Structural effects on surface and micellar properties of alkanediyl-α,ω-bis(sodium N-acyl-β-alaninate) gemini surfactants

Tsubone, Kazuyuki; Arakawa, Yoshiko; Rosen, Milton J.

doi:10.1016/s0021-9797(03)00078-x

Cited by 138 publications

(106 citation statements)

References 22 publications

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“…The value of n (the number of species whose concentration at the interface changes with c) is taken as 2, although for divalent geminis (having 1 surfactant ion and 2 non surfactant counterions), the values of both 2 and 3 have been proposed [22]. For gemini surfactants, it was found that one of the two counterions is frequently firmly wedged in between the two charged headgroups, especially when the spacer is quite short [23].…”

Section: Surface Tension Measurementsmentioning

confidence: 99%

Is the counterion responsible for the unusual thermodynamic behaviour of the aqueous solutions of gemini bispyridinium surfactants?

Fisicaro

Compari

Bacciottini

et al. 2014

Colloids and Surfaces A: Physicochemical and Engineering Aspect

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Apparent and partial molar enthalpies at 298 K of the aqueous solutions of cationic gemini surfactants 1,1′-didodecyl-2,2′-trimethylenebispyridinium dichloride (12-Py(2)-3-(2)Py-12 Cl); 1,1′-didodecyl-2,2′-tetramethylenebispyridinium dichloride (12-Py(2)-4-(2)Py-12 Cl); 1,1′-didodecyl-2,2′-octamethylenebispyridinium dichloride (12-Py(2)-8-(2)Py-12 Cl); 1,1′-didodecyl-2,2′-dodecamethylenebispyridinium dichloride (12-Py(2)-12-(2)Py-12 Cl) were measured as a function of concentration and are here reported for the first time. The curve of the compound with the four carbon atoms spacer lies between those of the compound with spacer of 2 and 3 carbon atoms, not below the latter, as expected. This behaviour, we have already found for the same compounds here studied, but having methanesulfonate as counterion, is interpreted as an evidence of a conformation change of the molecule determined by stacking interactions between the two pyridinium rings, appearing at an optimum length of the spacer. The curves of apparent and molar enthalpies vs. concentration and surface tension measurements, here reported, show that this behaviour is independent on the counterion. On the contrary, the group contribution additivity for the counterion is respected, independently on the spacer length.Keywords. Apparent and partial molar enthalpies; cationic gemini surfactants; 1,1′-didodecyl-2,2′-trimethylenebispyridinium dichloride; 1,1′-didodecyl-2,2′-tetramethylenebispyridinium dichloride; 1,1′-didodecyl-2,2′-octamethylenebispyridinium dichloride; 1,1′-didodecyl-2,2′-dodecamethylenebispyridinium dichloride; micellization enthalpy, group contribution.Briefs. Apparent and partial molar enthalpies at 298 K of the aqueous solutions of cationic gemini surfactants 1,1′-didodecyl-2,2′-trimethylenebispyridinium dichloride (12-Py(2)-3-(2)Py-12 Cl);1,1′-didodecyl-2,2′-tetramethylenebispyridinium dichloride (12-Py(2)-4-(2)Py-12 Cl); 1,1′-didodecyl-2,2′-octamethylenebispyridinium dichloride (12-Py(2)-8-(2)Py-12 Cl); 1,1′-didodecyl-2,2′-dodecamethylenebispyridinium dichloride (12-Py(2)-12-(2)Py-12 Cl) have been measured as a function of concentration, in order to confirm the lack of methylene group additivity with respect to the enthalpic properties of the solutions, when it is added in the spacer, already found in the case of methansulfonates. The data obtained support the hypothesis of a conformation change dependent on the spacer length, but independent on the counterion.

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Section: Surface Tension Measurementsmentioning

confidence: 99%

Is the counterion responsible for the unusual thermodynamic behaviour of the aqueous solutions of gemini bispyridinium surfactants?

Fisicaro

Compari

Bacciottini

et al. 2014

Colloids and Surfaces A: Physicochemical and Engineering Aspect

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“…For several years, Tsubone and coworkers have studied the anionic gemini surfactant (CH 2 ) 2 [N(COC 11 H 23 )-CH 2 CH 2 (CO 2 Na)] 2 (compound 212), having N,N-dialkylamide and carboxylate groups, a dimer corresponding to SDMA, its homologs, and analogs (21)(22)(23)(24)(25). An interesting finding for the anionic gemini surfactants is that they show little or no break in their specific conductance vs. surfactant concentration plots.…”

mentioning

confidence: 99%

Micelle ionization degree of anionic gemini surfactant having N,N‐dialkylamide and carboxylate groups

Tsubone¹,

Ghosh

2003

J Surfact & Detergents

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The critical micelle concentration (cmc) behavior in aqueous NaCl solutions of the anionic gemini surfactant N, N'-ethylenebis(sodium N-dodecanoyl-β-alanate), (CH 2 ) 2 [N-(COC 11 H 23 )CH 2 CH 2 (CO 2 Na)] 2 (212), having N,N-dialkylamide and carboxylate groups in a molecule was investigated to measure the value of micelle ionization degree (α). For comparison, the behavior of sodium N-dodecanoyl-N-methyl-β-alanate (SDMA), a monomer corresponding to 212, also was investigated. The α value obtained from the Corrins-Harkins plot for 212 is 0.97 when [Na + ] ≤ 0.025 M and the value for SDMA is 0.51 when [Na + ] ≤ 0.1 M. That the α for 212 is larger than that for SDMA reflects the higher pK a1 value for 212 than the pK a value of SDMA. For 212, when [Na + ] ≤ 0.025 M the amount of Na + released during micellization is so large that the Na + concentration above the cmc is almost equal to that below the cmc, and therefore 212 nearly behaves as a nonionic surfactant.Paper no. S1330 in JSD 6, 225-229 (July 2003).KEY WORDS: Anionic gemini surfactant, Corrin-Harkins plot, degree of counter-ion binding, micelle ionization degree.Unusual interfacial behaviors are shown by two anionic surfactants, sodium N-dodecanoyl-N-methyl-β-alanate (SDMA) and sodium N-dodecanoylsarcosinate (SDSA), having N,Ndialkylamide and carboxylate groups, in comparison with those of sodium N-dodecanoyl-N-methyltaurate (SDMT), having a sulfonate group instead of a carboxylate group, and sodium decyloxyacetate (SDOA), containing an ether oxygen instead of an N-methyl adjacent to the methylenecarboxylate group (1). The unusual behaviors were found to be due to the simultaneous presence of the N,Ndialkylamide and carboxylate groups in the same molecule. Namely, the increasing order of conductance/surface tension critical micelle concentration (cmc) ratios is SDOA < SDMT < SDSA < SDMA. This order is the same as those of the parameters, A min (the minimum area occupied by the surfactant molecule at the air/water interface) and cmc/C 20 ratio (a measure of the factors inhibiting micellization relative to adsorption at the air/water interface), implying that there is a steric factor inhibiting micellization for the compounds having N,N-dialkylamide and carboxylate groups. The same order of increase in pH with surfactant concentration in the vicinity of the cmc appears to indicate H-bonded interaction between amide and protonated carboxylate groups. Thus, anionic surfactants having N,N-dialkylamide and carboxylate groups release Na + in micellization.In the past decade, a new type of surfactant called gemini surfactants has attracted considerable interest (2-19), since these compounds have much smaller cmc values and much greater efficiency in reducing surface tension than expected. They have two hydrophobic chains and two hydrophilic head groups in the molecule. The gemini surfactants are the subject of more studies, because of the extraordinary surface activity (3,9,13,14,19,20).For several years, Tsubone and coworkers have studied the anionic gemini surfa...

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“…Figure 5 show the plot of Log C 20 -pC 20 values versus n Carbon number 12 or 14 or 16 for the zwitterionic gemini surfactant with spacer value S 2 or 3. For S 2; 3a, 3b, and 3c surfactants, the Log C 20 value decreased steadily as n increased at cationic counterpart, whereas, for S 3; 4a, 4b, and 4c surfactants, Log C 20 value increased in small change as n increased at n 14 and more effectively increased at n 14 .The deviation when S 3 for the longer chain compound was the result of the decrease in monomer activity upon premicellar aggregation of the geminis 33 .…”

Section: Surface Activity Of Zwitterionic Amphiphilesmentioning

confidence: 92%

Diester-containing Zwitterionic Gemini Surfactants with Different Spacer and Its Impact on Micellization Properties and Viscosity of Aqueous Micellar Solution

Patil

Pratap

2016

J. Oleo Sci.

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Structural effects on surface and micellar properties of alkanediyl-α,ω-bis(sodium N-acyl-β-alaninate) gemini surfactants

Cited by 138 publications

References 22 publications

Is the counterion responsible for the unusual thermodynamic behaviour of the aqueous solutions of gemini bispyridinium surfactants?

Is the counterion responsible for the unusual thermodynamic behaviour of the aqueous solutions of gemini bispyridinium surfactants?

Micelle ionization degree of anionic gemini surfactant having N,N‐dialkylamide and carboxylate groups

Diester-containing Zwitterionic Gemini Surfactants with Different Spacer and Its Impact on Micellization Properties and Viscosity of Aqueous Micellar Solution

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