Page 86 - 《精细化工》2023年第9期

第 40 卷第 9 期 精 细 化 工 Vol.40, No.9
20 23 年 9 月 FINE CHEMICALS Sept. 2023

功能材料
查耳酮衍生物接枝改性的聚硅氧烷 UVA 滤光剂

吴 凡 1,2 ，陈凤凤 1,2 ，刘春环 1,2 ，杨 成 1,2*

（1. 江南大学 化学与材料工程学院，江苏 无锡 214026；2. 合成与生物胶体教育部重点实验室，江苏 无
锡 214026）

摘要：制备了查耳酮衍生物(E)-3-(4-烯丙氧基)苯基-1-苯基丙-2-烯-1-酮（Blank-Cha），(E)-3-(4-烯丙氧基)苯基-1-(4-
羟基苯基)丙-2-烯-1-酮（Oxhydryl-Cha）和(E)-3-(4-烯丙氧基)苯基-1-(4-甲氧基苯基)丙-2-烯-1-酮（Methoxy-Cha）。
再通过硅氢加成反应将 Methoxy-Cha 接枝到含氢硅油链上，制备了聚硅氧烷 UVA 滤光剂（WPUF）。采用 NMR、
LC-MS 及 FTIR 鉴定产物化学结构，通过 UV 吸收光谱测试了 WPUF 的性能，考察了不同取代基对查耳酮衍生
物的 UV 吸收性能和细胞毒性的影响。结果表明，查耳酮衍生物和 WPUF 已成功制备。查耳酮衍生物摩尔吸光
系数>10000 L/(mol·cm)，Methoxy-Cha 的细胞毒性最低；避光 6 个月和 90 ℃加热 12 h 后 WPUF 的化学结构无
变化，模拟阳光照射 240 min 后 UVA 吸收能力仅损失 30.46%，且 WPUF 在质量浓度≤250 mg/L 下未表现出细
胞毒性。体外皮肤穿透实验显示，WPUF 角质层平均渗透深度为 11 μm。体外测定 WPUF 的防晒指数为 36.21，
与商用防晒剂相当。
关键词：聚硅氧烷；查耳酮；UVA 滤光剂；皮肤渗透；稳定性；细胞毒性；功能材料
中图分类号：TQ658.24 文献标识码：A 文章编号：1003-5214 (2023) 09-1934-09

Chalcone derivatives graft-modified polysiloxane UVA filters

1,2
1,2
1,2
WU Fan , CHEN Fengfeng , LIU Chunhuan , YANG Cheng 1,2*
（1. School of Chemical and Materials Engineering, Jiangnan University, Wuxi 214026, Jiangsu, China; 2. Key
Laboratory of Synthesis and Biocolloids, Ministry of Education, Wuxi 214026, Jiangsu, China）

Abstract: Chalcone derivatives (E)-3-[4-(allyloxy)phenyl]-1-phenylprop-2-en-1-one (Blank-Cha), (E)-3-[4-
(allyloxy)phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one (Oxhydryl-Cha) and (E)-3-[4-(allyloxy)phenyl]-1-
(4-methoxyphenyl)prop-2-en-1-one (Methoxy-Cha) were firstly prepared. Then, polysiloxane UVA filter
(WPUF) was synthesized by grafting Methoxy-Cha onto polymethylhydrosiloxane chain via silica-
hydrogen addition reaction. The chemical structures of products obtained were identified by NMR, LC-MS
and FTIR，while the properties of WPUF were analyzed by UV adsorption spectrum. The effects of
different substituents on the UV absorption properties and cytotoxicity of chalcone derivatives were further
investigated. The results showed that the chalcone derivatives and WPUF were successfully synthesized. All
chalcone derivatives exhibited a molar absorbance coefficient>10000 L/(mol·cm), and Methoxy-Cha
showed the least cytotoxicity. The chemical structure of WPUF did not change after being stored in the dark
for 6 months and heated at 90 ℃ for 12 h. The loss of UVA absorption capacity was only 30.46% after
being exposed to simulated sunlight for 240 min. Moreover, WPUF did not exhibit cytotoxicity at a mass
concentration≤250 mg/L. In vitro penetration test revealed that an average penetration depth of 11 μm in
the stratum corneum of WPUF. Sun protection factor of WPUF determined in vitro was 36.21, which was
comparable to commercial sunscreens.
Key words: polysiloxane; chalcone; UVA filter; skin penetration; stability; cytotoxicity; function materials

收稿日期：2022-11-24; 定用日期：2023-02-03; DOI: 10.13550/j.jxhg.20221074
基金项目：中国博士后科学基金面上资助项目（2021M701464）；江苏省自然科学基金青年项目（BK20221069）
作者简介：吴 凡（1997—），男，硕士生，E-mail：wufan9707@qq.com。联系人：杨 成（1970—），男，教授，E-mail：
cyang@ jiangnan.edu.cn。