Abstract
The asymmetric hydrogenation of benzyl acetoacetate afforded benzyl (R)-3-hydroxybutanoate (II). Optically active ester-containing dicarboxylic acid V was newly prepared from II and terephthaloyl chloride, followed by debenzylation. The polycondensation of V with aromatic diamines was carried out in the presence of triphenyl phosphite, pyridine, and calcium chloride in N-methyl-2-pyrrolidone (NMP). The resulting optically active polyester-amides had inherent viscosities of 0.44–0.79 dl g−1, and specific rotations from −43.6° to −78.5°. The glass transition temperatures of the polymers were in the range from 129°C to 169°C, and their decomposition started at a temperature from 231°C to 249°C to afford biscrotonamide and terephthalic acid. The glass transition temperature of the optically active polymer derived from 4,4′-oxydianiline was 8°C higher than that of the corresponding inactive analogue.
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Kobayashi, T., Kakimoto, Ma. & Imai, Y. Synthesis and Properties of Optically Active Polyester-amides from Ester-Containing Chiral Dicarboxylic Acid and Aromatic Diamines. Polym J 25, 65–73 (1993). https://doi.org/10.1295/polymj.25.65
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DOI: https://doi.org/10.1295/polymj.25.65