Chinese Journal of Organic Chemistry >
Synthesis of CO2-Based Re-processable Slight Cross-Linked Polyurea Thermosets
Received date: 2024-05-29
Revised date: 2024-08-22
Online published: 2024-09-10
Supported by
National Natural Science Foundation of China(22172155)
The use of CO2 as monomer to synthesize polymer materials is an important and potential applications topic from the viewpoint of green and sustainable chemistry. A new kind of CO2-based polyurea (PUa) was synthesized by polycondensation of CO2 with 4,7,10-trioxa-1,13-tridecanediamine and tris(2-aminoethyl)amine (TAEA). TAEA was used as cross-link reagent. The mechanical properties of PUa were significantly improved by inserted the crosslink agent of TAEA. The formed slight cross-linked PUa exhibited excellent mechanical properties with tensile strength of 26.8 MPa, elongation at break of 34% and Young’s modulus of 351 MPa. Moreover, it could be remolded for 3 times without obvious change in the mechanical properties, which are ascribed to the hydrogen bonding interaction among the main chains and the slight cross-linked structure. In addition, the synthesized CO2-based PUa is of outstanding thermal performance with an initial decomposition temperature above 300 ℃, besides it is tolerance for a variety of organic solvents.
Key words: CO2; polyurea; non-isocyanate; re-processable; thermoset; slight cross-linking
Wenhan Huang , Shan Jiang , Hui Li , Fengyu Zhao , Haiyang Cheng . Synthesis of CO2-Based Re-processable Slight Cross-Linked Polyurea Thermosets[J]. Chinese Journal of Organic Chemistry, 2024 , 44(10) : 3178 -3184 . DOI: 10.6023/cjoc202405045
| [1] | Donphai, W.; Phichairatanaphong, O.; Fujii, R.; Li, P.; Chang, T.; Yabushita, M.; Nakagawa, Y.; Tomishige, K. Mater. Today Sustain. 2023, 24, 100549. |
| [2] | (a) Dai, X.; Qi, K.; Liu, C.; Lu, X.; Qi, W. Carbon 2023, 202, 51. |
| [2] | (b) Wang, R.; Wan, J.; Guo, H.; Tian, B.; Li, S.; Li, J.; Liu, S.; James, T. D.; Chen, Z. Carbon 2023, 211, 118118. |
| [2] | (c) Zhang, F.; Bulut, S.; Shen, X.; Dong, M.; Wang, Y.; Cheng, X.; Liu, H.; Han, B. Green Chem. 2021, 23, 1147. |
| [3] | (a) Chen, X. W.; Yue, J. P.; Wang, K.; Gui, Y. Y.; Niu, Y. N.; Liu, J.; Ran, C. K.; Kong, W.; Zhou, W. J.; Yu, D. G. Angew. Chem., Int. Ed. 2021, 60, 14068. |
| [3] | (b) Zhang, W.; Liao, L. L.; Li, L.; Liu, Y.; Dai, L. F.; Sun, G. Q.; Ran, C. K.; Ye, J. H.; Lan, Y.; Yu, D. G. Angew. Chem., Int. Ed. 2023, 62, e202301892. |
| [3] | (c) Pan, Y. Z.; Meng, X. J.; Wang, Y. C.; He, M. X. Chin. J. Org. Chem. 2023, 43, 1416. (in Chinese) |
| [3] | (潘永周, 蒙秀金, 王迎春, 何慕雪, 有机化学, 2023, 43, 1416.) |
| [4] | (a) Wu, C. Y.; Cheng, H. Y.; Liu, R. X.; Wang, Q.; Hao, Y. F.; Yu, Y. C.; Zhao, F. Y. Green Chem. 2010, 12, 1811. |
| [4] | (b) Wang, S.; Song, L.; Qu, Z. Chem. Eng. J. 2023, 469, 144008. |
| [5] | (a) Parra, O.; Portillo, A.; Ere?a, J.; Aguayo, A. T.; Bilbao, J.; Ateka, A. Fuel Process. Technol. 2023, 245, 107745. |
| [5] | (b) Kamkeng, A. D. N.; Wang, M. Chem. Eng. J. 2023, 462, 142048. |
| [5] | (c) Huang, W B.; Qiu, L. Q.; Ren, F. Y.; He, L. N. Chin. J. Org. Chem. 2021, 41, 3914. (in Chinese) |
| [5] | (黄文斌, 邱丽琪, 任方煜, 何良年, 有机化学, 2021, 41, 3914.) |
| [5] | (d) Du, J.; Xin, Y.; Dong, M.; Yang, J.; Xu, Q.; Liu, H.; Han, B. Small 2021, 17, 2102629. |
| [6] | (a) Wang, M.; Liu, S.; Chen, X.; Wang, X.; Wang, F. Polym. Chem. 2022, 13, 1731. |
| [6] | (b) Yang, G. W.; Wu, G. P. ACS Sustainable Chem. Eng. 2018, 7, 1372. |
| [6] | (c) Liu, J.; Jia, M.; Gnanou, Y.; Feng, X. Macromolecules 2024, 57, 5380. |
| [7] | (a) Dong, J.; Liu, B.; Ding, H.; Shi, J.; Liu, N.; Dai, B.; Kim, I. Polym. Chem. 2020, 11, 7524. |
| [7] | (b) Poussard, L.; Mariage, J.; Grignard, B.; Detrembleur, C.; Jér?me, C.; Calberg, C.; Heinrichs, B.; De Winter, J.; Gerbaux, P.; Raquez, J. M.; Bonnaud, L.; Dubois, P. Macromolecules 2016, 49, 2162. |
| [7] | (c) Ren, F. Y.; You, F.; Gao, S.; Xie, W. H.; He, L. N.; Li, H. R. Eur. Polym. J. 2021, 153, 110501. |
| [7] | (d) Jiang, S.; Liu, L. Polymer 2022, 244, 124652. |
| [8] | (a) Ou, X.; Zou, X.; Liu, Q.; Li, L.; Li, S.; Cui, Y.; Zhou, Y.; Yan, F. Chem. Mater. 2023, 35, 1218. |
| [8] | (b) Ou, X.; Pan, J.; Liu, Q.; Niu, Y.; Zhou, Y.; Yan, F. Adv. Mater. 2024, 36, 2312906. |
| [8] | (c) Ou, X.; Niu, Y.; Liu, Q.; Li, L.; Wei, F.; Cui, Y.; Zhou, Y.; Yan, F. Prog. Polym. Sci. 2024, 149, 101780. |
| [8] | (d) Wu, P. X.; Wang, X. C.; Shi, R. H.; Cheng, H. Y.; Zhao, F. Y. Green Chem. 2022, 24, 1561. |
| [8] | (e) Li, H.; Huang, W. H.; Zhao, F. Y., Cheng, H. Y. ACS Sustainable Chem. Eng. 2024, 12, 8552. |
| [9] | (a) Inoue, S.; Koinuma, H.; Tsuruta, T. J. Polym. Sci., Part B: Polym. Lett. 1969, 7, 287. |
| [9] | (b) Shi, R. H.; Cheng, H. Y.; Li, H. X.; Wu, P. X.; Zhang, C.; Arai, M.; Zhao, F. Y. Green Energy Environ. 2022, 7, 477. |
| [10] | Grignard, B.; Gennen, S.; Jér?me, C.; Kleij, A. W.; Detrembleur, C. Chem. Soc. Rev. 2019, 48, 4466. |
| [11] | (a) Alagi, P.; Ghorpade, R.; Choi, Y. J.; Patil, U.; Kim, I.; Baik, J. H.; Hong, S. C. ACS Sustainable Chem. Eng. 2017, 5, 3871. |
| [11] | (b) Seychal, G.; Ocando, C.; Bonnaud, L.; De Winter, J.; Grignard, B.; Detrembleur, C.; Sardon, H.; Aramburu, N.; Raquez, J. M. ACS Appl. Polym. Mater. 2023, 5, 5567. |
| [12] | Wu, D.; Martin, R. T.; Pi?a, J.; Kwon, J.; Crockett, M. P.; Thomas, A. A.; Gutierrez, O.; Park, N. H.; Hedrick, J. L.; Campos, L. M. Angew. Chem., Int. Ed. 2024, 63, e202401281. |
| [13] | (a) Xie, S.; Wang, D.; Zhang, S.; Xu, J.; Fu, J. J. Mater. Chem. A 2022, 10, 9457. |
| [13] | (b) Wang, D.; Wang, Z.; Ren, S.; Xu, J.; Wang, C.; Hu, P.; Fu, J. Mater. Horiz. 2021, 8, 2238. |
| [13] | (c) Li, H.; Xu, F.; Wang, J.; Zhang, J.; Wang, H.; Li, Y.; Sun, J. Nano Energy 2023, 108, 108243. |
| [14] | Ritter, B. S.; Mülhaupt, R. Macromol. Mater. Eng. 2016, 302, 1600338. |
| [15] | Li, H.; Cheng, H. Y.; Zhao, F. Y. Asian J. Org. Chem. 2022, 11, e202200338. |
| [16] | Wu, P. X.; Cheng, H. Y.; Shi, R. H.; Jiang, S.; Wu, Q. F.; Zhang, C.; Arai, M.; Zhao, F. Y. Adv. Synth. Catal. 2019, 361, 317. |
| [17] | Zhao, B.; Mei, H.; Wang, H.; Li, L.; Zheng, S. ACS Appl. Polym. Mater. 2021, 4, 509. |
| [18] | (a) Jiang, S.; Cheng, H. Y.; Shi, R. H.; Wu, P. X.; Lin, W. W.; Zhang, C.; Arai, M.; Zhao, F. Y. ACS Appl. Mater. Interfaces 2019, 11, 47413. |
| [18] | (b) Shi, R. H.; Jiang, S.; Cheng, H. Y.; Wu, P. X.; Zhang, C.; Arai, M.; Zhao, F. Y. ACS Sustainable Chem. Eng. 2020, 8, 18626. |
| [19] | Jiang, S.; Shi, R. H.; Cheng, H. Y.; Zhang, C.; Zhao, F. Y. Green Energy Environ. 2017, 2, 370. |
| [20] | Guo, Z.; Bao, C.; Wang, X.; Lu, X.; Sun, H.; Li, X.; Li, J.; Sun, J. J. Mater. Chem. A 2021, 9, 11025. |
/
| 〈 |
|
〉 |