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Poly(lactic acid): Synthesis, Structures, Properties, Processing, and Applications

Rafael A. Auras (Editor), Loong-Tak Lim (Editor), Susan E. M. Selke (Editor), Hideto Tsuji (Editor)
ISBN: 978-0-470-29366-9
528 pages
October 2010
Poly(lactic acid): Synthesis, Structures, Properties, Processing, and Applications (0470293667) cover image
This book describes the synthesis, properties, and processing methods of poly(lactic acid) (PLA), an important family of degradable plastics. As the need for environmentally-friendly packaging materials increases, consumers and companies are in search for new materials that are largely produced from renewable resources, and are recyclable. To that end, an overall theme of the book is the biodegradability, recycling, and sustainability benefits of PLA. The chapters, from a base of international expert contributors, describe specific processing methods, spectroscopy techniques for PLA analysis, and and applications in medical items, packaging, and environmental use.
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List of Contributors.



Chapter 1. Production and Purification of Lactic Acid and Lactide.

1.1 Introduction.

1.2 Lactic acid.

1.3 Lactide.


Chapter 2. Chemistry and Thermodynamic Properties of Lactic acid and Lactide and Solvent Miscibility.

2.1 General properties.

2.2 Thermodynamic properties.

2.3 Miscibility properties of lactic acid and lactide.


Chapter 3. Industrial Production of High Molecular Weight Poly(lactic acid).

3.1 Introduction.

3.2 Lactic acid based polymers by polycondensation.

3.3 Lactic acid based polymers by chain-extension.

3.4 Lactic acid based polymers by ring-opening polymerization.


Chapter 4. Design and Synthesis of Different types of poly(lactic acid).

4.1 Introduction.

4.2 Copolymerization.

4.3. Properties of copolymers.


Chapter 5. Structure and Properties of Stereocomplex-type Poly(lactic acid).

5.1 Introduction.

5.2 Formation of stereocomplex crystals.

5.3 Thermal properties of sc-PLA.

5.4 Crystal structure of sc-PLA.

5.5 Formation of sb-PLA.

5.6 Applications of sc-PLA.



Chapter 6. Chemical Structure of Poly(lactic acid).

6.1 Introduction.

6.2 Chain structure and configuration.

6.3 Syndiotactic polymerization and syndiotacticity.

6.4 Conformation.

6.5 Amorphous structure and thermal properties.

6.6 Orientation structure of PLA.

6.7 Semi-crystalline structure.

6.8 Frustrated structure.

6.9 Molecular weight.

6.10 Summary.


Chapter 7. Chemical Compatibility of Poly(lactic acid) A Practical Framework using Hansen Solubility Parameters.

7.1 A practical framework?

7.2 Solvent compatibility.

7.3 Plasticizers.

7.4 Polymer compatibility.

7.5 Environmental stress cracking.

7.6 Rational composite/nanocomposite design.

7.7 Diffusion & Barrier properties.

7.8 Pharmacological transport.

7.9 Summary.


Chapter 8. Optical Properties.

8.1 Introduction.

8.2 Absorption and Transmission of UV-Vis Radiation.

8.3 Refractive Index.

8.4 Specific Optical Rotation.

8.5 Infrared and Raman Spectroscopy.

8.6 1H and 13C NMR Spectroscopy


Chapter 9. Crystallization and Thermal Properties.

9.1 Introduction.

9.2 Crystallinity and crystallization.

9.3 Crystallization regimes.

9.4 Fibers.

9.5 Hydrolytic degradation.


Chapter 10. Rheology of Poly(lactic acid).

10.1 Introduction.

10.2 Fundamental chain properties from dilute solution viscometry.

10.3 Processing of PLA: General Considerations.

10.4 Melt Rheology: An Overview.

10.5 Processing of PLA: Melt Rheology.

10.6 Conclusions.


Appendix A: Description of the Software.

Chapter 11. Mechanical Properties.

11.1 Introduction.

11.2 General mechanical properties and molecular weight effect.

11.3 Temperature effect.

11.4 Annealing.

11.5 Orientation.

11.6 Stereoregularity.

11.7 Plasticization.

11.8 Relaxation and aging.

11.9 Conclusions.


Chapter 12. Permeation, Sorption, and Diffusion in Poly(lactic acid).

12.1 Introduction.

12.2 Factors affecting permeability, sorption, and diffusion in PLA.

12.3 Permeability, sorption, and diffusion of pure PLA.

12.4 Copolymers.

12.5 PLA blends.

12.6 PLA laminations.

12.7 Coated PLA.

12.8 PLA composites and fibers.

12.9 PLA nanocomposites.

12.10 Future of PLA membranes.


Chapter 13. Migration.

13.1 Migration principles.

13.2 Legislation.

13.3 Migration and toxicological data of lactic acid, lactide, dimers and oligomers.

13.4 Estimated daily intake of lactic acid.

13.5 Other potential migrants from PLA.

13.6 Conclusions.



Chapter 14. Properties of Poly(lactic acid).

14.1 Introduction.

14.2 Properties of PLA Relevant to Processing.

14.3 Modification of PLA Properties by Process Aids and Other Additives.

14.4 Drying.

14.5 Extrusion.

14.6 Injection Molding.

14.7 Film and Sheet Casting.

14.8 Stretch Blow Molding.

14.9 Extrusion Blown Film.

14.10 Thermoforming.

14.11 Electrospinning.



Chapter 15. Poly(lactic acid)/Starch Blends.

15.1 Introduction.

15.2 Blending Hydrophobic PLA with Hydrophilic Starch.

15.3 Compatibilizers Used for Starch/PLA Blends.

15.4 Enhancing Function of Compatibilizer through Controlling Its Distribution.

15.5 Reactive Blending.

15.6 Summary.


Chapter 16. Poly(lactic acid) Blends.

16.1 Introduction.

16.2 PLA/non-biodegradable polymer blends.

16.3 PLA/biodegradable polymer blends.

16.4 Plasticization of PLA.

16.5 Final Remarks.


Chapter 17. Foaming.

17.1 Introduction.

17.2 Plastic foams.

17.3 Foaming agents.

17.4 Formation of cellular plastics.

17.5 Plastic foams expanded with physical foaming agents.

17.6 PLA foamed with chemical foaming agents.

17.7 Mechanical properties of PLA foams.

17.8 Foaming of PLA/starch blends.


Chapter 18. Composites.

18.1 Introduction.

18.2 PLA Matrix.

18.3 Reinforcements.

18.4 Fiber/matrix adhesion.

18.5 PLA nanocomposites.

18.6 Processing.

18.7 Properties.

18.8 Applications.

18.9 Future developments and concluding remarks .


Chapter 19. Nanocomposites.

19.1 Introduction.

19.2 PLA Nanocomposites based on Clay.

19.3 PLA Nanocomposites based on Carbon Nanotubes.

19.4 PLA Nanocomposites based on Various other Nanofillers.

19.5 Properties of PLA-based Nanocomposites.

19.6 Biodegradability.

19.7 Melt Rheology.

19.8 Foam Processing.

19.9 Possible Applications and Future Prospects.


Chapter 20. Spinning of Poly(lactic acid) Fibers.

20.1 Definition of Fiber and Fiber Spinning.

20.2 Melt Spinning Line.

20.3 Fluid dynamics during spinning.

20.4 Structure development during melt spinning.

20.5 Post Spinning Operation.

20.6 Structure development during Drawing.

20.7 Solution Spinning of PLLA.

20.8 Mechanical Properties.



Chapter 21. Hydrolytic Degradation.

21.1 Introduction.

21.2 Degradation Mechanism.

21.3 Parameters for Hydrolytic Degradation.

21.4 Structural and Property Changes during Hydrolytic Degradation.

21. 5 Applications of Hydrolytic Degradation.

21.6 Conclusions.


Chapter 22. Enzymatic Degradation.

22.1 Introduction.

22.2 Enzymatic degradation of PLA films.

22.3 Enzymatic degradation of thin films.

22.4 Enzymatic degradation of lamellar crystals.

22.5 Future perspectives.


Chapter 23. Thermal Degradation.

23.1 Introduction.

23.2 Kinetic analysis of thermal degradation.

23.3 Thermal degradation behavior of PLA based on molecular weight change.

23.4 Thermal degradation behavior of PLA based on weight loss.

23.5 Conclusions.


Chapter 24. Photodegradation and Radiation Degradation .

24.1 Introduction.

24.2 Photodegradation Mechanism.

24.3 Radiation Degradation Mechanism.

24.4 Photodegradation of PLA.

24.5 Photosensitized Degradation of PLA.

24.6 Radiation Effects on PLA.

24.7 Modification of PLA by Irradiation.


Chapter 25. Biodegradation.

25.1 Introduction.

25.2 Microbial Degradation.

25.3 Poly(L-lactide) (PLLA)-degrading enzymes.

25.4 Conclusion and Future Prospects.


Chapter 26. Cradle to Gate Environmental Footprint and Life Cycle Assessment of Poly(lactic acid).

26.1 Introduction to LCA and environmental footprints.

26.2 Life cycle considerations for PLA.

26.3 Review of PLA LCA studies.

26.4 Improving PLA’s environmental footprint.

26.5 Further Reading on LCA.



Chapter 27. Medical Applications.

27.1 Introduction.

27.2 Minimal Requirements for Medical Devices.

27.3 Preclinical and Clinical Applications of PLA Devices.

27.4 Conclusions.


Chapter 28. Packaging and Other Commercial Applications.

28.1 Introduction.

28.2 Applications in Packaging and containers.

28.3 Agricultural and engineering work materials.

28.4 Conclusions.


Chapter 29. Textile Industry Applications.


29.2 Manufacturing, Structure and Properties of PLA Fibers.

29.3 Key Performance Features of PLA Fibers.

29.4 Potential Applications.

29.5 Conclusions.


Chapter 30. Environmental Applications.

30.1 Introduction.

30.2 Application to water and wastewater treatment.

30.3 Application to bioremediation.

30.4 Concluding remarks and perspective.



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Rafael Auras is an Assistant Professor in the School of Packaging at Michigan State University. He has authored or coauthored more than sixty publications. His research areas include mass transfer in polymers, biodegradable and compostable polymers, life cycle assessment, packaging waste, and sustainable packaging systems.

Loong-Tak Lim is an Associate Professor in the Department of Food Science at the University of Guelph. Dr. Lim is author and coauthor of more than twenty journal articles, a holder of three patents, and has given twenty-one conference presentations.

Susan Selke is Professor and Associate Director in the School of Packaging at Michigan State University. Her research activities and interests include life-cycle analysis, biodegradable and biobased plastics, plastics composites, active packaging, microcellular foaming of plastics, plastics recycling, and related areas. She has authored or coauthored more than 170 publications, including nine books.

Hideto Tsuji is a Professor in the Department of Ecological Engineering, Graduate School of Engineering at Toyohashi University of Technology. He has authored or coauthored more than a hundred academic papers, has edited three books, and holds twelve patents.

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"In summary, I found this book to be a valuable, one-source reference to the chemistry of polylactides. It should serve as an excellent compilation for researchers and prospective researchers in this growing field of polymer chemistry. I recommend this book to all who are interested in these biodegradable polymers." (Journal of the American Chemical Society, 15 April 2011)
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