Patent GB-1096392-A (GB)
Title: Mixed esters of dihydric alcohols with perfluoroalkanoic acid ethylenically unsaturated carboxylic acids
Inventor: EYGEN CYRILLE VAN
IPC: C04B41/48
Filed: 1965-07-07
Abstract: Addition polymers are obtain by polymerizing novel esters of the formula R1COO-Y-OOCR11 wherein R1COO is a perfluoroalkanoic acid residue, R11COO is a residue of a polymerisable alkenoic acid and Y is a residue of an aliphatic, alphatic-aromatic or aromatic dihydric alcohol, the carbon chain of which may be interrupted by oxygen atoms.  The polymers may be homopolymers or co-polymers with each other or with other co-polymerisable monomers, e.g. acrylic derivatives, vinyl derivatives or allyl derivatives, and may be produced in organic solution or aqueous emulsion, in the presence of polymerization catalysts e.g. organic and inorganic peroxides, hydroperoxides, per salts, diazo compounds or redox systems.  The polymers are useful for treating any porous or non-porous material in order to protect it from dirt or to make it resistant to wetting by oil or grease (see Division D1).  In examples, the preparation is described of homopolymers of ethylene glycol acrylate perfluoro-octanoate and ethylene glycol methacrylate perfluoro-octanoate, of a copolymer of 2,2 - dimethyl - propane - 1,3 - diol methacrylate perfluoro-octanoate and N-methylol-acrylamide and of a block polymer of 2,2-dimethyl-propane-1,3-diol methacrylate perfluoro-octanoate, 2-ethyl-hexyl acrylate and N-methylol-acrylamide.ALSO:Novel esters of the formula R1COO-Y-OOCR11 wherein R1COO is a perfluoroalkanoic acid residue, R11COO is a residue of a polymerizable alkenoic acid and Y is a residue of an aliphatic aliphatic-aromatic or aromatic dihydric alcohol, the carbon chain of which may be interrupted by oxygen atoms, are prepared by reacting glycol monoesters of alkenoic acids, R11COO.Y.OH, with perfluoroalkenoic acids R1COOH, or their acid halides.  The esters and their addition polymers (see Division C3) are useful for treating any porous or non-porous material in order to protect it from dirt or to make it resistant to wetting by oil or grease.  2,2 - Dimethyl - propane - 1,3 - diol monomethacrylate, 2 - methyl - 2 - propyl - propane - 1,3-diol monomethacrylate and 2,2-diethyl-propane-1,3-diol monomethacrylate, used as starting materials, are prepared by reacting methacrylyl chloride with the appropriate diols.ALSO:Textile materials, e.g. natural and synthetic fibres, paper, wood, brick, asbestos, asbestos cement, concrete, leather and hides, are given oleophobic properties by treatment with a polymer derived from a fluorine-containing monomer of the formula R1COOYOOCR11 wherein R1COO is a perfluoroalkanoic acid residue; R11COO is a residue of a polymerisable alkenoic acid; and Y is a residue of an aliphatic, aliphatic-aromatic or aromatic dihydric alcohol, the carbon chain of which may be interrupted by oxygen atoms.  The polymers, which may be homopolymers or co-polymers with each other or with other monomers, e.g. acrylic, vinyl or allyl derivatives, may be applied in the form of a solution in an organic solvent or as an aqueous emulsion, a specified emulsifying agent being trimethyl octadecyl ammonium chloride.