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Coatings derived from novel, soybean oil-based polymers produced using carbocationic polymerization

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An Erratum to this article was published on 15 February 2012

Abstract

In this study, a process was developed to obtain vinylether-functional monomers containing fatty acid pendent groups directly from soybean oil (SBO) using base-catalyzed transesterification. In addition, a carbocationic polymerization process was developed for the vinylether monomers, which allowed for high molecular weight polymers to be produced without consuming any of the vinyl groups present in the fatty acid portion of the monomers. Compared to SBO, which possesses on average 4.5 vinyl groups per molecule, the polyvinylethers based on the soybean oil-derived vinylether monomers (polyVESFA) possess tens to thousands of vinyl groups per molecule depending on the polymer molecular weight produced. As a result of this difference, coatings based on polyVESFA were shown to possess much higher crosslink density at a given degree of functional group conversion compared with analogs based on conventional SBO. In addition, the dramatically higher number of functional groups per molecule associated with polyVESFA results in gel-points being reached at much lower functional group conversion, which was shown to dramatically reduce cure-time compared with SBO-based analogs. Based on the results obtained, it appears that these new renewable materials may have tremendous commercial utility in the coatings industry.

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References

  1. Xu, Y, Hanna, MA, Isom, L, “Green Chemicals from Renewable Agricultural Biomass—A Mini Review.” Open Agric. J., 2 54–61 (2008)

    Article  CAS  Google Scholar 

  2. Dodds, DR, Gross, RA, “Chemicals from Biomass.” Science, 318 1250–1251 (2007)

    Article  CAS  Google Scholar 

  3. Meier, MAR, Metzger, JO, Schubert, US, “Plant Oil Renewable Resources as Green Alternatives in Polymer Science.” Chem. Soc. Rev., 36 1788–1802 (2007)

    Article  CAS  Google Scholar 

  4. Gast, LE, Fatty Acids. AOCS Monograph 7, p. 564. American Oil Chemists’ Society, Champaign, IL, 1979

  5. Derksen, JTP, Cuperus, FP, Kolster, P, “Renewable Resources in Coatings Technology: A Review.” Prog. Org. Coat., 27 45–53 (1996)

    Article  CAS  Google Scholar 

  6. Solomon, DH, The Chemistry of Organic Film Formers, 2nd ed., pp. 36–37. Robert E. Krieger, Malabar, FL, 1982

    Google Scholar 

  7. Mallegol, J, Lemaire, J, Gardette, JL, “Drier Influence on the Curing of Linseed Oil.” Prog. Org. Coat., 39 107–113 (2000)

    Article  CAS  Google Scholar 

  8. Mallegol, J, Gardette, JL, Lemaire, J, “Long-Term Behavior of Oil-Based Varnishes and Paints. I. Spectroscopic Analysis of Curing Drying Oils.” J. Am. Oil Chem. Soc., 76 967–976 (1999)

    Article  CAS  Google Scholar 

  9. Mallegol, J, Gardette, JL, Lemaire, J, “Long-Term Behavior of Oil-Based Varnishes and Paints. Fate of Hydroperoxides in Drying Oils.” J. Am. Oil Chem. Soc., 77 249–255 (2000)

    Article  CAS  Google Scholar 

  10. Mallegol, J, Gardette, JL, Lemaire, J, “Long-Term Behavior of Oil-Based Varnishes and Paints. Photo- and Thermooxidation of Cured Linseed Oil.” J. Am. Oil Chem. Soc., 77 257–263 (2000)

    Article  CAS  Google Scholar 

  11. Baumann, H, Buhler, M, Fochem, H, Hirsinger, F, Zoebelein, H, Falbe, J, “Natural Fats and Oils—Renewable Raw Materials for the Chemical Industry.” Angew. Chem. Int. Ed. Engl., 27 41–62 (1988)

    Article  Google Scholar 

  12. Liu, ZS, Erhan, SZ, Calvert, PD, “Solid Freeform Fabrication of Epoxidized Soybean Oil/Epoxy Composites with Di-, Tri-, and Polyethylene Amine Curing Agents.” J. Appl. Polym. Sci., 93 356–363 (2004)

    Article  CAS  Google Scholar 

  13. Liu, ZS, Erhan, SZ, Xu, J, Calvert, PD, “Development Of Soybean Oil-Based Composites by Solid Freeform Fabrication Method: Epoxidized Soybean Oil with Bis or Polyalkyleneamine Curing Agents System.” J. Appl. Polym. Sci., 85 2100–2107 (2002)

    Article  CAS  Google Scholar 

  14. Gerbase, AE, Petzhold, CL, Costa, APO, “Dynamic Mechanical and Thermal Behavior of Epoxy Resins Based on Soybean Oil.” J. Am. Oil Chem. Soc., 79 797–802 (2002)

    Article  CAS  Google Scholar 

  15. Thames, SF, Yu, H, “Cationic UV-Cured Coatings of Epoxide-Containing Vegetable Oils.” Surf. Coat. Technol., 115 208–214 (1999)

    Article  CAS  Google Scholar 

  16. Wan Rosli, WD, Kumar, RN, Mek Zah, S, Hilmi, MM, “UV Radiation Curing of Epoxidized Palm Oil-Cycloaliphatic Diepoxide System Induced by Cationic Photoinitiators for Surface Coatings.” Eur. Polym. J., 39 593–600 (2003)

    Article  CAS  Google Scholar 

  17. Thames, SF, Yu, H, Subramanian, R, “Cationic Ultraviolet Curable Coatings from Castor Oil.” J. Appl. Polym. Sci., 77 8–13 (2000)

    Article  CAS  Google Scholar 

  18. Bajpai, M, Shukla, V, Singh, DK, Singh, M, Shukla, R, “A Study of the Film Properties Of Pigmented UV-Curable Epoxidised Soybean Oil.” Pigm. Resin Technol., 33 160–164 (2004)

    Article  CAS  Google Scholar 

  19. Dzunuzovic, E, Tasic, S, Bozic, B, Babic, D, Dunjic, B, “UV-Curable Hyperbranched Urethane Acrylate Oligomers Containing Soybean Fatty Acids.” Prog. Org. Coat., 52 136–143 (2005)

    Article  CAS  Google Scholar 

  20. Zlatanic, A, Lava, C, Zhang, W, Petrovic, ZS, “Effect of Structure on Properties of Polyols and Polyurethanes Based on Different Vegetable Oils.” J. Polym. Sci., Part B: Polym. Phys., 42 809–819 (2004)

    Article  CAS  Google Scholar 

  21. Javni, I, Zhang, W, Petrovic, ZS, “Effect of Different Isocyanates on the Properties of Soy-Based Polyurethanes.” J. Appl. Polym. Sci., 88 2912–2916 (2003)

    Article  CAS  Google Scholar 

  22. Flory, PJ, Principles of Polymer Chemistry, pp. 347–398. Cornell University Press, Ithaca, NY, 1953

    Google Scholar 

  23. Aoshima, S, Higashimura, T, “Living Cationic Polymerization of Vinyl Monomers by Organoaluminum Halides. 3. Living Polymerization of Isobutyl Vinyl Ether by Ethyldichloroaluminum in the Presence of Ester Additives.” Macromolecules, 22 1009–1013 (1989)

    Article  CAS  Google Scholar 

  24. Klaasen, RP, van der Leeuw, RPC, “Fast Drying Cobalt-Free High Solids Alkyd Paints.” Prog. Org. Coat., 55 149–153 (2006)

    Article  CAS  Google Scholar 

  25. Dmytryshyn, SL, Dalai, AK, Chaudhari, ST, Mishra, HK, Reaney, MJ, “Synthesis and Characterization of Vegetable Oil Derived Esters: Evaluation for Their Diesel Additive Properties.” Bioresour. Technol., 92 55–64 (2004)

    Article  CAS  Google Scholar 

  26. Ficek, B, Thiesen, AM, Scranton, AB, “Cationic Photopolymerizations of Thick Polymer Systems: Active Center Lifetime and Mobility.” Eur. Polym. J., 44 98–105 (2008)

    Article  CAS  Google Scholar 

  27. Ito, H, Kidokoro, N, Ishikawa, H, “Differential Photocalorimetric Study of Cationic Photopolymerization.” J. Photopolym. Sci. Technol., 5 235–246 (1992)

    Article  CAS  Google Scholar 

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Acknowledgment

The authors acknowledge the financial support received from the North Dakota Soybean Council.

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Authors and Affiliations

  1. Department of Coatings and Polymeric Materials, North Dakota State University, Fargo, ND, USA

    Samim Alam & Bret J. Chisholm

  2. Center for Nanoscale Science and Engineering, North Dakota State University, Fargo, ND, USA

    Bret J. Chisholm

Authors
  1. Samim Alam
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  2. Bret J. Chisholm
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Corresponding author

Correspondence to Bret J. Chisholm.

Additional information

This paper was awarded First Place in the John A. Gordon Best Paper competition at the 2011 CoatingsTech Conference, sponsored by ACA, on March 14–16, 2011 in Rosemont, IL.

An erratum to this article can be found at http://dx.doi.org/10.1007/s11998-012-9399-5.

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Alam, S., Chisholm, B.J. Coatings derived from novel, soybean oil-based polymers produced using carbocationic polymerization. J Coat Technol Res 8, 671–683 (2011). https://doi.org/10.1007/s11998-011-9360-z

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