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.