Patent GB-853013-A (GB)
Title: Monoazo dyestuffs containing triazole rings
IPC: C09B43/06
Filed: 1958-07-03
Abstract: The preparation of nitro-and amino-triazole compounds used as intermediates in the preparation of azo dyes (see Group IV(c)) is specified.  In an Example, 2-amino-6-nitronaphthalene-4 : 8-disulphonic acid is diazotised and coupled (in the 1-position) with 2-aminonaphthalene-6-sulphonic acid, the o-aminoazo dye triazolised by heating with ammoniacal copper sulphate solution, to give the nitrotriazole compound which is reduced with iron and acetic acid to the aminotriazole compound.  Further components used in the reaction are specified.ALSO:The invention comprises monoazo dyes of formula: <FORM:0853013/IV (c)/1> wherein R is a benzene or naphthalene residue having the azo group and triazole ring in the p-position, R1 and R2 are the radicals of aminonaphthalene coupling components having the nitrogen atoms of the triazole ring in o-position and n is 1 or 2. The dyes may be prepared by coupling a diazotised 2- amino -6- nitro- or -acetylamino-naphthalenesulphonic acid with a naphthylamine, in o-position to the amino group, triazolising the o-aminoazo compound converting the nitro or acetylamino group of the triazole compound into an amino group, diazotising, coupling with an aminobenzene or -naphthalene in p-position, diazotising, and coupling with a naphthylamine in o-position to the amino group and triazolising.  The order of the various steps of the process may be modified.  The dyes give yellow shades on cellulose fibres.  In Examples: (1) the monoazo dye 2-amino -6- nitronaphthalene -4 : 8- disulphonic acid --> 2- aminonaphthalene -6- sulphonic acid (2) is heated with ammoniacal copper sulphate solution to give the nitrotriazole compound, which is reduced with iron and acetic acid to the aminotriazole compound, which is diazotised and coupled with m-toluidine (3), the product diazotised and coupled with 2-aminonaphthalene -6- sulphonic acid (4) and finally triazolised as above; alternative components specified are: component (2) 1- aminonaphthalene -4- sulphonic acid, 2- aminonaphthalene -5- sulphonic acid and 2- aminonaphthalene -3 : 6- disulphonic acid; component (3) aniline, 1- aminobenzene -2- sulphonic acid, anthranilic acid, 1- amino -2- methoxy -5- methylbenzene, 1- amino -2 : 5- dimethoxybenzene, 1-aminonaphthalene -6- sulphonic acid, 1- amino-2- methoxynaphthalene -6- or -7- sulphonic acid; component (4) 2- aminonaphthalene -3 : 6- disulphonic acid, 1- aminonaphthalene -4- sulphonic acid and 2- aminonaphthalene -5- sulphonic acid; (2) the disazo dyestuff 2- amino -6-nitronaphthalene -4 : 8- disulphonic acid --> m-toluidine --> 2- amino-naphthalene -3 : 6- disulphonic acid is triazolised as in (1), the nitrotriazole reduced with aqueous sodium sulphide, diazotised, coupled with 2- aminonaphthalene -6- sulphonic acid and triazolised; (3) the monoazo dye 2- amino -6- nitronaphthalene -4 : 8- disulphonic acid --> mtoluidine is reduced with aqueous sodium sulphide, the diaminoazo dye tetrazotised and coupled with 2- aminonaphthalene -6- sulphonic acid and the trisazo dye triaolised; (4) the monoazo dye 2- amino -6-nitronaphthalene -8- sulphonic acid --> 2- aminonaphthalene -3 : 6- disulphonic acid is triazolised, reduced to the aminotriazole, diazotised and coupled with mtoluidine, diazotised again, coupled with 2- aminonaphthalene -6- sulphonic acid and triazolised.