Synthesis, interfacial property, and application of new hybrid anion surfactant containing fluorocarbon and hydrocarbon chains

Eun-kyung Kang; Eun-Ho Sohn; Ga Young Jung; Seon Hwa Jung; Jong-Wook Ha; Soo-Bok Lee; In Jun Park; Byung Min Lee

Journal of Industrial and Engineering Chemistry, Vol.67, 72-79, November, 2018

DOI10.1016/j.jiec.2018.06.016 Export Citation

Synthesis, interfacial property, and application of new hybrid anion surfactant containing fluorocarbon and hydrocarbon chains

Eun-kyung Kang^{1, 2}, Eun-Ho Sohn^{1, 2, †}, Ga Young Jung^{1, 2}, Seon Hwa Jung^{2, 3}, Jong-Wook Ha², Soo-Bok Lee², In Jun Park^{1, 2, †}, and Byung Min Lee^{1, 2, †}

¹Advanced Materials and Chemical Engineering, University of Science and Technology, 217, Gajeong-ro, Yuseong-gu, Daejeon 34113, Republic of Korea
²Center for Interface Chemistry and Engineering, Korea Research Institute of Chemical Technology, 141, Gajeong-ro, Yuseong-gu, Daejeon 34114, Republic of Korea
³Department of Applied Chemistry, Kyungpook National University, 80, Daehakro, Bukgu, Daegu 41566, Republic of Korea

E-mail:, ,

Hybrid F2HX surfactants bearing a sulfate moiety and both hydrocarbon and fluorocarbon chains were prepared by the reaction of alkyl glycidyl ethers with fluoro-alcohol, and subsequent sulfation. The fluorocarbon number in F2HX was fixed at the shortest number possible (i.e., 2), while the hydrocarbon number (X) in the second chain was varied between 2, 4, 6, and 8. Their surface-active properties and emulsion stabilities were systematically estimated as a function of the X. Among them, F2H8 exhibited the optimal surfactant performance, which was comparable to previously reported surfactants and it was successfully applied in the emulsion polymerization of vinylidene fluoride.

Keywords:Hybrid anion surfactant;Fluorocarbon chain;Surface-active property;Emulsion polymerization;Vinylidene fluoride

[References]

Griffiths PC, Cheung AYF, Jenkins RL, Howe AM, Pitt AR, Heenan RK, King SM, Langmuir, 20(4), 1161 (2004)
Abe M, Curr. Opin. Colloid Interface Sci., 4, 354 (1999)
Kissa E, Fluorinated Surfactants and Repellents, Second ed., Marcel Dekker, 2001.
Badr MZ, Birnbaum LS, Mech. Ageing Dev., 125, 69 (2004)
Kawashima Y, Suzuki S, Kozuka H, Sato M, Suzuki Y, Toxicology, 93, 85 (1994)
Kannan K, Corsolini S, Falandysz J, Oehme G, Focardi S, Giesy JP, Environ. Sci. Technol., 36, 3210 (2002)
Midasch O, Drexler H, Hart N, Beckmann MW, Int. Arch. Occup. Environ. Health, 80, 643 (2007)
U.S. Environmental Protection Agency Home Page. https://www.epa.gov/.(Accessed 24 November 2016).
Tan B, Lehmler HJ, Vyas SM, Knutson BL, Rankin SE, Nanotechnology, 16, 502 (2005)
Schuster T, Krumpfer JW, Schellenberger S, Friedrich R, Klapper M, Mullen K, J. Colloid Interface Sci., 428, 276 (2014)
Schuster T, Schellenberger S, Friedrich R, Klapper M, Mullen K, J. Fluor. Chem., 154, 30 (2013)
Sha M, Xing P, Jiang B, Chin. Chem. Lett., 26, 491 (2015)
Micich TJ, Linfield WM, J. Am. Oil Chem. Soc., 65, 820 (1988)
Menger FM, Littau CA, J. Am. Chem. Soc., 113, 1451 (1991)
Sommerdijk NA, Hoeks TH, Synak M, Feiters MC, Nolte RJ, Zwanenburg B, J. Am. Chem. Soc., 119(19), 4338 (1997)
Kang EK, Lee BM, Hwang HA, Lim JC, J. Ind. Eng. Chem., 17(5-6), 845 (2011)
Menger FM, Mbadugha BNA, J. Am. Chem. Soc., 123(5), 875 (2001)
Zhu YP, Masuyama A, Okahara M, J. Am. Oil Chem. Soc., 67, 459 (1990)
Lim JC, Kang EK, Park JM, Kang HC, Lee BM, J. Ind. Eng. Chem., 18(4), 1406 (2012)
Yoshino N, Hamano K, Omiya Y, Kondo Y, Ito A, Abe M, Langmuir, 11(2), 466 (1995)
Kondo Y, Miyazawa H, Sakai H, Abe M, Yoshino N, J. Am. Chem. Soc., 124(23), 6516 (2002)
Kang EK, Jung GY, Jung SH, Lee BM, J. Ind. Eng. Chem., 61, 216 (2018)
Heo HJ, Park IJ, Lee SG, Ha JW, Lee SB, Sohn EH, Green Chem., 20, 502 (2018)
Yoshino N, Morita M, Ito A, Abe M, J. Fluor. Chem., 70, 187 (1995)
Sagisaka M, Ito A, Kondo Y, Yoshino N, Kwond KO, Sakai H, Abe M, Colloids Surf. A: Physicochem. Eng. Asp., 183-185, 749 (2001)
Yoshimura T, Bong M, Matsuoka K, Honda C, Endo K, J. Colloid Interface Sci., 339(1), 230 (2009)
Zhang L, Geng B, Lu Q, Xu A, Zhang S, J. Surfactants Deterg., 19, 559 (2016)
Kirsch P, Modern Fluoroorganic Chemistry, Second ed., Wiley-VCH, 2001.
Lee JY, Shin YJ, Ryu SR, Nanoemulsion eyedrop composition containing cycloporin and method for preparing same, PCT WO 2014/189251 A1, Nov 27, 2014.
Zhou Z, Wang J, Polymer, 40, 201 (2016)
Wisniewska M, Terpilowski K, Chibowski S, Urban T, Zarko VI, Gun'ko VM, J. Macromol. Sci. A Pure Appl. Chem., 50, 639 (2013)

[Referenced By]

[Related Articles]

[1] Griffiths PC, Cheung AYF, Jenkins RL, Howe AM, Pitt AR, Heenan RK, King SM, Langmuir, 20(4), 1161 (2004)

[2] Abe M, Curr. Opin. Colloid Interface Sci., 4, 354 (1999)

[3] Kissa E, Fluorinated Surfactants and Repellents, Second ed., Marcel Dekker, 2001.

[4] Badr MZ, Birnbaum LS, Mech. Ageing Dev., 125, 69 (2004)

[5] Kawashima Y, Suzuki S, Kozuka H, Sato M, Suzuki Y, Toxicology, 93, 85 (1994)

[6] Kannan K, Corsolini S, Falandysz J, Oehme G, Focardi S, Giesy JP, Environ. Sci. Technol., 36, 3210 (2002)

[7] Midasch O, Drexler H, Hart N, Beckmann MW, Int. Arch. Occup. Environ. Health, 80, 643 (2007)

[8] U.S. Environmental Protection Agency Home Page. https://www.epa.gov/.(Accessed 24 November 2016).

[9] Tan B, Lehmler HJ, Vyas SM, Knutson BL, Rankin SE, Nanotechnology, 16, 502 (2005)

[10] Schuster T, Krumpfer JW, Schellenberger S, Friedrich R, Klapper M, Mullen K, J. Colloid Interface Sci., 428, 276 (2014)

[11] Schuster T, Schellenberger S, Friedrich R, Klapper M, Mullen K, J. Fluor. Chem., 154, 30 (2013)

[12] Sha M, Xing P, Jiang B, Chin. Chem. Lett., 26, 491 (2015)

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

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

[15] Sommerdijk NA, Hoeks TH, Synak M, Feiters MC, Nolte RJ, Zwanenburg B, J. Am. Chem. Soc., 119(19), 4338 (1997)

[16] Kang EK, Lee BM, Hwang HA, Lim JC, J. Ind. Eng. Chem., 17(5-6), 845 (2011)

[17] Menger FM, Mbadugha BNA, J. Am. Chem. Soc., 123(5), 875 (2001)

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

[19] Lim JC, Kang EK, Park JM, Kang HC, Lee BM, J. Ind. Eng. Chem., 18(4), 1406 (2012)

[20] Yoshino N, Hamano K, Omiya Y, Kondo Y, Ito A, Abe M, Langmuir, 11(2), 466 (1995)

[21] Kondo Y, Miyazawa H, Sakai H, Abe M, Yoshino N, J. Am. Chem. Soc., 124(23), 6516 (2002)

[22] Kang EK, Jung GY, Jung SH, Lee BM, J. Ind. Eng. Chem., 61, 216 (2018)

[23] Heo HJ, Park IJ, Lee SG, Ha JW, Lee SB, Sohn EH, Green Chem., 20, 502 (2018)

[24] Yoshino N, Morita M, Ito A, Abe M, J. Fluor. Chem., 70, 187 (1995)

[25] Sagisaka M, Ito A, Kondo Y, Yoshino N, Kwond KO, Sakai H, Abe M, Colloids Surf. A: Physicochem. Eng. Asp., 183-185, 749 (2001)

[26] Yoshimura T, Bong M, Matsuoka K, Honda C, Endo K, J. Colloid Interface Sci., 339(1), 230 (2009)

[27] Zhang L, Geng B, Lu Q, Xu A, Zhang S, J. Surfactants Deterg., 19, 559 (2016)

[28] Kirsch P, Modern Fluoroorganic Chemistry, Second ed., Wiley-VCH, 2001.

[29] Lee JY, Shin YJ, Ryu SR, Nanoemulsion eyedrop composition containing cycloporin and method for preparing same, PCT WO 2014/189251 A1, Nov 27, 2014.

[30] Zhou Z, Wang J, Polymer, 40, 201 (2016)

[31] Wisniewska M, Terpilowski K, Chibowski S, Urban T, Zarko VI, Gun'ko VM, J. Macromol. Sci. A Pure Appl. Chem., 50, 639 (2013)