Synthesis of polyaminoquinones by vinylogous nucleophilic substitution polymerization of 2,5-disubstituted p-benzoquinones with diamines

Vinylogous nucleophilic substitution polymerization of 2,5-dihydroxy-p-benzoquinone and 2,5-dimethoxy-p-benzoquinone with various diamines in m-cresol afforded polyaminoquinones with inherent viscosities as high as 0,5 dl.g^?1 in quantitative yields. The polyaminoquinones, except for the polymer derived from 1,3-bis(aminomethyl)benzene, were partially soluble or practically insoluble in organic solvents, but were solubilized by alkaline hydrosulfite reduction. Thermal analyses showed an initial weight loss at around 200°C in both air and nitrogen atmospheres, followed by gradual decomposition.