アクリル酸エステルとイミダゾリンとの反応による両性界面活性剤の合成

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A study was made on preparation of amphoteric surfactants by the reaction of 1- (2-hydroxyethyl) -2-undecyl-2-imidazoline (1) with ethyl acrylate. Imidazolines are easily hydrolyzed with water, especially in the presence of a base, to afford amidoamines. After (1) was hydrolyzed, the reaction mixture was allowed to react with ethyl acrylate and then saponified. Only sodium salts of N- [N'- (2-carboxyethyl) -N'- (2-hydroxyethyl) aminoethyl] laurylamide (4) was obtained. However, when the reaction of (1) with ethylacrylate was carried out in the presence of water, followed by saponification, ring cleavage of (1) occurred at 2, 3 position, different from hydrolysis of (1) where the cleavage occurred at 1, 2 position, to give sodium salts of N- [N'- (2-carboxyethyl) ami-noethyl] -N- (2-hydroxyethyl) laurylamide (5) and N- [N', N'-bis (2-carboxyethyl) aminoethyl] -N- (2-hydroxyethyl) laurylamide (6) as main products. In case of the reaction of (1) with ethyl acrylate under unhydrous condition, 1- (ethylcarboxyethoxyethyl) -2-undecyl-2-imidazoline (7) was obtained as a major product, however, the reaction was rather slow, and gave sodium salt of N- [N'- (carboxyethoxyethyl) aminoethyl] laurylamide (8) and N- [N'- (2-hydroxyethyl) aminoethyl] -laurylamide (2) by saponification. By the reaction of (7) with ethyl acrylate in the presence of water, followed by saponification, sodium salt of N- [N'- (carboxyethoxyethyl) -N'- (2-carboxyethyl) aminoethyl] laurylamide (9) was obtained.

アクリル酸エステルとイミダゾリンとの反応による両性界面活性剤の合成

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