E.i. Dupont De Nemours and Company

Hercules Corporation

Brent Ryan Gonska

Stephan James McLain

Peter Michael Murphy

Alexander Borisovich Shtarov

Axel Hans-Joachim Herzog

Janice Jianzhao Wang

Hollis Thomas Warren

Ryan Vincent Blazewicz

The invention provides polymers comprising repeating units derived from at least one monomer comprising at least one functionalized or unfunctionalized acryloyl moiety and at least one lactam moiety; at least one monomer comprising at least one sulfonic acid moiety or a salt thereof; and at least one crosslinker. The invention further provides various compositions comprising the polymers. The invention furthermore provides applications of these compositions in various industrial arts, particularly in oilfield operations such as drilling and cementing.

Crosslinked polymers derived from monomers having acryloyl and lactam moieties and sulfonic acid/sulfonate comonomers, compositions thereof, and applications thereof

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. The present invention provides a method of making a polyfluorosulfonamido amine without the production of a bis-sulfonamide by-product by reacting a polyfluoroalkylsulfonic compound with a monoamino amide rather than with a diamine reactant as in previously known methods.

Polyfluorosulfonamido amine and intermediate

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 CF(CF)(CH)I (an iodo-fluoroalkyl) with HS&#x2014;CHCH&#x2014;NH(an aminoalkyl thiol) to make CF(CF)(CH)&#x2014;S&#x2014;CHCH&#x2014;NH(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. 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.

Sulfur containing fluoroalkyl amines and isocyanates

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Wilmington, DE, United States of America

Brent Ryan Gonska