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US5248447A Expired / Lapsed US ⏱️ 0.0 years remaining

2,3-difluorohydroquinone derivatives

Assignee: Merck Patent GmbH
•
Filing: 1989-02-27
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Granted: 1993-09-28
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Expires: 2009-02-27
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Abstract

Abstract 2,3-difluorohydroquinone compounds of the formula I ##STR1## in which R 1 and R 2 , in each case independently of one another, are alkyl having 1 to 15 C atoms or alkenyl having 3 to 15 C atoms which are unsubstituted, monosubstituted by cyano or at least monosubstituted by fluorine or chlorine, it also being possible for one CH 2 group in these radicals to be replaced by --O--, --CO--, --CO--O--, --O--CO-- or --O--CO--O--, A 1 , A 2 and A 3 , in each case independently of one another, are (a) trans-1,4-cyclohexylene, in which, in addition, one or two non-adjacent CH 2 groups may be replaced by --O-- and/or --S--, (b) 1,4-phenylene, in which, in addition, one or two CH groups may be replaced by N, or (c) a radical from the group comprising piperidine-1,4-diyl, 1,4-bicylo (2,2,2)-octylene (sic), 1,3,4-thiadiazole-2,5-diyl, napththalene-2,6-diyl, decahydronaphthalene-2,6-diyl and 1,2,3,4-tetrahydronaphthalene-2,6-diyl, it being possible for the radicals (a) and (b) to be monosubstituted or polysubstituted by F, Cl, CH 3 or CN, Z 1 is --CO--O--, --O--CO--, --CH 2 CH 2 --, --OCH 2 --, --CH 2 O--, --C.tbd.C-- or a single bond, Q 1 and Q 2 , in each case independently of one another, are --CO-- or --CH 2 --, m and n are each 0, 1 or 2, and (m+n) is 0, 1 or 2, are suitable as components of liquid-crystalline phases.

Inventors

  • 👤 Volker Reiffenrath
  • 👤 Joachim Krause
  • 👤 Andreas Wachtler
  • 👤 Georg Weber
  • 👤 Thomas Geelhaar
  • 👤 David Coates
  • 👤 Ian C. Sage
  • 👤 Simon Greenfield

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-06 14:39
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/02; C07D239/24; C07D239/26; C07C; C07C43/00; C07C43/02; C07C43/20; C07C43/225; C09; C09K; C09K19/00; C09K19/04; C09K19/06; C09K19/08; C09K19/10; C09K19/20; C09K19/2007; C09K19/2021; C09K19/30; C09K19/3001; C09K19/3066; C09K19/3068; C09K19/34; C09K19/3441; C09K19/345; C09K19/3458; C07C2601/00; C07C2601/12; C07C2601/14; C09K19/0403; C09K2019/0407

Claims Analysis

Total Claims: 19
Claim 1
Independent Claim 146 words
A 2,3-difluorohydroquinone compound of the formula I, ##STR6## wherein R 1 and R 2 , in each case independently of one another, are alkyl having 1 to 15 C atoms or a alkenyl having 3 to 15 C atoms which are unsubstituted, monosubstituted by cyano or at least monosubstituted by fluorine or chlorine, it also being possible for one CH 2 group in these radicals to be replaced by --O--, --CO--, --CO--O--, --O--CO-- or --O--CO--O--; A 1 , A 2 and A 3 in each case are independently trans-1,4-cyclohexylene; Z 1 is --CO--O--, --O--CO--, --CH 2 --CH 2 13 , --OCH 2 --, --CH 2 O--, --C.tbd.C-- or a single bond; Q 1 and Q 2 , in each case independently of one another, are --CO-- or --CH 2 --; m and n are each 0, 1 or 2; and (m+n) is 0, 1 or 2.
Claim 2
Dependent Claim 146 words
A 2,3-difluorohydroquinone compound of the formula I, ##STR6## wherein R 1 and R 2 , in each case independently of one another, are alkyl having 1 to 15 C atoms or a alkenyl having 3 to 15 C atoms which are unsubstituted, monosubstituted by cyano or at least monosubstituted by fluorine or chlorine, it also being possible for one CH 2 group in these radicals to be replaced by --O--, --CO--, --CO--O--, --O--CO-- or --O--CO--O--; A 1 , A 2 and A 3 in each case are independently trans-1,4-cyclohexylene; Z 1 is --CO--O--, --O--CO--, --CH 2 --CH 2 13 , --OCH 2 --, --CH 2 O--, --C.tbd.C-- or a single bond; Q 1 and Q 2 , in each case independently of one another, are --CO-- or --CH 2 --; m and n are each 0, 1 or 2; and (m+n) is 0, 1 or 2.
Claim 3
Dependent Claim 25 words
A 2,3-difluorohydroquinone compound of claim 1, wherein m is 0 or 1 and Z 1 is --CH 2 CH 2 -- or a single bond.
Claim 4
Dependent Claim 28 words
A 2,3-difluorohydroquinone compound of claim 1, wherein R 1 and R 2 in each case are, independently of one another, straight-chain alkyl of 2 to 7 C atoms.
Claim 5
Dependent Claim 10 words
A 2,3-difluorohydroquinone compound of claim 1, wherein n is 0.
Claim 6
Dependent Claim 12 words
A 2,3-difluorohydroquinone compound of claim 4, wherein m is 1 or 2.
Claim 7
Dependent Claim 47 words
A 2,3-difluorohydroquinone compound, wherein said compound is: 2,3-difluoro-4-ethoxyphenyl trans-4-pentylcyclohexanoate, 2,3-difluoro-4-ethoxyphenyl trans-4-propylcyclohexanoate, 2,3-difluoro-4-ethoxyphenyl trans-4-ethylcyclohexanoate,, 2,3-difluoro-4-ethoxyphenyl trans-4-butylcyclohexanoate, 2,3-difluoro-4-ethoxyphenyl trans-4-heptylcyclohexanoate, 2,3-difluoro-4-methoxyphenyl trans-4-ethylcyclohexanoate, 2,3-difluoro-4-methoxyphenyl trans-4-propylcyclohexanoate, 2,3-difluoro-4-methoxyphenyl trans-4-butylcyclohexanoate, 2,3-difluoro-4-methoxyphenyl trans-4-pentylcyclohexanoate, 2,3-difluoro-4-methoxyphenyl trans-4-heptylcyclohexanoate, 2,3-difluoro-4-propoxyphenyl trans-4-ethylcyclohexanoate, 2,3-difluoro-4-propoxyphenyl trans-4-propylcyclohexanoate, 2,3-difluoro-4-propoxyphenyl trans-4-butylcyclohexanoate, 2,3-difluoro-4-propoxyphenyl trans-4-pentylcyclohexanoate, 2,3-difluoro-4-propoxyphenyl trans-4-heptylcyclohexanoate, 2,3-difluoro-4-butoxyphenyl trans-4-ethylcyclohexanoate, 2,3-difluoro-4-butoxyphenyl trans-4-propylcyclohexanoate, 2,3-difluoro-4-butoxyphenyl trans-4-butylcyclohexanoate, 2,3-difluoro-4-butoxyphenyl trans-4-pentylcyclohexanoate, 2,3-difluoro-4-butoxyphenyl trans-4-heptylcyclohexanoate,
Claim 8
Dependent Claim 47 words
A 2,3-difluorohydroquinone compound, wherein said compound is: 2,3-difluoro-4-ethoxyphenyl trans-4-pentylcyclohexanoate, 2,3-difluoro-4-ethoxyphenyl trans-4-propylcyclohexanoate, 2,3-difluoro-4-ethoxyphenyl trans-4-ethylcyclohexanoate,, 2,3-difluoro-4-ethoxyphenyl trans-4-butylcyclohexanoate, 2,3-difluoro-4-ethoxyphenyl trans-4-heptylcyclohexanoate, 2,3-difluoro-4-methoxyphenyl trans-4-ethylcyclohexanoate, 2,3-difluoro-4-methoxyphenyl trans-4-propylcyclohexanoate, 2,3-difluoro-4-methoxyphenyl trans-4-butylcyclohexanoate, 2,3-difluoro-4-methoxyphenyl trans-4-pentylcyclohexanoate, 2,3-difluoro-4-methoxyphenyl trans-4-heptylcyclohexanoate, 2,3-difluoro-4-propoxyphenyl trans-4-ethylcyclohexanoate, 2,3-difluoro-4-propoxyphenyl trans-4-propylcyclohexanoate, 2,3-difluoro-4-propoxyphenyl trans-4-butylcyclohexanoate, 2,3-difluoro-4-propoxyphenyl trans-4-pentylcyclohexanoate, 2,3-difluoro-4-propoxyphenyl trans-4-heptylcyclohexanoate, 2,3-difluoro-4-butoxyphenyl trans-4-ethylcyclohexanoate, 2,3-difluoro-4-butoxyphenyl trans-4-propylcyclohexanoate, 2,3-difluoro-4-butoxyphenyl trans-4-butylcyclohexanoate, 2,3-difluoro-4-butoxyphenyl trans-4-pentylcyclohexanoate, 2,3-difluoro-4-butoxyphenyl trans-4-heptylcyclohexanoate,
Claim 9
Dependent Claim 38 words
3-difluoro-4-hexoxyphenyl trans-4-ethylcyclohexanoate, 2,3-difluoro-4-hexoxyphenyl trans-4-propylcyclohexanoate, 2,3-difluoro-4-hexoxyphenyl trans-4-butylcyclohexanoate, 2,3-difluoro-4-hexoxyphenyl trans-4-pentylcyclohexanoate, 2,3-difluoro-4-hexoxyphenyl trans-4-heptylcyclohexanoate, 2,3-difluoro-4-octoxyphenyl trans-4-ethylcyclohexanoate, 2,3-difluoro-4-octoxyphenyl trans-4-propylcyclohexanoate, 2,3-difluoro-4-octoxyphenyl trans-4-butylcyclohexanoate, 2,3-difluoro-4-octoxyphenyl trans-4-heptylcyclohexanoate, 2,3-difluoro-4-ethoxyphenyl trans-4-(trans-4-propylcyclohexyl)-cyclohexanoate, 2,3-difluoro-4-ethoxyphenyl trans-4-(trans-4-ethylcyclohexyl)-cyclohexanoate, 2,3-difluoro-4-ethoxyphenyl trans-4-(trans-4-butylcyclohexyl)-cyclohexanoate, 2,3-difluoro-4-ethoxyphenyl trans-4-(trans-4-pentylcyclohexyl)-cyclohexanoate, 2,3-difluoro-4-ethoxyphenyl trans-4-(trans-4-heptylcyclohexyl)-cyclohexanoate, 2,3-difluoro-4-methoxyphenyl trans-4-(trans-4-ethylcyclohexyl)-cyclohexanoate, 2,3-difluoro-4-methoxyphenyl trans-4-(trans-4-propylcyclohexyl)-cyclohexanoate, 2,3-difluoro-4-methoxyphenyl trans-4-(trans-4-butylcyclohexyl)-cyclohexanoate, 2,3-difluoro-4-methoxyphenyl trans-4-(trans-4-pentylcyclohexyl)-cyclohexanoate, 2,3-difluoro-4-methoxyphenyl trans-4-(trans-4-heptylcyclohexyl)-cyclohexanoate,
Claim 10
Dependent Claim 38 words
3-difluoro-4-hexoxyphenyl trans-4-ethylcyclohexanoate, 2,3-difluoro-4-hexoxyphenyl trans-4-propylcyclohexanoate, 2,3-difluoro-4-hexoxyphenyl trans-4-butylcyclohexanoate, 2,3-difluoro-4-hexoxyphenyl trans-4-pentylcyclohexanoate, 2,3-difluoro-4-hexoxyphenyl trans-4-heptylcyclohexanoate, 2,3-difluoro-4-octoxyphenyl trans-4-ethylcyclohexanoate, 2,3-difluoro-4-octoxyphenyl trans-4-propylcyclohexanoate, 2,3-difluoro-4-octoxyphenyl trans-4-butylcyclohexanoate, 2,3-difluoro-4-octoxyphenyl trans-4-heptylcyclohexanoate, 2,3-difluoro-4-ethoxyphenyl trans-4-(trans-4-propylcyclohexyl)-cyclohexanoate, 2,3-difluoro-4-ethoxyphenyl trans-4-(trans-4-ethylcyclohexyl)-cyclohexanoate, 2,3-difluoro-4-ethoxyphenyl trans-4-(trans-4-butylcyclohexyl)-cyclohexanoate, 2,3-difluoro-4-ethoxyphenyl trans-4-(trans-4-pentylcyclohexyl)-cyclohexanoate, 2,3-difluoro-4-ethoxyphenyl trans-4-(trans-4-heptylcyclohexyl)-cyclohexanoate, 2,3-difluoro-4-methoxyphenyl trans-4-(trans-4-ethylcyclohexyl)-cyclohexanoate, 2,3-difluoro-4-methoxyphenyl trans-4-(trans-4-propylcyclohexyl)-cyclohexanoate, 2,3-difluoro-4-methoxyphenyl trans-4-(trans-4-butylcyclohexyl)-cyclohexanoate, 2,3-difluoro-4-methoxyphenyl trans-4-(trans-4-pentylcyclohexyl)-cyclohexanoate, 2,3-difluoro-4-methoxyphenyl trans-4-(trans-4-heptylcyclohexyl)-cyclohexanoate,
Claim 11
Dependent Claim 21 words
3-difluoro-4-propoxyphenyl trans-4-(trans-4-ethylcyclohexyl)-cyclohexanoate, 2,3-difluoro-4-propoxyphenyl trans-4-(trans-4-propylcyclohexyl)-cyclohexanoate, 2,3-difluoro-4-propoxyphenyl trans-4-(trans-4-butylcyclohexyl)-cyclohexanoate, 2,3-difluoro-4-propoxyphenyl trans-4-(trans-4-pentylcyclohexyl)-cyclohexanoate, 2,3-difluoro-4-propoxyphenyl trans-4-(trans-4-heptylcyclohexyl)-cyclohexanoate, 2,3-difluoro-4-butoxyphenyl trans-4-(trans-4-ethylcyclohexyl)-cyclohexanoate, 2,3-difluoro-4-butoxyphenyl trans-4-(trans-4-propylcyclohexyl)-cyclohexanoate, 2,3-difluoro-4-butoxyphenyl trans-4-(trans-4-butylcyclohexyl)-cyclohexanoate, 2,3-difluoro-4-butoxyphenyl trans-4-(trans-4-pentylcyclohexyl)-cyclohexanoate, or 2,3-difluoro-4-butoxyphenyl trans-4-(trans-4-heptylcyclohexyl)-cyclohexanoate.
Claim 12
Dependent Claim 21 words
3-difluoro-4-propoxyphenyl trans-4-(trans-4-ethylcyclohexyl)-cyclohexanoate, 2,3-difluoro-4-propoxyphenyl trans-4-(trans-4-propylcyclohexyl)-cyclohexanoate, 2,3-difluoro-4-propoxyphenyl trans-4-(trans-4-butylcyclohexyl)-cyclohexanoate, 2,3-difluoro-4-propoxyphenyl trans-4-(trans-4-pentylcyclohexyl)-cyclohexanoate, 2,3-difluoro-4-propoxyphenyl trans-4-(trans-4-heptylcyclohexyl)-cyclohexanoate, 2,3-difluoro-4-butoxyphenyl trans-4-(trans-4-ethylcyclohexyl)-cyclohexanoate, 2,3-difluoro-4-butoxyphenyl trans-4-(trans-4-propylcyclohexyl)-cyclohexanoate, 2,3-difluoro-4-butoxyphenyl trans-4-(trans-4-butylcyclohexyl)-cyclohexanoate, 2,3-difluoro-4-butoxyphenyl trans-4-(trans-4-pentylcyclohexyl)-cyclohexanoate, or 2,3-difluoro-4-butoxyphenyl trans-4-(trans-4-heptylcyclohexyl)-cyclohexanoate.
Claim 13
Dependent Claim 20 words
A 2,3-difluorohydroquinone compound of claim 1, wherein at least one of Q 1 and Q 2 is --CH 2 --.
Claim 14
Dependent Claim 13 words
A 2,3-difluorohydroquinone compound of claim 1, wherein Q 1 is --CH 2 --.
Claim 15
Dependent Claim 20 words
A 2,3-difluorohydroquinone compound of claim 1, wherein at least one of R 1 and R 2 is alkenyl or oxaalkyl.
Claim 16
Dependent Claim 24 words
In a liquid-crystalline medium comprising at least two liquid-crystalline components, the improvement wherein at least one component is a compound according to claim 6.
Claim 17
Dependent Claim 20 words
In an electrooptical display element, comprising a dielectric, the improvement wherein said dielectric is a medium according to claim 10.
Claim 18
Dependent Claim 24 words
In a liquid-crystalline medium comprising at least two liquid-crystalline components, the improvement wherein at least one component is a compound according to claim 1.
Claim 19
Dependent Claim 20 words
In an electrooptical display element, comprising a dielectric, the improvement wherein said dielectric is a medium according to claim 12.

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