Patent GB-794366-A (GB)
Title: Improvements in or relating to polyazo dyestuffs
IPC: C09B35/46
Filed: 1955-10-07
Abstract: The invention comprises dyestuffs of formula: <FORM:0794366/IV (b)/1> where X is OH, OCH3, OC2H5, OCH2COOH or COOH, R1 is alkyl, hydroxyalkyl, alkoxyalkyl, cycloalkyl, aralkyl or aryl, E may be substituted, 21 is the residue of a coupling component, which may be of the formula of 2, which contains one or more metallizable groups. They may be made by coupling 1 mol. of a tetrazo compound of an appropriate diaminodiphenyl with 2 mols. of an aminoazo dyestuff corresponding to Z or with 1 mol. of the dyestuff corresponding to 2 and 1 mol. of any other appropriate coupling component.  When coupling is effected in two stages the first coupling is preferably effected in a sodium carbonate medium and the second in the presence of an organic tertiary base.  Coupling in a one-stage operation is preferably effected in the presence of an organic tertiary base. Indicated as substituents for E are chlorine atoms, nitro, methylsulphonyl, sulphonic acid, sulphonamide, sulphon-lower alkyl- and dialkylamides and sulphon-mononuclear arylamides which may contain halogen atoms, lower alkoxy groups, or a hydroxy and carboxy group in vicinal positions, "lower" meaning containing 1-4 carbon atoms per molecule.  Specified diphenyls are 4,41-diamino-3,31-dihydroxy - dimethoxy -, diethoxy -, dicarboxymethoxy - and dicarboxy - 1,11 - diphenyl the dimethoxy and dicarboxy derivatives being preferred.  Aminoazo compounds corresponding to Z are made by the acidic coupling of diazotized 2 - aminophenol - 6 - carboxylic acids with appropriate 2 - amino - 5 - naphthol - 7 - sulphonic acids. Specified diazo components are 2-aminophenol-6-carboxylic acid and its 4-sulpho -, nitro -, chloro -, methylsulphonyl -, sulphonamido - and -N- methyl -, ethyl-, dimethyl - and diethyl - sulphonamido -, N-phenylsulphonamido and N - (3 - carboxy - 4-hydroxy) - phenyl - sulphonamido - derivatives. Specified substituents for the N atom of the naphthol sulphonic acid are methyl, ethyl, propyl, hydroxyethyl, cyclohexyl, phenyl, 21-31- and 41-methyl-, 31- and 41-chloro-, sulpho-, methylsulphonyl- and sulphonamido-, 41-amino- and carboxy- and 31-carboxy-41-hydroxyphenyl, benzyl and 411-amino-11,111-diphenyl, preferred being phenyl and substituted phenyl.  Specified coupling components which do not correspond to Z are salicylic acid, 1-hydroxy-6-methyl-2-carboxybenzene, 1-naphthol-2- and 2-naphthol-3-carboxylic acids, 1-naphthol-4-sulphonic acid and its amide, 2-naphthol and its 4, 6, 7 and 8 sulphonic acids and their amides and methyl sulphones, 1 - and 2 - amino - 5 - naphthol - 7-sulphonic acid, 2 - phenyl -, (41 - hydroxy - 31-carboxy) - phenyl -, methyl -, ethyl -, acetyl- and benzoyl - amino - 5 - naphthol - 7 - sulphonic acids, 2 - phenylamino - 5 - naphthol - 7,41 - disulphonic acid, 2-amino-, benzoylamino-, methylamino - and hydroxyethylamino - 8-naphthol - 6 - sulphonic acids, 1 - amino - 8-naphthol - 4 - mono - and 2,4 - disulphonic acids, 1 - amino - and butylamino - 8 - naphthol - 3,6 - disulphonic acids, 3 - methyl - 5-pyrazolone, 1 - phenyl - 3 - methyl - 5 - pyrazolone and its 31 - and 41 - sulphonamides, 1-(31 - and 41 - methylsulphonyl -, nitro - and chloro -) - and (21,51 - dichloro) - phenyl - 3-methyl - 5 - pyrazolones, acetoacetylaminobenzene the nucleus of which may contain halogen atoms, amino, nitro, sulphonic acid, alkylsulphonyl, sulphonamido, carboxy and/or azo groups and 2-acetoacetylaminonaphthalenes and their mono- and di-sulphonic acids.  The dyestuffs are used in one bath or after-coppering processes to dye cotton and fibres of regenerated cellulose in blue, grey and black shades.  Examples are provided of the preparation of the dyestuffs from certain of the above indicated components and their use in dyeing cellulosic fibres, additional other components used being 4 - methyl - phenol, 1 - phenyl - and acetylamino - 8 - naphthol - 4 - sulphonic acids, 2-t41 - (411 - amino) - phenyl] - phenylamino - 5-naphthol - 7,311 - disulphonic acid, 2 - (41-methyl) - phenylamino - 8 - naphthol - 6 - sulphonic acid, 1 - phenylamino - and (21 - hydroxy - 51 - sulphonamido) - phenylazo - 2-phenylamino - 5 - naphthol - 7 - sulphonic acids and 1 - (41 - methyl) - phenyl - 3 - methyl - 5-pyrazolone an additional value for R1 being 3-methoxypropyl.  Specifications 657,753, 727,745 and 791,532 are referred to.