Abstract
New isocyanates bearing the carbamate group, 6-(butoxycarbonylamino)hexyl isocyanate (nBAHI), 6-((S)-(+)-s-butoxycarbonylamino)hexyl isocyanate ((+)-BAHI), and 4-((S)-(+)-s-butoxycarbonylamino)butyl isocyanate ((+)-BABI), were synthesized by reaction of a diisocyanate with an alcohol and polymerized with various anionic initiators in THF at −98°C. The polymerization afforded soluble polymers mainly consisting of a 1-nylon structure. The CD spectral patterns of poly((+)-BAHI) and poly((+)-BABI) were similar to those of optically active helical poly(alkyl isocyanate)s, indicating that the optical rotation of poly((+)-BAHI) and poly((+)-BABI) is determined mainly by the prevailing helicity of the polymer chain. The chiral center in the side group separated by ten or eight σ-bonds from the polymer main chain appears to influence the helical sense of the polymer through intramolecular effect.
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Maeda, K., Matsunaga, M., Yamada, H. et al. Synthesis and Anionic Polymerization of Isocyanates Bearing a Carbamate Group. Polym J 29, 333–338 (1997). https://doi.org/10.1295/polymj.29.333
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DOI: https://doi.org/10.1295/polymj.29.333