Abstract
This article describes the synthesis of some novel coumarin compounds to use as acid dyes by using compounds 1 - 4 as starting materials, which were prepared by interaction of 2-hydroxybenzaldehyde with ethyl 3-oxobutanoate, diethylmalonate, 4-nitrobenzenediazonium chloride and 4-sulfobenzenediazonium chloride, respectively. Compound 1 reacted with bromine and 2-cyanoacetohydrazide 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) diazenyl)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-disulfonaphthalene-1-diazonium chloride gave coumarin acid dyes 9 and 10, respectively. Interaction 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. Cyclocondensation of compound 3 with ethyl 3-oxobutanoate, diethyl malonate and malononitrile afforded derivatives 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 derivative 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, 1H 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 rubbing, 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.
Highlights
The considerable innovation has been witnessed in past three decades in the field of azo dye chemistry based on heterocyclic systems and studies in the synthesis of such derivatives have been reported [1]-[5]
The present work was carried out with the following objectives, synthesis and identification of some newly acid dyes based on coumarin derivatives, and the possibility of its use in dyeing of wool and silk fabrics
The present investigation deals with the synthesis of novel coumarin compounds to use as acid dyes by using compounds 1-4 as a starting materials, which were prepared by interaction of 2-hydroxybenzaldehyde with ethyl 3-oxobutanoate, diethylmalonate, 4-nitrobenzenediazonium chloride and 4-sulfobenzenediazonium chloride, respectively (Scheme 1)
Summary
The considerable innovation has been witnessed in past three decades in the field of azo dye chemistry based on heterocyclic systems and studies in the synthesis of such derivatives have been reported [1]-[5]. Most heterocyclic dyes of technical interest for application to textiles are derived from diazo components consisting of five-membered rings containing one sulphur heteroatom and to which a diazotisable amino group is directly attached. The ring may possess one or more nitrogen heteroatoms and be fused to another aromatic ring These diazo components are capable of providing red to blue color dyes that meet the rigorous technical and economical requirements demanded of them by both manufacturer and user. The free dye acids are difficult to isolate and are hydroscopic in nature making it difficult to pack and store them. The present work was carried out with the following objectives, synthesis and identification of some newly acid dyes based on coumarin derivatives, and the possibility of its use in dyeing of wool and silk fabrics
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