Perfluoroaminoolefins and methods of making and using the same

Patent metadata

Field	Value
Publication number	US-11629133-B2
Application number	US-201917055498-A
Country	US
Kind code	B2
Filing date	May 10, 2019
Priority date	May 15, 2018
Publication date	Apr 18, 2023
Grant date	Apr 18, 2023

Abstract

Described herein is a perfluorinated aminoolefin compound of general formula (I): CFY═CXN(Rf)CF2Rf′ where: (a) Rf and Rf′ are (i) independently selected from a linear or branched perfluoroalkyl group having 1-8 carbon atoms, optionally comprising at least one catenated O or N atom, or (ii) bonded together to form a perfluorinated ring structure having 4-8 ring carbon atoms, optionally comprising at least one catenated O atom; and (b) X and Y are (i) independently selected from a perfluoroalkyl group having 1-4 carbon atoms, or (ii) bonded together to form a perfluorinated ring structure having 5-6 ring carbon atoms. Such compounds may be used in heat transfer, foam blowing or immersion cooling applications, or as a working fluid in a Rankine cycle, a coating or lubricant, or as a dielectric fluid. Also disclosed herein is a method for making such compounds.

First claim

What is claimed is:

1. A perfluorinated aminoolefin compound represented by the following general formula (I): CFY=CXN(R f )CF 2 R f ′
where:
(a) R f and R f ′ are (i) independently selected from a linear or branched perfluoroalkyl group having 1-8 carbon atoms, optionally comprising at least one catenated O or N atom, or (ii) bonded together to form a perfluorinated ring structure having 4-8 ring carbon atoms, optionally comprising at least one catenated O atom; and
(b) X and Y are (i) independently selected from a perfluoroalkyl group having 1-4 carbon atoms, or (ii) bonded together to form a perfluorinated ring structure having 5-6 ring carbon atoms.

2. The compound according to claim 1 , wherein R f and R f ′ are bonded together to form a five- or six-membered ring.

3. The compound according to claim 1 , wherein the perfluorinated ring structure having 4-8 ring carbon atoms further comprises at least one perfluorinated alkyl substituent.

4. The compound according to claim 1 , wherein R f and R f ′ are independently selected from —CF 3 , —CF 2 CF 3 , or —CF 2 CF 2 CF 3 .

5. The compound according to claim 1 , wherein X and Y are bonded together to form a 5-membered ring.

6. The compound according to claim 1 , wherein the perfluorinated ring structure having 5-6 ring carbon atoms further comprises at least one perfluorinated alkyl substituent.

7. The compound according to claim 1 , wherein X and Y is —CF 3 .

8. The compound according to claim 1 , wherein (i) X is —CF 3 and Y is —CF 2 CF 3 or (ii) X is —CF 2 CF 3 and Y is —CF 3 .

9. The compound of claim 1 , wherein the perfluorinated aminoolefin compound is at least one of:

10. The compound of claim 1 , wherein the perfluorinated aminoolefin compound is at least one of:

11. The compound of claim 1 , wherein the perfluorinated aminoolefin compound has a dielectric constant of less than 2.3.

12. The compound of claim 1 , wherein the perfluorinated aminoolefin compound has a pour point of less than −30° C.

13. A foamable composition comprising:
a blowing agent;
a foamable polymer or a precursor composition thereof; and
a nucleating agent, wherein said nucleating agent comprises the perfluorinated aminoolefin compound according to claim 1 .

14. An apparatus for converting thermal energy into mechanical energy in a Rankine cycle comprising:
a working fluid;
a heat source to vaporize the working fluid and form a vaporized working fluid;
a turbine through which the vaporized working fluid is passed thereby converting thermal energy into mechanical energy;
a condenser to cool the vaporized working fluid after it is passed through the turbine; and
a pump to recirculate the working fluid,
wherein the working fluid comprises the perfluorinated aminoolefin compound according to claim 1 .

15. An immersion cooling system comprising:
a housing having an interior space;
a heat-generating component disposed within the interior space; and
a working fluid liquid disposed within the interior space such that the heat-generating component is in contact with the working fluid liquid;
wherein the working fluid comprises the perfluorinated aminoolefin compound according to claim 1 .

16. A thermal management system for a lithium-ion battery pack comprising:
a lithium-ion battery pack; and
a working fluid in thermal communication with the lithium-ion battery pack;
wherein the working fluid comprises the perfluorinated aminoolefin compound according to claim 1 .

17. The system according to claim 16 , wherein the perfluorinated aminoolefin compound is present in the working fluid at an amount of at least 25% by weight based on the total weight of the working fluid.

18. A thermal management system for an electronic device, the system comprising:
an electronic device selected from a microprocessor, a semiconductor wafer used to manufacture a semiconductor device, a power control semiconductor, an electrochemical cell, an electrical distribution switch gear, a power transformer, a circuit board, a multi-chip module, a packaged or unpackaged semiconductor device, a fuel cell, or a laser; and
a working fluid in thermal communication with the electronic device;
wherein the working fluid comprises the perfluorinated aminoolefin compound according to claim 1 .

19. A working fluid comprising the perfluorinated aminoolefin compound according to claim 1 , wherein the unsaturated fluorinated compound is present in the working fluid in an amount of at least 5% by weight based on the total weight of the working fluid.

20. 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 that comprises the perfluorinated aminoolefin compound according to claim 1 .

Assignees

• 3M Innovative Properties Company

Inventors

• Smith Sean M
• Bulinski Michael J
• Costello Michael G
• Hintzer Klaus
• Hirscherg Markus E
• Lamanna William M

Classifications

• C07C211/24

  the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups · CPC title

• C07C2601/10

  the ring being unsaturated · CPC title

• C09D7/40

  Additives · CPC title

• C08J2203/162

  Halogenated unsaturated hydrocarbons, e.g. H2C=CF2 · CPC title

• C08J9/143

  Halogen containing compounds · CPC title