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Fatty Acid Methyl Esters as Biosolvents of Epoxy Resins: A Physicochemical Study

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Abstract

The C8 to C18 fatty acid methyl esters (FAME) have been compared as solvents for two epoxy resin pre-polymers, bisphenol A diglycidyl ether (DGEBA) and triglycidyl p-aminophenol ether (TGPA). It was found that the solubilization limits vary according to the ester and that methyl caprylate is the best solvent of both resins. To explain these solubility performances, physical and chemical properties of FAME were studied, such as the Hansen parameters, viscosity, binary diffusion coefficient and vaporization enthalpy. Determination of the physicochemical parameters of FAME was carried out by laboratory experimentations and by calculation from bibliographic data. The Hansen parameters of FAME and epoxy resins pre-polymers were theoretically and experimentally determined. The FAME chain length showed a long dependence on the binary diffusion parameters and kinematic viscosity, which are mass and momentum transport properties. Moreover, the vaporization enthalpy of these compounds was directly correlated with the solubilization limits.

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References

  1. Grayson, M.: Industrial Solvents. Wiley, New York (1983)

    Google Scholar 

  2. Gateau, P., Van Dievoet, F., Bouillon, V., Vermeersch, G., Claude, S., Staat, F.: Environmentally friendly properties of vegetable oil methyl esters. OCL 12(4), 308–313 (2005)

    CAS  Google Scholar 

  3. Ahluwalia, V.K., Kidwai, M.: New Trends in Green Chemistry. Kluwer Academic, Boston (2004)

    Google Scholar 

  4. Abraham, M.A., Moens, L. (eds): Clean Solvents, Alternative Media for Chemical Reactions and Processing. ACS Symposium Series, vol. 819. American Chemical Society, Washington (2002)

    Google Scholar 

  5. Beck, H.N., Mahand, R.W., Sanders, E.S.: Relative solubility of tetrachlorohexafluoro-bisphenol-A polycarbonate in various compounds. J. Appl. Polymer Sci. 47, 2161–2167 (1993)

    Article  CAS  Google Scholar 

  6. Archer, W.: Determination of Hansen solubility parameters for selected cellulose ether derivatives. Ind. Eng. Chem. Res. 30, 2292–2298 (1991)

    Article  CAS  Google Scholar 

  7. Remigy, J.C., Nakache, E., Brechot, P.D.: Computer-aided method for the determination of Hansen solubility parameters. Application to the miscibility of refrigerating lubricant and new refrigerant. Ind. Eng. Chem. Res. 38, 4470–4476 (1999)

    Article  Google Scholar 

  8. Barton, A.: CRC Handbook of Solubility Parameters and Other Cohesion Parameters. CRC Press, Boca Raton (1991)

    Google Scholar 

  9. Hansen, C.M.: Three-dimensional solubility parameter-key to paint-component affinities. J. Paint. Tech. 39(511), 505–514 (1967)

    CAS  Google Scholar 

  10. Becke, A.D.: Density-functional thermochemisty. III—The role of exact exchange. J. Chem. Phys. 98, 5648–5652 (1993)

    Article  CAS  Google Scholar 

  11. Lee, C., Yang, W., Parr, R.G.: Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B Condens. Mater Phys. 37, 785–789 (1988)

    CAS  Google Scholar 

  12. Dunning, T.H., Jr., Hay, P.J.: In: Schaefer, H.F. III (ed.) Modern Theoretical Chemistry, vol. 3(1). Plenum, New York (1976)

    Google Scholar 

  13. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery, J.A., Jr., Vreven, T., Kudin, K.N., Burant, J.C., Millam, J.M., Iyengar, S.S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G.A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J.E., Hratchian, H.P., Cross, J.B., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Ayala, P.Y., Morokuma, K., Voth, G.A., Salvador, P., Dannenberg, J.J., Zakrzewski, V.G., Dapprich, S., Daniels, A.D., Strain, M.C., Farkas, O., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., Clifford, S., Cioslowski, J., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Gonzalez, C., Pople, J.A.: Gaussian 03. Gaussian Inc., Pittsburgh, Revision B.04 (2003)

    Google Scholar 

  14. Van Krevelen, D.W.: Properties of Polymers. Elsevier, Amsterdam (1990)

    Google Scholar 

  15. Fagerquist, C.K., Neese, R.A., Hellerstein, M.K.: Molecular ion fragmentation and its effects on mass isotope abundances of fatty acid methyl esters ionized by electron impact. J. Am. Soc. Mass Spectrom. 10, 430–439 (1999)

    Article  CAS  Google Scholar 

  16. Beran, J.A., Kevan, L.: Semiempirical calculation of molecular polarizabilities and diamagnetic susceptibilities of fluorocarbons, substituted fluorocarbons, ethers, esters, ketones and aldehydes. J. Phys. Chem. 73, 3860–3866 (1969)

    Article  CAS  Google Scholar 

  17. Beran, J.A., Kevan, L.: Molecular electron ionization cross sections at 70 eV. J. Phys. Chem. 73, 3866–3876 (1969)

    Article  CAS  Google Scholar 

  18. Roussis, S.G.: Relative collision cross sections of organic ions. J. Am. Chem. Soc. Mass Spectrom. 6, 803–811 (1995)

    Article  CAS  Google Scholar 

  19. CRC Handbook of Chemistry and Physics, 66th edn. CRC Press, Boca Raton (1985–1986)

  20. Medina Gonzalez, Y.: PhD Thesis, Institut National Polytechnique de Toulouse (INPT), France (2006)

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Correspondence to P. de Caro.

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Medina Gonzalez, Y., de Caro, P., Thiebaud-Roux, S. et al. Fatty Acid Methyl Esters as Biosolvents of Epoxy Resins: A Physicochemical Study. J Solution Chem 36, 437–446 (2007). https://doi.org/10.1007/s10953-007-9126-5

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  • DOI: https://doi.org/10.1007/s10953-007-9126-5

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