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To evaluate the biomodification ability of lignin used as pre-treatment in human dentin before the application of an etch-and-rinse adhesive. Experimental hydroethanolic solutions with different cross-linking agents were used: 6.5% proanthocyanidins (PAC, from grape-seed extract); 2% cardanol (CARD, from cashew-nut shell liquid); lignin (LIG, from eucalyptus) at 1, 2 or 4% concentrations. The negative control (NC) was ethanol 50 v%. Extracted molars were prepared, and dentin microtensile bond strength (μTBS) was evaluated after 24 h water storage or 10,000 thermocycling aging. Further specimens were processed for SEM nanoleakage, micropermeability confocal microscopy evaluation and in situ degree of conversion (DC) through micro-Raman spectroscopy. Demineralized dentin sticks were submitted to a three-point bending test to evaluate the elastic modulus (E) before and after 1 min biomodification using the tested solutions. Moreover, it was also evaluated the mass changes and hydroxyproline (HYP) release after 4-weeks of water storage. Vibrational collagen crosslinking identification was evaluated through micro-Raman spectroscopy. The results were analyzed by analysis of variance (ANOVA) and Tukey’s test (α = 0.05). A significant reduction in μTBS was observed in groups NC (p < 0.001) and CARD (p = 0.026). LIG-4% showed no significant reduction in μTBS after aging (p = 0.022). Nanoleakage micrographs showed hybrid layer protection with all agents, but reduced micropermeability was attained only with lignin. Polymerization was negatively affected in the presence of all tested cross-linking agents, except LIG-1%. Lignin and cardanol increased the dentin E values, but only lignin reduced the mass loss in dentin specimens. Effective collagen crosslinking (1117 cm−1 and 1235 cm−1) was detected for all agents. HYP release was significantly lower with LIG-1% than NC (p < 0.001). Lignin was able to perform collagen cross-linking and prevent the degradation of unprotected dentin collagen, thereby improving the bonding performance of the composite restorations performed in this study.

The aim of the study was to evaluate how the association of solvents (tetrahydrofuran [THF], dimethyl sulfoxide [DMSO], ethanol [ET] or acetone [ACT]) with experimental dental adhesives affects selected properties of experimental dental adhesives and dentin bond durability. Six adhesive combinations were prepared containing: 30 % ET, 30 % ACT, 30 % THF, 28 % ET + 2 % DMSO (ET+DMSO), 15 % ethanol + 15 % THF (ET+THF), or 28 % THF + 2 % DMSO (THF+DMSO). Thirty-six molars (n = 6) were cut to expose the coronary dentin, and were randomly divided according to the adhesives. They were restored, and then cut into resindentin sticks (1 mm²), and stored in distilled water for 24 h or 6 months, until conducting the microtensile bond strength and nanoleakage tests. Other experiments performed with adhesives included viscosity assessment using a rheometer, and degree of conversion using Fourier-transform infrared spectroscopy (FTIR). The data were analyzed statistically using two-way ANOVA and Tukey's test (p < 0.05). The adhesive formulated exclusively with THF showed the highest viscosity, followed by ET+THF, which obtained the highest degree of conversion compared to ET, and THF alone. ET+DMSO obtained the highest 24-h and aged bond strengths (p < 0.05). ET+THF increased the nanoleakage slightly after 6 months, but attained the only gap-free adhesive interface among all the groups. The combination of alternative solvents, particularly THF, with conventional ones (ET) has improved chemical properties, and the dentin bonding of experimental simplified adhesives.