Journal of the American Oil Chemists' Society

, Volume 91, Issue 8, pp 1425–1432 | Cite as

Di-Hydroxylated Soybean Oil Polyols with Varied Hydroxyl Values and Their Influence on UV-Curable Pressure-Sensitive Adhesives

Original Paper

Abstract

Di-hydroxylated soybean oil (DSO) polyols with three different hydroxyl values (OHV) of 160, 240, and 285 mg KOH/g were synthesized from epoxidized soybean oils (ESO) by oxirane cleavage with water catalyzed by perchloric acid. The DSO were clear, viscous liquids at room temperature. The structure and physical properties of DSO were characterized using titration methods, Fourier-transform infrared spectroscopy (FTIR), gel permeation chromatography, rheometer, differential scanning calorimetry, and thermogravimetric analysis. The number average molecular weight of DSO160, DSO240, and DSO285 were 1,412, 1,781, and 1,899 g/mol, respectively, indicating that oligomerization occurred during DSO synthesis, which was further confirmed by FTIR. All DSO polyols exhibited non-Newtonian, shear thinning behavior. DSO with higher OHV were more viscous than those with lower OHV. All DSO were thermally stable up to 380 °C. These three DSO were formulated into pressure-sensitive adhesives (PSA) by copolymerizing with ESO using UV curing. The peel adhesion strength of the PSA was significantly affected by the OHV of DSO and DSO content. Maximal PSA adhesion strength of 4.6 N/inch was obtained with DSO285 and a DSO/ESO weight ratio of 0.75.

Keywords

Epoxidized soybean oil(s) (ESO) Di-hydroxylated soybean oil Polyol Hydroxyl value(s) (OHV) Physical properties UV-curing Pressure-sensitive adhesive(s) (PSA) Peel adhesion strength Biobased product 

Notes

Acknowledgments

The authors appreciate the funding support from Kansas Soybean Commission/United Soybean Board. Contribution No. 14-254-J from the Kansas Agricultural Experimental Station.

References

  1. 1.
    Johnston J (2003) Pressure sensitive adhesive tapes: A guide to their function, design, manufacture, and use. Pressure Sensitive Tape Council, NorthbrookGoogle Scholar
  2. 2.
    Aranyi C, Gutfreud K, Hawryiewicz EJ, Wall JS (1971) Pressure-sensitive adhesive tape comprising gluten hydrolypate derivatives. US Patent 3607370Google Scholar
  3. 3.
    Cohen E, Binshtok O, Dotan A, Dodiuk H (2013) Prospective materials for biodegradable and/or biobased pressure-sensitive adhesives: a review. J Adhes Sci Technol 27:1998–2013Google Scholar
  4. 4.
    Bunker S, Staller C, Willenbacher N, Wool R (2003) Miniemulsion polymerization of acrylated methyl oleate for pressure sensitive adhesives. Int J Adhes Adhes 23:29–38CrossRefGoogle Scholar
  5. 5.
    Shin J, Martello M, Shrestha M, Wissinger J, Tolman W, Hillmyer M (2011) Pressure-sensitive adhesives from renewable triblock copolymers. Macromolecules 44:87–94CrossRefGoogle Scholar
  6. 6.
    Ahn K, Sung J, Kim N, Kraft S, Sun X (2012) UV-curable pressure-sensitive adhesives derived from functionalized soybean oils and rosin ester. Polym Int. doi: 10.1002/pi.4420 Google Scholar
  7. 7.
    Petrovic ZS (2008) Polyurethanes from vegetable oils. Polym Rev 48:109–155CrossRefGoogle Scholar
  8. 8.
    Guo A, Cho Y, Petrovic Z (2000) Structure and properties of halogenated and nonhalogenated soy-based polyols. J Polym Sci Part A: Polym Chem 38:3900–3910CrossRefGoogle Scholar
  9. 9.
    Stemmelen M, Pessel F, Lapinte V, Caillol S, Habas JP, Robin JJ (2011) A fully biobased epoxy resin from vegetable oils: from the synthesis of the precursors by thiol-ene reaction to the study of the final material. J Polym Sci Part A: Polym Chem 49:2434–2444CrossRefGoogle Scholar
  10. 10.
    Xia Y, Larock RC (2010) Vegetable oil-based polymeric materials: synthesis, properties, and applications. Green Chem 12:1893–1909CrossRefGoogle Scholar
  11. 11.
    Desroches M, Escouvois M, Auvergne R, Caillol S, Boutevin B (2012) From vegetable oils to polyurethanes: synthetic routes to polyols and main industrial products. Polym Rev 52:38–79CrossRefGoogle Scholar
  12. 12.
    Sinadinovic-Fiser S, Jankovic M, Petrovic ZS (2001) Kinetics of in situ epoxidation of soybean oil in bulk catalyzed by ion exchange resin. J Am Oil Chem Soc 78:725–731CrossRefGoogle Scholar
  13. 13.
    Pfister D, Xia Y, Larock R (2011) Recent advances in vegetable oil-based polyurethanes. Chemsuschem 4:703–717CrossRefGoogle Scholar
  14. 14.
    Guo Y, Hardesty J, Mannari V, Massingill J Jr (2007) Hydrolysis of epoxidized soybean oil in the presence of phosphoric acid. J Am Oil Chem Soc 84:929–935CrossRefGoogle Scholar
  15. 15.
    Godoy S, Ferrao M, Gerbase A (2007) Determination of the hydroxyl value of soybean polyol by attenuated total reflectance/Fourier transform infrared spectroscopy. J Am Oil Chem Soc 84:503–508CrossRefGoogle Scholar
  16. 16.
    Harry-O’kuru RE, Carriere CJ (2002) Synthesis, polyhydroxy triglycerides derived from milkweed oil. J Agric Food Chem 50:3214–3221CrossRefGoogle Scholar
  17. 17.
    Lozada Z, Suppes G, Tu Y, Hsieh F (2009) Soy-based polyols from oxirane ring opening by alcoholysis reaction. J Appl Polym Sci 113:2552–2560CrossRefGoogle Scholar
  18. 18.
    Lin B, Yang L, Dai H, Yi A (2008) Kinetic studies on oxirane cleavage of epoxidized soybean oil by methanol and characterization of polyols. J Am Oil Chem Soc 85:113–117CrossRefGoogle Scholar
  19. 19.
    Monteavaro L, Silva E, Costa A, Samios D, Gerbase A, Petzhold C (2005) Polyurethane networks from formiated soy polyols: synthesis and mechanical characterization. J Am Oil Chem Soc 82:365–371CrossRefGoogle Scholar
  20. 20.
    Ahn BK, Kraft S, Wang D, Sun XS (2011) Thermally stable, transparent, pressure-sensitive adhesives from epoxidized and dihydroxyl soybean oil. Biomacromolecules 12:1839–1843CrossRefGoogle Scholar
  21. 21.
    Kong X, Liu G, Qi H, Curtis JM (2013) Preparation and characterization of high-solid polyurethane coating systems based on vegetable oil derived polyols. Prog Org Coat 76:1151–1160CrossRefGoogle Scholar
  22. 22.
    Caillol S, Desroches M, Boutevin G, Loubat C, Auvergne R, Boutevin B (2012) Synthesis of new polyester polyols from epoxidized vegetable oils and biobased acids. Eur J Lipid Sci Technol 114:1447–1459CrossRefGoogle Scholar
  23. 23.
    Creton C (2003) Pressure-sensitive adhesives: an introductory course. MRS Bull 28:434–439CrossRefGoogle Scholar

Copyright information

© AOCS 2014

Authors and Affiliations

  1. 1.Bio-Materials and Technology Lab, Department of Grain Science and IndustryKansas State UniversityManhattanUSA

Personalised recommendations