Rigid Chain Vinyl Polymers from Multi-Substituted Ethylenes

  • Takayuki Otsu
  • Akikazu Matsumoto
  • Masahiro Yoshioka

Abstract

Novel vinyl polymers were synthesized from 1,1- or 1,2-disubstituted and 1,1,2-trisubstituted ethylenes by radical polymerization. The polymers obtained consist of a rigid chain structure on account of the bulky side groups compared with flexible poly(monosubstituted ethylene)s. The substituted polymethylenes obtained from 1,2-disubstituted ethylenes such as fumaric and maleic derivatives were revealed to have new properties different from ordinary vinyl polymers. Radical polymerization behaviors of these multi-substituted ethylenes and some properties of the resulting polymers were investigated.

Keywords

Benzene Vinyl Anhydride Macromolecule Styrene 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    T. Otsu, “Radical Polymerization (I) Elementary Reaction Mechanism”, Kagaku Dojin, Kyoto, 1971Google Scholar
  2. 2.
    T. Otsu, O. Ito, N. Toyoda, and S. Mori, Makromol. Chem., Rapid Commun., 2, 725 (1981)CrossRefGoogle Scholar
  3. 3.
    T. Otsu, T. Yasuhara, and A. Matsumoto, J. Macromol. Sci.-Chem, A25, 537 (1988), and references cited thereinGoogle Scholar
  4. 4.
    A. Shimizu, T. Otsu, and M. Imoto, J. Polym. Sci., B3, 449 (1965)Google Scholar
  5. 5.
    T. Otsu, A. Shimizu, and M. Imoto, J. Polym. Sci., A1, 4, 1579 (1966)Google Scholar
  6. 6.
    J. P. Kennedy and T. Otsu, Adv. Polym. Sci., 7, 369 (1970)CrossRefGoogle Scholar
  7. 7.
    K. Endo and T. Otsu, “Monomer-Isomerization Polymerization”, in Handbook of Mass and Heat Transfer, Ed., N. P. Cheremisinoff, Vol.3., pp.553–581, Gulf Publishing, 1988Google Scholar
  8. 8.
    K. J. Ivin, “Cycloalkenes and Bicycloalkenes”, in Ring-Opening Polymerization, Eds., K. J. Ivin and T. Saegusa, Chapter 3, Elsevier, 1984Google Scholar
  9. 9.
    H. K. Hall, Jr. A. B. Padias, A. Pandya, and H. Tanaka, Macromolecules, 20, 247 (1987)CrossRefGoogle Scholar
  10. 10.
    C. Lee and H. K. Hall, Jr., Macromolecules, 22, 21 (1989)CrossRefGoogle Scholar
  11. 11.
    T. Otsu, Makromol. Chem., Macromol. Symp., 10/11, 235 (1987)CrossRefGoogle Scholar
  12. 12.
    M. Yoshioka and T. Otsu, Macromolecules, in pressGoogle Scholar
  13. 13.
    T. Otsu and M. Yoshioka, Macromolecules, submittedGoogle Scholar
  14. 14.
    M. Yoshioka, A. Matsumoto, and T. Otsu, Polym. J., 23, 1249 (1991)CrossRefGoogle Scholar
  15. 15.
    T. Otsu, B. Yamada, and T. Ishikawa, Macromolecules, 24, 415 (1991)CrossRefGoogle Scholar
  16. 16.
    B. Yamada, E. Yoshikawa, H. Miura, K. Shiraishi, and T. Otsu, Polymer, 32, 1892 (1991)CrossRefGoogle Scholar
  17. 17.
    B. Yamada, E. Yoshikawa, H. Miura, and T. Otsu, Polym. Bull., 26, 543 (1991)CrossRefGoogle Scholar
  18. 18.
    M. S. Matheson, E. E. Auer, E. B. Bevilacqua, and E. J. Hart, J. Am. Chem. Soc, 73, 1700 (1951)CrossRefGoogle Scholar
  19. 19.
    M. S. Matheson, E. E. Auer, E. B. Bevilacqua, and E. J. Hart, J. Am. Chem. Soc, 71, 497 (1949)CrossRefGoogle Scholar
  20. 20.
    M. Yoshioka and T. Otsu, Macromolecules, submittedGoogle Scholar
  21. 21.
    G. Natta, P. Pino, P. Corradini, E. Danusso, E. Mantica, G. Mazzanti, and G. Moraglio, J. Am. Chem. Soc, 77, 1708 (1955)CrossRefGoogle Scholar
  22. 22.
    G. Natta, Makromol. Chem., 16, 213 (1955); J. Polym. Sci., 16, 143 J. Polym. Sci., 35, 94 (1960)CrossRefGoogle Scholar
  23. 23.
    X. Wang, T. Komoto, I. Ando, and T. Otsu, Makromol. Chem., 189, 1845 (1988)CrossRefGoogle Scholar
  24. 24.
    M. Yoshioka, A. Matsumoto, T. Otsu, and I. Ando, Polymer, 32, 2741 (1991)CrossRefGoogle Scholar
  25. 25.
    M. Yoshioka, A. Matsumoto, and T. Otsu, Polym. J., 23, 1191 (1991)CrossRefGoogle Scholar
  26. 26.
    A. Matsumoto, T. Tarui, and T. Otsu, Macromolecules, 23, 5102 (1990)CrossRefGoogle Scholar
  27. 27.
    K. Shigehara, M. Hara, H. Nakahama, S. Miyata, Y. Murata, and A. Yamada, J. Am. Chen. Soc., 109, 1237 (1987)CrossRefGoogle Scholar
  28. 28.
    S. B. Choi, A. Takahara, N. Amaya, Y. Murata, and T. Kajiyama, Polym. J., 21, 433 (1989)CrossRefGoogle Scholar
  29. 29.
    N. Toyoda, M. Yoshida, and T. Otsu, Polym. J., 15, 255 (1983)CrossRefGoogle Scholar
  30. 30.
    A. Matsumoto and T. Otsu, Polym. Commun., in pressGoogle Scholar
  31. 31.
    A. Matsumoto, K. Fukushima, and T. Otsu, J. Polym. Sci., Part A: Polym. Chem., 29, 1697 (1991)CrossRefGoogle Scholar
  32. 32.
    A. Matsumoto, R. Kotaki, and T. Otsu, J. Polym. Sci., Part A: Polym. Chem., 29, 1707 (1991)CrossRefGoogle Scholar
  33. 33.
    F. M. Lewis and F. R. Mayo, J. Am. Chem. Soc., 70, 1533 (1948)CrossRefGoogle Scholar
  34. 34.
    A. R. Bader, R. P. Buckley, F. Leavitt, and M. Szware, J. Am. Chem. Soc, 79, 5621 (1957)CrossRefGoogle Scholar
  35. 35.
    B. Giese, Angew. Chem. Int. Ed. Engl., 22, 753 (1983)CrossRefGoogle Scholar
  36. 36.
    O. Ito and M. Matsuda, J. Polym. Sci., Polym. Chem. Ed., 28, 1947 (1990)CrossRefGoogle Scholar
  37. 37.
    M. S. Newman and R. W. Addor, J. Am. Chem. Soc., 75, 1263 (1953)CrossRefGoogle Scholar
  38. 38.
    K. Hayashi and G. Smets, J. Polym. Sci., 27, 626 (1958)CrossRefGoogle Scholar
  39. 39.
    N. D. Field and J. R. Schaefgen, J. Polym. Sci., 58, 533 (1962)CrossRefGoogle Scholar
  40. 40.
    N. G. Gaylord, J. Macromol. Sci.-Rev., C13, 235 (1975)Google Scholar
  41. 41.
    P. O. Tawney, R. H. Snyder, R. P. Conger, K. A. Leibbrand, C. H. Stiteler, and A. R. Williams, J. Org. Chem., 26, 15 (1961)CrossRefGoogle Scholar
  42. 42.
    R. C. P. Cubbon, Polymer, 6, 419 (1965)CrossRefGoogle Scholar
  43. 43a.
    M. Yamada, and I. Takase, Kobunshi Kagaku, 22, 626 (1965)Google Scholar
  44. 43b.
    M. Yamada, I. Takase, and T. Mishima, Kobunshi Kagaku, 26, 393 (1969)CrossRefGoogle Scholar
  45. 44.
    J. M. G. Cowie, “Alternating Copolymers”, Plenum, New York, 1985Google Scholar
  46. 45.
    T. Otsu, A. Matsumoto, T. Kubota, and S. Mori, Polym. Bull., 23, 43 (1990)CrossRefGoogle Scholar
  47. 46.
    A. Matsumoto, T. Kubota, and T. Otsu, Polym. Bull., 24, 459 (1990)CrossRefGoogle Scholar
  48. 47.
    A. Matsumoto, Y. Oki, and T. Otsu, Polym. J., 23, 201 (1991)CrossRefGoogle Scholar
  49. 48.
    T. Otsu, A. Matsumoto, and T. Kubota, Polym. International, 25, 179 (1991)CrossRefGoogle Scholar
  50. 49.
    T. Otsu, A. Matsumoto, and A. Tatsumi, Polym. Bull., 24, 467 (1990)CrossRefGoogle Scholar
  51. 50.
    A. Matsumoto, Y. Oki, and T. Otsu, Polym. J., 23, 1371 (1991)CrossRefGoogle Scholar
  52. 51.
    A. Matsumoto, T. Kubota, and T. Otsu, Macromolecules, 23, 4508 (1990)CrossRefGoogle Scholar
  53. 52a.
    S. Nagai, T. Uno, and K. Yoshida, Kobunshi Kagaku, 15, 550 (1958)Google Scholar
  54. 52b.
    S. Nagai and K. Yoshida, Kobunshi Kagaku, 17, 77, 79, 748 (1960)CrossRefGoogle Scholar
  55. 52c.
    S. Nagai, Bull. Chem. Soc. Jpn., 36, 1459 (1963); 37, 369 (1964)CrossRefGoogle Scholar
  56. 53.
    T. Otsu, H. Watanabe, J. -Z. Yang, M. Yoshioka, and A. Matsumoto, Makromol. Chem., Macromol. Symp., in pressGoogle Scholar
  57. 54.
    T. Otsu, M. Okuo, H. Watanabe, and J. -Z. Yang, Chem. Express, 5, 953 (1990)Google Scholar
  58. 55.
    J. -Z. Yang and T. Otsu, Makromol. Chem., Rapid Commun., 12, 205 (1991)CrossRefGoogle Scholar
  59. 56.
    J. -Z. Yang and T. Otsu, Polym. Bull., 25, 145 (1991)CrossRefGoogle Scholar
  60. 57.
    T. Sato, S. Inui, H. Tanaka, T. Ota, M. Kamachi, and K. Tanaka, J. Polym. Sci., Polym. Chem. Ed., 25, 637 (1987)CrossRefGoogle Scholar
  61. 58.
    T. Sato, N. Morita, H. Tanaka, and T. Ota, J. Polym. Sci., Part A; Polym. Chem., 27, 2497 (1989)CrossRefGoogle Scholar
  62. 59.
    T. Sato, K. Morino, H. Tanaka, and T. Ota, Makromol. Chem., 188, 2951 (1987)CrossRefGoogle Scholar
  63. 60.
    T. Otsu, K. Yamagishi, and M. Yoshioka, to be publishedGoogle Scholar
  64. 61.
    T. Otsu and H. Yamazaki, unpublished dataGoogle Scholar
  65. 62.
    A. Matsumoto, S. Umehara, and T. Otsu, to be publishedGoogle Scholar
  66. 63.
    J. -Z. Yang, O. Nakatsuka, and T. Otsu, Chem. Express, 5, 805 (1990).Google Scholar
  67. 64.
    T. Otsu and J. -Z. Yang, Polym. International, 25, 245 (1991)CrossRefGoogle Scholar
  68. 65.
    J. -Z. Yang and Otsu, Makromol. Chem., Rapid Commun., 11, 549 (1990)CrossRefGoogle Scholar
  69. 66.
    J. -Z. Yang and Otsu, Macromolecules, in pressGoogle Scholar
  70. 67.
    J. -Z. Yang and Otsu, Polym. International, 26, 636 (1991)CrossRefGoogle Scholar
  71. 68.
    J. -Z. Yang and Otsu, Polym. Bull., 26, 509 (1991)CrossRefGoogle Scholar
  72. 69.
    T. Otsu and J. -Z. Yang, Polym. Bull., 24, 475 (1990)CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 1992

Authors and Affiliations

  • Takayuki Otsu
    • 1
  • Akikazu Matsumoto
  • Masahiro Yoshioka
  1. 1.Department of Applied Chemistry, Faculty of EngineeringOsaka City UniversitySumiyoshi-ku, OsakaJapan

Personalised recommendations