Rearrangements in macromolecules containing an azomethyne bond

Aim of this work was to obtain thermo- and heat-resistant polymers with azomethine bond and to establish general regularities of their rearrangements into polymers with complex of valuable functional properties and capable of being processed by modern industrial methods. Initial task was development of methods for obtaining matrix polymers of required structure. Aromatic dinitriles, bisimidoyl chlorides, N-phenyldichloriminocarbonate as well as bisphenols and aromatic dicarboxylic acids were used as precursor monomers. Based on these monomers, polyimidates, polycarboxyimidates and polyiminocarbonates were synthesized, rearrangements of which at high temperatures led to polyamides, linear polyimides or polyurethanes, respectively. It was assumed that these rearrangements occurred intramolecularly without evolving by-products and according to mechanism of Chapman or Mumm-Hess rearrangements. Both initial polyimidates, polycarboxyimidates, polyiminocarbonates and rearranged polyamides, linear polyimides, polyurethanes possess high thermal stability, good solubility in common polar organic solvents and concentrated mineral acids. Materials based of them have high physico-mechanical characteristics.