

FOLLOWUS
State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, Shanghai Belt and Road Joint Laboratory of Advanced Fiber and Low-dimension Materials (Donghua University), College of Materials Science and Engineering, Shanghai Engineering Research Center of Nano-Biomaterials and Regenerative Medicine, Donghua University, Shanghai 201620, China
zyou@dhu.edu.cn
Received:13 May 2021,
Revised:2021-6-17,
Accepted:23 June 2021,
Online First:17 August 2021,
Published:20 August 2021
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Zhang, L.; You, Z. Dynamic oxime-urethane bonds, a versatile unit of high performance self-healing polymers for diverse applications. Chinese J. Polym. Sci. 2021, 39, 1281–1291
Luzhi Zhang, Zhengwei You. Dynamic Oxime-Urethane Bonds, a Versatile Unit of High Performance Self-healing Polymers for Diverse Applications[J]. Chinese Journal of Polymer Science, 2021, 39(10): 1281-1291.
Zhang, L.; You, Z. Dynamic oxime-urethane bonds, a versatile unit of high performance self-healing polymers for diverse applications. Chinese J. Polym. Sci. 2021, 39, 1281–1291 DOI: 10.1007/s10118-021-2625-9.
Luzhi Zhang, Zhengwei You. Dynamic Oxime-Urethane Bonds, a Versatile Unit of High Performance Self-healing Polymers for Diverse Applications[J]. Chinese Journal of Polymer Science, 2021, 39(10): 1281-1291. DOI: 10.1007/s10118-021-2625-9.
Oxime-urethane bond featuring with high reversibility even at room temperature and multiple reactivity is an emerging dynamic covalent bond
and has shown great potential for self-healing polymers
which are one of the most attractive development directions for next generation of polymeric materials. In this review
recent progresses on the oxime-urethane-based self-healing polymers
including their designs and applications in diverse fields such as biomedicine
flexible electronics
soft robots
3D printing
protective materials
and adhesives
are summarized
and outlooks on the future development of this field are discussed.
Diesendruck, C. E.; Sottos, N. R.; Moore, J. S. White S. R. . Biomimetic self-healing . Angew. Chem. Int. Ed. , 2015 . 54 10428 - 10447 . DOI: 10.1002/anie.201500484 http://doi.org/10.1002/anie.201500484 .
Patrick, J. F.; Robb, M. J.; Sottos, N. R.; Moore, J. S. White, S. R. . Polymers with autonomous life-cycle control . Nature , 2016 . 540 363 - 370 . DOI: 10.1038/nature21002 http://doi.org/10.1038/nature21002 .
Aguirresarobe, R. H.; Nevejans, S.; Reck, B.; Irusta, L.; Sardon, H.; Asua, J. M. Ballard, N. . Healable and self-healing polyurethanes using dynamic chemistry . Prog. Polym. Sci. , 2021 . 114 101362 DOI: 10.1016/j.progpolymsci.2021.101362 http://doi.org/10.1016/j.progpolymsci.2021.101362 .
Zheng, N.; Xu, Y.; Zhao, Q. Xie, T. . Dynamic covalent polymer networks: a molecular platform for designing functions beyond chemical recycling and self-healing . Chem. Rev. , 2021 . 121 1716 - 1745 . DOI: 10.1021/acs.chemrev.0c00938 http://doi.org/10.1021/acs.chemrev.0c00938 .
Li, C. H. Zuo, J. L. . Self-healing polymers based on coordination bonds . Adv. Mater. , 2020 . 32 1903762 .
White, S. R.; Sottos, N. R.; Geubelle, P. H.; Moore, J. S.; Kessler, M. R.; Sriram, S. R.; Brown, E. N. Viswanathan, S. . Autonomic healing of polymer composites . Nature , 2001 . 409 794 - 797 . DOI: 10.1038/35057232 http://doi.org/10.1038/35057232 .
Toohey, K. S.; Sottos, N. R.; Lewis, J. A.; Moore, J. S. White, S. R. . Self-healing materials with microvascular networks . Nat. Mater. , 2007 . 6 581 - 585 . DOI: 10.1038/nmat1934 http://doi.org/10.1038/nmat1934 .
Hansen, C. J.; Wu, W.; Toohey, K. S.; Sottos, N. R.; White, S. R. Lewis, J. A. . Self-healing materials with interpenetrating microvascular networks . Adv. Mater. , 2009 . 21 4143 - 4147 . DOI: 10.1002/adma.200900588 http://doi.org/10.1002/adma.200900588 .
Utrera-Barrios, S.; Verdejo, R.; Lopez-Manchado, M. A. Hernandez Santana, M. . Evolution of self-healing elastomers, from extrinsic to combined intrinsic mechanisms: a review . Mater. Horiz. , 2020 . 7 2882 - 2902 . DOI: 10.1039/D0MH00535E http://doi.org/10.1039/D0MH00535E .
Chen, S.; Bi, X.; Sun, L.; Gao, J.; Huang, P.; Fan, X.; You, Z. Wang, Y. . Poly(sebacoyl diglyceride) cross-linked by dynamic hydrogen bonds: a self-healing and functionalizable thermoplastic bioelastomer . ACS Appl. Mater. Interfaces , 2016 . 8 20591 - 20599 . DOI: 10.1021/acsami.6b05873 http://doi.org/10.1021/acsami.6b05873 .
Zhang, L.; Liang, J.; Jiang, C.; Liu, Z.; Sun, L.; Chen, S.; Xuan, H.; Lei, D.; Guan, Q.; Ye, X. You, Z. . Peptidoglycan-inspired autonomous ultrafast self-healing bio-friendly elastomers for bio-integrated electronics . Natl. Sci. Rev. , 2021 . 8 nwaa154 DOI: 10.1093/nsr/nwaa154 http://doi.org/10.1093/nsr/nwaa154 .
Shi, Z.; Wang, Q.; Li, G. F.; Shou, Y. F.; Zong, H. J.; Yan, S. F.; Zhang, K. X. Yin, J. B. . Preparation and characterization of attractive poly(amino acid) hydrogels based on 2-ureido-4[1 H ]-pyrimidinone . Chinese J. Polym. Sci. , 2021 . 39 327 - 336 . DOI: 10.1007/s10118-021-2498-y http://doi.org/10.1007/s10118-021-2498-y .
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. . A self-repairing, supramolecular polymer system: Healability as a consequence of donor-acceptor π-π stacking interactions . Chem. Commun. , 2009 . 6717 - 6719 . .
Burattini, S.; Greenland, B. W.; Merino, D. H.; Weng, W.; Seppala, J.; Colquhoun, H. M.; Hayes, W.; Mackay, M. E.; Hamley, I. W. Rowan, S. J. . A healable supramolecular polymer blend based on aromatic π-π stacking and hydrogen-bonding interactions . J. Am. Chem. Soc. , 2010 . 132 12051 - 12058 . DOI: 10.1021/ja104446r http://doi.org/10.1021/ja104446r .
Wang, J. J.; Zhang, Q.; Ji, X. X. Liu, L. B. . Highly stretchable, compressible, adhesive, conductive self-healing composite hydrogels with sensor capacity . Chinese J. Polym. Sci. , 2020 . 38 1221 - 1229 . DOI: 10.1007/s10118-020-2472-0 http://doi.org/10.1007/s10118-020-2472-0 .
Peng, L.; Zhang, H.; Feng, A.; Huo, M.; Wang, Z.; Hu, J.; Gao, W. Yuan, J. . Electrochemical redox responsive supramolecular self-healing hydrogels based on host-guest interaction . Polym. Chem. , 2015 . 6 3652 - 3659 . DOI: 10.1039/C5PY00296F http://doi.org/10.1039/C5PY00296F .
Wang, Z.; An, G.; Zhu, Y.; Liu, X.; Chen, Y.; Wu, H.; Wang, Y.; Shi, X. Mao, C. . 3D-printable self-healing and mechanically reinforced hydrogels with host–guest non-covalent interactions integrated into covalently linked networks . Mater. Horiz. , 2019 . 6 733 - 742 . DOI: 10.1039/C8MH01208C http://doi.org/10.1039/C8MH01208C .
Lai, J. C.; Jia, X. Y.; Wang, D. P.; Deng, Y. B.; Zheng, P.; Li, C. H.; Zuo, J. L. Bao, Z. . Thermodynamically stable whilst kinetically labile coordination bonds lead to strong and tough self-healing polymers . Nat. Commun. , 2019 . 10 1164 DOI: 10.1038/s41467-019-09130-z http://doi.org/10.1038/s41467-019-09130-z .
Li, C. H.; Wang, C.; Keplinger, C.; Zuo, J. L.; Jin, L.; Sun, Y.; Zheng, P.; Cao, Y.; Lissel, F.; Linder, C.; You, X. Z. Bao, Z. . A highly stretchable autonomous self-healing elastomer . Nat. Chem. , 2016 . 8 618 - 624 . DOI: 10.1038/nchem.2492 http://doi.org/10.1038/nchem.2492 .
Li, M. X.; Rong, M. Z. Zhang, M. Q. . Reversible mechanochemistry enabled autonomous sustaining of robustness of polymers-an example of next generation self-healing strategy . Chinese J. Polym. Sci. , 2021 . 39 545 - 553 . DOI: 10.1007/s10118-021-2532-0 http://doi.org/10.1007/s10118-021-2532-0 .
Yin, Q. Y.; Dai, C. H.; Chen, H.; Gou, K.; Guan, H. Z.; Wang, P. H.; Jiang, J. T. Weng, G. S. . Tough double metal-ion cross-linked elastomers with temperature-adaptable self-healing and luminescence properties . Chinese J. Polym. Sci. , 2021 . 39 554 - 565 . DOI: 10.1007/s10118-021-2517-z http://doi.org/10.1007/s10118-021-2517-z .
Sun, L.; Huang, H.; Ding, Q.; Guo, Y.; Sun, W.; Wu, Z.; Qin, M.; Guan, Q.; You, Z . Highly transparent, stretchable, and self-healable ionogel for multifunctional sensors, triboelectric nanogenerator, and wearable fibrous electronics . Adv. Fiber Mater. , 2021 . DOI: 10.1007/s42765-021-00086-8 DOI: 10.1007/s42765-021-00086-8 http://doi.org/10.1007/s42765-021-00086-8 .
Bose, R. K.; Hohlbein, N.; Garcia, S. J.; Schmidt, A. M. van der Zwaag, S. . Connecting supramolecular bond lifetime and network mobility for scratch healing in poly(butyl acrylate) ionomers containing sodium, zinc and cobalt . Phys. Chem. Chem. Phys. , 2015 . 17 1697 - 1704 . DOI: 10.1039/C4CP04015E http://doi.org/10.1039/C4CP04015E .
Urban, M.W.; Davydovich, D.; Yang, Y.; Demir, T.; Zhang, Y. Casabianca, L. . Key-and-lock commodity self-healing copolymers . Science , 2018 . 362 220 - 225 . DOI: 10.1126/science.aat2975 http://doi.org/10.1126/science.aat2975 .
Susa, A.; Bose, R. K.; Grande, A. M.; van der Zwaag, S. Garcia, S. J. . Effect of the dianhydride/branched diamine ratio on the architecture and room temperature healing behavior of polyetherimides . ACS Appl. Mater. Interfaces , 2016 . 8 34068 - 34079 . DOI: 10.1021/acsami.6b10433 http://doi.org/10.1021/acsami.6b10433 .
Zou, Z.; Zhu, C.; Li, Y.; Lei, X.; Zhang, W. Xiao, J. . Rehealable, fully recyclable, and malleable electronic skin enabled by dynamic covalent thermoset nanocomposite . Sci. Adv. , 2018 . 4 eaaq0508 DOI: 10.1126/sciadv.aaq0508 http://doi.org/10.1126/sciadv.aaq0508 .
Taynton, P.; Yu, K.; Shoemaker, R. K.; Jin, Y.; Qi, H. J. Zhang, W. . Heat- or water-driven malleability in a highly recyclable covalent network polymer . Adv. Mater. , 2014 . 26 3938 - 3942 . DOI: 10.1002/adma.201400317 http://doi.org/10.1002/adma.201400317 .
Zhang, Y.; Ying, H.; Hart, K. R.; Wu, Y.; Hsu, A.J.; Coppola, A. M.; Kim, T. A.; Yang, K.; Sottos, N. R.; White, S. R. Cheng, J. . Malleable and recyclable poly(urea-urethane) thermosets bearing hindered urea bonds . Adv. Mater. , 2016 . 28 7646 - 7651 . DOI: 10.1002/adma.201601242 http://doi.org/10.1002/adma.201601242 .
Ying, H.; Zhang, Y. Cheng, J. . Dynamic urea bond for the design of reversible and self-healing polymers . Nat. Commun. , 2014 . 5 3218 DOI: 10.1038/ncomms4218 http://doi.org/10.1038/ncomms4218 .
Lai, J. C.; Mei, J. F.; Jia, X. Y.; Li, C. H.; You, X. Z. Bao, Z. . A stiff and healable polymer based on dynamic-covalent boroxine bonds . Adv. Mater. , 2016 . 28 8277 - 8282 . DOI: 10.1002/adma.201602332 http://doi.org/10.1002/adma.201602332 .
Cash, J. J.; Kubo, T.; Bapat, A. P. Sumerlin, B. S. . Room-temperature self-healing polymers based on dynamic-covalent boronic esters . Macromolecules , 2015 . 48 2098 - 2106 . DOI: 10.1021/acs.macromol.5b00210 http://doi.org/10.1021/acs.macromol.5b00210 .
Sun, Y.; Ren, Y. Y.; Li, Q.; Shi, R. W.; Hu, Y.; Guo, J. N.; Sun, Z. Yan, F. . Conductive, stretchable, and self-healing ionic gel based on dynamic covalent bonds and electrostatic interaction . Chinese J. Polym. Sci. , 2019 . 37 1053 - 1059 . DOI: 10.1007/s10118-019-2325-x http://doi.org/10.1007/s10118-019-2325-x .
Kim, S. M.; Jeon, H.; Shin, S. H.; Park, S. A.; Jegal, J.; Hwang, S.Y.; Oh, D. X. Park, J. . Superior toughness and fast self-healing at room temperature engineered by transparent elastomers . Adv. Mater. , 2018 . 30 1705145 DOI: 10.1002/adma.201705145 http://doi.org/10.1002/adma.201705145 .
Lei, Z. Q.; Xiang, H. P.; Yuan, Y. J.; Rong, M. Z. Zhang, M. Q. . Room-temperature self-healable and remoldable cross-linked polymer based on the dynamic exchange of disulfide bonds . Chem. Mater. , 2014 . 26 2038 - 2046 . DOI: 10.1021/cm4040616 http://doi.org/10.1021/cm4040616 .
Guo, Y.; Chen, S.; Sun, L.; Yang, L.; Zhang, L.; Lou, J. You, Z. . Degradable and fully recyclable dynamic thermoset elastomer for 3d-printed wearable electronics . Adv. Funct. Mater. , 2021 . 31 2009799 DOI: 10.1002/adfm.202009799 http://doi.org/10.1002/adfm.202009799 .
Reutenauer, P.; Buhler, E.; Boul, P. J.; Candau, S. J. Lehn, J. M. . Room temperature dynamic polymers based on Diels-Alder chemistry . Chemistry , 2009 . 15 1893 - 1900 . DOI: 10.1002/chem.200802145 http://doi.org/10.1002/chem.200802145 .
Capelot, M.; Montarnal, D.; Tournilhac, F. Leibler, L. . Metal-catalyzed transesterification for healing and assembling of thermosets . J. Am. Chem. Soc. , 2012 . 134 7664 - 7667 . DOI: 10.1021/ja302894k http://doi.org/10.1021/ja302894k .
Montarnal, D.; Capelot, M.; Tournilhac, F. Leibler, L. . Silica-like malleable materials from permanent organic networks . Science , 2011 . 334 965 - 968 . DOI: 10.1126/science.1212648 http://doi.org/10.1126/science.1212648 .
Zhang, L.; Liu, Z.; Wu, X.; Guan, Q.; Chen, S.; Sun, L.; Guo, Y.; Wang, S.; Song, J.; Jeffries, E. M.; He, C.; Qing, F. L.; Bao, X. You, Z. . A highly efficient self-healing elastomer with unprecedented mechanical properties . Adv. Mater. , 2019 . 31 1901402 DOI: 10.1002/adma.201901402 http://doi.org/10.1002/adma.201901402 .
Liu, W. X.; Zhang, C.; Zhang, H.; Zhao, N.; Yu, Z. X. Xu, J. . Oxime-based and catalyst-free dynamic covalent polyurethanes . J. Am. Chem. Soc. , 2017 . 139 8678 - 8684 . DOI: 10.1021/jacs.7b03967 http://doi.org/10.1021/jacs.7b03967 .
Liu, Z.; Zhang, L.; Guan, Q.; Guo, Y.; Lou, J.; Lei, D.; Wang, S.; Chen, S.; Sun, L.; Xuan, H.; Jeffries, E. M.; He, C.; Qing, F. L. You, Z. . Biomimetic materials with multiple protective functionalities . Adv. Funct. Mater. , 2019 . 29 1901058 DOI: 10.1002/adfm.201901058 http://doi.org/10.1002/adfm.201901058 .
Wicks, D. A.; Wicks, Z. W. . Blocked isocyanates iii: Part A . Mechan. Chem. Prog. Org. Coat. , 1999 . 36 148 - 172 . DOI: 10.1016/S0300-9440(99)00042-9 http://doi.org/10.1016/S0300-9440(99)00042-9 .
Delebecq, E.; Pascault, J. P.; Boutevin, B. Ganachaud, F. . On the versatility of urethane/urea bonds: reversibility, blocked isocyanate, and non-isocyanate polyurethane . Chem. Rev. , 2013 . 113 80 - 118 . DOI: 10.1021/cr300195n http://doi.org/10.1021/cr300195n .
Fu, D.; Pu, W.; Wang, Z.; Lu, X.; Sun, S.; Yu, C. Xia, H. . A facile dynamic crosslinked healable poly(oxime-urethane) elastomer with high elastic recovery and recyclability . J. Mater. Chem. A , 2018 . 6 18154 - 18164 . DOI: 10.1039/C8TA06059B http://doi.org/10.1039/C8TA06059B .
Wang, S.; Liu, Z.; Zhang, L.; Guo, Y.; Song, J.; Lou, J.; Guan, Q.; He, C. You, Z. . Strong, detachable, and self-healing dynamic crosslinked hot melt polyurethane adhesive . Mater. Chem. Front. , 2019 . 3 1833 - 1839 . DOI: 10.1039/C9QM00233B http://doi.org/10.1039/C9QM00233B .
Liu, X.; Liu, X.; Li, W.; Ru, Y.; Li, Y.; Sun, A.; Wei, L. . Engineered self-healable elastomer with giant strength and toughness via phase regulation and mechano-responsive self-reinforcing . Chem. Eng. J. , 2021 . 410 128300 DOI: 10.1016/j.cej.2020.128300 http://doi.org/10.1016/j.cej.2020.128300 .
Meng, X.; Xing, Z.; Hu, X.; Huang, Z.; Hu, T.; Tan, L.; Li, F. Chen, Y. . Stretchable perovskite solar cells with extremely recoverable performance . Angew. Chem. Int. Ed. , 2020 . 59 16602 - 16608 . DOI: 10.1002/anie.202003813 http://doi.org/10.1002/anie.202003813 .
Gao, H.; Xu, J.; Liu, S.; Song, Z.; Zhou, M.; Liu, S.; Li, F.; Li, F.; Wang, X.; Wang, Z. Zhang, Q. . Stretchable, self-healable integrated conductor based on mechanical reinforced graphene/polyurethane composites . J. Colloid Interface Sci. , 2021 . 597 393 - 400 . DOI: 10.1016/j.jcis.2021.04.005 http://doi.org/10.1016/j.jcis.2021.04.005 .
Lou, J.; Liu, Z.; Yang, L.; Guo, Y.; Lei, D. You, Z. . A new strategy of discretionarily reconfigurable actuators based on self-healing elastomers for diverse soft robots . Adv. Funct. Mater. , 2021 . 31 2008328 DOI: 10.1002/adfm.202008328 http://doi.org/10.1002/adfm.202008328 .
Wang, M.; Zhou, J.; Jiang, X.; Sheng, Y.; Xu, M. Lu, X. . Preparation of mechanically robust and autonomous self-healable elastomer based on multiple dynamic interactions . Eur. Polym. J. , 2021 . 146 110257 DOI: 10.1016/j.eurpolymj.2020.110257 http://doi.org/10.1016/j.eurpolymj.2020.110257 .
Zuo, H.; Liu, Z.; Zhang, L.; Liu, G.; Ouyang, X.; Guan, Q.; Wu, Q. You, Z. . Self-healing materials enable free-standing seamless large-scale 3D printing . Sci. China Mater. , 2021 . 64 1791 - 1800 . DOI: 10.1007/s40843-020-1603-y http://doi.org/10.1007/s40843-020-1603-y .
Wang, W.; Song, Q.; Liu, Q.; Zheng, H.; Li, C.; Yan, Y. Zhang, Q. . A novel reprocessable and recyclable acrylonitrile-butadiene rubber based on dynamic oxime-carbamate bond . Macromol. Rapid Commun. , 2019 . 40 1800733 DOI: 10.1002/marc.201800733 http://doi.org/10.1002/marc.201800733 .
Guo, Z.; Wang, W.; Yang, Y.; Majeed, K.; Zhang, B.; Zhou, F. Zhang, Q. . Preparation of multi-functional polyamide vitrimers via the ugi four-component polymerization and oxime-promoted transcarbamoylation reaction . Polym. Chem. , 2021 . 12 2009 - 2015 . DOI: 10.1039/D0PY01733G http://doi.org/10.1039/D0PY01733G .
Zhang, L.; Liu, Z.; Sun, L.; Xiao, L.; Guan, Q. You, Z. . Simple solvent-free strategy for synthesizing covalent adaptable networks from commodity vinyl monomers . Macromolecules , 2021 . 54 4081 - 4088 . DOI: 10.1021/acs.macromol.0c02766 http://doi.org/10.1021/acs.macromol.0c02766 .
Jiang, C.; Zhang, L.; Yang, Q.; Huang, S.; Shi, H.; Long, Q.; Qian, B.; Liu, Z.; Guan, Q.; Liu, M.; Yang, R.; Zhao, Q.; You, Z.; Ye, X . Self-healing polyurethane-elastomer with mechanical tunability for multiple biomedical applications in vivo . Nat. Commun. , 2021 . 12 4395 DOI: 10.1038/s41467-021-24680-x http://doi.org/10.1038/s41467-021-24680-x .
Qiao, Z.; Yang, Z.; Liu, W.; Wang, X.; Gao, Y.; Yu, Z.; Zhu, C.; Zhao, N. Xu, J. . Molecular weight switchable polyurethanes enable melt processing . Chem. Eng. J. , 2020 . 384 123287 DOI: 10.1016/j.cej.2019.123287 http://doi.org/10.1016/j.cej.2019.123287 .
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