Synthesis and characterization of new poly(diketone imide)s derived from 1,4-bis(3,4-dicarboxybenzoyl)benzene dianhydride and various diamines

Abstract

1,4-Bis(3,4-dicarboxybenzoyl)benzene dianhydride, an aromatic bis(ketone anhydride) monomer, was synthesized by the Friedel–Crafts reaction of terephthaloyl dichloride and o-xylene, followed by the oxidation of the intermediate tetramethylated compound and cyclodehydration of the resulting tetraacid. A series of new poly(diketone imide)s (PDKIs) were prepared from this dianhydride with various aromatic diamines via a conventional two-stage process that included ring-opening polyaddition to form the poly(amic acid)s followed by thermal or chemical imidization. Most of the PDKIs through chemical imidization were soluble in aprotic amide solvents, such as N, N-dimethylacetamide, N-methyl-2-pyrrolidone, m-cresol, and so on. The resulting PDKIs had good thermal property with the glass transition temperature of 203–275°C, the temperature at 5% weight loss of 500–539°C, and the residue of 51–60% at 800°C in nitrogen. Additionally, strong and flexible PDKI films obtained by thermal imidization exhibited outstanding mechanical property with the tensile strength of 88.8–158.5 MPa, tensile modulus of 1.9–3.5 GPa, and elongation at breakage of 7–21%.