US5238602A
Expired / Lapsed
US
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Liquid crystals
Assignee: Rolic Technologies Ltd
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Filing: 1987-05-26
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Granted: 1993-08-24
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Expires: 2007-05-26
Abstract
Abstract Compounds of the formula <IMAGE> I wherein n stands for the number 0 or 1; the rings A1, A2 and A3 represent 1,4-phenylene, 2-fluoro-1,4-phenylene or trans-1,4-cyclohexylene or one of these rings also represents a 2,5-disubstituted pyrimidine ring or a trans-2,5-disubstituted m-dioxane ring; X1 represents a single covalent bond, -COO-, -OOC-, -CH2CH2-, p-C6H4-, -CH2CH2-p- C6H4-, -CH2CH2-p-C6H4-CH2CH2- or, insofar as the rings A1 and A2 represent 1,4-phenylene, also -NON-; R2 represents 1E-alkenyl, 2Z-alkenyl, 3E-alkenyl, 4-alkenyl or alkenyloxy, with the proviso that the oxygen atom in alkenyloxy is linked with a saturated carbon atom; and R1 signifies 1E-alkenyl, 2Z-alkenyl, 3E-alkenyl, 4-alkenyl or, insofar as R2 represents alkenyloxy, also alkyl, their manufacture, as well as liquid crystalline mixtures and the use for electro-optical purposes.
Inventors
- 👤 Martin Petrzilka
- 👤 Martin Schadt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 23:31
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/02; C07D239/24; C07D239/26; C07C; C07C43/00; C07C43/02; C07C43/20; C07C43/215; C07C43/225; C07D303/00; C07D303/02; C07D303/12; C07D303/14; C07D319/00; C07D319/04; C07D319/06; C09; C09K; C09K19/00; C09K19/04; C09K19/06; C09K19/08; C09K19/30; C09K19/3001; C09K19/34; C09K19/3441; C09K19/345; C09K19/3458; C09K19/3469
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
148 words
A compound of the formula ##STR18## wherein n is the integer 0 or 1; rings A 1 , A 2 and A 3 independently are 1,4-phenylene, 2-fluoro-1,4-phenylene or trans-1,4-cyclohexylene or one of these rings also is 2,5-disubstituted pyrimidine or trans-2,5-disubstituted m--dioxane; X 1 is a single covalent bond, --COO--, --OOC--, --CH 2 CH 2 --, p--C 6 H 4 --, --CH 2 CH 2 --p--C 6 H 4 --, --CH 2 CH 2 --p--C 6 H 4 --CH 2 CH 2 --or, when rings A 1 and A 2 are 1,4-phenylene, X 1 also can be --NON--; R 2 is 1E-alkenyl, 2Z-alkenyl, 3E-alkenyl, 4-alkenyl, (2E-alkenyl)oxy or (3alkenyl)oxy; R 1 is 1E-alkenyl, 2Z-alkenyl, 3E-alkenyl, 4-alkenyl or, when R 2 is alkenyloxy, R 1 also can be alkyl; and --NON-- is --N═N(O)--or --N(O)═N--; with the proviso that the 1E-alkenyl or 2Z-alkenyl moiety is attached to other than an aromatic ring.
Claim 2
Dependent Claim
148 words
A compound of the formula ##STR18## wherein n is the integer 0 or 1; rings A 1 , A 2 and A 3 independently are 1,4-phenylene, 2-fluoro-1,4-phenylene or trans-1,4-cyclohexylene or one of these rings also is 2,5-disubstituted pyrimidine or trans-2,5-disubstituted m--dioxane; X 1 is a single covalent bond, --COO--, --OOC--, --CH 2 CH 2 --, p--C 6 H 4 --, --CH 2 CH 2 --p--C 6 H 4 --, --CH 2 CH 2 --p--C 6 H 4 --CH 2 CH 2 --or, when rings A 1 and A 2 are 1,4-phenylene, X 1 also can be --NON--; R 2 is 1E-alkenyl, 2Z-alkenyl, 3E-alkenyl, 4-alkenyl, (2E-alkenyl)oxy or (3alkenyl)oxy; R 1 is 1E-alkenyl, 2Z-alkenyl, 3E-alkenyl, 4-alkenyl or, when R 2 is alkenyloxy, R 1 also can be alkyl; and --NON-- is --N═N(O)--or --N(O)═N--; with the proviso that the 1E-alkenyl or 2Z-alkenyl moiety is attached to other than an aromatic ring.
Claim 3
Dependent Claim
82 words
The compound of claim 1, wherein the rings A 1 , A 2 and A 3 independently are 1,4-phenylene or trans-1,4-cyclohexylene or one of these rings also is 2,5-disubstituted pyrimidine or trans-2,5-disubstituted m-dioxane; R 2 is 1E-alkenyl, 2Z-alkenyl, 3E-alkenyl, 4-alkenyl, (2E-alkenyl)oxy or (3-alkenyl)oxy; and R 1 is 1E-alkenyl, 2Z-alkenyl, 3E-alkenyl, 4-alkenyl or, when R 2 is (2E-alkenyl)oxy or (3-alkenyl)oxy, R 1 also can be alkyl; with the proviso that the 1E-alkenyl or 2Z-alkenyl moiety is attached to other than an aromatic ring.
Claim 4
Dependent Claim
25 words
The compound of claim 1, wherein R 1 and R 2 are straight-chain residues defined in claim 1 having a maximum of 12 carbon atoms.
Claim 5
Dependent Claim
18 words
The compound of claim 3 wherein R 1 and R 2 have a maximum of 7 carbon atoms.
Claim 6
Dependent Claim
22 words
The compound of claim 1, wherein R 2 is (2E-alkenyl)oxy or one of R 1 and R 2 is 1E-alkenyl or 3E-alkenyl.
Claim 7
Dependent Claim
26 words
The compound of claim 1, wherein X 1 is a single covalent bond, --COO--, --OOC--, --CH 2 CH 2 -- or p--C 6 H 4 --.
Claim 8
Dependent Claim
11 words
The compound of claim 1, wherein n is the integer O.
Claim 9
Dependent Claim
21 words
The compound of claim 7, wherein n is the integer O and ring A 2 is 1,4-phenylene, trans-1,4-cyclohexylene or 2,4-disubstituted pyrimidine.
Claim 10
Dependent Claim
41 words
The compound of claim 8, wherein n is the integer O, ring A 1 is trans-1,4-cyclohexylene, ring A 2 is 1,4-phenylene and X 1 is a single covalent bond, --COO--, --CH 2 CH 2 -- or p--C 6 H 4 --.
Claim 11
Dependent Claim
30 words
The compound of claim 1, wherein ring A 1 is 2,5-disubstituted pyrimidine or trans-2,5-disubstituted m-dioxane, ring A 2 is 1,4-phenylene or trans-1,4-cyclohexylene and X 1 is a single covalent bond.
Claim 12
Dependent Claim
20 words
The compound of claim 1, wherein n is the integer 1 and ring A 2 is 1,4-phenylene or 2,5-disubstituted pyrimidine.
Claim 13
Dependent Claim
180 words
A liquid crystalline mixture with at least 2 components, wherein at least one of said components is a compound of formula ##STR19## wherein n is the integer 0 or 1; rings A 1 , A 2 and A 3 independently are 1,4-phenylene, 2-fluoro-1,4-phenylene or trans-1,4-cyclohexylene or one of these rings also is 2,5-disubstituted pyrimidine or trans-2,5-disubstituted m-dioxane; X 1 is a single covalent bond, --COO--, --OOC--, --CH 2 CH 2 --, p--C 6 H 4 --, --CH 2 CH 2 --p--C 6 H 4 --, --CH 2 CH 2 --p--C 6 H 4 --CH 2 CH 2 -- or, when rings A 1 and A 2 are 1,4-phenylene, X 1 also can be --NON--; R 2 is 1E-alkenyl, 2Z-alkenyl, 3E-alkenyl, 4-alkenyl or alkenyloxy, with the proviso that the oxygen atom in alkenyloxy is linked with a saturated carbon atom; R 1 is 1E-alkenyl, 2Z-alkenyl, 3E-alkenyl, 4-alkenyl or, when R 2 is alkenyloxy, R 1 also can be alkyl; and --NON-- is --N═N(O)--or --N(O)═N--; with the proviso that the 1E-alkenyl or 2Z-alkenyl moiety is attached to other than an aromatic ring.
Claim 14
Dependent Claim
180 words
A liquid crystalline mixture with at least 2 components, wherein at least one of said components is a compound of formula ##STR19## wherein n is the integer 0 or 1; rings A 1 , A 2 and A 3 independently are 1,4-phenylene, 2-fluoro-1,4-phenylene or trans-1,4-cyclohexylene or one of these rings also is 2,5-disubstituted pyrimidine or trans-2,5-disubstituted m-dioxane; X 1 is a single covalent bond, --COO--, --OOC--, --CH 2 CH 2 --, p--C 6 H 4 --, --CH 2 CH 2 --p--C 6 H 4 --, --CH 2 CH 2 --p--C 6 H 4 --CH 2 CH 2 -- or, when rings A 1 and A 2 are 1,4-phenylene, X 1 also can be --NON--; R 2 is 1E-alkenyl, 2Z-alkenyl, 3E-alkenyl, 4-alkenyl or alkenyloxy, with the proviso that the oxygen atom in alkenyloxy is linked with a saturated carbon atom; R 1 is 1E-alkenyl, 2Z-alkenyl, 3E-alkenyl, 4-alkenyl or, when R 2 is alkenyloxy, R 1 also can be alkyl; and --NON-- is --N═N(O)--or --N(O)═N--; with the proviso that the 1E-alkenyl or 2Z-alkenyl moiety is attached to other than an aromatic ring.
Claim 15
Dependent Claim
196 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 ##STR20## wherein n is the integer 0 or 1; rings A 1 , A 2 and A 3 independently are 1,4-phenylene, 2-fluoro-1,4-phenylene or trans-1,4-cyclohexylene or one of these rings also is 2,5-disubstituted pyrimidine or trans-2,5-disubstituted m-dioxane; X 1 is a single covalent bond, --COO--, --OOC--, --CH 2 CH 2 --, p--C 6 H 4 --, --CH 2 CH 2 --p--C 6 H 4 --, --CH 2 CH 2 --p--C 6 H 4 --CH 2 CH 2 -- or, when rings A 1 and A 2 are 1,4-phenylene, X 1 also can be --NON--; R 2 is 1E-alkenyl, 2Z-alkenyl, 3E-alkenyl, 4-alkenyl or alkenyloxy, with the proviso that the oxygen atom in alkenyloxy is linked with a saturated carbon atom; R 1 is 1E-alkenyl, 2Z-alkenyl, 3E-alkenyl, 4-alkenyl or, when R 2 is alkenyloxy, R 1 also can be alkyl; and --NON-- is --N═N(O)--or --N(O)═N--; with the proviso that the 1E-alkenyl or 2Z-alkenyl moiety is attached to other than an aromatic ring; c) means to apply an electric potential to the two plate means.
Claim 16
Dependent Claim
196 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 ##STR20## wherein n is the integer 0 or 1; rings A 1 , A 2 and A 3 independently are 1,4-phenylene, 2-fluoro-1,4-phenylene or trans-1,4-cyclohexylene or one of these rings also is 2,5-disubstituted pyrimidine or trans-2,5-disubstituted m-dioxane; X 1 is a single covalent bond, --COO--, --OOC--, --CH 2 CH 2 --, p--C 6 H 4 --, --CH 2 CH 2 --p--C 6 H 4 --, --CH 2 CH 2 --p--C 6 H 4 --CH 2 CH 2 -- or, when rings A 1 and A 2 are 1,4-phenylene, X 1 also can be --NON--; R 2 is 1E-alkenyl, 2Z-alkenyl, 3E-alkenyl, 4-alkenyl or alkenyloxy, with the proviso that the oxygen atom in alkenyloxy is linked with a saturated carbon atom; R 1 is 1E-alkenyl, 2Z-alkenyl, 3E-alkenyl, 4-alkenyl or, when R 2 is alkenyloxy, R 1 also can be alkyl; and --NON-- is --N═N(O)--or --N(O)═N--; with the proviso that the 1E-alkenyl or 2Z-alkenyl moiety is attached to other than an aromatic ring; c) means to apply an electric potential to the two plate means.
Claim 17
Dependent Claim
17 words
The compound of claim 1, wherein R 2 is (2E-alkenyl)oxy, or (3-alkenyl)oxy; and R 1 is alkyl.
References Cited (Backward Citations)
US4001137A
Cited
US3819531A
Cited
US3810879A
Cited
GB1432692A
Cited
US3947375A
Cited
US4065489A
Cited
FR2377441A1
Cited
US4147655A
Cited
DE2944591A1
Cited
US4358391A
Cited
US4363767A
Cited
JPS5767538A
Cited
US4410570A
Cited
US4388453A
Cited
US4528114A
Cited
EP0122389A2
Cited
US4565425A
Cited
US4676604A
Cited
JPS59199649A
Cited
DE3331515A1
Cited
JPS60112723A
Cited
US4629581A
Cited
US4621901A
Cited
US4709030A
Cited
JPS6127929A
Cited
JPS6127931A
Cited
JPS6127928A
Cited
US4726911A
Cited
US4707295A
Cited
US4719032A
Cited
US4654421A
Cited
US4710015A
Cited
US5013477A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1996-08-23 | 1997-02-22 | 1997-08-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2000-08-23 | 2001-02-22 | 2001-08-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2004-08-23 | 2005-02-22 | 2005-08-24 | $7700.00 | Window Closed / Lapsed |