Preparation of polyimides utilizing the diels–alder reaction. I. Bis(3,4‐dimethylenepyrrolidyl) arylenes with bismaleimides

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Abstract
Bis(exocyclic)dienes were prepared by the reaction of 2,3‐dibromomethyl‐1,3‐butadiene with aromatic diamines. The diamines were 4,4′‐methylene dianiline, 4,4′‐oxy dianiline, benzidine, and α, α′‐bis(4‐aminophenyl)‐p‐isopropyl benzene (EPON HPT 1061). Polymers were synthesized by the Diels–Alder reaction of these bisdienes with bis(4‐maleimidylphenyl) methane. Flexible films were obtained for diene: dienophile ratios ranging from 0.7 : 1 to 0.8 : 1. Films were found to be insoluble in organic solvents and those cured above 120°C were insoluble in concentrated sulfuric acid. The polymers were characterized by IR, TGA, and elemental analysis.