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Antioxidant Polymers

Synthesis, Properties, and Applications
Edited by Giuseppe Cirillo and Francesca Iemma
Series: Polymer Science and Plastics Engineering
Copyright: 2012   |   Status: Published
ISBN: 9781118208540  |  Hardcover  |  
518 pages | 180 illustrations
Price: $195 USD
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One Line Description
Provides an exhaustive overview on the synthesis, characterization and practical applicability of antioxidant polymers.

The volume will be of prime interest to a wide variety of scientists and engineers including those in biomedical, pharmaceutical and food research groups; polymer science and materials science research groups; research and development divisions in the pharmaceutical, cosmetic, plastics materials, and food industries; botanical and marine researchers as well as nano engineers.

Antioxidant Polymers provides a complete and detailed overview of the recent development in the field of polymeric materials showing antioxidant properties. Research into antioxidant polymers has grown enormously in the last decade because they have demonstrated a wide range of applications, from materials science to biomedical, pharmaceutical, cosmetic and personal care, as well as the food packaging industry.

After an introductory overview on the antioxidant compounds, the volume goes in detail with the description of the natural and synthetic polymeric antioxidants, with a particular attention to both their chemical and biological properties. The extraction and modification of natural occurring polymers, as well as the fabrication of totally synthetic compounds, is treated as well.

The 15 chapters are all written by acknowledged experts from both the university research environment and industry R & D labs located around the world.

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Author / Editor Details
Giuseppe Cirillo obtained his PhD on "Methodologies for the Development of Molecules of Pharmaceutical Interest" in 2008 from University of Calabria, Italy. He is currently in a post-doc position at the same university and is CEO of Macrofarm, a University of Calabria spin-off company. He is also a visiting researcher at the Leibniz Institute for Solid State and Materials Research Dresden, Germany). He is author and co-author of more than 50 publications, including research and review articles as well as invited book chapters.

Francesca Iemma obtained her PhD in Chemical Sciences in 1997 from University of Calabria. She currently an associate professor in pharmaceutical technology at the faculty of Pharmacy, Nutrition and Health Sciences of University of Calabria. She is a founding member of Macrofarm, a University of Calabria spin-off company. She has extensive teaching activity in the field of organic chemistry and pharmaceutical technology and is author or co-author of more than 80 publications, including research and review article as well as invited book chapters.

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Table of Contents
Preface 1. Antioxidants: Introduction
Chunhuan He, Yingming Pan, Xiaowen Ji and Hengshan Wang

1.1 The Meaning of Antioxidant
1.2 The Category of Antioxidants and Introduction
of often Used Antioxidants
1.2.1 BHT
1.2.2 Quercetin
1.2.3 BHA
1.2.4 2-tert-Butylhydroquinone (TBHQ)
1.2.5 Gallic Acid
1.2.6 Resveratrol
1.2.7 Luteolin
1.2.8 Caffeic Acid
1.2.9 Catechin
1.3 Antioxidant Evaluation Methods
1.3.1 DPPH Radical Scavenging Assay
1.3.2 ABTS Radical Scavenging Activity
1.3.3 Phosphomolybdenum Assay
1.3.4 Reducing Power Assay
1.3.5 Total Phenols Assay by Folin-Ciocalteu Reagent 0
1.3.6 Hydroxyl Radical Scavenging Assay
1.3.7 β-carotene–linoleic Acid Assay
1.3.8 Superoxide Radical Scavenging Assay
1.3.9 Metal Ion Chelating Assay
1.3.10 Determination of Total Flavonoid Content
1.4 Antioxidant and its Mechanisms
1.4.1 Mechanism of Scavenging Free Radicals
1.4.2 Mechanism of Metal Chelating Properties
1.5 Adverse Effects of Antioxidants
2. Natural Polyphenol and Flavonoid Polymers
Kelly C. Heim

2.1 Introduction
2.2 Structural Classification of Polyphenols
2.2.1 Simple Phenolics
2.2.2 Stilbenes
2.2.3 Lignin
2.2.4 Flavonoids
2.2.5 Tannins
2.3 Polyphenol Biosynthesis and Function in Plants
2.3.1 Biosynthesis
2.3.2 Protective Roles
2.4 Tannins in Human Nutrition
2.4.1 Dietary Sources and Intake
2.4.2 Absorption and Metabolism
2.5 Antioxidant Activity of Tannins
2.5.1 Mechanisms
2.5.2 Structure-activity Relationships
2.6 Protective Effects of Proanthocyanidins in Human Health
2.7 Conclusion
3. Synthesis and Applications of Polymeric Flavonoids
Hiroshi Uyama and Young-Jin Kim

3.1 Introduction
3.2 Polycondensates of Catechin with Aldehydes
3.3 Enzymatically Polymerized Flavonoids
3.4 Biopolymer-flavonoid Conjugates
3.5 Conclusion
4. Antioxidant Polymers: Metal Chelating Agents
Hiba M. Zalloum and Mohammad S. Mubarak

4.1 Introduction
4.1.1 Antioxidants
4.1.2 Natural Polymers as Antioxidants
4.1.3 Chelating Polymers and Heavy Metal Ions
4.2 Chitin and Chitosan
4.2.1 Chitin and Chitosan Derivatives
4.2.2 Chitin and Chitosan as Chelating Agents
4.3 Alginates
4.4 Chelation Studies
4.4.1 Chitosan Derivatives as Chelating Agents
4.4.2 Alginates as Chelating Agents
4.5 Conclusions
5. Antioxidant Polymers by Chitosan Modification
Jarmila Vinšova and Eva Vavrikova

5.1 Introduction
5.2 Chitosan Characteristics
5.3 Reactive Oxygen Species and Chitosan as Antioxidant
5.4 Structure Modifications
5.4.1 N-Carboxymethyl Chitosan Derivatives
5.4.2 Quaternary Salts
5.4.3 Sulphur Derivatives
5.4.4 Chitosan Containing Phenolic Compounds
5.4.5 Schiff Bases of Chitosan
5.5 Conclusion
6. Cellulose and Dextran Antioxidant Polymers for Biomedical Applications
Sonia Trombino, Roberta Cassano and Teresa Ferrarelli

6.1 Introduction
6.2 Antioxidant Polymers Cellulose-based
6.2.1 Cellulose
6.2.2 Antioxidant Biomaterials Carboxymethylcellulose-based
6.2.3 Ferulate Lipoate and Tocopherulate Cellulose
6.2.4 Cellulose Hydrogel Containing Trans-ferulic Acid
6.2.5 Polymeric Antioxidant Membranes Based on Modified Cellulose and PVDF/cellulose
6.2.6 Synthesis of Antioxidant Novel Broom and Cotton Fibers Derivatives
6.3 Antioxidant Polymers Dextran-based
6.3.1 Dextran
6.3.2 Biocompatible Dextran-coated Nanoceria with pH-dependent Antioxidant Properties
6.3.3 Coniugates of Dextran with Antioxidant Properties
6.3.4 Dextran Hydrogel Linking Trans-ferulic Acid for the Stabilization and Transdermal
Delivery of Vitamin E
7. Antioxidant Polymers by Free Radical Grafting on Natural Polymers
Manuela Curcio, Ortensia Ilaria Parisi, Francesco Puoci, Ilaria Altimari, Umile Gianfranco Spizzirri and Nevio Picci

7.1 Introduction
7.2 Grafting of Antioxidant Molecules on Natural Polymers
7.3 Proteins-based Antioxidant Polymers
7.4 Polysaccharides-based Antioxidant Polymers
7.4.1 Chitosan
7.4.2 Starch
7.4.3 Inulin and Alginate
7.5 Conclusions
8. Natural Polymers with Antioxidant Properties: Poly-oligosaccharides of Marine Origin
Guangling Jiao, Guangli Yu, Xiaoliang Zhao, Junzeng Zhang and H. Stephen Ewart

8.1 Introduction to Polysaccharides from Marine Sources
8.1.1 Polysaccharides from Marine Algae
8.1.2 Polysaccharides from Marine Invertebrates
8.1.3 Marine Bacteria Polysaccharides
8.2 Antioxidant Activities of Marine Polysaccharides and their Derivatives
8.2.1 Antioxidant Evaluation Methods
8.2.2 Marine Sulfated Polysaccharides
8.2.3 Marine Uronic Acid-containing Polysaccharides
8.2.4 Marine Non-acidic Polysaccharides and their Oligomers
8.2.5 Marine Glycoconjugates
8.3 Applications of Marine Antioxidant Polysaccharides and their Derivatives
8.3.1 Applications in Food Industry
8.3.2 Applications as Medicinal Materials
8.3.3 Applications as Cosmetic Ingredients
8.3.4 Applications in Other Fields
8.4 Structure-antioxidant Relationships of Marine Poly-/oligosaccharides
8.5 Conclusions
9. Antioxidant Peptides from Marine Origin: Sources, Properties and Potential Applications
Begona Gimenez, M. Elvira Lopez-Caballero, M. Pilar Montero and M. Carmen Gomez-Guillen

9.1 Introduction
9.2 Whole Fish Hydrolysates
9.3 Marine Invertebrate Hydrolysates
9.4 Fish Frames Hydrolysates
9.5 Viscera Hydrolysates
9.6 Muscle Hydrolysates
9.7 Collagen and Gelatin Hydrolysates
9.8 Seaweeds Hydrolysates
9.9 Potential Applications
9.10 Conclusions
10. Synthetic Antioxidant Polymers: Enzyme Mimics
Cheng Wang, Gang-lin Yan and Gui-min Luo

10.1 Introduction
10.2 Organo-selenium/tellurium Compound Mimics
10.2.1 Chemistry of Organo-selenium/tellurium
10.2.2 Synthetic Organo-selenium/tellurium Compounds as GPX Mimics
10.2.3 Cyclodextrin-based Mimics
10.3 Metal Complex Mimics
10.3.1 The Role of Metal Ions in Complexes
10.3.2 Manganese Complexes Mimics
10.3.3 Other Metal Complex Mimics
10.4 Selenoprotein Mimics
10.4.1 Strategies of Selenoprotein Synthesis
10.4.2 Synthetic Selenoproteins
10.5 Supramolecular Nanoenzyme Mimics
10.5.1 Advantages of Supramolecular Nanoenzyme Mimics
10.5.2 Supramolecular Nanoenzyme Mimics with Antioxidant Activity
10.6 Conclusion
11. Synthetic Polymers with Antioxidant Properties
Ashveen V. Nand and Paul A. Kilmartin

11.1 Introduction
11.2 Intrinsically Conducting Polymers
11.3 Intrinsically Conducting Polymers with Antioxidant Properties
11.4 Synthesis of Antioxidant Intrinsically Conducting Polymers
11.4.1 Chemical Synthesis
11.4.2 Electrochemical Synthesis
11.4.3 Other Polymerization Techniques
11.5 Polymer Morphologies
11.5.1 Polyaniline
11.5.2 Polypyrrole
11.5.3 Poly(3,4-ethylenedioxythiophene)
11.6 Mechanism of Radical Scavenging
11.7 Assessment of Free Radical Scavenging Capacity
11.7.1 DPPH Assay
11.7.2 ABTS Assay
11.8 Factors Affecting the Radical Scavenging Activity
11.9 Polymer Blends and Practical Applications
12. Synthesis of Antioxidant Monomers Based on Sterically Hindered Phenols, a-Tocopherols, Phosphites and Hindered Amine Light Stabilizers (HALS) and their Copolymerization with Ethylene, Propylene or Styrene
Carl-Eric Wilen

12.1 Introduction
12.2 Synthesis of Antioxidant Monomers to Enhance Physical Persistence and Performance
of Stabilizers
12.2.1 Copolymerization of Antioxidants with α-Olefins Using Coordination Catalysts
12.2.2 Synthesis of Antioxidant Monomers
12.3 Phenolic Antioxidant Monomers and their Copolymerization with Coordination Catalysts
12.3.1 Copolymerization of Antioxidant Monomers with Ethylene or Propylene using Traditional Ziegler-Natta Catalysts
12.4 Copolymerization of Antioxidant Monomers with Ethylene, Propylene, Styrene and Carbon
Monoxide Using Single Site Catalysts
12.4.1 Copolymerization of Phenolic Antioxidant Monomers
12.4.2 Copolymerization of HALS Monomers using Single Site Catalysts
12.5 Conclusions
13. Novel Polymeric Antioxidants for Materials
Ashish Dhawan, Vijayendra Kumar, Virinder S. Parmar and Ashok L. Cholli

13.1 Industrial Antioxidants
13.2 Antioxidants Used in Plastics (Polymer) Industry
13.2.1 Primary Antioxidants
13.2.2 Secondary Antioxidants
13.3 Antioxidants Used in Lubricant Industry
13.4 Antioxidants Used in Elastomer (Rubber) Industry
13.5 Antioxidants Used in Fuel Industry
13.6 Antioxidants Used in Food Industry
13.6.1 Natural Food Antioxidants
13.6.2 Synthetic Food Antioxidants
13.7 Limitations of Conventional Antioxidants
13.7.1 Performance Issues because of Antioxidant Efficiency Loss
13.7.2 Environmental Issues and Safety Concerns
13.7.3 Compatibility Issues
13.7.4 Poor Thermal Stability
13.8 Trends towards High Molecular Weight Antioxidants
13.8.1 Functionalization of Conventional Antioxidants with Hydrocarbon Chains
13.8.2 Macromolecular Antioxidants
13.8.3 Polymer-bound Antioxidants
13.8.4 Polymeric Antioxidants
13.9 Motivation, Design and Methodology for Synthesis of Novel Polymeric Antioxidant
13.9.1 Design of the Polymeric Antioxidants
13.9.2 Methodology
13.10 Biocatalytic Synthesis of Polymeric Antioxidants
13.11 General Procedure for Enzymatic Polymerization
13.11.1 Synthesis and Characterization of Polymeric Antioxidants
13.11.2 Antioxidant Activity of Polymeric Antioxidants
13.11.3 Evaluation of Polymeric Antioxidants in Vegetable Oils by Accelerated Oxidation
13.12 Conclusions
14. Biopolymeric Colloidal Particles Loaded with Polyphenolic Antioxidants
Ashok R. Patel and Krassimir P. Velikov

14.1 Introduction
14.2 Polyphenols: Antioxidant Properties and Health Benefits
14.3 Polyphenols: Formulation and Delivery Challenges
14.3.1 Solubility
14.3.2 Chemical Reactivity and Degradation
14.3.3 Stability in Physiological Conditions
14.3.4 First Pass Metabolism and Pharmacokinetics
14.3.5 Organoleptic Properties and Aesthetic Appeal
14.4 Polyphenols Loaded Biopolymeric Colloidal Particles
14.4.1 Curcumin Loaded Biopolymeric Colloidal Particles
14.4.2 Silibinin Loaded Biopolymeric Colloidal Particles
14.4.3 Quercetin Loaded Biopolymeric Colloidal Particles
14.5 Conclusion
15. Antioxidant Polymers for Tuning Biomaterial Biocompatibility: From Drug Delivery to Tissue Engineering
David Cochran and Thomas D. Dziubla

15.1 Introduction
15.2 Oxidative Stress in Relation to Biocompatibility
15.2.1 Mechanism of Immune Response
15.2.2 Examples in Practice
15.3 Antioxidant Polymers in Drug Delivery
15.3.1 Uses as Active Pharmaceutical Ingredients
15.3.2 Uses as Pharmaceutical Excipients
15.4 Antioxidant Polymers in Anti-cancer Therapies
15.5 Antioxidant Polymers in Wound Healing and Tissue Engineering
15.5.1 Antioxidant Polymers Incorporated into Biomaterials
15.6 Conclusions and Perspectives

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