GB1301942A - - Google Patents

Abstract

1301942 Fluoroalkyl sulphonamido alkyl esters NATIONAL STARCH & CHEMICAL CORP 9 July 1970 [11 July 1969] 33351/70 Heading C2C [Also in Divisions C3 and D1] The invention comprises segmented fluoroalkyl sulphonamido alkyl esters of the formula wherein Rf is a radical containing from 3 to 20 carbon atoms inclusive and is selected from straight and branched chain perfluoro alkyl radicals, perfluoro cyclo aliphatic radicals, perfluoro polycyclo aliphatic radicals and straight and branched chain perfluoro alkyl, perfluoro cyclo aliphatic and perfluoro polycyclo aliphatic radicals wherein the perfluoro group is substituted with at least one atom selected from hydrogen, chlorine, bromine and iodine atoms; Z is a radical selected from alkylene, alkenylene, cyclo-alkyl, bridged cycloalkyl, polycycloalkyl, bridged polycycloalkyl and radicals where R<SP>11</SP> is selected from hydrogen atoms, saturated and unsaturated hydrocarbon radicals containing from 1 to 20 carbon atoms, cycloalkyl radicals, bridged cycloalkyl radicals, polycycloalkyl radicals, bridged polycycloalkyl radicals, aryl and aralkyl radicals and n is an integer from 1 to 10, R is a radical selected from hydrogen and alkyl radicals containing from 1-6 carbon atoms, X is a radical selected from straight and branched chain alkylene radidals. corresponding to the formula CmH 2 m where m is an integer from 2 to 14 inclusive, cycloaliphatic radicals, bridged cycloaliphatic radicals, aralkyl radicals, aryl radicals and di-alkylene oxide radicals and R<SP>1</SP> is a radical selected from hydrogen and methyl radicals. The invention also comprises compounds of the formula where Rf, Z, R and X are as defined above. The latter compounds are produced by (a) reacting a segmented fluoroalkyl sulphonyl halide of the formula where Rf and Z are as defined above and Y is chlorine, bromine or iodine, with ammonia, ammonium carbonate or a C 1 -C 6 primary amine to produce a sulphonamide and (b) reacting the latter with an alkylene oxide or omega-haloalcohol in the presence of a base to produce the desired fluoroalkyl sulphonamido hydroxyl compound. Alternatively the sulphonyl halide is reacted with an amino alcohol in the presence of a proton acceptor to produce the desired product. The desired esters are produced by reacting the corresponding fluoroalkyl sulphonyl hydroxyl compounds with acrylic or methacrylic acid or their acid chlorides, or C 1 -C 4 alkyl acrylate or methacrylate esters. Examples are furnished. The esters are converted to homo- and co-polymers (see Division C3).