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

Abstract

A novel anionic gemini surfactant containing an ester bond in the spacer group was synthesized using cardanol as the raw material and characterized by IR, 1H NMR and 13C NMR. The surface properties of the gemini surfactant were investigated and compared with its corresponding single chain surfactant counterpart. It was found that this novel gemini surfactant exhibited a low critical micelle concentration value (1.9 mM) and good efficiency in reducing surface tension of water (33.6 mN/m). The gemini surfactant was found to have antimicrobial activity against Gram‐negative (Escherichia coli and Pseudomonas aeruginosa), Gram‐positive (Bacillus subtilis and Staphylococcus aureus) bacteria and fungi (Aspergillus niger, Aspergillus flavus, Candida albicans and Rhizopus stolonifer). The gemini as well as the corresponding single chain surfactant showed good antimicrobial activity against all pathogenic microorganisms studied and can be employed as an antimicrobial agent. The synthesized novel anionic gemini surfactant possesses an excellent wettability and low foamability.

Gemini Surfactants Virtual Issue

“…Cytotoxicity can be regulated by adjusting the spacer chain length. Ahire and Bhagwat () have seen similar antibacterial properties from anionic Gemini surfactants containing ester bonds in the spacer group. The Gemini surfactants also show excellent wettability and low foamability.…”

Synthesis, Surface Activity, and Antimicrobial Efficacy of Hydrogenated Cardanol‐Derived Positively Charged Asymmetric Gemini Surfactants

“…Furthermore, the maximum surface excess concentration τ max (μmol m −2 ) as well as the minimum surface area per molecule A min (nm 2 ) were calculated via the Gibb's adsorption isotherm equation (Rosen and Kunjappu, ): where N A denotes Avogadro's number, R means universal gas constant, T is the absolute temperature, C indicates the surfactant concentration, and (∂γ/ ∂ ln C ) T is the premicellar slope in the surface tension isotherm (Chauhan et al, ). n was set as 2 for C‐BP and 3 for the rest of the compounds based on the number of species formed after the dissolution of the test surfactant (Ahire and Bhagwat, ). CMC, γ CMC , π CMC , C 20 , CMC/C 20 , τ max , and A min values are listed in Table .…”

“…The meta ‐substituted long alkyl chain with odd‐numbered carbon atoms has brought cardanol with intrinsic hydrophobicity and amphiphilicity. And, various types of derivatization on the phenolic –OH group or aromatic ring have contributed to a vast library of cardanol‐based anionic surfactants (Ahire and Bhagwat, ; Bruce et al, ; Castro Dantas et al, ; Kattimuttathu et al, ; Peungjitton et al, ; Scorzza et al, ), nonionic surfactants (Atta et al, ; Tyman and Bruce, , ), and cationic amphiphilic compounds (Bhadani et al, ; Ezzat et al, ; Wang et al, ).…”

Polyoxazoline associated with cardanol for bio‐based linear alkyl benzene surfactants

“…The pre‐factor m is dependent on the surfactant type and structure, as well as the presence of extra electrolyte in the aqueous phase . For nonionic and zwitterionic surfactants, a value of 1 for the pre‐factor has been confirmed . The size of micelles in aqueous medium was measured with a Zetasizer Nano‐ZS (Malvern Instrument Ltd, UK) equipped with a He–Ne laser ( λ = 632.8 nm).…”

“…Otherwise, the synthesis of tertiary, secondary and primary amines has been reported and applied in the area of the organo‐modification of clays where they revealed a good efficiency in exfoliation and for the compatibilization with thermoset resins . Finally, some peculiar architectures based on cardanol such as gemini and betaine surfactants should be reported …”