High-Performance Recyclable Furan-based Epoxy Resin and Its Carbon Fiber Composites with Dense Hydrogen Bonding

Chang-Bo Zhao; Lu-Kun Feng; Hui Xie; Ming-Liang Wang; Bing Guo; Zhi-Yong Xue; Cai-Zhen Zhu; Jian Xu

doi:10.1007/s10118-023-3045-9

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High-Performance Recyclable Furan-based Epoxy Resin and Its Carbon Fiber Composites with Dense Hydrogen Bonding

RESEARCH ARTICLE | Updated：2023-12-26

- High-Performance Recyclable Furan-based Epoxy Resin and Its Carbon Fiber Composites with Dense Hydrogen Bonding
- Chinese Journal of Polymer Science Vol. 42, Issue 1, Pages: 73-86(2024)
- Affiliations：
  
  a.Advanced Materials Research Institute, North China Electric Power University, Beijing 102206, China
  b.Institute of Low-Dimensional Materials Genome Initiative, College of Chemistry and Environmental Engineering, Shenzhen University, Shenzhen 518060, China
  c.Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China
  d.School of Science and Shenzhen Key Laboratory of Flexible Printed Electronics Technology, and Shenzhen Key Laboratory of Advanced Functional Carbon Materials Research and Comprehensive Application, Harbin Institute of Technology, Shenzhen 518055, China
- Author bio：
  
  guobing2020@hit.edu.cn (B.G.)
  xuezy@ncepu.edu.cn (Z.Y.X.)
  czzhu@szu.edu.cn (C.Z.Z.)
- Funds：
- DOI：10.1007/s10118-023-3045-9
  CLC：
- Received：16 June 2023，
  
  Revised：2023-7-21，
  
  Accepted：03 August 2023，
  
  Online First：20 September 2023，
  
  Published：01 January 2024
- Accepted：
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Zhao, C. B.; Feng, L. K.; Xie, H; Wang, M. L.; Guo, B.; Xue, Z. Y.; Zhu, C. Z.; Xu, J. High-performance recyclable furan-based epoxy resin and its carbon fiber composites with dense hydrogen bonding. Chinese J. Polym. Sci. 2024, 42, 73–86

Chang-Bo Zhao, Lu-Kun Feng, Hui Xie, et al. High-Performance Recyclable Furan-based Epoxy Resin and Its Carbon Fiber Composites with Dense Hydrogen Bonding[J]. Chinese Journal of Polymer Science, 2024, 42(1): 73-86.
Zhao, C. B.; Feng, L. K.; Xie, H; Wang, M. L.; Guo, B.; Xue, Z. Y.; Zhu, C. Z.; Xu, J. High-performance recyclable furan-based epoxy resin and its carbon fiber composites with dense hydrogen bonding. Chinese J. Polym. Sci. 2024, 42, 73–86 DOI： 10.1007/s10118-023-3045-9.

Chang-Bo Zhao, Lu-Kun Feng, Hui Xie, et al. High-Performance Recyclable Furan-based Epoxy Resin and Its Carbon Fiber Composites with Dense Hydrogen Bonding[J]. Chinese Journal of Polymer Science, 2024, 42(1): 73-86. DOI： 10.1007/s10118-023-3045-9.

摘要

A new monomer (FCN) containing furan and Schiff base structure was designed to formulate recyclable and high-performance epoxy resins with high density of hydrogen bonding

while the resin performance was further examined in carbon-fiber composites.

Abstract

The emerging biomass-based epoxy vitrimers hold great potential to fulfill the requirements for sustainable development of society. Since the existence of dynamic chemical bonds in vitrimers often reduces both the thermal and mechanical properties of epoxy resins

it is challenging to produce recyclable epoxy vitrimers with both excellent mechanical properties and good thermal stability. Herein

a monomer 4-(((5-(hydroxymethyl)furan-2-yl)methylene)amino)phenol (FCN) containing furan ring with potential to form high density of hydrogen bonding among repeating units is designed and copolymerized with glycerol triglycidyl ether to yield epoxy resin (FCN-GTE)

which intrinsically has dual hydrogen bond networks

dynamic imine structure and resultant high performance. Importantly

as compared to the BPA-GTE

the FCN-GTE exhibits significantly improved mechanical properties owing to the increased density of hydrogen bond network and physical crosslinking interaction. Furthermore

density functional theory (DFT) calculation and

in situ

FTIR analysis is conducted to decipher the formation mechanism of hydrogen bond network. In addition

the FCN-GTE possesses superior UV shielding

chemical degradation

and recyclability because of the existence of abundant imine bonds. Notably

the FCN-GTE-based carbon fiber composites could be completely recycled in an amine solution. This study provides a facile strategy for synthesizing recyclable biomass-based high-performance epoxy vitrimers and carbon fiber composites.

关键词

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references

Filippidi,E.;Cristiani,T.R.;Eisenbach,C.D.;Waite,J.H.;Israelachvili,J.N.;Ahn,B.K.;Valentine,M.T.Tougheningelastomersusingmusselinspirediron-catecholcomplexes. Science 2017 , 358 ,502–505..

deKruijff,G.H.M.;Goschler,T.;Beiser,N.;Stenglein,A.;Türk,O.M.;Waldvogel,S.R.Sustainableaccesstobiobasedbiphenolepoxyresinsbyelectrochemicaldehydrogenativedimerizationofeugenol. Green Chem. 2019 , 21 ,4815−4823..

Tian,Y.;Wang,Q.;Shen,L.;Cui,Z.;Kou,L.;Cheng,J.;Zhang,J.Arenewableresveratrol-basedepoxyresinwithhigh T g ,excellentmechanicalpropertiesandlowflammability. Chem. Eng. J. 2020 , 383 ,123124..

Yu,S.;Zhang,G.;Wu,S.;Tang,Z.;Guo,B.;Zhang,L.Effectsofdynamiccovalentbondmultiplicityontheperformanceofvitrimericelastomers. J. Mater. Chem. A 2020 , 8 ,20503−20512..

Sun,Y.;Wang,M.;Wang,Z.;Mao,Y.;Jin,L.;Zhang,K.;Xia,Y.;Gao,H.Amine-curedglycidylestersasdualdynamicepoxyvitrimers. Macromolecules 2022 , 55 ,523−534..

Zou,W.;Dong,J.;Luo,Y.;Zhao,Q.;Xie,T.Dynamiccovalentpolymernetworks:fromoldchemistrytomoderndayinnovations. Adv. Mater. 2017 , 29 ,1606100..

Yang,Y.;Xu,Y.;Ji,Y.;Wei,Y.Functionalepoxyvitrimersandcomposites. Prog. Mater. Sci. 2021 , 120 ,100710..

Zhang,J.;Gong,Z.;Wu,C.;Li,T.;Tang,Y.;Wu,J.;Jiang,C.;Miao,M.;Zhang,D.Itaconicacid-basedhyperbranchedpolymertoughenedepoxyresinswithrapidstressrelaxation,superbsolventresistanceandclosed-looprecyclability. Green Chem. 2022 , 24 ,6900−6911..

Krishnakumar,B.;Sanka,R.V.S.P.;Binder,W.H.;Parthasarthy,V.;Rana,S.;Karak,N.Vitrimers:associativedynamiccovalentadaptivenetworksinthermosetpolymers. Chem. Eng. J. 2020 , 385 ,123820..

Trinh,T.E.;Ku,K.;Yeo,H.Reprocessableandchemicallyrecyclablehardvitrimersbasedonliquid-crystallineepoxides. Adv. Mater. 2023 , 35 ,e2209912..

Memon,H.;Liu,H.;Rashid,M.A.;Chen,L.;Jiang,Q.;Zhang,L.;Wei,Y.;Liu,W.;Qiu,Y.Vanillin-basedepoxyvitrimerwithhighperformanceandclosed-looprecyclability. Macromolecules 2020 , 53 ,621−630..

Thi-Nguyet,T.;DiMauro,C.;Graillot,A.;Mija,A.Chemicalreactivityandtheinfluenceofinitiatorsontheepoxidizedvegetableoil/dicarboxylicacidsystem. Macromolecules 2020 , 53 ,2526−2538..

Si,H.;Zhou,L.;Wu,Y.;Song,L.;Kang,M.;Zhao,X.;Chen,M.Rapidlyreprocessable,degradableepoxyvitrimerandrecyclablecarbonfiberreinforcedthermosetcompositesreliedonhighcontentsofexchangeablearomaticdisulfidecrosslinks. Compos. Part B: Eng. 2020 , 199 ,108278..

Xu,Z.;Liang,Y.;Ma,X.;Chen,S.;Yu,C.;Wang,Y.;Zhang,D.;Miao,M.Recyclablethermosethyperbranchedpolymerscontainingreversiblehexahydro-s-triazine. Nat. Sustain. 2019 , 3 ,29−34..

Wang,B.;Ma,S.;Li,Q.;Zhang,H.;Liu,J.;Wang,R.;Chen,Z.;Xu,X.;Wang,S.;Lu,N.;Liu,Y.;Yan,S.;Zhu,J.Facilesynthesisof"digestible",rigid-and-flexible,bio-basedbuildingblockforhigh-performancedegradablethermosettingplastics. Green Chem. 2020 , 22 ,1275−1290..

Warlin,N.;GarciaGonzalez,M.N.;Mankar,S.;Valsange,N.G.;Sayed,M.;Pyo,S.H.;Rehnberg,N.;Lundmark,S.;Hatti-Kaul,R.;Jannasch,P.;Zhang,B.Arigidspirocyclicdiolfromfructose-based5-hydroxymethylfurfural:synthesis,life-cycleassessment,andpolymerizationforrenewablepolyestersandpoly(urethane-urea)s. Green Chem. 2019 , 21 ,6667−6684..

Chen,Y.;Tang,Z.;Liu,Y.;Wu,S.;Guo,B.Mechanicallyrobust,self-healable,andreprocessableelastomersenabledbydynamicdualcross-links. Macromolecules 2019 , 52 ,3805−3812..

Röttger,M.;Domenech,T.;vanderWeegen,R.;Nicolaÿ,A.B.R.;Leibler,L.High-performancevitrimersfromcommoditythermoplasticsthroughdioxaborolanemetathesis. Science 2017 , 356 ,62−65..

Montarnal,D.;Capelot,M.;Tournilhac,F.;Leibler,L.Silica-likemalleablematerialsfrompermanentorganicnetworks. Science 2011 , 334 ,965−968..

Pei,Z.;Yang,Y.;Chen,Q.;Wei,Y.;Ji,Y.Regionalshapecontrolofstrategicallyassembledmultishapememoryvitrimers. Adv. Mater. 2016 , 28 ,156−160..

Kawai,K.;Ikeda,K.;Sato,A.;Kabasawa,A.;Kojima,M.;Kokado,K.;Kakugo,A.;Sada,K.;Yoshino,T.;Matsunaga,S.1,2-Disubstituted1,2-dihydro-1,2,4,5-tetrazine-3,6-dioneasadynamiccovalentbondingunitatroomtemperature. J. Am. Chem. Soc. 2022 , 144 ,1370−1379..

Lu,C.;Liu,Y.;Wang,C.;Yong,Q.;Wang,J.;Chu,F.Anintegratedstrategytofabricatebio-baseddual-cureandtoughenedepoxythermosetswithphotothermalconversionproperty. Chem. Eng. J. 2022 , 433 ,134582..

Tretbar,C.A.;Neal,J.A.;Guan,Z.B.Directsilylethermetathesisforvitrimerswithexceptionalthermalstability. J. Am. Chem. Soc. 2019 , 141 ,16595−16599..

Gao,S.;Liu,Y.;Feng,S.;Lu,Z.Reprocessableanddegradablethermosetwithhigh T g cross-linked via Si–O–Phbonds. J. Mater. Chem. A 2019 , 7 ,17498−17504..

Ji,S.;Cao,W.;Yu,Y.;Xu,H.Dynamicdiselenidebonds:exchangereactioninducedbyvisiblelightwithoutcatalysis. Angew. Chem. Int. Ed. 2014 , 126 ,6899−6903..

Liu,X.;Song,X.;Chen,B.;Liu,J.;Feng,Z.;Zhang,W.;Zeng,J.;Liang,L.Self-healingandshape-memoryepoxythermosetsbasedondynamicdiselenidebonds. React. Funct. Polym. 2022 , 170 ,105121..

Yang,L.;Li,Y.;Du,M.;He,Y.;Lan,Y.;Yin,Q.;Zhu,F.;Chang,G.Force-reversibleandenergeticindole-Mg-indolecation- π interactionfordesigningtoughenedandmultifunctionalhigh-performancethermosets. Adv. Funct. Mater. 2021 , 32 ,2111021..

Wang,S.;Ma,S.;Li,Q.;Xu,X.;Wang,B.;Yuan,W.;Zhou,S.;You,S.;Zhu,J.Facileinsitupreparationofhigh-performanceepoxyvitrimerfromrenewableresourcesanditsapplicationinnondestructiverecyclablecarbonfibercomposite. Green Chem. 2019 , 21 ,1484−1497..

Zhao,S.;Abu-Omar,M.M.Recyclableandmalleableepoxythermosetbearingaromaticiminebonds. Macromolecules 2018 , 51 ,9816−9824..

Memon,H.;Wei,Y.;Zhu,C.RecyclableandreformableepoxyresinsbasedondynamiccovalentbondsPresent,past,andfuture. Polym. Test. 2022 , 105 ,107420..

Liu,T.;Hao,C.;Zhang,S.;Yang,X.N.;Wang,L.W.;Han,J.R.;Li,Y.Z.;Xin,J.N.;Zhang,J.W.Aself-healablehighglasstransitiontemperaturebioepoxymaterialbasedonvitrimerchemistry. Macromolecules 2018 , 51 ,5577−5585..

Xu,X.;Ma,S.;Wu,J.;Yang,J.;Wang,B.;Wang,S.;Li,Q.;Feng,J.;You,S.;Zhu,J.High-performance,command-degradable,antibacterialSchiffbaseepoxythermosets:synthesisandproperties. J. Mater. Chem. A 2019 , 7 ,15420−15431..

Savonnet,E.;Grau,E.;Grelier,S.;Defoort,B.;Cramail,H.Divanillin-basedepoxyprecursorsasDGEBAsubstitutesforbiobasedepoxythermosets. ACS Sustainable Chem. Eng. 2018 , 6 ,11008−11017..

Wan,J.;Gan,B.;Li,C.;Molina-Aldareguia,J.;Kalali,E.N.;Wang,X.;Wang,D.-Y.Asustainable,eugenol-derivedepoxyresinwithhighbiobasedcontent,modulus,hardnessandlowflammability:synthesis,curingkineticsandstructure–propertyrelationship. Chem. Eng. J. 2016 , 284 ,1080−1093..

Qi,Y.;Weng,Z.H.;Zhang,K.W.;Wang,J.Y.;Zhang,S.H.;Liu,C.;Jian,X.G.Magnolol-basedbio-epoxyresinwithacceptableglasstransitiontemperature,processabilityandflameretardancy. Chem. Eng. J. 2020 , 387 ,124115..

Cao,Q.;Li,J.;Qi,Y.;Zhang,S.;Wang,J.;Wei,Z.;Pang,H.;Jian,X.;Weng,Z.Engineeringdoubleload-sharingnetworkinthermosetting:muchmorethanjusttoughening. Macromolecules 2022 , 21 ,9502−9512..

Nabipour,H.;Wang,X.;Song,L.;Hu,Y.Ahighperformancefullybio-basedepoxythermosetfromasyringaldehyde-derivedepoxymonomercuredbyfuran-derivedamine. Green Chem. 2021 , 23 ,501−510..

Zhong,L.;Hao,Y.;Zhang,J.;Wei,F.;Li,T.;Miao,M.;Zhang,D.Closed-looprecyclablefullybio-basedepoxyvitrimersfromferulicacid-derivedhyperbranchedepoxyresin. Macromolecules 2022 , 55 ,595−607..

Pansumdaeng,J.;Kuntharin,S.;Harnchana,V.;Supanchaiyamat,N.Fullybio-basedepoxidizedsoybeanoilthermosetsforhighperformancetriboelectricnanogenerators. Green Chem. 2020 , 22 ,6912−6921..

Qi,Y.;Weng,Z.;Kou,Y.;Song,L.;Li,J.;Wang,J.;Zhang,S.;Liu,C.;Jian,X.Synthesizeandintroducebio-basedaromatics-triazineinepoxyresin:enablingextremelyhighthermalstability,mechanicalproperties,andflameretardancytoachievehigh-performancesustainablepolymers. Chem. Eng. J. 2021 , 406 ,126881..

Cao,Q.;Weng,Z.;Qi,Y.;Li,J.;Liu,W.;Liu,C.;Zhang,S.;Wei,Z.;Chen,Y.;Jian,X.Achievinghigherperformanceswithoutanexternalcuringagentinnaturalmagnolol-basedepoxyresin. Chin. Chem. Lett. 2022 , 33 ,2195−2199..

Qi,Y.;Weng,Z.;Kou,Y.;Li,J.;Cao,Q.;Wang,J.;Zhang,S.;Jian,X.Facilesynthesisofbio-basedtetra-functionalepoxyresinanditspotentialapplicationashigh-performancecompositeresinmatrix. Compos. Part B: Eng. 2021 , 214 ,108749..

Lin,J.;Xu,P.;Wang,L.;Sun,Y.;Ge,X.;Li,G.;Yang,X.Multi-scaleinterphaseconstructionofself-assemblynaphthalenediimide/multi-wallcarbonnanotubeandenhancedinterfacialpropertiesofhigh-moduluscarbonfibercomposites. Composi. Sci. Technol. 2019 , 184 ,107855..

Chappuis,S.;Edera,P.;Cloitre,M.;Tournilhac,F.Enrichinganexchangeablenetworkwithoneofitscomponents:thekeytohigh- T g epoxyvitrimerswithacceleratedrelaxation. Macromolecules 2022 , 55 ,6982−6991..

He,J.;Li,L.;Zhou,J.;Tian,J.;Chen,Y.;Zou,H.;Liang,M.Ultra-highmodulusepoxyresinreinforcedbyintensivehydrogenbondnetwork:fromdesign,synthesis,mechanismtoapplications. Compos. Sci. Technol. 2023 , 231 ,109815..

Liu,Y.Y.;Liu,G.L.;Li,Y.D.;Weng,Y.;Zeng,J.B.Biobasedhigh-performanceepoxyvitrimerwithUVshieldingforrecyclablecarbonfiberreinforcedcomposites. ACS Sustainable Chem. Eng. 2021 , 9 ,4638−4647..

Liu,Y.Y.;He,J.;Li,Y.D.;Zhao,X.L.;Zeng,J.B.Biobasedepoxyvitrimerfromepoxidizedsoybeanoilforreprocessableandrecyclablecarbonfiberreinforcedcomposite. Compos. Commun. 2020 , 22 ,100445..

Zhao,X.L.;Liu,Y.Y.;Weng,Y.;Li,Y.D.;Zeng,J.B.Sustainableepoxyvitrimersfromepoxidizedsoybeanoilandvanillin. ACS Sustainable Chem. Eng. 2020 , 8 ,15020−15029..

Barone,V.;Adamo,C.;Lelj,F.Conformationalbehaviorofgaseousglycinebyadensityfunctionalapproach. J. Chem. Phys. 1995 , 102 ,364−370..

Becke;Axel,D.AnewmixingofHartree-Fockandlocaldensity-functionaltheories. J. Chem. Phys. 1993 , 98 ,1372−1377..

Becke;Axel,D.Density-functionalthermochemistry.III.Theroleofexactexchange. J. Chem. Phys. 1993 , 98 ,5648−5652..

Lee,C.;Yang,W.;Parr,R.DevelopmentoftheColle-Salvetticorrelation-energyformulaintoafunctionaloftheelectrondensity. Phys. Rev. B 1988 , 37 ,785−789..

Grimme,S.;Ehrlich,S.;Goerigk,L.Effectofthedampingfunctionindispersioncorrecteddensityfunctionaltheory. J. Comput. Chem. 2011 , 32 ,1456−1465..

Hu,F.;LaScala,J.J.;Sadler,J.M.;Palmese,G.R.Synthesisandcharacterizationofthermosettingfuran-basedepoxysystems. Macromolecules 2014 , 47 ,3332−3342..

Marotta,A.;Faggio,N.;Ambrogi,V.;Mija,A.;Gentile,G.;Cerruti,P.Biobasedfuran-basedepoxy/TiO 2 nanocompositesforthepreparationofcoatingswithimprovedchemicalresistance. Chem. Eng. J. 2021 , 406 ,127107..

Pezzana,L.;Melilli,G.;Guigo,N.;Sbirrazzuoli,N.;Sangermano,M.CationicUVcuringofbioderivedepoxyfuran-basedcoatings:tailoringthefinalpropertiesby in situ formationofhybridnetworkandadditionofmonofunctionalmonomer. ACS Sustainable Chem. Eng. 2021 , 9 ,17403−17412..

Guo,H.;Huang,S.;Yang,X.;Wu,J.;Kirk,T.B.;Xu,J.;Xu,A.;Xue,W.Injectableandself-healinghydrogelswithdouble-dynamicbondtunablemechanical,gel-soltransitionanddrugdeliverypropertiesforpromotingperiodontiumregenerationinperiodontitis. ACS Appl. Mater. Interfaces 2021 , 13 ,61638−61652..

Lee,S.H.;Shin,S.R.;Lee,D.S.Self-healingofcross-linkedPU via dual-dynamiccovalentbondsofaSchiffbasefromcystineandvanillin. Mater. Design 2019 , 172 ,107774..

Zou,Z.;Zhu,C.;Li,Y.;Lei,X.;Zhang,W.;Xiao,J.Rehealable,fullyrecyclable,andmalleableelectronicskinenabledbydynamiccovalentthermosetnanocomposite. Sci. Adv. 2018 , 4 ,eaaq0508..

Memon,H.;Wei,Y.;Zhu,C.Correlatingthethermomechanicalpropertiesofanovelbio-basedepoxyvitrimerwithitscrosslinkdensity. Mater. Today Commun. 2021 , 29 ,102814..

Sangroniz,L.;Sangroniz,A.;Alegria,A.;Fernandez,M.;Irusta,L.;Müller,A.J.;Etxeberria,A.;Santamaría,A.Effectofhydrogenbondingonthephysicochemicalandrheologicalfeaturesofchemicallymodifiedphenoxy. Polymer 2018 , 159 ,12−22..

Coleman,M.M.;Moskala,E.J.FTIRstudiesofpolymerblendscontainingthepoly(hydroxyetherofbisphenolA)andpoly(e-caprolactone). Polymer 1983 , 24 ,251−257..

Mora,A.S.;Tayouo,R.;Boutevin,B.;David,G.;Caillol,S.AperspectiveapproachontheaminereactivityandtheHydrogenbondseffectonepoxy-aminesystems. Eur. Polym. J. 2020 , 123 ,109460..

Qi,Y.;Wang,J.;Kou,Y.;Pang,H.;Zhang,S.;Li,N.;Liu,C.;Weng,Z.;Jian,X.Synthesisofanaromatic N -heterocyclederivedfrombiomassanditsuseasapolymerfeedstock. Nat. Commun. 2019 , 10 ,2107..

Tanaka,Y.;Kakiuchi,H.Studyofepoxycompounds.PartI.Curingreactionsofepoxyresinandacidanhydridewithamineandalcoholascatalyst. J. Appl. Polym. Sci. 1963 , 7 ,1063−1081..

Liu,Y.;Zhao,J.;Peng,Y.;Luo,J.;Cao,L.;Liu,X.Comparativestudyonthepropertiesofepoxyderivedfromaromaticandheteroaromaticcompounds:theroleofhydrogenbonding. Indust. Eng. Chem. Res. 2020 , 59 ,1914−1924..

Ma,X.;Liang,Y.;Xu,Z.;Chen,S.;Cheng,J.;Miao,M.;Zhang,D.Theversatilityofhyperbranchedepoxyresinscontaininghexahydro- s -triazineondiglycidyletherofbisphenol-Acomposites. Compos. Part B: Eng. 2020 , 196 ,108109..

diMauro,C.;Tran,T.N.;Graillot,A.;Mija,A.Enhancingtherecyclabilityofavegetableoil-basedepoxythermosetthroughinitiatorinfluence. ACS Sustainable Chem. Eng. 2020 , 8 ,7690−7700..

Wang,S.;Ma,S.;Xu,C.;Liu,Y.;Dai,J.;Wang,Z.;Liu,X.;Chen,J.;Shen,X.;Wei,J.;Zhu,J.Vanillin-derivedhigh-performanceflameretardantepoxyresins:facilesynthesisandproperties. Macromolecules 2017 , 50 ,1892−1901..

Meng,J.;Zeng,Y.;Zhu,G.;Zhang,J.;Chen,P.;Cheng,Y.;Fang,Z.;Guo,K.Sustainablebio-basedfuranepoxyresinwithflameretardancy. Polym. Chem. 2019 , 10 ,2370−2375..

Jiang,Y.;Ding,D.;Zhao,S.;Zhu,H.;Kenttamaa,H.I.;Abu-Omar,M.M.Renewablethermosetpolymersbasedonligninandcarbohydratederivedmonomers. Green Chem. 2018 , 20 ,1131−1138..

Zhang,Z.;Lei,D.;Zhang,C.;Wang,Z.;Jin,Y.;Zhang,W.;Liu,X.;Sun,J.Strongandtoughsupramolecularcovalentadaptablenetworkswithroom-temperatureclosed-looprecyclability. Adv. Mater. 2023 , 35 ,e2208619..

Shen,Y.;Xu,N.;Adraro,Y.A.;Wang,B.;Liu,Y.;Yuan,W.;Xu,X.;Huang,Y.;Hu,Z.Imineorsecondaryamine-deriveddegradablepolyaminal:low-costmatrixresinwithhighperformance. ACS Sustainable Chem. Eng. 2020 , 8 ,1943−1953..

Wang,S.;Ma,S.Q.;Li,Q.;Yuan,W.C.;Wang,B.B.;Zhu,J.Robust,fire-safe,monomer-recovery,highlymalleablethermosetsfromrenewablebioresources. Macromolecules 2018 , 51 ,8001−8012..

Yu,Q.Q.;Peng,X.H.;Wang,Y.L.;Geng,H.W.;Xu,A.C.;Zhang,X.;Xu,W.L.;Ye,D.Z.Vanillin-baseddegradableepoxyvitrimers:reprocessabilityandmechanicalpropertiesstudy. Eur. Polym. J. 2019 , 117 ,55−63..

Chao,A.;Negulescu,I.;Zhang,D.Dynamiccovalentpolymernetworksbasedondegenerativeiminebondexchange:tuningthemalleabilityandself-healingpropertiesbysolvent. Macromolecules 2016 , 49 ,6277−6284..

Ma,S.;Wei,J.;Jia,Z.;Yu,T.;Yuan,W.;Li,Q.;Wang,S.;You,S.;Liu,R.;Zhu,J.Readilyrecyclable,high-performancethermosettingmaterialsbasedonalignin-derivedspirodiacetaltrigger. J. Mater. Chem. A 2019 , 7 ,1233−1243..

Belowich,M.E.;Stoddart,J.F.Dynamiciminechemistry. Chem. Soc. Rev. 2012 , 41 ,2003−2024..

Zhang,Y.;Yang,B.;Zhang,X.;Xu,L.;Tao,L.;Li,S.;Wei,Y.Amagneticself-healinghydrogel. Chem. Commun. 2012 , 48 ,9305−9307..

Taynton,P.;Yu,K.;Shoemaker,R.K.;Jin,Y.;Qi,H.J.;Zhang,W.Heat-orwater-drivenmalleabilityinahighlyrecyclablecovalentnetworkpolymer. Adv. Mater. 2014 , 26 ,3938−3942..

Lei,Z.Q.;Xie,P.;Rong,M.Z.;Zhang,M.Q.Catalyst-freedynamicexchangeofaromaticSchiffbasebondsanditsapplicationtoself-healingandremoldingofcrosslinkedpolymers. J. Mater. Chem. A 2015 , 3 ,19662−19668..

Kathan,M.;Kovaricek,P.;Jurissek,C.;Senf,A.;Dallmann,A.;Thunemann,A.F.;Hecht,S.Controlofimineexchangekineticswithphotoswitchestomodulateself-healinginpolysiloxanenetworksbylightillumination. Angew. Chem. Int. Ed. 2016 , 55 ,13882−13886..

Taynton,P.;Ni,H.;Zhu,C.;Yu,K.;Loob,S.;Jin,Y.;Qi,H.J.;Zhang,W.Repairablewovencarbonfibercompositeswithfullrecyclabilityenabledbymalleablepolyiminenetworks. Adv. Mater. 2016 , 28 ,2904−2909..

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