Skip to main content

Novel coatings based on mixtures of blown soybean oil and acrylate prepolymers

Abstract

Commercial blown soybean oil (BSBO) was shown by titration to contain a substantial level of (hydro)peroxy groups, presumably formed during the blowing process. Thus, BSBO can initiate free-radical polymerization. To explore the potential for film formation, BSBO was blended with (meth)acrylate monomers and/or prepolymers in different proportions. The monomers were trimethylopropane triacrylate esters (TMPTAE), 1,6-hexanediol dimethacrylate (HDDMA), and isobornyl acrylate (IBOA); the prepolymers were ethoxylated bisphenol A dimethacrylate (EBDMAE), and a hydrophobic aromatic urethane acrylate (HAUA). All blends required a catalyst (cobalt naphthenate) and temperatures of about 100°C to induce crosslinking and film formation. Blends with monomers gave formulations that could be applied with no added solvent, but film properties (pencil hardness, MEK double rub resistance, adhesion, and impact resistance) were not very good. Better film properties were obtained by blending prepolymers with BSBO and TMPTAE; these formulations required solvent for application, but VOC levels as low at 140 g/L were possible. FTIR spectra showed that free radical polymerization of the monomers and prepolymers occurred during film formation. Gel content studies indicated that part of the BSBO is incorporated into the crosslinked film, but a substantial fraction is not chemically bound to the network.

This is a preview of subscription content, access via your institution.

References

  1. Akintayo, E.T., “Studies in the Synthesis of Oil Modified Alkyd Resin Using Crude Soybean Oil as Modifier,”Discovery and Innovation, 8, No. 2, 165 (1996).

    CAS  Google Scholar 

  2. Rosch, J. and Mulhaupt, R., “Polymers from Renewable Resources: Polyester Resins and Blends Based upon Anhydride-Cure Epoxidized Soybean Oil,”Poly. Bull., 31, 679 (1993).

    Article  Google Scholar 

  3. Refvik, M. D. and Larock, R. C., “Industrial Products and Application—The Chemistry of Metathesized Soybean Oil,”J. Am. Oil Chem., 76, 99 (1999).

    Article  CAS  Google Scholar 

  4. Erhan, S. Z., Bagby, M. O. and Nelsen, T. C., “Drying Properties of Metathesized Soybean Oil,”J. Am. Oil Chem., 74, 703 (1997).

    Article  CAS  Google Scholar 

  5. Miller, E., U.S. Patent 2,374,692 (1945).

  6. Farringtom, G.M., Jr. and Verduin, F.C., U.S. Patent 3,414,419 (1968).

    Google Scholar 

  7. Sedlacek, Z., Lavicky, V., and Danhel, S., C.S. Patent 128,234 (1968).

    Google Scholar 

  8. Epstein, D. and Watkins, L.A., G.B. Patent 1,160,746 (1969).

  9. Thames, S.F. and Yu, H., “Synthesis, Characterization, and Application of Lesquerella Oil and Its Derivative in Water-Reducible Coatings,”Journal of Coatings Technology,68, No. 858, 63 (1996).

    CAS  Google Scholar 

  10. Sharp, K., Mattson, G., and Jonsson, S., “Evaluation of the Degree of Cure of a Coating,”Journal of Coatings Technology,70, No. 877, 97 (1998).

    Article  CAS  Google Scholar 

  11. Wicks, Z.W., Jr., Jones, F.N., and Pappas, S.P.,Organic Coatings: Science and Technology, 2nd Ed., John Wiley & Sons, Inc., New York, p. 264, 1999.

    Google Scholar 

  12. Spiteller, G., “Linoleic Acid Peroxidation-The Dominant Lipid Peroxidation Process in Low Density Lipoprotein-And Its Relationship to Chronic Diseases,”Chem. and Phys. Lipids, 95, No. 2, 105–162 (1998).

    Article  CAS  Google Scholar 

  13. Falla, N.A.R., “Linoleic Based Coatings: A Study of the Dry Film Structure,”Journal of Coatings Technology,64, No. 815, 55 (1992).

    ADS  CAS  Google Scholar 

  14. Wexler, H., “Polymerization of Drying Oils,”Chem. Rev., 64, No. 6, 591–611 (1964).

    Article  CAS  Google Scholar 

  15. Muizebelt, W.J., Donkerbroek, J.J., Nielen, M.W.F., Hussem, J.B., Biermond, M.E.F., Klaasen, R.P., and Zabel, K.H., “Oxidative Crosslinking of Alkyd Resins Studied with Mass Spectrometry and NMR Using Model Compounds,”Journal of Coatings Technology,70, No. 876, 83 (1998).

    Article  CAS  Google Scholar 

  16. Chen, D., Liu, Y. and Hartman, D.R., “Examination of Fat Oxidation Products by FT-NMR and FT-IR,”Amer. Lab., 31, No. 10, 15–20 (1999).

    Google Scholar 

  17. Hartshorn, J.H., “Time-Lapse Spectroscopic Investigation of Alkyd and Linseed Oil Cure,”Journal of Coatings Technology,54, No. 687, 53 (1982).

    CAS  Google Scholar 

  18. Brandenburg, K. and Seyde, U., “Infrared Spectroscopy of Glycolipids,”Chem. Phys. Lipids, 96, 23–40 (1998).

    PubMed  Article  CAS  Google Scholar 

  19. Winnik, M.A., Pinenq, P., Kruger, C., Zhang, J., and Yaneff, P.V., “Crosslinking vs. Interdiffusion Rates in Melamine-Formaldehyde Cured Latex Coatings: A Model for Waterborne Automotive Basecoat,”Journal of Coatings Technology,71, No. 892, 47 (1999).

    Article  CAS  Google Scholar 

  20. Padmavathi, N. Ch. and Chatterji, P.R., “Structural Characteristics Swelling Behavior of Poly(ethylene glycol) Diacrylate Hydrogels,”Macromolecules, 29, 1976–1979 (1996).

    Article  ADS  CAS  Google Scholar 

  21. Neff, W.E., Frankel, E.N. and Miyashita, K., “Autooxidation of Polyunsaturated Triacylglycerols. I. Trilinoleoylglycerol,”Lipids, 25, No. 1, 33–39 (1990).

    Article  CAS  Google Scholar 

  22. Frankel, E.N., Neff, W.E. and Miyashita, K., “Autoxidation of Polyunsaturated Triacylglycerols. II. Trilinolenoylglycerol,”Lipids, 25, No. 1, 40–47 (1990).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Frank N. Jones.

Additional information

430 W. Forest Ave., Ypsilanti, MI 48197.

Department of Macromolecular Science, Shanghai, 200433 China.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Ni, P., Jones, F.N. & Fu, S. Novel coatings based on mixtures of blown soybean oil and acrylate prepolymers. Journal of Coatings Technology 73, 57–64 (2001). https://doi.org/10.1007/BF02698497

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02698497

Keywords

  • Methyl Ethyl Ketone
  • Film Property
  • Alkyd Resin
  • Pencil Hardness
  • Hewlett Packard