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Biobased Adhesives
Unique and comprehensive book edited by acknowledged leaders on biobased adhesives that will replace petroleum-based adhesives.
This book contains 23 chapters covering the various ramifications of biobased adhesives. The chapters are written by world-class scientists and technologists actively involved in the arena of biobased adhesives. The book is divided into three parts: Part 1: Fundamental Aspects; Part 2: Classes of Biobased Adhesives; and Part 3: Applications of Biobased Adhesives. Topics covered include: an introduction to biobased adhesives; adhesion theories and adhesion and surface issues with biobased adhesives; chemistry of adhesives; biorefinery products as biobased raw materials for adhesives; naturally aldehyde-based thermosetting resins; natural crosslinkers; curing and adhesive bond strength development in biobased adhesives; mimicking nature; bio-inspired adhesives; protein adhesives; carbohydrates as adhesives; natural polymer-based adhesives; epoxy adhesives from natural materials; biobased polyurethane adhesives; nanocellulose-modified adhesives; debondable, recyclable, and biodegradable biobased adhesives; 5-Hydroxymethylfurfural-based adhesives; adhesive precursors from tree-derived naval stores; and applications in various diverse arenas such as wood bonding, controlled drug delivery, and wearable bioelectronics.
Audience
This book will interest materials scientists, adhesionists, polymer chemists, marine biologists, food and agriculture scientists, and environmentalists. R&D personnel in a slew of wide-ranging industries such as aviation, shipbuilding, railway, automotive, packaging, construction, wood bonding, and composites should find this book a repository of current and much-needed information.
Unique and comprehensive book edited by acknowledged leaders on biobased adhesives that will replace petroleum-based adhesives.
This book contains 23 chapters covering the various ramifications of biobased adhesives. The chapters are written by world-class scientists and technologists actively involved in the arena of biobased adhesives. The book is divided into three parts: Part 1: Fundamental Aspects; Part 2: Classes of Biobased Adhesives; and Part 3: Applications of Biobased Adhesives. Topics covered include: an introduction to biobased adhesives; adhesion theories and adhesion and surface issues with biobased adhesives; chemistry of adhesives; biorefinery products as biobased raw materials for adhesives; naturally aldehyde-based thermosetting resins; natural crosslinkers; curing and adhesive bond strength development in biobased adhesives; mimicking nature; bio-inspired adhesives; protein adhesives; carbohydrates as adhesives; natural polymer-based adhesives; epoxy adhesives from natural materials; biobased polyurethane adhesives; nanocellulose-modified adhesives; debondable, recyclable, and biodegradable biobased adhesives; 5-Hydroxymethylfurfural-based adhesives; adhesive precursors from tree-derived naval stores; and applications in various diverse arenas such as wood bonding, controlled drug delivery, and wearable bioelectronics.
Audience
This book will interest materials scientists, adhesionists, polymer chemists, marine biologists, food and agriculture scientists, and environmentalists. R&D personnel in a slew of wide-ranging industries such as aviation, shipbuilding, railway, automotive, packaging, construction, wood bonding, and composites should find this book a repository of current and much-needed information.
Biobased Adhesives
Unique and comprehensive book edited by acknowledged leaders on biobased adhesives that will replace petroleum-based adhesives.
This book contains 23 chapters covering the various ramifications of biobased adhesives. The chapters are written by world-class scientists and technologists actively involved in the arena of biobased adhesives. The book is divided into three parts: Part 1: Fundamental Aspects; Part 2: Classes of Biobased Adhesives; and Part 3: Applications of Biobased Adhesives. Topics covered include: an introduction to biobased adhesives; adhesion theories and adhesion and surface issues with biobased adhesives; chemistry of adhesives; biorefinery products as biobased raw materials for adhesives; naturally aldehyde-based thermosetting resins; natural crosslinkers; curing and adhesive bond strength development in biobased adhesives; mimicking nature; bio-inspired adhesives; protein adhesives; carbohydrates as adhesives; natural polymer-based adhesives; epoxy adhesives from natural materials; biobased polyurethane adhesives; nanocellulose-modified adhesives; debondable, recyclable, and biodegradable biobased adhesives; 5-Hydroxymethylfurfural-based adhesives; adhesive precursors from tree-derived naval stores; and applications in various diverse arenas such as wood bonding, controlled drug delivery, and wearable bioelectronics.
Audience
This book will interest materials scientists, adhesionists, polymer chemists, marine biologists, food and agriculture scientists, and environmentalists. R&D personnel in a slew of wide-ranging industries such as aviation, shipbuilding, railway, automotive, packaging, construction, wood bonding, and composites should find this book a repository of current and much-needed information.
Unique and comprehensive book edited by acknowledged leaders on biobased adhesives that will replace petroleum-based adhesives.
This book contains 23 chapters covering the various ramifications of biobased adhesives. The chapters are written by world-class scientists and technologists actively involved in the arena of biobased adhesives. The book is divided into three parts: Part 1: Fundamental Aspects; Part 2: Classes of Biobased Adhesives; and Part 3: Applications of Biobased Adhesives. Topics covered include: an introduction to biobased adhesives; adhesion theories and adhesion and surface issues with biobased adhesives; chemistry of adhesives; biorefinery products as biobased raw materials for adhesives; naturally aldehyde-based thermosetting resins; natural crosslinkers; curing and adhesive bond strength development in biobased adhesives; mimicking nature; bio-inspired adhesives; protein adhesives; carbohydrates as adhesives; natural polymer-based adhesives; epoxy adhesives from natural materials; biobased polyurethane adhesives; nanocellulose-modified adhesives; debondable, recyclable, and biodegradable biobased adhesives; 5-Hydroxymethylfurfural-based adhesives; adhesive precursors from tree-derived naval stores; and applications in various diverse arenas such as wood bonding, controlled drug delivery, and wearable bioelectronics.
Audience
This book will interest materials scientists, adhesionists, polymer chemists, marine biologists, food and agriculture scientists, and environmentalists. R&D personnel in a slew of wide-ranging industries such as aviation, shipbuilding, railway, automotive, packaging, construction, wood bonding, and composites should find this book a repository of current and much-needed information.
Über den Autor
Manfred Dunky, PhD, has spent a 40-year career in the chemical and wood-based panels industry as a researcher and consultant. During the last 25 years, he has placed an emphasis on adhesives based on natural resources. Besides his industry career, in 2000 he received his habilitation (post-doctoral lecturing qualification) for "Wood Science with special consideration of wood-based panels" and was a lecturer at several universities. He is invited regularly to speak at many wood science conferences.
Kashmiri Lal Mittal was employed by the IBM Corporation from 1972 through 1993. Currently, he is teaching and consulting worldwide in the broad areas of adhesion, as well as surface cleaning. He has received numerous awards and honors, including the title of doctor honoris causa from Maria Curie-Sk3odowska University, Lublin, Poland. He is the editor of over 150 books dealing with adhesion measurement, adhesion of polymeric coatings, polymer surfaces, adhesive joints, adhesion promoters, thin films, polyimides, surface modification surface cleaning, and surfactants.
Inhaltsverzeichnis
Preface xvii
Part 1: Fundamental Aspects 1
1 Introduction to Naturally-Based (Bio-) Adhesives 3
Manfred Dunky
1.1 Introduction 3
1.2 Overview and Challenges For Adhesives Based on Natural Resources 6
1.2.1 Combined Use of Synthetic and Naturally-Based Adhesives 8
1.2.2 Overview on Adhesives Based on Natural Resources 9
1.2.3 Requirements, Limitations, and Opportunities for Wood Adhesives Based on Natural Resources 11
1.3 Biorefinery and Platform Chemicals 11
1.4 Lignin as Raw Material for Platform Chemicals 20
1.5 5-Hydroxymethylfurfural (5-HMF) as Platform Chemical 23
1.6 Mimicking Nature 27
1.7 Special Topics and Latest Developments 29
1.8 Prospects 30
1.9 Summary 30
General Literature on Biobased Adhesives 30
List of Abbreviations 34
References 35
2 Adhesion Theories in Naturally-Based Bonding: Adhesion and Surface Issues with Naturally-Based Adhesives 45
Douglas J. Gardner, Geeta Pokhrel and Alexander Collins
2.1 Introduction 45
2.2 Adhesion Theories 46
2.2.1 Mechanical Interlocking 47
2.2.2 Electrostatic Mechanism 48
2.2.3 Adsorption (Thermodynamic) or Wetting Mechanism 49
2.2.4 Diffusion Mechanism 50
2.2.5 Chemical (Covalent) Bonding Mechanism 50
2.2.5.1 Hydrogen Bonding 51
2.2.6 Acid-Base Theory 51
2.2.7 Weak Boundary Layers 52
2.2.8 Stickiness or Tackiness 53
2.3 Protein Adhesives 54
2.3.1 Animal-Sourced Proteins 55
2.3.2 Plant Proteins 57
2.4 Carbohydrate-Based Adhesives 59
2.5 Plant or Wood-Based Extractives 60
2.5.1 Rubber 60
2.5.2 Resins 61
2.5.2.1 Rosin 62
2.5.2.2 Terpene Resins 63
2.5.2.3 Tannins 64
2.5.2.4 Gums 65
2.6 Fats or Oils 66
2.6.1 Tung Oil 67
2.6.2 Linseed Oil 68
2.6.3 Soybean Oil 69
2.6.4 Castor Oil 70
2.6.5 Miscellaneous Oils 71
2.7 Summary 72
Acknowledgements 72
List of Abbreviations 72
References 74
3 The Chemistry of Bioadhesives 85
A. Pizzi
3.1 Introduction 85
3.2 Carbohydrate Bioadhesives 86
3.3 Protein Bioadhesives 91
3.4 Lignin-Based Bioadhesives 93
3.5 Tannin-Based Bioadhesives 95
3.5.1 Hydrolysable Tannins 96
3.5.1.1 Gallo-Tannins 96
3.5.1.2 Ellagi-Tannins 96
3.5.2 Condensed Polyflavonoid Tannins 96
3.5.3 Reactions of Condensed Flavonoid Tannins 99
3.6 Other Bio-Adhesives for Wood Composites 106
3.7 Summary 108
List of Abbreviations 109
References 110
4 Biorefinery Products as Naturally-Based Key Raw Materials for Adhesives 119
Johannes Karl Fink
4.1 Biorefinery Systems 119
4.1.1 History of Biomaterials 119
4.1.2 Classification of Biorefinery Systems 120
4.1.3 Biorefinery Processes 123
4.1.3.1 Hydrothermal Processes 123
4.1.3.2 Thermochemical Processes 123
4.1.3.3 Chemical Processes 124
4.1.3.4 Biochemical Processes 124
4.1.3.5 Bacterial Processes 124
4.1.4 Renewable Materials for Biorefinery 126
4.1.4.1 Carbohydrates 126
4.1.4.2 Lignin 126
4.1.4.3 Triglycerides 127
4.1.4.4 Mixed Organic Residues 127
4.2 Biobased Materials 128
4.2.1 Biobased Monomers 128
4.2.2 Synthesis Methods 129
4.2.2.1 L-3,4-Dihydroxyphenylalanine 135
4.2.2.2 2-Pyrone-4,6-dicarboxylic acid 136
4.3 Biobased Materials Suitable for Adhesives 137
4.3.1 Additives 137
4.3.2 Wood Adhesives 138
4.3.3 Lignin-Based Adhesives 139
4.3.4 Biorefinery Process of Kash 139
4.3.5 Lignin-Phenol Adhesives 140
4.3.5.1 Enzymatic Hydrolysis of Lignin 141
4.3.5.2 Biorefinery Residues 142
4.3.5.3 Phenol Replacement by Lignins 142
4.3.6 Lignin-Epoxy Adhesives 143
4.3.7 Lignosulfonates 145
4.3.8 Tannins 145
4.3.9 Protein-Based Adhesives 146
4.4 Synthesis Methods for Biobased Adhesives 147
4.4.1 Methylolated Wood-Derived Bio-Oil 147
4.4.2 Biosynthesis of Lignin 148
4.4.3 Soy-Based Adhesives 149
4.4.4 Bisphenol A-Glycidyl Methacrylate Replacement 149
4.5 Modification of Lignin for Better Performance 150
4.5.1 Functionalization with Aromatic Compounds 152
4.5.1.1 Functionalization of Lignin 153
4.5.1.2 Phenolation of Lignin 154
4.5.2 Organosolv Lignin-Based Materials 155
4.6 Pressure-Sensitive Adhesives 155
4.6.1 Lignin as Filler 156
4.6.2 Biobased Acrylic Compounds 156
4.6.3 UV-Tunable Pressure-Sensitive Adhesives 157
4.7 Summary 158
References 158
5 Natural Aldehyde-Based Thermosetting Resins 167
Manfred Dunky
5.1 Introduction 167
5.2 Aliphatic Aldehydes 168
5.2.1 Acetaldehyde 168
5.2.2 Glyoxal 169
5.2.2.1 Glyoxalation of Lignin 171
5.2.2.2 Glyoxylic Acid and Glyoxal 176
5.2.2.3 Glyoxal and Glutaraldehyde 176
5.2.2.4 Glyoxal and 5-Hydroxymethylfurfural (5-HMF) 177
5.2.3 Dimethoxy-Ethanal (Dimethoxy-Acetaldehyde, DME) 177
5.2.4 Propanal (Propionaldehyde) 178
5.2.5 Butyraldehyde 178
5.2.6 Isobutyraldehyde (Isobutanal) 179
5.2.7 Succinaldehyde (Butandial) 179
5.2.8 Glutar(di)aldehyde (GA) (Pentandial) 180
5.3 Aldehydes Based on Cyclic Structures 180
5.3.1 Furfural (Furfurylaldehyde) 180
5.3.2 Furfuryl Alcohol (FA) 184
5.3.3 5-Hydroxymethylfurfural (5-HMF) (see also Chapters 1 and 17) 185
5.3.4 2,5-Diformylfuran (2,5-Furan-Dicarbaldehyde) 192
5.3.5 Aromatic Aldehyde Precursors 193
5.3.6 Polymers with Pendent Aldehyde Groups 194
5.4 Summary 195
List of Abbreviations 195
References 198
6 Natural Crosslinkers for Naturally-Based Adhesives 207
Manfred Dunky
6.1 Introduction 207
6.2 Crosslinking Reactions 208
6.2.1 Proteins 208
6.2.2 Tannins 211
6.2.3 Carbohydrates 214
6.2.4 Lignins 217
6.3 Aliphatic Aldehydes as Crosslinkers 219
6.3.1 Formaldehyde 219
6.3.2 Higher Aldehydes 221
6.3.3 Glyoxal 221
6.3.4 Glutaraldehyde 223
6.3.5 Higher Aliphatic Aldehydes 226
6.4 Cyclic and Aromatic Aldehydes as Crosslinkers 226
6.4.1 Furfural 226
6.4.2 5-Hydroxymethylfurfural (5-HMF) 228
6.4.3 Non-Volatile Aldehydes from Carbohydrates 230
6.5 Crosslinkers Prepared from Biomass 231
6.5.1 Furfuryl Alcohol 231
6.5.2 Extracts as Crosslinkers 234
6.5.3 Glycerol Diglycidyl Ether (GDE), Glycerol Polyglycidyl Ether (GPE), and Ethylene Glycol Diglycidyl Ether (EGDE) 234
6.5.4 Triglycidylamine (TGA) 236
6.5.5 Diethylene-Triamine (DETA) 237
6.5.6 Citric Acid 237
6.6 Synthetic Crosslinkers 240
6.6.1 Polyamidoamine-Epichlorohydrin (PAE) Resins 240
6.6.2 Epoxy Resins 241
6.6.3 Polyethylenimine (PEI) 242
6.6.4 Polyamidoamine (PADA) 243
List of Abbreviations 243
References 245
7 Curing and Adhesive Bond Strength Development in Naturally-Based Adhesives 255
Milan Sernek and Jure ?igon
7.1 Introduction 255
7.2 Curing Monitoring Techniques 256
7.2.1 Gel Time Test 256
7.2.2 Differential Scanning Calorimetry (DSC) 257
7.2.3 Thermogravimetric Analysis (TGA) 258
7.2.4 Dielectric Analysis (DEA) 259
7.3 Bond Strength Development Monitoring Techniques 260
7.3.1 Dynamic Mechanical Analysis (DMA) 260
7.3.2 Thermomechanical Analysis (TMA) 261
7.3.3 Automated Bonding Evaluation System (ABES) 262
7.3.4 Tensile-Shear Strength 263
7.4 Curing Mechanisms in Naturally-Based Adhesives 263
7.4.1 Tannin-Based Adhesives 263
7.4.2 Lignin-Based Adhesives 265
7.4.3 Soy-Based Adhesives 267
7.4.4 Sucrose-Based Adhesives 269
7.4.5 Starch-Based Adhesives 270
7.4.6 Liquefied Wood (LW)-Based Adhesives 271
7.5 Summary 272
Acknowledgements 273
List of Abbreviations 273
References 274
8 Mimicking Nature: Bio-Inspired Adhesives 279
Manfred Dunky
8.1 Introduction 279
8.2 Improvement of Adhesive Performance 282
8.3 Underwater Adhesives (Wet Application Adhesives) 286
8.4 Detechable Bonding and Self-Healing Polymers 289
8.5 Medical Applications 292
8.6 Summary 294
List of Abbreviations 294
References 295
Part 2: Classes of Biobased Adhesives 305
9 Protein Adhesives - Composition, Structure and Performance 307
Charles R. Frihart
9.1 Introduction 307
9.2 Composition of Proteins 308
9.3 Types, Sources, Processing, and Properties of Proteins 309
9.3.1 Collagen (Animal) 309
9.3.2 Globular (Plant) 311
9.3.3 Globular (Milk) 315
9.3.4 Globular (Egg) 316
9.3.5 Globular (Blood) 317
9.3.6 Other Protein Sources 317
9.4 Conclusion (Future of Protein Adhesives) and Summary 317
List of Abbreviations 318
References 319
10 Carbohydrates (Polysaccharides) as Adhesives 325
Lee Seng Hua and Lum Wei Chen
10.1 Introduction 325
10.2 Cellulose Derivatives 326
10.3 Starch-Based Adhesives 330
10.4 Dextrin 331
10.5 Natural Gums 333
10.6 Chitosan 335
10.7 Summary and Prospects 339
Acknowledgements 340
List of Abbreviations 340
References 341
11 Natural Polymer-Based Adhesives 345
A.A. Shybi, Siby Varghese, Hanna J. Maria and Sabu Thomas
11.1 Introduction 345
11.2 Natural Rubber (NR)-Based Adhesives 346
11.2.1 Introduction to NR-Based Adhesives 346
11.2.2 NR-Based Wood Adhesives 350
11.2.3 NR-Based Pressure-Sensitive Adhesives 352
11.2.4 NR-Based Adhesives in Leather, Rubber, Textile and Metal Bonding Applications 353
11.3 Poly(lactic acid) (PLA)-Based Wood Adhesives 354
11.3.1 Introduction to PLA-Based Adhesives 354
11.3.2 PLA-Based Wood Adhesives 355
11.3.3 PLA-Based Hot-Melt Adhesives 356
11.3.4 PLA-Based Adhesives for Metal Bonding 357
11.4 Chitosan-Based Adhesives 357
11.4.1 Introduction to Chitosan-Based Adhesives 357
11.4.2 Chitosan-Based Wood Adhesives 358
11.5 Summary 359
List of Abbreviations 360
References 361
12 Epoxy Adhesives from Natural Materials 367
Charles R. Frihart
12.1 Introduction and Morphology 367
12.2 Basic Properties of Epoxies 369
12.3 Epoxy Synthesis 370
12.4 Epoxy Curing 373
12.4.1 One-Component Epoxies 375
12.4.2 Two-Component Epoxies 376
12.5 Aromatic Epoxies 376
12.5.1 Aromatic Bis-Phenol Epoxies 376
12.5.2 Aromatic Novolac Epoxies 377
12.5.3 Biobased Aromatic Epoxies from Polyphenols, Tannins, Cardanol, and Lignin 378
12.5.4 Aromatic Epoxies from Lignin and Woody Biomass 378
12.6 Aliphatic Epoxies 379
12.6.1 Aliphatic Epoxies from Vegetable Oils 380
12.6.2 Aliphatic Epoxies from Sugars 381
12.6.3 Aliphatic Epoxies from Terpenoids 382
12.6.4 Other Aliphatic Epoxies 382
12.7 Hardeners 383
12.7.1 Amines 383
12.7.1.1 Aliphatic Amines 383
12.7.1.2 Biobased Aliphatic Amines 384
12.7.1.3 Aromatic Amines 385
12.7.2 Anhydrides of Organic Acids...
Part 1: Fundamental Aspects 1
1 Introduction to Naturally-Based (Bio-) Adhesives 3
Manfred Dunky
1.1 Introduction 3
1.2 Overview and Challenges For Adhesives Based on Natural Resources 6
1.2.1 Combined Use of Synthetic and Naturally-Based Adhesives 8
1.2.2 Overview on Adhesives Based on Natural Resources 9
1.2.3 Requirements, Limitations, and Opportunities for Wood Adhesives Based on Natural Resources 11
1.3 Biorefinery and Platform Chemicals 11
1.4 Lignin as Raw Material for Platform Chemicals 20
1.5 5-Hydroxymethylfurfural (5-HMF) as Platform Chemical 23
1.6 Mimicking Nature 27
1.7 Special Topics and Latest Developments 29
1.8 Prospects 30
1.9 Summary 30
General Literature on Biobased Adhesives 30
List of Abbreviations 34
References 35
2 Adhesion Theories in Naturally-Based Bonding: Adhesion and Surface Issues with Naturally-Based Adhesives 45
Douglas J. Gardner, Geeta Pokhrel and Alexander Collins
2.1 Introduction 45
2.2 Adhesion Theories 46
2.2.1 Mechanical Interlocking 47
2.2.2 Electrostatic Mechanism 48
2.2.3 Adsorption (Thermodynamic) or Wetting Mechanism 49
2.2.4 Diffusion Mechanism 50
2.2.5 Chemical (Covalent) Bonding Mechanism 50
2.2.5.1 Hydrogen Bonding 51
2.2.6 Acid-Base Theory 51
2.2.7 Weak Boundary Layers 52
2.2.8 Stickiness or Tackiness 53
2.3 Protein Adhesives 54
2.3.1 Animal-Sourced Proteins 55
2.3.2 Plant Proteins 57
2.4 Carbohydrate-Based Adhesives 59
2.5 Plant or Wood-Based Extractives 60
2.5.1 Rubber 60
2.5.2 Resins 61
2.5.2.1 Rosin 62
2.5.2.2 Terpene Resins 63
2.5.2.3 Tannins 64
2.5.2.4 Gums 65
2.6 Fats or Oils 66
2.6.1 Tung Oil 67
2.6.2 Linseed Oil 68
2.6.3 Soybean Oil 69
2.6.4 Castor Oil 70
2.6.5 Miscellaneous Oils 71
2.7 Summary 72
Acknowledgements 72
List of Abbreviations 72
References 74
3 The Chemistry of Bioadhesives 85
A. Pizzi
3.1 Introduction 85
3.2 Carbohydrate Bioadhesives 86
3.3 Protein Bioadhesives 91
3.4 Lignin-Based Bioadhesives 93
3.5 Tannin-Based Bioadhesives 95
3.5.1 Hydrolysable Tannins 96
3.5.1.1 Gallo-Tannins 96
3.5.1.2 Ellagi-Tannins 96
3.5.2 Condensed Polyflavonoid Tannins 96
3.5.3 Reactions of Condensed Flavonoid Tannins 99
3.6 Other Bio-Adhesives for Wood Composites 106
3.7 Summary 108
List of Abbreviations 109
References 110
4 Biorefinery Products as Naturally-Based Key Raw Materials for Adhesives 119
Johannes Karl Fink
4.1 Biorefinery Systems 119
4.1.1 History of Biomaterials 119
4.1.2 Classification of Biorefinery Systems 120
4.1.3 Biorefinery Processes 123
4.1.3.1 Hydrothermal Processes 123
4.1.3.2 Thermochemical Processes 123
4.1.3.3 Chemical Processes 124
4.1.3.4 Biochemical Processes 124
4.1.3.5 Bacterial Processes 124
4.1.4 Renewable Materials for Biorefinery 126
4.1.4.1 Carbohydrates 126
4.1.4.2 Lignin 126
4.1.4.3 Triglycerides 127
4.1.4.4 Mixed Organic Residues 127
4.2 Biobased Materials 128
4.2.1 Biobased Monomers 128
4.2.2 Synthesis Methods 129
4.2.2.1 L-3,4-Dihydroxyphenylalanine 135
4.2.2.2 2-Pyrone-4,6-dicarboxylic acid 136
4.3 Biobased Materials Suitable for Adhesives 137
4.3.1 Additives 137
4.3.2 Wood Adhesives 138
4.3.3 Lignin-Based Adhesives 139
4.3.4 Biorefinery Process of Kash 139
4.3.5 Lignin-Phenol Adhesives 140
4.3.5.1 Enzymatic Hydrolysis of Lignin 141
4.3.5.2 Biorefinery Residues 142
4.3.5.3 Phenol Replacement by Lignins 142
4.3.6 Lignin-Epoxy Adhesives 143
4.3.7 Lignosulfonates 145
4.3.8 Tannins 145
4.3.9 Protein-Based Adhesives 146
4.4 Synthesis Methods for Biobased Adhesives 147
4.4.1 Methylolated Wood-Derived Bio-Oil 147
4.4.2 Biosynthesis of Lignin 148
4.4.3 Soy-Based Adhesives 149
4.4.4 Bisphenol A-Glycidyl Methacrylate Replacement 149
4.5 Modification of Lignin for Better Performance 150
4.5.1 Functionalization with Aromatic Compounds 152
4.5.1.1 Functionalization of Lignin 153
4.5.1.2 Phenolation of Lignin 154
4.5.2 Organosolv Lignin-Based Materials 155
4.6 Pressure-Sensitive Adhesives 155
4.6.1 Lignin as Filler 156
4.6.2 Biobased Acrylic Compounds 156
4.6.3 UV-Tunable Pressure-Sensitive Adhesives 157
4.7 Summary 158
References 158
5 Natural Aldehyde-Based Thermosetting Resins 167
Manfred Dunky
5.1 Introduction 167
5.2 Aliphatic Aldehydes 168
5.2.1 Acetaldehyde 168
5.2.2 Glyoxal 169
5.2.2.1 Glyoxalation of Lignin 171
5.2.2.2 Glyoxylic Acid and Glyoxal 176
5.2.2.3 Glyoxal and Glutaraldehyde 176
5.2.2.4 Glyoxal and 5-Hydroxymethylfurfural (5-HMF) 177
5.2.3 Dimethoxy-Ethanal (Dimethoxy-Acetaldehyde, DME) 177
5.2.4 Propanal (Propionaldehyde) 178
5.2.5 Butyraldehyde 178
5.2.6 Isobutyraldehyde (Isobutanal) 179
5.2.7 Succinaldehyde (Butandial) 179
5.2.8 Glutar(di)aldehyde (GA) (Pentandial) 180
5.3 Aldehydes Based on Cyclic Structures 180
5.3.1 Furfural (Furfurylaldehyde) 180
5.3.2 Furfuryl Alcohol (FA) 184
5.3.3 5-Hydroxymethylfurfural (5-HMF) (see also Chapters 1 and 17) 185
5.3.4 2,5-Diformylfuran (2,5-Furan-Dicarbaldehyde) 192
5.3.5 Aromatic Aldehyde Precursors 193
5.3.6 Polymers with Pendent Aldehyde Groups 194
5.4 Summary 195
List of Abbreviations 195
References 198
6 Natural Crosslinkers for Naturally-Based Adhesives 207
Manfred Dunky
6.1 Introduction 207
6.2 Crosslinking Reactions 208
6.2.1 Proteins 208
6.2.2 Tannins 211
6.2.3 Carbohydrates 214
6.2.4 Lignins 217
6.3 Aliphatic Aldehydes as Crosslinkers 219
6.3.1 Formaldehyde 219
6.3.2 Higher Aldehydes 221
6.3.3 Glyoxal 221
6.3.4 Glutaraldehyde 223
6.3.5 Higher Aliphatic Aldehydes 226
6.4 Cyclic and Aromatic Aldehydes as Crosslinkers 226
6.4.1 Furfural 226
6.4.2 5-Hydroxymethylfurfural (5-HMF) 228
6.4.3 Non-Volatile Aldehydes from Carbohydrates 230
6.5 Crosslinkers Prepared from Biomass 231
6.5.1 Furfuryl Alcohol 231
6.5.2 Extracts as Crosslinkers 234
6.5.3 Glycerol Diglycidyl Ether (GDE), Glycerol Polyglycidyl Ether (GPE), and Ethylene Glycol Diglycidyl Ether (EGDE) 234
6.5.4 Triglycidylamine (TGA) 236
6.5.5 Diethylene-Triamine (DETA) 237
6.5.6 Citric Acid 237
6.6 Synthetic Crosslinkers 240
6.6.1 Polyamidoamine-Epichlorohydrin (PAE) Resins 240
6.6.2 Epoxy Resins 241
6.6.3 Polyethylenimine (PEI) 242
6.6.4 Polyamidoamine (PADA) 243
List of Abbreviations 243
References 245
7 Curing and Adhesive Bond Strength Development in Naturally-Based Adhesives 255
Milan Sernek and Jure ?igon
7.1 Introduction 255
7.2 Curing Monitoring Techniques 256
7.2.1 Gel Time Test 256
7.2.2 Differential Scanning Calorimetry (DSC) 257
7.2.3 Thermogravimetric Analysis (TGA) 258
7.2.4 Dielectric Analysis (DEA) 259
7.3 Bond Strength Development Monitoring Techniques 260
7.3.1 Dynamic Mechanical Analysis (DMA) 260
7.3.2 Thermomechanical Analysis (TMA) 261
7.3.3 Automated Bonding Evaluation System (ABES) 262
7.3.4 Tensile-Shear Strength 263
7.4 Curing Mechanisms in Naturally-Based Adhesives 263
7.4.1 Tannin-Based Adhesives 263
7.4.2 Lignin-Based Adhesives 265
7.4.3 Soy-Based Adhesives 267
7.4.4 Sucrose-Based Adhesives 269
7.4.5 Starch-Based Adhesives 270
7.4.6 Liquefied Wood (LW)-Based Adhesives 271
7.5 Summary 272
Acknowledgements 273
List of Abbreviations 273
References 274
8 Mimicking Nature: Bio-Inspired Adhesives 279
Manfred Dunky
8.1 Introduction 279
8.2 Improvement of Adhesive Performance 282
8.3 Underwater Adhesives (Wet Application Adhesives) 286
8.4 Detechable Bonding and Self-Healing Polymers 289
8.5 Medical Applications 292
8.6 Summary 294
List of Abbreviations 294
References 295
Part 2: Classes of Biobased Adhesives 305
9 Protein Adhesives - Composition, Structure and Performance 307
Charles R. Frihart
9.1 Introduction 307
9.2 Composition of Proteins 308
9.3 Types, Sources, Processing, and Properties of Proteins 309
9.3.1 Collagen (Animal) 309
9.3.2 Globular (Plant) 311
9.3.3 Globular (Milk) 315
9.3.4 Globular (Egg) 316
9.3.5 Globular (Blood) 317
9.3.6 Other Protein Sources 317
9.4 Conclusion (Future of Protein Adhesives) and Summary 317
List of Abbreviations 318
References 319
10 Carbohydrates (Polysaccharides) as Adhesives 325
Lee Seng Hua and Lum Wei Chen
10.1 Introduction 325
10.2 Cellulose Derivatives 326
10.3 Starch-Based Adhesives 330
10.4 Dextrin 331
10.5 Natural Gums 333
10.6 Chitosan 335
10.7 Summary and Prospects 339
Acknowledgements 340
List of Abbreviations 340
References 341
11 Natural Polymer-Based Adhesives 345
A.A. Shybi, Siby Varghese, Hanna J. Maria and Sabu Thomas
11.1 Introduction 345
11.2 Natural Rubber (NR)-Based Adhesives 346
11.2.1 Introduction to NR-Based Adhesives 346
11.2.2 NR-Based Wood Adhesives 350
11.2.3 NR-Based Pressure-Sensitive Adhesives 352
11.2.4 NR-Based Adhesives in Leather, Rubber, Textile and Metal Bonding Applications 353
11.3 Poly(lactic acid) (PLA)-Based Wood Adhesives 354
11.3.1 Introduction to PLA-Based Adhesives 354
11.3.2 PLA-Based Wood Adhesives 355
11.3.3 PLA-Based Hot-Melt Adhesives 356
11.3.4 PLA-Based Adhesives for Metal Bonding 357
11.4 Chitosan-Based Adhesives 357
11.4.1 Introduction to Chitosan-Based Adhesives 357
11.4.2 Chitosan-Based Wood Adhesives 358
11.5 Summary 359
List of Abbreviations 360
References 361
12 Epoxy Adhesives from Natural Materials 367
Charles R. Frihart
12.1 Introduction and Morphology 367
12.2 Basic Properties of Epoxies 369
12.3 Epoxy Synthesis 370
12.4 Epoxy Curing 373
12.4.1 One-Component Epoxies 375
12.4.2 Two-Component Epoxies 376
12.5 Aromatic Epoxies 376
12.5.1 Aromatic Bis-Phenol Epoxies 376
12.5.2 Aromatic Novolac Epoxies 377
12.5.3 Biobased Aromatic Epoxies from Polyphenols, Tannins, Cardanol, and Lignin 378
12.5.4 Aromatic Epoxies from Lignin and Woody Biomass 378
12.6 Aliphatic Epoxies 379
12.6.1 Aliphatic Epoxies from Vegetable Oils 380
12.6.2 Aliphatic Epoxies from Sugars 381
12.6.3 Aliphatic Epoxies from Terpenoids 382
12.6.4 Other Aliphatic Epoxies 382
12.7 Hardeners 383
12.7.1 Amines 383
12.7.1.1 Aliphatic Amines 383
12.7.1.2 Biobased Aliphatic Amines 384
12.7.1.3 Aromatic Amines 385
12.7.2 Anhydrides of Organic Acids...
Details
| Erscheinungsjahr: | 2023 |
|---|---|
| Fachbereich: | Technik allgemein |
| Genre: | Technik |
| Rubrik: | Naturwissenschaften & Technik |
| Medium: | Buch |
| Seiten: | 768 |
| Inhalt: | 768 S. |
| ISBN-13: | 9781394174638 |
| ISBN-10: | 1394174632 |
| Sprache: | Englisch |
| Einband: | Gebunden |
| Redaktion: |
Mittal, K. L.
Dunky, Manfred |
| Herausgeber: | Manfred Dunky/K L Mittal |
| Hersteller: | John Wiley & Sons Inc |
| Maße: | 260 x 185 x 49 mm |
| Von/Mit: | K. L. Mittal (u. a.) |
| Erscheinungsdatum: | 19.05.2023 |
| Gewicht: | 1,578 kg |
Über den Autor
Manfred Dunky, PhD, has spent a 40-year career in the chemical and wood-based panels industry as a researcher and consultant. During the last 25 years, he has placed an emphasis on adhesives based on natural resources. Besides his industry career, in 2000 he received his habilitation (post-doctoral lecturing qualification) for "Wood Science with special consideration of wood-based panels" and was a lecturer at several universities. He is invited regularly to speak at many wood science conferences.
Kashmiri Lal Mittal was employed by the IBM Corporation from 1972 through 1993. Currently, he is teaching and consulting worldwide in the broad areas of adhesion, as well as surface cleaning. He has received numerous awards and honors, including the title of doctor honoris causa from Maria Curie-Sk3odowska University, Lublin, Poland. He is the editor of over 150 books dealing with adhesion measurement, adhesion of polymeric coatings, polymer surfaces, adhesive joints, adhesion promoters, thin films, polyimides, surface modification surface cleaning, and surfactants.
Inhaltsverzeichnis
Preface xvii
Part 1: Fundamental Aspects 1
1 Introduction to Naturally-Based (Bio-) Adhesives 3
Manfred Dunky
1.1 Introduction 3
1.2 Overview and Challenges For Adhesives Based on Natural Resources 6
1.2.1 Combined Use of Synthetic and Naturally-Based Adhesives 8
1.2.2 Overview on Adhesives Based on Natural Resources 9
1.2.3 Requirements, Limitations, and Opportunities for Wood Adhesives Based on Natural Resources 11
1.3 Biorefinery and Platform Chemicals 11
1.4 Lignin as Raw Material for Platform Chemicals 20
1.5 5-Hydroxymethylfurfural (5-HMF) as Platform Chemical 23
1.6 Mimicking Nature 27
1.7 Special Topics and Latest Developments 29
1.8 Prospects 30
1.9 Summary 30
General Literature on Biobased Adhesives 30
List of Abbreviations 34
References 35
2 Adhesion Theories in Naturally-Based Bonding: Adhesion and Surface Issues with Naturally-Based Adhesives 45
Douglas J. Gardner, Geeta Pokhrel and Alexander Collins
2.1 Introduction 45
2.2 Adhesion Theories 46
2.2.1 Mechanical Interlocking 47
2.2.2 Electrostatic Mechanism 48
2.2.3 Adsorption (Thermodynamic) or Wetting Mechanism 49
2.2.4 Diffusion Mechanism 50
2.2.5 Chemical (Covalent) Bonding Mechanism 50
2.2.5.1 Hydrogen Bonding 51
2.2.6 Acid-Base Theory 51
2.2.7 Weak Boundary Layers 52
2.2.8 Stickiness or Tackiness 53
2.3 Protein Adhesives 54
2.3.1 Animal-Sourced Proteins 55
2.3.2 Plant Proteins 57
2.4 Carbohydrate-Based Adhesives 59
2.5 Plant or Wood-Based Extractives 60
2.5.1 Rubber 60
2.5.2 Resins 61
2.5.2.1 Rosin 62
2.5.2.2 Terpene Resins 63
2.5.2.3 Tannins 64
2.5.2.4 Gums 65
2.6 Fats or Oils 66
2.6.1 Tung Oil 67
2.6.2 Linseed Oil 68
2.6.3 Soybean Oil 69
2.6.4 Castor Oil 70
2.6.5 Miscellaneous Oils 71
2.7 Summary 72
Acknowledgements 72
List of Abbreviations 72
References 74
3 The Chemistry of Bioadhesives 85
A. Pizzi
3.1 Introduction 85
3.2 Carbohydrate Bioadhesives 86
3.3 Protein Bioadhesives 91
3.4 Lignin-Based Bioadhesives 93
3.5 Tannin-Based Bioadhesives 95
3.5.1 Hydrolysable Tannins 96
3.5.1.1 Gallo-Tannins 96
3.5.1.2 Ellagi-Tannins 96
3.5.2 Condensed Polyflavonoid Tannins 96
3.5.3 Reactions of Condensed Flavonoid Tannins 99
3.6 Other Bio-Adhesives for Wood Composites 106
3.7 Summary 108
List of Abbreviations 109
References 110
4 Biorefinery Products as Naturally-Based Key Raw Materials for Adhesives 119
Johannes Karl Fink
4.1 Biorefinery Systems 119
4.1.1 History of Biomaterials 119
4.1.2 Classification of Biorefinery Systems 120
4.1.3 Biorefinery Processes 123
4.1.3.1 Hydrothermal Processes 123
4.1.3.2 Thermochemical Processes 123
4.1.3.3 Chemical Processes 124
4.1.3.4 Biochemical Processes 124
4.1.3.5 Bacterial Processes 124
4.1.4 Renewable Materials for Biorefinery 126
4.1.4.1 Carbohydrates 126
4.1.4.2 Lignin 126
4.1.4.3 Triglycerides 127
4.1.4.4 Mixed Organic Residues 127
4.2 Biobased Materials 128
4.2.1 Biobased Monomers 128
4.2.2 Synthesis Methods 129
4.2.2.1 L-3,4-Dihydroxyphenylalanine 135
4.2.2.2 2-Pyrone-4,6-dicarboxylic acid 136
4.3 Biobased Materials Suitable for Adhesives 137
4.3.1 Additives 137
4.3.2 Wood Adhesives 138
4.3.3 Lignin-Based Adhesives 139
4.3.4 Biorefinery Process of Kash 139
4.3.5 Lignin-Phenol Adhesives 140
4.3.5.1 Enzymatic Hydrolysis of Lignin 141
4.3.5.2 Biorefinery Residues 142
4.3.5.3 Phenol Replacement by Lignins 142
4.3.6 Lignin-Epoxy Adhesives 143
4.3.7 Lignosulfonates 145
4.3.8 Tannins 145
4.3.9 Protein-Based Adhesives 146
4.4 Synthesis Methods for Biobased Adhesives 147
4.4.1 Methylolated Wood-Derived Bio-Oil 147
4.4.2 Biosynthesis of Lignin 148
4.4.3 Soy-Based Adhesives 149
4.4.4 Bisphenol A-Glycidyl Methacrylate Replacement 149
4.5 Modification of Lignin for Better Performance 150
4.5.1 Functionalization with Aromatic Compounds 152
4.5.1.1 Functionalization of Lignin 153
4.5.1.2 Phenolation of Lignin 154
4.5.2 Organosolv Lignin-Based Materials 155
4.6 Pressure-Sensitive Adhesives 155
4.6.1 Lignin as Filler 156
4.6.2 Biobased Acrylic Compounds 156
4.6.3 UV-Tunable Pressure-Sensitive Adhesives 157
4.7 Summary 158
References 158
5 Natural Aldehyde-Based Thermosetting Resins 167
Manfred Dunky
5.1 Introduction 167
5.2 Aliphatic Aldehydes 168
5.2.1 Acetaldehyde 168
5.2.2 Glyoxal 169
5.2.2.1 Glyoxalation of Lignin 171
5.2.2.2 Glyoxylic Acid and Glyoxal 176
5.2.2.3 Glyoxal and Glutaraldehyde 176
5.2.2.4 Glyoxal and 5-Hydroxymethylfurfural (5-HMF) 177
5.2.3 Dimethoxy-Ethanal (Dimethoxy-Acetaldehyde, DME) 177
5.2.4 Propanal (Propionaldehyde) 178
5.2.5 Butyraldehyde 178
5.2.6 Isobutyraldehyde (Isobutanal) 179
5.2.7 Succinaldehyde (Butandial) 179
5.2.8 Glutar(di)aldehyde (GA) (Pentandial) 180
5.3 Aldehydes Based on Cyclic Structures 180
5.3.1 Furfural (Furfurylaldehyde) 180
5.3.2 Furfuryl Alcohol (FA) 184
5.3.3 5-Hydroxymethylfurfural (5-HMF) (see also Chapters 1 and 17) 185
5.3.4 2,5-Diformylfuran (2,5-Furan-Dicarbaldehyde) 192
5.3.5 Aromatic Aldehyde Precursors 193
5.3.6 Polymers with Pendent Aldehyde Groups 194
5.4 Summary 195
List of Abbreviations 195
References 198
6 Natural Crosslinkers for Naturally-Based Adhesives 207
Manfred Dunky
6.1 Introduction 207
6.2 Crosslinking Reactions 208
6.2.1 Proteins 208
6.2.2 Tannins 211
6.2.3 Carbohydrates 214
6.2.4 Lignins 217
6.3 Aliphatic Aldehydes as Crosslinkers 219
6.3.1 Formaldehyde 219
6.3.2 Higher Aldehydes 221
6.3.3 Glyoxal 221
6.3.4 Glutaraldehyde 223
6.3.5 Higher Aliphatic Aldehydes 226
6.4 Cyclic and Aromatic Aldehydes as Crosslinkers 226
6.4.1 Furfural 226
6.4.2 5-Hydroxymethylfurfural (5-HMF) 228
6.4.3 Non-Volatile Aldehydes from Carbohydrates 230
6.5 Crosslinkers Prepared from Biomass 231
6.5.1 Furfuryl Alcohol 231
6.5.2 Extracts as Crosslinkers 234
6.5.3 Glycerol Diglycidyl Ether (GDE), Glycerol Polyglycidyl Ether (GPE), and Ethylene Glycol Diglycidyl Ether (EGDE) 234
6.5.4 Triglycidylamine (TGA) 236
6.5.5 Diethylene-Triamine (DETA) 237
6.5.6 Citric Acid 237
6.6 Synthetic Crosslinkers 240
6.6.1 Polyamidoamine-Epichlorohydrin (PAE) Resins 240
6.6.2 Epoxy Resins 241
6.6.3 Polyethylenimine (PEI) 242
6.6.4 Polyamidoamine (PADA) 243
List of Abbreviations 243
References 245
7 Curing and Adhesive Bond Strength Development in Naturally-Based Adhesives 255
Milan Sernek and Jure ?igon
7.1 Introduction 255
7.2 Curing Monitoring Techniques 256
7.2.1 Gel Time Test 256
7.2.2 Differential Scanning Calorimetry (DSC) 257
7.2.3 Thermogravimetric Analysis (TGA) 258
7.2.4 Dielectric Analysis (DEA) 259
7.3 Bond Strength Development Monitoring Techniques 260
7.3.1 Dynamic Mechanical Analysis (DMA) 260
7.3.2 Thermomechanical Analysis (TMA) 261
7.3.3 Automated Bonding Evaluation System (ABES) 262
7.3.4 Tensile-Shear Strength 263
7.4 Curing Mechanisms in Naturally-Based Adhesives 263
7.4.1 Tannin-Based Adhesives 263
7.4.2 Lignin-Based Adhesives 265
7.4.3 Soy-Based Adhesives 267
7.4.4 Sucrose-Based Adhesives 269
7.4.5 Starch-Based Adhesives 270
7.4.6 Liquefied Wood (LW)-Based Adhesives 271
7.5 Summary 272
Acknowledgements 273
List of Abbreviations 273
References 274
8 Mimicking Nature: Bio-Inspired Adhesives 279
Manfred Dunky
8.1 Introduction 279
8.2 Improvement of Adhesive Performance 282
8.3 Underwater Adhesives (Wet Application Adhesives) 286
8.4 Detechable Bonding and Self-Healing Polymers 289
8.5 Medical Applications 292
8.6 Summary 294
List of Abbreviations 294
References 295
Part 2: Classes of Biobased Adhesives 305
9 Protein Adhesives - Composition, Structure and Performance 307
Charles R. Frihart
9.1 Introduction 307
9.2 Composition of Proteins 308
9.3 Types, Sources, Processing, and Properties of Proteins 309
9.3.1 Collagen (Animal) 309
9.3.2 Globular (Plant) 311
9.3.3 Globular (Milk) 315
9.3.4 Globular (Egg) 316
9.3.5 Globular (Blood) 317
9.3.6 Other Protein Sources 317
9.4 Conclusion (Future of Protein Adhesives) and Summary 317
List of Abbreviations 318
References 319
10 Carbohydrates (Polysaccharides) as Adhesives 325
Lee Seng Hua and Lum Wei Chen
10.1 Introduction 325
10.2 Cellulose Derivatives 326
10.3 Starch-Based Adhesives 330
10.4 Dextrin 331
10.5 Natural Gums 333
10.6 Chitosan 335
10.7 Summary and Prospects 339
Acknowledgements 340
List of Abbreviations 340
References 341
11 Natural Polymer-Based Adhesives 345
A.A. Shybi, Siby Varghese, Hanna J. Maria and Sabu Thomas
11.1 Introduction 345
11.2 Natural Rubber (NR)-Based Adhesives 346
11.2.1 Introduction to NR-Based Adhesives 346
11.2.2 NR-Based Wood Adhesives 350
11.2.3 NR-Based Pressure-Sensitive Adhesives 352
11.2.4 NR-Based Adhesives in Leather, Rubber, Textile and Metal Bonding Applications 353
11.3 Poly(lactic acid) (PLA)-Based Wood Adhesives 354
11.3.1 Introduction to PLA-Based Adhesives 354
11.3.2 PLA-Based Wood Adhesives 355
11.3.3 PLA-Based Hot-Melt Adhesives 356
11.3.4 PLA-Based Adhesives for Metal Bonding 357
11.4 Chitosan-Based Adhesives 357
11.4.1 Introduction to Chitosan-Based Adhesives 357
11.4.2 Chitosan-Based Wood Adhesives 358
11.5 Summary 359
List of Abbreviations 360
References 361
12 Epoxy Adhesives from Natural Materials 367
Charles R. Frihart
12.1 Introduction and Morphology 367
12.2 Basic Properties of Epoxies 369
12.3 Epoxy Synthesis 370
12.4 Epoxy Curing 373
12.4.1 One-Component Epoxies 375
12.4.2 Two-Component Epoxies 376
12.5 Aromatic Epoxies 376
12.5.1 Aromatic Bis-Phenol Epoxies 376
12.5.2 Aromatic Novolac Epoxies 377
12.5.3 Biobased Aromatic Epoxies from Polyphenols, Tannins, Cardanol, and Lignin 378
12.5.4 Aromatic Epoxies from Lignin and Woody Biomass 378
12.6 Aliphatic Epoxies 379
12.6.1 Aliphatic Epoxies from Vegetable Oils 380
12.6.2 Aliphatic Epoxies from Sugars 381
12.6.3 Aliphatic Epoxies from Terpenoids 382
12.6.4 Other Aliphatic Epoxies 382
12.7 Hardeners 383
12.7.1 Amines 383
12.7.1.1 Aliphatic Amines 383
12.7.1.2 Biobased Aliphatic Amines 384
12.7.1.3 Aromatic Amines 385
12.7.2 Anhydrides of Organic Acids...
Part 1: Fundamental Aspects 1
1 Introduction to Naturally-Based (Bio-) Adhesives 3
Manfred Dunky
1.1 Introduction 3
1.2 Overview and Challenges For Adhesives Based on Natural Resources 6
1.2.1 Combined Use of Synthetic and Naturally-Based Adhesives 8
1.2.2 Overview on Adhesives Based on Natural Resources 9
1.2.3 Requirements, Limitations, and Opportunities for Wood Adhesives Based on Natural Resources 11
1.3 Biorefinery and Platform Chemicals 11
1.4 Lignin as Raw Material for Platform Chemicals 20
1.5 5-Hydroxymethylfurfural (5-HMF) as Platform Chemical 23
1.6 Mimicking Nature 27
1.7 Special Topics and Latest Developments 29
1.8 Prospects 30
1.9 Summary 30
General Literature on Biobased Adhesives 30
List of Abbreviations 34
References 35
2 Adhesion Theories in Naturally-Based Bonding: Adhesion and Surface Issues with Naturally-Based Adhesives 45
Douglas J. Gardner, Geeta Pokhrel and Alexander Collins
2.1 Introduction 45
2.2 Adhesion Theories 46
2.2.1 Mechanical Interlocking 47
2.2.2 Electrostatic Mechanism 48
2.2.3 Adsorption (Thermodynamic) or Wetting Mechanism 49
2.2.4 Diffusion Mechanism 50
2.2.5 Chemical (Covalent) Bonding Mechanism 50
2.2.5.1 Hydrogen Bonding 51
2.2.6 Acid-Base Theory 51
2.2.7 Weak Boundary Layers 52
2.2.8 Stickiness or Tackiness 53
2.3 Protein Adhesives 54
2.3.1 Animal-Sourced Proteins 55
2.3.2 Plant Proteins 57
2.4 Carbohydrate-Based Adhesives 59
2.5 Plant or Wood-Based Extractives 60
2.5.1 Rubber 60
2.5.2 Resins 61
2.5.2.1 Rosin 62
2.5.2.2 Terpene Resins 63
2.5.2.3 Tannins 64
2.5.2.4 Gums 65
2.6 Fats or Oils 66
2.6.1 Tung Oil 67
2.6.2 Linseed Oil 68
2.6.3 Soybean Oil 69
2.6.4 Castor Oil 70
2.6.5 Miscellaneous Oils 71
2.7 Summary 72
Acknowledgements 72
List of Abbreviations 72
References 74
3 The Chemistry of Bioadhesives 85
A. Pizzi
3.1 Introduction 85
3.2 Carbohydrate Bioadhesives 86
3.3 Protein Bioadhesives 91
3.4 Lignin-Based Bioadhesives 93
3.5 Tannin-Based Bioadhesives 95
3.5.1 Hydrolysable Tannins 96
3.5.1.1 Gallo-Tannins 96
3.5.1.2 Ellagi-Tannins 96
3.5.2 Condensed Polyflavonoid Tannins 96
3.5.3 Reactions of Condensed Flavonoid Tannins 99
3.6 Other Bio-Adhesives for Wood Composites 106
3.7 Summary 108
List of Abbreviations 109
References 110
4 Biorefinery Products as Naturally-Based Key Raw Materials for Adhesives 119
Johannes Karl Fink
4.1 Biorefinery Systems 119
4.1.1 History of Biomaterials 119
4.1.2 Classification of Biorefinery Systems 120
4.1.3 Biorefinery Processes 123
4.1.3.1 Hydrothermal Processes 123
4.1.3.2 Thermochemical Processes 123
4.1.3.3 Chemical Processes 124
4.1.3.4 Biochemical Processes 124
4.1.3.5 Bacterial Processes 124
4.1.4 Renewable Materials for Biorefinery 126
4.1.4.1 Carbohydrates 126
4.1.4.2 Lignin 126
4.1.4.3 Triglycerides 127
4.1.4.4 Mixed Organic Residues 127
4.2 Biobased Materials 128
4.2.1 Biobased Monomers 128
4.2.2 Synthesis Methods 129
4.2.2.1 L-3,4-Dihydroxyphenylalanine 135
4.2.2.2 2-Pyrone-4,6-dicarboxylic acid 136
4.3 Biobased Materials Suitable for Adhesives 137
4.3.1 Additives 137
4.3.2 Wood Adhesives 138
4.3.3 Lignin-Based Adhesives 139
4.3.4 Biorefinery Process of Kash 139
4.3.5 Lignin-Phenol Adhesives 140
4.3.5.1 Enzymatic Hydrolysis of Lignin 141
4.3.5.2 Biorefinery Residues 142
4.3.5.3 Phenol Replacement by Lignins 142
4.3.6 Lignin-Epoxy Adhesives 143
4.3.7 Lignosulfonates 145
4.3.8 Tannins 145
4.3.9 Protein-Based Adhesives 146
4.4 Synthesis Methods for Biobased Adhesives 147
4.4.1 Methylolated Wood-Derived Bio-Oil 147
4.4.2 Biosynthesis of Lignin 148
4.4.3 Soy-Based Adhesives 149
4.4.4 Bisphenol A-Glycidyl Methacrylate Replacement 149
4.5 Modification of Lignin for Better Performance 150
4.5.1 Functionalization with Aromatic Compounds 152
4.5.1.1 Functionalization of Lignin 153
4.5.1.2 Phenolation of Lignin 154
4.5.2 Organosolv Lignin-Based Materials 155
4.6 Pressure-Sensitive Adhesives 155
4.6.1 Lignin as Filler 156
4.6.2 Biobased Acrylic Compounds 156
4.6.3 UV-Tunable Pressure-Sensitive Adhesives 157
4.7 Summary 158
References 158
5 Natural Aldehyde-Based Thermosetting Resins 167
Manfred Dunky
5.1 Introduction 167
5.2 Aliphatic Aldehydes 168
5.2.1 Acetaldehyde 168
5.2.2 Glyoxal 169
5.2.2.1 Glyoxalation of Lignin 171
5.2.2.2 Glyoxylic Acid and Glyoxal 176
5.2.2.3 Glyoxal and Glutaraldehyde 176
5.2.2.4 Glyoxal and 5-Hydroxymethylfurfural (5-HMF) 177
5.2.3 Dimethoxy-Ethanal (Dimethoxy-Acetaldehyde, DME) 177
5.2.4 Propanal (Propionaldehyde) 178
5.2.5 Butyraldehyde 178
5.2.6 Isobutyraldehyde (Isobutanal) 179
5.2.7 Succinaldehyde (Butandial) 179
5.2.8 Glutar(di)aldehyde (GA) (Pentandial) 180
5.3 Aldehydes Based on Cyclic Structures 180
5.3.1 Furfural (Furfurylaldehyde) 180
5.3.2 Furfuryl Alcohol (FA) 184
5.3.3 5-Hydroxymethylfurfural (5-HMF) (see also Chapters 1 and 17) 185
5.3.4 2,5-Diformylfuran (2,5-Furan-Dicarbaldehyde) 192
5.3.5 Aromatic Aldehyde Precursors 193
5.3.6 Polymers with Pendent Aldehyde Groups 194
5.4 Summary 195
List of Abbreviations 195
References 198
6 Natural Crosslinkers for Naturally-Based Adhesives 207
Manfred Dunky
6.1 Introduction 207
6.2 Crosslinking Reactions 208
6.2.1 Proteins 208
6.2.2 Tannins 211
6.2.3 Carbohydrates 214
6.2.4 Lignins 217
6.3 Aliphatic Aldehydes as Crosslinkers 219
6.3.1 Formaldehyde 219
6.3.2 Higher Aldehydes 221
6.3.3 Glyoxal 221
6.3.4 Glutaraldehyde 223
6.3.5 Higher Aliphatic Aldehydes 226
6.4 Cyclic and Aromatic Aldehydes as Crosslinkers 226
6.4.1 Furfural 226
6.4.2 5-Hydroxymethylfurfural (5-HMF) 228
6.4.3 Non-Volatile Aldehydes from Carbohydrates 230
6.5 Crosslinkers Prepared from Biomass 231
6.5.1 Furfuryl Alcohol 231
6.5.2 Extracts as Crosslinkers 234
6.5.3 Glycerol Diglycidyl Ether (GDE), Glycerol Polyglycidyl Ether (GPE), and Ethylene Glycol Diglycidyl Ether (EGDE) 234
6.5.4 Triglycidylamine (TGA) 236
6.5.5 Diethylene-Triamine (DETA) 237
6.5.6 Citric Acid 237
6.6 Synthetic Crosslinkers 240
6.6.1 Polyamidoamine-Epichlorohydrin (PAE) Resins 240
6.6.2 Epoxy Resins 241
6.6.3 Polyethylenimine (PEI) 242
6.6.4 Polyamidoamine (PADA) 243
List of Abbreviations 243
References 245
7 Curing and Adhesive Bond Strength Development in Naturally-Based Adhesives 255
Milan Sernek and Jure ?igon
7.1 Introduction 255
7.2 Curing Monitoring Techniques 256
7.2.1 Gel Time Test 256
7.2.2 Differential Scanning Calorimetry (DSC) 257
7.2.3 Thermogravimetric Analysis (TGA) 258
7.2.4 Dielectric Analysis (DEA) 259
7.3 Bond Strength Development Monitoring Techniques 260
7.3.1 Dynamic Mechanical Analysis (DMA) 260
7.3.2 Thermomechanical Analysis (TMA) 261
7.3.3 Automated Bonding Evaluation System (ABES) 262
7.3.4 Tensile-Shear Strength 263
7.4 Curing Mechanisms in Naturally-Based Adhesives 263
7.4.1 Tannin-Based Adhesives 263
7.4.2 Lignin-Based Adhesives 265
7.4.3 Soy-Based Adhesives 267
7.4.4 Sucrose-Based Adhesives 269
7.4.5 Starch-Based Adhesives 270
7.4.6 Liquefied Wood (LW)-Based Adhesives 271
7.5 Summary 272
Acknowledgements 273
List of Abbreviations 273
References 274
8 Mimicking Nature: Bio-Inspired Adhesives 279
Manfred Dunky
8.1 Introduction 279
8.2 Improvement of Adhesive Performance 282
8.3 Underwater Adhesives (Wet Application Adhesives) 286
8.4 Detechable Bonding and Self-Healing Polymers 289
8.5 Medical Applications 292
8.6 Summary 294
List of Abbreviations 294
References 295
Part 2: Classes of Biobased Adhesives 305
9 Protein Adhesives - Composition, Structure and Performance 307
Charles R. Frihart
9.1 Introduction 307
9.2 Composition of Proteins 308
9.3 Types, Sources, Processing, and Properties of Proteins 309
9.3.1 Collagen (Animal) 309
9.3.2 Globular (Plant) 311
9.3.3 Globular (Milk) 315
9.3.4 Globular (Egg) 316
9.3.5 Globular (Blood) 317
9.3.6 Other Protein Sources 317
9.4 Conclusion (Future of Protein Adhesives) and Summary 317
List of Abbreviations 318
References 319
10 Carbohydrates (Polysaccharides) as Adhesives 325
Lee Seng Hua and Lum Wei Chen
10.1 Introduction 325
10.2 Cellulose Derivatives 326
10.3 Starch-Based Adhesives 330
10.4 Dextrin 331
10.5 Natural Gums 333
10.6 Chitosan 335
10.7 Summary and Prospects 339
Acknowledgements 340
List of Abbreviations 340
References 341
11 Natural Polymer-Based Adhesives 345
A.A. Shybi, Siby Varghese, Hanna J. Maria and Sabu Thomas
11.1 Introduction 345
11.2 Natural Rubber (NR)-Based Adhesives 346
11.2.1 Introduction to NR-Based Adhesives 346
11.2.2 NR-Based Wood Adhesives 350
11.2.3 NR-Based Pressure-Sensitive Adhesives 352
11.2.4 NR-Based Adhesives in Leather, Rubber, Textile and Metal Bonding Applications 353
11.3 Poly(lactic acid) (PLA)-Based Wood Adhesives 354
11.3.1 Introduction to PLA-Based Adhesives 354
11.3.2 PLA-Based Wood Adhesives 355
11.3.3 PLA-Based Hot-Melt Adhesives 356
11.3.4 PLA-Based Adhesives for Metal Bonding 357
11.4 Chitosan-Based Adhesives 357
11.4.1 Introduction to Chitosan-Based Adhesives 357
11.4.2 Chitosan-Based Wood Adhesives 358
11.5 Summary 359
List of Abbreviations 360
References 361
12 Epoxy Adhesives from Natural Materials 367
Charles R. Frihart
12.1 Introduction and Morphology 367
12.2 Basic Properties of Epoxies 369
12.3 Epoxy Synthesis 370
12.4 Epoxy Curing 373
12.4.1 One-Component Epoxies 375
12.4.2 Two-Component Epoxies 376
12.5 Aromatic Epoxies 376
12.5.1 Aromatic Bis-Phenol Epoxies 376
12.5.2 Aromatic Novolac Epoxies 377
12.5.3 Biobased Aromatic Epoxies from Polyphenols, Tannins, Cardanol, and Lignin 378
12.5.4 Aromatic Epoxies from Lignin and Woody Biomass 378
12.6 Aliphatic Epoxies 379
12.6.1 Aliphatic Epoxies from Vegetable Oils 380
12.6.2 Aliphatic Epoxies from Sugars 381
12.6.3 Aliphatic Epoxies from Terpenoids 382
12.6.4 Other Aliphatic Epoxies 382
12.7 Hardeners 383
12.7.1 Amines 383
12.7.1.1 Aliphatic Amines 383
12.7.1.2 Biobased Aliphatic Amines 384
12.7.1.3 Aromatic Amines 385
12.7.2 Anhydrides of Organic Acids...
Details
| Erscheinungsjahr: | 2023 |
|---|---|
| Fachbereich: | Technik allgemein |
| Genre: | Technik |
| Rubrik: | Naturwissenschaften & Technik |
| Medium: | Buch |
| Seiten: | 768 |
| Inhalt: | 768 S. |
| ISBN-13: | 9781394174638 |
| ISBN-10: | 1394174632 |
| Sprache: | Englisch |
| Einband: | Gebunden |
| Redaktion: |
Mittal, K. L.
Dunky, Manfred |
| Herausgeber: | Manfred Dunky/K L Mittal |
| Hersteller: | John Wiley & Sons Inc |
| Maße: | 260 x 185 x 49 mm |
| Von/Mit: | K. L. Mittal (u. a.) |
| Erscheinungsdatum: | 19.05.2023 |
| Gewicht: | 1,578 kg |
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