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Soy-based UV-curable thiol–ene coatings

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Abstract

Novel soy-based thiols and enes were synthesized and characterized. Then, soy-based thiol–ene UV-curable coatings were formulated and their coating physiochemical properties were investigated in detail. The use of biorenewable resources, combined with environmentally friendly UV-curable technology, provides a “green + green” solution to the stricter regulations in the coatings industry. Novel soy-based thiols and enes were synthesized through the Lewis acid-catalyzed ring opening reaction of epoxidized soybean oil with multifunctional thiols or hydroxyl functional allyl compounds. FTIR and NMR confirmed the formation of the target compounds. The soy-based thiols and enes were formulated with petrochemical-based enes and thiols, respectively, to make thiol–ene UV-curable coatings. Typical coating film properties, thermal properties, and photopolymerization kinetics of these coatings were studied. Soy-based thiol–ene coatings having lower functionality thiols and enes have poor UV curability and coating properties, which was attributed to the lower crosslink density. Soy-based thiols and enes with higher functionality can be UV-cured in combination with petrochemical-based enes or thiols even without the presence of free radical photoinitiators. Better coating film properties were obtained from these higher functionality thiol–ene systems that were toughened by commercial hyperbranched acrylates.

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References

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

    Article  PubMed  CAS  Google Scholar 

  2. Liu, Z, Erhana, SZ, Xu, J, “Preparation, Characterization and Mechanical Properties of Epoxidized Soybean Oil/Clay Nanocomposites.” Polymer, 46 10119–10127 (2005)

    Article  CAS  Google Scholar 

  3. Fomin, VA, Guzeev, VV, “Biodegradable Polymers: Status and Prospects.” Plast. Massy, 2 42–48 (2001)

    Google Scholar 

  4. Schroeter, J, “Biodegradable (Plastic) Materials. A Status Report.” Kunststoffe, 90 64–66 (2000)

    CAS  Google Scholar 

  5. Mishra, DP, Mahanwar, PA, “Advances in Bioplastic Materials.” Pop. Plast. Packag., 45 68–76 (2000)

    CAS  Google Scholar 

  6. Wool, RP, “Development of Affordable Soy-Based Plastics, Resins, and Adhesives.” Chemtech., 29 44–48 (1999)

    CAS  Google Scholar 

  7. Gu, H, Ren, K, Martin, D, Marino, T, Neckers, DC, “Cationic UV-Cured Coatings Containing Epoxidized Soybean Oil Initiated by New Onium Salts Containing Tetrakis(pentafluorophenyl)gallate Anion.” J. Coat. Technol., 74 49–52 (2002)

    Article  CAS  Google Scholar 

  8. Teng, G, Soucek, MD, “Epoxidized Soybean Oil-Based Ceramer Coatings.” J. Am. Oil Chem. Soc., 77 381–387 (2000)

    Article  CAS  Google Scholar 

  9. Masayuki S, Hiroshi, U, Tadashi, H, Nobuo F, Mamoru S, Toppan Printing Co., Ltd., “Polyolefin-Based Adhesive Compositions for Lamination.” JP 99-352849 19991213, 2001.

  10. Lee, SH, Lee, SY, Lim, H, Nam, J, Kye, H, Lee, Y, “Preparation and Properties of Plasticized Cellulose Diacetate Using Triacetine/Epoxidized Soybean Oil.” Polymer (Korea), 30 202–206 (2006)

    CAS  Google Scholar 

  11. Ali, SM, Mahmoud, M, Saie, AS, “Mechanical and Thermal Properties of the Plasticized PVC-ESBO.” Iran Polym. J., 14 769–773 (2005)

    Google Scholar 

  12. Choi, JS, Park, WH, “Effect of Biodegradable Plasticizers on Thermal and Mechanical Properties of Poly(3-hydroxybutyrate).” Polym. Test., 23 455–460 (2004)

    Article  CAS  Google Scholar 

  13. Adhvaryu, A, Erhan, SE, “Epoxidized Soybean Oil as a Potential Source of High-Temperature Lubricants.” Industr. Crop Product, 15 247–254 (2002)

    Article  CAS  Google Scholar 

  14. Hwang, H, Erhan, SE, “Modification of Epoxidized Soybean Oil for Lubricant Formulations with Improved Oxidative Stability and Low Pour Point.” J. Am. Oil Chem. Soc., 78 1179–1184 (2001)

    Article  CAS  Google Scholar 

  15. Senyurt, AF, Wei, H, Phillips, B, Cole, M, Nazarenko, S, Hoyle, CE, Piland, SG, Gould, TE, “Physical and Mechanical Properties of Photopolymerized Thiol–Ene/Acrylates.” Macromolecules, 39 6315–6317 (2006)

    Article  ADS  CAS  Google Scholar 

  16. Lee, T, Roper, TM, Jonsson, ES, Guymon, CA, Hoyle, CE, “Thiol–Ene Photopolymerization Kinetics of Vinyl Acrylate/Multifunctional Thiol Mixtures.” Macromolecules, 37 3606–3613 (2004)

    Article  ADS  CAS  Google Scholar 

  17. Hoyle, CH, Lee, T, Roper, TM, “Thiol–Enes: Chemistry of the Past with Promise for the Future.” J. Polym. Sci. A, 42 5301–5338 (2004)

    Article  CAS  Google Scholar 

  18. Senyurt, AF, Warren, G, Whitehead, JB, Jr, Hoyle, CE, “Matrix Physical Structure Effect on the Electro-Optic Characteristics of Thiol–Ene Based H-PDLC Films.” Polymer, 47 2741–2749 (2006)

    Article  CAS  Google Scholar 

  19. Roper, TM, Kwee, T, Lee, T, Guymon, CA, Hoyle, CE, “Photopolymerization of Pigmented Thiol–Ene Systems.” Polymer, 45 2921–2929 (2004)

    Article  CAS  Google Scholar 

  20. Cramer, NB, Beckel, ER, Harant, AW, Davies, T, Williamson, DL, Bowman, CN, “Formation of a Host Nanostructure for Ferroelectric Liquid Crystals Using Thiol–Ene Polymers.” Liquid Crystal., 29 1291–1296 (2002)

    Article  CAS  Google Scholar 

  21. Li, Y, Birnkrant, MJ, Natarajan, LV, Tondigli, VP, Lloyd, PF, Sutherland, RL, Bunning, TJ, “Polymer Crystallization/Melting Induced Thermal Switching in a Series of Holographically Patterned Bragg Reflectors.” Soft Matter., 1 238–242 (2005)

    Article  CAS  Google Scholar 

  22. Cai, J, Shu, W, Yun, L, Jiu, L, “Influence of Reactive Diluents on UV Curing Acrylic Epoxidized Soybean Oil System.” Tuliao Gongye, 36 12–15 (2006)

    CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  24. Desai, D, Rahim, M, Massingill, JL, Jr, “Cationic UV Cured Coatings Using Epoxidized Soybean Oil.” In: Experience the World of UV/EB, RadTech 2000: The Premier UV/EB Conference & Exhibition, Baltimore, MD, United States, pp. 22–44 (2000)

  25. Klang, JA, Radiation Curable Hyperbranched Polyester Acrylates. Sartomer Company, Inc. Exton, PA, USA.

  26. Cramer, NB, Bowman, CN, “Kinetics of Thiol–Ene and Thiol–Acrylate Photopolymerizations with Real-Time Fourier Transform Infrared.” J. Polym. Sci. A, 39 3311–3319 (2001)

    Article  CAS  Google Scholar 

  27. Wei, H, Senyurt, AF, Jonsson, S, Hoyle, CE, “Photopolymerization of Ternary Thiol–Ene/Acrylate Systems: Film and Network Properties.” J. Polym. Sci. A, 45 822–829 (2007)

    Article  CAS  Google Scholar 

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Acknowledgment

We would like to thank the North Dakota Soybean Council for sponsoring this research.

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Authors and Affiliations

  1. Center for Nanoscale Science and Engineering, North Dakota State University, PO Box 6050, Fargo, ND, 58108, USA

    Zhigang Chen, Bret J. Chisholm, Radhika Patani, Jennifer F. Wu, Shashi Fernando, Katie Jogodzinski & Dean C. Webster

  2. Department of Coatings and Polymeric Materials, North Dakota State University, PO Box 6050, Fargo, ND, 58108, USA

    Bret J. Chisholm & Dean C. Webster

Authors
  1. Zhigang Chen
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  2. Bret J. Chisholm
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  3. Radhika Patani
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  4. Jennifer F. Wu
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  5. Shashi Fernando
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  6. Katie Jogodzinski
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  7. Dean C. Webster
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Corresponding author

Correspondence to Dean C. Webster.

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Chen, Z., Chisholm, B.J., Patani, R. et al. Soy-based UV-curable thiol–ene coatings. J Coat Technol Res 7, 603–613 (2010). https://doi.org/10.1007/s11998-010-9241-x

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  • DOI: https://doi.org/10.1007/s11998-010-9241-x

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