Direct Polycondensation of N -Trimellitylimido-L-isoleucine with Aromatic Diols.

Trimellitic anhydride (1) was reacted with L-isoleucine (2) in acetic acid and the resulting imide-acid [N-trimellitylimido-L-isoleucine] (4) was obtained in high yield. The direct polycondensation reaction of this diacid with several aromatic diols such as bisphenol A (Sa), phenolphthalein (5b), 4,4 -dihydroxybiphenyl (5c). 4,4 -dihydroxydiphenyl sulphide (5d), 4,4 -dihydroxydiphenyl suiphone (5e) and 1,4-dihydroxyanthraquinone (Sf) was carried out in a system of tosyl chloride (TsCI), pyridine (Py) and N,N-dimethylformamide (DMF). The reactions with TsCI were significantly promoted by controlling alcoholysis with diols in the presence of the catalytic amounts of DMF to give a series of optically active poly(ester-imide)s (PEI)s with good yield and moderate inherent viscosity ranging 0.18-0.28 dUg. The polycondensation reactions were significantly affected by the amounts of DMF, molar concentration of monomers, TsCI and pyridine, aging time, addition time of diols, temperature and the reaction time. All of the above polymers were fully characterized by 1H NMR, IR, elemental analysis and specific rotation. Some structural characterization and physical properties of these optically active poly(ester-imide)s are reported.