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Synthesis and Characterization of Biodegradable Cationic Esterquat Surfactants and the Evaluation of its Physico-Chemical Properties

  • Manickam Janarthana Umapathy , Venu Lakshimi Narayanan , P. Magesan , P. Chiranjeevi and Susan W. Jemima
Published/Copyright: May 9, 2016
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Abstract

Three biodegradable cationic esterquat surfactants such as 2-(dodecanoyloxy)-N,N-bis(2-hydroxyethyl)-N-(oxiran-2-ylmethyl)ethane-1-ammonium chloride (II-a), 2-hydroxy-N-(2-hydroxyethyl)-N-(oxiran-2-ylmethyl)-N-(2-(tetradecanoyloxy) ethyl) ethane-1-ammonium chloride (II-b) and 2-hydroxy-N-(2-hydroxyethyl)-N-(oxiran-2-ylmethyl)-N-palmitoyloxy) ethyl) ethane-1-ammonium chloride (II-c) have been synthesized. The synthesis involves the esterification of three different fatty acids (lauric, myristic and palmitic) with triethanolamine followed by the quaternization with epichlorohydrin. The synthesized surfactants have been characterized by FT-IR, 1H NMR, 13C NMR, and elementary analysis. Physico-chemical properties such as surface tension and interfacial tension, Critical Micelle Concentration (CMC), wetting time, foam stability, and emulsion stability have been evaluated. Based on the results of the physico-chemical properties, the efficacy of the surfactants is in the following order II-c > II-b > II-a.

Kurzfassung

Drei biologisch abbaubare Esterquattenside (2-(Dodecanoyloxy)-N,N-bis(2-hydroxyethyl)-N-(oxiran-2-ylmethyl)ethane-1-ammoniumchloride (II-a), 2-Hydroxy-N-(2-hydroxyethyl)-N-(oxiran-2-ylmethyl)-N-(2-(tetradecanoyloxy)ethyl)ethane-1-ammoniumchlorid (II-b) und 2-Hy-droxy-N-(2-hydroxyethyl)-N-(oxiran-2-ylmethyl)-N-palmitoyloxy)ethyl)ethane-1-ammoniumchlorid (II-c)) wurden synthetisiert. Drei verschiedene Fettsäuren (Laurin-, Myristin- und Palmitinsäure) wurden verestert; anschließend erfolgte eine Quaternisierung mit Epichlorhydrin. Die synthetisierten Tenside wurden mittels FT-IR, 1H NMR, 13C NMR und der Elementaranalyse charakterisiert. Die physico-chemischen Eigenschaften wie die Oberflächen- und Grenzflächenspannung, die kritische Mizellenkonzentration (CMC), die Benetzungszeit, die Schaum- und Emulsionsstabilität wurden bestimmt. Auf Basis der Ergebnisse ergab sich für die Wirksamkeit der Tenside die Reihenfolge II-c > II-b > II-a.


*Correspondence address Prof. Manickam Janarthanan Umapathy, Department of Chemistry, College of Engineering Guindy, Anna University, Chennai, India. E-Mail:

Dr. M. J. Umpathy, Ph. D., (corresponding author), Assistant Professor (S. Gr), Department of Chemistry, College of Engineering Guindy, Anna University, Chennai-25.

V. Lakshmi Narayanan, M. Sc. M. Phil., Research Scholar, Department of Chemistry, College of Engineering Guindy, Anna University, Chennai-25.

P. Magesan, M. Sc. M. Phil., Research Scholar, Department of Chemistry, College of Engineering Guindy, Anna University, Chennai-25.

P. Chiranjeevi, M. Sc., Research Scholar, Department of Chemistry, College of Engineering Guindy, Anna University, Chennai-25.

W. Susan Jemima, M. Sc., Research Scholar, Department of Chemistry, College of Engineering Guindy, Anna University, nnai-25.


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Received: 2014-12-23
Accepted: 2016-01-15
Published Online: 2016-05-09
Published in Print: 2016-05-17

© 2016, Carl Hanser Publisher, Munich

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