甲基丙烯酸(2-烷基-2-金刚烷)酯的合成及水解研究

doi:10.7517/j.issn.1674-0475.2007.05.357

影像科学与光化学 ›› 2007, Vol. 25 ›› Issue (5): 357-363.DOI: 10.7517/j.issn.1674-0475.2007.05.357

甲基丙烯酸(2-烷基-2-金刚烷)酯的合成及水解研究

回闯, 孟庆伟, 宫斌, 曲景平

大连理工大学, 精细化工国家重点实验室, 辽宁, 大连, 116012

收稿日期:2007-01-09 修回日期:2007-03-08 出版日期:2007-09-23 发布日期:2007-09-23
通讯作者: 孟庆伟(1964- ),男,副教授,通讯联系人,Tel:(0411)88993898,E-mail:Mengqw@chem.dlut.edu.cn.

The Synthesis and Hydrolysis Evaluation of 2-Alkyl Adamantine-2-yl Methacrylate

HUI Chuang, MENG Qing-wei, GONG Bin, QU Jing-ping

The State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116012, Liaoning, P. R. China

Received:2007-01-09 Revised:2007-03-08 Online:2007-09-23 Published:2007-09-23

摘要/Abstract

摘要： 甲基丙烯酸(2-甲基-2-金刚烷)酯和甲基丙烯酸(2-乙基-2-金刚烷)酯是两个重要的193nm光刻胶主体树脂的单体.两个化合物是由2-金刚酮与碘甲烷、碘乙烷的格氏试剂反应得到2-甲基-2-金刚醇、2-乙基-2-金刚醇,然后在氢化钠的作用下与甲基丙烯酰氯发生酯化反应制得.酯化产率50%—60%.产品结构经¹HNMR、IR、MS和元素分析表征.在对甲基苯磺酸-水合物的催化作用下对两个单体进行了水解测试,探讨了水解机理,计算出水解速率常数k,k值分别为-1.52和-3.90.

关键词: 193nm光刻胶, 甲基丙烯酸(2-烷基-2-金刚烷)酯, 2-金刚酮, 水解

Abstract: 2-methyl adamantine-2-yl methacrylate and 2-ethyl adamantine-2-yl methacrylate are two important monomers of matrix polymer for 193 nm photoresist. The two compounds are synthesized based on utilizing methylmagnesium iodide(ethylmagnesium iodide) as Grinard reagent reacted with 2-adamantone to provide 2-methyl(ethyl) adamantine-2-yl which then esterified with methacryloyl chloride in the presence of NaH to provide the target compounds with the yields of 50—60%. The structures of the compounds are confirmed by ¹HNMR, IR, MS and Elementary Analysis. The hydrolysis test was carried out using TsOH·H₂O as catalyst and the hydrolysis mechanism was discussed. The calculated hydrolysis rate constants k are -1.52 and -3.90, respectively.

Key words: 193 nm photoresist, 2-alkyl adamantine-2-yl methacrylate, 2-adamantone, hydrolysis

中图分类号:

回闯, 孟庆伟, 宫斌, 曲景平. 甲基丙烯酸(2-烷基-2-金刚烷)酯的合成及水解研究[J]. 影像科学与光化学, 2007, 25(5): 357-363.

HUI Chuang, MENG Qing-wei, GONG Bin, QU Jing-ping. The Synthesis and Hydrolysis Evaluation of 2-Alkyl Adamantine-2-yl Methacrylate[J]. Imaging Science and Photochemistry, 2007, 25(5): 357-363.

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甲基丙烯酸(2-烷基-2-金刚烷)酯的合成及水解研究

The Synthesis and Hydrolysis Evaluation of 2-Alkyl Adamantine-2-yl Methacrylate

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