US4629581A
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Cyclohexanecarbonitriles
Assignee: F Hoffmann La Roche AG
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Filing: 1985-06-26
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Granted: 1986-12-16
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Expires: 2005-06-26
Abstract
Abstract Compounds of the formula ##STR1## wherein R 1 is hydrogen or straight-chain alkyl; R 2 is --CN, --R, --COR, --COOR or when R 2 is positioned on an aromatic ring R 2 also can be --OR, --OOCR or --F; R is alkyl; A is a group with 1 to 4 six-membered rings, these rings being linked directly with one another and with ring B in each case via a single covalent bond or being linked at one or two positions also via --COO--, --OOC-- or --CH 2 CH 2 --; the six-membered rings in A and ring B each are 1,4-phenylene or trans-1,4-cyclohexylene or one of these rings also is trans-2,5-disubstituted m-dioxane, 2,5-disubstituted pyrimidine or 3,6-disubstituted pyridazine, with the proviso that a maximum of two adjacent trans-1,4-cyclohexylene rings are linked directly via a single covalent bond; and m is the integer 2, or when ring B is trans-1,4-cyclohexylene or trans-2,5-disubstituted m-dioxane, m also can be the integer 0, their manufacture, liquid crystalline mixtures which contain these compounds as well as the use of these compounds for electro-optical purposes are described. Additionally, compounds of the formula ##STR2## wherein R 8 is straight-chain C 1 -C 12 alkyl, their manufacture, liquid crystalline mixtures which contain these compounds and their use for electro-optical purposes are described.
Inventors
- 👤 Arthur Boller
- 👤 Martin Petrzilka
- 👤 Martin Schadt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 01:39
CPC Classifications
C; C07; C07C; C07C403/00; C07C403/02; C07C255/00; C07C403/06; C07C403/10; C07C45/00; C07C45/56; C07C45/57; C07C45/59; C07C45/61; C07C45/67; C07C45/68; C09; C09K; C09K19/00; C09K19/04; C09K19/06; C09K19/08; C09K19/30; C09K19/3001; C07C2601/00; C07C2601/12; C07C2601/14
Claims Analysis
Total Claims: 43
Claim 1
Independent Claim
139 words
A compound of the fomrula wherein X 1 is a single covalent bond, --CH 2 CH 2 --, --COO--, --OOC-- or 1,4-phenylene; one of Y 1 and Y 2 is hydrogen and the other is cyano; R 2 is trans-1-alkenyl, cis-2-alkenyl, trans-3-alkenyl, 4-alkenyl or alkyl; R 1 is R 11 --A 4 --A 5 --; A 4 and A 5 independently of each other are a single covalent bond, 1,4-phenylene or trans-1,4-cyclohexylene; R 11 is trans-1-alkenyl, cis-2-alkenyl, trans-3-alkenyl, 4-alkenyl, trans-2-alkenyloxy, 3-alkenyloxy or, when R 2 is alkenyl, R 11 also can be alkyl or alkoxy; ring A 1 is 1,4-phenylene or a group of the formula ##STR18## and Y 3 and Y 4 are hydrogen or, when X 1 is --CH 2 CH 2 --, --COO-- or --OOC--, one of Y 3 and Y 4 also can be cyano.
Claim 2
Dependent Claim
139 words
A compound of the fomrula wherein X 1 is a single covalent bond, --CH 2 CH 2 --, --COO--, --OOC-- or 1,4-phenylene; one of Y 1 and Y 2 is hydrogen and the other is cyano; R 2 is trans-1-alkenyl, cis-2-alkenyl, trans-3-alkenyl, 4-alkenyl or alkyl; R 1 is R 11 --A 4 --A 5 --; A 4 and A 5 independently of each other are a single covalent bond, 1,4-phenylene or trans-1,4-cyclohexylene; R 11 is trans-1-alkenyl, cis-2-alkenyl, trans-3-alkenyl, 4-alkenyl, trans-2-alkenyloxy, 3-alkenyloxy or, when R 2 is alkenyl, R 11 also can be alkyl or alkoxy; ring A 1 is 1,4-phenylene or a group of the formula ##STR18## and Y 3 and Y 4 are hydrogen or, when X 1 is --CH 2 CH 2 --, --COO-- or --OOC--, one of Y 3 and Y 4 also can be cyano.
Claim 3
Dependent Claim
60 words
The compounds of claim 1, wherein R 1 and R 2 independently of each other are trans-1-alkenyl, cis-2-alkenyl, trans-3-alkenyl or 4-alkenyl or one of R 1 and R 2 also can be alkyl; and Y 3 and Y 4 are hydrogen or when X 1 is --COO-- or --OOC--, one of Y 3 and Y 4 also can be cyano.
Claim 4
Dependent Claim
65 words
The compound of claim 1, wherein X 1 is --CH 2 CH 2 --, R 1 and R 2 independently of each other are trans-1-alkenyl, cis-2-alkenyl, trans-3-alkenyl or 4-alkenyl, or one of R 1 and R 2 also can be alkyl; ring A 1 is a group of formula II, and one of Y 3 and Y 4 is hydrogen and the other is cyano.
Claim 5
Dependent Claim
19 words
The compound of claim 2, wherein R 1 and R 2 each have a maximum of 12 carbon atoms.
Claim 6
Dependent Claim
19 words
The compound of claim 4, wherein R 1 and R 2 each have a maximum of 7 carbon atoms.
Claim 7
Dependent Claim
19 words
The compound of claim 3, wherein R 1 and R 2 each have a maximum of 12 carbon atoms.
Claim 8
Dependent Claim
19 words
The compound of claim 6 wherein R 1 and R 2 each have a maximum of 7 carbon atoms.
Claim 9
Dependent Claim
32 words
The compound of claim 2, wherein R 1 and R 2 independently of each other are trans-1-alkenyl, trans-3-alkenyl or 4-alkenyl or one of R 1 and R 2 also can be alkyl.
Claim 10
Dependent Claim
10 words
The compound of claim 8 wherein R 1 is alkyl.
Claim 11
Dependent Claim
32 words
The compound of claim 3, wherein R 1 and R 2 independently of each other are trans-1-alkenyl, trans-3-alkenyl or 4-alkenyl or one of R 1 and R 2 also can be alkyl.
Claim 12
Dependent Claim
10 words
The compound of claim 10 wherein R 1 is alkyl.
Claim 13
Dependent Claim
24 words
The compound of claim 8, wherein one of R 1 and R 2 is trans-3-alkenyl and the other is trans-1-alkenyl, trans-3-alkenyl, 4-alkenyl or alkyl.
Claim 14
Dependent Claim
24 words
The compound of claim 10, wherein one of R 1 and R 2 is trans-3-alkenyl and the other is trans-1-alkenyl, trans-3-alkenyl, 4-alkenyl or alkyl.
Claim 15
Dependent Claim
20 words
The compound of claim 1, wherein each of Y 1 and Y 3 is hydrogen and Y 2 is cyano.
Claim 16
Dependent Claim
20 words
The compound of claim 2, wherein each of Y 1 and Y 3 is hydrogen and Y 2 is cyano.
Claim 17
Dependent Claim
20 words
The compound of claim 3, wherein each of Y 1 and Y 3 is hydrogen and Y 2 is cyano.
Claim 18
Dependent Claim
13 words
The compound of claim 1 wherein A 5 is a single covalent bond.
Claim 19
Dependent Claim
15 words
The compond of claim 17 wherein A 4 and A 5 are single covalent bonds.
Claim 20
Dependent Claim
83 words
The compound of claim 1 having the formula ##STR19## wherein one of Y 1 and Y 2 is hydrogen and the other is cyano; R 2 is trans-1-alkenyl, cis-2-alkenyl, trans-3-alkenyl, 4-alkenyl or alkyl; R 1 is R 11 --A 4 --A 5 --; A 4 and A 5 independently of each other are a single covalent bond, 1,4-phenylene or trans-1,4-cyclohexylene; R 11 is trans-1-alkenyl, cis-2-alkenyl, trans-3-alkenyl, 4-alkenyl, trans-2-alkenyloxy, 3-alkenyloxy or, when R 2 is alkenyl, R 11 also can be alkyl or alkoxy.
Claim 21
Dependent Claim
13 words
The compound of claim 19 wherein R 1 is trans-3-alkenyl, 4-alkenyl or alkyl.
Claim 22
Dependent Claim
83 words
The compound of claim 1 having the formula ##STR20## wherein one of Y 1 and Y 2 is hydrogen and the other is cyano; R 2 is trans-1-alkenyl, cis-2-alkenyl, trans-3-alkenyl, 4-alkenyl or alkyl; R 1 is R 11 --A 4 --A 5 --; A 4 and A 5 independently of each other are a single covalent bond, 1,4-phenylene or trans-1,4-cyclohexylene; R 11 is trans-1-alkenyl, cis-2-alkenyl, trans-3-alkenyl, 4-alkenyl, trans-2-alkenyloxy, 3-alkenyloxy or, when R 2 is alkenyl, R 11 also can be alkyl or alkoxy.
Claim 23
Dependent Claim
83 words
The compound of claim 1 having the formula ##STR21## wherein one of Y 1 and Y 2 is hydrogen and the other is cyano; R 2 is trans-1-alkenyl, cis-2-alkenyl, trans-3-alkenyl, 4-alkenyl or alkyl; R 1 is R 11 --A 4 --A 5 --; A 4 and A 5 independently of each other are a single covalent bond, 1,4-phenylene or trans-1,4-cyclohexylene; R 11 is trans-1-alkenyl, cis-2-alkenyl, trans-3-alkenyl, 4-alkenyl, trans-2-alkenyloxy, 3-alkenyloxy or, when R 2 is alkenyl, R 11 also can be alkyl or alkoxy.
Claim 24
Dependent Claim
13 words
The compound of claim 22 wherein R 1 is trans-3-alkenyl, 4-alkenyl or alkyl.
Claim 25
Dependent Claim
105 words
The compound of claim 1 having the formula ##STR22## wherein one of Y 1 and Y 2 is hydrogen and the other is cyano; Y 3 and Y 4 are hydrogen or one of Y 3 and Y 4 is cyano and the other is hydrogen; R 2 is trans-1-alkenyl, cis-2-alkenyl, trans-3-alkenyl, 4-alkenyl or alkyl; R 1 is R 11 --A 4 --A 5 --; A 4 and A 5 independently of each other are a single covalent bond, 1,4-phenylene or trans-1,4cyclohexylene; R 11 is trans-1-alkenyl, cis-2-alkenyl, trans-3-alkenyl, 4-alkenyl, trans-2-alkenyloxy, 3-alkenyloxy or, when R 2 is alkenyl, R 11 also can be alkyl or alkoxy.
Claim 26
Dependent Claim
13 words
The compound of claim 24 wherein Y 3 and Y 4 are hydrogen.
Claim 27
Dependent Claim
13 words
The compound of claim 24 wherein Y 4 and Y 2 are cyano.
Claim 28
Dependent Claim
83 words
The compound of claim 1 having the formula ##STR23## wherein one of Y 1 and Y 2 are hydrogen and the other is cyano; R 2 is trans-1-alkenyl, cis-2-alkenyl, trans-3-alkenyl, 4-alkenyl or alkyl; R 1 is R 11 --A 4 --A 5 --; A 4 and A 5 independently of each other are a single covalent bond, 1,4-phenylene or trans-1,4-cyclohexylene; R 11 is trans-1-alkenyl, cis-2-alkenyl, trans-3-alkenyl, 4-alkenyl, trans-2-alkenyloxy, 3-alkenyloxy or, when R 2 is alkenyl, R 11 also can be alkyl or alkoxy.
Claim 29
Dependent Claim
12 words
The compound of 27 wherein R 1 is trans-3-alkenyl, 4-alkenyl or alkyl.
Claim 30
Dependent Claim
12 words
The compound of 27 wherein R 1 is trans-3-alkenyl, 4-alkenyl or alkyl.
Claim 31
Dependent Claim
105 words
The compound of claim 1 having the formula ##STR24## wherein one of Y 1 and Y 2 is hydrogen and the other is cyano; Y 3 and Y 4 are hydrogen or one of Y 3 and Y 4 is cyano and the other is hydrogen; R 2 is trans-1-alkenyl, cis-2-alkenyl, trans-3-alkenyl, 4-alkenyl or alkyl; R 1 is R 11 --A 4 --A 5 --; A 4 and A 5 independently of each other are a single covalent bond, 1,4-phenylene or trans-1,4-cyclohexylene; R 11 is trans-1-alkenyl, cis-2-alkenyl, trans-3-alkenyl, 4-alkenyl, trans-2-alkenyloxy, 3-alkenyloxy or, when R 2 is alkenyl, R 11 also can be alkyl or alkoxy.
Claim 32
Dependent Claim
13 words
The compound of claim 29 wherein Y 3 and Y 4 are hydrogen.
Claim 33
Dependent Claim
83 words
The compound of claim 1 having the formula ##STR25## wheein one of Y 1 and Y 2 is hydrogen and the other is cyano; R 2 is trans-1-alkenyl, cis-2-alkenyl, trans-3-alkenyl, 4-alkenyl or alkyl; R 1 is R 11 --A 4 --A 5 --; A 4 and A 5 independently of each other are a single covalent bond, 1,4-phenylene or trans-1,4-cyclohexylene; R 11 is trans-1-alkenyl, cis-2-alkenyl, trans-3-alkenyl, 4-alkenyl, trans-2-alkenyloxy, 3-alkenyloxy or, when R 2 is alkenyl, R 11 also can be alkyl or alkoxy.
Claim 34
Dependent Claim
13 words
The compound of claim 31 wherein R 1 is trans-2-alkenyl, 4-alkenyl or alkyl.
Claim 35
Dependent Claim
105 words
The compound of claim 1 having the formula ##STR26## wherein one of Y 1 and Y 2 is hydrogen and the other is cyano; Y 3 and Y 4 are hydrogen or one of Y 3 and Y 4 is cyano and the other is hydrogen; R 2 is trans-1-alkenyl, cis-2-alkenyl, trans-3-alkenyl, 4-alkenyl or alkyl; R 1 is R 11 --A 4 --A 5 --; A 4 and A 5 independently of each other are a single covalent bond, 1,4-phenylene or trans-1,4-cyclohexylene; R 11 is trans-1-alkenyl, cis-2-alkenyl, trans-3-alkenyl, 4-alkenyl, trans-2-alkenyloxy, 3-alkenyloxy or, when R 2 is alkenyl, R 11 also can be alkyl or alkoxy.
Claim 36
Dependent Claim
13 words
The compound of claim 33 wherein Y 3 and Y 4 are hydrogen.
Claim 37
Dependent Claim
83 words
The compound of claim 1 having the formula ##STR27## wherein one of Y 1 and Y 2 is hydrogen and the other is cyano; R 2 is trans-1-alkenyl, cis-2-alkenyl, trans-3-alkenyl, 4-alkenyl or alkyl; R 1 is R 11 --A 4 --A 5 --; A 4 and A 5 independently of each other are a single covalent bond, 1,4-phenylene or trans-1,4-cyclohexylene; R 11 is trans-1-alkenyl, cis-2-alkenyl, trans-3-alkenyl, 4-alkenyl, trans-2-alkenyloxy, 3-alkenyloxy or, when R 2 is alkenyl, R 11 also can be alkyl or alkoxy.
Claim 38
Dependent Claim
13 words
The compound of claim 35 wherein R 1 is trans-3-alkenyl, 4-alkenyl or alkyl.
Claim 39
Dependent Claim
83 words
The compound of claim 1 having the formula ##STR28## wherein one of Y 1 and Y 2 is hydrogen and the other is cyano; R 2 is trans-1-alkenyl, cis-2-alkenyl, trans-3-alkenyl, 4-alkenyl or alkyl; R 1 is R 11 --A 4 A 5 --; A 4 and A 5 independently of each other are a single covalent bond, 1,4-phenylene or trans-1,4-cyclohexylene; R 11 is trans-1-alkenyl, cis-2-alkenyl, trans-3-alkenyl, 4-alkenyl, trans-2-alkenyloxy, 3-alkenyloxy or, when R 2 is alkenyl, R 11 also can be alkyl or alkoxy.
Claim 40
Dependent Claim
123 words
A liquid crystalline mixture comprising at least two components at least one of which is a compound of the formula ##STR29## wherein X 1 is a single covalent bond, --CH 2 CH 2 --, --COO--, --OOC-- or 1,4-phenylene; one of Y 1 and Y 2 is hydrogen and the other is cyano; R 2 is trans-1-alkenyl, cis-2-alkenyl, trans-3-alkenyl, 4-alkenyl or alkyl; R 1 is R 11 --A 4 --A 5 --; A 4 and A 5 independently of each other are a single covalent bond, 1,4-phenylene or trans-1,4-cyclohexylene; R 11 is trans-1-alkenyl, cis-2-alkenyl, trans-3-alkenyl, 4-alkenyl, trans-2-alkenyloxy, 3-alkenyloxy or, when R 2 is alkenyl, R 11 also can be alkyl or alkoxy; ring A 1 is 1,4-phenylene or a group of the formula ##STR30##
Claim 41
Dependent Claim
123 words
A liquid crystalline mixture comprising at least two components at least one of which is a compound of the formula ##STR29## wherein X 1 is a single covalent bond, --CH 2 CH 2 --, --COO--, --OOC-- or 1,4-phenylene; one of Y 1 and Y 2 is hydrogen and the other is cyano; R 2 is trans-1-alkenyl, cis-2-alkenyl, trans-3-alkenyl, 4-alkenyl or alkyl; R 1 is R 11 --A 4 --A 5 --; A 4 and A 5 independently of each other are a single covalent bond, 1,4-phenylene or trans-1,4-cyclohexylene; R 11 is trans-1-alkenyl, cis-2-alkenyl, trans-3-alkenyl, 4-alkenyl, trans-2-alkenyloxy, 3-alkenyloxy or, when R 2 is alkenyl, R 11 also can be alkyl or alkoxy; ring A 1 is 1,4-phenylene or a group of the formula ##STR30##
Claim 42
Dependent Claim
173 words
An electro-optical cell comprising: (a) two plate means; (b) a liquid crystalline means disposed between the two plate means and including a compound of the formula ##STR31## wherein X 1 is a single covalent bond, --CH 2 CH 2 --, --COO--, --OOC-- or 1,4-phenylene; one of Y 1 and Y 2 is hydrogen and the other is cyano; R 2 is trans-1-alkenyl, cis-2-alkenyl, trans-3-alkenyl, 4-alkenyl or alkyl; R 1 is R 11 --A 4 --A 5 --; A 4 and A 5 independently of each other are a single covalent bond, 1,4-phenylene or trans-1,4-cyclohexylene; R 11 is trans-1-alkenyl, cis-2-alkenyl, trans-3-alkenyl, 4-alkenyl, trans-2-alkenyloxy, 3-alkenyloxy or, when R 2 is alkenyl, R 11 also can be alkyl or alkoxy; ring A 1 is 1,4-phenylene or a group of the formula ##STR32## and Y 3 and Y 4 are hydrogen or, when X 1 is --CH 2 CH 2 --, --COO-- or --OOC--, one of Y 3 and Y 4 also can be cyano; and (c) means for applying an electric potential to said plate means.
Claim 43
Dependent Claim
173 words
An electro-optical cell comprising: (a) two plate means; (b) a liquid crystalline means disposed between the two plate means and including a compound of the formula ##STR31## wherein X 1 is a single covalent bond, --CH 2 CH 2 --, --COO--, --OOC-- or 1,4-phenylene; one of Y 1 and Y 2 is hydrogen and the other is cyano; R 2 is trans-1-alkenyl, cis-2-alkenyl, trans-3-alkenyl, 4-alkenyl or alkyl; R 1 is R 11 --A 4 --A 5 --; A 4 and A 5 independently of each other are a single covalent bond, 1,4-phenylene or trans-1,4-cyclohexylene; R 11 is trans-1-alkenyl, cis-2-alkenyl, trans-3-alkenyl, 4-alkenyl, trans-2-alkenyloxy, 3-alkenyloxy or, when R 2 is alkenyl, R 11 also can be alkyl or alkoxy; ring A 1 is 1,4-phenylene or a group of the formula ##STR32## and Y 3 and Y 4 are hydrogen or, when X 1 is --CH 2 CH 2 --, --COO-- or --OOC--, one of Y 3 and Y 4 also can be cyano; and (c) means for applying an electric potential to said plate means.
References Cited (Backward Citations)
DE3231707A1
Cited
US4510069A
Cited
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