Polymer-to-Monomers Chemically Recyclable Poly(imide-imine) Plastics with Extreme-Condition Resistance and Flame Retardancy

Zhen-Yu Wang; Xiao-Kong Liu

doi:10.1007/s10118-024-3199-0

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Polymer-to-Monomers Chemically Recyclable Poly(imide-imine) Plastics with Extreme-Condition Resistance and Flame Retardancy

RESEARCH ARTICLE | Updated：2024-09-23

- Polymer-to-Monomers Chemically Recyclable Poly(imide-imine) Plastics with Extreme-Condition Resistance and Flame Retardancy
- Polymer-to-Monomers Chemically Recyclable Poly(imide-imine) Plastics with Extreme-Condition Resistance and Flame Retardancy
- 高分子科学（英文版） 2024年42卷第10期页码：1525-1535
- Affiliations：
  
  State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012, China
- Author bio：
  
  xiaokongliu@jlu.edu.cn
- Funds：
  
  This work was financially supported by Natural Science Foundation of Jilin Province (No. ***202302003), the National Natural Science Foundation of China (No. 22275069) and National Key R&D Program of China (No. 2023YFA1008804).;Electronic supplementary information (ESI) is available free of charge in the online version of this article at http://doi.org/10.1007/s10118-024-3199-0.
- DOI：10.1007/s10118-024-3199-0
  中图分类号： M
- 收稿：2024-05-01，
  
  修回：2024-06-14，
  
  录用：2024-06-21，
  
  网络首发：2024-09-02，
  
  纸质出版：2024-10-01
- Accepted：
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Wang, Z. Y.; Liu, X. K. Polymer-to-monomers chemically recyclable poly(imide-imine) plastics with extreme-condition resistance and flame retardancy. Chinese J. Polym. Sci. 2024, 42, 1525–1535

Zhen-Yu Wang, Xiao-Kong Liu. Polymer-to-Monomers Chemically Recyclable Poly(imide-imine) Plastics with Extreme-Condition Resistance and Flame Retardancy[J]. Chinese Journal of Polymer Science, 2024, 42(10): 1525-1535.
Wang, Z. Y.; Liu, X. K. Polymer-to-monomers chemically recyclable poly(imide-imine) plastics with extreme-condition resistance and flame retardancy. Chinese J. Polym. Sci. 2024, 42, 1525–1535 DOI： 10.1007/s10118-024-3199-0.

Zhen-Yu Wang, Xiao-Kong Liu. Polymer-to-Monomers Chemically Recyclable Poly(imide-imine) Plastics with Extreme-Condition Resistance and Flame Retardancy[J]. Chinese Journal of Polymer Science, 2024, 42(10): 1525-1535. DOI： 10.1007/s10118-024-3199-0.

摘要

A dynamic covalent poly(imide-imine) polymer with excellent flame retardancy is reported

exhibiting comparable properties to the commercial polyimides

including exceptional mechanical properties

high thermal stability

and outstanding chemical resistance. The plastic can be depolymerized and converted back into the initial pure monomers that can be used to regenerate new-generation plastics.

Abstract

Polyimides are a family of high-tech plastics that have irreplaceable applications in the fields of aerospace

defense

and opto-electronics

but polyimides are difficult to be reprocessed and recycled at the end of their service life

resulting in a significant waste of resources. Hence

it is of great significance to develop recyclable polyimides with comparable properties to the commercial products. Herein

we report a novel polymer-to-monomers chemically recyclable poly(imide-imine) (PtM-CR-PII) plastic

synthesized by cross-linking the amine-terminated aromatic bisimide monomer and the hexa-vanillin terminated cyclophosphazene monomer via dynamic imine bonds. The PtM-CR-PII plastic exhibits comparable mechanical and thermal properties as well as chemical stability to the commercial polyimides. The PtM-CR-PII plastic possesses a high Young’s modulus of ≈3.2 GPa and a tensile strength as high as ≈108 MPa

which also exhibits high thermal stability with a glass transition temperature of ≈220 °C. Moreover

the PtM-CR-PII plastic exhibits outstanding waterproofness

acid/alkali-resistance

and solvent-resistance

its appearance and mechanical properties can be well maintained after long-term soaking in water

highly concentrated acid and base

and various organic solvents. Furthermore

the cyclophosphazene moieties endow the PtM-CR-PII plastic with excellent flame retardancy. The PtM-CR-PII plastic exhibits the highest UL-94 flame-retarding rating of V-0 and a limiting oxygen index (LOI) value of 45.5%. Importantly

the PtM-CR-PII plastic can be depolymerized in an organic solvents-acid mixture medium at room temperature

allowing easy separation and recovery of both monomers in high purity. The recovered pure monomers can be used to regenerate new PtM-CR-PII plastics

enabling sustainable polymer-monomers-polymer circulation.

关键词

Keywords

references

Gibb, B. C. Plastics are forever. Nat. Chem. 2019 , 11 , 394−395..

Liu, Z.; Fang, Z.; Zheng, N.; Yang, K.; Sun, Z.; Li, S.; Li, W.; Wu, J.; Xie, T. Chemical upcycling of commodity thermoset polyurethane foams towards high-performance 3D photo-printing resins. Nat. Chem. 2023 , 15 , 1773−1779..

Wang, Y.; van Putten, R. J.; Tietema, A.; Parsons, J. R.; Gruter, G.-J. M. Polyester biodegradability: Importance and potential for optimisation. Green Chem. 2024 , 26 , 3698−3716..

Bachmann, M.; Zibunas, C.; Hartmann, J.; Tulus, V.; Suh, S.; Guillén-Gosálbez, G.; Bardow, A. Towards circular plastics within planetary boundaries. Nat. Sustain. 2023 , 6 , 599−610..

Borrelle, S. B.; Ringma, J.; Law, K. L.; Monnahan, C. C.; Lebreton, L.; McGivern, A.; Murphy, E.; Jambeck, J.; Leonard, G. H.; Hilleary, M. A.; Eriksen, M.; Possingham, H. P.; De Frond, H .; Gerber, L. R.; Polidoro, B.; Tahir, A.; Bernard, M.; Mallos, N.; Barnes, M.; Rochman, C. M. Predicted growth in plastic waste exceeds efforts tomitigate plastic pollution. Science 2020 , 369 , 1515−1518..

MacLeo, M.; Arp, H. P. H.; Tekman, M. B.; Jahnke, A. The global threat from plastic pollution. Science 2021 , 373 , 61−65..

Martín, A. J.; Mondelli, C.; Jaydev, S. D.; Pérez-Ramírez, J. Catalytic processing of plastic waste on the rise. Chem 2021 , 7 , 1487−1533..

Schneiderman, D. K.; Hillmyer, M. A. 50 th Anniversary perspective: There is a great future in sustainable polymers. Macromolecules 2017 , 50 , 3733−3749..

Wang, B.; Zhang, Q.; Wang, Z.; Shi, C.; Gong, X.; Tian, H.; Qu, D. Acid-catalyzed disulfide-mediated reversible polymerization for recyclable dynamic covalent materials. Angew. Chem. Int. Ed. 2023 , 62 , e202215329..

Zhang, Q.; Deng, Y.; Shi, C.; Feringa, B.; Tian, H.; Qu, D. Dual closed-loop chemical recycling of synthetic polymers by intrinsically reconfigura ble poly(disulfides). Matter 2021 , 4 , 1352−1364..

Cao, Q.; Tu, Y.; Fan, H.; Shan, S.; Cai, Z.; Zhu, J. Torsional strain enabled ring-opening polymerization towards axially chiral semiaromatic polyesters with chemical recyclability. Angew. Chem. Int. Ed. 2024 , 63 , e202400196..

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..

Lv, W.; Li, M.; Tao, Y. Bridged bicyclic lactam enables chemically recyclable nylon. Angew. Chem. Int. Ed. 2024 , 63 , e202402541..

Wang, Y.; Zhu, Y.; Lv, W.; Wang, X.; Tao, Y. Tough while recyclable plastics enabled by monothiodilactone monomers. J. Am. Chem. Soc. 2023 , 145 , 1877−1885..

Li, J.; Liu, F.; Liu, Y.; Shen, Y.; Li, Z. Functionalizable and chemically recyclable thermoplastics from chemoselective ring-opening polymerization of bio-renewable bifunctional α -methylene- δ -valerolactone. Angew. Chem. Int. Ed. 2022 , 61 , e202207105..

Li, Z.; Zhao, D.; Shen, Y.; Li, Z. Ring-opening polymerization of enantiopure bicyclic ether-ester monomers toward closed-loop recyclable and crystalline stereoregular polyesters via chemical upcycling of bioplastic. Angew. Chem. Int. Ed. 2023 , 62 , e202302101..

Li, Z.; Shen, Y.; Li, Z. Ring-opening polymerization of lactones to prepare closed-loop recyclable polyesters. Macromolecules 2024 , 57 , 1919−1940..

Rosetto, G.; Vidal, F.; McGuire, T. M.; Kerr, R. W. F.; Williams, C. K. High molar mass polycarbonates as closed-loop recyclable thermoplastics. J. Am. Chem. Soc. 2024 , 146 , 8381−8393..

Zhao, J.; Yue,T.; Ren, B.; Lu, X.; Ren, W. Closed-loop recycling of sulfur-rich polymers with tunable properties spanning thermoplastics, elastomers, and vitrimers. Nat. Commun. 2024 , 15 , 3002..

Liu, Y.; Yu, Z.; Wang, B.; Li, P.; Zhu, J.; Ma, S. Closed-loop chemical recycling of thermosetting polymers and the ir applications: a review. Green Chem. 2022 , 24 , 5691−5708..

Mangold, H.; von Vacano, B. The frontier of plastics recycling: Rethinking waste as a resource for high-value applications. Macromol. Chem. Phys. 2022 , 223 , 2100488..

Arifuzzaman, M.; Sumpter, B. G.; Demchuk, Z.; Do, C.; Arnould, M. A.; Rahman, M. A.; Cao, P. F.; Popovs, I.; Davis, R. J.; Dai, S.; Saito, T. Selective deconstruction of mixed plastics by a tailored organocatalyst. Mater. Horiz. 2023 , 10 , 3360−3368..

Wang, B.; Wang, Y.; Du, S.; Zhu, J.; Ma, S. Upcycling of thermosetting polymers into high-value materials. Mater. Horiz. 2023 , 10 , 41−51..

Li, J.; Li, W.; Zhang, W.; Zhu, S.; Luo, C.; Liu, W.; Zhang, L. Enhancing molecular chain entanglement and π - π stacking toward the improvement of shape memory performance of polyimide. Chinese J. Polym. Sci. 2023 , 41 , 1261−1268..

Wan, B.; Dong, X.; Yang, X.; Wang, J.; Zheng, M.; Dang, Z.; Chen, G.; Zha, J. Rising of dynamic polyimi de materials: a versatile dielectric for electrical and electronic applications. Adv. Mater. 2023 , 35 , 2301185..

Li, Y.; Sun, G.; Zhou, Y.; Liu, G.; Wang, J.; Han, S. Progress in low dielectric polyimide film-a review. Prog. Org. Coat. 2022 , 172 , 107103..

Liu, X.; Zheng, M.; Chen, G.; Dang, Z.; Zha, J. High-temperature polyimide dielectric materials for energy storage: Theory, design, preparation and properties. Energ. Environ. Sci. 2022 , 15 , 56−81..

Ruan, K.; Guo, Y.; Gu, J. Liquid crystalline polyimide films with high intrinsic thermal conductivitiesand robust toughness. Macromolecules 2021 , 54 , 4934−4944..

Gouzman, I.; Grossman, E.; Verker, R.; Atar, N.; Bolker, A.; Eliaz, N. Advances in polyimide-based materials for space applications. Adv. Mater. 2019 , 31 , 1807738..

Arrington, C. B.; Hegde, M.; Meenakshisundaram, V.; Dennis, J. M.; Williams, C. B.; Long, T. E. Supramolecular salts for additive manufacturing of polyimides. ACS Appl. Mater. Interfaces 2021 , 13 , 48061−48070..

Wan, B.; Yang, X.; Dong, X.; Zheng, M.; Zhao, Q.; Zhang, H.; Chen, G.; Zha, J. Dynamic sustainable polyimide film combining hardness with softness via a “mimosa-like” bionic strategy. Adv. Mater. 2022 , 35 , 2207451..

Lei, X.; Jin, Y.; Sun, H.; Zhang, W. Rehealable imide-imine hybrid polymers with full recyclability. J. Mater. Chem. A 2017 , 5 , 21140−21145..

Liaw, D. J.; Wang, K.; Huang, Y.; Lee, K. R.; Lai, J.; Ha, C. Advanced polyimide materials: Syntheses, physical properties and applications. Prog. Polym. Sci. 2012 , 37 , 907−974..

Guan, T.; Wang, X.; Zhao, X.; Lu, X.; Wang, X.; Wang, Y.; Sun, J. Reversibly cross-linking polyimide and cyclophosphazene toward closed-loop recyclable plastics with high mechanical strength, excellent flame retardancy, and chemical resistance. CCS Chem. 2024 , 6 , 976−987..

Wan, B.; Xiao, M.; Dong, X.; Yang, X.; Zheng, M.; Dang, Z.; Chen, G.; Zha, J. Dynamic covalent adaptable polyimide hybrid dielectric films with sup erior recyclability. Adv. Mater . 2023 , DOI: 10.1002/adma.202304175..

Zhang, X.; Zhang, S.; Liu, W.; Abbas, Y.; Wu, Z.; Eichen, Y.; Zhao, J. Thermally switchable polymers: From thermo-reversibly self-healing hybrid polymers to irreversibly crosslinked flame-retardant networks. Chem. Eng. J. 2021 , 411 , 128467..

Liu, T.; Peng, J.; Liu, J.; Hao, X.; Guo, C.; Ou, R.; Liu, Z.; Wang, Q. Fully recyclable, flame-retardant and high-performance carbon fiber composites based on vanillin-terminated cyclophosphazene polyimine thermosets. Compos. Part B-Eng. 2021 , 224 , 109188..

Lei, X.; Xiong, G.; Xiao, Y.; Huang, T.; Xin, X.; Xue, S.; Zhang, Q. High temperature shape memory poly(amide-imide)s with strong mechanical robustness. Polym. Chem. 2022 , 13 , 5082−5093..

Zhao, S.; Abu-Omar, M. M. Recyclable and malleable epoxy thermoset bearing aromatic imine bonds. Macromolecules 2018 , 51 , 9816−9824..

Yang, Z.; Zhang, Y.; Li, S.; Zhang, X.; Wang, T.; Wang, Q. Fully closed-loop recyclable thermosetting shape memory polyimide. ACS Sustainable Chem. Eng. 2020 , 8 , 18869−18878..

Halder, A.; Karak, S.; Addicoat, M.; Bera, S.; Chakraborty, A.; Kunjattu, S. H.; Pachfule, P.; Heine, T.; Banerjee, R. Ultrastable imine-based covalent organic frameworks for sulfuric acid recovery: an effect of interlayer hydrogen bonding. Angew. Chem. Int. Ed. 2018 , 57 , 5797−5802..

Yuan, Y.; Chen, H.; Jia, L.; Lu, X.; Yan, S.; Zhao, J.; Liu, S. Aromatic polyimine covalent adaptable networks with superior water and heat resistances. Eur. Polym. J. 2023 , 187 , 111912..

Lei, X.; Liu, Y.; Xiao, Y.; Zhang, Y.; Huang, T.; Zhang, Q. High-performance poly(imide-imine) vitrimers derived from semiaromatic bisimide diamines. Macromolecules 2023 , 56 , 9866−9880..

Wang, Y.; Li, M.; Chen, J.; Tao, Y.; Wang, X. O-to-S substitution enables dovetailing conflicting cyclizability, polymerizability, and recyclability: dithiolactone vs. dilactone. Angew. Chem. Int. Ed. 2021 , 60 , 22547−22553..

Shi, C.; Li, Z.; Caporaso, L. ; Cavallo, L.; Falivene, L.; Chen, E. Y.-X. Hybrid monomer design for unifying conflicting polymerizability, recyclability, and performance properties. Chem 2021 , 7 , 670−685..

Lu, X.; Xie, P.; Li, X.; Li, T.; Sun, J. Acid-cleavable aromatic polymers for the fabrication of closed-loop recyclable plastics with high mechanical strength and excellent chemical resistance. Angew. Chem. Int. Ed. 2024 , 63 , e202316453..

Li, X.; Clarke, R. W.; Jiang, J.; Xu, T.; Chen, E. Y.-X. A circular polyester platform based on simple gem-disubstituted valerolactones. Nat. Chem. 2022 , 15 , 278−285..

Li, X. L.; Clarke, R. W.; An, H. Y.; Gowda, R. R.; Jiang, J.; Xu, T.; Chen, E. Y.-X. Dual recycling of depolymerization catalyst and biodegradable polyester that markedly outperforms polyolefins. Angew. Chem. Int. Ed. 2023 , 62 , e202303791..

Häußler, M.; Eck, M.; Rothauer, D.; Mecking, S. Closed-loop recycling of polyethylene-like materials. Nature 2021 , 590 , 423−427..

Guo, Y.; Shi, C.; Du, T.; Che ng, X.; Du, F.; Li, Z. Closed-loop recyclable aliphatic poly(ester-amide)s with tunable mechanical properties. Macromolecules 2022 , 55 , 4000−4010..

Fan, H.; Yang, X.; Chen, J.; Tu, Y.; Cai, Z.; Zhu, J. Advancing the development of recyclable aromatic polyesters by functionalization and stereocomplexation. Angew. Chem. Int. Ed. 2022 , 61 , e202117639..

Zhu, J.; Watson, E. M.; Tang, J.; Chen, E. Y. X. A synthetic polymer system with repeatable chemical recyclability. Science 2018 , 360 , 398−403..

Zhang, Z.; Lei, D.; Zhang, C.; Wang, Z.; Jin, Y.; Zhang, W.; Liu, X.; Sun, J. Strong and tough supramolecular covalent adaptable networks with room-temperature closed-loop recyclability. Adv. Mater. 2022, 35, 2208619..

Yuan, Y.; Sun, Y.; Yan, S.; Zhao, J.; Liu, S.; Zhang, M.; Zheng, X.; Jia, L. Multiply fully recyclable carbon fibre reinforced heat-resistant covalent thermosetting advanced composites. Nat. Commun. 2017 , 8, 14657..

Saito, K.; Eisenre ich, F.; Türel, T.; Tomović, Ž. Closed-loop recycling of poly(imine-carbonate) derived from plastic waste and bio-based resources. Angew. Chem. Int. Ed. 2022 , 61 , e202211806..

Qin, B.; Liu, S.; Huang, Z.; Zeng, L.; Xu, J.; Zhang, X. Closed-loop chemical recycling of cross-linked polymeric materials based on reversible amidation chemistry. Nat. Commun. 2022 , 13 , 7595..

Ma, Y.; Jiang, X.; Shi, Z.; Berrocal, J. A.; Weder, C. Closed-loop recycling of vinylogous urethane vitrimers. Angew. Chem. Int. Ed. 2023 , 62 , e202306188..

Lu, X.; Xie, P.; Xiang, X.; Sun, J. Mechanically robust supramolecular plastics with energy-savingand highly efficient closed-loop recyclability. Macromolecules 2022 , 55 , 2557−2565..

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..

Lei, Z.; Chen, H.; Luo, C.; Rong, Y.; Hu, Y.; Jin, Y. ; Long, R.; Yu, K.; Zhang, W. Recyclable and malleable thermosets enabled by activating dormant dynamic linkages. Nat. Chem. 2022 , 14 , 1399−1404..

Hu, Z.; Hu, F.; Deng, L.; Yang, Y.; Xie, Q.; Gao, Z.; Pan, C.; Jin, Y.; Tang, J.; Yu, G.; Zhang, W. Reprocessible triketoenamine-based vitrimers with closed-loop recyclability. Angew. Chem. Int. Ed. 2023 , 62 , e202306039..

Christensen, P. R.; Scheuermann, A. M.; Loeffler, K. E.; Helms, B. A. Closed-loop recycling of plastics enabled by dynamic covalent diketoenamine bonds. Nat. Chem. 2019 , 11 , 442−448..

Chen, H.; Hu, Y.; Luo, C.; Lei, Z.; Huang, S.; Wu, J.; Jin, Y.; Yu, K.; Zhang, W. Spiroborate-linked ionic covalent adaptable networks with rapid reprocessability and closed-loop recyclability. J. Am. Chem. Soc. 2023 , 145 , 9112−9117..

Zhang, X.; Eichen, Y.; Miao, Z.; Zhang, S.; Cai, Q.; Liu, W.; Zhao, J.; Wu, Z. Novel phosphazene-based flame retardant polyimine vitrimers with monomer-recovery and high performances. Chem. Eng. J. 2022 , 440 , 135806..

Miao, Z.; Yan, D.; Zhang, T.; Yang, F.; Zhang, S.; Liu, W.; Wu, Z. High-efficiency flame retardants of a P–N-rich polyphosphazene elastomer nanocoating on cotton fabric. ACS Appl. Mater. 2021 , 13 , 32094−32105..

Duan, H.; Chen, Y.; Ji, S.; Hu, R.; Ma, H. A novel phosphorus/nitrogen-containing polycarboxylic acid endowing epoxy resin with excellent flame retardance and mechanical properties. Chem. Eng. J. 2019 , 375 , 121916..

Liu, H.; Wang, X.; Wu, D. Novel cyclotriphosphazene-based epoxy compound and its application in halogen-free epoxy thermosetting systems: synthesis, curing behaviors, and flame retardancy. Polym. Degrad. Stabil. 2014 , 103 , 96−112..

Teng, N.; Dai, J.; Wang, S.; Hu, J.; Liu, X. Hyperbranched flame retardant for epoxy resin modification: simultaneously improved flame retardancy, toughness and strength as well as glass transition temperature. Chem. Eng. J. 2022 , 428 , 131226..

Nishimura, Y.; Chung, J.; Muradyan, H.; Guan, Z. Silyl ether as a robust and thermally stable dynamic covalent motif for malleable polymer design. J. Am. Chem. Soc. 2017 , 139 , 14881−14884..

Delahaye, M.; Winne, J. M.; Du Prez, F. E. Internal catalysis in covalent adaptable networks: phthalate monoester transesterification as a versatile dynamic cross-linking chemistry. J. Am. Chem. Soc. 2019 , 141 , 15277−15287..

Li, Q.; Ma, S.; Li, P.; Wang, B.; Yu, Z.; Feng, H.; Liu, Y.; Zhu, J. Fast reprocessing of acetal covalent adaptable networks with high performance enabled by neighboring group participation. Macromolecules 2021 , 54 , 8423−8434..

He, C.; Shi, S.; Wang, D.; Helms, B. A.; Russell, T. P. Poly(oxime-ester) vitrimers with catalyst-free bond exchange. J. Am. Chem. Soc. 2019 , 141 , 13753−13757..

Yu, S.; Wu, S.; Zhang, C.; Tang, Z.; Luo, Y.; Guo, B.; Zhang, L. Catalyst-free metathesis of cyclic acetals and spirocyclic acetal covalent adaptable networks. ACS Macro Lett. 2020 , 9 , 1143−1148..

Yu, P.; Wang, H.; Li, T.; Wang, G.; Jia, Z.; Dong, X.; Xu, Y.; Ma, Q.; Zhang, D.; Ding, H.; Yu, B. Mechanically robust, recyclable, and self-healing polyimine networks. Adv. Sci. 2023 , 10 , 2 02300958..

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