Hydrofluoroolefins and methods of using same

Patent metadata

Field	Value
Publication number	US-11932589-B2
Application number	US-202017431590-A
Country	US
Kind code	B2
Filing date	Feb 12, 2020
Priority date	Feb 19, 2019
Publication date	Mar 19, 2024
Grant date	Mar 19, 2024

Abstract

A hydrofluoroolefin compound is represented by the following general formula (I): where R F 1 is a hydrogen atom or CH 3 , and (iii) R F 1 is a linear or branched perfluorinated alkyl group having 1 to 10 carbon atoms and optionally including one or more catenated heteroatoms; and R F 2 is a fluorine atom or a linear or branched perfluorinated alkyl group having 1 to 8 carbon atoms and optionally including one or more catenated heteroatoms; with the proviso that when RF2 is a fluorine atom, then RF1 includes at least 2 carbon atoms; or (iv) R F 1 and R F 2 are bonded together to form a ring structure having 4 to 8 carbon atoms and optionally including one or more catenated heteroatoms.

First claim

What is claimed is:

1. A hydrofluoroolefin compound represented by the following general formula (I):

where R H is a hydrogen atom or CH 3 ; and
(i) R F 1 is a linear or branched perfluorinated alkyl group having 1 to 10 carbon atoms and optionally including one or more catenated heteroatoms; and R F 2 is a linear or branched perfluorinated alkyl group having 1 to 8 carbon atoms and optionally including one or more catenated heteroatoms; or
(ii) R F 1 and R F 2 are bonded together to form a ring structure having 5 to 6 carbon atoms and optionally including one or more catenated heteroatoms.

2. The hydrofluoroolefin compound of claim 1 , wherein the hydrofluoroolefin compound has a solubility factor greater than 0.

3. The hydrofluoroolefin compound of claim 1 , wherein the hydrofluoroolefin compound is non-flammable according to ASTM D-3278-96 e-1 test method.

4. A working fluid comprising a hydrofluoroolefin according to claim 1 , wherein the hydrofluoolefin is present in the working fluid at an amount of at least 25% by weight based on the total weight of the working fluid.

5. A composition comprising:
a hydrofluoroolefin compound of claim 1 ; and
a contaminant;
wherein the hydrofluoolefin is present in the composition at an amount of at least 25% by weight, based on the total weight of the composition.

6. The composition of claim 5 , wherein the contaminant comprises a long chain hydrocarbon alkane.

7. A cleaning composition comprising:
a hydrofluoroolefin compound or working fluid according to claim 1 ; and
a co-solvent.

8. The cleaning composition of claim 7 , wherein said hydrofluoroolefin compound is greater than 50 percent by weight of said cleaning composition, based on the total weights of the hydrofluoroolefin compound and the co-solvent.

9. The composition according claim 7 , wherein said co-solvent comprises alcohols, ethers, alkanes, alkenes, haloalkenes, perfluorocarbons, perfluorinated tertiary amines, perfluoroethers, cycloalkanes, esters, ketones, oxiranes, aromatics, haloaromatics, siloxanes, hydrochlorocarbons, hydrochlorofluorocarbons, hydrofluorocarbons, hydrofluoroolefins, hydrochloroolefins, hydrochlorofluoroolefins, hydrofluoroethers, or mixtures thereof.

10. A cleaning composition comprising:
a hydrofluoroolefin compound according to claim 1 ; and
a surfactant.

11. The composition of claim 10 , wherein the cleaning composition comprises from 0.1 to 5 percent by weight surfactant, based on the total weights of the hydrofluoroolefin compound and the surfactant.

12. The composition of claim 10 , wherein the surfactant comprises a nonionic surfactant comprising an ethoxylated alcohol, an ethoxylated alkylphenol, an ethoxylated fatty acid, an alkylaryl sulfonate, a glycerolester, an ethoxylated fluoroalcohol, a fluorinated sulfonamide, or mixtures thereof.

13. An apparatus for heat transfer comprising:
a device; and
a mechanism for transferring heat to or from the device, the mechanism comprising a working fluid that comprises a hydrofluoroolefin compound of claim 1 .

14. The apparatus for heat transfer of claim 13 , wherein the device is selected from a microprocessor, a semiconductor wafer used to manufacture a semiconductor device, a power control semiconductor, an electrochemical cell, a battery pack, an electrical distribution switch gear, a power transformer, a circuit board, a multi-chip module, a packaged or unpackaged semiconductor device, a fuel cell, and a laser.

15. The apparatus for heat transfer of claim 13 , wherein the mechanism for transferring heat is a component in a system for maintaining a temperature or temperature range of an electronic device.

16. A method of transferring heat comprising:
providing a device; and
transferring heat to or from the device using a heat transfer fluid that comprises a hydrofluoroolefin compound of claim 1 .

17. A thermal management system for a battery pack comprising:
a battery pack; and
a working fluid in thermal communication with the battery pack;
wherein the working fluid comprises a hydrofluoroolefin compound of claim 1 .

18. A process for removing contaminants from a substrate, the process comprising the steps of:
contacting a substrate with a hydrofluoroolefin compound according to claim 1 ;
wherein the contaminant comprises a long chain hydrocarbon alkane.

Assignees

• 3M Innovative Properties Company

Inventors

• Toso Nicholas A
• Bulinski Michael J

Classifications

• Y02E60/10

  Energy storage using batteries · CPC title

• C07C21/18 Primary

  containing fluorine · CPC title

• C07C23/08 Primary

  with a five-membered ring · CPC title

• C07C23/10

  with a six-membered ring · CPC title

• C09K5/045

  containing only fluorine as halogen · CPC title