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Synthesis of Renewable Resource-derived Furan-based Epoxy Compounds and Their Adhesive Property  

Lee, Jae-Soung (Department of Life Chemistry, Catholic University of Daegu)
Lee, Sang-Hyeup (Department of Life Chemistry, Catholic University of Daegu)
Jeong, Jaewon (Green Chemistry & Manufacturing System Division, Green Process R&D Department, Korea Institute of Industrial Technology)
Kim, Baekjin (Green Chemistry & Manufacturing System Division, Green Process R&D Department, Korea Institute of Industrial Technology)
Cho, Jin Ku (Green Chemistry & Manufacturing System Division, Green Process R&D Department, Korea Institute of Industrial Technology)
Kim, Hyun Joong (Lab. of Adhesion & Bio-Composites, Program in Environmental Materials, Research Team for Biomass-based Bio-Materials, Seoul National University)
Publication Information
Journal of Adhesion and Interface / v.11, no.2, 2010 , pp. 41-49 More about this Journal
Abstract
Furan-containing epoxide monomers (8, 9) were designed and synthesized as carbon-neutral, environment-friendly adhesion material. Bicyclic skeleton were constructed using the Diels-Alder reaction of furan and methyl acrylate, both readily accessible starting material from a biomass via bio-refinery process. After reduction of ester functionality, resulting hydroxyl moieties were coupled to epichlorohydrin to provide the epoxy-functionalized furanic monomers (8, 9). The structure of new furanic monomers was confirmed by $^1H$ and $^{13}C$ NMR spectroscopy. As UV-curable monomers, basic properties such as UV curing time and the extent of UV curing were evaluated by photo DSC. Photo-curing shrinkages were measured by linear variable differential transformer transducer (LVDT) and the effect of molecular structure on shrinkage was considered. In addition, new synthetic compounds showed the shear strength over 3 MPa when they were photo-cured between polycarbonate plates, which indicates these compounds are feasible to use as photo-curable adhesive materials.
Keywords
Carbon-neutral; furan; Diels-Alder reaction; epoxy; curing rate; shrinkage;
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1 A. Corma, S. Iborra, and A. Velty, Chem. Rev., 107, 2411 (2007).   DOI   ScienceOn
2 J. N. Chheda, G. W. Huber, and J. A. Dumesic, Angew. Chem. Int. Ed., 46, 7164 (2007).   DOI   ScienceOn
3 D. E. Packham, Int. J. Adhes. Adhes., 29, 248 (2009).   DOI   ScienceOn
4 Y. Roman-Leshkov, J. N. Chheda, and J. A. Dumesic, Science, 312, 1933 (2006).   DOI   ScienceOn
5 H. Zhao, J. E. Holladay, H. Brown, and Z. C. Zhang, Science, 316, 1597 (2007).   DOI   ScienceOn
6 Y. R. Leshkov, C. J. Barrett, Z. Y. Liu, and J. A. Dumesic, Nature, 447, 982 (2007).   DOI   ScienceOn
7 A. Gandini and M. N. Belgacem, Prog. Polym. Sci., 22, 1203 (1997).   DOI   ScienceOn
8 A. Gandini and M. N. Belgacem, J. Polym. Environ., 10, 105 (2002).   DOI   ScienceOn
9 T. Ishimatsu, U. S. Patent, 6,827,880 (2004).
10 H. Kotsuki, K. Asao, and H. Ohnishi, Bull. Chem. Soc. Jpn., 57, 3339 (1984).   DOI   ScienceOn
11 W. H. Heath, F. Palmieri, J. R. Adams, B. K. Long, J. Chute, T. W. Holcombe, S. Zieren, M. J. Truitt, J. L. White, and C. G. Willson, Macromolecules, 41, 719 (2008).   DOI   ScienceOn
12 J. Das, T. Vu, D. N. Harris, and M. L. Ogletree, J. Med. Chem., 31, 930 (1988).   DOI
13 K. Okamoto, R. Akiyama, and S. Kobayashi, J. Org. Chem., 69, 2871 (2004).   DOI   ScienceOn
14 A. B. de Morais, A. B. Pereira, J. P. Teixeira, and N. C. Cavaleiro, Int. J. Adhes. Adhes., 27, 679 (2007).   DOI   ScienceOn
15 E. Arceo, P. Marsden, R. G. Bergman, and J. A. Ellman, Chem. Commun., 3357 (2009).