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

• US 6,361,713 B1
• Filed: 08/17/2000
• Issued: 03/26/2002
• Est. Priority Date: 05/20/1994
• Status: Expired due to Fees

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Guerra, Miguel A., Moore, George G. I., Owens, John G., Flynn, Richard M.
• Primary Examiner(s): Gupta, Yogendra N.
• Assistant Examiner(s): Hamlin, Derrick G.
• Application Number:
  US09/641,192
• Time in Patent Office: 586 Days
• Field of Search: 252/194, 568/615, 568/579, 568/677, 568/683, 813/7, 814/2, 815/0
• US Class Current: 252/194
• 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 method of displacing water from a surface which comprises contacting the surface with a liquid composition comprising a normally liquid omega-hydrofluoroalkyl ether compound represented by the general formula:

2. A method of removing a contaminant from an article comprising contacting said article with a composition comprising at least one normally liquid omega-hydrofluoroalkyl ether compound represented by the general formula:

 

X—

R_f—

O—

(R_f′

—

O)_n—

R_f″

—

H

wherein;

H is a primary hydrogen atom;

X is a fluorine atom, a primary hydrogen atom, or a primary chlorine atom;

n is an integer of 0 to 7; and

R_f, R_f′

, and R_f″

are independently selected from the group consisting of linear or branched, unsubstituted perfluoroalkylene groups;

linear or branched, perfluoroalkyl- or perfluorocycloalkyl-substituted perfluoroalkylene groups; and

linear or branched perfluoroalkylene groups substituted with an ether oxygen-containing moiety;

with the proviso that when X is H or Cl, R_f has 1 to 18 chain carbon atoms and each of R_f′ and

R_f″

independently has 1 to 12 chain carbon atoms; and

with the further proviso that when X is F, then R_f has at least 4 chain carbon atoms, and each of R_f′ and

R_f″

independently has 1 or more chain carbon atoms;

and with the still further proviso that when n is zero, then R_f is a perfluorocycloalkyl-substituted perfluoroalkylene group.