Fluoroalkyl silicones

Patent metadata

Field	Value
Publication number	US-9994740-B2
Application number	US-201414785355-A
Country	US
Kind code	B2
Filing date	May 15, 2014
Priority date	May 31, 2013
Publication date	Jun 12, 2018
Grant date	Jun 12, 2018

Abstract

Novel fluoroalkyl silicones, and use thereof in release coatings, are described. The fluoroalkyl silicones are of the general formula: (I).

First claim

The invention claimed is:

1. A fluoroalkyl silicone of the formula:

wherein
each R 1 is independently an alkyl or aryl;
R f is perfluoroalkyl of the formula
—CF 2 —C q F 2q —X—C r F 2r —F, where q and r are independently 0 to 4,
X is a covalent bond, —O—, or —NR f 1 where R f 1 is C 1 -C 3 perfluoroalkyl;
R 3 is —H, —OR 4 , or —(CH 2 ) 3 —R 4 , where R 4 is C 1 -C 50 alkyl;
n is 0 to 2000;
m may be zero;
p may be zero, and n+p is at least one;
R 5 is H, alkyl, aryl —(C 3 H 6 )—O—R f , or R 3 ;
wherein the fluoroalkyl silicone has at least one —(C 3 H 6 )—O—R f group.

2. The fluoroalkyl silicone of claim 1 where the ratio of n to m is greater than one.

3. The fluoroalkyl silicone of claim 1 where the ratio of n to m is greater than ten.

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

5. The fluoroalkyl silicone of claim 1 wherein R 5 is —(C 3 H 6 )—O—R f .

6. The fluoroalkyl silicone of claim 1 wherein p is at least 1 and R 3 is H.

7. The fluoroalkyl silicone of claim 1 wherein p is at least 1 and R 3 is —O—R 4 , where R 4 is C 1 -C 4 alkyl.

8. The fluoroalkyl silicone of claim 1 wherein p is at least 1 and R 3 is —(C 2 H 4 )—R′, where R′ is C 1 -C 48 alkyl.

9. The fluoroalkyl silicone of claim 1 wherein R f contains 2 to 6 perfluorinated carbon atoms.

10. The fluoroalkyl silicone of claim 1 wherein the ratio of m to p is 100:0 to 10:90.

11. A method of making the fluoroalkyl silicone of claim 1 , comprising
hydrosilylation in the presence of a hydrosilylation catalyst of a perfluoroalkyl allyl ether of the formula:
R f —OCH 2 CH═CH 2 , where R f is perfluoroalkyl of the formula
—CF 2 —C q F 2q —X—C r F 2r —F, where q and r are independently 0 to 4; X is a covalent bond, —O—, or NR f 1 , where R f 1 is a C 1 -C 50 alkyl,
with a hydrosilicone of the formula:

 where
each R 1 is independently an alkyl or aryl;
n is 0 to 2000; and
q may be zero;
R 6 is H, alkyl or aryl,
with the proviso that the hydrosilicone contains at least one Si—H group.

12. The method of claim 11 wherein the hydrosilylation product is of the formula:

where
n is 0 to 2000;
m may be zero;
s may be zero to 2000;
R 7 is H, alkyl, aryl or —(C 3 H 6 )—OR f
o is 1;
with the proviso that the silicone contains at least one Si—H group and at least one —(C 3 H 6 )—O—R f group.

13. The method of claim 12 comprising the further step of alkoxylation of the Si—H groups with an alcohol of the formula R 4 —OH, where R 4 is C 1 -C 4 alkyl.

14. A product made by the method claim 13 of the formula:

wherein
n is 0 to 2000;
m is at least one;
s may be zero;
t may be zero;
R 8 is H, alkyl or aryl or OR 4 , where R 4 is H or C 1 -C 15 alkyl;
t may be zero;
with the proviso that the silicone contains at least one, preferably at least two Si—OR 4 groups and at least 1 Si—H group.

15. The method of claim 12 comprising the further step of hydrosilylation of the Si—H groups with a compound of the formula CH 2 ═CH—R 4 , where R 4 is C 1 -C 50 alkyl in the presence of a hydrosilylation catalyst.

16. A product made by the method of claim 15 of the formula:

wherein
n is 0 to 2000;
m is at least one;
s may be zero;
R 9 is alkyl, aryl or —(C 3 H 6 )—R 4 , where R 4 is C 1 -C 50 alkyl;
with the proviso that the silicone contains at least one —(C 3 H 6 )—R 4 group.

17. The method of claim 12 comprising the further step of crosslinking the silicone with a vinyl silicone polymer.

18. 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.

19. The release liner of claim 18 wherein at least one of R 5 and R 3 of the fluoroalkyl silicone is —OR 4 , where R 4 is C 1 -C 4 alkyl.

20. The release liner of claim 18 , wherein at least one of R 5 and R 3 of the fluoroalkyl silicone is H, cured with a vinyl silicone.

21. The release liner of claim 18 wherein at least one of R 5 and R 3 of the fluoroalkyl silicone is H, and at least one of R 5 and R 3 of the fluoroalkyl silicone is —OR 4 and is cured by hydrosilylation with a vinyl silicone, and moisture or photo-acid cured from Si—OR 4 .

22. The release liner of claim 19 , wherein the fluoroalkyl silicone is photo irradiation cured in the presence of a photoacid generator.

23. 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.

Assignees

• 3M Innovative Properties Co

Inventors

• Qiu Zai-Ming
• Rathore Jitendra S

Classifications

• C09J2483/005

  in the release coating · CPC title

• C09J7/201 Primary

  characterised by the release coating composition on the carrier layer · CPC title

• C09D183/08 Primary

  containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen · CPC title

• C09J7/401

  characterised by the release coating composition · CPC title

• C09J2483/00

  Presence of polysiloxane · CPC title