Dynamic urea bond for the design of reversible and self-healing polymers

Hanze Ying; Yanfeng Zhang; Jianjun Cheng

doi:10.1038/ncomms4218

journal article Feb 04, 2014

Dynamic urea bond for the design of reversible and self-healing polymers

Hanze Ying Yanfeng Zhang

Jianjun Cheng

Nature Communications Vol. 5 No. 1 · Springer Science and Business Media LLC

View at Publisher Save 10.1038/ncomms4218

Topics

No keywords indexed for this article. Browse by subject →

References

43

[1]

Brunsveld, L., Folmer, B. J. B., Meijer, E. W. & Sijbesma, R. P. Supramolecular polymers. Chem. Rev. 101, 4071–4098 (2001). 10.1021/cr990125q

[2]

Dynamic Covalent Chemistry

Stuart J. Rowan, Stuart J. Cantrill, Graham R. L. Cousins et al.

Angewandte Chemie International Edition 2002 10.1002/1521-3773(20020315)41:6<898::aid-anie898>3.0.co;2-e

[3]

Lehn, J. M. Dynamers: dynamic molecular and supramolecular polymers. Prog. Polym. Sci. 30, 814–831 (2005). 10.1016/j.progpolymsci.2005.06.002

[4]

Wojtecki, R. J., Meador, M. A. & Rowan, S. J. Using the dynamic bond to access macroscopically responsive structurally dynamic polymers. Nat. Mater. 10, 14–27 (2011). 10.1038/nmat2891

[5]

Kloxin, C. J., Scott, T. F., Adzima, B. J. & Bowman, C. N. Covalent Adaptable Networks (CANS): a unique paradigm in cross-linked polymers. Macromolecules 43, 2643–2653 (2010). 10.1021/ma902596s

[6]

Habault, D., Zhang, H. & Zhao, Y. Light-triggered self-healing and shape-memory polymers. Chem. Soc. Rev. 42, 7244–7256 (2013). 10.1039/c3cs35489j

[7]

Sijbesma, R. P. et al. Reversible polymers formed from self-complementary monomers using quadruple hydrogen bonding. Science 278, 1601–1604 (1997). 10.1126/science.278.5343.1601

[8]

Hentschel, J., Kushner, A. M., Ziller, J. & Guan, Z. B. Self-healing supramolecular block copolymers. Angew. Chem. Int. Ed. 51, 10561–10565 (2012). 10.1002/anie.201204840

[9]

Burnworth, M. et al. Optically healable supramolecular polymers. Nature 472, 334–337 (2011). 10.1038/nature09963

[10]

Bode, S. et al. Self-healing polymer coatings based on crosslinked metallosupramolecular copolymers. Adv. Mater. 25, 1634–1638 (2013). 10.1002/adma.201203865

[11]

Harada, A., Kobayashi, R., Takashima, Y., Hashidzume, A. & Yamaguchi, H. Macroscopic self-assembly through molecular recognition. Nat. Chem. 3, 34–37 (2011). 10.1038/nchem.893

[12]

Nakahata, M., Takashima, Y., Yamaguchi, H. & Harada, A. Redox-responsive self-healing materials formed from host-guest polymers. Nat. Commun. 2, 551 (2011). 10.1038/ncomms1521

[13]

Skene, W. G. & Lehn, J. M. P. Dynamers: polyacylhydrazone reversible covalent polymers, component exchange, and constitutional diversity. Proc. Natl Acad. Sci. USA 101, 8270–8275 (2004). 10.1073/pnas.0401885101

[14]

Chen, X. X. et al. A thermally re-mendable cross-linked polymeric material. Science 295, 1698–1702 (2002). 10.1126/science.1065879

[15]

Scott, T. F., Schneider, A. D., Cook, W. D. & Bowman, C. N. Photoinduced plasticity in cross-linked polymers. Science 308, 1615–1617 (2005). 10.1126/science.1110505

[16]

Amamoto, Y., Kamada, J., Otsuka, H., Takahara, A. & Matyjaszewski, K. Repeatable photoinduced self-healing of covalently cross-linked polymers through reshuffling of trithiocarbonate units. Angew. Chem. Int. Ed. 50, 1660–1663 (2011). 10.1002/anie.201003888

[17]

Amamoto, Y., Otsuka, H., Takahara, A. & Matyjaszewski, K. Self-healing of covalently cross-linked polymers by reshuffling thiuram disulfide moieties in air under visible light. Adv. Mater. 24, 3975–3980 (2012). 10.1002/adma.201201928

[18]

Murphy, E. B. & Wudl, F. The world of smart healable materials. Prog. Polym. Sci. 35, 223–251 (2010). 10.1016/j.progpolymsci.2009.10.006

[19]

White, S. R. et al. Autonomic healing of polymer composites. Nature 409, 794–797 (2001). 10.1038/35057232

[20]

Toohey, K. S., Sottos, N. R., Lewis, J. A., Moore, J. S. & White, S. R. Self-healing materials with microvascular networks. Nat. Mater. 6, 581–585 (2007). 10.1038/nmat1934

[21]

Palleau, E., Reece, S., Desai, S. C., Smith, M. E. & Dickey, M. D. Self-healing stretchable wires for reconfigurable circuit wiring and 3D microfluidics. Adv. Mater. 25, 1589–1592 (2013). 10.1002/adma.201203921

[22]

Holten-Andersen, N. et al. pH-induced metal-ligand cross-links inspired by mussel yield self-healing polymer networks with near-covalent elastic moduli. Proc. Natl Acad. Sci. USA 108, 2651–2655 (2011). 10.1073/pnas.1015862108

[23]

Chen, Y., Kushner, A. M., Williams, G. A. & Guan, Z. Multiphase design of autonomic self-healing thermoplastic elastomers. Nat. Chem. 4, 467–472 (2012). 10.1038/nchem.1314

[24]

Huang, L. et al. Multichannel and repeatable self-healing of mechanical enhanced graphene-thermoplastic polyurethane composites. Adv. Mater. 25, 2224–2228 (2013). 10.1002/adma.201204768

[25]

Wang, Q. et al. High-water-content mouldable hydrogels by mixing clay and a dendritic molecular binder. Nature 463, 339–343 (2010). 10.1038/nature08693

[26]

Phadke, A. et al. Rapid self-healing hydrogels. Proc. Natl Acad. Sci. USA 109, 4383–4388 (2012). 10.1073/pnas.1201122109

[27]

Cordier, P., Tournilhac, F., Soulie-Ziakovic, C. & Leibler, L. Self-healing and thermoreversible rubber from supramolecular assembly. Nature 451, 977–980 (2008). 10.1038/nature06669

[28]

Fox, J. et al. High-strength, healable, supramolecular polymer nanocomposites. J. Am. Chem. Soc. 134, 5362–5368 (2012). 10.1021/ja300050x

[29]

Ghosh, B. & Urban, M. W. Self-repairing oxetane-substituted chitosan polyurethane networks. Science 323, 1458–1460 (2009). 10.1126/science.1167391

[30]

Imato, K. et al. Self-healing of chemical gels cross-linked by diarylbibenzofuranone-based trigger-free dynamic covalent bonds at room temperature. Angew. Chem. Int. Ed. 51, 1138–1142 (2012). 10.1002/anie.201104069

[31]

Adzima, B. J., Kloxin, C. J. & Bowman, C. N. Externally triggered healing of a thermoreversible covalent network via self-limited hysteresis heating. Adv. Mater. 22, 2784–2787 (2010). 10.1002/adma.200904138

[32]

Reutenauer, P., Buhler, E., Boul, P. J., Candau, S. J. & Lehn, J. M. Room temperature dynamic polymers based on Diels-Alder chemistry. Chem. Eur. J. 15, 1893–1900 (2009). 10.1002/chem.200802145

[33]

Oehlenschlaeger, K. K. et al. Fast and catalyst-free hetero-Diels-Alder chemistry for on demand cyclable bonding/debonding materials. Polym. Chem. 4, 4348–4355 (2013). 10.1039/c3py00476g

[34]

Zheng, P. W. & McCarthy, T. J. A surprise from 1954: siloxane equilibration is a simple, robust, and obvious polymer self-healing mechanism. J. Am. Chem. Soc. 134, 2024–2027 (2012). 10.1021/ja2113257

[35]

Lu, Y. X. & Guan, Z. Olefin metathesis for effective polymer healing via dynamic exchange of strong carbon-carbon double bonds. J. Am. Chem. Soc. 134, 14226–14231 (2012). 10.1021/ja306287s

[36]

Lu, Y. X., Tournilhac, F., Leibler, L. & Guan, Z. Making insoluble polymer networks malleable via olefin metathesis. J. Am. Chem. Soc. 134, 8424–8427 (2012). 10.1021/ja303356z

[37]

Silica-Like Malleable Materials from Permanent Organic Networks

Damien Montarnal, Mathieu Capelot, François Tournilhac et al.

Science 2011 10.1126/science.1212648

[38]

Capelot, M., Montarnal, D., Tournilhac, F. & Leibler, L. Metal-catalyzed transesterification for healing and assembling of thermosets. J. Am. Chem. Soc. 134, 7664–7667 (2012). 10.1021/ja302894k

[39]

Basso, A., De Martin, L., Ebert, C., Gardossi, L. & Linda, P. High isolated yields in thermodynamically controlled peptide synthesis in toluene catalysed by thermolysin adsorbed on celite R-640. Chem. Commun. 467–468 (2000). 10.1039/b000797h

[40]

Hutchby, M. et al. Switching pathways: room-temperature neutral solvolysis and substitution of amides. Angew. Chem. Int. Ed. 51, 548–551 (2012). 10.1002/anie.201107117

[41]

Stowell, J. C. & Padegimas, S. J. Urea dissociation. a measure of steric hindrance in secondary amines. J. Org. Chem. 39, 2448–2449 (1974). 10.1021/jo00930a039

[42]

Hutchby, M. et al. Hindered ureas as masked isocyanates: facile carbamoylation of nucleophiles under neutral conditions. Angew. Chem. Int. Ed. 48, 8721–8724 (2009). 10.1002/anie.200904435

[43]

Zhao, D. & Moore, J. S. Nucleation-elongation: a mechanism for cooperative supramolecular polymerization. Org. Biomol. Chem. 1, 3471–3491 (2003). 10.1039/b308788c

Cited By

944

Polyimide nanocomposites for next generation spacesuits

Priyanka Prakash, Janith Weerasinghe · 2025

Materials Horizons

Sustainable approaches in vat photopolymerization: advancements, limitations, and future opportunities

Mirko Maturi, Erica Locatelli · 2025

Green Chem.

Organic transistors-driven wearable electronics for smart life

Zixuan Liu, Chengyu Zhang · 2024

Wearable Electronics

New Advances in Covalent Network Polymers via Dynamic Covalent Chemistry

Zepeng Lei, Hongxuan Chen · 2024

Chemical Reviews

Self‐Healing Elastic Electronics: Materials Design, Mechanisms, and Applications

Yi Wan, Xiang‐Chun Li · 2024

Advanced Functional Materials

Polyether-based polyurethane electrolyte for lithium metal battery: a perspective

Peng Cui, Yifan Li · 2024

RSC Advances

Dynamic polymeric materials via hydrogen-bond cross-linking: Effect of multiple network topologies

Yuting Ren, Xia Dong · 2024

Progress in Polymer Science

Healable Ionic Conductors with Extremely Low‐Hysteresis and High Mechanical Strength Enabled by Hydrophobic Domain‐Locked Reversible Interactions

Tianqi Li, Xiang Li · 2023

Advanced Materials

Self-healing of fractured diamond

Keliang Qiu, Jingpeng Hou · 2023

Nature Materials

Intrinsically Self-Healing Polymers: From Mechanistic Insight to Current Challenges

Bingrui Li, Peng-Fei Cao · 2022

Chemical Reviews

Effect of diisocyanate structure on steric restructuring of hindered urea bonds for self-healable coating

Su Min Yun, Hyang Moo Lee · 2022

Progress in Organic Coatings

Self-healable recyclable thermoplastic polyurethane elastomers: Enabled by metal–ligand bonds between the cerium(III) triflate and phloretin

Gao-Fei Pan, Zhe Wang · 2022

Chemical Engineering Journal

Structure–Reactivity–Property Relationships in Covalent Adaptable Networks

Vivian Zhang, Boyeong Kang · 2022

Journal of the American Chemical So...

Coral-like Magnetic Particles for Chemoselective Extraction of Anionic Metabolites

Shuai Liu, Mo Zhang · 2022

ACS Applied Materials & Interfa...

Phosphate-based covalent adaptable networks with recyclability and flame retardancy from bioresources

Yanlin Liu, Binbo Wang · 2021

European Polymer Journal

Covalent Adaptable Liquid Crystal Networks Enabled by Reversible Ring-Opening Cascades of Cyclic Disulfides

Yikang Shen, Hari K. Bisoyi · 2021

Journal of the American Chemical So...

Self‐Healing Functional Electronic Devices

YanSong Gai, Hu Li · 2021

Small

Malleable, Recyclable, and Robust Poly(amide–imine) Vitrimers Prepared through a Green Polymerization Process

Kuan Liang, Ganggang Zhang · 2021

ACS Sustainable Chemistry & Eng...

Self-healing and self-cleaning clear coating

Ajmir Khan, Kun Huang · 2020

Journal of Colloid and Interface Sc...

Adaptable Strategy to Fabricate Self-Healable and Reprocessable Poly(thiourethane-urethane) Elastomers via Reversible Thiol–Isocyanate Click Chemistry

Cheng-Jie Fan, Zhi-Bin Wen · 2020

Macromolecules

Metrics

944

Citations

43

References

Details

Published: Feb 04, 2014
Vol/Issue: 5(1)
License: View

Authors

Department of Materials Science and Engineering; University of Illinois at Urbana-Champaign; Urbana; USA

Cite This Article

Hanze Ying, Yanfeng Zhang, Jianjun Cheng (2014). Dynamic urea bond for the design of reversible and self-healing polymers. Nature Communications, 5(1). https://doi.org/10.1038/ncomms4218

Dynamic urea bond for the design of reversible and self-healing polymers

You May Also Like