Patent GB-455352-A (GB)
Title: Improvements in the manufacture and production of water-soluble azo dyestuffs
IPC: C09B29/08
Filed: 1935-04-16
Abstract: Azo dyes soluble in water are made by coupling diazotized amines with amines of the general formula <FORM:0455352/IV/1> in which R=an aromatic residue, X=an alkyl, cycloalkyl, aralkyl or aryl group and Y=an alkyl radicle free from oxygen atoms doubly bound to carbon atoms to which is attached in direct combination with an alkyl carbon atom the nitrogen atom of the residue of a quaternary ammonium base or a quaternary ammonium salt, or in which X is the same as Y, and, if desired, diazotizing the dyestuffs which contain diazotizable amino groups and coupling with components.  In examples, the following dyes are described: (1) p-nitroaniline --> the condensation product from pyridine and N-n-butyl-o -chlorethylaniline (brilliant red on cotton, viscose or mixed fabrics, leather and paper); 2-chloro-4-nitroaniline, 4-chlor-2-nitroaniline, 2 : 6-dichloro-4-nitroaniline, 2 : 4 : 5-or 2 : 4 : 6-trichloraniline, 1-amino-2-methoxy-5-nitrobenzene, dianisidine, 2-toluidine-4-sulphonic acid, 5 - nitro - 3 : 6 - dimethoxyaniline, 2 : 3 : 5 : 6-tetrachloraniline, 2 : 4-dinitroaniline and 6 - bromo - 2 : 4 - dinitroaniline are also specified; (2) p-nitroaniline --> the product from trimethylamine and 1-methyl-3-(N-n-butyl-o -chloroethyl)-aminobenzene (red); other diazo components as in (1) may be used; (3) p-nitroaniline --> the product from pyridine and N - hydroxyethyl-N-(b -hydroxy-g -chlorpropyl)-aniline (red); (4) 2 : 4 : 6-trichloraniline --> the product from trimethylamine and N-o -chlorethyldiphenylamine (green - yellow on viscose and leather); other diazo components as above may be used; (5) p-nitroaniline --> the product from trimethylamine and N-ethyl-N-o -chlorethylaniline or the product from triethanolamine and N - hydroxyethyl - N - o -chlorethylaniline (orange-red); 4-aminoazotoluene, a -naphthylamine and 4-nitro-4<1>-aminoazobenzene are additional diazo components specified; the condensation product from triethanolamine and N-ethyl-N-o -chlorethylaniline may also be used as coupling component (these dyes are also soluble in nitrocellulose lacquers); (6) p-nitroaniline --> the product from trimethylamine (2 mols.) and N-di-(o -chlorethyl)-aniline (1 mol.) (yellowish orange on cotton and leather tanned with synthetic tanning agents); a -naphthylamine and 4-nitro-1-naphthylamine may also be used; (7) 6-bromo-2 : 4-dinitroaniline --> the product from trimethylamine and N-ethyl-N-o -chlorethyl-1-naphthylamine (bluish violet on leather) or the product from trimethylamine and N-n-butyl-N-o -chlorethyl-1-amino-2-methoxy-5-methylbenzene; (8) 2 : 3 : 5 : 6-tetrachloroaniline --> the condensation product from dimethylstearylamine and N - ethyl - N - chlorethylaniline (yellow-brown on leather); (9) the product from trimethylamine and N-ethyl-N-o -chlorethylaniline \sM 1 : 3-diamino-4-nitrobenzene --> 5 : 6-dihydro-1 : 3-dihydroxybenzene (brown on leather); (10) 2 : 3 : 5 : 6-tetrachloraniline --> the product from trimethylamine and N-n-butyl- or N-ethyl-N-(b  - hydroxy - g  - chlorpropyl) - aniline (deep yellow on leather); (11) 2 : 3 : 5 : 6-tetrachloraniline --> the product from trimethylamine and N - cyclohexyl - N - o  - chlorethylaniline (yellow); (12) the condensation product from trimethylamine (2 mols.) and N-di-(b -hydroxy-g -chlorpropyl)-aniline (1 mol.) \sM 4-nitro-1 : 3-diaminobenzene --> 5 : 6 - dihydro - 1 : 3-dihydroxybenzene (brown on leather).  Samples have been furnished under Sect. 2 (5) of the following dyestuffs: p-nitroaniline or o-chloro-p-nitroaniline --> the product from trimethylamine and N - benzyl - N - o  - chlorethylaniline (orange and red on viscose). Diazo components mentioned in general are aniline, m- and p-phenylene diamine, 4-amino-and 4 : 4<1>-diaminodiphenylamine, benzidine, naphthylamines, 4-aminoazobenzene or their homologues or derivatives.