We have investigated the morphology of novel 3,4-bis-alkyloxycarbonyl-hexanedioic acid monolayer (alkyl chain number n = 12, 14, and 16) formed on the water surface by dropping method using Surface Tension Measurement (STm) and Brewster Angle Microscopy (BAM). Surfactant of 3, 4-bis-alkyloxycarbonyl-hexanedioic acid has a gemini type structure. π-A isotherm curves (STm) of two gemini surfactants of n = 12 and 14 showed gradual increase in surface pressure, while that of n = 16 showed gradual increase, a stagnant range and finally steep increase. BAM observation showed each image corresponding to the result of STm measurement. From STm and BAM results of surfactants, it is found that surfactants of n = 12 and 14 formed Liquid-Expand (LE) type monolayer, while that of n = 16 formed Liquid-Condensed (LC) type monolayer including LE-LC phase transition.
References
[1]
Zana, R. and Talmon, Y. (1993) Dependence of Aggregate Morphology on Structure of Dimeric Surfactants. Nature, 362, 228-230. http://dx.doi.org/10.1038/362228a0
[2]
Menger, F.M. and Keiper, J.S. (2000) Gemini Surfactants. Angewandte Chemie International Edition, 39, 1906-1920.
http://dx.doi.org/10.1002/1521-3773(20000602)39:11<1906::AID-ANIE1906>3.0.CO;2-Q
[3]
In, M. and Zana, R. (2007) Phase Behavior of Gemini Surfactants. Journal of Dispersion Science and Technology, 28, 143-154.
[4]
McGregor, C., Perrin, C., Monck, M., Camilleri, P. and Kirby, A.J. (2001) Rational Approaches to the Design of Cationic Gemini Surfactants for Gene Delivery. Journal of the American Chemical Society, 123, 6215-6220.
http://dx.doi.org/10.1021/ja005681c
[5]
Sommerdijk, N.A.J.M., Hoeks, T.H.L., Synak, M., Feiters, M.C., Nolte, R.J.M. and Zwanenburg, B. (1997) Stereodependent Fusion and Fission of Vesicles: Calcium Binding of Synthetic Gemini Phospholipids Containing Two Phosphate Groups. Journal of the American Chemical Society, 119, 4338-4344. http://dx.doi.org/10.1021/ja962303s
[6]
Estroff, L.A. and Hamilton, A.D. (2000) Effective Gelation of Water Using a Series of Bis-urea Dicarboxylic Acids. Angewandte Chemie International Edition, 39, 3447-3450.
http://dx.doi.org/10.1002/1521-3773(20001002)39:19<3447::AID-ANIE3447>3.0.CO;2-X
[7]
Esumi, K., Hara, J., Aihara, N., Usui, K. and Torigoe, K. (1998) Preparation of Anisotropic Gold Particles Using a Gemini Surfactant Template. Journal of Colloid and Interface Science, 208, 578-581.
http://dx.doi.org/10.1006/jcis.1998.5852
[8]
Wang, Y., Desbat, B., Manet, S., Aimé, C., Labrot, T. and Oda, R. (2005) Aggregation Behaviors of Gemini Nucleotide at the Air-Water Interface and in Solutions Induced by Adenine-Uracil Interaction. Journal of Colloid and Interface Science, 283, 555-564. http://dx.doi.org/10.1016/j.jcis.2004.09.003
[9]
Chen, X., Wang, J., Shen, N., Luo, Y., Li, L., Liu, M. and Thomas, R.K. (2002) Gemini Surfactant/DNA Complex Monolayers at the Air-Water Interface: Effect of Surfactant Structure on the Assembly, Stability, and Topography of Monolayers, Langmuir, 18, 6222-6228. http://dx.doi.org/10.1021/la025600l
[10]
Li, R., Chen, Q., Zhang, D., Liu, H. and Hu, Y. (2008) Mixed Monolayers of Gemini Surfactants and Stearic Acid at the air/water interface. Journal of Colloid and Interface Science, 327, 162-168.
http://dx.doi.org/10.1016/j.jcis.2008.07.038
[11]
Acharya, D.P., Kunieda, H., Shiba, Y. and Aratani, K. (2004) Phase and Rheological Behavior of Novel Geini-Type Surfactant Systems. The Journal of Physical Chemistry B, 108, 1790-1797. http://dx.doi.org/10.1021/jp036096b
[12]
Rodriguez-Abreu, C., Rodriguez, E. and Solans, C. (2009) Monomeric and Dimeric Anionic Surfactants: A Comparative Study of Self-aggregation and Mineralization. Journal of Colloid and Interface Science, 340, 254-260.
http://dx.doi.org/10.1016/j.jcis.2009.08.043
[13]
Yoshida, D., Yokoyama, T., Shimoaki, T., Tomita, T., Yoshida, T., Yamamoto, Y., Taga, K., Sumino, A., Dewa, T., Nango, M., Yamamoto, M. and Shervani, Z. (2013) Morphology Observation of Dipalmitoyl Phosphatidyl Choline (DPPC) Monolayer on Water Surface by Dropping Method. Journal of Biophysical Chemistry, 4, 115-121.
http://dx.doi.org/10.4236/jbpc.2013.44016
[14]
Mingotaud, A.F., Mingotaud, C. and Patterson, L.K. (1993) Handbook of Monolayers, Volumes 1 and 2. Academic Press Inc., California.
[15]
Ohe, C., Ida, Y., Matsumoto, S., Sakaki, T., Goto, Y., Noi, M., Tsurumaru, T. and Itoh, K. (2004) Investigations of Polymyxin B-Phospholipid Interactions by Vibrational Sum Frequency Generation Spectroscopy. The Journal of Physical Chemistry B, 108, 18081-18087. http://dx.doi.org/10.1021/jp0404347
[16]
Frey, W., Schief Jr., W.R. and Vogel, V. (1996) Two-Dimensional Crystallization of Streptavidin Studied by Quantitative Brewster Angle Microscopy. Langmuir, 12, 1312-1320. http://dx.doi.org/10.1021/la9505374
[17]
Minones Jr., J., Dynarowicz-Latka, P., Minones, J., Patino, J.M.R. and Iribarnegaray, E. (2003) Orientational Changes in Dipalmitoyl Phosphatidyl Glycerol Langmuir Monolayers. Journal of Colloid and Interface Science, 265, 380-385.
http://dx.doi.org/10.1016/S0021-9797(03)00479-X
[18]
Harkins, W.D. (1952) The Physical Chemistry of Surface Films. Reinhold, New York.
[19]
Nakahara, H., Lee, S., Shoyama, Y. and Shibata, O. (2011) The Role of Palmitic Acid in Pulmonary Surfactant Systems by Langmuir Monolayer Study: Lipid-Peptide Interactions. Soft Matter, 7, 11351-11359.
http://dx.doi.org/10.1039/c1sm06345f
[20]
Nakahara, H. (2012) A Study on Novel Artificial Lung Surfactants Incorporated with Partially Fluorinated Amphiphiles. Yakugaku Zasshi, 132, 817-822. http://dx.doi.org/10.1248/yakushi.132.817
