Novel fluorinated gemini surfactants with γ-butyrolactone segments

Journal of Oleo Science
Tokuzo KawaseTatsuo Oida

Abstract

In this work, novel γ-butyrolactone-type monomeric and dimeric (gemini) surfactants with a semifluoroalkyl group [Rf- (CH2)3-; Rf = C4F9, C6F13, C8F17] as the hydrophobic group were successfully synthesized. Dimethyl malonate was dimerized or connected using Br(CH2)sBr (s = 0, 1, 2, 3) to give tetraesters, and they were bis-allylated. Radical addition of fluoroalkyl using Rf-I and an initiator, i.e., 2,2'-azobisisobutyronitrile for C4F9 or di-t-butyl peroxide for C6F13 and C8F17, was perform at high temperature, with prolonged heating, to obtain bis(semifluoroalkyl)-dilactone diesters. These dilactone diesters were hydrolyzed using KOH/EtOH followed by decarboxylation in AcOH to afford γ-butyrolactonetype gemini surfactants. Common 1 + 1 semifluoroalkyl lactone surfactants were synthesized using the same method. Their surfactant properties [critical micelle concentration (CMC), γCMC, pC20, ΓCMC, and AG] were investigated by measuring the surface tension of the γ-hydroxybutyrate form prepared in aqueous tetrabutylammonium hydroxide solution. As expected, the CMC values of the gemini surfactants were more than one order of magnitude smaller than those of the corresponding 1 + 1 surfactants. Other properties also showed the excell...Continue Reading

References

Aug 15, 2000·Angewandte Chemie·F M Menger, J S Keiper
May 25, 2002·Advances in Colloid and Interface Science·Raoul Zana
Jun 22, 2006·Environmental Science & Technology·Magali HoudeDerek C G Muir
Oct 23, 2008·Environmental Science & Technology·Hisao HoriShuzo Kutsuna

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Citations

Feb 20, 2019·Natural Product Research·Gang ChenYuehu Pei
Nov 19, 2019·Journal of Oleo Science·Malik Abdul Rub, Dileep Kumar
Feb 6, 2020·Langmuir : the ACS Journal of Surfaces and Colloids·Wei MaAtsushi Takahara

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