Processes for producing fluorinated ether compounds

Patent metadata

Field	Value
Publication number	US-11066517-B2
Application number	US-201916282406-A
Country	US
Kind code	B2
Filing date	Feb 22, 2019
Priority date	Aug 30, 2016
Publication date	Jul 20, 2021
Grant date	Jul 20, 2021

Abstract

Processes for producing a fluorinated ether compound are provided by which fluorinated ether compound capable of imparting excellent water/oil repellency, to a substrate surface or a hard coat layer can be easily produced in high yield. A process comprising reacting Rf(CF2)a—CF2OC(═O)Rf4 or Rf(CF2)a—C(═O)X1 with HN(—R1CH═CH2)2 to obtain Rf(CF2)a—C(═O)N(—R1CH2═CH2)2 and a process comprising obtaining the above product and reacting the product with HSiR2nL3-n to obtain Rf(CF2)a—C(═O)N(—R1CH2CH2SiR2nL3-n)2 wherein Rf is a linear polyfluoroalkyl group having at least two carbon atoms and at least one etheric oxygen atom between carbon atoms, Rf4 is a C1-30 perfluoroalkyl group or the like, X1 is a halogen atom, R1 is an alkylene group, a is an integer of from 1 to 5, R2 is a monovalent hydrocarbon group, L is a hydrolyzable group, and n is an integer of from 0 to 2.

First claim

What is claimed is:

1. A process for producing a fluorinated ether compound, which comprises reacting a compound represented by the following formula (3) with a compound represented by the following formula (5) to obtain a compound represented by the following formula (2):
R f (CF 2 ) a —CF 2 OC(═O)R f4   (3)

HN(—R 1 CH═CH 2 ) 2   (5)

R f (CF 2 ) a —C(═O)N(—R 1 CH═CH 2 ) 2   (2)

wherein R f is a linear polyfluoroalkoxy group having at least two carbon atoms and at least one etheric oxygen atom between carbon atoms,
R f4 is a C 1-30 perfluoroalkyl group or a C 2-30 perfluoroalkyl group having an etheric oxygen atom between carbon atoms,
R 1 is an alkylene group, and
a is an integer of from 1 to 5.

2. The process for producing a fluorinated ether compound according to claim 1 , wherein R f is a linear perfluoroalkoxy group having at least two carbon atoms and at least one etheric oxygen atom between carbon atoms.

3. The process for producing a fluorinated ether compound according to claim 1 , wherein R f (CF 2 ) a — is a group represented by the following formula (7):
R f1 O(R f2 O) m1 (R f3 O) m2 (CF 2 ) a —  (7)

wherein m1 is an integer of from 0 to 10, m2 is an integer of from 2 to 200,
R f1 is a C 1-20 linear perfluoroalkyl group when m1 is 0, or a C 1-20 linear perfluoroalkyl group or a C 2-20 linear perfluoroalkyl group having at least one etheric oxygen atom between carbon atoms when m1 is at least 1,
R f2 is a C 1-10 linear fluoroalkylene group having at least one hydrogen atom, 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, and
R f3 is a C 1-10 linear perfluoroalkylene group, 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.

4. The process for producing a fluorinated ether compound according to claim 3 , wherein m1 is an integer of from 0 to 3.

5. The process for producing a fluorinated ether compound according to claim 3 , wherein (R f3 O) m2 is {(CF 2 O) m21 (CF 2 CF 2 O) m22 } (wherein each of m21 and m22 is an integer of at least 1, and 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) or (CF 2 CF 2 OCF 2 CF 2 CF 2 CF 2 O) m25 CF 2 CF 2 O (wherein m25 is an integer of from 1 to 99).

6. The process for producing a fluorinated ether compound according to claim 3 , wherein R f (CF 2 ) a — is a group represented by the following formula (7-1), a group represented by the following formula (7-2) or a group represented by the following formula (7-3):
R f11 O{(CF 2 O) m21 (CF 2 CF 2 O) m22 }CF 2 —  (7-1)

R f11 OCHFCF 2 OCH 2 CF 2 O{(CF 2 O) m21 (CF 2 CF 2 O) m22 }CF 2 —  (7-2)

R f11 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 —  (7-3)

wherein R f11 is a C 1-20 perfluoroalkyl group,
each of m21 and m22 is an integer of at least 1, and 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 99.

7. The process for producing a fluorinated ether compound according to claim 3 , wherein m1 is 0.

8. The process for producing a fluorinated ether compound according to claim 1 , wherein the compound represented by the formula (5) is diallylamine.

9. The process for producing a fluorinated ether compound according to claim 1 , wherein the compound represented by the formula (3) is reacted with the compound represented by the formula (5) in a liquid medium.

10. A process for producing a fluorinated ether compound, which comprises obtaining a compound represented by the formula (2) by the process for producing a fluorinated ether compound as defined in claim 1 , and reacting the compound represented by the formula (2) with a compound represented by the following formula (6) to obtain a compound represented by the following formula (1):
HSiR 2 n L 3-n   (6)

R f (CF 2 ) a —C(═O)N(—R 1 CH 2 CH 2 SiR 2 n L 3-n ) 2   (1)

wherein R 2 is a monovalent hydrocarbon group,
L is a hydrolysable group, and
n is an integer of from 0 to 2.

11. The process for producing a fluorinated ether compound according to claim 10 , wherein R 2 is an alkyl group having at most 4 carbon atoms.

12. The process for producing a fluorinated ether compound according to claim 10 , wherein L is an alkoxy group having at most 4 carbon atoms or a chlorine atom.

13. The process for producing a fluorinated ether compound according to claim 1 , wherein the reacting is carried out in a fluorinated organic solvent.

Assignees

• Agc Inc

Inventors

• Hoshino Taiki
• Aoyama Motoshi
• Takao Kiyotaka

Classifications

• C08G2650/48

  containing fluorine, e.g. perfluropolyethers · CPC title

• C08G65/336 Primary

  containing silicon · CPC title

• C08G65/33306

  acyclic · CPC title

• C08G65/3236

  Fluorine · CPC title

• C08G65/007 Primary

  containing fluorine · CPC title