Preparation and Evaluation of Monodisperse Nonionic Surfactants Based on Fluorine-Containing Dicarbamates

• Published in: Journal of colloid and interface science Vol. 229; no. 2; pp. 440 - 444
• Main Authors: Mureau, Natacha, Trabelsi, Hédi, Guittard, Frédéric, Geribaldi, Serge
• Format: Journal Article
• Language: English
• Published: San Diego, CA Elsevier Inc 15-09-2000; Elsevier
• Subjects: Chemistry; dicarbamate; Exact sciences and technology; General and physical chemistry; malonic compounds; nonionic surfactant; oligooxyethyl surfactant; perfluorinated; Surface physical chemistry; Surface-active agents: properties; nonionic surfactant; dicarbamate; perfluorinated; malonic compounds; oligooxyethyl surfactant; Ethylene oxide polymer; Micellar critical concentration; Non ionic surfactant; Preparation; Bifunctional compound; Surface properties; Fluorine compound; Surface tension; Experimental study; Carbamate
• ISSN: 0021-9797; 1095-7103
• DOI: 10.1006/jcis.2000.7037

Novel bipodal surfactants of fluorine-containing carbamate type were synthesized with satisfactory yields from the action of fluorinated diisocyanates on oligooxyethylmonomethylated ethers without solvent. The synthetic pathways via malonic intermediates were elaborated in order to use low-price commercially available compounds such as 2-F-alkylethyl iodides and oligooxyethylmonomethylated ethers as starting materials. This new class of nonionic surfactants contains one hydrophobic part and one oleophobic part, and shows peculiar properties due to the presence of two hydrophilic parts (bipodal). All these compounds are monodisperse, i.e, include a perfectly defined number of oxyethylene units. Compared with their bipodal homologues previously described within the F-alkylated series, these new structures were easily obtained from commercial raw materials and are stable against pH media. The evaluation of their behavior at the air–water interface has been studied by measurements of surface tension versus concentration. This allows us to show clearly the variation of the critical micelle concentration (cmc) from 1.1×10−5 to 9.8×10−3 mol·l−1, and of the surface area per surfactant molecule versus studied structures. The dicarbamates of oligooxyethylmonomethylether of 3-(F-alkyl)propyl so realized exhibit noteworthy properties as nonionic fluorinated surfactants.