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US4734218A
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Dichroic azo dyestuffs and liquid crystal composition containing said dyestuffs
Assignee: Mitsui Chemicals Inc
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Filing: 1985-11-19
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Granted: 1988-03-29
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Expires: 2005-11-19
Abstract
Abstract PCT No. PCT/JP85/00644 Sec. 371 Date Jul. 18, 1986 Sec. 102(e) Date Jul. 18, 1986 PCT Filed Nov. 19, 1985 PCT Pub. No. WO86/03215 PCT Pub. Date Jun. 5, 1986.Provided are novel dichroic azo dyestuffs, which contain skeletons represented by the following general formula: <IMAGE> at one terminals of the long axes of the molecules of the azo dyestuffs, and liquid crystal compositions containing the dichroic azo dyestuffs in forms dissolved in liquid crystals. These dichroic azo dyestuffs have large dichroic ratios and high durability, and their compositions are employed as useful display devices.
Inventors
- 👤 Keisuke Takuma
- 👤 Kimitoshi Kato
- 👤 Hiroshi Aiga
- 👤 Yasuyuki Yamada
- 👤 Tsutomu Nishizawa
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 22:14
CPC Classifications
C; C09; C09K; C09K19/00; C09K19/52; C09K19/60; C09K19/601; C09B; C09B31/00; C09B31/02; C09B31/16; C09B56/00; C09B56/02
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
191 words
A dichroic azo dyestuff represented by the following formula: ##STR175## wherein A is --CN, --COOR 1 , ##STR176## R 1 is alkyl, alkoxyalkyl, phenyl, cyclohexyl, or phenyl or cyclohexyl which are substituted with alkyl or alkoxy at the p-position thereof; R 2 and R 3 are individually hydrogen alkyl, cycloalkyl, alkoxy, alkoxyalkoxy, cycloalkyloxyalkoxy, aryloxyalkoxy, aryl, halogen, cyano or dialkylamino; Y 1 and Y 2 are individually hydrogen, halogen, alkyl, alkoxy, cyano or hydroxyl; Ar 1 and Ar 2 are individually ##STR177## W 1 and W 2 are individually --N═N-- or --N═CH--, but W 1 is --N═N-- when W 2 is --N═CH--, m is 0 or 1, but m is 0 when W 1 is --N═CH--; and B is hydroxyl, alkoxy, alkoxyalkoxy, p-alkylbenzyloxy, ##STR178## but B is hydrogen, halogen, cyano, ##STR179## when W 1 or W 2 is --N═CN--, R 4 is alkyl, phenyl or cyclohexyl unsubstituted or substituted with alkyl or alkoxy at the p-position thereof, R 5 is hydrogen or alkyl, R 6 is alkyl or ##STR180## R 7 and R 8 are individually hydrogen, halogen, hydroxyl, cyano, alkyl, dialkylamino, alkoxy, alkoxyalkoxy, ##STR181## and R 9 is hydrogen or alkyl.
Claim 2
Dependent Claim
191 words
A dichroic azo dyestuff represented by the following formula: ##STR175## wherein A is --CN, --COOR 1 , ##STR176## R 1 is alkyl, alkoxyalkyl, phenyl, cyclohexyl, or phenyl or cyclohexyl which are substituted with alkyl or alkoxy at the p-position thereof; R 2 and R 3 are individually hydrogen alkyl, cycloalkyl, alkoxy, alkoxyalkoxy, cycloalkyloxyalkoxy, aryloxyalkoxy, aryl, halogen, cyano or dialkylamino; Y 1 and Y 2 are individually hydrogen, halogen, alkyl, alkoxy, cyano or hydroxyl; Ar 1 and Ar 2 are individually ##STR177## W 1 and W 2 are individually --N═N-- or --N═CH--, but W 1 is --N═N-- when W 2 is --N═CH--, m is 0 or 1, but m is 0 when W 1 is --N═CH--; and B is hydroxyl, alkoxy, alkoxyalkoxy, p-alkylbenzyloxy, ##STR178## but B is hydrogen, halogen, cyano, ##STR179## when W 1 or W 2 is --N═CN--, R 4 is alkyl, phenyl or cyclohexyl unsubstituted or substituted with alkyl or alkoxy at the p-position thereof, R 5 is hydrogen or alkyl, R 6 is alkyl or ##STR180## R 7 and R 8 are individually hydrogen, halogen, hydroxyl, cyano, alkyl, dialkylamino, alkoxy, alkoxyalkoxy, ##STR181## and R 9 is hydrogen or alkyl.
Claim 3
Dependent Claim
13 words
The dichroic azo dyestuff as claimed in claim 1, wherein A is --CN.
Claim 4
Dependent Claim
15 words
The dichroic azo dyestuff as claimed in claim 1, wherein A is --COOR 1 .
Claim 5
Dependent Claim
13 words
The dichroic azo dyestuff as claimed in claim 1, wherein A is ##STR182##
Claim 6
Dependent Claim
13 words
The dichroic azo dyestuff as claimed in claim 1, wherein A is ##STR183##
Claim 7
Dependent Claim
77 words
The dichroic azo dyestuff as claimed in claim 1, wherein R 1 is --CH 3 , --C 2 H 5 , --(CH 2 ) 3 CH 3 , --(CH 2 ) 7 CH 3 , --C 2 H 4 CH(CH 3 )CH 2 --(CH 3 ) 3 , --(CH 2 ) 10 CH 3 , ##STR184## --C 2 H 4 OC 2 H 5 , or --C 2 H 4 O(CH 2 ) 3 CH 3 .
Claim 8
Dependent Claim
23 words
A dichroic azo dyestuff as claimed in claim 1 or 2, wherein the carbon number of each alkyl group is 15 or smaller.
Claim 9
Dependent Claim
90 words
A dichroic azo dyestuff as claimed in claim 1, wherein R 2 and R 3 are individually a hydrogen atom, --CH 3 , --C 2 H 5 , --(CH 2 ) 2 CH 3 , --CH(CH 3 ) 2 , --(CH 2 ) 7 CH 3 , --CH 2 C(CH 3 ) 3 , --(CH 2 ) 10 CH 3 , --OCH 3 , --OC 2 H 5 , --O(CH 2 ) 7 CH 3 , --OC 2 H 4 CH(CH 3 )CH 2 C(CH 3 ) 3 , ##STR185##
Claim 10
Dependent Claim
32 words
The dichroic azo dyestuff as claimed in claim 1, wherein Y 1 and Y 2 are individually a hydrogen atom, --Cl, --Br, --I, --F, --CN, --OH, --OCH 3 or --CH 3 .
Claim 11
Dependent Claim
19 words
The dichroic azo dyestuff as claimed in claim 1, wherein Y 1 and Y 2 are both hydrogen atoms.
Claim 12
Dependent Claim
18 words
The dichroic azo dyestuff as claimed in claim 1, wherein Ar 1 and Ar 2 are individually ##STR186##
Claim 13
Dependent Claim
99 words
The dichroic azo dyestuff as claimed in claim 1, wherein B is a hydroxyl, --OCH 3 , --OC 2 H 5 , --OC 4 H 9 (n), --OC(CH 3 ) 3 , --O(CH 2 ) 5 CH 3 , --O(CH 2 ) 7 CH 3 , --OC 2 H 4 CH(CH 3 )CH 2 C(CH 3 ) 3 , --O(CH 2 ) 12 CH 3 , --OCH 2 CH 2 OC 2 H 5 , --OCH 2 CH 2 OCH 2 CH(CH 3 ) 2 , ##STR187## --N(CH 3 ) 2 or --N(C 2 H 5 ) 2 .
Claim 14
Dependent Claim
62 words
The dichroic azo dyestuff as claimed in claim 1, wherein when B is represented by ##STR188## R 4 is --CH 3 , --C 2 H 5 , --(CH 2 ) 3 CH 3 , --(CH 2 ) 7 CH 3 , --C 2 H 4 CH(CH 3 )CH 2 --(CH 3 ) 3 , --(CH 2 ) 10 CH 3 , ##STR189##
Claim 15
Dependent Claim
35 words
The dichroic azo dyestuff as claimed in claim 1, wherein when B is represented by ##STR190## R 5 is a hydrogen atom, --CH 3 , --C 2 H 5 or --C 4 H 9 .
Claim 16
Dependent Claim
40 words
The dichroic azo dyestuff as claimed in claim 1, wherein when B is represented by ##STR191## R 6 is --CH 3 , --C 2 H 5 , --C 4 H 9 (n), --CH 2 CH(CH 3 ) 2 , ##STR192##
Claim 17
Dependent Claim
207 words
A liquid crystal composition containing, in a form dissolved in a liquid crystal, at least one of dichroic azo dyestuffs represented by the following formula: ##STR193## wherein A is --CN, --COOR 1 , ##STR194## R 1 is alkyl, alkoxyalkyl, phenyl, cyclohexyl, or phenyl or cyclohexyl which are substituted with alkyl or alkoxy at the p-position thereof; R 2 and R 3 are individually hydrogen, alkyl, cycloalkyl, alkoxy, alkoxyalkoxy, cycloalkyloxyalkoxy, aryloxyalkoxy, aryl, halogen, cyano or dialkylamino; Y 1 and Y 2 denote individually hydrogen; halogen, alkyl, alkoxy, cyano or hydroxyl; Ar 1 and Ar 2 are individually ##STR195## W 1 and W 2 are individually --N═N-- or --N═CH--, but W 1 is --N═N-- when W 2 is --N═CH--, m is 0 or 1, but m is 0 when W 1 is --N═CH--; and B is hydroxyl, alkoxy, alkoxyalkoxy, p-alkylbenzyloxy, ##STR196## but B is hydrogen, halogen, cyano, ##STR197## when W 1 or W 2 is --N═CN--, R 4 is alkyl, phenyl or cyclohexyl unsubstituted or substituted with alkyl or alkoxy at the p-position thereof, R 5 is hydrogen or alkyl, R 6 is alkyl or ##STR198## R 7 and R 8 are individually hydrogen, halogen, hydroxyl, cyano, alkyl, dialkylamino, alkoxy, alkoxyalkoxy, ##STR199## and R 9 is hydrogen or alkyl.
Claim 18
Dependent Claim
207 words
A liquid crystal composition containing, in a form dissolved in a liquid crystal, at least one of dichroic azo dyestuffs represented by the following formula: ##STR193## wherein A is --CN, --COOR 1 , ##STR194## R 1 is alkyl, alkoxyalkyl, phenyl, cyclohexyl, or phenyl or cyclohexyl which are substituted with alkyl or alkoxy at the p-position thereof; R 2 and R 3 are individually hydrogen, alkyl, cycloalkyl, alkoxy, alkoxyalkoxy, cycloalkyloxyalkoxy, aryloxyalkoxy, aryl, halogen, cyano or dialkylamino; Y 1 and Y 2 denote individually hydrogen; halogen, alkyl, alkoxy, cyano or hydroxyl; Ar 1 and Ar 2 are individually ##STR195## W 1 and W 2 are individually --N═N-- or --N═CH--, but W 1 is --N═N-- when W 2 is --N═CH--, m is 0 or 1, but m is 0 when W 1 is --N═CH--; and B is hydroxyl, alkoxy, alkoxyalkoxy, p-alkylbenzyloxy, ##STR196## but B is hydrogen, halogen, cyano, ##STR197## when W 1 or W 2 is --N═CN--, R 4 is alkyl, phenyl or cyclohexyl unsubstituted or substituted with alkyl or alkoxy at the p-position thereof, R 5 is hydrogen or alkyl, R 6 is alkyl or ##STR198## R 7 and R 8 are individually hydrogen, halogen, hydroxyl, cyano, alkyl, dialkylamino, alkoxy, alkoxyalkoxy, ##STR199## and R 9 is hydrogen or alkyl.
Claim 19
Dependent Claim
26 words
The composition as claimed in claim 16, wherein the concentration of the dichroic azo dyestuff in the liquid crystal composition is a concentration of 0.01-10 wt.%.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-03-29 | 1991-09-28 | 1992-03-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-03-29 | 1995-09-28 | 1996-03-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-03-29 | 1999-09-28 | 2000-03-29 | $7700.00 | Window Closed / Lapsed |