Synthesis and polymerization of N,N-diallyl morpholinium bromide

N,N-diallyl morpholinium bromide has been synthesized in high yields (96%) by stepwise condensation of morpholine with allyl chloride and allyl bromide. Polymerizability of the quaternary ammonium salt has been studied using various solvents and radical initiators such as K₂S₂O₈ and t-butyl hydroperoxide. High yields of polymers have been obtained by precipitation polymerization in n-butanol with t-butyl hydroperoxide as radical initiator. This method gives low molecular weight polymers, whereas polymers with moderate molecular weights have been obtained in concentrated aqueous solutions. Copolymerization of the monomer with sulfur dioxide has also been studied. The structures of the monomer and polymers have been elucidated by elemental microanalysis, NMR and FT-IR spectroscopy.