Hydrofluoroolefin ethers, compositions, apparatuses and methods for using same

Patent metadata

Field	Value
Publication number	US-11535579-B2
Application number	US-201815733206-A
Country	US
Kind code	B2
Filing date	Dec 12, 2018
Priority date	Dec 13, 2017
Publication date	Dec 27, 2022
Grant date	Dec 27, 2022

Abstract

A hydrofluoroolefin ether represented by the general Formula (I), compositions that include such compounds, and apparatuses and methods for use that include such compositions and compounds, wherein Formula (I) is represented by: Rf—O—CH2CH═CHCH2—O—Rf (I) wherein each Rf group is independently a linear, branched, and/or cyclic perfluoroalkyl group having 2 to 9 carbon atoms and optionally further including 1 to 3 nitrogen and/or oxygen catenary heteroatoms.Rf—O—CH2CH═CHCH2—O—Rf  (I)

First claim

What is claimed is:

1. A hydrofluoroolefin ether represented by the following general formula (I):
R f —O—CH 2 CH═CHCH 2 —O—R f   (I)

wherein each R f group is independently a linear, branched, and/or cyclic perfluoroalkyl group having 2 to 9 carbon atoms and wherein each R f group contains a —CF 2 -group adjacent to the oxygen atom.

2. The hydrofluoroolefin ether of claim 1 wherein each R f group is the same.

3. The hydrofluoroolefin ether of claim 1 wherein each R f group is independently a linear, branched, and/or cyclic perfluoroalkyl group having 3 to 9 carbon atoms and optionally further including 1 to 3 nitrogen and/or oxygen catenary heteroatoms.

4. The hydrofluoroolefin ether of claim 3 wherein each R f group is independently a linear, branched, and/or cyclic perfluoroalkyl group having 4 to 9 carbon atoms and optionally further including 1 to 3 nitrogen and/or oxygen catenary heteroatoms.

5. The hydrofluoroolefin ether of claim 1 wherein each R f group is independently a linear or branched perfluoroalkyl group and optionally further including 1 to 3 nitrogen and/or oxygen catenary heteroatoms.

6. The hydrofluoroolefin ether of claim 1 which is in a cis configuration or a trans configuration.

7. The hydrofluoroolefin ether of claim 1 wherein each R f group is independently selected from —(CF 2 ) n CF 3 or —(CF 2 ) n CF(CF 3 ) 2 , wherein n=1 to 6.

8. The hydrofluoroolefin ether of claim 1 , wherein the hydrofluoroolefin is selected from at least one of the following:

9. The hydrofluoroolefin ether of claim 1 , wherein the hydrofluoroolefin ether has a global warming potential (GWP) of less than 300.

10. The hydrofluoroolefin ether of claim 1 , wherein the hydrofluoroolefin ether is non-flammable.

11. A composition comprising the hydrofluoroolefin ether compound of claim 1 .

12. The composition of claim 11 comprising a mixture of hydrofluoroolefin ether compounds of Formula (I), at least a portion of which includes linear R f groups and at least a portion of which includes branched R f groups.

13. The composition of claim 11 comprising a mixture of hydrofluoroolefin ether compounds of Formula (I), at least a portion of which are in the cis configuration and at least a portion of which are in the trans configuration.

14. The composition of claim 11 which is a heat transfer fluid.

15. The composition of claim 11 which is a cleaning composition.

16. An apparatus for heat transfer comprising:
a device; and
a mechanism for transferring heat to or from the device, the mechanism comprising a heat transfer fluid comprising a composition of claim 14 .

17. A method of transferring heat comprising:
providing a device; and
transferring heat to or from the device using a heat transfer fluid comprising a composition of claim 14 .

18. A method of cleaning a substrate, the method comprising:
providing substrate having one or more contaminants on a surface thereof; and
contacting the contaminated substrate with a cleaning composition of claim 17 to remove at least a portion of the contaminants.

Assignees

• 3M Innovative Properties Company

Inventors

• Smith Sean M

Classifications

• C09K5/10

  Liquid materials · CPC title

• C07D401/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D211/38

  Halogen atoms or nitro radicals · CPC title

• C07D265/30 Primary

  not condensed with other rings · CPC title

• C07D241/04

  having no double bonds between ring members or between ring members and non-ring members · CPC title