Micelle formation of imidazolium ionic liquids in aqueous solution

Jungnickel, Christian; Łuczak, Justyna; Ranke, Johannes; Fernández, J.F.; Müller, Anja; Thöming, Jorg

doi:10.1016/j.colsurfa.2007.09.020

Cited by 334 publications

(272 citation statements)

References 29 publications

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“…In the case of the cationic surfactant hexadecyltrimethylammonium bromide (CTAB) the effect of ILs on the surfactant cmc confirms the trend above described [8][9][10][11][12][13]. However, when IL posses surface activity as reported for long alkyl chain ionic liquids [14][15][16][17][18][19][20][21] and some short alkyl chain ILs [22,23] the ionic liquid / surfactant mixture behaves as a typical binary surfactant system [24][25][26]. In these binary systems the mixed micelle composition X 1 M as well as the  M interaction parameter quantifying the synergism can be obtained by applying the equations of the Regular Solution Theory [27].…”

Section: Introductionsupporting

confidence: 47%

Catanionic surfactant formation from the interaction of the cationic surfactant hexadecyltrimethylammonium bromide (CTAB) and the ionic liquid 1-butyl-3-methylimidazolium octyl sulfate (bmim-octyl SO4) in aqueous solution

Comelles

Ribosa

González

et al. 2015

Colloids and Surfaces A: Physicochemical and Engineering Aspect

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The interaction between the cationic surfactant Hexadecyltrimethylammonium bromide (CTAB) and the ionic liquid 1-butyl-3-methylimidazolium octyl sulfate (bmim-octylSO 4 ) in aqueous solution has been investigated at two total concentrations (0.5 and 10 mM) and different CTAB mole fractions ( CTAB ).Samples of different physical appearance were obtained depending on  CTAB suggesting different kind of aggregates. Bluish solutions ( CTAB from 0.1 to 0.6) were assigned to vesicles of the catanionic surfactant formed (CTA-octylSO 4 ), whereas clear and isotropic solutions ( CTAB  0.6) corresponded to mixed micelles. Surface tension, electrical conductivity, absorbance and dynamic light scattering (DLS) measurements were performed with the aim of correlating properties changes with the aggregation structures. The critical aggregation concentration (cac) and the surface tension value at the cac ( cac ) were much lower for the mixtures than for the individual components. Thiis finding reveals the 3 exceptional surface activity of these mixtures, attributable to the formation of the CTA-octylSO 4 catanionic surfactant. Once the catanionic surfactant is formed it makes no sense to consider anymore the initial CTAB / bmim-octylSO 4 binary system but a new one composed by CTA-octylSO 4 and the excess of bmimoctylSO 4 or CTAB. On the basis of this consideration the surface activity parameters have been recalculated.

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Section: Introductionsupporting

confidence: 47%

Catanionic surfactant formation from the interaction of the cationic surfactant hexadecyltrimethylammonium bromide (CTAB) and the ionic liquid 1-butyl-3-methylimidazolium octyl sulfate (bmim-octyl SO4) in aqueous solution

Comelles

Ribosa

González

et al. 2015

Colloids and Surfaces A: Physicochemical and Engineering Aspect

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“…[2][3][4][5][6] To date, the aggregation behavior of imidazolium derivatives with variable chain lengths and mainly chloride and bromide anions has been presented. [2,5,7,8] Several methods for determining the critical Abstract: Some ionic liquids (ILs) are structurally analogous to surfactants, especially those that consist of a combination of organic and inorganic ions. The critical micelle concentration (CMC) is a basic parameter of surface chemistry and colloid science.…”

Section: Introductionmentioning

confidence: 99%

Predicting the Critical Micelle Concentrations of Aqueous Solutions of Ionic Liquids and Other Ionic Surfactants

Preiss

Jungnickel

Thöming

et al. 2009

Chemistry A European J

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Some ionic liquids (ILs) are structurally analogous to surfactants, especially those that consist of a combination of organic and inorganic ions. The critical micelle concentration (CMC) is a basic parameter of surface chemistry and colloid science. A significant amount of research has already been carried out to determine the CMCs of ILs. However, because of the many varied cation/anion combinations, it is a daunting task to measure the CMCs of all possible ILs. Herein we suggest a general rule for predicting the CMCs of ionic surfactants in water based on data from COSMO-RS calculations. In accordance with the Stauff-Klevens rule, the molecular volume (V(m)) is sufficient to describe similar homologous series of cationic surfactants such as imidazolium- and ammonium-based ionic liquids with varying side-chain lengths. However, to also include anionic surfactants like Na[C(n)SO(4)] in a more general correlation, V(m) has to be exchanged by the cubed molecular radius (r3(m)) and the molecular surface has to be used as an additional descriptor. Furthermore, to describe double amphiphilic compounds like [C(4)MIm][C(8)SO(4)], the enthalpies of mixtures calculated by COSMO-RS have to be taken into account. The resulting equation had allowed us to predict the CMCs of all of the 36 tested surfactants with an error similar to or smaller than the usual experimental errors (18 different cations, 10 different anions: root mean squared error (rmse)=0.191 logarithmic units; R(2)=0.994). We discuss the factors governing micelle formation on the basis of our calculations and show that the structure of our equation can be related to Gibbs' theory of crystallization.

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“…tension), but it contributes also to cell signaling, and is therefore strongly involved in many cellular processes, such as cell adhesion, migration, division and differentiation. [43][44][45] In this study, we evaluated the morphological and mechanical modifications induced by three different 63 This protocol has been recently employed in our group to specifically detect modulations in the membrane/cytoskeleton interface during cell adhesion-and migrationrelated processes. 58,64,65 We focused our attention on the elastic properties of the cell outer envelope, composed by the cell membrane linked to the actin cytoskeleton, since this is the cell region where the first action of ILs is expected to take place.…”

Section: 42mentioning

confidence: 99%

Imidazolium-Based Ionic Liquids Affect Morphology and Rigidity of Living Cells: an Atomic Force Microscopy Study

Schulte¹,

Milani²,

Podestà

2018

Preprint

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The study of the toxicity, biocompatibility, and environmental sustainability of room-temperature Ionic Liquids (ILs) is still in its infancy. Understanding the impact of ILs on living organisms, especially from the aquatic ecosystem, is urgent, since on one side large amounts of these substances are widely employed as solvents in industrial chemical processes, and on the other side evidences of toxic effects of ILs on microorganisms and single cells have been observed. To date, the toxicity of ILs have been investigated by means of macroscopic assays aimed at characterizing the effective concentrations (like the EC50) that cause the dead of a significant fraction of the population of microorganisms and cells. These studies allowed to identify the cell membrane as the first target of the IL interaction, whose effectiveness was correlated to the lipophilicity of the cation, i.e. to the length of the lateral alkyl chain. Our study aimed at characterizing the molecular mechanisms of the toxicity of ILs. To this purpose, we carried out a combined topographic and mechanical analysis by Atomic Force Microscopy of living breast metastatic cancer cells (MDA-MB-231) upon interaction with imidazolium-based ILs. We showed that ILs are able to induce modifications of the overall rigidity (effective Young modulus) and morphology of the cells. Our results demonstrate that ILs act on the physical properties of the cell membrane, and possibly induce cytoskeletal reorganization, already at concentrations below the EC50. These potentially toxic effects are stronger at higher IL concentrations, as well as with longer lateral chains in the cation.

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Micelle formation of imidazolium ionic liquids in aqueous solution

Cited by 334 publications

References 29 publications

Catanionic surfactant formation from the interaction of the cationic surfactant hexadecyltrimethylammonium bromide (CTAB) and the ionic liquid 1-butyl-3-methylimidazolium octyl sulfate (bmim-octyl SO4) in aqueous solution

Catanionic surfactant formation from the interaction of the cationic surfactant hexadecyltrimethylammonium bromide (CTAB) and the ionic liquid 1-butyl-3-methylimidazolium octyl sulfate (bmim-octyl SO4) in aqueous solution

Predicting the Critical Micelle Concentrations of Aqueous Solutions of Ionic Liquids and Other Ionic Surfactants

Imidazolium-Based Ionic Liquids Affect Morphology and Rigidity of Living Cells: an Atomic Force Microscopy Study

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