Synthesis of Azo Disperse Dyes with High Absorption for Efficient Polyethylene Terephthalate Dyeing Performances in Supercritical Carbon Dioxide

Supercritical carbon dioxide dyeing (SCDD) not only enables strong dyeing performance for a versatile range of polymer material but is also regarded as a green chemical media due to its low environmental impact as well as low risk of product denaturation. Over the decades, azo disperse dyes have been revealed to be efficient dyes and represent the wide majority of dyeing material. Azo dyes possess a wide variety of functional groups to optimize dye synthesis and tune the light absorption properties. Using SCDD, end-chain of different lengths, and functional group exhibiting various electronic affinity, six disperse red azo dyes were synthesized to investigate dyeing performances as woven fabric type, color strain, and color fastness after dyeing are discussed. Dye structure synthesized through a coupling reaction was confirmed by (1)H NMR and mass spectroscopy. We found that the light absorption wavelength and absorption coefficient value variation are associated to the nature of the functional group. From the color strength values of the polyethylene terephthalate woven after dyeing, we find that the fiber host and dye dopant chemical structure greatly influence the dyeing process by providing enhanced woven, color strain, and color fastness. In comparison with commercial products, our approach not only improves the dyeing process but also guarantees a strong resistance of the dyed product against water, detergent, perspiration, abrasion, and friction.