US4708441A
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Assignee: Merck Patent GmbH
•
Filing: 1985-08-16
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Granted: 1987-11-24
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Expires: 2005-08-16
Abstract
Abstract Compounds of the formula <IMAGE> I wherein X2 is a single covalent bond or -COO-; X1 is a single covalent bond, -COO-, -CH2CH2- or when X2 is -COO-, X1 also can be p-C6H4-, p-C6H4-CH2CH2-, -CH2CH2-p-C6H4, p-C6H4-COO- or -COO-p-C6H4; ring A is a benzene ring or trans-1,4-cyclohexylene; ring B is a benzene ring or when X2 is -COO- and X1 is a single covalent bond, -COO- or -CH2CH2-, ring B also can be trans-1,4-cyclohexylene; Z1, Z2 and Z3 individually are hydrogen or when positioned on a benzene ring which is not linked directly with a further ring via a single covalent bond, Z1, Z2 and Z3 also can be halogen, cyano or methyl; Y2 is cyano, nitro, 2,2-dicyanovinyl or when Y1 is hydrogen Y2 also can be 2,2-dicyano-1-methylvinyl; Y1 is halogen, cyano, C1-C3-alkyl or, when X1 includes a benzene ring of -COO- or Y2 is nitro or at least one of Z1 and Z2 is other than hydrogen, Y1 also can be hydrogen; and R1 is C1-C12-alkyl or when positioned on a benzene ring R1 also can be C1-C12-alkoxy, their manufacture and use in liquid crystalline mixtures are described.
Inventors
- 👤 Martin Petrzilka
- 👤 Martin Schadt
- 👤 Alois Villiger
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 07:28
CPC Classifications
C; C07; C07C; C07C255/00; C07C205/00; C07C205/39; C07C205/42; C07C205/43; C07C29/00; C07C29/132; C07C29/136; C07C29/147; C07C309/00; C07C31/00; C07C31/13; C07C31/133; C07C31/135; C07C31/1355; C07C61/00; C07C61/12; C07C61/16; C07C61/39; C07C63/00; C07C63/33; C07C63/49; C07C63/68; C07C63/72; C09; C09K; C09K19/00; C09K19/04; C09K19/06; C09K19/08; C09K19/10; C09K19/20; C09K19/2007; C09K19/30; C09K19/3001; C09K19/3066; C09K19/3068; C07B; C07B2200/00; C07B2200/09; C07C2601/00; C07C2601/12; C07C2601/14
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
188 words
A compound of the formula ##STR26## wherein X 2 is a single covalent bond or --COO--; X 1 is a single covalent bond, --COO--, or --CH 2 CH 2 --; ring A is a benzene ring or trans-1,4-cyclohexylene; ring B is a benzene ring or when X 2 is --COO--, ring B also can be trans-1,4-cyclohexylene; Z 1 , Z 2 and Z 3 individually are hydrogen or when positioned on a benzene ring which is not linked directly with a further ring via a single covalent bond, Z 1 , Z 2 and Z 3 also can be halogen, cyano or methyl; Y 2 is cyano, nitro, 2,2-dicyanovinyl or when Y 1 is hydrogen Y 2 also can be 2,2-dicyano-1-methylvinyl; Y 1 is halogen, cyano, C 1 -C 3 -alkyl or when X 1 is --COO-- or Y 2 is nitro or at least one of Z 1 and Z 2 is other than hydrogen, Y 1 also can be hydrogen; and R 1 is C 1 -C 12 -alkyl or when positioned on a benzene ring R 1 also can be C 1 -C 12 -alkoxy.
Claim 2
Dependent Claim
188 words
A compound of the formula ##STR26## wherein X 2 is a single covalent bond or --COO--; X 1 is a single covalent bond, --COO--, or --CH 2 CH 2 --; ring A is a benzene ring or trans-1,4-cyclohexylene; ring B is a benzene ring or when X 2 is --COO--, ring B also can be trans-1,4-cyclohexylene; Z 1 , Z 2 and Z 3 individually are hydrogen or when positioned on a benzene ring which is not linked directly with a further ring via a single covalent bond, Z 1 , Z 2 and Z 3 also can be halogen, cyano or methyl; Y 2 is cyano, nitro, 2,2-dicyanovinyl or when Y 1 is hydrogen Y 2 also can be 2,2-dicyano-1-methylvinyl; Y 1 is halogen, cyano, C 1 -C 3 -alkyl or when X 1 is --COO-- or Y 2 is nitro or at least one of Z 1 and Z 2 is other than hydrogen, Y 1 also can be hydrogen; and R 1 is C 1 -C 12 -alkyl or when positioned on a benzene ring R 1 also can be C 1 -C 12 -alkoxy.
Claim 3
Dependent Claim
12 words
The compound of claim 1 wherein ring B is a benzene ring.
Claim 4
Dependent Claim
36 words
The compound of claim 1 wherein Z 1 , Z 2 and Z 3 are hydrogen or at most two of Z 1 , Z 2 and Z 3 are chlorine and the remainder are hydrogen.
Claim 5
Dependent Claim
15 words
The compound of claim 3 wherein Y 1 is hydrogen, fluorine, chlorine, cyano or methyl.
Claim 6
Dependent Claim
138 words
The compound of claim 1 having the formula ##STR27## in which X 2 is a single covalent bond or --COO--; Y 2 is cyano, nitro, 2,2-dicyanovinyl or when Y 1 is hydrogen Y 2 also can be 2,2-dicyano-1-methylvinyl; X 1 is a single covalent bond, or --COO--; ring A is p-phenylene or trans-1,4-cyclohexylene; Z 2 is hydrogen or when X 1 and X 2 are --COO--, Z 2 also can be chlorine; Z 3 is hydrogen or when X 2 is --COO--, Z 3 also can be chlorine; Y 1 is fluorine, chlorine, cyano, methyl or when X 1 is --COO-- or Y 2 is nitro, Y 1 also can be hydrogen; and R 1 is C 1 -C 12 -alkyl or when positioned on a benzene ring R 1 also can be C 1 -C 12 -alkoxy.
Claim 7
Dependent Claim
10 words
The compound of claim 5 wherein Z 2 is hydrogen.
Claim 8
Dependent Claim
29 words
The compound of claim 5 wherein Y 1 is chlorine or cyano, or when X 1 is --COO-- or Y 2 is nitro, Y 1 also can be hydrogen.
Claim 9
Dependent Claim
12 words
The compound of claim 5 wherein Y 2 is cyano or nitro.
Claim 10
Dependent Claim
10 words
The compound of claim 8 wherein Y 1 is chlorine.
Claim 11
Dependent Claim
19 words
The compound of claim 5 wherein X 1 is --COO--; Y 1 is hydrogen and Y 2 is 2,2-dicyano-1-methylvinyl.
Claim 12
Dependent Claim
10 words
The compound of claim 5 wherein ring A is trans-1,4-cyclohexylene.
Claim 13
Dependent Claim
19 words
The compound of claim 5 wherein R 1 is a straight-chain alkyl group of 1 to 12 carbon atoms.
Claim 14
Dependent Claim
20 words
The compound of claim 5 wherein the alkyl or akoxy group of R 1 contains 3 to 10 carbon atoms.
Claim 15
Dependent Claim
20 words
The compound of claim 13 wherein the alkyl or alkoxy group of R 1 contains 5 to 9 carbon atoms.
Claim 16
Dependent Claim
40 words
The compound of claim 5 wherein X 1 is a single covalent bond, or --COO--; ring A is trans-1,4-cyclohexylene; Z 2 is hydrogen, X 2 is --COO--; Y 2 is cyano or nitro; and Z 3 is hydrogen or chlorine.
Claim 17
Dependent Claim
205 words
A liquid crystalline mixture comprising at least two components wherein at least one of the components is a compound of the formula ##STR28## wherein X 2 is a single covalent bond or --COO--; X 1 is a single covalent bond, --COO--, or --CH 2 CH 2 --; ring A is a benzene ring or trans-1,4-cyclohexylene; ring B is a benzene ring or when X 2 is --COO--, ring B also can be trans-1,4-cyclohexylene; Z 1 , Z 2 and Z 3 individually are hydrogen or when positioned on a benzene ring which is not linked directly with a further ring via a single covalent bond, Z 1 , Z 2 and Z 3 also can be halogen, cyano or methyl; Y 2 is cyano, nitro, 2,2-dicyanovinyl or when Y 1 is hydrogen Y 2 also can be 2,2-dicyano-1-methylvinyl; Y 1 is halogen, cyano, C 1 -C 3 -alkyl or when X 1 is --COO-- or Y 2 is nitro or at least one of Z 1 and Z 2 is other than hydrogen, Y 1 also can be hydrogen; and R 1 is C 1 -C 12 -alkyl or when positioned on a benzene ring R 1 also can be C 1 -C 12 -alkoxy.
Claim 18
Dependent Claim
205 words
A liquid crystalline mixture comprising at least two components wherein at least one of the components is a compound of the formula ##STR28## wherein X 2 is a single covalent bond or --COO--; X 1 is a single covalent bond, --COO--, or --CH 2 CH 2 --; ring A is a benzene ring or trans-1,4-cyclohexylene; ring B is a benzene ring or when X 2 is --COO--, ring B also can be trans-1,4-cyclohexylene; Z 1 , Z 2 and Z 3 individually are hydrogen or when positioned on a benzene ring which is not linked directly with a further ring via a single covalent bond, Z 1 , Z 2 and Z 3 also can be halogen, cyano or methyl; Y 2 is cyano, nitro, 2,2-dicyanovinyl or when Y 1 is hydrogen Y 2 also can be 2,2-dicyano-1-methylvinyl; Y 1 is halogen, cyano, C 1 -C 3 -alkyl or when X 1 is --COO-- or Y 2 is nitro or at least one of Z 1 and Z 2 is other than hydrogen, Y 1 also can be hydrogen; and R 1 is C 1 -C 12 -alkyl or when positioned on a benzene ring R 1 also can be C 1 -C 12 -alkoxy.
Claim 19
Dependent Claim
109 words
The liquid crystalline mixture of claim 16 comprising three components A, B and C, each of which contains one or more compounds, wherein component A has a viscosity of at most about 40 cp, a clearing point of at least about 40° C. and a dielectric anisotropy between about -2 and about +1, component B has a dielectric anisotropy below about -2, component C has a dielectric anisotropy above about +10, a clearing point of at least about 100° C. and a cross-over frequency in the total mixture of at most about 15 kHz at 20° C., and wherein component C contains at least one compound of formula I.
Claim 20
Dependent Claim
29 words
The liquid crystalline mixture of claim 17 comprising at least about 30 wt.% of component A, about 3-50 wt.% of component B and about 5-40 wt.% of component C.
Claim 21
Dependent Claim
223 words
An electro-optical cell comprising: (a) two plate means; (b) liquid crystal means disposed between the two plate means and including a compound of the formula ##STR29## wherein X 2 is a single covalent bond or --COO--; X 1 is a single covalent bond, --COO--, or --CH 2 CH 2 --; ring A is a benzene ring or trans-1,4-cyclohexylene; ring B is a benzene ring or when X 2 is --COO--, ring B also can be trans-1,4-cyclohexylene; Z 1 , Z 2 and Z 3 individually are hydrogen or when positioned on a benzene ring which is not linked directly with a further ring via a single covalent bond, Z 1 , Z 2 and Z 3 also can be halogen, cyano or methyl; Y 2 is cyano, nitro, 2,2-dicyanovinyl or when Y 1 is hydrogen Y 2 also can be 2,2-dicyano-1-methylvinyl; Y 1 is halogen, cyano, C 1 -C 3 -alkyl or when X 1 is --COO-- or Y 2 is nitro or at least one of Z 1 and Z 2 is other than hydrogen, Y 1 also can be hydrogen; and R 1 is C 1 -C 12 -alkyl or when R 1 is positioned on a benzene ring R 1 also can be C 1 -C 12 -alkoxy; and (c) means for applying an electrical potential to said plate means.
Claim 22
Dependent Claim
223 words
An electro-optical cell comprising: (a) two plate means; (b) liquid crystal means disposed between the two plate means and including a compound of the formula ##STR29## wherein X 2 is a single covalent bond or --COO--; X 1 is a single covalent bond, --COO--, or --CH 2 CH 2 --; ring A is a benzene ring or trans-1,4-cyclohexylene; ring B is a benzene ring or when X 2 is --COO--, ring B also can be trans-1,4-cyclohexylene; Z 1 , Z 2 and Z 3 individually are hydrogen or when positioned on a benzene ring which is not linked directly with a further ring via a single covalent bond, Z 1 , Z 2 and Z 3 also can be halogen, cyano or methyl; Y 2 is cyano, nitro, 2,2-dicyanovinyl or when Y 1 is hydrogen Y 2 also can be 2,2-dicyano-1-methylvinyl; Y 1 is halogen, cyano, C 1 -C 3 -alkyl or when X 1 is --COO-- or Y 2 is nitro or at least one of Z 1 and Z 2 is other than hydrogen, Y 1 also can be hydrogen; and R 1 is C 1 -C 12 -alkyl or when R 1 is positioned on a benzene ring R 1 also can be C 1 -C 12 -alkoxy; and (c) means for applying an electrical potential to said plate means.
Claim 23
Dependent Claim
10 words
The compound of claim 5 wherein ring A is p-phenylene.
Claim 24
Dependent Claim
35 words
The compound of claim 20 wherein Y 1 and Z 3 are chlorine, Y 2 is cyano or nitro, Z 2 is hydrogen, X 2 is --COO and X 1 is a single covalent bond.
Claim 25
Dependent Claim
9 words
The compound of claim 5, 4'-hexyl-4-biphenylcarboxylic acid 3-chloro-4-[(3-chloro-4-cyanophenoxy)carbonyl]phenyl ester.
Claim 26
Dependent Claim
9 words
The compound of claim 5, 4'heptyl-4-biphenylcarboxylic acid 3-chloro-4-[(3-chloro-4-cyanophenoxy)carbonyl]phenyl ester.
Claim 27
Dependent Claim
9 words
The compound of claim 5, 4'-hexyl-4-biphenylcarboxylic acid 3-chloro-4-[(3-chloro-4-nitrophenoxy)carbonyl]phenyl ester.
Claim 28
Dependent Claim
9 words
The compound of claim 5, 4'-heptyl-4-biphenylcarboxylic acid 3-chloro-4-[(3-chloro-4-nitrophenoxy)carbonyl]phenyl ester.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1990-11-23 | 1991-05-25 | 1991-11-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-11-23 | 1995-05-25 | 1995-11-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-11-23 | 1999-05-25 | 1999-11-24 | $7700.00 | Window Closed / Lapsed |