DD204100A5 - Dichroitische anthrachinonfarbstoffe enthaltende fluessigkeitskristalline dielektika - Google Patents

Dichroitische anthrachinonfarbstoffe enthaltende fluessigkeitskristalline dielektika Download PDF

Info

Publication number: DD204100A5
Authority: DD; German Democratic Republic
Prior art keywords: deep; alkoxy; phenyl; dyes; trans
Prior art date: 1981-04-18

Application number

DD23902382A

Other languages

German (de)

English (en)

Inventor

Rudolf Eidenschink

Joachim Krause

Georg Weber

Original Assignee

Merck Patent Gmbh

Priority date (The priority date 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 date listed.)

1981-04-18

Filing date

1982-04-15

Publication date

1983-11-16

1982-04-15 Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh

1983-11-16 Publication of DD204100A5 publication Critical patent/DD204100A5/de

Links

239000000975 dye Substances 0.000 title description 30
239000007788 liquid Substances 0.000 title description 5
125000000217 alkyl group Chemical group 0.000 claims abstract description 14
125000003545 alkoxy group Chemical group 0.000 claims abstract description 13
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
125000001424 substituent group Chemical group 0.000 claims abstract description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 6
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
239000001257 hydrogen Substances 0.000 claims abstract description 4
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 4
239000001000 anthraquinone dye Substances 0.000 abstract description 9
239000003989 dielectric material Substances 0.000 abstract description 9
239000000463 material Substances 0.000 abstract description 7
230000000694 effects Effects 0.000 abstract description 5
125000004430 oxygen atom Chemical group O* 0.000 abstract description 2
-1 amino, methylamino Chemical group 0.000 description 23
239000004973 liquid crystal related substance Substances 0.000 description 21
239000012071 phase Substances 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
150000001875 compounds Chemical class 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
150000003254 radicals Chemical class 0.000 description 9
238000009835 boiling Methods 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
238000010521 absorption reaction Methods 0.000 description 7
239000000126 substance Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
238000003756 stirring Methods 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
238000000034 method Methods 0.000 description 4
DIUJNXCPDGGFQD-UHFFFAOYSA-N 2-ethoxyethoxybenzene Chemical compound CCOCCOC1=CC=CC=C1 DIUJNXCPDGGFQD-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
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 3
150000004056 anthraquinones Chemical class 0.000 description 3
239000000987 azo dye Substances 0.000 description 3
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 3
239000004327 boric acid Substances 0.000 description 3
230000003098 cholesteric effect Effects 0.000 description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
230000005684 electric field Effects 0.000 description 3
239000011159 matrix material Substances 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
229910052979 sodium sulfide Inorganic materials 0.000 description 3
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 3
238000006467 substitution reaction Methods 0.000 description 3
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
HUFBCFYTBUGLQO-QAQDUYKDSA-N C(CC)[C@@H]1CC[C@H](CC1)C1=CC=2C(C3=CC=C(C=C3C(C=2C=C1)=O)C)=O Chemical compound C(CC)[C@@H]1CC[C@H](CC1)C1=CC=2C(C3=CC=C(C=C3C(C=2C=C1)=O)C)=O HUFBCFYTBUGLQO-QAQDUYKDSA-N 0.000 description 2
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
238000005727 Friedel-Crafts reaction Methods 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
150000001555 benzenes Chemical class 0.000 description 2
230000008033 biological extinction Effects 0.000 description 2
239000001045 blue dye Substances 0.000 description 2
239000001110 calcium chloride Substances 0.000 description 2
229910001628 calcium chloride Inorganic materials 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000003086 colorant Substances 0.000 description 2
239000000470 constituent Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical class C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 2
239000005457 ice water Substances 0.000 description 2
230000031700 light absorption Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
230000005855 radiation Effects 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
PKORYTIUMAOPED-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinazoline Chemical compound C1=CC=C2NCNCC2=C1 PKORYTIUMAOPED-UHFFFAOYSA-N 0.000 description 1
VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical group C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 1
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
IHFFAAMKORYJQC-UHFFFAOYSA-N 1,5-diamino-2-[4-(2-ethoxyethoxy)phenyl]-4,8-dihydroxyanthracene-9,10-dione Chemical compound C1=CC(OCCOCC)=CC=C1C1=CC(O)=C(C(=O)C=2C(=C(O)C=CC=2N)C2=O)C2=C1N IHFFAAMKORYJQC-UHFFFAOYSA-N 0.000 description 1
LPOMYDARLRFKPI-UHFFFAOYSA-N 1,5-dihydroxy-2-methyl-4,8-dinitroanthracene-9,10-dione Chemical compound C1=CC([N+]([O-])=O)=C2C(=O)C3=C(O)C(C)=CC([N+]([O-])=O)=C3C(=O)C2=C1O LPOMYDARLRFKPI-UHFFFAOYSA-N 0.000 description 1
CUIHODIOWPLCMG-UHFFFAOYSA-N 1,5-dihydroxy-4,8-dinitroanthracene-9,10-dione Chemical compound O=C1C2=C(O)C=CC([N+]([O-])=O)=C2C(=O)C2=C1C([N+]([O-])=O)=CC=C2O CUIHODIOWPLCMG-UHFFFAOYSA-N 0.000 description 1
SHFGENOBPXWUJF-UHFFFAOYSA-N 2-(2-phenylphenyl)benzonitrile Chemical group N#CC1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 SHFGENOBPXWUJF-UHFFFAOYSA-N 0.000 description 1
SMHSPYVJAUGNOI-UHFFFAOYSA-N 2-cyclohexyl-1,4-dioxane Chemical class C1CCCCC1C1OCCOC1 SMHSPYVJAUGNOI-UHFFFAOYSA-N 0.000 description 1
YJDDXMSIMBMMGY-UHFFFAOYSA-N 2-cyclohexylpyrimidine Chemical class C1CCCCC1C1=NC=CC=N1 YJDDXMSIMBMMGY-UHFFFAOYSA-N 0.000 description 1
NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-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
ZZISXVSRADUTCW-UHFFFAOYSA-N 4,8-diamino-2,6-bis[4-(2-ethoxyethoxy)phenyl]-1,5-dihydroxyanthracene-9,10-dione Chemical compound C1=CC(OCCOCC)=CC=C1C1=CC(N)=C(C(=O)C=2C(=C(N)C=C(C=2O)C=2C=CC(OCCOCC)=CC=2)C2=O)C2=C1O ZZISXVSRADUTCW-UHFFFAOYSA-N 0.000 description 1
OPSNIDFWZWSWRU-UHFFFAOYSA-N 4,8-diamino-2,6-bis[4-(3-ethoxypropoxy)phenyl]-1,5-dihydroxyanthracene-9,10-dione Chemical compound C1=CC(OCCCOCC)=CC=C1C1=CC(N)=C(C(=O)C=2C(=C(N)C=C(C=2O)C=2C=CC(OCCCOCC)=CC=2)C2=O)C2=C1O OPSNIDFWZWSWRU-UHFFFAOYSA-N 0.000 description 1
KHNZQDZAIUHIFC-UHFFFAOYSA-N 4,8-diamino-2,6-bis[4-[2-(2-ethoxyethoxy)ethoxy]phenyl]-1,5-dihydroxyanthracene-9,10-dione Chemical compound C1=CC(OCCOCCOCC)=CC=C1C1=CC(N)=C(C(=O)C=2C(=C(N)C=C(C=2O)C=2C=CC(OCCOCCOCC)=CC=2)C2=O)C2=C1O KHNZQDZAIUHIFC-UHFFFAOYSA-N 0.000 description 1
VRZJGENLTNRAIG-UHFFFAOYSA-N 4-[4-(dimethylamino)phenyl]iminonaphthalen-1-one Chemical compound C1=CC(N(C)C)=CC=C1N=C1C2=CC=CC=C2C(=O)C=C1 VRZJGENLTNRAIG-UHFFFAOYSA-N 0.000 description 1
ZOXBWJMCXHTKNU-UHFFFAOYSA-N 5-methyl-2-benzofuran-1,3-dione Chemical compound CC1=CC=C2C(=O)OC(=O)C2=C1 ZOXBWJMCXHTKNU-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
UYMHKCRRNQZNAW-QAQDUYKDSA-N CCCCCCC[C@H](CC1)CC[C@@H]1C(C=C(C(C(C(C1=C(C=C2C)N)=C2O)=O)=C2C1=O)N)=C2O Chemical compound CCCCCCC[C@H](CC1)CC[C@@H]1C(C=C(C(C(C(C1=C(C=C2C)N)=C2O)=O)=C2C1=O)N)=C2O UYMHKCRRNQZNAW-QAQDUYKDSA-N 0.000 description 1
LJLFOYHXCOZDCH-IYARVYRRSA-N CCCCCCC[C@H](CC1)CC[C@@H]1C(C=CC(C(C(C1=CC=C2OC)=C2N)=O)=C2C1=O)=C2N Chemical compound CCCCCCC[C@H](CC1)CC[C@@H]1C(C=CC(C(C(C1=CC=C2OC)=C2N)=O)=C2C1=O)=C2N LJLFOYHXCOZDCH-IYARVYRRSA-N 0.000 description 1
FBSJDCULRVGMHS-QAQDUYKDSA-N CCCCC[C@H](CC1)CC[C@@H]1C(C=CC(C(C(C1=CC=C2C)=C2N)=O)=C2C1=O)=C2N Chemical compound CCCCC[C@H](CC1)CC[C@@H]1C(C=CC(C(C(C1=CC=C2C)=C2N)=O)=C2C1=O)=C2N FBSJDCULRVGMHS-QAQDUYKDSA-N 0.000 description 1
RKCSXLUOSSXLAN-WKILWMFISA-N CCCC[C@H](CC1)CC[C@@H]1C(C=C(C(C(C(C1=C(C=C2CCCC)N)=C2O)=O)=C2C1=O)N)=C2O Chemical compound CCCC[C@H](CC1)CC[C@@H]1C(C=C(C(C(C(C1=C(C=C2CCCC)N)=C2O)=O)=C2C1=O)N)=C2O RKCSXLUOSSXLAN-WKILWMFISA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
NZNMSOFKMUBTKW-UHFFFAOYSA-N Cyclohexanecarboxylic acid Natural products OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 1
235000000177 Indigofera tinctoria Nutrition 0.000 description 1
YKNOVGHKJGKCHX-SHTZXODSSA-N NC1=C(C=CC=2C(C3=C(C(=CC=C3C(C1=2)=O)C)N)=O)[C@@H]1CC[C@H](CC1)CCC Chemical compound NC1=C(C=CC=2C(C3=C(C(=CC=C3C(C1=2)=O)C)N)=O)[C@@H]1CC[C@H](CC1)CCC YKNOVGHKJGKCHX-SHTZXODSSA-N 0.000 description 1
239000004988 Nematic liquid crystal Substances 0.000 description 1
NTZCPYLYLCYNKJ-JOCQHMNTSA-N OC1=C(C=C(C=2C(C3=C(C(=CC(=C3C(C1=2)=O)N)C)O)=O)N)[C@@H]1CC[C@H](CC1)CCC Chemical compound OC1=C(C=C(C=2C(C3=C(C(=CC(=C3C(C1=2)=O)N)C)O)=O)N)[C@@H]1CC[C@H](CC1)CCC NTZCPYLYLCYNKJ-JOCQHMNTSA-N 0.000 description 1
XTSWNGXCJFHMBE-SHTZXODSSA-N OC1=C(C=CC=2C(C3=C(C(=CC=C3C(C1=2)=O)C)O)=O)[C@@H]1CC[C@H](CC1)CCC Chemical compound OC1=C(C=CC=2C(C3=C(C(=CC=C3C(C1=2)=O)C)O)=O)[C@@H]1CC[C@H](CC1)CCC XTSWNGXCJFHMBE-SHTZXODSSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000011149 active material Substances 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
125000004183 alkoxy alkyl group Chemical group 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
150000008359 benzonitriles Chemical class 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
150000001482 benzyl phenyl ethers Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
150000004074 biphenyls Chemical class 0.000 description 1
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical class CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
230000008859 change Effects 0.000 description 1
235000013985 cinnamic acid Nutrition 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid group Chemical class C(C=CC1=CC=CC=C1)(=O)O WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
239000002131 composite material Substances 0.000 description 1
VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 1
DQZKGSRJOUYVPL-UHFFFAOYSA-N cyclohexyl benzoate Chemical class C=1C=CC=CC=1C(=O)OC1CCCCC1 DQZKGSRJOUYVPL-UHFFFAOYSA-N 0.000 description 1
WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical compound C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000003203 everyday effect Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
229940097275 indigo Drugs 0.000 description 1
COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
UVEWQKMPXAHFST-UHFFFAOYSA-N n,1-diphenylmethanimine Chemical class C=1C=CC=CC=1C=NC1=CC=CC=C1 UVEWQKMPXAHFST-UHFFFAOYSA-N 0.000 description 1
AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
230000005693 optoelectronics Effects 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000008569 process Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000006462 rearrangement reaction Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
239000002002 slurry Substances 0.000 description 1
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
150000001629 stilbenes Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
150000001911 terphenyls Chemical class 0.000 description 1
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
150000001608 tolans Chemical class 0.000 description 1
239000001043 yellow dye Substances 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
- 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
- C09B1/16—Amino-anthraquinones
- C09B1/20—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
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- 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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD23902382A 1981-04-18 1982-04-15 Dichroitische anthrachinonfarbstoffe enthaltende fluessigkeitskristalline dielektika DD204100A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19813115762 DE3115762A1 (de)	1981-04-18	1981-04-18	"dichroitische anthrachinonfarbstoffe, diese enthaltende fluessigkristalline dielektrika und elektrooprisches anzeigeelement"

Publications (1)

Publication Number	Publication Date
DD204100A5 true DD204100A5 (de)	1983-11-16

Family

ID=6130469

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD23902382A DD204100A5 (de)	1981-04-18	1982-04-15	Dichroitische anthrachinonfarbstoffe enthaltende fluessigkeitskristalline dielektika

Country Status (4)

Country	Link
EP (1)	EP0063713A1 (fr)
JP (1)	JPS57182355A (fr)
DD (1)	DD204100A5 (fr)
DE (1)	DE3115762A1 (fr)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2118203B (en) *	1982-04-07	1985-10-02	Secr Defence	Guest-host liquid crystal mixtures with anthraquinone dyes
KR102171901B1 (ko)	2012-12-13	2020-11-02	메르크 파텐트 게엠베하	액정 매질
CN105103046A (zh)	2013-03-05	2015-11-25	默克专利股份有限公司	用于调节光学能量穿透量的装置
US10108058B2 (en)	2013-05-08	2018-10-23	Merck Patent Gmbh	Device for regulating the passage of energy
KR102234246B1 (ko)	2013-05-24	2021-04-01	메르크 파텐트 게엠베하	이색성 염료를 함유하는, 에너지 통과를 조절하기 위한 장치
KR102254011B1 (ko)	2013-12-19	2021-05-20	메르크 파텐트 게엠베하	광의 통과를 조절하기 위한 장치
DE102015005800A1 (de)	2015-05-06	2016-11-10	Merck Patent Gmbh	Thiadiazolochinoxalinderivate
EP3319964B1 (fr)	2015-07-10	2020-07-22	Merck Patent GmbH	Dithioalkylpyrrolopyrroles et leur utilisation en tant que colorants
KR20190023089A (ko)	2016-06-28	2019-03-07	메르크 파텐트 게엠베하	액정 매질
JP6972103B2 (ja)	2016-07-19	2021-11-24	メルク・パテント・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツングMerck Patent GmbH	液晶媒体
WO2019238567A1 (fr)	2018-06-11	2019-12-19	Merck Patent Gmbh	Milieu cristallin liquide
CN112313311B (zh)	2018-06-20	2024-08-06	默克专利股份有限公司	液晶介质
JP7447099B2 (ja)	2018-09-25	2024-03-11	メルクパテントゲゼルシャフトミットベシュレンクテルハフツング	アゾ色素
CN113166652B (zh)	2018-11-23	2025-01-21	默克专利股份有限公司	二色性染料组合物
CN113195683B (zh)	2018-12-19	2025-01-10	默克专利股份有限公司	用于切换元件的切换层
EP3983501B1 (fr)	2019-06-17	2025-02-26	Merck Patent GmbH	Modulateur de lumière à base de cristaux liquides
EP3839620B1 (fr)	2019-12-16	2025-02-26	Merck Patent GmbH	Dispositif de régulation de transmission de lumière
WO2022122871A1 (fr)	2020-12-11	2022-06-16	Merck Patent Gmbh	Dispositif de régulation de la transmission de lumière
WO2023094404A1 (fr)	2021-11-24	2023-06-01	Merck Patent Gmbh	Milieu de cristaux liquides et dispositif d'affichage à cristaux liquides
EP4720220A1 (fr)	2023-06-05	2026-04-08	Merck Patent GmbH	Milieu cristallin liquide
WO2025061649A1 (fr)	2023-09-20	2025-03-27	Merck Patent Gmbh	Milieu à cristaux liquides
KR20250113342A (ko)	2024-01-18	2025-07-25	메르크 파텐트 게엠베하	액정 매질
WO2025190813A1 (fr)	2024-03-11	2025-09-18	Merck Patent Gmbh	Milieu à cristaux liquides
WO2026052594A1 (fr)	2024-09-05	2026-03-12	Merck Patent Gmbh	Valve optique à base de cristaux liquides

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH351253A (de) *	1958-03-19	1961-01-15	Sandoz Ag	Haltbares Dispersionsfarbstoffpräparat
FR1431311A (fr) *	1964-03-25	1966-03-11	Ici Ltd	Colorants à base d'anthraquinone
NL6815799A (fr) *	1967-11-09	1969-05-13
DE2806733A1 (de) *	1978-02-17	1979-08-23	Bayer Ag	Anthrachinonfarbstoffe
DE2846229A1 (de) *	1978-10-24	1980-05-08	Bayer Ag	Verfahren zum faerben und bedrucken von cellulosefasern
US4304683A (en) *	1979-03-16	1981-12-08	Mitsui Toatsu Chemicals, Inc.	Composition for liquid crystal color display element
DE3014933A1 (de) *	1980-04-18	1981-10-29	Bayer Ag, 5090 Leverkusen	Fluessigkristalline materialien enthaltend anthrachinonfarbstoffe

1981
- 1981-04-18 DE DE19813115762 patent/DE3115762A1/de not_active Withdrawn
1982
- 1982-04-02 EP EP82102805A patent/EP0063713A1/fr not_active Withdrawn
- 1982-04-15 DD DD23902382A patent/DD204100A5/de unknown
- 1982-04-16 JP JP6263282A patent/JPS57182355A/ja active Pending

Also Published As

Publication number	Publication date
DE3115762A1 (de)	1982-11-11
JPS57182355A (en)	1982-11-10
EP0063713A1 (fr)	1982-11-03

Publication	Publication Date	Title
DD204100A5 (de)	1983-11-16	Dichroitische anthrachinonfarbstoffe enthaltende fluessigkeitskristalline dielektika
EP0069257B1 (fr)	1984-09-26	Diélectrique à base de cristaux liquides et dispositif d'affichage électrooptique
CH647252A5 (de)	1985-01-15	Dichroitische anthrachinonfarbstoffe und deren verwendung in fluessigkristallinen dielektrika fuer elektrooptisches anzeigeelement.
DE3401320C2 (fr)	1992-06-11
EP0085335B1 (fr)	1986-04-02	Diélectrique à cristaux liquides, nouveaux colorants, procédé pour leur préparation et élément d'affichage électro-optique
DE3009940C2 (fr)	1988-04-14
EP0047027A1 (fr)	1982-03-10	Mélange de cristaux liquides
EP0064193B1 (fr)	1984-07-25	Dérivés du 4,4'-bis-(cyclohexyl)-biphényl)-biphényle contenant du fluor, diélectriques contenant ces dérivés et élément indicateur électro-optique
DE3042391A1 (de)	1982-06-16	Fluorhaltige cyclohexylbiphenylderivate, diese enthaltende dielektrika und elektrooptisches anzeigeelement
DE68909922T2 (de)	1994-02-10	Thermochromische gemische.
CH642345A5 (de)	1984-04-13	2,3-dicyano-hydrochinon derivate.
DD148059A5 (de)	1981-05-06	Fluessigkristallmischung
DD204101A5 (de)	1983-11-16	Fluessigkristalline halogenverbindungen enthaltende dielektrika
DE3447359A1 (de)	1986-07-03	Fluessigkristalline phase
EP0019060B1 (fr)	1982-04-21	Dicétones, procédé pour leur préparation et leur utilisation comme composés de diélectriques à cristaux liquides
DE2834846A1 (de)	1979-03-01	Zweifarbige fluessigkeitskristall- zusammensetzungen
DD200090A5 (de)	1983-03-16	Fluessigkristallzusammensetzungen und ihre verwendung in anzeigevorrichtungen
CH645916A5 (de)	1984-10-31	Pleochroitische farbstoffe enthaltende fluessigkristallmassen.
EP0087056B1 (fr)	1986-01-15	Benzonitriles
DE3141309C2 (fr)	1991-05-02
EP0158252A2 (fr)	1985-10-16	Phase liquide cristalline
DE3510733A1 (de)	1986-09-25	Fluessigkristallphase
EP0031021B1 (fr)	1983-05-18	Tétrahydroquinazolines, procédé pour leur préparation, diélectriques à cristaux liquides les contenant et élément d'affichage électro-optique
DE3434335A1 (de)	1986-03-27	Fluessigkristalline phase
DD209643A5 (de)	1984-05-16	Dielektrische materialien