Polymers derived from 2‐furaldehyde and aromatic diamines. I

Abstract

AbstractPoly[imino (cyclopent‐2‐en‐1‐one‐2,4‐diyl) iminoarylenes] were prepared by the condensation of 2‐furaldehyde with various aromatic diamines in solution at room temperature. All polycondensations were carried out in one step and under identical conditions. It was observed that the most likely condensation reaction is through the furan rearrangement that leads to poly[imino (cyclopent‐2‐en‐1‐one‐2,4‐diyl) iminoarylenes]. The structures of all the polymer samples were confirmed by elemental analyses and by comparison of IR spectral characteristics with those of a model compound derived from 2‐furaldehyde and aniline. Number average molecular weights of all polymer samples were estimated from nonaqueous conductometric titration. The viscometric measurements of solutions of polymer samples in a formic acid–acetic acid (85 : 15) (v/v) mixture exhibited polyelectrolyte behavior. The thermal properties of polymer samples were revealed by thermogravimetry. The formation of the polymeric product is also explained. The result of preliminary tests for glass reinforcement of commercial epoxy resin and produced polymer samples suggest that laminate sheets with good mechanical strength can be obtained.