Synthesis and properties of a new photoinitiator of polymerization by visible irradiation based on 3,5-di-tert-butyl-o-benzoquinone

IF 1.7 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Russian Chemical Bulletin Pub Date : 2025-01-14 DOI:10.1007/s11172-024-4460-y
M. P. Shurygina, M. V. Arsenyev, E. V. Baranov, M. A. Baten’kin, M. Yu. Zakharina, E. R. Zhiganshina, A. N. Konev, S. A. Chesnokov
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Abstract

A new sterically hindered trialkyl-substituted o-benzoquinone, 4,6-di-tert-butyl-3-[(3,5-di-tert-butyl-1H-pyrazol-1-yl)methyl]cyclohexane-3,5-diene-1,2-dione was synthesized. Its spectral, electronic, and structural characteristics were determined, which were found to be similar to those for analogous 3,6- and 3,5-di-tert-butyl-o-benzoquinones. The following sequence was observed for the reactivity in the photoreduction reaction in the presence of N,N-dimethylaniline (DMA): 3,6-di-tert-butyl-o-benzoquinone > 4,6-di-tert-butyl-3-[(3,5-di-tert-butyl-1H-pyrazol-1-yl)methyl]cyclohexane-3,5-diene-1,2-dione > 3,5-di-tert-butyl-o-benzoquinone. The new quinone, like 3,6- and 3,5-di-tert-butyl-o-benzoquinones, in combination with DMA was found to initiate radical polymerization under the irradiation by LED sources in the range from 395 to 630 nm. It was found that the introduction of the pyrazole-containing fragment at position 6 of the quinonoid ring of 3,5-di-tert-butyl-o-benzoquinone led to a sharp increase in the activity of the new compound as a photoinitiator compared to 3,5-di-tert-butyl-o-benzoquinone and made the new quinone comparable with 3,6-di-tert-butyl-o-benzoquinone in the photoinitiating activity. At the same time, a photopolymerizable composition containing a photoinitiating system based on 4,6-di-tert-butyl-3-[(3,5-di-tert-butyl-1H-pyrazol-1-yl)methyl]cyclohexane-3,5-diene-1,2-dione was found to be more stable than the photoinitiating system based on 3,6-di-tert-butyl-o-benzoquinone.

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基于3,5-二叔丁基邻苯并醌的新型可见光聚合引发剂的合成及性能研究
合成了一种新的位阻三烷基取代邻苯醌,4,6-二叔丁基-3-[(3,5-二叔丁基- 1h -吡唑-1-基)甲基]环己烷-3,5-二烯-1,2-二酮。测定了其光谱、电子和结构特征,发现其与类似的3,6-和3,5-二叔丁基-邻苯醌相似。在N,N-二甲基苯胺(DMA)存在下,光还原反应的反应活性观察如下顺序:3,6-二叔丁基-邻苯醌;4, 6-di-tert-butyl-3 - [(3 5-di-tert-butyl-1H-pyrazol-1-yl)甲基]cyclohexane-3 5-diene-1, 2-dione祝辞3, 5-di-tert-butyl-o-benzoquinone。在LED光源照射下,在395 ~ 630 nm范围内,发现新的醌类化合物如3,6-和3,5-二叔丁基-邻苯并醌类化合物与DMA结合可引发自由基聚合。结果表明,在3,5-二叔丁基-邻苯并醌类环第6位引入含吡唑的片段,使得新化合物的光引发活性比3,5-二叔丁基-邻苯并醌明显提高,与3,6-二叔丁基-邻苯并醌的光引发活性相当。同时,发现以4,6-二叔丁基-3-[(3,5-二叔丁基- 1h -吡唑-1-基)甲基]环己烷-3,5-二烯-1,2-二酮为光引发体系的光聚合组合物比以3,6-二叔丁基-邻苯醌为光引发体系的光聚合组合物更稳定。
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来源期刊
Russian Chemical Bulletin
Russian Chemical Bulletin 化学-化学综合
CiteScore
2.70
自引率
47.10%
发文量
257
审稿时长
3-8 weeks
期刊介绍: Publishing nearly 500 original articles a year, by leading Scientists from Russia and throughout the world, Russian Chemical Bulletin is a prominent international journal. The coverage of the journal spans practically all areas of fundamental chemical research and is presented in five sections: General and Inorganic Chemistry; Physical Chemistry; Organic Chemistry; Organometallic Chemistry; Chemistry of Natural Compounds and Bioorganic Chemistry.
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