JP4011652B2 - 架橋結合しうる光活性の重合体材料 - Google Patents
架橋結合しうる光活性の重合体材料 Download PDFInfo
- Publication number
- JP4011652B2 JP4011652B2 JP23871196A JP23871196A JP4011652B2 JP 4011652 B2 JP4011652 B2 JP 4011652B2 JP 23871196 A JP23871196 A JP 23871196A JP 23871196 A JP23871196 A JP 23871196A JP 4011652 B2 JP4011652 B2 JP 4011652B2
- Authority
- JP
- Japan
- Prior art keywords
- methylethylene
- methoxycarbonylvinyl
- poly
- phenoxy
- diyl
- 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
- 239000002861 polymer material Substances 0.000 title claims description 7
- 238000004132 cross linking Methods 0.000 title claims description 3
- -1 siloxanes Chemical class 0.000 claims description 256
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 143
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 99
- 229920000642 polymer Polymers 0.000 claims description 65
- 125000000217 alkyl group Chemical group 0.000 claims description 63
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 62
- 125000005935 hexyloxycarbonyl group Chemical group 0.000 claims description 60
- 125000003545 alkoxy group Chemical group 0.000 claims description 45
- 229920001577 copolymer Polymers 0.000 claims description 31
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 29
- 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 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 239000004973 liquid crystal related substance Substances 0.000 claims description 22
- 239000000178 monomer Substances 0.000 claims description 19
- 125000002947 alkylene group Chemical group 0.000 claims description 18
- 229920001519 homopolymer Polymers 0.000 claims description 15
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 13
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 230000003287 optical effect Effects 0.000 claims description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 5
- 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 4
- 125000005907 alkyl ester group Chemical group 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims description 4
- 238000004581 coalescence Methods 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 239000000463 material Substances 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
- 150000007513 acids Chemical class 0.000 claims description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 5
- 239000004472 Lysine Substances 0.000 claims 5
- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 68
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 60
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- 239000000460 chlorine Chemical group 0.000 description 44
- 239000011737 fluorine Substances 0.000 description 38
- 229910052731 fluorine Inorganic materials 0.000 description 38
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 37
- 229910052801 chlorine Inorganic materials 0.000 description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 125000004093 cyano group Chemical group *C#N 0.000 description 36
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 30
- 238000000034 method Methods 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 16
- 238000001914 filtration Methods 0.000 description 15
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical group [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 11
- 235000013985 cinnamic acid Nutrition 0.000 description 10
- 229930016911 cinnamic acid Natural products 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 9
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 125000005647 linker group Chemical group 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000002835 absorbance Methods 0.000 description 8
- 125000001153 fluoro group Chemical group F* 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 239000011541 reaction mixture Substances 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
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 229910052786 argon Inorganic materials 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- 238000004809 thin layer chromatography Methods 0.000 description 7
- NITWSHWHQAQBAW-QPJJXVBHSA-N (E)-4-coumaric acid methyl ester Chemical compound COC(=O)\C=C\C1=CC=C(O)C=C1 NITWSHWHQAQBAW-QPJJXVBHSA-N 0.000 description 6
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 150000003440 styrenes Chemical class 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- NGSWKAQJJWESNS-ZZXKWVIFSA-N trans-4-coumaric acid Chemical class OC(=O)\C=C\C1=CC=C(O)C=C1 NGSWKAQJJWESNS-ZZXKWVIFSA-N 0.000 description 5
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 4
- YBXYCBGDIALKAK-UHFFFAOYSA-N 2-chloroprop-2-enamide Chemical class NC(=O)C(Cl)=C YBXYCBGDIALKAK-UHFFFAOYSA-N 0.000 description 4
- VVYHWYFUTOHXRH-UHFFFAOYSA-N 4-(6-hydroxyhexoxy)benzoic acid Chemical compound OCCCCCCOC1=CC=C(C(O)=O)C=C1 VVYHWYFUTOHXRH-UHFFFAOYSA-N 0.000 description 4
- KAGIRXVDTGQWKF-UHFFFAOYSA-N 4-[6-(2-methylprop-2-enoyloxy)hexoxy]benzoic acid Chemical compound CC(=C)C(=O)OCCCCCCOC1=CC=C(C(O)=O)C=C1 KAGIRXVDTGQWKF-UHFFFAOYSA-N 0.000 description 4
- QXZIOUAINSTHGI-UHFFFAOYSA-N 4-but-3-enoxybenzoic acid Chemical compound OC(=O)C1=CC=C(OCCC=C)C=C1 QXZIOUAINSTHGI-UHFFFAOYSA-N 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- MRGWVMDNONJEFW-UAPYVXQJSA-N OCCC[C@H]1CC[C@@H](CC1)c1ccc(cc1)-c1ccc(C=O)cc1 Chemical compound OCCC[C@H]1CC[C@@H](CC1)c1ccc(cc1)-c1ccc(C=O)cc1 MRGWVMDNONJEFW-UAPYVXQJSA-N 0.000 description 4
- VZDIIUILJKUBAU-UAPYVXQJSA-N OCCC[C@H]1CC[C@@H](CC1)c1ccc(cc1)-c1ccc(cc1)C#N Chemical compound OCCC[C@H]1CC[C@@H](CC1)c1ccc(cc1)-c1ccc(cc1)C#N VZDIIUILJKUBAU-UAPYVXQJSA-N 0.000 description 4
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 150000001851 cinnamic acid derivatives Chemical class 0.000 description 4
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Substances [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- AUJXJFHANFIVKH-GQCTYLIASA-N trans-methylferulate Chemical compound COC(=O)\C=C\C1=CC=C(O)C(OC)=C1 AUJXJFHANFIVKH-GQCTYLIASA-N 0.000 description 4
- 229920001567 vinyl ester resin Polymers 0.000 description 4
- IMOLAGKJZFODRK-UHFFFAOYSA-N 2-phenylprop-2-enamide Chemical class NC(=O)C(=C)C1=CC=CC=C1 IMOLAGKJZFODRK-UHFFFAOYSA-N 0.000 description 3
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- CHGRQRLUYUEKOG-AQYVVDRMSA-N CC(=C)C(=O)OCCC[C@H]1CC[C@@H](CC1)c1ccc(cc1)-c1ccc(C=O)cc1 Chemical compound CC(=C)C(=O)OCCC[C@H]1CC[C@@H](CC1)c1ccc(cc1)-c1ccc(C=O)cc1 CHGRQRLUYUEKOG-AQYVVDRMSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 3
- NITWSHWHQAQBAW-UHFFFAOYSA-N MpCA Natural products COC(=O)C=CC1=CC=C(O)C=C1 NITWSHWHQAQBAW-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- 125000005396 acrylic acid ester group Chemical group 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 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 3
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 3
- 238000006471 dimerization reaction Methods 0.000 description 3
- 238000006266 etherification reaction Methods 0.000 description 3
- 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 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 2
- 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 2
- BIPLQYGBSOIAHY-RMKNXTFCSA-N 2-[4-[(e)-3-methoxy-3-oxoprop-1-enyl]phenoxy]ethyl 2-methylprop-2-enoate Chemical compound COC(=O)\C=C\C1=CC=C(OCCOC(=O)C(C)=C)C=C1 BIPLQYGBSOIAHY-RMKNXTFCSA-N 0.000 description 2
- SZTBMYHIYNGYIA-UHFFFAOYSA-N 2-chloroacrylic acid Chemical class OC(=O)C(Cl)=C SZTBMYHIYNGYIA-UHFFFAOYSA-N 0.000 description 2
- NGSWKAQJJWESNS-UHFFFAOYSA-N 4-coumaric acid Chemical compound OC(=O)C=CC1=CC=C(O)C=C1 NGSWKAQJJWESNS-UHFFFAOYSA-N 0.000 description 2
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- DSPSRFYXRHPOLV-RMKNXTFCSA-N [4-[(e)-3-methoxy-3-oxoprop-1-enyl]phenyl] 2-methylprop-2-enoate Chemical compound COC(=O)\C=C\C1=CC=C(OC(=O)C(C)=C)C=C1 DSPSRFYXRHPOLV-RMKNXTFCSA-N 0.000 description 2
- 150000003926 acrylamides Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 229920001002 functional polymer Polymers 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000000819 phase cycle Methods 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
- ONPJWQSDZCGSQM-UHFFFAOYSA-N 2-phenylprop-2-enoic acid Chemical class OC(=O)C(=C)C1=CC=CC=C1 ONPJWQSDZCGSQM-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 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
- NGSWKAQJJWESNS-ZZXKWVIFSA-M 4-Hydroxycinnamate Natural products OC1=CC=C(\C=C\C([O-])=O)C=C1 NGSWKAQJJWESNS-ZZXKWVIFSA-M 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- DMAYBPBPEUFIHJ-UHFFFAOYSA-N 4-bromobut-1-ene Chemical compound BrCCC=C DMAYBPBPEUFIHJ-UHFFFAOYSA-N 0.000 description 1
- GWNGSICURHEYDV-UHFFFAOYSA-N 6-benzoylperoxyhexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCOOC(=O)C1=CC=CC=C1 GWNGSICURHEYDV-UHFFFAOYSA-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
- JNTPTNNCGDAGEJ-UHFFFAOYSA-N 6-chlorohexan-1-ol Chemical compound OCCCCCCCl JNTPTNNCGDAGEJ-UHFFFAOYSA-N 0.000 description 1
- DFYRUELUNQRZTB-UHFFFAOYSA-N Acetovanillone Natural products COC1=CC(C(C)=O)=CC=C1O DFYRUELUNQRZTB-UHFFFAOYSA-N 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- VVQODUPIZLUKEM-MHWRWJLKSA-N CC(C(OCCCCCCOc(cc1)ccc1C(Oc1ccc(/C=C/C(OC)=O)cc1OC)=O)=O)=C Chemical compound CC(C(OCCCCCCOc(cc1)ccc1C(Oc1ccc(/C=C/C(OC)=O)cc1OC)=O)=O)=C VVQODUPIZLUKEM-MHWRWJLKSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 238000006751 Mitsunobu reaction Methods 0.000 description 1
- HIBUFSVQQCEDFE-UAPYVXQJSA-N O=CCC[C@H]1CC[C@@H](CC1)c1ccc(cc1)-c1ccc(cc1)C#N Chemical compound O=CCC[C@H]1CC[C@@H](CC1)c1ccc(cc1)-c1ccc(cc1)C#N HIBUFSVQQCEDFE-UAPYVXQJSA-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
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- QBLVDHOINDPTGM-VGOFMYFVSA-N [4-[(e)-3-methoxy-3-oxoprop-1-enyl]phenyl] 4-but-3-enoxybenzoate Chemical compound C1=CC(/C=C/C(=O)OC)=CC=C1OC(=O)C1=CC=C(OCCC=C)C=C1 QBLVDHOINDPTGM-VGOFMYFVSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 230000008033 biological extinction 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
- DSVRVHYFPPQFTI-UHFFFAOYSA-N bis(ethenyl)-methyl-trimethylsilyloxysilane;platinum Chemical compound [Pt].C[Si](C)(C)O[Si](C)(C=C)C=C DSVRVHYFPPQFTI-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 229920005565 cyclic polymer Polymers 0.000 description 1
- 230000000254 damaging effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 description 1
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 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
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 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
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 238000006552 photochemical reaction Methods 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002338 polyhydroxyethylmethacrylate Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920001843 polymethylhydrosiloxane Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229920006301 statistical copolymer Polymers 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000005730 thiophenylene group Chemical group 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
-
- 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
- C08F220/00—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
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
- C08F220/303—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety and one or more carboxylic moieties in the chain
-
- 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
- C08F220/00—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
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
-
- 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
- C08F246/00—Copolymers in which the nature of only the monomers in minority is defined
-
- 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
- C08F220/00—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
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
- C08F220/305—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety
-
- 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
- G02F1/13378—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by treatment of the surface, e.g. embossing, rubbing or light irradiation
- G02F1/133788—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by treatment of the surface, e.g. embossing, rubbing or light irradiation by light irradiation, e.g. linearly polarised light photo-polymerisation
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Nonlinear Science (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Mathematical Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Liquid Crystal Substances (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Silicon Polymers (AREA)
- Liquid Crystal (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH261595 | 1995-09-15 | ||
| CH66496 | 1996-03-13 | ||
| CH02615/95-1 | 1996-03-13 | ||
| CH00664/96 | 1996-03-13 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPH09118717A JPH09118717A (ja) | 1997-05-06 |
| JPH09118717A5 JPH09118717A5 (https=) | 2004-09-09 |
| JP4011652B2 true JP4011652B2 (ja) | 2007-11-21 |
Family
ID=25685298
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP23871196A Expired - Lifetime JP4011652B2 (ja) | 1995-09-15 | 1996-09-10 | 架橋結合しうる光活性の重合体材料 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US6107427A (https=) |
| EP (1) | EP0763552B1 (https=) |
| JP (1) | JP4011652B2 (https=) |
| KR (1) | KR100456707B1 (https=) |
| CN (1) | CN1109053C (https=) |
| DE (1) | DE59607712D1 (https=) |
| SG (1) | SG45498A1 (https=) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2012018121A1 (ja) * | 2010-08-05 | 2013-10-28 | 日産化学工業株式会社 | 樹脂組成物、液晶配向材および位相差材 |
| US9575232B2 (en) | 2013-08-09 | 2017-02-21 | Sumitomo Chemical Company, Limited | Method for producing optically anisotropic laminated body |
| JP2019082703A (ja) * | 2013-08-09 | 2019-05-30 | 住友化学株式会社 | 長尺位相差フィルムの製造方法 |
| US10353128B2 (en) | 2013-08-09 | 2019-07-16 | Sumitomo Chemical Company, Limited | Laminated body |
Families Citing this family (121)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE59707681D1 (de) * | 1996-10-28 | 2002-08-14 | Rolic Ag Zug | Vernetzbare, photoaktive Silanderivate |
| DE59814236D1 (de) * | 1997-02-24 | 2008-07-17 | Rolic Ag | Photovernetzbare Polymere |
| WO1999015576A1 (en) * | 1997-09-25 | 1999-04-01 | Rolic Ag | Photocrosslinkable polyimides |
| WO1999049360A1 (en) * | 1998-03-20 | 1999-09-30 | Rolic Ag | LlQUID CRYSTAL ORIENTATION LAYER |
| FR2777899A1 (fr) * | 1998-04-28 | 1999-10-29 | Thomson Csf | Materiaux d'alignement de cristaux liquides a partir de derives du biphenyl et du napthtalene |
| US6376467B1 (en) * | 1998-10-09 | 2002-04-23 | The Regents Of The University Of California | Use of inhibitors of protein kinase C epsilon to treat pain |
| GB9817272D0 (en) * | 1998-08-07 | 1998-10-07 | Rolic Ag | Liquid crystalline compounds |
| US20040120040A1 (en) | 1998-11-13 | 2004-06-24 | Rolic Ag | Optical component |
| GB9907801D0 (en) * | 1999-04-06 | 1999-06-02 | Rolic Ag | Photoactive polymers |
| EP1070731A1 (en) | 1999-07-23 | 2001-01-24 | Rolic AG | Compound |
| EP1079244A3 (en) * | 1999-08-23 | 2001-10-04 | Fuji Photo Film Co., Ltd. | Orientation layer containing (meth)acrylic copolymer having hydrophobic repeating units |
| JP4208168B2 (ja) * | 1999-12-17 | 2009-01-14 | 日東電工株式会社 | コレステリック性液晶組成物、配向フィルムおよび多色反射板 |
| EP1170624A1 (en) * | 2000-07-05 | 2002-01-09 | Rolic AG | Nematic liquid crystal electrooptical element and device |
| JP4817589B2 (ja) * | 2000-07-05 | 2011-11-16 | ロリク アーゲー | ネマチック液晶電気光学要素及びデバイス |
| EP1219651A1 (en) * | 2000-12-29 | 2002-07-03 | Rolic AG | Photoactive copolymer |
| EP1227347A1 (en) | 2001-01-29 | 2002-07-31 | Rolic AG | Optical device and method for manufacturing same |
| KR100420786B1 (ko) | 2001-03-09 | 2004-03-02 | 한국과학기술원 | 액정배향막 제조용 고분자 |
| KR100441154B1 (ko) * | 2001-07-11 | 2004-07-19 | 엘지전선 주식회사 | 2개 이상의 광활성 그룹을 갖는 광배향성 고분자 조성물,이 조성물을 포함 하는 액정배향막 및 이 배향막을 사용한액정표시소자 |
| EP1277770A1 (en) * | 2001-07-17 | 2003-01-22 | Rolic AG | Photoactive materials |
| US6919404B2 (en) * | 2002-05-31 | 2005-07-19 | Elsicon, Inc. | Hybrid polymer materials for liquid crystal alignment layers |
| US6900271B2 (en) * | 2002-05-31 | 2005-05-31 | Elsicon, Inc | Hybrid polymer materials for liquid crystal alignment layers |
| JP4524458B2 (ja) | 2002-05-31 | 2010-08-18 | エルシコン・インコーポレーテッド | 光学配向層調製用分岐ハイブリッドポリマー材料 |
| KR20050084084A (ko) * | 2002-12-06 | 2005-08-26 | 롤리크 아게 | 가교성, 광활성 중합체 및 그의 용도 |
| US7385017B2 (en) * | 2003-03-27 | 2008-06-10 | Nippon Steel Chemical Co., Ltd. | Silicone resin compositions and molded articles thereof |
| KR101110090B1 (ko) * | 2003-07-16 | 2012-02-15 | 롤리크 아게 | 배향층용의 중합 가능한 공중합체 |
| CN100396728C (zh) * | 2003-10-23 | 2008-06-25 | 日产化学工业株式会社 | 液晶定向处理剂及液晶显示元件 |
| JP4537718B2 (ja) * | 2004-01-22 | 2010-09-08 | 大日本印刷株式会社 | 液晶表示素子 |
| EP1715371B1 (en) * | 2004-01-22 | 2010-11-03 | Dai Nippon Printing Co., Ltd. | Liquid crystal display device |
| US7553521B2 (en) * | 2004-01-22 | 2009-06-30 | Dai Nippon Printing Co., Ltd. | Liquid crystal displays |
| JP4930370B2 (ja) | 2005-03-04 | 2012-05-16 | 大日本印刷株式会社 | 光学素子 |
| JP5389355B2 (ja) * | 2005-03-09 | 2014-01-15 | Ｈｏｙａ株式会社 | （メタ）アクリレート化合物およびその製造方法、（メタ）アクリレート系共重合体、（メタ）アクリレート系共重合体の製造方法ならびに軟性眼内レンズ |
| KR101128123B1 (ko) * | 2005-06-22 | 2012-06-12 | 엘지디스플레이 주식회사 | 광배향 물질 |
| EP1764405A1 (en) * | 2005-09-20 | 2007-03-21 | Rolic AG | Functionalized photoreactive compounds |
| DE102006023084B4 (de) * | 2006-05-16 | 2019-07-18 | Leonhard Kurz Stiftung & Co. Kg | Wertdokument mit Sicherheitselement |
| KR101436795B1 (ko) | 2006-09-13 | 2014-09-03 | 롤리크 아게 | 체적 광-정렬 지연판 |
| EP2094815B1 (en) | 2006-12-22 | 2012-06-27 | Rolic AG | Patternable liquid crystal polymer comprising thio-ether units |
| EP1970734B1 (en) * | 2007-03-12 | 2011-09-14 | JDS Uniphase Corporation | A method of fabricating a space-variant liquid-crystal waveplate |
| 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 |
| JP5075483B2 (ja) * | 2007-04-27 | 2012-11-21 | 林テレンプ株式会社 | 高分子フィルム、分子配向素子の作製方法、および液晶配向膜 |
| JP4918447B2 (ja) * | 2007-09-28 | 2012-04-18 | 富士フイルム株式会社 | 配向膜、その製造方法及び配向膜形成用組成物、ならびにそれを有する液晶セル及び液晶表示装置 |
| CN101903494B (zh) * | 2007-12-21 | 2016-03-02 | 罗利克有限公司 | 光校准组合物 |
| EP2222740B1 (en) * | 2007-12-21 | 2017-10-11 | Rolic AG | Functionalized photoreactive compounds |
| JP5245118B2 (ja) * | 2008-03-07 | 2013-07-24 | 和歌山県 | 新規な重合性化合物およびその製造方法 |
| JP2009258578A (ja) * | 2008-03-18 | 2009-11-05 | Jsr Corp | 液晶配向剤、液晶配向膜とその形成方法ならびに液晶表示素子および光学部材 |
| KR101587125B1 (ko) * | 2008-08-21 | 2016-02-03 | 삼성디스플레이 주식회사 | 광반응성 화합물 및 그것을 이용한 액정 표시 소자 |
| JP5626510B2 (ja) * | 2009-02-18 | 2014-11-19 | Jsr株式会社 | 液晶配向剤、液晶配向膜の形成方法および液晶表示素子の製造方法 |
| WO2010150748A1 (ja) | 2009-06-23 | 2010-12-29 | 日産化学工業株式会社 | 光配向性を有する熱硬化膜形成組成物 |
| 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 |
| EP2272937A1 (en) | 2009-07-09 | 2011-01-12 | Rolic AG | Ester group containing compounds for optical or electro optical devices |
| CN102471629B (zh) * | 2009-07-21 | 2015-09-09 | 日产化学工业株式会社 | 形成具有光取向性的热固化膜的组合物 |
| KR101666622B1 (ko) * | 2009-08-26 | 2016-10-17 | 삼성디스플레이 주식회사 | 광배향제 및 그것을 이용한 액정 표시 장치 |
| US9475901B2 (en) | 2009-12-08 | 2016-10-25 | Transitions Optical, Inc. | Photoalignment materials having improved adhesion |
| JP5713213B2 (ja) * | 2010-04-08 | 2015-05-07 | 日産化学工業株式会社 | 光配向性を有する熱硬化膜形成組成物 |
| EP2557119B1 (en) * | 2010-04-08 | 2015-12-09 | Nissan Chemical Industries, Ltd. | Composition forming heat-cured film having photo-alignment properties |
| EP2557102B1 (en) | 2010-04-08 | 2017-06-07 | Nissan Chemical Industries, Ltd. | Composition for forming thermoset film having photo-alignment properties |
| TWI495648B (zh) * | 2010-07-28 | 2015-08-11 | Osaka Organic Chemical Ind Ltd | 共聚合性〈甲基〉丙烯酸聚合物、光配向膜以及相位差膜 |
| JP5557028B2 (ja) * | 2010-09-09 | 2014-07-23 | Ｄｉｃ株式会社 | 光学異方体 |
| JP5712856B2 (ja) * | 2010-09-22 | 2015-05-07 | Jnc株式会社 | 感光性化合物および該化合物からなる感光性ポリマー |
| US10465116B2 (en) * | 2010-12-23 | 2019-11-05 | Rolic Ag | Photoactive polymer materials |
| JP5784323B2 (ja) * | 2011-02-23 | 2015-09-24 | 大阪有機化学工業株式会社 | 位相差フィルム用組成物 |
| JP5892323B2 (ja) * | 2011-03-02 | 2016-03-23 | Jsr株式会社 | 液晶表示素子の製造方法 |
| JP5549781B2 (ja) | 2011-05-31 | 2014-07-16 | Ｄｉｃ株式会社 | 桂皮酸誘導体およびその重合体、ならびにその硬化物からなる液晶配向層 |
| EP2727903B1 (en) * | 2011-06-30 | 2018-01-10 | DIC Corporation | Cinnamic acid derivative, polymer thereof, and liquid crystal alignment layer comprising hardened product of said polymer |
| WO2013002260A1 (ja) | 2011-06-30 | 2013-01-03 | Dic株式会社 | 共重合体、ならびにその硬化物からなる液晶配向層 |
| KR101945053B1 (ko) * | 2011-07-07 | 2019-02-01 | 스미또모 가가꾸 가부시키가이샤 | 광반응성 액정 배향제, 및 액정 배향 소자 및 그의 제조 방법 |
| JP6525590B2 (ja) | 2011-08-25 | 2019-06-05 | ロリク アーゲーＲｏｌｉｃ Ａｇ | 光反応性化合物 |
| WO2013050120A1 (en) | 2011-10-03 | 2013-04-11 | Rolic Ag | Photo-alignment layers with strong uv-dichroism |
| JP5884618B2 (ja) * | 2012-04-20 | 2016-03-15 | Jsr株式会社 | 液晶配向剤、液晶配向膜、液晶表示素子及び液晶表示素子の製造方法 |
| KR20130123308A (ko) | 2012-05-02 | 2013-11-12 | 한양대학교 산학협력단 | 광배향성 중합체, 이를 포함하는 광학필름 및 그 제조방법 |
| CN104364682B (zh) | 2012-05-30 | 2018-06-01 | 罗利克有限公司 | 具有单独构图的各向异性的元件的快速生成 |
| US20130331482A1 (en) | 2012-06-06 | 2013-12-12 | Jnc Petrochemical Corporation | Polymer composition having photoalignable group, liquid crystal alignment film formed of the polymer composition, and optical device having phase difference plate formed of the liquid crystal alignment film |
| KR102042441B1 (ko) * | 2012-06-20 | 2019-11-08 | 닛산 가가쿠 가부시키가이샤 | 신규 중합성 화합물 및 그의 제조방법 |
| JP6089512B2 (ja) * | 2012-09-07 | 2017-03-08 | 住友化学株式会社 | 積層体および光学フィルム |
| CN105408450B (zh) * | 2013-05-13 | 2019-11-08 | 日产化学工业株式会社 | 具有横向电场驱动型液晶表示元件用液晶取向膜的基板的制造方法 |
| WO2014191292A1 (en) | 2013-05-28 | 2014-12-04 | Rolic Ag | Cyanostilbenes |
| US10286616B2 (en) | 2013-08-19 | 2019-05-14 | Rolic Ag | Photo-alignable object |
| JP5839147B2 (ja) | 2013-11-29 | 2016-01-06 | Dic株式会社 | 化合物、重合体、液晶配向膜、液晶表示素子、及び光学異方体 |
| JP6326787B2 (ja) * | 2013-11-29 | 2018-05-23 | Dic株式会社 | 液晶配向膜用ポリマー、液晶配向膜、液晶表示素子及び光学異方体 |
| CN106030355B (zh) * | 2014-02-28 | 2019-06-18 | 日产化学工业株式会社 | 相位差材形成用树脂组合物、取向材及相位差材 |
| EP3126883B1 (en) | 2014-04-03 | 2023-07-12 | ROLIC Technologies AG | Optical devices with patterned anisotropy incorporating parallax optic |
| JP2017518413A (ja) | 2014-05-21 | 2017-07-06 | ロリク アーゲーＲｏｌｉｃ Ａｇ | 重合性二色性染料 |
| WO2015186562A1 (ja) * | 2014-06-02 | 2015-12-10 | Dic株式会社 | 液晶配向膜 |
| ES2983074T3 (es) | 2014-07-31 | 2024-10-21 | Basf Coatings Gmbh | Estructura de encapsulación para una pantalla OLED que incorpora propiedades antirreflectantes |
| WO2016052490A1 (ja) * | 2014-10-01 | 2016-04-07 | Dic株式会社 | 積層体、およびそれを使用した光学フィルムまたは液晶配向膜 |
| US10557085B2 (en) | 2015-03-31 | 2020-02-11 | Rolic Ag | Photoalignment composition |
| JP6672608B2 (ja) * | 2015-04-08 | 2020-03-25 | Jsr株式会社 | 潜像形成体、潜像形成体セット、潜像形成体の製造方法、画像表示方法及び装飾用積層体 |
| WO2017080977A1 (en) | 2015-11-11 | 2017-05-18 | Rolic Ag | Compositions of photo-alignable materials |
| JP2019505496A (ja) | 2015-12-17 | 2019-02-28 | メルク・パテント・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ ＧｍｂＨ | ケイ皮酸誘導体 |
| CN109477930A (zh) | 2016-07-29 | 2019-03-15 | 罗利克技术有限公司 | 在液晶聚合物材料上产生取向的方法 |
| CN110997614B (zh) | 2017-08-09 | 2023-06-02 | 罗利克技术有限公司 | 制备光配向聚合物材料和组合物的方法 |
| CN120484181A (zh) | 2017-08-09 | 2025-08-15 | 罗利克技术有限公司 | 光配向聚合物材料 |
| CN111247111A (zh) | 2017-11-02 | 2020-06-05 | 大日本印刷株式会社 | 夹层玻璃的制造方法、夹层玻璃、调光膜 |
| WO2019206789A1 (en) | 2018-04-23 | 2019-10-31 | Merck Patent Gmbh | Liquid crystal mixture and liquid crystal display |
| WO2019206788A1 (en) | 2018-04-23 | 2019-10-31 | Merck Patent Gmbh | Liquid crystal mixture and liquid crystal display |
| WO2019206791A1 (en) | 2018-04-23 | 2019-10-31 | Merck Patent Gmbh | Liquid crystal mixture and liquid crystal display |
| KR20210005122A (ko) | 2018-04-23 | 2021-01-13 | 메르크 파텐트 게엠베하 | 액정 혼합물 및 액정 디스플레이 |
| WO2020038861A1 (en) | 2018-08-22 | 2020-02-27 | Merck Patent Gmbh | Liquid crystal mixture and liquid crystal display |
| WO2020038859A1 (en) | 2018-08-22 | 2020-02-27 | Merck Patent Gmbh | Liquid crystal mixture and liquid crystal display |
| WO2020043643A1 (en) | 2018-08-28 | 2020-03-05 | Merck Patent Gmbh | Liquid crystal mixture and liquid crystal display |
| US20220106525A1 (en) | 2018-10-10 | 2022-04-07 | Merck Patent Gmbh | Liquid crystal mixture and liquid crystal display |
| US20230068853A1 (en) | 2018-12-12 | 2023-03-02 | Merck Patent Gmbh | Liquid crystal mixture and liquid crystal display |
| CN113412251B (zh) * | 2019-02-12 | 2023-11-28 | 罗利克技术有限公司 | 用于制备光致配向聚合物材料的方法和组合物 |
| US20220251448A1 (en) | 2019-06-04 | 2022-08-11 | Merck Patent Gmbh | Liquid Crystal Mixture and Liquid Crystal Display |
| CN114026074B (zh) | 2019-06-28 | 2024-02-09 | 罗利克技术有限公司 | 新的具有喹喔啉-腙核的可聚合液晶 |
| EP3990430A1 (en) | 2019-06-28 | 2022-05-04 | Rolic Technologies AG | New polymerizable liquid crystal having a carbazole core |
| EP3990569B1 (en) | 2019-06-28 | 2024-12-04 | Rolic Technologies AG | New polymerizable liquid crystal |
| CN118259397A (zh) | 2019-07-24 | 2024-06-28 | 罗利克技术有限公司 | 可光致配向的正c板延迟器 |
| JP7564192B2 (ja) | 2019-08-28 | 2024-10-08 | ロリク・テクノロジーズ・アーゲー | 重合性液晶の組成物 |
| EP3792334B1 (en) | 2019-09-16 | 2022-01-19 | Merck Patent GmbH | Liquid crystal mixture and liquid crystal display |
| EP4259748B1 (en) | 2020-12-11 | 2025-07-30 | Merck Patent GmbH | Liquid crystal mixture and liquid crystal display |
| US11639432B2 (en) | 2021-01-13 | 2023-05-02 | International Business Machines Corporation | Hydroxycinnamic acid-derived crosslinking dimers |
| US11732136B2 (en) | 2021-01-13 | 2023-08-22 | International Business Machines Corporation | Hydroxycinnamic acid-derived crosslinkers |
| TWI895581B (zh) | 2021-02-02 | 2025-09-01 | 瑞士商羅立克科技股份公司 | 用於在光學感測器裝置之光敏元件上製造包含至少一個光學各向異性膜之空間受限的膜堆疊之方法，電子裝置，電子裝置之用途及電子裝置在顯示器裝備中之用途 |
| WO2022210639A1 (ja) * | 2021-03-30 | 2022-10-06 | 日産化学株式会社 | パターン化された単層位相差膜の製造方法及び単層位相差膜形成用重合体組成物 |
| CN117561474A (zh) | 2021-07-05 | 2024-02-13 | 大日本印刷株式会社 | 调光构件、调光装置 |
| CN115322795A (zh) * | 2021-12-29 | 2022-11-11 | 上海先认新材料合伙企业(有限合伙) | 一种液晶组合物及其应用 |
| CN115322796B (zh) * | 2022-06-16 | 2024-05-10 | 上海先认新材料合伙企业(有限合伙) | 一种液晶组合物、蛾眼膜及其制备方法 |
| CN116083090B (zh) * | 2022-10-18 | 2024-07-05 | 上海先幻高科新材料有限公司 | 自分层液晶组合物、消色差四分之一波片膜及制备方法 |
| TW202448972A (zh) | 2023-05-12 | 2024-12-16 | 瑞士商羅立克科技股份公司 | 可聚合液晶組成物 |
| JPWO2025013896A1 (https=) | 2023-07-11 | 2025-01-16 | ||
| KR20260004443A (ko) | 2023-07-11 | 2026-01-08 | 후지필름 가부시키가이샤 | 액정 조성물, 광학 이방성층, 경화막, 회절 소자, 화합물 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH203695A (fr) | 1937-12-24 | 1939-03-31 | Rhodiaceta | Procédé de préparation de la 1, 4, 5, 8 tétraminoanthraquinone. |
| JPS5156025A (en) * | 1974-11-11 | 1976-05-17 | Fuji Telecasting Co Ltd | Jishintono hatsuseiji niokeru kotsukuno jidoshadansochi |
| FR2609993B1 (fr) * | 1987-01-27 | 1989-05-19 | Ppg Industries Inc | Nouveaux polysiloxanes modifies, leur procede de preparation et leurs applications comme cristaux liquides et comme supports de medicaments |
| US4925589A (en) * | 1987-12-29 | 1990-05-15 | Hoffmann-La Roche Inc. | Amide side-chain polymers |
| US4974941A (en) * | 1989-03-08 | 1990-12-04 | Hercules Incorporated | Process of aligning and realigning liquid crystal media |
| US5252695A (en) * | 1992-06-03 | 1993-10-12 | The United States Of America As Represented By The Secretary Of The Navy | Fast switching ferroelectric liquid crystalline polymers |
| JPH06509889A (ja) * | 1992-06-19 | 1994-11-02 | エフ・ホフマン−ラ ロシュ アーゲー | 光学的非線形ポリマー |
| DE59408097D1 (de) * | 1993-02-17 | 1999-05-20 | Rolic Ag | Orientierungsschicht für Flüssigkristalle |
| SG50569A1 (en) | 1993-02-17 | 2001-02-20 | Rolic Ag | Optical component |
| DE4408170A1 (de) * | 1994-03-11 | 1995-09-14 | Basf Ag | Neue polymerisierbare flüssigkristalline Verbindungen |
| DE59510708D1 (de) | 1994-06-24 | 2003-07-10 | Rolic Ag Zug | Optisches Bauelement aus Schichten vernetzter flüssigkristalliner Monomere und Verfahren zu seiner Herstellung |
| DE59509361D1 (de) | 1994-06-24 | 2001-08-02 | Rolic Ag Zug | Optisches Bauelement |
-
1996
- 1996-09-04 US US08/708,333 patent/US6107427A/en not_active Expired - Lifetime
- 1996-09-06 EP EP96114275A patent/EP0763552B1/de not_active Expired - Lifetime
- 1996-09-06 DE DE59607712T patent/DE59607712D1/de not_active Expired - Lifetime
- 1996-09-10 JP JP23871196A patent/JP4011652B2/ja not_active Expired - Lifetime
- 1996-09-13 SG SG1996010612A patent/SG45498A1/en unknown
- 1996-09-14 CN CN96111550A patent/CN1109053C/zh not_active Expired - Lifetime
- 1996-09-14 KR KR1019960039982A patent/KR100456707B1/ko not_active Expired - Lifetime
-
2000
- 2000-07-11 US US09/614,185 patent/US6335409B1/en not_active Expired - Lifetime
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2012018121A1 (ja) * | 2010-08-05 | 2013-10-28 | 日産化学工業株式会社 | 樹脂組成物、液晶配向材および位相差材 |
| US9575232B2 (en) | 2013-08-09 | 2017-02-21 | Sumitomo Chemical Company, Limited | Method for producing optically anisotropic laminated body |
| JP2019082703A (ja) * | 2013-08-09 | 2019-05-30 | 住友化学株式会社 | 長尺位相差フィルムの製造方法 |
| US10353128B2 (en) | 2013-08-09 | 2019-07-16 | Sumitomo Chemical Company, Limited | Laminated body |
| JP2019204101A (ja) * | 2013-08-09 | 2019-11-28 | 住友化学株式会社 | 長尺位相差フィルムの製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH09118717A (ja) | 1997-05-06 |
| EP0763552A2 (de) | 1997-03-19 |
| KR970015632A (ko) | 1997-04-28 |
| EP0763552A3 (de) | 1998-04-01 |
| EP0763552B1 (de) | 2001-09-19 |
| US6107427A (en) | 2000-08-22 |
| SG45498A1 (en) | 1998-01-16 |
| CN1109053C (zh) | 2003-05-21 |
| US6335409B1 (en) | 2002-01-01 |
| CN1151411A (zh) | 1997-06-11 |
| HK1011035A1 (en) | 1999-07-02 |
| KR100456707B1 (ko) | 2005-04-06 |
| DE59607712D1 (de) | 2001-10-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4011652B2 (ja) | 架橋結合しうる光活性の重合体材料 | |
| JP7189296B2 (ja) | 光活性高分子材料 | |
| JP4369533B2 (ja) | 液晶配向層を製造するためのクマリン及びキノリノン誘導体 | |
| JP4205195B2 (ja) | 光架橋性シラン誘導体 | |
| US6632909B2 (en) | Photocrosslinkable polymers | |
| JPH10130282A (ja) | 光反応性基を包含するシラン誘導体 | |
| US10095066B2 (en) | Cinnamic acid derivative, polymer thereof, and liquid crystal alignment layer comprising cured product thereof | |
| CN103732638B (zh) | 共聚物及包含该共聚物的固化物的液晶取向层 | |
| TWI513714B (zh) | 液晶垂直配向層用聚合物、液晶垂直配向層及液晶顯示元件 | |
| TWI532713B (zh) | 包含桂皮酸衍生物、其聚合物及其硬化物之液晶配向層 | |
| CN105518035A (zh) | 化合物、聚合物、液晶取向膜、液晶显示元件以及光学各向异性体 | |
| KR100503236B1 (ko) | 광가교성중합체 | |
| KR20130123308A (ko) | 광배향성 중합체, 이를 포함하는 광학필름 및 그 제조방법 | |
| HK1011035B (en) | Curable, photoactive polymeric materials |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20060704 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20061004 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20061010 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20070104 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20070206 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20070507 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20070606 |
|
| A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20070731 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20070828 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20070906 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20100914 Year of fee payment: 3 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110914 Year of fee payment: 4 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110914 Year of fee payment: 4 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120914 Year of fee payment: 5 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120914 Year of fee payment: 5 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130914 Year of fee payment: 6 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| EXPY | Cancellation because of completion of term |