Synthesis and characterization of novel poly(amide-imide)s based on bis(p-amidobenzoic acid)-N-trimellitylimido-L-leucine

N-Trimellitylimido-L-leucine 3 was reacted with thionyl chloride and diacid chloride 4 was obtained in quantitative yield. The reaction of this diacid chloride with p-aminobenzoic acid was performed in dry THF and bis(p-amidobenzoic acid)-N-trimellitylimido-L-leucine 5 was obtained as an optically active aromatic imide-amide diacid in high yield. The diacid 5 was converted to diacid chloride 6 in quantitative yield by reacting with thionyl chloride. The polycondensation reaction of the new monomer imide-amide diacid chloride 6 with several aromatic diols such as bisphenol-A 7a, 4,4'-hydroquinone 7b, phenol phthalein 7c, 1,4-dihydroxyanthraquinone 7d, 1,8-dihydroxyanthraquinone 7e, and 2,4-dihydroxyacelophenone 7f was carried out under phase transfer conditions. The resulting novel poly(amide-ester-imide)s (PAEI)s having inherent viscosities 0.10-0.29 dig were obtained in high yield and are optically active and thermally stable. All of the above compounds were fully characterized by IR spectroscopy, elemental analyses and specific rotation. Key Words: bis(p-amidobenzoyl chloride)-N-trimellitylimido-L-leucine, poly(amide-ester-imide)s, phase transfer catalysis, optically active polymers, inherent viscosities, thermally stable polymer