Green, Formaldehyde-Free Bio-Adhesive from Soybean Meal and Laccase-Oxidized Tannin via Quinone-Amine Crosslinking

To develop a fully green and non-toxic wood adhesive with improved water resistance and bonding performance for soybean meal (Glycine max (L.) Merr.)-based adhesives, oxidized tannin (OTN) was obtained by the laccase treatment of waxberry tannin (TN), a natural polyphenolic polymer, and then blended with soybean meal (SM) to prepare an oxidized tannin-soybean meal adhesive (OTS). Laccase-mediated oxidation converted the tannin polymer into quinone-rich oxidized polymeric structures, which reacted with amino groups in soybean meal proteins through Michael addition and Schiff base reactions to form a covalently crosslinked polymeric network. Under the optimal conditions of a laccase dosage of 10%, an oxidation time of 6 h, an OTN:SM mass ratio of 0.5:1, and a hot-pressing temperature of 160 °C, plywood bonded with OTS exhibited a wet shear strength of 0.85 MPa at 63 °C, representing a 136% increase over that of the neat soybean meal adhesive, and showed slightly higher bonding performance than the commercial urea-formaldehyde (UF) resin under boiling-water conditions. Structural analyses (FT-IR and XPS) verified quinone formation and carbon-nitrogen single and double bonds. Thermal analyses (DSC and TGA) revealed improved curing reactivity and significantly enhanced thermal stability compared with the neat soybean meal adhesive.