# US 9,752,060 B2 · Fluoroalkyl silicone compositions

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- Number: US 9,752,060 B2
- Document ID: US9752060B2
- Status: Granted
- Kind: B2
- Application number: 15/023,737
- Filed: 2014-10-01
- Published: 2016-08-11
- Granted: 2017-09-05
- Earliest claimed: 2013-10-04
- Assignees: 3M Innovative Properties Company
- Applicants: 3M Innovative Properties Company
- Inventors: Zai-Ming Qiu; Jitendra S. Rathore
- Web page: https://patentgrep.com/patent/US9752060B2

## CPC

- C09D 183/08: containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
- C08G 77/385: containing halogens
- C08L 83/08: containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C09J 7/401: {characterised by the release coating composition}
- C08G 77/12: containing silicon bound to hydrogen
- C08G 77/18: to alkoxy or aryloxy groups
- C09J 2427/005: in the release coating
- C09J 2433/00: Presence of (meth)acrylic polymer
- C09J 2483/00: Presence of polysiloxane
- C09J 2483/005: in the release coating
- 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)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H)

## Abstract

Provided is fluoroalkyl silicone of the formula (I): wherein each R1 is independently an alkyl or aryl; Rf is a perfluoroalkyl group, optionally substituted by one or more in-chain —O—, .S— or —NRf1— heteroatoms, where Rf1 is a perfluoroalkyl preferably a C1-C6 perfluoroalkyl; R3 is —H, —OR4; where R4 is a C1-C4 alkyl n is 0 to 2000; m may be zero; p may be zero, n+m+p is at least one; q is at least 3; R5 is H, alkyl, aryl-(CH2)n—CF2CHF—O—Rf; or R3; wherein the fluoroalkyl silicone has at least one fluorinated group of the formula (CH2)q—O—CF2CHF—O—Rf.

## Claims

### Claim 1

A fluoroalkyl silicone of the formula:
wherein
each R1 is independently an alkyl or aryl;
Rf is a perfluoroalkyl group, optionally substituted by one or more in-chain —O—, —S— or —NRf1— heteroatoms, where Rf1 is a perfluoroalkyl, preferably a C1-C6 perfluoroalkyl;
R3 is —H, —OR4; where R4 is a C1-C4 alkyl
n is 0 to 2000;
m may be zero;
p is at least one,
n+m+p is at least two;
q is at least 3;
R5 is H, alkyl, aryl, —(CH2)q—O—CF2CHF—O—Rf, or R3;
wherein the fluoroalkyl silicone has at least two fluorinated groups of the formula —(CH2)q—O—CF2CHF—O—Rf.

### Claim 2 (depends on 1)

The fluoroalkysilane of claim 1 wherein Rf is a C1-C6 perfluorolkyl group.

### Claim 3 (depends on 1)

The fluoroalkyl silicone of claim 1, wherein Rf is selected from —CF3, —CF2CF3, —C3F7, —C4F9, —C5F11, —C6F13, CF3O(CF2)2CF2—, (CF3)2N(CF2)2CF2—, —CF2CF(CF3)2 and C3F7OCF(CF3)CF2—.

### Claim 4 (depends on 1)

The fluoroalkyl silicone of claim 1 wherein Rf is of the formula CrF2r+1—(O—CsF2s)t, where r is at least 1, s is at least 2, and t is from 1 to 10.

### Claim 5 (depends on 4)

The fluoroalkyl silicone of claim 4 wherein each of subscripts r and s are 3 to 6.

### Claim 6 (depends on 1)

The fluoroalkyl silicone of claim 1 wherein Rf is of the formula CrF2r+1N(CrF2r+1)—CsF2r+1)—CsF2s—, where r is at least 1, and s is at least 2.

### Claim 7 (depends on 6)

The fluoroalkyl silicone of claim 6 wherein each of subscripts r, and s are 3 to 6.

### Claim 8 (depends on 1)

The fluoroalkyl silicone of claim 1 where the ratio of m to p is from 50:50 to 20:80.

### Claim 9 (depends on 1)

The fluoroalkyl silicone of claim 1 having a Mw of at least 400.

### Claim 10 (depends on 1)

The fluoroalkyl silicone of claim 1 wherein m is at least 2.

### Claim 11 (depends on 1)

The fluoroalkyl silicone of claim 1 wherein R5 is —(CH2)q—O—CF2CHF—O—Rf where q is at least 3 and Rf is a perfluoroalkyl group, optionally substituted by one or more in-chain —O—, —S— or —NRf1— heteroatoms.

### Claim 12 (depends on 1)

The fluoroalkyl silicone of claim 1 wherein p is at least 1 and R3 is H.

### Claim 13 (depends on 1)

The fluoroalkyl silicone of claim 1 wherein p is at least 1 and R3 is —O—R4, where R4 is C1-C4 alkyl.

### Claim 14 (depends on 1)

The fluoroalkyl silicone of claim 1 wherein p is 10 to 2000.

### Claim 15 (depends on 1)

A method of making the fluoroalkyl silicone of claim 1, comprising
hydrosilylation of a perfluoroalkyl alkenyl ether of the formula:
Rf—O—CHFCF2—O—(CH2)q−2CH═CH2, wherein
Rf is a perfluoroalkyl group, optionally substituted by one or more in-chain —O—, —S— or —NRf1— heteroatoms, where Rf1 is a perfluoroalkyl;
and q is at least 3;
with a with a hydrosilicone of the formula:
where
each R1 is independently an alkyl or aryl;
n is 0 to 2000; and
v may be zero;
R6 is H, alkyl, or aryl,
said hydrosilylation in the presence of a hydrosilylation catalyst;
with the proviso that the hydrosilicone contains at least two Si—H groups.

### Claim 16 (depends on 1)

A release liner comprising a backing and a layer of the cured coating of the fluoroalkyl silicone of claim 1 on at least one major surface of the backing.

### Claim 17 (depends on 16)

The release liner of claim 16 wherein at least one of R5 and R3 of the fluoroalkyl silicone is —OR4, where R4 is C1-C4 alkyl.

### Claim 18 (depends on 16)

The release liner of claim 16, wherein at least one of R5 and R3 of the fluoroalkyl silicone is H, cured with a vinyl silicone.

### Claim 19 (depends on 18)

The release liner of claim 18 wherein at least one of R5 and R3 of the fluoroalkyl silicone is H, and at least one of R5 and R3 of the fluoroalkyl silicone is —OR4 and is cured by hydrosilylation with a vinyl silicone, and moisture or photo-acid cured from Si—OR4.

### Claim 20 (depends on 1)

An adhesive article comprising (I) a release liner comprising a backing and a cured release coating comprising the fluoroalkyl silicone of claim 1 on at least one surface of the backing, and (II) a pressure-sensitive adhesive in contact with a surface of the release liner.

### Claim 21 (depends on 20)

The adhesive article according to claim 20, wherein the adhesive comprises a silicone adhesive, or an acrylate adhesive.