Fluorine-containing organopolysiloxane, a surface treatment composition comprising the same and an article treated with the composition
An organopolysiloxane represented by the following general formula (A), (B) or(C) Si n R 1 2n+2 O n−1 (A) Si n R 1 2n O n (B) Si n R 1 2n+2 R 2 k O n−k (C) wherein R 1 may be the same with or different from each other and is a hydrogen atom or a monovalent organic group, R 2 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 R 1 's are represented by the following formula (i): wherein X is a hydrolyzable group, R 3 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 f 2 QSi (iii) wherein R f 1 is a monovalent group containing a perfluoroether residue, R f 2 is a divalent group containing a perfluoroether residue, and Q is a divalent organic group.
1. An organopolysiloxane represented by the following general formula (A), (B) or (C)
Si n R 1 2n+2 O n−1 (A)
Si n R 1 2n O n (B)
Si n R 1 2n+2 R 2 k O n−k−1 (C)
wherein R 1 may be the same with or different from each other and is a hydrogen atom or a monovalent organic group, R 2 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—R 2 —Si bond,
characterized in that at least two R 1 's are groups represented by the following formula (i):
wherein X is a hydrolyzable group, R 3 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 f 2 QSi (iii)
wherein R f 2 is a divalent group containing a perfluoroether residue, and Q is a divalent organic group.
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 (SiO 2 ) unit.
4. The organopolysiloxane according to claim 1 , wherein R 1 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 g F 2g O—
wherein g is independently an integer of from 1 to 6.
6. The organopolysiloxane according to according to claim 1 , wherein R f 2 is selected from the groups represented by the following general formulas (5), (6), and (7):
wherein Y may be the same with or different from each other and is a fluorine atom or a CF 3 group, r is an integer of from 2 to 6, d is an integer of from 1 to 3, each of m and n is an integer of from 0 to 200 with m+n ranging from 2 to 200, s is an integer of from 0 to 6, and the repeating units may be bonded randomly;
—C d F 2d (CF 2 CF 2 CF 2 O) 1 C d F 2d — (6)
wherein 1 is an integer of from 1 to 200 and d is an integer of from 1 to 3; and
wherein Y is a fluorine atom or a CF 3 group, d is an integer of from 1 to 3, each of m and n is an integer of from 0 to 200 with m+n ranging from 2 to 200, and the repeating units may be bonded randomly.
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 n R 1 2n+2 O n−1 (A)
Si n R 1 2n O n (B)
Si n R 1 2n+2 R 2 k O n−k−1 (C)
wherein R 1 may be the same with or different from each other and is a hydrogen atom or a monovalent organic group, R 2 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—R 2 —Si bond,
characterized in that at least two R 1 's are groups represented by the following formula (i):
wherein X is a hydrolyzable group, R 3 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 f 2 QSi (iii)
wherein R f 2 is a divalent group containing a perfluoroether residue, and Q is a divalent organic group;
and/or a partial condensate of hydrolyzates of the organopolysiloxane.
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 (SiO 2 ) unit.
13. The surface treatment composition according to claim 10 , wherein R 1 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 g F 2g O—
wherein g is independently an integer of from 1 to 6.
15. The surface treatment composition according to claim 10 , wherein R f 2 is selected from the groups represented by the following general formulas (5), (6), and (7):
wherein Y may be the same with or different from each other and is a fluorine atom or a CF 3 group, r is an integer of from 2 to 6, d is an integer of from 1 to 3, each of m and n is an integer of from 0 to 200 with m+n ranging from 2 to 200, s is an integer of from 0 to 6, and the repeating units may be bonded randomly;
—C d F 2d (CF 2 CF 2 CF 2 O) l C d F 2d — (6)
wherein l is an integer of from 1 to 200 and d is an integer of from 1 to 3; and
wherein Y is a fluorine atom or a CF 3 group, d is an integer of from 1 to 3, each of m and n is an integer of from 0 to 200 with m+n ranging from 2 to 200, and the repeating units may be bonded randomly.
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 n R 1 2n+2 O n−1 (A)
Si n R 1 2n O n (B)
Si n R 1 2n+2 R 2 k O n−k−l (C)
wherein R 1 may be the same with or different from each other and is a hydrogen atom or a monovalent organic group, R 2 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—R 2 —Si bond,
characterized in that at least two R 1 's are groups represented by the following formula (i):
wherein X is a hydrolyzable group, R 3 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 f 2 QSi (iii)
wherein R f 2 is a divalent group containing a perfluoroether residue, and Q is a divalent organic group;
and/or a partial condensate of hydrolyzates of the organopolysiloxane.
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 (SiO 2 ) unit.
22. The coated article according to claim 19 , wherein R 1 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 g F 2g O—
wherein g is independently an integer of from 1 to 6.
24. The coated article according to claim 19 , wherein R f 2 is selected from the groups represented by the following general formulas (5), (6), and (7):
wherein Y may be the same with or different from each other and is a fluorine atom or a CF 3 group, r is an integer of from 2 to 6, d is an integer of from 1 to 3, each of m and n is an integer of from 0 to 200 with m+n ranging from 2 to 200, s is an integer of from 0 to 6, and the repeating units may be bonded randomly;
—C d F 2d (CF 2 CF 2 CF 2 O) l C d F 2d — (6)
wherein 1 is an integer of from 1 to 200 and d is an integer of from 1 to 3; and
wherein Y is a fluorine atom or a CF 3 group, d is an integer of from 1 to 3, each of m and n is an integer of from 0 to 200 with m+n ranging from 2 to 200, and the repeating units may be bonded randomly.
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.