Skip to main content

Cyclic Oligomers of Polycarbonates and Polyesters

  • Chapter
Cyclic Polymers

Conclusion

Recent chemistry has been developed for the efficient preparation of oligomeric cyclic esters and carbonates. The current techniques have made it possible to prepare hundreds of kilograms of the cyclic oligomers per batch, and have made these materials available for study. Both methods of synthesis have been studied mechanistically. Purification to polymerization quality has been simply achieved in both cases, with selective reactions for removal of linear oligomers. The cyclic oligomers melt at 130–180°C (polyesters) or 180–200°C (polycarbonates), and have melt viscosities about 4 orders of magnitude lower than the parent high molecular weight polymers. Polymerization of the cyclic oligomers has been achieved with a variety of initiators, and using various techniques. Polymerization can be complete within minutes, and leads to very high molecular weight polyesters or polycarbonates without formation of byproducts, and with essentially no exotherm. The ring opening chemistry facilitates a variety of new copolymer reactions, and has made the fabrication of composite structures with very high fiber loadings possible.

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

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. H. Schnell, L. Bottenbruch, Ger. Pat. 1,229,101 (1966).

    Google Scholar 

  2. H. Schnell, L. Bottenbruch, Belg. Pat., 620 620, (1960).

    Google Scholar 

  3. H. Schnell, L. Bottenbruch, Makromol. Chem., 57, 1 (1962).

    Article  CAS  Google Scholar 

  4. R. J. Prochaska, U. S. Pat. 3,274,214 (1966).

    Google Scholar 

  5. L. S. Moody, U. S. Pat, 3,155,683 (1964).

    Google Scholar 

  6. D. J. Brunelle, T. G. Shannon, Macromolecules, 24, 3035 (1991).

    Article  CAS  Google Scholar 

  7. D. J. Brunelle, T. L. Evans, T. G. Shannon, E. P. Boden, et al., Polym. Prepr., 30(#2), 569 (1989).

    CAS  Google Scholar 

  8. D. J. Brunelle, E. P. Boden, T. G. Shannon, J. Am. Chem. Soc., 112, 2399 (1990)

    Article  CAS  Google Scholar 

  9. D. J. Brunelle and M. F. Garbauskas, Macromolecules, 26, 2724 (1993).

    Article  CAS  Google Scholar 

  10. D. J. Brunelle, Makromol. Chem., Macromol. Symp., 64, 65 (1992).

    CAS  Google Scholar 

  11. D. J. Brunelle and E. P. Boden, Polym. Prepr., 31, 399 (1991).

    Google Scholar 

  12. D. J. Brunelle and E. P. Boden, Makromol. Chem., Macromol. Symp., 54/55, 397 (1992).

    CAS  Google Scholar 

  13. E. P. Boden and D. J. Brunelle, Contemporary Topics in Polymer Science, Vol. 7, pp. 21–34, J. C. Salamone and J. S. Riffle, Eds, Plenum Press: New York (1992).

    Google Scholar 

  14. E. Aquino, W. J. Brittain, D. J. Brunelle, Polym. Prepr., 33 (#1), 1185 (1992).

    CAS  Google Scholar 

  15. E. Aquino, W. J. Brittain, D. J. Brunelle, Macromolecules, 25, 3827 (1992)

    Article  CAS  Google Scholar 

  16. E. Aquino, W. J. Brittain, D. J. Brunelle, Polym. Prepr. 34 (#1): 865 (1993).

    CAS  Google Scholar 

  17. E. A. Aquino, W. J. Brittain, D. J. Brunelle, Polymer International, 33, 161 (1994).

    Article  CAS  Google Scholar 

  18. E. C. Aquino, W. J. Brittain, D. J. Brunelle, Jour. Poly. Sci: Part A: Poly. Chem., 32, 741 (1994).

    CAS  Google Scholar 

  19. T. L. Evans, C. B. Berman, J. C. Carpenter, D. Y. Choi, D. A. Williams, Polym. Prep., 30 (#2), 573 (1989).

    CAS  Google Scholar 

  20. D. J. Brunelle and T. L. Evans, Contemporary Topics in Polymer Science, Vol. 7, pp 5–19, J._C. Salamone and J. Riffle, Eds., Plenum Press, New York (1992).

    Google Scholar 

  21. K. R. Stewart, Polym. Prepr., 30(#2), 140 (1989).

    CAS  Google Scholar 

  22. J. E. Bartmess, R. L. Hays, G. Caldwell, J. Am. Chem. Soc., 103, 1338 (1981).

    CAS  Google Scholar 

  23. T. L. Evans, D. J. Brunelle, A. J. Salem, K. R. Stewart, Polymer Preprints, 32(# 2), 176 (1991).

    CAS  Google Scholar 

  24. D. J. Brunelle, T. L. Evans, M. A. Vallance, K. R. Stewart, T. G. Shannon, D. A. Williams, D. J. Patterson, N. R. Rosenquist, W. Hilakos, U. S. Patent 4,740,583 (1988).

    Google Scholar 

  25. D. J. Brunelle and T. G. Shannon, Polymer Preprints, 31(# 1), 14 (1990).

    CAS  Google Scholar 

  26. D. J. Brunelle and T. G. Shannon, Makromol. Chem., Macromol. Symp., 42/43, 155 (1991).

    CAS  Google Scholar 

  27. D. J. Brunelle, T. L. Guggenheim, J. A. Cella, T. L. Evans, et al., U. S. Patent 4,980,453 (1990).

    Google Scholar 

  28. D. J. Brunelle and D. K. Bonauto, U. S. Patent 4,920,200 (1990).

    Google Scholar 

  29. D. J. Brunelle, H. O. Krabbenhoft, and D. K. Bonauto, Polym. Prepr., 34 (#1), 73 (1993).

    CAS  Google Scholar 

  30. D. J. Brunelle, H. O. Krabbenhoft, and D. K. Bonauto, Macromol. Symp., 77, 117–124 (1994).

    CAS  Google Scholar 

  31. D. J. Brunelle, Trends in Polymer Science, 3, 154 (1995).

    CAS  Google Scholar 

  32. T. L. Guggenheim, J. M. Fukuyama, J. J. Kelly, Eur. Pat. Appl., 402676 (1990); CA, 114:208077k.

    Google Scholar 

  33. T. L. Evans, U. S. Patent 4,699,974 (1987).

    Google Scholar 

  34. T. L. Evans and J. C. Carpenter, Polym. Prepr., 31(#1): 18 (1990). (b) T. L. Evans and J. C. Carpenter, Makromol. Chem. Macromol. Symp., 42/43: 177 (1991).

    CAS  Google Scholar 

  35. T. L. Evans and J. C. Carpenter, Makromol. Chem. Macromol. Symp., 42/43, 177 (1991).

    CAS  Google Scholar 

  36. T. L. Evans, T. J. Shea, C. B. Wasserman, J. R. Campbell, U. S. Patent 5,010,143 (1991).

    Google Scholar 

  37. T. L. Evans, N. R. Rosenquist, E. E. Bostick, U. S. Patent 4,746,724 (1988).

    Google Scholar 

  38. T. L. Evans, Eur. Pat. Appl., EP 249,809 (1987); CA 108:187816j.

    Google Scholar 

  39. T. Takekoshi, P. P. Anderson, U. S. Patents 4,695,612 and 4,766,199 (1988).

    Google Scholar 

  40. H. O. Krabbenhoft, E. P. Boden, Polym. Prep., 31(#1), 16 (1990).

    CAS  Google Scholar 

  41. N. R. Rosenquist, L. P. Fontana, Polym. Prep., 30(#2), 577 (1989)

    CAS  Google Scholar 

  42. D. J. Brunelle and T. G. Shannon, U. S. Patents 4,755,586 (1988), 4,794,160 (1988), 4,888,411 (1989), and 4,972,039 (1990).

    Google Scholar 

  43. S. D. Ross, E. R. Coburn, W. A. Leach, W. B. Robinson, J. Polym. Sci., 13, 406 (1954).

    Article  CAS  Google Scholar 

  44. E. Repin and E. Papanikolau, J. Polym. Sci.,A-1, 7, 3426 (1969).

    Article  CAS  Google Scholar 

  45. G. Wick and H. Zeitler, Angew. Makromol. Chem., 112, 59 (1983).

    CAS  Google Scholar 

  46. I. Goodman and B. F. Nesbitt, Polymer, 1, 384 (1960).

    Article  CAS  Google Scholar 

  47. L. H. Peebles, M. W. Huffman, C. T. Ablett, J. Polym. Sci. (A-1), 7, 479 (1969).

    CAS  Google Scholar 

  48. G. C. East, A. M. Girshab, Polymer, 23, 323 (1982).

    CAS  Google Scholar 

  49. G. Montaudo, C. Puglisi, F. Samperi, Polymer Degradation and Stability, 42, 13 (1993).

    Article  CAS  Google Scholar 

  50. E. Meraskentis and H. Zahn, Chem. Ber., 103, 3034 (1970).

    CAS  Google Scholar 

  51. F.-J. Muller, P. Kusch, J. Windeln, H. Zahn, Makromol. Chem., 184, 2487 (1983).

    Google Scholar 

  52. Y. Kitano, A. Ishitani, T. Ashida, Polymer Journal, 23, 949 (1991).

    Article  CAS  Google Scholar 

  53. D. J. Brunelle, J. E. Bradt, J. Serth-Guzzo, T. Takekoshi, T. L. Evans, E. J. Pearce, Macromolecules, 31, 4782 (1998).

    Article  CAS  Google Scholar 

  54. J. W. Hill, W. H. Carothers, J. Am. Chem. Soc., 55, 5031 (1933).

    CAS  Google Scholar 

  55. W. H. Carothers, J. W. Hill, J. Am. Chem. Soc., 55, 5043 (1933).

    CAS  Google Scholar 

  56. E. W. Spanagel, W. H. Carothers, J. Am. Chem. Soc., 57, 929 (1935).

    CAS  Google Scholar 

  57. G. L. Warner, D. J. Brunelle, P. R. Wilson, U. S. Patent 5,446,122 (1995).

    Google Scholar 

  58. Nippon Gijutsu Boeki Co., Japanese Patent 21873 (1971)

    Google Scholar 

  59. H. Jacobson, W. H. Stockmayer, J. Chem. Phys., 18, 1600 (1950).

    CAS  Google Scholar 

  60. D. J. Brunelle and T. Takekoshi, U. S. Patent 5,407,984 (1995).

    Google Scholar 

  61. D. J. Brunelle, G. Kailasam, J. Serth-Guzzo, P. Wilson, U. S. Patent 5,668,186(1997).

    Google Scholar 

  62. J. J. L. Bryant and J. A. Semlyen, Polymer, 38, 2475 (1997).

    CAS  Google Scholar 

  63. J. J. L. Bryant and J. A. Semlyen, Polymer, 38, 4531 (1997).

    CAS  Google Scholar 

  64. S. C. Hamilton, J. A. Semlyen, and D. M. Haddleton, Polymer, 39, 3241 (1998).

    CAS  Google Scholar 

  65. P. A. Hubbard, W. J. Britain, W. L. Mattice, D. J. Brunelle, Macromolecules, 31, 1518 (1998).

    Article  CAS  Google Scholar 

  66. Measurement taken using a Brookfield viscometer, Carbone, J. and Pearce, E. J., personal communication.

    Google Scholar 

  67. Kambour, R.P., personal communication.

    Google Scholar 

  68. T. L. Evans, D. J. Brunelle, J. E. Bradt, E. J. Pearce, P. R. Wilson, U. S. Patent 5,466,744 (1995).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2000 Kluwer Academic Publishers

About this chapter

Cite this chapter

Brunelle, D.J. (2000). Cyclic Oligomers of Polycarbonates and Polyesters. In: Semlyen, J.A. (eds) Cyclic Polymers. Springer, Dordrecht. https://doi.org/10.1007/0-306-47117-5_6

Download citation

  • DOI: https://doi.org/10.1007/0-306-47117-5_6

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-0-412-83090-7

  • Online ISBN: 978-0-306-47117-9

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics