US4583826A
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Phenylethanes
Assignee: F Hoffmann La Roche AG
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Filing: 1982-10-01
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Granted: 1986-04-22
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Expires: 2002-10-01
Abstract
Abstract Compounds of the formula ##STR1## wherein R 1 signifies trans-4-alkylcyclohexyl, 4'-alkyl-4-biphenylyl, p-(trans-4-alkylcyclohexyl)phenyl, 2-(trans-4-alkylcyclohexyl)ethyl or p-[2-(trans-4-alkylcyclohexyl)ethyl]phenyl and R 2 signifies trans-4-alkylcyclohexyl; or R 1 signifies trans-4-alkylcyclohexyl and R 2 signifies p-(trans-4-alkylcyclohexyl)phenyl, p-[2-(trans-4-alkylcyclohexyl)ethyl]phenyl or 4'-(trans-4-alkylcyclohexyl)-4-biphenylyl; or R 1 signifies p-alkylphenyl and R 2 signifies p-[2-(trans-4-alkylcyclohexyl)ethyl]phenyl, and the alkyl groups in the substituents R 1 and R 2 are straight-chain groups containing 1 to 7 carbon atoms, liquid crystalline mixtures which contain these compounds and their use for electro-optical purposes are described. The novel compounds of formula I are especially valuable as components in liquid crystal mixtures and themselves have liquid crystalline properties.
Inventors
- 👤 Martin Petrzilka
- 👤 Martin Schadt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 02:55
CPC Classifications
C; C09; C09K; C09K19/00; C09K19/04; C09K19/42; C07; C07C; C07C1/00; C07C1/32; C07C1/325; C07C1/326; C07C13/00; C07C13/28; C07C45/00; C07C45/44; C07C5/00; C07C5/02; C07C5/03; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/54; C07F9/5456; C09K19/06; C09K19/08; C09K19/30; C09K19/3001; C09K19/3028; C07C2601/00; C07C2601/12; C07C2601/14
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
65 words
A compound of the formula ##STR18## wherein R 1 is trans-4-alkylcyclohexyl, 4'-alkyl-4-biphenylyl, p-(trans-4-alkylcyclohexyl)phenyl, 2-(trans-4-alkylcyclohexyl)ethyl or p-[2-(trans-4-alkylcyclohexyl)ethyl]phenyl and R 2 is trans-4-alkylcyclohexyl; or R 1 is trans-4-alkylcyclohexyl and R 2 is p-(trans-4-alkylcyclohexyl)phenyl, p-[2-(trans-4-alkylcyclohexyl)ethyl]phenyl or 4'-(trans-4-alkylcyclohexyl)-4-biphenylyl; or R 1 is p-alkylphenyl and R 2 is p-[2-(trans-4-alkylcyclohexyl)ethyl]phenyl, and the alkyl groups in the substituents R 1 and R 2 are straight-chain groups of 1 to 7 carbon atoms.
Claim 2
Dependent Claim
65 words
A compound of the formula ##STR18## wherein R 1 is trans-4-alkylcyclohexyl, 4'-alkyl-4-biphenylyl, p-(trans-4-alkylcyclohexyl)phenyl, 2-(trans-4-alkylcyclohexyl)ethyl or p-[2-(trans-4-alkylcyclohexyl)ethyl]phenyl and R 2 is trans-4-alkylcyclohexyl; or R 1 is trans-4-alkylcyclohexyl and R 2 is p-(trans-4-alkylcyclohexyl)phenyl, p-[2-(trans-4-alkylcyclohexyl)ethyl]phenyl or 4'-(trans-4-alkylcyclohexyl)-4-biphenylyl; or R 1 is p-alkylphenyl and R 2 is p-[2-(trans-4-alkylcyclohexyl)ethyl]phenyl, and the alkyl groups in the substituents R 1 and R 2 are straight-chain groups of 1 to 7 carbon atoms.
Claim 3
Dependent Claim
20 words
The compound of claim 1 wherein R 1 is trans-4-alkylcyclohexyl, 4'-alkyl-4-biphenylyl, p-(trans-4-alkylcyclohexyl)phenyl, 2-(trans-4-alkylcyclohexyl)ethyl or p-[2-(trans-4-alkylcyclohexyl)ethyl]phenyl and R 2 is trans-4-alkylcyclohexyl.
Claim 4
Dependent Claim
18 words
The compound of claim 1 wherein R 1 is trans-4-alkylcyclohexyl and R 2 is p-(trans-4-alkylcyclohexyl)phenyl, p-[2-(trans-4-alkylcyclohexyl)ethyl]phenyl or 4'-(trans-4-alkylcyclohexyl)-4-biphenylyl.
Claim 5
Dependent Claim
15 words
The compound of claim 1 wherein R 1 is p-alkylphenyl and R 2 is p-[2-(trans-4-alkylcyclohexyl)ethyl]phenyl.
Claim 6
Dependent Claim
31 words
The compound of claim 1 wherein R 1 is trans-4-alkylcyclohexyl, p-(trans-4-alkylcyclohexyl)phenyl, 2-(trans-4-alkylcyclohexyl)ethyl or p-[2-(trans-4-alkylcyclohexyl)ethyl]phenyl and R 2 is trans-4-alkylcyclohexyl; or R 1 is trans-4-alkylcyclohexyl and R 2 is p-(trans-4-alkylcyclohexyl)phenyl or p-[2-(trans-4-alkylcyclohexyl)ethyl]phenyl.
Claim 7
Dependent Claim
13 words
The compound of claim 1 wherein R 1 and R 2 are trans-4-alkylcyclohexyl.
Claim 8
Dependent Claim
15 words
The compound of claim 1 wherein R 1 is 4'-alkyl-4-biphenylyl and R 2 is trans-4-alkylcyclohexyl.
Claim 9
Dependent Claim
15 words
The comound of claim 1 wherein R 1 is p-(trans-4-alkylcyclohexyl)phenyl and R 2 is trans-4-alkylcyclohexyl.
Claim 10
Dependent Claim
15 words
The compound of claim 1 wherein R 1 is trans-4-alkylcyclohexyl and R 2 is 4'-(trans-4-alkylcyclohexyl)-4-biphenylyl.
Claim 11
Dependent Claim
34 words
The compound of claims 1, 2, 3, 4, 5 or 6 wherein the sum of the carbon atoms in the alkyl groups of the substituents R 1 and R 2 is 5 to 10.
Claim 12
Dependent Claim
6 words
The compound of claim 1, 1-[2-(trans-4-butylcyclohexyl)ethyl]-4-(trans-4-pentylcyclohexyl)benzene.
Claim 13
Dependent Claim
6 words
The compound of claim 1, 4-[2-(trans-4-butylcyclohexyl)ethyl]-4'-(trans-4-pentylcyclohexyl)-1,1'-ethylenedibenzene.
Claim 14
Dependent Claim
6 words
The compound of claim 1, 4-(trans-4-pentylcyclohexyl)-4'-[2-(trans-4-butylcyclohexyl)ethyl]biphenyl.
Claim 15
Dependent Claim
82 words
A liquid crystalline mixture comprising at least two components wherein at least one of said components is a compound of the formula ##STR19## wherein R 1 is trans-4-alkylcyclohexyl, 4'-alkyl-4-biphenylyl, p-(trans-4-alkylcyclohexyl)phenyl, 2-(trans-4-alkylcyclohexyl)ethyl or p-[2-(trans-4-alkylcyclohexyl)ethyl]phenyl and R 2 is trans-4-alkylcyclohexyl; or R 1 is trans-4-alkylcyclohexyl and R 2 is p-(trans-4-alkylcyclohexyl)phenyl, p-[2-(trans-4-alkylcyclohexyl)ethyl]phenyl or 4'-(trans-4-alkylcyclohexyl)-4-biphenylyl; or R 1 is p-alkylphenyl and R 2 is p-[2-(trans-4-alkylcyclohexyl)ethyl]phenyl, and the alkyl groups in the substituents R 1 and R 2 are straight-chain groups of 1 to 7 carbon atoms.
Claim 16
Dependent Claim
82 words
A liquid crystalline mixture comprising at least two components wherein at least one of said components is a compound of the formula ##STR19## wherein R 1 is trans-4-alkylcyclohexyl, 4'-alkyl-4-biphenylyl, p-(trans-4-alkylcyclohexyl)phenyl, 2-(trans-4-alkylcyclohexyl)ethyl or p-[2-(trans-4-alkylcyclohexyl)ethyl]phenyl and R 2 is trans-4-alkylcyclohexyl; or R 1 is trans-4-alkylcyclohexyl and R 2 is p-(trans-4-alkylcyclohexyl)phenyl, p-[2-(trans-4-alkylcyclohexyl)ethyl]phenyl or 4'-(trans-4-alkylcyclohexyl)-4-biphenylyl; or R 1 is p-alkylphenyl and R 2 is p-[2-(trans-4-alkylcyclohexyl)ethyl]phenyl, and the alkyl groups in the substituents R 1 and R 2 are straight-chain groups of 1 to 7 carbon atoms.
Claim 17
Dependent Claim
114 words
The liquid crystalline mixture of claim 14 comprising one or more compounds of formula I and one or more compounds of the formulae ##STR20## wherein R 7 is a straight-chain alkyl or alkoxy group of 2 to 7 carbons atoms, R 8 is a straight-chain alkyl group of 2 to 7 carbon atoms, R 9 is cyano or a straight-chain alkoxy group of 1 to 6 carbon atoms, R 10 is a straight-chain alkyl group of 3 to 7 carbon atoms, R 11 is cyano or a straight-chain alkyl or alkoxy group of 1 to 7 carbon atoms and R 12 is cyano or a straight-chain alkyl group of 1 to 7 carbon atoms.
Claim 18
Dependent Claim
18 words
The liquid crystalline mixture of claim 14 comprising 4'-propyl-4-cyanobiphenyl, 4'-pentyl-4-cyanobiphenyl, 2-(trans-4-propylcyclohexyl)-1-(p-ethoxyphenyl)ethane, 2-(trans-4-pentylcyclohexyl)-1-(p-ethoxyphenyl)ethane, 4"-pentyl-4-cyano-p-terphenyl, 4'-(trans-4-pentylcyclohexyl)-4-cyanobiphenyl, 1-[2-(trans-4-butylcyclohexyl)ethyl]-4-(trans-4-pentylcyclohexyl)benzene, 4-[2-(trans-4-butylcyclohexyl)ethyl]-4'-(trans-4-pentylcyclohexyl)-1,1'-ethylenedibenzene and 4-(trans-4-pentylcyclohexyl)-4'-[2-(trans-4-butylcyclohexyl)ethyl]biphenyl.
Claim 19
Dependent Claim
102 words
In an improved electro-optical cell having two plate means, liquid crystal means disposed between the two plate means and means for applying an electrical potential to said plate means, the improvement comprising the liquid crystal means including a compound of the formula ##STR21## wherein R 1 is trans-4-alkylcyclohexyl, 4'-alkyl-4-biphenylyl, p-(trans-4-alkylcyclohexyl)phenyl, 2-(trans-4-alkylcyclohexyl)ethyl or p-[2-(trans-4-alkylcyclohexyl)ethyl]phenyl and R 2 is trans-4-alkylcyclohexyl; or R 1 is trans-4-alkylcyclohexyl and R 2 is p-(trans-4-alkylcyclohexyl)phenyl, p-[2-(trans-4-alkylcyclohexyl)ethyl]phenyl or 4'-(trans-4-alkylcyclohexyl)-4-biphenyl; or R 1 is p-alkylphenyl and R 2 is p-[2-(trans-4-alkylcyclohexyl)ethyl]phenyl, and the alkyl groups in the substituents R 1 and R 2 are straight-chain groups of 1 to 7 carbon atoms.
Claim 20
Dependent Claim
102 words
In an improved electro-optical cell having two plate means, liquid crystal means disposed between the two plate means and means for applying an electrical potential to said plate means, the improvement comprising the liquid crystal means including a compound of the formula ##STR21## wherein R 1 is trans-4-alkylcyclohexyl, 4'-alkyl-4-biphenylyl, p-(trans-4-alkylcyclohexyl)phenyl, 2-(trans-4-alkylcyclohexyl)ethyl or p-[2-(trans-4-alkylcyclohexyl)ethyl]phenyl and R 2 is trans-4-alkylcyclohexyl; or R 1 is trans-4-alkylcyclohexyl and R 2 is p-(trans-4-alkylcyclohexyl)phenyl, p-[2-(trans-4-alkylcyclohexyl)ethyl]phenyl or 4'-(trans-4-alkylcyclohexyl)-4-biphenyl; or R 1 is p-alkylphenyl and R 2 is p-[2-(trans-4-alkylcyclohexyl)ethyl]phenyl, and the alkyl groups in the substituents R 1 and R 2 are straight-chain groups of 1 to 7 carbon atoms.
References Cited (Backward Citations)
US4035056A
Cited
US4130502A
Cited
US4337999A
Cited
US4261651A
Cited
DE3003256A1
Cited
US4330426A
Cited
GB2065104A
Cited
US4331552A
Cited
DE3006666A1
Cited
GB2086385A
Cited
US4400293A
Cited
GB2092169A
Cited
EP0056113A1
Cited
US4419263A
Cited
US4431853A
Cited
US4439015A
Cited
GB2092146A
Cited
GB2093057A
Cited
JPS57163324A
Cited
US4460770A
Cited
JPS588023A
Cited
JPS5810529A
Cited
JPS588022A
Cited
EP0072204A1
Cited
US4482472A
Cited
US4455443A
Cited
EP0084194A1
Cited
US4393258A
Cited
US4472592A
Cited
US4514044A
Cited
JPS59110631A
Cited
JPS59110630A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-04-21 | 1989-10-21 | 1990-04-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-04-21 | 1993-10-21 | 1994-04-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-04-21 | 1997-10-21 | 1998-04-22 | $7700.00 | Window Closed / Lapsed |