Synthesis of Novel Thermostable Polyamideimides from Bis(2-aminoethyl)terephthalamide and Dianhydrides

Abstract

Bis(2-aminoethyl)terephthalamide, an amide-containing diamine, was obtained from the aminolysis of waste poly(ethylene terephthalate) bottles. This diamine reacts with various aromatic dianhydrides to form novel polyamideimides (PAIs). The formation of amic acid or ammonium carboxylate salt intermediates depends strongly on the substituents of the dianhydrides. The electron-withdrawing substituents promote the creation of an ammonium carboxylate salt, whereas the electron donors assist with the amic acid intermediate formation. These salts and amic acids were further converted into polyimides by thermal treatment. The structures of the intermediates and PAIs were characterized by Fourier transform infrared, 1H nuclear magnetic resonance (NMR), and 13C NMR spectroscopies, and their thermal properties were determined by differential scanning calorimetry and thermogravimetry. X-ray diffraction patterns and inherent viscosity values of these PAIs were also reported. By using these chemical transformations, waste poly(ethylene terephthalate) bottles were converted into high-performance PAIs. These PAIs can be used as membrane-modifying agents for industrial separation applications.