Simple synthesis of a library of zwitterionic surfactants via michael-type addition of methacrylate and alkane thiol compounds

Ryosuke Matsuno, Kimiaki Takami, Kazuhiko Ishihara

Research output: Contribution to journalArticlepeer-review

30 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)13028-13032
Number of pages5
JournalLangmuir
Volume26
Issue number16
DOIs
Publication statusPublished - Aug 17 2010
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Materials Science(all)
  • Condensed Matter Physics
  • Surfaces and Interfaces
  • Spectroscopy
  • Electrochemistry

Fingerprint Dive into the research topics of 'Simple synthesis of a library of zwitterionic surfactants via michael-type addition of methacrylate and alkane thiol compounds'. Together they form a unique fingerprint.

Cite this