Synthesis and properties of polyamides based on 5,5′-bis[4-(4-aminophenoxy)phenyl]-hexahydro-4,7-methanoindan

A new diamine 5,5'-bis[4-(4-aminophenoxy)phenyl]-hexahydro-4, 7-methanoindan (3) was prepared through the nucleophilic displacement of 5,5'-bis (4-hydroxylphenyl) -hexahydro-4,7-methanoindan (1) with p-halonitrobenzene in the presence of K2CO3 in N,N-dimethylformamide (DMF), followed by catalytic reduction with hydrazine and Pd/C in ethanol. A series of new polyamides were synthesized by the direct polycondensation of diamine 3 with various aromatic dicarboxylic acids. The polymers were obtained in quantitative yields with inherent viscosities of 0.76-1.02dlg(-1). All the polymers were soluble in aprotic dipolar solvents such as N,N-dimethylacetamide (DMAc) and N-methyl-2-pyrrolidone (NMP), and could be solution cast into transparent, flexible and tough films. The glass transition temperatures of the polyamides were in the range 245-282 degrees C nitrogen and above 465 degrees C in air. (C) 2000 Society of Chemical Industry.