Partially fluorinated ketones and methods of making and using the same

Patent metadata

Field	Value
Publication number	US-9796691-B2
Application number	US-201214123788-A
Country	US
Kind code	B2
Filing date	May 22, 2012
Priority date	Jun 10, 2011
Publication date	Oct 24, 2017
Grant date	Oct 24, 2017

Abstract

Partially fluorinated ketones are provided that include a terminal alkyl group having from 1 to 6 carbon atoms bonded to a carbonyl group and a hydrofluoroether moiety having from 2 to 4 carbon atoms that contains at least one hydrogen substituent. The hydrofluoroether moiety is bonded to the carbonyl group with a carbon-carbon bond. The ether oxygen is bonded to a carbon atom that is at least two carbon atoms removed from the carbonyl group. Additionally, a fluorinated alkyl group having from 1 to 10 carbon atoms is bonded to the ether oxygen of the hydrofluoroether moiety. These partially fluorinated ketones can be used in a wide variety of electronics applications.

First claim

What is claimed is:

1. A partially fluorinated ketone having the formula:
R H C(═O)CF 2 CFHOR f ,

or
R H 1 C(═O)CF 2 CFHOR f OCFHCF 2 C(═O)R H 2

wherein each R H , R H 1 , and R H 2 is, independently, a terminal alkyl group having from 1 to 4 carbon atoms, and
wherein R f is a fluorinated alkyl moiety having from 1 to 6 carbon atoms.

2. The partially fluorinated ketone according to claim 1 , wherein each R H , R H 1 , and R H 2 is, independently, linear, branched, cyclic, or a combination thereof.

3. The partially fluorinated ketone according to claim 2 , wherein each R H , R H 1 , and R H 2 is, independently, linear.

4. The partially fluorinated ketone according to claim 3 , wherein each R H , R H 1 , and R H 2 is, independently, ethyl or methyl.

5. The partially fluorinated ketone according to claim 3 , wherein R f is perfluorinated.

6. The partially fluorinated ketone according to claim 3 , wherein at least one of R H , R H 1 , R H 2 and, R f , comprise at least one catenated nitrogen or oxygen atom.

7. The partially fluorinated ketone according to claim 3 , wherein R H is methyl and R f is selected from:

8. The partially fluorinated ketone according to claim 3 , wherein R H 1 and R H 2 are each methyl and R f is —CF 2 CF 2 CF 2 CF 2 —.

9. A process for removing a contaminant from an article comprising contacting said article with a composition comprising at least one partially fluorinated ketone compound of claim 1 .

10. A process for preparing a foamed plastic comprising vaporizing a blowing agent mixture in the presence of at least one foamable polymer or the precursors of at least one foamable polymer, said blowing agent mixture comprising at least one partially fluorinated ketone compound of claim 1 .

11. 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 at least one partially fluorinated ketone compound of claim 1 .

12. A process for depositing a coating on a substrate comprising:
applying to at least a portion of at least one surface of said substrate a composition comprising (a) a solvent composition comprising at least partially fluorinated ketone compound of claim 1 and (b) at least one coating material that is soluble or dispersible in said solvent composition.

13. A polymerization process comprising polymerizing at least one monomer in the presence of at least one polymerization initiator and at least one partially fluorinated ketone compound of claim 1 .

Assignees

• Costello Michael G
• Bulinski Michael J
• Flynn Richard M
• 3M Innovative Properties Co

Inventors

• Costello Michael G
• Bulinski Michael J
• Flynn Richard M

Classifications

• C09K5/10

  Liquid materials · CPC title

• C07D307/12

  Radicals substituted by oxygen atoms · CPC title

• C07D211/38

  Halogen atoms or nitro radicals · CPC title

• C07C49/175 Primary

  containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups · CPC title

• C07D307/18

  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