A novel cationic surfactant having two quaternary ammonium ions

Eun-kyung Kang; Byung Min Lee; Hyun Ah Hwang; Jong Choo Lim

Journal of Industrial and Engineering Chemistry, Vol.17, No.5-6, 845-852, December, 2011

DOI10.1016/j.jiec.2011.09.001 Export Citation

A novel cationic surfactant having two quaternary ammonium ions

Eun-kyung Kang¹, Byung Min Lee^{1, 2, †}, Hyun Ah Hwang¹, and Jong Choo Lim^{3, †}

¹Department of Green Chemistry and Environmental Biotechnology, University of Science and Technology, 113, Gwahak-ro, Yuseong-gu, Daejeon 305-333, Republic of Korea
²Chemical Biotechnology Research Center, Green Chemistry Division, Korea Research Institute of Chemical Technology, 141, Gajeong-ro, Yuseong-gu, Daejeon 305-600, Republic of Korea
³Department of Chemical and Biochemical Engineering, Dongguk University-Seoul, Seoul 100-715, Republic of Korea

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Novel cationic surfactants having two hydrophobic groups and two quaternary ammonium ions which are in the middle of alkyl group were prepared by two-step reactions. Three kinds of N,N-bis-(3-nalkoxy-2-hydroxypropyl)-N,N-dimethyl-1,3-propylenediamine were prepared quantitatively as the intermediate by the condensation reaction between alkyl glycidyl ether and 3-(dimethylamino)-1-propylamine under mild conditions without solvent and catalyst. The intermediates were quaternized with dimethyl sulfate. The structures of the products were characterized by 1H NMR, FAB/MS and FT-IR. The interfacial properties of the synthesized cationic surfactants were measured such as critical micelle concentration, surface tension, interfacial tension, contact angle and foam stability.

Keywords:Gemini surfactants;Cationic surfactants;Quaternary ammonium;Interfacial properties

[References]

Porter MR, Handbook of Surfactants, Sully, South Wales (1994)
Zana R, Benrraou M, Rueff R, Langmuir., 7, 1072 (1991)
Menger FM, Littau CA, J. Am. Chem. Soc., 113, 1451 (1991)
Menger FM, Littau CA, J. Am. Chem. Soc., 115, 10083 (1993)
Zana R, Talmon Y, Nature., 362, 228 (1993)
Rosen MJ, Song LD, J. Colloid Interface Sci., 179(1), 261 (1996)
Karaborni S, Esselink K, Hilbers PA, Smit B, Karthauser J, Vanos NM, Zana R, Science, 266(5183), 254 (1994)
Micich TJ, Lintield WM, J. Am. Oil Chem. Soc., 65, 820 (1988)
Menger FM, Keiper JS, Angew. Chem. Int. Ed., 39, 1906 (2000)
Zana R, Adv. Colloid Interface Sci., 97, 203 (2002)
Zhu YP, Masuyama A, Okahara M, J. Am. Oil Chem. Soc., 67, 459 (1990)
Zhu YP, Masuyama A, Okahara M, J. Am. Oil Chem. Soc., 68, 168 (1990)
Rang MJ, Kim JD, Oh SG, Lee BM, Lim JC, Hong JD, Kang HH, Lee JG, Recent Research Trends in Colloid and Interface Chemistry, vol. 80, The Korean Federation of Science and Technology Societies, Seoul (2007)
Rosen MJ, Zhu ZH, J. Am. Oil. Chem. Soc., 70, 65 (1993)
Menger MF, Keiper JS, Angew. Chem. Int. Ed., 39, 1906 (2000)
Song LD, Rosen MJ, J. Colloid Interface Sci., 12, 1149 (1996)
Alami E, Holmberg K, Eastoe J, J. Colloid Interface Sci., 247(2), 447 (2002)
Korean Patent 10-2000-0023327 (2000)
Kielman HS, Van Steen PHF, Surface Active Agents, Society Chemical Industry, London (1979)
Miller CA, Neogi P, Interfacial Phenomena: Equilibrium and Dynamic Effects, Marcel Decker Inc., New York (1985)
Vick KM, Soap Cosmet. Chem. Special. May, 36 (1984)
Kanner B, Reid WG, Peterson IH, Ind. Eng. Chem. Prod. Res. Dev., 6, 88 (1967)
Dahms GH, Zombeck A, Cosmet. Toiletries Mag., 110, 91 (1995)
Shukla D, Tyagi VK, J. Oleo Sci., 55, 381 (2006)
Mori F, Lim JC, Miller CA, Prog. Colloid Polym. Sci., 82, 114 (1990)
Mori F, Lim JC, Raney OG, Elsik CM, Miller CA, Colloid Surf. A., 440, 323 (1989)
Lim JC, J. Korean Ind. Eng. Chem., 6(4), 610 (1995)

[Referenced By]

[Related Articles]

[1] Porter MR, Handbook of Surfactants, Sully, South Wales (1994)

[2] Zana R, Benrraou M, Rueff R, Langmuir., 7, 1072 (1991)

[3] Menger FM, Littau CA, J. Am. Chem. Soc., 113, 1451 (1991)

[4] Menger FM, Littau CA, J. Am. Chem. Soc., 115, 10083 (1993)

[5] Zana R, Talmon Y, Nature., 362, 228 (1993)

[6] Rosen MJ, Song LD, J. Colloid Interface Sci., 179(1), 261 (1996)

[7] Karaborni S, Esselink K, Hilbers PA, Smit B, Karthauser J, Vanos NM, Zana R, Science, 266(5183), 254 (1994)

[8] Micich TJ, Lintield WM, J. Am. Oil Chem. Soc., 65, 820 (1988)

[9] Menger FM, Keiper JS, Angew. Chem. Int. Ed., 39, 1906 (2000)

[10] Zana R, Adv. Colloid Interface Sci., 97, 203 (2002)

[11] Zhu YP, Masuyama A, Okahara M, J. Am. Oil Chem. Soc., 67, 459 (1990)

[12] Zhu YP, Masuyama A, Okahara M, J. Am. Oil Chem. Soc., 68, 168 (1990)

[13] Rang MJ, Kim JD, Oh SG, Lee BM, Lim JC, Hong JD, Kang HH, Lee JG, Recent Research Trends in Colloid and Interface Chemistry, vol. 80, The Korean Federation of Science and Technology Societies, Seoul (2007)

[14] Rosen MJ, Zhu ZH, J. Am. Oil. Chem. Soc., 70, 65 (1993)

[15] Menger MF, Keiper JS, Angew. Chem. Int. Ed., 39, 1906 (2000)

[16] Song LD, Rosen MJ, J. Colloid Interface Sci., 12, 1149 (1996)

[17] Alami E, Holmberg K, Eastoe J, J. Colloid Interface Sci., 247(2), 447 (2002)

[18] Korean Patent 10-2000-0023327 (2000)

[19] Kielman HS, Van Steen PHF, Surface Active Agents, Society Chemical Industry, London (1979)

[20] Miller CA, Neogi P, Interfacial Phenomena: Equilibrium and Dynamic Effects, Marcel Decker Inc., New York (1985)

[21] Vick KM, Soap Cosmet. Chem. Special. May, 36 (1984)

[22] Kanner B, Reid WG, Peterson IH, Ind. Eng. Chem. Prod. Res. Dev., 6, 88 (1967)

[23] Dahms GH, Zombeck A, Cosmet. Toiletries Mag., 110, 91 (1995)

[24] Shukla D, Tyagi VK, J. Oleo Sci., 55, 381 (2006)

[25] Mori F, Lim JC, Miller CA, Prog. Colloid Polym. Sci., 82, 114 (1990)

[26] Mori F, Lim JC, Raney OG, Elsik CM, Miller CA, Colloid Surf. A., 440, 323 (1989)

[27] Lim JC, J. Korean Ind. Eng. Chem., 6(4), 610 (1995)