양쪽성계면활성제의 유도체합성 및 계면성에 관한 연구(제3보)

Syntheses and Surface Active Properties of Amphoteric Surfactant(3) - Syntheses of Carboxylated Amides from Imidazoline -

Amphoteric surfactants were synthesized by the cyclization of 1-(2-hydroxyethyl)-2-undecyl-2-imidazoline [Ⅰ] with acrylic acid ethyl ester. Compound [Ⅰ] was easily hydrolyzed with water, especially in the presence of a alkali, to afford amidoamines. After [Ⅰ] was hydrolyzed, the reaction mixture was allowed to react with acrylic acid ethyl ester and then soapoinfied. Only sodium salts of N- -(2-carboxyethyl)-N -(2-hydroxyethyl)aminoethyl]dodecanoyl amide [Ⅲ] was obtained. However, when the reacton of [Ⅰ] with acrylic acid ethyl ester was carried out in the presence of water, followed by soapnification, ring cleavage of [Ⅰ] occurred at 2, 3 position, different from hydrolysis of [Ⅰ] where the cleavage occurred at 1, 2 position, to give sodium salts of N-〔N -(2-carboxyethyl)aminoethyl〕-N-(2-hydroxyethyl)dodecanoyl amide [Ⅳ] and N-〔N , N -bis(2-carboxyethyl)aminoethyl〕-N-(2-hydroxyethyl)dodecanoyl amide [Ⅴ] as main products.