Abstract: Current methods for making polyfluorosulfonamido amines, which involve the use of a diamine reactant, provide low yields and produce an undesirable fluorine containing bis-sulfonamide by-product representing an economic loss. The bis-sulfonamide by-product is particularly undesirable because it shares very similar physical properties with the desired monoamine product thus making isolation of the desired polyfluorosulfonamido amine product difficult and costly. Furthermore, instead of the efficient incorporation of fluorine to make the desired polyfluorosulfonamido amine product, the bis-sulfonamide by-product constitutes a substantial loss of costly fluorinated starting material. The bis-sulfonamide by-product also constitutes an undesirable impurity that can worsen surfactancy, repellency, or other performance characteristics of the desired polyfluorosulfonamido amine product.

Abstract: The present invention provides a method of making sulfur containing fluoroalkyl amines which overcomes the problems of previously known methods. Sulfur containing fluoroalkyl amines are useful as intermediates for compounds which are in turn useful for imparting water and oil repellency to textiles. Sulfur containing fluoroalkyl amines used in this manner may be found in Example 8 of Rondestvedt et al. (U.S. Pat. No. 3,655,732) wherein they are made by reacting an iodo-fluoroalkyl with an aminoalkyl thiol. Specifically, Rondestvedt et al. teaches reacting CF3(CF2)5(CH2)2I (an iodo-fluoroalkyl) with HS—CH2CH2—NH2 (an aminoalkyl thiol) to make CF3(CF2)5(CH2)2—S—CH2CH2—NH2 (a sulfur containing fluoroalkyl amine). Unlike previously known methods, the method of the present invention can achieve higher yields of sulfur containing fluoroalkyl amines without resorting to costly solvents.

Abstract: Current methods for making polyfluorosulfonamido amines, which involve the use of a diamine reactant, provide low yields and produce an undesirable fluorine containing bis-sulfonamide by-product representing an economic loss. The bis-sulfonamide by-product is particularly undesirable because it shares very similar physical properties with the desired monoamine product thus making isolation of the desired polyfluorosulfonamido amine product difficult and costly. Furthermore, instead of the efficient incorporation of fluorine to make the desired polyfluorosulfonamido amine product, the bis-sulfonamide by-product constitutes a substantial loss of costly fluorinated starting material. The bis-sulfonamide by-product also constitutes an undesirable impurity that can worsen surfactancy, repellency, or other performance characteristics of the desired polyfluorosulfonamido amine product.

Abstract: The present invention provides a method of making sulfur containing fluoroalkyl amines which overcomes the problems previously known methods. Unlike previously known methods, the method of the present invention can achieve higher yields of sulfur containing fluoroalkyl amines without resorting to costly solvents. Furthermore, unlike previously known methods, the method of the present invention can produce oxidized forms of sulfur containing fluoroalkyl amines wherein the sulfur atom thereof is oxidized.