IP Library Granted Patent US 12,448,540
Granted Patent B2
US 12,448,540 · App. 18/761,449 · Granted Oct 21, 2025

Fluorinated ether compound, fluorinated ether composition, coating liquid and article

Inventors: Taiki Hoshino (Tokyo, JP); Kiyotaka Takao (Tokyo, JP); Kazue Toda (Tokyo, JP); Kenji Ishizeki (Tokyo, JP); Akira Isobe (Tokyo, JP)
Assignee: AGC Inc.
C09D201/04B32B33/00C07F7/1804C08F259/08C08G65/007C08G65/329C08G65/336C09D171/00C09D201/10B32B2307/7265B32B2307/746
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Quick Facts
Patent No.
US 12,448,540
App. No.
18/761,449
Granted
Oct 21, 2025
Kind
B2
Abstract

A fluorinated ether compound is represented by formula: [X 2 3-n2 R 23 n2 Si—R 22 —] 3 C—R 21 —[N(R 2 )C(O)] p2 —(R f2 O) m2 -Q 2 -[C(O)N(R 2 )] p2 —R 21 —C[—R 22 —SiR 23 n2 X 2 3-n2 ] 3 . R f2 is a fluoroalkylene group having no branched structure, Q 2 is a fluoroalkylene group having no branched structure, R 2 is a hydrogen atom or an alkyl group, R 21 is a single bond, an alkylene group, an alkylene group comprising an etheric oxygen atom at its terminal on the side bonded to [X 2 3-n2 R 23 n2 Si—R 22 —] 3 C, an alkylene group with at least two carbon atoms comprising an etheric oxygen atom between its carbon-carbon atoms, or an alkylene group with at least two carbon atoms comprising an etheric oxygen atom between its carbon-carbon atoms and at its terminal on the side bonded to [X 2 3-n2 R 23 n2 Si—R 22 —] 3 C, R 22 is an alkylene group, or the like, R 23 is a hydrogen atom or a monovalent hydrocarbon group, and X 2 is a hydrolyzable group.

Claims (54)

1. A fluorinated ether compound represented by formula (2):

[X 2 3-n2 R 23 n2 Si—R 22 —] 3 C—R 21 —[N(R 2 )C(O)] p2 —(R f2 O) m2 -Q 2 -[C(O)N(R 2 )] p2 —R 21 —C[—R 22 —SiR 23 n2 X 2 3-n2 ] 3   (2)

wherein R f2 is a fluoroalkylene group having no branched structure,

m2 is an integer of from 2 to 210,

(R f2 O) m2 is one composed of the same type or at least two types of R f2 O different in number of carbon atoms,

Q 2 is a fluoroalkylene group having no branched structure,

R 2 is a hydrogen atom or an alkyl group,

p2 is 0 or 1, and two p2 are the same or different,

R 21 is a single bond, an alkylene group, an alkylene group comprising an etheric oxygen atom at its terminal on the side bonded to [X 2 3-n2 R 23 n2 Si—R 22 —] 3 C, an alkylene group with at least two carbon atoms comprising an etheric oxygen atom between its carbon-carbon atoms, or an alkylene group with at least two carbon atoms comprising an etheric oxygen atom between its carbon-carbon atoms and at its terminal on the side bonded to [X 2 3-n2 R 23 n2 Si—R 22 —] 3 C,

two R 21 are the same group or different groups,

R 22 is an alkylene group or an alkylene group with at least two carbon atoms comprising an etheric oxygen atom between its carbon-carbon atoms,

R 23 is a hydrogen atom or a monovalent hydrocarbon group,

X 2 is a hydrolyzable group,

n2 is an integer of from 0 to 2, and

six [—R 22 —SiR 23 n2 X 2 3-n2 ] are the same group or different groups.

2. The fluorinated ether compound according to claim 1 , wherein R 22 is an alkylene group.

3. The fluorinated ether compound according to claim 1 , wherein p2 is 1.

4. The fluorinated ether compound according to claim 2 , wherein p2 is 1.

5. The fluorinated ether compound according to claim 1 , wherein

(R f2 O) m2 -Q 2 - is -Q 21 -(R F2 O) m20 -Q 22 -:

wherein Q 21 is a single bond, a fluoroalkylene group comprising at least one hydrogen atom and having no branched structure, a fluoroalkylene group comprising at least one hydrogen atom and having no branched structure, which has an etheric oxygen atom at its terminal on the side bonded to (R F2 O) m20 , a fluoroalkylene group with at least two carbon atoms comprising at least one hydrogen atom and having no branched structure, which has an etheric oxygen atom between its carbon-carbon atoms, or a fluoroalkylene group with at least two carbon atoms comprising at least one hydrogen atom and having no branched structure, which has 10 or less etheric oxygen atoms between its carbon-carbon atoms and at its terminal on the side bonded to (R F2 O) m20 ,

R F2 is a perfluoroalkylene group having no branched structure,

m20 is an integer of from 2 to 200,

(R F2 O) m20 is one composed of the same type or at least two types of R F2 O different in number of carbon atoms, and

Q 22 is a perfluoroalkylene group having no branched structure, a fluoroalkylene group comprising at least one hydrogen atom and having no branched structure, or a fluoroalkylene group with at least two carbon atoms comprising at least one hydrogen atom and having no branched structure, which has an etheric oxygen atom between its carbon-carbon atoms.

6. The fluorinated ether compound according to claim 5 , wherein R F2 is a C 1-6 perfluoroalkylene group.

7. The fluorinated ether compound according to claim 5 , wherein m20 is at least 5.

8. The fluorinated ether compound according to claim 6 , wherein m20 is at least 5.

9. The fluorinated ether compound according to claim 4 , wherein

—(R f2 O) m2 -Q 2 - is -Q 21 -(R F2 O) m20 -Q 22 -:

wherein Q 21 is a single bond, a fluoroalkylene group comprising at least one hydrogen atom and having no branched structure, a fluoroalkylene group comprising at least one hydrogen atom and having no branched structure, which has an etheric oxygen atom at its terminal on the side bonded to (R F2 O) m20 , a fluoroalkylene group with at least two carbon atoms comprising at least one hydrogen atom and having no branched structure, which has an etheric oxygen atom between its carbon-carbon atoms, or a fluoroalkylene group with at least two carbon atoms comprising at least one hydrogen atom and having no branched structure, which has 10 or less etheric oxygen atoms between its carbon-carbon atoms and at its terminal on the side bonded to (R F2 O) m20 ,

R F2 is a perfluoroalkylene group having no branched structure,

m20 is an integer of from 2 to 200,

(R F2 O) m20 is one composed of the same type or at least two types of R F2 O different in number of carbon atoms, and

Q 22 is a perfluoroalkylene group having no branched structure, a fluoroalkylene group comprising at least one hydrogen atom and having no branched structure, or a fluoroalkylene group with at least two carbon atoms comprising at least one hydrogen atom and having no branched structure, which has an etheric oxygen atom between its carbon-carbon atoms.

10. The fluorinated ether compound according to claim 9 , wherein R F2 is a C 1-6 perfluoroalkylene group.

11. The fluorinated ether compound according to claim 9 , wherein m20 is at least 5.

12. The fluorinated ether compound according to of claim 10 , wherein m20 is at least 5.

13. The fluorinated ether compound according to any of claim 1 , wherein

when p2 is 0, R 21 is a C 1-4 alkylene group, and

when p2 is 1, R 21 is a single bond or a C 1-4 alkylene group.

14. The fluorinated ether compound according to claim 4 , wherein

when p2 is 0, R 21 is a C 1-4 alkylene group, and

when p2 is 1, R 21 is a single bond or a C 1-4 alkylene group.

15. The fluorinated ether compound according to claim 5 , wherein

when p2 is 0, R 21 is a C 1-4 alkylene group, and

when p2 is 1, R 21 is a single bond or a C 1-4 alkylene group.

16. The fluorinated ether compound according to claim 12 , wherein

when p2 is 0, R 21 is a C 1-4 alkylene group, and

when p2 is 1, R 21 is a single bond or a C 1-4 alkylene group.

17. The fluorinated ether compound according to claim 1 , wherein R 22 is a C 2-6 alkylene group, or a C 3-8 alkylene group comprising an etheric oxygen atom between carbon atoms.

18. The fluorinated ether compound according to claim 4 , wherein R 22 is a C 2-6 alkylene group, or a C 3-8 alkylene group comprising an etheric oxygen atom between carbon atoms.

19. The fluorinated ether compound according to claim 5 , wherein R 22 is a C 2-6 alkylene group, or a C 3-8 alkylene group comprising an etheric oxygen atom between carbon atoms.

20. The fluorinated ether compound according to claim 16 , wherein R 22 is a C 2-6 alkylene group, or a C 3-8 alkylene group comprising an etheric oxygen atom between carbon atoms.

Priority Claims (1)
JP 2015-171986 · Sep 1, 2015 · national
Continuity (5)
Continuation 17038304 · Sep 30, 2020
Continuation 16715155 · Dec 16, 2019
Continuation 15877489 · Jan 23, 2018
Continuation PCTJP2016075354 · Aug 30, 2016
Related Publication 20240352278A1 · Oct 24, 2024
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