Abstract
A new N, N′-disubstituted bismalonimide was synthesized by the cycloaddition of methylenebis(4-phenylisocyanate) with pentamethyleneketene. Ringopening polyaddition reaction of the bismalonimide with aliphatic diamines was carried out in N-methyl-2-pyrrolidone to give a new class of alternating copolymalonamides having inherent viscosity of 0.5—1.0 in quantitative yield. The solution polymerization was almost completed at room temperature within 24 hr, or at 80°C within an hour. In methyl ethyl ketone, precipitation of polymer occurred to yield the polymer with rather lower inherent viscosity. The alternating copolymalonamides were amorphous, and showed melt temperature in the range of 150—200°C.
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T. Kagiya, M. Izu, T. Matsuda, and K. Fukui, J. Polym. Sci., Part A-1, 5, 15 (1967).
T. V. Sheremeteva, G. N. Larina, M. G. Zhenevskaya, and V. A. Gusinskaya, J. Polym. Sci., Part C, 16, 1631 (1967).
J. Sambeth and F. Grundschober, Preprints, International Symposium on Macromolecular Chemistry, Tokyo-Kyoto, 1966, p I-269.
S. A. Ballard and D. S. Melstrom, “Heterocyclic Compounds,” Vol. I, R. C. Elderfield, Ed., John Wiley and Sons, Inc., New York, N. Y., 1950, p 111.
A. Ebnöther, E. Jucker, E. Rissi, J. Rutschmann, E. Schreier, R. Steiner, R. Süess, and A. Vogel, Helv. Chim. Acta, 42, 918 (1959).
A. C. Poshkus and J. E. Herweh, J. Org. Chem., 30, 2466 (1965).
J. C. Martin, R. D. Burpitt, P. G. Gott, M. Harris, and R. H. Meen, J. Org. Chem., 36, 2205 (1971).
Y. Imai and H. Uchiyama, J. Polym. Sci., Part B, 8, 559 (1970).
Y. Imai and H. Uchiyama, Kobunshi Kagaku (Chem. High Polymers) 28, 73 (1971).
W. F. Charnicki and J.B. Data, J. Am. Pharm. Assoc, 45, 65 (1956).
W. F. Charnicki and J.B. Data, Chem. Abstr., 50, 13834 b (1956).
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Imai, Y., Hirukawa, H. Synthesis of Alternating Copolymalonamides by Ring-Opening Polyaddition Reaction of Bismalonimide with Diamines. Polym J 4, 93–99 (1973). https://doi.org/10.1295/polymj.4.93
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DOI: https://doi.org/10.1295/polymj.4.93