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Carraher’s Polymer Chemistry
Tenth Edition
Carraher’s Polymer Chemistry
Tenth Edition
Charles E. Carraher, Jr.

CRC Press
Taylor & Francis Group
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Boca Raton, FL 33487-2742
© 2018 by Taylor & Francis Group, LLC

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Library of Congress Cataloging-in-Publication Data
Names: Carraher, Charles E., Jr., 1941-

Title: Carraher’s polymer chemistry.
Other titles: Polymer chemistry
Description: Tenth edition. | Boca Raton : CRC Press, 2017.
Identifiers: LCCN 2017017296 | ISBN 9781498737388 (hb)
Subjects: LCSH: Polymers. | Polymers--Textbooks. | Polymerization. |
Polymerization--Textbooks.
Classification: LCC QD381 .S483 2017 | DDC 547/.7--dc23
LC record available at https://lccn.loc.gov/2017017296
Visit the Taylor & Francis Web site at

http://www.taylorandfrancis.com
and the CRC Press Web site at
http://www.crcpress.com
Contents
Preface............................................................................................................................................xvii
Acknowledgments............................................................................................................................xix
Author..............................................................................................................................................xxi
Chapter 1 Introduction to Polymers...............................................................................................1

1.1 History of Polymers............................................................................................ 1
1.2 Why Polymers?................................................................................................. 11
1.3 Today’s Marketplace......................................................................................... 15
1.4 Environmental Assessment.............................................................................. 18
1.5 Summary.......................................................................................................... 23
Glossary.......................................................................................................................24
Exercises......................................................................................................................24
Answers.......................................................................................................................25
Additional Reading.....................................................................................................25
General Encyclopedias and Dictionaries.....................................................................26
Chapter 2 Polymer Structure (Morphology)................................................................................ 27

2.1 Stereochemistry of Polymers............................................................................28
2.1.1 Chain Length...................................................................................... 29
2.1.2 Pendant Groups and Branching.......................................................... 31
2.1.3 Tacticity.............................................................................................. 31
2.2 Molecular Interactions......................................................................................34
2.2.1 Glass Transition and Melt Transition................................................. 39
2.2.2 Secondary Structure........................................................................... 42
2.3 Polymer Crystals.............................................................................................. 42
2.4 Amorphous Bulk State.....................................................................................46
2.5 Polymer Structure–Property Relationships......................................................46
2.6 Crosslinking..................................................................................................... 50
2.7 Crystalline and Amorphous Combinations...................................................... 51
2.8 Summary.......................................................................................................... 53
Glossary....................................................................................................................... 54
Exercises...................................................................................................................... 55
Answers....................................................................................................................... 56
Additional Reading..................................................................................................... 58
Chapter 3 Molecular Weight of Polymers.................................................................................... 59

3.1 Introduction...................................................................................................... 59
3.2 Solubility.......................................................................................................... 61
3.2.1 Polymer Solubility: Actual................................................................. 65
3.3 Average Molecular Weight Values................................................................... 68
3.4 Fractionation of Polydisperse Systems............................................................. 71
3.5 Chromatography............................................................................................... 71
3.6 Colligative Molecular Weights......................................................................... 75
3.6.1 Osmometry......................................................................................... 75
v
vi Contents
3.6.2 End-Group Analysis........................................................................... 77

3.6.3 Ebulliometry and Cryometry............................................................. 77
3.7 Light Scattering Photometry............................................................................ 77
3.8 Other Techniques.............................................................................................. 83
3.8.1 Ultracentrifugation............................................................................. 83
3.8.2 Mass Spectrometry............................................................................. 85
3.9 Viscometry....................................................................................................... 86
3.10 Summary..........................................................................................................92
Glossary....................................................................................................................... 93
Exercises...................................................................................................................... 95
Answers.......................................................................................................................97
Additional Reading..................................................................................................... 98
Chapter 4 Polycondensation Polymers (Step-Reaction Polymerization)................................... 101

4.1 Comparison between Polymer Types and Kinetics of Polymerization.......... 101
4.2 Introduction.................................................................................................... 106
4.3 Stepwise Kinetics........................................................................................... 106
4.4 Polycondensation Mechanisms....................................................................... 111
4.5 Polyesters........................................................................................................ 113
4.6 Polycarbonates................................................................................................ 122
4.7 Synthetic Polyamides..................................................................................... 126
4.8 Polyimides...................................................................................................... 135
4.9 Polyamide-Imide............................................................................................ 137
4.10 Polybenzimidazoles and Related Polymers.................................................... 138
4.11 Polyurethanes and Polyureas.......................................................................... 141
4.12 Polysulfides..................................................................................................... 145
4.13 Polyethers and Epoxys.................................................................................... 145
4.14 Polysulfones.................................................................................................... 150
4.15 Poly(Ether Ether Ketone) and Polyketones.................................................... 151
4.16 Phenolic and Amino Plastics.......................................................................... 152
4.17 Furan Resins................................................................................................... 155
4.18 Synthetic Routes............................................................................................. 156
4.19 Liquid Crystals............................................................................................... 157
4.20 Microfibers..................................................................................................... 160
4.21 Summary........................................................................................................ 162
Glossary..................................................................................................................... 163
Exercises.................................................................................................................... 164
Answers..................................................................................................................... 166
Additional Reading................................................................................................... 167
Chapter 5 Ionic Chain-Reaction and Complex Coordination Polymerization (Addition

Polymerization)......................................................................................................... 169
5.1 Chain Growth Polymerization: General......................................................... 170
5.2 Cationic Polymerization................................................................................. 171
5.3 Anionic Polymerization.................................................................................. 177
5.4 Stereoregularity.............................................................................................. 182
5.5 Polymerization with Complex Coordination Catalysts.................................. 183
5.6 Soluble Stereoregulating Catalysis................................................................. 184
5.7 Polyethylenes.................................................................................................. 188
Contents vii
5.8 Polypropylene................................................................................................. 196

5.9 Polymers from 1,4-Dienes..............................................................................202
5.10 Polyisobutylene...............................................................................................205
5.11 Metathesis Reactions......................................................................................206
5.12 Zwitterionic Polymerization...........................................................................207
5.13 Isomerization Polymerization.........................................................................208
5.14 Precipitation Polymerization..........................................................................208
5.15 Summary........................................................................................................209
Glossary..................................................................................................................... 210
Exercises.................................................................................................................... 210
Answers..................................................................................................................... 213
Chapter 6 Free Chain Polymerization (Addition Polymerization)............................................. 217

6.1 Initiators for Free Radical Chain Polymerization.......................................... 217
6.2 Mechanism for Free Radical Chain Polymerization...................................... 221
6.3 Chain Transfer................................................................................................ 228
6.4 Polymerization Techniques............................................................................ 230
6.5 Fluorine-Containing Polymers....................................................................... 234
6.6 Polystyrene..................................................................................................... 239
6.7 Poly(Vinyl Chloride)...................................................................................... 241
6.8 Poly(Methyl Methacrylate)............................................................................. 245
6.9 Poly(Vinyl Alcohol) and Poly(Vinyl Acetals)................................................ 250
6.10 Polyacrylonitrile............................................................................................. 251
6.11 Solid-State Irradiation Polymerization........................................................... 252
6.12 Plasma Polymerizations.................................................................................. 253
6.13 Controlled Radical Polymerizations............................................................... 253
6.14 Summary........................................................................................................ 254
Glossary..................................................................................................................... 254
Exercises.................................................................................................................... 255
Answers..................................................................................................................... 257
References................................................................................................................. 258
Chapter 7 Copolymerization...................................................................................................... 261

7.1 Kinetics of Copolymerization........................................................................ 262
7.2 The Q–e Scheme............................................................................................266
7.3 Commercial Copolymers................................................................................ 268
7.4 Block Copolymers.......................................................................................... 268
7.5 Graft Copolymers........................................................................................... 270
7.6 Elastomers...................................................................................................... 271
7.7 Thermoplastic Elastomers.............................................................................. 273
7.8 Blends............................................................................................................. 274
7.8.1 Immiscible Blends............................................................................ 274
7.8.2 Miscible Blends................................................................................ 276
7.9 Fluoroelastomers............................................................................................ 278
7.10 Nitrile Rubber................................................................................................. 278
7.11 Acrylonitrile–Butadiene–Styrene Terpolymers............................................. 279
7.12 EPDM Rubber................................................................................................280
7.13 Networks: General..........................................................................................280
viii Contents
7.14 Polymer Mixtures........................................................................................... 282

7.15 Dendrites........................................................................................................ 282
7.16 Ionomers.........................................................................................................284
7.17 Laboratory Gloves.......................................................................................... 286
7.18 Summary........................................................................................................ 286
Glossary..................................................................................................................... 288
Exercises.................................................................................................................... 289
Answers..................................................................................................................... 290
Chapter 8 Composites and Fillers.............................................................................................. 293

8.1 Fillers.............................................................................................................. 293
8.2 Types of Composites....................................................................................... 294
8.3 Long Fiber Composites: Theory..................................................................... 296
8.4 Fibers and Resins............................................................................................ 298
8.5 Long Fiber Composites: Applications............................................................300
8.6 Nanocomposites.............................................................................................302
8.7 Fabrication......................................................................................................306
8.7.1 Processing of Fiber-Reinforced Composites....................................306
8.7.2 Structural Composites......................................................................306
8.7.3 Laminating.......................................................................................307
8.7.4 Particulate.........................................................................................307
8.8 Summary........................................................................................................308
Glossary.....................................................................................................................308
Exercises....................................................................................................................309
Answers.....................................................................................................................309
Chapter 9 Naturally Occurring Polymers—Plants.................................................................... 313

9.1 Polysaccharides.............................................................................................. 314
9.2 Cellulose......................................................................................................... 316
9.3 Paper............................................................................................................... 319
9.4 Cellulose-Regenerating Processes.................................................................. 323
9.4.1 Rayon................................................................................................ 324
9.4.2 Cellophane........................................................................................ 326
9.5 Esters and Ethers of Cellulose........................................................................ 326
9.5.1 Wrinkle-Free Fabric......................................................................... 327
9.5.2 Inorganic Esters................................................................................ 327
9.5.3 Organic Esters.................................................................................. 328
9.5.4 Organic Ethers.................................................................................. 330
9.6 Starch.............................................................................................................. 332
9.7 Homopolysaccharides..................................................................................... 335
9.7.1 Fructans............................................................................................ 337
9.7.2 Chitin and Chitosan.......................................................................... 338
9.7.3 Others............................................................................................... 339
9.8 Heteropolysaccharides.................................................................................... 339
9.9 Synthetic Rubbers........................................................................................... 343
9.10 Naturally Occurring Polyisoprenes................................................................ 349
9.11 Resins............................................................................................................. 354
Contents ix
9.12 Balloons.......................................................................................................... 355

9.13 Lignin............................................................................................................. 356
9.14 Melanins......................................................................................................... 358
9.15 Asphalt............................................................................................................ 359
9.16 Castor Oil.......................................................................................................360
9.17 Summary........................................................................................................ 361
Glossary..................................................................................................................... 362
Exercises.................................................................................................................... 363
Answers.....................................................................................................................364
Chapter 10 Naturally Occurring Polymers—Animals................................................................ 367

10.1 Proteins........................................................................................................... 368
10.2 Levels of Protein Structure............................................................................. 371
10.2.1 Primary Structure............................................................................. 372
10.2.2 Secondary Structure......................................................................... 372
10.2.2.1 Keratins.............................................................................. 373
10.2.2.2 Silk and Spider Webs......................................................... 375
10.2.2.3 Wool................................................................................... 378
10.2.2.4 Collagen............................................................................. 380
10.2.2.5 Elastin................................................................................ 381
10.2.3 Tertiary Structure............................................................................. 381
10.2.3.1 Globular Proteins............................................................... 382
10.2.3.2 Fibrous Proteins................................................................. 383
10.2.3.3 Membrane Proteins............................................................ 383
10.2.4 Quaternary Structure........................................................................ 383
10.3 Nucleic Acids.................................................................................................. 386
10.4 Flow of Biological Information...................................................................... 391
10.5 RNA Interference........................................................................................... 393
10.6 Polymer Structure........................................................................................... 394
10.7 Protein Folding............................................................................................... 399
10.8 Genetic Engineering....................................................................................... 401
10.9 DNA Profiling................................................................................................403
10.10 The Human Genome—General.....................................................................405
10.11 Chromosomes................................................................................................. 410
10.11.1 The Next Steps.................................................................................. 422
10.12 Spliceosomes.................................................................................................. 423
10.13 Proteomics...................................................................................................... 423
10.14 Protein Site Activity Identification................................................................. 425
10.15 Summary........................................................................................................ 425
Glossary..................................................................................................................... 426
Exercises.................................................................................................................... 429
Answers..................................................................................................................... 430
Chapter 11 Organometallic and Inorganic–Organic Polymers................................................... 433

11.1 Introduction.................................................................................................... 433
11.2 Inorganic Reaction Mechanisms.................................................................... 433
x Contents
11.3 Condensation Organometallic Polymers........................................................ 437

11.3.1 Polysiloxanes.................................................................................... 438
11.3.2 Organotin and Related Condensation Polymers............................... 441
11.4 Coordination Polymers...................................................................................444
11.4.1 Platinum-Containing Polymers........................................................446
11.5 Addition Polymers.......................................................................................... 447
11.5.1 Ferrocene-Containing and Related Polymers..................................449
11.5.2 Polyphosphazenes and Related Polymers......................................... 451
11.5.3 Boron-Containing Polymers............................................................. 452
11.6 Ion-Exchange Resins...................................................................................... 453
11.7 Summary........................................................................................................ 455
Glossary..................................................................................................................... 455
Exercises.................................................................................................................... 455
Answers..................................................................................................................... 456
Chapter 12 Inorganic Polymers................................................................................................... 459

12.1 Introduction.................................................................................................... 459
12.2 Portland Cement............................................................................................. 459
12.3 Other Cements................................................................................................ 462
12.4 Silicates........................................................................................................... 463
12.4.1 Network............................................................................................465
12.4.2 Layer.................................................................................................466
12.4.3 Chain................................................................................................ 467
12.5 Silicon Dioxide (Amorphous)......................................................................... 467
12.6 Kinds of Amorphous Glass............................................................................ 470
12.7 Safety Glass.................................................................................................... 473
12.7.1 New Applications of Glass............................................................... 475
12.8 Lenses............................................................................................................. 475
12.9 Sol–Gel........................................................................................................... 478
12.10 Aerogels.......................................................................................................... 479
12.11 Silicon Dioxide (Crystalline Forms): Quartz Forms...................................... 481
12.12 Silicon Dioxide in Electronic Chips............................................................... 482
12.13 Silicon Dioxide in Optical Fibers................................................................... 483
12.14 Asbestos..........................................................................................................484
12.15 Fly Ash and Aluminosilicates........................................................................ 485
12.16 Polymeric Carbon: Diamond.......................................................................... 487
12.17 Polymeric Carbon: Graphite........................................................................... 487
12.18 Internal Cyclization: Carbon Fibers and Related Materials........................... 489
12.19 Carbon Nanotubes.......................................................................................... 490
12.19.1 Structures.......................................................................................... 491
12.20 Bitumens......................................................................................................... 496
12.21 Carbon Black.................................................................................................. 497
12.22 Polysulfur....................................................................................................... 499
12.23 Ceramics......................................................................................................... 499
12.24 High-Temperature Superconductors............................................................... 501
12.24.1 Discovery of the 123-Compound..................................................... 501
12.24.2 Structure of the 123-Compound....................................................... 501
12.25 Zeolites........................................................................................................... 502
12.26 Summary........................................................................................................ 503
Contents xi
Glossary.....................................................................................................................504
Exercises.................................................................................................................... 505
Answers.....................................................................................................................506
Further Reading......................................................................................................... 508
Chapter 13 Testing and Spectrometric Characterization of Polymers.........................................509

13.1 Introduction....................................................................................................509
13.2 Spectronic Characterization of Polymers....................................................... 510
13.2.1 Infrared Spectroscopy...................................................................... 510
13.2.2 Raman Spectroscopy........................................................................ 511
13.2.3 Nuclear Magnetic Resonance Spectroscopy.................................... 512
13.2.4 NMR Applications........................................................................... 513
13.2.5 Electron Paramagnetic Resonance Spectroscopy............................ 514
13.2.6 X-Ray Spectroscopy......................................................................... 514
13.3 Surface Characterization................................................................................ 514
13.3.1 Auger Electron Spectroscopy and X-Ray Photoelectron
Spectroscopy..................................................................................... 515
13.3.2 Near-Field Scanning Optical Microscopy........................................ 516
13.3.3 Electron Microscopy........................................................................ 516
13.3.4 Scanning Probe Microscopy............................................................ 517
13.3.5 Superresolution Fluorescence Microscopy....................................... 519
13.3.6 Secondary Ion Mass Spectroscopy................................................... 520
13.4 Amorphous Region Determinations............................................................... 520
13.5 Mass Spectrometry......................................................................................... 521
13.6 Thermal Analysis........................................................................................... 521
13.7 Thermal Property Tests.................................................................................. 523
13.7.1 Softening Range............................................................................... 523
13.7.2 Heat Deflection Temperature............................................................ 524
13.7.3 Glass Transition Temperatures......................................................... 524
13.7.4 Thermal Conductivity...................................................................... 525
13.7.5 Thermal Expansion.......................................................................... 526
13.8 Flammability.................................................................................................. 526
13.9 Electrical Properties: Theory......................................................................... 527
13.10 Electric Measurements................................................................................... 529
13.10.1 Dielectric Constant........................................................................... 530
13.10.2 Electrical Resistance........................................................................ 530
13.10.3 Dissipation Factor and Power Loss.................................................. 530
13.10.4 Electrical Conductivity and Dielectric Strength.............................. 531
13.11 Optical Properties Tests.................................................................................. 532
13.11.1 Index of Refraction........................................................................... 532
13.11.2 Optical Clarity.................................................................................. 533
13.11.3 Absorption and Reflectance............................................................. 533
13.12 Weatherability................................................................................................ 534
13.13 Chemical Resistance...................................................................................... 534
13.14 Measurement of Particle Size......................................................................... 534
13.15 Measurement of Adhesion.............................................................................. 536
13.16 Permeability and Diffusion............................................................................ 537
13.17 Summary........................................................................................................ 539
Glossary..................................................................................................................... 539
Exercises.................................................................................................................... 541
xii Contents
Answers..................................................................................................................... 541
Chapter 14 Rheology and Physical Tests..................................................................................... 545

14.1 Rheology........................................................................................................ 545
14.1.1 Rheology and Physical Tests............................................................ 548
14.1.2 Response Time................................................................................. 551
14.2 Typical Stress–Strain Behavior...................................................................... 552
14.3 Stress–Strain Relationships............................................................................ 554
14.4 Specific Physical Tests.................................................................................... 556
14.4.1 Tensile Strength................................................................................ 556
14.4.2 Tensile Strength of Inorganic and Metallic Fibers and Whiskers.... 557
14.4.3 Compressive Strength....................................................................... 558
14.4.4 Impact Strength................................................................................ 559
14.4.5 Hardness........................................................................................... 560
14.4.6 Brinell Hardness............................................................................... 561
14.4.7 Rockwell Hardness........................................................................... 561
14.4.8 Shear Strength.................................................................................. 562
14.4.9 Abrasion Resistance......................................................................... 562
14.4.10 Failure............................................................................................... 563
14.5 Summary........................................................................................................ 563
Glossary.....................................................................................................................564
Exercises.................................................................................................................... 565
Answers..................................................................................................................... 566
Chapter 15 Additives.................................................................................................................... 569

15.1 Plasticizers...................................................................................................... 569
15.2 Antioxidants................................................................................................... 573
15.3 Heat Stabilizers.............................................................................................. 575
15.4 Ultraviolet Stabilizers..................................................................................... 575
15.5 Flame Retardants............................................................................................ 576
15.6 Colorants......................................................................................................... 577
15.7 Curing Agents................................................................................................. 578
15.8 Antistatic Agents: Antistats............................................................................ 578
15.9 Chemical Blowing Agents.............................................................................. 579
15.10 Compatibilizers.............................................................................................. 579
15.11 Impact Modifiers............................................................................................ 580
15.12 Processing AIDS............................................................................................ 580
15.13 Lubricants....................................................................................................... 580
15.14 Microorganism Inhibitors............................................................................... 580
15.15 Summary........................................................................................................ 580
Glossary..................................................................................................................... 581
Exercises.................................................................................................................... 582
Answers..................................................................................................................... 583
Chapter 16 Reactions on Polymers.............................................................................................. 585

16.1 Reactions with Polyolefines and Polyenes...................................................... 585
Contents xiii
16.2 Reactions of Aromatic and Aliphatic Pendant Groups.................................. 586

16.3 Degradation.................................................................................................... 586
16.4 Reactivities of End Groups............................................................................. 589
16.5 Supramolecules and Self-Assembly............................................................... 590
16.6 Transfer and Retention of Oxygen.................................................................. 594
16.7 Nature’s Macromolecular Catalysts................................................................ 598
16.8 Photosynthesis................................................................................................ 601
16.8.1 Purple Photosynthetic Bacteria........................................................604
16.8.2 Green Sulfur Bacteria.......................................................................606
16.9 Mechanisms of Physical Energy Absorption.................................................606
16.10 Breakage of Polymeric Materials...................................................................608
16.11 Summary........................................................................................................ 610
Glossary..................................................................................................................... 610
Exercises.................................................................................................................... 611
Answers..................................................................................................................... 612
Chapter 17 Synthesis of Reactants and Intermediates for Polymers........................................... 615

17.1 Monomer Synthesis from Basic Feedstocks................................................... 615
17.2 Reactants for Step-Reaction Polymerization.................................................. 622
17.3 Synthesis of Vinyl Monomers........................................................................ 629
17.4 Synthesis of Free Radical Initiators............................................................... 634
17.5 Hunting for Less Expensive Feedstock.......................................................... 636
17.6 Summary........................................................................................................ 637
Glossary..................................................................................................................... 637
Exercises.................................................................................................................... 637
Answers..................................................................................................................... 638
Chapter 18 Polymer Technology.................................................................................................. 645

18.1 Polymer Processing........................................................................................ 645
18.2 Secondary Structures: Mesophases................................................................648
18.3 Fibers.............................................................................................................. 649
18.3.1 Polymer Processing: Spinning and Fiber Production.......................649
18.3.1.1 Introduction.......................................................................649
18.3.1.2 Melt Spinning.................................................................... 649
18.3.1.3 Dry Spinning..................................................................... 652
18.3.1.4 Wet Spinning..................................................................... 652
18.3.1.5 Other Spinning Processes.................................................. 652
18.3.1.6 Nonspinning Fiber Production.......................................... 653
18.3.1.7 Natural Fibers.................................................................... 654
18.4 Elastomers...................................................................................................... 654
18.4.1 Elastomer Processing....................................................................... 655
18.5 Films and Sheets............................................................................................. 657
18.5.1 Calendering...................................................................................... 658
18.6 Polymeric Foams............................................................................................ 658
18.7 Reinforced Plastics (Composites) and Laminates.......................................... 659
18.7.1 Composites....................................................................................... 659
18.7.2 Particle-Reinforced Composites: Large-Particle Composites.......... 659
18.7.3 Fiber-Reinforced Composites...........................................................660
xiv Contents
18.7.4 Processing of Fiber-Reinforced Composites....................................660

18.7.5 Structural Composites...................................................................... 661
18.7.6 Laminating....................................................................................... 662
18.7.7 Natural Composites.......................................................................... 662
18.8 Molding..........................................................................................................664
18.8.1 Injection Molding.............................................................................664
18.8.2 Blow Molding...................................................................................666
18.8.3 Rotational Molding........................................................................... 667
18.8.4 Compression and Transfer Molding.................................................668
18.8.5 Thermoforming................................................................................ 670
18.9 Casting............................................................................................................ 672
18.10 Extrusion........................................................................................................ 672
18.11 Coatings.......................................................................................................... 673
18.11.1 Processing......................................................................................... 675
18.11.2 Rainwear........................................................................................... 677
18.12 Adhesives........................................................................................................ 678
18.13 Summary........................................................................................................ 683
Glossary.....................................................................................................................684
Exercises.................................................................................................................... 685
Answers..................................................................................................................... 686
Chapter 19 Selected Topics.......................................................................................................... 689

19.1 Conductive Polymeric Materials.................................................................... 689
19.1.1 Photoconductive and Photonic Polymers......................................... 689
19.1.2 Electrically Conductive Polymers....................................................690
19.1.3 Electrochromism.............................................................................. 696
19.1.4 Nanowires......................................................................................... 696
19.2 Nonlinear Optical Behavior........................................................................... 698
19.3 Photophysics and Photochemistry: Basics...................................................... 699
19.4 Drug Design and Activity............................................................................... 704
19.4.1 General............................................................................................. 705
19.4.2 Drug Testing..................................................................................... 705
19.5 Synthetic Biomedical Polymers...................................................................... 708
19.5.1 Dentistry........................................................................................... 711
19.6 Sutures............................................................................................................ 713
19.7 Geotextiles...................................................................................................... 718
19.8 Smart Materials.............................................................................................. 719
19.9 High-Performance Thermoplastics................................................................ 720
19.10 Flame-Resistant Textiles................................................................................ 722
19.11 Water-Soluble Polymers................................................................................. 724
19.12 Hydrogels........................................................................................................ 725
19.13 Emerging Polymers........................................................................................ 725
19.14 Green Materials.............................................................................................. 730
19.15 New Materials: Additional Aspects............................................................... 737
19.16 Summary........................................................................................................ 740
Glossary..................................................................................................................... 741
Exercises.................................................................................................................... 741
Answers..................................................................................................................... 742
Contents xv
Appendix A: Symbols................................................................................................................... 747

Appendix B: Structures of Common Polymers.......................................................................... 753
Appendix C: Mathematical Values and Units............................................................................ 757
Appendix D: Comments on Health............................................................................................. 759
Appendix E: ISO 9000 and 14000............................................................................................... 761
Appendix F: Electronic Education Websites.............................................................................. 763
Index............................................................................................................................................... 765
Preface
As with most sciences, and chemistry in particular, there is an explosive broadening and increase
in the importance of the application of the foundational principles of polymers. This broadening is
seen in ever-increasing vistas allowing the advancement of our increasingly technologically depen-
dent society and solutions to society’s most important problems in areas such as the environment
and medicine. Some of this broadening is the result of the extended understanding and application
of already-known principles, but it also includes the development of basic principles and materials
known to us hardly a decade ago. Most of the advancements in communication and computers,
medicine, and air and water purity are tied to macromolecules and the fundamental understand-
ing of the principles that govern their behavior. Much of this revolution is of a fundamental nature
and is explored in this latest edition. This book contains these basic principles as well as touches
upon their application to real-life situations. Technology is the application of scientific principles.
In polymers, there is often little, if any, division between science and technology.
The importance of the environment and our interaction with it is becoming increasingly evident.
Industry is increasingly emphasizing green science and practices that are favorable to the environ-
ment. Polymer science is part of this increased emphasis and contributes critical components to
solutions. This book continues to emphasize these measures, including special sections that deal
directly with environmental issues as well as integrating green science appropriately woven within
the fabric that is polymer chemistry. Consistent with the continued emphasis on green chemistry,
new sections that deal with photochemistry and green materials have been added.
Polymers are found in the organic natural world as building blocks for life itself. They are also
found as inorganic building blocks that allow the construction of homes, skyscrapers, and roads.
Synthetic polymers serve as basic building blocks of society today and tomorrow. This book includes
all three of these critical segments of polymeric materials.
A basic understanding of polymers is essential to the training of today’s science, biomedical,
and engineering students. This book complies with the American Chemical Society’s Committee
on Professional Training guidelines as an advanced or in-depth course. It naturally integrates and
interweaves the important foundational areas, since polymers are critical to all of the foundational
areas, with all of these foundational areas contributing to the growth of polymer science. Most of
the fundamental principles of polymers extend and enhance similar principles found throughout the
undergraduate and graduate training of students. This allows students to integrate their chemical
knowledge, illustrating the connection between fundamental and applied chemical information.
Thus, along with the theoretical information, application is integrated as an essential part of the
information. As in other areas such as business and medicine, short case studies are integrated as
historical material.
While this book is primarily written as an introductory graduate-level text, it can also be used as
an undergraduate text, or as an introductory undergraduate–graduate text. The topics are written so
that the order and inclusion or exclusion of chapters or parts of chapters will still allow the students
an adequate understanding of the science of polymers. Most of the chapters are written beginning
with the theory followed by application. The most important topics are generally at the beginning of
the chapter followed by important, but less critical, sections. Some will choose to take the synthesis-
intense chapters first, others will take the analytical/analysis/properties chapters first, and others
will simply take the chapters as they appear in the text. The book contains all of the elements of an
introductory text with synthesis, property, application, and characterization all present, allowing
this to be the only polymer course taken by an individual or the first in a series of polymer-related
courses taken by a student.
This edition continues in the “user-friendly” mode with special sections in each chapter
containing definitions, learning objectives, questions, and additional reading. Application and
xvii
xviii Preface
theory are integrated so that they reinforce one another. There is a continued emphasis on picturing,
reinforcing, interweaving, and integrating the basic concepts. The initial chapter is shorter, allow-
ing the students to become acclimated. Other chapters are written so they can be covered in about
a week’s time or less. Where possible, difficult topics are distributed and reinforced over several
topics. Case studies are woven into the text fabric.
The basic principles that apply to synthetic polymers apply equally well to inorganic and
biological polymers and are present in each of the chapters covering these important polymer
groupings.
The updating of analytical, physical, and special characterization techniques continues. The
coverage of a number of topics has been increased, including carbon nanotubes, tapes and glues,
butyl rubber, polystyrene, polypropylene, polyethylene, poly(ethylene glycols), shear-thickening
fluids, photochemistry and photophysics, dental materials, and aramids. Expanded sections on a
number of copolymers have been added, including fluoroelastomers, nitrile rubbers, acrylonitrile–
butadiene–styrene terpolymers, and EPDM rubber. New units on spliceosomes, asphalt, and flyash
and aluminosilicates have been included. The emphasis on the molecular behavior of materials,
that is, nanoscale behavior, has been expanded as has been the emphasis on nanotechnology and
nanomaterials. PowerPoint presentations, instructor materials, and test banks will be hosted on a
companion website. Visit the book’s CRC Press website for further details: http://www.crcpress.
com/9781498737388. Advanced material to accompany this textbook can be found on the CRC
Press Website at http://www.crcpress.com/9781498737388.
Acknowledgments
The author gratefully acknowledges the contributions and assistance of the following in prepar-
ing this book: John Droske, Eli Pearce, Charles Pittman, Edward Kresge, Gerry Kirshenbaum,
Sukumar Maiti, Alan MacDiarmid, Les Sperling, Eckhard Hellmuth, Mike Jaffe, Otto Vogel,
Thomas Miranda, Murry Morello, and Graham Allan; and a number of our children who assisted
in giving suggestions for the text—Charles Carraher III, Shawn Carraher, Colleen Carraher,
Erin Carraher, and Cara Carraher—Erin for discussions on materials, Cara for her help with the
biomedical material, and Shawn for his help in relating the business and industrial aspects. Special
thanks to Gerry Kirshenbaum for his kind permission to utilize portions of articles by me that
appeared in Polymer News. This book could not have been written if not for those who have gone
before us, especially Raymond Seymour, Herman Mark, Charles Gebelein, Paul Flory, and Linus
Pauling; all of these friends shepherded and helped me. My thanks to them. I especially thank my
editor Barbara Knox for her encouragement and guidance through these many volumes we have
published together. We have traveled many miles together, and they have been good and fruitful
miles.
I thank my wife Mary Carraher for her help in proofing and allowing this edition to be written. I
thank my researchers and others for their help in proofing—Jessica Frank, Paul Slawek, Francesca
Mosca, Jeffrey Einkauf, Dhruvin Patel, Elaine Quiles, Zachary M. Rabinowitz, Natalie Ezzell,
Kendra Black, Ryan Crichton, and Elohise St-Fort. And I thank some of my grandchildren for
their help in proofing—John Carraher, Lydia Gunter, Paul Gunter, Timothy Carraher, Caleb Kvale,
Abigail Kvale, Isaac Kvale, Herman Gunter V, Shawn Carraher, Jr., Charles Carraher IV, Elizabeth
Kvale, Christian Schwarz, Luke Schwarz, Grace Schwarz, Hannah Steinberg, and Rachel Steinberg.
Comments on Pictures: Other than pictures of several of the polymer pioneers taken from
Wikipedia, the pictures were taken by the author with the exception of the picture of the sheep
that was taken by Barbara Knott. The objects are intended, for the most part, to be items of general
familiarity to the reader, illustrating the prevalence of polymers in our everyday life. I thank Home
Depot (Coconut Creek, Florida) and Walmart (Coconut Creek, Florida) for allowing me to take
pictures. I also thank Cara Carraher and Erin Carraher for their help with directions as to how to
take better pictures.
xix
Author
Charles E. Carraher, Jr., is a professor of chemistry and biochemistry at Florida Atlantic University,
Boca Raton. He has been recognized as the Outstanding Chemist in Southeast USA (1992) by the
American Chemical Society (ACS) and is the recipient of a distinguished service award for his
efforts in science education (1995) from the ACS’s Divisions of Polymer Chemistry and Polymeric
Materials: Science and Engineering. He is a fellow of the American Institute of Chemists (1975),
Polymeric Materials (2006), Polymer Chemistry (2010), and the American Chemical Society
(2010). Currently, he serves as cochair of the ACS’s Joint Polymer Education Committee, is on the
board of the Intersocietal Polymer Education Committee, and has been a member of the ACS’s
Committee on Professional Training (CPT). He is an associate editor of the Journal of Polymeric
Materials and is on the board of the Journal of Inorganic and Organometallic Polymers and
Materials and the Journal of Chinese Advanced Materials Society. He has authored or coauthored
over 75 books and over 1100 articles and has chaired/cochaired numerous national and interna-
tional symposia. His research has led to the synthesis of over 85 new families of polymers. In 1984,
he received the Outstanding Scientist and Engineering Award from the Engineers and Scientists
Affiliate Societies Council for his work in science education and research, and in 1992, he received
the Saltarilli Sigma Xi Award for his research efforts. Dr. Carraher was the recipient of the 2002
Distinguished Researcher Award from Allied Technologies; award for Outstanding Contributions
in Polymer Chemistry from the Division of Polymer Chemistry in 2016; and award for Outstanding
Contributions in Polymeric Materials and Engineering from the Division of Polymeric Materials:
Science and Engineering in 2017.
xxi
1 Introduction to Polymers
1.1 HISTORY OF POLYMERS

Since most materials are polymeric and most of the recent advances in science and technology
involve polymers, some have called this the polymer age. Actually, we have always lived in a poly-
mer age. The ancient Greeks classified all matter as animal, vegetable, and mineral. Minerals were
emphasized by the alchemists, but medieval artisans emphasized animal and vegetable matter. All
three are largely polymeric and are important to life as we know it. Most chemists, biochemists, and
chemical engineers are now involved in some phases of polymer science or technology.
The word polymer is derived from the Greek poly and meros, meaning many and parts, respec-
tively. Some scientists prefer to use the word macromolecule, or large molecule, instead of polymer.
Others maintain that naturally occurring polymers, or biopolymers, and synthetic polymers should
be studied in different courses. Others name these large molecules as simply “giant molecules.”
However, the same principles apply to all polymers. If one discounts the end uses, the differences
between all polymers, including plastics, fibers, and elastomers or rubbers, are determined primar-
ily by the intermolecular and intramolecular forces between the molecules and within the individual
molecule, respectively, by the functional groups present, and most of all, by their size, allowing an
accumulation of these forces.
In addition to being the basis of life itself, protein is used as a source of amino acids and energy.
The ancients degraded or depolymerized the protein in meat by aging and cooking, and they dena-
tured egg albumin by heating or adding vinegar to the eggs. Early humans learned how to process,
dye, and weave the natural proteinaceous fibers of wool and silk and the carbohydrate fibers from
flax and cotton. Early South American civilizations, such as the Aztecs, used natural rubber (Hevea
brasiliensis) for making elastic articles and for waterproofing fabrics.
There has always been an abundance of natural fibers and elastomers but few plastics. Of course,
early humans employed a crude plastic art in tanning the protein in animal skins to make leather
and in heat-formed tortoise shells. They also used naturally occurring tars as caulking materials and
extracted shellac from the excrement of small coccid insects (Coccus lacca).
Until Wohler synthesized urea from inorganic compounds in 1828, there had been little progress
in organic chemistry since the alchemists emphasized the transmutation of base metals to gold and
believed in a vital force theory. Despite this essential breakthrough, significant progress was not
made in understanding the organic compounds until the 1850s when Kekule developed the pres-
ently accepted technique for writing structural formulas. However, polymer scientists displayed a
talent for making empirical discoveries before the science was developed.
The original connection between rubber and sulfur is often attributed to Nathaniel Hayward, an
American businessman and investor. He is reported to have dusted rubber with sulfur powder and
exposed the dusted rubber to sunlight as a way to remove the rubber’s stickiness. Hayward patented
his discovery. He turned over his discovery to Charles Goodyear, who transformed the connection
between sulfur and rubber into the rubber industry.
Charles Goodyear grew up in poverty. He was a Connecticut Yankee, born in 1800. He began
work in his father’s farm implement business. Later, he moved to Philadelphia where he opened a
retail hardware store that soon went bankrupt. Charles then turned to being an inventor. As a child,
he had noticed the magic material that had formed a rubber bottle. He visited the Roxbury India
Rubber Company to try and interest them in his efforts to improve the properties of rubber. They
assured him that there was no need to do so.
1
2 Carraher’s Polymer Chemistry
He started his experiments with a malodorous gum from South America in debtor’s prison. In a
small cottage on the grounds of the prison, he blended the gum, the raw rubber called hevea rubber,
with anything he could find—ink, soup, castor oil, etc. While rubber-based products were available,
they were either sticky or became sticky in the summer’s heat. He found that treatment of the raw
rubber with nitric acid allowed the material to resist heat and not to adhere to itself. This success
attracted backers who helped form a rubber company. After some effort, he obtained a contract to
supply the U.S. Post Office with 150 rubber mailbags. He made the bags and stored them in a hot
room while he and his family were away. When they returned, they found the bags in a corner of the
room, joined together as a single mass. The nitric acid treatment was sufficient to prevent surface
stickiness, but the internal rubber remained tacky and susceptible to heat.
While doing experiments in 1839 at a Massachusetts rubber factory, Charles accidentally
dropped a lump of rubber mixed with sulfur on the hot stove. The rubber did not melt, but rather
charred. He had discovered vulcanization, the secret that was to make rubber a commercial suc-
cess. Despite this progress, it would take several years of ongoing experimentation before the
process was really commercially useful. During this time, he and his family were nearly penni-
less. While he patented the process, the process was too easily copied and pirated so that he was
not able to fully profit from his invention and years of hard work. Even so, he was able to develop
a number of items.
Charles Goodyear, and his brother Nelson, transformed natural rubber, hevea rubber, from a
heat-“softenable” thermoplastic to a less heat-sensitive product through the creation of crosslinks
between the individual polyisoprene chain-like molecules using sulfur as the crosslinking agent.
Thermoplastics are two-dimensional molecules that may be softened by heat. Thermosets are mate-
rials that are three-dimensional networks that cannot be reshaped by heating. Rather than melting,
thermosets degrade. As the amount of sulfur was increased, the rubber became harder, becoming a
hard rubber-like (ebonite) material.
The spring of 1851 found the construction of a remarkable building on the lawns of London’s
Hyde Park. The building was designed by a maker of greenhouses, so it was not unexpected that it
had a “greenhouse look.” This Crystal Palace was to house almost 14,000 exhibitors from all over
the world. It was the chance for exhibitors to show their wares. Charles Goodyear, then 50 years old,
used this opportunity to show off his over two decades’ worth of rubber-related products. He deco-
rated his Vulcanite Court with rubber walls, roof, furniture, buttons, toys, carpet, combs, etc. Above
it hung a giant six-foot rubber raft and assorted balloons. The European public was introduced to the
world of new man-made materials.
Within a little more than a decade, Charles Goodyear was dead. Within a year of his death, the
American Civil War broke out. The Union military used about $27 million worth of rubber products
by 1865, helping launch the American rubber industry.
In 1862, Queen Victoria, while in mourning for her recently departed husband Albert, opened a
world’s fair in London. One of the exhibitors was Alexander Parks. He was displeased with the lim-
ited colors available for rubber products—generally dull and dark. In his workshop in Birmingham,
England, he was working with nitrocellulose, a material made from the treatment of cotton and
nitric and sulfuric acids. Nitrocellulose solutions were made from dissolving nitrocellulose in
organic liquids such as ethanol and ether. Thin films and coatings were made by simply pouring
the nitrocellulose solutions onto the desired item or surface and allowing the solvent to evaporate.
He wanted to make solid objects from nitrocellulose. After years of work, he developed a material
he called Parkensine from which he made buttons, combs, and in fact many other of the items that
were often made of rubber—except that his materials could be brightly colored, clear, or made to
shine like mother-of-pearl. At the world’s fair in London, he advertised “PATENT PARKESINE of
various colours: hard elastic, transparent, opaque, and waterproof.” Even with all his work, he had
not developed a material that could be “worked” or was stable and even with his hype, the material
never caught on except within exhibition halls.
Introduction to Polymers 3
About this time, John Wesley Hyatt, a printer from Albany, New York, who was seeking a $10,000
prize for anyone who could come up with a material that was a substitute for ivory billiard balls,
developed a material that was stable and could be “worked” from shellac and wood pulp. He then
turned to nitrocellulose, discovering that shredded nitrocellulose could be mixed with camphor, and
heated under pressure, to produce a tough white mass that retained its shape. This material, dubbed
celluloid, could be made into the usual rubber-like products, and also solid pieces such as boxes,
wipe-clean linen, collars, cuffs, and ping-pong balls. Celluloid could also, like the shellac–wood
pulp mixture, be worked—cut, drilled, and sawed. But celluloid was flammable, and did not stand
up well in hot water. The wearers of celluloid dentures truly could have their “teeth curled” when
drinking a hot cup of coffee. One of its best qualities was that it could be made to “look like” other
materials—it could be dyed to look like marble, swirled to mimic tortoiseshell and mother-of-pearl,
and even look and feel like ivory. It did not make good billiard balls. One account has billiard balls
hitting and exploding like a shot that caused cowboys to draw their guns.
Both cellulose and cellulose nitrate are linear, or two-dimensional, polymers, but the former can-
not be softened because of the presence of multitudinous hydrogen bonds between the chain-like
molecules. When used as an explosive, the cellulose nitrate is essentially completely nitrated, but
the material used by Parks and Hyatt was a dinitrate, still potentially explosive, but less so. Parks
added castor oil and Hyatt added camphor to plasticize—reduce the effect of the hydrogen bond-
ing—the cellulose nitrate, allowing it some flexibility.
Worldwide, rubber gained importance with the invention of air-filled or pneumatic tires by a
Scotsman, John Dunlop, in 1888. He had a successful veterinarian practice in Belfast. In his off
time, he worked to improve the ride of his son’s tricycle. His invention happened at the right time.
The automobile was emerging and the air-filled tires offered a gentler ride. Thus began the tire
industry.
All of these inventions utilized natural material as at least one ingredient. After years of work
in his chemistry labs in Yonkers, New York, Leo Baekeland in 1907 announced in an American
Chemical Society meeting the synthesis of the first truly synthetic polymeric material, later dubbed
Bakelite.
Baekeland was born in Belgium in 1863, the son of an illiterate shoe repairman and a maid. He
was bright and received, with highest honors, his doctorate degree at the age of 20. He could have
spent the remaining part of his life in academics in Europe, but heeding the words of Benjamin
Franklin, he sailed to America. In the 1890s, he developed the first photographic paper, called
Velox, which could be developed in synthetic light rather than sunlight. George Eastman saw the
importance of this discovery and paid Bakeland $750,000 for the rights to use this invention.
Another issue was developing that would capture Baekeland’s attention. It was generally rec-
ognized by the leading organic chemists of the nineteenth century that phenol would condense
with formaldehyde. Since they did not recognize the concept of functionality, Baeyer, Michael, and
Kleeberg produced useless crosslinked goos, gunks, and messes and then returned to their research
on reactions of monofunctional reactants. However, by the use of a large excess of phenol, Smith,
Luft, and Blumer were able to obtain a hard but meltable thermoplastic material.
With his $750,000, Baekeland set up a lab next to his home. He then sought to solve the problem
of making the hard material made from phenol and formaldehyde soluble. After many failures, he
thought about circumventing the problem by placing the reactants in a mold of the desired shape
and allowing them to form the intractable solid material. After much effort, he found the conditions
under which a hard, clear solid could be made—Bakelite was discovered. Bakelite could be worked;
it was resistant to acids and organic liquids, stood up well to heat and electrical charge, and could be
dyed to give colorful products. It was used to make bowling balls, phonograph records, telephones
housings, gears, and cookware. His materials also made excellent billiard balls. Bakelite also acted
as a binder for sawdust, textiles, and paper, forming a wide range of composites, including Formica
laminates, many of which are still used today. It was also used as an adhesive, giving us plywood.
While there is no evidence that Baekeland recognized what polymers were, he appeared to have
a grasp on functionality and how to “use” it to produce thermoplastic materials that could later be
converted to thermosets. Through control of the ratio of phenol to formaldehyde, he was able to
form a material that was a thermoplastic. He coined the term A-stage resole resin to describe this
thermoplastic. This A-stage resole resin was converted to a thermoset crosslink, C-stage Bakelite,
by additional heating. Baekeland also prepared thermoplastic resins called novolacs by the conden-
sation of phenol with a lesser amount of formaldehyde under acidic conditions. The thermoplastic
novolacs were converted to thermosets by the addition of more formaldehyde. While other polymers
had been synthesized in the laboratory, Bakelite was the first truly synthetic plastic. The “recipes”
used today differ little from the ones developed by Baekeland, showing his ingenuity and knowledge
of the chemistry of the condensation of the trifunctional phenol and difunctional formaldehyde.
While poly(vinyl chloride) was initially formed by Baumann in 1872, it awaited interest until
1926 when B. F. Goodrich discovered how to make sheets and adhesives from poly(vinyl chlo-
ride)—and the “vinyl age” began. While polystyrene was probably first formed by Simon in 1839,
it was almost 100 years later, in 1930, that the giant German company I. G. Farben placed polysty-
rene on the market. Polystyrene-molded parts became commonplace. Rohm and Haas bought out
Plexiglass from a British firm in 1935 and began the production of clear plastic parts and goods,
including replacements for glass as camera lenses, aircraft windows, clock faces, and car tail lights.
Up to this time, polymer science was largely empirical, instinctive, and intuitive. Prior to World
War I, celluloid, shellac, Galalith (casein), Bakelite, and cellulose acetate plastics; hevea rubber, cot-
ton, wool, silk rayon fibers; Glyptal polyester coatings; bitumen or asphalt; and coumarone-indene
and petroleum resins were all commercially available. However, as evidenced by the chronological
data shown in Table 1.1, there was little additional development in polymers prior to World War
II because of a general lack of fundamental knowledge of polymers. But the theoretical basis was
being built. Only a few of many giants will be mentioned.
Over a century ago, Graham coined the term colloid for aggregates with dimensions in the range
of 10−9–10−7 m. Unfortunately, the size of many macromolecules is in this range, but it is important
to remember that unlike colloids, whose connective forces are ionic and/or secondary forces, poly-
mers are individual molecules whose size cannot be reduced without breaking the covalent bonds
that hold the atoms together. In 1860, an oligomer, a small polymer, was prepared from ethylene
glycol and its structure correctly given as H–(–OCH2CH2–)n–OH. But when poly(methacrylic acid)
was made by Fittig and Engelhorn in 1880, it was incorrectly assigned a cyclic structure. Polymers
were thought of as being colloids, or cyclic compounds such as cyclohexane. By the use of the
Raoult and van’t Hoff concepts, several scientists obtained high-molecular-weight values for these
materials and for a number of other polymeric materials. But since the idea of large molecules was
not yet accepted, they concluded that these techniques were not applicable to these molecules rather
than accepting the presence of giant molecules.
Much of the early progress with polymers occurred in industry. Before the mid-twentieth century,
European academic scientists held the notion that polymers were actually colloids. Many American
chemists studied in European universities before returning to the United States and were infected
with the inaccurate “colloid” idea. During this time, both the European and American industries
were pushing the knowledge, production, and discovery of polymers.
The initial “tire-track in the sand” with respect to tires was the discovery of vulcanization of rub-
ber by Charles Goodyear in 1844. The first rubber tires appeared in the mid-1880s. These tires were
solid rubber with the rubber itself absorbing the bumps and potholes. John Dunlop invented the
first practical pneumatic or inflatable tire with his patent granted in 1888. Andre Michelin was the
first person to use the pneumatic tire for automobiles. The Michelin brothers, Andre and Edouard,
equipped a racing car with pneumatic tires and drove it in the 1895 Paris–Bordeaux road race. They
did not win but it was sufficient advertising to begin interest in pneumatic tires for automobiles.
Further, because they did not cause as much damage to the roads, pneumatic tires were favored by
legislation. It is interesting to see that the names of these pioneers still figure prominently in the
Introduction to Polymers 5
TABLE 1.1
Chronological Developments of Commercial Polymers (to 1992)
Before 1800 Cotton, flax, wool, and silk fibers; bitumen caulking materials; glass and hydraulic cements; leather
and cellulose sheet (paper); natural rubber (Hevea brasiliensis), gutta percha, balata, and shellac
1839 Vulcanization of rubber (Charles Goodyear)
1845 Cellulose esters (Schonbein)
1846 Nitration of cellulose (Schonbein)
1851 Ebonite (hard rubber; Nelson Goodyear)
1860 Molding of shellac and gutta percha
1868 Celluloid (plasticized cellulose nitrate; Hyatt)
1888 Pneumatic tires (Dunlop)
1889 Cellulose nitrate photographic films (Reinchenbach)
1890 Cuprammonia rayon fibers (Despeisses)
1892 Viscose rayon fibers (Cross, Bevan, and Beadle)
1903 First tubeless tire (Litchfield of Goodyear Tire Co.)
1897 Poly(phenylene sulfide)
1901 Glyptal polyesters
1907 Phenol–formaldehyde resins (Bakelite; Baekeland)
1908 Cellulose acetate photographic fibers
1912 Regenerated cellulose sheet (cellophane)
1913 Poly(vinyl acetate)
1914 Simultaneous interpenetrating network (SIN)
1920 Urea–formaldehyde resins
1923 Cellulose nitrate automobile lacquers
1924 Cellulose acetate fibers
1926 Alkyd polyester (Kienle)
1927 Poly(vinyl chloride) wall covering
1927 Cellulose acetate sheet and rods
1927 Graft copolymers
1928 Nylon (Carothers, DuPont)
1929 Polysulfide synthetic elastomer (Thiokol; Patrick)
1929 Urea–formaldehyde resins
1930 Polyethylene (Friedrich/Marvel)
1931 Poly(methyl methacrylate) (PMMA) plastics
1931 Polychloroprene elastomer (Neoprene; Carothers)
1934 Epoxy resins (Schlack)
1935 Ethylcellulose
1936 Poly(vinyl acetate)
1936 Poly(vinyl butyral) (safety glass)
1937 Polystyrene
1937 Styrene–butadiene (Buna-S) and styrene–acrylonitrile (Buna-N) copolymer elastomers
1939 Melamine–formaldehyde resins
1939 Nylon 6 (Schlack)
1939 Nitrile rubber (NR)
1940 Isobutylene–isoprene elastomer (butyl rubber; Sparks and Thomas)
1941 Low-density polyethylene (LDPE)
1941 Poly(ethylene terephthalate) (PET)
1942 Butyl rubber
1942 Unsaturated polyesters (Ellis and Rust)
1943 Fluorocarbon resins (Teflon; Plunket)
(Continued)
TABLE 1.1 (Continued)

Chronological Developments of Commercial Polymers (to 1992)
1943 Silicones
1945 SBR
1946 Polysulfide rubber (Thiokol)
1948 Copolymers of acrylonitrile, butadiene, and styrene (ABS)
1949 Cyanoacrylate (Goodrich)
1950 Polyester fibers (Winfield & Dickson)
1950 Polyacrylonitrile fibers
1952 Block copolymers
1953 High-impact polystyrene (HIPS)
1953 Polycarbonates (Whinfield & Dickson)
1956 Poly(phenylene ether); poly(phenylene oxide) (GE)
1957 High-density polyethylene (HDPE)
1957 Polypropylene
1957 Polycarbonate
1958 Poly(dihydroxymethylcyclohexyl terephthalate) (Kodel, Eastman Kodak)
1960 Ethylene–propylene copolymer elastomers
1961 Aromatic nylons (Aramids, Nomex, DuPont)
1962 Polyimide resins
1964 Poly(phenylene oxide)
1964 Ionomers
1965 Polysulfone
1965 Styrene–butadiene block copolymers
1966 Liquid crystals
1970 Poly(butylene terephthalate)
1974 Polyacetylene
1982 Polyetherimide (GE)
1991 Carbon nanotubes (Iijima; NEC Lab)
2003 Carbon fiber (graphene)
tire industry. Even so, another inventor, Thompson, had actually been given the first patent for a
vulcanized rubber pneumatic tire in 1845 but it did not take off. Thompson was a prolific inventor,
having also patented a fountain pen in 1849 and a steam traction engine in 1867.
A number of the giant tire companies were started at the turn of the century. In America, many
of these companies centered around Akron Ohio, resulting in Akron becoming the rubber tire capi-
tal. In 1898, the Goodyear Tire and Rubber Company was started. The Firestone Tire and Rubber
Company was started by Harvey Firestone in 1900. Other tire companies followed shortly.
Hermann Staudinger (Picture 1.1) studied the polymerization of isoprene as early as 1910.
Intrigued by the difference between this synthetic material and natural rubber, he began to focus
more of his studies on such materials. His turn toward these questionable materials, of interest to
industry but surely not academically important, was viewed unkindly by his fellow academics. He
was told by one of his fellow scientists: “Dear Colleague, Leave the concept of large molecules well
alone … There can be no such thing as a macromolecule.”
Staudinger systematically synthesized a variety of polymers. In the paper “Uber Polymerization”
in 1920, he summarized his findings and correctly proposed linear structures for important poly-
mers such as polyoxymethylene and polystyrene. X-ray studies of many natural and synthetic mate-
rials were used as structural proof that polymers existed. Foremost in these efforts were Herman
Mark and Linus Pauling. Both of these giants contributed to other important areas of science.
Pauling contributed to the fundamental understanding of bonding and the importance of vitamins.
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fell and prepare timber, it was pretended that it was for pleasure-
boats wherewith to entertain him. Under the able direction of Martin
Lopez aided by Alonso Nuñez, the master carpenters, they were
completed within a few weeks, and provided with four guns and tiers
of oars, affording transport for three hundred men.
A hunting-trip to one of the imperial reserves across the lake was
at once arranged.[553] The largest vessel had been provided with
awnings and other comforts for the reception of Montezuma, his
suite, and a strong guard, while other notables were accommodated
in the other craft. A volley from the guns announced their arrival, and
did more probably to inspire respect than even the presence of
majesty. The vessels were accompanied by a fleet of canoes, some
holding forty or more courtiers, hunters, or attendants. All were
curious to see how the winged water-houses would behave, for their
immense size was supposed to render them slow and clumsy. A fair
breeze was blowing, however, and as the large sails unfurled, the
vessels bounded forward with a speed that in a few moments left the
occupants of the canoes far behind. Montezuma was delighted, and
the trip was repeated. Hunting parties were likewise formed; for the
royal captive enjoyed the chase and used the blow-pipe with great
skill.[554]
FOOTNOTES
[517] ‘Le dió en guarda á un capitan, é de noche é de dia siempre estaban
españoles en su presencia.’ Tapia, Rel., in Icazbalceta, Col. Doc., ii. 580. This
captain appears to have been Juan Velazquez, whose place was taken by Olid,
when required. Bernal Diaz, Hist. Verdad., 77, 86.
[518] ‘Se quiso echar de vna açutea de diez estados en alto, para que los suyos le
recibiessen, sino le detuuiera vn Castellano.... Denoche y de dia procurauan de
sacarle, oradando a cada passo las paredes, y echando fuego por las azuteas.’
The result was an increase of the guard, Álvarez Chico being placed with 60
men to watch the rear of the quarters, and Andrés de Monjarraz the front, with the
same number, each watch consisting of twenty men. Herrera, dec. ii. lib. viii. cap.
iii. Bernal Diaz intimates that the guarding of Montezuma proved a severe strain
on the soldiers; but, situated as they were, vigilance was ever required, and still
greater must have been the danger had he not been in their power.
[519] Herrera calls him Peña, which may have been one of his names, dec. ii. lib.
viii. cap. v. Bernal Diaz assumes that Montezuma asked Cortés to give him the
page, after the execution of Quauhpopoca. Hist. Verdad., 75.
[520] The bride was named Francisca. Hist. Verdad., 77. As an instance of
Montezuma’s eagerness to gratify the Spaniards, and at the same time to exhibit
his own power, it is related that one day a hawk pursued a pigeon to the very cot
in the palace, amid the plaudits of the soldiers. Among them was Francisco the
dandy, former maestresala to the admiral of Castile, who loudly expressed the
wish to obtain possession of the hawk and to tame him for falconry. Montezuma
heard him, and gave his hunters orders to catch it, which they did. Id.; Gomara,
Hist. Mex., 125.
[521] Duran states that the soldiers discovered a house filled with women,
supposed to be wives of Montezuma, and hidden to be out of the reach of the
white men. He assumes that gratitude would have made the Spaniards respect
them; or, if the women were nuns, that respect for virtue must have obtained.
[522] Cortés’ protégée being named Ana. Quite a number of the general’s
followers declare in their testimony against him, in 1528, that he assumed the
intimate protectorship of two or even three of Montezuma’s daughters, the second
being called Inés, or by others Isabel, the wife of Grado, and afterward of Gallego.
‘Tres fijas de Montezuma e que las dos dellas an parido del e la otra murio
preñada del quando se perdio esta cibdad.’ Tirado, in Cortés, Residencia, ii. 39,
241, 244; i. 63, 99, 221, 263. Intrigues are mentioned with other Indian princesses.
Vetancurt assumes that two noble maidens were given, one of whom Olid
received. Teatro Mex., pt. iii. 133; Torquemada, i. 462. Bernal Diaz supposes that
this is the first daughter offered by Montezuma, and he believes evidently that
Cortés accepts her, to judge by a later reference. Hist. Verdad., 85, 102.
[523] Herrera states that Cortés’ order was prompted by a consideration for the
heavy expense to Montezuma. The latter remonstrated at this economical fit, and
commanded that double rations should be provided for the exiled. dec. ii. lib. viii.
cap. iv.
[524] Tapia, Rel., in Icazbalceta, Col. Doc., ii. 580. ‘Purchè non tocchino disse il
Re, le immagini degli Dei, nè ciò che è destinato al loro culto, prendano quanto
vogliono,’ is Clavigero’s free interpretation of Ojeda’s version. Storia Mess., iii. 97;
Gomara, Hist. Mex., 125.
[525] ‘Lo q̄ vna vez daua no lo auia de tornar a recibir.’ ‘Las caxas donde la ropa
estaua, eran tan grandes que llegauan a las vigas de los aposentos, y tan anchas,
q̄ despues de vacias, se alojauã en cada vna dos Castellanos. Sacaron al patio
mas de mil cargas de ropa.’ Herrera, ii. viii. iv.
[526] ‘Casa de Cacao, de Motecuhçuma, adonde avia mas de quarenta mil

Cargas, que era Gran Riqueça, porque solia valer cada Carga quarenta
Castellanos.’ Alvarado alone emptied six jars of 600 loads. Torquemada, i. 472.
[527] The man had insisted that Montezuma should have a search made for two of
his missing female attendants. The emperor did not wish Spaniards punished for
pilfering, as he told Cortés, only for offering insult and violence. In such cases he
would have his own courtiers lashed. Herrera, dec. ii. lib. viii. cap. v.
[528] ‘Tinie el marques tan recogida su gente, que ninguno salie un tiro de
arcabuz del aposento sin licencia, é asimismo la gente tan en paz, que se
averiguó nunca reñir uno con otro.’ Tapia, Rel., in Icazbalceta, Col. Doc., ii. 586.
[529] Bernal Diaz, Hist Verdad., 77. ‘Un giuoco, che gli Spagnuoli chiamavano il
bodoque.’ Clavigero, Storia Mess., iii. 97. Bodoque signifies balls in this
connection. When Alvarado lost, he with great show of liberality paid in
chalchiuites, stones which were highly treasured by the natives, but worth nothing
to the Spaniards. Montezuma paid in quoits, worth at least 50 ducats. One day he
lost 40 or 50 quoits, and with pleasure, since it gave him the opportunity to be
generous. B. V. de Tapia testifies that Alvarado used to cheat in playing cards with
him and others. Cortés, Residencia, i. 51-2. Another way of gratifying this bent
was to accept trifles from the Spaniards and liberally compensate them. Alonso de
Ojeda, for instance, had a silk-embroidered satchel with many pockets, for which
Montezuma gave him two pretty slaves, beside a number of robes and jewels.
Ojeda wrote a memoir on the conquest, of which Herrera makes good use. dec. ii.
lib. viii. cap. v.
[530] ‘Fué muchas veces á holgar con cinco ó seis españoles á una y dos leguas
fuera de la ciudad.’ Cortés, Cartas, 92. Both the times and the number of the
Spaniards are doubtful, however. ‘Quando salia a caçar.... Lleuaua ocho o diez
Españoles en guarda de la persona, y tres mil Mexicanos entre señores,
caualleros, criados, y caçadores.’ Gomara, Hist. Mex., 124; Ixtlilxochitl, Hist.
Chich., 297.
[531] Bernal Diaz intimates that more sacrifices were made in their presence. ‘Y
no podiamos en aquella sazon hazer otra cosa sino dissimular con èl.’ Hist.
Verdad., 78.
[532] Bernal Diaz admits that he knows not what occurred between governor and
monarch, but Herrera claims to be better informed. Barefooted, and with eyes
upon the floor, Quauhpopoca approached the throne and said: ‘Most great and
most powerful lord, thy slave Quauhpopoca has come at thy bidding, and awaits
thy orders.’ He had done wrong, was the reply, to kill the Spaniards, and then
declare that he had orders so to do. For this he should suffer as a traitor to his
sovereign and to the strangers. He was not allowed to make any explanations,
dec. ii. lib. viii. cap. ix. It is not unlikely that Montezuma commanded him not to
reveal anything that might implicate his master, hoping that Cortés would out of
regard for his generous host inflict a comparatively light punishment.
[533] ‘Examinaron los segunda vez, con mas rigor, y amenazas de tormento, y sin
discrepar todos confessaron,’ says Herrera, loc. cit.
[534] ‘En vna de las casas reales dicha Tlacochalco.’ Herrera, loc. cit. ‘É serien
mas que quinientas carretadas.’ Tapia, Rel., in Icazbalceta, Col. Doc., ii. 584.
[535] ‘Me has negado no auer mãdado a Couatlpopocà q̄ matasse a mis

compañeros, no lo has hecho como tan gran señor que eres, ... porque no quedes
sin algun castigo, y tu y los tuyos sepays quanto vale el tratar verdad, te mãdare
echar prisiones.’ Herrera implies with this that Cortés laid more weight on the
disregard for truth than on the authorization of the outrage. dec. ii. lib. viii. cap. ix.
‘Que ya que aquella culpa tuuiesse, que antes la pagaria el Cortès por su
persona, que versela passar al Monteçuma.’ Bernal Diaz, Hist. Verdad., 75.
[536] ‘Esto hizo por ocuparle el pensamiento en sus duelos, y dexasse los ajenos.’
Gomara, Hist. Mex., 129. ‘Todo à fin de espantarle mas.’ Ixtlilxochitl, Hist. Chich.,
298.
[537] Solis seems to say that the bodies were burned after execution, Hist. Mex., i.
461-2, but Cortés and others are frank enough about the actual burning, which
was not regarded in that cruel age with the same aversion as by us. Instances are
to be found in the Native Races, ii.-iii., where this ordeal was undergone by
criminals as well as temple victims among the Aztecs. Bernal Diaz gives the
names of two of Quauhpopoca’s companions in misfortune, Quiabuitle and Coatl.
Hist. Verdad., 75. Prescott, Mex., ii. 173, states that the execution took place in
the court-yard; but this is probably a misprint, to judge by his own text.
[538] ‘Á lo que entendimos, ê lo mas cierto, Cortés auia dicho á Aguilar la lengua,
que le dixesse de secreto, que aunque Malinche le mandasse salir de la prision,
que los Capitanes nuestros, è soldados no querriamos.’ Bernal Diaz, Hist.
Verdad., 75.
[539] ‘Fué tanto el buen tratamiento que yo le hice, y el contentamiento que de mí
tenia, que algunas veces y muchas le acometi con su libertad, rogándole que
fuese á su casa, y me dijo todas las veces que se lo decia, que él estaba bien allí,’
etc. Cortés, Cartas, 91. ‘No osaua, de miedo que los suyos no le matassen ... por
auerse dexado prender,’ is one of the suppositions of Gomara, who calls him a
man of little heart. Hist. Mex., 129-30. Peter Martyr appears to be moved rather by
pity for him. dec. v. cap. iii. ‘Non gli conveniva ritornare al suo palagio, mentre
fossero nella Corte gli Spagnuoli.’ Clavigero, Storia Mess., iii. 102.
[540] ‘Como este castigo se supo en todas las Prouincias de la Nueua-España,

temieron, y los pueblos de la costa, adonde mataron nuestros soldados, bolvieron
á servir.’ Bernal Diaz, Hist. Verdad., 75-6, comments upon the daring of the
Spaniards in carrying out these and similar high-handed acts. For a short time
after this, says Herrera, the soldiers were ordered to sleep on their arms, in case
of any demonstration. dec. ii. lib. viii. cap. ix. Clavigero regards the burning as
unjustifiable, since the emperor was regarded as having authorized it. If he was
not guilty, the Spaniards were ungrateful to treat him as they did. Storia Mess., iii.
101. Robertson finds some excuse for Quauhpopoca’s punishment, but calls the
humiliation of Montezuma a wanton display of power. Hist. Am., ii. 63, 453-4.
Prescott, on the other hand, regards the humiliation as politic, on the ground that
by rendering the monarch contemptible in the eyes of his subjects, he was obliged
to rely more on the Spaniards. Mex., ii. 177. But this would hardly have been
necessary since he was in their power, and considering that the object of keeping
him so was to control the country, it would have been better not to degrade him.
[541] ‘Donde mas oro se solia traer, que era de vna Provincia que se dize,
Zacatula ... de otra Provincia, que se dize Gustepeque, cerca de donde
desembarcamos ... é que cerca de aquella Provincia ay otras buenas minas, en
parte que no son sujetos, que se dizen, los Chinatecas, y Capotecas.’ Bernal
Diaz, Hist. Verdad., 81. Montezuma detailed two persons for each of four
provinces where gold was to be had, and Cortés gave two Spaniards for each
couple. The provinces named were Cuzula, Tamazulapa, Malinaltepeque, Tenis.
Cortés, Cartas, 92-3. Of the eight Indians, four were miners or goldsmiths, and the
others guides. Gomara, Hist. Mex., 130. Chimalpain names the provinces:
Tamazólan, in upper Miztecapan, Malinaltepec and Tenich, both on the same river,
and Tututepec, twelve leagues farther, in the Xicayan country. Hist. Conq., i. 254-
5.
[542] ‘Con tal, que los de Culùa no entrassen en su tierra.’ They were reassured
and dismissed with presents. Herrera, dec. ii. lib. ix. cap. i.
[543] ‘Cortés se holgô tanto con el oro como si fueran treinta mil pesos, en saber
cierto que avia buenas minas.’ Bernal Diaz intimates beside that Umbría and his
two companions had provided themselves with plenty of gold. Hist. Verdad., 81-2.
[544] A young man of 25 years, whom Cortés treated as a relative. With him went
four Spaniards who understood mining, and four chiefs. Id.
[545] ‘En granos crespillos, porque dixeron los mineros, que aquello era de mas
duraderas minas como de nacimiento.’ Id., 82.
[546] Bernal Diaz names them, ‘Barriẽtos, y Heredia el viejo, y Escalona el moço,
y Cervantes el chocarrero,’ and says that Cortés, displeased at soldiers being left
to raise fowl and cacao, sent Alonso Luis to recall them. Hist. Verdad., 82;
Herrera, dec. ii. lib. ix. cap. i. He is evidently mistaken, as shown by his own later
text, for Cortés himself states that he sought to form plantations in that direction.
The recall was made later and for a different reason.
[547] ‘Estaban sembradas sesenta hanegas de maíz y diez de frijoles, y dos mil
piés de cacap [cacao] ... hicieron un estanque de agua, y en él pusieron
quinientos patos ... y pusieron hasta mil y quinientas gallinas.’ Cortés, Cartas, 94;
Peter Martyr, dec. v. cap. iii. Oviedo writes that farms were established for the king
in two or three provinces, one in Chimanta [Chimantla]. The two Spaniards left in
the latter were saved, but elsewhere, subject to the Aztecs, they were killed during
the uprising originated by Alvarado. iii. 376. Tapia refers to an expedition at this
time against a revolted province, 80 leagues off. Rel., in Icazbalceta, Col. Doc., ii.
584.
[548] ‘Por aquella causa llaman oy en dia, donde aquella guerra passò,
Cuilonemiqui.’ Bernal Diaz, Hist. Verdad., 82.
[549] Herrera, loc. cit. ‘Creyan lo que desseauan,’ remarks Gomara, Hist. Mex.,
131.
[550] Cortés, Cartas, 95, 116; Gomara, Hist. Mex., 131-2. Bernal Diaz throws
doubt on the expedition of Velazquez, but is evidently forgetful. Hist. Verdad., 81-
2. ‘El señor de la provinçia ... luego hiço seys [casas] en el assiento é parte que
para el pueblo se señaló.’ Oviedo, iii. 293. Peter Martyr calls these buildings
‘Tributaries’ houses.’ dec. v. cap. iii.; Cortés, Residencia, ii. 6, 49.
[551] He had served as equerry in the noble houses of the Conde de Ureña and
Pedro Giron, of whose affairs he was always prating. His propensity for tale-telling
lost him many friends, but he managed to keep intimate with Sandoval, whose
favors he afterward repaid with ingratitude. Bernal Diaz, Hist. Verdad., 76, 246.
Gomara insists on naming him as the comandante, but this dignity he attained
only after Sandoval and Rangel had held it. Cortés, Residencia, i. 256;
Torquemada, i. 456.
[552] ‘Luego que entré en la dicha ciudad di mucha priesa á facer cuatro
bergantines ... tales que podian echar trecientos hombres en la tierra y llevar los
caballos.’ Cortés, Cartas, 103; Peter Martyr, dec. v. cap. iv. ‘Quatro fustas.’
Gomara, Hist. Mex., 146. ‘Dos vergantines.’ Bernal Diaz, Hist. Verdad., 76. The
cedars of Tacuba, numerous enough at this period, yielded much of the timber,
and the slopes of Iztaccihuatl and Telapon the harder portion for masts, keels, etc.
Mora, in Soc. Mex. Geog., Boletin, ix. 301.
[553] ‘En la laguna á vn peñol, que estaua acotado, q̄ no ossauan entrar en èl á

montear, por muy principales que fuessen, so pena de muerte.’ Bernal Diaz, Hist.
Verdad., 78.
[554] Native Races, ii. 411. ‘Qãdo yua a caça de monteria, le lleuauan en ombros,
con las guardas de Castellanos, y tres mil Indios Tlascaltecas.... Acompañauanle
los señores sus vassallos.’ Herrera, dec. ii. lib. viii. cap. iv.
CHAPTER XIX.
POLITICS AND RELIGION.
1520.
Growing Discontent among the Mexicans—Cacama’s Conspiracy—He

openly Defies both Montezuma and Cortés—The Council of Tepetzinco
—Seizure of Cacama—The Tezcucan Ruler Deposed—Cuicuitzcatl
Elevated—Montezuma and his People Swear Fealty to the Spanish King
—Gathering in the Tribute—Division of Spoils—The Spaniards Quarrel
over their Gold—Uncontrollable Religious Zeal—Taking of the
Temple—Wrath of the Mexicans.
With their hand so securely on the spring that moved a mighty

empire, there is little wonder that these Spanish adventurers became
somewhat insolent toward the people they so injured. The Mexicans
were not slow to mark this, and there were those among them, and
others beside them, who began to think of taking matters into their
own hands, of destroying the invaders and releasing the emperor.
Montezuma’s occasional appearance in public, and the assertion
that he remained with the Spaniards of his free-will, and because the
gods desired it, had for a time satisfied the nobles; but the hard irons
on his limbs and the cruel burning of patriotic men had opened their
eyes somewhat to the true state of affairs. No one knew when his
turn might come. Life was insecure enough subject to the caprice of
their own sovereign, but the dark uncertain ways of these emissaries
of evil were past finding out. These things were thought of and talked
of in high places. Race aversions and the political systems of the
tripartite alliance caused more than one party to be formed, each
with aspirations that could not be entertained by the others. The
most prominent leader at this time was Cacama, who had at first
favored the strangers in their character as envoys. And now he
began the endeavor to direct the movement of the Aztec nobility, but
jealousy of Acolhua influence rose uppermost, and his efforts tended
only to create a reaction in favor of abiding by the will of the emperor.
[555]
Although there were enough of sympathizers in Mexico for his

purpose, Cacama found that he must rely almost wholly on the
northern provinces, and in connection with Cuitlahuatzin,
Totoquihuatzin II. of Tlacopan, his own brothers, and others, he
organized a conspiracy which had for its aim the expulsion of the
Spaniards and the release of his uncle. Beneath this was harbored a
design upon the Aztec throne, which would probably become vacant;
and even if Cacama was not sure of gaining this for himself, he had
at least the expectation of assuming the leadership of the Anáhuac
confederacy.[556] He presented to the council in the most dismal
aspect the purposes of the Spaniards, who evidently sought to
become absolute masters and reduce them all to slavery. It was time
to rise for religion and liberty. Their honor and welfare demanded it,
and this before the Spaniards rendered themselves too powerful by
reinforcements and alliances. With heedless confidence he vaunted
that Mexico should be his within a few hours after setting out against
her, for there were many of her citizens ready to aid in such a work.
The Spaniards were overrated, and could effect little, surrounded as
they were on all sides, and without other supplies than those
provided by the Mexicans.
The motives and the necessity were recognized, though the
means proposed met with some objections; but when the question of
spoils and rewards came forward there were still greater differences.
Among others, the brave and powerful lord of Matlaltzinco advanced
pretensions, founded in part on his close relationship to Montezuma,
which Cacama above all could not admit. The result was
disagreement, followed by the withdrawal of several members.[557]
No attempt had been made to keep the movement, or its
ostensible motive, a secret from Montezuma, nor could it have been
kept from him who was the still powerful ruler of a servile race; but,
even if the deeper lying aim was not revealed him, he could not fail
to foresee the troubles that might arise, particularly under such a
leader. He still hoped the Spaniards would soon leave, or that his
release might be effected by other means, for he dreaded a conflict
with the powerful invaders, involving perhaps the destruction of the
city and his own death. He sent to tell the conspirators that they
need not concern themselves about his imprisonment. The
Spaniards had more than once proposed that he should return to his
own palace, but the gods had decreed it otherwise. He could not
allow his people to be needlessly exposed to war, or his capital to
destruction. Remember Cholula. Their stay would not be long.
This message was not without its effect even among the
Tezcucans, for, although the fate of the Aztec capital and king may
have concerned them but little, there were many who could not
forget that the impetuous and proud Cacama had obtained the
throne by favor of Montezuma, to the prejudice of an elder brother,
Tetlahuehuetquizitzin.Their father, Nezahualpilli, had died in 1515,
without naming a successor, and the choice devolving on the royal
council, in conjunction with the rulers of Mexico and Tlacopan,
Cacama was elected. Cohuanacoch, the third brother, acquiesced,
but the youngest, the fiery Ixtlilxochitl, protested in favor of the eldest
heir, and denounced the selection as due to Montezuma, who hoped
to mould the new king to his own will and so again to control. He
even resorted to arms in support of his views, and enlisting the
northern provinces in his favor, after a short campaign he obliged
Cacama to consent to a division of the kingdom with himself.[558]
His ready success proved that Cacama had no very great hold
on the people, and now, when came the warning of Montezuma,
more than one chief counselled prudence from other motives than
fear. But the king stamped all these objections as cowardly, and
appears even to have placed under restraint several of those whose
want of sympathy he had reason to suspect.[559] His blood was hot,
and relying on the promises of his supporters, he considered himself
strong enough to bid defiance to his opponents. He sent word to his
uncle that if he had any regard for the dignity of his station and the
honor of his person and ancestry, he would not quietly submit to the
bondage imposed by a handful of robbers, who with smooth tongue
sought to cover their outrages against him and the gods. If he
refused to rise in defence of his religion, throne, and liberty, Cacama
would not.[560]
This outspoken utterance of the nephew whom he had assisted
to rulership amazed Montezuma as much as it wounded his pride,
and he no longer hesitated to take counsel with Cortés, who had
already obtained an inkling that something was stirring.[561] With
characteristic promptness the latter suggested that, since Cacama’s
real object was evidently to usurp the throne, a Mexican army should
be given to aid the Spaniards in laying waste the territory of the
conspirators and in capturing them. The emperor had probably
entertained a hope that the news would frighten his guest and make
it safe to urge a retreat from Mexico, thus ending the whole trouble.
He was therefore somewhat startled by this proposal, the true tenor
of which he well understood. He feared a fratricidal war of doubtful
result, wherein he would appear as arrayed against the defenders of
national religion and liberty; and being now weak and cowed he
hesitated to arm at all, preferring peaceful measures. To this Cortés
was not averse, for he recognized on second thought that
aggressive steps might become the signal for a general uprising
which would overwhelm him, since Aztec troops could never be
relied on.
He accordingly sent messages to Cacama, reminding him of
their friendly intercourse, and representing the danger of offending
the Spanish king by proceedings which could only react on himself
and lead to the destruction of his kingdom. Montezuma supported
this by asking the king to come to Mexico and arrange the difficulty.
Cacama had not gone so far to be restrained by what he termed an
empty threat, and regardless of the warnings from a timid minority he
replied that he knew not the king of the Spaniards, and would never
accept the friendship of men who had oppressed his country and
outraged his blood and religion. He had had enough of their
promises, but would declare his determination when he saw them.
[562] To Montezuma he sent word that he would come, “not with the
hand on the heart, however, but on the sword.”[563]
There was considerable meaning in this threat, for Cacama had
with great energy set about to mass his forces at Oztoticpac, and
they in conjunction with those of his allies would make a formidable
host.[564] Cortés was aware of this, and seeing that no time was to
be lost he firmly represented to Montezuma the necessity of securing
the person of the king, openly or by stealth; and when he still
hesitated, the significant hint was given that the Spaniards would
regard a refusal with suspicion. This decided him, and he promised
that it should be done, if possible. Cortés broke forth in expressions
of good-will, and again offered him that freedom which Montezuma
well knew he would never grant.
In placing Cacama on the throne, the emperor had seized the
opportunity to introduce into the Acolhua government offices several
creatures of his own, who were paid to maintain Aztec influence in
the council[565] and to watch operations. To these men he sent an
order, weighted with presents, to seize the king and bring him to
Mexico.[566] They accordingly prevailed on their victim to hold a
council at Tepetzinco for finally arranging the campaign. This palace
was situated on the lake, near Tezcuco, and approached by canals.
Here Cacama was seized and thrown into a boat prepared for the
occasion, and carried to the Aztec capital.[567]
Ashamed, perhaps, of his share in the transaction, and unwilling
to face the taunts of the captive, Montezuma refused to see him, and
he was surrendered to Cortés, who, regardless of royalty, applied the
fetters as the surest means against escape.[568] This seizure
scattered the conspirators and their schemes to the winds, and the
demoralization was completed by the arrest of several of the more
important personages, such as the king of Tlacopan and the lords of
Iztapalapan and Coyuhuacan, who were also shackled.[569] Thus we
see that Montezuma’s captivity did not greatly affect his power, since
he could so readily place under restraint the confederate kings, in
their own provinces; and it was not wholly unwelcome to him to find
his misfortune shared by other prominent men, since this made his
disgrace less conspicuous.
He now resolved, with the approval of Cortés, to depose the
Tezcucan ruler, as a rebel against his authority, and to place on the
throne a more dutiful subject, a younger natural brother of Cacama,
named Cuicuetzcatl,[570] whom his ill-treatment had driven to Mexico
for protection. The nomination was for the sake of appearance
submitted for ratification to a convention of loyal Tezcucan chiefs,
many of whom hoped no doubt to obtain greater influence under this
youth. The new king was escorted to the gates of Mexico by Cortés
and Montezuma, and received at Tezcuco with triumphal arches and
processions.[571]
And now, with the three confederate rulers and a number of
leading caciques in his power, the great king-maker thought the time
had come to exact a formal acknowledgment of Spanish sovereignty.
He reminded Montezuma of his promises to pay tribute, and
demanded that he and his vassals should tender allegiance. Instead
of the objections expected, Cortés was surprised to hear a prompt
acquiescence. Montezuma had evidently been long prepared for the
demand, and said that he would at once convene his chiefs for
consultation. Within little more than a week the summoned
dignitaries had arrived, and at a meeting, attended by no Spaniards
save the page, he intimated to the leading personages, so far as he
dared before this witness, that the concession demanded of them
was to satisfy the importunate jailers. “The gods, alas! are mute,”
concluded Montezuma; “but by and by they may signify their will
more clearly, and I will then say what further is to be done.”[572] All
declared sorrowfully that they would do as he bade, and Cortés was
informed that on the following day the required ceremony would take
place.
On this occasion the chiefs mustered in force before
Montezuma, who was seated on a throne having on either side the
new king of Tezcuco and he of Tlacopan.[573] All being prepared, the
Spanish general entered with his captains and a number of soldiers.
The emperor now addressed his vassals, reminding them of the
relation so long and happily maintained between them—as dutiful
subjects on the one side, and a line of loving monarchs on the other.
Comparing the Quetzalcoatl myth and other indications with the
advent of white men from the region of the rising sun, he showed
that they must be the long expected race, sent to claim allegiance for
their king, to whom the sovereignty evidently belonged. The gods
had willed it that their generation should repair the omission of their
ancestors. “Hence I pray that as you have hitherto held and obeyed
me as your lord, so you will henceforth hold and obey this great king,
for he is your legitimate ruler, and in his place accept this captain of
his. All the tribute and service hitherto tendered me give to him, for I
also have to contribute and serve with all that he may require. In
doing this you will fulfil not only your duty, but give me great
pleasure.”[574]
His concluding words were almost lost in the sobs which his
humiliated soul could no longer stifle. The chiefs were equally
affected, and the sympathies even of the flint-hearted Spaniards
were aroused to a degree which moistened many an eye. With some
of the lately arrived dignitaries, who had not had time to fully grasp
the situation at the capital, indignation struggled with grief at the
dismal prospect. Others recalled the prophecy that the empire would
terminate with Montezuma, whose very name appeared fraught with
evil omen,[575] and were quite reconciled to the inevitable. So were
most of them, for that matter, either through belief in the myth or from
a sense of duty to their master. One of the eldest nobles broke the
oppressive silence by declaring his sorrow at witnessing the grief of
their beloved sovereign and hearing the announcement of coming
changes. But since the time had come for the fulfilment of divine
decrees, they, as devout and dutiful subjects, could only submit.
Again their grief broke forth, though many a bitter glance was called
up by the allusion to changes in store for them. Observing the bad
impression, Cortés hastened to assure them that Montezuma would
not only remain the great emperor he had always been, and his
vassals be confirmed in their dignities and possessions, but that their
domain and power would be increased. The changes proposed were
merely intended to stop wars, to enlighten them on matters with
which they were as yet unacquainted, and to promote general
welfare. One after another, beginning with Montezuma, they now
swore allegiance, and gave promise of service and tribute, after
which they were dismissed with thanks for their compliance.[576]
The submission of the sovereigns appears to have been quietly
accepted throughout the country, and the impunity with which even
single Spaniards moved about shows that no hostility had been
aroused by the act, in the provinces at least. Evidently the people
hovered between fear of men who so few in number could yet
perform so great achievements, and awe of divine will as indicated
by the prophecies and traditions. Cortés was not slow in making use
of his new power by representing to the emperor that, his king being
in need of gold for certain projects, it would be well for the new
vassals to begin tribute payments as an earnest of their loyalty.
Montezuma had expected this, and it was readily agreed that he
should send officers, accompanied by Spaniards, to the different
provinces and towns of the empire for contributions.[577] These
demands were met with more or less alacrity, and in poured gold and
silver, in dust, and quoits, and leaves, and trinkets, which formed to a
certain extent a medium for trade. Many towns remote from the
mines had nothing to offer save a few jewels, which were perhaps
heirlooms among the chiefs.[578]
When the collectors returned, Montezuma summoned the
Spanish leaders, and surrendered what they had brought. In addition
to this, he offered them the treasures kept in his own palace,
regretting that he had not more to give; but previous offerings had
diminished what he possessed. “When you transmit it to your king,”
he said, “tell him that it comes from his good vassal, Montezuma.”
He requested that certain fine chalchiuite stones, each valued at two
loads of gold, and some finely chased and inlaid blow-pipes, should
be given to the king alone.[579] This liberality evoked the most
profound protestations of gratitude, as may be supposed, for they
had not expected so great an addition to the glittering heaps already
in their possession. Tapia and another officer were despatched in all
haste with the imperial mayordomo to receive the treasure. It was
stored in a hall and two smaller chambers of the aviary building,[580]
and consisted of gold, silver, and precious stones, in setting and in
separate form, with feathers, robes, and other articles, all of which
were transferred to the Spanish quarters.[581]
These valuables, together with the collections from the provinces
and the previously surrendered treasures of Axayacatl, were given to
Cortés, who placed them in charge of the treasurer, Gonzalo Mejía,
and the contador, Alonso de Ávila. The famed smiths of Azcapuzalco
were called in to separate the gold and silver settings from the jewels
of less delicacy and beauty, which it had been determined to melt.
This took about three days. They were then melted into bars, three
fingers in breadth, and stamped with the royal arms.[582] Iron weights
were made of one arroba and downward, not very exact, it seems,
yet suitable for the purpose, and with these the value of the melted
gold was found to be somewhat over 162,000 pesos de oro,
according to Cortés’ statement; the silver weighed over 500 marcos,
and the unbroken jewels and other effects were estimated at over
500,000 ducats, not counting the workmanship.[583] The jewels were
set with feathers, pearls, and precious stones, fashioned chiefly in
animal forms, “so perfect as to appear natural.” A number of trinkets
for the royal share had also been fashioned by the goldsmiths after
designs by the Spaniards, such as saintly images, crucifixes,
bracelets, and chains, all made with wonderful fidelity to originals.
The silver for the same share was made into plates, spoons, and
similar articles. The feathers presented a brilliant variety of colors
and forms, and the cotton, some of the most delicate texture and
color, was both plain and embroidered, and made into robes,
tapestry, covers, and other articles. Turquoises, pearls, toys, and
trinkets were also among the treasures.[584]
Cortés proposed to defer the distribution till more gold and better
weights were obtained; but the men, who with good reason, perhaps,
suspected that a delay might diminish rather than increase the
treasures, clamored for an immediate division. The troops were
accordingly called, and in their presence the partition was made: first
of the royal fifth;[585] then of the fifth promised to Cortés when
appointed captain-general; after this a large sum was set apart to
cover expenditures by Cortés and Velazquez on the fleet and its
outfit, and the value of the horses killed during the campaign,[586]
and another sum for the expenses and shares of the procuradores in
Spain, while double or special shares were assigned to the priests,
the captains, those owning horses, and the men with fire-arms and
cross-bows.[587] After all these deductions but little remained for the
rank and file—a hundred pesos, if we may credit Bernal Diaz.[588]
This, many indignantly refused to accept; others took it, but joined in
the clamors of the discontented.
It is almost too much to ask of vultures not to quarrel over their
prey. The murmur against the royal fifth was loud enough, but the
second fifth for Cortés raised quite an outcry. “Are we to have a
second king?” they asked. Others inquired, “For whose fleet are we
paying?” They further wished to know whether the fame and
promotion acquired for the general by his men could not satisfy
some of his claims, for the present, at least. They had once before
surrendered hard-earned money to please him and to promote his
credit with the king, and now, when they had been led to expect
reward, it was again snatched from them. Some said that a large
proportion of the treasures had been secured by Cortés and his
favorites before the distribution began; and the value of the heavy
gold chains and other ornaments displayed by them was significantly
pointed at as out of proportion to their share.
The suspicion was confirmed by a quarrel which occurred shortly
after between Velazquez de Leon and Treasurer Mejía respecting
the payment of the royal fifth on certain unbroken jewels found in
Velazquez’ possession, and received by him before the
apportionment. It was enough, said Mejía, for Cortés to appropriate
unassessed treasures. Velazquez refusing to comply, they came to
blows, and if friends had not interfered there might have been an
officer or two less in the camp. As it was, both received slight
wounds, and subsequently shackles. Mejía was released within a
few hours; but his antagonist retained the fetters for two days,
persuaded to submit with grace thereto by Cortés, it was said, in
order to allay suspicions and to show that the general could be just,
even when it affected a friend.[589]
Finding that the murmurs were becoming serious, Cortés
brought his soothing eloquence to bear upon the troubled spirits. He
represented that all his thoughts, efforts, and possessions were for
the honor of his God, his king, and his companions. With them he
had shared every danger and hardship, and for their welfare he had
watched, rendering justice to all. The division had been fairly made
in accordance with previous arrangement. But he was not avaricious;
all he had was theirs, and he would employ it for them as might a
father. He would surrender the fifth which had been assigned him, if
they wished it, retaining only his share as captain-general; and he
would also help any one in need. The treasure thus far secured was
insignificant compared to what lay before them. What mattered a few
hundred pesos more or less in view of the rich mines, the large
tracts, and the immense number of towns, which were all theirs, so
long as they held loyally together? “I will make a lord of every one of
you,” he concluded, “if you will but have peace and patience.”[590]
And to give greater effect to this harangue he bribed with gifts and
promises the more influential to sound his praises; whereupon the
murmurs died away, though rancor still remained with many, awaiting
opportunity.[591]
A large proportion of the soldiers imitated the example of the
heavy sharers in the spoils by converting their allotment, with the aid
of Azcapuzalcan goldsmiths, into chains, crosses, and other
adornments for their persons, so that the display of wealth became
quite dazzling. Others yielded to the infatuation for gambling, then so
prevalent, and lost without a murmur the hard-earned share.[592]
But one thing now remained to complete the triumph of the
conqueror. The manacled kings were subservient, and the people
displayed their loyalty by pouring tribute into his coffers. But his god
was not theirs, and this the pious pilferer could not endure. He and
his priests had lost no opportunity to preach the faith to emperor and
subjects;[593] but the hearts of the natives were obdurately fixed on
the idols of the pyramid. He never beheld the temple without being
tempted to lay low the effigies of Satan, and it was owing only to
Father Olmedo’s prudent counsel that the temptation was resisted.
Repeatedly had he urged on the weak emperor to begin the great
work by some radical reform, but could obtain only the promise that
human sacrifices would be stopped. Finding that even this was not
observed, he consulted with his captains, and it was agreed to
demand the surrender of the great temple for Christian worship, so
that the natives might be made to feel the holy influence of its
symbols and rites. Montezuma was prepared with excuses, but the
deputation declared with fierce vehemence that if this were refused
they would forcibly remove the idols and kill the priests who resisted.
“Malinche,” exclaimed the monarch in alarm, “do you then seek the
destruction of the city? Our gods are incensed against us, and the
people imbittered. Even your lives will not be safe. Wait, I entreat
you, till I call the priests for consultation.”[594]
Cortés saw that nothing more could then be attained, but with
the indiscreet zeal for religion which often blinded him he determined
that there should be no further delay. He apprehended no uprising
among a people which had so patiently submitted to all exactions,
yet he feared that the priests, if warned, might prevent an entry into

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Carraher's polymer chemistry 10ed.

Tenth Edition Carraher Charles E. Jr.

Introduction to Polymer Chemistry Third Edition

Introduction to Polymer Chemistry, Fourth Edition

Carraher s polymer chemistry Ninth Edition. Edition

Introduction to polymer chemistry Carraher

Environmental chemistry Tenth Edition Manahan Stanley

Polymer Chemistry 1st Edition Sebastian Koltzenburg

Introduction to Criminology (Tenth Edition) Frank E.

New venture creation : entrepreneurship for the 21st

Charles E. Carraher, Jr.

© 2018 by Taylor & Francis Group, LLC

No claim to original U.S. Government works

Printed on acid-free paper

International Standard Book Number-13: 978-1-4987-3738-8 (Hardback)

Library of Congress Cataloging-in-Publication Data

Names: Carraher, Charles E., Jr., 1941-

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

Chapter 2 Polymer Structure (Morphology)................................................................................ 27

Chapter 3 Molecular Weight of Polymers.................................................................................... 59

3.6.2 End-Group Analysis........................................................................... 77

Chapter 4 Polycondensation Polymers (Step-Reaction Polymerization)................................... 101

Chapter 5 Ionic Chain-Reaction and Complex Coordination Polymerization (Addition

5.8 Polypropylene................................................................................................. 196

Chapter 6 Free Chain Polymerization (Addition Polymerization)............................................. 217

Chapter 7 Copolymerization...................................................................................................... 261

7.14 Polymer Mixtures........................................................................................... 282

Chapter 8 Composites and Fillers.............................................................................................. 293

Chapter 9 Naturally Occurring Polymers—Plants.................................................................... 313

9.12 Balloons.......................................................................................................... 355

Chapter 10 Naturally Occurring Polymers—Animals................................................................ 367

Chapter 11 Organometallic and Inorganic–Organic Polymers................................................... 433

11.3 Condensation Organometallic Polymers........................................................ 437

Chapter 12 Inorganic Polymers................................................................................................... 459

Chapter 13 Testing and Spectrometric Characterization of Polymers.........................................509

Chapter 14 Rheology and Physical Tests..................................................................................... 545

Chapter 15 Additives.................................................................................................................... 569

Chapter 16 Reactions on Polymers.............................................................................................. 585

16.2 Reactions of Aromatic and Aliphatic Pendant Groups.................................. 586

Chapter 17 Synthesis of Reactants and Intermediates for Polymers........................................... 615

Chapter 18 Polymer Technology.................................................................................................. 645

18.7.4 Processing of Fiber-Reinforced Composites....................................660

Chapter 19 Selected Topics.......................................................................................................... 689

Appendix A: Symbols................................................................................................................... 747

1.1 HISTORY OF POLYMERS

TABLE 1.1 (Continued)

[526] ‘Casa de Cacao, de Motecuhçuma, adonde avia mas de quarenta mil

[535] ‘Me has negado no auer mãdado a Couatlpopocà q̄ matasse a mis

[540] ‘Como este castigo se supo en todas las Prouincias de la Nueua-España,

[553] ‘En la laguna á vn peñol, que estaua acotado, q̄ no ossauan entrar en èl á

Growing Discontent among the Mexicans—Cacama’s Conspiracy—He

With their hand so securely on the spring that moved a mighty

Although there were enough of sympathizers in Mexico for his

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16.2 Reactions of Aromatic and Aliphatic Pendant Groups.................................. 586