Synthesis of Some Novel Biologically Active Disperse Dyes Derived from 4-Methyl-2,6-dioxo-1-propyl-1,2,5,6-tetrahydro-pyridine-3-carbonitrile as Coupling Component and Their Colour Assessment on Polyester Fabrics

Abstract

A series of novel azo-disperse dyes containing alkylhydrazonopyridinone structures were synthesized. 4-Methyl-2,6-dioxo-1-propyl-1,2,5,6-tetrahydropyridine-3-carbonitrile (8) is synthesized by one-pot synthesis using ethyl cyanoacetate, propylamine, and ethyl acetoacetate. Compound 8 is then coupled with aromatic and heteroaromatic diazonium salts to afford the corresponding aryl- and heteroaryl-4-methyl-2,6-dioxo-1-propyl-1,2,5,6-tetrahydropyridine-3-carbonitriles 12a,b and 13a–c. Structural assignments to the dyes were made using NMR spectroscopic methods. A high temperature dyeing method was employed to apply these dyes to polyester fabrics. Most of the dyed fabrics tested displayed very good light fastness levels and good wash fastness. Finally, the biological activity of the prepared dyes against Gram positive bacteria and Gram negative bacteria were evaluated.

The effect of dispersing agent on the dyeing of polyester fabrics with disperse dyes derived from 1,4-diethyl-2,6-dioxo-1,2,5,6-tetrahydropyridine-3-carbonitrile

“…In addition, the stability of the dye dispersion, the equilibrium between dye dispersion and dye in true solution in the dyebath, and the rate of dyeing are all affected by the type and concentration of the dispersing agents [5]. Pyridinone disperse dye derivatives have found many applications on different fabrics [6][7][8][9]. Keeping in mind the biological importance of the above mentioned heterocyclic compounds and in continuation to our endeavour towards environmentally benign synthesis [10][11][12][13][14][15], we report herein, the synthesis of 1,4-diethyl-2,6-dioxo-1,2,5,6-tetrahydropyridine-3-carbonitrile, 8, as a good precursors to novel arylhydrazono-1,4-diethyl-2,6-dioxo-1,2,5,6-tetrahydropyridine-3-carbonitriles and their application as disperse dyes for the dyeing of polyester fabrics.…”

A Facile Synthesis of New Monoazo Disperse Dyes Derived from 4-Hydroxyphenylazopyrazole-5-amines: Evaluation of Microwave Assisted Dyeing Behavior

“…Several reports [22,23,24] suggest that fading of azo dyes is mainly a consequence of decomposition of the –N=N– moiety by either oxidation, reduction or photolysis. The rates of these processes should be sensitive to the chemical structure of the dye, the type of substrate and treatment conditions.…”

Synthesis, characterization and antimicrobial activity, and applications of new azo pyridone disperse dyes on polyester fabric

“…On the other hand, the use of heteroaromatic amines as diazo components in the generation of disperse dyes having essentially colour deepening effect is well established [7]. Pyridinone disperse dye derivatives have found many applications on different fabrics [8][9][10].…”