Skip to main content
Log in

Cationic Polymerization of Epoxides using Novel Xanthenyl Phosphonium Salts as Thermo-latent Initiator

  • Published:
Polymer Bulletin Aims and scope Submit manuscript

Abstract

The present article describes the effect of steric and electronic factors on the efficiency of initiators based on novel xanthenyl phosphonium salts for cationic polymerization of epoxide monomers. 2-substituted (IH, ICl, IMe, and IOMe) xanthenyl phosphonium hexafluoroantimonate were synthesized and characterized by NMR (1H, 13C and 31P) and IR spectroscopy. The order of initiator activity in polymerization of glycidyl phenyl ether (GPE), was found as IH> ICl>IMe>IOMe. To understand the effect of steric factor, the polymerization of cyclohexene oxide (CHO) was performed and the order of activity was found as ICl>IH>IMe >IOMe. All the initiators were found to be latent at ambient temperature and initiates polymerization on thermal initiation. The order of initiator activity was influenced by electronic and steric factors in the system. The thermal stability of these salts was measured by Thermo gravimetric analysis (TGA). The solubility of the initiators in various organic solvents and epoxy monomers is also discussed.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Lee H, Neville K (1967) Handbook of Epoxy Resins. McGraw-Hill, New York

    Google Scholar 

  2. Mark HF, Gaylord NG, Bikajes NM (1968) Encyclopedia of Polymer Science and Technology. Eds. Interscience, New York, vol 8, p 303

  3. Crivello JV (1999) J Polym Sci Part A Polym Chem 37:4241

    Article  CAS  Google Scholar 

  4. Yagci Y, Endo T (1997) Adv Polym Sci 127:59

    CAS  Google Scholar 

  5. Yagci Y, Reetz I (1998) Prog Polym Sci 23:1485

    Article  CAS  Google Scholar 

  6. Gupta MK, Singh RP (2006) Macmol Symp 240:186

    Article  CAS  Google Scholar 

  7. Murai S, Nakano Y, Hayase S (2000) J Appl Polym Sci 80:181

    Article  Google Scholar 

  8. Park SJ, Heo GY (2005) Macromol Chem Phys 206:1134

    Article  CAS  Google Scholar 

  9. Hamazu F, Akashi S, Koizumi T, Takata T, Endo T (1991) J Polym Sci Polym Chem 29:1675

    Article  CAS  Google Scholar 

  10. Shimomura O, Sato T, Tomita I, Endo T (1998) Macromolecules 31:2013

    Article  CAS  Google Scholar 

  11. Shimomura O, Tomita I, Endo T (1998) Macromol. Rapid Commun 19:493

    Article  CAS  Google Scholar 

  12. Lee SB, Takata T, Endo T (1990) Macromolecules 23:431

    Article  CAS  Google Scholar 

  13. Lee SB, Takata T, Endo T (1991) Macromolecules 24:2689

    Article  CAS  Google Scholar 

  14. Nakano S, Endo T (1996) J Polym Sci Part A Polym Chem 34:475

    Article  CAS  Google Scholar 

  15. Nakano S, Endo T (1995) J Polym Sci Polym Chem 33:505

    Article  CAS  Google Scholar 

  16. Kim MS, Lee SB, Lee KB, Endo T (2005) J Appl Polym Sci 95:1439

    Article  CAS  Google Scholar 

  17. Takuma K, Takata T, Endo T (1993) Macromolecules 26:862

    Article  CAS  Google Scholar 

  18. Kim M, Sanda F, Endo T (2001) J Appl Polym Sci 81:2347

    Article  CAS  Google Scholar 

  19. Morikawa H, Sudo A, Nishida H, Endo T (2005) J Appl Polym Sci 96:72

    Article  CAS  Google Scholar 

  20. Kosolapoff GM, Maier L (1972) Organic Phosphorus Compounds. Wiley-Interscience, New York

    Google Scholar 

  21. Toneri T, Sanda F, Endo T (1998) J Polym Sci Part A Polym Chem 36:1957

    Article  CAS  Google Scholar 

  22. Toneri T, Watanabe K, Sanda F, Endo T (1999) Macromolecules 32:1293

    Article  CAS  Google Scholar 

  23. Toneri T, Sanda F, Endo T (2001) Macromolecules 34:1518

    Article  CAS  Google Scholar 

  24. Gupta MK, Singh RP (2007) J Appl Polym Sci Communicated

  25. Pellon RF, Carrasco R, Milian V, Rodes L (1995) Synth Commun 25:1077

    Article  CAS  Google Scholar 

  26. Pickert M, Frahm AW (1998) Arch Pharma Pharm Med Chem 331:177

    Article  CAS  Google Scholar 

  27. Hamanzu F, Akashi S, Koizumi T, Takata T, Endo T (1992) Macromol Chem Rapid Commun 13:203

    Article  Google Scholar 

  28. Ottar B (1947) Acta Chem Scand 1:283

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Raj Pal Singh.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Gupta, M.K., Singh, R.P. Cationic Polymerization of Epoxides using Novel Xanthenyl Phosphonium Salts as Thermo-latent Initiator . Polym. Bull. 60, 755–763 (2008). https://doi.org/10.1007/s00289-008-0910-1

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00289-008-0910-1

Keywords

Navigation