Healable polymer systems

166 Pages·2013·6.652 MB·English

by  Wayne Hayes, Barnaby W Greenland

Healable Polymer Systems
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RSC Polymer Chemistry Series
Series Editors:
Professor Ben Zhong Tang (Editor-in-Chief), The Hong Kong University of
Science and Technology, Hong Kong, China
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0 Professor Alaa S. Abd-El-Aziz, University of Prince Edward Island, Canada
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0-F Professor Stephen L. Craig, Duke University, USA
47 ProfessorJianhua Dong,NationalNaturalScience FoundationofChina,China
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73 Professor Toshio Masuda, Fukui University of Technology, Japan
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4 Professor Christoph Weder, University of Fribourg, Switzerland
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9/ Titles in the Series:
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1 1: Renewable Resources for Functional Polymers and Biomaterials
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1 2:Molecular Design and Applications of Photofunctional Polymers and
doi: Materials
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c. 4: Fundamentals of Controlled/Living Radical Polymerization
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s.r 5: Healable Polymer Systems
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Healable Polymer Systems
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18 Department of Chemistry, University of Reading, Reading, UK
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97 Email: [email protected]; [email protected]
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htt RSCPolymerChemistrySeriesNo.5
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bli Apartfromfairdealingforthepurposesofresearchfornon-commercialpurposesorfor
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PublishedbyTheRoyalSocietyofChemistry,
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Forfurtherinformationseeourwebsiteatwww.rsc.org
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70- Preface
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oi:1 It is without question that polymer chemistry has made a tremendous impact
d upon society in the last century and the way in which day-to-day duties are
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or carriedout.Afteronlyapproximately100years,polymerchemistshaverefined
sc. theirartandlearnthowtomanipulatereactionsandfabricationtechniquesto
bs.r beabletomakematerialsinahighlydesignedandpredictivefashion.Reliable
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p:// polymer chemistries now enable everyday items that are taken for granted,
htt ranging from simple polyethylene carrier bags to complex block copolymers
on usedintheproductionofsiliconmicrochips,tobemadetospecificationandon
13 largescale.However,mankindfindsitselfinthe21stcenturyinanenvironment
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d y 2 thatdoesnothaveendlesspetroleumfeedstocks/energysupplieswithwhichto
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au continue synthesising new organic-based materials and thus there is a need
wnloFebr toexamineroutestorecyclablematerialsthatcanbere-healed/mendedinorder
o2
D2 to re-attain the desired function of the component or device.
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d o The primary objective of this monograph is to provide a reference text on
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h healable polymers that have been reported to date and cover these develop-
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bli ments from a chemist’s perspective. Healable materials span a wide range of
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technologies (i.e. inorganic-based materials as well as organic polymers) – this
particular review focuses upon the development of organic healable polymer
systems.Themonographisdividedintofourspecialistchaptersthatfollowon
from a general introduction to the field. The introductory chapter also
provides, for chemists who do not have an engineering background, an
overview of the key material assessments methods that are used to study
healablepolymericmaterialsinorderthatsomeonenewtothefieldcanstartto
appreciate and put into perspective the physical parameters thus described. In
thisrespect,weenvisagethatthismonographwillbesuitedtoawidereadership
baseand willbe asignificantassettonew researchers tothis field. Eachofthe
specialistchaptershasbeenwrittenbyleadersintheirrespectivefieldsandthese
RSCPolymerChemistrySeriesNo.5
HealablePolymerSystems
EditedbyWayneHayesandBarnabyWGreenland
rTheRoyalSocietyofChemistry2013
PublishedbytheRoyalSocietyofChemistry,www.rsc.org
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vi Preface
reviews serve to provide a critical assessment of the healable polymer systems
that have been reported to date:–
Encapsulated monomer approaches to Healable Polymers and Composites –
5 this chapter provides a comprehensive review of the encapsulated
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P monomer approach to healable polymer composites and also summarizes
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7 Reversible covalent bond formation as Strategies for Healable Polymers –
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9 highlyefficientreversiblecovalentbondformationprocessessuchasDiels-
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1 Alder cycloadditions or thiol-ene reactions have afforded successfully
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9 healablepolymerandchemicallyadaptivenetworks.Thischapterassesses
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03 the reversible covalent bond formation processes that have used to
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oi: Healable Supramolecular Polymeric Materials – this chapter reviews the use
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c.or hydrogen bonding, metal-ligand binding and p-p aromatic stacking in
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s.r order to assemble healable polymeric networks that are constructed from
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pu relatively low molecular weight oligomeric components.
p:// ThermodynamicsofSelf-HealingReactionsandtheirApplicationinPolymeric
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n Materials–thisreviewconsidersthethermodynamicparametersneededto
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3 achievesuccessfulhealablepolymers.Entropicandenthalpiccontributions
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d y 20 to the Gibbs free energy during self-healing events are evaluated in the
dear context of the chemical reactions within the material that contribute to
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n Weareextremelygratefultotheauthorsofthefourspecialistchapters,ithas
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ed been a pleasure to work with them in the preparation of this monograph.
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blis Finally, we would both like to thank our families (Kerry and Louisa, Emma
Pu and William, respectively) for their considerable patience and understanding
forthetimethatwehavespentawayfromdomesticdutiesduringtheassembly
and editing of the chapters for this detailed review.
Wayne Hayes and Barnaby W Greenland
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70- Contents
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0 Chapter 1 Healable Polymeric Materials 1
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c. 1.2 Healable Polymers – Potential Applications 3
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http:// 1.5 Measuring Healing 6
n 1.5.1 Cantilever Beam Tests to Determine Healing 7
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dear 1.5.4 Rheology – Background 11
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2.1 Introduction 16
2.2 Microencapsulation 18
2.2.1 InsituPoly(urea-formaldehyde)Encapsulation 18
2.2.2 Interfacial Polymerization 21
2.2.3 Hollow Fiber Encapsulation 23
2.2.4 Microcapsule Characterization 27
2.3 Chemistry of Encapsulated Self-Healing Materials 29
2.3.1 Ring-Opening Metathesis Polymerization 30
2.3.2 Siloxane-Based Healing Systems 34
2.3.3 Radical-Initiated Healing Chemistries 35
RSCPolymerChemistrySeriesNo.5
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viii Contents
2.3.4 Isocyanate-Based Healing Systems 36
2.3.5 Epoxy-Based Healing Systems 37
2.3.6 ‘‘Click-Chemistry’’-Based Healing Agents 38
2.3.7 Solvent or Plasticizer-Based Healing
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03 2.4.3 Tear Testing 51
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http:// Chapter 3 Reversible Covalent Bond Formation as a Strategy for
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nloebr 3.2 A Brief Historical Account 63
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3.4.2 Radical-Mediated Addition–Fragmentation
Reactions 74
3.4.3 Disulfides 77
3.4.4 The Diels-Alder Reaction 79
3.4.5 Other Reversible Chemistries 81
3.5 Kinetics and Mechanical Properties 84
3.6 Conclusion and Outlook 86
References 87
Chapter 4 Healable Supramolecular Polymeric Materials 92
Barnaby W.Greenland,Gina L. Fiore, Stuart J. Rowan and
Christoph Weder
4.1 Introduction 92
4.1.1 Supramolecular Polymer Chemistry:
A Concise History 93
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Contents ix
4.2 Healable Supramolecular Polymers Utilizing
Hydrogen Bonding 97
4.2.1 Supramolecular Polymers Containing
Hydrogen Bonding Motifs with Low
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doi: 4.6.1 Healable Supramolecular Polymeric Gels 114
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c. 4.6.3 Healable Molecular Gels 119
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and Thermosetting Polymers 135
5.3.2 Supramolecular Approaches to Healable
Thermoplastic and Thermosetting Polymers 143
5.4 Summary 145
References 146
Subject Index 149
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