Patent GB-776711-A (GB)
Title: Process for the preparation of polyazo dyestuffs and their metal complex compounds
IPC: C09B33/26
Filed: 1955-07-11
Abstract: The invention comprises dyestuffs of formula <FORM:0776711/IV(b)/1> where R1, R2 and R3 are benzene, or naphthalene residues, X is methoxy or ethoxy, y is an alkyl, cycloalkyl, aralkyl or aryl group which may be substituted, Z is OH or COOH, - azo - and -N = N- are in p-positions, X is o to -azo1-, A may be substituted and there is present a sufficiency of groups causing the dyestuffs to be water-soluble and metal complexes thereof.  They may be made by alkaline coupling, optionally in the presence of a tertiary base, a diazo compound of an appropriate disazo dyestuff of formula <FORM:0776711/IV(b)/2> with an aminoazo compound of formula <FORM:0776711/IV(b)/3> or a metal derivative thereof, with subsequent metallization if necessary.  Metallization may be effected on the fibre or in substance, nickel and copper compounds being mentioned. Specified substituents for R1, R2 and R3 are fluorine, chlorine and bromine atoms and methyl, ethyl, methoxy, ethoxy, acetyl-, propionyl-, benzoyl-, carbomethoxy- and carboethoxy - amino-, hydroxy, carboxy, sulpho, sulphonamido, N-methyl-, -ethyl-, -dimethyl-, -hydroxyethyl - and - methoxypropyl - sulphonamido and methylsulphonyl groups.  When y is alkyl it may be substituted with advantage by a hydroxy or methoxy group and when y is an aryl group amino or aryl residues may advantageously be present.  Specified values for y are (21-hydroxy) - ethyl, (31 - methoxy)-propyl, (41 - amino) - phenyl and (411 - amino) - 11, 111 - diphenyl.  The disazo dyestuff may be made by coupling a diazotized amine R1 NH2 in a weakly acid medium with an amine R2NH1 and coupling a diazo compound of the aminoazo dyestuff thus produced in a weakly acid medium with the component X - R3 - NH2.  The aminoazo compounds are made by coupling a diazotized 2 - amino - 1 - hydroxy - or - carboxy - benzene in an acid medium with an appropriately substituted J acid. The aminoazo compound derived from J acid and the final products may be metallized by usual methods.  The dyestuffs, before and after metallization dye cotton and regenerated cellulose fibres in gray shades.  Examples are provided of the preparation of the metal-free and coppered dye-stuffs and their use in dyeing, R1 being derived from aniline - 3 - and - 4 - sulphonic acids, 1 - amino - 4 - phenol - 3 carboxylic acid, 1 - amino - 4 - and - 2 - phenol - 3 - carboxy - 5 - sulphonic acids, 1 - naphthylamine - 4,- - 5 - and - 8 - mono - and - 3, 8 - di - sulphonic acids and 2 - naphthylamine - 3,6 -, - 4,8 -, -5,7 - and - 6,8 - disulphonic acids.  R2 is derived from 1 amino-3 - methylbenzene, a - naphthylamine and 1 - naphthylamine - 6 - and - 7 - sulphonic acids, R3 is derived from 2 amino - 1 - methoxy - 4 - methyl - and - ethoxy - benzene, 2 - amino - 1,4 - di - methoxy - and -ethoxy - benzene and 1 - amino - 2 -methoxy - and - ethoxy - naphthalene - 6 - sulphonic acid, y is phenyl, (41 - methoxy, - chloro, - carboxy and - sulpho)-, (31 - carboxy) - and (41 - methyl - 31 - sulpho) - phenyl, methyl, cyclobenzyl and benzyl and nucleus A is derived from 1-amino-2 - hydroxy - 3 - carboxy - benzene - 5 - sulphonic acid, 2 - amino - 4 - chloro - and - nitro - 1 - phenols, 2 - amino - 4 - chloro - 6 - nitro - phenol, 2 - amino - 1 - phenol - 4 - and - 5 - sulphonic acids, 2 - amino - 1 - phenol - 5 - N - ethylsulphonamide and - sulphonic acid morpholide, 2-amino - 1 phenol - 4 - sulphonamide, - N - methyl -, - 21 - hydroxyethyl-, - 31 - methoxypropyl-, - cyclohexyl-, - benzyl - and - phenyl - sulphonamides and 2 - amino - 1 - hydroxy - 4 - methylsulphonyl benzene.