# US 2010/0168300 A1 · Aqueous compositions of fluorinated surfactants and methods of using the same

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- Number: US 2010/0168300 A1
- Document ID: US20100168300A1
- Status: Published application
- Kind: A1
- Application number: 12/601,143
- Filed: 2008-05-21
- Published: 2010-07-01
- Earliest claimed: 2007-05-23
- Assignees: 3M Innovative Properties Company
- Inventors: Rudolf J. Dams; Michael S. Terrazas
- Web page: https://patentgrep.com/patent/US20100168300A1

## CPC

- C11D 1/004: {Surface-active compounds containing F}
- C09D 5/027: {Dispersing agents (anti-settling agents C09D7/45)}
- C09D 7/45: Anti-settling agents
- C09D 7/47: Levelling agents
- C09G 1/04: Aqueous dispersions (C09G1/02 takes precedence)
- C11D 3/37: Polymers {(polymeric surface-active agents C11D1/008; polysaccharides C11D3/222)}
- C11D: DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- C09G: POLISHING COMPOSITIONS (French polish C09F11/00); SKI WAXES

## Abstract

Aqueous compositions comprising surfactant represented by a formula selected from the group consisting of: [Rf—(O)t—CHF—(CF2)n—COO−]iXi+; {[Rf—(O)t—CQH—CF2—O]m—R—COO−}iXi+; {[Rf—(O)t—CQH—CF2—O]m—R—SO3−)i, Xi+; and [CF3CFH—O—(CF2)p—COO−]iXi+; wherein Rf represents a partially or fully fluorinated aliphatic group optionally interrupted with at least one oxygen atom; Q is selected from the group consisting of F and CF3; R is selected from the group consisting of alkylene and arylene; X1+ represents a cation having a valence i, wherein i is 1, 2 or 3; t is O or 1; m is 1, 2, or 3; n is O or 1; and p is an integer from 1 to 6. In some aspects, the aqueous composition comprises a non-fluorinated polymer and is essentially free of fluoropolymers. In another aspect, the aqueous composition has a pH of greater than 11. In another aspect, the aqueous composition has a pH of at least 8 and is essentially free of fluorinated olefins. Methods of coating a surface and an article having a surface in contact with the composition are provided. Methods of cleaning a surface, and methods of lowering the surface tension of a liquid having a pH greater than 11 using aqueous compositions comprising the surfactants are also provided.

## Claims

### Claim 1

An aqueous composition comprising a non-fluorinated polymer and a surfactant, wherein the surfactant is represented by a formula selected from the group consisting of:
[Rf—(O)t—CHF—(CF2)n—COO−]iXi+;
{[Rf—(O)t—CQH—CF2—O]m—R—COO−}iXi+;
{[Rf—(O)t—CQH—CF2—O]m—R—SO3−}iXi+; and
[CF3CFH—O—(CF2)p—COO−]iXi+;
wherein
Rf represents a partially or fully fluorinated aliphatic group optionally interrupted with at least one oxygen atom;
Q is selected from the group consisting of F and CF3;
R is selected from the group consisting of alkylene and arylene;
Xi+ represents a cation having a valence i, wherein i is 1, 2 or 3;
t is 0 or 1, wherein when the surfactant is represented by formula [Rf—(O)t—CHF—(CF2)n—COO−]iXi+ and t is 0, then Rf is interrupted with at least one oxygen atom;
m is 1, 2, or 3;
n is 0 or 1; and
p is an integer from 1 to 6; and
wherein the aqueous composition is essentially free of fluoropolymers.

### Claim 2 (depends on 1)

The aqueous composition according to claim 1, wherein the non-fluorinated polymer is at least one of an acrylic polymer, a polyurethane, a polyolefin, a styrene-acrylate copolymer, a polyester, a polyamide, a vinyl polymer, a polydiene, or a cellulosic polymer.

### Claim 3

(canceled)

### Claim 4 (depends on 1)

The aqueous composition according to claim 1, further comprising a coalescing solvent.

### Claim at position 5

5-6. (canceled)

### Claim 7 (depends on 1)

The aqueous composition according to claim 1, wherein t is 1, and wherein Rf is selected from the group consisting of:
fully fluorinated aliphatic groups having from 1 to 6 carbon atoms; and
fully fluorinated groups represented by formula:
Rf1—[ORf2]x—[ORf3]y—,
wherein
Rf1 is a perfluorinated aliphatic group having from 1 to 6 carbon atoms;
Rf2 and Rf3 are each independently perfluorinated alkylene having from 1 to 4 carbon atoms; and
x and y are each independently an integer having a value from 0 to 4, wherein the sum of x and y is at least 1.

### Claim 8 (depends on 1)

The aqueous composition according to claim 1, wherein t is 0, and wherein Rf is a fully fluorinated group represented by formula:
Rf4—[ORf5]a—[ORf6]b—O—CF2—,
wherein
Rf4 is a perfluorinated aliphatic group having from 1 to 6 carbon atoms;
Rf5 and Rf6 are each independently perfluorinated alkylene having from 1 to 4 carbon atoms; and
a and b are each independently integers having a value from 0 to 4.

### Claim 9 (depends on 1)

The aqueous composition according to claim 1, wherein the surfactant is represented by formula:
[Rf—(O)t—CHF—(CF2)n—COO−]iXi+.

### Claim 10 (depends on 1)

The aqueous composition according to claim 1, wherein the surfactant is represented by formula:
{[Rf—(O)t—CQH—CF2—O]m—R—COO−}iXi+;
wherein Q is F, m is 1, and wherein R is alkylene.

### Claim 11 (depends on 1)

The aqueous composition according to claim 1, wherein the surfactant is represented by formula:
[CF3CFH—O—(CF2)p—COO−]iXi+.

### Claim 12 (depends on 1)

The aqueous composition according to claim 1, wherein the surfactant is selected from the group consisting of:
[C3F7—O—CHF—COO−]iXi+;
[CF3—O—CF2CF2—CF2—O—CHF—COO−]iXi+;
[CF3CF2CF2—O—CF2CF2—CF2—O—CHF—COO−]iXi+;
[CF3—O—CF2—CF2—O—CHF—COO−]iXi+;
[CF3—O—CF2—O—CF2—CF2—O—CHF—COO−]iXi+;
[CF3—(O—CF2)2—O—CF2—CF2—O—CHF—COO−]iXi+;
[CF3—(O—CF2)3—O—CF2—CF2—O—CHF—COO−]iXi+;
[CF3—O—CHF—CF2—COO−]iXi+;
[CF3—O—CF2—CF2—O—CHF—CF2—COO−]iXi+;
[CF3—CF2—O—CHF—CF2—COO−]iXi+;
[CF3—O—CF2—CF2—CF2—O—CHF—CF2—COO−]iXi+;
[CF3—O—CF2—O—CF2—CF2—O—CHF—CF2—COO−]iXi+;
[CF3—(O—CF2)2—O—CF2—CF2—O—CHF—CF2—COO−]iXi+;
[CF3—(O—CF2)3—O—CF2—CF2—O—CHF—CF2—COO−]iXi+;
[CF3—O—CF2—CHF—COO−]iXi+;
[C3F7—O—CF2—CHF—COO−]iXi+;
[CF3—O—CF2—CF2—CF2—O—CF2—CHF—COO−]iXi+;
[CF3—O—CF2—O—CF2—CF2—O—CF2—CHF—COO−]iXi+;
[CF3—(O—CF2)2—O—CF2—CF2—O—CF2—CHF—COO−]iXi+;
[CF3—(O—CF2)3—O—CF2—CF2—O—CF2—CHF—COO−]iXi+;
[CF3—O—CF2—CHF—CF2—COO−]iXi+;
[C2F5—O—CF2—CHF—CF2—COO−]iXi+;
[C3F7—O—CF2—CHF—CF2—COO−]iXi+;
[CF3—O—CF2—CF2—CF2—O—CF2—CHF—CF2—COO−]iXi+;
[CF3—O—CF2—O—CF2—CF2—O—CF2—CHF—CF2—COO−]iXi+;
[CF3—(O—CF2)2—O—CF2—CF2—O—CF2—CHF—CF2—COO−]iXi+; and
[CF3—(O—CF2)3—O—CF2—CF2—O—CF2—CHF—CF2—COO−]iXi+.

### Claim 13 (depends on 1)

The aqueous composition according to claim 1, wherein the surfactant is selected from the group consisting of:
[CF3—O—CHF—CF2—O—CH2—COO−]iXi+;
[CF3—O—CF2—CF2—CF2—O—CHF—CF2—O—CH2—COO−]iXi+;
[C3F7—O—CHF—CF2—O—CH2—COO−]iXi+;
[C3F7—O—CHF—CF2—O—CH2—CH2—COO−]iXi+;
[C3F7—O—CF2—CF2—O—CHF—CF2—OCH2COO−]iXi+;
[C3F7—O—CF2—CF2—CF2—O—CHF—CF2—OCH2COO−]iXi+;
[C3F7—O—CF2—CHF—CF2—OCH2COO−]iXi+;
[CF3—CHF—CF2—O—CH2COO−]iXi+; and
[C3F7—CF2—CHF—CF2—OCH2—COO−]iXi+.

### Claim 14 (depends on 1)

A method of coating a surface, the method comprising applying to the surface an aqueous composition according to claim 1.

### Claim 15

An article having a surface, wherein at least a portion of the surface is in contact with a composition comprising a non-fluorinated polymer and a surfactant, wherein the surfactant is represented by a formula selected from the group consisting of:
[Rf—(O)t—CHF—(CF2)n—COO−]iXi+;
{[Rf—(O)t—CQH—CF2—O]m—R—COO−}iXi+;
{[Rf—(O)t—CQH—CF2—O]m—R—SO3−}iXi+; and
[CF3CFH—O—(CF2)p—COO−]iXi+;
wherein
Rf represents a partially or fully fluorinated aliphatic group optionally interrupted with at least one oxygen atom;
Q is selected from the group consisting of F and CF3;
R is selected from the group consisting of alkylene and arylene;
Xi+ represents a cation having a valence i, wherein i is 1, 2 or 3;
t is 0 or 1, wherein when the surfactant is represented by formula [Rf—(O)t—CHF—(CF2)n—COO−]iXi+ and t is 0, then Rf is interrupted with at least one oxygen atom;
m is 1, 2, or 3;
n is 0 or 1; and
p is an integer from 1 to 6; and
wherein the composition is essentially free of fluoropolymers.

### Claim 16 (depends on 15)

The article according to claim 15, wherein the non-fluorinated polymer is at least one of an acrylic polymer, a polyurethane, a polyolefin, a styrene-acrylate copolymer, a polyester, a polyamide, a vinyl polymer, a polydiene, or a cellulosic polymer.

### Claim 17

(canceled)

### Claim 18 (depends on 15)

The article according to claim 15, wherein t is 1, and wherein Rf is selected from the group consisting of:
fully fluorinated aliphatic groups having from 1 to 6 carbon atoms; and
fully fluorinated groups represented by formula:
Rf1—[ORf2]x—[ORf3]y—,
wherein
Rf1 is a perfluorinated aliphatic group having from 1 to 6 carbon atoms;
Rf2 and Rf3 are each independently perfluorinated alkylene having from 1 to 4 carbon atoms; and
x and y are each independently an integer having a value from 0 to 4, wherein the sum of x and y is at least 1.

### Claim 19 (depends on 15)

The article according to claim 15, wherein t is 0, and wherein Rf is a fully fluorinated group represented by formula:
Rf4—[ORf5]a—[ORf6]b—O—CF2—,
wherein
Rf4 is a perfluorinated aliphatic group having from 1 to 6 carbon atoms;
Rf5 and Rf6 are each independently perfluorinated alkylene having from 1 to 4 carbon atoms; and
a and b are each independently integers having a value from 0 to 4.

### Claim 20 (depends on 15)

The article according to claim 15, wherein the surfactant is represented by formula:
[Rf—(O)t—CHF—(CF2)n—COO−]iXi+.

### Claim 21 (depends on 15)

The article according to claim 15, wherein the surfactant is represented by formula:
{[Rf—(O)t—CQH—CF2—O]m—R—COO−}iXi+;
wherein Q is F, m is 1, and wherein R is alkylene.

### Claim 22 (depends on 15)

The article according to claim 15, wherein the surfactant is represented by formula:
[CF3CFH—O—(CF2)p—COO−]iXi+.

### Claim at position 22

23-26. (canceled)

### Claim 27

A method of reducing the surface tension of a liquid having a pH greater than 11, the method comprising combining the liquid with a surfactant to reduce the surface tension of the liquid, wherein the surfactant is represented by a formula selected from the group consisting of:
[Rf—(O)t—CHF—(CF2)n—COO−]iXi+;
{[Rf—(O)t—CQH—CF2—O]m—R—COO−}iXi+;
{[Rf—(O)t—CQH—CF2—O]m—R—SO3−}iXi+; and
[CF3CFH—O—(CF2)p—COO−]iXi+;
wherein
Rf represents a partially or fully fluorinated aliphatic group optionally interrupted with at least one oxygen atom;
Q is selected from the group consisting of F and CF3;
R is selected from the group consisting of alkylene and arylene;
Xi+ represents a cation having a valence i, wherein i is 1, 2 or 3;
t is 0 or 1, wherein when the surfactant is represented by formula [Rf—(O)t—CHF—(CF2)n—COO−]iXi+ and t is 0, then Rf is interrupted with at least one oxygen atom;
m is 1, 2, or 3;
n is 0 or 1; and
p is an integer from 1 to 6.

### Claim 28 (depends on 27)

The method according to claim 27, wherein the liquid is essentially free of fluoropolymers.

### Claim at position 25

29-35. (canceled)

### Claim 36

An aqueous composition comprising a surfactant represented by a formula selected from the group consisting of:
[Rf—(O)t—CHF—(CF2)n—COO−]iXi+;
{[Rf—(O)t—CQH—CF2—O]m—R—COO−}iXi+;
{[Rf—(O)t—CQH—CF2—O]m—R—SO3−}iXi+; and
[CF3CFH—O—(CF2)p—COO−]iXi+;
wherein
Rf represents a partially or fully fluorinated aliphatic group optionally interrupted with at least one oxygen atom;
Q is selected from the group consisting of F and CF3;
R is selected from the group consisting of alkylene and arylene;
Xi+ represents a cation having a valence i, wherein i is 1, 2 or 3;
t is 0 or 1, wherein when the surfactant is represented by formula [Rf—(O)t—CHF—(CF2)n—COO−]iXi+ and t is 0, then Rf is interrupted with at least one oxygen atom;
m is 1, 2, or 3;
n is 0 or 1; and
p is an integer from 1 to 6;
wherein the aqueous composition has a pH greater than 11, or wherein the aqueous composition has a pH of at least 8 and is essentially free of fluoropolymers and fluorinated olefins.