Diethanolamine → Isobutylene para-methylstyrene

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Isobutylene/para-methylstyrene/para-diethanolaminomethylstyrene copolymer was prepared in accordance with the technique of U.S. Pat. No. 5,162,445 which is incorporated by reference herein. In the nucleophilic substitution reaction, 500 g of isobutylene/p-methylstyrene/p-bromomethylstyrene copolymer (1.7 mole % p-methylstyrene, 0.7 mole % p-bromomethylstyrene 30 ML @ 125° C.) was dissolved in 2267 g of toluene in a 5-liter resin flask under nitrogen to form an 18 wt. % solution. Then 24.6 g diethanol amine (Aldrich, 99%) in 567 g of isopropanol was added slowly with stirring at room temperature to give a 14.9 wt % polymer solution in an 80/20 (weight/weight) toluene/isopropanol solvent blend. The solution was heated with stirring under nitrogen to reflux at about 87° C. for 3 hours before being allowed to cool. The polymer was recovered by precipitation and kneading in isopropanol. The recovered "wet" polymer was further purified by washing and kneading in a 50/50, water/methanol mixture to complete the removal of unreacted diethanolamine and then vacuum-oven dried at 70° C. for 48 hours with 0.2 wt. % BHT mixed as an antioxidant. The polymer was characterized by 'H NMR and showed the complete conversion of p-bromomethyl to diethanolaminomethyl functionality (0.7 mole % DEA).

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