Citation: Xin Song, Ze-Peng Deng, Chun-Bo Li, Fei Song, Xiu-Li Wang, Li Chen, De-Ming Guo, Yu-Zhong Wang. A bio-based epoxy resin derived from p-hydroxycinnamic acid with high mechanical properties and flame retardancy[J]. Chinese Chemical Letters, ;2022, 33(11): 4912-4917. doi: 10.1016/j.cclet.2021.12.067 shu

A bio-based epoxy resin derived from p-hydroxycinnamic acid with high mechanical properties and flame retardancy

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

songfei520@gmail.com

yzwang@scu.edu.cn

Received Date: 26 November 2021
Revised Date: 22 December 2021
Accepted Date: 23 December 2021
Available Online: 29 December 2021

Figures(11)

Recent advances in epoxy resins have been forward to achieving high mechanical performance, thermal stability, and flame retardancy. However, seeking sustainable bio-based epoxy precursors and avoiding introduction of additional flame-retardant agents are still of increasing demand. Here we report the synthesis of p-hydroxycinnamic acid-derived epoxy monomer (HCA-EP) via a simple one-step reaction, and the HCA-EP can be cured with 4, 4′-diaminodiphenylmethane (DDM) to prepare epoxy resins. Compared with the typical petroleum-based epoxy resin, bisphenol A epoxy resin, the HCA-EP-DDM shows a relatively high glass transition temperature (192.9 ℃) and impressive mechanical properties (tensile strength of 98.3 MPa and flexural strength of 158.9 MPa). Furthermore, the HCA-EP-DDM passes the V-1 flammability rating in UL-94 test and presents the limiting oxygen index of 32.6%. Notably, its char yield is as high as 31.6% under N₂, and the peak heat rate release is 60% lower than that of bisphenol A epoxy resin. Such findings provide a simple way of using p-hydroxycinnamic acid instead of bisphenol A to construct high-performance bio-based thermosets.
- Epoxy resin,
- Bio-based,
- p-Hydroxycinnamic acid,
- Mechanical performance,
- Intrinsic flame retardancy
1. [1]
  L.L. Hia, E.S. Chan, S.P. Chai, P. Pasbakhsh, J. Mater. Chem. A 6 (2018) 8470–8478. doi: 10.1039/C8TA01783B
2. [2]
  D. Cespi, R. Cucciniello, M. Ricciardi, et al., Green Chem. 18 (2016) 4559–4570. doi: 10.1039/C6GC00882H
3. [3]
  R.W. Stahlhut, W.V. Welshons, S.H. Swan, et al., Environ. Health Perspect. 117 (2009) 784–789. doi: 10.1289/ehp.0800376
4. [4]
  P. Roy, H. Salminen, P. Koskimies, et al., J. Sreroid Biochem. 88 (2004) 157–166.
5. [5]
  R. Urbatzka, A.V. Cauwenberge, S. Maggioni, et al., Chemosphere 67 (2007) 1080–1087. doi: 10.1016/j.chemosphere.2006.11.041
6. [6]
  Q.X. Zhang, M. Molenda, T.M. Reineke, Macromolecules 49 (2016) 8397–8406. doi: 10.1021/acs.macromol.6b01861
7. [7]
  J.T. Wan, J.Q. Zhao, B. Gan, et al., ACS Sustain. Chem. Eng. 4 (2016) 2869–2880. doi: 10.1021/acssuschemeng.6b00479
8. [8]
  C. Li, H. Fan, T. Aziz, et al., ACS Sustain. Chem. Eng. 6 (2018) 8856–8867. doi: 10.1021/acssuschemeng.8b01212
9. [9]
  T. Liu, C. Hao, S. Zhang, et al., Macromolecules 51 (2018) 5577–5585. doi: 10.1021/acs.macromol.8b01010
10. [10]
  X.W. Xu, S.Q. Ma, J.H. Wu, et al., J. Mater. Chem. A 7 (2019) 15420–15431. doi: 10.1039/C9TA05293C
11. [11]
  X.W. Xu, S.Q. Ma, J.H. Wu, et al., J. Mater. Chem. A 8 (2020) 11261–11274. doi: 10.1039/D0TA01419B
12. [12]
  M. Fache, R. Auvergne, B. Boutevin, S. Caillol, Eur. Polym. J. 67 (2015) 527–538. doi: 10.1016/j.eurpolymj.2014.10.011
13. [13]
  Y. Ecochard, M. Decostanzi, C. Negrell, R. Sonnier, S. Caillol, Molecules 24 (2019) 1818. doi: 10.3390/molecules24091818
14. [14]
  J.T. Miao, L. Yuan, Q.B. Guan, G.Z. Liang, A.J. Gu, ACS Sustain. Chem. Eng. 5 (2017) 7003–7011. doi: 10.1021/acssuschemeng.7b01222
15. [15]
  A. Toldy, P. Anna, I. Csontos, A. Szabó, G. Marosi, Polym. Degrad. Stab. 92 (2007) 2223–2230. doi: 10.1016/j.polymdegradstab.2007.04.017
16. [16]
  J.Y. Yang, Y. Xia, J. Zhao, et al., Chin. J. Polym. Sci. 38 (2020) 1294–1304. doi: 10.1007/s10118-020-2444-4
17. [17]
  Z.P. Cheng, M.H. Fang, X.X. Chen, et al., ACS Omega 5 (2020) 4200–4212. doi: 10.1021/acsomega.9b04050
18. [18]
  X. Zhou, X.W. Mu, W. Cai, et al., ACS Appl. Mater. Interfaces 11 (2019) 41736–41749. doi: 10.1021/acsami.9b16482
19. [19]
  H. Zhang, J. Mao, M. Li, et al., Compos. Part A Appl. Sci. Manuf. 130 (2020) 105751. doi: 10.1016/j.compositesa.2019.105751
20. [20]
  L. Chen, C. Ruan, R. Yang, Y.Z. Wang, Polym. Chem. 5 (2014) 3737–3749. doi: 10.1039/c3py01717f
21. [21]
  Y. Tian, Q. Wang, L. Shen, et al., Chem. Eng. J. 383 (2020) 123124. doi: 10.1016/j.cej.2019.123124
22. [22]
  J.J. Meng, Y.S. Zeng, P.F. Chen, Macromol. Mater. Eng. 305 (2019) 1900587.
23. [23]
  T.Y. Gao, F.D. Wang, Y. Xu, et al., Chem. Eng. J. 428 (2022) 131173. doi: 10.1016/j.cej.2021.131173
24. [24]
  S. Wang, S.Q. Ma, C.X. Xu, et al., Macromolecules 50 (2017) 1892–1901. doi: 10.1021/acs.macromol.7b00097
25. [25]
  J.Y. Dai, Y.Y. Peng, N. Teng, et al., ACS Sustain. Chem. Eng. 6 (2018) 7589–7599. doi: 10.1021/acssuschemeng.8b00439
26. [26]
  Y. Qi, J.Y. Wang, Y. Kou, et al., Nat. Commun. 10 (2019) 2107. doi: 10.1038/s41467-019-10178-0
27. [27]
  J.Y. Dai, N. Teng, J.K. Liu, et al., Compos. Part B: Eng. 179 (2019) 107523. doi: 10.1016/j.compositesb.2019.107523
28. [28]
  W. Xie, D.L. Tang, S.M. Liu, J.Q. Zhao, Polym. Test. 86 (2020) 106466. doi: 10.1016/j.polymertesting.2020.106466
29. [29]
  Z.H. Chi, Z.W. Guo, Z. Xu, et al., Polym. Degrad. Stabil. 176 (2020) 109151. doi: 10.1016/j.polymdegradstab.2020.109151
30. [30]
  J.K. Liu, J.Y. Dai, S.P. Wang, et al., Compos. Part B: Eng. 190 (2020) 107926. doi: 10.1016/j.compositesb.2020.107926
31. [31]
  X.C. Tan, Q. Zou, Y.Z. Huang, et al., Ind. Eng. Chem. Res. 57 (2018) 7898–7904. doi: 10.1021/acs.iecr.8b01312
32. [32]
  S.S. Xu, Y. Han, Y. Guo, et al., Eur. Polym. J. 95 (2017) 394–405. doi: 10.1016/j.eurpolymj.2017.08.010
33. [33]
  H.E. Kissinger, Anal. Chem. 29 (1957) 1702–1706. doi: 10.1021/ac60131a045
34. [34]
  Y.L. Liu, S.Q. Ma, Q. Li, et al., Eur. Polym. J. 135 (2020) 109881. doi: 10.1016/j.eurpolymj.2020.109881
35. [35]
  Y. Qi, Z.H. Weng, K.W. Zhang, et al., Chem. Eng. J. 387 (2020) 124115. doi: 10.1016/j.cej.2020.124115
36. [36]
  W.J. Liang, B. Zhao, P.H. Zhao, C.Y. Zhang, Y.Q. Liu, Polym. Degrad. Stab. 135 (2017) 140–151. doi: 10.1016/j.polymdegradstab.2016.11.023
37. [37]
  Y. Qi, Z.H. Weng, Y. Kou, et al., Chem. Eng. J. 406 (2021) 126881. doi: 10.1016/j.cej.2020.126881
38. [38]
  J.R. Pels, F. Kapteijn, J.A. Moulijn, Q. Zhu, K.M. Thomas, Carbon 33 (1995) 1641–1653. doi: 10.1016/0008-6223(95)00154-6
39. [39]
  F.K. Chu, C. Ma, T. Zhang, et al., Compos. Part B: Eng. 190 (2020) 107925. doi: 10.1016/j.compositesb.2020.107925
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]
  Dongmei Yao , Junsheng Zheng , Liming Jin , Xiaomin Meng , Zize Zhan , Runlin Fan , Cong Feng , Pingwen Ming . Effect of surface oxidation on the interfacial and mechanical properties in graphite/epoxy composites composite bipolar plates. Chinese Chemical Letters, 2024, 35(11): 109382-. doi: 10.1016/j.cclet.2023.109382
3. [3]
  Xinpin Pan , Yongjian Cui , Zhe Wang , Bowen Li , Hailong Wang , Jian Hao , Feng Li , Jing Li . Robust chemo-mechanical stability of additives-free SiO₂ anode realized by honeycomb nanolattice for high performance Li-ion batteries. Chinese Chemical Letters, 2024, 35(10): 109567-. doi: 10.1016/j.cclet.2024.109567
4. [4]
  Maitri Bhattacharjee , Rekha Boruah Smriti , R. N. Dutta Purkayastha , Waldemar Maniukiewicz , Shubhamoy Chowdhury , Debasish Maiti , Tamanna Akhtar . Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007
5. [5]
  Jianmei Guo , Yupeng Zhao , Lei Ma , Yongtao Wang . Ultra-long room temperature phosphorescence, intrinsic mechanisms and application based on host-guest doping systems. Chinese Journal of Structural Chemistry, 2024, 43(9): 100335-100335. doi: 10.1016/j.cjsc.2024.100335
6. [6]
  Pei Cao , Yilan Wang , Lejian Yu , Miao Wang , Liming Zhao , Xu Hou . Dynamic asymmetric mechanical responsive carbon nanotube fiber for ionic logic gate. Chinese Chemical Letters, 2024, 35(6): 109421-. doi: 10.1016/j.cclet.2023.109421
7. [7]
  Yanyu Jin , Wenzhe Si , Xing Yuan , Hongjun Cheng , Bin Zhou , Li Cai , Yu Wang , Qibao Wang , Junhua Li . Tuning TM–O interaction by acid etching in perovskite catalysts boosting catalytic performance. Chinese Chemical Letters, 2025, 36(5): 110260-. doi: 10.1016/j.cclet.2024.110260
8. [8]
  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
9. [9]
  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
10. [10]
  Guan-Nan Xing , Di-Ye Wei , Hua Zhang , Zhong-Qun Tian , Jian-Feng Li . Pd-based nanocatalysts for oxygen reduction reaction: Preparation, performance, and in-situ characterization. Chinese Journal of Structural Chemistry, 2023, 42(11): 100021-100021. doi: 10.1016/j.cjsc.2023.100021
11. [11]
  Jaeyong Ahn , Zhenping Li , Zhiwei Wang , Ke Gao , Huagui Zhuo , Wanuk Choi , Gang Chang , Xiaobo Shang , Joon Hak Oh . Surface doping effect on the optoelectronic performance of 2D organic crystals based on cyano-substituted perylene diimides. Chinese Chemical Letters, 2024, 35(9): 109777-. doi: 10.1016/j.cclet.2024.109777
12. [12]
  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
13. [13]
  A-Yang Wang , Sheng-Hua Zhou , Mao-Yin Ran , Xin-Tao Wu , Hua Lin , Qi-Long Zhu . Regulating the key performance parameters for Hg-based IR NLO chalcogenides via bandgap engineering strategy. Chinese Chemical Letters, 2024, 35(10): 109377-. doi: 10.1016/j.cclet.2023.109377
14. [14]
  Pingping HAO , Fangfang LI , Yawen WANG , Houfen LI , Xiao ZHANG , Rui LI , Lei WANG , Jianxin LIU . Hydrogen production performance of the non-platinum-based MoS₂/CuS cathode in microbial electrolytic cells. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1811-1824. doi: 10.11862/CJIC.20240054
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]
  Lihang Wang , Mary Li Javier , Chunshan Luo , Tingsheng Lu , Shudan Yao , Bing Qiu , Yun Wang , Yunfeng Lin . Research advances of tetrahedral framework nucleic acid-based systems in biomedicine. Chinese Chemical Letters, 2024, 35(11): 109591-. doi: 10.1016/j.cclet.2024.109591
17. [17]
  Panke Zhou , Hong Yu , Mun Yin Chee , Tao Zeng , Tianli Jin , Hongling Yu , Shuo Wu , Wen Siang Lew , Xiong Chen . Electron push-pull effects induced performance promotion in covalent organic polymer thin films-based memristor for neuromorphic application. Chinese Chemical Letters, 2024, 35(5): 109279-. doi: 10.1016/j.cclet.2023.109279
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]
  Xiangan Song , Shaogang Shen , Mengyao Lu , Ying Wang , Yong Zhang . Trifluoromethyl enable high-performance single-emitter white organic light-emitting devices based on quinazoline acceptor. Chinese Chemical Letters, 2024, 35(4): 109118-. doi: 10.1016/j.cclet.2023.109118
20. [20]
  Pu Zhang , Xiang Mao , Xuehua Dong , Ling Huang , Liling Cao , Daojiang Gao , Guohong Zou . Two UV organic-inorganic hybrid antimony-based materials with superior optical performance derived from cation-anion synergetic interactions. Chinese Chemical Letters, 2024, 35(9): 109235-. doi: 10.1016/j.cclet.2023.109235

Get Citation

PDF

XML

Metrics

PDF Downloads(14)
Abstract views(891)
HTML views(125)

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