Citation: Xiao-Min Ding, Li Chen, Xi Luo, Feng-Ming He, Yan-Fang Xiao, Yu-Zhong Wang. Biomass-derived dynamic covalent epoxy thermoset with robust mechanical properties and facile malleability[J]. Chinese Chemical Letters, ;2022, 33(6): 3245-3248. doi: 10.1016/j.cclet.2021.10.079 shu

Biomass-derived dynamic covalent epoxy thermoset with robust mechanical properties and facile malleability

The Collaborative Innovation Center for Eco-Friendly and Fire-Safety Polymeric Materials (MoE), National Engineering Laboratory of Eco-Friendly Polymeric Materials (Sichuan), State Key Laboratory of Polymer Materials Engineering, College of Chemistry, Sichuan University, Chengdu 610064, China

l.chen.scu@gmail.com

yzwang@scu.edu.cn

Received Date: 20 August 2021
Revised Date: 7 October 2021
Accepted Date: 26 October 2021
Available Online: 29 October 2021

Figures(5)

Biomass-derived dynamic covalent thermoset has been considered as a promising solution to the high dependence on fossil resources and the difficulty in recyclability after curing of conventional bisphenol A epoxy resins. However, the design and preparation of a dynamic covalent biobased epoxy thermoset with both comparable thermal and mechanical performances to bisphenol A epoxy resins and reprocessibility remains a significant challenge. Herein, based on imine chemistry, a novel Schiff base-containing dynamic covalent epoxy thermoset was facilely fabricated from biobased protocatechualdehyde and synthetic siloxane diamine. Due to the more reactive epoxides in the epoxy monomer than in bisphenol A epoxy oligomer, the thermoset exhibited a high cross-linking density, resulting in high thermal stability and glass transition temperature. The rigid aromatic Schiff base moieties endowed the thermoset with excellent mechanical properties: Thanks to the plasticization of the flexible siloxane, the thermoset displayed high impact strength. Meanwhile, owing to the high segmental mobility, the fast exchange of imine bonds was guaranteed; and the thermoset was able to be recycled through reprocessing. Taking these features, this work provided great potential for designing and preparing sustainable substitutes for bisphenol A epoxy resins in the high-performance applications.
- Epoxy resin,
- Dynamic covalent thermoset,
- Protocatechualdehyde,
- Imine chemistry,
- High-performance
1. [1]
  T. Vidil, F. Tournilhac, S. Musso, et al., Prog. Polym. Sci.62 (2016) 126-179. doi: 10.1016/j.progpolymsci.2016.06.003
2. [2]
  Y.F. Lei, X.L. Wang, B.W. Liu, et al., Chin. Chem. Lett. 32 (2021) 875-879. doi: 10.1016/j.cclet.2020.06.015
3. [3]
  Y.F. Lei, X.L. Wang, B.W. Liu, et al., ACS Sustain. Chem. Eng. 8 (2020) 13261-13270. doi: 10.1021/acssuschemeng.0c03451
4. [4]
  X.M. Ding, L. Chen, D.M. Guo, et al., ACS Sustain. Chem. Eng. 9 (2021) 3267-3277. doi: 10.1021/acssuschemeng.0c08852
5. [5]
  R. Auvergne, S. Caillol, G. David, et al., Chem. Rev. 114 (2014) 1082-1115. doi: 10.1021/cr3001274
6. [6]
  J.R. Rochester, Reprod. Toxicol. 42 (2013) 132-155. doi: 10.1016/j.reprotox.2013.08.008
7. [7]
  D. Chen, K. Kannan, H. Tan, et al., Environ. Sci. Technol. 50 (2016) 5438-5453. doi: 10.1021/acs.est.5b05387
8. [8]
  Z.P. Zhang, M.Z. Rong, M.Q. Zhang, Prog. Polym. Sci. 80 (2018) 39-93. doi: 10.1016/j.progpolymsci.2018.03.002
9. [9]
  J. Zhang, V.S. Chevali, H. Wang, et al., Compos. B. Eng. 193 (2020) 108053. doi: 10.1016/j.compositesb.2020.108053
10. [10]
  Y. Yang, Y. Xu, Y. Ji, et al., Prog. Mater Sci. 120 (2021) 100710. doi: 10.1016/j.pmatsci.2020.100710
11. [11]
  C.J. Kloxin, C.N. Bowman, Chem. Soc. Rev. 42 (2013) 7161-7173. doi: 10.1039/C3CS60046G
12. [12]
  D.W.R. Balkenende, R.A. Olson, S. Balog, et al., Macromolecules 49 (2016) 7877-7885. doi: 10.1021/acs.macromol.6b01491
13. [13]
  Z. Hu, D. Zhang, F. Lu, et al., Macromolecules 51 (2018) 5294-5303. doi: 10.1021/acs.macromol.8b01124
14. [14]
  X. Chen, M.A. Dam, K. Ono, et al., Science 295 (2002) 1698-1702. doi: 10.1126/science.1065879
15. [15]
  H. Hou, J. Yin, X. Jiang, Adv. Mater. 28 (2016) 9126-9132. doi: 10.1002/adma.201602105
16. [16]
  G.I. Peterson, J. Lee, T.L. Choi, Macromolecules 52 (2019) 9561-9568. doi: 10.1021/acs.macromol.9b01996
17. [17]
  D. Montarnal, M. Capelot, F. Tournilhac, et al., Science 334 (2011) 965-968. doi: 10.1126/science.1212648
18. [18]
  X. Feng, J. Fan, A. Li, et al., ACS Appl. Mater. Interfaces 11 (2019) 16075-16086. doi: 10.1021/acsami.9b03092
19. [19]
  S. Wang, H. Wang, P. Zhang, et al., Mater. Horiz. 8 (2021) 1481-1487. doi: 10.1039/d0mh02024a
20. [20]
  M. Roettger, T. Domenech, R. van der Weegen, et al., Science 356 (2017) 62-65. doi: 10.1126/science.aah5281
21. [21]
  M.O. Saed, A. Gablier, E.M. Terentejv, Adv. Funct. Mater. 30 (2019) 1906458.
22. [22]
  A. Ruiz de Luzuriaga, R. Martin, N. Markaide, et al., Mater. Horiz. 3 (2016) 241-247. doi: 10.1039/C6MH00029K
23. [23]
  H. Si, L. Zhou, Y. Wu, et al., Compos. B. Eng. 199 (2020) 108278. doi: 10.1016/j.compositesb.2020.108278
24. [24]
  S. Zhao, M.M. Abu-Omar, Macromolecules 51 (2018) 9816-9824. doi: 10.1021/acs.macromol.8b01976
25. [25]
  P. Taynton, K. Yu, R.K. Shoemaker, et al., Adv. Mater. 26 (2014) 3938-3942. doi: 10.1002/adma.201400317
26. [26]
  Z. Zou, C. Zhu, Y. Li, et al., Sci. Adv. 4 (2018) eaaq0508. doi: 10.1126/sciadv.aaq0508
27. [27]
  L. Zhang, Z. Liu, X. Wu, et al., Adv. Mater. 31 (2019) 1901402. doi: 10.1002/adma.201901402
28. [28]
  Y. Chen, P.G. Miller, X. Ding, et al., Adv. Mater. (2020) 2003761. doi: 10.1002/adma.202003761
29. [29]
  C.H. Li, C. Wang, C. Keplinger, et al., Nat. Chem. 8 (2016) 618-624. doi: 10.1038/nchem.2492
30. [30]
  C. Hao, T. Liu, S. Zhang, et al., Macromolecules 53 (2020) 3110-3118. doi: 10.1021/acs.macromol.9b02243
31. [31]
  H. Liu, H. Zhang, H. Wang, et al., Chem. Eng. J. 368 (2019) 61-70. doi: 10.1016/j.cej.2019.02.177
32. [32]
  X. Li, J. Zhang, L. Zhang, et al., Compos. Commun. 25 (2021) 100754. doi: 10.1016/j.coco.2021.100754
33. [33]
  S. Wang, S. Ma, Q. Li, et al., Green Chem. 21 (2019) 1484-1497. doi: 10.1039/c8gc03477j
34. [34]
  H. Memon, H. Liu, M.A. Rashid, et al., Macromolecules 53 (2020) 621-630. doi: 10.1021/acs.macromol.9b02006
35. [35]
  X. Xu, S. Ma, S. Wang, et al., J. Mater. Chem. A 8 (2020) 11261-11274. doi: 10.1039/d0ta01419b
36. [36]
  X.L. Zhao, Y.Y. Liu, Y. Weng, et al., ACS Sustain. Chem. Eng. 8 (2020) 15020-15029. doi: 10.1021/acssuschemeng.0c05727
37. [37]
  J. Wu, X. Yu, H. Zhang, et al., ACS Sustain. Chem. Eng. 8 (2020) 6479-6487. doi: 10.1021/acssuschemeng.0c01047
38. [38]
  Y. Tao, L. Fang, M. Dai, et al., Polym. Chem. 11 (2020) 4500-4506. doi: 10.1039/d0py00545b
39. [39]
  T. Liu, C. Hao, L. Wang, et al., Macromolecules 50 (2017) 8588-8597. doi: 10.1021/acs.macromol.7b01889
40. [40]
  Y. Oh, K.M. Lee, D. Jung, et al., ACS Macro Lett. 8 (2019) 239-244. doi: 10.1021/acsmacrolett.9b00008
41. [41]
  Y. Liu, B. Wang, S. Ma, et al., Eur. Polym. J. 144 (2021) 110236. doi: 10.1016/j.eurpolymj.2020.110236
42. [42]
  T. Liu, S. Zhang, C. Hao, et al., Macromol. Rapid Commun. 40 (2019) 1800889. doi: 10.1002/marc.201800889
43. [43]
  Y.Y. Liu, J. He, Y.D. Li, et al., Ind. Crop. Prod. 153 (2020) 112576. doi: 10.1016/j.indcrop.2020.112576
44. [44]
  W. Xie, S. Huang, D. Tang, et al., Chem. Eng. J. 394 (2020) 123667. doi: 10.1016/j.cej.2019.123667
45. [45]
  W. Xie, S. Huang, S. Liu, et al., Chem. Eng. J. 404 (2021) 126598. doi: 10.1016/j.cej.2020.126598
46. [46]
  X. Xu, S. Ma, J. Wu, et al., J. Mater. Chem. A 7 (2019) 15420-15431. doi: 10.1039/c9ta05293c
47. [47]
  C. Aouf, C.L. Guernevé, S. Caillol, et al., Tetrahedron 69 (2013) 1345-1353. doi: 10.1016/j.tet.2012.11.079
48. [48]
  X.F. Liu, B.W. Liu, X. Luo, et al., Chem. Eng. J. 380 (2020) 122471. doi: 10.1016/j.cej.2019.122471
49. [49]
  J. Zhang, X. Mi, S. Chen, et al., Chem. Eng. J. 381 (2020) 122719. doi: 10.1016/j.cej.2019.122719
50. [50]
  Q. Yu, X. Peng, Y. Wang, et al., Eur. Polym. J. 117 (2019) 55-63. doi: 10.1016/j.eurpolymj.2019.04.053
1. [1]
  Zhaoru Chen , Xiaoxu Liu , Haonan Chen , Jialong Li , Xiaofeng Wang , Jianfeng Zhu . Application of epoxy resin in cultural relics protection. Chinese Chemical Letters, 2024, 35(4): 109194-. doi: 10.1016/j.cclet.2023.109194
2. [2]
  Fangzhou Wang , Wentong Gao , Chenghui Li . A weak but inert hindered urethane bond for high-performance dynamic polyurethane polymers. Chinese Chemical Letters, 2024, 35(5): 109305-. doi: 10.1016/j.cclet.2023.109305
3. [3]
  Kunsong Hu , Yulong Zhang , Jiayi Zhu , Jinhua Mai , Gang Liu , Manoj Krishna Sugumar , Xinhua Liu , Feng Zhan , Rui Tan . Nano-engineered catalysts for high-performance oxygen reduction reaction. Chinese Chemical Letters, 2024, 35(10): 109423-. doi: 10.1016/j.cclet.2023.109423
4. [4]
  Wen LUO , Lin JIN , Palanisamy Kannan , Jinle HOU , Peng HUO , Jinzhong YAO , Peng WANG . Preparation of high-performance supercapacitor based on bimetallic high nuclearity titanium-oxo-cluster based electrodes. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 782-790. doi: 10.11862/CJIC.20230418
5. [5]
  Zhe Wang , Li-Peng Hou , Qian-Kui Zhang , Nan Yao , Aibing Chen , Jia-Qi Huang , Xue-Qiang Zhang . High-performance localized high-concentration electrolytes by diluent design for long-cycling lithium metal batteries. Chinese Chemical Letters, 2024, 35(4): 108570-. doi: 10.1016/j.cclet.2023.108570
6. [6]
  Hang Chen , Chengzhi Cui , Hebo Ye , Hanxun Zou , Lei You . Enhancing hydrolytic stability of dynamic imine bonds and polymers in acidic media with internal protecting groups. Chinese Chemical Letters, 2024, 35(5): 109145-. doi: 10.1016/j.cclet.2023.109145
7. [7]
  Xinyu Huai , Jingxuan Liu , Xiang Wu . Cobalt-Doped NiMoO4 Nanosheet for High-performance Flexible Supercapacitor. Chinese Journal of Structural Chemistry, 2023, 42(10): 100158-100158. doi: 10.1016/j.cjsc.2023.100158
8. [8]
  Yu ZHANG , Fangfang ZHAO , Cong PAN , Peng WANG , Liangming WEI . Application of double-side modified separator with hollow carbon material in high-performance Li-S battery. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1218-1232. doi: 10.11862/CJIC.20230412
9. [9]
  Yuchen Wang , Yaoyu Liu , Xiongfei Huang , Guanjie He , Kai Yan . Fe nanoclusters anchored in biomass waste-derived porous carbon nanosheets for high-performance supercapacitor. Chinese Chemical Letters, 2024, 35(8): 109301-. doi: 10.1016/j.cclet.2023.109301
10. [10]
  Pingping Wang , Huixian Miao , Kechuan Sheng , Bin Wang , Fan Feng , Xuankun Cai , Wei Huang , Dayu Wu . Efficient blue-light-excitable copper(Ⅰ) coordination network phosphors for high-performance white LEDs. Chinese Chemical Letters, 2024, 35(4): 108600-. doi: 10.1016/j.cclet.2023.108600
11. [11]
  Guiyang Zheng , Xuelian Kang , Haoran Ye , Wei Fan , Christian Sonne , Su Shiung Lam , Rock Keey Liew , Changlei Xia , Yang Shi , Shengbo Ge . Recent advances in functional utilisation of environmentally friendly and recyclable high-performance green biocomposites: A review. Chinese Chemical Letters, 2024, 35(4): 108817-. doi: 10.1016/j.cclet.2023.108817
12. [12]
  Jiayu Bai , Songjie Hu , Lirong Feng , Xinhui Jin , Dong Wang , Kai Zhang , Xiaohui Guo . Manganese vanadium oxide composite as a cathode for high-performance aqueous zinc-ion batteries. Chinese Chemical Letters, 2024, 35(9): 109326-. doi: 10.1016/j.cclet.2023.109326
13. [13]
  Ningning Zhao , Yuyan Liang , Wenjie Huo , Xinyan Zhu , Zhangxing He , Zekun Zhang , Youtuo Zhang , Xianwen Wu , Lei Dai , Jing Zhu , Ling Wang , Qiaobao Zhang . Separator functionalization enables high-performance zinc anode via ion-migration regulation and interfacial engineering. Chinese Chemical Letters, 2024, 35(9): 109332-. doi: 10.1016/j.cclet.2023.109332
14. [14]
  Xiaoxing Ji , Xiaojuan Li , Chenggang Wang , Gang Zhao , Hongxia Bu , Xijin Xu . Ni_xB/rGO as the cathode for high-performance aqueous alkaline zinc-based battery. Chinese Chemical Letters, 2024, 35(10): 109388-. doi: 10.1016/j.cclet.2023.109388
15. [15]
  Jie Zhou , Chuanxiang Zhang , Changchun Hu , Shuo Li , Yuan Liu , Zhu Chen , Song Li , Hui Chen , Rokayya Sami , Yan Deng . Electrochemical aptasensor based on black phosphorus-porous graphene nanocomposites for high-performance detection of Hg²⁺. Chinese Chemical Letters, 2024, 35(11): 109561-. doi: 10.1016/j.cclet.2024.109561
16. [16]
  Wenhao Feng , Chunli Liu , Zheng Liu , Huan Pang . In-situ growth of N-doped graphene-like carbon/MOF nanocomposites for high-performance supercapacitor. Chinese Chemical Letters, 2024, 35(12): 109552-. doi: 10.1016/j.cclet.2024.109552
17. [17]
  Min LUO , Xiaonan WANG , Yaqin ZHANG , Tian PANG , Fuzhi LI , Pu SHI . Porous spherical MnCo₂S₄ as high-performance electrode material for hybrid supercapacitors. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 413-424. doi: 10.11862/CJIC.20240205
18. [18]
  Tong Su , Yue Wang , Qizhen Zhu , Mengyao Xu , Ning Qiao , Bin Xu . Multiple conductive network for KTi₂(PO₄)₃ anode based on MXene as a binder for high-performance potassium storage. Chinese Chemical Letters, 2024, 35(8): 109191-. doi: 10.1016/j.cclet.2023.109191
19. [19]
  Rui Cheng , Xin Huang , Tingting Zhang , Jiazhuang Guo , Jian Yu , Su Chen . Solid superacid catalysts promote high-performance carbon dots with narrow-band fluorescence emission for luminescence solar concentrators. Chinese Chemical Letters, 2024, 35(8): 109278-. doi: 10.1016/j.cclet.2023.109278
20. [20]
  Ya Song , Mingxia Zhou , Zhu Chen , Huali Nie , Jiao-Jing Shao , Guangmin Zhou . Integrated interconnected porous and lamellar structures realized fast ion/electron conductivity in high-performance lithium-sulfur batteries. Chinese Chemical Letters, 2024, 35(6): 109200-. doi: 10.1016/j.cclet.2023.109200

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(502)
HTML views(19)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142