Method for producing fluorinated compounds

Patent metadata

Field	Value
Publication number	US-11814347-B2
Application number	US-202117553256-A
Country	US
Kind code	B2
Filing date	Dec 16, 2021
Priority date	Sep 26, 2017
Publication date	Nov 14, 2023
Grant date	Nov 14, 2023

Abstract

The present invention relates to a process for the preparation of fluorinated compounds, to novel compounds containing fluorinated end groups, to the use thereof and to compositions comprising novel compounds containing fluorinated end groups.

First claim

The invention claimed is:

1. A compound of formula (I′)

where
Rf is CF 3 —(CF 2 ) a —O b —(CF 2 ) c —O d —,
a=1 or 2,
b=1,
c=0,
d=0,
R is a linear or branched alkyl or siloxane group, optionally containing one or more heteroatoms, or a group Rf′,
Rf′ is a fluorinated, linear or branched alkyl group, optionally containing one or more heteroatoms,
and, if R is a group Rf′, Rf and Rf′ are different,

or
of formula (VI′)

where
Rf is a fluorinated, linear or branched alkyl group, optionally containing one or more heteroatoms, R is a linear or branched alkyl or siloxane group, optionally containing one or more heteroatoms,
L is a single bond or a divalent organic group, and
X is a cationic, amphoteric or anionic group.

2. A compound of formula (I′)

where
Rf is CF 3 —(CF 2 ) a —O b —(CF 2 ) c —O d —,
a=1 or 2,
b=1,
c=0,
d=0,
R is a linear or branched alkyl or siloxane group, optionally containing one or more heteroatoms, or a group Rf′,
Rf′ is a fluorinated, linear or branched alkyl group, optionally containing one or more heteroatoms,
and, if R is a group Rf′, Rf and Rf′ are different.

3. The compound according to claim 2 , wherein Rf is CF 3 —(CF 2 )—O—.

4. The compound according to claim 2 , wherein R is a C1-C20 alkyl group.

5. The compound according to claim 2 , wherein Rf′ is of the following formula
CF 3 —(CF 2 ) a —O b —(CF 2 ) c —O d —(CR 1 R 2 ) e —(CR 3 R 4 ) f —O g —,

where
R 1 , R 2 , R 3 and R 4 , independently of one another, are hydrogen or an alkyl group,
a=0, 1, 2 or 3,
b=0 or 1,
c=0, 1, 2 or 3,
d=0 or 1,
e=0, 1, 2, 3 or 4,
f=0, 1, 2, 3 or 4 and
g=0 or 1.

6. The compound according to claim 2 , wherein Rf is CF 3 —(CF 2 ) 2 —O—.

7. The compound according to claim 1 , which is a compound of formula (VI′).

8. The compound according to claim 4 , wherein Rf is CF 3 —(CF 2 ) 0-3 — or CF 3 —(CF 2 ) 0-3 —O—.

9. The compound according to claim 7 , wherein R is a C1-C20 alkyl group.

10. The compound according to claim 7 , which is a compound of formula (VI′), wherein Rf is CF 3 —(CF 2 ) 0-3 —O—.

11. A product selected from the group consisting of paints, coatings, printing inks, protective coatings, special coatings in electronic or optical applications, photoresists, top antireflective coatings or bottom antireflective coatings, developer solutions and wash solutions and photoresists for photolithographic processes, cosmetic products, agrochemicals, floor polishes, photographic coatings and coatings of optical elements, comprising a compound according to claim 7 .

12. A composition comprising one or more compounds according to claim 7 and a vehicle which is suitable for an application.

13. The composition according to claim 12 , which is selected from the group consisting of paints, coating preparations, fire-extinguishing compositions, lubricants, washing compositions, cleaning compositions, de-icers, developer solutions, wash solutions, photoresists for photolithographic processes, cosmetic products, agrochemicals, floor polishes, hydrophobicising compositions for textile finishing and hydrophobicising compositions for glass treatment.

14. A compound of formula (VI′)

wherein
Rf′ is of the following formula
CF 3 —(CF 2 ) a —O b —(CF 2 ) c —O d —(CR 1 R 2 ) e —(CR 3 R 4 ) f —O g —,

where
R 1 , R 2 , R 3 and R 4 , independently of one another, are hydrogen or an alkyl group,
a=0, 1, 2 or 3,
b=0 or 1,
c=0, 1, 2 or 3,
d=0 or 1,
e=0, 1, 2, 3 or 4,
f=0, 1, 2, 3 or 4, and
g=0 or 1,
R is a linear or branched alkyl or siloxane group, optionally containing one or more heteroatoms, or a group Rf′,
Rf′ is a fluorinated, linear or branched alkyl group, optionally containing one or more heteroatoms,
L is a single bond or a divalent organic group, and
X is a cationic, non-ionic, amphoteric or anionic group,
and, if R is a group Rf′, Rf and Rf′ are different.

15. A compound of formula (VI′)

wherein
Rf is CF 3 —(CF 2 ) 0-3 —,
R is a linear or branched alkyl or siloxane group, optionally containing one or more heteroatoms, or a group Rf′,
Rf′ is a fluorinated, linear or branched alkyl group, optionally containing one or more heteroatoms,
L is a single bond or a divalent organic group and
X is a cationic, non-ionic, amphoteric or anionic group
and, if R is a group Rf′, Rf and Rf′ are different.

16. A method for preparing a compound of formula (VI)

where
Rf is a fluorinated, linear or branched alkyl group, optionally containing one or more heteroatoms,
R is a linear or branched alkyl group, optionally containing one or more heteroatoms, or a group Rf′,
Rf′ is a fluorinated, linear or branched alkyl group, optionally containing one or more heteroatoms,
L is a single bond or a divalent organic group and
X is a cationic, non-ionic, amphoteric or anionic group,
comprising
reacting a compound of formula (I)

where
Rf is a fluorinated, linear or branched alkyl group, optionally containing one or more heteroatoms,
R is a linear or branched alkyl or siloxane group, optionally containing one or more heteroatoms, or a group Rf′, and
Rf′ is a fluorinated, linear or branched alkyl group, optionally containing one or more heteroatoms.

Assignees

• Merck Patent Gmbh

Inventors

• Friedrich Reiner
• Koch Fabian

Classifications

• C07C41/14 Primary

  by exchange of organic parts on the ether-oxygen for other organic parts, e.g. by trans-etherification · CPC title

• C07C17/2637

  between a compound containing only oxygen and possibly halogen as hetero-atoms and a halogenated hydrocarbon · CPC title

• C07C17/272

  by addition reactions · CPC title

• C07C41/03

  by reaction of oxirane rings with hydroxy groups · CPC title

• C07C43/137

  containing halogen · CPC title