POLYMER CHEMISTRY AN INTRODUCTION. Malcolm P. Stevens. University of Hartford. New York Oxford OXFORD UNIVERSITY PRESS
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1 T H I R D E D I T I O N POLYMER CHEMISTRY AN INTRODUCTION Malcolm P. Stevens University of Hartford New York Oxford OXFORD UNIVERSITY PRESS 1999
2 CONTENTS Preface, PART I xvii POLYMER STRUCTURE AND PROPERTIES I. Basic principles, Introduction and historical development, Definitions, Polymerization processes, Step-reaction polymerization, Chain-reaction polymerization, Step-reaction addition and chain-reaction condensation, Nomenclature, Vinyl polymers, Vinyl copolymers, Nonvinyl polymers, Nonvinyl copolymers, End groups, Abbreviations, Industrial polymers, Plastics, fifaers, Rubber (elastomers), Coatings and adhesives, Polymer recycling, 30 References, 31 Review exercises, 32 vii
3 Vlll Contents 2. Molecular weight and polymer Solutions, Number average and weight average molecular weight, Polymer Solutions, Measurement of number average molecular weight, End-group analysis, Membrane osmometry, Cryoscopy and ebulliometry, Vapor pressure osmometry, Mass spectrometry, Refractive index measurements, Measurement of weight average molecular weight, Light scattering, Ulcentrifugation, Viscometry, Molecular weight distribution, Gel permeation chromatography (GPC), Fractional Solution, Fractional preäpitation, Thin-layer chromatography (TLC), 58 References, 58 Review exercises, Chemical structure and polymer morphology, Introduction, Molecular weight and intermolecular forces, The amorphous State rheology, Glass transition temperature, Stereochemistry, Crystallinity, Liquid crystallinity, Chemical crosslinking, Physical crosslinking, Polymer blends, 87 References, 91 Review exercises, 93
4 Contents ix 4. Chemical structure and polymer properties, Introduction, Fabrication methods, Mechanical properties, Thermal stability, Flammability and flame resistance, I Chemical resistance, I Degradability, I Electrical conductivity, I Nonlinear optical properties, Additives, 121 References, 124 Review exercises, Evaluation, characterization, and analysis of polymers, Introduction, Chemical methods of analysis, Spectroscopic methods of analysis, Infrared, Raman, Nuclear magnetic resonance, Electron spin resonance, Ultraviolet (UV)-visible, Fluorescence, X-ray, electron, and neutron scattering, Characterization and analysis of polymer surfaces, Scanning electron microscopy (SEM), Attenuated total reflectance spectroscopy (ATR), Photoacoustic spectroscopy (PAS), Electron spectroscopy for chemical analysis (or applications) (ESCA) and Auger electron spectroscopy (AES), Secondary-ion mass spectrometry (SIMS) and ion-scattering spectroscopy (ISS), Atomic force microscopy (AFM), Thermal analysis, Differential scanning calorimetry (DSC) and differential thermal analysis (DTA), 149
5 X Contents Thermomechanical analysis (TMA), Thermogravimetric analysis (TGA), Pyrolysis-gas chromatography (PGC), Flammability testing, Measurement of mechanical properties, Evaluation of chemical resistance, Evaluation of electrical properties, 159 References, 160 Review exercises, 163 PART II VINYL POLYMERS 6. Free radical polymerization, Introduction, Free radical initiators, Peroxides and hydroperoxides, Azo Compounds, Redox initiators, Photoinitiators, Thermal polymerization, Electrochemical polymerization, Techniques of free radical polymerization, Bulk, Suspension, Solution, Emulsion, Kinetics and mechanism of polymerization, Stereochemistry of polymerization, Polymerization of dienes, / Isolated dienes, Conjugated dienes, Monomer reactivity, Copolymerization, 194 References, 201 Review exercises, 202
6 Contents xi 7. lonic polymerization, Introduction, Cationic polymerization, Cationic initiators, Mechanism, kinetics, and reactivity in cationic polymerization, Stereochemistry of cationic polymerization, Cationic copolymerization, Isomerization in cationic polymerization, Anionic polymerization, Anionic initiators, Mechanism, kinetics, and reactivity in anionic polymerization, Stereochemistry of anionic polymerization, Anionic copolymerization, Group transfer polymerization, 227 References, 230 Review exercises, Vinyl polymerization with complex coordination catalysts, Introduction, Heterogeneous Ziegler-Natta polymerization, Heterogeneous catalysts, Mechanism and reactivity in heterogeneous polymerization, Stereochemistry of heterogeneous polymerization, Polymerization ofdienes, Homogeneous Ziegler-Natta polymerization, Metallocene catalysts, Mechanism and reactivity with metallocene catalysts, Stereochemistry of metallocene-catalyzed polymerization, Ziegler-Natta copolymerization, Supported metal oxide catalysts, Alfin catalysts, Metathesis polymerization, 252
7 xii Contents Ring-opening metathesis polymerization, Acyclic diene metathesis polymerization, 255 References, 255 Review exercises, Reactions of vinyl polymers, Introduction, Functional group reactions, Introduction of new functional groups, Conversion of functional groups, Ring-forming reactions, Crosslinking, Vulcanization, Radiation crosslinking, Photochemical crosslinking, Crosslinking through labile functional groups, lonic crosslinking, Block and graft copolymer formation, Block copolymers, Graft copolymers, Polymer degradation, Chemical degradation, Thermal degradation, Degradation by radiation, 278 References, 279 Review exercises, 281 PART III NONVINYL POLYMERS 10. Step-reaction and ring-opening polymerization, Introduction, Step-reaction polymerization kinetics, Stoichiometric imbalance, Molecular weight distribution, Network step polymerization, Step-reaction copolymerization, Step polymerization techniques, 298
8 Contents 10.8 Dendritic polymers, Ring-opening polymerization, 304 References, 306 Review exercises, Polyethers, polysulfides, and related polymers, 309 ll.l Introduction, 309 I 1.2 Preparation of polyethers by chain-reaction and ring-opening polymerization, Polymerization of carbonyl Compounds, 309 /1.2.2 Stereochemistry ofaldehyde polymerization, 313 /1.2.3 Polymerization ofcyclic ethers, 3 14 /1.2.4 Stereochemistry of epoxide polymerization, Preparation of polyethers by step-reaction polymerization, 321 /1.3.1 Synthesis of polyethers from glycols and bisphenols, Polyacetals and polyketals, Poly(phenylene oxide)s, 324 /1.3.4 Epoxy resins, Polysulfides, poly(alkylene polysulfide)s, and polysulfones, Polysulfides, Poly(alkylene polysulfide)s, 331 /1.4.3 Polysulfones, 332 References, 333 Review exercises, Polyesters, Introduction, Linear polyesters, Preparation of polyesters by polycondensation reactions, Polycarbonates, 346 / Preparation of polyesters by ring-opening polymerizavon, Microbial polyesters, Hyperbranched polyesters, Crosslinked polyesters, Saturated polyester resins, Unsaturated polyesters, 356 References, 359 Review exercises, 360
9 XIV Contents 13. Polyamides and related polymers, Introduction, Polyamides, Preparation ofpolyamides by polycondensation reactions, Polymerization oflactams, Miscellaneous methods of preparing polyamides, Properties of polyamides, Polyureas, Polyurethanes, Polyhydrazides, Polyimides, 382 References, 388 Review exercises, Phenol-, urea-, and melamine-formaldehyde polymers, Introduction, Phenol-formaldehyde polymers: resoles, Phenol-formaldehyde polymers: novolacs, Chemical modifications of phenolic resins, Urea-formaldehyde polymers, Melamine-formaldehyde polymers, 406 References, 407 Review exercises, Heterocyclic polymers, Introduction, Polypyrrole, polyfuran, and polythiophene, Polycyanurate and polyphthalocyanine resins, Heterocyclic polymers formed from precursor polymers, Heterocyclic polymers formed from polyfunctional monomers, Polybenzimidazoles, Polybenzoxazoles and polybenzothiazoles, Polyhydantoins, Poly(parabanic aäd)s, Polyquinoxalines and polypyrazines, Polypyrazoles and polyimidazoles, Poly(as-triazine)s and polytriazolines, 420
10 Contents Polyquinolines and polyanthrazolines, 421 References, 421 Review exercises, Inorganic and partially inorganic polymers, Introduction, Poly(sulfur nitride), Polysiloxanes, Polysilanes, Polyphosphazenes, Carborane polymers, Organometallic polymers, Coordination polymers, 438 References, 442 Review exercises, Miscellaneous organic polymers, Introduction, Miscellaneous unsaturated polymers, 447 / Polycarbodiimides, 447 / Polyimines, 449 / Polymers containing carbon-carbon double bonds, 450 / Azo polymers, 450 / Polymers containing carbon-carbon triple bonds, Poly(p-phenylene) and poly(p-xylylene), 452 / Poly(p-phenylene), 452 / Poly(p-xylylene), Friedel-Crafts polymers, Cycloaddition polymerization, 456 / Diels-Alder polymerization, 456 / Cycloaddition polymerization, Polyanhydrides, Polyamines, Charge-transfer polymers, lonic polymers, 467 References, 469 Review exercises, 471
11 xvi Contents 18. Natural polymers, Introduction, Miscellaneous natural polymers, Rubber, Lignin, humus, coal, and kerogen, Asphaltenes, Shellac, Amber, Tall oil-derived polymers, Polysaccharides, Cellulose, Regenerated cellulose, Derivatives of cellulose, Starch, Derivatives of starch, Other Polysaccharides, Proteins, 492 / Amino acids, Polypeptides, and proteins, Protein structure, Synthesis of Polypeptides and proteins, Wool, silk, Collagen, and regenerated protein, Nucleic acids, Nucleic acid structure, Nucleic acid synthesis, Conclusion, 510 References, 510 Review exercises, 513 Appendix A Commonly used polymer abbreviations, 515 Appendix B Polymer literature, 517 Appendix C Index, 535 Sources of laboratory experiments in polymer chemistry, 526
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