Omega-hydrofluoroalkyl ethers, precursor carboxylic acids and derivatives thereof, and their preparation and application

• US 6,214,253 B1
• Filed: 12/02/1999
• Issued: 04/10/2001
• Est. Priority Date: 05/20/1994
• Status: Expired due to Term

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Moore, George G. I., Owens, John G., Flynn, Richard M., Guerra, Miguel A.
• Primary Examiner(s): Gupta, Yogendra
• Assistant Examiner(s): HAMLIN, DERRICK G
• Application Number:
  US09/452,711
• Time in Patent Office: 495 Days
• Field of Search: 252/70, 252/72, 252/380, 252/194, 169/46, 169/47, 169/14, 510/415
• US Class Current: 252/70
• CPC Class Codes: A61K 49/0461 Dispersions, colloids, emulsions or suspensions
• CPC Class Codes: A61K 49/1806 Suspensions, emulsions, colloids, dispersions
• CPC Class Codes: A61K 49/226 Solutes, emulsions, suspensions, dispersions, semi-solid forms, e.g. hydrogels
• CPC Class Codes: A61K 9/0026 Blood substitute; Oxygen transporting formulations; Plasma extender
• CPC Class Codes: A62D 1/00 Fire-extinguishing compositions; Use of chemical substances in extinguishing fires fireproof paints C09D5/18; fireproofing materials C09K21/00
• CPC Class Codes: A62D 1/0028 Liquid extinguishing substances A62D1/0092 takes precedence
• CPC Class Codes: A62D 1/0035 Aqueous solutions
• CPC Class Codes: A62D 1/0085 containing perfluoroalkyl-terminated surfactant
• CPC Class Codes: B01D 12/00 Displacing liquid, e.g. from wet solids or from dispersions of liquids or from solids in liquids, by means of another liquid
• CPC Class Codes: B23K 35/386 for condensation soldering
• CPC Class Codes: C07C 2601/14 The ring being saturated
• CPC Class Codes: C07C 2602/28 Hydrogenated naphthalenes
• CPC Class Codes: C07C 41/16 by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
• CPC Class Codes: C07C 41/18 by reactions not forming ether-oxygen bonds
• CPC Class Codes: C07C 41/22 by introduction of halogens; by substitution of halogen atoms by other halogen atoms
• CPC Class Codes: C07C 41/24 by elimination of halogens, e.g. elimination of HCl
• CPC Class Codes: C07C 43/12 containing halogen
• CPC Class Codes: C07C 43/123 both carbon chains are substituted by halogen atoms
• CPC Class Codes: C07C 43/126 having more than one ether bond
• CPC Class Codes: C07C 43/13 containing hydroxy or O-metal groups C07C43/11 takes precedence
• CPC Class Codes: C07C 43/192 : containing halogen
• CPC Class Codes: C07C 43/313 : containing halogen
• CPC Class Codes: C07C 59/135 : containing halogen
• CPC Class Codes: C07C 69/708 : Ethers
• CPC Class Codes: C07D 319/06 : not condensed with other rings
• CPC Class Codes: C08J 2203/146 : Saturated hydrocarbons containing oxygen and halogen atoms, e.g. F3C-O-CH2-CH3
• CPC Class Codes: C08J 9/143 : Halogen containing compounds
• CPC Class Codes: C11D 1/004 : Surface-active compounds containing F
• CPC Class Codes: C11D 7/28 : containing halogen

Abstract

Normally liquid, omega-hydrofluoroalkyl ether compounds (and selected mixtures thereof) have a saturated perfluoroaliphatic chain of carbon atoms interrupted by one or more ether oxygen atoms. The compounds can be prepared, e.g., by decarboxylation of the corresponding fluoroalkyl ether carboxylic acids and are useful, e.g., in cleaning and drying applications.

Claims

1. A process for transferring heat comprising the step of transferring heat between a heat source and a heat sink through the use of a heat transfer agent comprising at least one normally liquid omega-hydrofluoroalkyl ether compound having a saturated perfluoroaliphatic chain of carbon atoms interrupted by one or more ether oxygen atoms, the chain carbon atom at one end (the proximal end) of the chain being that of a difluoromethyl group which is bonded to another chain carbon atom or to a said ether-oxygen atom, the carbon atom at the other end (the distal end) of the chain being part of a distal group selected from the group consisting of difluoromethyl, difluorochloromethyl, a straight-chain perfluoroalkyl, a branched-chain perfluoroalkyl, and a perfluoroalkyl substituted with a saturated perfluoroalicyclic moiety, with the proviso that where said difluoromethyl group at the proximal end is bonded to a said ether-oxygen atom, then said straight-chain perfluoroalkyl has at least 6 chain carbon atoms and said branched-chain perfluoroalkyl has at least 4 carbon atoms.

2. The process of claim 1 wherein said normally liquid omega-hydrofluoroalkyl ether compound is represented by the general formula:

3. The process of claim 2 wherein said X is a fluorine atom.

4. The process of claim 2 wherein said normally liquid omega-hydrofluoroalkyl ether compound is represented by the formula:

5. The process of claim 2 wherein said normally liquid omega-hydrofluoroalkyl ether compound is represented by the formula:

6. The process of claim 2 wherein said normally liquid omega-hydrofluoroalkyl ether compound is represented by a formula selected from the group consisting of

C₈F₁₇—

O—

C₂F₄H, C₇F₁₅—

O—

C₂F₄H, C₆F₁₃—

O—

C₂F₄—

O—

CF₂H, C₄F₉—

O—

C₂F₄H, HCF₂CF₂—

O—

CF₂CF₂—

O—

CF₂CF₂H, C₄F₉—

O—

(CF₂)₅H, C₅F₁₁—

O—

(CF₂)₅H, C₈F₁₇—

O—

(CF₂)₅H, C₄F₉—

O—

CF₂C(CF₃)₂CF₂H, H(CF₂)₄—

O—

(CF₂)₄H, Cl(CF₂)₄—

O—

(CF₂)₄H, C₆F₁₃—

O—

C₂F₄H C₄F₉—

O—

(CF₂)₄—

O—

(CF₂)₃H, (C₂F₅)₂CFCF₂—

O—

C₂F₄H, c—

C₆F₁₁CF₂—

O—

C₂F₄H, C₄F₉—

O—

C₂F₄—

O—

C₃F₆H, C₆F₁₃—

O—

C₄F₈H, C₆F₁₃—

O—

C₃F₆H, C₅F₁₁—

O—

(CF₂)₄H, C₄F₉—

O—

C₃F₆H, C₈F₁₇OCF₂OC₃F₆H, HC₃F₆OC₃F₆H,

C₅F₁₁OCF₂C(CF₃)₂CF₂H, (C₄F₉O)₂CFCF₂H, CF₃O(CF₂)₉H, and (iso-C₃F₇)₂CFOC₂F₄H.

7. The process of claim 1 wherein said normally liquid omega-hydrofluoroalkyl ether compound is represented by the general formula: