CH624705A5 - - Google Patents
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- Publication number
- CH624705A5 CH624705A5 CH777076A CH777076A CH624705A5 CH 624705 A5 CH624705 A5 CH 624705A5 CH 777076 A CH777076 A CH 777076A CH 777076 A CH777076 A CH 777076A CH 624705 A5 CH624705 A5 CH 624705A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- compound
- methyl
- liquid crystal
- hydrogen
- Prior art date
Links
- 239000004973 liquid crystal related substance Substances 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000000463 material Substances 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 230000005684 electric field Effects 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 101100234408 Danio rerio kif7 gene Proteins 0.000 claims description 2
- 101100221620 Drosophila melanogaster cos gene Proteins 0.000 claims description 2
- 101100398237 Xenopus tropicalis kif11 gene Proteins 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 5
- 229910052801 chlorine Inorganic materials 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 2
- 239000000969 carrier Substances 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 239000012777 electrically insulating material Substances 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000000956 methoxy group Chemical class [H]C([H])([H])O* 0.000 claims 1
- 239000000975 dye Substances 0.000 description 56
- 239000000243 solution Substances 0.000 description 30
- 238000000034 method Methods 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 230000007704 transition Effects 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- -1 lithium aluminum hydride Chemical compound 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 150000002828 nitro derivatives Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 230000003098 cholesteric effect Effects 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000001005 nitro dye Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- TZTDJBMGPQLSLI-UHFFFAOYSA-N (4-nitrophenyl)-phenyldiazene Chemical compound C1=CC([N+](=O)[O-])=CC=C1N=NC1=CC=CC=C1 TZTDJBMGPQLSLI-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- NSGVPXKWKUZSAY-UHFFFAOYSA-N 1-nitro-2-nitrosobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1N=O NSGVPXKWKUZSAY-UHFFFAOYSA-N 0.000 description 1
- IDZTUECABAHWLE-UHFFFAOYSA-N 1-nitro-4-nitrosobenzene Chemical compound [O-][N+](=O)C1=CC=C(N=O)C=C1 IDZTUECABAHWLE-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- WLPATYNQCGVFFH-UHFFFAOYSA-N 2-phenylbenzonitrile Chemical group N#CC1=CC=CC=C1C1=CC=CC=C1 WLPATYNQCGVFFH-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- QPQKUYVSJWQSDY-UHFFFAOYSA-N 4-phenyldiazenylaniline Chemical class C1=CC(N)=CC=C1N=NC1=CC=CC=C1 QPQKUYVSJWQSDY-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- NRJPVIOTANUINF-UHFFFAOYSA-N chembl2204743 Chemical class C1=CC(O)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1 NRJPVIOTANUINF-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- WCLNGBQPTVENHV-MKQVXYPISA-N cholesteryl nonanoate Chemical compound C([C@@H]12)C[C@]3(C)[C@@H]([C@H](C)CCCC(C)C)CC[C@H]3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)CCCCCCCC)C1 WCLNGBQPTVENHV-MKQVXYPISA-N 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- NLRKCXQQSUWLCH-UHFFFAOYSA-N nitrosobenzene Chemical compound O=NC1=CC=CC=C1 NLRKCXQQSUWLCH-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/08—Preparation of azo dyes from other azo compounds by reduction
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0083—Solutions of dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/60—Pleochroic dyes
- C09K19/601—Azoic
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S534/00—Organic compounds -- part of the class 532-570 series
- Y10S534/02—Azo compounds containing chains of eight or more carbon atoms not provided for elsewhere in this class
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Liquid Crystal (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2584375A GB1555954A (en) | 1975-06-17 | 1975-06-17 | Solutions of pleochroic azo dye in liquid crystal material and devices incorporating such solutions |
GB2585975A GB1555955A (en) | 1975-06-17 | 1975-06-17 | Solutions of pleochroic azo dye in liquid crystals material and devices incorporating such solutions |
GB5339775 | 1975-12-31 | ||
GB5339875 | 1975-12-31 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH624705A5 true CH624705A5 (ja) | 1981-08-14 |
Family
ID=27448672
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH777076A CH624705A5 (ja) | 1975-06-17 | 1976-06-17 |
Country Status (5)
Country | Link |
---|---|
US (1) | US4145114A (ja) |
JP (1) | JPS522885A (ja) |
CH (1) | CH624705A5 (ja) |
DE (1) | DE2627215C2 (ja) |
FR (1) | FR2438676A1 (ja) |
Families Citing this family (68)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH594897A5 (ja) * | 1976-06-23 | 1978-01-31 | Bbc Brown Boveri & Cie | |
US4128496A (en) * | 1976-09-09 | 1978-12-05 | General Electric Company | Dichroic liquid crystal compositions |
US4128497A (en) * | 1976-09-09 | 1978-12-05 | General Electric Company | Dichroic liquid crystal compositions |
US4179395A (en) * | 1976-09-09 | 1979-12-18 | General Electric Company | Dichroic dyes having a plurality of azo bonding groups |
US4208106A (en) * | 1976-09-27 | 1980-06-17 | Beckman Instruments, Inc. | Fluorescent displays |
US4122027A (en) * | 1976-11-08 | 1978-10-24 | General Electric Company | Dichroic liquid crystal composition with 4,4-bis (substituted naphthylazo)azobenzene dichroic dyes |
US4184750A (en) * | 1976-11-12 | 1980-01-22 | Rca Corporation | Novel liquid crystal dyestuffs and electro-optic devices incorporating same |
FR2373076A1 (fr) * | 1976-12-03 | 1978-06-30 | Thomson Csf | Cellule a cristal liquide |
US4141627A (en) * | 1977-01-06 | 1979-02-27 | Rca Corporation | Electro-optic device |
US4702561A (en) * | 1977-04-11 | 1987-10-27 | Minnesota Mining And Manufacturing Company | Pleochroic dyes and electro-optical displays therewith |
US4105299A (en) * | 1977-04-11 | 1978-08-08 | Minnesota Mining And Manufacturing Company | Electro-optical devices containing methine arylidene dyes |
DE2815860A1 (de) * | 1977-04-15 | 1978-10-19 | Hoffmann La Roche | Fluessigkristalline mischungen |
US4153343A (en) * | 1977-06-09 | 1979-05-08 | Rca Corporation | Liquid crystal dyestuffs and electro-optic devices incorporating same |
US4116861A (en) * | 1977-08-18 | 1978-09-26 | General Electric Company | Dichroic liquid crystal compositions |
US4337999A (en) * | 1977-08-29 | 1982-07-06 | Sharp Corporation | Fluorescent liquid crystal display compositions and devices |
US4253740A (en) * | 1977-09-12 | 1981-03-03 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland | Liquid crystal materials and devices containing them |
DE2862064D1 (en) * | 1977-10-14 | 1982-11-25 | Bdh Chemicals Ltd | Pleochroic dyes suitable for use in solution with liquid crystal materials for electro-optic device applications |
US4291948A (en) * | 1977-11-10 | 1981-09-29 | International Standard Electric Corporation | Liquid crystal display incorporating positive and negative smectic material |
DD137118B1 (de) * | 1978-02-06 | 1980-10-01 | Hermann Schubert | Elektrooptische anordnung zur lichtmodulation oder symbolanzeige |
GB1549584A (en) * | 1978-03-02 | 1979-08-08 | Standard Telephones Cables Ltd | Temperature responsive device |
CH638624A5 (de) * | 1978-04-12 | 1983-09-30 | Secr Defence Brit | Elektrooptisches fluessigkristall-anzeigegeraet. |
DD137242B1 (de) * | 1978-06-16 | 1980-10-29 | Dietrich Demus | Nematische kristallin-fluessige mischungen |
US4288147A (en) * | 1978-12-20 | 1981-09-08 | Timex Corporation | Electro-optical composition of the guest-host type |
DE2902177A1 (de) * | 1978-12-21 | 1980-07-17 | Bbc Brown Boveri & Cie | Fluessigkristallmischung |
US4358589A (en) * | 1979-02-02 | 1982-11-09 | Veb Werk Fur Fernsehelektronik Im Veb Kombinat Mikroelektronik | Nematic liquid crystal compounds |
CA1120478A (en) * | 1979-02-05 | 1982-03-23 | Arthur Boller | Cyclohexyl pyrimidines |
US4232950A (en) * | 1979-02-23 | 1980-11-11 | Minnesota Mining And Manufacturing Company | Liquid crystal compositions including pleochroic dye |
US4232949A (en) * | 1979-02-23 | 1980-11-11 | Minnesota Mining And Manufacturing Company | Liquid crystal compositions containing pleochroic dye |
US4364838A (en) * | 1979-11-14 | 1982-12-21 | Hoffmann-La Roche Inc. | Liquid crystal mixtures |
US4350603A (en) * | 1980-06-30 | 1982-09-21 | General Electric Company | Novel tris-azo dyes and liquid crystal compositions made therewith |
EP0043904A3 (de) * | 1980-07-10 | 1982-03-31 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Farbstoffhaltige Mischungen, neue Farbstoffe und deren Verwendung in Flüssigkristallmischungen |
US4394070A (en) * | 1980-07-16 | 1983-07-19 | Minnesota Mining And Manufacturing Company | Helichromic compounds and displays |
US4308161A (en) * | 1980-08-04 | 1981-12-29 | General Electric Company | Novel yellow azo dyes and dichroic liquid crystal compositions made therewith |
US4308164A (en) * | 1980-08-04 | 1981-12-29 | General Electric Company | Novel yellow azo dyes and dichroic liquid crystal composition made therewith |
US4308163A (en) * | 1980-08-04 | 1981-12-29 | General Electric Company | Novel yellow azo dyes and dichroic liquid crystal composition made therewith |
US4308162A (en) * | 1980-12-08 | 1981-12-29 | General Electric Company | Novel yellow azo dyes and dichroic liquid crystal compositions made therewith |
US4565424A (en) * | 1980-12-12 | 1986-01-21 | Minnesota Mining And Manufacturing Company | Asymmetric dichroic dye molecules having poly(arylazo) linking groups, a bis-substituted aryl thiazyl end group, and another end group |
US4378302A (en) * | 1980-12-16 | 1983-03-29 | General Electric Company | Red perylene dichroic dye containing liquid crystal formulations |
US4359398A (en) * | 1980-12-22 | 1982-11-16 | General Electric Company | Liquid crystal compositions with novel tris-azo dichroic dyes |
DE3049454A1 (de) | 1980-12-30 | 1982-07-29 | Bayer Ag, 5090 Leverkusen | Fluessigkristallines material enthaltend disazofarbstoffe |
JPS57155282A (en) * | 1981-03-20 | 1982-09-25 | Mitsubishi Chem Ind Ltd | Liquid crystal composition |
US4461715A (en) * | 1981-04-06 | 1984-07-24 | Minnesota Mining And Manufacturing Company | Thermally addressed cholesteric-smectic liquid crystal device and composition |
DE3123519A1 (de) * | 1981-06-13 | 1982-12-30 | Bayer Ag, 5090 Leverkusen | Fluessigkristallines material enthaltend azofarbstoffe |
US4514045A (en) * | 1981-06-22 | 1985-04-30 | Minnesota Mining And Manufacturing Company | Helichromic-smectic liquid crystal compositions and display cells |
JPS5857489A (ja) * | 1981-10-01 | 1983-04-05 | Alps Electric Co Ltd | カラ−液晶組成物 |
JPS5857488A (ja) * | 1981-10-02 | 1983-04-05 | Mitsubishi Chem Ind Ltd | ゲスト−ホスト型液晶組成物 |
US4401369A (en) * | 1981-10-19 | 1983-08-30 | Electronic Display Systems, Inc. | Class of dichroic dyes for use with liquid crystals |
US4411812A (en) * | 1981-11-12 | 1983-10-25 | General Electric Company | Dichroic liquid crystal compositions made with asymmetric tris-azo dyes |
EP0080153B1 (en) * | 1981-11-16 | 1987-04-08 | Mitsubishi Kasei Corporation | Pleochroic azo dyes, a liquid crystal composition containing the azo dyes and a display device using the liquid crystal composition |
DE3149129A1 (de) * | 1981-12-11 | 1983-06-16 | Bayer Ag, 5090 Leverkusen | Fluessigkristalline phase eines azoreaktivfarbstoffs und deren verwendung zum faerben und bedrucken von natuerlichen und synthetischen substraten |
JPS58111882A (ja) * | 1981-12-25 | 1983-07-04 | Alps Electric Co Ltd | カラ−液晶表示装置 |
JPS58138767A (ja) * | 1982-02-10 | 1983-08-17 | Hitachi Ltd | 液晶組成物及び表示素子 |
JPS5947261A (ja) * | 1982-09-13 | 1984-03-16 | Nippon Kanko Shikiso Kenkyusho:Kk | 液晶用アゾ色素の二色性改良法 |
EP0098522B1 (en) * | 1982-06-30 | 1989-06-07 | Hitachi, Ltd. | Liquid crystal composition |
JPH0613703B2 (ja) * | 1982-06-30 | 1994-02-23 | 三菱化成株式会社 | ゲスト―ホスト型液晶組成物 |
EP0099014A3 (fr) * | 1982-07-16 | 1984-12-12 | Asulab S.A. | Composition de couleur foncée à base de cristaux liquides |
JPH0613704B2 (ja) * | 1982-10-21 | 1994-02-23 | 三菱化成株式会社 | アゾ系多色性色素を含む液晶組成物 |
EP0110205B1 (de) * | 1982-11-29 | 1987-12-09 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Farbige Flüssigkristallmischungen enthaltend Phenyläthane |
DE3245751A1 (de) * | 1982-12-10 | 1984-06-14 | Bayer Ag, 5090 Leverkusen | Azofarbstoffe und fluessigkristallines material enthaltend azofarbstoffe |
DE3342040A1 (de) * | 1983-11-22 | 1985-05-30 | Basf Ag, 6700 Ludwigshafen | Azofarbstoffe und fluessigkristalline materialien, enthaltend diese farbstoffe |
GB2154024B (en) * | 1984-02-07 | 1987-03-18 | Standard Telephones Cables Ltd | Dynamic hologram recording |
DE3665732D1 (en) * | 1985-03-22 | 1989-10-26 | Matsushita Electric Ind Co Ltd | Liquid crystal compositions |
DE3639156A1 (de) * | 1986-11-15 | 1988-05-26 | Basf Ag | Trisazofarbstoffe |
DE3825066A1 (de) * | 1988-07-23 | 1990-01-25 | Roehm Gmbh | Verfahren zur herstellung von duennen, anisotropen schichten auf oberflaechenstrukturierten traegern |
JPH0397571U (ja) * | 1990-01-25 | 1991-10-08 | ||
WO1997026919A2 (en) * | 1996-01-24 | 1997-07-31 | Warner-Lambert Company | Method of imaging amyloid deposits |
US7754295B2 (en) | 2006-06-29 | 2010-07-13 | Industrial Technology Research Institute | Single substrate guest-host polymer dispersed liquid crystal displays |
KR101647510B1 (ko) * | 2007-11-28 | 2016-08-10 | 메르크 파텐트 게엠베하 | 액정 매질 및 액정 디스플레이 |
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US2659719A (en) * | 1951-06-23 | 1953-11-17 | Eastman Kodak Co | 2-amino-5-nitrothiazole azo dye compounds |
DE1019415B (de) * | 1951-06-23 | 1957-11-14 | Eastman Kodak Co | Verfahren zur Herstellung von Monoazofarbstoffen |
NL250565A (ja) * | 1959-04-16 | |||
US3597044A (en) * | 1968-09-03 | 1971-08-03 | Rca Corp | Electro-optic light modulator |
US3549305A (en) * | 1969-09-22 | 1970-12-22 | American Aniline Prod | Aromatic polyester fiber dyed with disazo dyestuff |
US3703329A (en) * | 1969-12-29 | 1972-11-21 | Rca Corp | Liquid crystal color display |
JPS4731883U (ja) * | 1971-04-20 | 1972-12-09 | ||
GB1452826A (en) * | 1973-10-17 | 1976-10-20 | Secr Defence | Liquid crystal compositions |
GB1433130A (en) * | 1972-11-09 | 1976-04-22 | Secr Defence | Substituted biphenyl and polyphenyl compounds and liquid crystal materials and devices containing them |
JPS5942287B2 (ja) * | 1972-12-19 | 1984-10-13 | 松下電器産業株式会社 | 色相変調表示装置 |
US3833287A (en) * | 1973-03-08 | 1974-09-03 | Bell Telephone Labor Inc | Guest-host liquid crystal device |
JPS5328102B2 (ja) * | 1973-04-16 | 1978-08-12 | ||
JPS605630B2 (ja) * | 1973-07-06 | 1985-02-13 | セイコーエプソン株式会社 | 表示装置 |
JPS5031845A (ja) * | 1973-07-20 | 1975-03-28 | ||
JPS5043076A (ja) * | 1973-08-20 | 1975-04-18 | ||
DE2441296C3 (de) * | 1973-08-31 | 1978-11-02 | Dai Nippon Toryo K.K., Osaka (Japan) | Nematische Flüssigkristallmassen und deren Verwendung |
US3960751A (en) * | 1973-09-19 | 1976-06-01 | Matsushita Electric Industrial Co., Ltd. | Electro-optical display element |
US3941560A (en) * | 1973-12-07 | 1976-03-02 | American Aniline Products, Inc. | Trisazo polyester materials |
GB1459046A (en) * | 1974-03-15 | 1976-12-22 | Secr Defence | Liquid crystal devices |
JPS5435780B2 (ja) * | 1974-07-23 | 1979-11-05 | ||
GB1507030A (en) * | 1974-10-21 | 1978-04-12 | Secr Defence | Liquid crystal display devices |
-
1976
- 1976-06-14 US US05/695,404 patent/US4145114A/en not_active Expired - Lifetime
- 1976-06-16 FR FR7618334A patent/FR2438676A1/fr active Granted
- 1976-06-17 JP JP51072087A patent/JPS522885A/ja active Granted
- 1976-06-17 CH CH777076A patent/CH624705A5/de not_active IP Right Cessation
- 1976-06-18 DE DE2627215A patent/DE2627215C2/de not_active Expired
Also Published As
Publication number | Publication date |
---|---|
DE2627215C2 (de) | 1985-09-19 |
DE2627215A1 (de) | 1977-01-20 |
US4145114A (en) | 1979-03-20 |
JPS522885A (en) | 1977-01-10 |
FR2438676A1 (fr) | 1980-05-09 |
FR2438676B1 (ja) | 1984-11-23 |
JPS6119672B2 (ja) | 1986-05-19 |
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Legal Events
Date | Code | Title | Description |
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PL | Patent ceased |