High temperature resins based on allylamine/bismaleimides

Abstract

Synthesis, curing, and physical/mechanical properties of 4,4′-bismaleimidodiphenylmethane (BDM), 4,4′-bismaleimidodiphenylether (BDE), 3,3′-bismaleimidodiphenylsulfone (3-BDS), and 4,4′-bismaleimidodiphenylsulfone (4-BDS) adducted with various amount of allylamines were investigated and compared with each other. BDM was reacted with allylamines exclusively through the Michael addition reaction, whereas 3-BDS and 4-BDS were reacted with allylamines by amidation along with the cleavage of an imide-ring CN bond. Only BDE underwent both reactions to yield BDE/allylamine adducts. Three types of curing reactions might occur depending on the amount of adducted allylamines: (1) thermal homopolymerization through the maleimide double bonds; (2) accelerated homopolymerization by allylamines; and (3) polymerization of the cleaved allylamines by themselves or with the maleimido groups. Of all the BMIs/allylamines adducts under study, the cured BDM/50 mol% allylamine and BDE/50 mol% allylamine adducts have superior mechanical properties. In addition, the former resin has a glass transition temperature ( T g) of 335°C and a degradation temperature ( T d) of 471°C, whereas the latter has a T g of 349°C and a T d of 436°C.