US4659502A
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Ethane derivatives
Assignee: Merck Patent GmbH
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Filing: 1985-01-17
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Granted: 1987-04-21
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Expires: 2005-01-17
Abstract
Abstract Ethane derivatives of the formula I R.sup.1 --A.sup.1 --CH.sub.2 CH.sub.2 --A.sup.2 --(A.sup.3).sub.n --R.sup.2 I wherein R 1 is H, an alkyl group with 1-12 C atoms, in which one or two non adjacent CH 2 groups can also be replaced by O atoms and/or CO groups and/or --O--CO-- groups and/or --CO--O groups, F, Cl, Br or R 3 --A 4 --Z 1 --, R 2 is --CN or --Z 2 --A 4 --CN, A 1 is --A--, --A--A 5 -- or --A 5 --A--, A 2 is an 1,4-phenylene group which is unsubstituted or substituted by one or two F and/or Cl atoms and/or CH 3 groups and/or CN groups and in which one or two CH groups can also be replaced by N atoms, A is a 1,4-cyclohexylene group, in which one or two non adjacent CH 2 groups can also be replaced by O atoms, or is a 1,3-dithiane-2,5-diyl group or 1,4-bicyclo(2,2,2)-octylene group, A 3 , A 4 are each a 1,4-cyclohexylene group, in which one or two non adjacent CH 2 groups can also be replaced by O atoms, or are each a 1,3-dithiane-2,5-diyl group, and A 5 or a 1,4-phenylene group which is unsubstituted or substituted by one or two F and/or Cl atoms and/or CH 3 groups and/or CN groups, and in which one or two CH groups can also be replaced by N atoms, n is 0 or 1, Z 1 is --CO--O--, --O--CO--, --CH 2 CH 2 --, --CH 2 O--, --OCH 2 or a single bond, Z 2 is --CH 2 CH 2 --, --CH 2 O--, --OCH 2 --, --O--CO-- or a single bond and R 3 is H or an alkyl group with 1-12 C atoms, in which one or two non adjacent CH 2 groups can also be replaced by O atoms and/or CO groups and/or --CO--O-- groups and/or --O--CO-- groups, with the proviso that (a) if A 2 =A 3 =1,4-phenylene (n=1) and/or if R 1 -A 1 =p-(trans-4-alkylcyclohexyl)-phenyl, at least one of the groups A 2 and/or A 3 is laterally substituted, and (b) if A 1 =A and/or R 1 -A 1 =trans-4-(trans-4-alkylcyclohexyl)-cyclohexyl, n is 1, can be used as components of liquid crystal phases.
Inventors
- 👤 Julie E. Fearon
- 👤 Wendy E. Smith
- 👤 George W. Gray
- 👤 David Lacey
- 👤 Kenneth J. Toyne
- 👤 Georg Weber
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 15:34
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/02; C07D239/24; C07D239/26; C07C; C07C255/00; C07D241/00; C07D241/02; C07D241/10; C07D241/12; C07D263/00; C07D263/02; C07D263/08; C07D263/10; C07D263/14; C09; C09K; C09K19/00; C09K19/04; C09K19/06; C09K19/08; C09K19/30; C09K19/3001; C09K19/3028; C09K19/32; C09K19/321; C09K19/34; C09K19/3402; C09K19/3441; C09K19/345; C09K19/3452; C09K19/3458; C09K19/3469; C09K19/3491; C09K2019/3422
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
240 words
In a liquid crystalline phase comprising at least two liquid crystal components, the improvement wherein at least one liquid crystal component is an ethane derivative of the formula R.sup.1 --A.sup.1 --CH.sub.2 CH.sub.2 --A.sup.2 --(A.sup.3).sub.n --R.sup.2 wherein R 1 is H; alkyl of 1-12 C atoms; alkyl of 1-12 C atoms in which one or two non-adjacent CH 2 groups are independently replaced by O, alkylcarbonyl of 1-12 c atoms; alkylcarbonyloxy of 1-12 c atoms; alkoxycarbonyl of 1-12 c atoms; F; Cl; or Br; R 2 is --CN or --Z 2 --A 4 --CN, A 1 is --A--, --A--A 5 -- or --A 5 --A--, A 2 is 1,4-phenylene; 1,4-phenylene substituted by one of F, Cl, CH 3 , or CN; or 1,4-phenylene wherein two CH groups are replaced by N atoms, A is 1,4-cyclohexylene or 1,4-bicyclo(2,2,2)-octylene, A 3 and A 4 each independently is 1,4-cyclohexylene; 1,4-phenylene; 1,4-phenylene substituted by one of F, Cl, CH 3 , or CN; or 1,4-phenylene wherein two CH groups are replaced by N atoms, A 5 is 1,4-phenylene or 1,4-phenylene wherein two CH groups are replaced by N atoms, n is 0 or 1, Z 2 is --CH 2 CH 2 --, --CH 2 O--, --OCH 2 -- or --O--CO-- and with the provisos that: (a) at least one of the groups A 2 and A 3 is laterally substituted, and (b) if A 1 =A, or R 1 --A 1 =trans-4-(trans-4-alkylcyclohexyl)-cyclohexyl, n is 1.
Claim 2
Dependent Claim
240 words
In a liquid crystalline phase comprising at least two liquid crystal components, the improvement wherein at least one liquid crystal component is an ethane derivative of the formula R.sup.1 --A.sup.1 --CH.sub.2 CH.sub.2 --A.sup.2 --(A.sup.3).sub.n --R.sup.2 wherein R 1 is H; alkyl of 1-12 C atoms; alkyl of 1-12 C atoms in which one or two non-adjacent CH 2 groups are independently replaced by O, alkylcarbonyl of 1-12 c atoms; alkylcarbonyloxy of 1-12 c atoms; alkoxycarbonyl of 1-12 c atoms; F; Cl; or Br; R 2 is --CN or --Z 2 --A 4 --CN, A 1 is --A--, --A--A 5 -- or --A 5 --A--, A 2 is 1,4-phenylene; 1,4-phenylene substituted by one of F, Cl, CH 3 , or CN; or 1,4-phenylene wherein two CH groups are replaced by N atoms, A is 1,4-cyclohexylene or 1,4-bicyclo(2,2,2)-octylene, A 3 and A 4 each independently is 1,4-cyclohexylene; 1,4-phenylene; 1,4-phenylene substituted by one of F, Cl, CH 3 , or CN; or 1,4-phenylene wherein two CH groups are replaced by N atoms, A 5 is 1,4-phenylene or 1,4-phenylene wherein two CH groups are replaced by N atoms, n is 0 or 1, Z 2 is --CH 2 CH 2 --, --CH 2 O--, --OCH 2 -- or --O--CO-- and with the provisos that: (a) at least one of the groups A 2 and A 3 is laterally substituted, and (b) if A 1 =A, or R 1 --A 1 =trans-4-(trans-4-alkylcyclohexyl)-cyclohexyl, n is 1.
Claim 3
Dependent Claim
28 words
A phase of claim 1 wherein said formula is R.sup.1 --A--A.sup.5 --CH.sub.2 CH.sub.2 --A.sup.2 --CN R.sup.1 --A.sup.5 --A--CH.sub.2 CH.sub.2 --A.sup.2 --CN or R.sup.1 --A--CH.sub.2 CH.sub.2 --A.sup.2 --A.sup.3 --CN.
Claim 4
Dependent Claim
32 words
A phase of claim 1 wherein said formula is R.sup.1 --A--CH.sub.2 CH.sub.2 --A.sup.2 --A.sup.3 --Z.sup.2 --A.sup.4 --CN R.sup.1 --A--A.sup.5 --CH.sub.2 CH.sub.2 --A.sup.2 --A.sup.3 --CN or R.sup.1 --A.sup.5 --A--CH.sub.2 CH.sub.2 --A.sup.2 --A.sup.3 --CN.
Claim 5
Dependent Claim
29 words
A phase of claim 1 wherein said formula is R.sup.1 --A--A.sup.5 --CH.sub.2 CH.sub.2 --A.sup.2 --A.sup.3 --Z.sup.2 --A.sup.4 --CN or R.sup.1 --A.sup.5 --A--CH.sub.2 CH.sub.2 --A.sup.2 --A.sup.3 --Z.sup.2 --A.sup.4 --CN .
Claim 6
Dependent Claim
34 words
A phase of claim 1 wherein said formula is R.sup.1 --Cy--Phe--CH.sub.2 CH.sub.2 --PhX--CN wherein Phe is 1,4-phenylene, Cy is 1,4-cyclohexylene, and PhX is Phe substituted by one of F, Cl, CH 3 or CN.
Claim 7
Dependent Claim
50 words
A phase of claim 1 wherein said formula is R.sup.1 --A--CH.sub.2 CH.sub.2 --Pyr--PhX--CN R.sup.1 --A--CH.sub.2 CH.sub.2 --PhX--Phe--CN R.sup.1 --A--CH.sub.2 CH.sub.2 --Phe--PhX--CN or R.sup.1 --A--CH.sub.2 CH.sub.2 --PhX--Cy--CN wherein Phe is 1,4-phenylene, Cy is 1,4-cyclohexylene, Pyr is pyrimidine-2,5-diyl and PhX is Phe substituted by one of F, Cl, CH 3 or CN.
Claim 8
Dependent Claim
39 words
A phase of claim 1 wherein said formula is R.sup.1 --A--CH.sub.2 CH.sub.2 --PhX--Phe--Cy--CN or R.sup.1 --A--CH.sub.2 CH.sub.2 --Phe--PhX--Cy--CN wherein Phe is 1,4-phenylene, Cy is 1,4-cyclohexylene and PhX is Phe substituted by one of F, Cl, CH 3 or CN.
Claim 9
Dependent Claim
47 words
A phase of claim 1 wherein said formula is R.sup.1 --A--Phe--CH.sub.2 CH.sub.2 --PhX--Phe--CN R.sup.1 --A--Phe--CH.sub.2 CH.sub.2 --Phe--PhX--CN R.sup.1 --A--Phe--CH.sub.2 CH.sub.2 --Phe--PhX--CN or R.sup.1 --A--Phe--CH.sub.2 CH.sub.2 --PhX--Cy--CN wherein Phe is 1,4-phenylene, Cy is 1,4-cyclohexylene and PhX is Phe substituted by one of F, Cl, CH 3 or CN.
Claim 10
Dependent Claim
43 words
A phase of claim 1 wherein said formula is R.sup.1 --Cy--A--CH.sub.2 CH.sub.2 --PhX--Phe--CN R.sup.1 --Cy--A--CH.sub.2 CH.sub.2 --Phe--PhX--CN or R.sup.1 --Cy--A--CH.sub.2 CH.sub.2 --PhX--Cy--CN wherein Phe is 1,4-phenylene, Cy is 1,4-cyclohexylene and PhX is Phe substituted by one of F, Cl, CH 3 or CN.
Claim 11
Dependent Claim
17 words
A phase of claim 1 wherein in said formula R 1 is alkyl, alkoxy or oxa-containing alkyl.
Claim 12
Dependent Claim
15 words
A phase of claim 1 wherein in said formula A.sup.1 is --A-- or --A--A.sup.5 --.
Claim 13
Dependent Claim
12 words
A phase of claim 1 wherein in said formula, A is 1,4-cyclohexylene.
Claim 14
Dependent Claim
44 words
A phase of claim 1 wherein in said formula A 2 is Phe, PhX, Pyr, or Pyn wherein Phe is 1,4-phenylene, Pyn is pyridazine-3,6-diyl, Pyr is pyrimidine-2,5-diyl and PhX is Phe substituted in the 2- or 3-position by F, Cl or CH 3 .
Claim 15
Dependent Claim
48 words
A phase of claim 1 wherein in said formula A 3 and A 4 and A 5 each independently is Phe, PhX, or Cy wherein Phe is 1,4-phenylene, Cy is 1,4-cyclohexylene, and PhX is Phe substituted in the 2- or 3-position by F, Cl or CH 3 .
Claim 16
Dependent Claim
15 words
A phase of claim 1 wherein Z 1 and Z 2 is a single bond.
Claim 17
Dependent Claim
21 words
In a liquid crystal display element, comprising a liquid crystal phase, the improvement wherein the phase is one of claim 1.
Claim 18
Dependent Claim
23 words
In a liquid crystal electro-optical display element, comprising a liquid crystal dielectric, the improvement wherein the dielectric is a phase of claim 1.
Claim 19
Dependent Claim
9 words
A phase of claim 1, wherein A is 1,4-bicyclo(2,2,2)-octylene.
Claim 20
Dependent Claim
20 words
A phase according to claim 1, wherein only one of the groups A 2 and A 3 is laterally substituted.
Claim 21
Dependent Claim
15 words
A phrase according to claim 1, wherein said phase comprises a laterally fluorinated ethane derivative.
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