DOI QR코드

DOI QR Code

Bio-based Photopolymer Synthesis: Epoxidized Soybean Oil (ESO) Modified with Itaconic Acid and Vinyl Acetate

  • Shinhee Choi (Department of Packaging, Yonsei University) ;
  • Gunhee Park (Department of Packaging, Yonsei University) ;
  • Nohjin Park (Department of Packaging, Yonsei University) ;
  • Taesung Choi (Department of Packaging, Yonsei University) ;
  • Sangwon Lim (Department of Packaging, Yonsei University) ;
  • Su-il Park (Department of Packaging, Yonsei University)
  • 투고 : 2025.04.02
  • 심사 : 2025.04.13
  • 발행 : 2025.04.30

초록

This study aimed to synthesize a bio-based UV-curable polymer, itaconated epoxidized soybean oil (IESO), using epoxidized soybean oil (ESO) and itaconic acid (IA) as replacements for acrylic polymers. Vinyl acetate (VAc) was added to improve the polymerization rate, adhesion, and water resistance of IESO. The itaconated epoxidized soybean oil/Vinyl acetate (IESO/VAc) content was adjusted to ratios of 9:1, 7:3, and 5:5, then IESO/VAc coated paper and standalone films were produced using a UV curing system. Fourier transform infrared spectroscopy analysis confirmed a decrease in C=C bond intensity after UV curing, indicating successful radical polymerization. The adhesion test demonstrated stable adhesive performance, and the water contact angle confirmed that the coating exhibits significant hydrophobicity. In the recycling test, all samples dissolved, indicating that IESO/VAc is a bio-based material that can be chemically recycled. Consequently, IESO/VAc blends have the potential to replace fossil-based curable polymer and may be used as coatings for paper packaging.

키워드

참고문헌

  1. Shen, M., Huang, W., Chen, M., Song, B., Zeng, G., and Zhang, Y. 2020. (Micro)plastic crisis: Un-ignorable contribution to global greenhouse gas emissions and climate change. J Clean Prod 254: 120138.
  2. Dong, X., Ren, J., Duan, Y., Wu, D., Lin, L., Shi, J., Jia, R., Xu, X., and He, X. 2022. Preparation and properties of green UV‐curable itaconic acid cross‐linked modified waterborne polyurethane coating. J Appl Polym Sci 139 (17): 52042.
  3. Wang, Z., Liang, H., Yang, H., Xiong, L., Zhou, J., Huang, S., Zhao, C., Zhong, J., and Fan, X. 2019. UV-curable self-healing polyurethane coating based on thiol-ene and Diels-Alder double click reactions. Prog Org Coat 137: 105282.
  4. Vitale, A., Trusiano, G., and Bongiovanni, R. 2017. UV-curing of adhesives: A critical review. Rev Adhes Adhes 5: 105-161.
  5. Fortune Business Insights. 2025. Industrial Coatings Market Size, Share & Industry Analysis, By Resin (Acrylic, Alkyd, Polyurethane, Epoxy, Polyester, and Others), By Technology (Solvent-borne, Water-borne, Powder, and Others), By End-use (General Industrial, Powder, Automotive OEM, Automotive Refinish, Protective, Wood, Marine, Coil, Packaging, and Others), and Regional Forecast, 2024-2032.
  6. Liu, F., Liu, A., Tao, W., and Yang, Y. 2020. Preparation of UV curable organic/inorganic hybrid coatings-a review. Prog Org Coat 145: 105685.
  7. Patil, R. S., Thomas, J., Patil, M., and John, J. 2023. To shed light on the UV curable coating technology: Current state of the art and perspectives. J Compos Sci 7 (12): 513.
  8. Li, P., Ma, S., Dai, J., Liu, X., Jiang, Y., Wang, S., Wei, J., Chen, J., and Zhu, J. 2017. Itaconic Acid as a Green Alternative to Acrylic Acid for Producing a Soybean Oil-Based Thermoset: Synthesis and Properties. ACS Sustain Chem Eng 5 (1): 1228-1236. https://doi.org/10.1021/acssuschemeng.6b02654
  9. Habib, F., and Bajpai, M. 2011. Synthesis characterization of acrylated epoxidized soybean oil for UV-cured coatings. Chem Chem Technol 5.
  10. Zhou, Y., Feng, L., and Qu, J. 2023. Preparation of high-performance epoxy soybean oil-based UV-curable oligomers and coatings. J Coat Technol Res 20 (6): 1923-1933. https://doi.org/10.1007/s11998-023-00787-2
  11. Dai, J., Liu, X., Ma, S., Wang, J., Shen, X., You, S., and Zhu, J. 2016. Soybean oil-based UV-curable coatings strengthened by crosslink agent derived from itaconic acid together with 2-hydroxyethyl methacrylate phosphate. Prog Org Coat 97: 210-215. https://doi.org/10.1016/j.porgcoat.2016.04.014
  12. Yang, X., Li, S., Xia, J., Song, J., Huang, K., and Li, M. 2015. Renewable Myrcene-based UV-curable Monomer and its Copolymers with Acrylated Epoxidized Soybean Oil: Design, Preparation, and Characterization. Bioresources 10(2).
  13. Zhang, C., Yan, M., Cochran, E. W., and Kessler, M. R. 2015. Biorenewable polymers based on acrylated epoxidized soybean oil and methacrylated vanillin. Mater Today Commun 5: 18-22. https://doi.org/10.1016/j.mtcomm.2015.09.003
  14. Zhang, Y., Li, Y., Wang, L., Gao, Z., and Kessler, M. R. 2017. Synthesis and Characterization of Methacrylated Eugenol as a Sustainable Reactive Diluent for a Maleinated Acrylated Epoxidized Soybean Oil Resin. ACS Sustain Chem Eng 5 (10): 8876-8883. https://doi.org/10.1021/acssuschemeng.7b01673
  15. Di Mauro, C., Genua, A., and Mija, A. 2022. Fully bio-based reprocessable thermosetting resins based on epoxidized vegetable oils cured with itaconic acid. Ind Crops Prod 185: 115116.
  16. Gadhave, R. V. 2024. Polyvinyl Acetate and Vinyl Acetate-Ethylene Hybrid Adhesive: Synthesis, Characterization, and Properties. OJPChemen 14 (1): 1-18. https://doi.org/10.4236/ojpchem.2024.141001
  17. Halligan, S. C., Dalton, M. B., Murray, K. A., Dong, Y., Wang, W., Lyons, J. G., and Geever, L. M. 2017. Synthesis, characterisation and phase transition behaviour of temperature-responsive physically crosslinked poly (N-vinylcaprolactam) based polymers for biomedical applications. Mater Sci Eng C Mater Biol Appl 79: 130-139. https://doi.org/10.1016/j.msec.2017.03.241
  18. Di Mauro, C., Malburet, S., Genua, A., Graillot, A., and Mija, A. 2020. Sustainable Series of New Epoxidized Vegetable Oil-Based Thermosets with Chemical Recycling Properties. Biomacromolecules 21 (9): 3923-3935. https://doi.org/10.1021/acs.biomac.0c01059
  19. Xi, X., Pizzi, A., and Delmotte, L. 2018. Isocyanate-free polyurethane coatings and adhesives from mono-and di-saccharides. Polymers (Basel) 10 (4): 402.
  20. Sen, P., Suresh, K., Vinoth Kumar, R., Kumar, M., and Pugazhenthi, G. 2016. A simple solvent blending coupled sonication technique for synthesis of polystyrene (PS)/multiwalled carbon nanotube (MWCNT) nanocomposites: Effect of modified MWCNT content. J Sci: Adv Mater Devices 1(3): 311-323. https://doi.org/10.1016/j.jsamd.2016.06.016
  21. Tee, Y. B., Talib, R. A., Abdan, K., Chin, N. L., Basha, R.K., and Yunos, K. F. M. 2016. Comparative study of chemical, mechanical, thermal, and barrier properties of poly (lactic acid) plasticized with epoxidized soybean oil and epoxidized palm oil. Bioresources 11 (1): 1518-1540.
  22. Maia, D. L. H., and Fernandes, F. A. N. 2022. Influence of carboxylic acid in the production of epoxidized soybean oil by conventional and ultrasound-assisted methods. Biomass Convers Biorefin 12 (12): 5861-5868. https://doi.org/10.1007/s13399-020-01130-0
  23. Li, Y., Ma, Q., Li, G., Lou, J., Chen, X., He, Y., and Peng, W. 2022. Pyrolysis of Aesculus chinensis Bunge Leaves as for Extracted Bio-Oil Material. Polymers (Basel) 14 (22): 5003.
  24. Acik, G., Kamaci, M., and Cansoy, C. E. 2018. Superhydrophobic EVA copolymer fibers: the impact of chemical composition on wettability and photophysical properties. Colloid Polym Sci 296 (11): 1759–1766. https://doi.org/10.1007/s00396-018-4395-7
  25. Ziegenbalg, N., Gruschwitz, F. V, Adermann, T., Mayr, L., Guriyanova, S., and Brendel, J. C. 2022. Vinyl mercaptoethanol as a reactive monomer for the preparation of functional homo- and copolymers with (meth)acrylates. Polym Chem 13 (34): 4934-4943. https://doi.org/10.1039/D2PY00598K
  26. Marasinghe, L., Croutxé-Barghorn, C., Allonas, X., and Criqui, A. 2018. Effect of reactive monomers on polymer structure and abrasion resistance of UV cured thin films. Prog Org Coat 118: 22-29. https://doi.org/10.1016/j.porgcoat.2017.09.020
  27. Belhassen, R., Vilaseca, F., Mutjé, P., and Boufi, S. 2014. Thermoplasticized starch modified by reactive blending with epoxidized soybean oil. Ind Crops Prod 53: 261-267. https://doi.org/10.1016/j.indcrop.2013.12.039
  28. Sim, Y. J., Seo, E. K., Choi, G. J., Yoon, S. J., and Jang, J. H. 2009. UV-induced Crosslinking of Poly(vinyl acetate) Films Containing Benzophenone. Textile Coloration and Finishing 21 (4): 33-38. https://doi.org/10.5764/TCF.2009.21.4.033
  29. Abu-Saied, M. A., Khalil, K. A., and Al-Deyab, S. S. 2012. Preparation and Characterization of Poly Vinyl Acetate Nanofiber Doping Copper Metal. Int J Electrochem Sci 7(3): 2019-2027. https://doi.org/10.1016/S1452-3981(23)13859-4
  30. Holland, B. J., and Hay, J. N. 2002. The thermal degradation of poly(vinyl acetate) measured by thermal analysis–Fourier transform infrared spectroscopy. Polymer (Guildf) 43(8): 2207-2211. https://doi.org/10.1016/S0032-3861(02)00038-1
  31. Rimez, B., Rahier, H., Van Assche, G., Artoos, T., Biesemans, M., and Van Mele, B. 2008. The thermal degradation of poly(vinyl acetate) and poly(ethylene-co-vinyl acetate), Part I: Experimental study of the degradation mechanism. Polym Degrad Stab 93 (4): 800-810. https://doi.org/10.1016/j.polymdegradstab.2008.01.010
  32. Bredin, A., Larcher, A.V, and Mullins, B.J. 2011. Thermo-gravimetric analysis of carbon black and engine soot-Towards a more robust oil analysis method. Tribol Int 44(12): 1642-1650. https://doi.org/10.1016/j.triboint.2011.06.002