CN1091795C - 光聚合液晶 - Google Patents
光聚合液晶 Download PDFInfo
- Publication number
- CN1091795C CN1091795C CN95116875A CN95116875A CN1091795C CN 1091795 C CN1091795 C CN 1091795C CN 95116875 A CN95116875 A CN 95116875A CN 95116875 A CN95116875 A CN 95116875A CN 1091795 C CN1091795 C CN 1091795C
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- Prior art keywords
- phenylcarbonyloxy
- ooc
- coo
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- Prior art date
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 21
- 150000001875 compounds Chemical class 0.000 claims abstract description 51
- 239000000203 mixture Substances 0.000 claims abstract description 16
- 230000003287 optical effect Effects 0.000 claims abstract description 12
- -1 nitro, acetyl Chemical group 0.000 claims description 95
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 239000004593 Epoxy Substances 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 6
- 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 6
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 6
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 5
- 150000002237 fumaric acid derivatives Chemical class 0.000 claims description 5
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 5
- 229920001567 vinyl ester resin Polymers 0.000 claims description 5
- SZTBMYHIYNGYIA-UHFFFAOYSA-M 2-chloroacrylate Chemical compound [O-]C(=O)C(Cl)=C SZTBMYHIYNGYIA-UHFFFAOYSA-M 0.000 claims description 4
- IMOLAGKJZFODRK-UHFFFAOYSA-N 2-phenylprop-2-enamide Chemical compound NC(=O)C(=C)C1=CC=CC=C1 IMOLAGKJZFODRK-UHFFFAOYSA-N 0.000 claims description 4
- ONPJWQSDZCGSQM-UHFFFAOYSA-N 2-phenylprop-2-enoic acid Chemical compound OC(=O)C(=C)C1=CC=CC=C1 ONPJWQSDZCGSQM-UHFFFAOYSA-N 0.000 claims description 4
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 claims description 4
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- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 4
- 150000002688 maleic acid derivatives Chemical class 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 150000003440 styrenes Chemical class 0.000 claims description 4
- 125000005407 trans-1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])[C@]([H])([*:2])C([H])([H])C([H])([H])[C@@]1([H])[*:1] 0.000 claims description 4
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 claims description 3
- 235000005513 chalcones Nutrition 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000005451 3-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:1])C([H])=C(F)C([*:2])=C1[H] 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical group C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 43
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 229910052799 carbon Inorganic materials 0.000 description 13
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- FLPSQLAEXYKMGQ-UHFFFAOYSA-N 4-(6-prop-2-enoyloxyhexoxy)benzoic acid Chemical compound OC(=O)C1=CC=C(OCCCCCCOC(=O)C=C)C=C1 FLPSQLAEXYKMGQ-UHFFFAOYSA-N 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- XTDRXXOCFOAXEV-UHFFFAOYSA-N [4-(1-hydroxyethoxy)phenyl] 4-(6-prop-2-enoyloxyhexoxy)benzoate Chemical compound C1=CC(OC(O)C)=CC=C1OC(=O)C1=CC=C(OCCCCCCOC(=O)C=C)C=C1 XTDRXXOCFOAXEV-UHFFFAOYSA-N 0.000 description 3
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- QCXCCZXEMOPNTQ-UHFFFAOYSA-N (4-formylphenyl) 4-(6-prop-2-enoyloxyhexoxy)benzoate Chemical compound C1=CC(OCCCCCCOC(=O)C=C)=CC=C1C(=O)OC1=CC=C(C=O)C=C1 QCXCCZXEMOPNTQ-UHFFFAOYSA-N 0.000 description 2
- MNTKWYBPDFGVIV-UHFFFAOYSA-N 2,5-bis[[4-(6-prop-2-enoyloxyhexoxy)benzoyl]oxy]benzoic acid Chemical compound C=1C=C(OC(=O)C=2C=CC(OCCCCCCOC(=O)C=C)=CC=2)C(C(=O)O)=CC=1OC(=O)C1=CC=C(OCCCCCCOC(=O)C=C)C=C1 MNTKWYBPDFGVIV-UHFFFAOYSA-N 0.000 description 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- FRSGEGGAAANZII-UHFFFAOYSA-N 7-phenoxyheptyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCCOC1=CC=CC=C1 FRSGEGGAAANZII-UHFFFAOYSA-N 0.000 description 2
- PGJZKRAPOFBHPS-UHFFFAOYSA-N 8-phenoxyoctyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCCCOC1=CC=CC=C1 PGJZKRAPOFBHPS-UHFFFAOYSA-N 0.000 description 2
- VKDMWMYGKLGAHI-UHFFFAOYSA-N 9-phenoxynonyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCCCCOC1=CC=CC=C1 VKDMWMYGKLGAHI-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000004990 Smectic liquid crystal Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- OMHAXAGZXQLHOB-UHFFFAOYSA-N [3,4-bis[[4-(6-prop-2-enoyloxyhexoxy)benzoyl]oxy]phenyl] 4-(6-prop-2-enoyloxyhexoxy)benzoate Chemical compound C1=CC(OCCCCCCOC(=O)C=C)=CC=C1C(=O)OC(C=C1OC(=O)C=2C=CC(OCCCCCCOC(=O)C=C)=CC=2)=CC=C1OC(=O)C1=CC=C(OCCCCCCOC(=O)C=C)C=C1 OMHAXAGZXQLHOB-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 150000001789 chalcones Chemical group 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NRSAXKWSRGFKAT-UHFFFAOYSA-N 10-phenoxydecyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCCCCCOC1=CC=CC=C1 NRSAXKWSRGFKAT-UHFFFAOYSA-N 0.000 description 1
- SZTBMYHIYNGYIA-UHFFFAOYSA-N 2-chloroacrylic acid Chemical class OC(=O)C(Cl)=C SZTBMYHIYNGYIA-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- JRJNSEMUYTUGLA-UHFFFAOYSA-N 3-phenoxypropyl prop-2-enoate Chemical compound C=CC(=O)OCCCOC1=CC=CC=C1 JRJNSEMUYTUGLA-UHFFFAOYSA-N 0.000 description 1
- REPOBJYFXIYYSV-UHFFFAOYSA-N 4-(1-hydroxyethoxy)phenol Chemical compound CC(O)OC1=CC=C(O)C=C1 REPOBJYFXIYYSV-UHFFFAOYSA-N 0.000 description 1
- QDBFCZCIBRFQBR-UHFFFAOYSA-N 4-hydroxybutyl benzoate Chemical compound OCCCCOC(=O)C1=CC=CC=C1 QDBFCZCIBRFQBR-UHFFFAOYSA-N 0.000 description 1
- RGLHEMZXTOODQW-UHFFFAOYSA-N 4-phenoxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC1=CC=CC=C1 RGLHEMZXTOODQW-UHFFFAOYSA-N 0.000 description 1
- SWBBFSRVWQYYDA-UHFFFAOYSA-N 5-phenoxypentyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCOC1=CC=CC=C1 SWBBFSRVWQYYDA-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- HSXBZNHNNPLBFF-UHFFFAOYSA-N [3,4-bis[[4-(10-prop-2-enoyloxydecoxy)benzoyl]oxy]phenyl] 4-(10-prop-2-enoyloxydecoxy)benzoate Chemical compound C1=CC(OCCCCCCCCCCOC(=O)C=C)=CC=C1C(=O)OC(C=C1OC(=O)C=2C=CC(OCCCCCCCCCCOC(=O)C=C)=CC=2)=CC=C1OC(=O)C1=CC=C(OCCCCCCCCCCOC(=O)C=C)C=C1 HSXBZNHNNPLBFF-UHFFFAOYSA-N 0.000 description 1
- FWCOIHKBJBSOJW-UHFFFAOYSA-N [3,4-bis[[4-(11-prop-2-enoyloxyundecoxy)benzoyl]oxy]phenyl] 4-(11-prop-2-enoyloxyundecoxy)benzoate Chemical compound C1=CC(OCCCCCCCCCCCOC(=O)C=C)=CC=C1C(=O)OC(C=C1OC(=O)C=2C=CC(OCCCCCCCCCCCOC(=O)C=C)=CC=2)=CC=C1OC(=O)C1=CC=C(OCCCCCCCCCCCOC(=O)C=C)C=C1 FWCOIHKBJBSOJW-UHFFFAOYSA-N 0.000 description 1
- OWBBTUWWYISFDK-UHFFFAOYSA-N [3,4-bis[[4-(3-prop-2-enoyloxypropoxy)benzoyl]oxy]phenyl] 4-(3-prop-2-enoyloxypropoxy)benzoate Chemical compound C1=CC(OCCCOC(=O)C=C)=CC=C1C(=O)OC(C=C1OC(=O)C=2C=CC(OCCCOC(=O)C=C)=CC=2)=CC=C1OC(=O)C1=CC=C(OCCCOC(=O)C=C)C=C1 OWBBTUWWYISFDK-UHFFFAOYSA-N 0.000 description 1
- WAZFJMQZBTZIEW-UHFFFAOYSA-N [3,4-bis[[4-(4-prop-2-enoyloxybutoxy)benzoyl]oxy]phenyl] 4-(4-prop-2-enoyloxybutoxy)benzoate Chemical compound C1=CC(OCCCCOC(=O)C=C)=CC=C1C(=O)OC(C=C1OC(=O)C=2C=CC(OCCCCOC(=O)C=C)=CC=2)=CC=C1OC(=O)C1=CC=C(OCCCCOC(=O)C=C)C=C1 WAZFJMQZBTZIEW-UHFFFAOYSA-N 0.000 description 1
- NQCSXQAJJVRQDL-UHFFFAOYSA-N [3,4-bis[[4-(5-prop-2-enoyloxypentoxy)benzoyl]oxy]phenyl] 4-(5-prop-2-enoyloxypentoxy)benzoate Chemical compound C1=CC(OCCCCCOC(=O)C=C)=CC=C1C(=O)OC(C=C1OC(=O)C=2C=CC(OCCCCCOC(=O)C=C)=CC=2)=CC=C1OC(=O)C1=CC=C(OCCCCCOC(=O)C=C)C=C1 NQCSXQAJJVRQDL-UHFFFAOYSA-N 0.000 description 1
- NTVOHYDLPGKOBP-UHFFFAOYSA-N [3,4-bis[[4-(7-prop-2-enoyloxyheptoxy)benzoyl]oxy]phenyl] 4-(7-prop-2-enoyloxyheptoxy)benzoate Chemical compound C1=CC(OCCCCCCCOC(=O)C=C)=CC=C1C(=O)OC(C=C1OC(=O)C=2C=CC(OCCCCCCCOC(=O)C=C)=CC=2)=CC=C1OC(=O)C1=CC=C(OCCCCCCCOC(=O)C=C)C=C1 NTVOHYDLPGKOBP-UHFFFAOYSA-N 0.000 description 1
- GREBKHWAVIHQFL-UHFFFAOYSA-N [3,4-bis[[4-(8-prop-2-enoyloxyoctoxy)benzoyl]oxy]phenyl] 4-(8-prop-2-enoyloxyoctoxy)benzoate Chemical compound C1=CC(OCCCCCCCCOC(=O)C=C)=CC=C1C(=O)OC(C=C1OC(=O)C=2C=CC(OCCCCCCCCOC(=O)C=C)=CC=2)=CC=C1OC(=O)C1=CC=C(OCCCCCCCCOC(=O)C=C)C=C1 GREBKHWAVIHQFL-UHFFFAOYSA-N 0.000 description 1
- XFWCBHGHIFFJCH-UHFFFAOYSA-N [3,4-bis[[4-(9-prop-2-enoyloxynonoxy)benzoyl]oxy]phenyl] 4-(9-prop-2-enoyloxynonoxy)benzoate Chemical compound C1=CC(OCCCCCCCCCOC(=O)C=C)=CC=C1C(=O)OC(C=C1OC(=O)C=2C=CC(OCCCCCCCCCOC(=O)C=C)=CC=2)=CC=C1OC(=O)C1=CC=C(OCCCCCCCCCOC(=O)C=C)C=C1 XFWCBHGHIFFJCH-UHFFFAOYSA-N 0.000 description 1
- YPEWZIDIXXUVIX-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl] 4-(6-prop-2-enoyloxyhexoxy)benzoate Chemical compound C1=CC(CO)=CC=C1OC(=O)C1=CC=C(OCCCCCCOC(=O)C=C)C=C1 YPEWZIDIXXUVIX-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
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- 239000000835 fiber Substances 0.000 description 1
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- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000012720 spontaneous thermal polymerization Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
- C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
- C09K19/2014—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups containing additionally a linking group other than -COO- or -OCO-, e.g. -CH2-CH2-, -CH=CH-, -C=C-; containing at least one additional carbon atom in the chain containing -COO- or -OCO- groups, e.g. -(CH2)m-COO-(CH2)n-
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/92—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with etherified hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F20/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/38—Polymers
- C09K19/3833—Polymers with mesogenic groups in the side chain
- C09K19/3842—Polyvinyl derivatives
- C09K19/3852—Poly(meth)acrylate derivatives
- C09K19/3871—Poly(meth)acrylate derivatives containing amino acid derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Liquid Crystal Substances (AREA)
- Polarising Elements (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH2771/94 | 1994-09-12 | ||
| CH277194 | 1994-09-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1129245A CN1129245A (zh) | 1996-08-21 |
| CN1091795C true CN1091795C (zh) | 2002-10-02 |
Family
ID=4241245
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN95116875A Expired - Fee Related CN1091795C (zh) | 1994-09-12 | 1995-09-11 | 光聚合液晶 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5593617A (enExample) |
| EP (1) | EP0700981B1 (enExample) |
| JP (1) | JP3973707B2 (enExample) |
| KR (1) | KR100391530B1 (enExample) |
| CN (1) | CN1091795C (enExample) |
| DE (1) | DE59508919D1 (enExample) |
| SG (1) | SG38876A1 (enExample) |
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3954098B2 (ja) * | 1995-02-06 | 2007-08-08 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | 二反応性メソゲン化合物および中間体 |
| JP3599815B2 (ja) * | 1995-03-15 | 2004-12-08 | アルプス電気株式会社 | 紫外線架橋化合物、液晶表示素子用配向膜及び液晶表示素子 |
| US5707544A (en) * | 1995-06-07 | 1998-01-13 | Rolic Ag | Chromophore-containing photo cross-linkable liquid crystals |
| DE59605841D1 (de) * | 1995-07-28 | 2000-10-12 | Rolic Ag Zug | Photovernetzbare Chirale Dotierstoffe |
| EP0755918B1 (de) * | 1995-07-28 | 2000-09-06 | Rolic AG | Photovernetzbare flüssigkristalline 1,2-Phenylen-Derivate |
| DE19649056A1 (de) * | 1996-11-27 | 1998-05-28 | Basf Ag | Polymerisierbare Oligomesogene |
| DE19714119A1 (de) * | 1997-04-05 | 1998-10-08 | Daimler Benz Ag | Verbindungen, Verfahren zu deren Herstellung sowie Verfahren zur Herstellung flüssigkristalliner Polymere unter Verwendung dieser Verbindungen |
| JP2000515201A (ja) * | 1997-04-29 | 2000-11-14 | コーニンクレッカ フィリップス エレクトロニクス エヌ ヴィ | 巨視的に配向した架橋ポリマーの製造方法 |
| CN1213989C (zh) | 1997-05-22 | 2005-08-10 | 罗列克股份公司 | 新的可聚合的液晶化合物 |
| GB9817272D0 (en) * | 1998-08-07 | 1998-10-07 | Rolic Ag | Liquid crystalline compounds |
| GB9828124D0 (en) * | 1998-12-22 | 1999-02-17 | Secr Defence Brit | Photoactive propane derivatives and orientation layers |
| GB9903670D0 (en) * | 1999-02-17 | 1999-04-14 | Rolic Ag | Liquid crystal compounds |
| GB9906168D0 (en) * | 1999-03-17 | 1999-05-12 | Rolic Ag | Liquid crystal compounds |
| GB9908934D0 (en) * | 1999-04-19 | 1999-06-16 | Rolic Ag | Liquid crystalline compounds |
| KR100370814B1 (ko) * | 2000-01-11 | 2003-02-05 | 충청북도 농업기술원 | 삼백초 과립 추출차와 그 제조방법 |
| JP2002069450A (ja) * | 2000-08-29 | 2002-03-08 | Dainippon Ink & Chem Inc | 重合性液晶組成物 |
| KR20010073975A (ko) * | 2000-10-02 | 2001-08-04 | 이창환 | 카스카라사그라다 추출분말을 함유하는 혼합침출차의제조방법 |
| KR100451567B1 (ko) * | 2000-10-23 | 2004-10-14 | 김병진 | 엽록소 음료의 제조 방법 |
| KR100418390B1 (ko) * | 2000-12-11 | 2004-02-11 | 김도훈 | 녹차로부터 추출된 항암효과가 우수한 폴리페놀류 화합물 |
| KR100423241B1 (ko) * | 2001-09-21 | 2004-03-18 | 한미향료화학주식회사 | 차추출물의 정제 및 마이크로캡슐화 방법 |
| GB0127252D0 (en) * | 2001-11-13 | 2002-01-02 | Vantico Ag | Production of composite articles composed of thin layers |
| DE10257711B4 (de) * | 2001-12-27 | 2019-09-26 | Merck Patent Gmbh | Polymerisierbare monocyclische Verbindungen enthaltende Flüssigkristallmischungen |
| KR100407037B1 (ko) * | 2002-06-26 | 2003-11-28 | (주)현덕비엔티 | 녹차 추출물을 함유하는 비만 치료제 |
| KR100407036B1 (ko) * | 2002-06-26 | 2003-11-28 | (주)현덕비엔티 | 녹차 추출물을 함유하는 혈당 강하제 |
| US7927671B2 (en) * | 2006-09-21 | 2011-04-19 | Chisso Corporation | Trifunctional compound, composition and polymer thereof |
| JPWO2008105538A1 (ja) | 2007-03-01 | 2010-06-03 | 日本ゼオン株式会社 | 重合性液晶化合物、重合性液晶組成物、液晶性高分子及び光学異方体 |
| EP2143710B1 (en) | 2007-04-24 | 2014-07-09 | Zeon Corporation | Polymerizable liquid crystal compound, polymerizable liquid crystal composition, liquid crystalline polymer, and optically anisotropic material |
| WO2009080147A1 (en) * | 2007-12-21 | 2009-07-02 | Rolic Ag | Functionalized photoreactive compounds |
| EP2222815B1 (en) | 2007-12-21 | 2019-05-29 | ROLIC Technologies AG | Photoalignment composition |
| CN102998733B (zh) | 2008-03-11 | 2016-09-07 | 罗利克有限公司 | 光学生物测量安全元件 |
| CN102076721B (zh) | 2008-06-30 | 2013-04-24 | 日本瑞翁株式会社 | 聚合性液晶化合物、聚合性液晶组合物、液晶性高分子和光学各向异性体 |
| WO2010038591A1 (ja) | 2008-10-01 | 2010-04-08 | 日本ゼオン株式会社 | 重合性キラル化合物、重合性液晶組成物、液晶性高分子及び光学異方体 |
| TWI490316B (zh) | 2009-07-09 | 2015-07-01 | Rolic Ag | 用於光學或光電元件之含酯基液晶 |
| US8257639B2 (en) * | 2009-09-22 | 2012-09-04 | Kent State University | Method of making stimuli responsive liquid crystal-polymer composite fibers |
| US9200201B2 (en) | 2009-10-22 | 2015-12-01 | Zeon Corporation | Heat-insulating particulate pigment and infrared-reflective coating solution |
| JP2011148762A (ja) * | 2009-12-22 | 2011-08-04 | Jnc Corp | 重合性液晶化合物、重合性液晶組成物および異方性ポリマー |
| US8895151B2 (en) | 2010-03-09 | 2014-11-25 | Zeon Corporation | Heat insulating member, heat insulating laminated glass, and heat insulating laminated glass article |
| WO2011122298A1 (ja) | 2010-03-31 | 2011-10-06 | 日本ゼオン株式会社 | 重合性キラル化合物、重合性液晶組成物、液晶性高分子及び光学異方体 |
| KR20150013217A (ko) * | 2012-05-17 | 2015-02-04 | 고쿠리쓰다이가쿠호진 규슈다이가쿠 | 신규 화합물, 중합성 액정성 화합물, 모노머/액정 혼합재료 및 고분자/액정 복합재료 |
| US11181674B2 (en) | 2016-07-29 | 2021-11-23 | Rolic Technologies AG | Method for generating alignment on top of a liquid crystal polymer material |
| JP6988809B2 (ja) | 2016-08-19 | 2022-01-05 | 日本ゼオン株式会社 | 識別用表示媒体及びその製造方法 |
| JP6907654B2 (ja) | 2017-03-31 | 2021-07-21 | 日本ゼオン株式会社 | コレステリック液晶樹脂微粒子の製造方法 |
| CN109467643A (zh) * | 2018-09-29 | 2019-03-15 | 苏州市新广益电子有限公司 | 一种用于fpc行业的lcp胶膜及其制备方法 |
| CN113631686B (zh) | 2019-04-08 | 2024-10-29 | 罗利克技术有限公司 | 液晶化合物 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5202053A (en) * | 1991-02-22 | 1993-04-13 | Hercules Incorporated | Polymerizable nematic monomer compositions |
| EP0611981A1 (de) * | 1993-02-17 | 1994-08-24 | F. Hoffmann-La Roche Ag | Optisches Bauelement |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH201694A (de) | 1936-10-01 | 1938-12-15 | Aluminium Lab Ltd | Verfahren zur Verhinderung der bei der Wärmebehandlung von Aluminium und Aluminiumlegierungen mit mehr als 50% Aluminium auftretenden Blasenbildung durch hohe Temperaturen. |
| CH201794A (de) | 1937-10-02 | 1938-12-15 | E Herzer Alfred | Tube. |
| US4615962A (en) * | 1979-06-25 | 1986-10-07 | University Patents, Inc. | Diacetylenes having liquid crystal phases |
| NL8802832A (nl) * | 1988-02-29 | 1989-09-18 | Philips Nv | Methode voor het vervaardigen van een gelaagd element en het aldus verkregen element. |
| US5210630A (en) * | 1989-10-18 | 1993-05-11 | U.S. Philips Corporation | Liquid-crystal display device |
| DE4124859A1 (de) * | 1991-07-26 | 1993-01-28 | Merck Patent Gmbh | Fluessigkristalline elastomere oder duomere mit fixierter anisotroper netzwerkstruktur |
| DE69325555D1 (de) * | 1992-04-27 | 1999-08-12 | Merck Patent Gmbh | Elektrooptisches fluessigkristallsystem |
| DE4233660A1 (de) * | 1992-10-08 | 1994-07-07 | Hoechst Ag | Glasartig erstarrende chiral smektische Flüssigkristalle für NLO Anwendungen |
-
1995
- 1995-08-21 US US08/517,480 patent/US5593617A/en not_active Expired - Fee Related
- 1995-08-28 JP JP21872995A patent/JP3973707B2/ja not_active Expired - Fee Related
- 1995-09-02 DE DE59508919T patent/DE59508919D1/de not_active Expired - Fee Related
- 1995-09-02 EP EP95113802A patent/EP0700981B1/de not_active Expired - Lifetime
- 1995-09-07 KR KR1019950029377A patent/KR100391530B1/ko not_active Expired - Fee Related
- 1995-09-08 SG SG1995001310A patent/SG38876A1/en unknown
- 1995-09-11 CN CN95116875A patent/CN1091795C/zh not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5202053A (en) * | 1991-02-22 | 1993-04-13 | Hercules Incorporated | Polymerizable nematic monomer compositions |
| EP0611981A1 (de) * | 1993-02-17 | 1994-08-24 | F. Hoffmann-La Roche Ag | Optisches Bauelement |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0700981A3 (enExample) | 1996-03-27 |
| EP0700981B1 (de) | 2000-12-27 |
| US5593617A (en) | 1997-01-14 |
| CN1129245A (zh) | 1996-08-21 |
| JP3973707B2 (ja) | 2007-09-12 |
| JPH08104870A (ja) | 1996-04-23 |
| KR100391530B1 (ko) | 2003-11-20 |
| HK1011043A1 (en) | 1999-07-02 |
| KR960010608A (ko) | 1996-04-20 |
| SG38876A1 (en) | 1997-04-17 |
| EP0700981A2 (de) | 1996-03-13 |
| DE59508919D1 (de) | 2001-02-01 |
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| C53 | Correction of patent of invention or patent application | ||
| COR | Change of bibliographic data |
Free format text: CORRECT: APPLICANT; FROM: HOFFMAN-LALUOAI LTD. TO: RALEIGHCO STOCK CO., LTD. |
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Address after: Swiss Swiss Applicant after: Rolic AG Address before: Basel Applicant before: F. Hoffmann-La Roche AG |
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| C14 | Grant of patent or utility model | ||
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