Fluorinated ether compound, coating liquid, article and novel compounds

Patent metadata

Field	Value
Publication number	US-10696848-B2
Application number	US-201816152450-A
Country	US
Kind code	B2
Filing date	Oct 5, 2018
Priority date	Apr 25, 2016
Publication date	Jun 30, 2020
Grant date	Jun 30, 2020

Abstract

The present invention provides: a fluorinated ether compound and a coating liquid capable of forming a surface layer excellent in water/oil repellency, abrasion resistance, fingerprint stain removability and lubricity and an article having a surface layer excellent in water/oil repellency, abrasion resistance, fingerprint stain removability and lubricity. Provided is a fluorinated ether compound represented by [R f -G-] a Z[—(O—R 2 ) c —SiR 3 n L 3−n ] b wherein R f : a linear polyfluoroalkyl group having at least two carbon atoms, which has at least one etheric oxygen between carbon-carbon atoms, G: —R 1 —O—, —R 1 —CONH—, —CONH— or a single bond, R 1 : an alkylene group, Z: a hydrocarbon group having a valence of (a+b) or the like, R 2 : an alkylene group, R 3 : a monovalent hydrocarbon group or the like, L: a hydrolyzable group, n: from 0 to 2, a: an integer of at least 1, b: an integer of at least 1, (a+b): at least 3, when a is 1, b is at least 4, and when a is at least 2, b is at least 1, and c: 0 or 1.

First claim

What is claimed is:

1. A fluorinated ether compound represented by the following formula (1):
[R f -G-] a Z[—(O—R 2 ) c —SiR 3 n L 3−n ] b   (1)

wherein R f is a linear polyfluoroalkyl group having at least two carbon atoms, which has at least one etheric oxygen between carbon-carbon atoms and has at least one fluorine atoms on a carbon atom bonded to G or Z,
G is —R 1 —O—, —R 1 —CONH—, —CONH— or a single bond,
R 1 is an alkylene group,
Z is a hydrocarbon group having a valence of (a+b) or a hydrocarbon group having at least two carbon atoms, having at least one etheric oxygen atom between carbon-carbon atoms and having a valence of (a+b),
R 2 is an alkylene group,
R 3 is a hydrogen atom or a monovalent hydrocarbon group,
L is a hydrolyzable group,
n is an integer of from 0 to 2,
a is an integer of at least 1,
b is an integer of at least 1,
(a+b) is at least 3,
when a is 1, b is at least 4, and when a is at least 2, b is at least 1,
provided that when a is at least 2, each [R f -G-] may be identical with or different from one another, and
when b is at least 2, each [—(O—R 2 )—SiR 3 n L 3−n ] may be identical with or different from one another, and
c is 0 or 1.

2. The fluorinated ether compound according to claim 1 , wherein c is 1 and R 2 is a C 4-14 alkylene group.

3. The fluorinated ether compound according to claim 1 , wherein Z is a group represented by the following formula (Z-1), a group represented by the following formula (Z-2), a group represented by the following formula (Z-3), a group represented by the following formula (Z-4) or a group represented by the following formula (Z-5):

wherein R 4 is an alkyl group.

4. The fluorinated ether compound according to claim 1 , wherein R 1 is —CH 2 —.

5. The fluorinated ether compound according to claim 1 , wherein R f is a group represented by the following formula (R f -0):
R f1 O(R f2 O) m1 (R f3 O) m2 R f4 —  (R f -0)

wherein when m1 is 0, R f is a C 1-20 linear perfluoroalkyl group, and when m1 is at least 1, R f1 is a C 1-20 linear perfluoroalkyl group or a C 2-20 linear perfluoroalkyl group having at least one etheric oxygen atom between carbon-carbon atoms,
R f2 is a C 1-10 linear fluoroalkylene group having at least one hydrogen atom,
m1 is an integer of from 0 to 10, provided that when m1 is at least 2, (R f2 O) m1 may be composed of at least two kinds of R f2 O different in either or both of the number of carbon atoms and the number of hydrogen atoms,
R f3 is a C 1-10 linear perfluoroalkylene group,
m2 is an integer of from 2 to 200, provided that (R f3 O) m2 may be composed of at least two kinds of R f3 O different in the number of carbon atoms, and
R f4 is a C 1-10 linear perfluoroalkylene group.

6. The fluorinated ether compound according to claim 1 , wherein R f is a linear perfluoroalkyl group having at least two carbon atoms and having at least one etheric oxygen atoms between carbon-carbon atoms.

7. The fluorinated ether compound according to claim 1 , wherein R f is a group represented by the following formula (R f -1), a group represented by the following formula (R f -2) or a group represented by the following formula (R f -3):
R f1 O{(CF 2 O) m21 (CF 2 CF 2 O) m22 }CF 2 —  (R f -1)

R f1 OCHFCF 2 OCH 2 CF 2 O{(CF 2 O) m21 (CF 2 CF 2 O) m22 }CF 2 —  (R f -2)

R f1 O(CF 2 CF 2 OCF 2 CF 2 CF 2 CF 2 O) m25 CF 2 CF 2 OCF 2 CF 2 CF 2 —  (R f -3)

wherein R f1 is a C 1-20 perfluoroalkyl group,
each of m21 and m22 is an integer of at least 1, m21+m22 is an integer of from 2 to 200, provided that each CF 2 O and each CF 2 CF 2 O may be bonded in any order, and
m25 is an integer of from 1 to 100.

8. The fluorinated ether compound according to claim 1 , which has a number average molecular weight of from 1,000 to 30,000.

9. A coating liquid comprising the fluorinated ether compound as defined in claim 1 and a liquid medium.

10. A process for producing an article having a surface layer formed from a fluorinated ether compound, which comprises treating the surface of a substrate with the coating liquid as defined in claim 9 by wet coating.

11. An article having a surface layer formed from the fluorinated ether compound as defined in claim 1 .

12. A process for producing an article having a surface layer formed from the fluorinated ether compound as defined in claim 1 , which comprises treating the surface of a substrate with the fluorinated ether compound by dry coating.

13. The fluorinated ether compound according to claim 1 , which is represented by one of the following formulae:

Assignees

• Agc Inc

Inventors

• Hoshino Taiki
• Toda Kazue
• ANRAKU Eiichiro
• Itoh Masahiro

Classifications

• C07C255/06

  of an acyclic and unsaturated carbon skeleton · CPC title

• B05D1/60

  Deposition of organic layers from vapour phase (vapour phase deposition in general C23C14/00, C23C16/00) · CPC title

• B05D5/083

  involving the use of fluoropolymers · CPC title

• C08G65/007

  containing fluorine · CPC title

• C23C14/24

  Vacuum evaporation · CPC title