Synthesis of an urushiol derivative and its use for hydrolysis resistance in dentin adhesive

Hydrolysis resistance is essential to the durability of the dentin bonding interface. Urushiol is a natural monomer that has been used in different fields over thousands of years but has the disadvantage of a long drying time. In this study, we evaluated a novel photocurable derivative of urushiol as the main monomer for polymerization in dentin adhesive and its effect on hydrolysis resistance. The derivative was characterized by Fourier transform infrared spectroscopy and ¹H nuclear magnetic resonance spectroscopy. Compared with the Adper Single Bond 2, the experimentally synthesized adhesives had higher contact angles. In particular, the water sorption/solubility of the experimental samples were significantly lower than that of Adper Single Bond 2. The microtensile bond strengths of the test groups were higher than that of the control group, even after 5000 thermocycles. Cytotoxicity test results showed that adhesives based on the original derivative induced low toxicity to L929 cells. The results of this study may shift the focus of future research to natural monomers and even their derivatives which may perform well in dentistry.