Simple Synthesis of a Library of Zwitterionic Surfactants via Michael-Type Addition of Methacrylate and Alkane Thiol Compounds

Simple Synthesis of a Library of Zwitterionic Surfactants via Michael-Type Addition of Methacrylate and Alkane Thiol Compounds

A library of zwitterionic phosphorylcholine surfactants with various alkyl chain lengths and compositions was readily prepared from a combination of 2-(methacryloyloxy)ethyl phosphorylcholine (MPC) and various alkanethiol compounds via Michael-type addition. The critical micelle concentration (CMC)...

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Veröffentlicht in:Langmuir 2010-08, Vol.26 (16), p.13028-13032
Hauptverfasser: Matsuno, Ryosuke, Takami, Kimiaki, Ishihara, Kazuhiko
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Sprache:eng
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Alkanes - chemistry
Magnetic Resonance Spectroscopy
Methacrylates - chemistry
Models, Chemical
Sulfhydryl Compounds - chemistry
Surface-Active Agents - chemical synthesis
Surface-Active Agents - chemistry
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container_issue 16
container_start_page 13028
container_title Langmuir
container_volume 26
creator Matsuno, Ryosuke
Takami, Kimiaki
Ishihara, Kazuhiko
description A library of zwitterionic phosphorylcholine surfactants with various alkyl chain lengths and compositions was readily prepared from a combination of 2-(methacryloyloxy)ethyl phosphorylcholine (MPC) and various alkanethiol compounds via Michael-type addition. The critical micelle concentration (CMC) was evaluated by surface tensiometry. At the CMC, the surface tension of these aqueous solutions decreased significantly to below 40 mN/m. For the zwitterionic surfactants composed of MPC, and fluoroalkane and alkanedithiol, the surface tension was approximately 24, and 50 mN/m, respectively. From the equation log (CMC) = A − Bn, where n is the number of carbon atoms in the alkyl chain, A and B were calculated as 1.09 and 0.44, respectively. The value of the slope B was between that of ionic (B = 0.30) and nonionic surfactants (B = 0.50). Despite the ionic nature of the surfactants, their behavior was closer to that of nonionic surfactants.
doi_str_mv 10.1021/la1015466
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subjects Alkanes - chemistry
Magnetic Resonance Spectroscopy
Methacrylates - chemistry
Models, Chemical
Sulfhydryl Compounds - chemistry
Surface-Active Agents - chemical synthesis
Surface-Active Agents - chemistry
title Simple Synthesis of a Library of Zwitterionic Surfactants via Michael-Type Addition of Methacrylate and Alkane Thiol Compounds
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