Amine-containing acyclic hydrofluoroethers and methods of using the same

Patent metadata

Field	Value
Publication number	US-10344006-B2
Application number	US-201716073854-A
Country	US
Kind code	B2
Filing date	Feb 22, 2017
Priority date	Mar 11, 2016
Publication date	Jul 9, 2019
Grant date	Jul 9, 2019

Abstract

An acyclic fluorinated compound of formula (I) is amine-containing acyclic hydrofluoroethers. The acyclic fluorinated compound is useful as heat transfer, solvent cleaning, fire extinguishing agents and electrolyte solvents and additives.

First claim

What is claimed is:

1. A acyclic fluorinated compound of formula (I)

where:
each R h is independently H or CH 3 ;
X is selected from F or CF 3 , and Y is selected from H, F, or CF 3 , wherein when X is CF 3 then Y is F and when Y is CF 3 then X is F;
each R f 1 is independently selected from a linear or branched perfluorinated alkyl group comprising 1-8 carbon atoms and optionally comprising at least one catenated atom selected from O, N, or combinations thereof; or the two R f 1 groups are bonded together to form a fluorinated ring structure comprising 4-8 carbon atoms and optionally comprising at least one catenated atom selected from O, N, or combinations thereof;
A is selected from F, or CF 3 ;
Z is selected from H, F or CF 3 ; and
Q is selected from (i) a F atom, (ii) a Cl atom, (iii) a linear, cyclic, or branched perfluorinated alkyl group comprising 1-8 carbon atoms and optionally comprising at least one catenated atom selected from O, N, or combinations thereof, or (iv) a G(R f 2 ) e group, where G is an O atom or a N atom wherein:
when Q is a Cl atom, then Z and A are F atoms;
when G is O then e is 1, Z is H, F or CF 3 ; A is F; and R f 2 is a linear or branched perfluorinated alkyl group comprising 1-10 carbon atoms and optionally comprising at least one catenated atom selected from O, N, or combinations thereof;
when G is N then e is 2, and each R f 2 group is independently a linear or branched perfluorinated alkyl group comprising 1-8 carbon atoms and optionally comprising at least one catenated atom selected from O, N, or combinations thereof or the two R f 2 groups are bonded together to form a fluorinated ring structure comprising 4-8 carbon atoms and optionally comprising at least one catenated atom selected from O, N, or combinations thereof, with the proviso that when A is CF 3 then Z is F, and when Z is CF 3 then A is F.

2. The acyclic fluorinated compound of claim 1 , wherein Q =N(R f 1 ) 2 .

3. The acyclic fluorinated compound of claim 2 , wherein N(R f 1 ) 2 is a perfluorinated morpholine group.

4. The acyclic fluorinated compound of claim 1 , wherein Q is a perfluorinated alkyl group comprising less than 4 carbon atoms.

5. The acyclic fluorinated compound of claim 1 , wherein X and Y are both F.

6. The acyclic fluorinated compound of claim 1 , wherein A and Z are both F.

7. The acyclic fluorinated compound of claim 1 , wherein the acyclic fluorinated compound comprises at least one of the following:

where Me refers to a methyl group.

8. A working fluid comprising the acyclic fluorinated compound according to claim 1 , wherein the acyclic fluorinated compound is present in the working fluid in an amount of at least 25% by weight based on the total weight of the working fluid.

9. A composition comprising a purified form of the acyclic fluorinated compound according to claim 1 .

10. The acyclic fluorinated compound of claim 1 , wherein the acyclic fluorinated compound has a global warming potential of less than 100.

11. A working fluid comprising the acyclic fluorinated compound according to claim 1 , wherein the acyclic fluorinated compound is present in the working fluid in an amount of at least 25% by weight based on the total weight of the working fluid.

12. The working fluid of claim 11 , wherein the working fluid further comprises a co-solvent.

13. An apparatus for heat transfer comprising a mechanism for transferring heat to or from a device, the mechanism comprising a heat transfer fluid that comprises the acyclic fluorinated compound according to claim 1 .

14. An apparatus for heat transfer according to 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, 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. An apparatus according to 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. An apparatus according to claim 13 , wherein the device comprises a soldered electronic component.

17. An apparatus according to claim 13 , wherein the mechanism comprises vapor phase soldering.

Assignees

• 3M Innovative Properties Co

Inventors

• Smith Sean M
• Bulinski Michael J
• Costello Michael G
• Lamanna William M

Classifications

• C07D207/10

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms · CPC title

• C07D211/38

  Halogen atoms or nitro radicals · CPC title

• C11D7/28

  containing halogen · CPC title

• C07C217/26

  having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is further substituted by halogen atoms or by nitro or nitroso groups · CPC title

• C11D3/245

  containing fluorine · CPC title