Phosphate surfactants

1. A compound of Formula 1

R f -A-OP(O)(O − M + )(OROH)  Formula 1

wherein

R f is a C 2 to C 6 linear or branched perfluoroalkyl optionally interrupted by one, two or three ether oxygen atoms;

A is (CH 2 CF 2 ) m (CH 2 ) n —, (CH 2 ) o SO 2 N(CH 3 )(CH 2 ) p —, O(CF 2 ) q (CH 2 ) r —, or OCHFCF 2 OE-;

m is 0 to 4; n, o, p, and r are each independently 2 to 20; q is 2;

E is a C 2 to C 20 linear or branched alkyl group optionally interrupted by oxygen, sulfur, or nitrogen atoms; a cyclic alkyl group, or a C 6 to C 10 aryl group;

M is H or a Group I metal or an ammonium cation (NH x R 2 y ) + wherein R 2 is a C 1 to C 4 alkyl, x is 0 to 4, y is 0 to 4 and x+y is 4; and

R is a C 2 to C 60 linear or branched alkyl group optionally interrupted by hetero atoms selected from the group consisting of an oxygen, sulfur, or nitrogen atom; a cyclic alkyl; or a C 6 to C 10 aryl; provided that when R is greater than 8 carbons, the ratio of hetero atoms to carbon atoms is at least 1:2.

2. The compound of claim 1 wherein R is a C 2 to C 8 linear or branched alkyl.

3. The compound of claim 1 wherein R is a C 8 to C 40 linear or branched alkyl interrupted by from about 2 to about 20 oxygen atoms, wherein the ratio of oxygen atoms to carbon atoms is from about 1:2 to about 1:4.

4. The compound of claim 1 wherein M is H, sodium, potassium, or an ammonium cation (NH x R 2 y ) + wherein R 2 is a C 1 to C 4 alkyl, x is 0 to 4, y is 0 to 4 and x+y is 4.

5. The compound of claim 1 wherein A is (CH 2 CF 2 ) m (CH 2 ) n —; m=0, 1, or 2; n is 2; R f is C 4 F 9 or C 6 F 13 ; and R is a C 3 alkyl or a C 8 to C 40 linear or branched alkyl interrupted by from about 2 to about 20 oxygen atoms.

6. The compound of claim 1 wherein A is (CH 2 ) o SO 2 N(CH 3 )(CH 2 ) p —, o and p are each 2, R f is C 4 F 9 or C 6 F 13 , and R is a C 3 alkyl or a C 8 to C 40 linear or branched alkyl interrupted by from about 2 to about 20 oxygen atoms.

7. The compound of claim 1 wherein A is O(CF 2 ) q (CH 2 ) r —, q and r are each 2, R f is C 2 F 5 or C 3 F 7 , and R is a C 3 alkyl or a C 8 to C 40 linear or branched alkyl interrupted by from about 2 to about 20 oxygen atoms.

8. The compound of claim 1 wherein A is OCHFCF 2 OE-, R f is C 2 F 5 or C 3 F 7 , and R is a C 3 alkyl or a C 8 to C 40 linear or branched alkyl interrupted by from about 2 to about 20 oxygen atoms.

9. The compound of claim 1 having a surface tension of about 22 mN/m or less at a concentration of 0.1% by weight in water.

10. The compound of claim 1 having a surface tension of about 18 mN/m or less at a concentration of 0.5% by weight in water.

11. A method of lowering the surface tension of an aqueous medium comprising contacting the medium with a composition of Formula 1

R f -A-OP(O)(O − M + )(OROH)  Formula 1

wherein

R f is a C 2 to C 6 linear or branched perfluoroalkyl optionally interrupted by one, two or three ether oxygen atoms;

A is (CH 2 CF 2 ) m (CH 2 ) n —, (CH 2 ) o SO 2 N(CH 3 )(CH 2 ) p —, O(CF 2 ) q (CH 2 ) r —, or OCHFCF 2 OE-;

m is 0 to 4; n, o, p, and r are each independently 2 to 20; q is 2;

E is a C 2 to C 20 linear or branched alkyl group optionally interrupted by oxygen, sulfur, or nitrogen atoms; a cyclic alkyl group, or a C 6 to C 10 aryl group;

M is H or a Group I metal or an ammonium cation (NH x R 2 y ) + wherein R 2 is a C 1 to C 4 alkyl, x is 0 to 4, y is 0 to 4 and x+y is 4; and

R is a C 2 to C 60 linear or branched alkyl group optionally interrupted by hetero atoms selected from the group consisting of an oxygen, sulfur, or nitrogen atom; a cyclic alkyl; or a C 6 to C 10 aryl; provided that when R is greater than 8 carbons, the ratio of hetero atoms to carbon atoms is at least 1:2.

12. The method of claim 11 wherein the medium is a coating composition, latex, polymer, floor finish, ink, emulsifying agent, foaming agent, release agent, repellency agent, flow modifier, film evaporation inhibitor, wetting agent, penetrating agent, cleaner, grinding agent, electroplating agent, corrosion inhibitor, etchant solution, soldering agent, dispersion aid, microbial agent, pulping aid, rinsing aid, polishing agent, personal care composition, drying agent, antistatic agent, floor polish, or bonding agent.

13. The method of claim 11 wherein the compound of Formula 1 is applied to a substrate prior to contacting with the medium.

14. The method of claim 11 wherein the medium is an acid, base, or brine.

15. A method of providing soil repellency, leveling, and resistance to blocking to a coated substrate comprising adding to a coating base prior to deposition on the substrate a compound of Formula 1

R f -A-OP(O)(O − M + )(OROH)  Formula 1

wherein

R f is a C 2 to C 6 linear or branched perfluoroalkyl optionally interrupted by one, two or three ether oxygen atoms;

A is (CH 2 CF 2 ) m (CH 2 ) n —, (CH 2 ) o SO 2 N(CH 3 )(CH 2 ) p —, O(CF 2 ) q (CH 2 ) r —, or OCHFCF 2 OE-;

m is 0 to 4; n, o, p, and r are each independently 2 to 20; q is 2;

E is a C 2 to C 20 linear or branched alkyl group optionally interrupted by oxygen, sulfur, or nitrogen atoms; a cyclic alkyl group, or a C 6 to C 10 aryl group;

M is H or a Group I metal or an ammonium cation (NH x R 2 y ) + wherein R 2 is a C 1 to C 4 alkyl, x is 0 to 4, y is 0 to 4 and x+y is 4; and

R is a C 2 to C 60 linear or branched alkyl group optionally interrupted by hetero atoms selected from the group consisting of an oxygen, sulfur, or nitrogen atom; a cyclic alkyl; or a C 6 to C 10 aryl; provided that when R is greater than 8 carbons, the ratio of hetero atoms to carbon atoms is at least 1:2.

16. The method of claim 14 wherein the coating base is a water dispersed coating, alkyd coating, Type I urethane coating, unsaturated polyester coating, or a floor polish.

17. A method of providing foaming in a medium comprising contacting the medium with a compound of Formula 1

R f -A-OP(O)(O − M + )(OROH)  Formula 1

wherein

R f is a C 2 to C 6 linear or branched perfluoroalkyl optionally interrupted by one, two or three ether oxygen atoms;

A is (CH 2 CF 2 ) m (CH 2 ) n —, (CH 2 ) o SO 2 N(CH 3 )(CH 2 ) p —, O(CF 2 ) q (CH 2 ) r —, or OCHFCF 2 OE-;

m is 0 to 4; n, o, p, and r are each independently 2 to 20; q is 2;

E is a C 2 to C 20 linear or branched alkyl group optionally interrupted by oxygen, sulfur, or nitrogen atoms; a cyclic alkyl group, or a C 6 to C 10 aryl group;

M is H or a Group I metal or an ammonium cation (NH x R 2 y ) + wherein R 2 is a C 1 to C 4 alkyl, x is 0 to 4, y is 0 to 4 and x+y is 4; and

R is a C 2 to C 60 linear or branched alkyl group optionally interrupted by hetero atoms selected from the group consisting of an oxygen, sulfur, or nitrogen atom; a cyclic alkyl; or a C 6 to C 10 aryl; provided that when R is greater than 8 carbons, the ratio of hetero atoms to carbon atoms is at least 1:2.

18. The method of claim 17 wherein the medium is an aqueous or brine medium.

19. The method of claim 18 wherein the medium is a cleaning solution or a medium used in stimulation treatment in oil or gas wells or in drilling applications in oil or gas wells.

20. The method of claim 17 wherein the medium is an aggressive medium and the foam disintegrates within 15 minutes.

21. The method of claim 20 wherein the medium is an etching solution or a cleaning solution.