Synthesis, surface active properties and applications of cationic gemini surfactants from triethylenetetramine

Abstract

The 2-Alkyl-1-diethylenediaminimidazoline based Gemini amphiphiles were successfully synthesized in a two step methodology. In the first steps, triethylenetetramine was reacted with fatty acids namely viz. caprylic acid, lauric acid, myristic acid & palmitic acid to get the corresponding amides which on continuous heating results into 2-alkyl-1-diethylenediaminimidazoline. These imidazolines in second step were reacted with 1, 6-dibromohexane to form targeted cationic Gemini surfactants. The chemical structure of compounds was confirmed by means of FTIR, ¹H-NMR and 13C-NMR spectroscopy. The effect of alkyl chain length of synthesized surfactants on the basic characteristics such as surface tension, foaming, emulsifying capability, lime soap dispersing power and wetting were studied. These new surfactants were investigated for their biodegradability, anticorrosion and antimicrobial activity. They have capacity to reduce surface tension of water from 71.8 mN.m⁻¹ to 27.42 mN.m⁻¹. The 2-octyl-1-diethylenediaminimidazoline based Gemini surfactant (GSCTDH) showed good biocidal activity against gram positive Bacteria Bacillis subtilis (16.57 mm) & Staphylococcus aureus (19.46 mm). The 2-dodecyl-1-diethylenediaminimidazoline based Gemini surfactant GSLTDH has good inhibition against gram negative bacteria Pseudomonas aeruginosa (14.33 mm) and Escherichia coli (18.31 mm). The biodegradation results allowed classification of synthesis compounds as readily biodegradable. The Gemini surfactant GSCTDH has 96.71% inhibition efficiency against carbon steel. It can be used as an anticorrosion agent.

Graphical Abstract

Keywords:

• Gemini surfactant
• synthesis
• surface active properties
• antimicrobial activity
• biodegradability
• corrosion inhibition

Acknowledgments

Authors are thankful to University Grants Commission, India [Project F. No. 41-373/2012 (SR)] for providing the research grant and UICT (University Institute of Chemical Technology, NMU, Jalgaon-425001, India) for providing the laboratory facilities for this research work.

Additional information

Notes on contributors

Ishwar T. Gawali

Ishwar T. Gawali has got his master degree M. Sc. (Organic Chemistry) in 2010 from Nabira Mahavidyalaya, Katol, R. T. M. University, Nagpur and M. Tech. (Oleochemical and Surfactant Technology) in 2014 from UICT, NMU, Jalgaon. He is currently working on his Ph. D. degree in the field of surfactant chemistry from UICT, NMU, Jalgaon India. He had presented and published his research papers in several conference and journals.

Ghayas A. Usmani

Ghayas A. Usmani has got his bachelor degree B. Tech. (Chem. Tech.), master degree M. Tech (Oil Tech) and Ph.D. (Oil Tech) from HBTI, Kanpur India. He is currently working as professor and Head, Department of oil Technology, at UICT, NMU, Jalgaon, India. He had completed several research projects. He had presented and published his research papers in several seminars and journals.