Patent US4528114A successfully refreshed from Google Patents.
US4528114A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Acetylenes
Assignee: F Hoffmann La Roche AG
•
Filing: 1982-12-03
•
Granted: 1985-07-09
•
Expires: 2002-12-03
Abstract
Abstract Compounds of the formula <IMAGE> I wherein ring B stands for 1,4-phenylene or a trans-1,4-disubstituted cyclohexane ring and A stands for a group with 1 to 3 six-membered rings, which together with ring B represents a central group of formulae II-XIII; R1 signifies a straight-chain alkyl group containing 1 to 9 carbon atoms or when R1 is attached to a benzene, monofluorinated benzene or pyrimidine, ring R1 also signifies a straight-chain alkoxy group with 1 to 9 carbon atoms; and R2 signifies hydrogen, cyano or a straight-chain alkyl group containing 1 to 7 carbon atoms, their manufacture, liquid crystalline mixtures which contain said compounds and their use for electro-optical purposes are described. The compounds of formula I are especially valuable as components in liquid crystal mixtures and for the most part themselves have liquid crystalline properties.
Inventors
- 👤 Martin Petrzilka
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 19:14
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/02; C07D239/24; C07D239/26; C07C; C07C13/00; C07C13/28; C07C15/00; C07C15/40; C07C15/50; C07C17/00; C07C17/26; C07C17/263; C07C17/2637; C07C255/00; C07C43/00; C07C43/02; C07C43/20; C07C43/215; C07C45/00; C07C45/44; C07D239/28; C07D239/32; C07D239/34; C07D317/00; C07D317/08; C07D317/10; C07D317/14; C07D317/16; C07D317/26; C07D317/30; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/0803; C07F7/081; C07F9/00; C07F9/02; C07F9/28; C07F9/54; C07F9/5456; C09; C09K; C09K19/00; C09K19/04; C09K19/06; C09K19/08; C09K19/10; C09K19/14; C09K19/30; C09K19/3001; C09K19/32; C09K19/322; C07C2601/00; C07C2601/12; C07C2601/14; C09K2019/325; C09K2019/326
Claims Analysis
Total Claims: 73
Claim 1
Independent Claim
156 words
A compound of the formula ##STR22## wherein A together with ring B comprise a central group of the formula: ##STR23## wherein ring A 12 is trans-1,4-disubstituted cyclohexane, trans-2,5-disubstituted 1,3-dioxane linked in the 2-position with ring B, or when ring B is trans-1,4-disubstituted cyclohexane or R 2 is straight-chain alkyl of 1 to 7 carbon atoms, ring A 12 also can be 1,4-phenylene or 2,5-disubstituted pyrimidine linked in the 2-position with ring B; ##STR24## wherein ring A 1 is 1,4-phenylene, or trans-1,4-disubstituted cyclohexane; or ##STR25## wherein ring A 2 is 1,4-phenylene or trans-1,4-disubstituted cyclohexane and E is --COO-- or --OOC--; ring B is 1,4-phenylene or trans-1,4-disubstituted cyclohexane; R 1 is straight-chain alkyl of 1 to 9 carbon atoms or when R 1 is attached to a benzene or a pyrimidine ring, R 1 also is straight-chain alkoxy of 1 to 9 carbon atoms; and R 2 is cyano or straight-chain alkyl of 1 to 7 carbon atoms.
Claim 2
Dependent Claim
156 words
A compound of the formula ##STR22## wherein A together with ring B comprise a central group of the formula: ##STR23## wherein ring A 12 is trans-1,4-disubstituted cyclohexane, trans-2,5-disubstituted 1,3-dioxane linked in the 2-position with ring B, or when ring B is trans-1,4-disubstituted cyclohexane or R 2 is straight-chain alkyl of 1 to 7 carbon atoms, ring A 12 also can be 1,4-phenylene or 2,5-disubstituted pyrimidine linked in the 2-position with ring B; ##STR24## wherein ring A 1 is 1,4-phenylene, or trans-1,4-disubstituted cyclohexane; or ##STR25## wherein ring A 2 is 1,4-phenylene or trans-1,4-disubstituted cyclohexane and E is --COO-- or --OOC--; ring B is 1,4-phenylene or trans-1,4-disubstituted cyclohexane; R 1 is straight-chain alkyl of 1 to 9 carbon atoms or when R 1 is attached to a benzene or a pyrimidine ring, R 1 also is straight-chain alkoxy of 1 to 9 carbon atoms; and R 2 is cyano or straight-chain alkyl of 1 to 7 carbon atoms.
Claim 3
Dependent Claim
174 words
A liquid crystalline mixture comprising at least two components, wherein at least one of those components is a compound of the formula: ##STR26## wherein A together with ring B comprise a central group of the formula: ##STR27## wherein ring A 12 is trans-1,4-disubstituted cyclohexane, trans-2,5-disubstituted 1,3-dioxane linked in the 2-position with ring B, or when ring B is trans-1,4-disubstituted cyclohexane or R 2 is straight-chain alkyl of 1 to 7 carbon atoms, ring A 12 l also can be 1,4-phenylene or 2,5-disubstituted pyrimidine linked in the 2-position with ring B; ##STR28## wherein ring A 1 is 1,4-phenylene, or trans-1,4-disubstituted cyclohexane; or ##STR29## wherein ring A 2 is 1,4-phenylene or trans-1,4-disubstituted cyclohexane and E is --COO-- or --OOC--; ring B is 1,4-phenylene or trans-1,4-disubstituted cyclohexane; R 1 is straight-chain alkyl of 1 to 9 carbon atoms or when R 1 is attached to a benzene or a pyrimidine ring, R 1 also is straight-chain alkoxy of 1 to 9 carbon atoms; and R 2 is cyano or straight-chain alkyl of 1 to 7 carbon atoms.
Claim 4
Dependent Claim
174 words
A liquid crystalline mixture comprising at least two components, wherein at least one of those components is a compound of the formula: ##STR26## wherein A together with ring B comprise a central group of the formula: ##STR27## wherein ring A 12 is trans-1,4-disubstituted cyclohexane, trans-2,5-disubstituted 1,3-dioxane linked in the 2-position with ring B, or when ring B is trans-1,4-disubstituted cyclohexane or R 2 is straight-chain alkyl of 1 to 7 carbon atoms, ring A 12 l also can be 1,4-phenylene or 2,5-disubstituted pyrimidine linked in the 2-position with ring B; ##STR28## wherein ring A 1 is 1,4-phenylene, or trans-1,4-disubstituted cyclohexane; or ##STR29## wherein ring A 2 is 1,4-phenylene or trans-1,4-disubstituted cyclohexane and E is --COO-- or --OOC--; ring B is 1,4-phenylene or trans-1,4-disubstituted cyclohexane; R 1 is straight-chain alkyl of 1 to 9 carbon atoms or when R 1 is attached to a benzene or a pyrimidine ring, R 1 also is straight-chain alkoxy of 1 to 9 carbon atoms; and R 2 is cyano or straight-chain alkyl of 1 to 7 carbon atoms.
Claim 5
Dependent Claim
175 words
An electro-optical cell comprising: (a) two-plate means; (b) a liquid crystal disposed between the plate means and including a dielectric of the formula: ##STR30## wherein A together with ring B comprise a central group of the formula: ##STR31## wherein ring A 12 is trans-1,4-disubstituted cyclohexane, trans-2,5-disubstituted 1,3-dioxane linked in the 2-position with ring B, or when ring B is trans-1,4-disubstituted cyclohexane or R 2 is straight-chain alkyl of 1 to 7 carbon atoms, ring A 12 also can be 1,4-phenylene or 2,5-disubstituted pyrimidine linked in the 2-position with ring B; ##STR32## wherein ring A 1 is 1,4-phenylene, or trans-1,4-disubstituted cyclohexane; or ##STR33## wherein ring A 2 is 1,4-phenylene or trans-1,4-disubstituted cyclohexane and E is --COO-- or --OOC--; ring B is 1,4-phenylene or trans-1,4- disubstituted cyclohexane; R 1 is straight-chain alkyl of 1 to 9 carbon atoms or when R 1 is attached to a benzene or a pyrimidine ring, R 1 also is straight-chain alkoxy of 1 to 9 carbon atoms; and R 2 is cyano or straight-chain alkyl of 1 to 7 carbon atoms.
Claim 6
Dependent Claim
175 words
An electro-optical cell comprising: (a) two-plate means; (b) a liquid crystal disposed between the plate means and including a dielectric of the formula: ##STR30## wherein A together with ring B comprise a central group of the formula: ##STR31## wherein ring A 12 is trans-1,4-disubstituted cyclohexane, trans-2,5-disubstituted 1,3-dioxane linked in the 2-position with ring B, or when ring B is trans-1,4-disubstituted cyclohexane or R 2 is straight-chain alkyl of 1 to 7 carbon atoms, ring A 12 also can be 1,4-phenylene or 2,5-disubstituted pyrimidine linked in the 2-position with ring B; ##STR32## wherein ring A 1 is 1,4-phenylene, or trans-1,4-disubstituted cyclohexane; or ##STR33## wherein ring A 2 is 1,4-phenylene or trans-1,4-disubstituted cyclohexane and E is --COO-- or --OOC--; ring B is 1,4-phenylene or trans-1,4- disubstituted cyclohexane; R 1 is straight-chain alkyl of 1 to 9 carbon atoms or when R 1 is attached to a benzene or a pyrimidine ring, R 1 also is straight-chain alkoxy of 1 to 9 carbon atoms; and R 2 is cyano or straight-chain alkyl of 1 to 7 carbon atoms.
Claim 7
Dependent Claim
63 words
The compound of claim 1 wherein A together with ring B is a central group of formula II in which ring A 12 is trans-1,4-disubstituted cyclohexane, trans-2,5-disubstituted 1,3-dioxane linked in the 2-position with ring B or when ring B is trans-1,4-disubstituted cyclohexane or R 2 is alkyl, ring A 12 also is 1,4-phenylene or 2,5-disubstituted pyrimidine linked in the 2-position with ring B.
Claim 8
Dependent Claim
28 words
The compound of claim 1 wherein A together with ring B is a central group of formula III in which ring A 1 is 1,4-phenylene or trans-1,4-disubstituted cyclohexane.
Claim 9
Dependent Claim
34 words
The compound of claim 1 wherein A together with ring B is a central group of formula IV in which ring A 2 is 1,4-phenylene or trans-1,4-disubstituted cyclohexane and E is an ester group.
Claim 10
Dependent Claim
10 words
The compound of claim 1 wherein ring B is saturated.
Claim 11
Dependent Claim
84 words
The compound of claim 1 having the formula ##STR34## wherein each of rings B and C is 1,4-phenylene or trans-1,4-disubstituted cyclohexane; R 1 is straight-chain alkyl of 1 to 9 carbon atoms or when R 1 is attached to a benzene ring, R 1 also is straight-chain alkoxy of 1 to 9 carbon atoms; and R 2 is straight-chain alkyl of 1 to 7 carbon atoms or, when at least one of rings B and C is trans-1,4-disubstituted cyclohexane, R 2 also is cyano.
Claim 12
Dependent Claim
20 words
The compound of claim 8 wherein one of rings B and C is trans-1,4-disubstituted cyclohexane and the other is 1,4-phenylene.
Claim 13
Dependent Claim
10 words
The compound of claim 8 wherein ring B is saturated.
Claim 14
Dependent Claim
14 words
The compound of claim 1 wherein R 2 is cyano, methyl, ethyl or propyl.
Claim 15
Dependent Claim
12 words
The compound of claim 11 wherein R 2 is cyano or methyl.
Claim 16
Dependent Claim
41 words
The compound of claim 1 wherein R 1 is straight-chain alkyl of 3 to 7 carbon atoms or when R 1 is attached to a benzene or pyrimidine ring, R 1 also is straight-chain alkoxy of 2 to 6 carbon atoms.
Claim 17
Dependent Claim
41 words
The compound of claim 12 wherein R 1 is straight-chain alkyl of 3 to 7 carbon atoms or when R 1 is attached to a benzene, or pyrimidine ring, R 1 also is straight-chain alkoxy of 2 to 6 carbon atoms.
Claim 18
Dependent Claim
71 words
The compound of claim 1 having the formula ##STR35## wherein ring C is 1,4-phenylene or trans-1,4-disubstituted cyclohexane; ring B is 1,4-phenylene or trans-1,4-disubstituted cyclohexane; R 1 is straight-chain alkyl of 1 to 9 carbon atoms or when R 1 is attached to a benzene ring, R 1 also is straight-chain alkoxy of 1 to 9 carbon atoms; and R 2 is cyano or straight-chain alkyl of 1 to 7 carbon atoms.
Claim 19
Dependent Claim
17 words
The compound of claim 15 wherein at least one of rings B and C is trans-1,4-disubstituted cyclohexane.
Claim 20
Dependent Claim
10 words
The compound of claim 15 wherein ring B is saturated.
Claim 21
Dependent Claim
14 words
The compound of claim 15 wherein R 2 is cyano, methyl, ethyl or propyl.
Claim 22
Dependent Claim
12 words
The compound of claim 18 wherein R 2 is cyano or methyl.
Claim 23
Dependent Claim
39 words
The compound of claim 15 wherein R 1 is straight-chain alkyl of 3 to 7 carbon atoms or when R 1 is attached to a benzene ring, R 1 also is straight-chain alkoxy of 2 to 6 carbon atoms.
Claim 24
Dependent Claim
39 words
The compound of claim 19 wherein R 1 is straight-chain alkyl of 3 to 7 carbon atoms or when R 1 is attached to a benzene ring, R 1 also is straight-chain alkoxy of 2 to 6 carbon atoms.
Claim 25
Dependent Claim
71 words
The compound of claim 1 having the formula ##STR36## wherein ring C is 1,4-phenylene or trans-1,4-disubstituted cyclohexane; ring B is 1,4-phenylene or trans-1,4-disubstituted cyclohexane; R 1 is straight-chain alkyl of 1 to 9 carbon atoms or when R 1 is attached to a benzene ring, R 1 also is straight-chain alkoxy of 1 to 9 carbon atoms; and R 2 is cyano or straight-chain alkyl of 1 to 7 carbon atoms.
Claim 26
Dependent Claim
10 words
The compound of claim 22 wherein ring B is 1,4-phenylene.
Claim 27
Dependent Claim
10 words
The compound of claim 22 wherein ring B is saturated.
Claim 28
Dependent Claim
14 words
The compound of claim 22 wherein R 2 is cyano, methyl, ethyl or propyl.
Claim 29
Dependent Claim
12 words
The compound of claim 25 wherein R 2 is cyano or methyl.
Claim 30
Dependent Claim
39 words
The compound of claim 22 wherein R 1 is straight-chain alkyl of 3 to 7 carbon atoms or when R 1 is attached to a benzene ring, R 1 also is straight-chain alkoxy of 2 to 6 carbon atoms.
Claim 31
Dependent Claim
39 words
The compound of claim 26 wherein R 1 is straight-chain alkyl of 3 to 7 carbon atoms or when R 1 is attached to a benzene ring, R 1 also is straight-chain alkoxy of 2 to 6 carbon atoms.
Claim 32
Dependent Claim
71 words
The compound of claim 1 having the formula ##STR37## wherein ring C is 1,4-phenylene or trans-1,4-disubstituted cyclohexane; ring B is 1,4-phenylene or trans-1,4-disubstituted cyclohexane; R 1 is straight-chain alkyl of 1 to 9 carbon atoms or when R 1 is attached to a benzene ring, R 1 also is straight-chain alkoxy of 1 to 9 carbon atoms; and R 2 is cyano or straight-chain alkyl of 1 to 7 carbon atoms.
Claim 33
Dependent Claim
10 words
The compound of claim 29 wherein ring B is saturated.
Claim 34
Dependent Claim
14 words
The compound of claim 29 wherein R 2 is cyano, methyl, ethyl or propyl.
Claim 35
Dependent Claim
12 words
The compound of claim 31 wherein R 2 is cyano or methyl.
Claim 36
Dependent Claim
39 words
The compound of claim 29 wherein R 1 is straight-chain alkyl of 3 to 7 carbon atoms or when R 1 is attached to a benzene ring, R 1 also is straight-chain alkoxy of 2 to 6 carbon atoms.
Claim 37
Dependent Claim
39 words
The compound of claim 32 wherein R 1 is straight-chain alkyl of 3 to 7 carbon atoms or when R 1 is attached to a benzene ring, R 1 also is straight-chain alkoxy of 2 to 6 carbon atoms.
Claim 38
Dependent Claim
10 words
The compound of claim 29 wherein ring B is 1,4-phenylene.
Claim 39
Dependent Claim
42 words
The compound of claim 1 having the formula ##STR38## wherein ring B is 1,4-phenylene or trans-1,4-disubstituted cyclohexane; R 1 is straight-chain alkyl of 1 to 9 carbon atoms and R 2 is cyano or straight-chain alkyl of 1 to 7 carbon atoms.
Claim 40
Dependent Claim
10 words
The compound of claim 36 wherein ring B is saturated.
Claim 41
Dependent Claim
14 words
The compound of claim 36 wherein R 2 is cyano, methyl, ethyl or propyl.
Claim 42
Dependent Claim
12 words
The compound of claim 38 wherein R 2 is cyano or methyl.
Claim 43
Dependent Claim
15 words
The compound of claim 36 wherein R 1 is straight-chain alkyl of 3 to 7.
Claim 44
Dependent Claim
15 words
The compound of claim 39 wherein R 1 is straight-chain alkyl of 3 to 7.
Claim 45
Dependent Claim
61 words
The compound of claim 1 having the formula ##STR39## wherein ring B is 1,4-phenylene or trans-1,4-disubstituted cyclohexane; R 1 is straight-chain alkyl of 1 to 9 carbon atoms or straight-chain alkoxy of 1 to 9 carbon atoms; and R 2 is straight-chain alkyl of 1 to 7 carbon atoms or, when ring B is trans-1,4-disubstituted cyclohexane, R 2 also is cyano.
Claim 46
Dependent Claim
10 words
The compound of claim 42 wherein ring B is saturated.
Claim 47
Dependent Claim
14 words
The compound of claim 42 wherein R 2 is cyano, methyl, ethyl or propyl.
Claim 48
Dependent Claim
12 words
The compound of claim 44 wherein R 2 is cyano or methyl.
Claim 49
Dependent Claim
26 words
The compound of claim 42 wherein R 1 is straight-chain alkyl of 3 to 7 carbon atoms or straight-chain alkoxy of 2 to 6 carbon atoms.
Claim 50
Dependent Claim
26 words
The compound of claim 45 wherein R 1 is straight-chain alkyl of 3 to 7 carbon atoms or straight-chain alkoxy of 2 to 6 carbon atoms.
Claim 51
Dependent Claim
10 words
The compound of claim 1 wherein ring B is aromatic.
Claim 52
Dependent Claim
17 words
The compound of claim 48 wherein R 2 is straight-chain alkyl of 1 to 7 carbon atoms.
Claim 53
Dependent Claim
14 words
The compound of claim 8 wherein R 2 is cyano, methyl, ethyl or propyl.
Claim 54
Dependent Claim
12 words
The compound of claim 50 wherein R 2 is cyano or methyl.
Claim 55
Dependent Claim
39 words
The compound of claim 8 wherein R 1 is straight-chain alkyl of 3 to 7 carbon atoms or when R 1 is attached to a benzene ring, R 1 also is straight-chain alkoxy of 2 to 6 carbon atoms.
Claim 56
Dependent Claim
39 words
The compound of claim 51 wherein R 1 is straight-chain alkyl of 3 to 7 carbon atoms or when R 1 is attached to a benzene ring, R 1 also is straight-chain alkoxy of 2 to 6 carbon atoms.
Claim 57
Dependent Claim
6 words
The compound of claim 1, p-(trans-4-pentylcyclohexyl)phenylpropiolonitrile.
Claim 58
Dependent Claim
6 words
The compound of claim 1, p-[2-(trans-4-pentylcyclohexyl)ethyl]phenylpropiolonitrile.
Claim 59
Dependent Claim
6 words
The compound of claim 1, p-(trans-5-pentyl-1,3-dioxan-2-yl)phenylpropiolonitrile.
Claim 60
Dependent Claim
6 words
The compound of claim 1, p-(trans-5-butyl-1,3-dioxan-2-yl)phenylpropiolonitrile.
Claim 61
Dependent Claim
9 words
The compound of claim 1, trans-4-pentylcyclohexanecarboxylic acid p-(2-cyanoethynyl)phenyl ester.
Claim 62
Dependent Claim
6 words
The compound of claim 1, trans-4-[2-(trans-4-pentylcyclohexyl)ethyl]cyclohexanepropiolonitrile.
Claim 63
Dependent Claim
6 words
The compound of claim 1, 1-(1-propynyl)-4-(trans-4-propylcyclohexyl)benzene.
Claim 64
Dependent Claim
6 words
The compound of claim 1, 1-(1-propynyl)-4-(trans-4-pentylcyclohexyl)benzene.
Claim 65
Dependent Claim
6 words
The compound of claim 1, 1-(1-propynyl)-4-(trans-4-heptylcyclohexyl)benzene.
Claim 66
Dependent Claim
6 words
The compound of claim 1, 1-(1-butynyl)-4-(trans-4-pentylcyclohexyl)benzene.
Claim 67
Dependent Claim
6 words
The compound of claim 1, 1-(1-pentynyl)-4-(trans-4-pentylcyclohexyl)benzene.
Claim 68
Dependent Claim
6 words
The compound of claim 1, 4-(1-propynyl)-4'-pentylbiphenyl.
Claim 69
Dependent Claim
6 words
The compound of claim 1, 1-(1-propynyl)-4-[2-(trans-4-butylcyclohexyl)ethyl]benzene.
Claim 70
Dependent Claim
6 words
The compound of claim 1, 1-(1-propynyl)-4-[2-(trans-4-pentylcyclohexyl)ethyl]benzene.
Claim 71
Dependent Claim
6 words
The compound of claim 1, 1-(1-propynyl)-4-[2-(trans-4-heptylcyclohexyl)ethyl]benzene.
Claim 72
Dependent Claim
6 words
The compound of claim 1, trans-4-[2-(p-pentylphenyl)ethyl]cyclohexanepropiolonitrile.
Claim 73
Dependent Claim
6 words
The compound of claim 1, trans-4-[2-(p-butyloxyphenyl)ethyl]cyclohexanepropiolonitrile.
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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) | 1988-07-08 | 1989-01-07 | 1989-07-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-07-08 | 1993-01-07 | 1993-07-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-07-08 | 1997-01-07 | 1997-07-09 | $7700.00 | Window Closed / Lapsed |