アントラキノンアゾール系建染メ染料の研究(第3報)

アントラキノンアゾール系赤色建染メ染料の合成と性質

抄録

Anthraquinone-azole type dyes having anthraquinone (2:3) oxazole (1a), :anthraquinone (1:2) oxazole (1b), anthraquinone (2:1) oxazole (1c), anthraquinone (2:3) thiazole (1d), and anthraquinone (2:1) thiazole (1e) in 2-position of 1-aminoanthraquinone were synthesized. The dye having anthraquinone-(1:2) thiazole could not be obtained in a pure form. From the N-H stretching-vibration range in infrared absorption spectra, it was indicated the presence of intramolecular hydrogen bonding between amino group and oxazole or thiazole and it was clarified that the intensity was in the order of (1b) > (1c) > (1a), and (1e) > (1d). There was no simple regularity between oxazole and thiazole. The visible spectra of dyes in trichlorobenzene were investigated and it was found that anthraquinone-azole ring had electron-attractive property and λmax shifted to longer wave length side by the extension of conjugated system and intramolecular hydrogen bonding. The λmax was in order of (1b) > (1a) > (1a), .and (1e) > (1d). Following results were obtained from dyed cloths dyed with IW method: kind of dye (vat color, fastnesses against chlorine and light, respectively, given) :1a (brown, 5, 7-8) ; 1b (red, 5, 7-8): 1e (red, 5, 5-6) ; 1d (red, 5, 5-6) ; 1e (red, 5, 7-8). Good fastnesses shown by the dye in spite of having amino group was attributed to the protection of the amino group by the intramolecular hydrogen bonding. However, the fastness against the light cannot be explained from hydrogen bonding alone. Vat color of oxazole type was red brown and that of thiazole type was reddish purple.