Chain Extender-induced Hydrogen Bonding Organization Determines the Morphology and Properties of Thermoplastic Polycarbonate Polyurethane

Yi-Lang Qin; Ping Zhu; Chen-Xi Ouyang; Xia Dong

doi:10.1007/s10118-023-3010-7

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Chain Extender-induced Hydrogen Bonding Organization Determines the Morphology and Properties of Thermoplastic Polycarbonate Polyurethane

RESEARCH ARTICLE | Updated：2023-12-26

- Chain Extender-induced Hydrogen Bonding Organization Determines the Morphology and Properties of Thermoplastic Polycarbonate Polyurethane
- Chain Extender-induced Hydrogen Bonding Organization Determines the Morphology and Properties of Thermoplastic Polycarbonate Polyurethane
- 高分子科学（英文版） 2024年42卷第1期页码：87-96
- Affiliations：
  
  a.Fuwai Hospital, Chinese Academy of Medical Sciences & Peking Union Medical College/National Center for Cardiovascular Diseases, Beijing 100037, China
  b.CAS Key Laboratory of Engineering Plastics, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
  c.University of Chinese Academy of Sciences, Beijing 100049, China
- Author bio：
  
  ouyangchx@nccd.org.cn (C.X.O.)
  xiadong@iccas.ac.cn (X.D.)
- Funds：
  
  This work was financially supported by the National Natural Science Foundation of China (No. 21774135). Beijing Synchrotron Radiation Facility (BSRF) is acknowledged for kindly providing beam time and assistance.;Electronic supplementary information (ESI) is available free of charge in the online version of this article at http://doi.org/10.1007/s10118-023-3010-7.
- DOI：10.1007/s10118-023-3010-7
  中图分类号：
- 收稿：2023-05-28，
  
  修回：2023-6-25，
  
  录用：2023-7-1，
  
  网络首发：2023-08-22，
  
  纸质出版：2024-01-01
- Accepted：
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Qin, Y. L.; Zhu, P.; Ouyang, C. X.; Dong, X. Chain extender-induced hydrogen bonding organization determines the morphology and properties of thermoplastic polycarbonate polyurethane. Chinese J. Polym. Sci. 2024, 42, 87–96

Yi-Lang Qin, Ping Zhu, Chen-Xi Ouyang, et al. Chain Extender-induced Hydrogen Bonding Organization Determines the Morphology and Properties of Thermoplastic Polycarbonate Polyurethane[J]. Chinese Journal of Polymer Science, 2024, 42(1): 87-96.
Qin, Y. L.; Zhu, P.; Ouyang, C. X.; Dong, X. Chain extender-induced hydrogen bonding organization determines the morphology and properties of thermoplastic polycarbonate polyurethane. Chinese J. Polym. Sci. 2024, 42, 87–96 DOI： 10.1007/s10118-023-3010-7.

Yi-Lang Qin, Ping Zhu, Chen-Xi Ouyang, et al. Chain Extender-induced Hydrogen Bonding Organization Determines the Morphology and Properties of Thermoplastic Polycarbonate Polyurethane[J]. Chinese Journal of Polymer Science, 2024, 42(1): 87-96. DOI： 10.1007/s10118-023-3010-7.

摘要

Thermoplastic polycarbonate polyurethanes (PCUs) with symmetric CEs

i.e.

4-butanediol and ethanediol demonstrate good phasing and tensile strength. PCUs with asymmetric CE

aminoethanol demonstrate less phasing but the bidentate H-bonding compensate for the asymmetry. At large strains

the PCU with MEA showed morphology of higher orientation.

Abstract

Thermoplastic polycarbonate polyurethanes (PCUs) are multiblock copolymers that have been applied for medical devices for long time. Aliphatic diols are common chain extenders (CE) involved in the composition of the hard segments of PCU. However

limited knowledge was discovered about how the chemical structure of CE affects the hydrogen bonding organization within PCUs and their mechanical properties. To investigate this problem

a group of PCUs were synthesized respectively by extending the polymer chain with 1

4-butanediol (BDO)

aminoethanol (MEA)

ethanediol (EO) as three kinds of chain extenders. Tiny differences in the CE chemical structure results in remarkable variations in phase separation

condensed morphologies

thermal and mechanical properties

which are characterized by Fourier transform infrared spectrometer

atomic force microscopy

small-angle X-ray scattering

differential scanning calorimetry

and tensile tests. The microstructural evolution during unilateral deformation and the different mechanism induced by the different CEs was probed and unveil by

in situ

wide- and small-angle X-ray diffraction. Symmetry of CE can improve the organization of the hydrogen bonding. The coherence strength of the urethane/urea group also plays a key role by comparing the two PCUs with ethanediol and aminoethanol.

关键词

Keywords

references

Berezkin,Y.;Urick,M.In modern polyurethanes: overview of structure property relationship .ACSSymp.Ser.,ACSPublications, 2013 ,p.65−81..

Yilgor,I.;Yilgor,E.;Wilkes,G.L.Criticalparametersindesigningsegmentedpolyurethanesandtheireffectonmorphologyandproperties:acomprehensivereview. Polymer 2015 , 58 ,A1−A36..

Cheng,B.X.;Gao,W.C.;Ren,X.M.;Ouyang,X.Y.;Zhao,Y.;Zhao,H.;Wu,W.;Huang,C.X.;Liu,Y.;Liu,X.Y.;Li,H.N;Robert,K.Y.L.Areviewofmicrophaseseparationofpolyurethane:characterizationandapplications. Polym. Test. 2022 , 107 ,107489..

Simmonsa,A.;Hyvarinena,J.;Odella,R.A.;Martinc,D.J.;Gunatillakeb,P.A.;Noblea,K.R.;Poole-Warren,L.A.Long-term in vivo biostabilityofpoly(dimethylsiloxane)/poly(hexamethyleneoxide)mixedmacrodiol-basedpolyurethaneelastomers. Biomaterials 2004 , 25 ,4887−4900..

Jenney,C.;Millson,P.;Grainger,D.W.;Grubbs,R.;Gunatillake,P.;McCarthy,S.J.;Runt,J.;Beith,J.Assessmentofasiloxanepoly(urethane-urea)elastomerdesignedforimplantableheartvalveleaflets. Adv. Nano Biomed. Res. 2021 , 1 ,2000032..

Kojio,K.;Furukawa,M.;Nonaka,Y.;Nakamura,S.Controlofmechanicalpropertiesofthermoplasticpolyurethaneelastomersbyrestrictionofcrystallizationofsoftsegment. Materials 2010 , 3 ,5097−5110..

Bonab,V.S.;Manas-Zloczower,I.Revisitingthermoplasticpolyurethane,fromcompositiontomorphologyandproperties. J. Polym. Sci., Part B: Polym. Phys. 2017 , 55 ,1553−1564..

Ginzburg,V.V.;Bicerano,J.;Christenson,C.P.;Schrock,A.K.;Patashinski,A.Z.TheoreticalmodelingoftherelationshipbetweenYoung’smodulusandformulationvariablesforsegmentedpolyurethanes. J. Polym. Sci., Part B: Polym. Phys. 2009 , 47 ,2198−2205..

Xu,W.;Zhang,R.Y.;Liu,W.;Zhu,J.;Dong,X.;Guo,H.X.;Hu,G.H.AMultiscaleinvestigationonthemechanismofshaperecoveryforIPDItoPPDIhardsegmentsubstitutioninpolyurethane. Macromolecules 2016 , 49 ,5931−5944..

Zhang,Z.Y.;Liu,L.;Xu,D.H.;Zhang,R.Y.;Shia,H.C.;Luana,S.;Yina,J.Researchprogressinpreparationandbiomedicalapplicationoffunctionalmedicalpolyurethaneelastomers. Acta Chim. Sinica 2022 , 80 ,1436−1447..

Zdrahala,R.J.;Zdrahala,I.J.Biomedicalapplicationsofpolyurethanes:areviewofpastpromises,presentrealities,andavibrantfuture. J. Biomater. Appl. 1999 , 14 ,67−90..

Hiob,M.A.;She,S.;Muiznieks,L.D.;Weiss,A.S.Biomaterialsandmodificationsinthedevelopmentofsmall-diametervasculargrafts. ACS Biomater. Sci. Eng. 2017 , 3 ,712−723..

Osman,A.F.;Edwards,G.A.;Schiller,T.L.;Andriani,Y.;Jack,K.S.;Morrow,I.C.;Halley,P.J.;Martin,D.J.Structure-propertyrelationshipsinbiomedicalthermoplasticpolyurethanenanocomposites. Macromolecules 2012 , 45 ,198−210..

Fatima,J.K.;Pakkanen,T.T.Incorporationofpolydimethylsiloxaneintopolyurethanesandcharacterizationofcopolymers. Eur. Polym. J. 2011 , 47 ,1694−1708..

Hong,Y.;Guan,J.J.;Fujimoto,K.L.;Hashizume,R.;Pelinescu,A.L.;Wagner,W.R.Tailoringthedegradationkineticsofpoly(estercarbonateurethane)ureathermoplasticelastomersfortissueengineeringscaffolds. Biomaterials 2010 , 31 ,4249−4258..

Wang,Q;McGoron,A.J.;Bianco,R.;Kato,Y.;Pinchuk,L.;Schoephoerster,R.T. In-vivo assessmentofanovelpolymer(SIBS)trileafletheartvalve. J. Heart Valve Dis. 2010 , 19 ,499−505..

Kidane,A.G.;Burriesci,G.;Edirisinghe,M.;Ghanbari,H.;Bonhoeffer,P.;Seifalian,A.M.Anovelnanocompositepolymerfordevelopmentofsyntheticheartvalveleaflets. Acta Biomater. 2009 , 5 ,2409−2417..

Dandeniyage,L.S.;Gunatillake,P.A.;Adhikari,R.;Bown,M.;Shanks,R.;Adhikari,B.Developmentofhighstrengthsiloxanepoly(urethane-urea)elastomersbasedonlinkedmacrodiolsforheartvalveapplication. J. Biomed. Mater. Res. B Appl. Biomater. 2018 , 106 ,1712−1720..

Cooper,S.L.;Guan,J.J. Advances in polyurethane biomaterials. WoodheadPublishing, 2016 ..

Xie,F.W.;Zhang,T.L.;Bryant,P.;Kurusingal,V.;Colwell,J.M.;Laycock,B.Degradationandstabilizationofpolyurethaneelastomers. Prog. Polym. Sci. 2019 , 90 ,211−268..

Lai,Y.;Kuang,X.;Zhu,P.;Huang,M.M.;Dong,X.;Wang,D.J.Colorless,transparent,robust,andfastscratch-self-healingelastomers via aphase-lockeddynamicbondsdesign. Adv. Mater. 2018 , 30 ,1802556..

Song,Y.;Liu,Y.;Qi,T.;Li,G.L.Towardsdynamic,butsupertoughhealablepolymers via biomimetichierarchicalhydrogenbondinginteraction. Angew. Chem. Int. Ed. 2018 , 57 ,13838−13842..

Hornat,C.C.;Urban,M.W.Shapememoryeffectsinself-healingpolymers. Prog. Polym. Sci. 2020 , 102 ,101208..

Kojio,K.;Nozaki,S.;Takahara,A.;Yamasaki,S.Influenceofchemicalstructureofhardsegmentsonphysicalpropertiesofpolyurethaneelastomers:areview. J. Polym. Res. 2020 , 27 ,140..

Wiggins,M.J.;MacEwan,M.;Anderson,J.M.;Hiltner,A.Effectofsoft-segmentchemistryonpolyurethanebiostabilityduringinvitrofatigueloading. J. Biomed. Mater. Res. A 2004 , 68 ,668−683..

Castagna,A.M.;Pangon,A.;Choi,T.;Dillon,G.P.;Runt,J.Theroleofsoftsegmentmolecularweightonmicrophaseseparationanddynamicsofbulkpolymerizedpolyureas. Macromolecules 2012 , 45 ,8438−8444..

Yilgor,I.;Yilgor,E.;Guler,I.G.;Ward,T.C.;Wilkes,G.L.FTIRinvestigationoftheinfluenceofdiisocyanatesymmetryonthemorphologydevelopmentinmodelsegmentedpolyurethanes. Polymer 2006 , 47 ,4105−4114..

Liu,X.;Ding,S.S.;Wang,F.;Shi,Y.L.;Wang,X.H.;Wang,Z.G.Controllingenergydissipationduringdeformationbyselectionofthehard-segmentcomponentforthermoplasticpolyurethanes. Ind. Eng. Chem. Res. 2022 , 61 ,8821−8831..

Nozaki,S.;Masuda,S.;Kamitani,K.;Ken,K.;Takahara,A.;Kuwamura,G.;Hasegawa,D.;Moorthi,K.;Mita,K.;Yamasaki,A.Superiorpropertiesofpolyurethaneelastomerssynthesizedwithaliphaticdiisocyanatebearingasymmetricstructure. Macromolecules 2017 , 50 ,1008−1015..

Crago,M.;Lee,A.;Farajikhah,S.;Oveissi,F.;Fletcher,D.F.;Dehghani,F.;Winlaw,D.S.;Naficy,S.Theevolutionofpolyurethaneheartvalvereplacements:howchemistrytranslatestotheclinic. Mater. Today Commun. 2022 , 33 ,104916..

Hu,S.K.;Shou,T.;Zhao,X.Y.;Wang,Z.;Zhang,S.J.;Qin,X.;Guo,M.M.;Zhang.L.Q.RationaldesignofanovelNDI-basedthermoplasticpolyurethaneelastomerwithsuperiorheatresistance. Polymer 2020 , 205 ,122764..

Zhao,Q.;Jesus,C.B.;Urbanski,P.;Stokes,K.Glasswool-H 2 O 2 /CoCl 2 testsystemforinvitroevaluationofbiodegradativestresscrackinginpolyurethaneelastomers. J. Biomed. Mater. Res. 1995 , 29 ,467−475..

Tanzi,M.C.;Mantovani,D.;Petrini,P.;Guidoin,R.;Laroche,G.Chemicalstabilityofpolyetherurethanesversuspolycarbonateurethanes. J. Biomed. Mater. Res. 1997 , 36 ,550−559..

Eceiza,A.;Larranaga,M.;delaCaba,K.;Kortaberria,G.;Marieta,C.;Corcuera,M.A.;Mondragon,I.Structure–propertyrelationshipsofthermoplasticpolyurethaneelastomersbasedonpolycarbonatediols. J. Appl. Polym. Sci. 2008 , 108 ,3092−3103..

Kojio,K.;Furukawa,M.;Motokucho,S.;Shimada,M.;Sakai,M.Structure-mechanicalpropertyrelationshipsforpoly(carbonateurethane)elastomerswithnovelsoftsegments. Macromolecules 2009 , 42 ,8322−8327..

Kultys,A.;Rogulska,M.Newthermoplasticpoly(carbonate-urethane)elastomers. Polish J. Chem. Technol. 2011 , 13 ,23−30..

Liu,Y.;Peng,L.;Lin,J.L.;Zhou,Y.;Wang,D.J.;Han,C.;Huang,X.B.;Dong,X.Thecrystallizationbehaviourregulatingnatureofhydrogenbondsinteractiononpolyamide6,6bypoly(vinylpyrrolidone). Chinese J. Polym. Sci. 2023 , 41 ,394−404..

Zhu,P.;Zhou,C.X.;Wang,Y.;Sauer,B.;Hu,W.B.;Dong,X.;Wang,D.J.Thereversible-irreversibletransitionofstrain-inducedcrystallizationinsegmentedcopolymers:thecriticalstrainandthechainconformation. ACS Appl. Polym. Mater. 2021 , 3 ,3576−3585..

Scetta,G.;Euchler,E.;Ju,J.Z.;Selles,N.;Heuillet,P.;Ciccotti,M.;Creton,C.Self-organizationatthecracktipoffatigue-resistantthermoplasticpolyurethaneelastomers. Macromolecules 2021 , 54 ,8726−8737..

Li,X.K.;Wang,H.;Xiong,B.J.;Pöselt,E.;Eling,B.;Men.Y.F.Destructionandreorganizationofphysicallycross-linkednetworkofthermoplasticpolyurethanedependingonitsglasstransitiontemperature. ACS Appl. Polym. Mater. 2019 , 1 ,3074−3083..

Rogulska,M.;Maciejewska,M.;Olszewska,E.Newthermoplasticpoly(carbonate-urethane)sbasedondiphenylethanederivativechainextender. J. Therm. Anal. Calorim. 2020 , 139 ,1049−1068..

Kong,Z.Y.;Tian,Q.;ZhangR.Y.;Yin,J.B.;Shi,L.;Ying,W.B.;Hu,H.;YaoC.K.;Wang,K.;Zhu,J.ReexaminationofthemicrophaseseparationinMDIandPTMGbasedpolyurethane:fastandcontinuousassociation/dissociationprocessesofhydrogenbonding. Polymer 2019 , 185 ,121943..

Xu,Z.C.;Wang,X.Y.;Huang,H.Thermoplasticpolyurethane–ureaelastomerswithsuperiormechanicalandthermalpropertiespreparedfromalicyclicdiisocyanateanddiamine. J. Appl. Polym. Sci. 2020 , 137 ,e49575..

He,Y.;Xie,D.L.;Zhang,X.Y.Thestructure,microphase-separatedmorphology,andpropertyofpolyurethanesandpolyureas. J. Mater. Sci. 2014 , 49 ,7339−7352..

Eceiza,A.;Martin,M.D.;delaCaba,K.;Kortaberria,G.;Gabilondo,N.;Corcuera,M.A.;Mondragon,I.Thermoplasticpolyurethaneelastomersbasedonpolycarbonatediolswithdifferentsoftsegmentmolecularweightandchemicalstructure:mechanicalandthermalproperties. Polym. Eng. Sci. 2008 , 48 ,297−306..

Kojio,K.;Matsuo,K.;Motokucho,S.;Yoshinaga,K.;Shimodaira,Y.;Kimura,K.Simultaneoussmall-angleX-rayscattering/wide-angleX-raydiffractionstudyofthemicrodomainstructureofpolyurethaneelastomersduringmechanicaldeformation. Polym. J. 2011 , 43 ,692−699..

Zhu,P.;Brückner,A.;Neumeyer,T.;Standau,T.;Ruckdäschel,H.;Altstädt,V.;Dong,X.;Wang,D.J.Fatiguecharacteristicsofpoly(ether- b -amide)elastomersduringcyclicdynamictestsandtheunderlyingmicrostructuralevolution. Ind. Eng. Chem. Res. 2022 , 61 ,14760−14771..

Hu,S.K.;He,S.Y.;Wang,Y.M.;Wu,Y.W.;Shou,T.;Yin,D.X.;Mu,G.Y.;Zhao,X.Y.;Gao,Y.Y.;Liu,J.;Li,F.Z.;Guo,M.M.;Zhang,L.Q.Self-repairable,recyclableandheat-resistantpolyurethaneforhigh-performanceautomobiletires. Nano Energy 2022 , 95 ,107012..

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