Synthesis of 4-hydroxy coumarin dyes and their applications

Abstract

Purpose

The present study aims to focus on the possibility of developing new eco-friendly azo dyes with good colouristic application properties, exhibiting biological and pharmacological activities.

Design/methodology/approach

Coupling of 4-hydroxycoumarin with a variety of aromatic diazonium salts of 2-aminothiazole, 2-aminobenzothiazole, 4-aminoantipyrine, 4-aminoacetophenone, adenine sulphate, a-naphthylamine and sulphadimidine to produce novel azo dyes. The compounds were fully characterised using spectroscopic and analytical methods. All of the compounds were tested for their antimicrobial, anticancer and antioxidant activities. The prepared dyestuffs were dyed on polyester fabrics and subsequently their dyeing properties, light, washing, perspiration, rubbing and sublimation fastness were determined.

Findings

The spectroscopic data of the synthesised compounds have provided decisive evidence that such compounds exist in the solid state as the azo-dike to form C and in solution in equilibrium tautomer forms A, B and D. The prepared dyestuffs are suitable for either heat transfer printing or traditional printing on polyester and nylon 6 fabrics. The prints obtained from the dyes possess high colour strength, as well as good overall fastness properties. Also the synthesised compounds exhibit good biological and pharmacology activity.

Research limitations/implications

Synthesis of these seven azo dyes for textile dyeing had never been reported previously.

Practical implications

The dyestuffs derived from 4-hydroxycoumarin are reasonable azo disperse dyestuffs giving good all round fastness properties on polyester fabrics.

Social implications

Production of less expensive and new eco-friendly dyes exhibit antimicrobial and anticancer activity.

Originality/value

It provided a potentially simple way to synthesize novel coumarin azo-dyes exhibit good biological and pharmacology activity and also exhibit good overall fastness properties.

Citation

Gaffer, H., Salem, M. and Marzouk, M. (2016), "Synthesis of 4-hydroxy coumarin dyes and their applications", Pigment & Resin Technology, Vol. 45 No. 5, pp. 320-329. https://doi.org/10.1108/PRT-09-2014-0071