DE3006744A1 - Pleochroitische farbstoffe enthaltende fluessigkristallmassen - Google Patents
Pleochroitische farbstoffe enthaltende fluessigkristallmassenInfo
- Publication number
- DE3006744A1 DE3006744A1 DE19803006744 DE3006744A DE3006744A1 DE 3006744 A1 DE3006744 A1 DE 3006744A1 DE 19803006744 DE19803006744 DE 19803006744 DE 3006744 A DE3006744 A DE 3006744A DE 3006744 A1 DE3006744 A1 DE 3006744A1
- Authority
- DE
- Germany
- Prior art keywords
- radicals
- bis
- liquid crystal
- value
- dye
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 239000004973 liquid crystal related substance Substances 0.000 title claims description 34
- 239000003086 colorant Substances 0.000 title description 4
- 239000000975 dye Substances 0.000 claims description 67
- 239000000203 mixture Substances 0.000 claims description 47
- 150000001875 compounds Chemical class 0.000 claims description 34
- 239000000460 chlorine Substances 0.000 claims description 28
- -1 1 -cyanphenyl Chemical group 0.000 claims description 19
- 239000004988 Nematic liquid crystal Substances 0.000 claims description 18
- 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 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 150000004056 anthraquinones Chemical class 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 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 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000374 eutectic mixture Substances 0.000 claims description 4
- 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 description 3
- 125000001153 fluoro group Chemical group F* 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
- UWCWUCKPEYNDNV-LBPRGKRZSA-N 2,6-dimethyl-n-[[(2s)-pyrrolidin-2-yl]methyl]aniline Chemical compound CC1=CC=CC(C)=C1NC[C@H]1NCCC1 UWCWUCKPEYNDNV-LBPRGKRZSA-N 0.000 claims 3
- FBMQNRKSAWNXBT-UHFFFAOYSA-N 1,4-diaminoanthracene-9,10-dione Chemical group O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2N FBMQNRKSAWNXBT-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 2
- 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 claims 1
- QIHMGEKACAOTPE-UHFFFAOYSA-N 1-amino-5-chloroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC=C2C(=O)C2=C1C=CC=C2N QIHMGEKACAOTPE-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 230000003287 optical effect Effects 0.000 description 11
- 150000003254 radicals Chemical class 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 8
- 230000005684 electric field Effects 0.000 description 8
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-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
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 3
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- MJVAVZPDRWSRRC-UHFFFAOYSA-N Menadione Chemical compound C1=CC=C2C(=O)C(C)=CC(=O)C2=C1 MJVAVZPDRWSRRC-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000004996 licristal® Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 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
- 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 description 2
- BTLXPCBPYBNQNR-UHFFFAOYSA-N 1-hydroxyanthraquinone Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2O BTLXPCBPYBNQNR-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
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004140 cleaning 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
- 150000001934 cyclohexanes Chemical class 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 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
- HDNTWLWRVIQCEG-UHFFFAOYSA-N 1,2,5-trihydroxy-6-methoxyanthracene-9,10-dione Chemical compound COC1=C(C=2C(C3=CC=C(C(=C3C(C=2C=C1)=O)O)O)=O)O HDNTWLWRVIQCEG-UHFFFAOYSA-N 0.000 description 1
- RCLVXKKDNUPATR-UHFFFAOYSA-N 1,4-bis(4-bromophenyl)-10-sulfanylideneanthracen-9-one Chemical compound BrC1=CC=C(C=C1)C1=CC=C(C=2C(C3=CC=CC=C3C(C12)=S)=O)C1=CC=C(C=C1)Br RCLVXKKDNUPATR-UHFFFAOYSA-N 0.000 description 1
- QTYOMVOCGVHYJF-UHFFFAOYSA-N 1,4-bis(4-decoxyphenyl)-10-sulfanylideneanthracen-9-one Chemical compound C(CCCCCCCCC)OC1=CC=C(C=C1)C1=CC=C(C=2C(C3=CC=CC=C3C(C12)=S)=O)C1=CC=C(C=C1)OCCCCCCCCCC QTYOMVOCGVHYJF-UHFFFAOYSA-N 0.000 description 1
- UJEJYVQRAMTWSP-UHFFFAOYSA-N 1,4-bis(4-methoxyphenyl)-10-sulfanylideneanthracen-9-one Chemical compound COC1=CC=C(C=C1)C1=CC=C(C=2C(C3=CC=CC=C3C(C12)=S)=O)C1=CC=C(C=C1)OC UJEJYVQRAMTWSP-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
- XNTPJDVHOCTRFY-UHFFFAOYSA-N 1,4-diamino-2-methyl-5-nitroanthracene-9,10-dione Chemical compound CC1=C(C=2C(C3=CC=CC(=C3C(C2C(=C1)N)=O)[N+](=O)[O-])=O)N XNTPJDVHOCTRFY-UHFFFAOYSA-N 0.000 description 1
- RAWWOPUQJFSOKA-UHFFFAOYSA-N 1,4-diphenyl-10-sulfanylideneanthracen-9-one Chemical compound C1(=CC=CC=C1)C1=CC=C(C=2C(C3=CC=CC=C3C(C12)=S)=O)C1=CC=CC=C1 RAWWOPUQJFSOKA-UHFFFAOYSA-N 0.000 description 1
- PKXURGPVLYNQOT-UHFFFAOYSA-N 1,5-bis(4-bromophenyl)-10-sulfanylideneanthracen-9-one Chemical compound BrC1=CC=C(C=C1)C1=CC=CC=2C(C3=C(C=CC=C3C(C12)=S)C1=CC=C(C=C1)Br)=O PKXURGPVLYNQOT-UHFFFAOYSA-N 0.000 description 1
- OIWBKBJWSLCTHN-UHFFFAOYSA-N 1,5-bis(4-chlorophenyl)-10-sulfanylideneanthracen-9-one Chemical compound ClC1=CC=C(C=C1)C1=CC=CC=2C(C3=C(C=CC=C3C(C12)=S)C1=CC=C(C=C1)Cl)=O OIWBKBJWSLCTHN-UHFFFAOYSA-N 0.000 description 1
- SCBZYTIZDZIWAP-UHFFFAOYSA-N 1,5-bis(4-decoxyphenyl)-10-sulfanylideneanthracen-9-one Chemical compound C(CCCCCCCCC)OC1=CC=C(C=C1)C1=CC=CC=2C(C3=C(C=CC=C3C(C12)=S)C1=CC=C(C=C1)OCCCCCCCCCC)=O SCBZYTIZDZIWAP-UHFFFAOYSA-N 0.000 description 1
- TYIKYKBGDHUWHK-UHFFFAOYSA-N 1,5-bis(4-decylphenyl)-10-sulfanylideneanthracen-9-one Chemical compound C(CCCCCCCCC)C1=CC=C(C=C1)C1=CC=CC=2C(C3=C(C=CC=C3C(C12)=S)C1=CC=C(C=C1)CCCCCCCCCC)=O TYIKYKBGDHUWHK-UHFFFAOYSA-N 0.000 description 1
- ONGPFKYKYVDZAI-UHFFFAOYSA-N 1,5-bis(4-methoxyphenyl)-10-sulfanylideneanthracen-9-one Chemical compound COC1=CC=C(C=C1)C1=CC=CC=2C(C3=C(C=CC=C3C(C12)=S)C1=CC=C(C=C1)OC)=O ONGPFKYKYVDZAI-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
- VWBVCOPVKXNMMZ-UHFFFAOYSA-N 1,5-diaminoanthracene-9,10-dione Chemical compound O=C1C2=C(N)C=CC=C2C(=O)C2=C1C=CC=C2N VWBVCOPVKXNMMZ-UHFFFAOYSA-N 0.000 description 1
- URGJPVFHRCGTGP-UHFFFAOYSA-N 1,8-bis(4-decylphenyl)-10-sulfanylideneanthracen-9-one Chemical compound C(CCCCCCCCC)C1=CC=C(C=C1)C1=CC=CC=2C(C3=CC=CC(=C3C(C12)=O)C1=CC=C(C=C1)CCCCCCCCCC)=S URGJPVFHRCGTGP-UHFFFAOYSA-N 0.000 description 1
- OLZZRVAIRUKZHY-UHFFFAOYSA-N 1,8-bis(4-methylphenyl)-10-sulfanylideneanthracen-9-one Chemical compound CC1=CC=C(C=C1)C1=CC=CC=2C(C3=CC=CC(=C3C(C12)=O)C1=CC=C(C=C1)C)=S OLZZRVAIRUKZHY-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
- XHWWVXZEALFXQA-UHFFFAOYSA-N 1-amino-4-chloro-2-methylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(N)C(C)=CC(Cl)=C3C(=O)C2=C1 XHWWVXZEALFXQA-UHFFFAOYSA-N 0.000 description 1
- WSPPHHAIMCTKNN-UHFFFAOYSA-N 1-amino-4-hydroxy-2-methoxyanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(N)C(OC)=CC(O)=C3C(=O)C2=C1 WSPPHHAIMCTKNN-UHFFFAOYSA-N 0.000 description 1
- ZKSQXZOGGFZDPU-UHFFFAOYSA-N 1-amino-5-chloro-2-methoxyanthracene-9,10-dione Chemical compound COC1=C(C=2C(C3=CC=CC(=C3C(C2C=C1)=O)Cl)=O)N ZKSQXZOGGFZDPU-UHFFFAOYSA-N 0.000 description 1
- YWXQQHWCNBVZPD-UHFFFAOYSA-N 1-chloro-5-hydroxyanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC=C2C(=O)C2=C1C=CC=C2O YWXQQHWCNBVZPD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- AUXIEQKHXAYAHG-UHFFFAOYSA-N 1-phenylcyclohexane-1-carbonitrile Chemical class C=1C=CC=CC=1C1(C#N)CCCCC1 AUXIEQKHXAYAHG-UHFFFAOYSA-N 0.000 description 1
- MFUVUMDPFHONBL-UHFFFAOYSA-N 2,5-dichloro-1,4-dihydroxy-7-methoxyanthracene-9,10-dione Chemical compound COC1=CC=2C(C3=C(C(=CC(=C3C(C2C(=C1)Cl)=O)O)Cl)O)=O MFUVUMDPFHONBL-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
- YDWVEMRZDJNCFW-UHFFFAOYSA-N 4,5-bis(4-bromophenyl)-10-sulfanylideneanthracen-9-one Chemical compound BrC1=CC=C(C=C1)C1=CC=CC=2C(C3=CC=CC(=C3C(C12)=S)C1=CC=C(C=C1)Br)=O YDWVEMRZDJNCFW-UHFFFAOYSA-N 0.000 description 1
- KSGVWZXAYATVEL-UHFFFAOYSA-N 4,5-bis(4-decoxyphenyl)-10-sulfanylideneanthracen-9-one Chemical compound C(CCCCCCCCC)OC1=CC=C(C=C1)C1=CC=CC=2C(C3=CC=CC(=C3C(C12)=S)C1=CC=C(C=C1)OCCCCCCCCCC)=O KSGVWZXAYATVEL-UHFFFAOYSA-N 0.000 description 1
- UCUVZHPDXYNERD-UHFFFAOYSA-N 4,5-bis(4-decylphenyl)-10-sulfanylideneanthracen-9-one Chemical compound C(CCCCCCCCC)C1=CC=C(C=C1)C1=CC=CC=2C(C3=CC=CC(=C3C(C12)=S)C1=CC=C(C=C1)CCCCCCCCCC)=O UCUVZHPDXYNERD-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
- XEVOVPMGGPPQCD-UHFFFAOYSA-N 4,5-bis(4-methoxyphenyl)-10-sulfanylideneanthracen-9-one Chemical compound COC1=CC=C(C=C1)C1=CC=CC=2C(C3=CC=CC(=C3C(C12)=S)C1=CC=C(C=C1)OC)=O XEVOVPMGGPPQCD-UHFFFAOYSA-N 0.000 description 1
- MRBYZCRWDZQXMC-UHFFFAOYSA-N 4,5-bis(4-methylphenyl)-10-sulfanylideneanthracen-9-one Chemical compound CC1=CC=C(C=C1)C1=CC=CC=2C(C3=CC=CC(=C3C(C12)=S)C1=CC=C(C=C1)C)=O MRBYZCRWDZQXMC-UHFFFAOYSA-N 0.000 description 1
- DGYPLYHNLJCZJB-UHFFFAOYSA-N 4,5-diphenyl-10-sulfanylideneanthracen-9-one Chemical compound C=12C(=S)C(C(=CC=C3)C=4C=CC=CC=4)=C3C(=O)C2=CC=CC=1C1=CC=CC=C1 DGYPLYHNLJCZJB-UHFFFAOYSA-N 0.000 description 1
- TUZDVLWHKCICIP-UHFFFAOYSA-N 4,8-diamino-1,5-dihydroxy-2-methoxyanthracene-9,10-dione Chemical compound OC1=CC=C(C=2C(C3=C(C(=CC(=C3C(C12)=O)N)OC)O)=O)N TUZDVLWHKCICIP-UHFFFAOYSA-N 0.000 description 1
- TWYYEGXSFYSRNP-UHFFFAOYSA-N 4-decylbenzenethiol Chemical compound CCCCCCCCCCC1=CC=C(S)C=C1 TWYYEGXSFYSRNP-UHFFFAOYSA-N 0.000 description 1
- WWQQPHUHTAZWDH-UHFFFAOYSA-N 4-ethylbenzenethiol Chemical compound CCC1=CC=C(S)C=C1 WWQQPHUHTAZWDH-UHFFFAOYSA-N 0.000 description 1
- FTZVZGXEBXVWMD-UHFFFAOYSA-N 4-octylbenzenethiol Chemical compound CCCCCCCCC1=CC=C(S)C=C1 FTZVZGXEBXVWMD-UHFFFAOYSA-N 0.000 description 1
- KRVHFFQFZQSNLB-UHFFFAOYSA-N 4-phenylbenzenethiol Chemical compound C1=CC(S)=CC=C1C1=CC=CC=C1 KRVHFFQFZQSNLB-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WYLVIERTMNVWAI-UHFFFAOYSA-N C(CCC)OC1=CC=C(C=C1)C1=CC=C(C=2C(C3=CC=CC=C3C(C12)=S)=O)C1=CC=C(C=C1)OCCCC Chemical compound C(CCC)OC1=CC=C(C=C1)C1=CC=C(C=2C(C3=CC=CC=C3C(C12)=S)=O)C1=CC=C(C=C1)OCCCC WYLVIERTMNVWAI-UHFFFAOYSA-N 0.000 description 1
- 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 1
- OOFOPUJLFHSMFA-UHFFFAOYSA-N CCCCC(C=C1)=CC=C1OC(C=CC=C1C(C2=C3C=CC=C2OC2=CC=C(CCCC)C=C2)=S)=C1C3=O Chemical compound CCCCC(C=C1)=CC=C1OC(C=CC=C1C(C2=C3C=CC=C2OC2=CC=C(CCCC)C=C2)=S)=C1C3=O OOFOPUJLFHSMFA-UHFFFAOYSA-N 0.000 description 1
- RYGQHRZGCUQXMU-UHFFFAOYSA-N COC1=C(C=2C(C3=CC=CC(=C3C(C2C(=C1)O)=O)[N+](=O)[O-])=O)O Chemical compound COC1=C(C=2C(C3=CC=CC(=C3C(C2C(=C1)O)=O)[N+](=O)[O-])=O)O RYGQHRZGCUQXMU-UHFFFAOYSA-N 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 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
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- VXAUWWUXCIMFIM-UHFFFAOYSA-M aluminum;oxygen(2-);hydroxide Chemical compound [OH-].[O-2].[Al+3] VXAUWWUXCIMFIM-UHFFFAOYSA-M 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal 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
- 125000004802 cyanophenyl group Chemical group 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- TUXJTJITXCHUEL-UHFFFAOYSA-N disperse red 11 Chemical compound C1=CC=C2C(=O)C3=C(N)C(OC)=CC(N)=C3C(=O)C2=C1 TUXJTJITXCHUEL-UHFFFAOYSA-N 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- SGDAAZJVSNIPOJ-UHFFFAOYSA-N hexoxysulfanylbenzene Chemical compound CCCCCCOSC1=CC=CC=C1 SGDAAZJVSNIPOJ-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 235000021190 leftovers Nutrition 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229960001156 mitoxantrone Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- FYKLSLRYPDLISN-UHFFFAOYSA-N propoxysulfanylbenzene Chemical compound CCCOSC1=CC=CC=C1 FYKLSLRYPDLISN-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 239000000979 synthetic dye Substances 0.000 description 1
- 239000001040 synthetic pigment Substances 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000001429 visible spectrum 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
- 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
-
- 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
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 |
|---|---|
| DE3006744A1 true DE3006744A1 (de) | 1980-09-04 |
Family
ID=26686214
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803006744 Withdrawn DE3006744A1 (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) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3109030A1 (de) * | 1980-03-14 | 1982-02-11 | Asulab S.A., 2502 Bienne | Zusammensetzungen auf fluessigkristallbasis und ihre verwendung in elektrooptischen vorrichtungen |
| EP0049035A1 (en) * | 1980-07-29 | 1982-04-07 | The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and | Organic compositions suitable for a guest-host liquid crystal device |
| DE3201120A1 (de) * | 1981-01-17 | 1982-10-21 | Hitachi, Ltd., Tokyo | Fluessigkristall-zusammensetzung |
| DE3314467A1 (de) * | 1982-07-17 | 1984-01-19 | Bayer Ag, 5090 Leverkusen | Dichroitisches material, enthaltend anthrachinonfarbstoffe und neue anthrachinonfarbstoffe |
| US4466899A (en) * | 1981-01-10 | 1984-08-21 | Basf Aktiengesellschaft | Dyes for use in liquid crystal mixtures |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3046904A1 (de) * | 1980-12-12 | 1982-07-15 | Bayer Ag, 5090 Leverkusen | Anthrachinonfarbstoffe, verfahren zu ihrer herstellung ihre verwendung sowie fluessigkristalline materialien enthaltend anthrachinonfarbstoffe |
| 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 |
| 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
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3109030A1 (de) * | 1980-03-14 | 1982-02-11 | Asulab S.A., 2502 Bienne | Zusammensetzungen auf fluessigkristallbasis und ihre verwendung in elektrooptischen vorrichtungen |
| EP0049035A1 (en) * | 1980-07-29 | 1982-04-07 | The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and | Organic compositions suitable for a guest-host liquid crystal device |
| US4466899A (en) * | 1981-01-10 | 1984-08-21 | Basf Aktiengesellschaft | Dyes for use in liquid crystal mixtures |
| DE3201120A1 (de) * | 1981-01-17 | 1982-10-21 | Hitachi, Ltd., Tokyo | Fluessigkristall-zusammensetzung |
| DE3314467A1 (de) * | 1982-07-17 | 1984-01-19 | Bayer Ag, 5090 Leverkusen | Dichroitisches material, enthaltend anthrachinonfarbstoffe und neue anthrachinonfarbstoffe |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2449720A1 (fr) | 1980-09-19 |
| GB2043097A (en) | 1980-10-01 |
| FR2449720B1 (enrdf_load_stackoverflow) | 1984-10-26 |
| CH645916A5 (de) | 1984-10-31 |
| IT8020131A0 (it) | 1980-02-22 |
| AU5582980A (en) | 1980-08-28 |
| 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 |
|---|---|---|---|
| 8141 | Disposal/no request for examination |