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 Introduction to
POLYMER
CHEMISTRY
Third Edition

Charles E. Carraher, Jr.

CRC Press
Taylor & Francis Group
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Boca Raton, FL 33487-2742
© 2013 by Taylor & Francis Group, LLC
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Contents
Preface............................................................................................................................................ xiii
Acknowledgments...........................................................................................................................................xv
Author.............................................................................................................................................xvii
How to Study Polymers...................................................................................................................xix
Polymer Nomenclature....................................................................................................................xxi

Chapter 1 Introduction to Polymers...............................................................................................1

1.1 History of Polymers............................................................................................1
1.2 Why Polymers?................................................................................................. 10
1.3 Today’s Marketplace......................................................................................... 13
1.4 Environmental Assessment.............................................................................. 17
1.4.1 Environmental Impact Assessment..................................................... 17
1.4.2 Ecological Footprint............................................................................ 17
1.4.3 Life Cycle Assessment........................................................................ 19
1.5 Managing Sustainability................................................................................... 19
1.6 Summary.......................................................................................................... 21
Glossary....................................................................................................................... 22
Exercises...................................................................................................................... 23
Further Readings......................................................................................................... 23
General Encyclopedias and Dictionaries.....................................................................24

Chapter 2 Polymer Structure (Morphology)................................................................................25

2.1 Stereochemistry of Polymers............................................................................26
2.2 Molecular Interactions...................................................................................... 32
2.3 Polymer Crystals.............................................................................................. 39
2.4 Amorphous Bulk State..................................................................................... 42
2.5 Polymer Structure–Property Relationships...................................................... 43
2.6 Crystalline and Amorphous Combinations......................................................44
2.7 Cross-linking.................................................................................................... 47
2.8 Summary.......................................................................................................... 48
Glossary....................................................................................................................... 49
Exercises...................................................................................................................... 51
Further Readings......................................................................................................... 52

Chapter 3 Molecular Weight of Polymers.................................................................................... 53

3.1 Introduction...................................................................................................... 53
3.2 Solubility.......................................................................................................... 54
3.3 Average Molecular Weight Values................................................................... 58
3.4 Fractionation of Polydisperse Systems............................................................. 63
3.5 Chromatography............................................................................................... 63
3.6 Colligative Molecular Weights.........................................................................66
3.6.1 Osmometry..........................................................................................66
3.6.2 End-Group Analysis............................................................................ 67
3.6.3 Ebulliometry and Cryometry.............................................................. 67
3.7 Light-Scattering Photometry............................................................................ 67

v
vi Contents

3.8 Other Techniques.............................................................................................. 74

3.8.1 Ultracentrifugation.............................................................................. 74
3.8.2 Mass Spectrometry.............................................................................. 75
3.9 Viscometry....................................................................................................... 76
3.10 Summary.......................................................................................................... 82
Glossary...................................................................................................................... 83
Exercises...................................................................................................................... 85
Further Readings......................................................................................................... 87

Chapter 4 Naturally Occurring Polymers.................................................................................... 89

4.1 Polysaccharides................................................................................................ 91
4.2 Cellulose........................................................................................................... 93
4.2.1 Paper.................................................................................................... 95
4.2.1.1 Paper Recycling...................................................................96
4.3 Cellulose-Regenerating Processes....................................................................97
4.4 Esters and Ethers of Cellulose..........................................................................99
4.4.1 Inorganic Esters................................................................................... 99
4.4.2 Organic Esters................................................................................... 100
4.4.3 Organic Ethers................................................................................... 102
4.5 Starch.............................................................................................................. 103
4.6 Other Polysaccharides.................................................................................... 106
4.7 Proteins........................................................................................................... 109
4.7.1 Primary Structure..............................................................................112
4.7.2 Secondary Structure.......................................................................... 112
4.7.2.1 Keratines............................................................................ 114
4.7.3 Tertiary Structure.............................................................................. 116
4.7.3.1 Globular Proteins............................................................... 116
4.7.3.2 Fibrous Proteins................................................................. 118
4.7.3.3 Elastin................................................................................ 119
4.7.3.4 Membrane Proteins............................................................ 119
4.7.4 Quaternary Structure........................................................................ 119
4.8 Nucleic Acids.................................................................................................. 122
4.8.1 Flow of Biological Information......................................................... 125
4.9 Naturally Occurring Polyisoprenes and Other Synthetic Elastomers............ 128
4.9.1 Balloons............................................................................................. 132
4.9.2 Resins................................................................................................ 133
4.10 Lignin............................................................................................................. 134
4.11 Melanins......................................................................................................... 135
4.12 Polymer Structure........................................................................................... 137
4.13 Genetic Engineering....................................................................................... 139
4.14 DNA Profiling................................................................................................ 141
4.15 Asphalt............................................................................................................ 142
4.16 Summary........................................................................................................ 143
Glossary..................................................................................................................... 144
Exercises.................................................................................................................... 147
Further Readings....................................................................................................... 148

Chapter 5 Step-Reaction Polymerization (Polycondensation Reactions).................................. 149

5.1 Comparison between Polymer Type and Kinetics of Polymerization............ 149
5.2 Introduction.................................................................................................... 154
Contents vii

5.3 Stepwise Kinetics........................................................................................... 154

5.4 Polycondensation Mechanisms....................................................................... 159
5.5 Polyesters and Polycarbonates........................................................................ 161
5.6 Synthetic Polyamides..................................................................................... 166
5.7 Polyimides...................................................................................................... 172
5.8 Polybenzimidazoles and Related Polymers.................................................... 173
5.9 Polyurethanes and Polyureas.......................................................................... 174
5.10 Polysulfides..................................................................................................... 176
5.11 Polyethers....................................................................................................... 176
5.12 Polysulfones.................................................................................................... 178
5.13 Poly(Ether Ether Ketone) and Polyketones.................................................... 179
5.14 Phenolic and Amino Plastics.......................................................................... 180
5.15 Synthetic Routes............................................................................................. 182
5.16 Liquid Crystals............................................................................................... 183
5.17 Microfibers..................................................................................................... 185
5.18 Summary........................................................................................................ 186
Glossary..................................................................................................................... 186
Exercises.................................................................................................................... 188
Further Readings....................................................................................................... 189

Chapter 6 Ionic Chain-Reaction and Complex Coordination Polymerization

(Addition Polymerization)......................................................................................... 191
6.1 Cationic Polymerization................................................................................. 193
6.2 Anionic Polymerization.................................................................................. 197
6.3 Stereoregularity and Stereogeometry............................................................. 199
6.4 Polymerization with Complex Coordination Catalysts..................................200
6.5 Soluble Stereoregulating Catalysis................................................................. 201
6.6 Polyethylenes..................................................................................................205
6.7 Polypropylene................................................................................................. 211
6.8 Polymers from 1,4-Dienes.............................................................................. 215
6.9 Polyisobutylene............................................................................................... 217
6.10 Metathesis Reactions...................................................................................... 218
6.11 Zwitterionic Polymerization........................................................................... 219
6.12 Isomerization Polymerization......................................................................... 219
6.13 Precipitation Polymerization.......................................................................... 220
6.14 Summary........................................................................................................ 220
Glossary..................................................................................................................... 221
Exercises.................................................................................................................... 222
Further Readings.......................................................................................................224

Chapter 7 Free Radical Chain Polymerization (Addition Polymerization)............................... 225

7.1 Initiators for Free Radical Chain Polymerization.......................................... 225
7.2 Mechanism for Free Radical Chain Polymerization...................................... 229
7.3 Chain Transfer................................................................................................ 235
7.4 Polymerization Techniques............................................................................ 237
7.4.1 Bulk Polymerization.......................................................................... 237
7.4.2 Suspension Polymerization...............................................................240
7.4.3 Solution Polymerization....................................................................240
7.4.4 Emulsion Polymerization.................................................................. 241
7.5 Fluorine-Containing Polymers....................................................................... 243
viii Contents

7.6 Polystyrene.....................................................................................................246
7.7 Poly(Vinyl Chloride)......................................................................................248
7.8 Poly(Methyl Methacrylate)............................................................................. 250
7.9 Polyacrylonitrile............................................................................................. 251
7.10 Solid-State Irradiation Polymerization........................................................... 252
7.11 Plasma Polymerizations.................................................................................. 252
7.12 Summary........................................................................................................ 253
Glossary..................................................................................................................... 254
Exercises.................................................................................................................... 255
Further Readings....................................................................................................... 256

Chapter 8 Copolymerization...................................................................................................... 257

8.1 Kinetics of Copolymerization........................................................................ 258
8.2 The Q–e Scheme............................................................................................ 261
8.3 Commercial Copolymers................................................................................ 262
8.4 Block Copolymers.......................................................................................... 263
8.5 Graft Copolymers...........................................................................................264
8.6 Elastomers......................................................................................................264
8.6.1 Thermoplastic Elastomers.................................................................266
8.7 Blends............................................................................................................. 267
8.7.1 Immiscible Blends............................................................................. 268
8.7.2 Miscible Blends................................................................................. 269
8.8 Polymer Mixtures: IPNS and Alloys.............................................................. 270
8.9 Dendrites........................................................................................................ 271
8.10 Ionomers......................................................................................................... 272
8.11 Fluoroelastomers............................................................................................ 273
8.12 Nitrile Rubber................................................................................................. 274
8.13 Acrylonitrile Butadiene Styrene Terpolymers................................................ 274
8.14 EPDM Rubber................................................................................................ 275
8.15 Summary........................................................................................................ 275
Glossary..................................................................................................................... 276
Exercises.................................................................................................................... 277
Further Readings....................................................................................................... 278

Chapter 9 Organometallic and Metalloid Polymers.................................................................. 281

9.1 Introduction.................................................................................................... 281
9.2 Inorganic Reaction Mechanisms.................................................................... 283
9.3 Condensation Organometallic Polymers........................................................284
9.4 Coordination Polymers................................................................................... 289
9.5 Addition Polymers.......................................................................................... 291
9.6 Summary........................................................................................................ 295
Glossary..................................................................................................................... 295
Exercises.................................................................................................................... 295
Further Readings....................................................................................................... 296

Chapter 10 Inorganic Polymers................................................................................................... 297

10.1 Introduction.................................................................................................... 297
10.2 Portland Cement............................................................................................. 297
10.3 Other Cements................................................................................................300
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