Functional, partially-fluorinated silanes

Patent metadata

Field	Value
Publication number	US-11267829-B2
Application number	US-201817274660-A
Country	US
Kind code	B2
Filing date	Dec 20, 2018
Priority date	Sep 10, 2018
Publication date	Mar 8, 2022
Grant date	Mar 8, 2022

Abstract

Functional, partially-fluorinated silane compound according to Formula (I): wherein: X is CH2=CH— or CHCH2—; R1 and R2 are linear or branched alkylenes having 1 to 4 carbon atoms; Rf is a perfluoro(alkylene) group having 1 to 8 carbon atoms and, optionally, at least one catenary heteroatom selected from the group consisting of O and N; c is equal to the number of carbon atoms in X; and Y is —Cl or —OR, wherein R is a linear or branched alkyl having 1 to 4 carbon atoms. In some embodiments, Y is —O(CH2)xCH3 wherein x is an integer from 0 to 3 are described. Methods of making and using such functional, partially-fluorinated silane compounds are also described

First claim

What is claimed is:

1. A functional, partially-fluorinated silane compound according to Formula I:
X—O—R 1 —R f —R 2 —O—(CH 2 ) c —Si—Y 3   (1)

wherein: X is CH 2 ═CH— or CH 2 ═CHCH 2 —;
R 1 and R 2 are linear or branched alkylenes having 1 to 4 carbon atoms;
R f is a perfluoro(alkylene) group having 1 to 8 carbon atoms and, optionally, at least one catenary heteroatom selected from the group consisting of O and N;
c is equal to the number of carbon atoms in X; and
Y is —Cl or —OR, wherein R is a linear or branched alkyl having 1 to 4 carbon atoms.

2. The compound of claim 1 , wherein R 1 and R 2 are linear alkylenes, and the compound is a functional, partially-fluorinated silane compound according to Formula II:
X—O—(CH 2 ) a —R f —(CH 2 ) b —O—(CH 2 ) c —Si—Y 3   (II)

wherein a and b are integers from 1 to 4.

3. The compound of claim 2 , wherein a is equal to b.

4. The compound of claim 3 , wherein a and b are both 1, and the compound is a functional, partially-fluorinated silane compound according to Formula III:
X—O—CH 2 —R f —CH 2 —O—(CH 2 ) c —Si—Y 3 .  (III)

5. The compound of claim 1 , wherein Y is —O(CH 2 ) x CH 3 , wherein x is an integer from 0 to 3.

6. The compound of claim 5 , wherein x is 0, such that Y is —OCH 3 .

7. The compound of claim 1 , wherein X is CH 2 ═CH—.

8. The compound of claim 1 , wherein X is CH 2 ═CHCH 2 —.

9. The compound of claim 1 , wherein R f is a linear or branched perfluoro(alkylene) group.

10. The compound of claim 9 , wherein R f is a linear perfluoro(alkylene) group having the formula (CF 2 ) n , wherein n is an integer from 1 to 4.

11. The compound 10, wherein X is CH 2 ═CH— and n is 2 or 3.

12. The compound 10, wherein X is CH 2 ═CH—CH 2 — and n is an integer from 2 to 4.

13. An article comprising a first composition comprising a fluoropolymer, a second composition comprising a silicone polymer, wherein the second composition is in contact with and bonded to the first composition, wherein at last one of the first composition and the second composition comprises a functional, partially-fluorinated silane compound according to of claim 1 .

14. The article of claim 13 , wherein the first composition comprises at least a portion of the partially-fluorinated silane compound.

15. The article of claim 13 , wherein the second composition comprises at least a portion of the partially-fluorinated silane compound.

16. The article according to claim 13 , wherein the first composition comprises at least a portion of the partially-fluorinated silane compound, and the second composition comprises at least a portion of the partially-fluorinated silane compound.

17. The article of claim 13 , wherein the fluoropolymer is a peroxide-curable fluoropolymer.

18. The article of claim 17 , wherein the peroxide-curable fluoropolymer comprises a curesite group selected from the group consisting of Br, I, CN or a combination thereof.

19. The article of claim 13 , wherein the article is a hose, an O-rings, a seal, a diaphragm, a valve, or a container, optionally wherein the hose is a turbo charger hose or a fuel line.

20. A method of preparing the functional, partially-fluorinated silane compound of claim 1 , comprising:
(i) providing a partially-fluorinated dialkylene having the formula:
X—O—R 1 —R f —R 2 —O—X

wherein X is CH 2 ═CH— or CH 2 ═CHCH 2 —;
R 1 and R 2 are linear or branched alkylenes having 1 to 4 carbon atoms; and
R f is a perfluoro(alkylene) group having 1 to 8 carbon atoms and, optionally, at least one catenary heteroatom selected from the group consisting of O and N; and
(ii) monohydrosilylating the partially-fluorinated dialkylene with trichlorosilane using a platinum catalyst to form a functional, partially-fluorinated, trichlorosilane compound

wherein c is equal to the number of carbon atoms in X.

21. The method of claim 20 , wherein providing a partially-fluorinated dialkylene comprises reacting a diol having a formula H—O—R 1 —R f —R 2 —O—H with a compound having a formula X—Z, wherein Z is selected from the group consisting of Br, Cl, I, and —OC(O)CH 3 to form the partially-fluorinated dialkylene having the formula X—O—R 1 —R f —R 2 —O—X.

22. The method according to claim 20 , wherein: R f is a linear perfluoro(alkylene) group having the formula (CF 2 ) n , wherein n is an integer from 2 to 4; and R 1 and R 2 are —(CH 2 )—.

Assignees

• 3M Innovative Properties Co

Inventors

• Mitchell Michael H
• Guerra Miguel A
• Nguyen Tho Q

Classifications

• C08G77/442

  containing vinyl polymer sequences · CPC title

• C08L83/04

  Polysiloxanes · CPC title

• C07F7/1892 Primary

  by reactions not provided for in C07F7/1876 - C07F7/1888 · CPC title

• C07F7/1804 Primary

  Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896) · CPC title

• C07F7/122

  by reactions involving the formation of Si-C linkages (hydrosilylation reactions C07F7/14; direct synthesis C07F7/16) · CPC title