In this study, furfural was used as a crosslinking agent to enhance the water resistance of lignin-phenol-formaldehyde (LPF) resin. The effect of the furfural content on the physicochemical properties of the adhesives was explored, and the possible synthesis mechanism of the furfural-modified lignin-phenol-formaldehyde (LPFF) resin adhesives was investigated. Compared with the LPF adhesive, the LPFF adhesive with 15% furfural content and 50% lignin substituent exhibited outstanding properties in all considered aspects; it had a high wet shear strength (1.30 MPa), moderate solid content (54.51%), and low viscosity (128 mPa∙s), which were 38.0% higher, 3.6% higher, and 37.5% lower than those of the LPF adhesive. Analyses via nuclear magnetic resonance and Fourier transform infrared (FTIR) spectroscopy confirmed that the furfural content improved water resistance of the lignin-based adhesive; this improvement was due to the formation of new chemical bonds between furfural and lignin to construct a dense crosslinked network structure. In addition, the decrease in viscosity and the increase in solid content enabled the adhesive to better penetrate into the wood porous structure, showing stronger adhesion. Therefore, the LPFF adhesive has superior water resistance, high strength, and good thermal stability; thus, it has a great potential for industrial applications.

Lignin is insoluble in water, thereby limiting its use in the synthesis of adhesives. Therefore, in this study, an aminated lignin compound was prepared through a lignin amination reaction to increase the amount of raw lignin material that can be used in the synthesis of adhesives; moreover, structural analysis was conducted. The main result of this was the introduction of amino groups into phenolic hydroxyl groups in the hydrolyzing lignin from the raw lignin materials, thus generating the product of aminated lignin. The resulting particle sizes were about 100 nm, the average molecular weight was 57,627 g/mol, and the water solubility of the aminated lignin was about 0.45 g/100 mL. Therefore, the water solubility of raw lignin was greatly improved. The proposed reaction mechanism of phenolic hydroxyl groups and carboxylic acid groups in lignin is a reaction with ammonia molecules; thus, the successful introduction of amino groups generated the aminated lignin compounds. Hence, this article enriches the scientific theory of lignin reactions and provides a reference for the widespread application of raw lignin materials in the field of adhesives.

There is increasing interest in furfurylated wood, but the polymerization mechanism between its internal polyfurfuryl alcohol (PFA) and lignin is still uncertain. This paper investigated the distribution of PFA and the feasibility of the polymerization of PFA with lignin in furfurylated balsa wood. The wood first immersed in the furfuryl alcohol (FA) solution followed by in situ polymerization and the distribution of PFA was characterized by Raman, fluorescence microscopy, SEM, and CLSM. Then, the mill wood lignin (MWL) of balsa wood and lignin model molecules were catalytically polymerized with PFA, respectively, studying the mechanism of interaction between PFA and lignin. It was concluded that PFA was mainly deposited in cell corner with high lignin concentration, and additionally partly deposited in wood cell cavity due to high concentration of FA and partial delignification. TGA, FTIR, and NMR analysis showed that the cross-linked network structure generated by the substitution of MWL aromatic ring free position by PFA hydroxymethyl enhanced the thermal stability. New chemical shifts were established between PFA and C₅/C₆ of lignin model A and C₂/C₆ of model B, respectively. The above results illustrated that lignin-CH₂-PFA linkage was created between PFA and lignin in the wood cell wall.

Lignin is insoluble in water, limiting its use in the synthesis of adhesives. Therefore, in order to increase the amount of lignin raw materials used in the synthesis of adhesives, a kind of aminated lignin compounds was prepared through lignin amination reaction, and conducting structural analysis in this paper. The particle size of the amino lignin is about 100 nm, with the weight average molecular weight of 57,627 g/mol and a water solubility of 0.45g/100ml. The reaction mechanisms were proposed that the phenolic hydroxyl groups of lignin react with ammonia molecules, and thereby successfully introducing amino groups to generate the aminated lignin compounds. Therefore, this article enriches the scientific theory of lignin reactions and provides reference for the widespread application of lignin raw materials in the field of adhesives.