Skip to main content
Log in

Effect of Tertiary Amines on Reactivity of Cycloaliphatic Epoxy Resins towards Methacrylic Acid

  • Published:
Journal of Polymer Research Aims and scope Submit manuscript

Abstract

The kinetics of the esterification of two cycloaliphatic epoxy resins containing glycidyl and epoxy cylohexane group, separately was studied using methacrylic acid in presence of triethyl-amine. The reaction was performed as a function of temperature to determine various kinetics and thermodynamic parameters such as reaction order, reaction rate constant, activation energy, frequency factor, entropy, enthalpy and free energy of the reaction. The reaction order was determined to be 2 and reaction rate constant for the resin containing epoxy cyclohexane group was found higher than that containing glycidyl epoxy group. The reaction was not found to proceed after ∼76% conversion due to the formation of adduct between nitrogen of amine and hydrogen of hydroxyl group of esterified resin. The rate of esterification reaction studied using higher homologue of triethyl-amine (tripropyl- and tributyl-) was found lower than that by triethyl-amine and conversion of acid into ester was ∼80% and ∼83% for tripropyl- and tributyl-amine, respectively due to the steric accessibility of nitrogen atom of higher amine. Based upon these kinetic data a suitable reaction mechanism is proposed for the system.

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. H. Lee and K. Neville, Handbook of Epoxy Resins, McGraw Hill Book Co., New York, 1967.

    Google Scholar 

  2. J. J. Stevens, in Epoxy Resin Technology, P. F. Bruin, Ed., Wiley, New York, 1968.

    Google Scholar 

  3. S. M. Lee, in Epoxy Resins Chemistry and Technology, C. A. May, Ed., Marcel Dekker, New York, 1988.

    Google Scholar 

  4. J. Mijovic, A. Fishbain and J. Wijaya, Macromolecules, 25, 979 (1992).

    Article  Google Scholar 

  5. J. Mijovic and J. Wijaya, Macromolecules, 27, 7589 (1994).

    Article  Google Scholar 

  6. H. Kakiuchi and Y. Tanaka, J. Org. Chem., 31, 1559 (1966).

    Google Scholar 

  7. E. F. Oleinik, Adv. Polym. Sci., 80, 50 (1985).

    Google Scholar 

  8. N. A. John and G. A. George, Prog. Polym. Sci., 19, 755 (1994).

    Article  Google Scholar 

  9. W. Shaobing and M. D. Soucek, J. Coat. Tech., 69, 43 (1997).

    Google Scholar 

  10. L. Matejka and K. Dusek, Polym. Bull., 15, 215 (1986).

    Google Scholar 

  11. L. Matejka, S. Pokorny and K. Dusek, Polym. Bull., 7, 123 (1982).

    Google Scholar 

  12. F. Le Blainvaux, P. J. Madec and E. Marechal, Polym. Bull., 13, 237 (1985).

    Article  Google Scholar 

  13. T. Liu, Z. Chem and F. Chem, Hangzhou Daxue Xuebao Ziran Kexuaben, 12, 91 (1985).

    Google Scholar 

  14. G. Jungang, J. Qing and Y. Biao, Huaxae Yu Zhanhe, 2, 91 (1991).

    Google Scholar 

  15. E. Aguilar, A. Rodolf and M. Castilo, Rev. Soc. Quim. Mexico, 35, 195 (1991).

    Google Scholar 

  16. A. Srivastava, S. Agrawal and J. S. P. Rai, J. Appl. Polym. Sci., 86, 3197 (2002).

    Article  Google Scholar 

  17. V. V. Korshak and S. V. Vinogradova, in Polyesters, Burdon, Ed., Pergamon, Oxford, 1965, p. 191.

    Google Scholar 

  18. G. Odian, Principle of Polymerization, Wiley, New York, 1981.

    Google Scholar 

  19. M. Singh and Sunita, Asian J. Chem., 9, 159 (1997).

    Google Scholar 

  20. O. Levenspiel, Chemical Reaction Engineering, Wiley Eastern Ltd., New Delhi, 1972.

    Google Scholar 

  21. N. B. Clothup, L. H. Daly and S. E. Wiberley, Introduction to Infrared and Raman Spectroscopy, Academic Press, London, 1990.

    Google Scholar 

  22. A. H. Haines, in Comprehensive Organic Chemistry, P. G. Sammes, Ed., Pergamon, Oxford, 1979, p. 853.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Jai Shankar Prasad Rai.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Srivastava, A., Rai, J.S.P. Effect of Tertiary Amines on Reactivity of Cycloaliphatic Epoxy Resins towards Methacrylic Acid. J Polym Res 12, 159–166 (2005). https://doi.org/10.1007/s10965-004-1863-1

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10965-004-1863-1

Keywords

Navigation