Synthesis and properties of polyamides based on 1,1-bis[4-(4-aminophenoxy)phenyl]cyclohexane

An ether diamine monomer containing the cyclohexane structure, 1,1-bis[4-(4-aminophenoxy)phenyl]cyclohexane (BAPC), was prepared through nucleophilic substitution reaction of 1,1-bis(4-hydroxyphenyl)cyclohexane and p-chloronitrobenzene in the presence of K2CO3, followed by catalytic hydrazine reduction. Using triphenyl phosphite and pyridine as condensing agent, novel polyamides were directly polycondensated from BAPC with various aromatic dicarboxylic acids in the N-methyl-7-pyrrolidone (NMP) solution containing dissolved calcium chloride. The resulting polyamides had inherent viscosities from 0.97 to 1.61 dL g(-1). Most had good solubility in polar organic solvents such as NMP and N,N-dimethylacetamide, and afforded transparent, flexible, and tough films by solution casting. The glass transition temperatures (T-g) of the polymers were 188-240 degrees C and 10% mass loss temperatures were recorded at 473-499 degrees C in air. A comparative study on the properties with corresponding polyamides derived from 1,1-bis[4-(4-carboxyphenoxy)phenyl]cyclohexane (BCPC) was made.