Patent US5658962A successfully refreshed from Google Patents.
US5658962A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Omega-hydrofluoroalkyl ethers, precursor carboxylic acids and derivatives thereof, and their preparation and application
Assignee: 3M Innovative Properties Co
•
Filing: 1995-05-12
•
Granted: 1997-08-19
•
Expires: 2015-05-12
Abstract
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.
Inventors
- 👤 George G. I. Moore
- 👤 Richard M. Flynn
- 👤 Miguel A. Guerra
- 👤 John G. Owens
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 21:47
CPC Classifications
A; A61; A61K; A61K9/00; A61K9/0012; A61K9/0019; A61K9/0026; A61K49/00; A61K49/04; A61K49/0433; A61K49/0447; A61K49/0461; A61K49/06; A61K49/18; A61K49/1806; A61K49/22; A61K49/222; A61K49/226; A62; A62D; A62D1/00; A62D1/0028; A62D1/0035; A62D1/0071; A62D1/0085; B; B01; B01D; B01D12/00; B23; B23K; B23K35/00; B23K35/22; B23K35/38; B23K35/386; C; C07; C07C; C07C41/00; C07C41/01; C07C41/16; C07C41/18; C07C41/22; C07C41/24; C07C43/00; C07C43/02; C07C43/03; C07C43/04; C07C43/12; C07C43/123; C07C43/126; C07C43/18; C07C43/192; C07C43/30; C07C43/313; C07C59/00; C07C59/125; C07C59/135; C07C69/00; C07C69/66; C07C69/67; C07C69/708; C07D; C07D319/00; C07D319/04; C07D319/06; C08; C08J; C08J9/00; C08J9/04; C08J9/12; C08J9/14; C08J9/143; C11; C11D; C11D1/00; C11D1/004; C11D7/00; C11D7/22; C11D7/28; C07C2601/00; C07C2601/12; C07C2601/14; C07C2602/00; C07C2602/02; C07C2602/14; C07C2602/26; C07C2602/28; C08J2203/00; C08J2203/14; C08J2203/146
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
155 words
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 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.
Claim 2
Independent Claim
155 words
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 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.
Claim 3
Independent Claim
155 words
A method of removing a contaminant from an article comprising contacting said article with a composition comprising at least one normally liquid omega-hydrofluoroalkylether 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.
Claim 4
Independent Claim
155 words
A method of removing a contaminant from an article comprising contacting said article with a composition comprising at least one normally liquid omega-hydrofluoroalkylether 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.
Claim 5
Dependent Claim
25 words
The method of claim 2 further comprising the step of contacting said article simultaneously or sequentially with a composition comprising at least one organic solvent.
Claim 6
Dependent Claim
178 words
The method of claim 1 wherein said normally liquid omega-hydrofluoroalkyl ether compound is represented by the general formula: X--R.sub.f --O--(R.sub.f '--O).sub.n --R.sub.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, R f ' has 1 to 12 chain carbon atoms, and R f " has 2 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, R f ' has 1 or more chain carbon atoms, and R f " has 2 or more chain carbon atoms.
Claim 7
Dependent Claim
12 words
The method of claim 4 wherein said X is a fluorine atom.
Claim 8
Dependent Claim
178 words
The method of claim 2 wherein said normally liquid omega-hydrofluoroalkyl ether compound is represented by the general formula: X--R.sub.f --O--(R.sub.f '--O).sub.n --R.sub.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, R f ' has 1 to 12 chain carbon atoms, and R f " has 2 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, R f ' has 1 or more chain carbon atoms, and R f " has 2 or more chain carbon atoms.
Claim 9
Dependent Claim
12 words
The method of claim 6 wherein said X is a fluorine atom.
References Cited (Backward Citations)
CA890944A
Cited
US2713593A
Cited
US3214478A
Cited
US3342875A
Cited
FR1373014A
Cited
US3250808A
Cited
US3393228A
Cited
GB1194431A
Cited
US3706773A
Cited
US3597359A
Cited
US4094911A
Cited
US3674800A
Cited
US3766274A
Cited
US3787351A
Cited
US3962460A
Cited
US3903012A
Cited
US3911138B1
Cited
US3911138A
Cited
US4118421A
Cited
US4173654A
Cited
US4169807A
Cited
US4357282A
Cited
US5023362A
Cited
US4686024A
Cited
US4729856A
Cited
US5077036A
Cited
EP0261501A2
Cited
US4973716A
Cited
US4940814A
Cited
EP0307087A1
Cited
FR2620445A1
Cited
US4847427A
Cited
US5055138A
Cited
WO1990001901A1
Cited
US5202480A
Cited
US5053536A
Cited
WO1990003357A1
Cited
US5093432A
Cited
WO1990006296A1
Cited
US5104034A
Cited
US5118494A
Cited
WO1992002560A1
Cited
EP0482938A1
Cited
US5125978A
Cited
US5089152A
Cited
WO1992022678A1
Cited
US5185473A
Cited
WO1993001798A1
Cited
US5210106A
Cited
WO1993011868A1
Cited
US5262082A
Cited
US5476974A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 2000-08-18 | 2001-02-17 | 2001-08-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2004-08-18 | 2005-02-17 | 2005-08-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2008-08-18 | 2009-02-17 | 2009-08-19 | $7700.00 | Window Closed / Lapsed |