Patent GB-1093415-A (GB)
Title: Perfluoralkyl-substituted compounds
IPC: D06M13/395
Filed: 1964-12-01
Abstract: Aqueous emulsions for proofing fibrous materials comprise a fluorinated product obtained by reacting a polyisocyanate, a sulphonamide and a compound containing a hydroxyl, carboxyl, amide or amino group, and an emulsifying agent which is an aqueous solution of a polyvinyl alcohol, which may be acylated or acetalized, or an aqueous solution or dispersion of an epoxy resin which is the neutralized or acidified reaction product of an epoxy compound and a polyamine, which epoxy resin may be further condensed with a C1- 3 mono- or dialdehyde The proofing emulsions may include melamine resins which impart a crease-resistant finish to the substrate. Examples 14-18 describe compositions containing epoxide resins derived from ethylene diamine or diethylenetriamine and the glycide ethers of 2,2-bis-(p-hydroxyphenyl) propane or ethylene glycol; in Example 16 the epoxy resin is condensed with formaldehyde.  Examples 19-21 relate to compositions including polyvinyl alcohol and partially acetalized polyvinyl alcohol.  Examples 16, 17, 19 and 21 describe emulsions containing resins derived from dimethylolethylene urea and hexamethylolmelamine; tetramethylol melamine and trimethylol melamine.ALSO:Perfluoroalkyl compounds containing free isocyanate groups are prepared by heating at at least 110 DEG  C. an aromatic, alicyclic or aliphatic di- or tri-isocyanate with a compound of the formula RfSO2NRR1, where Rf is a perfluoroalkyl group of at least 4 carbon atoms, R is hydrogen or an alkyl group having less than 7 carbon atoms, and R1 is hydrogen or a C2- 5 o -hydroxyalkyl group, and a compound of the formula R11X where R11 is an aliphatic hydrocarbon group of more than 12 carbon atoms and X represents a hydroxyl, carboxyl, carboxylic acid amine or amino group, the compounds being used in the proportions of 1 mol. isocyanate to 0.3-0.6 mol. per isocyanate group of RfSO2NRR1 and 0.1-0.5 mol. per isocyanate group of R11X, the total molar amount of compounds R+SO2NRR1 and R11X per mol. isocyanate being less than 1 per isocyanate group.  Specified isocyanates include tolylene diisocyanate, diphenylmethane - p,p1 - diisocyanate, triphenylmethane - p,p1,p11 - triisocyanate, hexamethylene diisocyanate, methyl cyclohexenyl diisocyanate and thiophosphoric acid-tris-(4-isocyanatophenyl)-esters. Preferred compounds of the formula R11X are C16- 18 straight chain alcohols.  The preferred sulphonamides are those in which R is a methyl or ethyl group and R1 is a b -hydroxyethyl group.ALSO:Fibrous materials are rendered oil- and water-repellent by treatment with a perfluoroalkyl compound containing free isocyanate groups obtained by reacting at a temperature of at least 110 DEG C (a) an aromatic, alicyclic or aliphatic di- or tri-isocyanate, (b) a sulphonamide RfSO2NRR\sv where Rf is a perfluoroalkyl group having at least 4 carbon atoms, R is hydrogen or a C1-5 alkyl group and R\sv is hydrogen or a C2-5 co-hydroxyalkyl group and (c) a compound R\yFX wherein R\yF is an aliphatic hydrocarbon group of more than 12 carbon atoms and X represents a hydroxyl, carboxyl, carboxlic acid amide or amino group, the compounds being reacted in the proportions of 1 mol isocyanate to 0.3-0.6 mol, per isocyanate p  group, of RfSO2NRR\sv, to 0.1-0.5 mol, per isocyanate group, of R\yFX; the total amount of RfSO2NRR\sv and R\yFX per mol isocyanate group being less than 1.  The fluorinated compounds may be applied as an organic solution or, preferably, as an aqueous emulsion using polyvinyl alcohol, or a derivative thereof, or an epoxide, polyamine and/or aldehyde condensation resin as emulsifying agents.  The treated materials may be cured at elevated temperatures.  The oil- and water-proofing treatment may be combined with other textile finishing processes, e.g. crease-resisting processes using a melamine resin.  Examples 12-21 describe the treatment of a variety of fabrics.