Synthesis and properties of novel polyamides based on a benzonorbornane dietheramine

A set of new aromatic polyamides containing ether and benzonorbornane units were synthesized by the direct phosphorylation polycondensation of 3,6-bis(4-aminophenoxy)benzonorbornane (BAPBN) with various aromatic dicarboxylic acids. The polymers were produced with high yields and medium inherent viscosities (0.40-0.82 dL g(-1)). The polyamides based on rigid diacids showed limited solubility in organic solvents and could not afford ductile films. The polyamides derived from less rigid diacids were readily soluble in polar organic solvents and gave flexible and tough films via solvent casting. These polyamides showed glass-transition temperatures in the range of 200-269degreesC (by DSC), softening temperatures in the range of 220-289degreesC (by TMA), and 10% weight loss temperatures in excess of 450degreesC (by TGA). For a comparative study, a series of analogous polyamides based on 1,4-bis(4-aminophenoxy)benzene (BAPB) were also prepared and characterized.