Acryloyl esters of emodin for waterless dyeing and toxicological studies

Abstract

Traditional textile dyeing processes usually require large quantities of water and energy and generate wastewater that can be harmful to the environment. Dyeing in supercritical carbon dioxide (sc-CO₂) media is promising in textile coloration due especially to it providing a waterless process and eliminating the need for an energy intensive drying step. The natural anthraquinone emodin showed promising results for dyeing different fibres through sc-CO₂ process. However, emodin is mutagenic. The aim of this study was to develop non-mutagenic derivatives of emodin that can be applied to textiles using sc-CO₂. Emodin structure was modified incorporating acryloyl groups, which are considered suitable for decreasing potential for DNA intercalation, and thus mutagenicity. The presence of acryloyl groups would also enable atmospheric plasma induced bonding with fibres. Molecular modelling studies showed that emodin derivatives became less planar with increasing number of attached acryloyl groups, making intercalation unlikely. The derivatives produced were tested to assess mutagenicity in vitro (Salmonella/microsome assay, TA1537, 10% S9) and in vivo (micronucleus test in hemocytes of aquatic crustacean). We found that emodin can be derivatised using acryloyl chlorides to give mono- and di-acrylate esters suitable for dyeing polyester fibres in sc-CO₂. However, the new dyes presented mutagenicity for both in vitro and in vivo. Although the derivatives provided greenish-yellow alternatives to emodin for dyeing synthetic fibres, they do not appear to be viable alternatives from the point of view of preserving human and environmental health. Plasma bonding studies are underway.