Recyclable Polyurea-Urethane Thermosets with De-Crosslinking Capability in Acetic Acid

Xinglei Tao; Wentian Yi; Xiao-Qi Xu; Yapei Wang

doi:10.1007/s10118-022-2872-4

Your Location：

Home >

Browse articles >

Recyclable Polyurea-Urethane Thermosets with De-Crosslinking Capability in Acetic Acid

RESEARCH ARTICLE | Updated：2023-05-26

- Recyclable Polyurea-Urethane Thermosets with De-Crosslinking Capability in Acetic Acid
- Recyclable Polyurea-Urethane Thermosets with De-Crosslinking Capability in Acetic Acid
- 高分子科学（英文版） 2023年41卷第6期页码：859-865
- Affiliations：
  
  Key Laboratory of Advanced Light Conversion Materials and Biophotonics, Department of Chemistry, Renmin University of China, Beijing 100872, China
- Author bio：
  
  xuxiaoqi@ruc.edu.cn (X.Q.X.)
  yapeiwang@ruc.edu.cn (Y.W.)
- Funds：
  
  This work was financially supported by the National Natural Science Foundation of China (No. 21825503).;Electronic supplementary information (ESI) is available free of charge in the online version of this article at http://doi.org/10.1007/s10118-022-2872-4.
- DOI：10.1007/s10118-022-2872-4
  中图分类号： M
- 收稿：2022-08-17，
  
  修回：2022-9-15，
  
  录用：2022-9-17，
  
  网络首发：2022-12-12，
  
  纸质出版：2023-06-01
- Accepted：
Scan QR Code
Tao, X.; Yi, W.; Xu, X.-Q.; Wang, Y. Recyclable polyurea-urethane thermosets with de-crosslinking capability in acetic acid. Chinese J. Polym. Sci. 2023, 41, 859–865

Xinglei Tao, Wentian Yi, Xiao-Qi Xu, et al. Recyclable Polyurea-Urethane Thermosets with De-Crosslinking Capability in Acetic Acid[J]. Chinese Journal of Polymer Science, 2023, 41(6): 859-865.
Tao, X.; Yi, W.; Xu, X.-Q.; Wang, Y. Recyclable polyurea-urethane thermosets with de-crosslinking capability in acetic acid. Chinese J. Polym. Sci. 2023, 41, 859–865 DOI： 10.1007/s10118-022-2872-4.

Xinglei Tao, Wentian Yi, Xiao-Qi Xu, et al. Recyclable Polyurea-Urethane Thermosets with De-Crosslinking Capability in Acetic Acid[J]. Chinese Journal of Polymer Science, 2023, 41(6): 859-865. DOI： 10.1007/s10118-022-2872-4.

摘要

A novel kind of polyurea-urethane thermoset was reported with borate ester as its crosslinking point to enable controllable de-crosslinking. Such a thermoset presents remarkable mechanical properties and outstanding solvent resistance capability

due to its high crosslinking density. The de-crosslinked product can be reporcessed to generate a new thermoplastic material.

Abstract

Covalent crosslinking points within thermosets generally result in excellent mechanical properties and solvent resistance yet lead to limited degradability and recyclability. Those thermosets become degradable or recyclable if crosslinking points are cleavable or reversible. Following this principle

we report a kind of polyurea-urethane thermoset with borate ester as its crosslinking point to enable a controllable de-crosslinking in response to acetate acid. Such a thermoset presents remarkable mechanical properties as well as outstanding solvent resistance capability

due to the high crosslinking density and intermolecular hydrogen bonding. Furthermore

the de-crosslinked product can be reporcessed to generate a brand new thermoplastic material.

关键词

Keywords

references

Auvergne,R.;Caillol,S.;David,G.;Boutevin,B.;Pascault,J.P.Biobasedthermosettingepoxy:presentandfuture. Chem. Rev. 2014 , 114 ,1082−1115..

Martín,A.J.;Mondelli,C.;Jaydev,S.D.;Pérez-Ramírez,J.Catalyticprocessingofplasticwasteontherise. Chem 2021 , 7 ,1487−1533..

Hong,M.;Chen,E.Y.X.Chemicallyrecyclablepolymers:acirculareconomyapproachtosustainability. Green Chem. 2017 , 19 ,3692−3706..

Schneiderman,D.K.;Vanderlaan,M.E.;Mannion,A.M.;Panthani,T.R.;Batiste,D.C.;Wang,J.Z.;Bates,F.S.;Macosko,C.W.;Hillmyer,M.A.Chemicallyrecyclablebiobasedpolyurethanes. ACS Macro Lett. 2016 , 5 ,515−518..

Zheng,N.;Xu,Y.;Zhao,Q.;Xie,T.Dynamiccovalentpolymernetworks:amolecularplatformfordesigningfunctionsbeyondchemicalrecyclingandself-healing. Chem. Rev. 2021 , 121 ,1716−1745..

Kloxin,C.J.;Bowman,C.N.Covalentadaptablenetworks:smart,reconfigurableandresponsivenetworksystems. Chem. Soc. Rev. 2013 , 42 ,7161−7173..

Capelot,M.;Montarnal,D.;Tournilhac,F.;Leibler,L.Metal-catalyzedtransesterificationforhealingandassemblingofthermosets. J. Am. Chem. Soc. 2012 , 134 ,7664−7667..

Yang,Y.;Terentjev,E.M.;Zhang,Y.;Chen,Q.;Zhao,Y.;Wei,Y.;Ji,Y.Reprocessablethermosetsoftactuators. Angew. Chem. Int. Ed. 2019 , 58 ,17474−17479..

Chen,J.H.;An,X.P.;Li,Y.D.;Wang,M.;Zeng,J.B.Reprocessibleepoxynetworkswithtunablephysicalproperties:synthesis,stressrelaxationandrecyclability. Chinese J. Polym. Sci. 2018 , 36 ,641−648..

Li,Z.J.;Zhong,J.;Liu,M.C.;Rong,J.C.;Yang,K.;Zhou,J.Y.;Shen,L.;Gao,F.;He,H.F.Investigationonself-healingpropertyofepoxyresinsbasedondisulfidedynamiclinks. Chinese J. Polym. Sci. 2020 , 38 ,932−940..

Xu,X.Q.;He,Y.;Liu,H.;Wang,Y.Polydiacetylene-polyurethanecrisscrosselastomerasanintrinsicshapememoryconductivepolymer. ACS Macro Lett. 2019 , 8 ,409−413..

Ma,Q.;Liao,S.;Ma,Y.;Chu,Y.;Wang,Y.Anultra-low-temperatureelastomerwithexcellentmechanicalperformanceandsolventresistance. Adv. Mater. 2021 , 33 ,2102096..

Chen,D.;Ni,C.;Xie,L.;Li,Y.;Deng,S.;Zhao,Q.;Xie,T.Homeostaticgrowthofdynamiccovalentpolymernetworktowardultrafastdirectsoftlithography. Sci. Adv. 2021 , 7 ,eabi7360..

Liu,X.;Li,Y.;Fang,X.;Zhang,Z.;Li,S.;Sun,J.Healableandrecyclablepolymericmaterialswithhighmechanicalrobustness. ACS Mater. Lett. 2022 , 4 ,554−571..

Miao,W.;Zou,W.;Jin,B.;Ni,C.;Zheng,N.;Zhao,Q.;Xie,T.Ondemandshapememorypolymer via lightregulatedtopologicaldefectsinadynamiccovalentnetwork. Nat. Commun. 2020 , 11 ,4257..

Li,Z.;Zhu,Y.-L.;Niu,W.;Yang,X.;Jiang,Z.;Lu,Z.Y.;Liu,X.;Sun,J.Healableandrecyclableelastomerswithrecord-highmechanicalrobustness,unprecedentedcracktolerance,andsuperhighelasticrestorability. Adv. Mater. 2021 , 33 ,2101498..

Niu,W.;Zhu,Y.;Wang,R.;Lu,Z.;Liu,X.;Sun,J.Remalleable,healable,andhighlysustainablesupramolecularpolymericmaterialscombiningsuperhighstrengthandultrahightoughness. ACS Appl. Mater. Interfaces 2020 , 12 ,30805−30814..

Schneiderman,D.K.;Hillmyer,M.A.50 th Anniversaryperspective:thereisagreatfutureinsustainablepolymers. Macromolecules 2017 , 50 ,3733−3749..

Vanbergen,T.;Verlent,I.;DeGeeter,J.;Haelterman,B.;Claes,L.;DeVos,D.Recyclingofflexiblepolyurethanefoambysplit-phasealcoholysis:identificationofadditivesandalcoholyzingagentstoreachhigherefficiencies. ChemSusChem 2020 , 13 ,3835−3843..

DiBisceglie,F.;Quartinello,F.;Vielnascher,R.;Guebitz,G.M.;Pellis,A.Cutinase-catalyzedpolyester-polyurethanedegradation:elucidationofthehydrolysismechanism. Polymers 2022 , 14 ,411..

Zhang,S.;Xu,X.-Q.;Liao,S.;Pan,Q.;Ma,X.;Wang,Y.Controllabledegradationofpolyurethanethermosetswithsilaketallinkagesinresponsetoweakacid. ACS Macro Lett. 2022 , 11 ,868−874..

Liao,S.;Lian,X.;Wang,Y.Self-healingionicliquid-basedelectronicsandbeyond. Chinese J. Polym. Sci. 2021 , 39 ,1235−1245..

Yin,Z.;Song,G.;Jiao,Y.;Zheng,P.;Xu,J.F.;Zhang,X.Dissipativesupramolecularpolymerizationpoweredbylight. CCS Chem. 2019 , 1 ,335−342..

Martinez,M.R.;Matyjaszewski,K.Degradableandrecyclablepolymersbyreversibledeactivationradicalpolymerization. CCS Chem. 2022 , 4 ,2176−2211..

Bapat,A.P.;Sumerlin,B.S.;Sutti,A.BulknetworkpolymerswithdynamicB–Obonds:healableandreprocessablematerials. Mater. Horiz. 2020 , 7 ,694−714..

Ogden,W.A.;Guan,Z.Recyclable,strong,andhighlymalleablethermosetsbasedonboroxinenetworks. J. Am. Chem. Soc. 2018 , 140 ,6217−6220..

Wang,S.;Xue,L.L.;Zhou,X.Z.;Cui,J.X.“Solid-liquid”vitrimersbasedondynamicboronicesternetworks. Chinese J. Polym. Sci. 2021 , 39 ,1292−1298..

Yang,X.;Guo,M.;Wu,Y.;Xue,S.;Li,Z.;Zhou,H.;Smith,A.T.;Sun,L.Biomimeticboroxine-basedmultifunctionalthermosets via one-potsynthesis. ACS Appl. Mater. Interfaces 2020 , 12 ,56445−56453..

Bao,C.;Guo,Z.;Sun,H.;Sun,J.Nitrogen-coordinatedboroxinesenablethefabricationofmechanicallyrobustsupramolecularthermosetscapableofhealingandrecyclingundermildconditions. ACS Appl. Mater. Interfaces 2019 , 11 ,9478−9486..

Kim,S.M.;Jeon,H.;Shin,S.H.;Park,S.A.;Jegal,J.;Hwang,S.Y.;Oh,D.X.;Park,J.Superiortoughnessandfastself-healingatroomtemperatureengineeredbytransparentelastomers. Adv. Mater. 2018 , 30 ,1705145..

Chen,Y.;Tang,Z.;Zhang,X.;Liu,Y.;Wu,S.;Guo,B.Covalentlycross-linkedelastomerswithself-healingandmalleableabilitiesenabledbyboronicesterbonds. ACS Appl. Mater. Interfaces 2018 , 10 ,24224−24231..

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

Kim,C.;Ejima,H.;Yoshie,N.Polymerswithautonomousself-healingabilityandremarkablereprocessabilityunderambienthumidityconditions. J. Mater. Chem. A 2018 , 6 ,19643−19652..

Bao,C.;Jiang,Y.-J.;Zhang,H.;Lu,X.;Sun,J.Room-temperatureself-healingandrecyclabletoughpolymercompositesusingnitrogen-coordinatedboroxines. Adv. Funct. Mater. 2018 , 28 ,1800560..

Zhang,X.;Wang,S.;Jiang,Z.;Li,Y.;Jing,X.Boronicesterbasedvitrimerswithenhancedstability via internalboron-nitrogencoordination. J. Am. Chem. Soc. 2020 , 142 ,21852−21860..

浏览量

270

Downloads

CSCD

文章被引用时，请邮件提醒。

Submit

工具集

关联资源

Energy Storage Performance of Supercapacitors with Polyelectrolyte Surface Coatings: Effects of Dielectric Contrast

Topology-regulated Co-assembly of Single Chain Polymer Nanoparticles and Block Copolymers into Hierarchical Micelle@Vesicle Composite Structures

Special Topic: Chirality in Polymers

Pyrimidoisoindigo-based Polymers for Ambipolar Charge Transport

A Paradigm for BF3 Co-initiated Cationic Polymerization with Low Dispersity: Introducing Acetonitrile and Lowering the Reaction Temperature