A novel synthesis of SO(3)H type gemini surfactant having semifluoroalkyl group as hydrophobic group.
In this work, novel SO(3)H type Gemini surfactants having semifluoroalkyl group (RfCH(2)CH-: Rf = C(4)F(9), C(6)F(13), C(8)F(17)) as hydrophobic group were successively synthesized by the radical addition of fluoroalkyl to 1,4-pentadiene using fluoroalkyl iodide and AIBN as initiator, and the following thiocyanization (-SCN), conversion to -SH, and oxidation to SO(3)H as hydrophilic group. Similarly, the common 1+1 type semifluoroalkyl surfactants having SO(3)H were synthesized. Surfactant properties of their sodium salts (cmc, gamma(cmc), pC(20), Gamma(cmc), and A) were investigated by measuring surface tension. As expected, the cmc value of Gemini surfactant whose fluoroalkyl is C(4)F(9) was more than one order of magnitude smaller than that of the corresponding 1+1 type. Other properties also showed the excellent efficiency of Gemini structure to reduce the surface tension.
Kawase
Tokuzo
T
Department of Chemistry and Materials Technology, Kyoto Institute of Technology, Sakyo-ku, Kyoto, Japan. kawase@chem.kit.ac.jp
Iidzuka
Jun-ichi
J
Oida
Tatsuo
T
D005459:Fluorides / Q000138:chemical synthesis / Q000737:chemistry*; D057927:Hydrophobic and Hydrophilic Interactions; D008954:Models, Biological; D013461:Sulfur Oxides / Q000737:chemistry*; D013499:Surface Properties; D013501:Surface-Active Agents / Q000138:chemical synthesis* / Q000737:chemistry*
D013461:Sulfur Oxides; D013501:Surface-Active Agents; C011118:sulfur trioxide; D005459:Fluorides