Abstract
The hydroformylation of seed oil based fatty acid methyl esters leads to aldehyde intermediates that can be hydrogenated to give novel seed oil based monomers. In this study, the seed oil based monomers were polymerized with low molecular weight diols to produce novel aliphatic polyester polyols with very low viscosities. The seed oil polyester polyols provide environmentally friendly (green) coating formulations with low volatile organic compound emissions which lead to coatings with superior physical properties, such as exceptional hydrolytic resistance and flexibility. From these polyester polyols, waterborne polyurethane dispersions were also developed with excellent stability resulting in coatings with superior physical properties (i.e., good toughness and abrasion resistance), and exceptional hydrolytic and acid resistance.
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®™ Trademark of the Dow Chemical Company.
®™ Trademark of the Dow Chemical Company.
References
Hare, CH, “Polyester Resins.” In: Protective Coatings, Fundamentals of Chemistry and Composition. Technology Publishing Company, Pittsburgh, PA (1994)
Goldberg, D., Eaton, R.F., “Caprolactone Polyols as Reactive Diluents for High-Solids,” Modern Paint and Coatings, 82, 36–42, 1992
Peacock, G.S., “Reactive Diluents for Higher Solids Thermoset Coatings,”. Modern Paint and Coatings, 74, 178–182, 1984
Oldring P, Hayward G, “Polyester Resins.” In: Resins for Surface Coatings. Sita Technology, London (1987)
Mannari VM, Massinghill JL, Jr, “Two-Component High-Solid Polyurethane Coating Systems Based on Soy Polyols.” In: Proceedings of the Twenty-Ninth International Waterborne, High-Solids, and Powder Coatings Symposium, p. 225, 2002
Honcoop, E, Appelman, E, “Polyester Polyols for Water Resistant Polyurethane Coatings.” In: Proceedings of the Thirtieth International Waterborne, High-Solids, and Powder Coatings Symposium, p. 459, 2003
Oostwal, MR, Minnee, JS, Mulder, GP, DeMooy, AC, “Oligomers of Fatty Acids.” EP 0,984,916 to Unichema Chemie, 2000
Lysenko, Z, et al., “Vegetable Oil Based Polyols and Polyurethanes Made Therefrom.” World Patent Application WO2004096882 A1, 2004
Argyropoulos, J, Spilman, G, Franca, M, Hayson, K, “UNOXOL™ Diol, A New Liquid Cycloaliphatic Diol for Coatings Applications.” Paint Coat. Ind., 22, 60–66 (2006)
Flory, P.J., “Molecular Size Distribution in Three Dimensional Polymers. VI. Branched Polymers Containing A-R-B Type Units”, in J. Am. Chem. Soc., 74, 2718–2723, 1952
Hoy, K.L., “New Values of the Solubility Parameters from Vapor Pressure Data”, in Journal Paint Technology, 42, 76–78, 1970
Hoy, K.L., “The Hoy Tables of Solubility Parameters”, Union Carbide Corp., 1985
Guner, A., “The Algorithmic Calculations of Solubility Parameter for the Determination of Interactions in Dextrin/Certain Polar Solvent Systems”, Eur. Polym. J., 40, 1587–1594, 2004
Argyropoulos, J, et al., “Hindered-Hydroxyl Functional (Meth)acrylate Compounds and Processes for the Preparation Thereof.” US Patent 5,420,341, 1995
Acknowledgments
Special thanks to Marty Beebe and Paul Foley for resin synthesis, and Amy Cooper and Kym Burgess for the preparation and evaluation of the coatings. In addition the authors are grateful to Alfredo Larre, Jorge Jimenez, Erin O’Driscoll, and Patty DeMattia for their helpful discussions and support. Finally we are indebted to Dr. Ken Hoy for his fundamental teachings in coatings.
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This paper was presented at the 2007 FutureCoat! Conference, sponsored by Federation of Societies for Coatings Technology, October 3–5, 2007, in Toronto, ON, Canada.
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Argyropoulos, J., Popa, P., Spilman, G. et al. Seed oil based polyester polyols for coatings. J Coat Technol Res 6, 501–508 (2009). https://doi.org/10.1007/s11998-008-9154-0
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DOI: https://doi.org/10.1007/s11998-008-9154-0