Poly(imine-amide) Hybrid Covalent Adaptable Networks <italic style="font-style: italic">via</italic> <italic style="font-style: italic">in situ</italic> Oxidation Polymerization

Hong-Xuan Chen; Ze-Peng Lei; Shao-Feng Huang; Huan Jiang; Kai Yu; Ying-Hua Jin; Wei Zhang

doi:10.1007/s10118-023-3022-3

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Poly(imine-amide) Hybrid Covalent Adaptable Networks via in situ Oxidation Polymerization

RESEARCH ARTICLE | Updated：2023-09-21

- Poly(imine-amide) Hybrid Covalent Adaptable Networks via in situ Oxidation Polymerization
- Chinese Journal of Polymer Science Vol. 41, Issue 10, Pages: 1577-1583(2023)
- Affiliations：
  
  a.Department of Chemistry, University of Colorado Boulder, Boulder, Colorado 80309, United States
  b.RockyTech Ltd. Boulder, Colorado 80309, United States
  c.Department of Mechanical Engineering, University of Colorado Denver, Denver, Colorado 80217, United States
- Author bio：
  
  jin@rockytechs.com (Y.H.J.)
  wei.zhang@colorado.edu (W.Z.)
- Funds：
- DOI：10.1007/s10118-023-3022-3
  CLC：
- Received：30 April 2023，
  
  Revised：2023-6-20，
  
  Accepted：23 June 2023，
  
  Online First：24 July 2023，
  
  Published：01 October 2023
- Accepted：
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Chen, H. X.; Lei, Z. P.; Huang, S. F.; Jiang, H.; Yu, K.; Jin, Y. H.; Zhang, W. Poly(imine-amide) hybrid covalent adaptable networks via in situ oxidation polymerization. Chinese J. Polym. Sci. 2023, 41, 1577–1583

Hong-Xuan Chen, Ze-Peng Lei, Shao-Feng Huang, et al. Poly(imine-amide) Hybrid Covalent Adaptable Networks via in situ Oxidation Polymerization[J]. Chinese Journal of Polymer Science, 2023, 41(10): 1577-1583. DOI: 10.1007/s10118-023-3022-3.
Chen, H. X.; Lei, Z. P.; Huang, S. F.; Jiang, H.; Yu, K.; Jin, Y. H.; Zhang, W. Poly(imine-amide) hybrid covalent adaptable networks via in situ oxidation polymerization. Chinese J. Polym. Sci. 2023, 41, 1577–1583 DOI： 10.1007/s10118-023-3022-3.

Hong-Xuan Chen, Ze-Peng Lei, Shao-Feng Huang, et al. Poly(imine-amide) Hybrid Covalent Adaptable Networks via in situ Oxidation Polymerization[J]. Chinese Journal of Polymer Science, 2023, 41(10): 1577-1583. DOI: 10.1007/s10118-023-3022-3. DOI：

摘要

We report the first example of

in situ

oxidation-polymerization that has enabled successful synthesis of mechanically strong poly(imine-amide) covalent adaptable networks. These hybrid materials exhibit high Young’s modulus and tensile strength while maintaining their reprocessibility and recyclability. This work demonstrates the great potential of the

in situ

transformation strategy.

Abstract

Polyimine represents a rapidly emerging class of readily accessible and affordable covalent adaptable networks (CANs) that have been extensively studied in the past few years. While being highly malleable and recyclable

the pioneering polyimine materials are relatively soft and not suitable for certain applications that require high mechanical performance. Recent studies have demonstrated the possibility of significantly improving polyimine properties by varying its monomer building blocks

but such component variations are usually not straightforward and can be potentially challenging and costly. Herein

we report an

in situ

oxidation polymerization strategy for preparation of mechanically strong poly(imine-amide) (PIA) hybrid CANs from simple amine and aldehyde monomers. By converting a portion of reversible imine bonds into high-strength amide linkages

in situ

the obtained hybrid materials exhibit gradually improved Young’s modulus and ultimate tensile strength as the oxidation level increased. Meanwhile

the PIAs remain reprocessable and can be depolymerized into small molecules and oligomers similar as polyimine. This work demonstrates the great potential of the

in situ

transformation strategy as a new approach for development of various mechanically tunable CANs from the same starting building blocks.

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Scott,T.F.;Schneider,A.D.;Cook,W.D.;Bowman,C.N.Photoinducedplasticityincross-linkedpolymers. Science 2005 , 308 ,1615−1617..

Lei,Z.;Chen,H.;Jin,Y.;Zhang,W.Dynamiccovalentchemistrytowardwearableelectronics. Cell Rep. Phys. Sci. 2023 ,101336..

Cash,J.J.;Kubo,T.;Bapat,A.P.;Sumerlin,B.S.Room-temperatureself-healingpolymersbasedondynamic-covalentboronicesters. Macromolecules 2015 , 48 ,2098−2106..

Denissen,W.;Rivero,G.;Nicolaÿ,R.;Leibler,L.;Winne,J.M.;DuPrez,F.E.Vinylogousurethanevitrimers. Adv. Funct. Mater. 2015 , 25 ,2451−2457..

Fortman,D.J.;Brutman,J.P.;Cramer,C.J.;Hillmyer,M.A.;Dichtel,W.R.Mechanicallyactivated,catalyst-freepolyhydroxyurethanevitrimers. J. Am. Chem. Soc. 2015 , 137 ,14019−14022..

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

Taynton,P.;Zhu,C.;Loob,S.;Shoemaker,R.;Pritchard,J.;Jin,Y.;Zhang,W.Re-healablepolyiminethermosets:polymercompositionandmoisturesensitivity. Polym. Chem. 2016 , 7 ,7052−7056..

Hendriks,B.;Waelkens,J.;Winne,J.M.;DuPrez,F.E.Poly(thioether)vitrimers via transalkylationoftrialkylsulfoniumsalts. ACS Macro Lett. 2017 , 6 ,930−934..

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

Jin,Y.;Lei,Z.;Taynton,P.;Huang,S.;Zhang,W.Malleableandrecyclablethermosets:thenextgenerationofplastics. Matter 2019 , 1 ,1456−1493..

Li,Q.;Ma,S.;Li,P.;Wang,B.;Yu,Z.;Feng,H.;Liu,Y.;Zhu,J.Fastreprocessingofacetalcovalentadaptablenetworkswithhighperformanceenabledbyneighboringgroupparticipation. Macromolecules 2021 , 54 ,8423−8434..

Lei,Z.;Chen,H.;Luo,C.;Rong,Y.;Hu,Y.;Jin,Y.;Long,R.;Yu,K.;Zhang,W.Recyclableandmalleablethermosetsenabledbyactivatingdormantdynamiclinkages. Nat. Chem. 2022 , 14 ,1399−1404..

Zhu,C.;Xi,C.;Doro,W.;Wang,T.;Zhang,X.;Jin,Y.;Zhang,W.Tuningthephysicalpropertiesofmalleableandrecyclablepolyiminethermosets:theeffectofsolventandmonomerconcentration. RSC Adv. 2017 , 7 ,48303−48307..

Dhers,S.;Vantomme,G.;Avérous,L.Afullybio-basedpolyiminevitrimerderivedfromfructose. Green Chem. 2019 , 21 ,1596−1601..

Su,Z.;Huang,S.;Wang,Y.;Ling,H.;Yang,X.;Jin,Y.;Wang,X.;Zhang,W.Robust,high-barrier,andfullyrecyclablecellulose-basedplasticreplacementenabledbyadynamiciminepolymer. J. Mater.Chem. A 2020 , 8 ,14082−14090..

Wang,S.;Ma,S.;Li,Q.;Xu,X.;Wang,B.;Huang,K.;liu,Y.;Zhu,J.Facilepreparationofpolyiminevitrimerswithenhancedcreepresistanceandthermalandmechanicalproperties via metalcoordination. Macromolecules 2020 , 53 ,2919−2931..

Liu,T.;Peng,J.;Liu,J.;Hao,X.;Guo,C.;Ou,R.;Liu,Z.;Wang,Q.Fullyrecyclable,flame-retardantandhigh-performancecarbonfibercompositesbasedonvanillin-terminatedcyclophosphazenepolyiminethermosets. Compos. B: Eng. 2021 , 224 ,109188..

Yu,L.;Lei,Z.;Sun,X.;Ding,P.;Wesche,A.;Jin,Y.;Zhang,W.;Long,R.Rapidfabricationoffiber-reinforcedpolyiminecompositeswithreprocessability,repairability,andrecyclability. ACS Appl. Polym. Mater. 2021 , 3 ,5808−5817..

Zhao,Q.;Zhang,M.;Gao,S.;Pan,Z.;Xue,Y.;Jia,P.;Bo,C.;Luo,Z.;Song,F.;Zhou,Y.Amussel-inspiredhighbio-contentthermosettingpolyiminepolymerwithexcellentadhesion,flameretardancy,room-temperatureself-healinganddiverserecyclability. J. Mater. Chem. A 2022 , 10 ,11363−11374..

Zhang,Z.;Lei,D.;Zhang,C.;Wang,Z.;Jin,Y.;Zhang,W.;Liu,X.;Sun,J.Strongandtoughsupramolecularcovalentadaptablenetworkswithroom-temperatureclosed-looprecyclability. Adv. Mater. 2023 , 35 ,2208619..

Lei,X.;Jin,Y.;Sun,H.;Zhang,W.Rehealableimide-iminehybridpolymerswithfullrecyclability. J. Mater. Chem. A 2017 , 5 ,21140−21145..

Murthy,N.S.Hydrogenbonding,mobility,andstructuraltransitionsinaliphaticpolyamides. J. Polym. Sci., Part B: Polym. Phys. 2006 , 44 ,1763−1782..

Krishnan,P.S.G.;Kulkarni,S.T.;Deopura,B.L.;Lin,C.A.;Agrawal,A.K.;Jassal,M.;Farrington,D.W.;Lunt,J.;Davies,S.;Blackburn,R.S.in Polyesters and Polyamides (inUnitedStates),WoodheadPublishing, 2008 ..

Bal,B.S.;Childers,W.E.;Pinnick,H.W.Oxidationof α , β -unsaturatedaldehydes. Tetrahedron 1981 , 37 ,2091−2096..

Waller,P.J.;Lyle,S.J.;OsbornPopp,T.M.;Diercks,C.S.;Reimer,J.A.;Yaghi,O.M.Chemicalconversionoflinkagesincovalentorganicframeworks. J. Am. Chem. Soc. 2016 , 138 ,15519−15522..

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Poly(imine-amide) Hybrid Covalent Adaptable Networks via in situ Oxidation Polymerization

DOI：10.1007/s10118-023-3022-3

摘要

Abstract

关键词

Keywords

references