Synthesis of Novel Acid Dyes with Coumarin Moiety and Their Utilization for Dyeing Wool and Silk Fabrics

Abstract

This article describes the synthesis of some novel coumarin compounds to use as acid dyes by us-ing compounds 1 -4 as starting materials, which were prepared by interaction of 2-hydroxyben-zaldehyde with ethyl 3-oxobutanoate, diethylmalonate, 4-nitrobenzenediazonium chloride and 4-sulfobenzene-diazonium chloride, respectively. Compound 1 reacted with bromine and 2-cyano-acetohydrazide to give phenacyl bromide derivative 5 and 2-cyanoacetohydrazone derivative 6, respectively. Coupling of compound 6 with equimolar amount of 2-sulfo-4-((4-sulfophenyl) di-azenyl)benzenediazonium chloride gave coumarin acid dye 8. Phenacyl bromide derivative 5 re-acted with potassium cyanide in refluxing ethanol to produce compound 7, which on coupling with equimolar amount of 8-hydroxy-6-sulfonaphthalene-2-diazonium chloride and 8-hydroxy-3,6-di-sulfonaphthalene-1-diazonium chloride gave coumarin acid dyes 9 and 10, respectively. Interac-tion of compound 2 with 2-amino-5-((4-sulfophenyl)diazenyl)benzenesulfonic acid, benzene-1,4-diamine and 3,3'-dimethoxy-[1,1'-biphenyl]-4,4'-diamine in refluxing ethanol afforded compounds 11, 12 and 14, respectively. Diazonium sulphate of compounds 12 and 14 coupling with 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid gave compounds 13 and 15, respectively. Cycloconden-sation of compound 3 with ethyl 3-oxobutanoate, diethyl malonate and malononitrile afforded de-rivatives of 3-acetyl-2H-chromen-2-one 16, ethyl 2-oxo-2H-chromene-3-carboxylate 17 and 2-imino-2H-chromene-3-carbonitrile 18, respectively. Reaction of sodium benzenesulfonate deriva-* Corresponding author. M. S. Bashandy et al. 19 tive 4 with ethyl 3-oxobutanoate and hydrazine hydrate gave compounds 19 and 20, respectively. The structures of the newly synthesized compounds were confirmed by elemental analysis, UV/ VIS, IR, 1 H NMR and Ms spectral data. The suitability of the prepared dyestuffs for dyeing of wool and silk fabrics has been investigated. The dyed fabric shows good light fastness, very good rub-bing, perspiration, washing and excellent sublimation fastness. These dyes have been color shade from blue to violet with very good depth and levelness on fabrics. The dye bath exhaustion and fixation on fabric has been found to be very good.