JPH0583593B2 - - Google Patents
Info
- Publication number
- JPH0583593B2 JPH0583593B2 JP1246428A JP24642889A JPH0583593B2 JP H0583593 B2 JPH0583593 B2 JP H0583593B2 JP 1246428 A JP1246428 A JP 1246428A JP 24642889 A JP24642889 A JP 24642889A JP H0583593 B2 JPH0583593 B2 JP H0583593B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- hours
- ether
- add
- derivatives
- 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
- 239000004973 liquid crystal related substance Substances 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 238000013329 compounding Methods 0.000 claims description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 72
- 150000001875 compounds Chemical class 0.000 description 32
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 238000003756 stirring Methods 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 230000003287 optical effect Effects 0.000 description 19
- -1 polycyclic hydrocarbon Chemical class 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical class CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 16
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 15
- 239000007864 aqueous solution Substances 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 238000010992 reflux Methods 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 239000013078 crystal Substances 0.000 description 9
- 150000002430 hydrocarbons Chemical class 0.000 description 9
- 238000001816 cooling Methods 0.000 description 8
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 229940116333 ethyl lactate Drugs 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 229910010082 LiAlH Inorganic materials 0.000 description 6
- 239000004990 Smectic liquid crystal Substances 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 239000000543 intermediate Substances 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 230000002269 spontaneous effect Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- RHDYQUZYHZWTCI-UHFFFAOYSA-N 1-methoxy-4-phenylbenzene Chemical group C1=CC(OC)=CC=C1C1=CC=CC=C1 RHDYQUZYHZWTCI-UHFFFAOYSA-N 0.000 description 4
- YGPUNMRFTJLFKI-UHFFFAOYSA-N 2-heptoxypropan-1-ol Chemical compound CCCCCCCOC(C)CO YGPUNMRFTJLFKI-UHFFFAOYSA-N 0.000 description 4
- FDPKGXQCDURRBM-UHFFFAOYSA-N 4-(4-methoxyphenyl)benzoic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C(O)=O)C=C1 FDPKGXQCDURRBM-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 230000003098 cholesteric effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- NKAVDXBGTXDQCB-UHFFFAOYSA-N 2-(4-octoxyphenyl)benzoic acid Chemical compound C1=CC(OCCCCCCCC)=CC=C1C1=CC=CC=C1C(O)=O NKAVDXBGTXDQCB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- KVJHGPAAOUGYJX-UHFFFAOYSA-N 1,1,3,3-tetraethoxypropane Chemical compound CCOC(OCC)CC(OCC)OCC KVJHGPAAOUGYJX-UHFFFAOYSA-N 0.000 description 2
- AITDOOYSOAAUPM-UHFFFAOYSA-N 1-[4-(4-methoxyphenyl)phenyl]ethanone Chemical group C1=CC(OC)=CC=C1C1=CC=C(C(C)=O)C=C1 AITDOOYSOAAUPM-UHFFFAOYSA-N 0.000 description 2
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 2
- SKIDNYUZJPMKFC-UHFFFAOYSA-N 1-iododecane Chemical compound CCCCCCCCCCI SKIDNYUZJPMKFC-UHFFFAOYSA-N 0.000 description 2
- GCDPERPXPREHJF-UHFFFAOYSA-N 1-iodododecane Chemical compound CCCCCCCCCCCCI GCDPERPXPREHJF-UHFFFAOYSA-N 0.000 description 2
- 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
- WGKZYJXRTIPTCV-UHFFFAOYSA-N 2-butoxypropan-1-ol Chemical compound CCCCOC(C)CO WGKZYJXRTIPTCV-UHFFFAOYSA-N 0.000 description 2
- QVPKRLUVWASUMA-UHFFFAOYSA-N 2-decoxypropan-1-ol Chemical compound CCCCCCCCCCOC(C)CO QVPKRLUVWASUMA-UHFFFAOYSA-N 0.000 description 2
- UKCFWUCWNZTUPT-UHFFFAOYSA-N 2-dodecoxypropan-1-ol Chemical compound CCCCCCCCCCCCOC(C)CO UKCFWUCWNZTUPT-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
- WJRHSYCQNCDYMN-UHFFFAOYSA-N 4'-Hydroxy-2-biphenylcarboxylic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=C(O)C=C1 WJRHSYCQNCDYMN-UHFFFAOYSA-N 0.000 description 2
- OJBZABCNFYYKGZ-UHFFFAOYSA-N 4-(5-heptylpyrimidin-2-yl)benzoic acid Chemical compound N1=CC(CCCCCCC)=CN=C1C1=CC=C(C(O)=O)C=C1 OJBZABCNFYYKGZ-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- MUCRYNWJQNHDJH-OADIDDRXSA-N Ursonic acid Chemical compound C1CC(=O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C MUCRYNWJQNHDJH-OADIDDRXSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 150000003862 amino acid derivatives Chemical group 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 2
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 150000001841 cholesterols Chemical class 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 230000001186 cumulative effect Effects 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- HMONIZCCNGYDDJ-UHFFFAOYSA-N ethyl 2-butoxypropanoate Chemical compound CCCCOC(C)C(=O)OCC HMONIZCCNGYDDJ-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
- PXEPVAGEOGKOQY-UHFFFAOYSA-N ethyl 2-heptoxypropanoate Chemical compound CCCCCCCOC(C)C(=O)OCC PXEPVAGEOGKOQY-UHFFFAOYSA-N 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-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
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 125000001165 hydrophobic group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000003903 lactic acid esters Chemical class 0.000 description 2
- SANDFJWTZYOLPM-UHFFFAOYSA-N methyl 4-carbamimidoylbenzoate;hydrochloride Chemical compound Cl.COC(=O)C1=CC=C(C(N)=N)C=C1 SANDFJWTZYOLPM-UHFFFAOYSA-N 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 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
- 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
- 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
- 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
- LAHAZKAMIBEVMR-UHFFFAOYSA-N 2-(4-butylphenyl)-3-ethoxyprop-2-enal Chemical compound CCCCC1=CC=C(C(C=O)=COCC)C=C1 LAHAZKAMIBEVMR-UHFFFAOYSA-N 0.000 description 1
- QPFDPJJNUKGHBB-UHFFFAOYSA-N 2-(ethoxymethylidene)nonanal Chemical compound CCCCCCCC(C=O)=COCC QPFDPJJNUKGHBB-UHFFFAOYSA-N 0.000 description 1
- ZBHDEKMTHBEIEJ-UHFFFAOYSA-N 2-decoxypropanoic acid Chemical compound CCCCCCCCCCOC(C)C(O)=O ZBHDEKMTHBEIEJ-UHFFFAOYSA-N 0.000 description 1
- IQRUSQUYPCHEKN-UHFFFAOYSA-N 2-iodobutane Chemical compound CCC(C)I IQRUSQUYPCHEKN-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- VDLKSWBHHFUWOT-UHFFFAOYSA-N 2-octadecoxypropan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCOC(C)CO VDLKSWBHHFUWOT-UHFFFAOYSA-N 0.000 description 1
- GPGUIPYKSRABPM-UHFFFAOYSA-N 4-[2-(3-heptoxypropyl)phenyl]-3-octoxybenzoic acid Chemical compound CCCCCCCCOC1=C(C=CC(=C1)C(=O)O)C2=CC=CC=C2CCCOCCCCCCC GPGUIPYKSRABPM-UHFFFAOYSA-N 0.000 description 1
- KSNPXQRQWMDHPH-UHFFFAOYSA-N 4-[5-(4-butylphenyl)pyrimidin-2-yl]benzoic acid Chemical compound C1=CC(CCCC)=CC=C1C1=CN=C(C=2C=CC(=CC=2)C(O)=O)N=C1 KSNPXQRQWMDHPH-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229910006124 SOCl2 Inorganic materials 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical class C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 1
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 1
- GAUZCKBSTZFWCT-UHFFFAOYSA-N azoxybenzene Chemical class C=1C=CC=CC=1[N+]([O-])=NC1=CC=CC=C1 GAUZCKBSTZFWCT-UHFFFAOYSA-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
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001788 chalcone derivatives Chemical class 0.000 description 1
- 230000002925 chemical effect Effects 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000001851 cinnamic acid derivatives Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 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
- 230000007547 defect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- VFNGKCDDZUSWLR-UHFFFAOYSA-N disulfuric acid Chemical compound OS(=O)(=O)OS(O)(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-N 0.000 description 1
- 229920006332 epoxy adhesive Polymers 0.000 description 1
- LIZTWFPKQKLMQT-UHFFFAOYSA-N ethyl 2-decoxypropanoate Chemical compound CCCCCCCCCCOC(C)C(=O)OCC LIZTWFPKQKLMQT-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000005621 ferroelectricity Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 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
- 239000004615 ingredient Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 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
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 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
- UMPPIGVRQUHHHG-UHFFFAOYSA-N methyl 4-[5-(4-butylphenyl)pyrimidin-2-yl]benzoate Chemical compound C1=CC(CCCC)=CC=C1C1=CN=C(C=2C=CC(=CC=2)C(=O)OC)N=C1 UMPPIGVRQUHHHG-UHFFFAOYSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical compound COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 1
- AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-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
- 238000000746 purification Methods 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
- 238000007650 screen-printing Methods 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
- 125000006850 spacer group Chemical group 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
- 239000000725 suspension Substances 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1246428A JPH02117988A (ja) | 1989-09-25 | 1989-09-25 | 乳酸誘導体を含有する液晶組成物 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1246428A JPH02117988A (ja) | 1989-09-25 | 1989-09-25 | 乳酸誘導体を含有する液晶組成物 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59233269A Division JPS61112038A (ja) | 1984-09-20 | 1984-11-07 | 液晶性化合物の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02117988A JPH02117988A (ja) | 1990-05-02 |
| JPH0583593B2 true JPH0583593B2 (enrdf_load_stackoverflow) | 1993-11-26 |
Family
ID=17148334
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1246428A Granted JPH02117988A (ja) | 1989-09-25 | 1989-09-25 | 乳酸誘導体を含有する液晶組成物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02117988A (enrdf_load_stackoverflow) |
-
1989
- 1989-09-25 JP JP1246428A patent/JPH02117988A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02117988A (ja) | 1990-05-02 |
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