# US 2015/0147579 A1 · Fluorinated compositions and surface treatments made therefrom

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- Number: US 2015/0147579 A1
- Document ID: US20150147579A1
- Status: Published application
- Kind: A1
- Application number: 14/610,727
- Filed: 2015-01-30
- Published: 2015-05-28
- Earliest claimed: 2007-06-06
- Assignees: 3M Innovative Properties Company
- Applicants: 3M Innovative Properties Company
- Inventors: Chetan P. Jariwala; Gregory D. Clark; Jason T. Petrin; Rudolf J. Dams; Steven J. Martin; Mark J. Pellerite
- Web page: https://patentgrep.com/patent/US20150147579A1

## CPC

- C08F 220/36: containing oxygen in addition to the carboxy oxygen {, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate}
- C08F 8/40: Introducing phosphorus atoms or phosphorus-containing groups
- C08F 14/185: {Monomers containing fluorine not covered by the groups C08F14/20 - C08F14/28}
- C08F 220/22: Esters containing halogen
- C08J 3/09: in organic liquids
- C09D 127/12: containing fluorine atoms
- C09D 133/06: of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D 133/14: of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
- C09D 133/16: Homopolymers or copolymers of esters containing halogen atoms
- C09D 143/02: Homopolymers or copolymers of monomers containing phosphorus
- C08F 220/10: Esters
- C08F 220/1818: {C13or longer chain (meth)acrylate, e.g. stearyl (meth)acrylate}
- C08J 2333/16: Homopolymers or copolymers of esters containing halogen atoms
- Y10T 428/3154: Of fluorinated addition polymer from unsaturated monomers
- Y10T 428/31678: Of metal
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- 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)
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

A composition comprising at least one first divalent unit represented by formula: and at least one of a second divalent unit comprising a pendant Z group or a monovalent unit comprising a thioether linkage and a terminal Z group, wherein each Z group is independently selected from the group consisting of —P(O)(OY)2 and —O—P(O)(OY)2. R″ and R′″ are each independently selected from the group consisting of hydrogen and alkyl having from 1 to 4 carbon atoms. Y is selected from the group consisting of hydrogen, alkyl, trialkylsilyl, and a counter cation. Methods of treating a surface using these compositions and articles with a surface in contact with these compositions are provided. Methods of making these compositions are also provided.

## Claims

### Claim 1

A polymeric or oligomeric composition comprising a first divalent unit represented by formula:
and
at least one of
a second divalent unit represented by formula:
and
a monovalent unit selected from the group consisting of —S—CtH2t+1 and —S—CrH2r-A; or
a monovalent unit represented by a formula selected from the group consisting of:
—S—CbH2bC(O)CbH2b—P(O)(OY2)2; and
—S—CbH2b−1[OC(O)CbH2b—P(O)(OY2)2]2,
wherein
R′, R″, and R′″ are each independently hydrogen or alkyl having from 1 to 4 carbon atoms;
V is alkylene that is optionally interrupted by at least one ether linkage or amine linkage;
t is an integer having a value from 4 to 22;
r is an integer having a value from 2 to 10;
A is selected from the group consisting of —OH, —COOY2, and —SO3Y2;
each Y2 is independently selected from the group consisting of hydrogen, alkyl, and a counter cation; and
each b is independently an integer from 1 to 5.

### Claim 2 (depends on 1)

The polymeric or oligomeric composition of claim 1, wherein the polymeric or oligomeric composition comprises the second divalent unit represented by formula:
and
the monovalent unit selected from the group consisting of —S—CtH2t+1 and —S—CrH2r-A.

### Claim 3 (depends on 1)

The polymeric or oligomeric composition of claim 1, wherein the polymeric or oligomeric composition comprises the second divalent unit represented by formula:
and
the monovalent unit selected from the group consisting of —S—CtH2r+1 and —S—CrH2r-A.

### Claim 4 (depends on 1)

The polymeric or oligomeric composition of claim 1, wherein the polymeric or oligomeric composition comprises the monovalent unit represented by a formula selected from the group consisting of:
—S—CbH2bOC(O)CbH2b—P(O)(OY)2; and
—S—CbH2b−1[OC(O)CbH2b—P(O)(OY)2]2.

### Claim 5 (depends on 1)

The polymeric or oligomeric composition of claim 1, further comprising at least one divalent unit represented by formula:
wherein
each R2 is independently selected from the group consisting of hydrogen and alkyl having from 1 to 4 carbon atoms; and
each R3 is independently alkyl having from 1 to 30 carbon atoms.

### Claim 6 (depends on 1)

A formulation comprising the polymeric or oligomeric composition of claim 1 and solvent, wherein the solvent comprises at least one of a lower alcohol or a hydrofluoroether.

### Claim 7 (depends on 1)

A formulation comprising the polymeric or oligomeric composition of claim 1 and water.

### Claim 8 (depends on 7)

The formulation of claim 7, further comprising at least one of a nonionic or an anionic surfactant.

### Claim 9 (depends on 1)

A method of treating a surface, the method comprising contacting the surface with the polymeric or oligomeric composition of claim 1.

### Claim 10 (depends on 9)

The method of claim 9, wherein the surface comprises at least one of metal, metal oxide, ceramic, natural stone, or a cementicious surface.

### Claim 11 (depends on 9)

The method of claim 9, wherein the surface comprises at least one of stainless steel, chromium, or chromium oxide.

### Claim 12

An article having a surface, wherein at least a portion of the surface is in contact with a polymeric or oligomeric composition, the polymeric or oligomeric composition comprising a first divalent unit represented by formula:
and
at least one of
a second divalent unit represented by formula:
and
a monovalent unit selected from the group consisting of —S—CtH2t+1 and —S—CrH2r-A; or
a monovalent unit represented by a formula selected from the group consisting of:
—S—CbH2bC(O)CbH2b—P(O)(OY1)2; and
—S—CbH2b−1[OC(O)CbH2b—P(O)(OY1)2]2,
wherein
R′, R″, and R′″ are each independently hydrogen or alkyl having from 1 to 4 carbon atoms;
V is alkylene that is optionally interrupted by at least one ether linkage or amine linkage;
t is an integer having a value from 4 to 22;
r is an integer having a value from 2 to 10;
A is selected from the group consisting of —OH, —COOY1, and —SO3Y1;
each Y1 is independently selected from the group consisting of hydrogen, alkyl, a counter cation, and a bond to the surface; and
each b is independently an integer from 1 to 5.

### Claim 13 (depends on 12)

The article of claim 12, wherein the surface comprises at least one of metal, metal oxide, ceramic, natural stone, or a cementicious surface.

### Claim 14 (depends on 12)

The article of claim 12, wherein the surface comprises at least one of a metal or metal oxide, and wherein the compound forms at least a partial monolayer on the surface.

### Claim 15 (depends on 12)

The article of claim 12, wherein the surface comprises at least one of chromium or chromium oxide.

### Claim 16 (depends on 12)

The article of claim 12, wherein the article is at least one of a faucet, a faucet handle, a sink, an oven range, an oven range hood, a countertop, flooring, or wall covering.

### Claim 17 (depends on 12)

The article of claim 12, wherein the surface of the article comprises stainless steel.

### Claim 18

A method of making a polymeric or oligomeric composition, the method comprising reacting components comprising at least one component represented by formula:
Rf—C(O)—N(R1)—X—O—C(O)—C(R)═CH2; and
at least one component represented by formula:
(YO)2—P(O)—C(R′)═CH2 or
(YO)2—P(O)—O—V—O—C(O)—C(R′)═CH2;
wherein
each Rf is independently a perfluoropolyether group;
R, R′, and R1 are each independently selected from the group consisting of hydrogen and alkyl having from 1 to 4 carbon atoms;
each V is independently alkylene that is optionally interrupted by at least one ether linkage or amine linkage; and
each Y is independently selected from the group consisting of hydrogen, alkyl, trialkylsilyl, and a counter cation.

### Claim 19 (depends on 18)

The method according to claim 18, wherein reacting is carried out in a medium comprising water.

### Claim 20 (depends on 19)

The method according to claim 19, wherein the medium further comprises an emulsifier.