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

• US 5,476,974 A
• Filed: 05/20/1994
• Issued: 12/19/1995
• Est. Priority Date: 05/20/1994
• Status: Expired due to Term

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Company
• Inventors: Moore, George G. I., Guerra, Miguel A.
• Primary Examiner(s): Acquah, Samuel A.
• Application Number:
  US08/246,962
• Time in Patent Office: 578 Days
• Field of Search: 528/271, 528/274, 528/361, 528/367, 528/368, 528/369, 528/370, 528/371, 528/401, 521/50, 106/18.11, 106/310, 252/380, 560/155, 560/161, 560/170, 560/172, 560/227, 568/677, 568/683, 568/704
• US Class Current: 568/677
• 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 1/0035 Aqueous solutions
• 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 41/18 by reactions not forming ether-oxygen bonds
• CPC Class Codes: C07C 41/24 by elimination of halogens, e.g. elimination of HCl
• CPC Class Codes: C07C 41/48 Preparation of compounds having groups
• 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 43/192 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

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 compound represented by the formula:

R_fs --O--(CF₂)_b --Z

where

R_fs is a linear or branched perfluoroalkyl group having from 1 to 18 carbon atoms;

"b" is an integer of at least 3; and

Z is selected from the group consisting of --COOH, --COOM_1/v, --COONH₄, --COOR, --CH₂ OH, --COF, --COCl, --COR, --CONRR, --CH₂ NH₂, --CH₂ NCO, --CN, --CH₂ OSO₂ R, --CH₂ OCOR, --CH₂ OCOCR═

CH₂, --CONH(CH₂)_m Si(OR)₃, and --CH₂ O(CH₂)_m Si(OR)₃, where M is an ammonium radical or a metal atom having a valence "v" of 1 to 4, each R is independently selected from the group consisting of alkyl groups having from 1 to 14 carbon atoms, fluoroalkyl groups having from 1 to 14 carbon atoms, aryl groups having from 6 to 10 ring-carbon atoms, and heteroatom-containing alkyl groups having from 1 to 14 carbon atoms, fluoroalkyl groups having from 1 to 14 carbon atoms, and aryl groups having from 6 to 10 ring-carbon atoms, and m is an integer of 1 to 11.

2. A compound according to claim 1 represented by the formula:

C₅ F₁₁ --O--(CF₂)₅ CO₂ H.

3. A compound represented by the formula:

R_ft --(O--R_ft '"'"')c--O--(CF₂)d--Z

wherein;

R_ft is a linear or branched perfluoroalkyl group having from 1 to 18 carbon atoms;

R_ft '"'"' is a linear or branched perfluoroalkylene group having from 1 to 11 carbon atoms;

c is an integer of at least 1;

d is an integer of at least 3; and

Z is selected from the group consisting of --COOH, --COOM_1/v, --COONH₄, --COOR, --CH₂ OH, --COF, --COCl, --COR, --CONRR, --CH₂ NH₂, --CH₂ NCO, --CN, --CH₂ OSO₂ R, --CH₂ OCOR, --CH₂ OCOCR=CH₂, --CONH (CH₂)_m Si(OR)₃, and --CH₂ O(CH₂)_m Si(OR)₃, where M is an ammonium radical or a metal atom having a valence "v" of 1 to 4, each R is independently selected from the group consisting of alkyl groups having from 1 to 14 carbon atoms, fluoroalkyl groups having from 1 to 14 carbon atoms, aryl groups having from 6 to 10 ring-carbon atoms, and heteroatom-containing alkyl groups having from 1 to 4 carbon atoms, fluoroalkyl groups having from 1 to 14 carbon atoms, and aryl groups having from 6 to 10 ring-carbon atoms, and m is an integer of 1 to 11.