Fluorine-containing ether compound, surface treatment agent, fluorine-containing ether composition, coating liquid, article, and production method thereof

Patent metadata

Field	Value
Publication number	US-12570677-B2
Application number	US-202217805554-A
Country	US
Kind code	B2
Filing date	Jun 6, 2022
Priority date	Dec 26, 2019
Publication date	Mar 10, 2026
Grant date	Mar 10, 2026

Abstract

Provided are a fluorine-containing ether compound, a fluorine-containing ether composition, and a coating liquid, which can form a surface layer having excellent durability, and an article and production method thereof having a surface layer that has excellent durability and that can maintain water and oil repellency, lubricity, and fingerprint stain removability for a long time. The fluorine-containing ether compound includes a polyfluoropolyether chain, a reactive silyl group, and a linking group that includes a group represented by *—O—C(═O)—**, in which the linking group links the polyfluoropolyether chain arranged on the * side and the reactive silyl group arranged on the ** side.

First claim

What is claimed is:

1 . A fluorine-containing ether compound represented by the following formula 1,
R f [—R 1 —O—C(═O)-Q 1 {-T} g ] j   Formula 1
wherein R f is a polyfluoropolyether chain in which at least one fluorine atom is bonded to a carbon atom bonded to R 1 , R 1 is an alkylene group having 1 to 10 carbon atoms optionally having a substituent (other than a fluorine atom), and a plurality of R 1 may be the same or different, Q 1 is a (g+1)-valent organic group having a carbon atom bonded to —O—C(═O)— in formula 1, and when there are a plurality of Q 1 , the plurality of Q 1 may be the same or different, T is —Si(R) 3-a (L) a , and when there are two or more T, the two or more T may be the same or different, R is an alkyl group, L is a hydrolyzable group or a hydroxyl group, and two or more L in T may be the same or different, a is 2 or 3, g is an integer of 1 or more, and when there are a plurality of g, the plurality of g may be the same or different, and j is 1 or 2.

2 . The fluorine-containing ether compound according to claim 1 , wherein
Q 1 is represented by any of the following formulas (Q1) to (Q7):
-A 1 -C(R e2 ) 3-g3 (-Q 22 -) g3   Formula (Q2)

-A 2 -N(-Q 23 -) 2   Formula (Q3)

-A 3 -Z 1 (-Q 24 -) g4   Formula (Q4)

-A 2 -Si(R e3 ) 3-g3 (-Q 25 -) g3   Formula (Q5)

-A 1 -Q 26 -  Formula (Q6)

-A 1 -CH(-Q 22 -)—Si(R e3 ) 3-g5 (-Q 25 -) g5   Formula (Q7)

wherein, in formulas (Q1) to (Q7), the A 1 , A 2 , or A 3 side is linked to —O—C(═O)— in formula 1, and the Q 22 , Q 23 , Q 24 , Q 25 , or Q 26 side is linked to T, A 1 is a single bond, an alkylene group, or a group having —C(O)NR e6 —, —C(O)—, —NR e6 —, or —O— between carbon-carbon atoms of an alkylene group having two or more carbon atoms, A 2 is an alkylene group or a group having —C(O)NR e6 —, —C(O)—, —NR e6 —, or —O-between carbon-carbon atoms of an alkylene group having two or more carbon atoms, A 3 is A 1 when the atom in Z 1 to which A 3 is bonded is a carbon atom, and is A 2 when the atom in Z 1 to which A 3 is bonded is a nitrogen atom, Q 11 is a single bond, —O—, an alkylene group, a group having —C(O)NR e6 —, —C(O)—, —NR e6 —, or —O-between carbon-carbon atoms of an alkylene group having two or more carbon atoms, Q 22 is an alkylene group, a group having —C(O)NR e6 —, —C(O)—, —NR e6 —, or —O-between carbon-carbon atoms of an alkylene group having two or more carbon atoms, a group having-C(O)NR e6 —, —C(O)—, —NR e6 —, or —O— at an end on the side not linked to the T of the alkylene group, or a group having —C(O) NR e6 —, —C(O)—, —NR e6 —, or —O— between carbon-carbon atoms of an alkylene group having two or more carbon atoms and having —C(O)NR e6 —, —C(O)—, —NR e6 —, or —O— at an end on the side not linked to the T of the alkylene group, and when Q 1 has two or more Q 22 , the two or more Q 22 may be the same or different, Q 23 is an alkylene group or a group having —C(O)NR e6 , —C(O)—, —NR e6 —, or —O— between carbon-carbon atoms of an alkylene group having two or more carbon atoms, and the two Q 23 may be the same or different, Q 24 is Q 22 when the atom in Z 1 to which Q 24 is bonded is a carbon atom, is Q 23 when the atom in Z 1 to which Q 24 is bonded is a nitrogen atom, and when Q 1 has two or more Q 24 , the two or more Q 24 may be the same or different, Q 25 is an alkylene group or a group having —C(O)NR e6 —, —C(O)—, —NR e6 —, or —O— between carbon-carbon atoms of an alkylene group having two or more carbon atoms, and when Q 1 has two or more Q 25 , the two or more Q 25 may be the same or different, Q 26 is an alkylene group or a group having —C(O)NR e6 —, —C(O)—, —NR e6 —, or —O— between carbon-carbon atoms of an alkylene group having two or more carbon atoms, Z 1 is a (g4+1)-valent group having a ring structure having a carbon atom or nitrogen atom to which A 3 is directly bonded and a carbon atom or nitrogen atom to which Q 24 is directly bonded, R e1 is a hydrogen atom or an alkyl group, and when Q 1 has two or more Rel, the two or more R e1 may be the same or different, R e2 is a hydrogen atom, a hydroxyl group, an alkyl group, or an acyloxy group, R e3 is an alkyl group, R e6 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group, g1 is an integer from 0 to 3, g2 is an integer from 0 to 3, and g1+g2 is an integer from 1 to 6, g3 is an integer from 1 to 3, g4 is an integer greater than or equal to one, and g5 is an integer from 0 to 3.

3 . A surface treatment agent comprising the fluorine-containing ether compound according to claim 1 .

4 . A fluorine-containing ether composition comprising:
one or more of the fluorine-containing ether compounds according to claim 1 ; and an additional fluorine-containing ether compound.

5 . A coating liquid comprising:
the fluorine-containing ether compound according to claim 1 ; and a liquid medium.

6 . An article comprising a surface layer formed from the fluorine-containing ether compound according to claim 1 .

7 . A method for producing an article, comprising forming a surface layer by a dry coating method or a wet coating method using the fluorine-containing ether compound according to claim 1 .

Assignees

• Agc Inc

Inventors

• ONO Hikaru
• Watanabe Koki
• Aoyama Motoshi
• Takashita Ryuta

Classifications

• C09D7/63

  organic · CPC title

• C09K3/18

  for application to surfaces to minimize adherence of ice, mist or water thereto (rendering particulate materials free flowing, in general, e.g. making them hydrophobic B01J2/30); Thawing or antifreeze materials for application to surfaces (used in liquids for heat-transfer, heat-exchange or heat-storage or for the production of heat or cold other than by combustion, e.g. radiator liquids, C09K5/00) · CPC title

• C09D5/16

  Antifouling paints; Underwater paints · CPC title

• C09D171/02

  Polyalkylene oxides · CPC title

• C07F7/1804

  Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896) · CPC title