a.Key Laboratory of Beijing City on Preparation and Processing of Novel Polymer Materials, Beijing University of Chemical Technology, Beijing 100029, China
b.Shandong Chambroad Sinopoly New Materials Co., Ltd., Binzhou 256600, China
shiyan@mail.buct.edu.cn (Y.S.)
zhanglq@mail.buct.edu.cn (L.Q.Z.)
收稿:2023-02-25,
修回:2023-4-17,
录用:2023-4-30,
网络首发:2023-06-12,
纸质出版:2023-11-01
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Gao, H.; Cui, B.C.; Zheng, H. B.; Hao, F. L.; Shi, Y.; Zhang, L. Q. Epoxidation functionalized isobutylene isoprene rubber toward green-curing pathway and high-performance composites. Chinese J. Polym. Sci. 2023, 41, 1818–1828
Han Gao, Bai-Chuan Cui, Hong-Bing Zheng, et al. Epoxidation Functionalized Isobutylene Isoprene Rubber toward Green-curing Pathway and High-performance Composites[J]. Chinese Journal of Polymer Science, 2023, 41(11): 1818-1828.
Gao, H.; Cui, B.C.; Zheng, H. B.; Hao, F. L.; Shi, Y.; Zhang, L. Q. Epoxidation functionalized isobutylene isoprene rubber toward green-curing pathway and high-performance composites. Chinese J. Polym. Sci. 2023, 41, 1818–1828 DOI: 10.1007/s10118-023-2986-3.
Han Gao, Bai-Chuan Cui, Hong-Bing Zheng, et al. Epoxidation Functionalized Isobutylene Isoprene Rubber toward Green-curing Pathway and High-performance Composites[J]. Chinese Journal of Polymer Science, 2023, 41(11): 1818-1828. DOI: 10.1007/s10118-023-2986-3.
A new modified species of butyl rubber (IIR)
epoxidized butyl rubber (EIIR) was synthesized by
in situ
epoxidation technique for the first time. The epoxidation degree of EIIR reached about 99 %. The EIIR/CB composite crosslinked by maleic anhydride had excellent mechanical properties
and the airtightness and fatigue life were substantially improved compared with those of IIR.
Epoxidation of the carbon-carbon double bonds on unsaturated rubber macromolecules can produce novel modified rubber species with special properties
and construct eco-friendly crosslinking pathway
via
the reaction of epoxide groups to solve the problems brought by conventional sulfur vulcanization system. In this contribution
a novel modified product of isobutylene isoprene rubber (IIR)
epoxy-functionalized IIR (EIIR) was successfully prepared by
in situ
epoxidation technique for the first time
and the crosslinking of EIIR was achieved by the reaction of oxirane groups with maleic anhydride (MAH) without additional additives. The reaction conditions for preparing EIIR were optimized through systematic research on the epoxidation process. Under optimal condition
the degree of epoxidation of the rubber reached around 99% without side reactions. The obtained EIIR/carbon black composites cured by MAH had excellent mechanical properties comparable to those of IIR composites. More importantly
compared with IIR composites
the air-tightness of the EIIR composites was improved by about 50%
and the flexural fatigue life of first-level cracks and sixth-level cracks was increased by several times. The significant improvement of these properties is of great significance for the application safety and energy saving of IIR materials.
Coran,A.Y.Vulcanization. Sci. Technol. Rubber 1994 ,339−385..
Roy,K.;Alam,M.N.;Mandal,S.K.;Debnath,S.C.Sol-gelderivednanozincoxideforthereductionofzincoxidelevelinnaturalrubbercompounds. J. Sol-Gel Sci. Technol. 2014 , 70 ,378−384..
Mostoni,S.;Milana,P.;Credico,B.D.;D’Arienzo,M.;Scotti,R.Zinc-basedcuringactivators:newtrendsforreducingzinccontentinrubbervulcanizationprocess. Catalysts 2019 , 9 ,664..
Lin,T.F.;Zhang,X.H.;Tang,Z.H.;Guo,B.C.Renewableconjugatedacidsascurativesforhigh-performancerubber/silicacomposites. Green Chem. 2015 , 17 ,3301−3305..
Hansson,C.Allergiccontactdermatitisfrom N -(1,3-dimethylbutyl)- N '-phenyl- p -phenylenediamineandfromcompoundsinpolymerized2,2,4-trimethyl-1,2-dihydroquinoline. Contact Dermatitis 1994 , 30 ,114−115..
Kroft,E.B.M.;VanDerValk,P.G.M.Occupationalcontactdermatitisofbothhandsbecauseofsensitizationofblackrubber. Contact Dermatitis 2008 , 58 ,125−126..
Yamano,T.;Shimizu,M.Skinsensitizationpotencyandcross-reactivityof p -phenylenediamineanditsderivativesevaluatedbynon-radioactivemurinelocallymphnodeassayandguinea-pigmaximizationtest. Contact Dermatitis 2009 , 60 ,193−198..
Zhang,G.G.;Zhou,X.X.;Zhang,Q.L.Editorialcorner-apersonalviewCurrentissuesforrubbercrosslinkinganditsfuturetrendsofgreenchemistrystrategy. Express Polym. Lett. 2019 , 13 ,406−406..
Naskar,K.ThermoplasticelastomersbasedonPP/EPDMblendsbydynamicvulcanization. Rubber Chem. Technol. 2007 , 80 ,504−519..
Zhang,X.H.;Tang,Z.H.;Guo,B.C.Regulationofmechanicalpropertiesofdienerubbercuredbyoxa-MichaelReaction via manipulatingnetworkstructure. Polymer 2018 , 144 ,57−64..
Zhang,G.G.;Feng,H.;Liang,K.;Wang,Z.;Li,X.L.;Zhou,X.X.;Guo,B.C.;Zhang,L.Q.Designofnext-generationcross-linkingstructureforelastomerstowardgreenprocessandarealrecyclingloop. Sci. Bull. 2020 , 65 ,889−898..
Feng,H.R.;Tian,C.;Zhang,G.G.;Zhang,L.Q.Catalyst-freecuringandclosed-looprecyclingofcarboxylatedfunctionalizedrubberbyagreencrosslinkingstrategy. Polymer 2021 , 234 ,124237−124247..
Pire,M.;Norvez,S.;Iliopoulos,I.;Rossignol,B.L.;Leibler,L.Epoxidizednaturalrubber/dicarboxylicacidself-vulcanizedblends. Polymer 2010 , 51 ,5903−5909..
Zhang,G.G.;Zhou,X.X.;Liang,K.;Guo,B.C.;Li,X.L.;Wang,Z.;Zhang,L.Q.MechanicallyrobustandrecyclableEPDMrubbercompositesbyagreencross-linkingstrategy. ACS Sustainable Chem. Eng. 2019 , 7 ,11712−11720..
Pire,M.;Norvez,S.;Iliopoulos,I.;Rossignol,B.L.;Leibler,L.Imidazole-promotedaccelerationofcrosslinkinginepoxidizednaturalrubber/dicarboxylicacidblends. Polymer 2011 , 52 ,5243−5249..
Pire,M.;Lorthioir,C.;Oikonomou,E.K.;Norvez,S.;Iliopoulos,I.;Rossignol,B.L.;Leibler,L.Imidazole-acceleratedcrosslinkingofepoxidizednaturalrubberbydicarboxylicacids:amechanisticinvestigationusingNMRspectroscopy. Polym. Chem. 2012 , 3 ,946−953..
Pire,M.;Norvez,S.;Iliopoulos,I.;Rossignol,B.L.;Leibler,L.Dicarboxylicacidsmaycompetewithstandardvulcanizationprocessesforcrosslinkingepoxidisednaturalrubber. Compos. Interface 2014 , 21 ,45−50..
Algaily,B.;Kaewsakul,W.;Sarkawi,S.S.;Kalkornsurapranee,E.EnablingreprocessabilityofENR-basedvulcanisatesbythermochemicallyexchangeableestercrosslinks. Plast. Rubber Compos. 2021 , 50 ,315−328..
Chilkoor,G.;Sarder,R.;Islam,J.;ArunKumar,K.E.;Ratnayake,I.Maleicanhydride-functionalizedgraphenenanofillersrenderepoxycoatingshighlyresistanttocorrosionandmicrobialattack. Carbon 2020 , 159 ,586−597..
Espana,J.M.;Sánchez-Nacher,L.;Boronat,T.;Fombuena,V.;Balart,R.Propertiesofbiobasedepoxyresinsfromepoxidizedsoybeanoil(ESBO)curedwithmaleicanhydride(MA). J. Am. Oil Chem. Soc. 2012 , 89 ,2067−2075..
Kolář,F.;Svítilová,J.Kineticsandmechanismofcuringepoxy/anhydridesystems. Acta Geodyn. Geomater. 2007 , 4 ,85−92..
Srirachya,N.;Kobayashi,T.;Boonkerd,K.Analternativecrosslinkingofepoxidizednaturalrubberwithmaleicanhydride. Key Eng. Mater. 2017 , 748 ,84−90..
Zhang,G.G.;Liang,K.;Feng,H.R.;Pang,J.X.;Liu,N.Q.;Li,X.L.Designofepoxy-functionalizedstyrene-butadienerubberwithbio-baseddicarboxylicacidasacross-linkertowardthegreen-curingprocessandrecyclability. Ind. Eng. Chem. Res. 2020 , 59 ,10447−10456..
Yang,C.L.;Li,T.;Li,Z.P.EffectofheatingonpropertiesofENR. China Rubber Ind. 2002 , 49 ,400−402..
Liu,Y.J.;Tang,Z.H.;Wu,S.W.;Guo,B.C.Integratingsacrificialbondsintodynamiccovalentnetworkstowardmechanicallyrobustandmalleableelastomers. ACS Macro Lett. 2019 , 8 ,193−199..
Tang,Z.H.;Liu,Y.J.;Guo,B.C.;Zhang,L.Q.Malleable,mechanicallystrong,andadaptiveelastomersenabledbyinterfacialexchangeablebonds. Macromolecules 2017 , 50 ,7584−7592..
Cao,L.M.;Fan,J.F.;Huang,J.R.;Chen,Y.K.Arobustandstretchablecross-linkedrubbernetworkwithrecyclableandself-healablecapabilitiesbasedondynamiccovalentbonds. J. Mater. Chem. A 2019 , 7 ,4922−4933..
Zhu,Y.;Gao,J.L.;Zhang,L.J.;Peng,Y.;Wang,H.;Ling,F.W.;Huang,G.S.;Wu,J.R.Aninterfacialdynamiccrosslinkingapproachtowardcatalyst-freeandmechanicallyrobustelastomericvitrimerwithasegregatedstructure. Chinese J. Polym. Sci. 2021 , 39 ,201−210..
Tanrattanakul,V.;Wattanathai,B.;Tiangjunya,A.;Muhamud,P. In situ epoxidizednaturalrubber:improvedoilresistanceofnaturalrubber. J. Appl. Polym. Sci. 2003 , 90 ,261−269..
Pu,L.;Zhang,R.;Zhu,Y.Developmentandoptimizationofepoxidationprocessfornaturalrubber. Yunnan Chem. Technol. 2021 , 48 ,46−49..
Li,C.B.;Wang,H.;Feng,Z.;Yang,S.T.Preparationandcharacterizationofepoxidizednaturalrubberby in-situ method. New Chem. Mater. 2012 , 40 ,124−126+130..
Puskas,J.E.;Wilds,C.Kineticsoftheepoxidationofbutylrubber;developmentofahighprecisionanalyticalmethodforunsaturationmeasurement. Rubber Chem. Technol. 1994 , 67 ,329−341..
Wu,J.;Cui,B.C.;Wang,Y.;Shi,Y.;Ren,X.B.;Xu,H.D.;Liu,Z.X.;Hao,F.L.;Zhang,L.Q.Synthesisandcharacterizationofepoxidizedbutylrubber. Acta Polymerica Sinica (inChinese) 2022 , 53 ,185−192..
Wang,Y.M.;Cao,R.W.;Wang,M.H.;Liu,X.M.;Zhao,X.Y.;Lu,Y.L.;Feng,A.C.;Zhang,L.Q.Designandsynthesisofphenylsiliconerubberwithfunctionalepoxygroupsthroughanioniccopolymerizationandsubsequentepoxidation. Polymer 2020 , 186 ,122077−12084..
James,A.P.;Johnstone,R.A.W.;McCarron,M.;Sankey,J.P.;Trenbirth,B.5-Hydroperoxycarbonylphthalimide:anewreagentforepoxidation. Chem. Commun. 1998 ,429−430..
Zhang,X.;Niu,K.J.;Song,W.X.;Yan,S.K.;Zhao,X.Y.;Lu,Y.L.;Zhang,L.Q.Theeffectofepoxidationonstrain-inducedcrystallizationofepoxidizednaturalrubber. Macromol. Rapid Commun. 2019 , 40 ,1900042−1900046..
Roy,S.;Gupta,B.R.;Maiti,B.R.Effectofacidconcentrationandotherreactionparametersonepoxidationofnaturalrubberlatex. Ind. Eng. Chem. Res. 1991 , 30 ,2573−2576..
Jacobi,M.M.;Santin,C.K.;Alegre,M.;Schuster,R.H.StudyoftheepoxidationofpolydienerubbersI.InfluenceofthemicrostructureontheepoxidationofSBRwithperformicacid. KGK-Kautsch. Gummi. Kunstst. 2002 , 55 ,590−595..
Chu,C.Y.;Vukov,R.DeterminationofthestructureofbutylrubberbyNMRspectroscopy. Macromolecules 1985 , 18 ,1423−1430..
Jacobi,M.M.;Schneider,L.K.;Freitas,L.L.;Schuster,R.H.PropertiesandmorphologyofthermoplasticvulcanizatesbasedonPP/SBRandPP/EpSBR. KGK-Kautsch. Gummi. Kunstst. 2006 , 59 ,49−54..
Johnson,T.;Thomas,S.Nitrogen/oxygenpermeabilityofnaturalrubber,epoxidisednaturalrubberandnaturalrubber/epoxidisednaturalrubberblends. Polymer 1999 , 40 ,3223−3228..
Li,Z.P.;Lan,J.Effectsofepoxidationofnaturalrubberonitsproperties. Chinese J. Appl. Chem. 1996 , 13 ,49−51..
Zhao,X.Y.;Niu,K.J.;Xu,Y.;Peng,Z.;Jia,L.;Hui,D.;Zhang,L.Q.MorphologyandperformanceofNR/NBR/ENRternaryrubbercomposites. Compos. Part B-Eng. 2016 , 107 ,106−112..
Wang,Y.Y.;Shi,M.X.;Sun,Y.;Tie,W.Y.;Zhang,L.S.Productiontechnologyandmarketanalysisofbutylrubber. China Elastomerics 2010 , 20 ,80−84..
Grubisic,V.Airtightnesscontrolofpassengercarwheels. Engineering 2017 , 9 ,171−180..
Roychoudhury,A.;De,P.P.Reinforcementofepoxidizednaturalrubberbycarbonblack:effectofsurfaceoxidationofcarbonblackparticles. J. Appl. Polym. Sci. 1993 , 50 ,181−186..
Wang,M.J.;Wolff,S.;Donnet,J.B.Filler-elastomerinteractions.PartIII.Carbon-black-surfaceenergiesandinteractionswithelastomeranalogs. Rubber Chem. Technol. 1991 , 64 ,714−736..
Bradbury,J.H.;Perera,M.C.S.EpoxidationofnaturalrubberstudiedbyNMRspectroscopy. J. Appl. Polym. Sci. 1985 , 30 ,3347−3364..
Hamzah,R.;Bakar,M,A.;Khairuddean,M.;Mohammed,I.A.;Adnan,R.Astructuralstudyofepoxidizednaturalrubber(ENR-50)anditscyclicdithiocarbonatederivativeusingNMRspectroscopytechniques. Molecules 2012 , 17 ,10974−10993..
Gan,S,N.;Hamid,Z,A.Partialconversionofepoxidegroupstodiolsinepoxidizednaturalrubber. Polymer 1997 , 38 ,1953−1956..
Dahham,O,S.;Hamzah,R.;Bakar,M,A.;Zulkepli,N.N.;Dahham,S.S.;Ting,S.S.NMRstudyofringopeningreactionofepoxidizednaturalrubberinpresenceofpotassiumhydroxide/isopropanolsolution. Polym. Test. 2017 , 59 ,55−66..
Vernekar,S.P.;Sabne,M.B.;Patil,S.D.;Patil,A.S.;Idage,S.B.;Avadhani,C.V.;Sivaram,S.Effectoflatexconcentrationonepoxidationofnaturalrubber(NR)latex. J. Appl. Polym. Sci. 1992 , 44 ,2107−2114..
Hashim,A.S.;Kohjiya,S.Preparationandpropertiesofepoxidizednaturalrubbernetworkcrosslinkedbyringopeningreaction. Polym. Gels Networks 1994 , 2 ,219−227..
Huang,C.;Ge,Z.;Zhao,B.B.;Wang,Z.;Luo,Y.J.EffectsofDMP-30oncuringbehaviorofepoxyresin/maleicanhydridesystems. J. Chem. Eng. Chinese Universities 2017 , 31 ,197−204..
Papirer,E.;Dentzer,J.;Li,S.;Donnet,J.B.Surfacegroupsonnitricacidoxidizedcarbonblacksamplesdeterminedbychemicalandthermodesorptionanalyses. Carbon 1991 , 29 ,69−72..
Manna,A.K.;De,P.P.;Tripathy,D.K.;De,S.K.Chemicalinteractionbetweensurfaceoxidizedcarbonblackandepoxidizednaturalrubber. Rubber Chem. Technol. 1997 , 70 ,624−633..
Menard,K.P.;Bilyeu,B.W.,in Encyclopedia of Analytical Chemistry: Applications, Theory and Instrumentation, JohnWiley & SonsLtd,NewYork, 2006 ,p.16..
Tang,Z.H.;Wu,X.H.;Guo,B.C.;Zhang,L.Q.;Jia,D.Preparationofbutadiene-styrene-vinylpyridinerubber-grapheneoxidehybridsthroughco-coagulationprocessand in situ interfacetailoring. J. Mater. Chem. 2012 , 22 ,7492−7501..
Qiao,H.;Wang,R.G.;Yao,H.;Zhou,X.X.;Lei,W.W.;Hu,X.R.;Zhang,L.Q.Preparationofgrapheneoxide/bio-basedelastomernanocompositesthroughpolymerdesignandinterfacetailoring. Polym. Chem. 2015 , 6 ,6140−6151..
Zheng,L.;Jerrams,S.;Su,T.;Xu,Z.C.;Zhang,L.Q.;Liu,L.;Wen,S.P.Enhancedcovalentinterface,crosslinkednetworkandgasbarrierpropertyoffunctionalizedgrapheneoxide/styrene-butadienerubbercompositestriggeredbythiol-eneclickreaction. Compos. Part B-Eng. 2020 , 197 ,108186..
Liu,W.;Lv,L.T.;Yang,Z.L.;Zheng,Y.Q.;Wang,H.TheeffectofOMMTonthepropertiesofvehicledampingcarbonblack-naturalrubbercomposites. Polymers 2020 , 12 ,1983−1993..
Huneau,B.;Masquelier,I.;Marco,Y.;Saux,V.L.;Noizet,S.;Schiel,C.;Charrier,P.Fatiguecrackinitiationinacarbonblack-fillednaturalrubber. Rubber Chem. Technol. 2016 , 89 ,126−141..
Dong,B.;Zhang,L.Q.;Wu,Y.P.Influencesofdifferentdimensionalcarbon-basednanofillersonfractureandfatigueresistanceofnaturalrubbercomposites. Polym. Test. 2017 , 63 ,281−288..
Ishak,Z.A.M.;Bakar,A.A.;Ishiaku,U.S.;Hashim,A.S.;Azahari,B.Aninvestigationofthepotentialofricehuskashasafillerforepoxidizednaturalrubber—II.Fatiguebehaviour. Eur. Polym. J. 1997 , 33 ,73−79..
Ismail,H.;Jaffri,R. M.;Rozman,H .D.Oilpalmwoodflourfillednaturalrubbercomposites:fatigueandhysteresisbehaviour. Polym. Int. 2000 , 49 ,618−622..
Sun,Y.N.;Cheng,P.F.;Cui,B.P.;Sun,X.H.EffectsofCBandcuringdegreeonfatiguepropertiesofNRvulcanizates. China Elastomerics 2017 , 27 ,34−38..
Wang,H.;Wei,Y.T.;Wang,J.Influencingfactorsandresearchmethodsofrubbermaterialfatiguelife. China Rubber Ind. 2020 , 67 ,723−735..
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