Synthesis of CO2-Based Re-processable Slight Cross-Linked Polyurea Thermosets

doi:10.6023/cjoc202405045

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (10): 3178-3184.DOI: 10.6023/cjoc202405045 Previous Articles Next Articles

ARTICLES

二氧化碳基可再加工微交联热固性聚脲的合成

黄文翰^a^,^b,†, 姜山^c,†, 李慧^a^,^b, 赵凤玉^a^,^b^,^*(), 程海洋^a^,^b^,^*()

a 中国科学院长春应用化学研究所电分析化学国家重点实验室吉林省绿色化学与过程重点实验室长春 130022
b 中国科学技术大学应用化学与工程学院合肥 230026
c 上海大学材料科学与工程学院上海 200444

收稿日期:2024-05-29 修回日期:2024-08-22 发布日期:2024-09-10
作者简介:^†共同第一作者
基金资助:
国家自然科学基金(22172155)

Synthesis of CO₂-Based Re-processable Slight Cross-Linked Polyurea Thermosets

Wenhan Huang^a^,^b,†, Shan Jiang^c,†, Hui Li^a^,^b, Fengyu Zhao^a^,^b,*(), Haiyang Cheng^a^,^b,*()

a Jilin Provincial Key Laboratory of Green Chemistry and Process, State Key Laboratory of Electroanalytical Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022
b School of Applied Chemistry and Engineering, University of Science and Technology of China, Hefei 230026
c School of Materials Science and Engineering, Shanghai University, Shanghai 200444

Received:2024-05-29 Revised:2024-08-22 Published:2024-09-10
Contact: *E-mail: zhaofy@ciac.ac.cn;hycyl@ciac.ac.cn
About author:^†These authors contributed equally to this work
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

Cite this article

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.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 9

Scheme 1. Synthesis of slight cross-linked polyurea from CO2 and diamine

Figure 1. FTIR spectra of (a) TTD100, (b) TTD100-TAEA1.9, (c) TTD100-TAEA3.7, (d) TTD100-TAEA5.5

Figure 2. Solid 13C NMR of TTD100 and TTD100-TAEA3.7

Figure 3. XRD of TTD100, TTD100-TAEA1.9, TTD100-TAEA3.7, TTD100-TAEA5.5

Figure 4. (a) DSC and (b) TGA of TTD100, TTD100-TAEA1.9, TTD100-TAEA3.7 and TTD100-TAEA5.5

Figure 5. (a) Hot-press recovery diagrams and (b) stress-strain curves of TTD100, TTD100-TAEA1.9, TTD100-TAEA3.7, TTD100-TAEA5.5; (c) Stress-strain curves of reprocessed TTD100-TAEA3.7

Figure 6. ATR-FTIR of TTD100-TAEA3.7 with increasing temperature

Figure 7. Stress-strain curves of aged samples and original TTD100-TAEA3.7

Figure 8. (a) Swelling test images, and (b) swelling ratio and gel fraction of TTD100-TAEA3.7 in different solvent

References 20

[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.
	(b) Wang, R.; Wan, J.; Guo, H.; Tian, B.; Li, S.; Li, J.; Liu, S.; James, T. D.; Chen, Z. Carbon 2023, 211, 118118.
	(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.
	(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.
	(c) Pan, Y. Z.; Meng, X. J.; Wang, Y. C.; He, M. X. Chin. J. Org. Chem. 2023, 43, 1416. (in Chinese)
	(潘永周, 蒙秀金, 王迎春, 何慕雪, 有机化学, 2023, 43, 1416.) doi: 10.6023/cjoc202208004
[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.
	(b) Wang, S.; Song, L.; Qu, Z. Chem. Eng. J. 2023, 469, 144008.
[5]	(a) Parra, O.; Portillo, A.; Ereña, J.; Aguayo, A. T.; Bilbao, J.; Ateka, A. Fuel Process. Technol. 2023, 245, 107745.
	(b) Kamkeng, A. D. N.; Wang, M. Chem. Eng. J. 2023, 462, 142048.
	(c) Huang, W B.; Qiu, L. Q.; Ren, F. Y.; He, L. N. Chin. J. Org. Chem. 2021, 41, 3914. (in Chinese)
	(黄文斌, 邱丽琪, 任方煜, 何良年, 有机化学, 2021, 41, 3914.)
	(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.
	(b) Yang, G. W.; Wu, G. P. ACS Sustainable Chem. Eng. 2018, 7, 1372.
	(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.
	(b) Poussard, L.; Mariage, J.; Grignard, B.; Detrembleur, C.; Jérôme, C.; Calberg, C.; Heinrichs, B.; De Winter, J.; Gerbaux, P.; Raquez, J. M.; Bonnaud, L.; Dubois, P. Macromolecules 2016, 49, 2162.
	(c) Ren, F. Y.; You, F.; Gao, S.; Xie, W. H.; He, L. N.; Li, H. R. Eur. Polym. J. 2021, 153, 110501.
	(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.
	(b) Ou, X.; Pan, J.; Liu, Q.; Niu, Y.; Zhou, Y.; Yan, F. Adv. Mater. 2024, 36, 2312906.
	(c) Ou, X.; Niu, Y.; Liu, Q.; Li, L.; Wei, F.; Cui, Y.; Zhou, Y.; Yan, F. Prog. Polym. Sci. 2024, 149, 101780.
	(d) Wu, P. X.; Wang, X. C.; Shi, R. H.; Cheng, H. Y.; Zhao, F. Y. Green Chem. 2022, 24, 1561.
	(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.
	(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.; Jérôme, C.; Kleij, A. W.; Detrembleur, C. Chem. Soc. Rev. 2019, 48, 4466. doi: 10.1039/c9cs00047j pmid: 31276137
[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.
	(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.; Piña, 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.
	(b) Wang, D.; Wang, Z.; Ren, S.; Xu, J.; Wang, C.; Hu, P.; Fu, J. Mater. Horiz. 2021, 8, 2238.
	(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.
	(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.

二氧化碳基可再加工微交联热固性聚脲的合成

Synthesis of CO₂-Based Re-processable Slight Cross-Linked Polyurea Thermosets

RichHTML

PDF

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 9

References 20

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Jinbin Gao, Yingqi Lu, Hui Zhang, Lizhu Gao, Xingquan Xiong. Application of Biobased Catalysts in Chemical Conversion of CO₂ [J]. Chinese Journal of Organic Chemistry, 2024, 44(9): 2732-2741.
[2]	Yingzhe Zhao, Zixuan Zhang, Jianling Zhang, Renjie Zhang, Meiling Li, Yunan Teng, Haoxiang Wang. Synthesis of Cerium Doped Zirconium-Based Metal-Organic Framework Nanoparticles and Their Photocatalytic Performance for Carbon Dioxide Cycloaddition [J]. Chinese Journal of Organic Chemistry, 2024, 44(10): 3169-3177.
[3]	Kaiyue Wang, Mingnuo Xu, Bo Li, Guangpeng Wu. Application of Bifunctional Thiourea Catalyst in One Pot Preparation of Polypeptides and Cyclic Carbonates [J]. Chinese Journal of Organic Chemistry, 2024, 44(10): 3206-3212.
[4]	Jianwen Li, Tao Wang, Sheng Tao, Fei Chen, Min Li, Ning Liu. N-Heterocyclic Carbene-Pyridine Molybdenum Complex Supported over SBA-15 for Converting of Carbon Dioxide into Cyclic Carbonates [J]. Chinese Journal of Organic Chemistry, 2024, 44(10): 3213-3222.
[5]	Jun He, Hongxing Wang, Chenglong Yu, Yanru Zhang, Ying Wang, Yanyan Wang, Longbo Zhang, Jia Guo, Qingli Qian, Buxing Han. Nanoflower-Shaped Ir/MoS₂ Catalyst for Highly Selective Production of Formate by CO₂ Hydrogenation [J]. Chinese Journal of Organic Chemistry, 2024, 44(10): 3223-3232.
[6]	Xuewei Chen, Fangcai Yu, Chuanhong Tian. 1,1'-Methylenediimidazolium-Based Multiple Hydrogen-Bond Donor Catalysts Facilitate the Cycloaddition of CO₂ with Epoxides under Atmospheric Pressure [J]. Chinese Journal of Organic Chemistry, 2024, 44(10): 3198-3205.
[7]	Yujia Zhou, Qiao Kong, Daoyong Zhu, Shaohua Wang. Synthesis of N-Arylpyrrolidines Using CO₂ as C1 Source [J]. Chinese Journal of Organic Chemistry, 2024, 44(10): 3185-3197.
[8]	Yanwei Wang, Weiwei Chen, Dan Yuan, Yong Zhang, Yingming Yao. Advances in the Reactions of CO₂ and Epoxides Catalyzed by Heterometallic Complexes [J]. Chinese Journal of Organic Chemistry, 2024, 44(10): 3063-3076.
[9]	Wenke Li, Beiqi Sun, Lei Zhang, Fanyang Mo. Recent Advances in Photocatalytic Carboxylation Based on Free Radical Process [J]. Chinese Journal of Organic Chemistry, 2024, 44(10): 2961-2996.
[10]	Qin Shi, Zhen Li, Lin He, Yudong Li, Yuehui Li. Boron-Promoted Co-Catalyzed N-Methylation of Secondary Aromatic Amines with CO₂ and H₂ [J]. Chinese Journal of Organic Chemistry, 2024, 44(10): 3233-3240.
[11]	Qiuting Zhao, Wenguang Wang. Iron-Catalyzed Selective Hydrogenation and Hydroboration/Hydrosilylation of CO₂ [J]. Chinese Journal of Organic Chemistry, 2024, 44(10): 3106-3116.
[12]	Hui Xu, Huixian Jiang, Lei Kan, Pei Xu, Xu Zhu. Visible-Light-Induced Selective Hydrocarboxylation of Alkynes with Formate [J]. Chinese Journal of Organic Chemistry, 2024, 44(10): 3241-3248.
[13]	Lu Liu, Shuguang Zhang, Renwei Hu, Xiaoxiao Zhao, Jingnan Cui, Weitao Gong. Synthesis and Properties of Phenolic Resin Polymers Based on Pillar[5]arene [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2808-2814.
[14]	Lijuan Xiao, Yanping Zhang, Miao Hong. Research Progress of Lewis Acid and Base Pairs Applied in Materials Chemistry [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 949-960.
[15]	Guijie Liu, Zhengqiang Fu, Fei Chen, Caixia Xu, Min Li, Ning Liu. N-Heterocyclic Carbene-Pyridine Manganese Complex/ Tetrabutylammonium Iodide Catalyzed Synthesis of Cyclic Carbonate from CO₂ and Epoxide [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 629-635.