Fluorine-containing organopolysiloxane, a surface treatment composition comprising the same and an article treated with the composition

• US 7,794,843 B2
• Filed: 12/22/2006
• Issued: 09/14/2010
• Est. Priority Date: 12/26/2005
• Status: Active Grant

• Current Assignee: Shin-Etsu Chemical Company Limited
• Original Assignee: Shin-Etsu Chemical Company Limited
• Inventors: Kishita, Hirofumi, Yamane, Yuji, Yamaguchi, Koichi, Koike, Noriyuki
• Primary Examiner(s): Zimmer; Marc S
• Application Number:
  US11/643,988
• Publication Number:
  US 20070149746A1
• Time in Patent Office: 1,362 Days
• Field of Search: 528/35, 528/25, 528/31, 528/34, 528/42
• US Class Current: 428/447
• CPC Class Codes: C07F 7/21 Cyclic compounds having at least one ring containing silicon, but no carbon in the ring
• CPC Class Codes: C08G 65/007 containing fluorine
• CPC Class Codes: C08G 65/336 containing silicon
• CPC Class Codes: C08G 77/385 containing halogens
• CPC Class Codes: C08G 77/50 by carbon linkages C08G77/485 takes precedence
• CPC Class Codes: Y10T 428/31663 As siloxane, silicone or silane

Abstract

An organopolysiloxane represented by the following general formula (A), (B) or(C)
Si_nR¹_2n+2O_n−1  (A)
Si_nR¹_2nO_n  (B)
Si_nR¹_2n+2R²_kO_n−k  (C)

• • wherein R¹ may be the same with or different from each other and is a hydrogen atom or a monovalent organic group, R² is an alkylene group having 2 to 6 carbon atoms, n is an integer of from 2 to 40 and k is an integer of 1 to 3,
  • characterized in that at least two R¹'"'"'s are represented by the following formula (i):

• • wherein X is a hydrolyzable group, R³ is an alkyl group having 1 to 4 carbon atoms or a phenyl group, y is an integer of from 1 to 5 and a is 2 or 3; and
  • one SiOSi bond is replaced with a bond represented by the following formula (iii):
    SiQR_f²QSi  (iii)
  • wherein R_f¹ is a monovalent group containing a perfluoroether residue, R_f² is a divalent group containing a perfluoroether residue, and Q is a divalent organic group.

Claims

1. An organopolysiloxane represented by the following general formula (A), (B) or (C)

Si_nR¹_2n+2O_n−

1 

 

(A)

Si_nR¹_2nO_n 

 

(B)

Si_nR¹_2n+2R²_kO<sub>n−

k−

1</sub> 

 

(C)

wherein R¹ may be the same with or different from each other and is a hydrogen atom or a monovalent organic group, R² is an alkylene group having 2 to 6 carbon atoms, n is an integer of from 2 to 40 and k is an integer of 1 to 3, the formula (C) represents an organopolysiloxane containing a Si—

R²—

Si bond,

characterized in that at least two R¹'"'"'s are groups represented by the following formula (i);

2. The organopolysiloxane according to claim 1, wherein n is an integer of from 2 to 10.

3. The organopolysiloxane according to claim 1, wherein the organopolysiloxane is represented by the formula (A) or (C), and has a (SiO₂) unit.

4. The organopolysiloxane according to claim 1, wherein R¹ is an alkyl group having 1 to 4 carbon atoms or a phenyl group.

5. The organopolysiloxane according to claim 1, wherein the perfluoroether residue contains 1 to 500 repeating units represented by the following general formula:

—

C_gF_2gO—

wherein g is independently an integer of from 1 to 6.

6. The organopolysiloxane according to according to claim 1, wherein R_f² is selected from the groups represented by the following general formulas (5), (6), and (7):

7. The organopolysiloxane according to claim 1, wherein Q is a hydrocarbon group having 3 to 12 carbon atoms and may contain a bond selected from the group consisting of amide, ether, ester and vinyl bonds.

8. The organopolysiloxane according to claim 1, wherein X is selected from the group consisting of alkoxy groups, oxyalkoxy groups, acyloxy groups, alkenyloxy groups, and halogen atoms.

9. The organopolysiloxane according to claim 1, wherein X is selected from the group consisting of methoxy group, ethoxy group, isopropenoxy group and chlorine atom.

10. A surface treatment composition comprising, as an active ingredient, an organopolysiloxane represented by the following general formula (A), (B) or (C)

Si_nR¹_2n+2O_n−

1 

 

(A)

Si_nR¹_2nO_n 

 

(B)

Si_nR¹_2n+2R²_kO<sub>n−

k−

1</sub> 

 

(C)

wherein R¹ may be the same with or different from each other and is a hydrogen atom or a monovalent organic group, R² is an alkylene group having 2 to 6 carbon atoms, n is an integer of from 2 to 40 and k is an integer of 1 to 3, the formula (C) represents an organopolysiloxane containing a Si—

R²—

Si bond,

characterized in that at least two R¹'"'"'s are groups represented by the following formula (i);

11. The surface treatment composition according to claim 10, wherein n is an integer of from 2 to 10.

12. The surface treatment composition according to claim 10, wherein the organopolysiloxane is represented by the formula (A) or (C), and has a (SiO₂) unit.

13. The surface treatment composition according to claim 10, wherein R¹ is an alkyl group having 1 to 4 carbon atoms or a phenyl group.

14. The surface treatment composition according to claim 10, wherein the perfluoroether residue contains 1 to 500 repeating units represented by the following general formula:

—

C_gF_2gO—

wherein g is independently an integer of from 1 to 6.

15. The surface treatment composition according to claim 10, wherein R_f² is selected from the groups represented by the following general formulas (5), (6), and (7):

16. The surface treatment composition according to claim 10, wherein Q is a hydrocarbon group having 3 to 12 carbon atoms and may contain a bond selected from the group consisting of amide, ether, ester and vinyl bonds.

17. The surface treatment composition according to claim 10, wherein X is selected from the group consisting of alkoxy groups, oxyalkoxy groups, acyloxy groups, alkenyloxy groups, and halogen atoms.

18. The surface treatment composition according to claim 10, wherein X is selected from the group consisting of methoxy group, ethoxy group, isopropenoxy group and chlorine atom.

19. A coated article treated with a cured composition formed from a surface treatment composition comprising, as an active ingredient, an organopolysiloxane represented by the following general formula (A), (B) or (C)

Si_nR¹_2n+2O_n−

1 

 

(A)

Si_nR¹_2nO_n 

 

(B)

Si_nR¹_2n+2R²_kO<sub>n−

k−

l</sub> 

 

(C)

wherein R¹ may be the same with or different from each other and is a hydrogen atom or a monovalent organic group, R² is an alkylene group having 2 to 6 carbon atoms, n is an integer of from 2 to 40 and k is an integer of 1 to 3, the formula (C) represents an organopolysiloxane containing a Si—

R²—

Si bond,

characterized in that at least two R¹'"'"'s are groups represented by the following formula (i);

20. The coated article according to claim 19, wherein n is an integer of from 2 to 10.

21. The coated article according to claim 19, wherein the organopolysiloxane is represented by the formula (A) or (C), and has a (SiO₂) unit.

22. The coated article according to claim 19, wherein R¹ is an alkyl group having 1 to 4 carbon atoms or a phenyl group.

23. The coated article according to claim 19, wherein the perfluoroether residue contains 1 to 500 repeating units represented by the following general formula:

—

C_gF_2gO—

wherein g is independently an integer of from 1 to 6.

24. The coated article according to claim 19, wherein R_f² is selected from the groups represented by the following general formulas (5), (6), and (7):

25. The coated article according to claim 19, wherein Q is a hydrocarbon group having 3 to 12 carbon atoms and may contain a bond selected from the group consisting of amide, ether, ester and vinyl bonds.

26. The coated article according to claim 19, wherein X is selected from the group consisting of alkoxy groups, oxyalkoxy groups, acyloxy groups, alkenyloxy groups, and halogen atoms.

27. The coated article according to claim 19, wherein X is selected from the group consisting of methoxy group, ethoxy group, isopropenoxy group and chlorine atom.