Patent GB-999795-A (GB)
Title: Fluorocarbon compounds
IPC: D21H17/11
Filed: 1961-09-04
Abstract: The invention comprises adducts obtained by reacting an organic isocyanate and a sulphonamide containing a perfluoroalkyl terminal group having at least 4 carbon atoms and containing active hydrogen, the isocyanate being substantially free of acid, alcohol, amine, unsubstituted amide, ethylene and carboxylic ester groups.  A preferred class of compounds is represented by the formula R[N(R1)SO2X]2 where R is an organic radical linked to the nitrogen atom via a carbon atom and contains a group derived from the isocyanate such as a urethane, a urea, a ureide or a mixed anhydride of carbamic acid, R1 is an alkyl radical containing less than 20 carbon atoms, and X is an organic radical containing a perfluoroalkyl grouo of the formula -(CF2)3- 17CF3. Suitable examples of fluorinated sulphonamides and isocyanates are given.  In addition, a third compound containing reactive hydrogen but which does not contain a perfluoroalkyl group may also be present during the reaction. Examples given are alcohols, amines and acids.  In detailed examples, urethanes or carbamic acid mixed anhydrides are made by reacting polyisocyanates with perfluoralkylsulphonamide-containing alcohols or acids. Specification 832,490 is referred to.ALSO:A process for imparting oil repellancy to a substrate comprises applying to the outer surface of said substrate an adduct obtained by reacting an organic isocyanate and a compound containing a sulphonamide group, a perfluoroalkyl terminal group having at least 4 carbon atoms, and a group containing an active hydrogen, for example an acid, alcohol, amine or amide group, with or without another compound containing a reactive hydrogen atom which does not contain a perfluoroalkyl group. The preferred adducts thus contain a urethane, urea, ureide or mixed anhydride of carbamic acid in addition to a sulphonamide and perfluoroalkyl group.  The adducts may be applied by known methods of coating, such as spraying, roll coating, brushing or dipping from an organc solvent, solution or anionic, cationic or non-ionic emulsion. In treatment of textile fabrics the adducts may be employed in combination with crease resisting resin, e.g. urea-formaldehyde, ethylene urea-formaldehyde, melamine-formaldehyde, triazine-formaldehyde, and triazone-formaldehyde resins, epoxy resins, and polyglycol acetals; sizes, e.g. polyethylene glycols, polyethylene, dimethyl polysiloxanes, amines and amides derived from fatty acids and ethylene oxide; water repellants, e.g. waxes, polyvalent metal salts of fatty acids, silicone resins, chromium complexes of fatty acids, N-alkyl amidomethyl pyridinium salts, and melamine-formaldehyde resin condensates with amides from fatty acids. In the treatment of paper the adduct may be present in a wax, starch, casein, elastomer or wet strength resin formulation.  The adduct may be mixed in an aqueous or oil type paint formulation and applied to unpainted asbestos siding, wood, metal and masonry.  In the treatment of floors and tile surfaces the adducts may be incorporated in a based emulsion or solution. Illustrative articles to be treated are papers, textiles, glass, wood, leather, fur, asbestos, bricks, concrete, metals, ceramics, plastics, painted surfaces, sponges, and plaster.  Illustrative papers are carbonizing tissue, wallpaper, asphalt laminates, liner board, cardboard and papers derived from synthetic fibres. Illustrative textiles are those based on cotton, wool, mohair, linen, jute, silk, ramie, sisal kenaf, rayon, acrylics, polyesters, "Saran" (Registered Trade Mark), azylon, nytril, nylon, spandex, vinal, reevon, vinyon, and glass fibres.  Detailed examples are given.ALSO:Textiles and leather are made oil-repellent by impreganting with an adduct obtained by reacting an organic isocyanate and a compound containing a sulphonamide group, a perfluoroalkyl terminal group having at least 4 carbon atoms, and a group containing an active hydrogen atom, with or without another compound containing a reactive hydrogen atom which does not contain a perfluoroalkyl group.  In examples, compounds made from totylene isocyanate and <FORM:0999795/D1-D2/1> are used to impregnate cloth and suede leather.