New ester based gemini surfactants: the effect of different cationic headgroups on micellization properties and viscosity of aqueous micellar solution

Abstract

A new series of ester functionalized cationic gemini surfactants having different cationic headgroups (i.e. piperidinium, pyrrolidinium, morpholinium and quaternary ammonium) have been synthesized and characterized using NMR and Mass spectroscopy. These new gemini surfactants were investigated for their micellization and viscosity properties using surface tension, conductivity, fluorescence and rheology thechniques. The physicochemical properties of the aqueous surfactant system were influenced by polarity, size and the nature of cationic headgroups as the surface, thermodynamic and viscosity properties of these gemini surfactants were found to be dependent on the type of cationic headgroup. The current research finding establishes the structure-property relationship of the surfactant molecule specifically taking into account the dominant role displayed by the nature of the cationic headgroup.

Synthesis and Characterization of Surface‐Active Ionic Liquids Used in the Disruption of Escherichia Coli Cells

“…These amphiphilic compounds showed a pronounced surface activity, presenting CMC values similar to the homologous series with trimethylammonium head group. Over the years, morpholinium gemini surfactants have also been the focus of deeper research, namely by analysing the influence of both the hydrophobic chain length and spacer on the properties of surface and bulk phase . Regarding the guanidinium cation, the alkylguanidinium chloride series was one of the most studied up to now ,.…”

“…Besides the imidazolium family, other types of SAILs have also been investigated, namely ammonium-, [35][36][37][38] phosphonium-, [23] morpholinium-, [38][39][40][41] and guanidinium-based SAILs. [42][43][44] Brown et al [35] reported a series of IL-based surfactants composed of tetraalkylammonium cations and common surfactant anions (derived from dodecyl sulfate and aerosol-OT) as alternatives to imidazolium-based systems, being claimed as cheaper and environmentally more benign.…”

“…Over the years, morpholinium gemini surfactants have also been the focus of deeper research, namely by analysing the influence of both the hydrophobic chain length and spacer on the properties of surface and bulk phase. [38][39][40] Regarding the guanidinium cation, the alkylguanidinium chloride series was one of the most studied up to now. [42,44] Bouchal et al studied the micellization behavior of alkylguanidinium chlorides containing 10, 12, 14 and 16 carbon atoms in the hydrophobic tail, [43] being these compounds less soluble in water and more surface-active than the analogous alkyltrimethylammonium bromides or chlorides.…”

Novel Ester‐linked Anionic Gemini Surfactant: Synthesis, Surface‐Active Properties and Antimicrobial Study

“…Therefore, readily cleavable gemini surfactants are more suitable for use compared to conventional surfactants. Although many chemists have reported studies of gemini or cleavable surfactants, only limited information is available regarding cleavable gemini surfactants [10][11][12][13][14].…”

Alcohol‐ and Amine‐Tolerant Synthesis of Six‐Membered Cyclic Quaternary Ammonium Salts by Using a Triazine‐Based Reagent

“…Six-membered cyclic quaternary ammoniums alts such as piperidinium, morpholinium, and piperazinium salts have versatile physical and chemical properties anda re used in many fields of science and industry. For example, amphiphilic compounds composed of such ammonium salts and hydrophobic moieties are employed as surfactants to form micelles [1] and also phase-transfer catalysts in biphasic organic-aqueous systems. [2] In addition, piperidinium salts have been studied as potent media for lithium-ion batteries [3] and chemical reactions, [4] as they are liquidso ver aw ide temperature range and have al ow viscosity,h igh thermala nd electrical stability, low hygroscopicity, and wide electrochemical window.M oreover, there are severala nticholinergic agents that consist of rigid six-membered cyclic quaternary ammonium salts.…”