Allylic terminally unsaturated hydrofluoroamine and allylic terminally unsaturated hydrofluoroether compounds and methods of using the same

Patent metadata

Field	Value
Publication number	US-10577335-B2
Application number	US-201615770289-A
Country	US
Kind code	B2
Filing date	Nov 28, 2016
Priority date	Dec 2, 2015
Publication date	Mar 3, 2020
Grant date	Mar 3, 2020

Abstract

Described herein is an unsaturated fluorinated compound of formula (I) where X is O or N; Y is F or H; Z is F or CF3; and A is F or CF3 wherein when X is O, then n is 1, Y is H, Z is F, A is F, and Rf is a linear or branched perfluorinated alkyl group comprising 1 to 10 carbon atoms and optionally comprising at least one catenated O or N; and when X is N, then n is 2 and each Rf group are (i) independently selected from a linear or branched perfluorinated alkyl group comprising 1 to 8 carbon atoms and optionally comprising at least one catenated O or N; or (ii) bonded together to form a ring structure comprising 4 to 8 carbon atoms and optionally comprising at least one catenated O or N with the proviso that when Z is CF 3 then A is F and when A is CF 3 then Z is F and methods of making and using the same.

First claim

What is claimed is:

1. An unsaturated fluorinated compound of formula (I):

where X is N;
Y is F or H;
Z is F or CF 3 ;
A is F or CF 3 ;
n is 2; and
each R f group is (i) independently selected from a linear or branched perfluorinated alkyl group comprising 1 to 8 carbon atoms and optionally comprising at least one catenated O or N atom; or (ii) bonded together to form a ring structure comprising 4 to 8 carbon atoms and optionally comprising at least one catenated O or N atom with the proviso that when Z is CF 3 then A is F and when A is CF 3 then Z is F.

2. The unsaturated fluorinated compound of claim 1 , wherein Y is F.

3. The unsaturated fluorinated compound of claim 1 , wherein A is F.

4. The unsaturated fluorinated compound of claim 1 , wherein the unsaturated fluorinated compound has a percent fluorine content of 75%.

5. The unsaturated fluorinated compound of claim 1 , wherein the unsaturated fluorinated compound is selected from the group consisting of:

6. The unsaturated fluorinated compound of claim 1 , wherein the unsaturated fluorinated compound is selected from the group consisting of:

7. An unsaturated fluorinated compound of formula (I):

where X is O;
Y is H;
Z is F;
A is F;
n is 1; and
R f is a linear or branched perfluorinated alkyl group comprising 1 to 10 carbon atoms and optionally comprising at least one catenated O or N atom.

8. A working fluid comprising the unsaturated fluorinated compound according to claim 1 , wherein the unsaturated 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 cleaning composition comprising the unsaturated fluorinated compound of claim 1 .

10. An electrolyte comprising an electrolyte solvent or additive comprising the unsaturated fluorinated compound of claim 1 .

11. A heat transfer fluid comprising the unsaturated fluorinated compound of claim 1 .

12. A fire extinguishing agent comprising the unsaturated fluorinated compound of claim 1 .

13. The unsaturated fluorinated compound of claim 1 , wherein the unsaturated fluorinated compound is nonflammable based on closed-cup flashpoint testing following ASTM D-327-96 e-1 standard test method.

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

15. The working fluid of claim 8 , wherein the working fluid further comprises a co-solvent.

16. The unsaturated fluorinated compound of claim 7 , wherein the unsaturated fluorinated compound is selected from the group consisting of:

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

• C07D241/04

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

• C09K5/10

  Liquid materials · CPC title

• C07D265/30 Primary

  not condensed with other rings · CPC title

• H01M2300/002

  Inorganic electrolyte · CPC title