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Polymers
Volume 15
Issue 6
10.3390/polym15061349
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Article

Click Synthesis of Triazole Polymers Based on Lignin-Derived Metabolic Intermediate and Their Strong Adhesive Properties to Cu Plate

by
Yijie Jin
1,
Manjusha Joshi
1,
Takuma Araki
2,
Naofumi Kamimura
3,
Eiji Masai
3,
Masaya Nakamura
2 and
Tsuyoshi Michinobu
1,*
1
Department of Materials Science and Technology, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8552, Japan
2
Department of Forest Resource Chemistry, Forestry and Forest Products Research Institute, Tsukuba 305-8687, Japan
3
Department of Materials Science and Bioengineering, Nagaoka University of Technology, Nagaoka 940-2188, Japan
*
Author to whom correspondence should be addressed.
Polymers 2023, 15(6), 1349; https://doi.org/10.3390/polym15061349
Submission received: 16 February 2023 / Revised: 3 March 2023 / Accepted: 5 March 2023 / Published: 8 March 2023
(This article belongs to the Special Issue Feature Papers in Polymer Applications)
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Abstract

2-Pyrone-4,6-dicarboxylic acid (PDC) is a chemically stable metabolic intermediate of lignin that can be produced on a large scale by transforming bacteria. Novel biomass-based polymers based on PDC were synthesized by Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) and fully characterized by nuclear magnetic resonance, infrared spectroscopies, thermal analysis, and tensile lap shear strength measurements. The onset decomposition temperatures of these PDC-based polymers were all above 200 °C. In addition, the PDC-based polymers exhibited strong adhesive properties to various metal plates, with the highest adhesion to a copper plate of 5.73 MPa. Interestingly, this result was in contrast to our previous findings that PDC-based polymers weakly adhere to copper. Furthermore, when bifunctional alkyne and azide monomers were polymerized in situ under hot-press conditions for 1 h, the resulting PDC-based polymer displayed a similar adhesion to a copper plate of 4.18 MPa. The high affinity of the triazole ring to copper ions improved the adhesive ability and selectivity of the PDC-based polymers to copper while still maintaining the strong adhesive ability to other metals, which is conducive to enhancing the versatility of PDC-based polymers as adhesives.
Keywords: adhesive; biomass; click chemistry; lignin; triazole polymer adhesive; biomass; click chemistry; lignin; triazole polymer
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MDPI and ACS Style

Jin, Y.; Joshi, M.; Araki, T.; Kamimura, N.; Masai, E.; Nakamura, M.; Michinobu, T. Click Synthesis of Triazole Polymers Based on Lignin-Derived Metabolic Intermediate and Their Strong Adhesive Properties to Cu Plate. Polymers 2023, 15, 1349. https://doi.org/10.3390/polym15061349

AMA Style

Jin Y, Joshi M, Araki T, Kamimura N, Masai E, Nakamura M, Michinobu T. Click Synthesis of Triazole Polymers Based on Lignin-Derived Metabolic Intermediate and Their Strong Adhesive Properties to Cu Plate. Polymers. 2023; 15(6):1349. https://doi.org/10.3390/polym15061349

Chicago/Turabian Style

Jin, Yijie, Manjusha Joshi, Takuma Araki, Naofumi Kamimura, Eiji Masai, Masaya Nakamura, and Tsuyoshi Michinobu. 2023. "Click Synthesis of Triazole Polymers Based on Lignin-Derived Metabolic Intermediate and Their Strong Adhesive Properties to Cu Plate" Polymers 15, no. 6: 1349. https://doi.org/10.3390/polym15061349

APA Style

Jin, Y., Joshi, M., Araki, T., Kamimura, N., Masai, E., Nakamura, M., & Michinobu, T. (2023). Click Synthesis of Triazole Polymers Based on Lignin-Derived Metabolic Intermediate and Their Strong Adhesive Properties to Cu Plate. Polymers, 15(6), 1349. https://doi.org/10.3390/polym15061349

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