n-Nylons Their Synthesis, Structure, and

This book describes the synthesis, structure and properties of the polyamide family known by the common term n-nylon. Both the chemistry and physics are combined, making it a unique contribution to literature in this field. After general chapters on thermodynamics, polycondensation and crystallinity, all nylons from n=1 to n=22 are discussed in detail and the book concludes with chapters discussing the similarities of different nylons and their technologically important properties.

Shaul M. Aharoni is the author of n-Nylons: Their Synthesis, Structure, and Properties, published by Wiley.

Preface

xiii

PART 1 INTRODUCTION AND GENERALITIES

1

(76)

Chapter 1.1 Nomenclature and Fundamental Structural Features

3

(12)

1.1.1 References

13

(2)

Chapter 1.2 A Little Thermodynamics

15

(19)

1.2.1 Polycondensation of XXX-amino acids

16

(5)

1.2.2 Ring-opening polymerizations of lactams

21

(11)

1.2.3 References

32

(2)

Chapter 1.3 Crystallinity and Polymorphism in the n-Nylon Family

34

(41)

1.3.1 References

70

(5)

PART 2 SPECIFICS OF THE n-NYLONS

75

(368)

Chapter 2.1 N-Substituted 1-Nylons

77

(42)

2.1.1 Monomers of N-substituted 1-nylons

80

(6)

2.1.2 Polymerization

86

(4)

2.1.3 Solution properties, liquid-crystal polymers

90

(17)

2.1.3.1 Stiffness and flexibility of polymer chains

90

(5)

2.1.3.2 Dilute-solution behavior of N-substituted 1-nylons

95

(8)

2.1.3.3 Concentrated-solution and liquid-crystal behavior of poly(alkyl and aralkyl-isocyanates)

103

(4)

2.1.4 Bulk structure and properties

107

(6)

2.1.5 References

113

(6)

Chapter 2.2 2-Nylons: Natural and Manufactured Structural Proteins

119

(31)

2.2.1 Monomers and their polymerization

124

(6)

2.2.2 Helices and sheets: secondary structure of synthetic polypeptides

130

(6)

2.2.3 Solution properties of 2-nylons

136

(7)

2.2.4 References

143

(7)

Chapter 2.3 3-Nylons

150

(9)

2.3.1 Monomers and their polymerization

150

(3)

2.3.2 Properties of 3-nylon polymers

153

(2)

2.3.3 Random copolymers of substituted 2-nylon and 3-nylon

155

(2)

2.3.4 References

157

(2)

Chapter 2.4 4-Nylon

159

(7)

2.4.1 The monomer and its polymerization

160

(2)

2.4.2 Properties of 4-nylon

162

(2)

2.4.3 References

164

(2)

Chapter 2.5 5-Nylon

166

(4)

2.5.1 The monomer and its polymerization

166

(1)

2.5.2 5-Nylon and its properties

167

(2)

2.5.3 References

169

(1)

Chapter 2.6 6-Nylon

170

(177)

2.6.1 Monomers and their preparation

170

(4)

2.6.2 Polymerizations

176

(32)

2.6.2.1 Hydrolytic polymerizations

178

(10)

2.6.2.1.1 Re-equilibration of hydrolytically polymerized polyamides

185

(3)

2.6.2.2 Anionic polymerization

188

(6)

2.6.2.3 Cationic polymerizations

194

(2)

2.6.2.4 Acidolytic and aminolytic polymerizations

196

(2)

2.6.2.5 Polymerization of N-substituted and C-substituted lactams

198

(2)

2.6.2.5.1 Polymerization of N-substituted lactams

198

(1)

2.6.2.5.2 Polymerization of C-substituted lactams

199

(1)

2.6.2.6 Lactam polymerization miscellanea

200

(1)

2.6.2.7 6-Aminocaproic acid polymerization

201

(1)

2.6.3 Molecular weights and their distribution; viscosity

202

(36)

2.6.3.1 Weights and sizes of macromolecules

204

(4)

2.6.3.2 Distributions

208

(2)

2.6.3.3 Brief description of the experimental methods for the determination of molecular weights

210

(15)

2.6.3.3.1 Sample preparation

210

(3)

2.6.3.3.2 Methods to determine M(n)

213

(1)

2.6.3.3.3 Methods to determine M(w)

214

(9)

2.6.3.3.4 Molecular-weight distributions of 6-nylon

223

(2)

2.6.3.4 Solution and melt viscosities

225

(13)

2.6.4 End-groups, additives, and so on

238

(9)

2.6.5 Structure, morphology, and some properties of 6-nylon

247

(49)

2.6.5.1 Structure and thermal properties

249

(28)

2.6.5.1.1 Aspects of the glassy state and glass transition

252

(25)

2.6.5.2 Morphology

277

(7)

2.6.5.3 Memory effects

284

(12)

2.6.6 Hydrogen bonds and chain mobility in solution and in the melt

296

(16)

2.6.7 6-Nylon monomer regeneration

312

(4)

2.6.8 Technologically important properties of 6-nylon

316

(9)

2.6.9 References

325

(22)

Chapter 2.7 7-Nylon

347

(20)

2.7.1 Monomers, their preparation, and polymerization

347

(9)

2.7.2 Characteristics and properties of 7-nylon

356

(8)

2.7.3 References

364

(3)

Chapter 2.8 8-Nylon

367

(14)

2.8.1 Monomers, their preparation, and polymerization

367

(7)

2.8.2 Properties of 8-nylon

374

(4)

2.8.3 References

378

(3)

Chapter 2.9 9-Nylon

381

(9)

2.9.1 Monomers, their preparation, and polymerization

381

(3)

2.9.2 Properties of 9-nylon

384

(3)

2.9.3 References

387

(3)

Chapter 2.10 10-Nylon

390

(7)

2.10.1 Monomers and their polymerization

390

(3)

2.10.2 Properties of 10-nylon

393

(2)

2.10.3 References

395

(2)

Chapter 2.11 11-Nylon

397

(16)

2.11.1 Monomers for 11-Nylon, their preparation, and polymerization

397

(4)

2.11.2 Characteristics and properties of 11-nylon

401

(8)

2.11.3 References

409

(4)

Chapter 2.12 12-Nylon

413

(20)

2.12.1 Monomers, their synthesis, and polymerization

414

(9)

2.12.2 Properties of 12-nylon

423

(7)

2.12.3 References

430

(3)

Chapter 2.13 The Higher Nylons: 13-Nylon to 22-Nylon

433

(10)

2.13.1 13-Nylon

433

(3)

2.13.1.1 The Monomer and its polymerization

434

(2)

2.13.1.2 Properties of 13-nylon

436

(1)

2.13.2 15-Nylon

436

(1)

2.13.3 17-Nylon

437

(1)

2.13.3.1 The monomers and their polymerization

437

(1)

2.13.3.2 Properties of 17-nylon

438

(1)

2.13.4 18-Nylon

438

(1)

2.13.4.1 Monomer and polymerization

438

(1)

2.13.4.2 Properties of 18-nylon

439

(1)

2.13.5 22-Nylon

439

(2)

2.13.5.1 The monomer and its polymerization

440

(1)

2.13.5.2 Properties of 22-nylon

440

(1)

2.13.6 References

441

(2)

PART 3 MISCELLANEA

443

(72)

Chapter 3.1 N-substituted and C-Substituted n-Nylons

445

(16)

3.1.1 N- and C-substituted monomers and their polymerization

448

(8)

3.1.2 Some properties of substituted n-nylons

456

(2)

3.1.3 References

458

(3)

Chapter 3.2 Miscibility of n-Nylons and Substituted n-Nylons

461

(6)

3.2.1 References

465

(2)

Chapter 3.3 Some n-Nylon Additives of Technological Interest

467

(22)

3.3.1 References

486

(3)

Chapter 3.4 Ferroelectricity of Odd n-Nylons

489

(13)

3.4.1 References

500

(2)

Chapter 3.5 Spectroscopic Identification of n-Nylons

502

(13)

3.5.1 Infrared and Raman spectroscopy

503

(5)

3.5.2 Simple NMR spectroscopies

508

(4)

3.5.3 References

512

(3)

PART 4 THE BACKBONE OF THE n-NYLON FAMILY: FROM STIFF AND EXTENDED TO FLEXIBLE AND FOLDABLE

515

(48)

Chapter 4.1 A Little Physics

517

(19)

4.1.1 References

532

(4)

Chapter 4.2 Some Effects of Main-Chain Flexibility

536

(27)

4.2.1 References

559

(4)

Glossary

563

(8)

Units and Some Conversion Factors

571

(8)

Index

579

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n-Nylons Their Synthesis, Structure, and Properties

Summary

Author Biography

Table of Contents

Supplemental Materials