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 18:06
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.
References Cited (Backward Citations)
DE2226376A1
Cited
US4001137A
Cited
DE2257588A1
Cited
US3923857A
Cited
CH585256A5
Cited
DE2309501A1
Cited
DE2334425A1
Cited
US3987116A
Cited
DD105701A1
Cited
CH614919A5
Cited
US3997536A
Cited
US4016214A
Cited
DE2504641A1
Cited
JPS5236642A
Cited
US4062798A
Cited
DE2626018A1
Cited
DE2636684A1
Cited
US4130502A
Cited
US4181625A
Cited
US4309539A
Cited
US4261651A
Cited
US4263457A
Cited
US4348324A
Cited
DE2944905A1
Cited
GB2041354A
Cited
US4273929A
Cited
DE3003256A1
Cited
US4322354A
Cited
GB2044767A
Cited
US4349452A
Cited
US4219256A
Cited
EP0025119A1
Cited
DE3034222A1
Cited
GB2065104A
Cited
DE2948836A1
Cited
EP0031796A2
Cited
US4450094A
Cited
GB2067188A
Cited
US4400061A
Cited
DE3006666A1
Cited
US4298528A
Cited
US4398803A
Cited
DE3131593A1
Cited
US4462923A
Cited
US4432885A
Cited
US4419263A
Cited
US4431853A
Cited
EP0056501A2
Cited
US4439015A
Cited
EP0058512A1
Cited
EP0058981A2
Cited
US4460770A
Cited
DE3151367A1
Cited
US4419262A
Cited
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 |