Stereoselective Polymerization With Single-Site Catalysts Baugh Canich PDF
Preview Stereoselective Polymerization With Single-Site Catalysts Baugh Canich
Edited by Lisa S. Baugh JoAnn M. Canich Stereoselective Polymerization with Single-Site Catalysts CRC Press is an imprint of the Taylor & Francis Group, an lnfonn• business DK3712: “dk3712_c000” — 2007/10/23 — 11:58 — page i — #1 DK3712: “dk3712_c000” — 2007/10/23 — 11:58 — page ii — #2 Stereoselective Polymerization with Single-Site Catalysts Edited by Lisa S. Baugh Jo Ann M. Canich f:2...cRC Press ~ Taylor & Francis Group Boca Raton London New York CRC Press is an imprint of the Taylor &: Francis Group, an lnforma business DK3712: “dk3712_c000” — 2007/10/23 — 11:58 — page iii — #3 On the cover is a space-filling model of an active rac-ethylenebis(indenyl)zirconium catalyst with an attached growing polypropylene chain. This represents one of the first discoveries of an ansa-metallocene catalyst capable of producing isotactic polypropylene. The transition structure of the modified Green-Rooney propylene insertion mechanism is also depicted. The enantioselectivity of the propylene insertion step requires a catalyst with both appropriate symmetry and stereorigidity. The cover background photograph shows a reactor in the laboratory of Professor Stephen A. Miller, containing syndiotac tic polypropylene prepared by graduate student Levi J.lrwin. The Miller-Bercaw metallocene catalyst employed (catalyst s-90 in Chapter 2) is one of the most syndioselective propylene polymerization catalysts currently known. Unlike isotac tic polypropylene, which can also be prepared with Ziegler-Natta initiators, syndiotactic polypropylene is only obtained in appreciable quantities using single-site catalysts. Cover design by Stephen A. Miller CRCPress Taylor & Francis Group 6000 Broken Sound Parkway NW, Suite 300 Boca Raton, FL 33487-2742 @ 2008 by Taylor & Francis Group, LLC CRC Press is an imprint of Taylor & Francis Group, an Informa business No claim to original U.S. Government works Printed in the United States of America on acid-free paper 10987654321 International Standard Book Nwnber-13: 978-1-57444-579-4 (Hardcover) This book contains information obtained from authentic and highly regarded sources. Reprinted material is quoted with permission. and sources are indicated. A wide variety of references are listed. Reasonable efforts have been made to publish reliable data and information, but the author and the publisher cannot assume responsibility for the validity of all materials or for the consequences of their use. 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Trademark Notice: Product or corporate names may be trademarks or registered trademarks, and are used only for identification and explanation without intent to infringe. Library of Congress Cataloging-in-Publication Data Stereoselective polymerization with single-site catalysts I edited by Lisa S. Baugh and JoAnn M. Canich. p.cm. Includes bibliographical references and index. ISBN-13: 978-1-57444-579-4 (hardcover: acid-free paper) ISBN-10: 1-57444-579-0 (hardcover: acid-free paper) 1. Polymerization--Research. 2. Polymer engineering--Research. 3. Stereochemistry--Research. 4. Catalysis--Research. I. Baugh, Lisa S. (Lisa Saunders) II. Canich, JoAnn M. TP156.P6S74 2008 668.9'2--dc22 2007018734 Visit the Taylor &c. Francis Web site at http://www.taylorandfrancis.com and the CRC Press Web site at http://www.crcpress.com DK3712: “dk3712_c000” — 2007/10/23 — 11:58 — page iv — #4 Contents Preface.............................................................................................. ix Editors.............................................................................................. xiii Contributors....................................................................................... xv I Polypropylene:CatalystsandMechanism ............................................ 1 Chapter1 IsotacticPolypropylenefromC -andPseudo-C -SymmetricCatalysts......... 3 2 2 RekoLeinoandShirleyLin Chapter2 Fluorenyl-ContainingCatalystsforStereoselectivePropylene Polymerization...................................................................... 37 CraigJ.Price,LeviJ.Irwin,DavidA.Aubry,andStephenA.Miller Chapter3 SubstitutedIndenylandCyclopentadienylCatalystsforStereoselective PropylenePolymerization.......................................................... 83 JohnJ.Esteb Chapter4 DoublyBridgedMetallocenesforStereoselectivePropylene Polymerization...................................................................... 101 DeannaL.Zubris Chapter5 MetalloceneswithDonor/AcceptorandOtherHeteroatomBridgesfor StereoselectivePropylenePolymerization......................................... 135 PamelaJ.Shapiro Chapter6 StereoselectivePropylenePolymerizationwithEarlyandLateTransition MetalCatalysts...................................................................... 157 HaruyukiMakioandTerunoriFujita Chapter7 CatalystStructureandPolymerTacticity:TheTheoryBehindSiteControlin PropylenePolymerization.......................................................... 169 AnthonyK.Rappé,OlegG.Polyakov,andLynnM.Bormann-Rochotte II Polypropylene:ApplicationsofTacticity............................................. 201 Chapter8 StereoblockPolypropylene......................................................... 203 VincenzoBusico Chapter9 ElastomericHomo-Polypropylene:SolidStatePropertiesandSynthesisvia ControlofReactionParameters.................................................... 231 SabineHild,CeciliaCobzaru,CarstenTroll,andBernhardRieger DK3712: “dk3712_c000” — 2007/10/23 — 11:58 — page v — #5 Chapter10 ControlofMolecularWeightandChain-EndGroupinTacticPolypropylenes UsingChainTransferAgents....................................................... 273 T.C.Chung Chapter11 FunctionalizationofTacticPolypropylenes ....................................... 297 ManfredBochmann Chapter12 InfluenceofTacticityofPropylenePlacementonStructureandPropertiesof Ethylene/PropyleneCopolymers................................................... 313 MaurizioGalimbertiandGaetanoGuerra III OtherMonoolefinMonomers.......................................................... 343 Chapter13 StereocontrolinthePolymerizationofHigherα-OlefinMonomers ............. 345 MosheKol,SharonSegal,andStanislavGroysman Chapter14 TacticPolystyreneandStyreneCopolymers....................................... 363 HaiyanMaandJilingHuang Chapter15 CyclopenteneHomo-andCopolymersMadewithEarlyandLateTransition MetalCatalysts...................................................................... 399 NaofumiNaga Chapter16 TacticNorborneneHomo-andCopolymersMadewithEarlyandLate TransitionMetalCatalysts.......................................................... 413 WalterKaminskyandMichaelArndt-Rosenau IV DieneMonomersandOlefin-ContainingPolymers............................... 445 Chapter17 TheStereoselectivePolymerizationofLinearConjugatedDienes............... 447 AntonioProtoandCarmineCapacchione Chapter18 TheStereoselectivePolymerizationofCyclicConjugatedDienes............... 475 MitsuruNakano Chapter19 TacticNonconjugatedDieneCyclopolymerizationand Cyclocopolymerization............................................................. 489 IlKim Chapter20 StereochemistryofPolymersFormedbyMetathesisPolymerizationof BicyclicandPolycyclicOlefins.................................................... 509 DarraghBreen,KatherineCurran,andWilhelmRisse Chapter21 StereoregularityofPolyacetyleneandItsDerivatives ............................ 553 ToshioMasuda,MasashiShiotsuki,andJunichiTabei V FunctionalandNon-OlefinicMonomers ............................................. 575 Chapter22 TacticityinEthylene/CarbonMonoxide/VinylCo-and Terpolymerizations.................................................................. 577 KyokoNozaki DK3712: “dk3712_c000” — 2007/10/23 — 11:58 — page vi — #6 Chapter23 StereoselectiveAcrylatePolymerization........................................... 593 EdwardL.MarshallandVernonC.Gibson Chapter24 DiscreteCatalystsforStereoselectiveEpoxidePolymerization.................. 627 HiroharuAjiro,ScottD.Allen,andGeoffreyW.Coates Chapter25 StereoselectivePolymerizationofLactide......................................... 645 MalcolmH.ChisholmandZhipingZhou Glossary............................................................................................ 661 Index................................................................................................ 667 DK3712: “dk3712_c000” — 2007/10/23 — 11:58 — page vii — #7 DK3712: “dk3712_c000” — 2007/10/23 — 11:58 — page viii — #8 Preface Polymersareoneofthemodernworld’smostintriguingandversatilematerials,abletoassumeanear- infinitevarietyofshapesandpropertiesthatpermeatealmosteveryaspectofourlivesasconsumers. Thecommutativenatureofplasticsisnotonlyafunctionoftheirmelt-processingcapabilities,butalso areflectionofthewidevarietyofpossiblemicrostructuresthateachpolymerchain(ordistribution ofchains)canassumeasauniquefingerprintofthepolymerizationmechanism. Among the many aspects of polymer chain microstructures, tacticity is arguably the most critical for determining polymer properties and uses. For example, atactic polypropylene is a soft, amorphous material, useful only in very limited applications such as adhesives or asphalt modifiers, while isotactic polypropylene is stiff and highly crystalline, possessing good heat res- istance and a high melting point. Isotactic polypropylene is one of today’s most commercially important polymers, used to make a wide range of products including fibers, food containers, molded auto parts, films, and nonwoven fabrics. These significant property differences arise principallyfromalignmentofthepolymer’spendantmethylgroupsintoaregularratherthanrandom arrangement. Today, the development of a new polymeric material requires a keen understanding of how to manipulate the most intimate features of individual polymer chains—tacticity, branching, comonomersequencedistribution,blocklength,regioerrors—toobtaindesirablephysicalproperties andperformance.Themodernpolymerchemistmustpossessagoodunderstandingoffundamental microstructuralstructure–propertyrelationshipsforanysystemunderstudy,bothfromthesynthetic perspective(relationshipsbetweenpolymerizationcatalystligand/activesitestructure,polymeriza- tionmechanism,andchainmicrostructure)andtheperformanceperspective(relationshipsbetween chainmicrostructure,phasebehavior,andbulkproperties). With this book, we have sought to create a one-volume reference containing information on the most important classes of tactic polymers and polymerizations carried out using single- site catalysis.1−5 This book contains 25 individual review chapters on tactic polymers and polymerizations,eachcontributedbytopresearchersinthearea,groupedintofiveparts. Thefirstpartdescribesthebasictypesoftacticpolypropylenesandcatalystsystemsusedtopre- parethem.Thesechaptersprovidethereaderwithanoverviewofknowncatalyststructure–polymer propertyrelationships,andexplainthecriticalligandmodificationstrategiesusedtoachievestereo- control. Newer classes of polypropylene polymerization catalysts, including nonmetallocene and latetransitionmetalprecatalysts,arealsohighlightedinordertoexemplifyemergingcatalystdesign techniques.Achapter discussing theoretical site-control studies is included to illustrate how such techniquesassistwithandcomplementcatalystdesign.Introductionstothefundamentalconceptsof tacticityandpolymerizationmechanismsarealsofeaturedintheearliestchapters.Thesecondpart containschaptershighlightingtheroleoftacticityinthedesignofpolypropyleneswithspecialphys- icalproperties(stereoblock,elastomeric,andfunctionaltacticmaterials).Tacticityconsiderationsin ethylene–propylenecopolymersarealsoexamined. Inthethirdpart,tacticityconsiderationsareexpandedtoothermonoolefinicmonomersandpoly- mers,withchapterscoveringtacticα-olefinandstyrenepolymerizations.Ditacticpolymerizations DK3712: “dk3712_c000” — 2007/10/23 — 11:58 — page ix — #9
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