The Preparation and Properties of Polyamines Prepared by the Reduction of Poly(4-vinylpyridine)

Abstract

Poly(4-vinylpyridine), both as a linear polymer and as a cross-linked resin was quaternized with methyl iodide (I, II) and reduced with sodium borohydride to poly(4-vinyltetrahydropyridine) (III, IV). The remaining double bonds in 111 or IV were inert to catalytic hydrogenation and to reduction with diborane or diimide. Catalytic hydrogenation of linear poly(4-vinylpyridine), quaternized with methyl iodide (I), gave irreproducible results; however, the fully saturated linear poly(4-vinylpiperidine) (V) was obtained in one experiment. Polyamine resins were also prepared by reacting dibromohexane with tetramethylene diamine (VI) and by reacting epichlorohydrin with tetramethylene-diamine (VII). The suitability of all these polyamines as the mine component in thermally regenerable resin systems was examined. The polyamines III, N, VI, and VII oxidized faster than polystyrene-based polyamines whereas V oxidized much more slowly. The amine capacities were all greater than polystyrene-based polyamines and were at least equal to those of poly(alkyldiallylamine)s.