Abstract
t-Butylacetylene was polymerized by MoCl5 and WCl6 as catalysts at 30°C or 0°C in hydrocarbon and halogenated hydrocarbon solvents. Poly(t-butylacetylene) was obtained in high yield especially with MoCl5, and the highest polymer molecular weight exceeded 3×105. The following relationship was obtained between the viscosity and molecular weight: [η]=10−5.12 Mn1.01. The polymer was soluble in nonpolar solvents, particularly in aliphatic hydrocarbons. The infrared (IR), 1H nuclear magnetic resonance (NMR), and 13C NMR spectra supported the expected polymer structure, –[–CH=C(t-Bu)–]–n. A pair of doublets were observed for the methyl carbon in the 13C NMR of polymer, making possible an evaluation of geometric structure.
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G. Natta, G. Mazzanti, and P. Pino, Angew. Chem., 69, 685 (1957).
G. Natta, G. Mazzanti, G. Pregaglia, and M. Peraldo, Gazz. Chim. Ital., 89, 465 (1959).
A. A. Berlin, E. F. Vainshtein, M. I. Cherkashin, and Yu. Sh. Moshkovskii, Vysokomol. Soedin., Ser., 5, 1354 (1963).
F. Ciardelli, E. Benedetti, and O. Pieroni, Makromol. Chem., 103, 1 (1967).
W. J. Trepka and R. J. Sonnenfeld, J. Polym. Sci., Part A-1, 8, 2721 (1970).
P. S. Woon and M. F. Farona, J. Polym. Sci., Polym. Chem. Ed., 12, 1749 (1974).
W. H. Watson, Jr., W. C. McMordie, Jr., and L. G. Lands, J. Polym. Sci., 55, 137 (1961).
W. Kawai, Kogyo Kagaku Zasshi, 69, 1994 (1966).
Y. Odaira, M. Hara, and S. Tsutsumi, Technol. Rep. Osaka Univ., 15, 325 (1965).
O. Pieroni, F. Matera, and F. Ciardelli, Tetrahedron Lett., 597 (1972).
F. Ciardelli, S. Lanzillo, and O. Pieroni, Macromolecules, 7, 174 (1974).
W. Hubel and C. Hoozand, Chem. Ber., 93, 103 (1960).
L. S. Meriwether, E. C. Colthup, G. W. Kennerly, and R. N. Reusch, J. Org. Chem., 26, 5155 (1961).
R. Tsumura and N. Hagihara, Bull. Chem. Soc. Jpn., 37, 1889 (1964).
T. J. Katz and S. J. Lee, J. Am. Chem. Soc., 102, 424 (1980).
T. Masuda, Y. Kuwane, K. Yamamoto, and T. Higashimura, Polym. Bull., 2, 823 (1980).
M. G. Voronkov, V. B. Pukhnarevich, S. P. Sushchinskaya, V. Z. Annenkova, V. M. Annenkova, and N. J. Andreeva, J. Polym. Sci., Polym. Chem., Ed., 18, 53 (1980).
T. Masuda, K. Hasegawa, and T. Higashimura, Macromolecules, 7, 728 (1974).
N. Sasaki, T. Masuda, and T. Higashimura, Macromolecules, 9, 664 (1976).
T. Ohtori, T. Masuda, and T. Higashimura, Polym. J., 11, 805 (1979).
T. Masuda, H. Kawai, T. Ohtori, and T. Higashimura, Polym. J., 11, 813 (1979).
P. D. Bartlett and L. J. Rosen, J. Am. Chem. Soc., 64, 543 (1942).
P. J. Kocienski, J. Org. Chem., 39, 3285 (1974).
H. Shirakawa and S. Ikeda, Polym. J., 2, 231 (1971).
H. Noguchi and S. Kambara, J. Polym. Sci., B, 1, 553 (1963).
T. Kitano, T. Fujimoto, and M. Nagasawa, Macromolecules, 7, 719 (1974).
Y. Kuwane, T. Masuda, and T. Higashimura, unpublished data.
T. Masuda, N. Sasaki, and T. Higashimura, Macromolecules, 8, 717 (1975).
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Masuda, T., Okano, Y., Kuwane, Y. et al. Polymerization of t-Butylacetylene Catalyzed by MoCl5 and WCl6. Polym J 12, 907–913 (1980). https://doi.org/10.1295/polymj.12.907
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DOI: https://doi.org/10.1295/polymj.12.907
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