Patent US4211666A successfully refreshed from Google Patents.
US4211666A
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Liquid crystal compounds
Assignee: JNC Corp
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Filing: 1978-11-14
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Granted: 1980-07-08
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Expires: 1998-11-14
Abstract
Abstract Novel compounds, 4-alkyl-cyclohexenes having at the 1-position thereof p-cyanophenyl group or 4'-cyano-4-biphenylyl group, expressed by the general formula ##STR1## wherein R represents a straight alkyl group having 1˜9 carbon atoms and n represents 1 or 2; methods for producing the same; and nematic liquid crystal (L.C.) compositions comprising at least one member selected from the group consisting of said compounds, are provided. Said compounds having a cyclohexene ring have a lower viscosity than conventional L.C. compounds, and have effectivenesses of short response time when applied to L.C. display apparatus; superior compatibility with other L.C. compounds to form convenient L.C. mixture; and no need of separating cis- and trans-forms in the midway step of the preparation as in the prior art.
Inventors
- 👤 Takashi Inukai
- 👤 Hiromichi Inoue
- 👤 Hideo Sato
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 03:14
CPC Classifications
C; C09; C09K; C09K19/00; C09K19/04; C09K19/06; C09K19/08; C09K19/30; C09K19/3098; C07; C07C; C07C17/00; C07C17/26; C07C17/263; C07C17/2637; C07C17/35; C07C29/00; C07C29/17; C07C29/19; C07C29/20; C07C29/36; C07C29/38; C07C29/40; C07C45/00; C07C45/27; C07C45/29; C07C45/292; C07C49/00; C07C49/385; C07C49/403; C12; C12C; C12C11/00; C12C11/02; C07B; C07B2200/00; C07B2200/09; C07C2601/00; C07C2601/12; C07C2601/14
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
34 words
4-Alkylcyclohexenes having at the 1-position thereof p-cyanophenyl group or 4'-cyano-4-biphenylyl group, expressed by the general formula ##STR6## wherein R represents a straight alkyl group having 1˜9 carbon atoms and n represents 1 or 2.
Claim 2
Dependent Claim
34 words
4-Alkylcyclohexenes having at the 1-position thereof p-cyanophenyl group or 4'-cyano-4-biphenylyl group, expressed by the general formula ##STR6## wherein R represents a straight alkyl group having 1˜9 carbon atoms and n represents 1 or 2.
Claim 3
Dependent Claim
19 words
1-(p-Cyanophenyl)-4-alkylcyclohexenes expressed by the general formula ##STR7## wherein R 1 represents a straight alkyl group having 3˜7 carbon atoms.
Claim 4
Dependent Claim
19 words
1-(p-Cyanophenyl)-4-alkylcyclohexenes expressed by the general formula ##STR7## wherein R 1 represents a straight alkyl group having 3˜7 carbon atoms.
Claim 5
Dependent Claim
19 words
1-(4'-Cyano-4-biphenylyl)-4-alkylcyclohexenes expressed by the general formula ##STR8## wherein R 2 represents a straight alkyl group having 3˜5 carbon atoms.
Claim 6
Dependent Claim
19 words
1-(4'-Cyano-4-biphenylyl)-4-alkylcyclohexenes expressed by the general formula ##STR8## wherein R 2 represents a straight alkyl group having 3˜5 carbon atoms.
Claim 7
Independent Claim
95 words
A method for producing 1-(p-cyanophenyl)-4-alkylcyclohexenes expressed by the general formula ##STR9## wherein R represents a straight alkyl group having 1˜9 carbon atoms, which method comprises: reacting a 4-alkylcyclohexanone (wherein the alkyl group has a straight chain of 1˜9 carbon atoms) with p-bromophenylmagnesium bromide or p-bromophenyllithium to form a mixture of cis- and trans-forms of 1-(p-bromophenyl)-4-alkylcyclohexanols (the first step); subjecting said mixture of cis- and trans-forms, as it is, to a dehydration reaction to form a 1-(p-bromophenyl)-4-alkylcyclohexene (the second step); and replacing the Br group of the compound thus prepared by cyano group (the third step).
Claim 8
Independent Claim
95 words
A method for producing 1-(p-cyanophenyl)-4-alkylcyclohexenes expressed by the general formula ##STR9## wherein R represents a straight alkyl group having 1˜9 carbon atoms, which method comprises: reacting a 4-alkylcyclohexanone (wherein the alkyl group has a straight chain of 1˜9 carbon atoms) with p-bromophenylmagnesium bromide or p-bromophenyllithium to form a mixture of cis- and trans-forms of 1-(p-bromophenyl)-4-alkylcyclohexanols (the first step); subjecting said mixture of cis- and trans-forms, as it is, to a dehydration reaction to form a 1-(p-bromophenyl)-4-alkylcyclohexene (the second step); and replacing the Br group of the compound thus prepared by cyano group (the third step).
Claim 9
Independent Claim
88 words
A method for producing 1-(4'-cyano-4-biphenylyl)-4-alkylcyclohexenes expressed by the general formula ##STR10## wherein R represents a straight alkyl group having 1˜9 carbon atoms, which method comprises: reacting a 4-alkylcyclohexanone (wherein the alkyl group has a straight chain of 1˜9 carbon atoms) with 4-bromo-4'-biphenyllithium to prepare a mixture of cis- and trans-forms of 1-(4'-bromo-4-biphenylyl)-4-alkylcyclohexanols (the first step); subjecting said mixture of cis-and trans-forms to a dehydration reaction to form a 1-(4'-bromo-4-biphenylyl)-4-alkylcyclohexene (the second step); and replacing the Br group of the compound thus prepared by cyano group (the third step).
Claim 10
Independent Claim
88 words
A method for producing 1-(4'-cyano-4-biphenylyl)-4-alkylcyclohexenes expressed by the general formula ##STR10## wherein R represents a straight alkyl group having 1˜9 carbon atoms, which method comprises: reacting a 4-alkylcyclohexanone (wherein the alkyl group has a straight chain of 1˜9 carbon atoms) with 4-bromo-4'-biphenyllithium to prepare a mixture of cis- and trans-forms of 1-(4'-bromo-4-biphenylyl)-4-alkylcyclohexanols (the first step); subjecting said mixture of cis-and trans-forms to a dehydration reaction to form a 1-(4'-bromo-4-biphenylyl)-4-alkylcyclohexene (the second step); and replacing the Br group of the compound thus prepared by cyano group (the third step).
Claim 11
Dependent Claim
42 words
A nematic liquid crystal composition containing at least one member selected from the group consisting of 1-(p-cyanophenyl)-4-alkylcyclohexenes and 1-(4'-cyano-4-biphenylyl)-4-alkylcyclohexenes, expressed by the general formula ##STR11## wherein R represents a straight alkyl group having 1˜9 carbon atoms and n represents 1 or 2.
Claim 12
Dependent Claim
42 words
A nematic liquid crystal composition containing at least one member selected from the group consisting of 1-(p-cyanophenyl)-4-alkylcyclohexenes and 1-(4'-cyano-4-biphenylyl)-4-alkylcyclohexenes, expressed by the general formula ##STR11## wherein R represents a straight alkyl group having 1˜9 carbon atoms and n represents 1 or 2.
References Cited (Backward Citations)
US3947375A
Cited
US4130502A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-07-08 | 1984-01-07 | 1984-07-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-07-08 | 1988-01-07 | 1988-07-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-07-08 | 1992-01-07 | 1992-07-08 | $7700.00 | Window Closed / Lapsed |