Patent GB-949316-A (GB)
Title: New polyazo dyestuffs
Inventor: LODGE FRANK
IPC: C09B43/26
Filed: 1960-07-14
Abstract: Di -b - (3-amino -4- methoxyphenyl sulphonylethyl) terephthalate is obtained by reacting terephthaloyl chloride with 2-nitroanisole -4-b -hydroxy-ethyl sulphone and reducing the product with hydrogen in the presence of Raney nickel. The corresponding oxalate, fumarate and succinate are prepared by similar methods.ALSO:The invention comprises azo dyes of the formula <FORM:0949316/C3/1> wherein A and A1 each represent substituted or unsubstituted alkylene radicals containing from 2 to 6 carbon atoms and may be the same or different; D and D1 each represent the residue of an azo dye molecule and may be the same or different, T and T1, which are directly attached to carbon atoms present in D and D1 each represent a -SO2- or SO2 <FORM:0949316/C3/2> group and may be the same or different; R represents a hydrogen atom or a substituted or unsubstituted hydrocarbon radical and Z represents a direct link or a divalent hydrocarbon radical which may contain substituents and process for the preparation thereof wherein (a) two molecular proportions of a dyestuff of the formula D-T-A-OH or one molecular proportion of a dyestuff of the formula D-T-OH and one molecular proportion of a different dyestuff of the formula D1-T1-A1-OH wherein A, A1, D, D1, T and T1 have the meanings stated above are reacted with one molecular proportion of a halide of an acid of the formula <FORM:0949316/C3/3> wherein Z has the meaning given above or (b) an aromatic diamine which contains the group <FORM:0949316/C3/4> is tetrazotized and the tetrazo compound is coupled with 2 molecular proportions of a coupling component, or which 2 molecular proportions of an aromatic amine is diazotized and the diazo compound is coupled with one molecular proportion of a coupling component which contains the group <FORM:0949316/C3/5> where A, A1, T, T1 and Z have the meanings stated above.  The carbon atom to which each of the groups T and T1 is linked may form part of an aryl radical present in the dye molecule or may form part of an alkyl chain directly attached to such an aryl radical or may be attached to an aryl radical through a group such as -O-, -S-, -NH-, <FORM:0949316/C3/6> alkyl -CO-and-CONH-.  The radicals D and D1 may be the residues of mono- or polyazo dyes optionally containing a water solubilizing group, e.g. a carboxylic acid, alkyl sulphone, sulphamyl or sulphonic group and may also contain co-ordinately bound metal, e.g. copper, chromium or cobalt. Examples relate to the preparation of dyes by coupling diazotized di - b  - (3 - amino - 4 - methoxyphenylsulphonylethyl) acid, 2-naphthol-3,6-disulphonic acid, 1 - (21 - chloro - 41 - sulpho - 61 - methylphenyl)-3 - methyl - 5 - pyrazolone, 2 - acetyl - amino-5 - naphthol - 7 - sulphonic acid, 1 - naphthol-5-sulphonic acid and 1-amino-8-naphthol-3,6-disulphonic acid (1-6); 3-amino-4-methoxyphenyl - b  - hydroxyethyl - sulphone with 2-naphthol-6-sulphonic acid and condensing with terephtholoyl chloride (7); or isophthaloyl chloride (8); or by reacting the copper complex of 2 - (21 - hydroxy - 51 - b  - hydroxyethyl-sulphonylphenylazo) - 1 - naphthol - 4 - sulphonic acid with terephthaloyl chloride (9); terephthaloyl chloride with [31-(b -hydroxyethylsulphonyl)phenyl] - 3 - methyl - 4 - (611-sulphonaphth - 211 - ylazo) - 5 - pyrazolone (10); or with 2 - [41 - (N - b  - hydroxyethylsulphamyl) phenylazo] - 1 - naphthol - 4 - sulphonic acid (11); and by coupling di-b -(3-amino-4-methoxyphenylsulphonylethyl)oxalate, succinate and fumarate with 2-naphthol-3,6-disulphonic acid (12-13) and di-b -(3-amino-4-chlorophenylsulphonyl - ethyl)terephthalate with 2 - naphthol-6-sulphonic acid.  The dyes are particularly suitable for colouring cellulose textile materials.