Micellization and Antimicrobial Properties of Surface-Active Ionic Liquids Containing Cleavable Carbonate Linkages.

Imidazolium-based ionic liquids (ILs) containing cleavable carbonate linkages, 1-alkyloxycarbonyloxyethyl-3-methylimidazolium chlorides with alkyl chains of 10, 12, and 14 carbon atoms, were synthesized, and their self-assembly behavior and antimicrobial activity were investigated. Differential scanning calorimetry and polarized optical microscopy studies reveal that carbonate-functionalized ILs form stable thermotropic smectic liquid-crystalline phases over a wide range of temperature. The surface activity and aggregation behavior of these new ILs were investigated by tensiometry, conductometry, potentiometry, and spectrofluorimetry.

Hexadecyltrimethylammonium bromide (CTA-Br) and 1-butyl-3-methylimidazolium tetrafluoroborate (bmim-BF) in aqueous solution: An ephemeral binary system.

Hypothesis: Mixtures of the cationic surfactant hexadecyltrimethylammonium bromide (CTA-Br) and the ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate (bmim-BF) in aqueous solutions are expected to behave as typical binary cationic surfactant system taking into account the surface activity displayed by the ionic liquid, instead of considering the IL as a water cosolvent.

Experiments: Surface tension and conductivity measurements have been conducted as a function of the total concentration of the mixtures at different surfactant mole fraction (α) to investigate the surface active properties.

Findings: Turbidity immediately appearing when the compounds are mixed in water suggests the spontaneous formation of the low soluble compound hexadecyltrimethylammonium tetrafluoroborate (CTA-BF), together with the salt formed by the respective counterions bmimand Br in solution.

Skin delivery of antioxidant surfactants based on gallic acid and hydroxytyrosol.

Objectives: The aim of this study has been to investigate the dermal absorption profile of the antioxidant compounds gallic acid and hydroxytyrosol as well as their derivatives, hexanoate (hexyl gallate and hydroxytyrosol hexanoate) and octanoate (octyl gallate and octanoate derivative) alkyl esters (antioxidant surfactants). Previously, the scavenging capacity of these compounds, expressed as efficient dose ED50, has also determined.

Methods: The percutaneous absorption of these compounds was obtained by an in vitro methodology using porcine skin biopsies on Franz static diffusion cells.

Self-assembly and antimicrobial activity of long-chain amide-functionalized ionic liquids in aqueous solution.

Surface active amide-functionalized ionic liquids (ILs) consisting of a long alkyl chain (C6C14) connected to a polar head group (methylimidazolium or pyridinium cation) via an amide functional group were synthesized and their thermal stability, micellar properties and antimicrobial activity in aqueous solution investigated. The incorporation of an amide group increased the thermal stability of the functionalized ionic liquids compared to simple alkyl chain substituted ionic liquids. The surface activity and aggregation behaviour in aqueous solution of amide-functionalized ionic liquids were examined by tensiometry, conductivity and spectrofluorimetry.

Micellization of sodium laurylethoxysulfate (SLES) and short chain imidazolium ionic liquids in aqueous solution.

In the present study the interactions between an anionic surfactant sodium laurylethoxysulfate (SLES) and three short chain imidazolium (1-butyl-3-methylimidazolium) based ionic liquids (bmim-octyl SO4, bmim-methyl SO4 and bmim-BF4) in aqueous solution have been investigated. Generally when a surfactant is dissolved in a hydrophilic ionic liquid aqueous solution the critical micelle concentration (cmc) obtained is attributed to the surfactant because the ionic liquid (IL) is considered to be only a cosolvent. However, some short hydrophilic ionic liquids posses surface activity in aqueous solution and behave like a surfactant.

Aggregation behavior and antimicrobial activity of ester-functionalized imidazolium- and pyridinium-based ionic liquids in aqueous solution.

Two series of long chain imidazolium- and pyridinium-based ionic liquids containing an ester functional group in the alkyl side chain, 3-methyl-1-alkyloxycarbonylmethylimidazolium bromides (C(n)EMeImBr) and 1-alkyloxycarbonylmethylpyridinium bromides (C(n)EPyrBr), were synthesized and their thermal stability, aggregation behavior in aqueous medium, and antimicrobial activity investigated. The introduction of an ester group decreased the thermal stability of the functionalized ILs compared to simple alkyl chain containing ILs (1-alkyl-3-methylimidazolium bromides and 1-alkylpyridinium bromides). Tensiometry, conductimetry, and spectrofluorimetry were applied to study the self-aggregation of the amphiphilic ILs in aqueous solution.

Self assembly of pH-sensitive cationic lysine based surfactants.

Three cationic surfactants of the type N(ε)-acyl lysine methyl ester hydrochloride have been studied with respect to solution behavior and adsorption on the air/water interface, as well as the thermolyotropic behavior. The self-assembly of these surfactants, which have the cationic charge on amine protonated groups, was assessed by different physicochemical methods. Depending on the pH value, these surfactants can dissociate in aqueous solutions, losing the cationic charge.

Interaction of nonionic surfactants and hydrophilic ionic liquids in aqueous solutions: can short ionic liquids be more than a solvent?

The interaction between an ethoxylated nonionic surfactant (C(12-14)EO(8)) and three conventional hydrophilic imidazolium-based ionic liquids (bmim-octyl SO(4), bmim-methyl SO(4), and bmim-BF(4)) in aqueous solution has been investigated. In most of the reported studies where a surfactant is dissolved in an ionic liquid aqueous solution, conventional ionic liquids are merely considered to be solvents. Consequently, the resulting critical micelle concentration (cmc) is considered to be that of the surfactant.

Formation of vesicles with an organometallic amphiphile bilayer by supramolecular arrangement of metal carbonyl metallosurfactants.

Metallo-vesicles are formed in water medium as a result of the supramolecular arrangement of molybdenum carbonyl metallosurfactants. These new kind of surfactants contain a hydrophobic metal carbonyl fragment and are easily prepared from surfactant phosphine ligands.

Self-aggregation and antimicrobial activity of imidazolium and pyridinium based ionic liquids in aqueous solution.

Two series of long-chain imidazolium and pyridinium based ionic liquids (1-alkyl-3-methylimidazolium and 1-alkylpyridinium bromides) were synthesised and the effect of the alkyl chain length and the nature of the cationic head group on micellization and antimicrobial activity of the ionic liquids (ILs) were investigated. Tensiometry, conductometry, spectrofluorimetry and PGSE-NMR were applied to study the self-aggregation of the amphiphilic ILs in aqueous solution. The ILs investigated displayed surface activity and the characteristic chain length dependence of the micellization process of surfactants.

New surfactant phosphine ligands and platinum(II) metallosurfactants. Influence of metal coordination on the critical micelle concentration and aggregation properties.

We have prepared the first platinum(II) metallosurfactants from a new family of linear surfactant phosphines Ph(2)P(CH(2))(n)SO(3)Na {1 (n = 2), 2 (n = 6), and 3 (n = 10)}, which were synthesized by reaction between the halosulfonates X(CH(2))(n)SO(3)Na and sodium diphenylphosphide. The metallosurfactants cis-[PtCl(2)L(2)] (L = 1-3) were obtained after reaction between the phosphines and PtCl(2) in dimethylsulfoxide. All compounds were fully characterized by the usual methods {NMR ((1)H, (13)C, (31)P, (195)Pt), IR, MS-ESI and HRMS}.

A monolayer study on interactions of docetaxel with model lipid membranes.

Docetaxel (DCT) is an antineoplastic drug for the treatment of a wide spectrum of cancers. DCT surface properties as well as miscibility studies with l-alpha-dipalmitoyl phosphatidylcholine (DPPC), which constitutes the main component of biological membranes, are comprehensively described in this contribution. Penetration studies have revealed that when DCT is injected under DPPC monolayers compressed to different surface pressures, it penetrates into the lipid monolayer promoting an increase in the surface pressure.

Chemical Modifications on Human Hair Studied by Means of Contact Angle Determination.

Wetting properties of a solid surface can change as a consequence of chemical treatment. There is a relationship between the molecular structure of a surface and the macroscopic properties of this surface such as wetting and adhesion. Information on the surface energy of a solid was obtained by calculating polar and dispersion force contributions by means of contact angle determination.