Monoazo disperse dyes containing ethyleneimine. Part 1: Synthesis and application of some monoazo disperse dyes derived from 3-amino-4-methoxyacetanilide

Abstract

Three aminoazobenzene disperse dyes containing a terminal ethyleneimine group derived from 3-amino-4-methoxyacetanilide were synthesised using Gabriel and Wenker’s method. One aminoazobenzene disperse dye containing a terminal N-hydroxyethylene group as a hydrolysed form and another azo disperse dye containing a terminal N-dihydroxyethylene group were also synthesised. The colour properties of these five dyes in acetone were investigated. As expected, attachment of the ethyleneimine ring to the terminal N-atom resulted in hypsochromic shifts and decreasing ϵmax values when compared with analogous compounds containing terminal N-hydroxyethyl and N,N-dihydroxyethyl groups. When one or two chloro substituents were attached on the diazo component of the aziridinyl azo disperse dyes, colour and fastness properties were affected. The rate of hydrolysis of three ethyleneimine dyes was investigated.