Novel Optically Active Poly(amide-imide)s Derived from N-Trimellitylimido-L-Isoleucine and Different Diisocyanates

Summary

A new class of optically active poly(amide-imide)s was synthesized via direct solution polycondensation of different aliphatic and aromatic diisocyanates with a chiral diacid monomer. The polymerization of N-trimellitylimido-L-isoleucine (TMIIL)(1) as an aromatic-aliphatic diacid monomer with 4,4’-methylenebis(phenyl isocyanate) (MDI)(2) was carried out by graduate heating as well as refluxing method in the presence of pyridine (Py), dibutyltin dilaurate (DBTDL), triethylamine (TEA) as a catalyst and without catalyst, respectively. In these solution polycondensations we used amino acids as chiral inducing agents. The optimized polymerization conditions of MDI were used for the polymerization of isophorone diisocyanate (IPDI)(3), tolylene-2,4-diisocyanate (TDI)(4), and hexamethylene diisocyanate (HDI)(5). The resulting polymers have inherent viscosities in a range of 0.17–0.48 dL/g. These polymers are optically active, thermally stable and soluble in amide type solvents.