Soluble polyimides from unsymmetrical diamine containing benzimidazole ring and trifluoromethyl pendent group

Abstract

New unsymmetrical diamine monomer containing both the benzimidazole ring and trifluoromethyl group, 6,4′-diamino-2′-trifluoromethyl-2-phenylbenzimidazole, was prepared from 2-bromo-5-nitrobenzotrifluoride and 4-nitro-1,2-phenylenediamine. The monomer was polymerized with ODPA, BTDA and 6FDA by using one-pot synthetic method to obtain corresponding polyimides. All the prepared polyimides were soluble in aprotic polar solvents. Incorporation of trifluoromethyl groups unsymmetrically in the rigid polyimides improves their solubility without decreasing their physical properties. The polymers showed high glass transition temperature (Tg=289–352°C), high thermal stability (Td10>500°C), and relatively low coefficient of thermal expansion (CTE=26.1–46.4ppm/°C) because of their rigid-rod like structure. Also, they showed low refractive indexes (n=1.46–1.68) and low birefringence (Δ≈0.02) due to the trifluoromethyl pendent groups that interrupt chain packing and increase free volume.