Citation: Yan Peng, Yu-jia Hou, Qiao-qiao Shen, Hui Wang, Gang Li, Guang-su Huang, Jin-rong Wu. Synthesis and Performance of a Double Network Self-healing Elastomer Based on Hydrogen Bonds and Diels-Alder Crosslinks[J]. Acta Polymerica Sinica, ;2020, 51(2): 158-165. doi: 10.11777/j.issn1000-3304.2019.19140 shu

Synthesis and Performance of a Double Network Self-healing Elastomer Based on Hydrogen Bonds and Diels-Alder Crosslinks

Yan Peng ^1,† ,
Yu-jia Hou ^1,† ,
Qiao-qiao Shen ¹ ,
Hui Wang ² ,
Gang Li ² ,
Guang-su Huang ¹ ,
Jin-rong Wu ^1,,

1.
State Key Laboratory of Polymer Materials Engineering, College of Polymer Science and Engineering,Sichuan University, Chengdu 610065
2.
Science and Technology on Reactor Fuel and Materials Laboratory, Nuclear Power Institute of China, Chengdu 610041

Corresponding author: Jin-rong Wu, wujinrong@scu.edu.cn
Received Date: 31 July 2019
Revised Date: 23 August 2019

Intrinsic self-healing elastomers, which can automatically heal themselves after damage without the addition of other reagents, have recently attracted increasing attention. However, a trade-off commonly exists between high mechanical properties and high self-healing efficiency, which is always the bottle-neck in advancing these high performance self-healing elastomers. To solve this problem, a high performance and high self-healing efficiency elastomer was developed in this work based on hydrogen bonds and Diles-Alder (DA) crosslinks. Firstly, a monomer (HM) functionalized with amido bond and carbamic acid ester for the generation of hydrogen bonds was synthesized by N-butyl isocyanate and N-(2-hydroxyethyl)acrylamide. Next, one-pot free-radical copolymerization of HM, butyl acrylate (BA), and furfuryl methacrylate (FMA) was carried out to afford a linear copolymer, which was only cross-linked with hydrogen bonds. Finally, bismaleimide (BMI) was used to crosslink the linear copolymer through DA reaction. A double network self-healing elastomer with two kinds of crosslinks, i.e. hydrogen bonds and DA bonds, was thus prepared. The heating-up and cooling down FTIR spectroscopy was used to characterize the hydrogen bonds, while the existence of DA bonds was proved by FTIR, DSC, and DMA techniques. When an external force was applied, the hydrogen bonds broke firstly to dissipate energy, which helped to increase the toughness by about 6.2 times, the tensile strength by about 12.3 times, and Young’s modulus of the elastomer by about 26 times. Meanwhile, DA crosslinks endowed the elastomer with certain elasticity and the capability of fast shape recovery. Moreover, thanks to the reversible ability of hydrogen bonds and DA crosslinks, the elastomer exhibited a high self-healing efficiency up to 98%.
- Mechanical properties,
- Self-healing,
- Elastomer,
- Double networks
1. [1]
  Murphy E B, Wudl F. Prog Polym Sci, 2010, 35: 223 − 251 doi: 10.1016/j.progpolymsci.2009.10.006
2. [2]
  Cordier P, Tournilhac F, Soulie-Ziakovic C, Leibler L. Nature, 2008, 451: 977 − 980 doi: 10.1038/nature06669
3. [3]
  Montarnal D, Tournilhac F, Hidalgo M, Couturier J L, Leibler L. J Am Chem Soc, 2009, 131: 7966 − 7967 doi: 10.1021/ja903080c
4. [4]
  Sun T L, Kurokawa T, Kuroda S, Bin Ihsan A, Akasaki T, Sato K, Haque M A, Nakajima T, Gong J P. Nat Mater, 2013, 12: 932 − 937 doi: 10.1038/nmat3713
5. [5]
  van Gemert G M L, Peeters J W, Sontjens S H M, Janssen H M, Bosman A W. Macromol Chem Phys, 2012, 213: 234 − 242 doi: 10.1002/macp.201100559
6. [6]
  Das A, Sallat A, Boehme F, Suckow M, Basu D, Wiessner S, Stoeckelhuber K W, Voit B, Heinrich G. ACS Appl Mater Interfaces, 2015, 7: 20623 − 20630 doi: 10.1021/acsami.5b05041
7. [7]
  Wang D, Guo J, Zhang H, Cheng B, Shen H, Zhao N, Xu J. J Mater Chem A, 2015, 3: 12864 − 12872 doi: 10.1039/C5TA01915J
8. [8]
  Burnworth M, Tang L, Kumpfer J R, Duncan A J, Beyer F L, Fiore G L, Rowan S J, Weder C. Nature, 2011, 472: 334 − 337 doi: 10.1038/nature09963
9. [9]
  Wang Z, Yang Y, Burtovyy R, Luzinov I, Urban M W. J Mater Chem A, 2014, 2: 15527 − 15534 doi: 10.1039/C4TA02417F
10. [10]
  Fox J, Wie J J, Greenland B W, Burattini S, Hayes W, Colquhoun H M, Mackay M E, Rowan S J. J Am Chem Soc, 2012, 134: 5362 − 5368 doi: 10.1021/ja300050x
11. [11]
  Burattini S, Colquhoun H M, Fox J D, Friedmann D, Greenland B W, Harris P J F, Hayes W, Mackay M E, Rowan S J. Chem Commun, 2009, 44: 6717 − 6719
12. [12]
  Tao Jie(陶杰), Lin Cuiling(林翠玲), Wang Zhaolong(王兆龙), Wei Bin(魏斌), Hua Qixia(华奇侠), Wan Xueting (万雪婷), Qiu Huayu(邱化玉), Yin Shouchun(尹守春). Acta Polymerica Sinica(高分子学报), 2017, (1): 93 − 100 doi: 10.11777/j.issn1000-3304.2017.16244
13. [13]
  Froidevaux V, Borne M, Laborbe E, Auvergne R, Gandini A, Boutevin B. RSC Adv, 2015, 5: 37742 − 37754 doi: 10.1039/C5RA01185J
14. [14]
  Zeng C, Seino H, Ren J, Hatanaka K, Yoshie N. Polymer, 2013, 54: 5351 − 5357 doi: 10.1016/j.polymer.2013.07.059
15. [15]
  Bai N, Simon G P, Saito K. New J Chem, 2015, 39: 3497 − 3506 doi: 10.1039/C5NJ00066A
16. [16]
  Deng G, Tang C, Li F, Jiang H, Chen Y. Macromolecules, 2010, 43: 1191 − 1194 doi: 10.1021/ma9022197
17. [17]
  Kim S M, Jeon H, Shin S H, Park S A, Jegal J, Hwang S Y, Oh D X, Park J. Adv Mater, 2018, 30: 1705145 doi: 10.1002/adma.201705145
18. [18]
  Sastri V R, Tesoro G C. J Appl Polym Sci, 2010, 39: 1439 − 1457
19. [19]
  Yuan C E, Rong M Z, Zhang M Q, Zhang Z P, Yuan Y C. Chem Mater, 2011, 23: 5076 − 5081 doi: 10.1021/cm202635w
20. [20]
  Peng Y, Yang Y, Wu Q, Wang S X, Huang G S, Wu J R. Polymer, 2018, 157: 172 − 179 doi: 10.1016/j.polymer.2018.09.038
21. [21]
  Wu J, Cai L H, Weitz D A. Adv Mater, 2017, 29: 1702616 doi: 10.1002/adma.201702616
22. [22]
  Wei Z, He J, Liang T, Oh H, Athas J, Tong Z, Wang C, Nie Z. Polym Chem, 2013, 4: 4601 − 4605 doi: 10.1039/c3py00692a
23. [23]
  Ding Xiaoya(丁晓亚), Wang Yu(王宇), Li Gao(李杲), Xiao Chunsheng(肖春生), Chen Xuesi(陈学思). Acta Polymerica Sinica(高分子学报), 2019, 50(5): 505 − 515 doi: 10.11777/j.issn1000-3304.2019.19015
24. [24]
  Tian Lirong(田丽蓉), Yang Li(杨莉), Wang Zhanhua(王占华), Xia Hesheng(夏和生). Acta Polymerica Sinica(高分子学报), 2019, 50(5): 527 − 534 doi: 10.11777/j.issn1000-3304.2019.19021
25. [25]
  Roy N, Buhler E, Lehn J M. Polym Int, 2014, 63: 1400 − 1405 doi: 10.1002/pi.4646
26. [26]
  Neal J A, Mozhdehi D, Guan Z. J Am Chem Soc, 2015, 137: 4846 − 4850 doi: 10.1021/jacs.5b01601
27. [27]
  Feng Z, Zuo H, Gao W, Ning N, Tian M, Zhang L. Macromol Rapid Commun, 2018, 39: 1800138 doi: 10.1002/marc.201800138
28. [28]
  Suematsu K, Kodama K, Ma N, Yuasa M, Kida T, Shimanoe K. RSC Adv, 2016, 6: 5169 − 5176 doi: 10.1039/C5RA20994C
29. [29]
  Liu Y L, Hsieh C Y. J Polym Sci, Part A: Polym Chem, 2006, 44: 905 − 913 doi: 10.1002/pola.21184
30. [30]
  Feng L, Yu Z, Bian Y, Lu J, Shi X, Chai C. Polymer, 2017, 124: 48 − 59 doi: 10.1016/j.polymer.2017.07.049
31. [31]
  Tian Q, Yuan Y C, Rong M Z, Zhang M Q. J Mater Chem, 2009, 19: 1289 − 1296 doi: 10.1039/b811938d
1. [1]
  Feng Zheng , Ruxun Yuan , Xiaogang Wang . “Research-Oriented” Comprehensive Experimental Design in Polymer Chemistry: the Case of Polyimide Aerogels. University Chemistry, 2024, 39(10): 210-218. doi: 10.12461/PKU.DXHX202404027
2. [2]
  Xuzhen Wang , Xinkui Wang , Dongxu Tian , Wei Liu . Enhancing the Comprehensive Quality and Innovation Abilities of Graduate Students through a “Student-Centered, Dual Integration and Dual Drive” Teaching Model: A Case Study in the Course of Chemical Reaction Kinetics. University Chemistry, 2024, 39(6): 160-165. doi: 10.3866/PKU.DXHX202401074
3. [3]
  Peifeng Su , Xin Lu . Development of Undergraduate Quantum Mechanics Module in Chemistry Department under the “Double First Class” Initiative. University Chemistry, 2024, 39(8): 99-103. doi: 10.3866/PKU.DXHX202401087
4. [4]
  Lei Shu , Zhengqing Hao , Kai Yan , Hong Wang , Lihua Zhu , Fang Chen , Nan Wang . Development of a Double-Carbon Related Experiment: Preparation, Characterization and Carbon-Capture Ability of Eggshell-Derived CaO. University Chemistry, 2024, 39(4): 149-156. doi: 10.3866/PKU.DXHX202310134
5. [5]
  Linjie ZHU , Xufeng LIU . Electrocatalytic hydrogen evolution performance of tetra-iron complexes with bridging diphosphine ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 321-328. doi: 10.11862/CJIC.20240207
6. [6]
  Juan WANG , Zhongqiu WANG , Qin SHANG , Guohong WANG , Jinmao LI . NiS and Pt as dual co-catalysts for the enhanced photocatalytic H₂ production activity of BaTiO₃ nanofibers. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1719-1730. doi: 10.11862/CJIC.20240102
7. [7]
  Yuanchao LI , Weifeng HUANG , Pengchao LIANG , Zifang ZHAO , Baoyan XING , Dongliang YAN , Li YANG , Songlin WANG . Effect of heterogeneous dual carbon sources on electrochemical properties of LiMn_0.8Fe_0.2PO₄/C composites. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 751-760. doi: 10.11862/CJIC.20230252
8. [8]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
9. [9]
  Fengqiao Bi , Jun Wang , Dongmei Yang . Specialized Experimental Design for Chemistry Majors in the Context of “Dual Carbon”: Taking the Assembly and Performance Evaluation of Zinc-Air Fuel Batteries as an Example. University Chemistry, 2024, 39(4): 198-205. doi: 10.3866/PKU.DXHX202311069
10. [10]
  Zhenyu Feng , Zhaozhen Cao , Jinhua Zhan . Exploration of Online Training System for Large-Scale Instrument in Open Laboratory of Universities. University Chemistry, 2024, 39(4): 1-6. doi: 10.3866/PKU.DXHX202311016
11. [11]
  Haolin Zhan , Qiyuan Fang , Jiawei Liu , Xiaoqi Shi , Xinyu Chen , Yuqing Huang , Zhong Chen . Noise Reduction of Nuclear Magnetic Resonance Spectroscopy Using Lightweight Deep Neural Networ. Acta Physico-Chimica Sinica, 2025, 41(2): 100017-. doi: 10.3866/PKU.WHXB202310045
12. [12]
  Qiqi Li , Su Zhang , Yuting Jiang , Linna Zhu , Nannan Guo , Jing Zhang , Yutong Li , Tong Wei , Zhuangjun Fan . 前驱体机械压实制备高密度活性炭及其致密电容储能性能. Acta Physico-Chimica Sinica, 2025, 41(3): 2406009-. doi: 10.3866/PKU.WHXB202406009
13. [13]
  Hongyi LI , Aimin WU , Liuyang ZHAO , Xinpeng LIU , Fengqin CHEN , Aikui LI , Hao HUANG . Effect of Y(PO₃)₃ double-coating modification on the electrochemical properties of Li[Ni_0.8Co_0.15Al_0.05]O₂. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1320-1328. doi: 10.11862/CJIC.20230480
14. [14]
  Cheng Zheng , Shiying Zheng , Yanping Zhang , Shoutian Zheng , Qiaohua Wei . Synthesis, Copper Content Analysis, and Luminescent Performance Study of Binuclear Copper (I) Complexes with Isomeric Luminescence Shift: A Comprehensive Chemical Experiment Recommendation. University Chemistry, 2024, 39(7): 322-329. doi: 10.3866/PKU.DXHX202310131
15. [15]
  Simin Fang , Wei Huang , Guanghua Yu , Cong Wei , Mingli Gao , Guangshui Li , Hongjun Tian , Wan Li . Integrating Science and Education in a Comprehensive Chemistry Design Experiment: The Preparation of Copper(I) Oxide Nanoparticles and Its Application in Dye Water Remediation. University Chemistry, 2024, 39(8): 282-289. doi: 10.3866/PKU.DXHX202401023
16. [16]
  Bowen Yang , Rui Wang , Benjian Xin , Lili Liu , Zhiqiang Niu . C-SnO₂/MWCNTs Composite with Stable Conductive Network for Lithium-based Semi-Solid Flow Batteries. Acta Physico-Chimica Sinica, 2025, 41(2): 100015-. doi: 10.3866/PKU.WHXB202310024
17. [17]
  Jiahong ZHENG , Jingyun YANG . Preparation and electrochemical properties of hollow dodecahedral CoNi₂S₄ supported by MnO₂ nanowires. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1881-1891. doi: 10.11862/CJIC.20240170
18. [18]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
19. [19]
  Tieping CAO , Yuejun LI , Dawei SUN . Surface plasmon resonance effect enhanced photocatalytic CO₂ reduction performance of S-scheme Bi₂S₃/TiO₂ heterojunction. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 903-912. doi: 10.11862/CJIC.20240366
20. [20]
  Jin Yan , Chengxia Tong , Yajie Li , Yue Gu , Xuejian Qu , Shigang Wei , Wanchun Zhu , Yupeng Guo . Construction of a “Dual Support, Triple Integration” Chemical Safety Practical Education System. University Chemistry, 2024, 39(7): 69-75. doi: 10.12461/PKU.DXHX202405008

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(150)
HTML views(25)

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