Novel self‐initiating UV‐curable acrylate monomers

Novel self‐initiating UV‐curable acrylate monomers
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新型自引发 UV 固化丙烯酸酯单体

DOI:
10.1002/app.49356
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发表时间:
2020-05
影响因子:
3
通讯作者:
Tao Zhang
Tao Zhang
中科院分区:
化学3区
文献类型:
--
作者:
Yuquan Zhao;Xingyu Tao;Xinyi Li;Tao Zhang

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基于双官能团丙烯氧乙基异氰酸酯中羟基和异氰酸酯基团的加成反应,以安息香和市售2‐hydroxy‐4′‐(2‐hydroxyethoxy)‐2‐methylpropiophenone为原料,合成了两种新型紫外光固化丙烯酸酯单体,分别命名为安息香和2959。产物的化学结构经核磁共振和傅里叶变换红外光谱确证。紫外-可见吸收光谱表明,自引发丙烯酸酯的最大吸收波长与安息香(250 nm)和Irgacure®2959(270 nm)相似。当产品连续暴露在汞灯下时,最大吸收峰逐渐蓝移,表明产品在紫外光照射下分解。光致差示扫描量热(Photo-DSC)分析表明,自引发单体引发1,6-己二醇二丙烯酸酯(HDDA)聚合的速度与原光引发剂一样快,且安息香AOI的聚合效率略低于安息香,而2959-AOI连接到AOI部分后,聚合效率保持稳定。对成纤维细胞株L929的细胞毒性试验表明,引入AOI结构后,2959-AOI在低剂量时的细胞毒性低于Irgacure®2959,但在高剂量时的细胞毒性高于Irgacure®2959。
Based on the addition reaction of hydroxyl groups and the isocyanate groups in the bi‐functional monomer acroyloxyethyl isocyanate (AOI), two novel self‐initiating ultraviolet (UV)‐curable acrylate monomers were synthesized from benzoin and 2‐hydroxy‐4′‐(2‐hydroxyethoxy)‐2‐methylpropiophenone (commercial‐available Irgacure® 2959), and the products were denoted as Benzoin‐AOI and 2959‐AOI, respectively. The chemical structures of the products were confirmed by nuclear magnetic resonance (NMR) and Fourier transform infrared spectroscopy (FTIR). The UV–visible absorption spectrum showed that the self‐initiating acrylates exhibited similar maximum absorption wavelengths to both benzoin (250 nm) and Irgacure® 2959 (270 nm). When the products were continually exposed to a mercury lamp, the maximum absorption peak gradually blue shifted, showing that the products decomposed under the UV radiation. The photo differential scanning calorimetry (Photo‐DSC) analysis showed that the self‐initiating monomers could initiate the polymerization of 1,6‐hexanediol diacrylate (HDDA) as quickly as the original photo‐initiator, and the efficiency of Benzoin‐AOI was slightly lower than that of benzoin, while for 2959‐AOI, the efficiency remained stable after being linked to the AOI moiety. The cytotoxicity assay against fibroblasts cell line L929 showed that 2959‐AOI exhibited lower cytotoxicity at low dosages but higher cytotoxicity at high dosages compared to Irgacure® 2959 after the introduction of the AOI structure.
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发表时间: 2018-12
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