Polyfluoroalkylated alkenes and silane compounds prepared therefrom

Patent metadata

Field	Value
Publication number	US-9938307-B2
Application number	US-201515324743-A
Country	US
Kind code	B2
Filing date	Aug 11, 2015
Priority date	Aug 27, 2014
Publication date	Apr 10, 2018
Grant date	Apr 10, 2018

Abstract

Novel polyfluoroalkylated alkenes and silane compounds prepared therefrom are described.

First claim

What is claimed is:

1. A fluoroalkyl silane of the formula:
[R f —O—CHFCF 2 —O] x —R*—Si(X) q R 2 3-q ,

wherein
R f is a perfluoroalkyl group, optionally substituted by one or more in-chain —O—, or —NR f 1 — heteroatoms, where R f 1 is a perfluoroalkyl as previously defined;
R* is a C 2 -C 10 alkylene of valence x+1;
subscript x is at least two;
X is a hydrolysable group;
R 2 is a C 1 -C 4 alkyl group; and
subscript q is 1 to 3.

2. The fluoroalkyl silane of claim 1 wherein R f is a C 1 -C 6 perfluorolkyl group.

3. The fluoroalkyl silane of claim 1 , wherein R f is selected from —CF 3 , —CF 2 CF 3 , C 3 F 7 , —C 6 F 13 , CF 3 O(CF 2 ) 2 CF 2 —, (CF 3 ) 2 N(CF 2 ) 2 CF 2 —, —CF 2 CF(CF 3 ) 2 and C 3 F 7 OCF(CF 3 )CF 2 —.

4. The fluoroalkyl silane of claim 1 wherein R f is of the formula C a F 2a+1 —(O—C b F 2b ) c —, where a is at least 1, b is at least 2, and c may be a number from 1 to 10.

5. The fluoroalkyl silane of claim 4 wherein each of subscripts a and b are 3 to 6.

6. The fluoroalkyl silane of claim 1 wherein R f is of the formula C a F 2a+1 N(C a F 2a+1 )—C b F 2b —, where each a is at least 1, and b is at least 2.

7. The fluoroalkyl silane of claim 6 wherein each of subscripts a and b are 3 to 6.

8. A coating composition comprising the fluoroalkyl silane of claim 1 , a solvent an optional acid catalyst and an optional inorganic oxide particulate filler.

9. The coating composition of claim 8 , further comprising silica.

10. The coating composition of claim 9 wherein the silica is nanoparticle silica.

11. The coating composition of claim 9 wherein the silica is surface modified.

12. The coating composition of claim 9 further comprising one or more silane crosslinkers of the formula:
Si(X 1 ) z R 12 4-z
wherein each X 1 is independently hydroxyl, a hydrolyzable group, or a combination thereof; each R 12 is independently a C 1 -C 4 alkyl group; z is an integer of one to four.

13. The coating composition of claim 12 wherein z is four.

14. The coating composition of claim 13 comprising a mixture of silane crosslinkers where z is 3 and 4.

15. The coating composition of claim 13 comprising 1 to 20 weight percent of silane crosslinkers.

16. The coating composition of claim 9 comprising 1 to 20 wt % of silica.

17. The coating composition of claim 9 comprising:
a) 0.25 to 10 wt. % fluoroalkyl silane
b) 0 to 20 wt. % silica
c) 0 to 20 wt. % a silane crosslinker,
d) 0 to 10 wt. % of an acid catalyst;
in an organic solvent.

18. The coating composition of claim 9 further comprising 0.01 to about 10 weight percent of an acid catalyst.

19. The coating composition of claim 9 comprising 0.5 to 5 wt % fluoroalkylsilane.

20. The coating composition of claim 9 comprising 1 to 10 wt % nanoparticle silica.

21. The coating composition of claim 9 comprising 1 to 10 wt % silane crosslinker.

Assignees

• 3M Innovative Properties Co

Inventors

• Qiu Zai-Ming

Classifications

• C09D183/08

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

• C07F7/1836 Primary

  Chemistry & Metallurgy · mapped topic

• C09D5/00

  Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced {(electrically insulating plastics, resins or waxes H01B3/30)}; Filling pastes · CPC title

• C08K3/36

  Silica · CPC title

• C08G77/24

  halogen-containing groups · CPC title