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PRINCIPLES OF
POLYMERIZATION
Fourth Edition

GEORGE ODIAN
College of Staten Island
City University of New York
Staten Island, New York

A JOHN WILEY & SONS, INC., PUBLICATION

PRINCIPLES OF
POLYMERIZATION
Fourth Edition
PRINCIPLES OF
POLYMERIZATION
Fourth Edition

GEORGE ODIAN
College of Staten Island
City University of New York
Staten Island, New York

A JOHN WILEY & SONS, INC., PUBLICATION

Copyright # 2004 by John Wiley & Sons, Inc. All rights reserved.

Published by John Wiley & Sons, Inc., Hoboken, New Jersey.

Published simultaneously in Canada.

No part of this publication may be reproduced, stored in a retrieval system, or transmitted in any form
or by any means, electronic, mechanical, photocopying, recording, scanning, or otherwise, except as
permitted under Section 107 or 108 of the 1976 United States Copyright Act, without either the prior
written permission of the Publisher, or authorization through payment of the appropriate per-copy fee
to the Copyright Clearance Center, Inc., 222 Rosewood Drive, Danvers, MA 01923, 978-750-8400,
fax 978-750-4470, or on the web at www.copyright.com. Requests to the Publisher for permission should
be addressed to the Permissions Department, John Wiley & Sons, Inc., 111 River Street, Hoboken,
NJ 07030, (201) 748-6011, fax (201) 748-6008, e-mail: [email protected].

Limit of Liability/Disclaimer of Warranty: While the publisher and author have used their best
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however, may not be available in electronic format.

Library of Congress Cataloging-in-Publication Data:

Principles of Polymerization, Fourth Edition
George Odian
ISBN 0-471-27400-3
Printed in the United States of America

10 9 8 7 6 5 4 3 2 1
CONTENTS

PREFACE xxiii

1 INTRODUCTION 1
1-1 Types of Polymers and Polymerizations / 1
1-1a Polymer Composition and Structure / 2
1-1b Polymerization Mechanism / 6
1-2 Nomenclature of Polymers / 9
1-2a Nomenclature Based on Source / 10
1-2b Nomenclature Based on Structure (Non-IUPAC) / 11
1-2c IUPAC Structure-Based Nomenclature System / 11
1-2d Trade Names and Nonnames / 16
1-3 Linear, Branched, and Crosslinked Polymers / 17
1-4 Molecular Weight / 19
1-5 Physical State / 24
1-5a Crystalline and Amorphous Behavior / 24
1-5b Determinants of Polymer Crystallinity / 27
1-5c Thermal Transitions / 29
1-6 Applications of Polymers / 32
1-6a Mechanical Properties / 32
1-6b Elastomers, Fibers, and Plastics / 35
References / 36

v
vi CONTENTS

2 STEP POLYMERIZATION 39
2-1 Reactivity of Functional Groups / 40
2-1a Basis for Analysis of Polymerization Kinetics / 40
2-1b Experimental Evidence / 41
2-1c Theoretical Considerations / 43
2-1d Equivalence of Groups in Bifunctional Reactants / 44
2-2 Kinetics of Step Polymerization / 44
2-2a Self-Catalyzed Polymerization / 46
2-2a-1 Experimental Observations / 47
2-2a-2 Reasons for Nonlinearity in Third-Order Plot / 48
2-2a-3 Molecular Weight of Polymer / 50
2-2b External Catalysis of Polymerization / 51
2-2c Step Polymerizations Other than Polyesterification:
Catalyzed versus Uncatalyzed / 53
2-2d Nonequivalence of Functional Groups in Polyfunctional
Reagents / 54
2-2d-1 Examples of Nonequivalence / 54
2-2d-2 Kinetics / 57
2-3 Accessibility of Functional Groups / 63
2-4 Equilibrium Considerations / 65
2-4a Closed System / 65
2-4b Open, Driven System / 67
2-4c Kinetics of Reversible Polymerization / 69
2-5 Cyclization versus Linear Polymerization / 69
2-5a Possible Cyclization Reactions / 69
2-5b Cyclization Tendency versus Ring Size / 70
2-5c Reaction Conditions / 72
2-5d Thermodynamic versus Kinetic Control / 73
2-5e Other Considerations / 74
2-6 Molecular Weight Control in Linear Polymerization / 74
2-6a Need for Stoichiometric Control / 74
2-6b Quantitative Aspects / 75
2-6c Kinetics of Nonstoichiometric Polymerization / 79
2-7 Molecular Weight Distribution in Linear Polymerization / 80
2-7a Derivation of Size Distributions / 80
2-7b Breadth of Molecular Weight Distribution / 82
2-7c Interchange Reactions / 83
2-7d Alternate Approaches for Molecular-Weight Distribution / 83
2-7e Effect of Reaction Variables on MWD / 86
2-7e-1 Unequal Reactivity of Functional Groups / 86
2-7e-2 Change in Reactivity on Reaction / 86
2-7e-3 Nonstoichiometry of Functional Groups / 86
 CONTENTS vii

2-8 Process Conditions / 87

2-8a Physical Nature of Polymerization Systems / 87
2-8b Different Reactant Systems / 89
2-8c Interfacial Polymerization / 90
2-8c-1 Description of Process / 90
2-8c-2 Utility / 92
2-8d Polyesters / 92
2-8e Polycarbonates / 96
2-8f Polyamides / 97
2-8g Historical Aspects / 101
2-9 Multichain Polymerization / 101
2-9a Branching / 101
2-9b Molecular Weight Distribution / 102
2-10 Crosslinking / 103
2-10a Carothers Equation: X n ! 1 / 105
2-10a-1 Stoichiometric Amounts of Reactants / 105
2-10a-2 Extension to Nonstoichiometric Reactant
Mixtures / 106
2-10b Statistical Approach to Gelation: X w ! 1 / 108
2-10c Experimental Gel Points / 111
2-10d Extensions of Statistical Approach / 112
2-11 Molecular Weight Distributions in Nonlinear Polymerizations / 114
2-12 Crosslinking Technology / 117
2-12a Polyesters, Unsaturated Polyesters, and Alkyds / 118
2-12b Phenolic Polymers / 120
2-12b-1 Resole Phenolics / 120
2-12b-2 Novolac Phenolics / 124
2-12b-3 Applications / 126
2-12c Amino Plastics / 126
2-12d Epoxy Resins / 128
2-12e Polyurethanes / 130
2-12f Polysiloxanes / 132
2-12g Polysulfides / 134
2-13 Step Copolymerization / 135
2-13a Types of Copolymers / 135
2-13b Methods of Synthesizing Copolymers / 138
2-13b-1 Statistical Copolymers / 138
2-13b-2 Alternating Copolymers / 138
2-13b-3 Block Copolymers / 139
2-13c Utility of Copolymerization / 140
2-13c-1 Statistical Copolymers / 141
2-13c-2 Block Copolymers / 142
viii CONTENTS

2-13c-3 Polymer Blends and Interpenetrating Polymer

Networks / 143
2-13c-4 Constitutional Isomerism / 144
2-14 High-Performance Polymers / 144
2-14a Requirements for High-Temperature Polymers / 144
2-14b Aromatic Polyethers by Oxidative Coupling / 146
2-14c Aromatic Polyethers by Nucleophilic Substitution / 149
2-14d Aromatic Polysulfides / 151
2-14e Aromatic Polyimides / 151
2-14f Reactive Telechelic Oligomer Approach / 155
2-14g Liquid Crystal Polymers / 157
2-14h 5-Membered Ring Heterocyclic Polymers / 159
2-14i 6-Membered Ring Heterocyclic Polymers / 162
2-14j Conjugated Polymers / 163
2-14j-1 Oxidative Polymerization of Aniline / 165
2-14j-2 Poly(p-phenylene) / 166
2-14j-3 Poly(p-phenylene Vinylene) / 167
2-15 Inorganic and Organometallic Polymers / 168
2-15a Inorganic Polymers / 168
2-15a-1 Minerals / 168
2-15a-2 Glasses / 169
2-15a-3 Ceramics / 170
2-15b Organometallic Polymers / 172
2-15b-1 Polymerization via Reaction at Metal Bond / 172
2-15b-2 Polymerization without Reaction at Metal
Bond / 173
2-15b-3 Polysilanes / 173
2-16 Dendritic (Highly Branched) Polymers / 174
2-16a Random Hyperbranched Polymers / 175
2-16b Dendrimers / 177
2-17 Miscellaneous Topics / 180
2-17a Enzymatic Polymerizations / 180
2-17a-1 In Vivo (within Living Cells) / 180
2-17a-2 In Vitro (outside Living Cells) / 181
2-17b Polymerization in Supercritical Carbon Dioxide / 183
2-17c Cycloaddition (Four-Center) Polymerization / 183
2-17d Spiro Polymers / 184
2-17e Pseudopolyrotoxanes and Polyrotoxanes / 184
References / 185

3 RADICAL CHAIN POLYMERIZATION 198

3-1 Nature of Radical Chain Polymerization / 199
 CONTENTS ix

3-1a Comparison of Chain and Step Polymerizations / 199

3-1b Radical versus Ionic Chain Polymerizations / 199
3-1b-1 General Considerations of Polymerizability / 199
3-1b-2 Effects of Substituents / 200
3-2 Structural Arrangement of Monomer Units / 202
3-2a Possible Modes of Propagation / 202
3-2b Experimental Evidence / 203
3-2c Synthesis of Head-to-Head Polymers / 204
3-3 Rate of Radical Chain Polymerization / 204
3-3a Sequence of Events / 204
3-3b Rate Expression / 206
3-3c Experimental Determination of Rp / 208
3-3c-1 Physical Separation and Isolation of Reaction
Product / 208
3-3c-2 Chemical and Spectroscopic Analysis / 208
3-3c-3 Other Techniques / 209
3-4 Initiation / 209
3-4a Thermal Decomposition of Initiators / 209
3-4a-1 Types of Initiators / 209
3-4a-2 Kinetics of Initiation and Polymerization / 212
3-4a-3 Dependence of Polymerization Rate on Initiator / 212
3-4a-4 Dependence of Polymerization Rate on Monomer / 214
3-4b Redox Initiation / 216
3-4b-1 Types of Redox Initiators / 216
3-4b-2 Rate of Redox Polymerization / 217
3-4c Photochemical Initiation / 218
3-4c-1 Bulk Monomer / 219
3-4c-2 Irradiation of Thermal and Redox Initiators / 220
3-4c-3 Rate of Photopolymerization / 221
3-4d Initiation by Ionizing Radiation / 224
3-4e Pure Thermal Initiation / 226
3-4f Other Methods of Initiation / 227
3-4g Initiator Efficiency / 228
3-4g-1 Definition of f / 228
3-4g-2 Mechanism of f < 1: Cage Effect / 228
3-4g-3 Experimental Determination of f / 232
3-4h Other Aspects of Initiation / 235
3-5 Molecular Weight / 236
3-5a Kinetic Chain Length / 236
3-5b Mode of Termination / 236
3-6 Chain Transfer / 238
3-6a Effect of Chain Transfer / 238
x CONTENTS

3-6b Transfer to Monomer and Initiator / 240

3-6b-1 Determination of CM and CI / 240
3-6b-2 Monomer Transfer Constants / 241
3-6b-3 Initiator Transfer Constants / 244
3-6c Transfer to Chain-Transfer Agent / 245
3-6c-1 Determination of CS / 245
3-6c-2 Structure and Reactivity / 246
3-6c-3 Practical Utility of Mayo Equation / 249
3-6d Chain Transfer to Polymer / 250
3-6e Catalytic Chain Transfer / 254
3-7 Inhibition and Retardation / 255
3-7a Kinetics of Inhibition or Retardation / 256
3-7b Types of Inhibitors and Retarders / 259
3-7c Autoinhibition of Allylic Monomers / 263
3-8 Determination of Absolute Rate Constants / 264
3-8a Non-Steady-State Kinetics / 264
3-8b Rotating Sector Method / 265
3-8c PLP-SEC Method / 267
3-8d Typical Values of Reaction Parameters / 269
3-9 Energetic Characteristics / 271
3-9a Activation Energy and Frequency Factor / 271
3-9a-1 Rate of Polymerization / 272
3-9a-2 Degree of Polymerization / 274
3-9b Thermodynamics of Polymerization / 275
3-9b-1 Significance of
G,
H, and
S / 275
3-9b-2 Effect of Monomer Structure / 276
3-9b-3 Polymerization of 1,2-Disubstituted Ethylenes / 277
3-9c Polymerization–Depolymerization Equilibria / 279
3-9c-1 Ceiling Temperature / 279
3-9c-2 Floor Temperature / 282
3-10 Autoacceleration / 282
3-10a Course of Polymerization / 282
3-10b Diffusion-Controlled Termination / 283
3-10c Effect of Reaction Conditions / 286
3-10d Related Phenomena / 287
3-10d-1 Occlusion (Heterogeneous) Polymerization / 287
3-10d-2 Template Polymerization / 287
3-10e Dependence of Polymerization Rate on Initiator and
Monomer / 288
3-10f Other Accelerative Phenomena / 289
3-11 Molecular Weight Distribution / 289
3-11a Low-Conversion Polymerization / 289
 CONTENTS xi

3-11b High-Conversion Polymerization / 292

3-12 Effect of Pressure / 292
3-12a Effect on Rate Constants / 293
3-12a-1 Volume of Activation / 293
3-12a-2 Rate of Polymerization / 294
3-12a-3 Degree of Polymerization / 295
3-12b Thermodynamics of Polymerization / 296
3-12c Other Effects of Pressure / 296
3-13 Process Conditions / 296
3-13a Bulk (Mass) Polymerization / 297
3-13b Solution Polymerization / 297
3-13c Heterogeneous Polymerization / 297
3-13d Other Processes; Self-Assembly and Nanostructures / 299
3-14 Specific Commercial Polymers / 300
3-14a Polyethylene / 300
3-14b Polystyrene / 302
3-14c Vinyl Family / 304
3-14c-1 Poly(vinyl chloride) / 304
3-14c-2 Other Members of Vinyl Family / 306
3-14d Acrylic Family / 307
3-14d-1 Acrylate and Methacrylate Products / 307
3-14d-2 Polyacrylonitrile / 308
3-14d-3 Other Members of Acrylic Family / 308
3-14e Fluoropolymers / 309
3-14f Polymerization of Dienes / 310
3-14g Miscellaneous Polymers / 311
3-14g-1 Poly(p-xylylene) / 311
3-14g-2 Poly(N-vinylcarbazole) / 313
3-14g-3 Poly(N-vinylpyrrolidinone) / 313
3-15 Living Radical Polymerization / 313
3-15a General Considerations / 313
3-15b Atom Transfer Radical Polymerization (ATRP) / 316
3-15b-1 Polymerization Mechanism / 316
3-15b-2 Effects of Components of Reaction System / 319
3-15b-3 Complex Kinetics / 321
3-15b-4 Block Copolymers / 322
3-15b-5 Other Polymer Architectures / 324
3-15c Stable Free-Radical Polymerization (SFRP) / 325
3-15d Radical Addition–Fragmentation Transfer (RAFT) / 328
3-15e Other Living Radical Polymerizations / 330
3-16 Other Polymerizations / 330
3-16a Organometallic Polymers / 330
xii CONTENTS

3-16b Functional Polymers / 330

3-16c Acetylenic Monomers / 332
References / 332

4 EMULSION POLYMERIZATION 350

4-1 Description of Process / 350
4-1a Utility / 350
4-1b Qualitative Picture / 351
4-1b-1 Components and Their Locations / 351
4-1b-2 Site of Polymerization / 353
4-1b-3 Progress of Polymerization / 354
4-2 Quantitative Aspects / 356
4-2a Rate of Polymerization / 356
4-2b Degree of Polymerization / 360
4-2c Number of Polymer Particles / 362
4-3 Other Characteristics of Emulsion Polymerization / 363
4-3a Initiators / 363
4-3b Surfactants / 363
4-3c Other Components / 364
4-3d Propagation and Termination Rate Constants / 364
4-3e Energetics / 365
4-3f Molecular Weight and Particle Size Distributions / 365
4-3g Surfactant-Free Emulsion Polymerization / 366
4-3h Other Emulsion Polymerization Systems / 367
4-3i Living Radical Polymerization / 368
References / 369

5 IONIC CHAIN POLYMERIZATION 372

5-1 Comparison of Radical and Ionic Polymerizations / 372
5-2 Cationic Polymerization of the Carbon–Carbon Double Bond / 374
5-2a Initiation / 374
5-2a-1 Protonic Acids / 374
5-2a-2 Lewis Acids / 375
5-2a-3 Halogen / 379
5-2a-4 Photoinitiation by Onium Salts / 379
5-2a-5 Electroinitiation / 380
5-2a-6 Ionizing Radiation / 381
5-2b Propagation / 382
5-2c Chain Transfer and Termination / 384
5-2c-1 b-Proton Transfer / 384
5-2c-2 Combination with Counterion / 386
 CONTENTS xiii

5-2c-3 Chain Transfer to Polymer / 387

5-2c-4 Other Transfer and Termination Reactions / 387
5-2d Kinetics / 388
5-2d-1 Different Kinetic Situations / 388
5-2d-2 Validity of Steady-State Assumption / 391
5-2d-3 Molecular Weight Distribution / 391
5-2e Absolute Rate Constants / 392
5-2e-1 Experimental Methods / 392
5-2e-2 Difficulty in Interpreting Rate Constants / 394
5-2e-3 Comparison of Rate Constants / 396
5-2e-4 CM and CS Values / 398
5-2f Effect of Reaction Medium / 399
5-2f-1 Propagation by Covalent Species;
Pseudocationic Polymerization / 399
5-2f-2 Solvent Effects / 401
5-2f-3 Counterion Effects / 403
5-2g Living Cationic Polymerization / 403
5-2g-1 General Requirements / 404
5-2g-2 Rate and Degree of Polymerization / 405
5-2g-3 Specific Living Cationic Polymerization Systems / 406
5-2h Energetics / 408
5-2i Commercial Applications of Cationic Polymerization / 410
5-2i-1 Polyisobutylene Products / 410
5-2i-2 Other Products / 411
5-3 Anionic Polymerization of the Carbon–Carbon Double Bond / 412
5-3a Initiation / 412
5-3a-1 Nucleophilic Initiators / 412
5-3a-2 Electron Transfer / 414
5-3b Termination / 416
5-3b-1 Polymerizations without Termination / 416
5-3b-2 Termination by Impurities and Deliberately Added
Transfer Agents / 416
5-3b-3 Spontaneous Termination / 417
5-3b-4 Termination and Side Reactions of Polar Monomers / 418
5-3c Group Transfer Polymerization / 420
5-3d Kinetics of Living Polymerization / 422
5-3d-1 Polymerization Rate / 422
5-3d-2 Effects of Reaction Media / 423
5-3d-3 Degree of Polymerization / 428
5-3d-4 Energetics: Solvent-Separated and Contact Ion Pairs / 429
5-3d-5 Association Phenomena in Alkyllithium / 433
5-3d-6 Other Phenomena / 435
xiv CONTENTS

5-4 Block and Other Polymer Architectures / 436

5-4a Sequential Monomer Addition / 436
5-4b Telechelic (End-Functionalized) Polymers / 439
5-4c Coupling Reactions / 441
5-4d Transformation Reactions / 443
5-5 Distinguishing Between Radical, Cationic, and Anionic
Polymerizations / 443
5-6 Carbonyl Polymerization / 444
5-6a Anionic Polymerization / 445
5-6a-1 Formaldehyde / 445
5-6a-2 Other Carbonyl Monomers / 446
5-6b Cationic Polymerization / 447
5-6c Radical Polymerization / 447
5-6d End Capping / 448
5-7 Miscellaneous Polymerizations / 449
5-7a Monomers with Two Different Polymerizable Groups / 449
5-7b Hydrogen-Transfer Polymerization of Acrylamide / 450
5-7c Polymerization and Cyclotrimerization of Isocyanates / 451
5-7d Monomers with Triple Bonds / 451
References / 452

6 CHAIN COPOLYMERIZATION 464

6-1 General Considerations / 465
6-1a Importance of Chain Copolymerization / 465
6-1b Types of Copolymers / 465
6-2 Copolymer Composition / 466
6-2a Terminal Model; Monomer Reactivity Ratios / 466
6-2b Statistical Derivation of Copolymerization Equation / 469
6-2c Range of Applicability of Copolymerization Equation / 470
6-2d Types of Copolymerization Behavior / 471
6-2d-1 Ideal Copolymerization: r1 r2 ¼ 1 / 471
6-2d-2 Alternating Copolymerization: r1 r2 ¼ 0 / 473
6-2d-3 Block Copolymerization: r1 > 1; r2 > 1 / 475
6-2e Variation of Copolymer Composition with Conversion / 475
6-2f Experimental Evaluation of Monomer Reactivity Ratios / 480
6-2g Microstructure of Copolymers / 481
6-2g-1 Sequence Length Distribution / 481
6-2g-2 Copolymer Compositions of Different Molecules / 484
6-2h Multicomponent Copolymerization / 485
6-3 Radical Copolymerization / 487
6-3a Effect of Reaction Conditions / 487
6-3a-1 Reaction Medium / 487
 CONTENTS xv

6-3a-2 Temperature / 489

6-3a-3 Pressure / 490
6-3b Reactivity / 490
6-3b-1 Resonance Effects / 490
6-3b-2 Steric Effects / 496
6-3b-3 Alternation; Polar Effects and Complex Participation / 497
6-3b-4 Q–e Scheme / 500
6-3b-5 Patterns of Reactivity Scheme / 503
6-3b-6 Other Quantitative Approaches to Reactivity / 505
6-3c Terminal Model for Rate of Radical Copolymerization / 505
6-4 Ionic Copolymerization / 506
6-4a Cationic Copolymerization / 507
6-4a-1 Reactivity / 507
6-4a-2 Effect of Solvent and Counterion / 508
6-4a-3 Effect of Temperature / 510
6-4b Anionic Copolymerization / 510
6-4b-1 Reactivity / 510
6-4b-2 Effects of Solvent and Counterion / 511
6-4b-3 Effect of Temperature / 512
6-5 Deviations from Terminal Copolymerization Model / 512
6-5a Kinetic Penultimate Behavior / 513
6-5b Depropagation during Copolymerization / 515
6-5c Copolymerization with Complex Participation / 518
6-5d Discrimination between Models / 521
6-6 Copolymerizations Involving Dienes / 521
6-6a Crosslinking / 521
6-6b Alternating Intra/intermolecular Polymerization;
Cyclopolymerization / 524
6-6c Interpenetrating Polymer Networks / 527
6-7 Other Copolymerizations / 528
6-7a Miscellaneous Copolymerizations of Alkenes / 528
6-7b Copolymerization of Carbonyl Monomers / 528
6-8 Applications of Copolymerization / 529
6-8a Styrene / 529
6-8b Ethylene / 530
6-8c Unsaturated Polyesters / 531
6-8d Allyl Resins / 532
6-8e Other Copolymers / 532
References / 533

7 RING-OPENING POLYMERIZATION 544

7-1 General Characteristics / 545
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