Insertion of Supramolecular Segments into Covalently Crosslinked Polyurethane Networks towards the Fabrication of Recyclable Elastomers

Lu-Ping Wang; Ming-Guang Zhang; Jing-Cheng Hao; Xu Wang

doi:10.1007/s10118-022-2651-2

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Insertion of Supramolecular Segments into Covalently Crosslinked Polyurethane Networks towards the Fabrication of Recyclable Elastomers

RESEARCH ARTICLE | Updated：2022-03-23

- Insertion of Supramolecular Segments into Covalently Crosslinked Polyurethane Networks towards the Fabrication of Recyclable Elastomers
- Chinese Journal of Polymer Science Vol. 40, Issue 3, Pages: 321-330(2022)
- Affiliations：
  
  a.National Engineering Research Center for Colloidal Materials, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, China
  b.Key Laboratory of Colloid and Interface Chemistry of the Ministry of Education, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, China
- Author bio：
  
  wangxu@sdu.edu.cn
- Funds：
- DOI：10.1007/s10118-022-2651-2
  CLC：
- Received：31 August 2021，
  
  Revised：2021-9-18，
  
  Accepted：05 October 2021，
  
  Online First：11 January 2022，
  
  Published：01 March 2022
- Accepted：
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Wang, L. P.; Zhang, M. G.; Hao, J. C.; Wang, X. Insertion of supramolecular segments into covalently crosslinked polyurethane networks towards the fabrication of recyclable elastomers. Chinese J. Polym. Sci. 2022, 40, 321–330

Lu-Ping Wang, Ming-Guang Zhang, Jing-Cheng Hao, et al. Insertion of Supramolecular Segments into Covalently Crosslinked Polyurethane Networks towards the Fabrication of Recyclable Elastomers[J]. Chinese Journal of Polymer Science, 2022, 40(3): 321-330.
Wang, L. P.; Zhang, M. G.; Hao, J. C.; Wang, X. Insertion of supramolecular segments into covalently crosslinked polyurethane networks towards the fabrication of recyclable elastomers. Chinese J. Polym. Sci. 2022, 40, 321–330 DOI： 10.1007/s10118-022-2651-2.

Lu-Ping Wang, Ming-Guang Zhang, Jing-Cheng Hao, et al. Insertion of Supramolecular Segments into Covalently Crosslinked Polyurethane Networks towards the Fabrication of Recyclable Elastomers[J]. Chinese Journal of Polymer Science, 2022, 40(3): 321-330. DOI： 10.1007/s10118-022-2651-2.

摘要

Abstract

Thermoset plastics have become one of the most important chemical products in the world. The consequent problem is that although the thermosets possess excellent performance in mechanical strength

they cannot be reprocessed because of the internal permanent network structures. Optimizing the molecular design of thermosets is one of the most feasible ways to improve their recyclability. Here we present a facile and robust strategy to engineer the reprocessability of thermoset polyurethanes without compromising their mechanical toughness and chemical resistance

via

adding supramolecular additives during the polymer synthesis process. By using a multiple hydrogen bonding moiety as the model supramolecular additive

we demonstrate that the mechanical properties

recyclability

and chemical resistance of the crosslinked polyurethanes can be precisely controlled by adjusting the contents of the supramolecular additive. Systematic studies on the relations between molecular design and material properties are performed

and the optimized polyurethane network with a moderate amount of the supramolecular additive achieves the right balance between the robustness and recyclability. This work provides a cost-effective and practical way to chemically engineer thermoset plastics

aiming to enable the recycling of mechanically tough and chemically stable polymer materials.

关键词

Keywords

references

Zhang, Y.; Zhang, L.; Yang, G.; Yao, Y.; Wei, X.; Pan, T.; Wu, J.; Tian, M.; Yin, P . Recent advances in recyclable thermosets and thermoset composites based on covalent adaptable networks . J. Mater. Sci. Technol. , 2021 . 92 75 - 87 . DOI: 10.1016/j.jmst.2021.03.043 http://doi.org/10.1016/j.jmst.2021.03.043 .

Zhu, J. B.; Watson, E. M.; Tang, J.; Chen, E. Y. X . A synthetic polymer system with repeatable chemical recyclability . Science , 2018 . 360 398 - 403 . DOI: 10.1126/science.aar5498 http://doi.org/10.1126/science.aar5498 .

Long, T. E . Toward recyclable thermosets . Science , 2014 . 344 706 - 707 . DOI: 10.1126/science.1254401 http://doi.org/10.1126/science.1254401 .

Liu, J.; Wang, S.; Peng, Y.; Zhu, J.; Zhao, W.; Liu, X . Advances in sustainable thermosetting resins: from renewable feedstock to high performance and recyclability . Prog. Polym. Sci. , 2021 . 113 101353 DOI: 10.1016/j.progpolymsci.2020.101353 http://doi.org/10.1016/j.progpolymsci.2020.101353 .

Jehanno, C.; Sardon, H . A step towards truly recyclable plastics . Nature , 2019 . 568 467 - 468 . DOI: 10.1038/d41586-019-01209-3 http://doi.org/10.1038/d41586-019-01209-3 .

Shieh, P.; Zhang, W.; Husted, K. E. L.; Kristufek, S. L.; Xiong, B.; Lundberg, D. J.; Lem, J.; Veysset, D.; Sun, Y.; Nelson, K. A.; Plata, D. L.; Johnson, J. A . Cleavable comonomers enable degradable, recyclable thermoset plastics . Nature , 2020 . 583 542 - 547 . DOI: 10.1038/s41586-020-2495-2 http://doi.org/10.1038/s41586-020-2495-2 .

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 .

Millican, J. M.; Agarwal, S . Plastic pollution: a material problem? . Macromolecules , 2021 . 54 4455 - 4469 . DOI: 10.1021/acs.macromol.0c02814 http://doi.org/10.1021/acs.macromol.0c02814 .

MacLeod, M.; Arp, H. P. H.; Tekman, M. B.; Jahnke, A . The global threat from plastic pollution . Science , 2021 . 373 61 - 65 . DOI: 10.1126/science.abg5433 http://doi.org/10.1126/science.abg5433 .

Chen, X.; Dam, M. A.; Ono, K.; Mal, A.; Shen, H.; Nutt, S. R.; Sheran, K.; Wudl, F . A thermally re-mendable cross-linked polymeric material . Science , 2002 . 295 1698 - 1702 . DOI: 10.1126/science.1065879 http://doi.org/10.1126/science.1065879 .

Stubbins, A.; Law, K. L.; Muñoz, S. E.; Bianchi, T. S.; Zhu, L . Plastics in the earth system . Science , 2021 . 373 51 - 55 . DOI: 10.1126/science.abb0354 http://doi.org/10.1126/science.abb0354 .

Sheppard, D. T.; Jin, K.; Hamachi, L. S.; Dean, W.; Fortman, D. J.; Ellison, C. J.; Dichtel, W. R . Reprocessing postconsumer polyurethane foam using carbamate exchange catalysis and twin-screw extrusion . ACS Cent. Sci. , 2020 . 6 921 - 927 . DOI: 10.1021/acscentsci.0c00083 http://doi.org/10.1021/acscentsci.0c00083 .

Luong, D. X.; Bets, K. V.; Algozeeb, W. A.; Stanford, M. G.; Kittrell, C.; Chen, W.; Salvatierra, R. V.; Ren, M.; McHugh, E. A.; Advincula, P. A.; Wang, Z.; Bhatt, M.; Guo, H.; Mancevski, V.; Shahsavari, R.; Yakobson, B. I.; Tour, J. M . Gram-scale bottom-up flash graphene synthesis . Nature , 2020 . 577 647 - 651 . DOI: 10.1038/s41586-020-1938-0 http://doi.org/10.1038/s41586-020-1938-0 .

Korley, L. T. J.; Epps, T. H.; Helms, B. A.; Ryan, A. J . Toward polymer upcycling-adding value and tackling circularity . Science , 2021 . 373 66 - 69 . DOI: 10.1126/science.abg4503 http://doi.org/10.1126/science.abg4503 .

Zhong, Y.; Li, P.; Wang, X.; Hao, J . Amoeba-inspired reengineering of polymer networks . Green Chem. , 2021 . 23 2496 - 2506 . DOI: 10.1039/D1GC00232E http://doi.org/10.1039/D1GC00232E .

Wang, X.; Zhan, S.; Lu, Z.; Li, J.; Yang, X.; Qiao, Y.; Men, Y.; Sun, J . Healable, recyclable, and mechanically tough polyurethane elastomers with exceptional damage tolerance . Adv. Mater. , 2020 . 32 2005759 DOI: 10.1002/adma.202005759 http://doi.org/10.1002/adma.202005759 .

Zhang, C.; Yang, Z.; Duong, N. T.; Li, X.; Nishiyama, Y.; Wu, Q.; Zhang, R.; Sun, P . Using dynamic bonds to enhance the mechanical performance: from microscopic molecular interactions to macroscopic properties . Macromolecules , 2019 . 52 5014 - 5025 . DOI: 10.1021/acs.macromol.9b00503 http://doi.org/10.1021/acs.macromol.9b00503 .

Rowan, S. J.; Cantrill, S. J.; Cousins, G. R. L.; Sanders, J. K. M.; Stoddart, J. F . Dynamic covalent chemistry . Angew. Chem. Int. Ed. , 2002 . 41 898 - 952 . DOI: 10.1002/1521-3773(20020315)41:6<898::AID-ANIE898>3.0.CO;2-E http://doi.org/10.1002/1521-3773(20020315)41:6<898::AID-ANIE898>3.0.CO;2-E .

Ma, S.; Webster, D. C . Degradable thermosets based on labile bonds or linkages: a review . Prog. Polym. Sci , 2018 . 76 65 - 110 . DOI: 10.1016/j.progpolymsci.2017.07.008 http://doi.org/10.1016/j.progpolymsci.2017.07.008 .

Lu, X.; Bao, C.; Xie, P.; Guo, Z.; Sun, J . Solution-processable and thermostable super-strong poly(aryl ether ketone) supramolecular thermosets cross-linked with dynamic boroxines . Adv. Funct. Mater. , 2021 . 31 2103061 DOI: 10.1002/adfm.202103061 http://doi.org/10.1002/adfm.202103061 .

Kuhl, N.; Bode, S.; Bose, R. K.; Vitz, J.; Seifert, A.; Hoeppener, S.; Garcia, S. J.; Spange, S.; van der Zwaag, S.; Hager, M. D.; Schubert, U. S . Acylhydrazones as reversible covalent crosslinkers for self-healing polymers . Adv. Funct. Mater , 2015 . 25 3295 - 3301 . DOI: 10.1002/adfm.201501117 http://doi.org/10.1002/adfm.201501117 .

Gao, Y.; Liu, W.; Zhu, S . Reversible shape memory polymer from semicrystalline poly(ethylene- co -vinyl acetate) with dynamic covalent polymer networks . Macromolecules , 2018 . 51 8956 - 8963 . DOI: 10.1021/acs.macromol.8b01724 http://doi.org/10.1021/acs.macromol.8b01724 .

Fortman, D. J.; Sheppard, D. T.; Dichtel, W. R . Reprocessing cross-linked polyurethanes by catalyzing carbamate exchange . Macromolecules , 2016 . 52 6330 - 6335 . .

Zhong, Y.; Li, P.; Hao, J.; Wang, X . Bioinspired self-healing of kinetically inert hydrogels mediated by chemical nutrient supply . ACS Appl. Mater. Interfaces , 2020 . 12 6471 - 6478 . DOI: 10.1021/acsami.9b20445 http://doi.org/10.1021/acsami.9b20445 .

Mocny, P.; Klok, H. A . Reversibly cross-linking polymer brushes using interchain disulfide bonds . Macromolecules , 2020 . 53 731 - 740 . DOI: 10.1021/acs.macromol.9b02199 http://doi.org/10.1021/acs.macromol.9b02199 .

Cui, C.; Chen, X.; Ma, L.; Zhong, Q.; Li, Z.; Mariappan, A.; Zhang, Q.; Cheng, Y.; He, G.; Chen, X.; Dong, Z.; An, L.; Zhang, Y . Polythiourethane covalent adaptable networks for strong and reworkable adhesives and fully recyclable carbon fiber-reinforced composites . ACS Appl. Mater. Interfaces , 2020 . 12 47975 - 47983 . DOI: 10.1021/acsami.0c14189 http://doi.org/10.1021/acsami.0c14189 .

Post, W.; Susa, A.; Blaauw, R.; Molenveld, K.; Knoop, R. J. I . A review on the potential and limitations of recyclable thermosets for structural applications . Polym. Rev. , 2019 . 60 359 - 388 . .

Yin, Z.; Song, G.; Jiao, Y.; Zheng, P.; Xu, J. F.; Zhang, X . Dissipative supramolecular polymerization powered by light . CCS Chem. , 2019 . 1 335 - 342 . DOI: 10.31635/ccschem.019.20190013 http://doi.org/10.31635/ccschem.019.20190013 .

Zhu, J.; Chen George, Y.; Yu, L.; Xu, H.; Liu, X.; Sun, J . Mechanically strong and highly stiff supramolecular polymer composites repairable at ambient conditions . CCS Chem. , 2019 . 2 280 - 292 . .

Zhang, S.; Qin, B.; Xu, J. F.; Zhang, X . Multi-recyclable shape memory supramolecular polyurea with long cycle life and superior stability . ACS Mater. Lett. , 2021 . 3 331 - 336 . DOI: 10.1021/acsmaterialslett.1c00053 http://doi.org/10.1021/acsmaterialslett.1c00053 .

Sun, P.; Li, Y.; Qin, B.; Xu, J. F.; Zhang, X . Super strong and multi-reusable supramolecular epoxy hot melt adhesives . ACS Mater. Lett. , 2021 . 3 1003 - 1009 . DOI: 10.1021/acsmaterialslett.1c00277 http://doi.org/10.1021/acsmaterialslett.1c00277 .

Du, L.; Xu, Z. Y.; Fan, C. J.; Xiang, G.; Yang, K. K.; Wang, Y. Z . A fascinating metallo-supramolecular polymer network with thermal/magnetic/light-responsive shape-memory effects anchored by Fe 3 O 4 nanoparticles . Macromolecules , 2018 . 51 705 - 715 . DOI: 10.1021/acs.macromol.7b02641 http://doi.org/10.1021/acs.macromol.7b02641 .

An, N.; Wang, X.; Li, Y.; Zhang, L.; Lu, Z.; Sun, J . Healable and mechanically super-strong polymeric composites derived from hydrogen-bonded polymeric complexes . Adv. Mater. , 2019 . 31 1904882 DOI: 10.1002/adma.201904882 http://doi.org/10.1002/adma.201904882 .

Liu, X.; Wu, D.; Wang, H.; Wang, Q . Self-recovering tough gel electrolyte with adjustable supercapacitor performance . Adv. Mater. , 2014 . 26 4370 - 4375 . DOI: 10.1002/adma.201400240 http://doi.org/10.1002/adma.201400240 .

Luo, F.; Sun, T. L.; Nakajima, T.; Kurokawa, T.; Ihsan, A. B.; Li, X.; Guo, H.; Gong, J. P . Free reprocessability of tough and self-healing hydrogels based on polyion complex . ACS Macro Lett. , 2015 . 4 961 - 964 . DOI: 10.1021/acsmacrolett.5b00501 http://doi.org/10.1021/acsmacrolett.5b00501 .

Xu, S.; Chang, P.; Zhao, B.; Adeel, M.; Zheng, S . Formation of poly( ε -caprolactone) networks via supramolecular hydrogen bonding interactions . Chinese J. Polym. Sci. , 2019 . 37 197 - 207 . DOI: 10.1007/s10118-019-2199-y http://doi.org/10.1007/s10118-019-2199-y .

Shi, J.; Zhao, N.; Yan, D.; Song, J.; Fu, W.; Li, Z . Design of a mechanically strong and highly stretchable thermoplastic silicone elastomer based on coulombic interactions . J. Mater. Chem. A , 2020 . 8 5943 - 5951 . DOI: 10.1039/D0TA01593H http://doi.org/10.1039/D0TA01593H .

Li, Z.; Zhu, Y. L.; Niu, W.; Yang, X.; Jiang, Z.; Lu, Z. Y.; Liu, X.; Sun, J . Healable and recyclable elastomers with record-high mechanical robustness, unprecedented crack tolerance, and superhigh elastic restorability . Adv. Mater. , 2021 . 33 2101498 DOI: 10.1002/adma.202101498 http://doi.org/10.1002/adma.202101498 .

Qin, B.; Zhang, S.; Sun, P.; Tang, B.; Yin, Z.; Cao, X.; Chen, Q.; Xu, J. F.; Zhang, X . Tough and multi-recyclable cross-linked supramolecular polyureas via incorporating noncovalent bonds into main-chains . Adv. Mater. , 2020 . 32 2000096 .

Street, D. P.; Ledford, W. K.; Allison, A. A.; Patterson, S.; Pickel, D. L.; Lokitz, B. S.; Messman, J. M.; Kilbey, S. M . Self-complementary multiple hydrogen-bonding additives enhance thermomechanical properties of 3D-printed PMMA structures . Macromolecules , 2019 . 52 5574 - 5582 . DOI: 10.1021/acs.macromol.9b00546 http://doi.org/10.1021/acs.macromol.9b00546 .

Söntjens, S. H. M.; Sijbesma, R. P.; van Genderen, M. H. P.; Meijer, E. W . Stability and lifetime of quadruply hydrogen bonded 2-ureido-4[1 H ]-pyrimidinone dimers . J. Am. Chem. Soc. , 2000 . 122 7487 - 7493 . DOI: 10.1021/ja000435m http://doi.org/10.1021/ja000435m .

Li, T.; Zheng, T. Z.; Guo, Z. X.; Xu, J.; Guo, B. H . A well-defined hierarchical hydrogen bonding strategy to polyureas with simultaneously improved strength and toughness . Chinese J. Polym. Sci. , 2019 . 37 1257 - 1266 . DOI: 10.1007/s10118-019-2275-3 http://doi.org/10.1007/s10118-019-2275-3 .

Li, X.; Li, J.; Wei, W.; Yang, F.; Wu, M.; Wu, Q.; Xie, T.; Chen, Y . Enhanced mechanochemiluminescence from end-functionalized polyurethanes with multiple hydrogen bonds . Macromolecules , 2021 . 54 1557 - 1563 . DOI: 10.1021/acs.macromol.0c02622 http://doi.org/10.1021/acs.macromol.0c02622 .

Sijbesma, R. P.; Beijer, F. H.; Brunsveld, L.; Folmer, B. J. B.; Hirschberg, J. H. K. K.; Lange, R. F. M.; Lowe, J. K. L.; Meijer, E. W . Reversible polymers formed from self-complementary monomers using quadruple hydrogen bonding . Science , 1997 . 278 1601 - 1604 . DOI: 10.1126/science.278.5343.1601 http://doi.org/10.1126/science.278.5343.1601 .

Zhang, L.; Qiu, T.; Sun, X.; Guo, L.; He, L.; Ye, J.; Li, X . Achievement of both mechanical properties and intrinsic self-healing under body temperature in polyurethane elastomers: a synthesis strategy from waterborne polymers . Polymers , 2020 . 12 989 DOI: 10.3390/polym12040989 http://doi.org/10.3390/polym12040989 .

Zhang, X.; Wang, Y.; Sun, S.; Hou, L.; Wu, P.; Wu, Z.; Zheng, Q . A tough and stiff hydrogel with tunable water content and mechanical properties based on the synergistic effect of hydrogen bonding and hydrophobic interaction . Macromolecules , 2018 . 51 8136 - 8146 . DOI: 10.1021/acs.macromol.8b01496 http://doi.org/10.1021/acs.macromol.8b01496 .

Guo, Y.; Qu, X.; Hu, Z.; Zhu, J.; Niu, W.; Liu, X . Highly elastic and mechanically robust polymer electrolytes with high ionic conductivity and adhesiveness for high-performance lithium metal batteries . J. Mater. Chem. A , 2021 . 9 13597 - 13607 . DOI: 10.1039/D1TA02579A http://doi.org/10.1039/D1TA02579A .

Liu, X.; Zhong, M.; Shi, F.; Xu, H.; Xie, X . Multi-bond network hydrogels with robust mechanical and self-healable properties . Chinese J. Polym. Sci. , 2017 . 35 1253 - 1267 . DOI: 10.1007/s10118-017-1971-0 http://doi.org/10.1007/s10118-017-1971-0 .

Song, Y.; Liu, Y.; Qi, T.; Li, G . Towards dynamic but supertough healable polymers through biomimetic hierarchical hydrogen-bonding interactions . Angew. Chem. Int. Ed. , 2018 . 57 13838 - 13842 . DOI: 10.1002/anie.201807622 http://doi.org/10.1002/anie.201807622 .

Zheng, N.; Fang, Z.; Zou, W.; Zhao, Q.; Xie, T . Thermoset shape-memory polyurethane with intrinsic plasticity enabled by transcarbamoylation . Angew. Chem. Int. Ed. , 2013 . 55 11421 - 11425 . .

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