DE69820612T2 - Neue polymerisierbare flüssigkristalline verbindungen - Google Patents
Neue polymerisierbare flüssigkristalline verbindungen Download PDFInfo
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- DE69820612T2 DE69820612T2 DE69820612T DE69820612T DE69820612T2 DE 69820612 T2 DE69820612 T2 DE 69820612T2 DE 69820612 T DE69820612 T DE 69820612T DE 69820612 T DE69820612 T DE 69820612T DE 69820612 T2 DE69820612 T2 DE 69820612T2
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- 239000004973 liquid crystal related substance Substances 0.000 title claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 42
- -1 pyridine-2,5-diyl Chemical group 0.000 claims description 38
- 230000003287 optical effect Effects 0.000 claims description 25
- 239000000460 chlorine Substances 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 12
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 12
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 239000011737 fluorine Substances 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 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 6
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000006850 spacer group Chemical group 0.000 claims description 3
- 125000005449 2-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:2])C([H])=C(F)C([*:1])=C1[H] 0.000 claims description 2
- 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
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 238000000034 method Methods 0.000 description 15
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 238000001953 recrystallisation Methods 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 239000007858 starting material Substances 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 8
- 239000003480 eluent Substances 0.000 description 8
- LSVLMFBVUQQWOQ-UMSPYCQHSA-N C1C[C@@H](O)CC[C@@H]1C1=CC=C(O)C=C1 Chemical compound C1C[C@@H](O)CC[C@@H]1C1=CC=C(O)C=C1 LSVLMFBVUQQWOQ-UMSPYCQHSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 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 5
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 5
- 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 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- VDZDJGMSXBFJKJ-UHFFFAOYSA-N 4-(3-fluoro-4-hydroxyphenyl)cyclohexan-1-one Chemical compound C1=C(F)C(O)=CC=C1C1CCC(=O)CC1 VDZDJGMSXBFJKJ-UHFFFAOYSA-N 0.000 description 4
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- VVLHJYUGDKBRJW-UHFFFAOYSA-N pentyl 2-hydroxy-5-(4-oxocyclohexyl)benzoate Chemical compound C1=C(O)C(C(=O)OCCCCC)=CC(C2CCC(=O)CC2)=C1 VVLHJYUGDKBRJW-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- FUCGFRGQQUSOFB-UHFFFAOYSA-N 2-hydroxy-5-(4-oxocyclohexyl)benzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(C2CCC(=O)CC2)=C1 FUCGFRGQQUSOFB-UHFFFAOYSA-N 0.000 description 3
- QMJAKYDVJXMKDN-UHFFFAOYSA-N 4-(3-acetyl-4-hydroxyphenyl)cyclohexan-1-one Chemical compound C1=C(O)C(C(=O)C)=CC(C2CCC(=O)CC2)=C1 QMJAKYDVJXMKDN-UHFFFAOYSA-N 0.000 description 3
- JVKPTVFUEQBSSO-UHFFFAOYSA-N 4-[4-(6-prop-2-enoyloxyhexoxy)phenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(OCCCCCCOC(=O)C=C)C=C1 JVKPTVFUEQBSSO-UHFFFAOYSA-N 0.000 description 3
- AUZPKZGIOYCYNV-UHFFFAOYSA-N 6-chlorohexyl prop-2-enoate Chemical compound ClCCCCCCOC(=O)C=C AUZPKZGIOYCYNV-UHFFFAOYSA-N 0.000 description 3
- RAYIHHANFDBPCF-UHFFFAOYSA-N 8-(3-fluoro-4-phenylmethoxyphenyl)-1,4-dioxaspiro[4.5]dec-7-ene Chemical compound FC1=CC(C=2CCC3(CC=2)OCCO3)=CC=C1OCC1=CC=CC=C1 RAYIHHANFDBPCF-UHFFFAOYSA-N 0.000 description 3
- JAZQZTVJAPQHOU-UHFFFAOYSA-N 8-(3-fluoro-4-phenylmethoxyphenyl)-1,4-dioxaspiro[4.5]decan-8-ol Chemical compound C1CC(O)(C=2C=C(F)C(OCC=3C=CC=CC=3)=CC=2)CCC21OCCO2 JAZQZTVJAPQHOU-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- GIRYDGKKTYGDAI-UHFFFAOYSA-N 2-fluoro-4-(4-hydroxycyclohexyl)phenol Chemical compound C1CC(O)CCC1C1=CC=C(O)C(F)=C1 GIRYDGKKTYGDAI-UHFFFAOYSA-N 0.000 description 2
- SLJYPZJZQIHNGU-UHFFFAOYSA-N 4-(4-hydroxyphenyl)cyclohexan-1-one Chemical compound C1=CC(O)=CC=C1C1CCC(=O)CC1 SLJYPZJZQIHNGU-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KRMSDYMQXPCPPL-CTYIDZIISA-N CCCCCOC(=O)c1cc(ccc1O)[C@H]1CC[C@H](O)CC1 Chemical compound CCCCCOC(=O)c1cc(ccc1O)[C@H]1CC[C@H](O)CC1 KRMSDYMQXPCPPL-CTYIDZIISA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 229940008309 acetone / ethanol Drugs 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000011097 chromatography purification Methods 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
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- 239000011521 glass Substances 0.000 description 2
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- 239000007788 liquid Substances 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 230000002269 spontaneous 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
- 229910052724 xenon Inorganic materials 0.000 description 2
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HKQTYQDNCKMNHZ-UHFFFAOYSA-N 1,4-dioxaspiro[4.5]decan-8-ol Chemical compound C1CC(O)CCC21OCCO2 HKQTYQDNCKMNHZ-UHFFFAOYSA-N 0.000 description 1
- VKRKCBWIVLSRBJ-UHFFFAOYSA-N 1,4-dioxaspiro[4.5]decan-8-one Chemical compound C1CC(=O)CCC21OCCO2 VKRKCBWIVLSRBJ-UHFFFAOYSA-N 0.000 description 1
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
- HEBDGRTWECSNNT-UHFFFAOYSA-N 2-methylidenepentanoic acid Chemical compound CCCC(=C)C(O)=O HEBDGRTWECSNNT-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- ARUBXNBYMCVENE-UHFFFAOYSA-N 4-(4-bromophenyl)phenol Chemical compound C1=CC(O)=CC=C1C1=CC=C(Br)C=C1 ARUBXNBYMCVENE-UHFFFAOYSA-N 0.000 description 1
- LSVLMFBVUQQWOQ-UHFFFAOYSA-N 4-(4-hydroxycyclohexyl)phenol Chemical compound C1CC(O)CCC1C1=CC=C(O)C=C1 LSVLMFBVUQQWOQ-UHFFFAOYSA-N 0.000 description 1
- DTBNPTQBRPZVCZ-UHFFFAOYSA-N 4-(7-oxonon-8-enoxy)benzoic acid Chemical compound OC(=O)C1=CC=C(OCCCCCCC(=O)C=C)C=C1 DTBNPTQBRPZVCZ-UHFFFAOYSA-N 0.000 description 1
- HCVUDNMNSPYSHS-UHFFFAOYSA-N 4-bromo-2-fluoro-1-phenylmethoxybenzene Chemical compound FC1=CC(Br)=CC=C1OCC1=CC=CC=C1 HCVUDNMNSPYSHS-UHFFFAOYSA-N 0.000 description 1
- HLXJEKPLQLVJGK-UHFFFAOYSA-N 4-ethynylphenol Chemical compound OC1=CC=C(C#C)C=C1 HLXJEKPLQLVJGK-UHFFFAOYSA-N 0.000 description 1
- 125000006043 5-hexenyl group Chemical group 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
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- OJJOBIOIMYXFNU-ZVTZDLPXSA-N OCCC[C@H]1CC[C@@H](CC1)c1ccc(cc1)C#Cc1ccc(cc1)[C@H]1CC[C@H](CCCO)CC1 Chemical compound OCCC[C@H]1CC[C@@H](CC1)c1ccc(cc1)C#Cc1ccc(cc1)[C@H]1CC[C@H](CCCO)CC1 OJJOBIOIMYXFNU-ZVTZDLPXSA-N 0.000 description 1
- VGYAAWYHVAAJNX-UMSPYCQHSA-N O[C@H]1CC[C@@H](CC1)c1ccc(Br)cc1 Chemical compound O[C@H]1CC[C@@H](CC1)c1ccc(Br)cc1 VGYAAWYHVAAJNX-UMSPYCQHSA-N 0.000 description 1
- KKNCFIKJIJQLKQ-CZMCAQCFSA-N O[C@H]1CC[C@@H](CC1)c1ccc(O)c(Cl)c1 Chemical compound O[C@H]1CC[C@@H](CC1)c1ccc(O)c(Cl)c1 KKNCFIKJIJQLKQ-CZMCAQCFSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- ZBTCSYDLYVZCDB-UHFFFAOYSA-N [3-chloro-4-[4-(6-prop-2-enoyloxyhexoxy)benzoyl]oxyphenyl] 4-(6-prop-2-enoyloxyhexoxy)benzoate Chemical compound C=1C=C(OC(=O)C=2C=CC(OCCCCCCOC(=O)C=C)=CC=2)C(Cl)=CC=1OC(=O)C1=CC=C(OCCCCCCOC(=O)C=C)C=C1 ZBTCSYDLYVZCDB-UHFFFAOYSA-N 0.000 description 1
- FQCKIWWAEIOPSD-UHFFFAOYSA-N [3-methyl-4-[4-(6-prop-2-enoyloxyhexoxy)benzoyl]oxyphenyl] 4-(6-prop-2-enoyloxyhexoxy)benzoate Chemical compound C=1C=C(OC(=O)C=2C=CC(OCCCCCCOC(=O)C=C)=CC=2)C(C)=CC=1OC(=O)C1=CC=C(OCCCCCCOC(=O)C=C)C=C1 FQCKIWWAEIOPSD-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000005253 cladding Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012468 concentrated sample Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 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
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005935 hexyloxycarbonyl group Chemical group 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000001400 nonyl 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])C([H])([H])[H] 0.000 description 1
- 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
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/54—Acrylic acid esters; Methacrylic acid esters
-
- 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
- C07C69/94—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of polycyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of six-membered aromatic rings
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- 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
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3059—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon triple bonds
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- 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
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
- C09K19/3068—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers chain containing -COO- or -OCO- groups
-
- 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
-
- 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
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- 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
- C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
-
- 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
- C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
- C09K2019/0448—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
-
- 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
- C09K2019/0477—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by the positioning of substituents on phenylene
- C09K2019/0481—Phenylene substituted in meta position
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- 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
- C09K2019/0477—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by the positioning of substituents on phenylene
- C09K2019/0485—Phenylene substituted in ortho position
-
- 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
- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
- Epoxy Compounds (AREA)
- Pyridine Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP97108259 | 1997-05-22 | ||
| EP97108259 | 1997-05-22 | ||
| PCT/IB1998/000789 WO1998052905A1 (en) | 1997-05-22 | 1998-05-22 | New polymerisable liquid crystalline compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69820612D1 DE69820612D1 (de) | 2004-01-29 |
| DE69820612T2 true DE69820612T2 (de) | 2004-10-14 |
Family
ID=8226813
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69820612T Expired - Fee Related DE69820612T2 (de) | 1997-05-22 | 1998-05-22 | Neue polymerisierbare flüssigkristalline verbindungen |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6395351B1 (enExample) |
| EP (1) | EP0983225B1 (enExample) |
| JP (1) | JP2001527570A (enExample) |
| KR (1) | KR100566684B1 (enExample) |
| CN (1) | CN1213989C (enExample) |
| AU (1) | AU7227698A (enExample) |
| DE (1) | DE69820612T2 (enExample) |
| WO (1) | WO1998052905A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100552259B1 (ko) * | 1998-01-27 | 2006-02-15 | 롤리크 아게 | 틸트 도메인의 형성 감소방법 |
| EP1046631A1 (en) * | 1999-04-19 | 2000-10-25 | Rolic AG | Liquid crystalline compounds |
| GB9908934D0 (en) | 1999-04-19 | 1999-06-16 | Rolic Ag | Liquid crystalline compounds |
| US6514578B1 (en) | 1999-06-30 | 2003-02-04 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Polymerizable mesogenic tolanes |
| GB2359809B (en) * | 1999-12-24 | 2004-01-14 | Sumitomo Chemical Co | Phenylacetylene compound liquid crystal composition, polymer optically anisotropic product, and liquid crystal or optical element |
| CN1230411C (zh) * | 2000-01-21 | 2005-12-07 | 大日本油墨化学工业株式会社 | 显示液晶相的聚合性组合物及使用其的光学各向异性体 |
| DE10016524A1 (de) * | 2000-04-03 | 2001-10-04 | Basf Ag | Polymerisierbare Flüssigkristalle |
| JP4836335B2 (ja) * | 2000-04-25 | 2011-12-14 | 住友化学株式会社 | フェニルアセチレン重合物、光学異方体及び光学又は液晶用素子 |
| DE10025782A1 (de) * | 2000-05-26 | 2001-12-06 | Basf Ag | Flüssigkristalline Stoffgemenge |
| JP2002003845A (ja) * | 2000-06-26 | 2002-01-09 | Fuji Photo Film Co Ltd | 液晶性組成物、カラーフィルタおよび光学フィルム |
| KR100694936B1 (ko) * | 2000-07-20 | 2007-03-14 | 메르크 파텐트 게엠베하 | 중합성 메소제닉 톨란 |
| JP2005534993A (ja) | 2002-08-07 | 2005-11-17 | 富士写真フイルム株式会社 | 位相差板および円偏光板 |
| DE10246774A1 (de) * | 2002-10-07 | 2004-04-15 | Merck Patent Gmbh | Flüssigkristalline Medien enthaltend Polymere |
| US7364670B2 (en) * | 2003-07-17 | 2008-04-29 | Fujifilm Corporation | Liquid crystalline compound, liquid crystalline composition and retardation film |
| DE602006020557D1 (de) * | 2005-04-13 | 2011-04-21 | Asahi Glass Co Ltd | Polymerisierbare flüssigkristalline zusammensetzung, optisch anisotropisches material, optisches element und optische kopfvorrichtung |
| JP5186116B2 (ja) * | 2006-06-12 | 2013-04-17 | 富士フイルム株式会社 | 化合物、それを含有する液晶組成物、異方性材料、偏光板保護フィルム、光学補償フィルムならびに液晶表示装置 |
| ES2494293T3 (es) | 2006-09-13 | 2014-09-15 | Rolic Ag | Retardador fotoalineado por volumen |
| JP5140991B2 (ja) * | 2006-10-31 | 2013-02-13 | Ｄｉｃ株式会社 | 重合性液晶化合物 |
| US8574454B2 (en) * | 2006-12-22 | 2013-11-05 | Rolic Ag | Patternable liquid crystal polymer comprising thio-ether units |
| TWI418613B (zh) * | 2007-02-23 | 2013-12-11 | Zeon Corp | A liquid crystal compound, a liquid crystal composition, an optical film, and an optical laminate |
| JP5186120B2 (ja) * | 2007-03-05 | 2013-04-17 | 富士フイルム株式会社 | 化合物、それを含有する液晶組成物、異方性材料、偏光板保護フィルム、光学補償フィルムならびに液晶表示装置 |
| JP5168976B2 (ja) * | 2007-03-28 | 2013-03-27 | Ｄｉｃ株式会社 | ビフェニル及びテルフェニル化合物、該化合物を含有する重合性液晶組成物 |
| JP5345293B2 (ja) * | 2007-03-29 | 2013-11-20 | 株式会社Ａｄｅｋａ | 重合性化合物及び重合性組成物 |
| KR101649088B1 (ko) * | 2007-08-30 | 2016-08-17 | 메르크 파텐트 게엠베하 | 액정 디스플레이 |
| CN105733606B (zh) | 2007-12-21 | 2018-04-03 | 罗利克有限公司 | 光校准组合物 |
| KR101499238B1 (ko) * | 2008-08-07 | 2015-03-05 | 삼성디스플레이 주식회사 | 액정 표시 장치 |
| JP2010196016A (ja) * | 2009-02-27 | 2010-09-09 | Mitsubishi Electric Corp | 樹脂組成物及び樹脂硬化物 |
| JP2010196015A (ja) * | 2009-02-27 | 2010-09-09 | Mitsubishi Electric Corp | 樹脂組成物及び樹脂硬化物 |
| JP5259501B2 (ja) | 2009-06-11 | 2013-08-07 | 富士フイルム株式会社 | 赤外光反射板、赤外光反射性合わせガラス、並びにコレステリック液晶層を有する積層体及び合わせガラス |
| CN102460241B (zh) | 2009-06-11 | 2014-05-21 | 富士胶片株式会社 | 光反射膜的制造方法 |
| JP5020289B2 (ja) | 2009-06-11 | 2012-09-05 | 富士フイルム株式会社 | 赤外光反射板、及び赤外光反射性合わせガラス |
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| 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 |
| KR20110021587A (ko) * | 2009-08-26 | 2011-03-04 | 삼성전자주식회사 | 액정 표시 장치 및 그 제조 방법 |
| KR101734598B1 (ko) * | 2009-09-03 | 2017-05-11 | 스미또모 가가꾸 가부시끼가이샤 | 디에폭시 화합물, 그 제조 방법 및 그 디에폭시 화합물을 함유하는 조성물 |
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| JP5961498B2 (ja) | 2012-09-18 | 2016-08-02 | 富士フイルム株式会社 | 熱線カットフィルムおよびその製造方法、合わせガラス並びに熱線カット部材 |
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-
1998
- 1998-05-22 WO PCT/IB1998/000789 patent/WO1998052905A1/en not_active Ceased
- 1998-05-22 AU AU72276/98A patent/AU7227698A/en not_active Abandoned
- 1998-05-22 JP JP55018298A patent/JP2001527570A/ja not_active Ceased
- 1998-05-22 CN CNB988053357A patent/CN1213989C/zh not_active Expired - Fee Related
- 1998-05-22 KR KR1019997010737A patent/KR100566684B1/ko not_active Expired - Fee Related
- 1998-05-22 EP EP98919404A patent/EP0983225B1/en not_active Expired - Lifetime
- 1998-05-22 DE DE69820612T patent/DE69820612T2/de not_active Expired - Fee Related
-
1999
- 1999-11-19 US US09/443,214 patent/US6395351B1/en not_active Expired - Fee Related
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| Publication number | Publication date |
|---|---|
| HK1026195A1 (en) | 2000-12-08 |
| JP2001527570A (ja) | 2001-12-25 |
| CN1213989C (zh) | 2005-08-10 |
| EP0983225A1 (en) | 2000-03-08 |
| KR100566684B1 (ko) | 2006-04-03 |
| EP0983225B1 (en) | 2003-12-17 |
| KR20010012775A (ko) | 2001-02-26 |
| DE69820612D1 (de) | 2004-01-29 |
| US6395351B1 (en) | 2002-05-28 |
| CN1257473A (zh) | 2000-06-21 |
| AU7227698A (en) | 1998-12-11 |
| WO1998052905A1 (en) | 1998-11-26 |
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