Radical Copolymerization of N-Substituted 2-Azanorborn-5-enes with N-Vinylpyrrolidone

Abstract

The radical copolymerization of N-methyl-2-azanorborn-5-ene, N-benzyl-2-azanorborn-5-ene, N-allyl-2-azanorborn-5-ene, and N-(2-azanorborn-5-en-2-yl)methyl acetate with N-vinylpyrrolidone is carried out in bulk in the presence of AIBN as an initiator. It is shown that the copolymerization yields statistical copolymers enriched in N-vinylpyrrolidone units. It is demonstrated that the rate of copolymerization decreases with increasing fraction of azanorbornene in the initial monomer mixture. Using 13С NMR spectroscopy, it is found that the copolymerization of azanorbornenes with N-vinylpyrrolidone occurs via the double bond of the norbornene ring. The allyl group of N-allyl-2-azanorborn-5-ene is uninvolved in copolymerization at both the equimolar comonomer ratio and the double excess of N-vinylpyrrolidone.