Cover -- Title Page -- Copyright Page -- Contents -- Preface -- Part 1: Fundamental Aspects -- Chapter 1 Introduction to Naturally-Based (Bio-) Adhesives -- 1.1 Introduction -- 1.2 Overview and Challenges For Adhesives Based on Natural Resources -- 1.2.1 Combined Use of Synthetic and Naturally-Based Adhesives -- 1.2.2 Overview on Adhesives Based on Natural Resources -- 1.2.3 Requirements, Limitations, and Opportunities for Wood Adhesives Based on Natural Resources -- 1.3 Biorefinery and Platform Chemicals -- 1.4 Lignin as Raw Material for Platform Chemicals -- 1.5 5-Hydroxymethylfurfural (5-HMF) as Platform Chemical -- 1.6 Mimicking Nature -- 1.7 Special Topics and Latest Developments -- 1.8 Prospects -- 1.9 Summary -- General Literature on Biobased Adhesives -- List of Abbreviations -- References -- Chapter 2 Adhesion Theories in Naturally-Based Bonding: Adhesion and Surface Issues with Naturally-Based Adhesives -- 2.1 Introduction -- 2.2 Adhesion Theories -- 2.2.1 Mechanical Interlocking -- 2.2.2 Electrostatic Mechanism -- 2.2.3 Adsorption (Thermodynamic) or Wetting Mechanism -- 2.2.4 Diffusion Mechanism -- 2.2.5 Chemical (Covalent) Bonding Mechanism -- 2.2.5.1 Hydrogen Bonding -- 2.2.6 Acid-Base Theory -- 2.2.7 Weak Boundary Layers -- 2.2.8 Stickiness or Tackiness -- 2.3 Protein Adhesives -- 2.3.1 Animal-Sourced Proteins -- 2.3.2 Plant Proteins -- 2.4 Carbohydrate-Based Adhesives -- 2.5 Plant or Wood-Based Extractives -- 2.5.1 Rubber -- 2.5.2 Resins -- 2.5.2.1 Rosin -- 2.5.2.2 Terpene Resins -- 2.5.2.3 Tannins -- 2.5.2.4 Gums -- 2.6 Fats or Oils -- 2.6.1 Tung Oil -- 2.6.2 Linseed Oil -- 2.6.3 Soybean Oil -- 2.6.4 Castor Oil -- 2.6.5 Miscellaneous Oils -- 2.7 Summary -- Acknowledgements -- List of Abbreviations -- References -- Chapter 3 The Chemistry of Bioadhesives -- 3.1 Introduction -- 3.2 Carbohydrate Bioadhesives.

3.3 Protein Bioadhesives -- 3.4 Lignin-Based Bioadhesives -- 3.5 Tannin-Based Bioadhesives -- 3.5.1 Hydrolysable Tannins -- 3.5.1.1 Gallo-Tannins -- 3.5.1.2 Ellagi-Tannins -- 3.5.2 Condensed Polyflavonoid Tannins -- 3.5.3 Reactions of Condensed Flavonoid Tannins -- 3.6 Other Bio-Adhesives for Wood Composites -- 3.7 Summary -- List of Abbreviations -- References -- Chapter 4 Biorefinery Products as Naturally-Based Key Raw Materials for Adhesives -- 4.1 Biorefinery Systems -- 4.1.1 History of Biomaterials -- 4.1.2 Classification of Biorefinery Systems -- 4.1.3 Biorefinery Processes -- 4.1.3.1 Hydrothermal Processes -- 4.1.3.2 Thermochemical Processes -- 4.1.3.3 Chemical Processes -- 4.1.3.4 Biochemical Processes -- 4.1.3.5 Bacterial Processes -- 4.1.4 Renewable Materials for Biorefinery -- 4.1.4.1 Carbohydrates -- 4.1.4.2 Lignin -- 4.1.4.3 Triglycerides -- 4.1.4.4 Mixed Organic Residues -- 4.2 Biobased Materials -- 4.2.1 Biobased Monomers -- 4.2.2 Synthesis Methods -- 4.2.2.1 L-3,4-Dihydroxyphenylalanine -- 4.2.2.2 2-Pyrone-4,6-dicarboxylic acid -- 4.3 Biobased Materials Suitable for Adhesives -- 4.3.1 Additives -- 4.3.2 Wood Adhesives -- 4.3.3 Lignin-Based Adhesives -- 4.3.4 Biorefinery Process of Kash -- 4.3.5 Lignin-Phenol Adhesives -- 4.3.5.1 Enzymatic Hydrolysis of Lignin -- 4.3.5.2 Biorefinery Residues -- 4.3.5.3 Phenol Replacement by Lignins -- 4.3.6 Lignin-Epoxy Adhesives -- 4.3.7 Lignosulfonates -- 4.3.8 Tannins -- 4.3.9 Protein-Based Adhesives -- 4.4 Synthesis Methods for Biobased Adhesives -- 4.4.1 Methylolated Wood-Derived Bio-Oil -- 4.4.2 Biosynthesis of Lignin -- 4.4.3 Soy-Based Adhesives -- 4.4.4 Bisphenol A-Glycidyl Methacrylate Replacement -- 4.5 Modification of Lignin for Better Performance -- 4.5.1 Functionalization with Aromatic Compounds -- 4.5.1.1 Functionalization of Lignin -- 4.5.1.2 Phenolation of Lignin.

4.5.2 Organosolv Lignin-Based Materials -- 4.6 Pressure-Sensitive Adhesives -- 4.6.1 Lignin as Filler -- 4.6.2 Biobased Acrylic Compounds -- 4.6.3 UV-Tunable Pressure-Sensitive Adhesives -- 4.7 Summary -- References -- Chapter 5 Natural Aldehyde-Based Thermosetting Resins -- 5.1 Introduction -- 5.2 Aliphatic Aldehydes -- 5.2.1 Acetaldehyde -- 5.2.2 Glyoxal -- 5.2.2.1 Glyoxalation of Lignin -- 5.2.2.2 Glyoxylic Acid and Glyoxal -- 5.2.2.3 Glyoxal and Glutaraldehyde -- 5.2.2.4 Glyoxal and 5-Hydroxymethylfurfural (5-HMF) -- 5.2.3 Dimethoxy-Ethanal (Dimethoxy-Acetaldehyde, DME) -- 5.2.4 Propanal (Propionaldehyde) -- 5.2.5 Butyraldehyde -- 5.2.6 Isobutyraldehyde (Isobutanal) -- 5.2.7 Succinaldehyde (Butandial) -- 5.2.8 Glutar(di)aldehyde (GA) (Pentandial) -- 5.3 Aldehydes Based on Cyclic Structures -- 5.3.1 Furfural (Furfurylaldehyde) -- 5.3.2 Furfuryl Alcohol (FA) -- 5.3.3 5-Hydroxymethylfurfural (5-HMF) (see also Chapters 1 and 17) -- 5.3.4 2,5-Diformylfuran (2,5-Furan-Dicarbaldehyde) -- 5.3.5 Aromatic Aldehyde Precursors -- 5.3.6 Polymers with Pendent Aldehyde Groups -- 5.4 Summary -- List of Abbreviations -- References -- Chapter 6 Natural Crosslinkers for Naturally-Based Adhesives -- 6.1 Introduction -- 6.2 Crosslinking Reactions -- 6.2.1 Proteins -- 6.2.2 Tannins -- 6.2.3 Carbohydrates -- 6.2.4 Lignins -- 6.3 Aliphatic Aldehydes as Crosslinkers -- 6.3.1 Formaldehyde -- 6.3.2 Higher Aldehydes -- 6.3.3 Glyoxal -- 6.3.4 Glutaraldehyde -- 6.3.5 Higher Aliphatic Aldehydes -- 6.4 Cyclic and Aromatic Aldehydes as Crosslinkers -- 6.4.1 Furfural -- 6.4.2 5-Hydroxymethylfurfural (5-HMF) -- 6.4.3 Non-Volatile Aldehydes from Carbohydrates -- 6.5 Crosslinkers Prepared from Biomass -- 6.5.1 Furfuryl Alcohol -- 6.5.2 Extracts as Crosslinkers -- 6.5.3 Glycerol Diglycidyl Ether (GDE), Glycerol Polyglycidyl Ether (GPE), and Ethylene Glycol Diglycidyl Ether (EGDE).

6.5.4 Triglycidylamine (TGA) -- 6.5.5 Diethylene-Triamine (DETA) -- 6.5.6 Citric Acid -- 6.6 Synthetic Crosslinkers -- 6.6.1 Polyamidoamine-Epichlorohydrin (PAE) Resins -- 6.6.2 Epoxy Resins -- 6.6.3 Polyethylenimine (PEI) -- 6.6.4 Polyamidoamine (PADA) -- List of Abbreviations -- References -- Chapter 7 Curing and Adhesive Bond Strength Development in Naturally-Based Adhesives -- 7.1 Introduction -- 7.2 Curing Monitoring Techniques -- 7.2.1 Gel Time Test -- 7.2.2 Differential Scanning Calorimetry (DSC) -- 7.2.3 Thermogravimetric Analysis (TGA) -- 7.2.4 Dielectric Analysis (DEA) -- 7.3 Bond Strength Development Monitoring Techniques -- 7.3.1 Dynamic Mechanical Analysis (DMA) -- 7.3.2 Thermomechanical Analysis (TMA) -- 7.3.3 Automated Bonding Evaluation System (ABES) -- 7.3.4 Tensile-Shear Strength -- 7.4 Curing Mechanisms in Naturally-Based Adhesives -- 7.4.1 Tannin-Based Adhesives -- 7.4.2 Lignin-Based Adhesives -- 7.4.3 Soy-Based Adhesives -- 7.4.4 Sucrose-Based Adhesives -- 7.4.5 Starch-Based Adhesives -- 7.4.6 Liquefied Wood (LW)-Based Adhesives -- 7.5 Summary -- Acknowledgements -- List of Abbreviations -- References -- Chapter 8 Mimicking Nature: Bio-Inspired Adhesives -- 8.1 Introduction -- 8.2 Improvement of Adhesive Performance -- 8.3 Underwater Adhesives (Wet Application Adhesives) -- 8.4 Detechable Bonding and Self-Healing Polymers -- 8.5 Medical Applications -- 8.6 Summary -- List of Abbreviations -- References -- Part 2: Classes of Biobased Adhesives -- Chapter 9 Protein Adhesives -- Composition, Structure and Performance -- 9.1 Introduction -- 9.2 Composition of Proteins -- 9.3 Types, Sources, Processing, and Properties of Proteins -- 9.3.1 Collagen (Animal) -- 9.3.2 Globular (Plant) -- 9.3.3 Globular (Milk) -- 9.3.4 Globular (Egg) -- 9.3.5 Globular (Blood) -- 9.3.6 Other Protein Sources.

9.4 Conclusion (Future of Protein Adhesives) and Summary -- List of Abbreviations -- References -- Chapter 10 Carbohydrates (Polysaccharides) as Adhesives -- 10.1 Introduction -- 10.2 Cellulose Derivatives -- 10.3 Starch-Based Adhesives -- 10.4 Dextrin -- 10.5 Natural Gums -- 10.6 Chitosan -- 10.7 Summary and Prospects -- Acknowledgements -- List of Abbreviations -- References -- Chapter 11 Natural Polymer-Based Adhesives -- 11.1 Introduction -- 11.2 Natural Rubber (NR)-Based Adhesives -- 11.2.1 Introduction to NR-Based Adhesives -- 11.2.2 NR-Based Wood Adhesives -- 11.2.3 NR-Based Pressure-Sensitive Adhesives -- 11.2.4 NR-Based Adhesives in Leather, Rubber, Textile and Metal Bonding Applications -- 11.3 Poly(lactic acid) (PLA)-Based Wood Adhesives -- 11.3.1 Introduction to PLA-Based Adhesives -- 11.3.2 PLA-Based Wood Adhesives -- 11.3.3 PLA-Based Hot-Melt Adhesives -- 11.3.4 PLA-Based Adhesives for Metal Bonding -- 11.4 Chitosan-Based Adhesives -- 11.4.1 Introduction to Chitosan-Based Adhesives -- 11.4.2 Chitosan-Based Wood Adhesives -- 11.5 Summary -- List of Abbreviations -- References -- Chapter 12 Epoxy Adhesives from Natural Materials -- 12.1 Introduction and Morphology -- 12.2 Basic Properties of Epoxies -- 12.3 Epoxy Synthesis -- 12.4 Epoxy Curing -- 12.4.1 One-Component Epoxies -- 12.4.2 Two-Component Epoxies -- 12.5 Aromatic Epoxies -- 12.5.1 Aromatic Bis-Phenol Epoxies -- 12.5.2 Aromatic Novolac Epoxies -- 12.5.3 Biobased Aromatic Epoxies from Polyphenols, Tannins, Cardanol, and Lignin -- 12.5.4 Aromatic Epoxies from Lignin and Woody Biomass -- 12.6 Aliphatic Epoxies -- 12.6.1 Aliphatic Epoxies from Vegetable Oils -- 12.6.2 Aliphatic Epoxies from Sugars -- 12.6.3 Aliphatic Epoxies from Terpenoids -- 12.6.4 Other Aliphatic Epoxies -- 12.7 Hardeners -- 12.7.1 Amines -- 12.7.1.1 Aliphatic Amines -- 12.7.1.2 Biobased Aliphatic Amines.