Gemini surfactants

Journal of Surfactants and Detergents

Volumn 1, Issue 4, 1998, Pages 547-554

  Rosen, Milton J ^a   Tracy, David J ^b  

^a CITY UNIVERSITY OF NEW YORK   (United States)

^b Surfactants Perf Ingredients RI   (United States)

Author keywords

Critical micelle concentration; Dispersion; Emulsification; Foaming; Gemini; Irritation; Surfactants; Synergism; Wetting

Indexed keywords

EID: 0001210907     PISSN: 10973958     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11743-998-0057-8     Document Type: Article

References (103)

1. Kreimeier, U.S. Patent 2,106,180 (1935).
2. Rosen, M.J., Geminis: A New Generation of Surfactants, CHEMTECH 23:30-33 (1993).
3. Parreira, H.C., E.R. Lukenbach, and M.O. Lindemann, Physical Chemical Properties of Solutions of Bis-(Quaternary) Ammonium Bromides, J. Am. Oil Chem. Soc. 56:1015-1021 (1979).
4. Hjelmeland, L.M., W.A. Klee, and J.C. Osborne, a New Class of Nonionic Detergents with a Gluconamide Polar Group, Anal. Biochem. 130:485-490 (1983).
5. Devinsky, F., I. Masarova, and I. Lacko, Surface Activity and Micelle Formation of Some New Bisquaternary Ammonium Salts, J. Colloid Interface Sci. 105:235-239 (1985).
6. Devinsky, F., I. Lacko, F.B. Bittererova, and L. Tomeckova, Relationship Between Structure, Surface Activity, and Micelle Formation of Some New Bisquaternary Isosteres of 1,5-Pentanediammonium Dibromides, Ibid. 114:314-322 (1986).
7. Okahara, M., A. Masuyama, Y. Sumida, and Y.-P. Zhu, Surface Active Properties of New Types of Amphipathic Compounds with Two Lipophilic Alkyl Chains, J. Jpn. Oil Chem. Soc (Yukagaka) 37:746-748 (1988).
8. Micich, T.J., and W.M. Linfield, Wetting Properties of Non-ionics from Branched Fatty Diamides, J. Am. Oil Chem. Soc. 65:820-825 (1988).
9. Rozycka-Roszak, B., S. Witek, and S. Przestalski, A Comparision of the Micellization of Selected Amphiphilic N,N'-Bisdimethyl-1,2-ethanediamine Derivatives with Some Amphiphilic Betaine Ester Derivatives, J. Colloid Interface Sci. 133:181-185 (1989).
10. Devinsky, F., and I. Lacko, Synthesis, Surface Activity, and Micelle Formation of Some Bis-quaternary Ammonium Salts of Glycine Derivatives, Tenside Surf. Det. 27:344-349 (1990).
11. Zhu, Y.-P., A. Masuyama, and M. Okahara, Preparation and Surface Active Properties of Amphipathic Compounds with Two Sulfate Groups and Two Lipophilic Alkyl Chains, J. Am. Oil Chem. Soc. 67:459-463 (1990).
12. 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, Ibid. 68:268-271 (1991).
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) 40:473-477 (1991).
14. Menger, F., and C.A. Littau, Gemini Surfactants: Synthesis and Properties, J. Am. Chem. Soc. 113:1451-1452 (1991).
15. Zhu, Y.-P., A. Masuyama, Y.-I. Kirito, and M. Okahara, Preparation and Properties of Double- or Triple- Chain Surfactants with Two Sulfonate Groups Derived from N-Acyldiethanolamines, Ibid. 68:539-543 (1991).
16. Zana, R., M. Benrraou, and R. Rueff, Alkanediyl-α,ω-bis(dimethylalkyl-ammonium bromide) Surfactants. 1. Effect of the Spacer Chain Length on the CMC and Micelle Ionization Degree, Langmuir 7:1072-1075 (1991).
17. Devinsky, F., I. Lacko, and T. Iman, Relationship Between Structure and Solubilization Properties of Some Bisquaternary Ammonium Amphiphiles, J. Colloid Interface Sci. 143:336-341 (1991).
18. Stein, T.M., and S.H. Gellman, Synthesis and Aggegation Properties of a New Family of Amphiphiles with an Unusual Headgroup Topology, J. Am. Chem. Soc. 114:3943-3950 (1992).
19. 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) 41:301-305 (1992).
20. Zhu, Y.-P., A. Masuyama, Y.-I. 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. 69:626-632 (1992).
21. Rosen, M.J., Z.H. Zhu, and X.Y. Hua, Relations of Structure to Properties of Surfactants, 16. Linear Decyldiphenylether Sulfonates, Ibid. 69:30-33 (1992).
22. Rosen, M.J., Z.H. Zhu, and T. Gao, Synergism in Binary Mixtures of Surfactants. 11. Mixtures Containing Mono- and Disulfonated Alkyl- and Dialkyldiphenylethers, J. Colloid Interface Sci. 157:254-259 (1993).
23. Ono, D., T. Tanaka, A. Masuyana, Y. Nakatsuji, and M. Okahara, Preparation and Properties of Bis (sodium carboxylate) Types of Cleavable Surfactants Derived from Diethyl Tartrate and Fatty Carbonyl Compounds, J. Jpn. Oil Chem. Soc. (Yakagaku) 42:10-16 (1993).
24. Zhu, Y.-P., A. Masuyama, Y. Nakatsuji, and M. Okahara, Synthesis and Properties of Bis (sulfonate) Types of Double-chain Surfactants Bearing a Sulfur Atom in the Connecting Part, Ibid. 42:86-94 (1993).
25. Zhu, Y.-P., A. Masuyama, Y. Kobata, Y. Nakatsuji, M. Okahara, and M.J. Rosen, Double-Chain Surfactants with Two Carboxylate Groups and Their Relation to Similar Doublechain Compounds, J. Colloid Interface Sci. 158:40-45 (1993).
26. Menger, F., and C.A. Littau, Gemini Surfactants: A New Class of Self-Assembling Molecules, J. Am. Chem. Soc. 115:10083-10090 (1993).
27. Alami, E., H. Levy, and R. Zana, Alkanediyl-bis (dimethylalkylamminonium bromide) Surfactants. 2. Structure of the Lyotropic Mesophases in the Presence of Water, Langmuir 9:940-944 (1993).
28. Alami, E., G. Beinert, P. Marie, and R. Zana, Alkanediyl-bis(dimethylalkylammonium bromide) Surfactants. 3. Behavior at the Water Interface, Ibid. 9:1465-1467 (1993).
29. Zana, R., and Y. Talmon, Dependence of Aggregate Morphology on Structure of Dimeric Surfactants, Nature 362:228-229 (1993).
30. Zhu, Y.-P. K. Ishikara, A. Masuyama, Y. Nakatsuji, and M. Okahara, Preparation and Properties of Double-chain Bis (quaternary ammonium) Compounds, J. Jpn. Oil Chem. Soc. (Yukagaku) 42:161-167 (1993).
31. a.R. Infante, Synthesis and Properties of Cationic Surfactants Containing a Disulfide Bond, J. Am. Oil Chem. Soc. 70:37-42 (1993).
32. a.R. Infante, Synthesis, Surface Active Properties and Antimicrobial Activity of New Bis Quaternary Ammonium Compounds, J. Chem. Soc. Perkin Trans. 2:1871-1876 (1994).
33. Karaborni, S., K. Esselink, P.A.J. Hilbers, B. Smit, J. Karthauser, N.M. van Os, and R. Zana, Simulating the Self-Assembly of Gemini (Dimeric) Surfactants, Science 266:254-256 (1994).
34. a..R. Infante, C.H. Chang, and E.I. Franses, Surface Tension Properties of Aqueous Solutions of Disulfur Betaine Derivatives, Colloids Surf. A 87:117-123 (1994).
35. a.R. Infante, New Non-ionic Surfactants from Lysine and Their Performance, J. Disp. Sci. Tech. 15:591-610 (1994).
36. 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. 71:771-776 (1994).
37. 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.:1435-1436 (1994).
38. Rosen, M.J., T. Gao, Y. Nakatsuji, and A. Masuyama, Synergism in Binary Mixtures of Surfactants. 12. Mixtures Containing Surfactants with Two Hydrophilic and Two or Three Hydrophobic Groups, Colloids Surf. 88:1-11 (1994).
39. Diamant, H., and D. Andelman, Dimeric Surfactants: Spacer Chain Conformation and Specific Area at the Air/Water Interface, Langmuir 10:2910-2916 (1994).
40. Eastoc, J., P. Rogueda, B.I. Harrison, A. M. Howe, and A.R. Pitt, Properties of a Dichained Sugar Surfactant, Ibid. 10:4429-4433 (1994).
41. Briggs, C.B.A., I.M. Newington, and A.R. Pitt, Synthesis and Properties of Some Novel Nonionic Polyol Surfactants, J. Chem. Soc. Chem. Commun.:379-380 (1995).
42. Danino, D., Y. Talmon, and R. Zana, Alkanediyl-α,ω-bis(dimethylalkylammonium bromide) Surfactants (dimeric surfactants): 5. Aggregation and Microstructure in Aqueous Solutions, Langmuir 11:1448-1456 (1995).
43. Schosseler, F., O. Anthony, G. Beinert, and R. Zana, Mixed Micelles of the Dimeric Surfactant Ethanediyl-1,2, -bis (dodecyldimethylammonium)bromide and Its Corresponding Monomer, the Dodecyltrimethylammonium Bromide: A Neutron Scattering Study, Ibid. 11:3347-3350 (1995).
44. Song, L.D., and M.J. Rosen, Surface Properties, Micellization, and Premicellar Aggregation of Gemini Surfactants with Rigid and Flexible Spacers, Ibid. 12:1149-1153 (1996).
45. Rosen, M.J., and L.D. Song, Dynamic Surface Tension of Aqueous Surfactant Solutions. 8. Effect of Spacer on Dynamic Properties of Gemini Surfactant Solutions, J. Colloid Interface Sci. 179:261-268 (1996).
46. Liu, L., and M.J. Rosen, The Interaction of Some Novel Di-quaternary Gemini Surfactants with Anionic Surfactants, Ibid. 179:454-159 (1996).
47. Eastoc, J., P. Rogueda, A. M. Howe, A. R. Pitt, and R.K. Heenan, Properties of New Glucamide Surfactants, Langmuir 12:2701-2705 (1996).
48. Dam, T., J.B.F.N. Engberts, J. Karthauser, S. Karaborni, and N.M. van Os, Synthesis, Surface Properties and Oil Solubilization Capacity of Cationic Gemini Surfactants, Colloids Surf. A 118:41-19 (1996).
49. Okano, T.N., Egawa, M. Fujiwara, and M. Fukuda, α-Sulfonated Fatty Acid Esters: II. Solution Behavior of α-Sulfonated Fatty Acid Polyethylene Glycol Esters, J. Am. Oil Chem. Soc. 73:31-37 (1996).
50. a.R. Infante, C. Selve, and M.P. Vinardell, Preliminary Studies of the Toxic Effects of Nonionic Surfactants Derived from Lysine, Toxicology 106:1-9 (1996).
51. Kim, T.S., T. Hirao, and I. Ikeda, Preparation of bis-Quaternary Ammonium Salts from Epicholorohydrin, J. Am. Oil Chem. Soc. 73:67-71 (1996).
52. a.R. Infante, Nonionic Amphiphilic Compounds from Lysine as Molecular Mimics of Lecithins, Ibid. 73:79-86 (1996).
53. a.R. Infante, J. Seguer, M.J. Stebe, and C. Selve, Nonionic Amphiphilic Compounds from Aspartic and Glutamic Acids as Structural Mimics of Lecithins, Ibid. 73:87-96 (1996).
54. Rosen, M.J., and L Liu, Surface Activity and Premicellar Aggregation of Some Novel Diquaternary Gemini Surfactants, Ibid. 73:885-890 (1996).
55. Kim, T.-S., T. Kida, Y. Nakatsuji, T. Hirao, and I. Ikeda, Surface-Active Properties of Novel Cationic Surfactants with Two Alkyl Chains and Two Ammonio Groups, Ibid. 73:907-911 (1996).
56. Jaeger, D.A., and E.L. Brown, Double-chain Surfactants with Two Carboxylate Head Groups That Form Vesicles, Langmuir 12:1976-1980 (1996).
57. a.R. Infante, Synthesis, Aggegation, and Biological Properties of a New Class of Gemini Cationic Amphiphilic Compounds from Arginine, bis (Args), Ibid. 12:5296-5301 (1996).
58. Danino, D., Y. Talmon, and R. Zana, Vesicle-to-Micelle Transformation in Systems Containing Dimeric Surfactants, J. Colloid Interface Sci. 185:84-93 (1997).
59. Duivenvoorde, F.L., M.C. Feiters, S.J. van der Gaast, and J.B.F.N. Engberts, Synthesis and Properties of Di-n-dodecylα,ω-alkyl Bisphosphate Surfactants, Langmuir 13:3737-3743 (1997).
60. Zana, R., M. In, H. Levy, and G. Duportail, Alkanediylbis(dimethylalkylammonium bromide). 7. Fluorescence Probing Studies of Micelle Micropolarity and Microviscosity. Ibid. 13:5552-5557 (1997).
61. Rico-Lattes, I., and A. Lattes, Synthesis of New Sugar-Based Surfactants Having Biological Applications: Key Role of Their Self-Association, Colloids Surf. A 123-124:37-48 (1997).
62. Castro, M.J.L., J. Kovensky, and A.F. Cirelli, Gemini Surfactants from Alkyl Glucosides, Tetrahedron Lett. 38:3995-3998 (1997).
63. Reitz, G., and G. Boehmke, Great Britain Patent 1,503,280 (1978).
64. Behler, A., R. Piorr, and M. Schaefer, U.S. Patent, 4,936,551 (1990).
65. Okahara, M., and A. Masuyama, U.S. Patent 5,160,450 (1992).
66. Gruber, B., Ger. Offen. DE 4,232,414 A1 (1994).
67. Wangemann, F. Ger. Offen. DE 4,321,022 A1 (1995).
68. Raths, H.C., and W.E. Noack, Ger. Offen. DE 4,401,565 (1995).
69. Kaiser, R.J., U.S. Patent 5,507,863 (1996).
70. Kaiser, R.J., U.S. Patent 5,487,778 (1996).
71. Varadaraj, R., and S. Zushma, U.S. Patent 5,585,516 (1996).
72. Varadaraj, R., and S. Zushma, U.S. Patent 5,493,050 (1996).
73. Kaiser, R.J., U.S. Patent 5,599,933 (1997).
74. Okano, T., M. Fukuda, J. Tanabe, M. Ono, Y. Akabane, H. Takahashi, N. Egawa, T. Sakotani, H. Kanao, and Y. Yoneyanna, U.S. Patent 5,681,803 (1997).
75. Raths, H., Ger. Offen. DE 19,622,612 (1997).
76. Tracy, D.J., R. Li, and J.M. Ricca, U.S. Patent 5,710,121 (1998).
77. Kitsubi, T., M. Uno, K. Kita, Y. Fujikura, A. Nakano, M. Tosaka, K. Yahagi, S. Tamura, and K. Maruta, U.S. Patent 5,714,457 (1998).
78. McConnell, R.B., U.S. Patent 3,855,235 (1974).
79. McConnell, R.B., U.S. Patent 3,887,476 (1975).
80. Login, R.B., U.S. Patent 4,764,306 (1988).
81. Login, R.B., U.S. Patent 4,734,277 (1988).
82. Login, R.B., U.S. Patent 4,812,263 (1989).
83. Chauhuri, R.K., D.J. Tracy, and R.B. Login, U.S. Patent 4,886,890 (1989).
84. Li, J., N. Dahanayake, R.L. Reierson, and D.J. Tracy, U.S. Patent 5,643,498 (1997).
85. Bersworth, F., U.S. Patent 2,524,218 (1950).
86. Bersworth, F., U.S. Patent 2,530,147 (1950).
87. Bersworth, F., U.S. Patent 2,532,391 (1950).
88. Schmitz, A. G.B. Patent 1,149,140 (1967).
89. Nakamo, A., T. Kitsuki, K. Kita, and M. Asuga, International Patent PCT WO 96/01800 (1996).
90. Kwetkat, K., International Patent PCT WO 97/31890 (1997).
91. Li, J., M. Dahanayake, R.L. Reierson, and D.J. Tracy, U.S. Patent 5,656,586 (1997).
92. Briggs, C.B., and A.R. Pitts, U.S. Patent 4,892,806 (1990).
93. Gorelli-Calvet, R., F. Brisset, J. Rico, A. Lattes, and L. Godefroy, U.S. Patent 5,403,922 (1995).
94. Adams, K., Eur. Pat. Appl. EPO 688781 (1995).
95. Scheibel, J., D.S. Connor, and E.Y. Fu, U.S. Patent 5,534,197 (1996).
96. Connor, D.S., Y. Fu, and J.J. Scheibel, U.S. Patent 5,512,699 (1996).
97. Tsubone, K., H. Nishio, and M. Kusumaru, Jpn. Kokai Tokkyo Koho JP 08,291,040 (1996).
98. Tsubone, K., H. Nishio, and M. Kusumaru, Jpn. Kokai Tokkyo Koho JP 08,319,262 (1996).
99. Wong, S., U.S. Patent 5,622,938 (1997).
100. Rosen, M.J., Surfactants and Interfacial Phenomena, 2nd edn., John Wiley, New York, 1989, pp. 84-85.
101. Draves, C.Z., and R.G. Clarkson, A New Method for the Evaluation of Wetting Agents, Amer. Dyestuff Rept. 20:201-209 (1931).
102. Rosen, M.J., and Z.H. Zhu, Enhancement of Wetting Properties of Water- Insoluble Surfactants via Solubilization, J. Am. Oil Chem. Soc. 70:65 (1993).
103. Dreja, M., and B. Tieke, Polymerization of Styrene in Ternary Microemulsion Using Cationic Gemini Surfactants, Langmuir 14:800-807 (1998).