Patent GB-1121905-A (GB)
Title: Chelate-forming polyfluorinated ketones, alcohols and esters
IPC: C07C49/167
Filed: 1965-08-04
Abstract: The invention comprises compounds of the general formulae <FORM:1121905/C2/1> <FORM:1121905/C2/2> <FORM:1121905/C2/3> <FORM:1121905/C2/4> <FORM:1121905/C2/5> <FORM:1121905/C2/6> <FORM:1121905/C2/7> <FORM:1121905/C2/8> and chelates thereof with Ti, Zr, Al, Sn and Zn, wherein X is F, Cl or H, R1 and R4 are alkyl, fluoroalkyl, aryl, aralkyl, or alkaryl, R2 is alkyl, fluoroalkyl, aryl, aralkyl, alkaryl, OH, alkoxy, aroxy, aralkoxy or alkaroxy, R3 is H, C1- 5 alkyl, aralkyl or aryl, n is 1-25, m is 1-6, and p is 0-4.  The compounds may be prepared by (a) reacting a compound CF2X(CF2)nI with a compound of the formula <FORM:1121905/C2/9> <FORM:1121905/C2/100> <FORM:1121905/C2/111> <FORM:1121905/C2/122> followed by conversion of the iodine substituent to hydrogen by exchange or reduction, or by dehydro-iodination of the product; (b) (when n is 5-25) reacting a compound of the formula CF2X(CF2)nCH=CH-CH2Y, CF2X(CF2)nCH2CH2Y or CF2X(CF2)nCH2I wherein X is F, Cl or H, and Y is Cl, Br or I, with the appropriate alkali metal-b -diketone, alkali metal-b -ketocarboxylic acid or derivative thereof, and, if desired, reducing the product to the corresponding b -glycol; (c) (for compounds of the 1st and 3rd formulae above) reacting the corresponding fluoralkyl metallic compound with the corresponding a -halo-b -diketone, g -halo-b -diketone, a -halo-b -ketocarboxylic acid or g  - halo - b  - ketocarboxylic acid.  The chelates may be obtained by mixing the organic chelating agent with an alcoholate of the metal in an organic solvent.ALSO:Chelates of Ti, Zr, Al, Sn and Zn with compounds of the formulae <FORM:1121905/B1-B2/1> wherein X is F, Cl or H, R1 and R4 are alkyl, fluoroalkyl, aryl, aralkyl or alkaryl, R2 is alkyl, fluoralkyl, aryl, aralkyl, alkaryl, OH, alkoxy, aroxy, aralkoxy or alkaroxy, R3 is H, C alkyl, aralkyl or aryl, n is 1-25, m is 1-6, and p is 0-4, may be emulsified in water by adding an emulsifier containing a long perfluorocarbon chain to a solution of the chelate in an organic solvent, evaporating to a viscous consistency and then emulsifying in water, to which a thickener has desirably been added, by the use of sound vibrations.  The emulsions may then be further diluted with water.  The above emulsions, or solutions of the chelates in organic solvents, may be used to render materials or surfaces anti-adhesive, indiffusible, and oilwater- and dirt-repellent, by impregnation or coating the materials or surfaces with said emulsions or solutions. Specified materials and surfaces so treated are varnished surfaces, car lacquers, metallic surfaces, polyethylene and regenerated cellulose films, adhesive strips of plastics or fabrics, and plastic combs.ALSO:Textile fabrics, leather, paper and wood are rendered oil-, water- and dirt-repellent by impregnation with chelates of Ti, Zr, Al, Sn and Zn with compounds of the formulae: <FORM:1121905/D1-D2/1> wherein X is F, Cl or H, R1 and R4 are alkyl, fluoroalkyl, aryl, aralkyl or alkaryl, R2 is alkyl, fluoroalkyl, aryl, aralkyl, alkaryl, OH, alkoxy, aroxy, aralkoxy or alkaroxy, R3 is H, C1-5 alkyl, aralkyl or aryl, n is 1-25, m is 1-6, and p is 0-4. The chelates are employed in the form of emulsions in water or solutions in organic solvents.