PHOSPHATE SURFACTANTS

• US 20100240920A1
• Filed: 03/20/2009
• Published: 09/23/2010
• Est. Priority Date: 03/20/2009
• Status: Active Grant

• Current Assignee: The Chemours Company FC, LLC (The Chemours Company)
• Original Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Inventors: Peng, Sheng, Yake, Allison Mary
• Granted Patent: US 8,022,238 B2
• Time in Patent Office: Days
• US Class Current: 558/169
• CPC Class Codes: C07F 9/091 with hydroxyalkyl compounds with further substituents on alkyl
• CPC Class Codes: C09D 7/47 Levelling agents
• CPC Class Codes: C09D 9/04 with surface-active agents
• CPC Class Codes: C09G 1/04 Aqueous dispersions C09G1/02 takes precedence
• CPC Class Codes: C09K 23/007 Organic compounds containing halogen
• CPC Class Codes: C09K 23/14 Derivatives of phosphoric acid
• CPC Class Codes: C11D 1/006 Surface-active compounds containing fluorine and phosphorus

Abstract

A compound of Formula 1

R_f-A-OP(O)(O⁻M⁺)(OROH)   Formula 1

wherein

• • R_f is a C₂ to C₆ linear or branched perfluoroalkyl optionally interrupted by one, two or three ether oxygen atoms;
  • A is (CH₂CF₂)_m(CH₂)_n—, (CH₂)_oSO₂N(CH₃)(CH₂)_p—, O(CF₂)_q(CH₂)_r—, or OCHFCF₂OE-;
  • m is 0 to 4; n, o, p, and r are each independently 2 to 20; q is 2;
  • E is a C₂ to C₂₀ linear or branched alkyl group optionally interrupted by oxygen, sulfur, or nitrogen atoms; a cyclic alkyl group, or a C₆ to C₁₀ aryl group;
  • M is H or a Group I metal or an ammonium cation (NH_xR²_y)⁺ wherein R² is a C₁ to C₄ alkyl, x is 0 to 4, y is 0 to 4 and x+y is 4; and
  • R is a C₂ to C₆₀ 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 C₆ to C₁₀ aryl; provided that when R is greater than 8 carbons, the ratio of hetero atoms to carbon atoms is at least 1:2.

Claims

1. A compound of Formula 1

R_f-A-OP(O)(O⁻

M⁺)(OROH)  

 

Formula 1

wherein

R_f is a C₂ to C₆ linear or branched perfluoroalkyl optionally interrupted by one, two or three ether oxygen atoms;

A is (CH₂CF₂)_m(CH₂)_n—

, (CH₂)_oSO₂N(CH₃)(CH₂)_p—

, O(CF₂)_q(CH₂)_r—

, or OCHFCF₂OE-;

m is 0 to 4;

n, o, p, and r are each independently 2 to 20;

q is 2;

E is a C₂ to C₂₀ linear or branched alkyl group optionally interrupted by oxygen, sulfur, or nitrogen atoms;

a cyclic alkyl group, or a C₆ to C₁₀ aryl group;

M is H or a Group I metal or an ammonium cation (NH_xR²_y)⁺ wherein R² is a C₁ to C₄ alkyl, x is 0 to 4, y is 0 to 4 and x+y is 4; and

R is a C₂ to C₆₀ 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 C₆ to C₁₀ 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 C₂ to C₈ linear or branched alkyl.

3. The compound of claim 1 wherein R is a C₈ to C₄₀ 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_xR²_y)⁺ wherein R² is a C₁ to C₄ 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 (CH₂CF₂)_m(CH₂)_n—

;

m=0, 1, or 2;

n is 2;

R_f is C₄F₉ or C₆F₁₃; and

R is a C₃ alkyl or a C₈ to C₄₀ linear or branched alkyl interrupted by from about 2 to about 20 oxygen atoms.

6. The compound of claim 1 wherein A is (CH₂)_oSO₂N(CH₃)(CH₂)_p—

, o and p are each 2, R_f is C₄F₉ or C₆F₁₃, and R is a C₃ alkyl or a C₈ to C₄₀ linear or branched alkyl interrupted by from about 2 to about 20 oxygen atoms.

7. The compound of claim 1 wherein A is O(CF₂)_q(CH₂)_r—

, q and r are each 2, R_f is C₂F₅ or C₃F₇, and R is a C₃ alkyl or a C₈ to C₄₀ linear or branched alkyl interrupted by from about 2 to about 20 oxygen atoms.

8. The compound of claim 1 wherein A is OCHFCF₂OE-, R_f is C₂F₅ or C₃F₇, and R is a C₃ alkyl or a C₈ to C₄₀ 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 C₂ to C₆ linear or branched perfluoroalkyl optionally interrupted by one, two or three ether oxygen atoms;

A is (CH₂CF₂)_m(CH₂)_n—

, (CH₂)_oSO₂N(CH₃)(CH₂)_p—

, O(CF₂)_q(CH₂)_r—

, or OCHFCF₂OE-;

m is 0 to 4;

n, o, p, and r are each independently 2 to 20;

q is 2;

E is a C₂ to C₂₀ linear or branched alkyl group optionally interrupted by oxygen, sulfur, or nitrogen atoms;

a cyclic alkyl group, or a C₆ to C₁₀ aryl group;

M is H or a Group I metal or an ammonium cation (NH_xR²_y)⁺ wherein R² is a C₁ to C₄ alkyl, x is 0 to 4, y is 0 to 4 and x+y is 4; and

R is a C₂ to C₆₀ 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 C₆ to C₁₀ 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.

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.

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 C₂ to C₆ linear or branched perfluoroalkyl optionally interrupted by one, two or three ether oxygen atoms;

A is (CH₂CF₂)_m(CH₂)_n—

, (CH₂)_oSO₂N(CH₃)(CH₂)_p—

, O(CF₂)_q(CH₂)_r—

, or OCHFCF₂OE-;

m is 0 to 4;

n, o, p, and r are each independently 2 to 20;

q is 2;

E is a C₂ to C₂₀ linear or branched alkyl group optionally interrupted by oxygen, sulfur, or nitrogen atoms;

a cyclic alkyl group, or a C₆ to C₁₀ aryl group;

M is H or a Group I metal or an ammonium cation (NH_xR²_y)⁺ wherein R² is a C₁ to C₄ alkyl, x is 0 to 4, y is 0 to 4 and x+y is 4; and

R is a C₂ to C₆₀ 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 C₆ to C₁₀ aryl;

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

2.

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 C₂ to C₆ linear or branched perfluoroalkyl optionally interrupted by one, two or three ether oxygen atoms;

A is (CH₂CF₂)_m(CH₂)_n—

, (CH₂)_oSO₂N(CH₃)(CH₂)_p—

, O(CF₂)_q(CH₂)_r—

, or OCHFCF₂OE-;

m is 0 to 4;

n, o, p, and r are each independently 2 to 20;

q is 2;

E is a C₂ to C₂₀ linear or branched alkyl group optionally interrupted by oxygen, sulfur, or nitrogen atoms;

a cyclic alkyl group, or a C₆ to C₁₀ aryl group;

M is H or a Group I metal or an ammonium cation (NH_xR²_y)⁺ wherein R² is a C₁ to C₄ alkyl, x is 0 to 4, y is 0 to 4 and x+y is 4; and

R is a C₂ to C₆₀ 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 C₆ to C₁₀ 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.