Handbook of Biodegradable Polymers E-Book

• Herausgeber: Wiley-VCH
• Kategorie: Fachliteratur
• Sprache: Englisch

Seitenzahl: 743

Veröffentlichungsjahr: 2011

Beschreibung

A comprehensive overview of biodegradable polymers, covering everything from synthesis, characterization, and degradation mechanisms while also introducing useful applications, such as drug delivery systems and biomaterial-based regenerative therapies. An introductory section deals with such fundamentals as basic chemical reactions during degradation, the complexity of biological environments and experimental methods for monitoring degradation processes. The result is a reliable reference source for those wanting to learn more about this important class of polymer materials, as well as scientists in the field seeking a deeper insight.

Leseprobe

Table of Contents

Cover

Series page

Title page

Copyright page

Preface

List of Contributors

1 Polyesters

1.1 Historical Background

1.2 Preparative Methods

1.3 Physical Properties

1.4 Degradation Mechanisms

1.5 Beyond Classical Poly(Hydroxycarboxylic Acids)

2 Biotechnologically Produced Biodegradable Polyesters

2.1 Introduction

2.2 History

2.3 Polyhydroxyalkanoates – Granules Morphology

2.4 Biosynthesis and Biodegradability of Poly(3-Hydroxybutyrate) and Other Polyhydroxyalkanoates

2.5 Extraction and Recovery

2.6 Physical, Mechanical, and Thermal Properties of Polyhydroxyalkanoates

2.7 Future Directions

3 Polyanhydrides

3.1 Introduction

3.2 Types of Polyanhydride

3.3 Synthesis

3.4 Properties

3.5 In Vitro Degradation and Erosion of Polyanhydrides

3.6 In Vivo Degradation and Elimination of Polyanhydrides

3.7 Toxicological Aspects of Polyanhydrides

3.8 Fabrication of Delivery Systems

3.9 Production and World Market

3.10 Biomedical Applications

4 Poly(Ortho Esters)

4.1 Introduction

4.2 POE II

4.3 POE IV

4.4 Solid Polymers

4.5 Gel-Like Materials

4.6 Polymers Based on an Alternate Diketene Acetal

4.7 Conclusions

5 Biodegradable Polymers Composed of Naturally Occurring α-Amino Acids

5.1 Introduction

5.2 Amino Acid-Based Biodegradable Polymers (AABBPs)

5.3 Conclusion and Perspectives

6 Biodegradable Polyurethanes and Poly(ester amide)s

Abbreviations

6.1 Chemistry and Properties of Biodegradable Polyurethanes

6.2 Biodegradation Mechanisms of Polyurethanes

6.3 Applications of Biodegradable Polyurethanes

6.4 New Polymerization Trends to Obtain Degradable Polyurethanes

6.5 Aliphatic Poly(ester amide)s: A Family of Biodegradable Thermoplastics with Interest as New Biomaterials

Acknowledgments

7 Carbohydrates

7.1 Introduction

7.2 Alginate

7.3 Carrageenan

7.4 Cellulose and Its Derivatives

7.5 Microbial Cellulose

7.6 Chitin and Chitosan

7.7 Dextran

7.8 Gellan

7.9 Guar Gum

7.10 Hyaluronic Acid (Hyaluronan)

7.11 Pullulan

7.12 Scleroglucan

7.13 Xanthan

7.14 Summary

Acknowledgments

In Memoriam

8 Biodegradable Shape-Memory Polymers

8.1 Introduction

8.2 General Concept of SMPs

8.3 Classes of Degradable SMPs

8.4 Applications of Biodegradable SMPs

9 Biodegradable Elastic Hydrogels for Tissue Expander Application

9.1 Introduction

9.2 Synthesis of Elastic Hydrogels

9.3 Physical Properties of Elastic Hydrogels

9.4 Applications of Elastic Hydrogels

9.5 Elastic Hydrogels for Tissue Expander Applications

9.6 Conclusion

10 Biodegradable Dendrimers and Dendritic Polymers

10.1 Introduction

10.2 Challenges for Designing Biodegradable Dendrimers

10.3 Design of Self-Immolative Biodegradable Dendrimers

10.4 Biological Implications of Biodegradable Dendrimers

10.5 Future Perspectives of Biodegradable Dendrimers

10.6 Concluding Remarks

11 Analytical Methods for Monitoring Biodegradation Processes of Environmentally Degradable Polymers

11.1 Introduction

11.2 Some Background

11.3 Defining Biodegradability

11.4 Mechanisms of Polymer Degradation

11.5 Measuring Biodegradation of Polymers

11.6 Conclusions

12 Modeling and Simulation of Microbial Depolymerization Processes of Xenobiotic Polymers

12.1 Introduction

12.2 Analysis of Exogenous Depolymerization

12.3 Materials and Methods

12.4 Analysis of Endogenous Depolymerization

12.5 Discussion

Acknowledgments

13 Regenerative Medicine: Reconstruction of Tracheal and Pharyngeal Mucosal Defects in Head and Neck Surgery

13.1 Introduction

13.2 Regenerative Medicine for the Reconstruction of the Upper Aerodigestive Tract

13.3 Methods and Novel Therapeutical Options in Head and Neck Surgery

13.4 Vascularization of Tissue-Engineered Constructs

13.5 Application of Stem Cells in Regenerative Medicine

13.6 Conclusion

14 Biodegradable Polymers as Scaffolds for Tissue Engineering

Abbreviations

14.1 Introduction

14.2 Short Overview of Regenerative Biology

14.3 Minimum Requirements for Tissue Engineering

14.4 Structure of Scaffolds

14.5 Biodegradable Polymers for Tissue Engineering

14.6 Some Examples for Clinical Application of Scaffold

14.7 Conclusions

15 Drug Delivery Systems

15.1 Introduction

15.2 The Clinical Need for Drug Delivery Systems

15.3 Poly(α-Hydroxyl Acids)

15.4 Polyanhydrides

15.5 Manufacturing Routes

15.6 Examples of Biodegradable Polymer Drug Delivery Systems Under Development

15.7 Concluding Remarks

16 Oxo-biodegradable Polymers: Present Status and Future Perspectives

16.1 Introduction

16.2 Controlled – Lifetime Plastics

16.3 The Abiotic Oxidation of Polyolefins

16.4 Enhanced Oxo-biodegradation of Polyolefins

16.5 Processability and Recovery of Oxo-biodegradable Polyolefins

16.6 Concluding Remarks

Index

Further Reading

Loos, K. (Ed.)

Biocatalysis in Polymer Chemistry

2011

Hardcover

ISBN: 978-3-527-32618-1

Mathers, R. T., Maier, M. A. R. (Eds.)

Green Polymerization Methods

Renewable Starting Materials, Catalysis and Waste Reduction

2011

Hardcover

ISBN: 978-3-527-32625-9

Yu, L.

Biodegradable Polymer Blends and Composites from Renewable Resources

2009

Hardcover

ISBN: 978-0-470-14683-5

Elias, H.-G.

Macromolecules

2009

Hardcover

ISBN: 978-3-527-31171-2

Matyjaszewski, K., Müller, A. H. E. (Eds.)

Controlled and Living Polymerizations

From Mechanisms to Applications

2009

ISBN: 978-3-527-32492-7

Matyjaszewski, K., Gnanou, Y., Leibler, L. (Eds.)

Macromolecular Engineering

Precise Synthesis, Materials Properties, Applications

2007

Hardcover

ISBN: 978-3-527-31446-1

Fessner, W.-D., Anthonsen, T. (Eds.)

Modern Biocatalysis

Stereoselective and Environmentally Friendly Reactions

2009

ISBN: 978-3-527-32071-4

Janssen, L., Moscicki, L. (Eds.)

Thermoplastic Starch

A Green Material for Various Industries

2009

Hardcover

ISBN: 978-3-527-32528-3

The Editors

Prof. Andreas Lendlein

GKSS Forschungszentrum

Inst. für Chemie

Kantstr. 55

14513 Teltow

Germany

Dr. Adam Sisson

GKSS Forschungszentrum

Zentrum f. Biomaterialentw.

Kantstraße 55

14513 Teltow

Germany

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A catalogue record for this book is available from the British Library.

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The Deutsche Nationalbibliothek lists this publication in the Deutsche Nationalbibliografie; detailed bibliographic data are available on the Internet at < http://dnb.d-nb.de>.

© 2011 Wiley-VCH Verlag & Co. KGaA, Boschstr. 12, 69469 Weinheim, Germany

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ISBN: 978-3-527-32441-5

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Preface

Degradable polyesters with valuable material properties were pioneered by Carothers at DuPont by utilizing ring-opening polymerization approaches for achieving high molecular weight aliphatic poly(lactic acid)s in the 1930s. As a result of various oil crises, biotechnologically produced poly(hydroxy alkanoates) were keenly investigated as greener, non-fossil fuel based alternatives to petrochemical based commodity plastics from the 1960s onwards. Shortly afterwards, the first copolyesters were utilized as slowly drug releasing matrices and surgical sutures in the medical field. In the latter half of the 20th century, biodegradable polymers developed into a core field involving different scientific disciplines such that these materials are now an integral part of our everyday lives. This field still remains a hotbed of innovation today. There is a burning interest in the use of biodegradable materials in clinical settings. Perusal of the literature will quickly reveal that such materials are the backbone of modern, biomaterial-based approaches in regenerative medicine. Equally, this technology is central to current drug delivery research through biodegradable nanocarriers, microparticles, and erodible implants, which enable sophisticated controlled drug release and targeting. Due to the long historic legacy of polymer research, this field has been able to develop to a point where material compositions and properties can be refined to meet desired, complex requirements. This enables the creation of a highly versatile set of materials as a key component of new technologies. This collected series of texts, written by experts, has been put together to showcase the state of the art in this ever-evolving area of science.

The chapters have been divided into three groups with different themes. Chapters 1–8 introduce specific materials and cover the major classes of polymers that are currently explored or utilized. Chapters 9–14 describe applications of biodegradable polymers, emphasizing the exciting potential of these materials. In the final chapters, 15–16, characterization methods and modelling techniques of biodegradation processes are depicted.

Materials: Lendlein et al., then Ienczak and Aragão, start with up-to-date reviews of the seminal polyesters and biotechnologically produced polyesters, respectively. Other chapters concern polymers with different scission moieties and behaviors. Domb et al. provide a comprehensive review of polyanhydrides, which is followed by an excellent overview of poly(ortho esters) contributed by Heller. Amino acid- based materials and degradable polyurethanes make up the subject of the next two chapters by Katsarava and Gomurashvili, then Puiggali et al., respectively. Synthetic polysaccharides, which are related to many naturally occurring biopolymers, are then described at length by Dumitriu, Dräger et al. To conclude the individual polymer-class section, biodegradable polyolefins, which are degraded oxidatively, and are intended as degradable commodity plastics, are covered by Wiles et al.

Applications: The two chapters by Ikada and Shakesheff give a critical update on the status of biodegradable materials applied in regenerative therapy and then in drug delivery systems. From there, further exciting applications are described; shape-memory polymers and their potential as implant materials in minimally invasive surgery are discussed by Lendlein et al.; Huh et al. highlight the importance of biodegradable hydrogels for tissue expander applications; Franke et al. cover how implants can be used to aid regenerative treatment of mucosal defects in surgery; Khandare and Kumar review the relevance of biodegradable dendrimers and dendritic polymers to the medical field.

Methods: Van der Zee gives a description of the methods used to quantify biodegradability and the implications of biodegradability as a whole; Watanabe and Kawai go on to explain methods used to explore degradation through modelling and simulations.

The aim of this handbook is to provide a reference guide for anyone practising in the exploration or use of biodegradable materials. At the same time, each chapter can be regarded as a stand alone work, which should be of great benefit to readers interested in each specific field. Synthetic considerations, physical properties, and erosion behaviours for each of the major classes of materials are discussed. Likewise, the most up to date innovations and applications are covered in depth. It is possible upon delving into the provided information to really gain a comprehensive understanding of the importance and development of this field into what it is today and what it can become in the future.

We wish to thank all of the participating authors for their excellent contributions towards such a comprehensive work. We would particularly like to pay tribute to two very special authors who sadly passed away during the production time of this handbook. Jorge Heller was a giant in the biomaterials field and pioneered the field of poly(ortho esters). Severian Dimitriu is well known for his series of books on biodegradable materials, which served to inspire and educate countless scientists in this area. Our sincerest thanks go to Gloria Heller and Daniela Dumitriu for their cooperation in completing these chapters. We also acknowledge the untiring administrative support of Karolin Schmälzlin, Sabine Benner and Michael Schroeter, and the expert cooperation from the publishers at Wiley, especially Elke Maase and Heike Nöthe.

Andreas Lendlein

Adam Sisson

Teltow, September 2010

List of Contributors

Gláucia Maria Falcão de Aragão

Federal University of Santa Catarina

Chemical and Food Engineering Department

Florianópolis, SC 88040-900

Brazil

Marc Behl

Center for Biomaterial Development, Institute of Polymer Research

Helmholtz-Zentrum Geesthacht

Kantstr. 55

14513 Teltow

Germany

Emo Chiellini

University of Pisa

Department of Chemistry and Industrial Chemistry

via Risorgimento 35

Pisa 56126

Italy

Andrea Corti

University of Pisa

Department of Chemistry and Industrial Chemistry

via Risorgimento 35

Pisa 56126

Italy

Salvatore D’Antone

University of Pisa

Department of Chemistry and Industrial Chemistry

via Risorgimento 35

Pisa 56126

Italy

Avi Domb

Hebrew University

School of Pharmacy

Department of Medicinal Chemistry

Jerusalem 91120

Israel

Gerald Dräger

Gottfried Wilhelm Leibniz Universität Hannover

Institut für Organische Chemie

Schneiderberg 1B

30167 Hannover

Germany

Severian Dumitriut

University of Sherbrooke

Department of Chemical Engineering

2400 Boulevard de l′Université

Sherbrooke, Quebec J1K 2R1

Canada

Lourdes Franco

Universitat Politècnica de Catalunya

Departament d’Enginyeria Química

Av. Diagonal 647

08028 Barcelona

Spain

Ralf-Peter Franke

Centre for Biomaterial Development and Berlin-Brandenburg Centre for Regenerative Therapies (BCRT)

Institute of Polymer Research

Helmholtz-Zentrum Geesthacht GmbH

Kantstr. 55

14513 Teltow

Germany

and

University of Ulm

Central Institute for Biomedical Engineering

Department of Biomaterials

89069 Ulm

Germany

Yourong Fu

Akina, Inc.

West Lafayette, IN 47906

USA

Rosemarie Fuhrmann

University of Ulm

Central Institute for Biomedical Engineering

Department of Biomaterials

89069 Ulm

Germany

John Garner

Akina, Inc.

West Lafayette, IN 47906

USA

Zaza Gomurashvili

PEA Technologies

709 Mockingbird Cr.

Escondido, CA 92025

USA

Jorge Hellert

PO Box 3519, Ashland, OR 97520

USA

Bernhard Hiebl

Centre for Biomaterial Development and Berlin-Brandenburg Centre for Regenerative Therapies (BCRT)

Institute of Polymer Research

Helmholtz-Zentrum Geesthacht

Kantstr. 55

14513 Teltow

Germany

Kang Moo Huh

Chungnam National University

Department of Polymer Science and Engineering

Daejeon 305-764

South Korea

Jaciane Lutz Ienczak

Federal University of Santa Catarina

Chemical and Food Engineering Department

Florianópolis, SC 88040-900

Brazil

Yoshito Ikada

Nara Medical University

Shijo-cho 840

Kashihara-shi

Nara 634-8521

Japan

Jay Prakash Jain

National Institute of Pharmaceutical Education and Research (NIPER)

Department of Pharmaceutics

Sector 67

S.A.S. Nagar (Mohali) 160062

India

Friedrich Jung

Centre for Biomaterial Development and Berlin-Brandenburg Centre for Regenerative Therapies (BCRT)

Institute of Polymer Research

Helmholtz-Zentrum Geesthacht

Kantstr. 55

14513 Teltow

Germany

Ramaz Katsarava

Iv. Javakhishvili Tbilisi State University

Institute of Medical Polymers and Materials

1, Chavchavadze ave.

Tbilisi 0179

Georgia

and

Georgian Technical University

Centre for Medical Polymers and Biomaterials

77, Kostava str.

Tbilisi 75

Georgia

Fusako Kawai

Kyoto Institute of Technology

Center for Nanomaterials and Devices

Matsugasaki

Sakyo-ku, Kyoto 606-8585

Japan

Jayant Khandare

Piramal Life Sciences Ltd.

Polymer Chem. Grp

1 Nirlon Complex

Off Western Express Highway

Goregaon (E), Mumbai 400063

India

Andreas Krause

Gottfried Wilhelm Leibniz Universität Hannover

Institut für Organische Chemie

Schneiderberg 1B

30167 Hannover

Germany

Neeraj Kumar

National Institute of Pharmaceutical Education and Research (NIPER)

Department of Pharmaceutics

Sector 67

S.A.S. Nagar (Mohali) 160062

India

Sanjay Kumar

Piramal Life Sciences Ltd.

Polymer Chem. Grp

1 Nirlon Complex

Off Western Express Highway

Goregaon (E), Mumbai 400063

India

Andreas Lendlein

Center for Biomaterial Development and Berlin-Brandenburg Center for Regenerative Therapies, Institute of Polymer Research

Helmholtz-Zemtrum Geesthacht

Kantstr. 55

14513 Teltow

Germany

Lena Möller

Gottfried Wilhelm Leibniz Universität Hannover

Institut für Organische Chemie

Schneiderberg 1B

30167 Hannover

Germany

Kinam Park

Purdue University

Department of Biomedical Engineering and Pharmaceutics

West Lafayette, IN 47907-2032

USA

Jordi Puiggalí

Universitat Politècnica de Catalunya

Departament d’Enginyeria Química

Av. Diagonal 647

08028 Barcelona

Spain

Dorothee Rickert

Marienhospital Stuttgart

Böheimstrasse 37

70199 Stuttgart

Germany

Alfonso Rodríguez-Galán

Universitat Politècnica de Catalunya

Departament d’Enginyeria Química

Av. Diagonal 647

08028 Barcelona

Spain

Michael Schroeter

Center for Biomaterial Development Institute of Polymer Research

Helmholtz-Zentrum Geesthacht

Kantstr. 55

14513 Teltow

Germany

Kevin M. Shakesheff

The University of Nottingham

School of Pharmacy, STEM

NG 7 2RD

UK

Adam L. Sisson

Center for Biomaterial Development and Berlin-Brandenburg Center for Regenerative Therapies, Institute of Polymer Research

Helmholtz-Zentrum Geesthacht

Kantstr. 55

14513 Teltow

Germany

Thanh Huyen Tran

Chungnam National University

Department of Polymer Science and Engineering

Daejeon 305-764

South Korea

Masaji Watanabe

Okayama University

Graduate School of Environmental Science

1-1, Naka 3-chome

Tsushima, Okayama 700-8530

Japan

David Mckeen Wiles

Plastichem Consulting

Victoria, BC V8N 5W9

Canada

Maarten van der Zee

Wageningen UR

Food & Biobased Research

P.O. Box 17

6700 AA Wageningen

The Netherlands

Jörg Zotzmann

Center for Biomaterial Development Institute of Polymer Research

Helmholtz-Zentrum Geesthacht

Kantstr. 55

14513 Teltow

Germany

2

Biotechnologically Produced Biodegradable Polyesters

Jaciane Lutz Ienczak and Gláucia Maria Falcão de Aragão

2.1 Introduction

Polyhydroxyalkanoates (PHAs) are polyesters synthesized by many microorganisms as a carbon and energy storage material [1].

The interest in establishing PHA as an alternative plastic to conventional petrochemical-based plastics was first motivated because it can be produced from renewable carbon sources and since they are biodegradable. Fuel-based polymers are extensively used due to their easy manufacturing and low cost of production. Unfortunately, these same qualities can transform them into an important environmental problem because they are cheap and disposable. The great demand for this kind of polymer production generates pollution and problems related with the disposal in landfills because these materials are resistant to degradation [2]. In response to rising public concern regarding the effects of fuel-based materials in the environment, biopolymers are a reality that can minimize these problems. Biopolymers are polymeric materials structurally classified as polysaccharides [3, 4], polyesters [5–7], or polyamides [8]. The main raw material for manufacturing them is a renewable carbon source, usually carbohydrates such as sugar cane, corn, potato, wheat, beet, or a vegetable oil extracted from soybean, sunflower, palm, or other plants. Currently, biopolymers of interest include thermoplastic starch [9], polylactides (PLA) [10], xanthan [3], polyamides cyanophycin, and the PHA class which includes the most studied biopolymer, poly(3-hydroxybutyric) (P[3HB]) and its copolymer poly(3-hydroxybutyrate-co-3-hydroxyvalerate) (P[3HB-co-3HV]) [7, 11, 12].