Preparation, surface‐active properties, and antimicrobial activities of bis‐quaternary ammonium salts from amines and epichlorohydrin

Abstract

A series of new cationic surfactants, bis-quaternary ammonium salts, were prepared from tert-alkylamine and a product of the reaction of epichlorohydrin with decyl-and dodecylamine, and their surface-active properties were measured. Specifically, the critical micelle concentration (CMC), effectiveness of surface tension reduction (γ CMC ), surface excess concentration (Γ), area per molecule at the interface (A), and standard free energies of adsorption (∆G ads°) and of micellization (∆G mic°) were determined. All these surfactants showed good water solubility and low CMC, more than one order of magnitude lower than those of corresponding monoalkylammonium salts. They also showed good foaming properties but worse wetting capabilities. Many of these compounds had antimicrobial activities against gram-positive bacteria (Staphylococcus aureus, Bacillus subtilis) and yeast (Candida albicans), but they were not active against molds.

Synthesis, Surface-Active Properties, and Antimicrobial Activities of New Double-Chain Gemini Surfactants

“…Thus, diverse articles focused on searching novel geminis with antibacterial and antifungal properties have lately been reported in the literature [11][12][13][14] . Some contributions in this connection involve gemini compounds having new active moieties, such as heteroatoms 15,16) , aromatic and non-aromatic cyclic substituents 17,18) , or perfluorinated chains [19][20][21][22][23] , among others. Nevertheless, it still remains an ample research area for synthesizing improved geminis efficiently and with low cost.…”

Preparation, Surface‐Active Properties and Antimicrobial Activities of Bis(Ester Quaternary Ammonium) Salts

“…Synthesis Bis (ester-ammonium) salts were prepared in two-step reactions as shown in Scheme 1, according to the procedure described in [4,7].…”

“…These salts have shown interesting physical properties such as very low critical micelle concentration, high viscoelasticity, detergency, high solubilization property, good wetting and foaming ability [1][2][3]. They are biologically active toward bacteria, yeasts and moulds [4][5][6]. In addition, these groups of cationic surfactants have excellent antistatic effects [7].…”

Preparation, surface‐active and antielectrostatic properties of multiple quaternary ammonium salts

“…Syntheses of bis-ammonium salts were carried out according to the method described by Chlebicki and colleagues (8).…”

“…They are named dimeric and trimeric ammonium salts, respectively. The dimeric (gemini) salts have been widely investigated and their properties are well known (2)(3)(4)(5)(6)(7)(8). However, trimeric salts that are synthesized in a low yield are investigated to a lesser extent and their surface activity, biological properties, antielectrostatic effect, and other physicochemical properties are poorly known (9)(10)(11).…”