Processable, high Tg polyimides from unsymmetrical diamines containing 4-phenoxy aniline and benzimidazole moieties

Two novel unsymmetric diamine isomers, 6-amino-2-(4-(4-aminophenoxy)phenyl)-1H-benzimidazole (3p) and 6-amino-2-(3-(4-aminophenoxy)phenyl)-1H-benzimidazole (3 m), were synthesized and employed to react with several aromatic dianhydrides to yield two new series of poly (benzimidazole imide)s (PBIPIs), PI-4 (a-e) and PI-5 (c-e) through two-step and one step polymerization method, respectively. The effect of chain isomerism on molecular packing and physical properties of PBIPIs is investigated. Both series exhibited excellent thermal stability ( T 5%  = 503–559 °C), high T g values (276–383 °C) and good mechanical properties (tensile strengths of 98–151 MPa and tensile moduli of 3.5–5.2 GPa). The PI-5 (c-e) showed high solubility compared to PI-4 (a-e) series. Such improved solubility attributed to the flexible ether connecting groups with non-coplanarity. Furthermore, controlled molecular weight ( Mw ) polymer PI-5e-PA derived from 3 m, demonstrated good solution and melt processability.