Citation: Xinyu Liu, Jialin Yang, Zonglin He, Jiaoyan Ai, Lina Song, Baohua Liu. Linear polyurethanes with excellent comprehensive properties from poly(ethylene carbonate) diol[J]. Chinese Chemical Letters, ;2025, 36(1): 110236. doi: 10.1016/j.cclet.2024.110236 shu

Linear polyurethanes with excellent comprehensive properties from poly(ethylene carbonate) diol

School of Materials and Energy, Guangdong University of Technology, Guangzhou 510006, China

songlina@gdut.edu.cn

baohua@gdut.edu.cn

Received Date: 29 May 2024
Revised Date: 5 July 2024
Accepted Date: 10 July 2024
Available Online: 10 July 2024

Figures(3)

The synthesis of polyurethanes (PUs) from the reaction of low molecular weight poly(ethylene carbonate) diol (PECD) is rarely investigated. This work reports a novel PU with excellent mechanical properties from the solution polymerization of 4,4′-diphenylmethane diisocyanate (MDI) with PECD that was derived from the copolymerization of carbon dioxide (CO₂) and ethylene oxide (EO). The tensile strength, the elongation at break and 300% constant tensile strength of the PECD-PU were up to 66 ± 2 MPa, 880% ± 50% and 13 MPa, respectively, higher than the control PUs from the reaction of MDI with commercial polyethers or polyesters. The PECD-PU with high CO₂ carbonate content exhibited good solvent resistance and chemical stability. Of importance, the mechanical properties and chemical resistance of PECD-PU were significantly enhanced with the increasing content of CO₂, i.e., the carbonate unit in PECD. This work provides comprehensive properties of PECD-derived PUs, indicating that PECD is a competitive precursor for the preparation of PU and has broad application prospects.
- Carbon dioxide,
- Poly(ethylene carbonate) diol,
- Polyurethane,
- Ethylene oxide,
- Copolymerization
1. [1]
  Y.N. Xia, C.J. Zhang, Y. Wang, S.J. Liu, X.H. Zhang, Chin. Chem. Lett. 35 (2024) 108860. doi: 10.1016/j.cclet.2023.108860
2. [2]
  Y.Y. Zhang, G.P. Wu, D.J. Darensbourg, Trends Chem. 2 (2020) 750–763. doi: 10.1016/j.trechm.2020.05.002
3. [3]
  M.U. Khan, S.U. Khan, J. Kiriratnikom, S. Zareen, X.H. Zhang, Chin. Chem. Lett. 33 (2022) 1081–1086. doi: 10.1016/j.cclet.2021.06.002
4. [4]
  G.A. Luinstra, Polym. Rev. 48 (2008) 192–219. doi: 10.1080/15583720701834240
5. [5]
  J. Kuyper, P.W. Lednor, G.A. Pogany, Patent, US4826953, 1989.
6. [6]
  N. von der Assena, A. Bardow, Green Chem. 16 (2014) 3272–3280. doi: 10.1039/C4GC00513A
7. [7]
  J. Wang, H.M. Zhang, Y.Y. Miao, et al., Polymer 100 (2016) 219–226. doi: 10.1016/j.polymer.2016.08.039
8. [8]
  J. Wang, H.M. Zhang, Y.Y. Miao, et al., Green Chem. 18 (2016) 524–530. doi: 10.1039/C5GC01373A
9. [9]
  R. Meys, A. Kaetelhoen, A. Bardow, Green Chem. 21 (2019) 3334–3342. doi: 10.1039/c9gc00267g
10. [10]
  G. Buchner, N. Wulfes, R. Schomäcker, J. CO₂ Util. 36 (2020) 153–168. doi: 10.1016/j.jcou.2019.11.010
11. [11]
  R.A. Gong, H. Cao, H.M. Zhang, L.J. Qiao, X.H. Wang, Polymer 218 (2021) 123536. doi: 10.1016/j.polymer.2021.123536
12. [12]
  X. Huang, K. Alferov, T. Zhao, et al., J. CO₂ Util. 75 (2023) 102571. doi: 10.1016/j.jcou.2023.102571
13. [13]
  X. Huang, T. Zhao, M. Xiao, et al., Chin. Sci. Bull. 69 (2024) 2923–2934. doi: 10.1360/TB-2023-1089
14. [14]
  B.H. Liu, W. Ba, J. Nanjing Univ. Technol. (Nat. Sci. Ed.) 29 (2007) 33–36.
15. [15]
  X.H. Zhang, R.J. Wei, X.K. Sun, et al., Polymer 52 (2011) 5494–5502. doi: 10.1016/j.polymer.2011.09.040
16. [16]
  Y.G. Gao, G. Lin, X.H. Wang, F.S. Wang, J. Polym. Sci. A: Polym. Chem. 50 (2012) 5177–5184. doi: 10.1002/pola.26366
17. [17]
  S.J. Liu, Y.S. Qin, X.S. Chen, X.H. Wang, F.S. Wang, Polym. Chem. 21 (2014) 6171–6179.
18. [18]
  S.J. Liu, Y.Y. Miao, L.J. Qiao, et al., Polym. Chem. 43 (2015) 7580–7585.
19. [19]
  M. Pohl, E. Danieli, M. Leven, et al., Macromolecules 49 (2016) 8995–9003. doi: 10.1021/acs.macromol.6b01601
20. [20]
  S.J. Liu, Y.S. Qin, L.J. Qiao, et al., Polym. Chem. 7 (2016) 146–152. doi: 10.1039/C5PY01338K
21. [21]
  P. Wang, S.J. Liu, Y.S. Chen, X.H. Wang, F.S. Wang, Acta Polym. Sin. 2 (2017) 259–265.
22. [22]
  S.B. Fu, Y.S. Qin, L.J. Qiao, X.H. Wang, F.S. Wang, Acta Polym. Sin. 4 (2019) 338–343.
23. [23]
  D.J. Darensbourg, Green Chem. 21 (2019) 2214–2223. doi: 10.1039/c9gc00620f
24. [24]
  N.G. Patil, S.K. Boopathi, P. Alagi, et al., Macromolecules 52 (2019) 2431–2438. doi: 10.1021/acs.macromol.9b00122
25. [25]
  N. Patil, S. Bhoopathi, V. Chidara, et al., ChemSusChem 13 (2020) 5080–5087. doi: 10.1002/cssc.202001395
26. [26]
  K. Böhm, S.G. Maerten, M.A. Liauw, T.E. Müller, Macromolecules 53 (2020) 6861–6865. doi: 10.1021/acs.macromol.0c00825
27. [27]
  H. Cao, R.N. Gong, Z.Z. Zhou, X.H. Wang, F.S. Wang, Acta Polym. Sin. 8 (2021) 1006–1014. doi: 10.3724/sp.j.1123.2021.06022
28. [28]
  C.W. Zhuo, H. Cao, Z.Z. Zhou, S.J. Liu, X.H. Wang, Acta Polym. Sin. 54 (2023) 601–611.
29. [29]
  C.J. Zhang, X.W. Geng, X.H. Zhang, Y. Gnanou, X.S. Feng, Pro. Polym. Sci. 136 (2023) 101644. doi: 10.1016/j.progpolymsci.2022.101644
30. [30]
  J.J. Liu, M.C. Jia, Y. Gnanou, X.S. Feng, Macromolecules 56 (2024) 892–898.
31. [31]
  N.G. Patil, Y. Gnanou, X.S. Feng, J. CO₂ Util. 83 (2024) 102795. doi: 10.1016/j.jcou.2024.102795
32. [32]
  R.F. Harris, M.D. Joseph, C. Davidson, C.D. Deporter, V.A. Dais, J. Appl. Polym. Sci. 41 (1990) 487–507. doi: 10.1002/app.1990.070410304
33. [33]
  S.P. Xu, M. Zhang, J. Appl. Polym. Sci. 27 (2007) 3818–3826. doi: 10.1002/app.25968
34. [34]
  Z.H. Huang, Z.L. He, C.Z. Wang, et al., Sustain. Polym. Energy 1 (2023) 10005.
35. [35]
  B.H. Liu, L.B. Chen, M.X. Zhang, A.F. Yu, Chin. Chem. Lett. 14 (2003) 752–754.
36. [36]
  Z.L. He, Z.H. Huang, J.H. Chen, et al., J. Appl. Polym. Sci. 140 (2023) e54671. doi: 10.1002/app.54671
37. [37]
  J.H. Chen, Y.Y. Cui, Z. Ding, et al., Prog. Org. Coat. 84 (2023) 107824.
38. [38]
  Z.J. Ding, J.H. Chen, Z.L. He, et al., J. Coat. Technol. Res. 20 (2023) 1569–1578. doi: 10.1007/s11998-023-00763-w
39. [39]
  C.Z. Wang, H.L. Li, Z.H. Huang, et al., Chem. Pap. 77 (2023) 3347–3359. doi: 10.1007/s11696-023-02708-4
40. [40]
  L. Ma, L.N. Song, H. Wang, L.Q. Fan, B.H. Liu, Prog. Org. Coat. 122 (2018) 38–44. doi: 10.1016/j.porgcoat.2018.05.003
41. [41]
  L. Ma, L.N. Song, F. Li, H. Wang, B.H. Liu, Colloid Polym. Sci. 295 (2017) 2299–2307.
42. [42]
  W.Q. Xian, L.N. Song, B.H. Liu, et al., J. Appl. Polym. Sci. 135 (2017) 45974.
43. [43]
  Z.H. Huang, C.Z. Wang, H.L. Li, et al., Prog. Org. Coat. 181 (2023) 107580. doi: 10.1016/j.porgcoat.2023.107580
44. [44]
  M.C. Jia, D.Y. Zhang, Y. Gnanou, X.S. Feng, ACS Sustain. Chem. Eng. 9 (2021) 10370–10380. doi: 10.1021/acssuschemeng.1c03751
1. [1]
  Yongheng Ren , Yang Chen , Hongwei Chen , Lu Zhang , Jiangfeng Yang , Qi Shi , Lin-Bing Sun , Jinping Li , Libo Li . Electrostatically driven kinetic Inverse CO2/C2H2 separation in LTA-type zeolites. Chinese Journal of Structural Chemistry, 2024, 43(10): 100394-100394. doi: 10.1016/j.cjsc.2024.100394
2. [2]
  Daheng Wen , Weiwei Fang , Yongmei Liu , Tao Tu . Valorization of carbon dioxide with alcohols. Chinese Chemical Letters, 2024, 35(7): 109394-. doi: 10.1016/j.cclet.2023.109394
3. [3]
  He Yao , Wenhao Ji , Yi Feng , Chunbo Qian , Chengguang Yue , Yue Wang , Shouying Huang , Mei-Yan Wang , Xinbin Ma . Copper-catalyzed and biphosphine ligand controlled 3,4-boracarboxylation of 1,3-dienes with carbon dioxide. Chinese Chemical Letters, 2025, 36(4): 110076-. doi: 10.1016/j.cclet.2024.110076
4. [4]
  Hailong He , Wenbing Wang , Wenmin Pang , Chen Zou , Dan Peng . Double stimulus-responsive palladium catalysts for ethylene polymerization and copolymerization. Chinese Chemical Letters, 2024, 35(7): 109534-. doi: 10.1016/j.cclet.2024.109534
5. [5]
  Yi Liu , Zhe-Hao Wang , Guan-Hua Xue , Lin Chen , Li-Hua Yuan , Yi-Wen Li , Da-Gang Yu , Jian-Heng Ye . Photocatalytic dicarboxylation of strained C–C bonds with CO₂ via consecutive visible-light-induced electron transfer. Chinese Chemical Letters, 2024, 35(6): 109138-. doi: 10.1016/j.cclet.2023.109138
6. [6]
  Tian-Yu Gao , Xiao-Yan Mo , Shu-Rong Zhang , Yuan-Xu Jiang , Shu-Ping Luo , Jian-Heng Ye , Da-Gang Yu . Visible-light photoredox-catalyzed carboxylation of aryl epoxides with CO₂. Chinese Chemical Letters, 2024, 35(7): 109364-. doi: 10.1016/j.cclet.2023.109364
7. [7]
  Li Li , Zhi-Xin Yan , Chuan-Kun Ran , Yi Liu , Shuo Zhang , Tian-Yu Gao , Long-Fei Dai , Li-Li Liao , Jian-Heng Ye , Da-Gang Yu . Electro-reductive carboxylation of CCl bonds in unactivated alkyl chlorides and polyvinyl chloride with CO₂. Chinese Chemical Letters, 2024, 35(12): 110104-. doi: 10.1016/j.cclet.2024.110104
8. [8]
  Zhen Zhang , Xue-ling Chen , Xiu-Mei Xie , Tian-Yu Gao , Jing Qin , Jun-Jie Li , Chao Feng , Da-Gang Yu . Iron-promoted carbonylation–rearrangement of α-aminoaryl-tethered alkylidenecyclopropanes with CO₂: Facile synthesis of quinolinofurans. Chinese Chemical Letters, 2025, 36(4): 110056-. doi: 10.1016/j.cclet.2024.110056
9. [9]
  Yueguang Chen , Wenqiang Sun . “Carbon” Adventures. University Chemistry, 2024, 39(9): 248-253. doi: 10.3866/PKU.DXHX202308074
10. [10]
  Junying Zhang , Ruochen Li , Haihua Wang , Wenbing Kang , Xing-Dong Xu . Photo-induced tunable luminescence from an aggregated amphiphilic ethylene-pyrene derivative in aqueous media. Chinese Chemical Letters, 2024, 35(6): 109216-. doi: 10.1016/j.cclet.2023.109216
11. [11]
  Jiahao Li , Guinan Chen , Chunhong Chen , Yuanyuan Lou , Zhihao Xing , Tao Zhang , Chengtao Gong , Yongwu Peng . Modulated synthesis of stoichiometric and sub-stoichiometric two-dimensional covalent organic frameworks for enhanced ethylene purification. Chinese Chemical Letters, 2025, 36(1): 109760-. doi: 10.1016/j.cclet.2024.109760
12. [12]
  Yao-Yu Ma , Wen-Juan Shi , Gang-Ding Wang , Xin Liu , Lei Hou , Yao-Yu Wang . Enhancing ethane/ethylene separation performance through the amino-functionalization of ethane-selective MOF. Chinese Chemical Letters, 2025, 36(3): 109729-. doi: 10.1016/j.cclet.2024.109729
13. [13]
  Yuan Dong , Mutian Ma , Zhenyang Jiao , Sheng Han , Likun Xiong , Zhao Deng , Yang Peng . Effect of electrolyte cation-mediated mechanism on electrocatalytic carbon dioxide reduction. Chinese Chemical Letters, 2024, 35(7): 109049-. doi: 10.1016/j.cclet.2023.109049
14. [14]
  Wei-Jia Wang , Kaihong Chen . Molecular-based porous polymers with precise sites for photoreduction of carbon dioxide. Chinese Chemical Letters, 2025, 36(1): 109998-. doi: 10.1016/j.cclet.2024.109998
15. [15]
  Yuchen Zhang , Lifeng Ding , Zhenghe Xie , Xin Zhang , Xiaofeng Sui , Jian-Rong Li . Porous sorbents for direct capture of carbon dioxide from ambient air. Chinese Chemical Letters, 2025, 36(3): 109676-. doi: 10.1016/j.cclet.2024.109676
16. [16]
  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
17. [17]
  Xiaoxiao Huang , Zhi-Long He , Yangpeng Chen , Lei Li , Zhenyu Yang , Chunyang Zhai , Mingshan Zhu . Novel P-doping-tuned Pd nanoflowers/S,N-GQDs photo-electrocatalyst for high-efficient ethylene glycol oxidation. Chinese Chemical Letters, 2024, 35(6): 109271-. doi: 10.1016/j.cclet.2023.109271
18. [18]
  Jian Yang , Guang Yang , Zhijie Chen . Capturing carbon dioxide from air by using amine-functionalized metal-organic frameworks. Chinese Journal of Structural Chemistry, 2024, 43(5): 100267-100267. doi: 10.1016/j.cjsc.2024.100267
19. [19]
  Yue Zhang , Xiaoya Fan , Xun He , Tingyu Yan , Yongchao Yao , Dongdong Zheng , Jingxiang Zhao , Qinghai Cai , Qian Liu , Luming Li , Wei Chu , Shengjun Sun , Xuping Sun . Ambient electrosynthesis of urea from carbon dioxide and nitrate over Mo₂C nanosheet. Chinese Chemical Letters, 2024, 35(8): 109806-. doi: 10.1016/j.cclet.2024.109806
20. [20]
  Xiaxia Xing , Xiaoyu Chen , Zhenxu Li , Xinhua Zhao , Yingying Tian , Xiaoyan Lang , Dachi Yang . Polyethylene imine functionalized porous carbon framework for selective nitrogen dioxide sensing with smartphone communication. Chinese Chemical Letters, 2024, 35(9): 109230-. doi: 10.1016/j.cclet.2023.109230

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(305)
HTML views(14)

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