New water-soluble polymer with allyl pendant groups

Abstract

Polymerization of N-allyl maleamic acid (AMA) is described. The monomer, AMA, was prepared by reaction of maleic anhydride with allyl amine. It was demonstrated for the first time that only maleate double bonds are involved in the radical polymerization and the allyl groups remain unreacted. Water-soluble oligomers (1800–2100 Da) with allyl pendant groups were obtained in reasonably high yields (up to 78% within 45 h) by using 2,2′-azobis(2-methylpropionamidine) dihydrochloride as a radical source. Notably no cyclo-polymers are formed in this polymerization. Experiments also showed that polymerization of this process is rather slow and proceeds with first-order kinetics (k = 1.03 × 10−6 s−1) in ethanol, at 75°C. Interestingly, in the co-polymerization with some other vinyl monomers, such as acrylamide, acrylic acid and vinyl acetate, AMA behaves as a bi-functional monomer and gives cross-linked polymers.