Partially fluorinated phosphates

1. A compound of formula (1), or mixtures thereof:

wherein

R f is C 1 to C 6 linear or branched fluoroalkyl,

X is F or Cl,

Y is O or a single bond,

A is —R 1 OH or ZR 2 ,

p is 0 to 1,

m is 0 or 2 to 10,

n is 0 to 30,

r is 1 or (3−x),

q is 0 or 1,

x is 1 to 2,

M is H, a Group I metal, an ammonium alkanol, an ammonium cation (NH z R 3 y ) + , or an ammonium cation (NH 2 R 4 R 5 ) + ; wherein R 3 is a C 1 to C 4 alkyl, z is 1 to 4, y is 0 to 3, z+y is 4; R 4 and R 5 are independently H or linear or branched organic groups containing at least one carboxylate moiety and one amino moiety, and R 4 and R 5 are independently optionally substituted, interrupted, or both with oxygen, sulfur, or nitrogen-containing moieties, or with cyclic, alkyl, or aryl moieties containing up to 10 carbon atoms,

R 1 is a C 2 to C 60 linear or branched alkylene 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;

R 2 is a linear, branched, or cyclic alkyl or a C 6 to C 10 aryl,

Z is —(CH 2 CHR 6 O) a ,

a is 1 to 20,

R 6 is H, CH 3 , or CH 2 CH 3 ,

wherein at least one of p or m is a positive integer,

provided that, when q is 0, r is (3−x), and when q is 1, r and x are each 1;

provided that, if n is greater than 2, then p is 1;

provided that, if m is 0 then Y is a single bond, and if m is a positive integer then Y is O; and

provided that when R 1 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 f is C 1 to C 3 linear fluoroalkyl.

3. The compound of claim 1 selected from the formula (1) such that (i) p is 1, m is 0 or 3 to 8, and n is 0; (ii) p is 0, m is 2 to 8, and n is 0; (iii) p is 1, m is 0, and n is 1 to 12; or (4) p is 0, m is 0, and n is 1 to 2.

4. A method for lowering the surface tension of coating compositions comprising contacting said coating compositions with one or more compounds of formula (1):

wherein

R f is C 1 to C 6 linear or branched fluoroalkyl,

X is F or Cl,

Y is O or a single bond,

A is —R 1 OH or ZR 2 ,

p is 0 to 1,

m is 0 or 2 to 10,

n is 0 to 30,

r is 1 or (3−x),

q is 0 or 1,

x is 1 to 2,

M is H, a Group I metal, an ammonium alkanol, an ammonium cation (NH z R 3 y ) + , or an ammonium cation (NH 2 R 4 R 5 ) + ; wherein R 3 is a C 1 to C 4 alkyl, z is 1 to 4, y is 0 to 3, z+y is 4; R 4 and R 5 are independently H or linear or branched organic groups containing at least one carboxylate moiety and one amino moiety, and R 4 and R 5 are independently optionally substituted, interrupted, or both with oxygen, sulfur, or nitrogen-containing moieties, or with cyclic, alkyl, or aryl moieties containing up to 10 carbon atoms,

R 1 is a C 2 to C 60 linear or branched alkylene 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;

R 2 is a linear, branched, or cyclic alkyl or a C 6 to C 10 aryl,

Z is —(CH 2 CHR 6 O) a ,

a is 1 to 20,

R 6 is H, CH 3 , or CH 2 CH 3 ,

wherein at least one of p or m is a positive integer,

provided that, when q is 0, r is (3−x), and when q is 1, r and x are each 1;

provided that, if n is greater than 2, then p is 1;

provided that, if m is 0 then Y is a single bond, and if m is a positive integer then Y is O; and

provided that when R 1 is greater than 8 carbons, the ratio of hetero atoms to carbon atoms is at least 1:2.

5. A method of imparting surface effects to substrates comprising contacting all or a portion of a surface of the substrate with a coating composition comprising one or more compounds of formula (1):

wherein

R f is C 1 to C 6 linear or branched fluoroalkyl,

X is F or Cl,

Y is O or a single bond,

A is —R 1 OH or ZR 2 ,

p is 0 to 1,

m is 0 or 2 to 10,

n is 0 to 30,

r is 1 or (3−x),

q is 0 or 1,

x is 1 to 2,

M is H, a Group I metal, an ammonium alkanol, an ammonium cation (NH z R 3 y ) + , or an ammonium cation (NH 2 R 4 R 5 ) + ; wherein R 3 is a C 1 to C 4 alkyl, z is 1 to 4, y is 0 to 3, z+y is 4; R 4 and R 5 are independently H or linear or branched organic groups containing at least one carboxylate moiety and one amino moiety, and R 4 and R 5 are independently optionally substituted, interrupted, or both with oxygen, sulfur, or nitrogen-containing moieties, or with cyclic, alkyl, or aryl moieties containing up to 10 carbon atoms,

R 1 is a C 2 to C 60 linear or branched alkylene 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;

R 2 is a linear, branched, or cyclic alkyl or a C 6 to C 10 aryl,

Z is —(CH 2 CHR 6 O) a ,

a is 1 to 20,

R 6 is H, CH 3 , or CH 2 CH 3 ,

wherein at least one of p or m is a positive integer,

provided that, when q is 0, r is (3−x), and when q is 1, r and x are each 1;

provided that, if n is greater than 2, then p is 1;

provided that, if m is 0 then Y is a single bond, and if m is a positive integer then Y is O; and

provided that when R 1 is greater than 8 carbons, the ratio of hetero atoms to carbon atoms is at least 1:2.

6. The method of claim 4 or 5 wherein R f is C 1 to C 3 linear fluoroalkyl.

7. The method of claim 4 or 5 , wherein the compound is selected from the formula (1) such that (i) p is 1, m is 0 or 3 to 8, and n is 0; (ii) p is 0, m is 2 to 8, and n is 0; (iii) p is 1, m is 0, and n is 1 to 12; or (4) p is 0, m is 0, and n is 1 to 2.

8. The method of claim 4 or 5 wherein the coating composition is selected from the group consisting of an alkyl coating, Type I urethane coating, unsaturated polyester coating, or water-dispersed coating.

9. The method of claim 8 wherein the coating composition is a floor finish, polishing agent, floor polish, or paint.

10. The method of claim 5 wherein the surface effect is resistance to blocking, oil repellency, water repellency, stain resistance, dirt pickup resistance, increased contact angle, or increased wetting and leveling of the coating surface.

11. A method of claim 5 , wherein the coating composition is applied to the substrate prior to contacting with a composition of formula (1).

12. The method of claim 4 wherein the contacting increases wetting and leveling in the coating composition.