Patent GB-1124538-A (GB)
Title: Novel fluorocarbon derivatives useful as oil-repellency agents
IPC: D06M13/408
Filed: 1966-08-23
Abstract: Cellulosic materials, e.g. cotton, linen, viscose, cuprammonium rayon, saponified cellulose acetate and salts of cellulose xanthate, are rendered oil and water repellant by treatment with a fluorocarbon derivative of the formula RfCONH[CxH2xNZ1]yCxH2x-NHZ, wherein Rf is a C3 to C17 perfluoroalkyl radical; x is an integer from 2 to 6; y is an integer from 1 to 4; Z is hydrogen, an acyl radical RfCO or a vinyl sulphone radical having the formula -CHR1-CHR1-SO2-[-RSO2]nCR1= CHR1 in which R is an alkylene, arylene or aralkylene radical, n is 0 or 1 and R1 is hydrogen or an alkyl, aryl or alkyl-, halo- or nitro-substituted aryl radical; and Z1 is hydrogen, an acyl radical RfCO, a vinyl sulphone radical as defined above or a radical of the formula -CxH2x-NHZ, provided that at least one of Z and Z1 is an acyl radical or Z1 is a radical of the formula -CxH2xNHCORf and that where y is 2 or more Z1 in adjacent groups may be the same or different. When the fluorocarbon derivative contains a vinyl sulphone radical, the cellulosic material may be contacted with the fluorocarbon derivative, optionally in aqueous solution or emulsion or in non-aqueous solution, and a basic catalyst, and reaction effected to produce a chemically cellulosic material.ALSO:Novel fluorocarbon derivatives of the formula <FORM:1124538/C2/1> wherein RF represents a C3-C17 perfluoralkyl radical; x is an integer from 2 to 6; y is an integer from 1 to 4; Z represents a hydrogen atom, an acyl radical RFCO- or a vinyl sulphone radical of the formula -CHR1-CHR1-SO2-(RSO2)n-CR1\h = CHR1 in which R represents an alkylene, arylene or aralkylene radical, n is 0 or 1 and R1 represents a hydrogen atom or an alkyl, aryl or alkyl-, halo-, or nitro-substituted aryl radical; and Z1 represents a hydrogen atom, an acyl radical RFCO-, a vinyl sulphone radical as defined above or a radical of the formula -CxH2x-NHZ; provided that at least one of Z and Z1 is an acyl radical or Z1 is a radical of the formula -CxH2x-NHZ in which Z is an acyl radical and that when y is 2 or more, Z1 in adjacent groups may be the same or different, are prepared by reacting perfluoroalkanoic acids containing 4 to 18 carbon atoms, or lower alkyl esters, acid halides or anhydrides thereof with polyamines of the formula NH2(CxH2x NQ)yCxH2xNH2 wherein Q represents a hydrogen atom or an aminoalkyl radical -CxH2x NH2 and, if desired, reacting the products obtained with vinyl sulphones of the formula CHR1=CR1-SO2-(RSO2)n-CR1 =CHR1.  The compounds have oil and water repellency properties (see Divisions B2, C3 and D1).ALSO:A composition for coating surfaces, e.g. of wood, plastics, glass, paper, metal or textile fibres or fabrics, to impart oil and water repellancy thereto, contains one or more fluorocarbon derivatives of the formula RfCONH (CxH2xNZ1)yCxH2xNHZ wherein Rf is a C3 to C17 perfluoroalkyl radical; x is an integer from 2 to 6; v is an integar from 1 to 4; Z is hydrogen, an acyl radical RfCO- or a vinyl sulphone radical of the formula -CHR1-CHR1 SO2(RSO2)nCR1=CHR1 in which R represents an alkylene, arylene or aralkylene radical, n is 0 or 1 and R1 represents hydrogen or an alkyl, aryl or alkyl-, halo- or nitro-substituted aryl radical; and Z1 represents hydrogen, an acyl radical RfCO, a vinyl sulphone radical as defined above or a radical of the formula -CxH2xNHZ, provided that at least one of Z and Z1 is an acyl radical or Z1 is a radical of the formula -CxH2xNHCORf and that when y is 2 or more, Z1 in adjacent groups may be the same or different.  The composition may be in the form of a solution, e.g. in acetone, methyl ethyl ketone, acetonitrile or dimethylformamide, or an aqueous emulsion.  The treated surface may be cured by heating to an elevated temperature.ALSO:A composition for treating textile materials (fabrics and fibres), e.g. cotton, nylon, wool, polyethylene terephthalate or polyacrylonitrile, to impart oil and water repellency thereto, contains one or more fluorocarbon derivatives of the formula RfCONH(CxH2x-NZ\sv)nCxH2x NHZ wherein Rf is a C3 to C17 perfluoroalkyl radical; x is an integer from 2 to 6; y is an integer from 1 to 4; Z is hydrogen, an acyl radical RfCO- or a vinyl sulphone radical having the formula -CHR\sv-CHR\sv-SO2-[RSO2]n-CR\sv=CHR\sv in which R is an alkylene, arylene or aralkylene radical, n is 0 or 1 and R\sv is hydrogen or an alkyl, aryl or alkyl; halo- or nitro-substituted aryl radical; and Z\sv is hydrogen, an acyl radical RfCO-, a vinyl sulphone radical as defined above or a radical of the formula -CxH2xNHZ; provided that at least one of Z and Z\sv is acyl or Z\sv is a radical of the formula -CxH2xNHZ in which Z is acyl and that, when y is 2 or more, Z\sv in adjacent groups may be the same or different.  The composition may be in the form of a solution, e.g. in acetone, methyl ethyl ketone, acetonitrile or dimethylformamide, or an aqueous emulsion and it may also contain auxiliary agents such as those imparting water repellency, crease resistance and softening properties.  The treated material may be cured by heating to an elevated temperature.