Polyimidines. XI. Polyimidines from 3,3′,4,4′-benzophenonetetracarboxylic dianhydride and 4,4′-(hexafluoroisopropylidene) diphthalic anhydride

Two new bis(benzylidenephthalide)monomers were synthesized by melt condensation of phenylacetic acid with 3,3′,4,4′-benzophenonetetracarboxylic dianhydride (BTDA) and with 4,4′-(hexafluoroisopropylidene)diphthalic anhydride (6FDA). A mixture of three isomers for each monomer was obtained and polymerized with diamines to produce new polyimidines. Polymerizations were conducted with m-xylylenediamine (MXDA) or 4,4′-oxydianiline (ODA) in quantitative yields for the undehydrated intermediate. Inherent viscosities ranged from 0.17 to 0.35 dL/g in N,N-dimethylformamide (DMF) or N-methyl-2-pyrrolidone (NMP). These intermediate poly(hydroxylactams) were thermally dehydrated to polyimidines which exhibited a 10% weight loss, as high as 546°C in nitrogen. Inherent viscosities of the dehydrated (cured) polyimidines ranged from 0.14 to 0.20 dL/g in NMP. Brittle films could be cast from NMP solutions.