Abstract
2-Pyrone-4,6-dicarboxylic acid (PDC), a chemically stable metabolic intermediate of lignin, its bis(hydroxyethyl) derivative (BHPDC) and bis(hydroxyethyl) terephthalate (BHT) were polymerized to prepare the corresponding polyesters carrying the oxyethyleneoxycarbonyl(2-pyrone-4,6-diyl)carbonyl and oxyethyleneoxy-terephthaloyl units [x and y units, resp., x + y = 1] by polycondensation eliminating water and/or 1,2-ethanediol molecules. The polyesters were mostly stable up to 210 °C, after that the degradation of pyrone ring commenced. These polyesters exhibited strong adhering properties against metal, glass and surfaces with increasing the x unit content to 0.4–0.6, such as about 50–60 MPa for SUS/polyester/SUS or Al/ polyester/Al samples, by the JIS K 6849:1994 testing method of tensile strength. As the fracturing plane was the midst of the polyester layer and at the interface, the polyester was tenaciously adhering to the metal surface.
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“Biopolymers,” A. Steinbuchel, Y. Doi, and M. Hofrichter, Ed., Vol. 3, Wiley-VCH, Weinheim, 2002.
E. T. H. Vink, K. R. Rabago, D. A. Glassner, and P. R. Gruber, Polym. Degrad. Stab., 80, 403 (2003).
“Biorefineries-Industrial Processes and Products,” B. Kamm, P. R. Gruber, and M. Kamm, Ed., Wiley-VCH, Weinheim, 2006.
A. J. Ragauskas, C. K. Williams, B. H. Davison, G. Britovsek, J. Cairney, C. A. Eckert, W. J. Frederick, Jr ., J. P. Hallett, D. J. Leak, C. L. Liotta, J. R. Mielenz, R. Murphy, R. Templer, and T. Tschaplinski, Science, 311, 484 (2006).
Y. Nishio, Adv. Polym. Sci., 205, 97 (2006).
S.-i. Hirota, T. Sato, Y. Tominaga, S. Asai, and M. Sumita, Polymer, 47, 3954 (2006).
B. Kamm, Angew. Chem., Int. Ed., 46, 5056 (2007).
J. N. Chheda, G. W. Huber, and J. A. Dumesic, Angew. Chem., Int. Ed., 46, 7164 (2007).
D. Riggle, BioCycle, 39, 64 (1998).
T. Kaneko, T. H. Thi, D. J. Shi, and M. Akashi, Nat. Mater., 5, 966 (2006).
M. Funaoka, Polym. Int., 47, 277 (1998).
Y. Román-Leshkov, C. J. Barrett, Z. Y. Liu, and J. A. Dumesic, Nature, 447, 982 (2007).
A. Corma, S. Iborra, and A. Velty, Chem. Rev., 107, 2411 (2007).
S. R. Boethling, E. Sommer, and D. DiFiore, Chem. Rev., 107, 2207 (2007).
Y. Otsuka, M. Nakamura, K. Shigehara, K. Sugimura, E. Masai, S. Ohara, and Y. Katayama, Appl. Microbiol. Biotechnol., 71, 608 (2006).
T. Michinobu, M. Hishida, M. Sato, Y. Katayama, K. Noguchi, E. Masai, M. Nakamura, Y. Otsuka, S. Ohara, and K. Shigehara, Polym. J., 40, 68 (2008).
T. Michinobu, M. Bito, Y. Yamada, Y. Katayama, K. Noguchi, E. Masai, M. Nakamura, S. Ohara, and K. Shigehara, Bull. Chem. Soc. Jpn., 80, 2436 (2007).
T. Kimura, T. Kimura, and M. Minabe, Koubunshi Ronbunshu, 55, 677 (1998).
T. Kimura, H. Miyata, A. Tanaka, and S. Nishikawa, Koubunshi Ronbunshu, 58, 86 (2001).
X. Chen, H. Zhong, L. Jia, J. Ling, R. Tang, J. Qiao, and Z. Zhang, J. Appl. Polym. Sci., 81, 2696 (2001).
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Hishida, M., Shikinaka, K., Katayama, Y. et al. Polyesters of 2-Pyrone-4,6-dicarboxylic Acid (PDC) as Bio-based Plastics Exhibiting Strong Adhering Properties. Polym J 41, 297–302 (2009). https://doi.org/10.1295/polymj.PJ2008291
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DOI: https://doi.org/10.1295/polymj.PJ2008291
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