IP Library › Granted Patent US 12,071,563

Granted Patent B2

US 12,071,563 · App. 17/038,304 · Granted Aug 27, 2024

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

Inventors: Taiki Hoshino (Chiyoda-ku, JP); Kiyotaka Takao (Chiyoda-ku, JP); Kazue Toda (Chiyoda-ku, JP); Kenji Ishizeki (Chiyoda-ku, JP); Akira Isobe (Chiyoda-ku, JP)

Assignee: AGC Inc.

C09D201/04 B32B33/00 C07F7/1804 C08F259/08 C08G65/007 C08G65/329 C08G65/336 C09D171/00 C09D201/10 B32B2307/7265 B32B2307/746

View Patent ↗

Loading inventors, assignments & file history…

Monitor This Case

Get email alerts when status or documents change.

Order Certified Copies

Most orders are placed with the USPTO same day — all within 24 business hours.

Order via The Patent Place →

Pre-filled with this patent's details

Quick Facts

Patent No.: US 12,071,563
App. No.: 17/038,304
Granted: Aug 27, 2024
Kind: B2

External Links

USPTO Patent Center↗ Full Patent PDF↗

Abstract

To provide a fluorinated ether compound, a fluorinated ether composition and a coating liquid that are able to form a surface layer which is excellent in water/oil repellency, abrasion resistance, fingerprint stain removability, lubricity and outer appearance, and an article having such a surface layer. A fluorinated ether compound represented by A 1 -O—(R f1 O) m1 Q 1 -[C(O)N(R 1 )] p1 —R 11 —C[—R 12 —SiR 13 n1 X 1 3-n1 ] 3 , wherein A 1 is a C 1-20 perfluoroalkyl group; R f1 is a fluoroalkylene group having no branched structure; m1 is an integer from 2 to 210; Q 1 is a single bond or a fluoroalkylene group having no branched structure; R 1 is a hydrogen atom, etc.; p1 is 0 or 1; R 11 is a single bond, an alkylene group, etc.; R 12 is an alkylene group, etc.; R 13 is a monovalent hydrocarbon group, etc.; X 1 is a hydrolyzable group; and n1 is an integer of from 0 to 2.

Claims (161)

1. A method for producing a compound represented by the following formula (17G), by reacting a compound represented by the following formula (14) with H 2 N—R 11 —C(—R 12′ —CH═CH 2 ) 3 ,

A 1 -O—(CF 2 CF 2 O)(CF 2 CF 2 O)(R F1 O) x —CF 2 —C(O)OR 10 (14)

A 1 -O—(CF 2 CF 2 O)(CF 2 CF 2 O)(R F1 O) x —CF 2 —C(O)NH—R 11 —C(R 12′ —CH═CH 2 ) 3 (17G)

wherein

A 1 is a C 1-20 perfluoroalkyl group,

R F1 is a perfluoroalkylene group having no branched structure,

x is an integer of from 1 to 198,

R 10 is an alkyl group,

R 11 is a single bond, an alkylene group, an alkylene group having an etheric oxygen atom at its terminal, which is the terminal on the side bonded to C(—R 12′ —CH═CH 2 ), an alkylene group with at least two carbon atoms, having an etheric oxygen atom between its carbon-carbon atoms, or an alkylene group with at least two carbon atoms, having an etheric oxygen atom between its carbon-carbon atoms and at its terminal, which is the terminal on the side bonded to C(—R 12′ —CH═CH 2 );

R 12′ is an alkylene group, an alkylene group having an etheric oxygen atom at its terminal, or an alkylene group with at least two carbon atoms, having an etheric oxygen atom between its carbon-carbon atoms, and

(R F1 O) x may be one composed of at least two types of R F1 O.

2. A method for producing a compound represented by the following formula (1G), by reacting a compound represented by the formula (17G) obtained in claim 1 with HSiR 13 n1 X 1 3-n1 ,

A 1 -O—(CF 2 CF 2 O)(CF 2 CF 2 O)(R F1 O) x —CF 2 —C(O)NH—R 11 —C[—R 12 —CH 2 CH 2 —SiR 13 n1 X 1 3-n1 ] 3 (1G)

wherein

R 13 is a hydrogen atom or a monovalent hydrocarbon group,

X 1 is a hydrolyzable group, and

n 1 is an integer of from 0 to 2.

3. A method for producing a compound represented by the following is formula (17H), by reacting a compound represented by the following formula (14H) with H 2 N—R 11 —C(—R 12′ —CH═CH 2 ) 3 ,

A 1 -O—CHFCF 2 OCH 2 —(CF 2 O)(R F1 O) x —CF 2 —C(O)OR 10 (14H)

A 1 -O—CHFCF 2 OCH 2 —(CF 2 O)(R F1 O) x —CF 2 —C(O)NH—R 11 —C(—R 12′ —CH═CH 2 ) 3 (17H)

wherein

A 1 is a C 1-20 perfluoroalkyl group,

R F1 is a perfluoroalkylene group having no branched structure,

x is an integer of from 1 to 198,

R 10 is an alkyl group,

R 11 is a single bond, an alkylene group, an alkylene group having an etheric oxygen atom at its terminal, which is the terminal on the side bonded to C(—R 12′ —CH═CF 2 ), an alkylene group with at least two carbon atoms, having an etheric oxygen atom between its carbon-carbon atoms, or an alkylene group with at least two carbon atoms, having an etheric oxygen atom between its carbon-carbon atoms and at its terminal, which is the terminal on the side bonded to C(—R 12′ —CH═CH 2 ),

(R F1 O) x may be one composed of at least two types of R F1 O.

4. A method for producing a compound represented by the following formula (1H), by reacting a compound represented by the formula (17H) obtained in claim 3 with HSiR 13 n1 X 1 3-n1 ,

A 1 -O—CHFCF 2 OCH 2 —(CF 2 O)(R F1 O) x —CF 2 —C(O)NH—R 11 —C[—R 12 —CH 2 CH 2 —SiR 13 n1 X 1 3-n1 ] 3 (1H)

wherein

R 13 is a hydrogen atom or a monovalent hydrocarbon group,

X 1 is a hydrolyzable group, and

n1 is an integer of from 0 to 2.

5. A method for producing a compound represented by the following formula (17I), by reacting a compound represented by the following formula (14I) with H 2 N—R 11 —C(—R 12′ —CH 2 CH═CH 2 ) 3 ,

A 1 -O—(R F1 O) x -Q 12 -C(O)OR 10 (14I)

A 1 -O—(R F1 O) x -Q 12 -C(O)NH—R 11 —C(—R 12′ —CH═CH 2 ) 3 (17I)

wherein

A 1 is a C 1-20 perfluoroalkyl group,

R F1 is a perfluoroalkylene group having no branched structure,

x is an integer of from 1 to 198,

Q 12 is a perfluoroalkylene group having no branched structure,

R 10 is an alkyl group,

R 11 is a single bond, an alkylene group, an alkylene group having an etheric is oxygen atom at its terminal, which is the terminal on the side bonded to C(—R 12′ —CH═CH 2 ), an alkylene group with at least two carbon atoms, having an etheric oxygen atom between its carbon-carbon atoms, or an alkylene group with at least two carbon atoms, having an etheric oxygen atom between its carbon-carbon atoms and at its terminal, which is the terminal on the side bonded to C(—R 12′ —CH═CH 2 ),

(R F1 O) x may be one composed of at least two types of R F1 O.

6. A method for producing a compound represented by the following formula (1I), by reacting a compound represented by the formula (17I) obtained in claim 5 with HSiR 13 n1 X 1 3-n1 ,

A 1 -O—(R F1 O) x -Q 12 -C(O)NH—R 11 —C[—R 12 —CH 2 CH 2 —SiR 13 n1 X 1 3-n1 ] 3 (1I)

wherein

R 13 is a hydrogen atom or a monovalent hydrocarbon group,

X1 is a hydrolyzable group, and

n1 is an integer of from 0 to 2.

7. A method for producing a compound represented by the following formula (17J), by reacting a compound represented by the following formula (15) with a compound represented by the following formula (30) in the presence of a basic compound,

A 1 -O—(CF 2 CF 2 O)(CF 2 CF 2 O)(R F1 O) x —CF 2 —CH 2 OH (15)

CF 2 ═CFOCF 2 CF 2 CF 2 —C(O)NH—R 11 —C(—R 12′ —CH═CH 2 ) 3 (30)

A 1 -O—(CF 2 CF 2 O)(CF 2 CF 2 O)(R F1 O) x —CF 2 CH 2 OCF 2 CHFOCF 2 CF 2 CF 2 —C(O)NH—R 11 —C(—R 12′ —CH═CH 2 ) 3 (17J)

wherein

A 1 is a C 1-20 perfluoroalkyl group,

R F1 is a perfluoroalkylene group having no branched structure,

x is an integer of from 1 to 198,

(R F1 O) x may be one composed of at least two types of R F1 O.

8. A method for producing a compound represented by the following formula (1J), by reacting a compound represented by the formula (17J) obtained in claim 7 with HSiR 13 n1 X 1 3-n1 ,

A 1 -O—(CF 2 CF 2 O)(CF 2 CF 2 O)(R F1 O) x —CF 2 CH 2 OCF 2 CHFOCF 2 CF 2 CF 2 —C(O)NH—R 11 —C[—R 12 —CH 2 CH 2 —SiR 13 n1 X 1 3-n1 ] 3 (1J)

wherein

R 13 is a hydrogen atom or a monovalent hydrocarbon group,

X 1 is a hydrolyzable group, and

n1 is an integer of from 0 to 2.

9. A method for producing a compound represented by the following formula (17K), by reacting a compound represented by the following formula (11) with a compound represented by the following formula (30) in the presence of a basic compound,

A 1 -O—CHFCF 2 OCH 2 —(CF 2 O)(R F1 O) x —CF 2 —CH 2 OH (11)

CF 2 ═CFOCF 2 CF 2 CF 2 —C(O)NH—R 11 —C(—R 12′ —CH═CH 2 ) 3 (30)

A 1 -O—CHFCF 2 OCH 2 —(CF 2 O)(R F1 O) x —CF 2 CH 2 OCF 2 CHFOCF 2 CF 2 CF 2 —C(O)NH—R 11 —C(—R 12 —CH—CH 2 ) 3 (17K)

wherein

A 1 is a C 1-20 perfluoroalkyl group,

R F1 is a perfluoroalkylene group having no branched structure,

x is an integer of from 1 to 198,

(R F1 O) x may be one composed of at least two types of R F1 O.

10. A method for producing a compound represented by the following is formula (1k), by reacting a compound represented by the formula (17K) obtained in claim 9 with HSiR 13 n1 X 1 3-n1 ,

A 1 -O—CHFCF 2 OCH 2 —(CF 2 O)(R F1 O) x —CF 2 CH 2 OCF 2 CHFOCF 2 CF 2 CF 2 —C(O)NH—R 11 —C—[R 12 —CH 2 CH 2 —SiR 13 n1 X 1 3-n1 ] 3 (1K)

wherein

R 13 is a hydrogen atom or a monovalent hydrocarbon group,

X 1 is a hydrolyzable group, and

n1 is an integer of from 0 to 2.

11. A method for producing a compound represented by the following formula (17I), by reacting a compound represented by the following formula (15C) with a compound represented by the following formula (30) in the presence of a basic compound,

A 1 O—(R F1 O) x —R F CH 2 OH (15C)

CF 2 ═CFOCF 2 CF 2 CF 2 —C(O)NH—R 11 —C(—R 12′ —CH═CH 2 ) 5 (30)

A 1 -O—(R F1 O) x —R F CH 2 OCF 2 CHFOCF 2 CF 2 CF 2 —C(O)NH—R 11 —C(—R 12′ —CH═CH 2 ) 3 (17L)

wherein

A 1 is a C 1-20 perfluoroalkyl group,

R F1 is a perfluoroalkylene group having no branched structure,

R F is a perfluoroalkylene group having no branched structure,

x is an integer of from 1 to 198,

R 10 is an alkyl group,

R 11 is a single bond, an alkylene group, an alkylene group having an etheric oxygen atom at its terminal (which is the terminal on the side bonded to C(—R 12′ —CH═CH 2 ), an alkylene group with at least two carbon atoms, having an etheric oxygen atom between its carbon-carbon atoms, or an alkylene group with at least two carbon atoms, having an etheric oxygen atom between its carbon-carbon atoms and at its terminal, which is the terminal on the side bonded to C(—R 12′ —CH═CH 2 ),

(R F1 O) x may be one composed of at least two types of R F1 O.

12. A method for producing a compound represented by the following formula (1L), by reacting a compound represented by the formula (17L) obtained in claim 11 with HSiR 13 n1 X 1 3-n1 ,

A 1 -O—(R F1 O) x —R F CH 2 OCF 2 CHFOCF 2 CF 2 CF 2 —C(O)NH—R 11 —C[(—R 12 —CH 2 CH 2 —SiR 13 n1 X 1 3-n1 ] 3 (1L)

wherein

R 13 is a hydrogen atom or a monovalent hydrocarbon group,

X 1 is a hydrolyzable group, and

n1 is an Integer of from 0 to 2.

13. A compound represented by the following formula (17G),

A 1 -O—(CF 2 CF 2 O)(CF 2 CF 2 O)(R F1 O) x —CF 2 —C(O)NH—R 11 —C(—R 12′ —CH═CH 2 ) 3 (17G)

wherein

A 1 is a C 1-20 perfluoroalkyl group,

R F1 is a perfluoroalkylene group having no branched structure,

x is an integer of from 1 to 198,

(R F1 O) k may be one composed of at least two types of R F1 O.

14. A compound represented by the following formula (17H),

A 1 -O—CHFCF 2 OCH 2 —(CF 2 O)(R F1 O) x —CF 2 —C(O)NH—R 11 —C(—R 12′ —CH═CH 2 ) 3 (17H)

wherein

A 1 is a C 1-20 perfluoroalkyl group,

R F1 is a perfluoroalkylene group having no branched structure,

to x is an integer of from 1 to 198,

(R F1 O) x may be one composed of at least two types of R F1 O.

15. A compound represented by the following formula (17I),

A 1 -O—(R F1 O) x -Q 12 -C(O)NH—R 11 —C(—R 12′ —CH═CH 2 ) 3 (17I)

wherein

A 1 is a C 1-20 perfluoroalkyl group,

R F1 is a perfluoroalkylene group having no branched structure,

x is an integer of from 1 to 198,

Q 12 is a perfluoroalkylene group having no branched structure,

R 11 is a single bond, an alkylene group, an alkylene group having an etheric oxygen atom at Its terminal (which is the terminal on the side bonded to C(—R 12′ —CH—CH 2 ), an alkylene group with at least two carbon atoms, having an etheric oxygen atom between its carbon-carbon atoms, or an alkylene group with at least two carbon atoms, having an etheric oxygen atom between its carbon-carbon atoms and at its to terminal, which is the terminal on the side bonded to C(—R 12′ —CH═CH 2 ),

R 12′ is an alkylene group, an alkylene group having an etheric oxygen atom at Its terminal, or an alkylene group with at least two carbon atoms, having an etheric oxygen atom between its carbon-carbon atoms, and

(R F1 O) x may be one composed of at least two types of R F1 O.

16. A compound represented by the following formula (17J),

A 1 O—(CF 2 CF 2 O)(CF 2 CF 2 O)(R F1 O) x —CF 2 CH 2 OCF 2 CHFOCF 2 CF 2 CF 2 —C(O)NH—R 11 —C(—R 12′ —CH═CH 2 ) 3 (17J)

wherein

A 1 is a C 1-20 perfluoroalkyl group,

R F1 is a perfluoroalkylene group having no branched structure,

x is an integer of from 1 to 198,

R 11 is a single bond, an alkylene group, an alkylene group having an etheric oxygen atom at its terminal, which is the terminal on the side bonded to C(—R 12′ —CH═CH 2 ), an alkylene group with at least two carbon atoms, having an etheric oxygen atom between its carbon-carbon atoms, on an alkylene group with at least two carbon atoms, having an etheric oxygen atom between its carbon-carbon atoms and at its terminal, which is the terminal on the side bonded to C(—R 12′ —CH═CH 2 ),

(R F1 O) x may be one composed of at least two types of R F1 O.

17. A compound represented by the following formula (17K),

A 1 -O—CHFCF 2 OCH r (CF 2 O)(R F1 O) x —CF 2 CH 2 OCF 2 CHFOCF 2 CF 2 CF 2 —C(O)NH—R 11 —C(—R 12′ —CH═CH 2 ) 3 (17K)

wherein

A 1 is a C 1-20 perfluoroalkyl group,

R F1 is a perfluoroalkylene group having no branched structure,

x is an integer of from 1 to 198,

(R F1 O) x may be one composed of at least two types of R F1 O.

18. A compound represented by the following formula (17L),

A 1 -O—(R F1 O) x —R F CH 2 OCF 2 CHFOCF 2 CF 2 CF 2 —C(O)NH—R 11 —C(—R 12′ —CH═CH 2 ) 3 (17L)

wherein

A 1 is a C 1-20 perfluoroalkyl group,

R F1 is a perfluoroalkylene group having no branched structure,

R F is a perfluoroalkylene group having no branched structure,

x is an integer of from 1 to 198,

R 11 is a single bond, an alkylene group, an alkylene group having an etheric oxygen atom at its terminal, which is the terminal on the side bonded to C(R 15 —CH═CH 2 ), an alkylene group with at least two carbon atoms, having an etheric oxygen atom between its carbon-carbon atoms, or an alkylene group with at least two carbon atoms, having an etheric oxygen atom between its carbon-carbon atoms and at its terminal, which is the terminal on the side bonded to C(—R 12′ —CH═CH 2 ),

(R F1 O) x may be one composed of at least two types of R F1 O.

Priority Claims (1)

JP 2015-171986 · Sep 1, 2015 · national

Continuity (4)

Continuation 16715155 · Dec 16, 2019

Continuation 15877489 · Jan 23, 2018

Continuation PCTJP2016075354 · Aug 30, 2016

Related Publication 20210047540A1 · Feb 18, 2021