JPH0428693B2 - - Google Patents
Info
- Publication number
- JPH0428693B2 JPH0428693B2 JP57070563A JP7056382A JPH0428693B2 JP H0428693 B2 JPH0428693 B2 JP H0428693B2 JP 57070563 A JP57070563 A JP 57070563A JP 7056382 A JP7056382 A JP 7056382A JP H0428693 B2 JPH0428693 B2 JP H0428693B2
- Authority
- JP
- Japan
- Prior art keywords
- compounds
- formula
- trans
- liquid crystal
- alkyl
- 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
- 150000001875 compounds Chemical class 0.000 claims abstract description 52
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- 125000001424 substituent group Chemical group 0.000 claims abstract description 10
- 239000011737 fluorine Substances 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract 5
- 239000004973 liquid crystal related substance Substances 0.000 claims description 34
- 239000003989 dielectric material Substances 0.000 claims description 20
- -1 tetrafluoroborate Chemical compound 0.000 claims description 18
- 239000000463 material Substances 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 210000002858 crystal cell Anatomy 0.000 claims description 3
- 230000000802 nitrating effect Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims description 2
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000007788 liquid Substances 0.000 abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 abstract description 3
- 239000002178 crystalline material Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 20
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- 239000012071 phase Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- OLUVNSGCKHZQJQ-UHFFFAOYSA-N 1-cyclohexyl-4-(4-cyclohexylphenyl)benzene Chemical group C1CCCCC1C1=CC=C(C=2C=CC(=CC=2)C2CCCCC2)C=C1 OLUVNSGCKHZQJQ-UHFFFAOYSA-N 0.000 description 7
- 230000003287 optical effect Effects 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 125000001153 fluoro group Chemical group F* 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000012954 diazonium Substances 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 4
- 229910017604 nitric acid Inorganic materials 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- FXUZMBFYPTWFNA-PCYFZWJMSA-N C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC(=C(C=C1)C1=C(C=C(C=C1)[C@@H]1CC[C@H](CC1)CCCCC)[N+](=O)[O-])[N+](=O)[O-] Chemical group C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC(=C(C=C1)C1=C(C=C(C=C1)[C@@H]1CC[C@H](CC1)CCCCC)[N+](=O)[O-])[N+](=O)[O-] FXUZMBFYPTWFNA-PCYFZWJMSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical class C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000006396 nitration reaction Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- FURZYCFZFBYJBT-UHFFFAOYSA-N 4-(4-pentylcyclohexyl)benzonitrile Chemical compound C1CC(CCCCC)CCC1C1=CC=C(C#N)C=C1 FURZYCFZFBYJBT-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VTSFTGCYPYGMDG-OEOGMAASSA-N C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC(=C(C=C1)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCCCC)N Chemical group C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC(=C(C=C1)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCCCC)N VTSFTGCYPYGMDG-OEOGMAASSA-N 0.000 description 2
- SRSXDINENLOAON-HDJSIYSDSA-N C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC(=C(N)C=C1)[N+](=O)[O-] Chemical compound C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC(=C(N)C=C1)[N+](=O)[O-] SRSXDINENLOAON-HDJSIYSDSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 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
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical class C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- PKORYTIUMAOPED-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinazoline Chemical class 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
- QQFSIGWYINAJOB-UHFFFAOYSA-N 1,4-dicyclohexylbenzene Chemical class C1CCCCC1C1=CC=C(C2CCCCC2)C=C1 QQFSIGWYINAJOB-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
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 1
- RAYZALBEMJMGEA-UHFFFAOYSA-N 1-cyclohexylnaphthalene Chemical class C1CCCCC1C1=CC=CC2=CC=CC=C12 RAYZALBEMJMGEA-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
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- PJPLBHHDTUICNN-UHFFFAOYSA-N 4-(4-butylphenyl)benzonitrile Chemical group C1=CC(CCCC)=CC=C1C1=CC=C(C#N)C=C1 PJPLBHHDTUICNN-UHFFFAOYSA-N 0.000 description 1
- BBHJTCADCKZYSO-UHFFFAOYSA-N 4-(4-ethylcyclohexyl)benzonitrile Chemical compound C1CC(CC)CCC1C1=CC=C(C#N)C=C1 BBHJTCADCKZYSO-UHFFFAOYSA-N 0.000 description 1
- DLLIPJSMDJCZRF-UHFFFAOYSA-N 4-(4-ethylphenyl)benzonitrile Chemical group C1=CC(CC)=CC=C1C1=CC=C(C#N)C=C1 DLLIPJSMDJCZRF-UHFFFAOYSA-N 0.000 description 1
- GQPFCPRCGONDNN-UHFFFAOYSA-N 4-(5-propyl-1,3-dioxan-2-yl)benzonitrile Chemical compound O1CC(CCC)COC1C1=CC=C(C#N)C=C1 GQPFCPRCGONDNN-UHFFFAOYSA-N 0.000 description 1
- 239000005243 4-(trans-4-Ethylcyclohexyl)benzonitrile Substances 0.000 description 1
- AITQOXOBSMXBRV-UHFFFAOYSA-N 4-[4-(4-pentylphenyl)phenyl]benzonitrile Chemical group C1=CC(CCCCC)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C#N)C=C1 AITQOXOBSMXBRV-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- WHMWGCAMRVNVTP-FVOQYNOISA-N C(C)O[C@@H]1CC[C@H](CC1)C1=CC(=C(C=C1)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCC)F Chemical group C(C)O[C@@H]1CC[C@H](CC1)C1=CC(=C(C=C1)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCC)F WHMWGCAMRVNVTP-FVOQYNOISA-N 0.000 description 1
- RGIBJVICJGCAFD-CHDDOINTSA-N C(C)[C@@H]1CC[C@H](CC1)C1=CC(=C(C=C1)C1=C(C=C(C=C1)[C@@H]1CC[C@H](CC1)CC)F)F Chemical group C(C)[C@@H]1CC[C@H](CC1)C1=CC(=C(C=C1)C1=C(C=C(C=C1)[C@@H]1CC[C@H](CC1)CC)F)F RGIBJVICJGCAFD-CHDDOINTSA-N 0.000 description 1
- KTZHXORABSNNBH-JENPDSIZSA-N C(C)[C@@H]1CC[C@H](CC1)C1=CC(=C(C=C1)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CC)F Chemical group C(C)[C@@H]1CC[C@H](CC1)C1=CC(=C(C=C1)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CC)F KTZHXORABSNNBH-JENPDSIZSA-N 0.000 description 1
- IPUJOIJNQUPKIJ-AKMOFFSESA-N C(C)[C@@H]1CC[C@H](CC1)C1=CC(=C(C=C1)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCC)F Chemical group C(C)[C@@H]1CC[C@H](CC1)C1=CC(=C(C=C1)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCC)F IPUJOIJNQUPKIJ-AKMOFFSESA-N 0.000 description 1
- LJNNEYIENVDADI-ZWGSZDQZSA-N C(CC)[C@@H]1CC[C@H](CC1)C1=CC(=C(C=C1)C1=C(C=C(C=C1)[C@@H]1CC[C@H](CC1)CCC)F)F Chemical group C(CC)[C@@H]1CC[C@H](CC1)C1=CC(=C(C=C1)C1=C(C=C(C=C1)[C@@H]1CC[C@H](CC1)CCC)F)F LJNNEYIENVDADI-ZWGSZDQZSA-N 0.000 description 1
- ZINLSGIRSNHDMF-AKMOFFSESA-N C(CC)[C@@H]1CC[C@H](CC1)C1=CC(=C(C=C1F)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCC)F Chemical group C(CC)[C@@H]1CC[C@H](CC1)C1=CC(=C(C=C1F)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCC)F ZINLSGIRSNHDMF-AKMOFFSESA-N 0.000 description 1
- VCLAXMQRVBWKFN-KKLUKGEUSA-N C(CCC)[C@@H]1CC[C@H](CC1)C1=CC(=C(C=C1)C1=C(C=C(C=C1)[C@@H]1CC[C@H](CC1)CCCC)F)F Chemical group C(CCC)[C@@H]1CC[C@H](CC1)C1=CC(=C(C=C1)C1=C(C=C(C=C1)[C@@H]1CC[C@H](CC1)CCCC)F)F VCLAXMQRVBWKFN-KKLUKGEUSA-N 0.000 description 1
- QXGNBFZHDIAWIP-AFMUELSESA-N C(CCC)[C@@H]1CC[C@H](CC1)C1=CC(=C(C=C1)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCCC)F Chemical group C(CCC)[C@@H]1CC[C@H](CC1)C1=CC(=C(C=C1)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCCC)F QXGNBFZHDIAWIP-AFMUELSESA-N 0.000 description 1
- RKIIZCXOHWYGCL-PCYFZWJMSA-N C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC(=C(C=C1)C1=C(C=C(C=C1)[C@@H]1CC[C@H](CC1)CCCCC)F)F Chemical group C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC(=C(C=C1)C1=C(C=C(C=C1)[C@@H]1CC[C@H](CC1)CCCCC)F)F RKIIZCXOHWYGCL-PCYFZWJMSA-N 0.000 description 1
- IDUIJLQLTMWWBV-OEOGMAASSA-N C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC(=C(C=C1)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCCCC)[N+](=O)[O-] Chemical group C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC(=C(C=C1)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCCCC)[N+](=O)[O-] IDUIJLQLTMWWBV-OEOGMAASSA-N 0.000 description 1
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- OGCKMDSDEJZJIZ-JCNLHEQBSA-N C(CCCCC)[C@H]1CO[C@@H](OC1)C1=CC=C(C#N)C=C1 Chemical compound C(CCCCC)[C@H]1CO[C@@H](OC1)C1=CC=C(C#N)C=C1 OGCKMDSDEJZJIZ-JCNLHEQBSA-N 0.000 description 1
- YYAVXASAKUOZJJ-KOMQPUFPSA-N C1C[C@@H](CCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 YYAVXASAKUOZJJ-KOMQPUFPSA-N 0.000 description 1
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- SYCNHFWYTQQMNG-AFMUELSESA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C=2C=CC(=CC=2)[C@@H]2CC[C@@H](CCC)CC2)C(F)=C1 Chemical group C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C=2C=CC(=CC=2)[C@@H]2CC[C@@H](CCC)CC2)C(F)=C1 SYCNHFWYTQQMNG-AFMUELSESA-N 0.000 description 1
- NSGMZTNTQKRAFA-UAPYVXQJSA-N C1C[C@@H](CCCCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCCCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 NSGMZTNTQKRAFA-UAPYVXQJSA-N 0.000 description 1
- NBOMAZVNDYECTP-DANJKSSVSA-N CCCCC[C@H]1CC[C@@H](CC1)c1ccc(cc1)-c1ccc(cc1)[C@H]1CC[C@H](CCCCC)CC1 Chemical group CCCCC[C@H]1CC[C@@H](CC1)c1ccc(cc1)-c1ccc(cc1)[C@H]1CC[C@H](CCCCC)CC1 NBOMAZVNDYECTP-DANJKSSVSA-N 0.000 description 1
- TYXZVPMEKLRAGX-OEOGMAASSA-N CCCCC[C@H]1CC[C@@H](CC1)c1ccc(cc1)-c1ccc(cc1F)[C@H]1CC[C@H](CCCCC)CC1 Chemical group CCCCC[C@H]1CC[C@@H](CC1)c1ccc(cc1)-c1ccc(cc1F)[C@H]1CC[C@H](CCCCC)CC1 TYXZVPMEKLRAGX-OEOGMAASSA-N 0.000 description 1
- SRJLZDPWUSOULH-LWPGTKICSA-N CCC[C@H]1CC[C@@H](CC1)c1ccc(cc1)-c1ccc(cc1F)[C@H]1CC[C@H](CCC)CC1 Chemical group CCC[C@H]1CC[C@@H](CC1)c1ccc(cc1)-c1ccc(cc1F)[C@H]1CC[C@H](CCC)CC1 SRJLZDPWUSOULH-LWPGTKICSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 150000001482 benzyl phenyl ethers Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 150000004074 biphenyls Chemical class 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 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
- 238000007796 conventional method Methods 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 125000002243 cyclohexanonyl group Chemical class *C1(*)C(=O)C(*)(*)C(*)(*)C(*)(*)C1(*)* 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
- 150000002666 cyclohexyl cyclohexanecarboxylates Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000002221 fluorine Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000031700 light absorption Effects 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
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 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
- 150000002790 naphthalenes Chemical class 0.000 description 1
- JCZMXVGQBBATMY-UHFFFAOYSA-N nitro acetate Chemical compound CC(=O)O[N+]([O-])=O JCZMXVGQBBATMY-UHFFFAOYSA-N 0.000 description 1
- JBCXQJHXIYZCNI-UHFFFAOYSA-N nitro benzoate Chemical compound [O-][N+](=O)OC(=O)C1=CC=CC=C1 JBCXQJHXIYZCNI-UHFFFAOYSA-N 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 229910001495 sodium tetrafluoroborate Inorganic materials 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 150000001629 stilbenes Chemical class 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 150000001911 terphenyls Chemical class 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical class C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 150000001608 tolans Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/12—Polycyclic non-condensed hydrocarbons
-
- 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
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/12—Polycyclic non-condensed hydrocarbons
- C07C15/14—Polycyclic non-condensed hydrocarbons all phenyl groups being directly linked
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/18—Polycyclic aromatic halogenated hydrocarbons
-
- 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
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/3021—Cy-Ph-Ph-Cy
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813117152 DE3117152A1 (de) | 1981-04-30 | 1981-04-30 | "fluorhaltige 4,4'-bis-(cyclohexyl)-biphenylderivate, diese enthaltende dielektrika und elektrooptisches anzeigeelement" |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57185231A JPS57185231A (en) | 1982-11-15 |
| JPH0428693B2 true JPH0428693B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-05-15 |
Family
ID=6131173
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57070563A Granted JPS57185231A (en) | 1981-04-30 | 1982-04-28 | Fluorine-containing 4,4'-bis-(cyclohexyl)- biphenyl derivative and dielectric body and electrooptical display element containing same |
Country Status (10)
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0084194B1 (de) * | 1982-01-14 | 1986-04-30 | MERCK PATENT GmbH | Flüssigkristallmischungen |
| DE3208089A1 (de) * | 1982-03-06 | 1983-09-08 | Merck Patent Gmbh, 6100 Darmstadt | Halogenbiphenylderivate |
| DE3209178A1 (de) * | 1982-03-13 | 1983-09-15 | Merck Patent Gmbh, 6100 Darmstadt | Polyhalogenaromaten |
| US4512636A (en) * | 1982-06-15 | 1985-04-23 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdon Of Great Britian And Northern Ireland Of Whitehall | Liquid crystal compounds |
| DE3370818D1 (en) * | 1982-07-16 | 1987-05-14 | Chisso Corp | High temperature liquid crystal substances having four rings and liquid crystal compositions containing the same |
| GB2134110B (en) * | 1983-01-26 | 1987-01-14 | Secr Defence | Liquid crystal 1-fluorophenyl-2-cyclohexyl-ethanes |
| GB8319849D0 (en) | 1983-07-22 | 1983-08-24 | Secr Defence | Compounds containing fluorobiphenyl group |
| EP0158252B1 (de) * | 1984-04-07 | 1988-12-21 | MERCK PATENT GmbH | Flüssigkristalline Phase |
| FR2595094B1 (fr) * | 1986-02-28 | 1988-08-12 | Commissariat Energie Atomique | Difluoro-2,2' alcoxy-4 hydroxy-4' biphenyles et leurs derives, leur procede de fabrication et leur utilisation dans des dispositifs d'affichage a cristaux liquides |
| JPS62155517U (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1986-03-25 | 1987-10-02 | ||
| US4879061A (en) * | 1986-09-29 | 1989-11-07 | Crystaloid Electronics Co. | Liquid crystalline materials and method of making same |
| GB8724458D0 (en) * | 1987-10-19 | 1987-11-25 | Secr Defence | Lateral cyano terphenyls |
| GB2216523B (en) * | 1988-03-10 | 1991-12-11 | Merck Patent Gmbh | Dihalogenobenzene liquid crystalline compounds |
| US5211878A (en) * | 1988-03-10 | 1993-05-18 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Difluorobenzonitrile derivatives |
| US5279764A (en) * | 1988-03-10 | 1994-01-18 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Dihalogenobenzene derivatives |
| EP0406468B1 (en) * | 1989-07-06 | 1992-10-21 | Sharp Corporation | Nematic-liquid-crystal composition for active matrix application |
| US5171469A (en) * | 1989-08-22 | 1992-12-15 | Merck Patent Gesellschaft Mit Beschraenkter Haftung | Liquid-crystal matrix display |
| DE4000534C2 (de) * | 1989-12-19 | 2003-08-14 | Merck Patent Gmbh | 1,4-Disubstituierte 2,6-Difluorbenzolverbindungen und flüssigkristallines Medium |
| KR0184869B1 (ko) | 1989-12-06 | 1999-05-15 | 위르겐 호이만 | 1,4-이치환된 2,6-디플루오로벤젠 화합물 및 액정 매질 |
| WO1991008184A2 (de) * | 1989-12-06 | 1991-06-13 | MERCK Patent Gesellschaft mit beschränkter Haftung | 1,4-disubstituierte 2,6-difluorbenzolverbindungen und flüssigkristallines medium |
| US5389289A (en) * | 1990-03-09 | 1995-02-14 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Liquid-crystalline medium |
| WO1991013947A2 (de) * | 1990-03-09 | 1991-09-19 | MERCK Patent Gesellschaft mit beschränkter Haftung | Flüssigkristallines medium |
| DE69206016T2 (de) * | 1991-03-04 | 1996-05-02 | Merck Patent Gmbh | Nematische Flüssigkristallzusammensetzung für aktiv matrix Verwendung. |
| TW386106B (en) | 1996-03-28 | 2000-04-01 | Chisso Corp | Alkenyl compounds, liquid crystal compositions, and liquid crystal display devices |
| DE19831865A1 (de) | 1998-07-16 | 2000-01-20 | Basf Ag | Verwendung von Schwefel-organischen Verbindungen als Mittel zur bathochromen Verschiebung der UV/Vis-Absorptionsbande von Carotinoiden |
| DE10032346A1 (de) | 2000-07-04 | 2002-01-17 | Merck Patent Gmbh | Flüssigkristallines Medium |
| JP5225531B2 (ja) * | 2000-12-19 | 2013-07-03 | 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 | 負のｄｃ異方性の四環式化合物および液晶媒体 |
| EP2337829B1 (en) * | 2008-09-17 | 2013-04-17 | Tetragon LC Chemie AG | Chiral compounds, cholesteric and ferroelectric liquid crystal compositions comprising these chiral compounds, and liquid crystal displays comprising these liquid crystal compositions |
| KR102588036B1 (ko) * | 2017-03-02 | 2023-10-11 | 닛산 가가쿠 가부시키가이샤 | 액정 배향제, 액정 배향막 및 액정 표시 소자 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2636684C3 (de) * | 1976-08-14 | 1980-06-19 | Merck Patent Gmbh, 6100 Darmstadt | Phenylcyclohexanderivate und ihre Verwendung in flüssigkristallinen Dielektrika |
| GB2039937A (en) * | 1979-01-17 | 1980-08-20 | Gray G | Liquid crystal composition |
| EP0019665B2 (de) * | 1979-05-28 | 1987-12-16 | MERCK PATENT GmbH | Flüssigkristalline Verbindungen |
| DE2927277A1 (de) * | 1979-07-06 | 1981-01-08 | Merck Patent Gmbh | Cyclohexylbiphenyle, verfahren zu ihrer herstellung, diese enthaltende dielektrika und elektrooptisches anzeigeelement |
| DE2933563A1 (de) * | 1979-07-18 | 1981-02-05 | Bbc Brown Boveri & Cie | Anisotrope verbindungen mit negativer dk-anisotropie |
| DE2939782A1 (de) * | 1979-09-07 | 1981-04-02 | BBC AG Brown, Boveri & Cie., Baden, Aargau | Aromatische verbindungen mit negativer dk-anisotropie |
| DE2948836A1 (de) * | 1979-12-05 | 1981-06-11 | Merck Patent Gmbh, 6100 Darmstadt | Partiell hydrierte oligo-1,4-phenylene, diese enthaltende dielektrika und elektrooptisches anzeigeelement |
| DE3001661A1 (de) * | 1979-12-17 | 1981-06-25 | BBC AG Brown, Boveri & Cie., Baden, Aargau | Anisotrope cyclohexylaether |
| JPS5749688A (en) * | 1980-09-10 | 1982-03-23 | Toshiba Corp | Liquid crystal display element |
| US4405488A (en) * | 1980-10-09 | 1983-09-20 | Chisso Corporation | Liquid-crystalline halogenobenzene derivatives |
| JPS57159730A (en) * | 1981-03-28 | 1982-10-01 | Chisso Corp | 3-(trans-4'-(trans-4"-alkylcyclohexyl)cyclohexyl) chlorobenzene |
| DE3040632A1 (de) * | 1980-10-29 | 1982-05-27 | Merck Patent Gmbh, 6100 Darmstadt | Cyclohexylphenylderivate, diese enthaltende dielektrika und elektrooptisches anzeigeelement |
| DE3042391A1 (de) * | 1980-11-10 | 1982-06-16 | Merck Patent Gmbh, 6100 Darmstadt | Fluorhaltige cyclohexylbiphenylderivate, diese enthaltende dielektrika und elektrooptisches anzeigeelement |
| US4422951A (en) * | 1981-04-02 | 1983-12-27 | Chisso Corporation | Liquid crystal benzene derivatives |
| JPS57165326A (en) * | 1981-04-03 | 1982-10-12 | Asahi Glass Co Ltd | Trans-4-alkyl-(4'-fluorobiphenyl-4)cyclohexane |
-
1981
- 1981-04-30 DE DE19813117152 patent/DE3117152A1/de not_active Withdrawn
-
1982
- 1982-04-16 EP EP82103206A patent/EP0064193B1/de not_active Expired
- 1982-04-16 AT AT82103206T patent/ATE8612T1/de not_active IP Right Cessation
- 1982-04-16 DE DE8282103206T patent/DE3260443D1/de not_active Expired
- 1982-04-28 DD DD82239383A patent/DD202302A5/de not_active IP Right Cessation
- 1982-04-28 JP JP57070563A patent/JPS57185231A/ja active Granted
- 1982-04-29 CA CA000401911A patent/CA1189539A/en not_active Expired
- 1982-04-30 KR KR8201920A patent/KR890001763B1/ko not_active Expired
- 1982-04-30 US US06/373,454 patent/US4419264A/en not_active Expired - Lifetime
-
1984
- 1984-11-12 SG SG812/84A patent/SG81284G/en unknown
-
1985
- 1985-03-07 HK HK153/85A patent/HK15385A/xx not_active IP Right Cessation
-
1988
- 1988-12-21 KR KR1019880017276A patent/KR890001805B1/ko not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| KR890001763B1 (ko) | 1989-05-19 |
| HK15385A (en) | 1985-03-15 |
| US4419264A (en) | 1983-12-06 |
| CA1189539A (en) | 1985-06-25 |
| EP0064193B1 (de) | 1984-07-25 |
| KR830010168A (ko) | 1983-12-26 |
| DE3117152A1 (de) | 1982-11-18 |
| KR890001805B1 (ko) | 1989-05-23 |
| JPS57185231A (en) | 1982-11-15 |
| DE3260443D1 (en) | 1984-08-30 |
| EP0064193A1 (de) | 1982-11-10 |
| ATE8612T1 (de) | 1984-08-15 |
| SG81284G (en) | 1985-04-26 |
| DD202302A5 (de) | 1983-09-07 |
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