Syntheses of Polymeric Azo Dyes of Pyrazolone Series-Homopolymers of 4-Arylazo-3-methy1-1-[p-(methacryloylamino)pheny1]-2-pyrazolin5-one and Their Properties

Abstract

To investigate polymeric dyes having excellent bleeding resistance and light fastness, polymeric azo dyes of pyrazolone series were prepared by homopolymerization of 4-arylazo-3methyl-1-[p-(methacryloylamino)pheny1]-2-pyrazolin-5-one, in which the aromatic moieties are C₆H₅, p-CH₃C₆H₄, m-CH₃C₆H₄, p-CH₃C₆H₄, m-CH₃OC₆H₄, p-ClC₆H₄, m-ClC₆H₄, p-NO2CH₄, m-NO2C₆H₄, p-(CH₃)2NC₆H₄.GPC analysis showed that polymeric azo dyes were oligomeric range. It was estimated from IR and NMR spectra that the polymeric azo dyes existed in hydrazone form similarly to the monomeric azo dyes. Light fastness of the polymeric azo dyes in MMA resin cast film was somewhat poor than that of the corresponding monomeric azo dyes, and the fading rate depended on aryl group at 4-position. The polymeric azo dyes, having p-NO₂C₆H₄ or m-NO₂C₆H₄, showed good light fastness. All of the polymeric azo dyes showed good bleeding resistance.