Synthesis and Application of Novel Reactive Disperse Dye Based on Tetrahydrobenzo[b] Thiophene Moiety

Abstract

Ethyl 2-diazo-4, 5, 6, 7-tetrahydrobenzo[b] thiophene-3-carboxylate is reacted with malononitrile to give a hydrazone derivative. The latter product is reacted with 1-diazobenzene-4-β-sulphatoethylsulphone (PABSES) to give a disperse dye. The dye is synthesised by diazotisation and coupling reactions. First, it is synthesised with the chromophoric moiety of ethyl 2-hydrazomalononitrilo-4,5,6,7-tetrahydrobenzo[b] thiopheen- 3-carboxylate and coupled with diazonium salts that have the aforementioned reactive groups, thus yielding the new target reactive. The synthesised dye is applied onto wool, polyester and wool-polyester (blend) fabrics under typical exhaust dyeing conditions and their dyeing properties are investigated. The structure of this dye is characterised and confirmed by melting point, elemental analysis, infrared, ultraviolet-visible spectroscopy (UV/VIS) and nuclear magnetic resonance (1H-NMR) data. The dyeing of polyester, wool and polyester/wool blend fabrics with a reactive disperse dye gives very good build up and fastness properties by using a nonionic vinylsulphone (VS) derivative, which increases the substantivity of the dye towards wool fabric. Maximum exhaustion as well as total fixation efficiency by using a sulfatoethylsulfone (SES)-based dye on wool fabric is achieved at a neutral pH of 7. This feature of the dye structure significantly improves the union dyeing of wool/polyester blend fabrics with very good build up and fastness properties.