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

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.

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 Nail to provide the target compounds with the yields of 50-60 %. The structures of the compounds are confirmed by 1^HNMR, 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.