Synthesis, Structure Elucidation and Application of Some New Azo Disperse Dyes Derived from 4-Hydroxycoumarin for Dyeing Polyester Fabrics

Abstract

As a part of our ongoing interest in disperse dyes and task specific azo dyes with better dyeing properties, we synthesized a series of 3-aryl(hetaryl)hydrazono-2,4-chromandiones 4a-k via Coupling of 4-hydroxycoumarin with diazotized aniline derivatives. Structures of the synthesized compounds have been investigated by means of UV, IR, 1 H-NMR and mass spectroscopy in order to elucidate their tautomeric and isomeric structures. The results of such spectral data indicated that compounds 4a-k exist predominantly in the hydrazo structure (D) as a mixture of Z and E-isomer with ratio ~ 84.5:15.5. Finally, the prepared dyestuffs 4a-k were applied as disperse dyes for dyeing polyester fabrics and their fastness properties were evaluated. Also, the position of color in CIELAB coordinates

Recent advances in 4-hydroxycoumarin chemistry. Part 1: Synthesis and reactions

“…A series of new azo coumarin dyes were prepared by coupling of basic solution (sodium hydroxide or pyridine) (Metwally et al, 2012e;Shoair, 2007;Yazdanbakhsh et al, 2007) of 4-hydroxycoumarin 1 with diazotized arylamines (Scheme 53). …”

Synthesis of Spirocyclic Pyrazolones by Oxidative C–N Bond Formation

“…The residue was chromatographed in a silica gel cartridge (50 g) eluting with dichloromethane/ethyl acetate 10%, 20%, and 30% to obtain 1.85 g (71%) of the title compound as a white solid (mixture of tautomers). 1 under nitrogen atmosphere. The mixture was stirred at 0°C for 45 min, and then the ester (1.05 equiv) was added.…”

“…Following the general procedure from 3a (500 mg, 2.85 mmol) and ethyl 4-methoxybenzoate (3 mmol), 708 mg (80%) of the title compound was obtained as a yellowish solid after washing with hexane: 1 13 1-(4-Chlorophenyl)-3-(4-methoxybenzoyl)piperidin-2-one (4f). Following the general procedure from 3f (1.2 g, 5.74 mmol) and ethyl 4-methoxybenzoate (6.02 mmol), 1.8 g (91%) of the title compound was obtained as a white solid after washing with hexane: 1 163.4, 147.1, 132.8, 131.2, 128.8, 126.3, 118.6, 113.9, 108.2, 55.6, 50. 4-(2-Oxo-1-phenylpiperidine-3-carbonyl)benzonitrile (4k).…”

“…Following the general procedure from 3a (500 mg, 2.85 mmol) and ethyl 4-methoxybenzoate (3 mmol), 708 mg (80%) of the title compound was obtained as a yellowish solid after washing with hexane: 1 13 1-(4-Chlorophenyl)-3-(4-methoxybenzoyl)piperidin-2-one (4f). Following the general procedure from 3f (1.2 g, 5.74 mmol) and ethyl 4-methoxybenzoate (6.02 mmol), 1.8 g (91%) of the title compound was obtained as a white solid after washing with hexane: 1 163.4, 147.1, 132.8, 131.2, 128.8, 126.3, 118.6, 113.9, 108.2, 55.6, 50. 4-(2-Oxo-1-phenylpiperidine-3-carbonyl)benzonitrile (4k). Following the general procedure from 3a (750 mg, 4.28 mmol) and methyl 4-cyanobenzoate (4.5 mmol), 1.1 g (84%) of the title compound was obtained as a white solid after chromatography on silica gel eluting with dichloromethane: 1 Experimental Procedure for the Synthesis of Spirocycles 2.…”

Synthesis, Spectral Property and Dyeing Assessment of Azo Disperse Dyes Containing Carbonyl and Dicyanovinyl Groups

“…The dyeing assessment of prepared dyes was carried out on polyester fabrics 4,22 and the results were listed in Table 2. The colors of dyes are well correlated with λ max values in Table 1.…”