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 Introduction to
POLYMER
CHEMISTRY
Third Edition

Charles E. Carraher, Jr.

CRC Press
Taylor & Francis Group
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© 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
Contents ix

10.4 Silicates...........................................................................................................300
10.4.1  Network............................................................................................. 303
10.4.2  Layer................................................................................................. 303
10.4.3  Chain.................................................................................................304
10.5 Silicon Dioxide (Amorphous).........................................................................304
10.5.1  Kinds of Glass...................................................................................306
10.5.2  Safety Glass......................................................................................308
10.6 Sol–Gel........................................................................................................... 310
10.6.1  Aerogels............................................................................................ 310
10.7 Silicon Dioxide (Crystalline Forms): Quartz Forms...................................... 312
10.8 Silicon Dioxide in Electronic Chips............................................................... 314
10.9 Asbestos.......................................................................................................... 314
10.10 Fly Ash and Aluminosilicates........................................................................ 315
10.11 Polymeric Carbon: Diamond.......................................................................... 317
10.12 Polymeric Carbon: Graphite........................................................................... 318
10.13 Internal Cyclization: Carbon Fibers and Related Materials........................... 319
10.14 Carbon Nanotubes.......................................................................................... 321
10.14.1  Structures.......................................................................................... 321
10.14.1.1 Electrical.......................................................................... 323
10.14.1.2 Mechanical....................................................................... 324
10.14.1.3 Field Emission................................................................. 324
10.14.1.4 Hydrogen and Ion Storage............................................... 324
10.14.1.5 Chemical and Genetic Probes.......................................... 324
10.14.1.6 Analytical Tools............................................................... 324
10.14.1.7 Superconductors............................................................... 324
10.15 Bitumens......................................................................................................... 325
10.16 Carbon Black.................................................................................................. 326
10.17 Polysulfur....................................................................................................... 327
10.18 Ceramics......................................................................................................... 327
10.19 High-Temperature Superconductors............................................................... 329
10.19.1  Discovery of the 123-Compound...................................................... 329
10.19.2  Structure of the 123-Compound....................................................... 329
10.20 Zeolites........................................................................................................... 330
10.21 Summary........................................................................................................ 331
Glossary..................................................................................................................... 332
Exercises.................................................................................................................... 333
Further Readings....................................................................................................... 333

Chapter 11 Reactions of Polymers............................................................................................... 335

11.1 Reactions with Polyolefins and Polyenes........................................................ 335
11.2 Reactions of Aromatic and Aliphatic Pendant Groups.................................. 336
11.3 Degradation.................................................................................................... 337
11.4 Cross-Linking................................................................................................. 339
11.5 Reactivities of End Groups............................................................................. 339
11.6 Supramolecules and Self-Assembly...............................................................340
11.7 Transfer and Retention of Oxygen..................................................................344
11.8 Nature’s Macromolecular Catalysts............................................................... 347
11.9 Photosynthesis................................................................................................ 352
11.9.1  Purple Photosynthetic Bacteria......................................................... 353
11.9.2 Green Sulfur Bacteria....................................................................... 355
x Contents

11.10 Mechanisms of Energy Physical Absorption................................................. 355

11.11 Breakage of Polymeric Materials................................................................... 356
11.12 Summary........................................................................................................ 358
Glossary..................................................................................................................... 358
Exercises.................................................................................................................... 359
Further Readings.......................................................................................................360

Chapter 12 Testing and Spectrometric Characterization of Polymers......................................... 361

12.1 Spectronic Characterization of Polymers....................................................... 362
12.1.1 Infrared Spectroscopy....................................................................... 362
12.1.2 Raman Spectroscopy......................................................................... 363
12.1.3 Nuclear Magnetic Resonance Spectroscopy..................................... 363
12.1.4 NMR Applications............................................................................ 365
12.1.5 Electron Paramagnetic Resonance Spectroscopy............................. 365
12.1.6 X-Ray Spectroscopy.......................................................................... 365
12.2 Surface Characterization................................................................................ 366
12.2.1 Auger Electron Spectroscopy and X-Ray Photoelectron
Spectroscopy..................................................................................... 367
12.2.2 Near-Field Scanning Optical Microscopy......................................... 367
12.2.3 Electron Microscopy......................................................................... 368
12.2.4 Scanning Probe Microscopy............................................................. 368
12.2.5 Secondary Ion Mass Spectroscopy................................................... 371
12.3 Amorphous Region Determinations............................................................... 371
12.4 Thermal Analysis........................................................................................... 372
12.5 Thermal Property Tests.................................................................................. 374
12.5.1 Thermal Conductivity....................................................................... 374
12.5.2 Thermal Expansion........................................................................... 374
12.5.3 Glass Transition Temperatures.......................................................... 375
12.6 Flammability.................................................................................................. 375
12.7 Electrical Properties: Theory......................................................................... 375
12.8 Electric Measurements................................................................................... 377
12.9 Weatherability................................................................................................ 378
12.10 Optical Properties Tests.................................................................................. 378
12.10.1 Index of Refraction............................................................................ 379
12.10.2 Optical Clarity................................................................................... 379
12.10.3 Absorption and Reflectance.............................................................. 379
12.11 Chemical Resistance...................................................................................... 380
12.12 Summary........................................................................................................ 381
Glossary..................................................................................................................... 381
Exercises.................................................................................................................... 383
Further Readings....................................................................................................... 383

Chapter 13 Rheology and Physical Tests..................................................................................... 385

13.1 Rheology........................................................................................................ 385
13.1.1 Rheology and Physical Tests............................................................. 388
13.1.2 Response Time.................................................................................. 391
13.2 Typical Stress–Strain Behavior...................................................................... 391
13.3 Stress–Strain Relationships............................................................................ 394
Contents xi

13.4 Specific Physical Tests.................................................................................... 396

13.4.1 Tensile Strength................................................................................. 396
13.4.2 Tensile Strength of Inorganic and Metallic Fibers and Whiskers..... 397
13.4.3 Compressive Strength........................................................................ 398
13.4.4 Impact Strength................................................................................. 398
13.4.5 Hardness............................................................................................ 398
13.4.6 Failure................................................................................................ 399
13.5 Summary........................................................................................................ 399
Glossary.....................................................................................................................400
Exercises....................................................................................................................400
Further Readings....................................................................................................... 401

Chapter 14 Additives....................................................................................................................403
14.1 Fillers..............................................................................................................403
14.2 Reinforcements...............................................................................................406
14.2.1 Fibers and Resins..............................................................................407
14.2.2 Applications.......................................................................................408
14.3 Nanocomposites............................................................................................. 411
14.4 Plasticizers...................................................................................................... 413
14.5 Antioxidants................................................................................................... 415
14.6 Heat Stabilizers.............................................................................................. 416
14.7 Ultraviolet Stabilizers..................................................................................... 416
14.8 Flame Retardants............................................................................................ 417
14.9 Colorants......................................................................................................... 418
14.10 Curing Agents................................................................................................. 418
14.11 Antistatic Agents: Antistats............................................................................ 419
14.12 Chemical Blowing Agents.............................................................................. 420
14.13 Compatibilizers.............................................................................................. 420
14.14 Impact Modifiers............................................................................................ 420
14.15 Processing Aids.............................................................................................. 420
14.16 Lubricants....................................................................................................... 420
14.17 Microorganism Inhibitors............................................................................... 421
14.18 Summary........................................................................................................ 421
Glossary..................................................................................................................... 422
Exercises.................................................................................................................... 424
Further Readings....................................................................................................... 425

Chapter 15 Synthesis of Reactants and Intermediates for Polymers........................................... 427

15.1 Monomer Synthesis from Basic Feedstocks................................................... 427
15.2 Reactants for Step-Reaction Polymerization.................................................. 434
15.3 Synthesis of Vinyl Monomers........................................................................440
15.4 Summary........................................................................................................ 445
Glossary..................................................................................................................... 445
Exercises.................................................................................................................... 445
Further Readings.......................................................................................................446

Chapter 16 Polymer Technology.................................................................................................. 447

16.1 Polymer Processing........................................................................................ 447
16.2 Secondary Structures: Mesophases................................................................449
xii Contents

16.3 Fibers.............................................................................................................. 450

16.3.1 Polymer Processing: Spinning and Fiber Production........................ 450
16.3.1.1 Introduction....................................................................... 450
16.3.1.2 Melt Spinning.................................................................... 451
16.3.1.3 Dry Spinning..................................................................... 452
16.3.1.4 Wet Spinning..................................................................... 453
16.4 Elastomers...................................................................................................... 453
16.4.1  Elastomer Processing........................................................................ 454
16.5 Films and Sheets............................................................................................. 456
16.5.1  Calendering....................................................................................... 456
16.6 Polymeric Foams............................................................................................ 457
16.7 Reinforced Plastics (Composites) and Laminates.......................................... 457
16.7.1  Composites........................................................................................ 457
16.7.2  Particle-Reinforced Composites, Large-Particle Composites.......... 458
16.7.3  Fiber-Reinforced Composites........................................................... 459
16.7.4  Processing of Fiber-Reinforced Composites..................................... 459
16.7.5  Structural Composites......................................................................460
16.7.6  Laminating........................................................................................460
16.8 Molding.......................................................................................................... 461
16.8.1  Injection Molding............................................................................. 461
16.8.2  Blow Molding................................................................................... 462
16.8.3  Rotational Molding...........................................................................464
16.8.4  Compression and Transfer Molding..................................................464
16.8.5  Thermoforming.................................................................................465
16.9 Casting............................................................................................................466
16.10 Extrusion........................................................................................................466
16.11 Coatings..........................................................................................................466
16.11.1  Processing.........................................................................................468
16.11.2  Rainwear........................................................................................... 470
16.12 Adhesives........................................................................................................ 470
16.13 Conductive Polymeric Materials.................................................................... 474
16.13.1  Photoconductive and Photonic Polymers.......................................... 474
16.13.2  Electrically Conductive Polymers..................................................... 475
16.14 Drug Design and Activity............................................................................... 479
16.15 Synthetic Biomedical Polymers...................................................................... 481
16.16 Dental Materials............................................................................................. 485
16.17 Emerging Polymers........................................................................................ 486
16.18 Green Materials.............................................................................................. 490
16.19 Summary........................................................................................................ 496
Glossary..................................................................................................................... 497
Exercises.................................................................................................................... 498
Further Readings....................................................................................................... 499
Appendix A: Structures of Common Polymers............................................................................. 501
Appendix B: Symbols.................................................................................................................... 505
Appendix C: Comments on Health and Toxicological Aspects of Polymers................................ 511
Appendix D: ISO 9000 and 14000................................................................................................ 515
Appendix E: Web Resources......................................................................................................... 517
Preface
There is an appropriate and necessary move toward green materials and green chemistry. This trend
is captured in this text, having been both integrated within the appropriate sections and with the
addition of a separate section on green materials. There also exists a greater awareness of health
concerns within our society, and this awareness is also mirrored in this text.
Polymers are all about us and are responsible for life itself—for communication (both natural
and synthetic), for our nutrition, clothing, recording history, buildings and highways, etc. In fact, it
is difficult to imagine society without synthetic polymers and life without natural polymers. Part of
being an educated and responsible citizen involves knowing the correct questions to ask and know-
ing (possible) correct answers. In our ever increasingly technological world, science plays a crucial
role in providing solutions to critical problems of food; clean and abundant water, energy, and air;
and health. This text provides both the information and insights that allow a better understanding of
these large molecules that are all about us.
Most polymer texts are aimed at either graduate students or are hybrids aimed at both the under-
graduate but mostly graduate students. This text is aimed mainly at undergraduate students but can
also serve graduate students. Thus, a strong bond is forged between science, history, and the cru-
cible that is today’s society. Information gained from the basic (foundational) core science courses
is brought to bear on understanding giant molecules. This information includes factual, theoretical,
and practical concepts presented in science. It is of use to those that want to be simply well educated,
as well as those wanting to pursue medicine, engineering, physics, chemistry, environmental sci-
ences, biomedical sciences, law, and business.
This text is inclusive in the treatment of polymers, including natural and synthetic giant mol-
ecules, inorganic and organic polymers, biomacromolecules, elastomers, adhesives, coatings, fibers,
plastics, blends, caulks, composites, ceramics, etc. The basic principles that apply to one polymer
grouping apply to all of the other groupings when applied with some simple fundamentals. These
fundamentals are integrated into the fabric of this text.
We remember the saying that we should be students of history so we do not repeat the same mis-
takes; we should also be students of history so that we might repeat the successes. Brief case studies
are woven within the fabric of the text as historical accounts illustrating the purposes in back of
change as well as the societal and scientific context within which these changes occurred.

xiii
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