Synthesis, characterization and gas transport properties of novel poly(amine-imide)s containing tetraphenylmethane pendant groups

Abstract

Two bis(amine anhydride) monomers containing tetraphenylmethane pendant groups were synthesized from the palladium-catalyzed amination reaction of N-methyl-4-chlorophthalimide with different arylamines, followed by alkaline hydrolysis of the intermediate bis(amine-imide)s and subsequent dehydration of the resulting tetraacids. These monomers were polymerized with the appropriate aromatic diamines to obtain a series of novel poly(amine-imide)s. The obtained polymers exhibited good solubility in many aprotic solvents and had glass transition temperatures in the range of 310 to 395 °C. Thermogravimetric analysis showed that all of the polymers were stable, with 10% weight loss recorded above 510 °C under nitrogen. The surface areas of these novel poly(amine-imide)s ranged from 78 to 290 m² g⁻¹. Films obtained by casting exhibited a combination of relatively high permeability and modest to good permselectivity with values close to Robeson’s upper bound limit for O₂/N₂ and CO₂/CH₄ gas pairs.