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Ring-opening polymerization of bicyclic acetals, oxalactone, and oxalactam

  • Hiroshi Sumitomo
  • Masahiko Okada
Conference paper
Part of the Advances in Polymer Science book series (POLYMER, volume 28)

Abstract

Reaction mechanisms of ring-opening polymerization and structures and properties of resulting polymers of bicyclic acetals including 6,8-dioxabicyclo[3.2.1]octane (abbreviated to DBO) and 6,8-dioxabicyclo[3.2.1]oct-3-ene (DBOE), bicyclic oxalactone 6,8-dioxabicyclo[3.2.1]octan-7-one (DBOO), bicyclic oxalactam 8-oxa-6-azabicyclo[3.2.1.]octan-7-one (BOL), and related hetero bicyclic compounds are reviewed. Polysaccharide analogues were prepared from DBO and DBOE. Novel macrocyclic oligoesters were obtained in high yields from DBOO. BOL yielded easily a novel hygroscopic polyamide membrane of high molecular weight.

Keywords

Apparent Diffusion Coefficient Inherent Viscosity Number Average Molecular Weight Cationic Polymerization Cyclic Dimer 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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V. References

  1. 1).
    Korshak, V. V., Golova, O. P., Sergeev, V. A., Merlis, N. A., Schneer, R. Y.: Vysokomol. Soedin. 3, 477 (1961)Google Scholar
  2. 2).
    Tu, C. C., Schuerch, C.: J. Polym. Sci. B1, 163 (1963)Google Scholar
  3. 3).
    Schuerch, C.: Adv. Polym. Sci. 10, 174 (1972)Google Scholar
  4. 4).
    Schuerch, C.: Acc. Chem. Res. 6, 184 (1973)CrossRefGoogle Scholar
  5. 5).
    Okada, M., Yamashita, Y., Ishii, Y.: Makromol. Chem. 80, 196 (1964)CrossRefGoogle Scholar
  6. 6).
    Firat, Y., Plesch, P. H.: J. Polym. Sci., Polym. Lett. Ed. 13, 135 (1975)CrossRefGoogle Scholar
  7. 7).
    Okada, M., Hisada, T., Sumitomo, H.: Makromol. Chem. 179, 959 (1978)CrossRefGoogle Scholar
  8. 8).
    Dainton, F. S., Ivin, K. J.: Quart. Rev. (Chem. Soc. London) 12, 61 (1968)CrossRefGoogle Scholar
  9. 9).
    Sweet, F., Brown, R. K.: Can. J. Chem. 46, 2289 (1968)CrossRefGoogle Scholar
  10. 10).
    Kops, J.: J. Polym. Sci. Part A-1, 10, 1275 (1972)Google Scholar
  11. 11).
    Hall, Jr., H. K., Steuck, M. J.: Polym. Sci., Polym. Chem. Ed. 11, 1035 (1973)CrossRefGoogle Scholar
  12. 12).
    Sumitomo, H., Okada, M., Hibino, Y.: Polym. Sci., Polym. Lett. Ed. 10, 871 (1972)CrossRefGoogle Scholar
  13. 13).
    Okada, M., Sumitomo, H., Hibino, Y.: Polym. J. 6, 256 (1974)CrossRefGoogle Scholar
  14. 14).
    Jackman, L. M., Sternhell, S.: Application of nuclear magnetic resonance spectroscopy in organic chemistry. 2nd edit. New York: Pergamon Press 1969, p. 238Google Scholar
  15. 15).
    Hall, Jr., H. K., Carr, L. J., Kellman, R., DeBlauwe, Fr.: J. Am. Chem. Soc. 96, 7265 (1974)CrossRefGoogle Scholar
  16. 16).
    Angyal, S. J.: The carbohydrates 2nd Edit. Pigman, W., Horton, D. (eds.). New York: Academic Press, 1972, Vol. IA, p. 202Google Scholar
  17. 17).
    Zachoval, J., Schuerch, C.: J. Am. Chem. Soc. 91, 1165 (1969)CrossRefGoogle Scholar
  18. 18).
    Yokoyama, Y., Okada, M., Sumitomo, H.: Makromol. Chem. 176, 795 (1975)CrossRefGoogle Scholar
  19. 19).
    Yokoyama, Y., Okada, M., Sumitomo, H.: Makromol. Chem. 178, 529 (1977)CrossRefGoogle Scholar
  20. 20).
    Okada, M., Sumitomo, H., Hibino, Y.: Polym. J. 7, 511 (1975)CrossRefGoogle Scholar
  21. 21).
    Plesch, P. H., Westermann, P. H.: J. Polym. Sci. Part C 16, 3837 (1968)Google Scholar
  22. 22).
    Okada, M., Mita, K., Sumitomo, H.: Makromol. Chem. 177, 2055 (1976)CrossRefGoogle Scholar
  23. 23).
    Hall, Jr., H. K.: J. Am. Chem. Soc. 80, 6412 (1958)CrossRefGoogle Scholar
  24. 24).
    Tamura, A., Nishi, T., Uehara, K., Murata, J.: Kogyo Kagaku Zasshi (J. Chem. Soc. Jpn., Ind. Chem. Sect.) 68, 2271 (1965)Google Scholar
  25. 25).
    Okada, M., Sumitomo, H., Komada, H.: Makromol. Chem. 178, 343 (1977)CrossRefGoogle Scholar
  26. 26).
    Okada, M., Sumitomo, H., Komada, H., Yamazaki, Y.: to be publishedGoogle Scholar
  27. 27).
    Okada, M., Sumitomo, H., Komada, H.: Makromol. Chem. 179, 949 (1978)CrossRefGoogle Scholar
  28. 28).
    Komada, H., Okada, M., Sumitomo, H.: Polymer Preprints Jpn. 26, 814 (1977)Google Scholar
  29. 29)a).
    Hall, Jr., H. K., DeBlauwe, Fr.: J. Am. Chem. Soc. 97, 655 (1975)CrossRefGoogle Scholar
  30. 29)b).
    Hall, Jr., H. K., DeBlauwe, Fr., Carr, L. J., Rao, V. S., Reddy, G. S.: J. Polym. Sci., Symposium No. 56, 101 (1976)Google Scholar
  31. 30).
    Okada, M., Sumitomo, H., Irii, S.: unpublishedGoogle Scholar
  32. 31).
    Okada, M., Sumitomo, H., Komada, H.: unpublishedGoogle Scholar
  33. 32).
    Okada, M., Sumitomo, H., Irii, S.: Makromol. Chem. 177, 2331 (1976)CrossRefGoogle Scholar
  34. 33).
    Kops, J., Schuerch, C.: J. Polym. Sci. Part C 11, 119 (1965)Google Scholar
  35. 34).
    Saegusa, T., Motoi, M., Suda, H.: Macromolecules 9, 231 (1976)CrossRefGoogle Scholar
  36. 35).
    Kops, J., Spanggard, H.: Makromol. Chem. 176, 299 (1975)CrossRefGoogle Scholar
  37. 36).
    Kops, J., Spanggard, H.: Makromol. Chem. 175, 3077 (1974)CrossRefGoogle Scholar
  38. 37).
    Okada, M., Mita, K., Sumitomo, H.: Makromol. Chem. 176, 859 (1975)CrossRefGoogle Scholar
  39. 38).
    Yamashita, Y., Okada, M., Suyama, K., Kasahara, H.: Makromol. Chem. 114, 146 (1968)CrossRefGoogle Scholar
  40. 39).
    Hall, Jr., H. K., Schneider, A. K.: J. Am. Chem. Soc. 80, 6409 (1958)CrossRefGoogle Scholar
  41. 40).
    Noyce, D. S., Weingarten, H.: J. Am. Chem. Soc. 79, 3101 (1957)Google Scholar
  42. 41).
    Collected Papers of W. H. Carothers. New York: Interscience 1940, p. 148Google Scholar
  43. 42).
    Hall, Jr., H. K., Brandt, M. K., Mason, R. M.: J. Am. Chem. Soc. 80, 6420 (1958)CrossRefGoogle Scholar
  44. 43).
    Hall, Jr., H. K. Banchard, Jr., E. P., Martin, E. L.: Macromolecules 4, 142 (1971)CrossRefGoogle Scholar
  45. 44).
    Okada, M., Sumitomo, H., Yamamoto, Y.: Makromol. Chem. 175, 3023 (1974)CrossRefGoogle Scholar
  46. 45).
    Okada, M., Sumitomo, H., Tajima, I.: Macromolecules 10, 505 (1977)CrossRefGoogle Scholar
  47. 46).
    Okada, M., Sumitomo, H., Tajima, I.: Polymer Preprints Jpn. 26, 878 (1977)Google Scholar
  48. 47).
    Ashida, T., et al.: to be publishedGoogle Scholar
  49. 48).
    Goethals, E. J.: Adv. Polym. Sci. 23, 103 (1977)Google Scholar
  50. 49).
    Okada, M., Sumitomo, H., Fujii, O.: unpublishedGoogle Scholar
  51. 50).
    Pedersen, C. J.: J. Am. Chem. Soc. 89, 7017 (1967)CrossRefGoogle Scholar
  52. 51).
    Lehninger, A. L.: Biochemistry. New York: Worth Publishers, Inc. 1970, p. 614Google Scholar
  53. 52).
    Okada, M., Sumitomo, H., Tajima, I.: Polymer Preprints Jpn. 25, 1669 (1976)Google Scholar
  54. 53).
    Moore, J. A., Kelly, J. E.: J. Polym. Sci., Polym. Lett. Ed. 13, 333 (1975)CrossRefGoogle Scholar
  55. 54).
    Hall, Jr., H. K.: J. Am. Chem. Soc. 82, 1209 (1960)CrossRefGoogle Scholar
  56. 55).
    Ogata, N., Tohoyama, S.: Bull. Chem. Soc. Jpn. 39, 1556 (1966)CrossRefGoogle Scholar
  57. 56).
    Ogata, N., Asahara, T., Tohoyama, S.: J. Polym. Sci., Part A-1 4, 1359 (1966)Google Scholar
  58. 57).
    Sumitomo, H., Hashimoto, K., Ando, M.: J. Polym. Sci., Polym. Lett. Ed. 11, 635 (1973)CrossRefGoogle Scholar
  59. 58).
    Sumitomo, H., Hashimoto, K.: Macromolecules 10, 1327 (1977)CrossRefGoogle Scholar
  60. 59).
    Sittler, E., Sebenda, J.: J. Polym. Sci., Part C 16, 67 (1967)Google Scholar
  61. 60).
    Odian, G.: Principles of polymerization. New York: McGraw-Hill 1970, Chapt. 7Google Scholar
  62. 61).
    Sebenda, J.: J. Macromol. Sci., Chem. 6, 1145 (1972)CrossRefGoogle Scholar
  63. 62).
    Stehlicek, J., Labsky, J., Sebenda, J.: Collect. Czech. Chem. Commun. 32, 545 (1967)Google Scholar
  64. 63).
    Hall, Jr., H. K.: J. Am. Chem. Soc. 80, 6404 (1958)CrossRefGoogle Scholar
  65. 64).
    Sorenson, W. R., Campbell, T. W.: Preparative methods of polymer chemistry. 2nd edit. New York: Wiley 1968Google Scholar
  66. 65).
    Overberger, C. G., Eliott, J. R., Gaylord, N. G., Bailey, W. J., Wittbecker, E. L. (eds.): Macromolecular syntheses. Vol. 3. New York: Wiley 1968Google Scholar
  67. 66).
    Morton, W. E., Heale, J. W. S.: Physical Properties of Textile Fibers, The Textile Institute, 1964, p. 164Google Scholar
  68. 67).
    Sumitomo, H., Hashimoto, K., Ohyama, T.: Polymer Preprints Jpn. 26, 1266 (1977)Google Scholar
  69. 68).
    Sumitomo, H., Hashimoto, K., Ohyama, T.: unpublishedGoogle Scholar
  70. 69).
    Noguchi, H., Satake, I.: Polymer Preprints Jpn. 25, 1665 (1976)Google Scholar
  71. 70).
    Sumitomo, H., Hashimoto, K.: Kobunshi Ronbunshu 34, 747 (1977)Google Scholar

Copyright information

© Springer-Verlag 1978

Authors and Affiliations

  • Hiroshi Sumitomo
    • 1
  • Masahiko Okada
    • 1
  1. 1.Faculty of AgricultureNagoya UniversityNagoyaJapan

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