US5364547A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Lubricants containing perfluorocyclobutane rings
Assignee: Dow Chemical Co
•
Filing: 1993-04-26
•
Granted: 1994-11-15
•
Expires: 2013-04-26
Abstract
Abstract A new lubricant comprises at least one compound having a perfluorocyclobutane group, preferably a perfluorovinyl aryl ether. The lubricant is conveniently applied from solvents which are not chlorofluorocarbons and is effective at high temperatures e.g., in engines and for magnetic media, either internally or topically.
Inventors
- 👤 David A. Babb
- 👤 Ted A. Morgan
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 10:18
CPC Classifications
C; C07; C07C; C07C43/00; C07C43/02; C07C43/03; C07C43/14; C07C43/17; C07C43/20; C07C43/225; C07C65/00; C07C65/21; C07C65/24; C08; C08F; C08F16/00; C08F16/12; C08F16/32; C08J; C08J5/00; C08J5/04; C09; C09D; C09D127/00; C09D127/02; C09D127/12; C09D157/00; C09D157/06; C09D157/08; C10; C10M; C10M105/00; C10M105/50; C10M105/54; C10M107/00; C10M107/38; C10M131/00; C10M131/08; C10M131/10; C10M147/00; C10M147/04; G; G11; G11B; G11B5/00; G11B5/62; G11B5/72; G11B5/725; G11B5/7253; G11B5/7257; C07C2603/00; C07C2603/02; C07C2603/04; C07C2603/06; C07C2603/10; C07C2603/12; C07C2603/18; C08J2327/00; C08J2327/02; C08J2327/12; C10M2213/00; C10M2213/04; C10M2213/06; C10N; C10N2040/00; C10N2040/14; C10N2040/16; C10N2040/17; C10N2040/175; C10N2040/18; C10N2040/185; C10N2040/25; C10N2040/251; C10N2040/255; C10N2040/28; C10N2050/00; C10N2050/015; C10N2050/02
Claims Analysis
Total Claims: 41
Claim 1
Independent Claim
22 words
A lubricant comprising at least one compound having a perfluorocyclobutane group, hydrocarbyl group, and at least one non-carbon atom in the backbone.
Claim 2
Dependent Claim
22 words
A lubricant comprising at least one compound having a perfluorocyclobutane group, hydrocarbyl group, and at least one non-carbon atom in the backbone.
Claim 3
Dependent Claim
15 words
The lubricant of claim 1 in which the perfluorocyclobutane groups comprise perfluorocyclobutane aryl ether groups.
Claim 4
Dependent Claim
14 words
The lubricant of claim 2 which comprises a dimer of a perfluorovinyl aryl ether.
Claim 5
Dependent Claim
11 words
The lubricant of claim 2 which comprises a poly(perfluorocyclobutane aryl ether).
Claim 6
Dependent Claim
16 words
The lubricant of claim 2 imparting a dynamic coefficient of friction of less than about 0.25.
Claim 7
Dependent Claim
24 words
The lubricant of claim 2 comprising a lubricant base stock and at least about 0.1 weight percent of a least one poly(perfluorocyclobutane aryl ether).
Claim 8
Dependent Claim
24 words
The lubricant of claim 6 wherein the base stock comprises at least one poly alpha olefin, polyglycol, polyphenyl ether, polyol esters or mixture thereof.
Claim 9
Dependent Claim
15 words
The lubricant of claim 7 wherein the base stock comprises at least one polyphenyl ether.
Claim 10
Dependent Claim
16 words
The lubricant of claim 7 which comprises at least about 50 weight percent poly(perfluorocyclobutane aryl ether).
Claim 11
Dependent Claim
16 words
The lubricant of claim 7 which comprises at least about 95 weight percent poly(perfluorocyclobutane aryl ether).
Claim 12
Dependent Claim
17 words
The lubricant of claim 2 which is a liquid comprising polymeric and oligomeric poly(perfluorocyclobutane aryl ether) compounds.
Claim 13
Dependent Claim
24 words
The lubricant of claim 11 wherein the poly(perfluorocyclobutane aryl ether), has a weight average molecular weight of equal to or greater than about 75,000,
Claim 14
Dependent Claim
32 words
The lubricant of claim 2 wherein the compound having perfluorocyclobutane aryl ether groups is a poly(perfluorocyclobutane aryl ether), and has a weight average molecular weight of from about 60,000 to about 600,000.
Claim 15
Dependent Claim
15 words
The lubricant of claim 13 wherein the poly(perfluorocyclobutane aryl ether) is a cured thermoset polymer
Claim 16
Dependent Claim
17 words
The lubricant of claim 11 which comprises a mixture of polymeric and dimeric poly(perfluorocyclobutane aryl ether) compounds.
Claim 17
Dependent Claim
8 words
The lubricant of claim 15 which is linear.
Claim 18
Dependent Claim
26 words
The lubricant of claim 16 which is prepared from a mixture of monomers having two dimerizable perfluorovinyl groups and end-capping agents having one dimerizable perfluorovinyl group.
Claim 19
Dependent Claim
25 words
The lubricant of claim 17 wherein the ratio of monomers having two dimerizable perfluorovinyl groups to end-capping agents are from about 1:10 to about 10:1,
Claim 20
Dependent Claim
25 words
The lubricant of claim 18 wherein the ratio of monomers having two dimerizable perfluorovinyl groups to end-capping agents are from about 1:5 to about 5:1.
Claim 21
Dependent Claim
11 words
The lubricant of claim 15 which has a branched molecular structure
Claim 22
Dependent Claim
28 words
The lubricant of claim 20 which is prepared from a mixture of monomers having three or more dimerizable perfluorovinyl groups and endcapping agents having one dimerizable perfluorovinyl group.
Claim 23
Dependent Claim
27 words
The lubricant of claim 21 wherein the ratio of monomers having three or more dimerizable perfluorovinyl groups to end-capping agents is from about 1:20 to about 1:1.5,
Claim 24
Dependent Claim
27 words
The lubricant of claim 22 wherein the ratio of monomers having three or more dimerizable perfluorovinyl groups to end-capping agents is from about 1:15 to about 1:2.
Claim 25
Dependent Claim
14 words
The lubricant of claim 15 which is a mixture of linear and branched structures.
Claim 26
Dependent Claim
28 words
The lubricant of claim 24 which is prepared from a mixture of monomers having two or more dimerizable perfluorovinyl groups and end-capping agents having one dimerizable perfluorovinyl group.
Claim 27
Dependent Claim
34 words
The lubricant of claim 25 wherein the ratio of monomers having two dimerizable perfluorovinyl groups to monomers having more than two dimerizable perfluorovinyl groups to end-capping agents is from about 1:0.1:1.5 to about 1:200:2000.
Claim 28
Dependent Claim
34 words
The lubricant of claim 26 wherein the ratio of monomers having two dimerizable perfluorovinyl groups to monomers having more than two dimerizable perfluorovinyl groups to end-capping agents is from about 1:0.5:2 to about 1:100:500.
Claim 29
Dependent Claim
21 words
The lubricant of claim 11 wherein the poly(perfluorocyclobutane aryl ether), has a weight average molecular weight of less than about 75,000.
Claim 30
Dependent Claim
23 words
The lubricant of claim 11 wherein the poly(perfluorocyclobutane aryl ether), has a weight average molecular weight of from about 348 to about 10,000.
Claim 31
Dependent Claim
23 words
The lubricant of claim 29 wherein the poly(perfluorocyclobutane aryl ether), has a weight average molecular weight of from about 348 to about 3000.
Claim 32
Dependent Claim
57 words
The lubricant of claim 2 in which the compound containing perfluorocyclobutane aryl ether groups is a poly(perfluorocyclobutane aryl ether) and has aryl groups substituted with at least one fluorine, trifluoromethyl, tetrafluoroethoxy, trifluoromethoxy, methoxy, cyano, carboxylic acid, carboxylate alkyl ester, sulfonate alkyl ester, alkyl or aryl sulfone, amide, pentafluorosulfanyl, alkyl phosphonate, piperanyl, amine group, alcohol or combination thereof.
Claim 33
Dependent Claim
92 words
The lubricant of claim 1 having a formula represented by Formula 2: [R--X--Q--X--].sub.v -[R'--X--Q--X].sub.m -[R"--X--Q--X].sub.n [R"'].sub.p. wherein each of R, and R"' are the same or different aromatic groups; R' is a branching group; R" is an unbranched chain extending group derived from compounds having 2 dimerizable perfluorovinyl groups; X is oxygen or sulfur and Q is a perfluorocyclobutane group; subscripts v, m, n, and p are integers representing the number of groups in the brackets preceeding them such that v+p=am+2 where (a+2) is the number of dimerizable perfluorovinyl groups on R'.
Claim 34
Dependent Claim
90 words
The lubricant of claim 32 wherein R is selected from perchlorophenylene, phenylene, biphenylene, naphthylene, dichlorophenylene, benzophenone, nitrophenylene, p,p'(2,2-diphenylene propane) trifluoroethenyloxyphenyl)-ethane [--C 6 H 4 --C(CH 3 ) 2 --C 6 H 4 ]; p,p'-(2,2-diphenylene-1,1,1,3,3,3 hexafluoropropane), [--C 6 H 4 --C(CF 3 ) 2 --C 6 H 4 --], 1,4-bis(hexafluoroisopropyl)benzene[--C(CF 3 ) 2 --C 6 H 4 --C(CF 3 ) 2 --], 1,3-bis(hexafluoroisopropyl)benzene [--C(CF 3 ) 2 --C 6 H 4 --C(CF 3 ) 2 --], biphenylene; phenylene; 9,9'-diphenylfluorene, oxydiphenylene; thiodiphenylene; 2,2-diphenylene propane; 2,2'-diphenylene, 1,1,1,3,3,3-hexafluoropropane; 1,1-diphenylene-1-phenylethane; naphthalene, anthracene and mixtures thereof.
Claim 35
Dependent Claim
21 words
The lubricant of claim 33 wherein R has at least one fluorine or fluorine-containing substituent in addition to the perfluorocyclobutane rings.
Claim 36
Dependent Claim
49 words
The lubricant of claim 1 having a structure represented by at least one of Formulas 3 or 4: ##STR4## wherein J is H, or an inert or reactive substituent; or ##STR5## wherein J is as described for Formula 3 and K is an unsubstituted or inertly substituted hydrocarbyl group.
Claim 37
Dependent Claim
57 words
The lubricant of claim 1 having a structure represented by Formula 5 ##STR6## wherein n is an integer of from about 0 to about 20 and L is independently trifluoromethyl, fluorine, trifluoromethoxy, tetrafluoroethoxy, perfluoroalkoxy, methoxy, cyano, carboxylic acid, carboxylate alkyl ester, sulfonate alkyl ester, alkyl or aryl sulfones, amide, pentafluorosulfanyl, alkyl phosphonate, piperaryl, amino or alcohol groups.
Claim 38
Dependent Claim
16 words
The lubricant of claim 36 wherein n is an integer of from 1 to about 20.
Claim 39
Dependent Claim
15 words
The lubricant of claim 36 wherein n is 0; and L is a trifluoromethyl group.
Claim 40
Independent Claim
17 words
A method of lubricating an engine using a composition comprising at least one poly(perfluorocyclobutane aryl ether) compound.
Claim 41
Independent Claim
17 words
A method of lubricating an engine using a composition comprising at least one poly(perfluorocyclobutane aryl ether) compound.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1997-11-14 | 1998-05-16 | 1998-11-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2001-11-14 | 2002-05-16 | 2002-11-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2005-11-14 | 2006-05-16 | 2006-11-15 | $7700.00 | Window Closed / Lapsed |