JPH0430938B2 - - Google Patents
Info
- Publication number
- JPH0430938B2 JPH0430938B2 JP59195770A JP19577084A JPH0430938B2 JP H0430938 B2 JPH0430938 B2 JP H0430938B2 JP 59195770 A JP59195770 A JP 59195770A JP 19577084 A JP19577084 A JP 19577084A JP H0430938 B2 JPH0430938 B2 JP H0430938B2
- Authority
- JP
- Japan
- Prior art keywords
- added
- liquid crystal
- derivatives
- group
- reduced pressure
- 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
Links
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical class CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 58
- 150000001875 compounds Chemical class 0.000 description 38
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 36
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- 239000000203 mixture Substances 0.000 description 32
- 239000004973 liquid crystal related substance Substances 0.000 description 31
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 25
- 239000007864 aqueous solution Substances 0.000 description 22
- 238000000034 method Methods 0.000 description 16
- 238000003756 stirring Methods 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 238000001035 drying Methods 0.000 description 12
- 230000003287 optical effect Effects 0.000 description 12
- 230000007704 transition Effects 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 11
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 10
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
- 239000003208 petroleum Substances 0.000 description 9
- 238000010898 silica gel chromatography Methods 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- MWGLMIHIMAZKRY-UHFFFAOYSA-N 3-[4-(2-methylbutyl)phenyl]-4-(4-octylphenyl)benzoic acid Chemical compound C1=CC(CCCCCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1C1=CC=C(CC(C)CC)C=C1 MWGLMIHIMAZKRY-UHFFFAOYSA-N 0.000 description 8
- RBADEBYNLRPXLQ-UHFFFAOYSA-N 4-[(4-hexoxyphenyl)diazenyl]phenol Chemical compound OC1=CC=C(C=C1)N=NC1=CC=C(C=C1)OCCCCCC RBADEBYNLRPXLQ-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- -1 polycyclic hydrocarbon Chemical class 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- PADLHDBOFPQDHI-UHFFFAOYSA-N 2-butoxypropanoyl chloride Chemical compound CCCCOC(C)C(Cl)=O PADLHDBOFPQDHI-UHFFFAOYSA-N 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 229940116333 ethyl lactate Drugs 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 150000004694 iodide salts Chemical class 0.000 description 5
- 239000008204 material by function Substances 0.000 description 5
- 230000010287 polarization Effects 0.000 description 5
- 235000010288 sodium nitrite Nutrition 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- LXSVWFRZICUOLU-UHFFFAOYSA-N 2-butoxypropanoic acid Chemical compound CCCCOC(C)C(O)=O LXSVWFRZICUOLU-UHFFFAOYSA-N 0.000 description 4
- KVXWKCZRKDPJTB-UHFFFAOYSA-N 2-heptoxypropanoic acid Chemical compound CCCCCCCOC(C)C(O)=O KVXWKCZRKDPJTB-UHFFFAOYSA-N 0.000 description 4
- NTGHUAVUJPIMOC-UHFFFAOYSA-N 2-heptoxypropanoyl chloride Chemical compound CCCCCCCOC(C)C(Cl)=O NTGHUAVUJPIMOC-UHFFFAOYSA-N 0.000 description 4
- GTRZPDPWJYIUOK-UHFFFAOYSA-N [4-[(4-hexoxyphenyl)diazenyl]phenyl] 3-butoxypropanoate Chemical compound C1=CC(OCCCCCC)=CC=C1N=NC1=CC=C(OC(=O)CCOCCCC)C=C1 GTRZPDPWJYIUOK-UHFFFAOYSA-N 0.000 description 4
- 238000013329 compounding Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000013081 microcrystal Substances 0.000 description 4
- YUAUWEGVKKQBNY-UHFFFAOYSA-N n-hexoxyaniline Chemical compound CCCCCCONC1=CC=CC=C1 YUAUWEGVKKQBNY-UHFFFAOYSA-N 0.000 description 4
- 230000002269 spontaneous effect Effects 0.000 description 4
- SKIDNYUZJPMKFC-UHFFFAOYSA-N 1-iododecane Chemical compound CCCCCCCCCCI SKIDNYUZJPMKFC-UHFFFAOYSA-N 0.000 description 3
- KWYKRCFXFADWBK-UHFFFAOYSA-N 4-[(4-octylphenyl)diazenyl]phenol Chemical compound CCCCCCCCc1ccc(cc1)N=Nc1ccc(O)cc1 KWYKRCFXFADWBK-UHFFFAOYSA-N 0.000 description 3
- ORKQJTBYQZITLA-UHFFFAOYSA-N 4-octylaniline Chemical compound CCCCCCCCC1=CC=C(N)C=C1 ORKQJTBYQZITLA-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- DLFJETOVZQERCN-UHFFFAOYSA-N [4-[(4-hexoxyphenyl)diazenyl]phenyl] 3-heptoxypropanoate Chemical compound C1=CC(OC(=O)CCOCCCCCCC)=CC=C1N=NC1=CC=C(OCCCCCC)C=C1 DLFJETOVZQERCN-UHFFFAOYSA-N 0.000 description 3
- SYTSGMLYKFXQQP-UHFFFAOYSA-N [4-[(4-octylphenyl)diazenyl]phenyl] 3-heptoxypropanoate Chemical compound C1=CC(CCCCCCCC)=CC=C1N=NC1=CC=C(OC(=O)CCOCCCCCCC)C=C1 SYTSGMLYKFXQQP-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- HMONIZCCNGYDDJ-UHFFFAOYSA-N ethyl 2-butoxypropanoate Chemical compound CCCCOC(C)C(=O)OCC HMONIZCCNGYDDJ-UHFFFAOYSA-N 0.000 description 3
- PXEPVAGEOGKOQY-UHFFFAOYSA-N ethyl 2-heptoxypropanoate Chemical compound CCCCCCCOC(C)C(=O)OCC PXEPVAGEOGKOQY-UHFFFAOYSA-N 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- LMHCYRULPLGEEZ-UHFFFAOYSA-N 1-iodoheptane Chemical compound CCCCCCCI LMHCYRULPLGEEZ-UHFFFAOYSA-N 0.000 description 2
- ZNJOCVLVYVOUGB-UHFFFAOYSA-N 1-iodooctadecane Chemical compound CCCCCCCCCCCCCCCCCCI ZNJOCVLVYVOUGB-UHFFFAOYSA-N 0.000 description 2
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical group OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- XXUQUCMOXUDEIL-UHFFFAOYSA-N 4-[(4-heptylphenyl)diazenyl]phenol Chemical compound OC1=CC=C(C=C1)N=NC1=CC=C(C=C1)CCCCCCC XXUQUCMOXUDEIL-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- BTVKCKPPLDCXBK-UHFFFAOYSA-N C(CCCCCCC)C1=CC=C(C=C1)N=NC1=CC=C(C=C1)O.[K] Chemical compound C(CCCCCCC)C1=CC=C(C=C1)N=NC1=CC=C(C=C1)O.[K] BTVKCKPPLDCXBK-UHFFFAOYSA-N 0.000 description 2
- 239000004990 Smectic liquid crystal Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- YCHUYYQXVGWKSS-UHFFFAOYSA-N [4-(3-butoxypropanoyloxy)phenyl]-(4-hexoxyphenyl)imino-oxidoazanium Chemical compound C(CCCCC)OC1=CC=C(C=C1)N=[N+]([O-])C1=CC=C(C=C1)OC(CCOCCCC)=O YCHUYYQXVGWKSS-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000003862 amino acid derivatives Chemical group 0.000 description 2
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 2
- GAUZCKBSTZFWCT-UHFFFAOYSA-N azoxybenzene Chemical class C=1C=CC=CC=1[N+]([O-])=NC1=CC=CC=C1 GAUZCKBSTZFWCT-UHFFFAOYSA-N 0.000 description 2
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 150000001841 cholesterols Chemical class 0.000 description 2
- 230000001186 cumulative effect Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- LIZTWFPKQKLMQT-UHFFFAOYSA-N ethyl 2-decoxypropanoate Chemical compound CCCCCCCCCCOC(C)C(=O)OCC LIZTWFPKQKLMQT-UHFFFAOYSA-N 0.000 description 2
- KCSRTDYOUZASCX-UHFFFAOYSA-N ethyl 2-dodecoxypropanoate Chemical compound CCCCCCCCCCCCOC(C)C(=O)OCC KCSRTDYOUZASCX-UHFFFAOYSA-N 0.000 description 2
- HLNIJAXCYZAJNK-UHFFFAOYSA-N ethyl 2-octadecoxypropanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(C)C(=O)OCC HLNIJAXCYZAJNK-UHFFFAOYSA-N 0.000 description 2
- 125000001165 hydrophobic group Chemical group 0.000 description 2
- 150000003903 lactic acid esters Chemical class 0.000 description 2
- AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- LXSVWFRZICUOLU-ZCFIWIBFSA-N (2r)-2-butoxypropanoic acid Chemical compound CCCCO[C@H](C)C(O)=O LXSVWFRZICUOLU-ZCFIWIBFSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- VYPCMVCNMJQSKV-UHFFFAOYSA-N 1-heptyl-4-phenyldiazenylcyclohexa-2,4-dien-1-ol Chemical compound CCCCCCCC1(CC=C(C=C1)N=NC2=CC=CC=C2)O VYPCMVCNMJQSKV-UHFFFAOYSA-N 0.000 description 1
- BTUGGGLMQBJCBN-UHFFFAOYSA-N 1-iodo-2-methylpropane Chemical compound CC(C)CI BTUGGGLMQBJCBN-UHFFFAOYSA-N 0.000 description 1
- BUZZUHJODKQYTF-UHFFFAOYSA-N 1-iodo-3-methylbutane Chemical compound CC(C)CCI BUZZUHJODKQYTF-UHFFFAOYSA-N 0.000 description 1
- ZQUIJUNLTMQRAA-UHFFFAOYSA-N 1-iodo-3-methylcyclohexane Chemical compound CC1CCCC(I)C1 ZQUIJUNLTMQRAA-UHFFFAOYSA-N 0.000 description 1
- GCDPERPXPREHJF-UHFFFAOYSA-N 1-iodododecane Chemical compound CCCCCCCCCCCCI GCDPERPXPREHJF-UHFFFAOYSA-N 0.000 description 1
- SWGRLCBZNPROCQ-UHFFFAOYSA-N 1-iodoheptadecane Chemical compound CCCCCCCCCCCCCCCCCI SWGRLCBZNPROCQ-UHFFFAOYSA-N 0.000 description 1
- KMWHQYDMBYABKL-UHFFFAOYSA-N 1-iodohexadecane Chemical compound CCCCCCCCCCCCCCCCI KMWHQYDMBYABKL-UHFFFAOYSA-N 0.000 description 1
- ANOOTOPTCJRUPK-UHFFFAOYSA-N 1-iodohexane Chemical compound CCCCCCI ANOOTOPTCJRUPK-UHFFFAOYSA-N 0.000 description 1
- UYBWORFIJZQKEP-UHFFFAOYSA-N 1-iodoicosane Chemical compound CCCCCCCCCCCCCCCCCCCCI UYBWORFIJZQKEP-UHFFFAOYSA-N 0.000 description 1
- LXFODWIENIOBLX-UHFFFAOYSA-N 1-iodononadecane Chemical compound CCCCCCCCCCCCCCCCCCCI LXFODWIENIOBLX-UHFFFAOYSA-N 0.000 description 1
- OGSJMFCWOUHXHN-UHFFFAOYSA-N 1-iodononane Chemical compound CCCCCCCCCI OGSJMFCWOUHXHN-UHFFFAOYSA-N 0.000 description 1
- UWLHSHAHTBJTBA-UHFFFAOYSA-N 1-iodooctane Chemical compound CCCCCCCCI UWLHSHAHTBJTBA-UHFFFAOYSA-N 0.000 description 1
- HHXJMIXXUWDKIA-UHFFFAOYSA-N 1-iodopentadecane Chemical compound CCCCCCCCCCCCCCCI HHXJMIXXUWDKIA-UHFFFAOYSA-N 0.000 description 1
- BLXSFCHWMBESKV-UHFFFAOYSA-N 1-iodopentane Chemical compound CCCCCI BLXSFCHWMBESKV-UHFFFAOYSA-N 0.000 description 1
- FHQCFGPKNSSISL-UHFFFAOYSA-N 1-iodotetradecane Chemical compound CCCCCCCCCCCCCCI FHQCFGPKNSSISL-UHFFFAOYSA-N 0.000 description 1
- XGAMQNYEIPCUIZ-UHFFFAOYSA-N 1-iodotridecane Chemical compound CCCCCCCCCCCCCI XGAMQNYEIPCUIZ-UHFFFAOYSA-N 0.000 description 1
- FKUQOQPBCHJHAP-UHFFFAOYSA-N 1-iodoundecane Chemical compound CCCCCCCCCCCI FKUQOQPBCHJHAP-UHFFFAOYSA-N 0.000 description 1
- ICEBAZPURYIURB-UHFFFAOYSA-N 2-(2-methylbutyl)benzoic acid Chemical compound CCC(C)CC1=CC=CC=C1C(O)=O ICEBAZPURYIURB-UHFFFAOYSA-N 0.000 description 1
- IQRUSQUYPCHEKN-UHFFFAOYSA-N 2-iodobutane Chemical compound CCC(C)I IQRUSQUYPCHEKN-UHFFFAOYSA-N 0.000 description 1
- YWILTCMUUXDNMA-UHFFFAOYSA-N 4-[(4-hexylphenyl)diazenyl]phenol Chemical compound CCCCCCc1ccc(cc1)N=Nc1ccc(O)cc1 YWILTCMUUXDNMA-UHFFFAOYSA-N 0.000 description 1
- BNEWZYZRLNNWNR-UHFFFAOYSA-N 4-heptylaniline Chemical compound CCCCCCCC1=CC=C(N)C=C1 BNEWZYZRLNNWNR-UHFFFAOYSA-N 0.000 description 1
- OVEMTTZEBOCJDV-UHFFFAOYSA-N 4-hexylaniline Chemical compound CCCCCCC1=CC=C(N)C=C1 OVEMTTZEBOCJDV-UHFFFAOYSA-N 0.000 description 1
- GFOAHCQVVPDRKF-UHFFFAOYSA-N C(CCCCC)OC1=CC=C(C=C1)N=[N+]([O-])C1=CC=C(C=C1)OC(CCOCCCCCCC)=O Chemical compound C(CCCCC)OC1=CC=C(C=C1)N=[N+]([O-])C1=CC=C(C=C1)OC(CCOCCCCCCC)=O GFOAHCQVVPDRKF-UHFFFAOYSA-N 0.000 description 1
- BOUKHIOVTCSXQI-UHFFFAOYSA-N C(CCCCCCC)C1=CC=C(C=C1)N=[N+]([O-])C1=CC=C(C=C1)OC(CCOCCCCCCC)=O Chemical compound C(CCCCCCC)C1=CC=C(C=C1)N=[N+]([O-])C1=CC=C(C=C1)OC(CCOCCCCCCC)=O BOUKHIOVTCSXQI-UHFFFAOYSA-N 0.000 description 1
- MOYCUFHKIBNXIC-UHFFFAOYSA-N CCCCCCC1(CC=C(C=C1)N=NC2=CC=CC=C2)O Chemical compound CCCCCCC1(CC=C(C=C1)N=NC2=CC=CC=C2)O MOYCUFHKIBNXIC-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- KUNFWFITKVJDGD-UHFFFAOYSA-N [4-[(4-hexylphenyl)diazenyl]phenyl] 3-butoxypropanoate Chemical compound C1=CC(CCCCCC)=CC=C1N=NC1=CC=C(OC(=O)CCOCCCC)C=C1 KUNFWFITKVJDGD-UHFFFAOYSA-N 0.000 description 1
- DBXALYWKOHHVLL-UHFFFAOYSA-N [4-[(4-octylphenyl)diazenyl]phenyl] 3-butoxypropanoate Chemical compound C1=CC(CCCCCCCC)=CC=C1N=NC1=CC=C(OC(=O)CCOCCCC)C=C1 DBXALYWKOHHVLL-UHFFFAOYSA-N 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical class C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-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
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001788 chalcone derivatives Chemical class 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 150000001851 cinnamic acid derivatives Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical class C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical class C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000005621 ferroelectricity Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 125000006480 iodobenzyl group Chemical group 0.000 description 1
- ZQCXCNPOYCQOEW-UHFFFAOYSA-N iodocycloheptane Chemical compound IC1CCCCCC1 ZQCXCNPOYCQOEW-UHFFFAOYSA-N 0.000 description 1
- FUCOMWZKWIEKRK-UHFFFAOYSA-N iodocyclohexane Chemical compound IC1CCCCC1 FUCOMWZKWIEKRK-UHFFFAOYSA-N 0.000 description 1
- LDKYPRVLJQWKBI-UHFFFAOYSA-N iodocyclooctane Chemical compound IC1CCCCCCC1 LDKYPRVLJQWKBI-UHFFFAOYSA-N 0.000 description 1
- PCEBAZIVZVIQEO-UHFFFAOYSA-N iodocyclopentane Chemical compound IC1CCCC1 PCEBAZIVZVIQEO-UHFFFAOYSA-N 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000001572 propyl (E)-3-phenylprop-2-enoate Substances 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59195770A JPS6176438A (ja) | 1984-09-20 | 1984-09-20 | 乳酸誘導体 |
| US06/776,963 US4775223A (en) | 1984-09-20 | 1985-09-17 | Lactic acid derivative, liquid crystal composition containing same and liquid crystal device |
| DE8585306724T DE3581992D1 (de) | 1984-09-20 | 1985-09-20 | Milchsaeurederivat, dieses enthaltende fluessigkristallkomposition und fluessigkristalleinrichtung. |
| EP85306724A EP0175591B1 (de) | 1984-09-20 | 1985-09-20 | Milchsäurederivat, dieses enthaltende Flüssigkristallkomposition und Flüssigkristalleinrichtung |
| US07/598,807 US5167857A (en) | 1984-09-20 | 1990-10-18 | Lactic acid derivative, liquid crystal composition containing same and liquid crystal device |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59195770A JPS6176438A (ja) | 1984-09-20 | 1984-09-20 | 乳酸誘導体 |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3131692A Division JPH0717591B2 (ja) | 1991-05-08 | 1991-05-08 | 乳酸誘導体 |
| JP3131693A Division JPH0768517B2 (ja) | 1991-05-08 | 1991-05-08 | カイラルスメクチック液晶組成物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6176438A JPS6176438A (ja) | 1986-04-18 |
| JPH0430938B2 true JPH0430938B2 (de) | 1992-05-25 |
Family
ID=16346668
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59195770A Granted JPS6176438A (ja) | 1984-09-20 | 1984-09-20 | 乳酸誘導体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6176438A (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8428653D0 (en) * | 1984-11-13 | 1984-12-19 | Secr Defence | Diesters |
| JPH0643374B2 (ja) * | 1986-07-28 | 1994-06-08 | 高砂香料工業株式会社 | 液晶性化合物 |
| JPH0717591B2 (ja) * | 1991-05-08 | 1995-03-01 | キヤノン株式会社 | 乳酸誘導体 |
| TR201905768T4 (tr) * | 2009-05-08 | 2019-05-21 | Basf As | Kardiyovasküler, metabolik ve enflamatuar hastalık alanları ile ilişkili hastalıkların tedavisinde çoklu doymamış yağlı asitleri. |
-
1984
- 1984-09-20 JP JP59195770A patent/JPS6176438A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6176438A (ja) | 1986-04-18 |
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