Click synthesis and adhesive properties of novel biomass-based polymers from lignin-derived stable metabolic intermediate

Polymer Journal

Volumn 43, Issue 7, 2011, Pages 648-653

  Michinobu, Tsuyoshi ^a,b   Hiraki, Kenta ^a   Inazawa, Yasunori ^a   Katayama, Yoshihiro ^a,e   Masai, Eiji ^c   Nakamura, Masaya ^d   Ohara, Seiji ^d   Shigehara, Kiyotaka ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^c NAGAOKA UNIVERSITY OF TECHNOLOGY   (Japan)

^d FORESTRY AND FOREST PRODUCTS RESEARCH INSTITUTE   (Japan)

^e NIHON UNIVERSITY   (Japan)

Author keywords

adhesive; biomass; click chemistry; polyaddition

Indexed keywords

ADHESIVE PROPERTIES; AZIDE-ALKYNE CYCLOADDITION; BIOMASS-BASED POLYMER; CLICK CHEMISTRY; CROSS-LINKING ABILITY; HIGH-MOLECULAR WEIGHT POLYMERS; IN-SITU; LIGAND-FREE; METABOLIC INTERMEDIATES; METAL SURFACES; POLYADDITION; TRIAZOLE RING;

ACETYLENE; BIOMASS; CHELATION; CROSSLINKING; CYCLOADDITION; GEL PERMEATION CHROMATOGRAPHY; LEACHING; LIGNIN; METABOLISM; ORGANIC SOLVENTS; POLYMERIZATION; REACTION INTERMEDIATES; SIZE EXCLUSION CHROMATOGRAPHY; SYNTHESIS (CHEMICAL); TENSILE STRENGTH;

ORGANIC POLYMERS;

EID: 79960137329     PISSN: 00323896     EISSN: 13490540     Source Type: Journal    
DOI: 10.1038/pj.2011.40     Document Type: Article

References (32)

1. Ragauskas, A. J., Williams, C. K., Davison, B. H., Britovsek, G., Cairney, J., Eckert, C. A., Frederick Jr, W. J., Hallett, J. P., Leak, D. J., Liotta, C. L., Mielenz, J. R., Murphy, R., Templer, R. & Tschaplinski, T. The path forward for biofuels and biomaterials. Science 311, 484-489 (2006). (Pubitemid 43158454)
2. Matsumura, S. Enzymatic synthesis of polyesters via ring-opening polymerization. Adv. Polym. Sci. 194, 95-132 (2006).
3. Nishio, Y. Material functionalization of cellulose and related polysaccharides. Adv. Polym. Sci. 205, 97-151 (2006).
4. Williams, C. K. Synthesis of functionalized biodegradable polyesters. Chem. Soc. Rev. 36, 1573-1580 (2007).
5. Gandini, A. Polymers from renewable resources: a challenge for the future of macromolecular materials. Macromolecules 41, 9491-9504 (2008).
6. Otsuka, Y., Nakamura, M., Shigehara, K., Sugimura, K., Masai, E., Ohara, S. & Katayama, Y. Efficient production of 2-pyrone 4,6-dicarboxylic acid as a novel polymer-based material from protocatechuate by microbial function. Appl. Microbiol. Biotechnol. 71, 608-614 (2006). (Pubitemid 44114788)
7. + ion. Bull. Chem. Soc. Jpn. 80, 2436-2442 (2007).
8. Bito, M., Michinobu, T., Katayama, Y., Otsuka, Y., Nakamura, M., Ohara, S., Masai, E. & Shigehara, K. 2-Pyranone-4,6-dicarboxylic acid as a source of green-plastics and antibacterial chemicals. Trans. Mater. Res. Soc. Jpn. 33, 1165-1168 (2008).
9. Michinobu, T., Hiraki, K., Fujii, N., Shikinaka, K., Katayama, Y., Masai, E., Nakamura, M., Otsuka, Y., Ohara, S. & Shigehara, K. Organogels of lignin-derived stable metabolic intermediate, 2-pyrone-4,6-dicarboxylic acid (PDC), bearing cholesteryl groups. Chem. Lett. 39, 400-401 (2010).
10. Michinobu, T., Hishida, M., Sato, M., Katayama, Y., Masai, E., Nakamura, M., Otsuka, Y., Ohara, S. & Shigehara, K. Polyesters of 2-pyrone-4,6- dicarboxylic acid (PDC) obtained from a metabolic intermediate of lignin. Polym. J. 40, 68-75 (2008). (Pubitemid 351421662)
11. Hishida, M., Shikinaka, K., Katayama, Y., Kajita, S., Masai, E., Nakamura, M., Otsuka, Y., Ohara, S. & Shigehara, K. Polyesters of 2-pyrone-4,6-dicarboxylic acid (PDC) as biobased plastics exhibiting strong adhering properties. Polym. J. 41, 297-302 (2009).
12. Michinobu, T., Bito, M., Tanimura, M., Katayama, Y., Masai, E., Nakamura, M., Otsuka, Y., Ohara, S. & Shigehara, K. Mechanical properties of poly(L-lactide) films controlled by blending with polyesters of lignin-derived stable metabolic intermediate, 2-pyrone- 4,6-dicarboxylic acid (PDC). Polym. J. 41, 843-848 (2009).
13. Michinobu, T., Bito, M., Yamada, Y., Tanimura, M., Katayama, Y., Masai, E., Nakamura, M., Otsuka, Y., Ohara, S. & Shigehara, K. Fusible, elastic, and biodegradable polyesters of 2-pyrone-4,6-dicarboxylic acid (PDC). Polym. J. 41, 1111-1116 (2009).
14. Hishida, M., Shikinaka, K., Inazawa, Y., Katayama, Y., Kajita, S., Masai, E., Nakamura, M., Otsuka, Y., Ohara, S. & Shigehara, K. [Conductive cements based polyesters of PDC (2-pyrone-4,6-dicarboxylic acid) obtained from a metabolic intermediate of lignin]. Kobunshi Ronbunshu 66, 141-146 (2009).
15. Hasegawa, Y., Shikinaka, K., Katayama, Y., Kajita, S., Masai, E., Nakamura, M., Otsuka, Y., Ohara, S. & Shigehara, K. [Tenacious epoxy adhesives prepared from lignin-derived stable metabolic intermediate]. Senai Gakkaishi 65, 359-362 (2009).
16. Michinobu, T., Bito, M., Tanimura, M., Katayama, Y., Masai, E., Nakamura, M., Otsuka, Y., Ohara, S. & Shigehara, K. Synthesis and characterization of hybrid biopolymers of L-lactic acid and 2-pyrone-4,6-dicarboxylic acid. J. Macromol. Sci, Part A; Pure Appl. Chem. 47, 564-570 (2010).
17. Kolb, H. C., Finn, M. G. & Sharpless, K. B. Click chemistry: diverse chemical function from a few good reactions. Angew. Chem. Int. Ed. 40, 2004-2021 (2001).
18. Liu, J., Lam, J. W. Y. & Tang, B. Z. Acetylenic polymers: syntheses, structures, and functions. Chem. Rev. 109, 5799-5867 (2009).
19. Qin, A., Lam, J. W. Y. & Tang, B. Z. Click polymerization. Chem. Soc. Rev. 39, 2522-2544 (2010).
20. Qin, A., Lam, J. W. Y. & Tang, B. Z. Click polymerization: progresses, challenges, and opportunities. Macromolecules 43, 8693-8702 (2010).
21. Nagao, Y. & Takasu, A. Click polyester: synthesis of polyesters containing triazole units in the main chain by click chemistry and improved thermal property. Macromol. Rapid Commun. 30, 199-203 (2009).
22. Nagao, Y. & Takasu, A. Click polyester: synthesis of polyesters containing triazole units in the main chain via safe and rapid click chemistry and their properties. J. Polym. Sci., Part A: Polym. Chem. 48, 4207-4218 (2010).
23. Golas, P. L., Tsarevsky, N. V., Sumerlin, B. S. & Matyjaszewski, K. Catalyst performance in click coupling reactions of polymers prepared by ATRP: ligand and metal effects. Macromolecules 39, 6451-6457 (2006). (Pubitemid 44555087)
24. Qin, A., Jim, C. K. W., Lu, W., Lam, J. W. Y., Häussler, M., Dong, Y., Sung, H. H. Y., Williams, I. D., Wong, G. K. L. & Tang, B. Z. Click polymerization: facile synthesis of functional poly(aroyltriazole)s by metal-free, regioselective 1,3-dipolar polycycloaddition. Macromolecules 40, 2308-2317 (2007). (Pubitemid 46608256)
25. Díaz, D. D., Punna, S., Holzer, P., Mcpherson, A. K., Sharpless, K. B., Fokin, V. V. & Finn, M. G. Click chemistry in materials synthesis. 1. adhesive polymers from copper-catalyzed azide-alkyne cycloaddition. J. Polym. Sci., Part A: Polym. Chem. 42, 4392-4403 (2004).
26. Liu, Y., Díaz, D. D., Accurso, A. A., Sharpless, K. B., Fokin, V. V. & Finn, M. G. Click chemistry in materials synthesis. III. metal-adhesive polymers from Cu(I)-catalyzed azide-alkyne cycloaddition. J. Polym. Sci., Part A: Polym. Chem. 45, 5182-5189 (2007). (Pubitemid 350044159)
27. Tang, Y., Jim, C. K. W., Liu, Y., Ye, L., Qin, A., Lam, J. W. Y., Zhao, C. & Tang, B. Z. Synthesis and curing of hyperbranched poly(triazole)s with click polymerization for improved adhesion strength. ACS Appl. Mater. Interfaces 2, 566-574 (2010).
28. Michinobu, T., Inazawa, Y., Hiraki, K., Katayama, Y., Masai, E., Nakamura, M., Ohara, S. & Shigehara, K. A novel biomass-based polymer prepared from lignin-derived stable metabolic intermediate by copper(I)-catalyzed azide-alkyne click reaction. Chem. Lett. 37, 154-155 (2008).
29. Gatto, V. J., Arnold, K. A., Viscariello, A. M., Miller, S. R., Morgan, C. R. & Gokel, G. W. Syntheses and binding properties of bibrachial lariat ethers (BiBLEs): survey of synthetic methods and cation selectivities. J. Org. Chem. 51, 5373-5384 (1986).
30. Besset, C., Bernard, J., Fleury, E., Pascault, J.- P., Cassagnau, P., Drockenmuller, E. & Williams, R. J. J. Bio-sourced networks from thermal polyaddition of a starch-derived a-azide-o-alkyne AB monomer with an A2B2 aliphatic cross-linker. Macromolecules 43, 5672-5678 (2010).
31. Lin, L., Shen, Q., Chen, G.- R. & Xie, J. Synthesis of triazole-linked b-C-glycosyl dimmers as inhibitors of PTB1B. Bioorg. Med. Chem. 16, 9757-9763 (2008).
32. Diaz, D. D., Marrero Tellado, J. J., Velazquez, D. G. & Ravelo, A. G. Polymer thermoreversible gels from organogelators enabled by click chemistry. Tetrahedron Lett. 49, 1340-1343 (2008).