Poly(lactic acid): Synthesis, Structures, Properties, Processing, and ApplicationsISBN: 978-0-470-29366-9
Hardcover
528 pages
October 2010
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Preface xvii
Contributors xxi
Part I Chemistry and Production of Lactic Acid, Lactide, and Poly(Lactic Acid) 1
1 Production and Purification of Lactic Acid and Lactide 3
Wim Groot, Jan van Krieken, Olav Sliekersl, and Sicco de Vos
1.1 Introduction 3
1.2 Lactic Acid 4
1.2.1 History of Lactic Acid 4
1.2.2 Physical Properties of Lactic Acid 4
1.2.3 Chemistry of Lactic Acid 4
1.2.4 Production of Lactic Acid by Fermentation 5
1.2.5 Downstream Processing/Purification of Lactic Acid 8
1.2.6 Quality/Specifications of Lactic Acid 10
1.3 Lactide 10
1.3.1 Physical Properties of Lactide 10
1.3.2 Production of Lactide 11
1.3.3 Purification of Lactide 13
1.3.4 Quality and Specifications of Polymer-Grade Lactide 14
1.3.5 Concluding Remarks on Polymer-Grade Lactide 16
References 16
2 Chemistry and Thermodynamic Properties of Lactic Acid and Lactide and Solvent Miscibility 19
Zhengyu Jin, Yaoqi Tian, and Jinpeng Wang
2.1 General Properties 19
2.1.1 Physical and Chemistry Properties of Lactic Acid 19
2.1.2 Physical and Chemical Properties of Lactide 19
2.2 Thermodynamic Properties 19
2.2.1 Vapor Pressures of Lactic Acids at Different Temperatures 19
2.2.2 Temperature Dependence of Densities of Lactic Acid 20
2.2.3 Temperature Dependence of Viscosity of Lactic Acid 20
2.2.4 Thermodynamic Properties 21
2.3 Miscibility Properties of Lactic Acid and Lactide 21
2.3.1 Miscibility of Lactic Acid with Different Solvents 21
2.3.2 Miscibility of Lactic Acid with Modifiers in Diluents 21
2.3.3 Physical and Chemical Equilibrium of Lactic Acid 22
2.3.4 Miscibility of Lactide with Solvents 25
References 25
3 Industrial Production of High Molecular Weight Poly(Lactic Acid) 27
Anders Södergård and Mikael Stolt
3.1 Introduction 27
3.2 Lactic Acid Based Polymers by Polycondensation 28
3.2.1 Direct Condensation 29
3.2.2 Solid-State Polycondensation 30
3.2.3 Azeotropic Dehydration 31
3.3 Lactic Acid Based Polymers by Chain Extension 32
3.3.1 Chain Extension with Diisocyanates 32
3.3.2 Chain Extension with Bis-2-oxazoline 33
3.3.3 Dual Linking Processes 34
3.3.4 Chain Extension with Bis-epoxies 34
3.4 Lactic Acid Based Polymers by Ring-Opening Polymerization 34
3.4.1 Polycondensation Processes 35
3.4.2 Lactide Manufacturing 35
3.4.3 Ring-Opening Polymerization 36
References 37
4 Design and Synthesis of Different Types of Poly(Lactic Acid) 43
Ann-Christine Albertsson, Indra Kumari Varma, Bimlesh Lochab, Anna Finne-Wistrand, and Kamlesh Kumar
4.1 Introduction 43
4.2 Copolymerization 43
4.2.1 Synthesis of Copolymers of Lactic Acid: Glycolic Acid 44
4.2.2 Synthesis of Copolymers of Lactic Acid: Poly(ethylene glycol) 44
4.2.3 Synthesis of Copolymers of Lactic Acid: d-Valerolactone and Lactic Acid: b-Butyrolactone 45
4.2.4 Synthesis of Copolymers of Lactic Acid: e-Caprolactone 46
4.2.5 Synthesis of Copolymers of Lactic Acid: 1,5-Dioxepan-2-one 46
4.2.6 Synthesis of Copolymers of Lactic Acid: Trimethylene Carbonate 46
4.2.7 Synthesis of Copolymers of Lactic Acid: Poly(N-isopropylacrylamide) 47
4.2.8 Synthesis of LA: Alkylthiophene (P3AT) Copolymers 47
4.2.9 Functional Poly(lactic acid) 47
4.2.10 Branched Copolymers 48
4.3 Properties of Copolymers 53
4.3.1 Degradation of Homo- and Copolymers 54
4.3.2 Drug Delivery from PLLA Copolymers 54
4.3.3 Radiation Effects 55
References 55
5 Structure and Properties of Stereocomplex-Type Poly(lactic acid) 59
Masayuki Hirata and Yoshiharu Kimura
5.1 Introduction 59
5.2 Formation of Stereocomplex Crystals 59
5.3 Thermal Properties of sc-PLA 60
5.4 Crystal Structure of sc-PLA 60
5.4.1 Unit Cell Parameters and Molecular Conformation of sc-PLA 60
5.4.2 Density and Heat of Fusion of Sccrystals 60
5.5 Formation of sb-PLA 61
5.5.1 ROP Routes to Diblock and Multiblock sb-PLA 61
5.5.2 SSP Routes to Multiblock sb-PLA 63
5.6 Applications of sc-PLA 64
References 65
Part II Properties of Poly(Lactic Acid) 67
6 Chemical Structure of Poly(lactic acid) 69
Xue Jiang, Yan Luo, Xiuzhi Tian, Dan Huang, Narendra Reddy, and Yiqi Yang
6.1 Introduction 69
6.2 Chain Structure and Configuration 69
6.2.1 Chain Structure 69
6.2.2 Configuration 70
6.2.3 Interlocked Structure, Polymer Blend, and Resistance to Hydrolysis 71
6.3 Syndiotactic Polymerization and Syndiotacticity 72
6.4 Conformation 74
6.5 Amorphous Structure and Thermal Properties 74
6.5.1 Amorphous and Three-Phase Models 74
6.5.2 Glass Transition 75
6.6 Orientation Structure of PLA 77
6.6.1 Mechanical Orientation by Stretching or Compression 77
6.6.2 Thermal Orientation (Phase Transition) 77
6.7 Semicrystalline Structure 78
6.7.1 General 78
6.7.2 Three Forms (a, b and c) of the Crystal Structure 78
6.8 Frustrated Structure 79
6.9 Molecular Weight 80
6.10 Summary 80
References 80
7 Chemical Compatibility of Poly(lactic acid): A Practical Framework Using Hansen Solubility Parameters 83
Steven Abbott
7.1 A Practical Framework 83
7.1.1 Thermodynamics Versus Kinetics 83
7.1.2 Hansen Solubility Parameters 83
7.2 Solvent Compatibility 84
7.3 Plasticizers 86
7.4 Polymer Compatibility 87
7.5 Environmental Stress Cracking 89
7.6 Rational Composite Design 89
7.7 Diffusion and Barrier Properties 90
7.7.1 Gases 91
7.7.2 Water 91
7.8 Pharmacological Transport 93
7.9 Summary 93
References 94
8 Optical Properties 97
Carla M. B. Gonçalves, João A. P. Coutinho, and Isabel M. Marrucho
8.1 Introduction 97
8.2 Absorption and Transmission of UV-Vis Radiation 97
8.3 Refractive Index 99
8.4 Specific Optical Rotation 100
8.5 Infrared and Raman Spectroscopy 100
8.5.1 Infrared Spectroscopy 101
8.5.2 Raman Spectroscopy 105
8.6 1H and 13C NMR Spectroscopy 108
References 111
9 Crystallization and Thermal Properties 113
Luca Fambri and Claudio Migliaresi
9.1 Introduction 113
9.2 Crystallinity and Crystallization 114
9.3 Crystallization Regime 118
9.4 Fibers 119
9.5 Hydrolytic Degradation 121
References 123
10 Rheology of Poly(lactic acid) 125
John R. Dorgan
10.1 Introduction 125
10.2 Fundamental Chain Properties from Dilute Solution Viscometry 126
10.2.1 Unperturbed Chain Dimensions 126
10.2.2 Real Chains 126
10.2.3 Solution Viscometry 127
10.2.4 Viscometry of PLA 128
10.3 Processing of PLA: General Considerations 130
10.4 Melt Rheology: An Overview 131
10.5 Processing of PLA: Rheological Properties 132
10.6 Conclusions 137
Appendix 10.A Description of the Software 138
References 138
11 Mechanical Properties 141
Gabriele Perego and Gian Domenico Cella
11.1 Introduction 141
11.2 General Mechanical Properties and Molecular Weight Effect 141
11.2.1 Tensile and Flexural Properties 141
11.2.2 Impact Resistance 143
11.2.3 Hardness 143
11.3 Temperature Effect 143
11.4 Annealing 144
11.5 Orientation 147
11.6 Stereoregularity 148
11.7 Plasticization 149
11.8 Relaxation and Aging 151
11.9 Conclusions 152
References 152
12 Permeation, Sorption, and Diffusion in Poly(lactic acid) 155
Eva Almenar and Rafael Auras
12.1 Introduction 155
12.2 Factors Affecting Permeability, Sorption, and Diffusion in PLA 157
12.2.1 L-Lactide Unit Content 157
12.2.2 Plasticizers 158
12.2.3 Crystallization 159
12.2.4 Orientation 160
12.2.5 Free volume 160
12.2.6 Branching 160
12.2.7 Environmental Factors 161
12.3 Permeability, Sorption, and Diffusion of Pure PLA 163
12.3.1 Gases 163
12.3.2 Water Vapor 165
12.3.3 Organics 167
12.4 Copolymers 169
12.5 PLA Blends 169
12.5.1 PLA/Starch Blends 169
12.5.2 PLA/Poly(€-caprolactone) Blends 170
12.5.3 PLA/Chitosan Blends 171
12.5.4 PLA/Poly((R)-3-hydroxybutyrate) Blends 171
12.6 PLA Laminations 171
12.7 Coated PLA 171
12.8 PLA Composites and Fibers 171
12.8.1 PLA Composites 172
12.8.2 Fiber-Reinforced PLA 172
12.9 PLA Nanocomposites 172
12.10 Future of PLA Membranes 176
References 176
13 Migration 181
Herlinda Soto-Valdez
13.1 Migration Principles 181
13.2 Legislation 182
13.3 Migration and Toxicological Data of Lactic Acid, Lactide, Dimers and Oligomers 182
13.3.1 Lactic Acid 182
13.3.2 Lactide 186
13.3.3 Oligomers 186
13.4 EDI of Lactic Acid 187
13.5 Other Potential Migrants from PLA 187
13.6 Conclusions 187
References 188
Part III Processing and Conversion of Poly(Lactic Acid) 189
14 Processing of Poly(lactic acid) 191
Loong-Tak Lim, Kevin Cink, and Tim Vanyo
14.1 Introduction 191
14.2 Properties of PLA Relevant to Processing 191
14.3 Modification of PLA Properties by Process Aids and Other Additives 193
14.4 Drying 194
14.5 Extrusion 195
14.6 Injection Molding 196
14.7 Film and Sheet Casting 201
14.8 Stretch Blow Molding 204
14.9 Extrusion Blown Film 207
14.10 Thermoforming 208
14.11 Electrospinning 209
14.12 Conclusion: Prospects of PLA Polymers 211
References 213
15 Poly(lactic acid)/Starch Blends 217
Long Yu, Eustathios Petinakis, Katherine Dean, and Hongshen Liu
15.1 Introduction 217
15.2 Blending Hydrophobic PLA with Hydrophilic Starch 218
15.3 Compatibilizers Used for Starch/PLA Blends 219
15.4 Enhancing Function of Compatibilizer by Controlling Compatibilizer Distribution 220
15.5 Reactive Blending 223
15.6 Summary 225
References 225
16 Poly(lactic acid) Blends 227
Sukeewan Detyothin, Ajay Kathuria, Waree Jaruwattanayon, Susan E. M. Selke, and Rafael Auras
16.1 Introduction 227
16.2 PLA/Nonbiodegradable Polymer Blends 227
16.2.1 Polyolefins 228
16.2.2 Vinyl and Vinylidene Polymers and Copolymers 229
16.2.3 Elastomers and Rubbers 238
16.2.4 PMMA/PLA Blends 239
16.3 PLA/Biodegradable Polymer Blends 240
16.3.1 Polyanhydrides 240
16.3.2 Vinyl and Vinylidene Polymers and Copolymers 242
16.3.3 Aliphatic Polyesters and Copolyesters 244
16.3.4 Aliphatic-Aromatic Copolyester 255
16.3.5 Elastomers and Rubbers 257
16.3.6 Poly(ester amide) 258
16.3.7 Polyethers and Copolymer 258
16.3.8 Annually Renewable Biodegradable Materials 261
16.4 Plasticization of PLA 264
16.5 Conclusion 266
References 266
17 Foaming 273
Laurent M. Matuana
17.1 Introduction 273
17.2 Plastic Foams 273
17.3 Foaming Agents 274
17.3.1 Physical Foaming Agents 274
17.3.2 Chemical Foaming Agents 274
17.4 Formation of Cellular Plastics 275
17.4.1 Dissolution of Blowing Agent in Polymer 275
17.4.2 Bubble Formation 275
17.4.3 Bubble Growth and Stabilization 276
17.5 Plastic Foams Expanded with Physical Foaming Agents 276
17.5.1 Microcellular Foamed Polymers 276
17.5.2 Solid State Batch Microcellular Foaming Process 277
17.5.3 Microcellular Foaming in a Continuous Process 282
17.6 PLA Foamed with Chemical Foaming Agents 286
17.6.1 Effect of CFA Content 286
17.6.2 Effect of Processing Conditions 287
17.7 Mechanical Properties of PLA Foams 288
17.7.1 Batch Microcellular Foamed PLA 288
17.7.2 Microcellular Extrusion of PLA 288
17.7.3 Microcellular Injection Molding of PLA 288
17.8 Foaming of PLA/starch Blends 289
References 289
18 Composites 293
Subrata Bandhu Ghosh, Sanchita Bandyopadhyay-Ghosh, and Mohini Sain
18.1 Introduction 293
18.2 PLA Matrix 293
18.3 Reinforcements 294
18.3.1 Natural Fiber Reinforcement 294
18.3.2 Synthetic Fiber Reinforcement 295
18.3.3 Organic Filler Reinforcement 296
18.3.4 Inorganic Filler Reinforcement 298
18.4 Fiber/Matrix Adhesion 298
18.4.1 Surface Modification 298
18.4.2 Compatibilizing Agent 299
18.5 PLA Nanocomposites 299
18.6 Processing 300
18.7 Properties 300
18.7.1 Mechanical Properties 300
18.7.2 Thermal Properties 303
18.7.3 Degradation 304
18.8 Applications 305
18.8.1 Biomedical Applications 305
18.8.2 Packaging Applications 306
18.8.3 Automotive Applications 306
18.8.4 Electronic Applications 307
18.9 Future Developments and Concluding Remarks 307
References 307
19 Nanocomposites 311
Suprakas Sinha Ray
19.1 Introduction 311
19.2 PLA Nanocomposites Based on Clay 312
19.2.1 Structure and Properties of Clay 312
19.2.2 Preparation and Characterization of PLA/Clay Nanocomposites 312
19.3 PLA Nanocomposites Based on Carbon Nanotubes 314
19.4 PLA Nanocomposites Based on Various Other Nanoparticles 315
19.5 Properties of PLA-Based Nanocomposites 316
19.6 Biodegradability 317
19.7 Melt Rheology 318
19.8 Foam Processing 319
19.9 Possible Applications and Future Prospects 320
Acknowledgments 321
References 321
20 Spinning of Poly(lactic acid) Fibers 323
Ashwini K. Agrawal
20.1 Defining Fiber and Fiber Spinning 323
20.2 Melt Spinning Line 323
20.3 Fluid Dynamics During Spinning 326
20.3.1 Instabilities During Flow Through Spinneret 326
20.3.2 Instabilities in the Spinning Zone: Draw Resonance 327
20.4 Structure Development During Melt Spinning 328
20.4.1 Spinning at Low Speeds 328
20.4.2 Spinning at High Speeds 328
20.5 Post-Spinning Operation 330
20.5.1 Drawing 330
20.5.2 Finish Application 330
20.5.3 Crimping 330
20.5.4 Heat Setting 330
20.6 Structure Development During Drawing 331
20.7 Solution Spinning of PLLA 333
20.7.1 Wet Spinning 334
20.7.2 Dry Spinning 335
20.7.3 Factors Affecting Solution Spinning 335
20.7.4 Dry-Jet Wet Spinning 337
20.7.5 Solution Spinning of Stereocomplex Fiber 337
20.8 Mechanical Properties 338
20.8.1 Melt-Spun PLLA 338
20.8.2 Solution-Spun PLLA 339
20.8.3 Stereocomplex Fiber 341
References 341
Part IV Degradation and Environmental Issues 343
21 Hydrolytic Degradation 345
Hideto Tsuji
21.1 Introduction 345
21.2 Degradation Mechanism 345
21.2.1 Molecular Degradation Mechanism 346
21.2.2 Material Degradation Mechanism 355
21.2.3 Degradation of Crystalline Residues 360
21.3 Parameters for Hydrolytic Degradation 362
21.3.1 Effects of Surrounding Media 362
21.3.2 Effects of Material Parameters 365
21.4 Structural and Property Changes During Hydrolytic Degradation 371
21.4.1 Fractions of Components 371
21.4.2 Crystallization 371
21.4.3 Mechanical Properties 372
21.4.4 Thermal Properties 372
21.4.5 Surface Properties 372
21.4.6 Morphology 373
21.5 Applications of Hydrolytic Degradation 373
21.5.1 Material Preparation 373
21.5.2 Recycling of PLA to Its Monomer 375
21.5.3 Miscellaneous Applications 376
21.6 Conclusions 376
References 376
22 Enzymatic Degradation 383
Tadahisa Iwata, Hideki Abe, and Yoshihiro Kikkawa
22.1 Introduction 383
22.1.1 Definition of Biodegradable Plastics 383
22.1.2 Enzymatic Degradation 383
22.2 Enzymatic Degradation of PLA Films 384
22.2.1 Structure and Substrate Specificity of Proteinase K 385
22.2.2 Enzymatic Degradability of PLLA Films 385
22.2.3 Enzymatic Degradability of PLA Stereoisomers and Their Blends 386
22.2.4 Effects of Surface Properties on Enzymatic Degradability of PLLA Films 388
22.3 Enzymatic Degradation of Thin Films 390
22.3.1 Thin Films and Analytical Techniques 390
22.3.2 Crystalline Morphologies of Thin Films 391
22.3.3 Enzymatic Adsorption and Degradation Rate of Thin Films 391
22.3.4 Enzymatic Degradation of LB Film 394
22.3.5 Application of Selective Enzymatic Degradation 394
22.4 Enzymatic Degradation of Lamellar Crystals 395
22.4.1 Enzymatic Degradation of PLLA Single Crystals 395
22.4.2 Thermal Treatment and Enzymatic Degradation of PLLA Single Crystals 396
22.4.3 Single Crystals of PLA Stereocomplex 397
22.5 Future Perspectives 397
References 398
23 Thermal Degradation 401
Haruo Nishida
23.1 Introduction 401
23.2 Kinetic Analysis of Thermal Degradation 401
23.2.1 Changes in Molecular Weight 401
23.2.2 Thermogravimetry 402
23.3 Thermal Degradation Behavior of PLA Based on Molecular Weight Change 403
23.4 Thermal Degradation Behavior of PLA Based on Weight Loss 403
23.4.1 Diverse Mechanisms of PLA Pyrolysis 403
23.4.2 Effects of Polymerization Catalyst Residues 404
23.4.3 Effects of Chain-End Structures 406
23.4.4 Thermal Degradation Catalysts 406
23.4.5 Thermal Degradation Behavior of PLA Stereocomplex: sc-PLA 408
23.4.6 Control of Racemization 409
23.4.7 Selective Depolymerization of PLA in Blends 409
23.5 Conclusions 410
References 410
24 Photodegradation and Radiation Degradation 413
Wataru Sakai and Naoto Tsutsumi
24.1 Introduction 413
24.2 Mechanisms of Photodegradation 413
24.2.1 Photon 413
24.2.2 Photon Absorption 414
24.2.3 Photochemical Reaction of Carbonyl Groups 415
24.3 Mechanism of Radiation Degradation 415
24.3.1 High Energy Radiation 415
24.3.2 Basic Mechanism of Radiation Degradation 415
24.4 Photodegradation of PLA 416
24.5 Photosensitized Degradation of PLA 418
24.6 Radiation Effects on PLA 419
24.7 Modification of PLA by Irradiation 420
References 420
25 Biodegradation 423
Buenaventurada P. Calabia, Yutaka Tokiwa, Charles U. Ugwu, and Seiichi Aiba
25.1 Introduction 423
25.2 Microbial Degradation 423
25.2.1 Field Test 423
25.2.2 ISO and ASTM Standards 424
25.2.3 PLLA Degrading Microorganisms 424
25.3 Poly(L-Lactide) Degrading Enzymes 426
25.3.1 Proteinase K 426
25.3.2 PLLA-Degrading Enzyme of Amycolatopsis sp. 426
25.3.3 Induction of PLLA Degrading Enzymes with Natural Substrates 426
25.3.4 Other Serine Proteases 426
25.3.5 Lipase 426
25.3.6 Enzymatic Degradation in Organic Solvents 427
25.3.7 Evolution of PLA Degrading Enzymes 428
25.4 Conclusion and Future Prospects 428
References 429
26 Cradle to Gate Environmental Footprint and Life Cycle Assessment of Poly(lactic acid) 431
Amy E. Landis
26.1 Introduction to LCA and Environmental Footprints 431
26.1.1 Life Cycle Assessment 431
26.1.2 Uncertainty in LCA 432
26.2 Life Cycle Considerations for PLA 432
26.2.1 The Life Cycle of PLA 432
26.2.2 Energy USE and Global Warming 433
26.2.3 Environmental Trade-Offs 434
26.3 Review of Biopolymer LCA Studies 434
26.4 Improving PLA’s Environmental Footprint 438
26.4.1 Agricultural Management 438
26.4.2 Feedstock Choice 439
26.4.3 Energy 439
Further Reading on LCA 440
References 440
Part V Applications 443
27 Medical Applications 445
Shuko Suzuki and Yoshito Ikada
27.1 Introduction 445
27.2 Minimal Requirements for Medical Devices 445
27.2.1 General 445
27.2.2 PLA as Medical Implants 446
27.3 Preclinical and Clinical Applications of PLA Devices 447
27.3.1 Fibers 447
27.3.2 Meshes 448
27.3.3 Bone Fixation Devices 448
27.3.4 Microspheres, Microcapsules, and Thin Coatings 453
27.4 Conclusions 454
References 454
28 Packaging and Other Commercial Applications 457
Shoji Obuchi and Shinji Ogawa
28.1 Introduction 457
28.2 Applications in Packaging and Containers 457
28.2.1 Oriented Film 457
28.2.2 Flexible Film 458
28.2.3 Shrink Labels and Film 461
28.2.4 Thermoforming 462
28.2.5 Lamination 462
28.3 Other Commercial Applications 462
28.3.1 Agricultural and Engineering Materials 462
28.3.2 Electrical Appliances 463
28.3.3 Automotive Materials 466
28.4 Conclusions 467
References 467
29 Textile Applications 469
Masatsugu Mochizuki
29.1 Introduction 469
29.2 Manufacturing, Properties, and Structure of PLA Fibers 469
29.2.1 PLA Fiber Manufacture 469
29.2.2 PLA Fibers and Textile Properties 469
29.2.3 Effects of Structure on Properties 470
29.2.4 PLA Stereocomplex Fibers 471
29.3 Key Performance Features of PLA Fibers 471
29.3.1 Biodegradability and the Biodegradation Mechanism 471
29.3.2 Moisture Management 472
29.3.3 Antibacterial/Antifungal Properties 472
29.3.4 Low Flammability 473
29.3.5 Weathering Stability 474
29.4 Potential Applications 474
29.4.1 Geotextiles 474
29.4.2 Industrial Fabrics 475
29.4.3 Filters 475
29.4.4 Towels and Wipes 475
29.4.5 Home Furnishings 475
29.4.6 Clothing and Personal Belongings 475
29.5 Conclusions 475
References 476
30 Environmental Applications 477
Akira Hiraishi
30.1 Introduction 477
30.2 Application to Water and Wastewater Treatment 477
30.2.1 Application as Sorbents 477
30.2.2 Application to Nitrogen Removal 479
30.3 Application to Bioremediation 482
30.3.1 Significance of PLA Use 482
30.3.2 Bioremediation of Organohalogen Pollution 482
30.3.3 Other Applications 483
30.4 Concluding Remarks and Prospects 484
Acknowledgments 484
References 484
Index 487
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