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Synthesis and Characterization of Novel Surfactants: Combination Products of Fatty Acids, Hydroxycarboxylic Acids and Alcohols
Author(s) -
Altenbach HansJosef,
Ihizane Rachid,
Jakob Bernd,
Lange Karsten,
Schneider Manfred,
Yilmaz Zeynep,
Nandi Sukhendu
Publication year - 2010
Publication title -
journal of surfactants and detergents
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.349
H-Index - 48
eISSN - 1558-9293
pISSN - 1097-3958
DOI - 10.1007/s11743-010-1185-8
Subject(s) - chemistry , triethylene glycol , organic chemistry , nucleophile , yield (engineering) , electrophile , polyol , tartaric acid , diethylene glycol , ether , citric acid , fatty acid , catalysis , ethylene glycol , polyurethane , materials science , metallurgy
Abstract The reaction of hydroxycarboxylic acids, such as citric, malic and tartaric species with an excess of fatty acid chlorides produces the corresponding O ‐acylated hydroxycarboxylic anhydrides in one step and in a near quantitative yield. These molecules are excellent electrophiles which react readily with a variety of nucleophiles including alcohols, diols and polyols. Their reaction with triethylene glycol and triethylene glycol monomethyl ether leads to two series of novel anionic surfactants, which are unsymmetrical gemini surfactants. The determination of their properties (CMC, foaming, HLB) revealed that these molecules are—depending on the chain length of the fatty acid—excellent emulsifiers, and that they also display interesting antimicrobial activity. These novel functional surfactants are of interest for applications in food and personal care products and for the formulation of pharmaceuticals.