Patent GB-1101049-A (GB)
Title: Unsaturated fluorocarbon esters and polymers thereof
IPC: C07C33/42
Filed: 1966-05-19
Abstract: Compounds of the general formula Rt-CH = CH-(CH2)m-O-CO-(CH2)n -CR = CH2 wherein Rt is a C3- 21 perfluoroalkyl group, R i H or CH3, m is 1-10 and n is 0-10, may be homopolymerized, or copolymerized with other ethylenic monomers such as acrylic and methacrylic acids and esters thereof, vinyl esters of aliphatic acids, styrene and substituted styrenes, halogenated vinyl or vinylidene compounds, allyl esters of aliphatic acids, vinyl alkyl ketones, methacrylamide, acrylamide and N-substituted derivatives thereof, dienes and fluorinated unsaturated esters. The polymerisation may be performed by bulk, emulsion, solution or suspension techniques using free-radical catalysts, such as peroxides, hydroperoxides, peroxy esters, per-salts and azo-compounds, ultraviolet rays or ionizing radiations. Emulsion polymerization is preferred using emulsifiers, such as soaps, sulphates, perfluoroalkanoates, sulphonates, quaternary ammonium salts and ethylene oxide condensates, and the aqueous emulsions resulting from such processes may be employed, either as such or after dilution or concentration and/or the addition of stabilizers, pH adjusters or oil or water-repellent compounds, as compositions for use in rendering solid articles oil- and water-repellent. Other compositions for this purpose may comprise the polymers in organic solvent solutions or in self-pressurized sprayable products.  The polymers are suitable as water- and oil-repellents.ALSO:Aerosol compositions comprise an organic solvent solution of a homopolymer or copolymer containing units of the formula <FORM:1101049/C4-C5/1> wherein RF is a C3- 21 perfluoroalkyl group, R is H or CH31 m is 1-10 and n is 0-10, plus a propellant, such as CHFCl2, CFCl3 or C2F4Cl2.ALSO:The invention comprises compounds of the general formula <FORM:1101049/C2/1> wherein Rf is a C3- 21 perfluoroalkyl group, R is H or CH3, m is 1-10 and n is 0-10. The compounds may be prepared by dehydrohalogenating a compound of the formula RfCH2CHX(CH2)mOH (2) and esterifying the resultant unsaturated alcohol with a compound of the formula CH2=CR(CH2)nCOY (3) or by esterification of the compounds of Formula 2 with the compounds of Formula 3 followed by dehydrohalogenation of the resul ting ester, X being Br or Cl and Y being halogen, -OH and -OR1 where R1 is C1- 5 alkyl.  The following preparations of starting materials and intermediates are described <FORM:1101049/C2/2>ALSO:Woven or knitted fabrics, paper, felt, fibreboard, of cellulose, cotton, wool, polyamides, polyesters, polyacrylonitrile, cellulose acetate, or propionate, leather, glass, and asbestos, are coated with compositions containing homopolymers or copolymers containing units of the formula:  <FORM:1101049/B1-B2/1> where in Rt is a C3-21 perfluoralkyl group, R is H or CH3, m is 1-10 and n is 0-10.  The compositions may be in the form of aqueous emulsions, organic solvent solutions or self-pressurized sprayable products, may contain stabilisers, pH adjusters and/or other water-or oil-repellent compounds and may be applied by painting, dipping or spraying.ALSO:Solid materials may be rendered water- and oil-repellent by the application thereto of compositions containing homopolymers or copolymers containing units of the formula: <FORM:1101049/D1-D2/1> wherein Rt is a C3-21 perfluoroalkyl group, R is H or CH3, m is 1-10 and n is 0-10.  The compositions may be in the form of aqueous emulsions, organic solvent solutions or self-pressurized sprayable products, may contain stabilisers, pH adjusters and/or other water-or oilrepellent compounds and may be applied by painting, dipping or spraying.  The materials treated may be leathers, asbestos, or woven fabrics, knitted fabrics, papers, fibreboards or felts made of natural, semi-synthetic or fully synthetic fibres.