CH645916A5 - Pleochroitische farbstoffe enthaltende fluessigkristallmassen. - Google Patents
Pleochroitische farbstoffe enthaltende fluessigkristallmassen. Download PDFInfo
- Publication number
- CH645916A5 CH645916A5 CH144680A CH144680A CH645916A5 CH 645916 A5 CH645916 A5 CH 645916A5 CH 144680 A CH144680 A CH 144680A CH 144680 A CH144680 A CH 144680A CH 645916 A5 CH645916 A5 CH 645916A5
- Authority
- CH
- Switzerland
- Prior art keywords
- liquid crystal
- pleochroic
- radicals
- dye
- bis
- Prior art date
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- 239000004973 liquid crystal related substance Substances 0.000 title claims description 33
- 239000003086 colorant Substances 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 66
- 239000000203 mixture Substances 0.000 claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 33
- 239000000460 chlorine Substances 0.000 claims description 30
- -1 ethoxybenzothiazolyl Chemical group 0.000 claims description 27
- 150000003254 radicals Chemical class 0.000 claims description 23
- 239000004988 Nematic liquid crystal Substances 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 230000003287 optical effect Effects 0.000 claims description 11
- 230000005684 electric field Effects 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 239000000374 eutectic mixture Substances 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- BOCJQSFSGAZAPQ-UHFFFAOYSA-N 1-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl BOCJQSFSGAZAPQ-UHFFFAOYSA-N 0.000 claims description 3
- 230000002349 favourable effect Effects 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- AQXYVFBSOOBBQV-UHFFFAOYSA-N 1-amino-4-hydroxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2N AQXYVFBSOOBBQV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- SDICTISQCKLMEB-UHFFFAOYSA-N 1,4-diamino-5-nitroanthracene-9,10-dione Chemical compound O=C1C=2C(N)=CC=C(N)C=2C(=O)C2=C1C=CC=C2[N+]([O-])=O SDICTISQCKLMEB-UHFFFAOYSA-N 0.000 claims 2
- FBMQNRKSAWNXBT-UHFFFAOYSA-N 1,4-diaminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2N FBMQNRKSAWNXBT-UHFFFAOYSA-N 0.000 claims 2
- 230000002745 absorbent Effects 0.000 claims 2
- 239000002250 absorbent Substances 0.000 claims 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- QENVQRYABLFZJR-UHFFFAOYSA-N biphenylene-1-carbonitrile Chemical class C12=CC=CC=C2C2=C1C=CC=C2C#N QENVQRYABLFZJR-UHFFFAOYSA-N 0.000 claims 1
- 238000005253 cladding Methods 0.000 claims 1
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- 238000000576 coating method Methods 0.000 claims 1
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- 230000000737 periodic effect Effects 0.000 claims 1
- 238000001429 visible spectrum Methods 0.000 claims 1
- 238000000034 method Methods 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 13
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 11
- 150000004056 anthraquinones Chemical class 0.000 description 10
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 8
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical class C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 5
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000001000 anthraquinone dye Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical class C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000004996 licristal® Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 125000000335 thiazolyl group Chemical group 0.000 description 3
- GVZVEQKCTXXZAU-UHFFFAOYSA-N 1,4-bis(4-decylphenyl)-10-sulfanylideneanthracen-9-one Chemical compound C(CCCCCCCCC)C1=CC=C(C=C1)C1=CC=C(C=2C(C3=CC=CC=C3C(C12)=S)=O)C1=CC=C(C=C1)CCCCCCCCCC GVZVEQKCTXXZAU-UHFFFAOYSA-N 0.000 description 2
- MQIUMARJCOGCIM-UHFFFAOYSA-N 1,5-dichloroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC=C2C(=O)C2=C1C=CC=C2Cl MQIUMARJCOGCIM-UHFFFAOYSA-N 0.000 description 2
- STJIWQOFZIYYFH-UHFFFAOYSA-N 1-(2-phenylphenyl)cyclohexane-1-carbonitrile Chemical compound C=1C=CC=C(C=2C=CC=CC=2)C=1C1(C#N)CCCCC1 STJIWQOFZIYYFH-UHFFFAOYSA-N 0.000 description 2
- YCANAXVBJKNANM-UHFFFAOYSA-N 1-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] YCANAXVBJKNANM-UHFFFAOYSA-N 0.000 description 2
- FGTYTUFKXYPTML-UHFFFAOYSA-N 2-benzoylbenzoic acid Chemical class OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 FGTYTUFKXYPTML-UHFFFAOYSA-N 0.000 description 2
- FURZYCFZFBYJBT-JCNLHEQBSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 FURZYCFZFBYJBT-JCNLHEQBSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 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 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- KAEZRSFWWCTVNP-UHFFFAOYSA-N (4-methoxyphenyl)-(4-methoxyphenyl)imino-oxidoazanium Chemical compound C1=CC(OC)=CC=C1N=[N+]([O-])C1=CC=C(OC)C=C1 KAEZRSFWWCTVNP-UHFFFAOYSA-N 0.000 description 1
- YWQRWDIHSVCFLY-UHFFFAOYSA-N 1,4-bis(4-methylphenyl)-10-sulfanylideneanthracen-9-one Chemical compound CC1=CC=C(C=C1)C1=CC=C(C=2C(C3=CC=CC=C3C(C12)=S)=O)C1=CC=C(C=C1)C YWQRWDIHSVCFLY-UHFFFAOYSA-N 0.000 description 1
- AOVJQCDDEHGNSK-UHFFFAOYSA-N 1,4-bis(4-tert-butylphenyl)-10-sulfanylideneanthracen-9-one Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C1=CC=C(C=2C(C3=CC=CC=C3C(C12)=S)=O)C1=CC=C(C=C1)C(C)(C)C AOVJQCDDEHGNSK-UHFFFAOYSA-N 0.000 description 1
- JLZARQYFYFOWSJ-UHFFFAOYSA-N 1,4-bis[4-(4-nonylphenyl)phenyl]-10-sulfanylideneanthracen-9-one Chemical compound C(CCCCCCCC)C1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=C(C=2C(C3=CC=CC=C3C(C12)=S)=O)C1=CC=C(C=C1)C1=CC=C(C=C1)CCCCCCCCC JLZARQYFYFOWSJ-UHFFFAOYSA-N 0.000 description 1
- JQPLBJGLNSQWFI-UHFFFAOYSA-N 1,4-diamino-5-hydroxyanthracene-9,10-dione Chemical compound NC1=CC=C(C=2C(C3=C(C=CC=C3C(C12)=O)O)=O)N JQPLBJGLNSQWFI-UHFFFAOYSA-N 0.000 description 1
- UTFIMYBQTGWFJU-UHFFFAOYSA-N 1,5-bis(4-methylphenyl)-10-sulfanylideneanthracen-9-one Chemical compound CC1=CC=C(C=C1)C1=CC=CC=2C(C3=C(C=CC=C3C(C12)=S)C1=CC=C(C=C1)C)=O UTFIMYBQTGWFJU-UHFFFAOYSA-N 0.000 description 1
- JGDLEVAYNWLIKN-UHFFFAOYSA-N 1,5-bis(phenylsulfanyl)anthracene-9,10-dione Chemical compound C=12C(=O)C3=CC=CC(SC=4C=CC=CC=4)=C3C(=O)C2=CC=CC=1SC1=CC=CC=C1 JGDLEVAYNWLIKN-UHFFFAOYSA-N 0.000 description 1
- XDFZEMHIGLBKAR-UHFFFAOYSA-N 1,8-dichloro-2-methylanthracene-9,10-dione Chemical compound CC1=C(C=2C(C3=C(C=CC=C3C(C2C=C1)=O)Cl)=O)Cl XDFZEMHIGLBKAR-UHFFFAOYSA-N 0.000 description 1
- CGKIRDOXDIZWEW-UHFFFAOYSA-N 1-amino-4-hydroxy-2-methylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(N)C(C)=CC(O)=C3C(=O)C2=C1 CGKIRDOXDIZWEW-UHFFFAOYSA-N 0.000 description 1
- NMFBXBSNLQNQKL-UHFFFAOYSA-N 1-chloro-2-methylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(Cl)C(C)=CC=C3C(=O)C2=C1 NMFBXBSNLQNQKL-UHFFFAOYSA-N 0.000 description 1
- BTLXPCBPYBNQNR-UHFFFAOYSA-N 1-hydroxyanthraquinone Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2O BTLXPCBPYBNQNR-UHFFFAOYSA-N 0.000 description 1
- UZPWZIYRTTWRAL-UHFFFAOYSA-N 4,5-bis(4-benzylphenyl)-10-sulfanylideneanthracen-9-one Chemical compound C(C1=CC=CC=C1)C1=CC=C(C=C1)C1=CC=CC=2C(C3=CC=CC(=C3C(C12)=S)C1=CC=C(C=C1)CC1=CC=CC=C1)=O UZPWZIYRTTWRAL-UHFFFAOYSA-N 0.000 description 1
- HYOCULUXTMEQKW-UHFFFAOYSA-N 4,5-bis(4-chlorophenyl)-10-sulfanylideneanthracen-9-one Chemical compound ClC1=CC=C(C=C1)C1=CC=CC=2C(C3=CC=CC(=C3C(C12)=S)C1=CC=C(C=C1)Cl)=O HYOCULUXTMEQKW-UHFFFAOYSA-N 0.000 description 1
- UUQDKMVZXASFSW-UHFFFAOYSA-N 4,5-bis(4-fluorophenyl)-10-sulfanylideneanthracen-9-one Chemical compound FC1=CC=C(C=C1)C1=CC=CC=2C(C3=CC=CC(=C3C(C12)=S)C1=CC=C(C=C1)F)=O UUQDKMVZXASFSW-UHFFFAOYSA-N 0.000 description 1
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- HOYWVKUPOCFKOT-UHFFFAOYSA-N [4-[(4-methoxyphenyl)methylideneamino]phenyl] acetate Chemical compound C1=CC(OC)=CC=C1C=NC1=CC=C(OC(C)=O)C=C1 HOYWVKUPOCFKOT-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
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- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
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- 125000004429 atom Chemical group 0.000 description 1
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
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- 239000000979 synthetic dye Substances 0.000 description 1
- 239000001040 synthetic pigment Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000005406 washing 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/02—Hydroxy-anthraquinones; Ethers or esters thereof
- C09B1/06—Preparation from starting materials already containing the anthracene nucleus
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/22—Dyes with unsubstituted amino groups
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/503—Amino-hydroxy-anthraquinones; Ethers and esters thereof unsubstituted amino-hydroxy anthraquinone
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/54—Amino-hydroxy-anthraquinones; Ethers and esters thereof etherified
- C09B1/545—Anthraquinones with aliphatic, cycloaliphatic or araliphatic ether groups
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/56—Mercapto-anthraquinones
- C09B1/58—Mercapto-anthraquinones with mercapto groups substituted by aliphatic, cycloaliphatic, araliphatic or aryl radicals
- C09B1/585—Mercapto-anthraquinones with mercapto groups substituted by aliphatic, cycloaliphatic, araliphatic or aryl radicals substituted by aryl radicals
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/56—Mercapto-anthraquinones
- C09B1/62—Mercapto-anthraquinones with mercapto groups substituted by a heterocyclic ring
-
- 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
- C09K19/603—Anthroquinonic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Liquid Crystal (AREA)
- Liquid Crystal Substances (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/014,541 US4232950A (en) | 1979-02-23 | 1979-02-23 | Liquid crystal compositions including pleochroic dye |
| US06/014,540 US4232949A (en) | 1979-02-23 | 1979-02-23 | Liquid crystal compositions containing pleochroic dye |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH645916A5 true CH645916A5 (de) | 1984-10-31 |
Family
ID=26686214
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH144680A CH645916A5 (de) | 1979-02-23 | 1980-02-22 | Pleochroitische farbstoffe enthaltende fluessigkristallmassen. |
Country Status (7)
| Country | Link |
|---|---|
| KR (1) | KR830000533B1 (enrdf_load_stackoverflow) |
| AU (1) | AU535899B2 (enrdf_load_stackoverflow) |
| CH (1) | CH645916A5 (enrdf_load_stackoverflow) |
| DE (1) | DE3006744A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2449720A1 (enrdf_load_stackoverflow) |
| GB (1) | GB2043097B (enrdf_load_stackoverflow) |
| IT (1) | IT1141378B (enrdf_load_stackoverflow) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH646452A5 (fr) * | 1980-03-14 | 1984-11-30 | Asulab Sa | Composition a base de cristal liquide pour dispositif electro-optique. |
| US4405211A (en) * | 1980-07-29 | 1983-09-20 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland | Liquid crystal compositions with pleochroic anthraquinone dyes |
| DE3046904A1 (de) * | 1980-12-12 | 1982-07-15 | Bayer Ag, 5090 Leverkusen | Anthrachinonfarbstoffe, verfahren zu ihrer herstellung ihre verwendung sowie fluessigkristalline materialien enthaltend anthrachinonfarbstoffe |
| EP0056492B1 (de) * | 1981-01-10 | 1984-12-12 | BASF Aktiengesellschaft | Farbstoffe für Flüssigkristallmischungen |
| DE3201120A1 (de) * | 1981-01-17 | 1982-10-21 | Hitachi, Ltd., Tokyo | Fluessigkristall-zusammensetzung |
| GB2093475B (en) * | 1981-02-25 | 1985-10-09 | Secr Defence | Liquid crystal materials containing pleochroic dithioanthraquinone dyes |
| US4446047A (en) * | 1981-02-25 | 1984-05-01 | Imperial Chemical Industries Plc | Pleochroic anthraquinone dyes |
| DE3276868D1 (de) * | 1981-02-25 | 1987-09-03 | Ici Plc | Pleochroic anthraquinone dyes |
| US4464282A (en) * | 1981-02-25 | 1984-08-07 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britian And Northern Ireland | Organic materials |
| GB2155489B (en) * | 1981-02-25 | 1986-05-29 | Ici Plc | Liquid crystal materials containing pleochroic dithioanthraquinone dyes |
| US4514045A (en) * | 1981-06-22 | 1985-04-30 | Minnesota Mining And Manufacturing Company | Helichromic-smectic liquid crystal compositions and display cells |
| DE3309045A1 (de) * | 1982-03-13 | 1983-09-15 | Kabushiki Kaisha Nippon Kanko Shikiso Kenkyusho, Okayama | Dichroitische farbstoffe fuer fluessigkristalle und fluessigkristall-zusammensetzungen |
| DE3314467A1 (de) * | 1982-07-17 | 1984-01-19 | Bayer Ag, 5090 Leverkusen | Dichroitisches material, enthaltend anthrachinonfarbstoffe und neue anthrachinonfarbstoffe |
| DE3378767D1 (de) * | 1982-08-18 | 1989-02-02 | Ici Plc | Pleochroic anthraquinone dyes |
| GB2126601B (en) * | 1982-08-18 | 1986-12-10 | Secr Defence | Guest-host liquid crystal materials |
| WO1987002688A1 (en) * | 1985-10-29 | 1987-05-07 | Mitsubishi Chemical Industries Limited | Anthraquinone compounds and liquid-crystal composition containing them |
| KR101524486B1 (ko) * | 2012-02-03 | 2015-06-01 | 제일모직주식회사 | 다색성 발현 착색용 수지 조성물 및 이를 이용하여 제조된 수지 성형품 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1446826A (fr) * | 1964-09-14 | 1966-07-22 | Allied Chem | Résines synthétiques colorées avec des colorants organiques stables à la chaleur, et procédé pour leur fabrication |
| US3975285A (en) * | 1972-10-30 | 1976-08-17 | Hodogaya Chemical Co., Ltd. | Liquid crystal composition |
| DE2360875A1 (de) * | 1973-12-06 | 1975-06-12 | Bayer Ag | Massefaerben von polyestern |
| CH638828A5 (de) * | 1978-12-21 | 1983-10-14 | Bbc Brown Boveri & Cie | Fluessigkristallmischung. |
-
1980
- 1980-02-22 IT IT20131/80A patent/IT1141378B/it active
- 1980-02-22 GB GB8006146A patent/GB2043097B/en not_active Expired
- 1980-02-22 DE DE19803006744 patent/DE3006744A1/de not_active Withdrawn
- 1980-02-22 FR FR8003986A patent/FR2449720A1/fr active Granted
- 1980-02-22 CH CH144680A patent/CH645916A5/de not_active IP Right Cessation
- 1980-02-22 AU AU55829/80A patent/AU535899B2/en not_active Ceased
- 1980-02-23 KR KR1019800000754A patent/KR830000533B1/ko not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2449720A1 (fr) | 1980-09-19 |
| GB2043097A (en) | 1980-10-01 |
| FR2449720B1 (enrdf_load_stackoverflow) | 1984-10-26 |
| IT8020131A0 (it) | 1980-02-22 |
| AU5582980A (en) | 1980-08-28 |
| DE3006744A1 (de) | 1980-09-04 |
| IT1141378B (it) | 1986-10-01 |
| GB2043097B (en) | 1983-08-17 |
| KR830000533B1 (ko) | 1983-03-12 |
| AU535899B2 (en) | 1984-04-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |