JPH0225894B2 - - Google Patents
Info
- Publication number
- JPH0225894B2 JPH0225894B2 JP59011809A JP1180984A JPH0225894B2 JP H0225894 B2 JPH0225894 B2 JP H0225894B2 JP 59011809 A JP59011809 A JP 59011809A JP 1180984 A JP1180984 A JP 1180984A JP H0225894 B2 JPH0225894 B2 JP H0225894B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compounds
- alkyl
- mixture
- liquid crystal
- 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 description 121
- 239000000203 mixture Substances 0.000 claims description 106
- 239000004973 liquid crystal related substance Substances 0.000 claims description 56
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims 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 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000000463 material Substances 0.000 description 86
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- 239000004990 Smectic liquid crystal Substances 0.000 description 35
- 230000000694 effects Effects 0.000 description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- 239000000243 solution Substances 0.000 description 25
- 239000003208 petroleum Substances 0.000 description 23
- 125000004093 cyano group Chemical group *C#N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 235000015096 spirit Nutrition 0.000 description 18
- -1 di-substituted ethane Chemical class 0.000 description 17
- 230000008859 change Effects 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 13
- 239000000975 dye Substances 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 230000007704 transition Effects 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 230000005684 electric field Effects 0.000 description 10
- 239000000284 extract Substances 0.000 description 10
- 239000011521 glass Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 229940126062 Compound A Drugs 0.000 description 8
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 230000003098 cholesteric effect Effects 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 6
- 239000007818 Grignard reagent Substances 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
- 238000010828 elution Methods 0.000 description 6
- 150000004795 grignard reagents Chemical class 0.000 description 6
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 239000004988 Nematic liquid crystal Substances 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 230000008520 organization Effects 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 4
- WLPATYNQCGVFFH-UHFFFAOYSA-N 2-phenylbenzonitrile Chemical group N#CC1=CC=CC=C1C1=CC=CC=C1 WLPATYNQCGVFFH-UHFFFAOYSA-N 0.000 description 4
- GEBUSPQBSWYLBN-UHFFFAOYSA-N 4-ethyl-2-fluoro-1-phenylbenzene Chemical group FC1=CC(CC)=CC=C1C1=CC=CC=C1 GEBUSPQBSWYLBN-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 230000000875 corresponding effect Effects 0.000 description 4
- 239000000374 eutectic mixture Substances 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 3
- XXUSEPRYHRDKFV-CTYIDZIISA-N C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(C#N)C=C1 XXUSEPRYHRDKFV-CTYIDZIISA-N 0.000 description 3
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 239000000039 congener Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 230000008014 freezing Effects 0.000 description 3
- 238000007710 freezing Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000000787 lecithin Substances 0.000 description 3
- 229940067606 lecithin Drugs 0.000 description 3
- 235000010445 lecithin Nutrition 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000010587 phase diagram Methods 0.000 description 3
- 125000006850 spacer group Chemical group 0.000 description 3
- 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 2
- 239000005217 4-Cyano-4'-ethylbiphenyl Substances 0.000 description 2
- HTRNHWBOBYFTQF-UHFFFAOYSA-N 4-bromo-2-fluoro-1-phenylbenzene Chemical group FC1=CC(Br)=CC=C1C1=CC=CC=C1 HTRNHWBOBYFTQF-UHFFFAOYSA-N 0.000 description 2
- OXMZZKBMFGEIKR-XYPYZODXSA-N C(CCC)[C@@H]1CC[C@H](CC1)CC(=O)Cl Chemical compound C(CCC)[C@@H]1CC[C@H](CC1)CC(=O)Cl OXMZZKBMFGEIKR-XYPYZODXSA-N 0.000 description 2
- LWAPZSAZOVPOIO-MGCOHNPYSA-N CCC[C@H]1CC[C@H](CC(Cl)=O)CC1 Chemical compound CCC[C@H]1CC[C@H](CC(Cl)=O)CC1 LWAPZSAZOVPOIO-MGCOHNPYSA-N 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- 239000013058 crude material Substances 0.000 description 2
- 239000002178 crystalline material Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 229940045803 cuprous chloride Drugs 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical class II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 230000010287 polarization Effects 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- YZVHGHFGYMRTAS-UHFFFAOYSA-N 1-(2-methylbutyl)-4-phenylbenzene Chemical group C1=CC(CC(C)CC)=CC=C1C1=CC=CC=C1 YZVHGHFGYMRTAS-UHFFFAOYSA-N 0.000 description 1
- KRCZDDKSWIWWGR-UHFFFAOYSA-N 1-(3-fluoro-4-phenylphenyl)-4-propylcyclohexan-1-ol Chemical compound C1CC(CCC)CCC1(O)C1=CC=C(C=2C=CC=CC=2)C(F)=C1 KRCZDDKSWIWWGR-UHFFFAOYSA-N 0.000 description 1
- ZLKQQDFLPVWFDT-UHFFFAOYSA-N 1-(3-fluoro-4-phenylphenyl)ethanone Chemical group FC1=CC(C(=O)C)=CC=C1C1=CC=CC=C1 ZLKQQDFLPVWFDT-UHFFFAOYSA-N 0.000 description 1
- DZXFFCVOJWAZKA-UHFFFAOYSA-N 1-bromo-2-fluoro-3-phenylbenzene Chemical group FC1=C(Br)C=CC=C1C1=CC=CC=C1 DZXFFCVOJWAZKA-UHFFFAOYSA-N 0.000 description 1
- QSVXXQNLMJMOPL-UHFFFAOYSA-N 1-bromo-2-fluoro-4-phenylbenzene Chemical group C1=C(Br)C(F)=CC(C=2C=CC=CC=2)=C1 QSVXXQNLMJMOPL-UHFFFAOYSA-N 0.000 description 1
- DLMYHUARHITGIJ-UHFFFAOYSA-N 1-ethyl-2-phenylbenzene Chemical group CCC1=CC=CC=C1C1=CC=CC=C1 DLMYHUARHITGIJ-UHFFFAOYSA-N 0.000 description 1
- KLECYOQFQXJYBC-UHFFFAOYSA-N 1-fluoro-2-phenylbenzene Chemical group FC1=CC=CC=C1C1=CC=CC=C1 KLECYOQFQXJYBC-UHFFFAOYSA-N 0.000 description 1
- PHLJVDMEAOWDTL-UHFFFAOYSA-N 1-phenyl-4-(2-propylphenyl)benzene Chemical group C(CC)C1=C(C=CC=C1)C1=CC=C(C=C1)C1=CC=CC=C1 PHLJVDMEAOWDTL-UHFFFAOYSA-N 0.000 description 1
- FMODYUFZGCBIJS-UHFFFAOYSA-N 1-phenyl-4-(4-propylphenyl)benzene Chemical group C(CC)C1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC=C1 FMODYUFZGCBIJS-UHFFFAOYSA-N 0.000 description 1
- YFNHOTZVDNNLFV-UHFFFAOYSA-N 2-(4-ethylcyclohexyl)acetyl chloride Chemical compound CCC1CCC(CC(Cl)=O)CC1 YFNHOTZVDNNLFV-UHFFFAOYSA-N 0.000 description 1
- JTNGTRJQFQXTLA-UHFFFAOYSA-N 2-(4-pentylcyclohexyl)acetyl chloride Chemical compound CCCCCC1CCC(CC(Cl)=O)CC1 JTNGTRJQFQXTLA-UHFFFAOYSA-N 0.000 description 1
- LWAPZSAZOVPOIO-UHFFFAOYSA-N 2-(4-propylcyclohexyl)acetyl chloride Chemical compound CCCC1CCC(CC(Cl)=O)CC1 LWAPZSAZOVPOIO-UHFFFAOYSA-N 0.000 description 1
- UPIDWCHSMUISCI-UHFFFAOYSA-N 2-fluoro-1-phenyl-4-(4-propylcyclohexyl)benzene Chemical group C1CC(CCC)CCC1C1=CC=C(C=2C=CC=CC=2)C(F)=C1 UPIDWCHSMUISCI-UHFFFAOYSA-N 0.000 description 1
- QCAZNOJAHCFLHI-UHFFFAOYSA-N 2-fluoro-4-(2-methylbutyl)-1-phenylbenzene Chemical group FC1=CC(CC(C)CC)=CC=C1C1=CC=CC=C1 QCAZNOJAHCFLHI-UHFFFAOYSA-N 0.000 description 1
- GIWWLDRRWWDXJH-UHFFFAOYSA-N 2-methylbutyl benzenesulfonate Chemical compound CCC(C)COS(=O)(=O)C1=CC=CC=C1 GIWWLDRRWWDXJH-UHFFFAOYSA-N 0.000 description 1
- GPGGNNIMKOVSAG-UHFFFAOYSA-N 4-(4-octoxyphenyl)benzonitrile Chemical group C1=CC(OCCCCCCCC)=CC=C1C1=CC=C(C#N)C=C1 GPGGNNIMKOVSAG-UHFFFAOYSA-N 0.000 description 1
- XFMPTZWVMVMELB-UHFFFAOYSA-N 4-(4-propylphenyl)benzonitrile Chemical group C1=CC(CCC)=CC=C1C1=CC=C(C#N)C=C1 XFMPTZWVMVMELB-UHFFFAOYSA-N 0.000 description 1
- 239000005215 4-Cyano-4'-n-octyloxybiphenyl Substances 0.000 description 1
- DNJQGRFZQMOYGM-UHFFFAOYSA-N 4-[4-(2-methylbutyl)phenyl]benzonitrile Chemical group C1=CC(CC(C)CC)=CC=C1C1=CC=C(C#N)C=C1 DNJQGRFZQMOYGM-UHFFFAOYSA-N 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
- HHPCNRKYVYWYAU-UHFFFAOYSA-N 4-cyano-4'-pentylbiphenyl Chemical group C1=CC(CCCCC)=CC=C1C1=CC=C(C#N)C=C1 HHPCNRKYVYWYAU-UHFFFAOYSA-N 0.000 description 1
- NQEDLIZOPMNZMC-UHFFFAOYSA-N 4-propylcyclohexan-1-one Chemical compound CCCC1CCC(=O)CC1 NQEDLIZOPMNZMC-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- UCTCTWLSDUFWSR-KKLUKGEUSA-N C(CC)[C@@H]1CC[C@H](CC1)CC(=O)C1=CC=C(C=C1)C1=C(C=C(C=C1)[C@@H]1CC[C@H](CC1)CCC)F Chemical group C(CC)[C@@H]1CC[C@H](CC1)CC(=O)C1=CC=C(C=C1)C1=C(C=C(C=C1)[C@@H]1CC[C@H](CC1)CCC)F UCTCTWLSDUFWSR-KKLUKGEUSA-N 0.000 description 1
- VGPMXCABVICGBL-MEMLXQNLSA-N C(CC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)C1=C(C=C(C=C1)CCC)F Chemical compound C(CC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)C1=C(C=C(C=C1)CCC)F VGPMXCABVICGBL-MEMLXQNLSA-N 0.000 description 1
- DGKVXIBFPYXSNI-MEELFCDTSA-N C(CCC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)C1=C(C=C(C=C1)CC(CC)C)F Chemical compound C(CCC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)C1=C(C=C(C=C1)CC(CC)C)F DGKVXIBFPYXSNI-MEELFCDTSA-N 0.000 description 1
- POYOTBCXXAUGDW-HZCBDIJESA-N C(CCCC)[C@@H]1CC[C@H](CC1)CC(=O)C1=CC=C(C=C1)C1=C(C=C(C=C1)CC)F Chemical group C(CCCC)[C@@H]1CC[C@H](CC1)CC(=O)C1=CC=C(C=C1)C1=C(C=C(C=C1)CC)F POYOTBCXXAUGDW-HZCBDIJESA-N 0.000 description 1
- LUKNUHJHSSUHFG-BUZHSDJQSA-N C(CCCCCC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)C1=C(C=C(C=C1)CC(CC)C)F Chemical compound C(CCCCCC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)C1=C(C=C(C=C1)CC(CC)C)F LUKNUHJHSSUHFG-BUZHSDJQSA-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
- QKEBUASRTJNJJS-XUTJKUGGSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C=2C=CC(=CC=2)C#N)C=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C=2C=CC(=CC=2)C#N)C=C1 QKEBUASRTJNJJS-XUTJKUGGSA-N 0.000 description 1
- KXVKHTYRWKADCL-YHBQERECSA-N C1C[C@@H](CCCCC)CC[C@@H]1CCC1=CC=C(C=2C(=CC(CC)=CC=2)F)C=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1CCC1=CC=C(C=2C(=CC(CC)=CC=2)F)C=C1 KXVKHTYRWKADCL-YHBQERECSA-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
- ZXMBUYORWIDMEI-YHBQERECSA-N CCCCCc1ccc(c(F)c1)-c1ccc(CC[C@H]2CC[C@H](CCC)CC2)cc1 Chemical compound CCCCCc1ccc(c(F)c1)-c1ccc(CC[C@H]2CC[C@H](CCC)CC2)cc1 ZXMBUYORWIDMEI-YHBQERECSA-N 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- 101000725988 Drosophila melanogaster COP9 signalosome complex subunit 3 Proteins 0.000 description 1
- UUKYDAIPGNYJAS-MXVIHJGJSA-N FC1=C(C=CC(=C1)CC[C@@H]1CC[C@H](CC1)CCC)C1=CC=C(C=C1)C(CC)=O Chemical compound FC1=C(C=CC(=C1)CC[C@@H]1CC[C@H](CC1)CCC)C1=CC=C(C=C1)C(CC)=O UUKYDAIPGNYJAS-MXVIHJGJSA-N 0.000 description 1
- GUAFUUUAODUMQE-AQYVVDRMSA-N FC1=C(C=CC(=C1)CC[C@@H]1CC[C@H](CC1)CCC)C1=CC=C(C=C1)CCC Chemical compound FC1=C(C=CC(=C1)CC[C@@H]1CC[C@H](CC1)CCC)C1=CC=C(C=C1)CCC GUAFUUUAODUMQE-AQYVVDRMSA-N 0.000 description 1
- NGVOQYLHNNHGBV-WGSAOQKQSA-N FC1=C(C=CC(=C1)CC[C@@H]1CC[C@H](CC1)CCC)C1=CC=CC=C1 Chemical compound FC1=C(C=CC(=C1)CC[C@@H]1CC[C@H](CC1)CCC)C1=CC=CC=C1 NGVOQYLHNNHGBV-WGSAOQKQSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 238000006856 Wolf-Kishner-Huang Minlon reduction reaction Methods 0.000 description 1
- NQSUQAQPOPPGIN-UHFFFAOYSA-M [Br-].FC1=CC([Mg+])=CC=C1C1=CC=CC=C1 Chemical compound [Br-].FC1=CC([Mg+])=CC=C1C1=CC=CC=C1 NQSUQAQPOPPGIN-UHFFFAOYSA-M 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000003491 array Methods 0.000 description 1
- MQTOSJVFKKJCRP-BICOPXKESA-N azithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 MQTOSJVFKKJCRP-BICOPXKESA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 150000001934 cyclohexanes Chemical group 0.000 description 1
- 229920006332 epoxy adhesive Polymers 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 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
- 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
- 230000007935 neutral effect Effects 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000013526 supercooled liquid Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8302119 | 1983-01-26 | ||
| GB838302119A GB8302119D0 (en) | 1983-01-26 | 1983-01-26 | Disubstituted ethanes |
| GB8328370 | 1983-10-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6069045A JPS6069045A (ja) | 1985-04-19 |
| JPH0225894B2 true JPH0225894B2 (xx) | 1990-06-06 |
Family
ID=10536967
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1180984A Granted JPS6069045A (ja) | 1983-01-26 | 1984-01-25 | ジ置換エタン並びに液晶材料及び装置に於けるその使用 |
| JP1181084A Granted JPS6069046A (ja) | 1983-01-26 | 1984-01-25 | 液晶化合物の製造用ビフェニル類 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1181084A Granted JPS6069046A (ja) | 1983-01-26 | 1984-01-25 | 液晶化合物の製造用ビフェニル類 |
Country Status (2)
| Country | Link |
|---|---|
| JP (2) | JPS6069045A (xx) |
| GB (1) | GB8302119D0 (xx) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61282328A (ja) * | 1985-06-10 | 1986-12-12 | Chisso Corp | シクロヘキサン誘導体 |
| FR2586422B1 (fr) * | 1985-08-26 | 1988-01-15 | Commissariat Energie Atomique | Melange de cristaux liquides nematiques comportant un 1-(alkyl cyclohexyl)-2-(alkyl fluorobiphenyly) ethane |
| JP4526605B2 (ja) * | 1996-08-28 | 2010-08-18 | チッソ株式会社 | ラテラルハロゲン置換基を有する４環化合物および液晶組成物 |
| WO2009145101A1 (ja) * | 2008-05-29 | 2009-12-03 | チッソ株式会社 | フッ素原子を有する液晶性四環化合物、液晶組成物、及び液晶表示素子 |
| JP2010111686A (ja) * | 2009-12-24 | 2010-05-20 | Chisso Corp | ラテラルハロゲン置換基を有する４環化合物および液晶組成物 |
| KR102274669B1 (ko) * | 2013-07-30 | 2021-07-09 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 유기 화합물, 액정 조성물, 액정 소자, 및 액정 표시 장치 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57114532A (en) * | 1980-11-10 | 1982-07-16 | Merck Patent Gmbh | Fluorine-containiing cyclohexylbiphenyl derivatives, dielectric body containing them and electronic optical display element |
| JPS57165326A (en) * | 1981-04-03 | 1982-10-12 | Asahi Glass Co Ltd | Trans-4-alkyl-(4'-fluorobiphenyl-4)cyclohexane |
| JPS59155485A (ja) * | 1983-02-22 | 1984-09-04 | Canon Inc | 液晶組成物 |
| JPS6048945A (ja) * | 1983-08-27 | 1985-03-16 | Chisso Corp | シクロヘキシルビフエニルのフッ素化物 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1460295A (en) * | 1973-06-01 | 1976-12-31 | Boots Co Ltd | Biphenyls and diphenyl ethers |
-
1983
- 1983-01-26 GB GB838302119A patent/GB8302119D0/en active Pending
-
1984
- 1984-01-25 JP JP1180984A patent/JPS6069045A/ja active Granted
- 1984-01-25 JP JP1181084A patent/JPS6069046A/ja active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57114532A (en) * | 1980-11-10 | 1982-07-16 | Merck Patent Gmbh | Fluorine-containiing cyclohexylbiphenyl derivatives, dielectric body containing them and electronic optical display element |
| JPS57165326A (en) * | 1981-04-03 | 1982-10-12 | Asahi Glass Co Ltd | Trans-4-alkyl-(4'-fluorobiphenyl-4)cyclohexane |
| JPS59155485A (ja) * | 1983-02-22 | 1984-09-04 | Canon Inc | 液晶組成物 |
| JPS6048945A (ja) * | 1983-08-27 | 1985-03-16 | Chisso Corp | シクロヘキシルビフエニルのフッ素化物 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6069046A (ja) | 1985-04-19 |
| JPS6069045A (ja) | 1985-04-19 |
| GB8302119D0 (en) | 1983-03-02 |
| JPH0446251B2 (xx) | 1992-07-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |