Citation: Beitao Liu, Qi Cao, Jiahui Li, Xigao Jian, Zhihuan Weng. Facile recycling of anhydride-cured epoxy thermoset under mild conditions with multifunctional hydrazine hydrate[J]. Chinese Chemical Letters, ;2023, 34(12): 108465. doi: 10.1016/j.cclet.2023.108465 shu

Facile recycling of anhydride-cured epoxy thermoset under mild conditions with multifunctional hydrazine hydrate

State Key Laboratory of Fine Chemicals, Frontiers Science Center for Smart Materials, Liaoning Technology Innovation Center of High Performance Resin Materials, Department of Polymer Science & Engineering, Dalian University of Technology, Dalian 116024, China

zweng@dlut.edu.cn

Received Date: 28 February 2023
Revised Date: 13 April 2023
Accepted Date: 17 April 2023
Available Online: 18 April 2023

Figures(7)

Environmental economics is accelerating the urgency to develop recycling technologies for the ever-growing quantity of discarded thermoset polymers. Herein, we developed a mild and energy-saving process for high-efficiency degradation and reuse of anhydride-cured epoxy thermoset with the aid of hydrazine hydrate. The degradation degree of the epoxy resin reached 99.6% at 120 ℃ within a short time of 60 min. During the reaction, the ester bonds in the cross-linked network were selectively cleaved by the amination of hydrazine hydrate, and the epoxy resin was fully converted to new monomers that contained hydrazide and hydroxyl groups, respectively. Moreover, the degradation mechanism of the epoxy resin in hydrazine hydrate was studied and a nucleation model was utilized to predict the actual degradation behavior of the system. Finally, the degradation products can be directly mixed with epoxy precursor to prepare a new waterborne epoxy coating with good comprehensive properties. This work not only demonstrates a new way to realize the efficient degradation of epoxy resins, but also provides a facile and efficient recycling protocol for thermosets.
- Anhydride-cured epoxy resin,
- Degradation,
- Recycling,
- Erosion mechanism,
- Waterborne epoxy coating
1. [1]
  R. Geyer, J.R. Jambeck, K.L. Law, Sci. Adv. 3 (2017) e1700782. doi: 10.1126/sciadv.1700782
2. [2]
  V. Tournier, C.M. Topham, A. Gilles, et al., Nature 580 (2020) 216–219. doi: 10.1038/s41586-020-2149-4
3. [3]
  B.C. Gibb, Nat. Chem. 11 (2019) 394–395. doi: 10.1038/s41557-019-0260-7
4. [4]
  P. Sahu, M.K. Gupta, Polym. Compos. 41 (2019) 668–681. doi: 10.1109/iccs45141.2019.9065857
5. [5]
  X. Bao, F. Wu, J. Wang, Polymers (Basel) 13 (2021) 1–16.
6. [6]
  C. Ma, D.S. Rodriguez, T. Kamo, J. Hazard. Mater. 412 (2021) 125329. doi: 10.1016/j.jhazmat.2021.125329
7. [7]
  P. Espeel, F.E. Du Prez, Macromolecules 48 (2014) 2–14.
8. [8]
  Z. Miao, D. Yan, X. Wang, et al., Chin. Chem. Lett. 33 (2022) 4026–4032. doi: 10.1016/j.cclet.2021.12.003
9. [9]
  X. Song, Z.P. Deng, C.B. Li, et al., Chin. Chem. Lett. 33 (2022) 4912–4917. doi: 10.1016/j.cclet.2021.12.067
10. [10]
  K. Moeser, Adv. Mater. Res. 1018 (2014) 131–136. doi: 10.4028/www.scientific.net/AMR.1018.131
11. [11]
  A. Saikia, N. Karak, Colloids Surf. A: Physicochem. Eng. Asp. 584 (2020) 124049. doi: 10.1016/j.colsurfa.2019.124049
12. [12]
  N. Xu, B. Wang, Z. An, et al., Chem. Mater. 34 (2022) 4732–4740. doi: 10.1021/acs.chemmater.2c00728
13. [13]
  Q. Zhao, L. An, C. Li, et al., Compos. Sci. Technol. 224 (2022) 109461. doi: 10.1016/j.compscitech.2022.109461
14. [14]
  X. Zhao, X. Liu, K. Feng, et al., ChemSusChem 15 (2022) e202101607. doi: 10.1002/cssc.202101607
15. [15]
  G. Oliveux, L.O. Dandy, G.A. Leeke, Prog. Mater. Sci. 72 (2015) 61–99. doi: 10.1016/j.pmatsci.2015.01.004
16. [16]
  F.L. Jin, X. Li, S.J. Park, J. Ind. Eng. Chem. 29 (2015) 1–11. doi: 10.1016/j.jiec.2015.03.026
17. [17]
  X.H. Shi, L. Chen, B.W. Liu, et al., Chin. J. Polym. Sci. 36 (2018) 1375–1384. doi: 10.1007/s10118-018-2164-1
18. [18]
  T. Hanaoka, Y. Arao, Y. Kayaki, et al., ACS Sustain. Chem. Eng. 9 (2021) 12520–12529. doi: 10.1021/acssuschemeng.1c01737
19. [19]
  V.D. Mai, S.R. Shin, D.S. Lee, et al., Polymers 11 (2019) 293. doi: 10.3390/polym11020293
20. [20]
  Y. Liu, J. Liu, Z. Jiang, et al., Polym. Degrad. Stab. 97 (2012) 214–220. doi: 10.1016/j.polymdegradstab.2011.12.028
21. [21]
  P. Yang, Q. Zhou, X.X. Yuan, et al., Polym. Degrad. Stab. 97 (2012) 1101–1106. doi: 10.1016/j.polymdegradstab.2012.04.007
22. [22]
  M. Das, R. Chacko, S. Varughese, A.C.S. Sustain. Chem. Eng. 6 (2018) 1564–1571. doi: 10.1021/acssuschemeng.7b01456
23. [23]
  D.H. Kim, M. Lee, M. Goh, A.C.S. Sustain. Chem. Eng. 8 (2019) 2433–2440.
24. [24]
  K. Li, L. Zhang, Z. Xu, J. Hazard. Mater. 374 (2019) 356–364. doi: 10.1016/j.jhazmat.2019.04.028
25. [25]
  I. Okajima, T. Sako, Polym. Degrad. Stab. 163 (2019) 1–6. doi: 10.1016/j.polymdegradstab.2019.02.018
26. [26]
  X. Kuang, E. Guo, K. Chen, et al., ACS Sustain. Chem. Eng. 7 (2019) 6880–6888. doi: 10.1021/acssuschemeng.8b06409
27. [27]
  X. Kuang, Q. Shi, Y. Zhou, et al., RSC Adv. 8 (2018) 1493–1502. doi: 10.1039/C7RA12787A
28. [28]
  K. Huang, W. Yuan, Y. Yang, et al., Waste Manag. 123 (2021) 60–68. doi: 10.1016/j.wasman.2021.01.024
29. [29]
  C.M. Hamel, X. Kuang, K. Chen, et al., Macromolecules 52 (2019) 3636–3645. doi: 10.1021/acs.macromol.9b00540
30. [30]
  X. Shi, C. Luo, H. Lu, et al., Polym. Eng. Sci. 59 (2019) E111–E119.
31. [31]
  X. Zhao, X.L. Wang, F. Tian, et al., Green Chem. 21 (2019) 2487–2493. doi: 10.1039/c9gc00685k
32. [32]
  Y.N. Kim, Y.O. Kim, S.Y. Kim, et al., Compos. Sci. Technol. 173 (2019) 66–72. doi: 10.1016/j.compscitech.2019.01.026
33. [33]
  H. Memon, H. Liu, M.A. Rashid, et al., Macromolecules 53 (2020) 621–630. doi: 10.1021/acs.macromol.9b02006
34. [34]
  H. Memon, Y. Wei, L. Zhang, et al., Compos. Sci. Technol. 199 (2020) 108314. doi: 10.1016/j.compscitech.2020.108314
35. [35]
  Q. Mu, L. An, Z. Hu, et al., Polym. Degrad. Stab. 199 (2022) 109895. doi: 10.1016/j.polymdegradstab.2022.109895
36. [36]
  K.S.K. Reddy, W.J. Gao, C.H. Chen, et al., ACS Sustain. Chem. Eng. 9 (2021) 5304–5314. doi: 10.1021/acssuschemeng.0c08998
37. [37]
  L. Zhang, J. Liu, W. Nie, et al., J. Mater. Cycles Waste Manag. 20 (2017) 568–577. doi: 10.1080/00222348.2017.1342971
38. [38]
  W. Zhao, L. An, S. Wang, Polymers 13 (2021) 296. doi: 10.3390/polym13020296
39. [39]
  A. Manakhov, J. Čechal, M. Michlíček, et al., Appl. Surf. Sci. 414 (2017) 390–397. doi: 10.1016/j.apsusc.2017.04.127
40. [40]
  K. Pareek, Q. Zhang, R. Rohan, et al., Adv. Mater. Interfaces 1 (2014) 1400107. doi: 10.1002/admi.201400107
41. [41]
  M. Shen, M.L. Robertson, ACS Sustain. Chem. Eng. 9 (2020) 438–447.
1. [1]
  Fengrui Yang , Debing Wang , Xinying Zhang , Jie Zhang , Zhichao Wu , Qiaoying Wang . Synergistic effects of peroxydisulfate on UV/O₃ process for tetracycline degradation: Mechanism and pathways. Chinese Chemical Letters, 2024, 35(10): 109599-. doi: 10.1016/j.cclet.2024.109599
2. [2]
  Yuqing Zhu , Haohao Chen , Li Wang , Liqun Ye , Houle Zhou , Qintian Peng , Huaiyong Zhu , Yingping Huang . Piezoelectric materials for pollutants degradation: State-of-the-art accomplishments and prospects. Chinese Chemical Letters, 2024, 35(4): 108884-. doi: 10.1016/j.cclet.2023.108884
3. [3]
  Menglu Guo , Ying-Qi Song , Junfei Cheng , Guoqiang Dong , Xun Sun , Chunquan Sheng . Hydrophobic tagging-induced degradation of NAMPT in leukemia cells. Chinese Chemical Letters, 2024, 35(9): 109392-. doi: 10.1016/j.cclet.2023.109392
4. [4]
  Shuo Li , Xinran Liu , Yongjie Zheng , Jun Ma , Shijie You , Heshan Zheng . Effective peroxydisulfate activation by CQDs-MnFe₂O₄@ZIF-8 catalyst for complementary degradation of bisphenol A by free radicals and non-radical pathways. Chinese Chemical Letters, 2024, 35(5): 108971-. doi: 10.1016/j.cclet.2023.108971
5. [5]
  Yinyin Xu , Yuanyuan Li , Jingbo Feng , Chen Wang , Yan Zhang , Yukun Wang , Xiuwen Cheng . Covalent organic frameworks doped with manganese-metal organic framework for peroxymonosulfate activation. Chinese Chemical Letters, 2024, 35(4): 108838-. doi: 10.1016/j.cclet.2023.108838
6. [6]
  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
7. [7]
  Xiaotao Jin , Yanlan Wang , Yingping Huang , Di Huang , Xiang Liu . Percarbonate activation catalyzed by nanoblocks of basic copper molybdate for antibiotics degradation: High performance, degradation pathways and mechanism. Chinese Chemical Letters, 2024, 35(10): 109499-. doi: 10.1016/j.cclet.2024.109499
8. [8]
  Yun-Xin Huang , Lin-Qian Yu , Ke-Yu Chen , Hao Wang , Shou-Yan Zhao , Bao-Cheng Huang , Ren-Cun Jin . Biochar with self-doped N to activate peroxymonosulfate for bisphenol-A degradation via electron transfer mechanism: The active edge graphitic N site. Chinese Chemical Letters, 2024, 35(9): 109437-. doi: 10.1016/j.cclet.2023.109437
9. [9]
  Weichen Zhu , Wei Zuo , Pu Wang , Wei Zhan , Jun Zhang , Lipin Li , Yu Tian , Hong Qi , Rui Huang . Fe-N-C heterogeneous Fenton-like catalyst for the degradation of tetracycline: Fe-N coordination and mechanism studies. Chinese Chemical Letters, 2024, 35(9): 109341-. doi: 10.1016/j.cclet.2023.109341
10. [10]
  Junchen Peng , Xue Yin , Dandan Dong , Zhongyuan Guo , Qinqin Wang , Minmin Liu , Fei He , Bin Dai , Chaofeng Huang . Promotion effect of epoxy group neighboring single-atom Cu site on acetylene hydrochlorination. Chinese Chemical Letters, 2024, 35(6): 109508-. doi: 10.1016/j.cclet.2024.109508
11. [11]
  Yun-Fei Zhang , Chun-Hui Zhang , Jian-Hui Xu , Lei Li , Dan Li , Jin-Hong Fan , Jiale Gao , Xin Quan , Qi Wu , Yue Zou , Yan-Ling Liu . Enhanced degradation of florfenicol by microscale SiC/Fe: Dechlorination via hydrogenolysis. Chinese Chemical Letters, 2024, 35(7): 109385-. doi: 10.1016/j.cclet.2023.109385
12. [12]
  Cunjun Li , Wencong Liu , Xianlei Chen , Liang Li , Shenyu Lan , Mingshan Zhu . Adsorption and activation of peroxymonosulfate on BiOCl for carbamazepine degradation: The role of piezoelectric effect. Chinese Chemical Letters, 2024, 35(10): 109652-. doi: 10.1016/j.cclet.2024.109652
13. [13]
  Qiang Zhang , Weiran Gong , Huinan Che , Bin Liu , Yanhui Ao . S doping induces to promoted spatial separation of charge carriers on carbon nitride for efficiently photocatalytic degradation of atrazine. Chinese Journal of Structural Chemistry, 2023, 42(12): 100205-100205. doi: 10.1016/j.cjsc.2023.100205
14. [14]
  Jian Peng , Yue Jiang , Shuangyu Wu , Yanran Cheng , Jingyu Liang , Yixin Wang , Zhuo Li , Sijie Lin . A nonradical oxidation process initiated by Ti-peroxo complex showed high specificity toward the degradation of tetracycline antibiotics. Chinese Chemical Letters, 2024, 35(5): 108903-. doi: 10.1016/j.cclet.2023.108903
15. [15]
  Dong Cheng , Youyou Feng , Bingxi Feng , Ke Wang , Guoxin Song , Gen Wang , Xiaoli Cheng , Yonghui Deng , Jing Wei . Polyphenol-mediated interfacial deposition strategy for supported manganese oxide catalysts with excellent pollutant degradation performance. Chinese Chemical Letters, 2024, 35(5): 108623-. doi: 10.1016/j.cclet.2023.108623
16. [16]
  Kai Han , Guohui Dong , Ishaaq Saeed , Tingting Dong , Chenyang Xiao . Morphology and photocatalytic tetracycline degradation of g-C3N4 optimized by the coal gangue. Chinese Journal of Structural Chemistry, 2024, 43(2): 100208-100208. doi: 10.1016/j.cjsc.2023.100208
17. [17]
  Si Ha , Jiacheng Zhu , Hua Xiang , Guoshun Luo . Hydrophobic tag tethering degrader as a promising paradigm of protein degradation: Past, present and future perspectives. Chinese Chemical Letters, 2024, 35(8): 109192-. doi: 10.1016/j.cclet.2023.109192
18. [18]
  Chunxiu Yu , Zelin Wu , Hongle Shi , Lingyun Gu , Kexin Chen , Chuan-Shu He , Yang Liu , Heng Zhang , Peng Zhou , Zhaokun Xiong , Bo Lai . Insights into the electron transfer mechanisms of peroxydisulfate activation by modified metal-free acetylene black for degradation of sulfisoxazole. Chinese Chemical Letters, 2024, 35(8): 109334-. doi: 10.1016/j.cclet.2023.109334
19. [19]
  Yiqian Jiang , Zihan Yang , Xiuru Bi , Nan Yao , Peiqing Zhao , Xu Meng . Mediated electron transfer process in α-MnO₂ catalyzed Fenton-like reaction for oxytetracycline degradation. Chinese Chemical Letters, 2024, 35(8): 109331-. doi: 10.1016/j.cclet.2023.109331
20. [20]
  Shiyu Pan , Bo Cao , Deling Yuan , Tifeng Jiao , Qingrui Zhang , Shoufeng Tang . Complexes of cupric ion and tartaric acid enhanced calcium peroxide Fenton-like reaction for metronidazole degradation. Chinese Chemical Letters, 2024, 35(7): 109185-. doi: 10.1016/j.cclet.2023.109185

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(252)
HTML views(17)

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