아미노산 모노글리세리드류의 합성 및 계면성

조경행; 김태영; 김성웅; 정노희; 남기대

Journal of the Korean Industrial and Engineering Chemistry, Vol.5, No.1, 99-104, February, 1994

Export Citation

아미노산 모노글리세리드류의 합성 및 계면성

Synthesis and Surface Active Properties of Amino Acid Monoglyceride

조경행, 김태영, 김성웅, 정노희, 남기대

초록

비이온성 계면활성제인 5종의 모노글리세릴 기로글루타메이트류는 초산나트륨 촉매하에 피로글루탐산과 모노글리세리드를 에스테르 반응시켜 높은 수율로 제조하였다. IR, ¹H-NMR로 그들의 구조를 확인하였고 계면장력, 유화력을 측정하였다. 반응 생성물들의 오일용액에서의 물에 대한 계면장력은 5∼9dyne/cm까지 저하되었고, 계면장력 저하능은 모노글리세리드 퍼로글루탐산 에스테르의 소수성 탄소부에 의존된다. 벤젠 및 대두유에서의 유화력을 측정한 결과 대두유보다 벤젠의 유화력이 우수하였으며 유화제로서의 응용이 기대된다.

Nonionic surfactants, monoglyceryl pyroglutamates, have been synthesized in a high yield by esterification of monoglyceride with pyroglutamic acid in the presence of sodium acetate catalyst. Their structures were confirmed by IR and ¹NMR studies. For these compounds surface active properties including interfacial tension and emulsifying power were measured. The interfacial tensions of their oil solution against water were decreased to 5∼9dyne/cm and hydrophobic alkyl chain of monoglyceryl pyroglutamates. The experimental results indicated that emulsifying power of the nonionic surfactant was better in benzene than in soybean oil. Due to the good surface properties, the nonionic sutfactants, monoglyceryl pyroglutamates, are expected to be used as emulsifiers.

[References]

Babayan VK, Kaufan TG, Lehman H, Tkaczak RJ, J. Soc. Cosmet. Sci., 15, 473 (1964)
Mcintyre RT, J. Am. Oil Chem. Soc., 56, 835A (1979)
Kaufmann HP, Kreishman J, Fetteoseifen Aust., 60, 3 (1958)
Horikawa K, Masuyama S, Imamura M, Toda Y, Sci. Ind., 51, 281 (1977)
U.S. Patent, 2,023,075 (1958)
U.S. Patent, 2,406,329 (1958)
Sci. Ind., 40, 198 (1966)
Sci. Ind., 42, 239 (1968)
Toda Y, Fragrance J., 68, 56 (1984)
Yoshiro T, Noriaki K, Tomoharu K, Nippon Nogei Ka., 55, 943 (1981)
KS M0000-1991
Rosano HL, John D, Whittam JH, J. Am. Oil Chem. Soc., 59, 360 (1982)
Davies JT, 2nd Inter. Congress of Surface Activity, 1, 426 (1957)
Stahl E, Chemiker-Z., 82, 323 (1958)
Wachs W, Tenside, 4, 40 (1967)

[Referenced By]

[1] Babayan VK, Kaufan TG, Lehman H, Tkaczak RJ, J. Soc. Cosmet. Sci., 15, 473 (1964)

[2] Mcintyre RT, J. Am. Oil Chem. Soc., 56, 835A (1979)

[3] Kaufmann HP, Kreishman J, Fetteoseifen Aust., 60, 3 (1958)

[4] Horikawa K, Masuyama S, Imamura M, Toda Y, Sci. Ind., 51, 281 (1977)

[5] U.S. Patent, 2,023,075 (1958)

[6] U.S. Patent, 2,406,329 (1958)

[7] Sci. Ind., 40, 198 (1966)

[8] Sci. Ind., 42, 239 (1968)

[9] Toda Y, Fragrance J., 68, 56 (1984)

[10] Yoshiro T, Noriaki K, Tomoharu K, Nippon Nogei Ka., 55, 943 (1981)

[11] KS M0000-1991

[12] Rosano HL, John D, Whittam JH, J. Am. Oil Chem. Soc., 59, 360 (1982)

[13] Davies JT, 2nd Inter. Congress of Surface Activity, 1, 426 (1957)

[14] Stahl E, Chemiker-Z., 82, 323 (1958)

[15] Wachs W, Tenside, 4, 40 (1967)