US4812258A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Fluorine-containing pyrimidine derivatives
Assignee: Merck Patent GmbH
•
Filing: 1987-04-08
•
Granted: 1989-03-14
•
Expires: 2007-04-08
Abstract
Abstract Liquid crystalline fluorine-containing pyrimidine compounds have the formula I ##STR1## wherein R 1 and R 2 are H, R, OR or OCOR, and one of them can also be CN or F, or, if A is a covalent bond, also one or both of R 1 and R 2 can be 4-R 4 -phenyl or 4-R-cyclohexyl, wherein R 4 is R, OR, cyano, f or OCOR; wherein R is an alkyl group of 1 to 12 C atoms; R 3 is F or, if one of the radicals R 1 or R 2 is F or 4-fluorophenyl, also H; Z is 1,3-pyrimidin-2,5-diyl; and A is 1,4-phenylene, 1,4-cyclohexylene or a covalent bond. Fluorine-containing pyrimidine compounds are useful components of liquid crystal dielectrics for electro-optical display devices.
Inventors
- 👤 Joachim Krause
- 👤 Michael Romer
- 👤 Ludwig Pohl
- 👤 Bernhard Scheuble
- 👤 Georg Weber
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 17:50
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/02; C07D239/24; C07D239/26; C09; C09K; C09K19/00; C09K19/04; C09K19/06; C09K19/34; C09K19/3441; C09K19/345; C09K19/3458; C09K19/3469
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
69 words
In a liquid crystal dielectric useful for electrooptical display elements and comprising at least two liquid crystal components, the improvement wherein at least one component is a fluorine-containing pyrimidine compound of the formula R 1 --PhF--R 2 wherein PhF is 2- or 3-fluoro-1,4-phenylene, one of the radicals R 1 and R 2 is alkyl of 1 to 12 C atoms and the other is CN and Z is 1,3-pyrimidine-2,5-diyl.
Claim 2
Dependent Claim
69 words
In a liquid crystal dielectric useful for electrooptical display elements and comprising at least two liquid crystal components, the improvement wherein at least one component is a fluorine-containing pyrimidine compound of the formula R 1 --PhF--R 2 wherein PhF is 2- or 3-fluoro-1,4-phenylene, one of the radicals R 1 and R 2 is alkyl of 1 to 12 C atoms and the other is CN and Z is 1,3-pyrimidine-2,5-diyl.
Claim 3
Dependent Claim
15 words
A dielectric of claim 1, wherein in said pyrimidine compound the alkyl group is straight-chained.
Claim 4
Dependent Claim
27 words
A dielectric of claim 1, wherein said pyrimidine compound is of the formula R--Z--PhF--CN or NC--Z--PhF--R wherein R is straight-chained alkyl of 2 to 8 C atoms.
Claim 5
Dependent Claim
8 words
A dielectric of claim 1, comprising 2-15 components.
Claim 6
Dependent Claim
20 words
In an electrooptical display element comprising a liquid crystalline dielectric, the improvement wherein the dielectric is one of claim 1.
Claim 7
Dependent Claim
36 words
A fluorine-containing pyrimidine compound of the formula ##STR5## wherein R 1 is alkyl of 4 to 12 C atoms, R 2 is alkyl or alkoxy of 8 to 12 C atoms, and R 3 is fluorine.
Claim 8
Dependent Claim
36 words
A fluorine-containing pyrimidine compound of the formula ##STR5## wherein R 1 is alkyl of 4 to 12 C atoms, R 2 is alkyl or alkoxy of 8 to 12 C atoms, and R 3 is fluorine.
Claim 9
Dependent Claim
13 words
A compound of claim 6, wherein ##STR6## is a 3-fluoro-4-R 2 -phenyl group.
Claim 10
Dependent Claim
14 words
A compound of claim 6, wherein R 1 and R 2 are straight-chained groups.
Claim 11
Dependent Claim
19 words
A compound of claim 8, wherein R 1 is n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl or n-dodecyl.
Claim 12
Dependent Claim
20 words
A compound of claim 9, wherein R 2 is n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-octyloxy, n-nonyloxy, n-decyloxy, n-undecyloxy or n-dodecyloxy.
Claim 13
Dependent Claim
18 words
2-(3-fluoro-4-n-dodecyloxyphenyl)-5-n-hexylpyrimidine 2-(3-fluoro-4-n-octyloxyphenyl)-5-n-butylpyrimidine 2-(3-fluoro-4-n-octyloxyphenyl)-5-n-pentylpyrimidine 2-(3-fluoro-4-n-octyloxyphenyl)-5-n-hexylpyrimidine 2-(3-fluoro-4-n-octyloxyphenyl)-5-n-heptylpyrimidine 2-(3-fluoro-4-n-octyloxyphenyl)-5-n-octylpyrimidine 2(3-fluoro-4-n-octylphenyl)-5-n-butylpyrimidine 2(3-fluoro-4-n-octylphenyl)-5-n-pentylpyrimidine 2(3-fluoro-4-n-octylphenyl)-5-n-hexylpyrimidine 2(3-fluoro-4-n-octylphenyl)-5-n-heptylpyrimidine and 2(3-fluoro-4-n-octylphenyl)-5-n-octylpyrimidine, each a compound of claim 6.
Claim 14
Dependent Claim
31 words
In a liquid crystal dielectric useful for electrooptical display elements and comprising at least two liquid crystal components, the improvement wherein at least one component is a compound of claim 6.
Claim 15
Dependent Claim
8 words
A dielectric of claim 12, comprising 2-15 components.
Claim 16
Dependent Claim
20 words
In an electrooptical display element comprising a liquid crystalline dielectric, the improvement wherein the dielectric is one of claim 12.
References Cited (Backward Citations)
DE2257588A1
Cited
US3997536A
Cited
US4062798A
Cited
US4309539A
Cited
US4273929A
Cited
US4302352A
Cited
US4358393A
Cited
DD159505A3
Cited
US4402849A
Cited
JPS56150030A
Cited
US4438268A
Cited
US4405488A
Cited
US4415470A
Cited
GB2092169A
Cited
US4493726A
Cited
US4564694A
Cited
US4490305A
Cited
EP0084194A1
Cited
US4551264A
Cited
US4512636A
Cited
US4510069A
Cited
US4533488A
Cited
US4536321A
Cited
EP0123907A2
Cited
DE3315295A1
Cited
JPS59216876A
Cited
US4713197A
Cited
DE3404117A1
Cited
WO1986000067A1
Cited
US4621901A
Cited
DE3500897A1
Cited
US4684476A
Cited
JPS62169765A
Cited
DE3606787A1
Cited
US4640795A
Cited
JPS62223171A
Cited
JPH0651778A
Cited
JPH0654371A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1992-03-13 | 1992-09-12 | 1993-03-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-03-13 | 1996-09-12 | 1997-03-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-03-13 | 2000-09-12 | 2001-03-14 | $7700.00 | Window Closed / Lapsed |