - sulphonic acid and the corresponding sulphonamides and methylsulphones, 1 - or 2 - amino - or - phenylamino - 5 - hydroxynaphthalene - 7 - sulphonic acid, 2 - methylamino - or - ethylamino - or - (41 - hydroxy - 31 - carboxy) - phenylamino - 5 - hydroxynaphthalene - 7 - sulphonic acid, 2 - phenylamino - 5 - hydroxynaphthalene - 7 : 41 - disulphonic acid, 2 - acetylamino - or - benzoylamino - 5 - hydroxynaphthalene - 7 - sulphonic acid, 2 - amino - or - benzoylamino - 8 - hydroxynaphthalene - 6 - sulphonic acid, 1 - benzoylamino - 8 - hydroxynaphthalene - 3 : 6 - disulphonic acid, 2 - methylamino - or - (411 - amino - 11 : 111 - diphenyl) - amino - or - hydroxyethylamino - 8 - hydroxynaphthalene - 6 - sulphonic acid, 1 - amino - 8 - hydroxy - naphthalene - 4 - sulphonic or - 2 : 4 - disulphonic acid, 1 - amino - or - 2 - butylamino - 8 - hydroxynaphthalene - 3 : 6 - disulphonic acid and 1 - (31 - carboxy - 41 - hydroxyphenyl - 11) - azo - 2 - phenylamino - 5 - hydroxynaphthalene - 7 - sulphonic acid. In examples dyestuffs are prepared using certain of the above components.  Specification 657,753 is referred to.