Skip to main content

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

  • Conference paper
  • First Online:
Polymerization Reactions

Part of the book series: Advances in Polymer Science ((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.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

V. References

  1. Korshak, V. V., Golova, O. P., Sergeev, V. A., Merlis, N. A., Schneer, R. Y.: Vysokomol. Soedin. 3, 477 (1961)

    CAS  Google Scholar 

  2. Tu, C. C., Schuerch, C.: J. Polym. Sci. B1, 163 (1963)

    Google Scholar 

  3. Schuerch, C.: Adv. Polym. Sci. 10, 174 (1972)

    Google Scholar 

  4. Schuerch, C.: Acc. Chem. Res. 6, 184 (1973)

    Article  CAS  Google Scholar 

  5. Okada, M., Yamashita, Y., Ishii, Y.: Makromol. Chem. 80, 196 (1964)

    Article  CAS  Google Scholar 

  6. Firat, Y., Plesch, P. H.: J. Polym. Sci., Polym. Lett. Ed. 13, 135 (1975)

    Article  CAS  Google Scholar 

  7. Okada, M., Hisada, T., Sumitomo, H.: Makromol. Chem. 179, 959 (1978)

    Article  CAS  Google Scholar 

  8. Dainton, F. S., Ivin, K. J.: Quart. Rev. (Chem. Soc. London) 12, 61 (1968)

    Article  Google Scholar 

  9. Sweet, F., Brown, R. K.: Can. J. Chem. 46, 2289 (1968)

    Article  CAS  Google Scholar 

  10. Kops, J.: J. Polym. Sci. Part A-1, 10, 1275 (1972)

    CAS  Google Scholar 

  11. Hall, Jr., H. K., Steuck, M. J.: Polym. Sci., Polym. Chem. Ed. 11, 1035 (1973)

    Article  CAS  Google Scholar 

  12. Sumitomo, H., Okada, M., Hibino, Y.: Polym. Sci., Polym. Lett. Ed. 10, 871 (1972)

    Article  CAS  Google Scholar 

  13. Okada, M., Sumitomo, H., Hibino, Y.: Polym. J. 6, 256 (1974)

    Article  CAS  Google Scholar 

  14. Jackman, L. M., Sternhell, S.: Application of nuclear magnetic resonance spectroscopy in organic chemistry. 2nd edit. New York: Pergamon Press 1969, p. 238

    Google Scholar 

  15. Hall, Jr., H. K., Carr, L. J., Kellman, R., DeBlauwe, Fr.: J. Am. Chem. Soc. 96, 7265 (1974)

    Article  CAS  Google Scholar 

  16. Angyal, S. J.: The carbohydrates 2nd Edit. Pigman, W., Horton, D. (eds.). New York: Academic Press, 1972, Vol. IA, p. 202

    Google Scholar 

  17. Zachoval, J., Schuerch, C.: J. Am. Chem. Soc. 91, 1165 (1969)

    Article  CAS  Google Scholar 

  18. Yokoyama, Y., Okada, M., Sumitomo, H.: Makromol. Chem. 176, 795 (1975)

    Article  CAS  Google Scholar 

  19. Yokoyama, Y., Okada, M., Sumitomo, H.: Makromol. Chem. 178, 529 (1977)

    Article  CAS  Google Scholar 

  20. Okada, M., Sumitomo, H., Hibino, Y.: Polym. J. 7, 511 (1975)

    Article  CAS  Google Scholar 

  21. Plesch, P. H., Westermann, P. H.: J. Polym. Sci. Part C 16, 3837 (1968)

    Google Scholar 

  22. Okada, M., Mita, K., Sumitomo, H.: Makromol. Chem. 177, 2055 (1976)

    Article  CAS  Google Scholar 

  23. Hall, Jr., H. K.: J. Am. Chem. Soc. 80, 6412 (1958)

    Article  CAS  Google Scholar 

  24. Tamura, A., Nishi, T., Uehara, K., Murata, J.: Kogyo Kagaku Zasshi (J. Chem. Soc. Jpn., Ind. Chem. Sect.) 68, 2271 (1965)

    CAS  Google Scholar 

  25. Okada, M., Sumitomo, H., Komada, H.: Makromol. Chem. 178, 343 (1977)

    Article  CAS  Google Scholar 

  26. Okada, M., Sumitomo, H., Komada, H., Yamazaki, Y.: to be published

    Google Scholar 

  27. Okada, M., Sumitomo, H., Komada, H.: Makromol. Chem. 179, 949 (1978)

    Article  CAS  Google Scholar 

  28. Komada, H., Okada, M., Sumitomo, H.: Polymer Preprints Jpn. 26, 814 (1977)

    Google Scholar 

  29. Hall, Jr., H. K., DeBlauwe, Fr.: J. Am. Chem. Soc. 97, 655 (1975)

    Article  CAS  Google Scholar 

  30. 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. Okada, M., Sumitomo, H., Irii, S.: unpublished

    Google Scholar 

  32. Okada, M., Sumitomo, H., Komada, H.: unpublished

    Google Scholar 

  33. Okada, M., Sumitomo, H., Irii, S.: Makromol. Chem. 177, 2331 (1976)

    Article  CAS  Google Scholar 

  34. Kops, J., Schuerch, C.: J. Polym. Sci. Part C 11, 119 (1965)

    Google Scholar 

  35. Saegusa, T., Motoi, M., Suda, H.: Macromolecules 9, 231 (1976)

    Article  CAS  Google Scholar 

  36. Kops, J., Spanggard, H.: Makromol. Chem. 176, 299 (1975)

    Article  CAS  Google Scholar 

  37. Kops, J., Spanggard, H.: Makromol. Chem. 175, 3077 (1974)

    Article  CAS  Google Scholar 

  38. Okada, M., Mita, K., Sumitomo, H.: Makromol. Chem. 176, 859 (1975)

    Article  CAS  Google Scholar 

  39. Yamashita, Y., Okada, M., Suyama, K., Kasahara, H.: Makromol. Chem. 114, 146 (1968)

    Article  CAS  Google Scholar 

  40. Hall, Jr., H. K., Schneider, A. K.: J. Am. Chem. Soc. 80, 6409 (1958)

    Article  CAS  Google Scholar 

  41. Noyce, D. S., Weingarten, H.: J. Am. Chem. Soc. 79, 3101 (1957)

    Google Scholar 

  42. Collected Papers of W. H. Carothers. New York: Interscience 1940, p. 148

    Google Scholar 

  43. Hall, Jr., H. K., Brandt, M. K., Mason, R. M.: J. Am. Chem. Soc. 80, 6420 (1958)

    Article  CAS  Google Scholar 

  44. Hall, Jr., H. K. Banchard, Jr., E. P., Martin, E. L.: Macromolecules 4, 142 (1971)

    Article  CAS  Google Scholar 

  45. Okada, M., Sumitomo, H., Yamamoto, Y.: Makromol. Chem. 175, 3023 (1974)

    Article  Google Scholar 

  46. Okada, M., Sumitomo, H., Tajima, I.: Macromolecules 10, 505 (1977)

    Article  CAS  Google Scholar 

  47. Okada, M., Sumitomo, H., Tajima, I.: Polymer Preprints Jpn. 26, 878 (1977)

    Google Scholar 

  48. Ashida, T., et al.: to be published

    Google Scholar 

  49. Goethals, E. J.: Adv. Polym. Sci. 23, 103 (1977)

    CAS  Google Scholar 

  50. Okada, M., Sumitomo, H., Fujii, O.: unpublished

    Google Scholar 

  51. Pedersen, C. J.: J. Am. Chem. Soc. 89, 7017 (1967)

    Article  CAS  Google Scholar 

  52. Lehninger, A. L.: Biochemistry. New York: Worth Publishers, Inc. 1970, p. 614

    Google Scholar 

  53. Okada, M., Sumitomo, H., Tajima, I.: Polymer Preprints Jpn. 25, 1669 (1976)

    Google Scholar 

  54. Moore, J. A., Kelly, J. E.: J. Polym. Sci., Polym. Lett. Ed. 13, 333 (1975)

    Article  CAS  Google Scholar 

  55. Hall, Jr., H. K.: J. Am. Chem. Soc. 82, 1209 (1960)

    Article  CAS  Google Scholar 

  56. Ogata, N., Tohoyama, S.: Bull. Chem. Soc. Jpn. 39, 1556 (1966)

    Article  CAS  Google Scholar 

  57. Ogata, N., Asahara, T., Tohoyama, S.: J. Polym. Sci., Part A-1 4, 1359 (1966)

    CAS  Google Scholar 

  58. Sumitomo, H., Hashimoto, K., Ando, M.: J. Polym. Sci., Polym. Lett. Ed. 11, 635 (1973)

    Article  CAS  Google Scholar 

  59. Sumitomo, H., Hashimoto, K.: Macromolecules 10, 1327 (1977)

    Article  CAS  Google Scholar 

  60. Sittler, E., Sebenda, J.: J. Polym. Sci., Part C 16, 67 (1967)

    Google Scholar 

  61. Odian, G.: Principles of polymerization. New York: McGraw-Hill 1970, Chapt. 7

    Google Scholar 

  62. Sebenda, J.: J. Macromol. Sci., Chem. 6, 1145 (1972)

    Article  CAS  Google Scholar 

  63. Stehlicek, J., Labsky, J., Sebenda, J.: Collect. Czech. Chem. Commun. 32, 545 (1967)

    CAS  Google Scholar 

  64. Hall, Jr., H. K.: J. Am. Chem. Soc. 80, 6404 (1958)

    Article  CAS  Google Scholar 

  65. Sorenson, W. R., Campbell, T. W.: Preparative methods of polymer chemistry. 2nd edit. New York: Wiley 1968

    Google Scholar 

  66. Overberger, C. G., Eliott, J. R., Gaylord, N. G., Bailey, W. J., Wittbecker, E. L. (eds.): Macromolecular syntheses. Vol. 3. New York: Wiley 1968

    Google Scholar 

  67. Morton, W. E., Heale, J. W. S.: Physical Properties of Textile Fibers, The Textile Institute, 1964, p. 164

    Google Scholar 

  68. Sumitomo, H., Hashimoto, K., Ohyama, T.: Polymer Preprints Jpn. 26, 1266 (1977)

    Google Scholar 

  69. Sumitomo, H., Hashimoto, K., Ohyama, T.: unpublished

    Google Scholar 

  70. Noguchi, H., Satake, I.: Polymer Preprints Jpn. 25, 1665 (1976)

    Google Scholar 

  71. Sumitomo, H., Hashimoto, K.: Kobunshi Ronbunshu 34, 747 (1977)

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

Copyright information

© 1978 Springer-Verlag

About this paper

Cite this paper

Sumitomo, H., Okada, M. (1978). Ring-opening polymerization of bicyclic acetals, oxalactone, and oxalactam. In: Polymerization Reactions. Advances in Polymer Science, vol 28. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-08885-7_2

Download citation

  • DOI: https://doi.org/10.1007/3-540-08885-7_2

  • Received:

  • Published:

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-08885-1

  • Online ISBN: 978-3-540-35798-8

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics