Synthesis and properties of soluble and light-colored poly(amide-imide-imide)s based on tetraimide-dicarboxylic acid (TIDA) and various aromatic diamines: TIDA from 4,4′-oxydiphthalic anhydride, 1,4-bis(4-amino-2-trifluoromethylphenoxy)benzene, and 3-aminobenzoic acid

Abstract

A new tetraimide-dicarboxylic acid (TIDA) I was synthesized starting from 3-aminobenzoic acid ( m-ABA), 4,4′-oxydiphthalic anhydride (ODPA), and 1,4-bis(4-amino-2-trifluoromethylphenoxy)benzene (BAFPB) at a 2:2:1 molar ratio in N-methyl-2-pyrrolidone (NMP). A series of organosoluble, light-colored poly(amide-imide-imide)s (PAII, III a– j ) was prepared by triphenyl phosphite-activated polycondensation from the tetraimide-diacid I with various aromatic diamines ( II a– j ). All the polymers were readily soluble in a variety of organic solvents such as NMP, N, N-dimethyl acetamide (DMAc), dimethyl sulfoxide, and even in less polar m-cresol and pyridine. Polymer films cast from DMAc had the cutoff wavelengths between 374 and 384 nm and had the b ∗ values in the range of 14.8–30.2. Polymers III a– j afforded tough, transparent, and flexible films, which had tensile strengths ranging from 87 to 103 MPa, elongations at break from 11% to 37%, and initial moduli from 1.9 to 2.3 GPa. The glass transition temperatures of these polymers were in the range of 242–274 °C. They had 10% weight loss temperature above 526 °C and showed the char yield more than 55% residue at 800 °C in nitrogen.