Role Evaluation of Active Groups in Lignin on UV-Shielding Performance
ACS SUSTAINABLE CHEMISTRY & ENGINEERING(2022)
摘要
The contribution of the active groups in lignin to ultraviolet (UV)-shielding performance still remains unclear. In this study, we employed 16 lignin model compounds and theoretical calculations to ascertain the contribution of different functional groups to UV-shielding performance. These results showed that the order of UV-shielding performance on functional groups was -C= C-CHO > -C=C-COOH >-C=C-CH2OH > -C=C > quinone > -COOH > -OCH3 asymptotic to -OH. Moreover, the synergism between the para-substituted electron-donating group -OH and the electron-withdrawing group allyl on the aromatic ring played a major role in UV-shielding performance of lignin models, whereas the additive effect of meta/ortho-substituted -OCH3 played a secondary role. Furthermore, we found that the hydrophile-lipophile balance (HLB) value of lignin models also greatly affected the sunscreen protection factor (SPF) of lignin model-based sunscreens. A closer HLB value of lignin to 8.89 corresponded with a higher SPF of the lignin model-based sunscreen. The commercial photoprotective ingredient ethylhexyl methoxycinnamate (EHMC) and lignin models had a synergistic effect on UV shielding performance caused by the pi-pi stacking interaction between the parallel-displaced stacked aromatic rings of lignin models and EHMC. Additionally, the UV irradiation test showed that these sunscreens prepared using lignin models and EHMC exhibited good photostability.
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关键词
sunscreen,lignin models,functional groups,UV-shielding performance,?-? stacking interaction
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