GB421975A - New monoazo dyestuffs - Google Patents

Abstract

Monoazo dyes for cellulose ester and ether materials are made by diazotizing 6-bromo- or 6 - chloro - 2 : 4 - dinitroaniline in concentrated sulphuric acid medium and adding the acid diazo solution directly to an acid solution of an amine of the benzene series which couples in p-position to the amino group, the said amino group carrying one or two alkyl groups at least one of which is hydroxylated. In examples, the following dyes are described: 6-chloro-2 : 4-dinitroaniline --> N-b b <1>-dihydroxydiethyl-m-toluidine, N - n - butyl - N - b - hydroxyethyl - 3 - amino-4-methoxytoluene, or N-ethyl-N-b g -dihydroxypropylaniline; 6-bromo-2 : 4-dinitroaniline --> N - b b <1> - dihydroxydiethyl - m - toluidine, N - n - butyl - N - b - hydroxyethyl - 3-amino-4-methoxytoluene or N-n-butyl-N-b -hydroxyethyl - m - toluidine. Specifications 181,750, 251,155, 274,823, 292,180, [all in Class 2 (iii)], and 409,921 are referred to. N - n - Butyl - N - b - hydroxyethyl - 3 - amino - 4-methoxytoluene is prepared from m-amino-p-cresolmethylether by reacting with ethylenechlorhydrin to form N-mono-b -hydroxyethyl-m-amino-p-cresolmethylether and then condensing with n-butylchloride. N-Ethyl-N-b g -dihydroxypropylaniline is made by condensing ethylaniline with glycerol chlorohydrin. N - n - Butyl - N - b - hydroxyethyl - m - toluidine is made by reacting N - b - hydroxyethyl - m - toluidine with n-butylbromide.