JPH0457694B2 - - Google Patents
Info
- Publication number
- JPH0457694B2 JPH0457694B2 JP62288476A JP28847687A JPH0457694B2 JP H0457694 B2 JPH0457694 B2 JP H0457694B2 JP 62288476 A JP62288476 A JP 62288476A JP 28847687 A JP28847687 A JP 28847687A JP H0457694 B2 JPH0457694 B2 JP H0457694B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- reaction
- ester
- synthesis
- yield
- 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
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 130
- 238000006243 chemical reaction Methods 0.000 description 96
- 230000015572 biosynthetic process Effects 0.000 description 64
- 238000003786 synthesis reaction Methods 0.000 description 60
- 229920000642 polymer Polymers 0.000 description 43
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 42
- 239000000178 monomer Substances 0.000 description 39
- 150000002148 esters Chemical class 0.000 description 37
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 32
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 31
- 239000000203 mixture Substances 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
- 150000001875 compounds Chemical class 0.000 description 22
- 230000004044 response Effects 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 239000002904 solvent Substances 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- 238000004440 column chromatography Methods 0.000 description 19
- -1 alkene halide Chemical class 0.000 description 18
- 230000005684 electric field Effects 0.000 description 18
- 230000010287 polarization Effects 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 18
- 230000002269 spontaneous effect Effects 0.000 description 17
- 230000007704 transition Effects 0.000 description 16
- 238000005160 1H NMR spectroscopy Methods 0.000 description 15
- 238000004458 analytical method Methods 0.000 description 15
- 230000006399 behavior Effects 0.000 description 15
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
- 235000019341 magnesium sulphate Nutrition 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 239000004973 liquid crystal related substance Substances 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 6
- QGFSQVPRCWJZQK-UHFFFAOYSA-N 9-Decen-1-ol Chemical compound OCCCCCCCCC=C QGFSQVPRCWJZQK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- LAEZQMVVQHICOO-UHFFFAOYSA-N 2-chloro-3-methylpentan-1-ol Chemical compound CCC(C)C(Cl)CO LAEZQMVVQHICOO-UHFFFAOYSA-N 0.000 description 5
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 5
- WYUVZDIOIFXZSJ-UHFFFAOYSA-N 2-methylbutyl 4-(4-hydroxyphenyl)benzoate Chemical compound C1=CC(C(=O)OCC(C)CC)=CC=C1C1=CC=C(O)C=C1 WYUVZDIOIFXZSJ-UHFFFAOYSA-N 0.000 description 5
- GDBUZIKSJGRBJP-UHFFFAOYSA-N 4-acetoxy benzoic acid Chemical compound CC(=O)OC1=CC=C(C(O)=O)C=C1 GDBUZIKSJGRBJP-UHFFFAOYSA-N 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
- 125000001033 ether group Chemical group 0.000 description 5
- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 5
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 5
- 229920000570 polyether Polymers 0.000 description 5
- QOCVTOZYTRKRHI-UHFFFAOYSA-N 10-chlorodec-1-ene Chemical compound ClCCCCCCCCC=C QOCVTOZYTRKRHI-UHFFFAOYSA-N 0.000 description 4
- PXUHUAWWMDRECM-UHFFFAOYSA-N 2-fluorooctan-1-ol Chemical compound CCCCCCC(F)CO PXUHUAWWMDRECM-UHFFFAOYSA-N 0.000 description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
- JTGCXYYDAVPSFD-UHFFFAOYSA-N 4-(4-hydroxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(O)C=C1 JTGCXYYDAVPSFD-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- QNXYZQSFDTZEBK-UHFFFAOYSA-N dodec-11-en-1-ol Chemical compound OCCCCCCCCCCC=C QNXYZQSFDTZEBK-UHFFFAOYSA-N 0.000 description 4
- 230000005621 ferroelectricity Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- SJWFXCIHNDVPSH-MRVPVSSYSA-N (2R)-octan-2-ol Chemical compound CCCCCC[C@@H](C)O SJWFXCIHNDVPSH-MRVPVSSYSA-N 0.000 description 3
- BTANRVKWQNVYAZ-BYPYZUCNSA-N (2S)-butan-2-ol Chemical compound CC[C@H](C)O BTANRVKWQNVYAZ-BYPYZUCNSA-N 0.000 description 3
- QPKMYSABIIWIIS-UHFFFAOYSA-N 12-chlorododec-1-ene Chemical compound ClCCCCCCCCCCC=C QPKMYSABIIWIIS-UHFFFAOYSA-N 0.000 description 3
- YCVMFKRVGOAHAA-UHFFFAOYSA-N 2-methylbutyl 4-hydroxybenzoate Chemical compound CCC(C)COC(=O)C1=CC=C(O)C=C1 YCVMFKRVGOAHAA-UHFFFAOYSA-N 0.000 description 3
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004990 Smectic liquid crystal Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical compound C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- FYXQIMAAEMCZLV-UHFFFAOYSA-N ethyl 4-(4-hydroxyphenyl)benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1C1=CC=C(O)C=C1 FYXQIMAAEMCZLV-UHFFFAOYSA-N 0.000 description 3
- GPOPHQSTNHUENT-UHFFFAOYSA-N methyl ethyl caproic acid Natural products CCC(C)CCCCC(O)=O GPOPHQSTNHUENT-UHFFFAOYSA-N 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- NBUCOPILRSUCHR-UHFFFAOYSA-N 2-(hydroxymethyl)butanenitrile Chemical compound CCC(CO)C#N NBUCOPILRSUCHR-UHFFFAOYSA-N 0.000 description 2
- VZIQXGLTRZLBEX-UHFFFAOYSA-N 2-chloro-1-propanol Chemical compound CC(Cl)CO VZIQXGLTRZLBEX-UHFFFAOYSA-N 0.000 description 2
- QMYSXXQDOZTXAE-UHFFFAOYSA-N 2-chloro-3-methylpentanoic acid Chemical compound CCC(C)C(Cl)C(O)=O QMYSXXQDOZTXAE-UHFFFAOYSA-N 0.000 description 2
- FTOKYBLHOYVORA-UHFFFAOYSA-N 2-chlorobutan-1-ol Chemical compound CCC(Cl)CO FTOKYBLHOYVORA-UHFFFAOYSA-N 0.000 description 2
- RVBUZBPJAGZHSQ-UHFFFAOYSA-N 2-chlorobutanoic acid Chemical compound CCC(Cl)C(O)=O RVBUZBPJAGZHSQ-UHFFFAOYSA-N 0.000 description 2
- XNINAOUGJUYOQX-UHFFFAOYSA-N 2-cyanobutanoic acid Chemical compound CCC(C#N)C(O)=O XNINAOUGJUYOQX-UHFFFAOYSA-N 0.000 description 2
- NVIVQGNQOLBSLT-UHFFFAOYSA-N 2-fluorohexan-1-ol Chemical compound CCCCC(F)CO NVIVQGNQOLBSLT-UHFFFAOYSA-N 0.000 description 2
- LRKCNYYCJZXSHR-UHFFFAOYSA-N 2-fluorononan-1-ol Chemical compound CCCCCCCC(F)CO LRKCNYYCJZXSHR-UHFFFAOYSA-N 0.000 description 2
- SASJUHYALINSSV-UHFFFAOYSA-N 2-fluorooctanoic acid Chemical compound CCCCCCC(F)C(O)=O SASJUHYALINSSV-UHFFFAOYSA-N 0.000 description 2
- BGSOIHDNGJTTCV-UHFFFAOYSA-N 2-fluorooctyl 4-hydroxybenzoate Chemical compound CCCCCCC(F)COC(=O)C1=CC=C(O)C=C1 BGSOIHDNGJTTCV-UHFFFAOYSA-N 0.000 description 2
- PFNHSEQQEPMLNI-UHFFFAOYSA-N 2-methyl-1-pentanol Chemical compound CCCC(C)CO PFNHSEQQEPMLNI-UHFFFAOYSA-N 0.000 description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 2
- OVBFMEVBMNZIBR-UHFFFAOYSA-N 2-methylvaleric acid Chemical compound CCCC(C)C(O)=O OVBFMEVBMNZIBR-UHFFFAOYSA-N 0.000 description 2
- IWTBVKIGCDZRPL-UHFFFAOYSA-N 3-methylpentanol Chemical compound CCC(C)CCO IWTBVKIGCDZRPL-UHFFFAOYSA-N 0.000 description 2
- IGIDLTISMCAULB-UHFFFAOYSA-N 3-methylvaleric acid Chemical compound CCC(C)CC(O)=O IGIDLTISMCAULB-UHFFFAOYSA-N 0.000 description 2
- NEQFBGHQPUXOFH-UHFFFAOYSA-N 4-(4-carboxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C=C1 NEQFBGHQPUXOFH-UHFFFAOYSA-N 0.000 description 2
- DQHUGAIXHZQNOJ-UHFFFAOYSA-N 4-dec-1-enoxybenzoyl chloride Chemical compound CCCCCCCCC=COC1=CC=C(C(Cl)=O)C=C1 DQHUGAIXHZQNOJ-UHFFFAOYSA-N 0.000 description 2
- YNPVNLWKVZZBTM-UHFFFAOYSA-N 4-methylhexan-1-ol Chemical compound CCC(C)CCCO YNPVNLWKVZZBTM-UHFFFAOYSA-N 0.000 description 2
- KFARNLMRENFOHE-UHFFFAOYSA-N 5-methylheptan-1-ol Chemical compound CCC(C)CCCCO KFARNLMRENFOHE-UHFFFAOYSA-N 0.000 description 2
- WWRGKAMABZHMCN-UHFFFAOYSA-N 6-methyloctan-1-ol Chemical compound CCC(C)CCCCCO WWRGKAMABZHMCN-UHFFFAOYSA-N 0.000 description 2
- SNMOMUYLFLGQQS-UHFFFAOYSA-N 8-bromooct-1-ene Chemical compound BrCCCCCCC=C SNMOMUYLFLGQQS-UHFFFAOYSA-N 0.000 description 2
- 229920000106 Liquid crystal polymer Polymers 0.000 description 2
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 230000002140 halogenating effect Effects 0.000 description 2
- UIZVMOZAXAMASY-UHFFFAOYSA-N hex-5-en-1-ol Chemical compound OCCCCC=C UIZVMOZAXAMASY-UHFFFAOYSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000005693 optoelectronics Effects 0.000 description 2
- 150000004965 peroxy acids Chemical class 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- URSAOWKEGRPVPC-UHFFFAOYSA-N (2-chloro-3-methylpentyl) 4-hydroxybenzoate Chemical compound CCC(C)C(Cl)COC(=O)C1=CC=C(O)C=C1 URSAOWKEGRPVPC-UHFFFAOYSA-N 0.000 description 1
- BTANRVKWQNVYAZ-SCSAIBSYSA-N (2R)-butan-2-ol Chemical compound CC[C@@H](C)O BTANRVKWQNVYAZ-SCSAIBSYSA-N 0.000 description 1
- SJWFXCIHNDVPSH-QMMMGPOBSA-N (2S)-octan-2-ol Chemical compound CCCCCC[C@H](C)O SJWFXCIHNDVPSH-QMMMGPOBSA-N 0.000 description 1
- GAWAYYRQGQZKCR-UWTATZPHSA-N (2r)-2-chloropropanoic acid Chemical compound C[C@@H](Cl)C(O)=O GAWAYYRQGQZKCR-UWTATZPHSA-N 0.000 description 1
- JYVLIDXNZAXMDK-YFKPBYRVSA-N (2s)-pentan-2-ol Chemical compound CCC[C@H](C)O JYVLIDXNZAXMDK-YFKPBYRVSA-N 0.000 description 1
- VTMXYYQJEPXEIM-UHFFFAOYSA-N (4-butan-2-yloxycarbonylphenyl) 4-dec-9-enoxybenzoate Chemical compound C1=CC(C(=O)OC(C)CC)=CC=C1OC(=O)C1=CC=C(OCCCCCCCCC=C)C=C1 VTMXYYQJEPXEIM-UHFFFAOYSA-N 0.000 description 1
- NNPICKDDMMMVQW-UHFFFAOYSA-N (4-pentan-2-yloxycarbonylphenyl) 4-dec-9-enoxybenzoate Chemical compound C1=CC(C(=O)OC(C)CCC)=CC=C1OC(=O)C1=CC=C(OCCCCCCCCC=C)C=C1 NNPICKDDMMMVQW-UHFFFAOYSA-N 0.000 description 1
- DIVCBWJKVSFZKJ-ZCFIWIBFSA-N (4r)-4-methylhexanoic acid Chemical compound CC[C@@H](C)CCC(O)=O DIVCBWJKVSFZKJ-ZCFIWIBFSA-N 0.000 description 1
- DIVCBWJKVSFZKJ-LURJTMIESA-N (4s)-4-methylhexanoic acid Chemical compound CC[C@H](C)CCC(O)=O DIVCBWJKVSFZKJ-LURJTMIESA-N 0.000 description 1
- GAWAYYRQGQZKCR-REOHCLBHSA-N (S)-2-chloropropanoic acid Chemical compound C[C@H](Cl)C(O)=O GAWAYYRQGQZKCR-REOHCLBHSA-N 0.000 description 1
- WLAMNBDJUVNPJU-BYPYZUCNSA-N (S)-2-methylbutyric acid Chemical compound CC[C@H](C)C(O)=O WLAMNBDJUVNPJU-BYPYZUCNSA-N 0.000 description 1
- AWRUMPCQJSCWRV-UHFFFAOYSA-N 2-methylbutyl 4-[4-(4-dec-9-enoxybenzoyl)oxyphenyl]benzoate Chemical compound C1=CC(C(=O)OCC(C)CC)=CC=C1C(C=C1)=CC=C1OC(=O)C1=CC=C(OCCCCCCCCC=C)C=C1 AWRUMPCQJSCWRV-UHFFFAOYSA-N 0.000 description 1
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 1
- DIVCBWJKVSFZKJ-UHFFFAOYSA-N 4-methylhexanoic acid Natural products CCC(C)CCC(O)=O DIVCBWJKVSFZKJ-UHFFFAOYSA-N 0.000 description 1
- LZIFXXVPLXFRNI-UHFFFAOYSA-N 4-oct-7-enoxybenzoic acid Chemical compound OC(=O)C1=CC=C(OCCCCCCC=C)C=C1 LZIFXXVPLXFRNI-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- RIMXEJYJXDBLIE-UHFFFAOYSA-N 6-bromohex-1-ene Chemical compound BrCCCCC=C RIMXEJYJXDBLIE-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 235000002597 Solanum melongena Nutrition 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- UNLWKCQMJLSQSS-UHFFFAOYSA-N [4-(2-chloro-3-methylpentoxy)carbonylphenyl] 4-dec-9-enoxybenzoate Chemical compound C1=CC(C(=O)OCC(Cl)C(C)CC)=CC=C1OC(=O)C1=CC=C(OCCCCCCCCC=C)C=C1 UNLWKCQMJLSQSS-UHFFFAOYSA-N 0.000 description 1
- IGXFONJVKZEWBP-UHFFFAOYSA-N [4-(2-fluorooctoxycarbonyl)phenyl] 4-dec-9-enoxybenzoate Chemical compound C1=CC(C(=O)OCC(F)CCCCCC)=CC=C1OC(=O)C1=CC=C(OCCCCCCCCC=C)C=C1 IGXFONJVKZEWBP-UHFFFAOYSA-N 0.000 description 1
- UIEWETXPGFWKAS-UHFFFAOYSA-N [4-(2-methylbutoxycarbonyl)phenyl] 4-(4-dec-9-enoxyphenyl)benzoate Chemical compound C1=CC(C(=O)OCC(C)CC)=CC=C1OC(=O)C1=CC=C(C=2C=CC(OCCCCCCCCC=C)=CC=2)C=C1 UIEWETXPGFWKAS-UHFFFAOYSA-N 0.000 description 1
- MUTQJZXDJHIEHQ-UHFFFAOYSA-N [4-(2-methylbutoxycarbonyl)phenyl] 4-dec-9-enoxybenzoate Chemical compound C1=CC(C(=O)OCC(C)CC)=CC=C1OC(=O)C1=CC=C(OCCCCCCCCC=C)C=C1 MUTQJZXDJHIEHQ-UHFFFAOYSA-N 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- ZUOTXZHOGPQFIU-UHFFFAOYSA-N butan-2-yl 4-hydroxybenzoate Chemical compound CCC(C)OC(=O)C1=CC=C(O)C=C1 ZUOTXZHOGPQFIU-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000010228 ethyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004403 ethyl p-hydroxybenzoate Substances 0.000 description 1
- 229940043351 ethyl-p-hydroxybenzoate Drugs 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- RBBOWEDMXHTEPA-UHFFFAOYSA-N hexane;toluene Chemical compound CCCCCC.CC1=CC=CC=C1 RBBOWEDMXHTEPA-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000015654 memory Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- WXPWPYISTQCNDP-UHFFFAOYSA-N oct-7-en-1-ol Chemical compound OCCCCCCC=C WXPWPYISTQCNDP-UHFFFAOYSA-N 0.000 description 1
- JNXAOLWWDAIBSE-UHFFFAOYSA-N octan-2-yl 4-hydroxybenzoate Chemical compound CCCCCCC(C)OC(=O)C1=CC=C(O)C=C1 JNXAOLWWDAIBSE-UHFFFAOYSA-N 0.000 description 1
- ZSSKNOXKMJCTRN-UHFFFAOYSA-N octan-2-yl 4-hydroxybenzoate;thionyl dichloride Chemical compound ClS(Cl)=O.CCCCCCC(C)OC(=O)C1=CC=C(O)C=C1 ZSSKNOXKMJCTRN-UHFFFAOYSA-N 0.000 description 1
- VIZHEHGQHCKXBS-UHFFFAOYSA-N pentan-2-yl 4-hydroxybenzoate Chemical compound CCCC(C)OC(=O)C1=CC=C(O)C=C1 VIZHEHGQHCKXBS-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
Landscapes
- Polyethers (AREA)
- Liquid Crystal Substances (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP28847687A JPS63264629A (ja) | 1986-12-29 | 1987-11-17 | ポリマー |
| EP87119309A EP0274128B1 (de) | 1986-12-29 | 1987-12-29 | Flüssigkristallines Polymer |
| DE3752264T DE3752264T2 (de) | 1986-12-29 | 1987-12-29 | Flüssigkristallines Polymer |
| US07/272,010 US4877858A (en) | 1986-12-29 | 1988-11-16 | Liquid-crystalline polymer |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30946686 | 1986-12-29 | ||
| JP61-309466 | 1986-12-29 | ||
| JP28847687A JPS63264629A (ja) | 1986-12-29 | 1987-11-17 | ポリマー |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63264629A JPS63264629A (ja) | 1988-11-01 |
| JPH0457694B2 true JPH0457694B2 (de) | 1992-09-14 |
Family
ID=26557197
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP28847687A Granted JPS63264629A (ja) | 1986-12-29 | 1987-11-17 | ポリマー |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63264629A (de) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0768337B2 (ja) * | 1988-05-11 | 1995-07-26 | ポリプラスチックス株式会社 | 溶融時に異方性を示す樹脂の製造法 |
| US4954600A (en) * | 1988-06-27 | 1990-09-04 | Idemitsu Kosan Co., Ltd. | Ferroelectric liquid-crystalline polymer and epoxide usable to preparation of the ferroelectric liquid-crystalline polymer |
| JPH0757845B2 (ja) * | 1989-02-22 | 1995-06-21 | 出光興産株式会社 | 強誘電性液晶組成物 |
| US5190686A (en) * | 1988-08-26 | 1993-03-02 | Idemitsu Kosan Co., Ltd. | Liquid-crystalline copolymer |
| JPH02101049A (ja) * | 1988-10-05 | 1990-04-12 | Idemitsu Kosan Co Ltd | 液晶化合物及び液晶ポリマー |
| JP2832864B2 (ja) * | 1989-08-08 | 1998-12-09 | キヤノン株式会社 | 高分子液晶組成物及び高分子液晶素子 |
| JP2806590B2 (ja) * | 1990-01-25 | 1998-09-30 | 出光興産株式会社 | 高分子液晶化合物及びその中間体エポキシ化合物 |
| JP2933805B2 (ja) * | 1992-09-30 | 1999-08-16 | シャープ株式会社 | 高分子分散型液晶複合膜および液晶表示素子並びにその製造方法 |
| JP2831521B2 (ja) * | 1992-12-17 | 1998-12-02 | シャープ株式会社 | 強誘電性液晶表示素子及びその製造方法 |
| US6277503B1 (en) | 1998-03-03 | 2001-08-21 | Matsushita Electric Idustrial Co., Ltd | Organic electroluminescent component |
| CN1962810A (zh) | 1998-12-28 | 2007-05-16 | 出光兴产株式会社 | 用于有机场致发光装置的材料 |
| JP4609032B2 (ja) * | 2004-10-20 | 2011-01-12 | チッソ株式会社 | 光重合性化合物およびそれを含む組成物 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62201419A (ja) * | 1986-01-24 | 1987-09-05 | ヘキスト・セラニーズ・コーポレーション | 非線形光学応答を示す側鎖形液晶性ポリマ− |
-
1987
- 1987-11-17 JP JP28847687A patent/JPS63264629A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62201419A (ja) * | 1986-01-24 | 1987-09-05 | ヘキスト・セラニーズ・コーポレーション | 非線形光学応答を示す側鎖形液晶性ポリマ− |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63264629A (ja) | 1988-11-01 |
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