Abstract
New amphoteric surfactants of N-(3-alkoxy-2-hydroxypropyl)-N-(2-hydroxyethyl)-β-alanine (APA) have been synthesized. The fundamental surface-active properties (critical micelle concentration and isoelectric point) and hemolysis tests were also investigated to examine the effects of differences in chain length of the alkoxy moiety. The hemolysis result of APA exhibited low constant values irrespective of the alkyl chain length. The amphoteric APA surfactant was confirmed to have a mild effect on human microorganisms and to possess excellent surface-active properties. In addition, a speculative model of micelle configuration was estimated by semiempirical molecular orbital simulations.
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Abbreviations
- APA:
-
N-(3-alkoxy-2-hydroxypropyl)-N-(2-hydroxyethyl)-β-alanine
- CMC:
-
critical micelle concentration
- HD50 :
-
concentration of surfactant required to hemolyze 50% of erythrocytes
- Na-APA:
-
sodium salt of APA
- Na-HAA:
-
N-(2-hydroxyalkyl)-N-(2-hydroxyethyl)-β-alanine sodium salt
References
Xia, J., I.A. Nnanna, and K. Sakamoto, Amino Acid Surfactants: Chemistry, Synthesis, and Properties, in Protein-Based Surfactants, Synthesis, Physicochemical Properties and Applications, edited by I.A. Nnanna and J. Xia, Marcel Dekker, New York, 2001, p. 75.
Takai, M., H. Hidaka, and M. Moriya, New Amphoteric Surfactants Containing a 2-Hydroxyalkyl Group: I. Preparation and Properties of N-(2-Hydroxyethyl)-N-(2-Hydroxyalkyl)-β-alanines. J. Am. Oil Chem. Soc. 66:537 (1979).
Hidaka, H., M. Moriya, and M. Takai, New Amphoteric Surfactants Containing a 2-Hydroxyalkyl Group: II. The Dependence of Physicochemical Properties on the pH Value for N-(2-Hydroxyethyl)-N-(2-hydroxyalkyl)-β-alanines, J. Am. Oil Chem. Soc. 56:914 (1979).
Takai, M., H. Hidaka, S. Ishikawa, M. Takada, and M. Moriya, New Amphoteric Surfactants Containing a 2-Hydroxyalkyl Group: III. Performance of Binary Systems of Amphoteric/Anionic Surfactants, J. Am. Oil Chem. Soc. 57:382 (1980).
Takai, M., H. Hidaka, S. Ishikawa, M. Takada, and M. Moriya, New Amphoteric Surfactants Containing a 2-Hydroxyalkyl Group: IV. Performance of Amphoteric Surfactant/Soap Blends, J. Am. Oil Chem. Soc. 57:183 (1980).
Hidaka, H., M. Moriya, and T. Onai, New Amphoteric Surfactants Containing a 2-Hydroxyalkyl Group: VII. Thermotropic Liquid Crystals of Amphoteric Surfactants, J. Jpn. Oil Chem. Soc. (Yukagaku) 34:58 (1985).
Moriya, M., A. Nishimura, K. Hosoda, M. Takai, and H. Hidaka, New Amphoteric Surfactants Containing a 2-Hydroxyalkyl Group: VIII. Synthesis and Surface Activities for Amphoteric Oligomeric or Polymeric Surfactants of β-Alanine Type, J. Am. Oil Chem. Soc. 63:263 (1986).
Hidaka, H., T. Onai, M. Murata, K. Fujiwara, M. Takai, and M. Moriya, New Amphoteric Surfactants Containing a 2-Hydroxyalkyl Group: IX. The pH Dependence of Micellar Assemblies Composed of Amphoteric Oligomeric and Polymeric Surfactants. J. Colloid Interface. Sci. 119:565 (1987).
Hidaka, H., Helical Aggregation of Chiral Amphoteric Surfactants Containing Hydroxyl Groups, Colloids Interfaces 58:1 (1991).
Hidaka, H., M. Murata, and T. Onai, Helical Aggregates of Chiral N-(2-Hydroxydodecyl) Amino Acids, J. Chem. Soc., Chem. Commun.:562 (1984).
Fukui, K., T. Yonezawa, and H. Shingu, A Molecular Orbital Theory of Reactivity in Aromatic Hydrocarbons, J. Chem. Phys. 20:722 (1952).
Fukui, K., T. Yonezawa, C. Nagata, and H. Shingu, A Molecular Orbital Theory of Reactivity in Aromatic, Heteroaromatic, and Other Conjugated Molecules, J. Chem. Phys. 22:1433 (1954).
Fukui, K., A Simple Quantum Theoretical Interpretation of the Chemical Reactivity of Organic Compounds, in Molecular Orbital in Chemistry, Physics, and Biology, edited by P.-O. Löwdin and B. Pullman, Academic Press, New York, 1964, p. 513.
Stewart, J.J.P., Optimization of Parameters for Semiempirical Methods I. Method, J. Comp. Chem. 10:209 (1989).
Stewart, J.J.P., Optimization of Parameters for Semiempirical Methods II. Applications, J. Comp. Chem. 10:221 (1989).
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Hidaka, H., Koike, T., Kurihara, M. et al. Preparation and properties of new tetrafunctional amphoteric surfactants bearing amino, carboxyl, and hydroxyl groups and an ether bond. J Surfact Deterg 6, 131–136 (2003). https://doi.org/10.1007/s11743-003-0256-3
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DOI: https://doi.org/10.1007/s11743-003-0256-3