Acetic Acid → 2-ethyl-2-adamantyl Methacrylate p-hydroxystyrene

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Into a flask were added 250 g of the 2-ethyl-2-adamantyl methacrylate and p-acetoxystyrene copolymer (20:80) obtained in Synthetic Example 1, 10.3 g (0.084 mol) of 4-dimethylaminopyridine and 202 g of methanol, followed by refluxing for 20 hours. After cooling, the reaction mixture was neutralized with 7.6 g (0.126 mol) of glacial acetic acid, and the product was precipitated by pouring the reaction mixture into a large amount of water. After the precipitated polymerized product was separated by filtration and redissolved in acetone, the procedure of precipitation by pouring polymer solution into a large amount of water was repeated for a total of 3 times to purify the polymerized product. The obtained copolymer of 2-ethyl-2-adamantyl methacrylate and p-hydroxystyrene was 95.9 g. This copolymer had a weight-average molecular weight of about 8,600 with dispersion of 1.65 (GPC method; on polystyrene basis), and its copolymerization ratio was determined to be about 20:80 by a nuclear magnetic resonance (13C-NMR) analyzer. This resin was referred to as Resin A1.

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