查耳酮衍生物接枝改性的聚硅氧烷UVA滤光剂  

Chalcone derivatives graft-modified polysiloxane UVA filters

作　　者：吴凡 陈凤凤 刘春环 杨成 WU Fan;CHEN Fengfeng;LIU Chunhuan;YANG Cheng(School of Chemical and Materials Engineering,Jiangnan University,Wuxi 214026,Jiangsu,China;Key Laboratory of Synthesis and Biocolloids,Ministry of Education,Wuxi 214026,Jiangsu,China)

机构地区：[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

出　　处：《精细化工》2023年第9期1934-1942,共9页Fine Chemicals

基　　金：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)。

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11μm。体外测定WPUF的防晒指数为36.21,与商用防晒剂相当。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 silicahydrogen 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 11μm in the stratum corneum of WPUF.Sun protection factor of WPUF determined in vitro was 36.21,which was comparable to commercial sunscreens.

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 

分 类 号：TQ658.24[化学工程—精细化工]