Synthesis of Highly Fluorinated Aryl N-Acylsulfamates and Evaluation of Their Surfactant Properties

Abstract

Reaction of highly fluorinated carboxylic acids with aroxysulfonylisocyanates in the presence of triethylamine allowed the preparation of the corresponding highly fluorinated aroxy-N-sulfonylsulfamates. The reaction proceeds with good yield in toluene at room temperature or more rapidly in the same solvent at 60 °C. Surface tension measurement at the air/water interface showed that these compounds constitute new excellent nonionic surfactants exhibiting high surface activity in the range of the best nonionic fluoro surfactants, already described in the literature. The critical micelle concentration (CMC) has been calculated from the surface tension measurements on surface aqueous solutions.

GRAPHICAL ABSTRACT

Keywords:

• Highly fluorinated carboxylic acids
• aroxysulfonylisocyanates
• highly fluorinated N-acylsulfamates
• surface tension
• critical micelle concentration