Citation: Kai-Ju Luo, Li-Bo Huang, Yan Wang, Jun-Rong Yu, Jing Zhu, Zu-Ming Hu. Tailoring the Properties of Diels-Alder Reaction Crosslinked High-performance Thermosets by Different Bismaleimides[J]. Chinese Journal of Polymer Science, ;2020, 38(3): 268-277. doi: 10.1007/s10118-019-2328-7 shu

Tailoring the Properties of Diels-Alder Reaction Crosslinked High-performance Thermosets by Different Bismaleimides

State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Material Science and Engineering, Donghua University, Shanghai 201620, China

Corresponding author: Yan Wang, wy@dhu.edu.cn Zu-Ming Hu, hzm@dhu.edu.cn
Received Date: 28 May 2019
Revised Date: 3 July 2019
Available Online: 19 September 2019

A series of Diels-Alder reaction cross-linked thermosets with recyclability and healability were prepared from furan-containing aromatic polyamide and bismaleimides with different chemical structures. The structures of synthesized bismaleimides were confirmed by ¹H nuclear magnetic resonance (¹H-NMR) spectroscopy; their reversible cross-linking with the furanic polyamide was further detected by ¹H-NMR technique and sol-gel transition behavior. The dynamic mechanical analysis and tensile test revealed the variable thermal and mechanical properties of thermosets cross-linked by different bismaleimides and with different molar ratios of maleimide group to furan group (I_ma/fur). The tensile test also demonstrated that the better recyclability and solvent-assisted healability of thermosets cross-linked could be achieved by more flexible bismaleimides. This work is expected to provide valuable information for design of recyclable and healable high-performance thermosets with desired properties.
- Recyclability,
- Reparability,
- Thermosets,
- Diels-Alder reaction
1. [1]
  Lu, Q.; He, Y. B.; Yu, Q.; Li, B.; Kaneti, Y. V.; Yao, Y.; Kang, F.; Yang, Q. H. Dendrite-free, high-rate, long-life lithium metal batteries with a 3D cross-linked network polymer electrolyte. Adv. Mater. 2017, 29, 1604460. doi: 10.1002/adma.201604460
2. [2]
  Chang, G.; Wang, C.; Du, M.; Liu, S.; Yang, L. Metal-coordination crosslinked N-polyindoles as recyclable high-performance thermosets and nondestructive detection for their tensile strength and glass transition temperature. Chem. Commun. 2018, 54, 2906−2909. doi: 10.1039/C7CC08510A
3. [3]
  Zhao, S.; Abu-Omar, M. M. Recyclable and malleable epoxy thermoset bearing aromatic imine bonds. Macromolecules 2018, 51, 9816−9824. doi: 10.1021/acs.macromol.8b01976
4. [4]
  Lin, C. H.; Chang, S. L.; Shen, T. Y.; Shih, Y. S.; Lin, H. T.; Wang, C. F. Flexible polybenzoxazine thermosets with high glass transition temperatures and low surface free energies. Polym. Chem. 2012, 3, 935−945. doi: 10.1039/c2py00449f
5. [5]
  Montarnal, D.; Capelot, M.; Tournilhac, C.; Leibler, L. Silica-like malleable materials from permanent organic networks. Science 2011, 334, 965−968. doi: 10.1126/science.1212648
6. [6]
  Colquhoun, H. M. Self-repairing polymers: materials that heal themselves. Nat. Chem. 2012, 4, 435−436. doi: 10.1038/nchem.1357
7. [7]
  Zhang, Y.; Ying, H.; Hart, K. R.; Wu, Y.; Hsu, A. J.; Coppola, A. M.; Kim, T. A.; Yang, K.; Sottos, N. R.; White, S. R.; Cheng, J. Malleable and recyclable poly(urea-urethane) thermosets bearing hindered urea bonds. Adv. Mater. 2016, 28, 7646−7651. doi: 10.1002/adma.201601242
8. [8]
  Ogden, W. A.; Guan, Z. Recyclable, strong, and highly malleable thermosets based on boroxine networks. J. Am. Chem. Soc. 2018, 140, 6217−6220. doi: 10.1021/jacs.8b03257
9. [9]
  Neal, J. A.; Mozhdehi, D.; Guan, Z. Enhancing mechanical performance of a covalent self-healing material by sacrificial noncovalent bonds. J. Am. Chem. Soc. 2015, 137, 4846−4850. doi: 10.1021/jacs.5b01601
10. [10]
  Ma, S.; Webster, D. C. Degradable thermosets based on labile bonds or linkages: a review. Prog. Polym. Sci. 2018, 76, 65−110. doi: 10.1016/j.progpolymsci.2017.07.008
11. [11]
  García, J. M.; Jones, J. O.; Virwani, K.; McCloskey, B. D.; Boday, D. J.; Huurne, G. M.; Horn, H. W.; Coady, D. J.; Bintaleb, A. M.; Alabdulrahman, A. M. S.; Alsewailem, F.; Hedrick, J. L. Recyclable, strong thermosets and organogels via paraformaldehyde condensation with diamines. Science 2014, 344, 732−735. doi: 10.1126/science.1251484
12. [12]
  Arslan, M.; Kiskan, B.; Yagci, Y. Benzoxazine-based thermosets with autonomous self-healing ability. Macromolecules 2015, 48, 1329−1334. doi: 10.1021/ma5025126
13. [13]
  Zhang, B.; Kowsari, K.; Serjouei, A.; Dunn, M. L.; Ge, Q. Reprocessable thermosets for sustainable three-dimensional printing. Nat. Commun. 2018, 9, 1831. doi: 10.1038/s41467-018-04292-8
14. [14]
  Mueller, E.; Alsop, R. J.; Scotti, A.; Bleuel, M.; Rheinstädter, M. C.; Richtering, W.; Hoare, T. Dynamically cross-linked self-assembled thermoresponsive microgels with homogeneous internal structures. Langmuir 2018, 34, 1601−1612. doi: 10.1021/acs.langmuir.7b03664
15. [15]
  Schmolke, W.; Perner, N.; Seiffert, S. Dynamically cross-linked polydimethylsiloxane networks with ambient-temperature self-healing. Macromolecules 2015, 48, 8781−8788. doi: 10.1021/acs.macromol.5b01666
16. [16]
  Zhang, C.; Liu Z.; Shi, Z.; Yin, J.; Tian, M. Versatile approach to building dynamic covalent polymer networks by stimulating the dormant groups. ACS Macro Lett. 2018, 7, 1371−1375. doi: 10.1021/acsmacrolett.8b00723
17. [17]
  Wang, Z.; Pan, Q. An omni-healable supercapacitor integrated in dynamically cross-linked polymer networks. Adv. Funct. Mater. 2017, 27, 1700690. doi: 10.1002/adfm.v27.24
18. [18]
  Roy, N.; Bruchmann, B.; Lehn, J. M. Dynamers: dynamic polymers as self-healing materials. Chem. Soc. Rev. 2015, 44, 3786−3807. doi: 10.1039/C5CS00194C
19. [19]
  Zou, W.; Dong, J.; Luo, Y.; Zhao, Q.; Xie, T. Dynamic covalent polymer networks: from old chemistry to modern day innovations. Adv. Mater. 2017, 29, 1606100.
20. [20]
  Chen, X.; Dam, M. A.; Ono, K.; Mal, J.; Shen, H.; Nutt, S. R.; Sheran, K.; Wudl, F. A thermally re-mendable cross-linked polymeric material. Science 2002, 295, 1698−1702. doi: 10.1126/science.1065879
21. [21]
  Heo, Y.; Malakooti, M. H.; Sodano, H. A. Self-healing polymers and composites for extreme environments. J. Mater. Chem. A 2016, 4, 17403−17411. doi: 10.1039/C6TA06213J
22. [22]
  Fu, G.; Li, Y.; Liang G.; Gu, A. Heat-resistant polyurethane films with great electrostatic dissipation capacity and very high thermally reversible self-healing efficiency based on multi-furan and liquid multi-maleimide polymers. J. Mater. Chem. A 2016, 4, 4232−4241. doi: 10.1039/C6TA00953K
23. [23]
  Yoon, J. A.; Kamada, J.; Koynov, K.; Mohin, J.; Nicolay, R.; Zhang, Y.; Balazs, A. C.; Kowalewski, T.; Matyjaszewski, K. Self-healing polymer films based on thiol-disulfide exchange reactions and self-healing kinetics measured using atomic force microscopy. Macromolecules 2012, 45, 142−149. doi: 10.1021/ma2015134
24. [24]
  Du, X.; Li, J.; Welle, A.; Li, L.; Feng, W.; Levkin, P. A. Reversible and rewritable surface functionalization and patterning via photodynamic disulfide exchange. Adv. Mater. 2015, 27, 4997−5001. doi: 10.1002/adma.201501177
25. [25]
  Black, S. P.; Sanders, J. K.; Stefankiewicz, A. R. Disulfide exchange: Exposing supramolecular reactivity through dynamic covalent chemistry. Chem. Soc. Rev. 2014, 43, 1861−1872. doi: 10.1039/C3CS60326A
26. [26]
  Zhang, H.; Cai, C.; Liu, W.; Li, D.; Zhang, J.; Zhao, N.; Xu, J. Recyclable polydimethylsiloxane network crosslinked by dynamic transesterification reaction. Sci. Rep. 2017, 7, 11833. doi: 10.1038/s41598-017-11485-6
27. [27]
  Gandini, A. The furan/maleimide Diels-Alder reaction: a versatile click-unclick tool in macromolecular synthesis. Prog. Polym. Sci. 2013, 38, 1−29. doi: 10.1016/j.progpolymsci.2012.04.002
28. [28]
  Dewar, M. J. S.; Pierini, A. B. Mechanism of the Diels-Alder reaction. Studies of the addition of maleic anhydride to furan and methylfurans. J. Am. Chem. Soc. 1984, 106, 203−208.
29. [29]
  Yu, S.; Zhang, R.; Wu, Q.; Chen, T.; Sun, P. Bio-inspired high-performance and recyclable cross-linked polymers. Adv. Mater. 2013, 25, 4912−4917. doi: 10.1002/adma.201301513
30. [30]
  Yang, Y.; Urban, M. W. Self-repairable polyurethane networks by atmospheric carbon dioxide and water. Angew. Chem. Int. Ed. 2014, 53, 12142−12147. doi: 10.1002/anie.201407978
31. [31]
  Li, J.; Zhang, G.; Deng, L.; Zhao, S.; Gao, Y.; Jiang, K.; Sun R.; Wong, C. In situ polymerization of mechanically reinforced, thermally healable graphene oxide/polyurethane composites based on Diels-Alder chemistry. J. Mater. Chem. A 2014, 2, 20642−20649. doi: 10.1039/C4TA04941A
32. [32]
  Zeng, C.; Seino, H.; Ren, J.; Hatanaka, K.; Yoshie, N. Bio-based furan polymers with self-healing ability. Macromolecules 2013, 46, 1794−1802. doi: 10.1021/ma3023603
33. [33]
  Zeng, C.; Seino, H.; Ren, J.; Hatanaka, K.; Yoshie, N. Self-healing bio-based furan polymers cross-linked with various bis-maleimides. Polymer 2013, 54, 5351−5357. doi: 10.1016/j.polymer.2013.07.059
34. [34]
  Trovatti, E.; Lacerda, T. M.; Carvalho, A. J.; Gandini, A. Recycling tires? Reversible crosslinking of poly(butadiene). Adv. Mater. 2015, 27, 2242−2245. doi: 10.1002/adma.201405801
35. [35]
  Polgar, L. M.; van Duin, M. ; Broekhuis, A. A.; Picchioni, F. Use of Diels-Alder chemistry for thermoreversible cross-linking of rubbers: the next step toward recycling of rubber products? Macromolecules 2015, 48, 7095−7105. doi: 10.1021/acs.macromol.5b01422
36. [36]
  Zhao, J.; Xu, R.; Luo, G.; Wu, J.; Xia, H. A self-healing, re-moldable and biocompatible crosslinked polysiloxane elastomer. J. Mater. Chem. B 2016, 4, 982−989. doi: 10.1039/C5TB02036K
37. [37]
  Bera, R.; Mondal, S.; Das, N. Nanoporous triptycene based network polyamides (TBPs) for selective CO₂ uptake. Polymer 2017, 111, 275−284. doi: 10.1016/j.polymer.2017.01.056
38. [38]
  Duan, J.; Pan, Y.; Pacheco, F.; Litwiller, E.; Lai, Z.; Pinnau, I. High-performance polyamide thin-film-nanocomposite reverse osmosis membranes containing hydrophobic zeolitic imidazolate framework-8. J. Memb. Sci. 2015, 476, 303−310. doi: 10.1016/j.memsci.2014.11.038
39. [39]
  García, J. M.; García F. C.; Serna, F.; de la Peña, J. High-performance aromatic polyamides. Prog. Polym. Sci. 2010, 35, 623−686. doi: 10.1016/j.progpolymsci.2009.09.002
40. [40]
  Luo, K.; Li, J.; Duan, G.; Wang, Y.; Yu, J.; Zhu, J.; Hu, Z. Comb-shaped aromatic polyamide cross-linked by Diels-Alder chemistry: towards recyclable and high-performance thermosets. Polymer 2018, 142, 33−42. doi: 10.1016/j.polymer.2018.03.026
41. [41]
  Li, J.; Zhang, G.; Deng, L.; Jiang, K.; Zhao, S.; Gao, Y.; Sun, R.; Wong, C. Thermally reversible and self-healing novolac epoxy resins based on Diels-Alder chemistry. J. Appl. Polym. Sci. 2015, 132, 42167.
42. [42]
  Wang, A.; Niu, H.; He, Z.; Li, Y. Thermoreversible cross-linking of ethylene/propylene copolymer rubbers. Polym. Chem. 2017, 8, 4494−4502. doi: 10.1039/C7PY00896A
43. [43]
  Toncelli, C.; De Reus, D. C.; Picchioni, F.; Broekhuis, A. A. Properties of reversible Diels-Alder furan/maleimide polymer networks as function of crosslink density. Macromol. Chem. Phys. 2012, 213, 157−165. doi: 10.1002/macp.201100405
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