JPH0237948B2 - - Google Patents
Info
- Publication number
- JPH0237948B2 JPH0237948B2 JP57028232A JP2823282A JPH0237948B2 JP H0237948 B2 JPH0237948 B2 JP H0237948B2 JP 57028232 A JP57028232 A JP 57028232A JP 2823282 A JP2823282 A JP 2823282A JP H0237948 B2 JPH0237948 B2 JP H0237948B2
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- alkyl
- dye
- formula
- groups
- 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.)
- Expired - Lifetime
Links
- 239000000975 dye Substances 0.000 claims description 94
- 239000000203 mixture Substances 0.000 claims description 69
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 43
- -1 4-t-butylphenyl Chemical group 0.000 claims description 41
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 125000004149 thio group Chemical group *S* 0.000 claims description 18
- 239000001000 anthraquinone dye Substances 0.000 claims description 15
- 230000008033 biological extinction Effects 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 239000004973 liquid crystal related substance Substances 0.000 description 57
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 54
- 239000000463 material Substances 0.000 description 51
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 46
- 239000000047 product Substances 0.000 description 46
- 150000001875 compounds Chemical class 0.000 description 35
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- 150000004056 anthraquinones Chemical class 0.000 description 32
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
- 150000003573 thiols Chemical class 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 16
- 238000000034 method Methods 0.000 description 16
- 239000000243 solution Substances 0.000 description 12
- 239000000126 substance Substances 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 10
- 239000003208 petroleum Substances 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 239000000543 intermediate Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 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 6
- 238000001816 cooling Methods 0.000 description 6
- 239000013058 crude material Substances 0.000 description 6
- 230000005684 electric field Effects 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000001044 red dye Substances 0.000 description 5
- 239000001043 yellow dye Substances 0.000 description 5
- WLHCBQAPPJAULW-UHFFFAOYSA-N 4-methylbenzenethiol Chemical compound CC1=CC=C(S)C=C1 WLHCBQAPPJAULW-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000003098 cholesteric effect Effects 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 230000007704 transition Effects 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- WLEIVDIWTWFRLQ-UHFFFAOYSA-N 1,4,5,8-tetrakis(phenylsulfanyl)anthracene-9,10-dione Chemical compound C1=CC(SC=2C=CC=CC=2)=C2C(=O)C3=C(SC=4C=CC=CC=4)C=CC(SC=4C=CC=CC=4)=C3C(=O)C2=C1SC1=CC=CC=C1 WLEIVDIWTWFRLQ-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 239000001045 blue dye Substances 0.000 description 3
- CMKBCTPCXZNQKX-UHFFFAOYSA-N cyclohexanethiol Chemical compound SC1CCCCC1 CMKBCTPCXZNQKX-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 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 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- DUJPMUKIEFLXRE-UHFFFAOYSA-N 1,4,5,8-tetrachloroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC(Cl)=C2C(=O)C2=C1C(Cl)=CC=C2Cl DUJPMUKIEFLXRE-UHFFFAOYSA-N 0.000 description 2
- HGBWYYMBPQTZNS-UHFFFAOYSA-N 1,4,5-tris[(4-tert-butylphenyl)sulfanyl]-8-phenylsulfanylanthracene-9,10-dione Chemical compound C1=CC(C(C)(C)C)=CC=C1SC(C=1C(=O)C2=C(SC=3C=CC(=CC=3)C(C)(C)C)C=CC(SC=3C=CC(=CC=3)C(C)(C)C)=C2C(=O)C=11)=CC=C1SC1=CC=CC=C1 HGBWYYMBPQTZNS-UHFFFAOYSA-N 0.000 description 2
- JGDLEVAYNWLIKN-UHFFFAOYSA-N 1,5-bis(phenylsulfanyl)anthracene-9,10-dione Chemical class 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 2
- ICQYRMKYGAVTCP-UHFFFAOYSA-N 1-(4-tert-butylphenyl)sulfanyl-5-phenylsulfanylanthracene-9,10-dione Chemical compound C1=CC(C(C)(C)C)=CC=C1SC1=CC=CC2=C1C(=O)C1=CC=CC(SC=3C=CC=CC=3)=C1C2=O ICQYRMKYGAVTCP-UHFFFAOYSA-N 0.000 description 2
- ZTQZFTFKOMOJIM-UHFFFAOYSA-N 1-chloro-5-phenylsulfanylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C=3C(Cl)=CC=CC=3C(=O)C2=C1SC1=CC=CC=C1 ZTQZFTFKOMOJIM-UHFFFAOYSA-N 0.000 description 2
- WLPATYNQCGVFFH-UHFFFAOYSA-N 2-phenylbenzonitrile Chemical group N#CC1=CC=CC=C1C1=CC=CC=C1 WLPATYNQCGVFFH-UHFFFAOYSA-N 0.000 description 2
- NIFAOMSJMGEFTQ-UHFFFAOYSA-N 4-methoxybenzenethiol Chemical compound COC1=CC=C(S)C=C1 NIFAOMSJMGEFTQ-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 125000005110 aryl thio group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000013375 chromatographic separation Methods 0.000 description 2
- HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 230000031700 light absorption Effects 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 230000000802 nitrating effect Effects 0.000 description 2
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 239000013014 purified material Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- CYCVXTXWERXGJY-UHFFFAOYSA-N 1,2-dichloro-3-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C([N+](=O)[O-])C(Cl)=C2Cl CYCVXTXWERXGJY-UHFFFAOYSA-N 0.000 description 1
- JTYJHBWDNMUPSP-UHFFFAOYSA-N 1,4,5-trichloro-8-nitroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC(Cl)=C2C(=O)C2=C1C(Cl)=CC=C2[N+](=O)[O-] JTYJHBWDNMUPSP-UHFFFAOYSA-N 0.000 description 1
- WSNXSZVGSATKJS-UHFFFAOYSA-N 1,4,5-tris[(4-phenylphenyl)sulfanyl]-8-phenylsulfanylanthracene-9,10-dione Chemical compound C1=CC(SC=2C=CC(=CC=2)C=2C=CC=CC=2)=C2C(=O)C3=C(SC=4C=CC(=CC=4)C=4C=CC=CC=4)C=CC(SC=4C=CC(=CC=4)C=4C=CC=CC=4)=C3C(=O)C2=C1SC1=CC=CC=C1 WSNXSZVGSATKJS-UHFFFAOYSA-N 0.000 description 1
- BBEQBQNWFVVYFS-UHFFFAOYSA-N 1,5-bis[(4-tert-butylphenyl)sulfanyl]anthracene-9,10-dione Chemical compound C1=CC(C(C)(C)C)=CC=C1SC1=CC=CC2=C1C(=O)C1=CC=CC(SC=3C=CC(=CC=3)C(C)(C)C)=C1C2=O BBEQBQNWFVVYFS-UHFFFAOYSA-N 0.000 description 1
- 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 1
- JWVYUCDXBHBMSI-UHFFFAOYSA-N 1-(4-heptylphenyl)cyclohexa-2,4-diene-1-carbonitrile Chemical group C1=CC(CCCCCCC)=CC=C1C1(C#N)C=CC=CC1 JWVYUCDXBHBMSI-UHFFFAOYSA-N 0.000 description 1
- LKAXNYHCEJFLEF-UHFFFAOYSA-N 1-(4-nonylphenyl)sulfanyl-5-phenylsulfanylanthracene-9,10-dione Chemical compound C1=CC(CCCCCCCCC)=CC=C1SC1=CC=CC2=C1C(=O)C1=CC=CC(SC=3C=CC=CC=3)=C1C2=O LKAXNYHCEJFLEF-UHFFFAOYSA-N 0.000 description 1
- DUWVOPSWFADBAU-UHFFFAOYSA-N 1-(4-octoxyphenyl)cyclohexa-2,4-diene-1-carbonitrile Chemical group C1=CC(OCCCCCCCC)=CC=C1C1(C#N)C=CC=CC1 DUWVOPSWFADBAU-UHFFFAOYSA-N 0.000 description 1
- QAYSSYLXPUKOAV-UHFFFAOYSA-N 1-(4-pentylphenyl)cyclohexa-2,4-diene-1-carbonitrile Chemical group C1=CC(CCCCC)=CC=C1C1(C#N)C=CC=CC1 QAYSSYLXPUKOAV-UHFFFAOYSA-N 0.000 description 1
- YQOKHEJRRIAJJZ-UHFFFAOYSA-N 1-(4-tert-butylphenyl)sulfanylanthracene-9,10-dione Chemical compound C1=CC(C(C)(C)C)=CC=C1SC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O YQOKHEJRRIAJJZ-UHFFFAOYSA-N 0.000 description 1
- XPESVNUBCSBIOW-UHFFFAOYSA-N 1-[2-(4-pentylphenyl)phenyl]cyclohexa-2,4-diene-1-carbonitrile Chemical group C(#N)C1(CC=CC=C1)C=1C(=CC=CC=1)C1=CC=C(C=C1)CCCCC XPESVNUBCSBIOW-UHFFFAOYSA-N 0.000 description 1
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- HMKWKLSAPLPDRS-UHFFFAOYSA-N 1-butyl-4,8-bis(butylamino)-5-phenylsulfanyl-10-sulfanylideneanthracen-9-one Chemical compound C1=2C(=S)C3=C(NCCCC)C=CC(CCCC)=C3C(=O)C=2C(NCCCC)=CC=C1SC1=CC=CC=C1 HMKWKLSAPLPDRS-UHFFFAOYSA-N 0.000 description 1
- VOZLLWQPJJSWPR-UHFFFAOYSA-N 1-chloro-5-nitroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] VOZLLWQPJJSWPR-UHFFFAOYSA-N 0.000 description 1
- 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 1
- NQDIFFUKLIFBDC-UHFFFAOYSA-N 1-dodecylsulfanyl-5-phenylsulfanylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C=3C(SCCCCCCCCCCCC)=CC=CC=3C(=O)C2=C1SC1=CC=CC=C1 NQDIFFUKLIFBDC-UHFFFAOYSA-N 0.000 description 1
- ADJALGQQZBTLSY-UHFFFAOYSA-N 1-naphthalen-2-ylsulfanyl-5-phenylsulfanylanthracene-9,10-dione Chemical compound C=12C(=O)C3=CC=CC(SC=4C=C5C=CC=CC5=CC=4)=C3C(=O)C2=CC=CC=1SC1=CC=CC=C1 ADJALGQQZBTLSY-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- CZJZMSRDRZJNSB-UHFFFAOYSA-N 4,5-diamino-1,8-dihydroxy-2,7-bis(2-methylpropyl)anthracene-9,10-dione Chemical compound C1=C(CC(C)C)C(O)=C2C(=O)C3=C(O)C(CC(C)C)=CC(N)=C3C(=O)C2=C1N CZJZMSRDRZJNSB-UHFFFAOYSA-N 0.000 description 1
- AUIVZGVKJOSWQE-UHFFFAOYSA-N 4-(1-pentylcyclohexyl)benzonitrile Chemical compound C=1C=C(C#N)C=CC=1C1(CCCCC)CCCCC1 AUIVZGVKJOSWQE-UHFFFAOYSA-N 0.000 description 1
- VKXBZDWMYOSYKP-UHFFFAOYSA-N 4-(1-propylcyclohexyl)benzonitrile Chemical compound C=1C=C(C#N)C=CC=1C1(CCC)CCCCC1 VKXBZDWMYOSYKP-UHFFFAOYSA-N 0.000 description 1
- AGMGXWMXLSMNCM-UHFFFAOYSA-N 4-(3-pentyl-4-bicyclo[2.2.2]octanyl)benzonitrile Chemical compound CCCCCC1CC(CC2)CCC12C1=CC=C(C#N)C=C1 AGMGXWMXLSMNCM-UHFFFAOYSA-N 0.000 description 1
- IWVULGGRWKQZTO-UHFFFAOYSA-N 4-(3-propyl-4-bicyclo[2.2.2]octanyl)benzonitrile Chemical compound CCCC1CC(CC2)CCC12C1=CC=C(C#N)C=C1 IWVULGGRWKQZTO-UHFFFAOYSA-N 0.000 description 1
- QZIFUYPVLZULNL-UHFFFAOYSA-N 4-[4-(1-pentylcyclohexyl)phenyl]benzonitrile Chemical group C=1C=C(C=2C=CC(=CC=2)C#N)C=CC=1C1(CCCCC)CCCCC1 QZIFUYPVLZULNL-UHFFFAOYSA-N 0.000 description 1
- UVFLEUVMFWRYAU-UHFFFAOYSA-N 4-anilino-5-(4-methylphenyl)sulfanyl-1-phenylsulfanylanthracene-9,10-dione Chemical compound C1=CC(C)=CC=C1SC1=CC=CC2=C1C(=O)C1=C(NC=3C=CC=CC=3)C=CC(SC=3C=CC=CC=3)=C1C2=O UVFLEUVMFWRYAU-UHFFFAOYSA-N 0.000 description 1
- PLXMOAALOJOTIY-FPTXNFDTSA-N Aesculin Natural products OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)[C@H]1Oc2cc3C=CC(=O)Oc3cc2O PLXMOAALOJOTIY-FPTXNFDTSA-N 0.000 description 1
- 241000277306 Esocidae Species 0.000 description 1
- 244000171726 Scotch broom Species 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 125000005366 cycloalkylthio group Chemical group 0.000 description 1
- NLUNLVTVUDIHFE-UHFFFAOYSA-N cyclooctylcyclooctane Chemical compound C1CCCCCCC1C1CCCCCCC1 NLUNLVTVUDIHFE-UHFFFAOYSA-N 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000012812 general test Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004708 n-butylthio group Chemical group C(CCC)S* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical class CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001048 orange dye Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000004758 synthetic textile Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001052 transient effect Effects 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
- C09B1/56—Mercapto-anthraquinones
- C09B1/58—Mercapto-anthraquinones with mercapto groups substituted by aliphatic, cycloaliphatic, araliphatic or aryl radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Liquid Crystal (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8105888 | 1981-02-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57158262A JPS57158262A (en) | 1982-09-30 |
| JPH0237948B2 true JPH0237948B2 (de) | 1990-08-28 |
Family
ID=10519947
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2823282A Granted JPS57158262A (en) | 1981-02-25 | 1982-02-25 | Water-soluble and ionic substituent-free anthraquinone dye and anthraquinone dye composition |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS57158262A (de) |
| GB (1) | GB2094822B (de) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| GB2155945B (en) * | 1981-02-25 | 1986-03-26 | Secr Defence | Substituted thioanthraquinone dyes |
| JPS5927956A (ja) * | 1982-07-17 | 1984-02-14 | バイエル・アクチエンゲゼルシヤフト | アントラキノン染料を含む二色性物質及び新規なアントラキノン染料 |
| DE3380962D1 (de) * | 1982-08-18 | 1990-01-18 | Secr Defence Brit | Organische materialien fuer eine fluessigkristallvorrichtung. |
| GB2126601B (en) * | 1982-08-18 | 1986-12-10 | Secr Defence | Guest-host liquid crystal materials |
| DE3244815A1 (de) * | 1982-12-03 | 1984-06-07 | Bayer Ag, 5090 Leverkusen | Anthrachinonfarbstoffe, ihre herstellung und verwendung sowie dichroitisches material enthaltend anthrachinonfarbstoffe |
| DE3603266A1 (de) * | 1986-02-04 | 1987-08-06 | Roehm Gmbh | Vorrichtung zur reversibeln, optischen datenspeicherung (ii) |
| DE3603268A1 (de) * | 1986-02-04 | 1987-09-24 | Roehm Gmbh | Verfahren zur reversiblen, optischen datenspeicherung (iii) |
| DE3603267A1 (de) * | 1986-02-04 | 1987-08-06 | Roehm Gmbh | Vorrichtung zur reversiblen, optischen datenspeicherung (i) |
| US4841057A (en) * | 1987-01-13 | 1989-06-20 | Mitsubishi Chemical Industries Limited | Cyclic imido anthraquinone compounds |
| US5595686A (en) * | 1994-09-02 | 1997-01-21 | Shin-Etsu Chemical Co., Ltd. | Silacyclohexane compounds, a liquid crystal composition comprising the same and a liquid crystal device comprising the composition |
| WO2014090373A1 (en) | 2012-12-13 | 2014-06-19 | Merck Patent Gmbh | Liquid-crystalline medium |
| US10114264B2 (en) | 2013-03-05 | 2018-10-30 | Merck Patent Gmbh | Device for regulating the passage of energy |
| US10108058B2 (en) | 2013-05-08 | 2018-10-23 | Merck Patent Gmbh | Device for regulating the passage of energy |
| JP6563384B2 (ja) | 2013-05-24 | 2019-08-21 | 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Ｍｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | 二色性色素化合物を含むエネルギー通過調節用デバイス |
| WO2015090506A1 (de) | 2013-12-19 | 2015-06-25 | Merck Patent Gmbh | Vorrichtung zur regulierung des lichtdurchtritts |
| DE102015005800A1 (de) | 2015-05-06 | 2016-11-10 | Merck Patent Gmbh | Thiadiazolochinoxalinderivate |
| KR102602326B1 (ko) | 2015-07-10 | 2023-11-16 | 메르크 파텐트 게엠베하 | 다이티오-알킬-피롤로-피롤 및 염료로서의 이의 용도 |
| WO2018001919A1 (en) | 2016-06-28 | 2018-01-04 | Merck Patent Gmbh | Liquid crystalline medium |
| 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 |
| US11667845B2 (en) | 2018-06-11 | 2023-06-06 | Merck Patent Gmbh | Liquid crystalline medium |
| US20220275277A1 (en) | 2018-06-20 | 2022-09-01 | Merck Patent Gmbh | Liquid crystalline medium |
| US11702597B2 (en) | 2018-09-25 | 2023-07-18 | Merck Patent Gmbh | Azo dye |
| CN113166652A (zh) | 2018-11-23 | 2021-07-23 | 默克专利股份有限公司 | 二色性染料组合物 |
| EP3898893A1 (de) | 2018-12-19 | 2021-10-27 | Merck Patent GmbH | Schaltschichten zur verwendung in einem schaltelement |
| KR20220024586A (ko) | 2019-06-17 | 2022-03-03 | 메르크 파텐트 게엠베하 | 액정-기반 광 밸브 |
| EP3839620A1 (de) | 2019-12-16 | 2021-06-23 | Merck Patent GmbH | Vorrichtung zur regelung der lichttransmission |
| US20240134218A1 (en) | 2020-12-11 | 2024-04-25 | Merck Patent Gmbh | Device for the regulation of light transmission |
| EP4306616A1 (de) * | 2021-03-11 | 2024-01-17 | Nippon Kayaku Kabushiki Kaisha | Anthrachinonverbindung, flüssigkristallzusammensetzung mit dieser verbindung und abdimmerelement |
| WO2023094404A1 (en) | 2021-11-24 | 2023-06-01 | Merck Patent Gmbh | Liquid crystal medium and liquid crystal display |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4986683A (de) * | 1972-12-07 | 1974-08-20 | ||
| JPS5551882A (en) * | 1978-10-06 | 1980-04-15 | Bayer Ag | Dyeing and printing of cellulosic fabric |
-
1982
- 1982-02-05 GB GB8203421A patent/GB2094822B/en not_active Expired
- 1982-02-25 JP JP2823282A patent/JPS57158262A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4986683A (de) * | 1972-12-07 | 1974-08-20 | ||
| JPS5551882A (en) * | 1978-10-06 | 1980-04-15 | Bayer Ag | Dyeing and printing of cellulosic fabric |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2094822B (en) | 1986-03-05 |
| JPS57158262A (en) | 1982-09-30 |
| GB2094822A (en) | 1982-09-22 |
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