Nitrogen containing hydrofluoroethers and methods of making same

Patent metadata

Field	Value
Publication number	US-9540316-B2
Application number	US-201414904446-A
Country	US
Kind code	B2
Filing date	Jul 21, 2014
Priority date	Jul 25, 2013
Publication date	Jan 10, 2017
Grant date	Jan 10, 2017

Abstract

Provided are amine-containing hydrofluoroether compounds represented by the following general formula (I), wherein (I) Y is a single bond or CF2 and wherein (i) Rf.1 and Rf2 are independently linear or branched perfluoroalkyl groups having with 1-8 carbon atoms and optionally comprise at least one catenated heteroatom, or (ii) Rf1 and Rf2 are bonded together to form a ring structure having 4-6 carbon atoms and optionally comprise one or more catenated heteroatoms; with the proviso that if Rf1 and Rf2 are bonded together to form a ring structure comprising a nitrogen heteroatom, said nitrogen heteroatom is tertiary and is bonded to a perfluoroalkyl group having 1-3 carbon atoms.

First claim

The invention claimed is:

1. A hydrofluoroether compound of the following general formula (I)

wherein (i) Rf 1 and Rf 2 are independently linear or branched perfluoroalkyl groups having with 1-8 carbon atoms and optionally comprise at least one catenated heteroatom, or (ii) Rf 1 and Rf 2 are bonded together to form a ring structure having 4-6 carbon atoms and optionally comprise one or more catenated heteroatoms;
wherein Y is CF 2 or a single bond; and
wherein Rh is a linear or a branched alkyl group having with 1-3 carbon atoms and optionally comprises at least one catenated heteroatom;
with the proviso that if Rf 1 and Rf 2 are bonded together to form a ring structure comprising a nitrogen heteroatom, said nitrogen heteroatom is tertiary and is bonded to a perfluoroalkyl group having 1-3 carbon atoms.

2. The hydrofluoroether compound of claim 1 , wherein Rf 1 and Rf 2 are bonded together to form a ring structure having 4-6 carbon atoms and optionally comprise one or more catenated heteroatoms.

3. The hydrofluoroether compound of claim 1 , wherein Rf 1 and Rf 2 are independently linear or branched perfluoroalkyl groups having with 1-8 carbon atoms and optionally comprise at least one catenated heteroatom.

4. The hydrofluoroether compound of claim 1 , wherein Rf 1 and Rf 2 are independently linear or branched perfluoroalkyl groups having 2-4 carbon atoms and optionally comprise at least one catenated heteroatom.

5. The hydrofluoroether compound according to claim 1 , wherein Rh has 1-2 carbon atoms.

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

and combinations thereof.

7. A process for transferring heat comprising transferring heat between a heat source and a heat sink through the use of a heat transfer agent comprising a hydrofluoroether compound according to claim 1 .

8. A process for depositing a coating on a substrate, the process comprising applying to at least a portion of at least one surface of said substrate a composition comprising (a) a solvent composition comprising a hydrofluoroether compound according to claim 1 ; and (b) at least one coating material that is soluble or dispersible in said solvent composition.

9. A process for removing a contaminant from an article, the process comprising contacting the article with a hydrofluoroether compound according to claim 1 .

Assignees

• 3M Innovative Properties Co

Inventors

• Bulinski Michael J
• Costello Michael G

Classifications

• C07D265/30

  not condensed with other rings · CPC title

• C07C217/46 Primary

  the carbon skeleton being acyclic and unsaturated · CPC title

• C11D1/004

  Surface-active compounds containing F · CPC title

• 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