Surface and aqueous properties of anionic gemini surfactants having dialkyl amide, carboxyl, and carboxylate groups

Journal of Surfactants and Detergents

Volumn 6, Issue 1, 2003, Pages 39-46

  Tsubone, Kazuyuki ^a   Ogawa, Tomoyasu ^a   Mimura, Kunio ^a  

^a KANEBO LTD   (Japan)

Author keywords

Anionic gemini surfactant; Aqueous property; Human patch test; Premicellar formation; Premicelle; Skin irritation potential; Surface activity; Surfactant irritation

Indexed keywords

ANIONIC GEMINI SURFACTANT; ANIONIC SURFACTANT; GA 12; SURFACTANT; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONDUCTANCE; CRITICAL MICELLE CONCENTRATION; HUMAN; HUMAN EXPERIMENT; MICELLE; PATCH TEST; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; SKIN IRRITATION; STRUCTURE ANALYSIS; SURFACE PROPERTY; SURFACE TENSION;

EID: 0037234247     PISSN: 10973958     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11743-003-0246-5     Document Type: Article

References (26)

1. Rosen, M.J., Surfactants and Interfacial Phenomena, 2nd edn., Wiley & Sons, New York, 1989.
2. Rosen, M.J., A New Generation of Surfactants, CHEMTECH 30:23 (1993).
3. Zana, R., M. Benrraou, and R. Rueff, Alkanediyl-α,β-bis(dimethylalkylammnonium bromide) Surfactants 1. Effect of the Spacer Chain Length on the Critical Micelle Concentration and Micelle Ionization Degree, Langmuir 7:1072 (1991).
4. Menger, F.M., and C.A., Littau, Gemini Surfactants: Synthesis and Properties, J. Am. Chem. Soc. 113:1451 (1991).
5. Menger, F.M, and C.A. Littau, A New Class of Self-Assembling Molecules, J. Am. Chem. Soc. 115:10083 (1993).
6. Gao, T., and M.J. Rosen, Dynamic Surface Tension of Aqueous Surfactant Solutions. 6. Compounds Containing Two Hydrophilic Head Groups and Two or Three Hydrophobic Groups and Their Mixtures with Other Surfactants, J. Am. Oil Chem. Soc. 71:771 (1994).
7. Zhu, Y.-P., A. Masuyama, Y. Kobata, Y. Nakatsuji, M. Okahara, and M.J. Rosen, Synthesis and Properties of Bis(sulfonate) Types of Double-Chain Surfactants Bearing a Sulfur Atom in the Connecting Part, J. Colloid Interface Sci. 158:40 (1993).
8. Alami, E., H. Levy, and R. Zana, Alkanediyl-α,β-bis(dimethylalkylammonium bromide) Surfactants 2. Structure of the Lyotropic Mesophases in the Presence of Water, Langmuir 9:940 (1993).
9. Frindi, M., B. Michels, H. Levy, and R. Zana, Alkanediyl-α,β-bis (dimethylalkylammonium bromide) Surfactants 4. Ultrasonic Absorption Studies of Amphiphile Exchange Between Micelles and Bulk Phase in Aqueous Micellar Solutions, Langmuir 10:1140 (1994).
10. Rosen, M.J., and L. Liu, Surface Activity and Premicellar Aggregation of Some Novel Diquaternary Gemini Surfactants, J. Am. Oil Chem. Soc. 73:885 (1996).
11. Kim, T.-S., T. Kida, Y. Nakatsuji, T. Hirano, and I. Ikeda, Surface-Active Properties of Novel Cationic Surfactants with Two Alkyl Chains and Two Ammonio Groups, J. Am. Oil Chem. Soc. 73:907 (1996).
12. Masuyama, A., M. Yokota, Y.-P. Zhu, T. Kida, and Y. Nakatsuji, Unique Interfacial Properties of a Homologous Series of Novel Triple-Chain Amphiphiles Bearing Three Anionic Head Groups Derived from 1,1,1-Tris(hydroxymethyl)ethane, J. Chem. Soc., Chem. Commun. 1435 (1994).
13. Zhu, Y.-P., A. Masuyama, T. Nagata, and M. Okahara, Preparation and Properties of Double-Chain Surfactants Bearing Two Sulfonate Groups, J. Jpn. Oil Chem. Soc. (Yukagaku) 40:473 (1991).
14. Song, L.D., and M.J. Rosen, Surface Properties, Micellization, and Premicellar Aggregation of Gemini Surfactants with Rigid and Flexible Spacers, Langmuir 12:1149 (1996).
15. Zhu, Y.-P., A. Masuyama, and M. Okahara, Preparation and Surface-Active Properties of New Amphipathic Compounds with Two Phosphate Groups and Two Long-Chain Alkyl Groups, J. Am. Oil Chem. Soc. 68:268 (1991).
16. Zhu, Y.-P., A. Masuyama, Y. Kirito, M. Okahara, and M.J. Rosen, Preparation and Properties of Glycerol-Based Double- or Triple-Chain Surfactants with Two Hydrophilic Ionic Groups, J. Am. Oil Chem. Soc. 69:626 (1992).
17. Masuyama, A., T. Hirono, Y.-P. Zhu, M. Okahara, and M.J. Rosen, Synthesis and Properties of Bis(taurine) Types of Double-Chain Surfactants, J. Jpn Oil Chem. Soc. (YUKAGAKU) 41:301 (1992).
18. Diamant, H., and D. Andelman, Dimeric Surfactants: Spacer Chain Conformation and Specific Area at the Air/Water Interface, Langmuir 10:2910 (1994).
19. Perez, L., A. Pinazo, M.J. Rosen, and M.R. Infante, Surface Active Properties at Equilibrium of Novel Gemini Cationic Amphiphilic Compounds from Arginine, Bis(Args), Langmuir 14:2307 (1998).
20. Rosen, M.J., J.H. Mathias, and L. Davenport, Aberrant Aggregation Behavior in Cationic Gemini Surfactants Investigated by Surface Tension, Interfacial Tension, and Fluorescence Methods, Langmuir 15:7340 (1999).
21. Uhle, F., and S. Harris, The Synthesis of α-Methyamino Acids, J. Org. Chem. 78:381 (1956).
22. Tsubone, K., and M.J. Rosen, Structural Effect on Surface Activities of Anionic Surfactants Having N-Acyl-N-methylamide and Carboxylate Groups, J. Colloid Interface Sci. 244:394 (2001).
23. Rapaport, M., Patch Testing in Japanese Subjects, Contact Dermatitis 11:93 (1984).
24. Rhein, L.D., F.A. Simion, H. Robert, C. Robert, M. Jairajh, and M. Howard, Human Cutaneous Response to a Mixed Surfactant System: Role of Solution Phenomena in Controlling Surfactant Irritation, Dermatologica 180:18 (1990).
25. Sugihara, G., and M. Tanaka, A pH and pNa Study of Aqueous Solutions of Sodium Deoxycholate, Bull Chem. Soc. Jpn. 49: 3457 (1976).
26. Murata, Y., G. Sugihara, K. Fukushima, M. Tanaka, and K. Matsushita, Study of the Micelle Formation of Sodium Deoxycholate, Concentration Dependence of Carbon-13 Nuclear Magnetic Chemical Shift, J. Phys. Chem. 86:4690 (1982).