KR100609200B1 - 광가교성 실란 유도체 - Google Patents
광가교성 실란 유도체 Download PDFInfo
- Publication number
- KR100609200B1 KR100609200B1 KR1019980003265A KR19980003265A KR100609200B1 KR 100609200 B1 KR100609200 B1 KR 100609200B1 KR 1019980003265 A KR1019980003265 A KR 1019980003265A KR 19980003265 A KR19980003265 A KR 19980003265A KR 100609200 B1 KR100609200 B1 KR 100609200B1
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- diyl
- fluorine
- alkoxy
- acid
- 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
- 150000004756 silanes Chemical class 0.000 title claims abstract description 38
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 33
- 239000000203 mixture Substances 0.000 claims abstract description 28
- 230000003287 optical effect Effects 0.000 claims abstract description 11
- -1 cyano- Chemical class 0.000 claims description 296
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 91
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 88
- 229930016911 cinnamic acid Natural products 0.000 claims description 88
- 235000013985 cinnamic acid Nutrition 0.000 claims description 88
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims description 76
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 239000011737 fluorine Substances 0.000 claims description 37
- 229910052731 fluorine Inorganic materials 0.000 claims description 37
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 31
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 28
- 125000001153 fluoro group Chemical group F* 0.000 claims description 26
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 26
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000006850 spacer group Chemical group 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 13
- 229910000077 silane Inorganic materials 0.000 claims description 13
- 125000004959 2,6-naphthylene group Chemical group [H]C1=C([H])C2=C([H])C([*:1])=C([H])C([H])=C2C([H])=C1[*:2] 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- 125000000843 phenylene group Chemical class C1(=C(C=CC=C1)*)* 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000005714 2,5- (1,3-dioxanylene) group Chemical group [H]C1([H])OC([H])([*:1])OC([H])([H])C1([H])[*:2] 0.000 claims description 6
- HJBWJAPEBGSQPR-GQCTYLIASA-N 3,4-dimethoxycinnamic acid Chemical compound COC1=CC=C(\C=C\C(O)=O)C=C1OC HJBWJAPEBGSQPR-GQCTYLIASA-N 0.000 claims description 5
- HJBWJAPEBGSQPR-UHFFFAOYSA-N DMCA Natural products COC1=CC=C(C=CC(O)=O)C=C1OC HJBWJAPEBGSQPR-UHFFFAOYSA-N 0.000 claims description 5
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 125000005731 2,5-thiophenylene group Chemical group [H]C1=C([*:1])SC([*:2])=C1[H] 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052809 inorganic oxide Inorganic materials 0.000 abstract description 2
- 238000002444 silanisation Methods 0.000 abstract description 2
- 239000000758 substrate Substances 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 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 18
- 229920000642 polymer Polymers 0.000 description 17
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000011521 glass Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- 230000002441 reversible effect Effects 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 7
- 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 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 230000010287 polarization Effects 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- ZODPRHWKXOVAAN-XYOKQWHBSA-N (e)-3-(6-heptoxynaphthalen-2-yl)prop-2-enoic acid Chemical compound C1=C(\C=C\C(O)=O)C=CC2=CC(OCCCCCCC)=CC=C21 ZODPRHWKXOVAAN-XYOKQWHBSA-N 0.000 description 4
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- MRAXWDSTXQQMQQ-UHFFFAOYSA-N 2-bromo-6-heptoxynaphthalene Chemical compound C1=C(Br)C=CC2=CC(OCCCCCCC)=CC=C21 MRAXWDSTXQQMQQ-UHFFFAOYSA-N 0.000 description 3
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CVNSFOPHIIRNBE-KESTWPANSA-N CCCCCCC[C@H]1CC[C@H](COc2ccc(C=O)cc2)CC1 Chemical compound CCCCCCC[C@H]1CC[C@H](COc2ccc(C=O)cc2)CC1 CVNSFOPHIIRNBE-KESTWPANSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 238000006471 dimerization reaction Methods 0.000 description 3
- 238000006317 isomerization reaction Methods 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 description 2
- RIMXEJYJXDBLIE-UHFFFAOYSA-N 6-bromohex-1-ene Chemical compound BrCCCCC=C RIMXEJYJXDBLIE-UHFFFAOYSA-N 0.000 description 2
- JNTPTNNCGDAGEJ-UHFFFAOYSA-N 6-chlorohexan-1-ol Chemical compound OCCCCCCCl JNTPTNNCGDAGEJ-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 150000001851 cinnamic acid derivatives Chemical class 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000006459 hydrosilylation reaction Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 2
- 239000005052 trichlorosilane Substances 0.000 description 2
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 2
- FEGVSPGUHMGGBO-VOTSOKGWSA-N (E)-2-methoxycinnamic acid Chemical compound COC1=CC=CC=C1\C=C\C(O)=O FEGVSPGUHMGGBO-VOTSOKGWSA-N 0.000 description 1
- AFDXODALSZRGIH-QPJJXVBHSA-N (E)-3-(4-methoxyphenyl)prop-2-enoic acid Chemical compound COC1=CC=C(\C=C\C(O)=O)C=C1 AFDXODALSZRGIH-QPJJXVBHSA-N 0.000 description 1
- VLSRUFWCGBMYDJ-ONEGZZNKSA-N (e)-3-(3,5-dimethoxyphenyl)prop-2-enoic acid Chemical compound COC1=CC(OC)=CC(\C=C\C(O)=O)=C1 VLSRUFWCGBMYDJ-ONEGZZNKSA-N 0.000 description 1
- FFKGOJWPSXRALK-SNAWJCMRSA-N (e)-3-(3-chlorophenyl)prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=CC=CC(Cl)=C1 FFKGOJWPSXRALK-SNAWJCMRSA-N 0.000 description 1
- WUUPSYGVGNAJEM-WYMLVPIESA-N (e)-3-(3-decoxy-4-methoxyphenyl)prop-2-enoic acid Chemical compound CCCCCCCCCCOC1=CC(\C=C\C(O)=O)=CC=C1OC WUUPSYGVGNAJEM-WYMLVPIESA-N 0.000 description 1
- VKZYEBQHWQTZKA-HWKANZROSA-N (e)-3-(3-fluoro-4-methoxyphenyl)prop-2-enoic acid Chemical compound COC1=CC=C(\C=C\C(O)=O)C=C1F VKZYEBQHWQTZKA-HWKANZROSA-N 0.000 description 1
- RTSIUKMGSDOSTI-SNAWJCMRSA-N (e)-3-(3-fluorophenyl)prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=CC=CC(F)=C1 RTSIUKMGSDOSTI-SNAWJCMRSA-N 0.000 description 1
- RNBDPKQLDZUYSE-ZRDIBKRKSA-N (e)-3-(3-methoxy-4-octoxyphenyl)prop-2-enoic acid Chemical compound CCCCCCCCOC1=CC=C(\C=C\C(O)=O)C=C1OC RNBDPKQLDZUYSE-ZRDIBKRKSA-N 0.000 description 1
- KLKIYWLHYABZHD-VAWYXSNFSA-N (e)-3-(3-octoxyphenyl)prop-2-enoic acid Chemical compound CCCCCCCCOC1=CC=CC(\C=C\C(O)=O)=C1 KLKIYWLHYABZHD-VAWYXSNFSA-N 0.000 description 1
- MBEDYQIDCOTTOZ-FNORWQNLSA-N (e)-3-(4-acetamido-3-ethoxyphenyl)prop-2-enoic acid Chemical compound CCOC1=CC(\C=C\C(O)=O)=CC=C1NC(C)=O MBEDYQIDCOTTOZ-FNORWQNLSA-N 0.000 description 1
- WGMFHSADKZJPGR-QPJJXVBHSA-N (e)-3-(4-acetamidophenyl)prop-2-enoic acid Chemical compound CC(=O)NC1=CC=C(\C=C\C(O)=O)C=C1 WGMFHSADKZJPGR-QPJJXVBHSA-N 0.000 description 1
- AAHNIBROSVVFRO-RMKNXTFCSA-N (e)-3-(4-butoxyphenyl)prop-2-enoic acid Chemical compound CCCCOC1=CC=C(\C=C\C(O)=O)C=C1 AAHNIBROSVVFRO-RMKNXTFCSA-N 0.000 description 1
- MNELKRQRBRYHBV-DUXPYHPUSA-N (e)-3-(4-chloro-3-fluorophenyl)prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=CC=C(Cl)C(F)=C1 MNELKRQRBRYHBV-DUXPYHPUSA-N 0.000 description 1
- ROHQNWKGFWNNJX-SAPNQHFASA-N (e)-3-(4-dodecoxyphenyl)prop-2-enoic acid Chemical compound CCCCCCCCCCCCOC1=CC=C(\C=C\C(O)=O)C=C1 ROHQNWKGFWNNJX-SAPNQHFASA-N 0.000 description 1
- YUPOGZHOMDSGCD-DHZHZOJOSA-N (e)-3-(4-hexoxyphenyl)prop-2-enoic acid Chemical compound CCCCCCOC1=CC=C(\C=C\C(O)=O)C=C1 YUPOGZHOMDSGCD-DHZHZOJOSA-N 0.000 description 1
- ACXHPHWHQQQLPZ-NTCAYCPXSA-N (e)-3-[4-(decanoylamino)phenyl]prop-2-enoic acid Chemical compound CCCCCCCCCC(=O)NC1=CC=C(\C=C\C(O)=O)C=C1 ACXHPHWHQQQLPZ-NTCAYCPXSA-N 0.000 description 1
- XIUDFSXFTLDPHB-JXMROGBWSA-N (e)-3-[4-(pentanoylamino)phenyl]prop-2-enoic acid Chemical compound CCCCC(=O)NC1=CC=C(\C=C\C(O)=O)C=C1 XIUDFSXFTLDPHB-JXMROGBWSA-N 0.000 description 1
- JPQWWJZORKTMIZ-ZZXKWVIFSA-N 2,5-Dimethoxycinnamic acid Chemical compound COC1=CC=C(OC)C(\C=C\C(O)=O)=C1 JPQWWJZORKTMIZ-ZZXKWVIFSA-N 0.000 description 1
- 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 1
- HLAUCEOFCOXKNF-UHFFFAOYSA-N 2-bromoheptane Chemical compound CCCCCC(C)Br HLAUCEOFCOXKNF-UHFFFAOYSA-N 0.000 description 1
- 125000005449 2-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:2])C([H])=C(F)C([*:1])=C1[H] 0.000 description 1
- YTFVRYKNXDADBI-SNAWJCMRSA-N 3,4,5-trimethoxycinnamic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC(OC)=C1OC YTFVRYKNXDADBI-SNAWJCMRSA-N 0.000 description 1
- 125000005451 3-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:1])C([H])=C(F)C([*:2])=C1[H] 0.000 description 1
- ISMMYAZSUSYVQG-ZZXKWVIFSA-N 4-Fluorocinnamic acid Chemical compound OC(=O)\C=C\C1=CC=C(F)C=C1 ISMMYAZSUSYVQG-ZZXKWVIFSA-N 0.000 description 1
- GXLIFJYFGMHYDY-ZZXKWVIFSA-N 4-chlorocinnamic acid Chemical compound OC(=O)\C=C\C1=CC=C(Cl)C=C1 GXLIFJYFGMHYDY-ZZXKWVIFSA-N 0.000 description 1
- YLDFTMJPQJXGSS-UHFFFAOYSA-N 6-bromo-2-naphthol Chemical compound C1=C(Br)C=CC2=CC(O)=CC=C21 YLDFTMJPQJXGSS-UHFFFAOYSA-N 0.000 description 1
- LCTBFKIWHKAAHM-KESTWPANSA-N CCCCCCC[C@H]1CC[C@H](COc2ccc(cc2)C#N)CC1 Chemical compound CCCCCCC[C@H]1CC[C@H](COc2ccc(cc2)C#N)CC1 LCTBFKIWHKAAHM-KESTWPANSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- YTFVRYKNXDADBI-UHFFFAOYSA-N O-Methylsinapic acid Natural products COC1=CC(C=CC(O)=O)=CC(OC)=C1OC YTFVRYKNXDADBI-UHFFFAOYSA-N 0.000 description 1
- QDFKDDCKKXSMEJ-UHFFFAOYSA-N OC(=O)C=CC1=CC=CC=C1.OC(=O)C(=C)C1=CC=CC=C1 Chemical compound OC(=O)C=CC1=CC=CC=C1.OC(=O)C(=C)C1=CC=CC=C1 QDFKDDCKKXSMEJ-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
- 229940005991 chloric acid Drugs 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000005429 filling process Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004687 hexahydrates Chemical class 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- SIGOIUCRXKUEIG-UHFFFAOYSA-N methyl 2-dimethoxyphosphorylacetate Chemical compound COC(=O)CP(=O)(OC)OC SIGOIUCRXKUEIG-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- AFDXODALSZRGIH-UHFFFAOYSA-N p-coumaric acid methyl ether Natural products COC1=CC=C(C=CC(O)=O)C=C1 AFDXODALSZRGIH-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 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 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-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
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
- G02F1/133711—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by organic films, e.g. polymeric films
- G02F1/133719—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by organic films, e.g. polymeric films with coupling agent molecules, e.g. silane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/12—Organo silicon halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- 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
- C09K19/40—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen or sulfur, e.g. silicon, metals
- C09K19/406—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen or sulfur, e.g. silicon, metals containing silicon
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Nonlinear Science (AREA)
- Materials Engineering (AREA)
- Mathematical Physics (AREA)
- Engineering & Computer Science (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Liquid Crystal (AREA)
- Liquid Crystal Substances (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP97101757 | 1997-02-05 | ||
| EP97101757.9 | 1997-02-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR19980071102A KR19980071102A (ko) | 1998-10-26 |
| KR100609200B1 true KR100609200B1 (ko) | 2007-05-14 |
Family
ID=8226437
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019980003265A Expired - Lifetime KR100609200B1 (ko) | 1997-02-05 | 1998-02-05 | 광가교성 실란 유도체 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6277502B1 (enExample) |
| JP (1) | JP4205195B2 (enExample) |
| KR (1) | KR100609200B1 (enExample) |
| CN (1) | CN1213053C (enExample) |
| DE (1) | DE59807348D1 (enExample) |
| SG (1) | SG90026A1 (enExample) |
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE59814236D1 (de) * | 1997-02-24 | 2008-07-17 | Rolic Ag | Photovernetzbare Polymere |
| DE19948475A1 (de) | 1999-10-08 | 2001-04-19 | Jac Products Deutschland Gmbh | Dachreling für Fahrzeuge und Herstellungsverfahren |
| DE19948476C1 (de) | 1999-10-08 | 2001-03-01 | Jac Products Deutschland Gmbh | Dachreling für Fahrzeuge |
| US8282912B2 (en) * | 2002-03-22 | 2012-10-09 | Kuros Biosurgery, AG | Compositions for tissue augmentation |
| ATE541595T1 (de) * | 2002-03-22 | 2012-02-15 | Kuros Biosurgery Ag | Zusammensetzung für die verstärkung von hartem gewebe |
| US20050282814A1 (en) * | 2002-10-03 | 2005-12-22 | Targegen, Inc. | Vasculostatic agents and methods of use thereof |
| AU2005231507B2 (en) | 2004-04-08 | 2012-03-01 | Targegen, Inc. | Benzotriazine inhibitors of kinases |
| NZ588896A (en) | 2004-08-25 | 2012-05-25 | Targegen Inc | Heterocyclic compounds and methods of use |
| JP2006209073A (ja) * | 2004-12-28 | 2006-08-10 | Dainippon Printing Co Ltd | 光学素子及びその製造方法 |
| WO2006101977A2 (en) * | 2005-03-16 | 2006-09-28 | Targegen, Inc. | Pyrimidine compounds and methods of use |
| WO2006133411A1 (en) * | 2005-06-08 | 2006-12-14 | Targegen, Inc. | Methods and compositions for the treatment of ocular disorders |
| WO2007025059A1 (en) * | 2005-08-26 | 2007-03-01 | Surmodics, Inc. | Silane coating compositions, coating systems, and methods |
| US20070141365A1 (en) * | 2005-08-26 | 2007-06-21 | Jelle Bruce M | Silane Coating Compositions, Coating Systems, and Methods |
| WO2007053452A1 (en) | 2005-11-01 | 2007-05-10 | Targegen, Inc. | Bi-aryl meta-pyrimidine inhibitors of kinases |
| US8604042B2 (en) * | 2005-11-01 | 2013-12-10 | Targegen, Inc. | Bi-aryl meta-pyrimidine inhibitors of kinases |
| US8133900B2 (en) * | 2005-11-01 | 2012-03-13 | Targegen, Inc. | Use of bi-aryl meta-pyrimidine inhibitors of kinases |
| US20070149508A1 (en) * | 2005-11-02 | 2007-06-28 | Targegen, Inc. | Six membered heteroaromatic inhibitors targeting resistant kinase mutations |
| WO2008125655A1 (en) * | 2007-04-13 | 2008-10-23 | Kuros Biosurgery Ag | Polymeric tissue sealant |
| KR101469572B1 (ko) * | 2007-05-25 | 2014-12-05 | 롤리크 아게 | 지환족 그룹을 포함하는 광가교결합 가능한 재료 |
| JP5071644B2 (ja) * | 2007-08-01 | 2012-11-14 | Ｊｓｒ株式会社 | ポリオルガノシロキサン、液晶配向膜および液晶表示素子 |
| EP2222740B1 (en) * | 2007-12-21 | 2017-10-11 | Rolic AG | Functionalized photoreactive compounds |
| WO2009080271A1 (en) * | 2007-12-21 | 2009-07-02 | Rolic Ltd. | Photoalignment composition |
| US9847243B2 (en) * | 2009-08-27 | 2017-12-19 | Corning Incorporated | Debonding a glass substrate from carrier using ultrasonic wave |
| JP5525213B2 (ja) | 2009-08-28 | 2014-06-18 | 富士フイルム株式会社 | 偏光膜、積層体、及び液晶表示装置 |
| JP5657243B2 (ja) | 2009-09-14 | 2015-01-21 | ユー・ディー・シー アイルランド リミテッド | カラーフィルタ及び発光表示素子 |
| JP5442518B2 (ja) | 2010-03-31 | 2014-03-12 | 富士フイルム株式会社 | 光吸収異方性膜、偏光フィルム及びその製造方法、並びにそれを用いた表示装置 |
| JP5300776B2 (ja) | 2010-03-31 | 2013-09-25 | 富士フイルム株式会社 | 偏光フィルム、表示装置、及びその製造方法 |
| KR101829479B1 (ko) * | 2010-04-06 | 2018-02-14 | 닛산 가가쿠 고교 가부시키 가이샤 | 액정 배향제, 액정 배향막 및 액정 표시 소자 |
| AU2010363329A1 (en) | 2010-11-07 | 2013-05-09 | Targegen, Inc. | Compositions and methods for treating myelofibrosis |
| JP2013246405A (ja) * | 2012-05-29 | 2013-12-09 | Jsr Corp | 液晶配向剤 |
| JP6146100B2 (ja) * | 2012-06-21 | 2017-06-14 | Jsr株式会社 | 液晶配向剤、液晶配向膜、位相差フィルム、液晶表示素子及び位相差フィルムの製造方法 |
| KR20140115180A (ko) * | 2013-03-20 | 2014-09-30 | 삼성디스플레이 주식회사 | 액정 표시 장치 및 그 제조 방법 |
| US10557085B2 (en) | 2015-03-31 | 2020-02-11 | Rolic Ag | Photoalignment composition |
| KR20180082540A (ko) * | 2015-11-11 | 2018-07-18 | 롤릭 테크놀로지스 아게 | 광-정렬가능 물질의 조성물 |
| EP3374416A1 (en) | 2015-11-11 | 2018-09-19 | ROLIC Technologies AG | Photoalignment materials |
| CN108368426B (zh) * | 2015-12-17 | 2022-03-11 | 默克专利股份有限公司 | 肉桂酸衍生物 |
| CN112272613B (zh) | 2018-07-02 | 2023-03-28 | 富士胶片株式会社 | 装饰膜、装饰方法、装饰成型体的制造方法及装饰成型膜 |
| CN113490594A (zh) | 2019-02-27 | 2021-10-08 | 富士胶片株式会社 | 层叠体 |
| WO2020262474A1 (ja) | 2019-06-27 | 2020-12-30 | 富士フイルム株式会社 | 成型用加飾フィルム、成型物、及びディスプレイ |
| JPWO2023276679A1 (enExample) * | 2021-06-28 | 2023-01-05 | ||
| CN113666956B (zh) * | 2021-08-25 | 2023-04-25 | 上海橡实化学有限公司 | 一种水杨醛亚胺硅烷偶联剂及其制备方法和应用 |
| WO2024121658A1 (en) * | 2022-12-06 | 2024-06-13 | Solventum Intellectual Properties Company | Surface-treated filler, dental composition containing such a filler, process of production and use thereof |
| WO2025013901A1 (ja) | 2023-07-11 | 2025-01-16 | 富士フイルム株式会社 | 液晶組成物、光学異方性層、硬化膜、回折素子、化合物 |
| KR20260011736A (ko) | 2023-07-11 | 2026-01-23 | 후지필름 가부시키가이샤 | 조성물, 광학 이방성층, 경화막, 회절 소자 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3865588A (en) * | 1971-02-20 | 1975-02-11 | Dainippon Printing Co Ltd | Planographic plate with a polymerizable organopolysiloxane compound |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3179612A (en) | 1962-02-02 | 1965-04-20 | Dow Corning | alpha, beta-unsaturated carboxylicester-substituted organosilicon compounds |
| GB960534A (en) * | 1961-08-28 | 1964-06-10 | Dow Corning | Organosilicon compounds |
| FR1337516A (fr) | 1962-08-22 | 1963-09-13 | Dow Corning | Composés organosiliciques substitués par des groupements esters carboxyliques alpha, beta-non saturés |
| US4974941A (en) * | 1989-03-08 | 1990-12-04 | Hercules Incorporated | Process of aligning and realigning liquid crystal media |
| US5539074A (en) | 1993-02-17 | 1996-07-23 | Hoffmann-La Roche Inc. | Linear and cyclic polymers or oligomers having a photoreactive ethene group |
| SG50569A1 (en) | 1993-02-17 | 2001-02-20 | Rolic Ag | Optical component |
-
1998
- 1998-01-29 DE DE59807348T patent/DE59807348D1/de not_active Expired - Lifetime
- 1998-01-30 US US09/016,376 patent/US6277502B1/en not_active Expired - Lifetime
- 1998-02-04 JP JP02357198A patent/JP4205195B2/ja not_active Expired - Lifetime
- 1998-02-04 SG SG9800241A patent/SG90026A1/en unknown
- 1998-02-05 KR KR1019980003265A patent/KR100609200B1/ko not_active Expired - Lifetime
- 1998-02-05 CN CNB98107099XA patent/CN1213053C/zh not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3865588A (en) * | 1971-02-20 | 1975-02-11 | Dainippon Printing Co Ltd | Planographic plate with a polymerizable organopolysiloxane compound |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1213053C (zh) | 2005-08-03 |
| KR19980071102A (ko) | 1998-10-26 |
| DE59807348D1 (de) | 2003-04-10 |
| JPH10324690A (ja) | 1998-12-08 |
| JP4205195B2 (ja) | 2009-01-07 |
| SG90026A1 (en) | 2002-07-23 |
| US6277502B1 (en) | 2001-08-21 |
| CN1195015A (zh) | 1998-10-07 |
| HK1010884A1 (en) | 1999-07-02 |
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