New aryloxy-substituted condensation polymers

Abstract Large family of new aromatic diamines containing aryloxy side groups was developed. All the diamines were obtained on the basis of 2,4,6-trinitrotoluene (TNT) — very cheap and available explosive material. TNT was converted into 1,3,5-trinitrobenzene (TNB); subsequent aromatic nucleophilic nitro-displacement reactions led to mono- and diaryloxy-substituted mono- and dinitrobenzenes which were converted into the final aryloxy-substituted diamines. Interaction of the diamines obtained with aromatic dicarboxylic acids chlorides and aromatic tetracarboxylic acids dianhydrides led to the formation of new aryloxy-substituted polyimides and polyimides combining high thermal properties with solubility in organic solvents.