Synthesis and radical polymerization of bifunctionalized aziridinic methacrylates

The synthesis and controlled radical polymerization of 2-(1-aziridinyl)ethyl methacrylate (AZMA) and (1-phenylaziridin-2-yl)methyl methacrylate (PAZMA), which have two polymerizable groups in their structures, were performed. RAFT polymerization using CPDB as chain transfer agent (CTA) and AIBN as initiator was carried out in bulk and in solution at 60 °C with a good control of the molecular weight. A living behavior was observed for both monomers. ATRP polymerization (CuBr/PMDETA/EBiB) of AZMA led to a crosslinked material. For PAZMA a nonliving behavior in ATRP polymerization was reached, however no crosslink was observed due to higher stability of its aziridine ring.