Biobased Adhesives: Sources, Characteristics, and Applications

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
12.7.1.3 Aromatic Amines
12.7.2 Anhydrides of Organic Acids
12.8 Other Curing Mechanisms
12.9 Other Additives
12.9.1 Tougheners
12.9.2 Modifiers
12.10 Status of Biobased Epoxy Adhesives
12.11 Summary
List of Abbreviations
References
Chapter 13 Naturally-Based Polyurethane Bioadhesives
13.1 Introduction
13.2 Biopolyols-Isocyanate Polyurethanes
13.3 Non-Isocyanate Polyurethanes (NIPUs)
13.4 NIPUs as Adhesives
13.5 Summary
References
Chapter 14 Nanocellulose-Modified Wood Adhesives
14.1 Introduction
14.2 Nanocellulose as Additive for Conventional and Biobased Wood Adhesives
14.3 Nanocellulose-Derived Wood Adhesives
14.4 Prospects
14.5 Summary
Note
List of Abbreviations
References
Chapter 15 Debondable, Recyclable and/or Biodegradable Naturally-Based Adhesives
15.1 Introduction
15.2 Debondable Adhesives
15.2.1 Types of Debonding Adhesives
15.2.2 Reversible Covalent Bonds Containing Adhesives
15.3 Biobased Debondable and Recyclable Adhesives
15.3.1 Biodegradable Adhesives
15.3.2 Biobased Reversible Covalent Bonds Containing Adhesives
15.4 Summary
List of Abbreviations
References
Chapter 16 Fungal Mycelia as Bioadhesives
16.1 Introduction
16.2 Basics of Fungal Mycelia
16.2.1 Fungal Species
16.2.2 Fungal Cell Wall
16.2.3 Effects of Fungal Mycelia on Lignocellulosic Substrates
16.3 Production Procedure
16.4 Adhesive Performance
16.4.1 As-Grown Foams
16.4.2 Hot-Pressed Panels
16.4.3 Engineered Living Materials
16.5 Improvement Strategies
16.5.1 Incorporating Natural Fibers
16.5.2 Infusing Bio-Resin
16.5.3 Incorporating Natural Reinforcement Particles
16.6 Prospects
16.7 Summary
Acknowledgements
List of Abbreviations
References
Chapter 17 5-Hydroxymethylfurfural-Based Adhesives: Challenges and Opportunities
17.1 Introduction
17.2 5-Hydroxymethylfurfural as Biobased Platform Chemical
17.2.1 Potential as Chemical Building Block
17.2.2 Challenges in the Implementation of an Industrial 5-HMF Production
17.3 5-HMF-Based Adhesive Systems
17.3.1 Wood Adhesives
17.3.2 Non-Wood Applications of 5-HMF-Based Adhesives
17.3.3 Examples of Adhesives Produced from 5-HMF Derivatives
17.4 Prospects
17.5 Summary
Acknowledgements
List of Abbreviations
References
Chapter 18 Adhesive Precursors from Tree-Derived Naval Stores
18.1 Introduction
18.2 Sources and Structures
18.2.1 Rosins
18.2.2 Fatty Acids
18.2.3 Terpenes
18.3 Pressure-Sensitive Adhesives
18.4 Chemistry and Products
18.4.1 Rosins
18.4.2 Modification of the Carboxylic Acid
18.4.3 Modification of the Olefinic Portion
18.4.4 Ink Pigment Binders
18.4.5 Tall Oil Fatty Acids
18.4.6 Terpenes
18.5 Summary
List of Abbreviations
References
Part 3: Applications of Biobased Adhesives
Chapter 19 Naturally-Based Adhesives for Wood and Wood-Based Panels
19.1 Introduction
19.2 Protein-Based Wood Adhesives
19.2.1 Wood Bonding with Proteins
19.2.2 Plant-Based Proteins (for Soy Proteins see Section 19.2.3)
19.2.3 Soy Proteins
19.2.4 Animal-Based Proteins
19.2.5 Denaturation and Modification of Proteins
19.2.6 Crosslinking of Proteins
19.3 Wood Adhesives Based on Carbohydrates
19.3.1 Types and Sources of Carbohydrates for Use as Wood Adhesives
19.3.2 Modification of Starch for Possible Use as Wood Adhesive
19.3.3 Combination and Crosslinking of Carbohydrates with Natural and Synthetic Components
19.3.4 Degradation and Repolymerization of Carbohydrates
19.4 Tannin-Based Wood Adhesives
19.4.1 Types and Chemistry of Condensed Tannins
19.4.2 Hardening and Crosslinking of Tannins
19.4.3 Combination of Tannins with Other Components
19.5 Wood Adhesives Based on Lignin
19.5.1 Chemistry and Structure of Lignin
19.5.2 Modification of Lignin
19.5.3 Lignin as Adhesive
19.5.4 Lignin as Sole Adhesive
19.5.5 Reactions of Lignin with Various Aldehydes and Other Naturally-Based Components
19.6 Summary
List of Abbreviations
References
Chapter 20 Activation of Wood Surfaces and “Binderless” Wood Composites
20.1 Introduction
20.2 Self-Adhesion and “Binderless” Boards
20.2.1 Wood and Non-Wood Components for “Binderless” Boards
20.2.2 Thermal and Physical Pretreatments of Wood Material and the Wood Surface
20.2.3 Chemical Treatments of the Wood Surface
20.2.4 Enzymatic Pretreatment of the Wood Surface
20.2.5 Degradation and Re-Polymerization of Carbohydrates
20.2.6 Citric Acid
20.2.6.1 Sugars and Starch in Combination with Citric Acid
20.2.6.2 Wood in Combination with Citric Acid
20.2.7 Hardboards (Wet Fiber Process)
20.2.8 Wood Welding
20.3 Summary
List of Abbreviations
References
Chapter 21 Bonding of Solid Wood-Based Materials for Timber Construction
21.1 Introduction
21.2 Brief Overview of Solid Wood-Based Materials
21.3 Adhesives Used for Materials in Structural Timber Engineering
21.3.1 Adhesives for the Production of Glued-Laminated Timber (Surface Bonding)
21.3.2 Casein Adhesives
21.4 Factors Influencing the Quality of Adhesively-Bonded Wood
21.4.1 Short Overview
21.4.2 Influence of the Wood Substrate (Structure and Wood Species)
21.4.3 Influence of Adhesives
21.4.4 Influence of Wood Machining
21.4.5 Quality Control of Bonded Wood Joints
21.4.6 Influence of Service Conditions
21.4.7 Aging of Bonded Wood
21.5 Trends in the Use of Biobased Adhesives
21.6 Summary
List of Abbreviations
References
Chapter 22 Applications and Industrial Implementations of Naturally-Based Adhesives
22.1 Introduction
22.2 Wood-Based Panels
22.3 Shoe Fabrication (Footwear Industry)
22.4 Bonding of Metals
22.5 Composites in Automotive, Aircraft, and Aeronautical Industries
22.6 Natural Composites with Matrices Based on Natural Resources
22.7 Mineral Wool
22.8 Packaging and Other Applications
22.9 Biomedical Applications
22.10 Biodegradability and Recycling
22.11 Life Cycle Analysis (LCA)
22.12 Summary
List of Abbreviations
References
Chapter 23 Bioadhesives for the Advancement of Controlled Drug Delivery and Wearable Bioelectronics
23.1 Introduction
23.1.1 History of Bioadhesives and their Evolution
23.1.2 Classification of Bioadhesives
23.1.2.1 Natural Bioadhesives
23.1.2.2 Biological and Biocompatible Bioadhesives
23.1.2.3 Biomimetic and Bioinspired Bioadhesives
23.1.3 Mechanism of Bioadhesives
23.2 Bioadhesives in Controlled Drug Delivery
23.3 Bioadhesives in Bioelectronics
23.4 Limitations of Bioadhesives for Biomedical Applications
23.5 Summary and Future Prospects
List of Abbreviations
References
Index
EULA