Synthesis and Polymerization of Allyl Monomers Containing Pyrrole Ring

Abstract

3-(2-Pyrrolylmethylenimino)propene-1 (PIP) and 2-diallylamino-methylpyrrole (DAMP) were synthesized and the copolymerizability of these monomers was examined. The parameters of the copolymerization of PIP and DAMP with acfylonitrile (AN) were obtaind as follows.
In the copolymerization of DAMP with fumaronitrile (FN), the maximum rate ef the copolymerizatien Rp(max) appeared at the lower concentration of DAMP in monomer feed. This can be explained by assuming that the degradative chain transfer to DAMP occurs remarkably at the higher concentration of DAMP. The copolymer composition DAMP/FN was 1/2, because DAMP is a diallyl monomer.
In the copolymerization of PIP with FN, Rp(max) appeared at the higher concentration of PIP. This is because the azomethine group of PIP may participate in the copolymerization as a propagating radical in addition to the allyl group of PIP. This assumption might be supported by the fact that the absorption of the vinyl group in IR spectra (δcH 990, 910cm^-1)remains slightly and that absorption ef the azomethine group in IR spectra (Vc=n 1640 cm^-1)is weakened.