Eco-friendly Synthesis of New Polyfunctional Azo Dyes Using Shrimp Chitin as a Catalyst: Application on Polyester Fabrics and Their Biological Activities

A series of varying and poly-functionalized heterocyclic compounds 3a-c, 4d-k, 6a, b, 8, 9, and 12 containing azo function have been synthesized using 2-(1-(4-aminophenyl)ethylidene)malononitrile (1) and/or its diazonium salt as building blocks. In addition, new pyridazine derivatives 4a-c, 7a, b, and 13a-f were synthesized. Subsequent treating of the resulted azo dyes moieties with different reagents in conventional and green conditions using microwave irradiation and shrimp chitin as a green catalyst; homo- and hetero-molecules containing azo dyes were gathered. The obtained azo dyes were applied on fabrics at high temperatures and their properties such as washing fastness using standard soap (SDS) and rubbing fastness (wet and dry) under controlled conditions of pressure, speed, and moisture were studied. In addition, they were screened for their biological activities on two bacterial and two mycolic species. The synthesized products were characterized by their elemental and spectral analyses such as IR, MS, 1 H-NMR, and 13 C-NMR spectra. The produced dyestuffs 3a-c, 4d, f, h, i, j, 6a, b, 8, and 12 were dyed on polyester fabrics, and subsequently their dyeing properties and their light, washing, perspiration, rubbing, and sublimation fastness was determined and the dyed samples showed very good fastness levels to rubbing, washing, thermal fixation, good light, and possessed very good perspiration fastness.