N-methylolmaleimide-benzene photoadduct: A novel monomer for the synthesisof functionally modified polyimides

A novel polycyclic dihydroxy diimide monomer was synthesized through the ph otocycloaddition of N-methylolmaleimide to benzene and the reaction of male imide-benzene photoadduct with formaldehyde. The monomer, which evolved for maldehyde at about 165 degrees C, was subsequently used to prepare low mole cular weight polyamineimides and polyurethaneimides. Soluble polyamineimide s, prepared with three different aromatic diamine monomers, exhibited initi al decomposition temperatures between 277 and 329 degrees C and glass-trans ition temperatures between 180 and 219 degrees C. An aliphatic polyamineimi de prepared from 1,6-hexanediamine was insoluble and had glass-transition a nd initial decomposition temperatures of 225 degrees C and 294 degrees C, r espectively, with prior loss of formaldehyde from end groups. Polyurethanei mides prepared with two aromatic diisocyanates showed loss of formaldehyde in the approximate range of 160-169 degrees C followed by loss of CO2 and g lass-transition temperatures of 219 and 233 degrees C. Attempts to prepare polyamideimides resulted in oligomers with a low nitrogen content. Attempts to prepare polyesterimides were unsuccessful. (C) 2000 John Wiley & Sons, Inc.