GB498878A - Manufacture of water-soluble mono-azo-dyestuffs - Google Patents

Abstract

Monoazo dyestuffs soluble in water are manufactured by coupling with 2-amino-8-naphthol-6-sulphonic acid in an acid solution a diazo compound of an aminodiphenyl ether not containing a nitro group but substituted by the radicle <FORM:0498878/IV/1> where X1 and X2 are hydrogen, alkyl, cycloalkyl or aryl groups or form with the nitrogen atom a piperidine ring. The products dye wool red shades. The following diazo components are specified: 4 - aminodiphenyl ether - 2 - sulphonic acid N-ethylanilide, N-methylanilide, anilide, o-toluidide, N - ethyl - p - chloranilide, piperidide, diphenylamide, n-butylamide and cyclohexylamide, 4 - amino - 4 - chlorodiphenyl ether-2-sulphodiethylamide, 2 - aminodiphenyl ether-4-sulphodiethylamide, 2-amino-41-chlorodiphenyl ether - 4 - sulphodimethylamide, 4-amino-41-methoxydiphenyl ether-2-sulphamide, 4-amino-41-methyld phenyl ether-2-sulpho-N-methyl-o-toluidide, 2-aminodiphenyl ether-41-sulphodiethylamide, 4-aminodiphenyl ether-31-sulpho-N-methylanilide, 4-aminodiphenyl ether-41-sulphodimethylamide and 2-aminodiphenyl ether - 31 - sulphoethylamide. Specification 312,582, [Class 2 (iii)], is referred to. Aminodiphenyl ethers of the type defined above are obtainable by condensing 1-halogen-2-nitrobenzene - 4 - sulphamides or 1 - halogen-4-nitrobenzene-2-sulphamides with phenols and reducing the nitro group, or, in the case of the last four diazo components specified above, by condensing 1-halogen-2- or 4-nitrobenzene with the appropriate phenol-3- or 4-sulphonic acid, converting the product to the sulphochloride, reacting this with the appropriate primary or secondary amine, and reducing the nitro group.