Patent US4707295A successfully refreshed from Google Patents.
US4707295A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Bicyclooctane derivatives
Assignee: Merck Patent GmbH
•
Filing: 1986-03-24
•
Granted: 1987-11-17
•
Expires: 2006-03-24
Abstract
Abstract Bicyclooctane derivatives of the formula I R.sup.1 --A.sup.1 --A.sup.2 --R.sup.2 I wherein R 1 and R 2 independently of one another are each an alkyl group which has 1-12 C atoms and in which it is also possible for one or two non-adjacent CH 2 groups to be replaced by O atoms and/or CO groups and/or --O13 CO groups and/or --CO--O groups and/or --CH═CH-- groups, one of the radicals R 1 and R 2 being also --A 3 --R 3 , A 1 is a 1,4-cyclohexylene group which is unsubstituted or substituted in the 1-position and/or 2-position and/or 3-position and/or 4-position by alkyl which has in each case 1-5 C atoms and is unsubstituted or substituted or fluorinated, and in which it is also possible for one or two non-adjacent CH 2 groups to be replaced by one or two different groupings from the group --O--, --CO--, --CH═CH--, --S--, --SO-- or --SO 2 --, or is substituted by F, Cl, Br, CN and/or CHO, A 2 is a 1,4-bicyclo[2.2.2] octylene group, --A 3 --R 3 is --Cy--R 3 , --Ph--R 3 , --Cy--Ph--R 3 or --Ph--Cy--R 3 , Cy is 1,4-cyclohexylene or one of the other groups recited for A 1 , Ph is 1,4-phenylene which is unsubstituted or substituted by or one two F atoms and/or CH 3 groups and R 3 is an alkyl group which has 1-12 C atoms and in which it is also possible for one or two non-adjacent CH 2 groups to be replaced by O atoms and/or CO groups and/or O--CO groups and/or --CO--O groups and/or --CH═CH-- groups are suitable for use as components of liquid-crystal phases for field effect and/or bistability effect displys.
Inventors
- 👤 Ludwig Pohl
- 👤 Bernhard Scheuble
- 👤 Andreas Wachtler
- 👤 Reinhard Hittich
- 👤 Peter Fuss
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 14:30
CPC Classifications
C; C07; C07C; C07C255/00; C07C13/00; C07C13/28; C07C13/32; C07C13/44; C07C23/00; C07C23/18; C07C23/20; C09; C09K; C09K19/00; C09K19/04; C09K19/06; C09K19/32; C09K19/321
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
194 words
In a liquid crystalline phase comprising at least two liquid crystalline components, the improvement wherein at least one of said components is a bicyclooctane derivative of the formula R.sup.1 --A.sup.1 --A.sup.2 --R.sup.2 wherein R 1 and R 2 independently are each C 1-12 alkyl, C 1-10 alkoxy or C 1-12 alkyl in which one or two non-adjacent CH 2 groups are replaced by CO, --O--CO, --CO--O or --CH═CH--, or one of R 1 and R 2 can also be --A 3 --R 3 , A l is a 1,4-cyclohexylene group which is unsubstituted or substituted in the 2--, 3-- position or a combination thereof by F, Cl, Br, CN, C 1-5 -alkyl, C 1-5 -alkoxy, or C 1-5 perfluorinated alkyl, A 2 is a 1,4-bicyclo(2.2.2)octylene group; A 3 is --Cy, --Ph, --Cy--Ph or --Ph--Cy, Cy is 1,4-cyclohexylene or one of the other groups recited for A 1 , Ph is 1,4-phenylene which is unsubstituted, or monosubstitited by F, CH 3 , or a combination thereof, R 3 is C 1-12 alkyl, C 1-10 alkoxy or C 1-12 alkyl wherein one or two non-adjacent CH 2 groups are replaced by CO, O--CO, --CO--O, or --CH═CH--.
Claim 2
Dependent Claim
194 words
In a liquid crystalline phase comprising at least two liquid crystalline components, the improvement wherein at least one of said components is a bicyclooctane derivative of the formula R.sup.1 --A.sup.1 --A.sup.2 --R.sup.2 wherein R 1 and R 2 independently are each C 1-12 alkyl, C 1-10 alkoxy or C 1-12 alkyl in which one or two non-adjacent CH 2 groups are replaced by CO, --O--CO, --CO--O or --CH═CH--, or one of R 1 and R 2 can also be --A 3 --R 3 , A l is a 1,4-cyclohexylene group which is unsubstituted or substituted in the 2--, 3-- position or a combination thereof by F, Cl, Br, CN, C 1-5 -alkyl, C 1-5 -alkoxy, or C 1-5 perfluorinated alkyl, A 2 is a 1,4-bicyclo(2.2.2)octylene group; A 3 is --Cy, --Ph, --Cy--Ph or --Ph--Cy, Cy is 1,4-cyclohexylene or one of the other groups recited for A 1 , Ph is 1,4-phenylene which is unsubstituted, or monosubstitited by F, CH 3 , or a combination thereof, R 3 is C 1-12 alkyl, C 1-10 alkoxy or C 1-12 alkyl wherein one or two non-adjacent CH 2 groups are replaced by CO, O--CO, --CO--O, or --CH═CH--.
Claim 3
Dependent Claim
25 words
A liquid crystalline phase of claim 1, wherein R 1 , R 2 and R 3 are independently C 1-10 -alkyl, or C 1-10 -alkoxy.
Claim 4
Dependent Claim
25 words
A liquid crystalline phase of claim 2, wherein R 1 , R 2 and R 3 are independently C 3-8 -alkyl, or C 2-8 -alkoxy.
Claim 5
Dependent Claim
31 words
A liquid crystalline phase of claim 3, wherein R 1 , R 2 and R 3 are independently propyl, butyl, pentyl, hexyl, heptyl, octyl, ethoxy, propoxy, butoxy, pentyloxy, heptyloxy, or octyloxy.
Claim 6
Dependent Claim
39 words
A liquid crystalline phase of claim 3, wherein R 1 , R 2 and R 3 are independently isopropyl, 1-methylpropyl, 2-methylpropyl, 2-methylbutyl, 3-methylbutyl, 2-methylpentyl, 3-methylpentyl, 1-methylhexyl, 2-ethylhexyl, 2-propylpentyl, 1-methylheptyl, isopropoxy, 2-methylpropoxy, 2-methylbutoxy, 3-methylbutoxy, 2-methylpentyloxy, 3-methylpentyloxy, 2-ethylhexyloxy, 1-methylhexyloxy, or 1-methylheptyloxy.
Claim 7
Dependent Claim
15 words
A phase of claim 1, wherein the bicyclooctane derivative has the formula R.sup.1 --Cy--A.sup.2 --R.sup.2.
Claim 8
Dependent Claim
25 words
A phase of claim 1, wherein the bicyclooctane derivative has the formula R.sup.1 --Cy--A.sup.2 --Ph--R.sup.3, R.sup.1 --Cy--A.sup.2 --Cy--R.sup.3, R.sup.3 --Cy--Cy--A.sup.2 --R.sup.3, or R.sup.3 --Ph--Cy--A.sup.2 --R.sup.2.
Claim 9
Dependent Claim
25 words
A phase of claim 1, wherein the bicyclooctane derivative has the formula R.sup.1 --Cy--A.sup.2 --Ph--Cy--R.sup.3, R.sup.1 --Cy--A.sup.2 --Cy--Ph--R.sup.3. R.sup.3 --Cy--Ph--Cy--A.sup.2 --R.sup.2, or R.sup.3 --Ph--Cy--Cy--A.sup.2 --R.sup.2.
Claim 10
Dependent Claim
42 words
A phase of claim 1, wherein A 1 is unsubstituted 1,4-cyclohexylene or 1,4-cyclohexylene of the formula ##STR2## or a mirror image thereof, wherein X 1 and X 2 independently are F, Cl, CN, CF 3 , CH 3 or OCH 3 .
Claim 11
Dependent Claim
20 words
A liquid crystalline phase of claim 9, wherein X 1 and X 2 are independently F or CH 3 .
Claim 12
Dependent Claim
12 words
A liquid crystalline phase of claim 10, wherein A 1 is ##STR3##
Claim 13
Dependent Claim
15 words
A liquid crystalline phase of claim 9, wherein A 1 is an unsubstituted trans-1,4-cyclohexylene group.
Claim 14
Dependent Claim
16 words
A liquid crystalline phase of claim 1, wherein Ph is 1,4-phenylene or 1,4-phenylene substituted by fluorine.
Claim 15
Dependent Claim
34 words
A liquid crystalline phase of claim 9, wherein, in R 1 , R 2 or R 3 , a CH 2 is replaced by --CH═CH-- in the ω--, (ω-1)-, (ω-2)-, (ω-3)-, (ω-4)-, or (ω-5)-position.
Claim 16
Dependent Claim
16 words
A liquid crystalline phase of claim 1, further comprising at least one nematic or nematogenic compound.
Claim 17
Dependent Claim
108 words
A liquid crystalline phase of claim 15, wherein the nematic or nematogenic compound has the formula R'--L--G--E--R" wherein L and E are independently 1,4-disubstituted benzene, 1,4-disubstituted cyclohexane, 4,4'-disubstituted biphenyl, 4,4'-phenylcyclohexane, 4,4'-cyclohexylcyclohexane, 2,5-disubstituted pyrimidine, 1,3-dioxane, 2,6-disubstituted naphthalene, dihydro naphtnalene tetrahydronaphthalene, quinazoline or tetrahydroquinazoline, ______________________________________
G is --CH═CH--,
--N(O)--N--,
--CH═CY--,
--CH═N(O)--,
--C.tbd.C--, --CH.sub.2 --CH.sub.2 --,
--CO--O--, --CH.sub.2 --O--,
--CO--S--, --CH.sub.2 --S--,
--CH═N--, --COO--Phe--COO--,
______________________________________ or a C-C single bond, Y is chlorine or --CN, and R' and R" are alkyl, alkoxyl, alkanoyloxy, alkoxycarbonyl or alkoxycarbonyloxy having up to 18 carbon atoms, or one of R' or R" is CN, NC, NO 2 , CF 3 , F, Cl or Br.
Claim 18
Dependent Claim
20 words
In a display element, based on a liquid crystal phase, the improvement wherein the phase is one of claim 1.
Claim 19
Dependent Claim
22 words
In an electrooptical display element based in a liquid crystalline dielectric, the improvement wherein the dielectric is a phase of claim 1.
Claim 20
Dependent Claim
171 words
A bicyclooctane derivative of the formula formula R.sup.1 --A.sup.1 --A.sup.2 --R.sup.2 wherein R 1 and R 2 independently are each C 1-12 alkyl, C 1-10 alkoxy or C 1-12 alkyl in which one or two non-adjacent CH 2 groups are replaced by CO, or --CH═CH--, or one of R 1 and R 2 can also be --A 3 --R 3 , A 1 is a 1,4-cyclohexylene group which is unsubstituted or substituted in the 2-, 3- position or a combination thereof by F, Cl, Br, CN, C 1-5 -alkyl, C 1-5 -alkoxy, or C 1-5 perflurinated alkyl, A 2 is a 1,4-bicyclo(2.2.2)octylene group; A 3 is --Cy, --Ph, --Cy--Ph or --Ph--Cy, Cy is 1,4-cyclohexylene or one of the other groups recited for A 1 , Ph is 1,4-phenylene which is unsubstituted, or monosubstituted by F, CH 3 , or a combination thereof, R 3 is C 1-12 alkyl, C 1-10 alkoxy or C 1-12 alkyl wherein one or two non-adjacent CH 2 groups are replaced by CO, O-CO, -CO-O, or -CH═CH-.
Claim 21
Dependent Claim
171 words
A bicyclooctane derivative of the formula formula R.sup.1 --A.sup.1 --A.sup.2 --R.sup.2 wherein R 1 and R 2 independently are each C 1-12 alkyl, C 1-10 alkoxy or C 1-12 alkyl in which one or two non-adjacent CH 2 groups are replaced by CO, or --CH═CH--, or one of R 1 and R 2 can also be --A 3 --R 3 , A 1 is a 1,4-cyclohexylene group which is unsubstituted or substituted in the 2-, 3- position or a combination thereof by F, Cl, Br, CN, C 1-5 -alkyl, C 1-5 -alkoxy, or C 1-5 perflurinated alkyl, A 2 is a 1,4-bicyclo(2.2.2)octylene group; A 3 is --Cy, --Ph, --Cy--Ph or --Ph--Cy, Cy is 1,4-cyclohexylene or one of the other groups recited for A 1 , Ph is 1,4-phenylene which is unsubstituted, or monosubstituted by F, CH 3 , or a combination thereof, R 3 is C 1-12 alkyl, C 1-10 alkoxy or C 1-12 alkyl wherein one or two non-adjacent CH 2 groups are replaced by CO, O-CO, -CO-O, or -CH═CH-.
References Cited (Backward Citations)
US4261652A
Cited
US4330426A
Cited
US4219256A
Cited
US4400061A
Cited
GB2092169A
Cited
US4564694A
Cited
US4482472A
Cited
US4528114A
Cited
US4514317A
Cited
US4478740A
Cited
US4617140A
Cited
US4551264A
Cited
US4510069A
Cited
US4544497A
Cited
US4565425A
Cited
US4622164A
Cited
WO1985001295A1
Cited
US4659502A
Cited
DE3407013A1
Cited
US4663073A
Cited
DE3510434A1
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-11-16 | 1991-05-18 | 1991-11-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-11-16 | 1995-05-18 | 1995-11-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-11-16 | 1999-05-18 | 1999-11-17 | $7700.00 | Window Closed / Lapsed |