Citation: Xiao-Jian Xu, Jian-Wei Guo, Xing Zhong. Synthesis and properties of novel cationic gemini surfactants with adamantane spacer[J]. Chinese Chemical Letters, ;2014, 25(2): 367-369. shu

Synthesis and properties of novel cationic gemini surfactants with adamantane spacer

1.
School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006, China

Corresponding author: Jian-Wei Guo,
Received Date: 24 July 2013
Available Online: 31 October 2013
Fund Project:

Novel quaternary ammonium cationic gemini surfactants, with two hydrocarbon chains and an adamantane core, were designed and synthesized by three-step reactions from adamantane. The structure of obtained surfactants were confirmed by ¹H NMR, FTIR and elements analysis and the surface properties of these surfactants were also studied by surface tension measurements. These target surfactants exhibit much lower critical micelle concentrations (CMC) and higher efficiency in lowering the surface tension of water than typical surfactants.
- Gemini surfactants,
- Adamantane,
- Synthesis
1. [1]
  [1] E.O. Alami, K. Holmberg, Heterogemini surfactants, Adv. Colloid Interface Sci. 100-102 (2003) 13-46.
2. [2]
  [2] R. Zana, Dimeric (Gemini) surfactants: effect of the spacer group on the association behavior in aqueous solution, J. Colloid Interface Sci. 248 (2002) 203-220.
3. [3]
  [3] T. Yoshimura, K. Esumi, Synthesis and surface properties of anionic gemini surfactants with amide groups, J. Colloid Interface Sci. 276 (2004) 231-238.
4. [4]
  [4] E.M. Menger, C.A. Littau, Gemini surfactants: a new class of self-assembling molecules, J. Am. Chem. Soc. 115 (1993) 10083-10090.
5. [5]
  [5] K. Esumi, M. Goino, Y. Koide, Adsorption and adsolubilization by monomeric, dimeric, or trimeric quaternary ammonium surfactant at silica/water interface, J. Colloid Interface Sci. 183 (1996) 539-545.
6. [6]
  [6] M.S. Ali, M. Suhail, G. Ghosh, M. Kamil, K.U. Din, Interactions between cationic gemini/conventional surfactants with polyvinylpyrrolidone: specific conductivity and dynamic light scattering studies, Colloids Surf. A: Physicochem. Eng. Aspects 350 (2009) 51-56.
7. [7]
  [7] M.J. Rosen, J.H. Mathias, L. Davenport, Aberrant aggregation behavior in cationic gemini surfactants investigated by surface tension, interfacial tension, and fluorescence methods, Langmuir 15 (1999) 7340-7346.
8. [8]
  [8] D. Shukla, V.K. Tyagi, Cationic gemini surfactants: a review, J. Oleo Sci. 55 (2006) 381-390.
9. [9]
  [9] S.H. Hsiao, C.T. Li, Synthesis and characterization of new adamantane-based polyimides, Macromolecules 31 (1998) 7213-7217.
10. [10]
  [10] T. Ishizone, H. Tajima, S. Matsuoka, S. Nakahama, Synthesis of tetramers of 1,3- adamantane derivatives, Tetrahedron Lett. 42 (2001) 8645-8647.
11. [11]
  [11] M. Aoyama, S. Hara, Synthesis of functionalized adamantanes from fluoroadamantanes, Tetrahedron 65 (2009) 3682-3687.
12. [12]
  [12] Y. You, J.X. Zhao, R. Jiang, J.J. Cao, Strong effect of NaBr on self-assembly of quaternary ammonium gemini surfactants at air/water interface and in aqueous solution studied by surface tension and fluorescence techniques, Colloid Polym. Sci. 287 (2009) 839-846.
13. [13]
  [13] J.W. Guo, X. Zhong, H. Zhu, L.J. Feng, C.Y. De, Synthesis of novel quaternary ammonium surfactants containing adamantane, Chin. Chem. Lett. 23 (2012) 653-656.
14. [14]
  [14] T. Yoshimura, T. Kusano, H. Iwase, et al., Star-shaped trimeric quaternary ammonium bromide surfactants: adsorption and aggregation properties, Langmuir 28 (2012) 9322-9331.
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沈阳化工大学材料科学与工程学院沈阳 110142