A triaziridine containing compound, trimethylolpropane tris(1-aziridinepropionate) (TMPTA-AZ), is prepared from a Michael addition of aziridine (AZ) with trimethylolpropane triacrylate (TMPTA). A rapid polymerization of acrylic acid (AA) with TMPTA-AZ occurred at ambient temperature without catalyst. This polymerization process involves three subsequent reactions are proposed: (1) An exothermic neutralization takes place between AA and TMPTA-AZ. (2) That neutralization heat triggers AZ ring-opening reaction and that carboxyl group (of AA) plays as a nucleophile and results in an amino ester bond formation. (3) A final crosslinked polymer is obtained from that amino group reacts with its acrylic double bond via an intermolecular Michael addition reaction. These new crosslinked polymers with various performance properties are obtained from a mixture of AA and TMPTA-AZ in different ratios and post-heating.
Journal of Applied Polymer Science 104(2), pp.809-815