• Journal of the Korean Chemical Society
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• v.56 no.3
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• pp.348-356
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• 2012

In an attempt to find a new class of bisazo disperse dyes with better dyeing properties, a series of novel bisazo dyestuffs based on 4-arylhydrazono-3-(2'-hydroxyphenyl)-1-phenyl-2-pyrazolin-5-ones $\mathbf{3a-f}$ were prepared by diazocoupling of p-nitrophenyl diazonium chloride with 4-arylhydrazono-3-(2'-hydroxyphenyl)-1-phenyl-2-pyrazolin-5-ones $\mathbf{2a-f}$. Compounds $\mathbf{3a-f}$ were subsequently reacted with acetic anhydride in the presence of p-toluenesulfonic acid afford the corresponding O-acetyl derivatives $\mathbf{4a-f}$. The latter products as well as spectral data indicated that compounds $\mathbf{3a-f}$ exist predominantly in the azo-hydrazone tautomeric form (H) as the ZE-configuration. Additionally, two series of the synthesized dyes $\mathbf{3a-f}$ and $\mathbf{4a-f}$ were applied as disperse dyes for dyeing polyester fabrics and their fastness properties were evaluated. Also the position of color in CIELAB coordinates ($L^*$, $a^*$, $b^*$, $H^*$, $C^*$*) was assessed.