# US 2014/0154519 A1 · Non-aqueous composition comprising partially fluorinated methacrylic polymers

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- Number: US 2014/0154519 A1
- Document ID: US20140154519A1
- Status: Published application
- Kind: A1
- Application number: 14/071,700
- Filed: 2013-11-05
- Published: 2014-06-05
- Earliest claimed: 2012-12-05
- Assignees: E. I. Du Pont de Nemours and Company
- Applicants: E I Du Pont De Nemours and Company
- Inventors: Michael Henry Ober; John Christopher Sworen; Ernest Byron Wysong; Kathleen L. Kanetsky
- Web page: https://patentgrep.com/patent/US20140154519A1

## CPC

- C09D 139/00: Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Coating compositions based on derivatives of such polymers
- C08F 220/24: containing perhaloalkyl radicals
- C09D 133/16: Homopolymers or copolymers of esters containing halogen atoms
- Y10T 428/4935: Impregnated naturally solid product [e.g., leather, stone, etc.]
- 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)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

A solvent-based non-aqueous fluorinated methacrylate polymer comprising repeating units in any sequence from (1) at least one fluorinated methacrylate, and (2) at least one non-fluorinated alkyl acrylate and (3) at least one non-fluorinated hydroxyalkyl methacrylate, provided that a) the repeating unit of fluorinated methacrylate is present in a range of about 40%-80% by weight of total monomers added, b) the repeating unit of non-fluorinated alkyl acrylate is present in a range of about 10%-35% by weight of total monomers added, and c) the repeating unit of non-fluorinated hydroxyalkyl methacrylate is present in a range of about 5%-25% by weight of total monomers added, and d) the total of all repeating units is 100% by weight.

## Claims

### Claim 1

A solvent-based non-aqueous fluorinated methacrylate polymer comprising repeating units in any sequence from (1) at least one fluorinated methacrylate, (2) at least one non-fluorinated alkyl acrylate, (3) at least one non-fluorinated hydroxyalkyl methacrylate, and 4) at least one amino-containing (meth)acrylate
provided that
a) the repeating unit of fluorinated methacrylate is present in a range of from 40% to 80% by weight of total monomers added,
b) the repeating unit of non-fluorinated alkyl acrylate is present in a range of from 10% to 35% by weight of total monomers added, and
c) the repeating unit of non-fluorinated hydroxyalkyl methacrylate is present in a range of from 5% to 25% by weight of total monomers added,
d) the repeating unit of the amino-containing (meth)acrylate is present in a range of from 0.5% to 15% by weight of total monomers added and
e) the total of all repeating units is 100% by weight.

### Claim 2 (depends on 1)

The polymer of claim 1 wherein the fluorinated methacrylate is:
wherein Rf is C2 to C10 fluoroalkyl optionally interrupted by 1 to 3 —O—, —CH2—, —CHF—, or combinations thereof;
Q is —R2-A-, —SO2—N(R2)—R2—O—, —CO—N(R3)—R2—O—, —CH2CH(OR3)CH—O—, —R2—SO2—N(R3)—O—, or —R2—O—C(O)—N(R3)—R2—O—;
A is O or S;
R1 is CH3;
R2 is C1 to C10 alkylene; and
R3 is H or C1 to C4 acyl.

### Claim 3 (depends on 2)

The polymer of claim 2 wherein Rf is C2 to C6, Q is —R2-A-, R1 is H or CH3.

### Claim 4 (depends on 3)

The composition of claim 3, wherein Rf is C6, R2 is C2 alkylene, and A is O.

### Claim 5 (depends on 1)

The polymer of claim 1 wherein the non-fluorinated alkyl acrylate is:
where R4 is C8 to C40 linear or branched alkyl; and R5 is H, or mixtures thereof.

### Claim 6 (depends on 5)

The polymer of claim 5 wherein R4 is selected from the group consisting of octyl, 2-ethylhexyl, decyl, isodecyl, lauryl, cetyl, or stearyl.

### Claim 7 (depends on 5)

The polymer of claim 5 wherein R4 is selected is selected from the group consisting of 2-ethylhexyl acrylate, lauryl acrylate and stearyl acrylate.

### Claim 8 (depends on 1)

The polymer of claim 1 wherein the hydroxyalkyl methacrylate is
wherein R6 is C2 to C4 alkyl; and
R7 is CH3 has an alkyl chain length in the range between 2 and 4 carbon atoms.

### Claim 9 (depends on 8)

The polymer of claim 8 is 2-hydroxyethyl methacrylate.

### Claim 10 (depends on 1)

The polymer of claim 1 wherein the amino-containing (meth)acrylate is:
wherein R8 is an ethylene or propylene group;
R9 is H or CH3;
R10 and R11 are each independently methyl, ethyl, or propyl groups.

### Claim 11 (depends on 10)

The polymer of claim 10, wherein the amino-containing (meth)acrylate is dimethylaminoethyl(meth)acrylate or diethylaminoethyl(meth)acrylate.

### Claim 12

A method for treating a leather substrate comprising contacting the leather substrate with a solvent-based fluorinated methacrylate polymer to provide water and oil repellency, wherein the fluorinated methacrylate polymer comprises repeating units in any sequence from (1) at least one fluorinated methacrylate, (2) at least one non-fluorinated alkyl acrylate, (3) at least one non-fluorinated hydroxyalkyl methacrylate, and 4) at least one amino-containing (meth)acrylate, provided that
a) the repeating unit of fluorinated methacrylate is present in a range of from 40% to 80% by weight of total monomers added,
b) the repeating unit of non-fluorinated alkyl acrylate is present in a range of from 10% to 35% by weight of total monomers added, and
c) the repeating unit of non-fluorinated hydroxyalkyl methacrylate is present in a range of from 5% to 25% by weight of total monomers added,
d) the repeating unit of the amino-containing (meth)acrylate is present in a range of from 1% to 20% by weight of total monomers added and
e) the total of all repeating units is 100% by weight.

### Claim 13 (depends on 12)

The method of claim 12 wherein the contacting is by spray, dipping, foam, nip, immersion, brush, roller, sponge, mat techniques.

### Claim 14 (depends on 12)

The method of claim 12 wherein the contacting is by spray, dipping, and brush techniques.

### Claim 15

A method for treating a hard surface substrate comprises contacting the hard surface substrate with a solvent-based fluorinated methacrylate polymer to provide water repellency, oil repellency, and stain resistance wherein the fluorinated methacrylate polymer comprises repeating units in any sequence from (1) at least one fluorinated methacrylate, (2) at least one non-fluorinated alkyl acrylate, (3) at least one non-fluorinated hydroxyalkyl methacrylate, and 4) at least one amino-containing (meth)acrylate,
provided that
a) the repeating unit of fluorinated methacrylate is present in a range of from 40% to 80% by weight of total monomers added,
b) the repeating unit of non-fluorinated alkyl acrylate is present in a range of from 10% to 35% by weight of total monomers added, and
c) the repeating unit of non-fluorinated hydroxyalkyl methacrylate is present in a range of from 5% to 25% by weight of total monomers added,
d) the repeating unit of the amino-containing (meth)acrylate is present in a range of from 1% to 20% by weight of total monomers added and
e) the total of all repeating units is 100% by weight.

### Claim 16 (depends on 15)

The method of claim 15 wherein the contacting is by brush, spray, roller, doctor blade, wipe and dip techniques.

### Claim 17 (depends on 15)

The method of claim 15 wherein the contacting is by spray and wet-on-wet techniques.

### Claim 18 (depends on 15)

The method of claim 15 wherein the hard surface substrate is unglazed concrete, brick, tile, stone, granite, limestone, grout, mortar, composite materials, terrazzo, gypsum board, marble, statuary, monuments, or wood.

### Claim 19 (depends on 14)

A substrate treated with the method of claim 14 which is unglazed concrete, brick, tile, stone, granite, limestone, grout, mortar, composite materials, terrazzo, gypsum board, marble, statuary, monuments, or wood.

### Claim 20 (depends on 1)

The polymer of claim 1 wherein the polymer excludes any repeating units derived from vinylidene chloride.