Langmuir
. CONCLUSIONS
In summary, a novel family of pH-sensitive Gemini surfactants
containing 2-pyrrolidone head groups N,N′-dialkyl-N,N′-dipyr-
Article
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4
1
413.
rolidone ethylenediamine (Di-C P, where n = 6, 8 10, 12) were
n
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successfully synthesized and characterized. Comparing with
ionic type Gemini surfactants m-2-m and nonionic glucona-
mide-type Gemini surfactants Glu(n)-2-Glu(n), surfactants
with pyrrolidone heterocyclic headgroup have slightly superior
surface activity. It provides more evidence to understand the
structure−property relationship of Gemini surfactant at the
molecular level. As the pH changes from 2.5 to 11.0, the surface
activity improves remarkably, which possess a nice potential
application in the process of emulsion and demulsification by
simply changing pH. Moreover, owing to the existence of 2-
pyrrolidone heterocyclic in head groups, the new surfactants
might find special applications in nanomaterial development
and industrial technologies such as pesticide formulation,
controlled release, and wastewater treatment. Further inves-
tigation on the aggregates morphology and applications of this
novel family of Gemini surfactant is in progress.
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ASSOCIATED CONTENT
Supporting Information
■
(
*
S
Details on the synthesis and characterizations of pH-sensitive
Gemini surfactants containing 2-pyrrolidone head groups
(
Shifts of Common Laboratory Solvents as Trace Impurities. J. Org.
Chem. 1997, 62, 7512−7515.
(
Figures S1−S5), curves of pH titration experiments (Figures
1
S6−S8), H NMR spectrum of Di-C P in CDCl and in D O at
different pD (Figures S9 and S10), the A and pC of Di-C P
6
3
2
(17) Zhang, X. L.; Penfold, J.; Thomas, R. K.; Tucker, I. M.; Petkov,
J. T.; Bent, J.; Cox, A.; Campbell, R. A. Adsorption Behavior of
Hydrophobin and Hydrophobin/Surfactant Mixtures at the Air-Water
Interface. Langmuir 2011, 27, 11316−11323.
min
20
n
in absence of salt at pH 2.5, 7.0, and 11.0 (Table S1), the γ−log
c plots of Di-C P aqueous solutions in presence of 0, 5, and 50
10
mM NaCl at pH 2.5 (Figure S11), pressure−area isotherms of
(18) Rosen, M. J. Surfactants and Interfacial Phenomena, 2nd ed.; John
Wiley &Sons: New York, 1989.
spread Di-C P monolayer at pH 11.0 (Figure S12). This
12
(19) Menger, F. M.; Shi, L.; Rizvi, S. A. A. Re-evaluating the Gibbs
Analysis of Surface Tension at the Air/Water Interface. J. Am. Chem.
Soc. 2009, 131, 10380−10381.
(20) Menger, F. M.; Shi, L.; Rizvi, S. A. A. Additional Support for a
AUTHOR INFORMATION
■
Revised Gibbs Analysis. Langmuir 2010, 26, 1588−1589.
21) Laven, J.; With, G. D. Should the Gibbs Analysis Be Revised.
Langmuir 2011, 27, 7958−7962.
22) Menger, F. M.; Rizvi, S. A. A.; Shi, L. Reply to “Should the
Gibbs Analysis Be Revised? Langmuir 2011, 27, 7963−7965.
23) Zana, R. Alkanediyl-α,ω-bis(dimethylalkylammonium bromide)
(
*
(
Notes
The authors declare no competing financial interest.
(
Surfactants. J. Colloid Interface Sci. 2002, 246, 182−190.
ACKNOWLEDGMENTS
This work was supported by the National Natural Science
Foundation of China (NSFC20973129).
■
(24) Rosen, M. J.; Zhu, Z. H.; Gu, B.; Murphy, D. S. Relationship of
Structure to Properties of Surfactants. 14. Some N-Alkyl-2-
pyrrolidones at Various Interfaces. Langmuir 1988, 4, 1273−1277.
(25) Wettig, S. D.; Verrall, R. E. Thermodynamic Studies of Aqueous
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dx.doi.org/10.1021/la3008156 | Langmuir 2012, 28, 7174−7181