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1 PrefaceFigure 1 Basic wood elements from largest to smallest (i.e., breakdown of solid wood into…

2 Chapter 1Figure 1.1 Earlywood and latewood [5].Figure 1.2 Schematic model of the cell wall layers [16].Figure 1.3 Chemical composition of wood.Figure 1.4 The three monolignols.Figure 1.5 Radicals and units—nomenclature.Figure 1.6 Various degradation products of lignin.Figure 1.7 Enzymatic dehydrogenation of coniferyl alcohol yielding phenoxy radicals.Figure 1.8 Typical dilignol structures [25].Figure 1.9 Arrays of cells aligned along the longitudinal and radial directions.

3 Chapter 2Figure 2.1 Potential energy diagram for different forces [4].Figure 2.2 Various wood elements.Figure 2.3 Wetting phenomenon.Figure 2.4 Wetting, spreading, and dewetting for different contact angles.Figure 2.5 Equilibrium contact angle based on balance of forces.Figure 2.6 Zisman’s plot…Figure 2.7 Different links in adhesive bonding.

4 Chapter 3Figure 3.1 Reaction between urea and formaldehyde: mononuclear methylol ureas.Figure 3.2 Reaction mechanism.Figure 3.3 Effect of pH on the rate of addition and condensation reactions [24].Figure 3.4 Reaction chemistry.Figure 3.5 Reaction mechanism for chain extension.Figure 3.6 Monomeric species.Figure 3.7 Oligomeric species.Figure 3.8 General chemical structure of commercial UF resin.Figure 3.9 Cross-linked structure of cured UF resin.Figure 3.10 Synthesis of PILs.Figure 3.11 Structure of polyamines.

5 Chapter 4Figure 4.1 Ammeline, ammelide, and cyanuric acid.

6 Chapter 5Figure 5.1 Resol, resitol, and resite.Figure 5.2 Resonance structures of phenol.Figure 5.3 Formation of ortho-methylolphenol.Figure 5.4 Mononuclear phenol alcohols.Figure 5.5 Mechanism of methylolphenol formation in alkaline medium.Figure 5.6 Chain extension.Figure 5.7 A dinuclear structure.Figure 5.8 Formation of quinine–methide as intermediate.Figure 5.9 Typical structure of a commercial phenolic resol.Figure 5.10 Structure of ammonia-catalyzed resol.Figure 5.11 Three-dimensional response surface relating the heat of P–F condensation…Figure 5.12 Interaction of resin synthesis, structure, and property relationships [36].

7 Chapter 6Figure 6.1 Reaction of resorcinol with formaldehyde through its different methylol derivatives…Figure 6.2 Possible quinone methide intermediates formed by reaction of resorcinol with…Figure 6.3 Reaction of resorcinol with formaldehde to form HMR trimer.

8 Chapter 7Figure 7.1 Isocyanurate and allophenate.Figure 7.2 Aliphatic isocyanates.Figure 7.3 Biuret of HDI.Figure 7.4 TDIs 2,4 and 2,6 isomers (65:35).Figure 7.5 TDIs 2,4 and 2,6 isomers (80:20).Figure 7.6 Polymeric MDI.Figure 7.7 Catalysts for reactions of isocyanates.Figure 7.8 Multiple pathways for the formation of a wood/isocyanate adhesive bond.Figure 7.9 MDI reaction with wood hydroxyls.Figure 7.10 Schematic reaction of formation of a PU from a polyisocianate and a polyol.Figure 7.11 “Green” pressure-sensitive PU adhesive prepared from glycerol and…Figure 7.12 Reaction of P. pinaster bark tannin with propylene oxide to produce…Figure 7.13 Formation of PU adhesive and resins by reaction of a hydroxypropylated polypheno…Figure 7.14 Reaction of the flavonoid tannin/formaldehyde system with isocyanates to form…Figure 7.15 Formation of PU by reaction of a glyoxalated flavonoid tannin with a polyisocyan…Figure 7.16 Non-isocyanate PU formation by reaction of a dicyclic organic carbonate with a…Figure 7.17 Non-isocyanate diurethane obtained by reacting a precarbonated flavonoid tannin…Figure 7.18 Non-isocyanate urethane bridge linking a precarbonated flavonoid tannin dimer…Figure 7.19 Non-isocyanate diurethane obtained by reaction of a carbonated carbohydrate…Figure 7.20 Non-isocyanate diurethane obtained by reaction of a carbonated carbohydrate…Figure 7.21 Examples of linear and branched oligomer structures identified for glucose-based…

9 Chapter 10Figure 10.1 Hydrophobization of wood.Figure 10.2 Sol-gel reaction scheme.

10 Chapter 11Figure 11.1 MALDI mass spectrum of (a) natural mimosa tannin extract. (b) Details of the 600…Scheme 11.1

11 Chapter 12Figure 12.1 Schematic representation of the decomposition of hexamine to iminoamino methylen…Figure 12.2 Dry IB strength as a function of tannin solution pH of laboratory particleboards…Figure 12.3 Dry IB strength of laboratory particleboards prepared with mixtures of different…Figure 12.4 Chemical composition and type of compounds in CNSL.Figure 12.5 Ozonolysis of CNSL to produce cardanolaldehyde and a hydroperoxide, the latter…Figure 12.6 Example of the relative movement of two pieces of wood during wood welding witho…

12 Chapter 13Figure 13.1 Susceptible bonds in UF.Figure 13.2 Susceptible bonds in MF and PF.Figure 13.3 Reaction between chromotropic acid and formaldehyde.Figure 13.4 Emission according to gas analysis.Figure 13.5 Test apparatus for the flask method.Figure 13.6 Reaction between acetylacetone and formaldehyde.Figure 13.7 Japanese desiccator method.Figure 13.8 The perforator method.

13 Chapter 14Figure 14.1 Viscous flow between two parallel plates.Figure 14.2 Ostwald’s viscometer.Figure 14.3 Ford cup.Figure 14.4 Non-Newtoninan fluids.Figure 14.5 Maxwell element.Figure 14.6 Voigt element.Figure 14.7 Maxwell-Voigt mixed model.Figure 14.8 Macroscopic development of rheological and mechanical properties during network…Figure 14.9 Response of elastic and viscous materials to sinusoidal stresses.Figure 14.10 Strain response to sinusoidal stress.Figure 14.11 Graphical representation of storage and loss moduli (Argand diagram).Figure 14.12 Significance of elastic response and energy loss.Figure 14.13 Details of a TTT diagram of an epoxy resin adhesive on a non-interacting glass…Figure 14.14 Generalized TTT diagram of water-carried PF resin adhesives on an interacting…Figure 14.15 Generalized CHT diagram of water-carried PF resin adhesives on an interacting…Figure 14.16 TMA curve of the hardening of a PF resin in situ in a beech wood joint…Figure 14.17 Wire mesh geometry.Figure 14.18 Sample configuration for the DMTA (three-point bending mode) test.

14 Chapter 15Figure 15.1 Ethylene vinyl acetate copolymer.Figure 15.2 Two-phase morphology of SBC.Figure 15.3 Formation of dimer acid.Figure 15.4 Dimer acid polyamide.Figure 15.5 Terpenes for producing tackifiers.Figure 15.6 Three major classes of terpene resins.Figure 15.7 Rosin acids.

15 Chapter 16Figure 16.1 Acetylation of lignocellulosic fibers.Figure 16.2 Structure of silane coupling agent.Figure 16.3 Fiber modification by acrylonitrile.Figure 16.4 Fiber modification by isocyanate.Figure 16.5 MAA-g-polypropylene.Figure 16.6 Fiber modification by GMA.Figure 16.7 mTMI unsaturated aliphatic isocyanate.Figure 16.8 Isocyanate modification of fiber.

16 Chapter 17Figure 17.1 Diols employed for UP resins.Figure 17.2 Other speciality chemicals used for UP synthesis.Figure 17.3 Vinyl ester resin.Figure 17.4 Formation of monoester.Figure 17.5 Formation of diester.Figure 17.6 Unsaturated polyester oligomer.Figure 17.7 Benzoyl peroxide and tert-butylperbenzoate.Figure 17.8 Production of free radicals.Figure 17.9 Room temperature curing free radical initiators.Figure 17.10 UP thickening reaction.Figure 17.11 BAPO photoinitiator.

17 Chapter 18Figure 18.1 Raw materials for epoxy resin.Figure 18.2 Structure of DGEBA.Figure 18.3 Epoxy oligomer based on bisphenol A.Figure 18.4 Tertiary amines curing agents.Figure 18.5 Scheme of reaction of epoxy resin with tertiary amines.Figure 18.6 Polyamines as curing agents.Figure 18.7 Polyamines–epoxy curing reaction.Figure 18.8 Special amines.Figure 18.9 Anhydrides for epoxy resin curing.Figure 18.10 Epoxidized novolac.Figure 18.11 Peroxy-acids for epoxidizing unsaturated compounds.Figure 18.12 Reactivity of peroxy-acids.

18 Chapter 19Figure 19.1 Schematic molecular structure. (a) LDPE, (b) LLDPE, and (c) HDPE [2].

19 Chapter 20Figure 20.1 PP manufacturing process: (a) 1st generation solvent polymerization process,…

20 Chapter 21Figure 21.1 Simplified structures of PHAs.Figure 21.2 Polyhydroxybutyrate-co-valerate.Figure 21.3 D- and L-lactic acid.Figure 21.4 Polyesterification of lactic acid.Figure 21.5 ROP of lactic acid.Figure 21.6 Polybutylene adipate terephthalate.Figure 21.7 PHB/valerate.

Adhesives for Wood and Lignocellulosic Materials

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