Patent US5084204A successfully refreshed from Google Patents.
US5084204A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Naphthylacetylenes
Assignee: Merck Patent GmbH
•
Filing: 1988-11-10
•
Granted: 1992-01-28
•
Expires: 2008-11-10
Abstract
Abstract Naphthylacetylenes of the formula I R.sup.1 --(A.sup.1 --Z.sup.1).sub.m --A.sup.2 --C.tbd.C--A.sup.3 --(Z.sup.2 --A 4 ) n --R 2 I in which R 1 , A 1 , Z 1 , m, A 2 , A 3 , Z 2 , A 4 , n and R 2 have the meanings described herein, are suitable as components of liquid crystal phases.
Inventors
- 👤 Volker Reiffenrath
- 👤 Joachim Krause
- 👤 Georg Weber
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 17:21
CPC Classifications
C; C07; C07C; C07C43/00; C07C43/02; C07C43/20; C07C43/215; C07C13/00; C07C13/28; C07C15/00; C07C15/40; C07C15/56; C07C15/58; C09; C09K; C09K19/00; C09K19/04; C09K19/06; C09K19/32; C09K19/322; C07C2601/00; C07C2601/12; C07C2601/14; C09K2019/325
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
177 words
A naphthyl)acetylene compound of the formula R.sup.1 --A.sup.2 --C.tbd.C--A.sup.3 --R.sup.2 in which R 1 and R 2 are in each case independently of one another an alkyl group or polyfluoroalkyl group having up to 15 C atoms, in which one or more CH 2 groups or CF 2 groups respectively can also be replaced by --O--, --S--, --CO--, --O--CO--, --O--COO--, --CO--O--, --C.tbd.C--, --CH═CH--, --CH-halogen- and --CHCN--, where two heteroatoms are not directly connected with one another, and one of the radicals R 1 and R 2 can also be halogen, CN or NCS; and A 2 and A 3 are in each case independently of one another (a) 2,6-naphthylene radical, (b) 1,2,3,4-tetrahydro-2,6-naphthylene radical, (c) 1,4-phenylene radical, in which one or more CH groups can also be replaced by N, (d) 1,4-cyclohexylene radical, or (e) radical from the group comprising 1,4-cyclohexenylene, 1,4-cyclohexadienylene or 1,4-bicyclo(2.2.2)-octylene, where these radicals (a)-(e) can be substituted one or more times by halogen and/or cyano; with the proviso that at least one of the groups A 2 or A 3 is 2,6-naphthylene or 1,2,3,4-tetrahydro-2,6-naphthylene.
Claim 2
Dependent Claim
177 words
A naphthyl)acetylene compound of the formula R.sup.1 --A.sup.2 --C.tbd.C--A.sup.3 --R.sup.2 in which R 1 and R 2 are in each case independently of one another an alkyl group or polyfluoroalkyl group having up to 15 C atoms, in which one or more CH 2 groups or CF 2 groups respectively can also be replaced by --O--, --S--, --CO--, --O--CO--, --O--COO--, --CO--O--, --C.tbd.C--, --CH═CH--, --CH-halogen- and --CHCN--, where two heteroatoms are not directly connected with one another, and one of the radicals R 1 and R 2 can also be halogen, CN or NCS; and A 2 and A 3 are in each case independently of one another (a) 2,6-naphthylene radical, (b) 1,2,3,4-tetrahydro-2,6-naphthylene radical, (c) 1,4-phenylene radical, in which one or more CH groups can also be replaced by N, (d) 1,4-cyclohexylene radical, or (e) radical from the group comprising 1,4-cyclohexenylene, 1,4-cyclohexadienylene or 1,4-bicyclo(2.2.2)-octylene, where these radicals (a)-(e) can be substituted one or more times by halogen and/or cyano; with the proviso that at least one of the groups A 2 or A 3 is 2,6-naphthylene or 1,2,3,4-tetrahydro-2,6-naphthylene.
Claim 3
Dependent Claim
27 words
In a liquid crystal phase having at least two liquid crystal components, the improvement wherein at least one component is a naphthyl)acetylene compound according to claim 1.
Claim 4
Dependent Claim
24 words
In a liquid crystal display element comprising a liquid crystal phase, the improvement wherein the liquid crystal phase is one according to claim 2.
Claim 5
Dependent Claim
75 words
A compound according to claim 1 of the formulae Iaa to Iag: R.sup.1 --Nap--C.tbd.C--Phe--R.sup.2 Iaa R.sup.1 --Nap--C.tbd.C--Cyc--R.sup.2 Iab R.sup.1 --Nap--C.tbd.C--Che--R.sup.2 Iac R.sup.1 --Nap--C.tbd.C--Cha--R.sup.2 Iad R.sup.1 --Nap--C.tbd.C--Pyd--R.sup.2 Iae R.sup.1 --Nap--C.tbd.C--Pyr--R.sup.2 Iaf R.sup.1 --Tet--C.tbd.C--Phe--R.sup.2 Iag, wherein Nap is a 2,6-naphthylene group, Phe is a 1,4-phenylene group, Cyc is a 1,4-cyclohexylene group, Tet is a 1,2,3,4-tetrahydro-2,6-naphthylene group, Pyd is a pyridine-2,5-diyl group, Pyr is a pyrimidine-2,5-diyl group, Che is a 1,4-cyclohexylene group, and Cha is a 1,4-cyclohexadienylene group.
Claim 6
Dependent Claim
51 words
A compound according to claim 1 of the formulae 1 to 6: Alkyl--Nap--C.tbd.C--Phe--Alkyl 1 Alkoxy--Nap--C.tbd.C--Phe--Alkyl 2 Alkyl--Nap--C.tbd.C--Cyc--Alkyl 3 Alkoxy--Nap--C.tbd.C--Cyc--Alkyl 4 Alkoxy--Nap--C.tbd.C--Pyd--Alkyl 5 Alkyl--Nap--C.tbd.C--Pyr--Alkyl 6, wherein Nap is a 2,6-naphthylene group, Phe is a 1,4-phenylene group, Cyc is a 1,4-cyclohexylene group, Pyd is a pyridine-2,5-diyl group, and Pyr is a pyrimidine-2,5-diyl group.
Claim 7
Dependent Claim
17 words
A compound according to claim 1, wherein R 1 and R 2 independently have 2-10 C atoms.
Claim 8
Dependent Claim
20 words
A compound according to claim 1, wherein neither of the radicals R 1 and R 2 is halogen or CN.
Claim 9
Dependent Claim
17 words
A compound according to claim 7, wherein R 1 and R 2 together have 4-16 C atoms.
Claim 10
Dependent Claim
16 words
A compound according to claim 1, wherein one of A 2 or A 3 is 2,6-naphthylene.
Claim 11
Dependent Claim
59 words
A compound according to claim 1, wherein A 2 and A 3 are independently Cyc, Phe, Nap, Pyd, Tet, Pyr or Che, wherein Nap is a 2,6-naphthylene group, Phe is a 1,4-phenylene group, Cyc is a 1,4-cyclohexylene group, Tet is a 1,2,3,4-tetrahydro-2,6-naphthylene group, Pyd is a pyridine-2,5-diyl group, Pyr is a pyrimidine-2,5-diyl group, and Che is a 1,4-cyclohexylene group.
Claim 12
Dependent Claim
27 words
A compound according to claim 1, wherein A 2 or A 3 is a 1,2,3,4 tetrahydro-2,6-naphthylene group and is attached to the acetylene group at the 6-position.
Claim 13
Dependent Claim
15 words
A compound according to claim 1, wherein the 1,4-cyclohexylene radical has the following structure: ##STR4##
Claim 14
Dependent Claim
15 words
A compound according to claim 1, wherein the 1,4-cyclohexadienylene radical has the following structure: ##STR5##
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1995-01-27 | 1995-07-29 | 1996-01-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-01-27 | 1999-07-29 | 2000-01-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-01-27 | 2003-07-29 | 2004-01-28 | $7700.00 | Window Closed / Lapsed |