Synthesis, Surface Active Properties of Novel Gemini Surfactants with Amide Groups and Rigid Spacers

Abstract

A series of novel cationic gemini surfactants, bis‐(N‐(3‐alkylamido‐propyl)‐N,N‐dimethyl)‐p‐phenylenediammonium dichloride, were synthesized. The structures of the gemini surfactants were characterized by IR, 1H NMR and 13C NMR. The Krafft temperatures of surfactants were determined through conductivity, the surface active properties in aqueous solution were studied at various temperatures by surface tension and conductivity. The thermodynamic functions of micellization process of the surfactants were also calculated by conductivity. The Krafft temperatures of the surfactants were 12, 13 and 28 °C. The values of CMC and Γmax decreased with increasing the length of hydrophobic chains, but the values of CMC and α increased with increasing temperature. The process of micellization is a spontaneous, exothermic and entropy‐driven process.

Self-Assembly Properties of Cationic Gemini Surfactants with Biodegradable Groups in the Spacer

“…Ester-based gemini surfactants also show potent biological activity such as antimicrobial activity and cytotoxicity [20,21]. Research interest is also devoted to cleavable gemini surfactants bearing amide groups which are located either in the gemini spacer [23,24] or are part of hydrocarbon tails [25,26,27]. Synthesis and physicochemical investigations of novel cationic gemini surfactants with diamide spacers are reported [23,24].…”

Preparation, Characterization and Properties of Novel Cationic Gemini Surfactants with Rigid Amido Spacer Groups

“…Recently, gemini surfactants with different types of spacers have been developed with different physical and chemical properties [15][16][17]. Zhu et al [15] prepared four anionic gemini surfactants with long rigid or semi-rigid spacers, and found that all these gemini surfactants showed lower CMC and C 20 values, and that gemini surfactants with rigid spacers preferred to form vesicles.…”

“…This was the first report of sponge-like aggregates in the cationic gemini surfactant-water binary system which was probably caused by adhesion and fusion of vesicles at high surfactant concentration. Hu et al [17] synthesized a class of quaternary ammonium salt gemini surfactants with para-xylene as a rigid spacer. These gemini surfactants possessed high surface activity.…”

Synthesis and Properties of N‐Alkyl–N,N‐Dimethyl‐N‐(o‐Hydroxymethyl)Benzylammonium Chlorides

“…As expected, increasing the length of hydrophobic chain, the values of CMC decreased for DHBA-m resulting from the reinforcing of the hydrophobic interaction among amphiphilic molecules. The saturated adsorption (C max ) of DHBA-m decreased, yet the area of per molecular adsorption (A min ) increased along with the length of alkyl chain from 12 to 18, which likely originates from the longer hydrophobic chain tending to curl, thus increasing the A min values [30].…”