THERMAL LATENCY AND STRUCTURE-ACTIVITY RELATIONSHIP OF AMINIMIDES THEPOLYMERIZATION OF EPOXIDE

1,1-Dimethyl-1-( 2-hydroxypropyl) amine p-substituted benzimide (''ami nimide'') derivatives were prepared by the reaction of p-substituted m ethyl benzoates with equimolar amounts of 1,1-dimethylhydrazine and pr opylene oxide. These ylide compounds are shown to be useful as thermal ly latent initiators for the polymerization of glycidyl phenyl ether ( GPE). Bulk polymerization of GPE with 3 mol % of these aminimides was carried out at 40-150 degrees C for 8 h, showing greater than or equal to 100 degrees C was required for an effective rate. No consumption o f the monomer could be observed at temperatures lower than 80 degrees C. p-Methoxy substituted 1 showed the :Largest thermal latency among f our aminimides tested. The activities of the aminimides increased with an increase of electron-donating ability of the substituents on the b enzene ring, according to the following order: 1(p-MeO) > 2(p-Me) > 3( H) > 4(p-NO2). (C) 1997 John Wiley & Sons, Inc.