Fluorinated surfactants

Abstract

A composition of formula I [Rf(CH 2 )m(O)n]x-A wherein R f is a straight or branched perfluoroalkyl group having from about 2 to about 20 carbon atoms, or a mixture thereof, m is a positive integer equal to or greater than 3, n is 0 or 1, x is 1 to about 3, and A is —P(O)(OR 1 ) y (OM + ) 3-y-x , —C(O)CH(SO 3 − M + )CH 2 C(O) − , —(CH 2 CH 2 O) d (CH 2 CHR 2 O) e R 3 , or − SO 2 B, M + is an alkali metal ion, NH 4 + , or NH 2 (CH 2 CH 2 OH) 2 , B is N(R) 2 or N(CH 2 CH 3 )(CH 2 CH 2 OH), R 1 is C 1 to C 3 alkyl, and R 2 is C 1 to C 4 alkyl, R 3 is H or CH 3 , y is 0 to about 1, d is 0 to about 16, e is 0 to about 16, provided that (d+e) is from about 3 to about 16 is disclosed.

1 . A composition of formula I
   [Rf(CH2)m(O)n]x-A   
       wherein
 R f  is a straight or branched perfluoroalkyl group having from about 2 to about 20 carbon atoms, or a mixture thereof, 
 m is a positive integer equal to or greater than 3, 
 n is 0 or 1, 
 x is 1 to about 3, and 
 A is —C(O)CH(SO 3   − M + )CH 2 C(O) − , or  − SO 2 B, 
 M +  is an alkali metal ion, NH 4   + , or NH 2   + (CH 2 CH 2 OH) 2 , 
 B is N(R 2 ) 2  or N(CH 2 CH 3 )(CH 2 CH 2 OH), and 
 R 2  is C 1  to C 4  alkyl. 
 
     
     
         2 . (canceled) 
     
     
         3 . The composition of  claim 1  wherein n is 1, x is 2, and A is —C(O)CH(SO 3   − M + )CH 2 C(O) − . 
     
     
         4 . (canceled) 
     
     
         5 . The composition of  claim 1  wherein n is 0, x is 1,A is SO 3 B and B is N(R 2 ) 2  or N(CH 2 CH 3 )(CH 2 CH 2 OH). 
     
     
         6 . The composition of  claim 1  further comprising a surface treatment agent. 
     
     
         7 . The composition of  claim 6  wherein the surface treatment agent provides a surface effect with or without ironing which is shrinkage control, wrinkle free, permanent press, moisture control, softness, strength, anti-slip, antistatic, anti-snag, anti-pill, stain repellency, stain release, soil repellency, soil release, water repellency, oil repellency, odor control, antimicrobial, or sun protection. 
     
     
         8 . A method of lowering the tension at the surface of contact between two phases comprising contacting said surface with a composition of Formula I
   [R f (CH 2 ) m (O) n ] x -A   
       wherein
 R f  is a straight or branched perfluoroalkyl group having from about 2 to about 20 carbon atoms, or a mixture thereof,
 m is a positive integer equal to or greater than 3, 
 n is 0 or 1, 
 x is 1 to about 3, and 
 A is —C(O)CH(SO 3   − M + )CH 2 C(O) − , or  − SO 2 B, 
 
 M +  is an alkali metal ion, NH 4   + , or NH 2   + (CH 2 CH 2 OH) 2 , 
 B is N(R 2 ) 2  or N(CH 2 CH 3 )(CH 2 CH 2 OH), and 
 R 2  is C 1  to C 4  alkyl. 
 
     
     
         9 . The method of  claim 8  wherein the composition acts as a leveling agent. 
     
     
         10 . The method of  claim 8  wherein the phases are each independently a fibrous surface or a hard surface. 
     
     
         11 . The method of  claim 8  wherein the composition is applied as a coating to a surface. 
     
     
         12 . An improved process for the preparation of perfluoroalkylalkyl acrylate or perfluoroalkylalkyl methacrylate by reaction of a) sodium acrylate or ppotassium acrylate, or b) sodium methacrylate or potassium methacrylate, respectively, with perfluoroalkylalkyliodide wherein the improvement comprises use of a long chain iodide of formula R f (CH 2 ) m I wherein R f  is a straight or branched perfluoroalkyl group having from about 2 to about 20 carbon atoms, or a mixture thereof, which is optionally interrupted by at least one oxygen atom, and m is a positive integer equal or greater than 3. 
     
     
         13 . The process of  claim 12  wherein m is 3 to about 10. 
     
     
         14 . The process of  claim 12  wherein the reaction is conducted in a monohydric secondary or tertiary alcohol solvent. 
     
     
         15 . The process of  claim 14  wherein the solvent is anhydrous. 
     
     
         16 . The process of  claim 14  wherein the solvent is t-butanol. 
     
     
         17 . The process of  claim 14  conducted at a reaction temperature of from about 125° C. to about 200° C. 
     
     
         18 . The process of  claim 17  further comprising recovering the perfluoroalkylalkyl acrylates or perfluoroalkylalkyl methacrylates from the reaction mixture. 
     
     
         19 . The process of  claim 12  wherein the perfluoroalkylalkyl acrylates and perfluoroalkylalkyl methacrylates are obtained at a higher yield compared to a process using an iodide of formula R f (CH 2 ) m I wherein m is 2. 
     
     
         20 . The product of the process of  claim 12 .