Skip to main content
SpringerLink
Log in

An efficient method for synthesis of PEO-based macromonomer and macroinitiator

  • Published:
Macromolecular Research Aims and scope Submit manuscript

Abstract

Then-butyllithium-initiated ring-opening polymerization of ethylene oxide, in a mixture of benzene and dimethylsulfoxide (DMSO), between 25-45°C, with potassiumtert-butoxide, is a useful and powerful method to control the molecular weight as well as achieve a quantitative chain-end functionalization yield of the resulting polymeric alkoxidevia a one pot synthesis. The molecular weight of the product could be controlled by adjusting the ratio of grams of monomer to moles of initiators, such asn-butyllithium ([n-BuLi]) and potassiumt-butoxide ([t-BuOK]). The yields for the macromonomer and?-brominated poly(ethylene oxide) (PEO) were quantitative in relation to the chain-end functionalizations of the polymeric alkoxide formed. The resulting products were characterized by a combination of1H-NMR spectroscopic and size exclusion chromatographic analyses.

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Advances in lithium-ion batteries, B. Scrosati and W. Schalkwijk, Eds., Plenum, New York, 2002.

    Google Scholar 

  2. J.-M. Tarascon and M. Armand,Nature,414, 359 (2001).

    Article  CAS  Google Scholar 

  3. F. Croce, R. Curini, A. Martinelli, L. Persi, F. Ronci, B. Scrosati, and R. Caminiti,J. Phys. Chem. B,103, 10632 (1999).

    Article  CAS  Google Scholar 

  4. D. Swierczynski, A. Zalewska, and W. Wieczorek,Chem. Mater.,13, 1560 (2001).

    Article  CAS  Google Scholar 

  5. H.-M. Xiong, D.-P. Liu, H. Zhang, and J.-S. Chen,J. Mater. Chem.,14, 2775 (2004).

    Article  CAS  Google Scholar 

  6. J. M. Harris and R. B. Chess,Nature Rev. Drug Disc.,2, 214 (2003).

    Article  CAS  Google Scholar 

  7. R. Duncan,Nature Rev. Drug Disc.,2, 347 (2003).

    Article  CAS  Google Scholar 

  8. M. Sharpe, S. E. Easthope, G. M. Keating, and H. M. Lamb,Drugs,62, 2089 (2002).

    Article  CAS  Google Scholar 

  9. R. Satchi-Tainaro, R. Duncan, and C. M. Barnes,Adv. Polym. Sci.,193, 1 (2006).

    Article  Google Scholar 

  10. J.-F. Lutz and A. Hoth,Macromolecules,39, 893 (2006). (a) T.-L. Cheng, C.-M. Cheng, B.-M. Chen, S.-A. Tsao, K.-H. Chuang, S.-W. Hsiao, Y.-H. Lin, and S. R. Roffler,Biconjugate Chem.,16, 1225 (2005); (b) W. S. Shim, J. S. Lee, and D. S. Lee,Macromol. Res.,13, 344 (2005).

    Article  CAS  Google Scholar 

  11. R. P. Quirk,Anionic synthesis of polymers with functional groups, inComprehensive Polymer Science, S. L. Aggarwal and S. Russo, Eds., Pregamon Press, Seoul, 1992, Suppl.

    Google Scholar 

  12. R. P. Quirk and J. Kim,Macromonmers and Macroinitiators, inRing-opening Polymerization; Mechanisms, Catalysis, Structure, Utility, D. J. Brunelle, Ed., Hanser, New York, 1993, Chap. 9, pp 263–293.

    Google Scholar 

  13. S. Slomkowski and A. Duda,Anionic Ring-Opening Polymerization, inRing-opening Polymerization; Mechanisms, Catalysis, Structure, Utility, D. J. Brunelle, Ed., Hanser, New York, 1993, Chap. 3, pp 87–128.

    Google Scholar 

  14. H. L. Hsieh and R. P. Quirk,Anionic Polymerization: Principles and Practical Applications, Marcel Dekker, New York, 1996, Chap. 24, pp 685–710.

    Google Scholar 

  15. D. H. Richards and M. Szwarc,Trans. Faraday Soc.,55, 1644 (1959);

    Article  CAS  Google Scholar 

  16. L. E. St. Pierre and C. C. Price,J. Am. Chem. Soc.,78, 3432 (1956).

    Article  Google Scholar 

  17. B. Esswein and M. Moller,Angew. Chem. Int. Ed. Engl.,35, 623 (1996).

    Article  CAS  Google Scholar 

  18. R. P. Quirk, J. Kim, C. Kausch, and M. Chun,Polym. Int.,39, 3 (1996).

    Article  CAS  Google Scholar 

  19. R. P. Quirk, J. Kim, K. Rodrigues, and W. L. Mattice,Makromol. Chem., Macromol. Symp.,42/43, 463 (1991).

    Article  CAS  Google Scholar 

  20. M. Morton and L. J. Fetters,Rubber Chem. Technol.,48, 359 (1975).

    Article  CAS  Google Scholar 

  21. J. M. Stouffer and T. J. McCarthy,Macromolecules,21, 1204 (1988).

    Article  CAS  Google Scholar 

  22. H. Gilman and F. K. Cartledge,J. Organomet. Chem.,2, 447 (1964).

    Article  CAS  Google Scholar 

  23. A. Napoli, N. Tirelli, G. Kilcher, and J. A. Hubbell,Macromolecules,34, 8913 (2001).

    Article  CAS  Google Scholar 

  24. R. P. Quirk and J. J. Ma,J. Polym. Sci.; Part A: Polym. Chem.,24, 2031 (1988).

    Article  Google Scholar 

  25. V. Halaska, L. Lochmann, and D. Lim,Collect. Czec. Chem. Commun.,33, 3245 (1968).

    CAS  Google Scholar 

  26. J. E. Figueruelo and D. J. Worsfold,Eur. Polym. J.,4, 439 (1968).

    Article  CAS  Google Scholar 

  27. M. Schlosser,J. Organomet. Chem.,8, 9 (1967).

    Article  CAS  Google Scholar 

  28. L. Brandsma and H. Verkruijsse,Preparative Polar Organometallic Chemistry 1, Springer-Verlag, Berlin Heidelberg, 1987, Chap. II, p 41.

    Google Scholar 

  29. C. E. H. Bawn, A. Ledwith, and N. McFarlane,Polymer,10, 653 (1969).

    Article  CAS  Google Scholar 

  30. C. C. Price and D. D. Carmelite,J. Am. Chem. Soc.,88, 4039 (1966).

    Article  CAS  Google Scholar 

  31. H. L. Hsieh and R. P. Quirk,Anionic Polymerization: Principles and Practical Applications, Marcel Dekker, New York, 1996, Chap. 4, pp 71–92.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Research Institute of Basic Sciences, Kyung Hee University, 130-701, Seoul, Korea

    Jungahn Kim, Song-yee Choi, Kyung Min Kim, Da Hyeon Go, Hee Jeong Jeon & Jae Yeol Lee

  2. Department of Chemistry, Kyung Hee University, 130-701, Seoul, Korea

    Jungahn Kim, Song-yee Choi, Kyung Min Kim, Da Hyeon Go, Hee Jeong Jeon & Jae Yeol Lee

  3. Department of Chemical Engineering, Sogang University, 121-742, Seoul, Korea

    Hyeong Soo Park, Cheol Han Lee & Heung Mok Park

Authors
  1. Jungahn Kim
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Song-yee Choi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Kyung Min Kim
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Da Hyeon Go
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Hee Jeong Jeon
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Jae Yeol Lee
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Hyeong Soo Park
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Cheol Han Lee
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Heung Mok Park
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Jungahn Kim.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kim, J., Choi, Sy., Kim, K.M. et al. An efficient method for synthesis of PEO-based macromonomer and macroinitiator. Macromol. Res. 15, 337–342 (2007). https://doi.org/10.1007/BF03218796

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF03218796

Keywords

Search

Navigation