Chitin and Chitosan: Properties and Applications

List of Contributors xvii Series Preface xxi Preface xxiii 1 Sources of Chitin and Chitosan and their Isolation 1 Leen Bastiaens, Lise Soetemans, Els D'Hondt, and Kathy Elst 1.1 Chitin and Chitosan 2 1.1.1 Chemical Structure 2 1.1.2 Different Crystalline Forms of Chitin 2 1.2 Sources of Chitin and Chitosan 5 1.2.1 Sources of Chitin 5 1.2.2 Sources for Chitosan 10 1.3 Isolation of Chitin 11 1.3.1 Technology Principles 11 1.3.2 Isolation of Chitin from Crustaceans 13 1.3.3 Isolation of Chitin from Insects 16 1.3.4 Isolation of Chitin from Other Biomass Types 16 1.4 Production of Chitosan 19 1.4.1 Conversion of Chitin to Chitosan 19 1.4.2 Chitosan Extracted from Fungi 24 1.5 Towards Commercial Applications 25 1.6 Outlook 28 References 28 2 Methods of Isolating Chitin from Sponges (Porifera) 35 Sonia ?o?towska, Christine Klinger, Iaroslav Petrenko, Marcin Wysokowski, Yvonne Joseph, Teofil Jesionowski, and Hermann Ehrlich 2.1 Introduction 35 2.2 Brief Overview of Classical Methods of Isolating Chitin from Invertebrates 38 2.3 The Modern Approach to Chitin Isolation from Sponges 40 2.3.1 Methods of Isolating Chitin from Glass Sponges (Hexactinellida) 41 2.3.2 Methods of Isolating Chitin from Demosponges (Demospongiae) 43 2.4 Prospective Applications of Poriferan Chitin 49 2.4.1 Poriferan Chitin and Modern Bioinspired Materials Science 49 2.4.2 Chitinous 3D Scaffolds of Sponge Origin for Tissue Engineering 51 2.5 Outlook 54 Acknowledgment 54 References 54 3 Physicochemical Properties of Chitosan and its Degradation Products 61 Karolina Gzyra?Jagie?a, Bo?enna P?czek, Maria Wi?niewska?Wrona, and Natalia Gutowska 3.1 Physicochemical Properties of Chitosan 62 3.1.1 Determination of Molar Mass 62 3.1.2 Determination of the Deacetylation Degree 67 3.1.3 Determination of Dynamic Viscosity 70 3.1.4 Determination of Nitrogen 70 3.1.5 Determination of Ash Content 71 3.1.6 Determination of Heavy Metal Content 71 3.1.7 Determination of Water Retention Value (WRV) 72 3.1.8 Determination of Solubility in Hydrochloric Acid 72 3.1.9 Determination of Water Content 72 3.1.10 Determination of Protein Content 73 3.1.11 Quantitative Determination of Chitosan by Ninhydrin 73 3.2 Products of Degradation and their Application 74 3.3 Outlook 77 References 77 4 New Developments in the Analysis of Partially Acetylated Chitosan Polymers and Oligomers 81 Stefan Cord?Landwehr, Anna Niehues, Jasper Wattjes, and Bruno M. Moerschbacher 4.1 Introduction 82 4.2 Chitosan Oligomers 83 4.2.1 Degree of Polymerisation (DP), Fraction and Pattern of Acetylation (FA and PA) 83 4.3 Chitosan Polymers 86 4.3.1 Molecular Weight (MW) / Degree of Polymerisation (DP) and its Dispersity (DMW / DDP) 86 4.3.2 Fraction of Acetylation (FA) and its Dispersity (DFA) 87 4.3.3 Pattern of Acetylation (PA) 89 4.4 Outlook 91 References 92 5 Chitosan?Based Hydrogels 97 Zhengke Wang, Ling Yang, and Wen Fang 5.1 Introduction 97 5.2 Chitosan?Based Multilayered Hydrogels 98 5.2.1 Periodic Precipitation 99 5.2.2 Alternating Process 100 5.2.3 Induced by Electrical Signals 100 5.2.4 Layer?by?Layer (LbL) Assembly 101 5.2.5 Sequential Curing 101 5.3 Chitin/Chitosan Physical Hydrogels Based on Alkali/Urea Solvent System 103 5.3.1 Chitin Hydrogels Based on Alkali/Urea Solvent System 104 5.3.2 Chitosan Hydrogels Based on Alkali/Urea Solvent System 104 5.4 Chitosan?Based Injectable Hydrogels 108 5.4.1 Physical Association Networks 108 5.4.2 Chemical Association Networks 110 5.4.3 Double?Network Hydrogels 116 5.5 Chitosan?Based Self?Healing Hydrogels 119 5.5.1 Physical Interactions 119 5.5.2 Dynamic Chemical Bonds 121 5.6 Chitosan?Based Shape Memory Hydrogels 125 5.6.1 Water?/Solvent?Triggered Shape Recovery 126 5.6.2 pH?triggered Shape Recovery 126 5.6.3 Ultrasound Triggered Shape Recovery 126 5.6.4 Self?Actuated Shape Memory Hydrogels 127 5.6.5 Chitosan?Based Hydrogels with Triple Shape Memory Effect 127 5.7 Superabsorbent Chitosan?Based Hydrogels 131 5.7.1 Cross?Linked Chitosan?Based Hydrogels 132 5.7.2 Hydrogels by Graft Copolymerization 133 5.7.3 Chitosan?Based Composite Hydrogels 134 5.7.4 Pure Chitosan?Based Materials 135 5.8 Outlook 136 References 136 6 Beneficial Health Effects of Chitin and Chitosan 145 Liyou Dong, Harry J. Wichers, and Coen Govers 6.1 Immunomodulatory Effects of Chitin and Chitosan as Demonstrated with In Vitro Studies 146 6.2 Beneficial Health Effects Mediated by Chitin and Chitosan as Demonstrated with Animal Studies 149 6.2.1 Immune Modulation 149 6.2.2 Anti?Pathogenic Effects 155 6.2.3 Anti?Tumour Effects 157 6.3 Beneficial Health Effects Mediated by Chitin and Chitosan as Demonstrated with Clinical Trials 158 6.3.1 Cholesterol Reduction and CVD Preventive Effects 158 6.3.2 Other Health Effects 160 6.4 Requirements to forward the Field of Study Towards the Beneficial Health Effects of Chitin and Chitosan 163 6.5 Outlook 164 Acknowledgement 164 References 164 7 Antimicrobial Properties of Chitin and Chitosan 169 Magdalena Kucharska, Monika Sikora, Kinga Brzoza?Malczewska, and Monika Owczarek 7.1 Microbiological Activity of Chitosan - The Mechanism of its Antibacterial and Antifungal Activity 169 7.2 The use of Chitin/Chitosan's Microbiological Activity in Medicine and Pharmacy 171 7.3 Microbiological Activity of Chitosan in the Food Industry 174 7.4 Microbiological Activity of Chitosan in Paper and Textile Industries 176 7.5 Microbiological Activity of Chitosan in Agriculture 177 7.6 Outlook 181 References 181 8 Enzymes for Modification of Chitin and Chitosan 189 Gustav Vaaje?Kolstad, Tina Rise Tuveng, Sophanit Mekasha, and Vincent G.H. Eijsink 8.1 CAZymes in Chitin Degradation and Modification 190 8.1.1 Chitinases 191 8.1.2 ?N?acetylhexosaminidases 195 8.1.3 Exo? ?glucosaminidases 195 8.1.4 Chitosanases 197 8.1.5 Lytic Polysaccharide Monooxygenases 199 8.1.6 Carbohydrate Esterases 200 8.1.7 Carbohydrate?Binding Modules 204 8.2 Modular Diversity in Chitinases, Chitosanases and LPMOs 204 8.3 Biological Roles of Chitin?Active Enzymes 205 8.4 Microbial Degradation and Utilisation of Chitin 208 8.4.1 Chitin Degradation by Serratia marcescens 209 8.4.2 Chitin Degradation by Bacteria in the Bacteroidetes Phylum 211 8.4.3 Chitin Degradation by Thermococcus Kodakarensis 211 8.4.4 Chitin Degradation by Fungi 212 8.5 Biotechnological Perspectives 213 8.6 Biorefining of Chitin?Rich Biomass 214 8.7 Outlook 216 References 216 9 Chitin and Chitosan as Sources of Bio?Based Building Blocks and Chemicals 229 Malgorzata Kaisler, Lambertus A.M. van den Broek, and Carmen G. Boeriu 9.1 Introduction 230 9.2 Chitin Conversion into Chitosan, Chitooligosaccharides and Monosaccharides 232 9.2.1 Chitosan Production 232 9.2.2 Production of Chitooligosaccharides 234 9.2.3 Production of GlcNAc and GlcN from Chitin 235 9.3 Building Blocks for Polymers from Chitin and its Derivatives 238 9.3.1 Furan?Based Monomers 238 9.3.2 Amino Alcohol and Amino Acid Building Blocks 239 9.4 Outlook 239 Acknowledgement 240 References 240 10 Chemical and Enzymatic Modification of Chitosan to Produce New Functional Materials with Improved Properties 245 Carmen G. Boeriu and Lambertus A.M. van den Broek 10.1 Introduction 245 10.2 Functional Chitosan Derivatives by Chemical and Enzymatic Modification 246 10.2.1 Anionic Chitosan Derivatives 248 10.2.2 Hydroxyalkylchitosans 250 10.2.3 Quaternised and Highly Cationic Chitosan Derivatives 250 10.2.4 Hydroxyaryl Chitosan Derivatives 250 10.2.5 Carbohydrate?Modified Chitosan 251 10.3 Graft Co?Polymers of Chitosan 251 10.4 Cross?Linked Chitosan and Chitosan Polymer Networks 254 10.5 Outlook 254 References 255 11 Chitosan?Based Drug Delivery Systems 259 Cristian Peptu, Andra Cristina Humelnicu, Razvan Rotaru, Maria Emiliana Fortuna, Xenia Patras, Mirela Teodorescu, Bogdan Ionel Tamba, and Valeria Harabagiu 11.1 Introduction 260 11.2 Beneficial Effects of Chitosan 261 11.2.1 Interaction with Anionic Drugs 263 11.2.2 Mucoadhesive Properties 263 11.2.3 Transfection Activity 263 11.2.4 Efflux Pump Inhibitory Properties 265 11.2.5 Permeation?Enhancing Properties 265 11.3 Chitosan-an Active Polymer for Bypassing Biological Barriers 265 11.3.1 Skin Barrier 266 11.3.2 Mucosa Barrier 267 11.3.3 Ophthalmic Barrier 269 11.3.4 Blood-Brain Barrier 270 11.4 Chitosan?Based DDS Formulations 271 11.4.1 Hydrogels 275 11.4.2 Micro/NPs 275 11.4.3 Nanofibers 275 11.4.4 Scaffolds and Membranes 275 11.5 Outlook 276 Acknowledgment 276 References 276 12 The Application of Chitin and its Derivatives for the Design of Advanced Medical Devices 291 Marcin H. Struszczyk, Longina Madej?Kie?bik, and Dorota Zieli?ska 12.1 Selection of the Raw Sources: Safety Criteria 291 12.1.1 Aspect of Animal Tissue?Originated Derivatives 292 12.1.2 General Requirements for Chitinous Biopolymers Applied in Designing Medical Devices 292 12.1.3 Characterisation of the Biopolymer for Application in Wound Dressing Designing 293 12.1.4 Aspect of the Sterilization of the Final Wound Dressing 295 12.2 Types of Wound Dressings Consisting of Chitin?Derived Biopolymers Available in the Market 297 12.3 Performance and Safety Assessment 297 12.4 New Ideas and Concepts 301 12.5 Risk Acceptance and Design Process Aspects 306 12.6 Outlook 308 Acknowledgements 308 References 308 13 Food Applications of Chitosan and its Derivatives 315 Suse Botelho da Silva, Daiana de Souza, and Liziane Dantas Lacerda 13.1 Introduction 315 13.2 Chitosan and its Derivatives as Food Additive 316 13.2.1 Antioxidant 318 13.2.2 Antimicrobial 319 13.2.3 Stabilizer and Thickener 319 13.3 Functional Ingredient and Health Beneficial Effects 320 13.4 Active Packaging 321 13.5 Enzyme Immobilization 331 13.6 Encapsulation and Delivering of Bioactive Ingredients 332 13.7 Adsorption and Chelation of Toxic and Undesirable Compounds 334 13.8 Outlook 339 References 340 14 Potential of Chitosans in the Development of Edible Food Packaging 349 Veronique Coma and Artur Bartkowiak 14.1 Potential Limitations for Real Introduction into the Market 350 14.1.1 Generally Recognized as Safe (GRAS) 351 14.1.2 Solubility 351 14.1.3 Source-Origin 352 14.1.4 Structure Variability 352 14.2 Films and Coatings for Food Preservation 353 14.2.1 Definitions and Interests 353 14.2.2 Main Relevant Chitosan?Based Material Properties 353 14.3 Specific Case of Chitosan Nanoparticles (CSNPs) 357 14.3.1 CSNPs 357 14.3.2 CSNPs in Various Edible Films 358 14.3.3 Antimicrobial Activities of CSNPs in Edible Films 359 14.3.4 Toxicity Studies of CSNPs 360 14.4 Applications to Sensitive Real Food Products 360 14.4.1 Fruits and Vegetables 361 14.4.2 Meat and Meat Products 362 14.4.3 Fish and Seafood Products 362 14.5 Conclusions 364 References 364 15 The Use of Chitosan?Based Nanoformulations for Controlling Fungi During Storage of Horticultural Commodities 371 Silvia Bautista?Banos, Zormy Nacary Correa?Pacheco, and Rosa Isela Ventura?Aguilar 15.1 Introduction 372 15.2 Importance of Fruits and Vegetables 372 15.3 Storage Disorders and Diseases of Horticultural Products 374 15.4 Plant Fungi Inhibition by Chitosan Application 375 15.5 Chitosan Integrated with Other Alternative Methods for Controlling Postharvest Fungi 376 15.6 Chitosan?Based Formulations 376 15.7 Physiological Response and Quality Retention of Horticultural Commodities to Chitosan Coating Application 376 15.8 Influence of Chitosan Coatings on the Shelf Life of Horticultural Products 378 15.9 Effects of Chitosan Coatings with Additional Compounds on Quality and Microorganisms Development 379 15.10 Integration of Chitosan Nanoparticles into Coating Formulations and their Effects on the Quality of Horticultural Commodities and Development of Microorganisms 384 15.11 Outlook 387 Acknowledgments 387 References 387 16 Chitosan Application in Textile Processing and Fabric Coating 395 Thomas Hahn, Leonie Bossog, Tom Hager, Werner Wunderlich, Rudi Breier, Thomas Stegmaier, and Susanne Zibek 16.1 Chitosan in the Textile Industry 396 16.2 Textile Production 398 16.3 General Test Methods 400 16.4 Fibres and Yarns from Chitin and Chitosan 401 16.4.1 Chitin and Chitosan Solubilisation for Spinning Purposes 402 16.4.2 Chitosan Spinning Processes 402 16.4.3 Mechanical Properties of Chitosan Fibres/Yarns 404 16.5 Sizing with Chitosan 406 16.5.1 Miscibility of Chitosan with Other Sizing Agents 407 16.5.2 Viscosity of Chitosan?Containing Sizing Agents 408 16.5.3 Adhesion and Wetting 410 16.5.4 Mechanical-Physical Properties of Chitosan Films 411 16.5.5 Removal and Processing of Chitosan Sizing after Weaving 412 16.6 Chitosan as a Finishing Agent or Coating 414 16.6.1 Chitosan as a Carrier and Linker 415 16.6.2 Formation of a Durable Finish with Chitosan 416 16.6.3 Chitosan as an Active Agent 417 16.7 Outlook 419 Nomenclature 420 References 421 17 Chitin and Chitosan for Water Purification 429 Petrisor Samoila, Andra Cristina Humelnicu, Maria Ignat, Corneliu Cojocaru, and Valeria Harabagiu 17.1 Introduction 430 17.2 Wastewater Treatment by Adsorption 432 17.2.1 Principle of the Adsorption Process 432 17.2.2 Adsorption of Organic Compounds 434 17.2.3 Adsorption of Heavy Metals 437 17.3 Wastewater Treatment by Coagulation/Flocculation 440 17.4 Wastewater Treatment by Membrane Separation 446 17.4.1 Principle of Ultrafiltration Process 446 17.4.2 Fabrication of Ultrafiltration Blend Membranes 448 17.4.3 Chitosan?Enhanced Ultrafiltration 450 17.5 Outlook 452 Acknowledgement 452 References 453 18 Chitosan for Sensors and Electrochemical Applications 461 Suse Botelho da Silva, Guilherme Lopes Batista, and Cristiane Krause Santin 18.1 Introduction 461 18.2 Chitosan: A Biopolymer with Unique Properties 462 18.3 Modification and Preparation of Chitosan?Based Materials for Electrochemical Applications 463 18.4 The Proton Conductivity of Chitosan 465 18.5 Selected Applications 467 18.5.1 Electrochemical Sensors 467 18.5.2 Spectroscopic Sensors 470 18.5.3 Other Electrochemical Devices 471 18.6 Outlook 472 References 473 19 Marketing and Regulations of Chitin and Chitosan from Insects 477 Nathalie Berezina and Antoine Hubert 19.1 Historical Outline 477 19.2 Natural Origins of Chitin 478 19.3 Specificities of Chitin Biopolymer 479 19.4 Differences Among Chitins from Insects and Other Sources 479 19.4.1 Differences of Chemical Compositions of the Cuticles 479 19.4.2 Differences of Physical Assemblies of Chains and Molecules 480 19.5 Extraction and Purification Specificities of Chitins from Insects 480 19.5.1 Different Cuticle Structures and Contents of Insects 480 19.5.2 Chemical Extraction 480 19.5.3 Biological Extraction 481 19.5.4 Characterization and Transformation into Chitosan 481 19.6 Market Opportunities and its Regulations 482 19.6.1 Agriculture Applications 482 19.6.2 Water Treatment Applications 483 19.6.3 Material Applications 483 19.6.4 Biomedical Applications 484 19.7 Outlook 485 References 485 Index 491

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• Engenharia mecânica e dos materiais