Macromolecules, Vol.43, No.21, 8821-8827, 2010
Aminimides Derived from Benzoylformic Acid Esters as Thermally Latent Base Catalysts
As a novel thermal latent anionic initiator for lower temperature applications, a new class of aminimide, 1,1-dimethyl-1-(2-hydroxypropyl)amine benzoylformimide (BFI), was synthesized from benzoylformic acid methyl ester in 95% yield, and its thermal rearrangement behavior was studied in detail. Thermal rearrangement of BFI proved to take place on heating above 80 degrees C via the Curtius rearrangement mechanism, generating the corresponding isocyanate, hydroxyamine, and their further reaction products. BFI proved to catalyze the polymerization of epoxides and epoxide/thiol system on heating above 80 degrees C. They exhibit both the long pot life and the low-temperature rapid polymerization in the presence of BFI which supported the promising applications of BFI as an efficient thermal latent base catalyst for anionically polymerizable/curable systems.