JP6824160B2 - アゾ化合物及びそれらを含有する染料系偏光膜並びに偏光板 - Google Patents
アゾ化合物及びそれらを含有する染料系偏光膜並びに偏光板 Download PDFInfo
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- JP6824160B2 JP6824160B2 JP2017519412A JP2017519412A JP6824160B2 JP 6824160 B2 JP6824160 B2 JP 6824160B2 JP 2017519412 A JP2017519412 A JP 2017519412A JP 2017519412 A JP2017519412 A JP 2017519412A JP 6824160 B2 JP6824160 B2 JP 6824160B2
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- -1 azo compound Chemical class 0.000 claims description 56
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 45
- 239000004973 liquid crystal related substance Substances 0.000 claims description 44
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 42
- 125000004432 carbon atom Chemical group C* 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 31
- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- 230000007935 neutral effect Effects 0.000 claims description 25
- 239000000758 substrate Substances 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000003277 amino group Chemical group 0.000 claims description 14
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 12
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 239000011241 protective layer Substances 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004442 acylamino group Chemical class 0.000 claims description 5
- 229920005989 resin Polymers 0.000 claims description 5
- 239000011347 resin Substances 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 238000010030 laminating Methods 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- 239000000975 dye Substances 0.000 description 70
- 150000001875 compounds Chemical class 0.000 description 49
- 230000010287 polarization Effects 0.000 description 39
- 238000010521 absorption reaction Methods 0.000 description 32
- 238000002834 transmittance Methods 0.000 description 28
- VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 26
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
- 239000007864 aqueous solution Substances 0.000 description 22
- 239000000853 adhesive Substances 0.000 description 16
- 230000001070 adhesive effect Effects 0.000 description 16
- 238000000034 method Methods 0.000 description 16
- 229920006254 polymer film Polymers 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000004043 dyeing Methods 0.000 description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
- 210000002858 crystal cell Anatomy 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
- 238000005859 coupling reaction Methods 0.000 description 9
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 230000001681 protective effect Effects 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 7
- 239000004327 boric acid Substances 0.000 description 7
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
- 229920002284 Cellulose triacetate Polymers 0.000 description 6
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 6
- 150000001448 anilines Chemical class 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 229910052740 iodine Inorganic materials 0.000 description 6
- 239000011630 iodine Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 239000003086 colorant Substances 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000010446 mirabilite Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 235000010288 sodium nitrite Nutrition 0.000 description 5
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 5
- MKARNSWMMBGSHX-UHFFFAOYSA-N 3,5-dimethylaniline Chemical compound CC1=CC(C)=CC(N)=C1 MKARNSWMMBGSHX-UHFFFAOYSA-N 0.000 description 4
- CMOLPZZVECHXKN-UHFFFAOYSA-N 7-aminonaphthalene-1,3-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(N)=CC=C21 CMOLPZZVECHXKN-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- 230000007774 longterm Effects 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 description 3
- IMUUNYPYNWXUBO-UHFFFAOYSA-N 4-aminobenzene-1,3-disulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1S(O)(=O)=O IMUUNYPYNWXUBO-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000005185 salting out Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- KZKGEEGADAWJFS-UHFFFAOYSA-N 2-amino-5-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(N)C(S(O)(=O)=O)=C1 KZKGEEGADAWJFS-UHFFFAOYSA-N 0.000 description 2
- MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 2
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- YOSMJAZSUZAKTA-UHFFFAOYSA-N 6-amino-4-(3-sulfopropoxy)naphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(OCCCS(O)(=O)=O)C2=CC(N)=CC=C21 YOSMJAZSUZAKTA-UHFFFAOYSA-N 0.000 description 2
- KZCSUEYBKAPKNH-UHFFFAOYSA-N 6-aminonaphthalene-1,3-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KZCSUEYBKAPKNH-UHFFFAOYSA-N 0.000 description 2
- SEMRCUIXRUXGJX-UHFFFAOYSA-N 6-aminonaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=CC(N)=CC=C21 SEMRCUIXRUXGJX-UHFFFAOYSA-N 0.000 description 2
- GFPQSWFFPRQEHH-UHFFFAOYSA-N 7-aminonaphthalene-1,3,6-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(N)=CC2=C1S(O)(=O)=O GFPQSWFFPRQEHH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 150000007945 N-acyl ureas Chemical class 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000010724 Wisteria floribunda Nutrition 0.000 description 2
- 238000010306 acid treatment Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 150000001925 cycloalkenes Chemical class 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 150000005002 naphthylamines Chemical class 0.000 description 2
- 150000004291 polyenes Chemical class 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229950000244 sulfanilic acid Drugs 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- ULHFFAFDSSHFDA-UHFFFAOYSA-N 1-amino-2-ethoxybenzene Chemical compound CCOC1=CC=CC=C1N ULHFFAFDSSHFDA-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- HEAHMJLHQCESBZ-UHFFFAOYSA-N 2,5-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(N)C(S(O)(=O)=O)=C1 HEAHMJLHQCESBZ-UHFFFAOYSA-N 0.000 description 1
- VBUBGTCJRMYYRA-UHFFFAOYSA-N 2,5-diethylaniline Chemical compound CCC1=CC=C(CC)C(N)=C1 VBUBGTCJRMYYRA-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- GRGSHONWRKRWGP-UHFFFAOYSA-N 2-amino-4-sulfobenzoic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1C(O)=O GRGSHONWRKRWGP-UHFFFAOYSA-N 0.000 description 1
- BMYYVVBDTDHTGJ-UHFFFAOYSA-N 2-amino-5-(3-sulfopropoxy)naphthalene-1,7-disulfonic acid Chemical compound OS(=O)(=O)CCCOC1=CC(S(O)(=O)=O)=CC2=C(S(O)(=O)=O)C(N)=CC=C21 BMYYVVBDTDHTGJ-UHFFFAOYSA-N 0.000 description 1
- REZUOOCBJKWTSZ-UHFFFAOYSA-N 2-amino-5-(diethylamino)benzenesulfonic acid Chemical compound CCN(CC)C1=CC=C(N)C(S(O)(=O)=O)=C1 REZUOOCBJKWTSZ-UHFFFAOYSA-N 0.000 description 1
- JHCGWBYXULGUSQ-UHFFFAOYSA-N 2-amino-5-(dimethylamino)benzenesulfonic acid Chemical compound CN(C)C1=CC=C(N)C(S(O)(=O)=O)=C1 JHCGWBYXULGUSQ-UHFFFAOYSA-N 0.000 description 1
- ISDHKUXEPQGCGX-UHFFFAOYSA-N 2-amino-5-bromobenzenesulfonic acid Chemical compound NC1=CC=C(Br)C=C1S(O)(=O)=O ISDHKUXEPQGCGX-UHFFFAOYSA-N 0.000 description 1
- AHUKRNXIUGDTQZ-UHFFFAOYSA-N 2-amino-5-butylbenzenesulfonic acid Chemical compound CCCCC1=CC=C(N)C(S(O)(=O)=O)=C1 AHUKRNXIUGDTQZ-UHFFFAOYSA-N 0.000 description 1
- ZCGVPUAAMCMLTM-UHFFFAOYSA-N 2-amino-5-chlorobenzenesulfonic acid Chemical compound NC1=CC=C(Cl)C=C1S(O)(=O)=O ZCGVPUAAMCMLTM-UHFFFAOYSA-N 0.000 description 1
- KTFUNVBAGAPLLC-UHFFFAOYSA-N 2-amino-5-ethoxybenzenesulfonic acid Chemical compound CCOC1=CC=C(N)C(S(O)(=O)=O)=C1 KTFUNVBAGAPLLC-UHFFFAOYSA-N 0.000 description 1
- CAFUHBWYTBNBEY-UHFFFAOYSA-N 2-amino-5-ethylbenzenesulfonic acid Chemical compound CCC1=CC=C(N)C(S(O)(=O)=O)=C1 CAFUHBWYTBNBEY-UHFFFAOYSA-N 0.000 description 1
- HIVUAOXLSJITPA-UHFFFAOYSA-N 2-amino-5-hydroxynaphthalene-1,7-disulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=C(S(O)(=O)=O)C(N)=CC=C21 HIVUAOXLSJITPA-UHFFFAOYSA-N 0.000 description 1
- LTPSRQRIPCVMKQ-UHFFFAOYSA-N 2-amino-5-methylbenzenesulfonic acid Chemical compound CC1=CC=C(N)C(S(O)(=O)=O)=C1 LTPSRQRIPCVMKQ-UHFFFAOYSA-N 0.000 description 1
- LTASFWDWBYFZQQ-UHFFFAOYSA-N 2-amino-5-nitrobenzenesulfonic acid Chemical compound NC1=CC=C([N+]([O-])=O)C=C1S(O)(=O)=O LTASFWDWBYFZQQ-UHFFFAOYSA-N 0.000 description 1
- NLYAHXJZURHDIN-UHFFFAOYSA-N 2-amino-5-propoxybenzenesulfonic acid Chemical compound CCCOC1=CC=C(N)C(S(O)(=O)=O)=C1 NLYAHXJZURHDIN-UHFFFAOYSA-N 0.000 description 1
- NWHDCCSQTQOTNP-UHFFFAOYSA-N 2-amino-5-propylbenzenesulfonic acid Chemical compound CCCC1=CC=C(N)C(S(O)(=O)=O)=C1 NWHDCCSQTQOTNP-UHFFFAOYSA-N 0.000 description 1
- MJNYPLCGWXFYPD-UHFFFAOYSA-N 2-amino-5-sulfobenzoic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1C(O)=O MJNYPLCGWXFYPD-UHFFFAOYSA-N 0.000 description 1
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 1
- IRTONKUCLPTRNS-UHFFFAOYSA-N 2-butoxyaniline Chemical compound CCCCOC1=CC=CC=C1N IRTONKUCLPTRNS-UHFFFAOYSA-N 0.000 description 1
- HDVUPIFFKAHPJY-UHFFFAOYSA-N 2-butylaniline Chemical compound CCCCC1=CC=CC=C1N HDVUPIFFKAHPJY-UHFFFAOYSA-N 0.000 description 1
- AXXYMKMFXNCXGM-UHFFFAOYSA-N 2-propoxyaniline Chemical compound CCCOC1=CC=CC=C1N AXXYMKMFXNCXGM-UHFFFAOYSA-N 0.000 description 1
- WKURVXXDGMYSDP-UHFFFAOYSA-N 2-propyl-aniline Chemical compound CCCC1=CC=CC=C1N WKURVXXDGMYSDP-UHFFFAOYSA-N 0.000 description 1
- WNRGWPVJGDABME-UHFFFAOYSA-N 3,5-Dimethoxyaniline Chemical compound COC1=CC(N)=CC(OC)=C1 WNRGWPVJGDABME-UHFFFAOYSA-N 0.000 description 1
- PANHXTZXRKSGQN-UHFFFAOYSA-N 3-amino-7-(3-sulfopropoxy)naphthalene-1,5-disulfonic acid Chemical compound C1=C(OCCCS(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 PANHXTZXRKSGQN-UHFFFAOYSA-N 0.000 description 1
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 1
- ZIZHOYOBASUITD-UHFFFAOYSA-N 3-butoxyaniline Chemical compound CCCCOC1=CC=CC(N)=C1 ZIZHOYOBASUITD-UHFFFAOYSA-N 0.000 description 1
- WMIQWIJPGVVMII-UHFFFAOYSA-N 3-butylaniline Chemical compound CCCCC1=CC=CC(N)=C1 WMIQWIJPGVVMII-UHFFFAOYSA-N 0.000 description 1
- WEZAHYDFZNTGKE-UHFFFAOYSA-N 3-ethoxyaniline Chemical compound CCOC1=CC=CC(N)=C1 WEZAHYDFZNTGKE-UHFFFAOYSA-N 0.000 description 1
- AMKPQMFZCBTTAT-UHFFFAOYSA-N 3-ethylaniline Chemical compound CCC1=CC=CC(N)=C1 AMKPQMFZCBTTAT-UHFFFAOYSA-N 0.000 description 1
- VPAHCDXFLUSULH-UHFFFAOYSA-N 3-propoxyaniline Chemical compound CCCOC1=CC=CC(N)=C1 VPAHCDXFLUSULH-UHFFFAOYSA-N 0.000 description 1
- IPWGAPCYYMTTLT-UHFFFAOYSA-N 3-propylaniline Chemical compound CCCC1=CC=CC(N)=C1 IPWGAPCYYMTTLT-UHFFFAOYSA-N 0.000 description 1
- ZDIRCGKEOWZBIM-UHFFFAOYSA-N 4-amino-2-methylbenzenesulfonic acid Chemical compound CC1=CC(N)=CC=C1S(O)(=O)=O ZDIRCGKEOWZBIM-UHFFFAOYSA-N 0.000 description 1
- BGMUQSQTQVRFMT-UHFFFAOYSA-N 4-amino-3-ethoxybenzenesulfonic acid Chemical compound CCOC1=CC(S(O)(=O)=O)=CC=C1N BGMUQSQTQVRFMT-UHFFFAOYSA-N 0.000 description 1
- MRFIZCRITUQJQJ-UHFFFAOYSA-N 4-amino-3-ethylbenzenesulfonic acid Chemical compound CCC1=CC(S(O)(=O)=O)=CC=C1N MRFIZCRITUQJQJ-UHFFFAOYSA-N 0.000 description 1
- DFFMMDIDNCWQIV-UHFFFAOYSA-N 4-amino-3-methoxybenzenesulfonic acid Chemical compound COC1=CC(S(O)(=O)=O)=CC=C1N DFFMMDIDNCWQIV-UHFFFAOYSA-N 0.000 description 1
- WQTCZINVPXJNEL-UHFFFAOYSA-N 4-amino-3-methylbenzenesulfonic acid Chemical compound CC1=CC(S(O)(=O)=O)=CC=C1N WQTCZINVPXJNEL-UHFFFAOYSA-N 0.000 description 1
- CMFKVLFKISGCPX-UHFFFAOYSA-N 4-amino-3-propylbenzenesulfonic acid Chemical compound CCCC1=CC(S(O)(=O)=O)=CC=C1N CMFKVLFKISGCPX-UHFFFAOYSA-N 0.000 description 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
- KBZFDRWPMZESDI-UHFFFAOYSA-N 5-aminobenzene-1,3-dicarboxylic acid Chemical compound NC1=CC(C(O)=O)=CC(C(O)=O)=C1 KBZFDRWPMZESDI-UHFFFAOYSA-N 0.000 description 1
- UWPJYQYRSWYIGZ-UHFFFAOYSA-N 5-aminonaphthalene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(N)=CC=CC2=C1 UWPJYQYRSWYIGZ-UHFFFAOYSA-N 0.000 description 1
- HBZVNWNSRNTWPS-UHFFFAOYSA-N 6-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(N)=CC=C21 HBZVNWNSRNTWPS-UHFFFAOYSA-N 0.000 description 1
- GLTDEMYMIMGCLY-UHFFFAOYSA-N 6-aminonaphthalene-1,4-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC=C21 GLTDEMYMIMGCLY-UHFFFAOYSA-N 0.000 description 1
- FDIKFUSYIBDMTK-UHFFFAOYSA-N 7-amino-3-(3-sulfopropoxy)naphthalene-1-sulfonic acid Chemical compound C1=C(OCCCS(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(N)=CC=C21 FDIKFUSYIBDMTK-UHFFFAOYSA-N 0.000 description 1
- IXGNUZVXNZDYPN-UHFFFAOYSA-N 7-amino-3-(4-sulfobutoxy)naphthalene-1-sulfonic acid Chemical compound C1=C(OCCCCS(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(N)=CC=C21 IXGNUZVXNZDYPN-UHFFFAOYSA-N 0.000 description 1
- XOQYBLQTFIAIJP-UHFFFAOYSA-N 7-amino-4-(3-sulfopropoxy)naphthalene-2-sulfonic acid Chemical compound OS(=O)(=O)CCCOC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 XOQYBLQTFIAIJP-UHFFFAOYSA-N 0.000 description 1
- ZRHQESITNFNBQL-UHFFFAOYSA-N 7-amino-4-(4-sulfobutoxy)naphthalene-2-sulfonic acid Chemical compound OS(=O)(=O)CCCCOC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 ZRHQESITNFNBQL-UHFFFAOYSA-N 0.000 description 1
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 1
- UBDHSURDYAETAL-UHFFFAOYSA-N 8-aminonaphthalene-1,3,6-trisulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 UBDHSURDYAETAL-UHFFFAOYSA-N 0.000 description 1
- YDEOXZHCPCPPJG-UHFFFAOYSA-N 8-aminonaphthalene-1,6-disulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 YDEOXZHCPCPPJG-UHFFFAOYSA-N 0.000 description 1
- QEZZCWMQXHXAFG-UHFFFAOYSA-N 8-aminonaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(N)=CC=CC2=C1 QEZZCWMQXHXAFG-UHFFFAOYSA-N 0.000 description 1
- 0 C*C(C(NC(Nc(c(*)c1)cc(*)c1N=N[C@](CC1*)C(*)=C[C@@]1N=Nc1ccccc1)=O)=CC1*)=C[C@]1N=NC(C(*)=C1)=CC(*)[C@@]1N=Nc1ccccc1 Chemical compound C*C(C(NC(Nc(c(*)c1)cc(*)c1N=N[C@](CC1*)C(*)=C[C@@]1N=Nc1ccccc1)=O)=CC1*)=C[C@]1N=NC(C(*)=C1)=CC(*)[C@@]1N=Nc1ccccc1 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PYVHTIWHNXTVPF-UHFFFAOYSA-N F.F.F.F.C=C Chemical compound F.F.F.F.C=C PYVHTIWHNXTVPF-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- RDZZCUQPVLDLSG-UHFFFAOYSA-N NC1=C(C=C(C=C1)OCCCC)S(=O)(=O)O Chemical compound NC1=C(C=C(C=C1)OCCCC)S(=O)(=O)O RDZZCUQPVLDLSG-UHFFFAOYSA-N 0.000 description 1
- CBWBBTQRPZVAQW-UHFFFAOYSA-N NC1=C(C=C(C=C1)S(=O)(=O)O)CCCC Chemical compound NC1=C(C=C(C=C1)S(=O)(=O)O)CCCC CBWBBTQRPZVAQW-UHFFFAOYSA-N 0.000 description 1
- AODXEMOJFNWGIR-UHFFFAOYSA-N NC1=C(C=C(C=C1)S(=O)(=O)O)OCCC Chemical compound NC1=C(C=C(C=C1)S(=O)(=O)O)OCCC AODXEMOJFNWGIR-UHFFFAOYSA-N 0.000 description 1
- LPAJQJDOXKZSLZ-UHFFFAOYSA-N NC1=C(C=C(C=C1)S(=O)(=O)O)OCCCC Chemical compound NC1=C(C=C(C=C1)S(=O)(=O)O)OCCCC LPAJQJDOXKZSLZ-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- SQISUZWPWJHTEP-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1.NC1=CC=CC=C1 SQISUZWPWJHTEP-UHFFFAOYSA-N 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 239000005388 borosilicate glass Substances 0.000 description 1
- VVPQDWNJHAVPDN-UHFFFAOYSA-N c(cc1)cc2c1C=C=[I]C=C2 Chemical compound c(cc1)cc2c1C=C=[I]C=C2 VVPQDWNJHAVPDN-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229920006317 cationic polymer Polymers 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000011159 matrix material Substances 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
- WFWWBGDDTJRGQF-UHFFFAOYSA-N naphthalen-1-amine Chemical compound C1=CC=C2C(N)=CC=CC2=C1.C1=CC=C2C(N)=CC=CC2=C1 WFWWBGDDTJRGQF-UHFFFAOYSA-N 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- NRZRRZAVMCAKEP-UHFFFAOYSA-N naphthionic acid Chemical compound C1=CC=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 NRZRRZAVMCAKEP-UHFFFAOYSA-N 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052594 sapphire Inorganic materials 0.000 description 1
- 239000010980 sapphire Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 239000011029 spinel Substances 0.000 description 1
- 229910052596 spinel Inorganic materials 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
- C09B43/124—Preparation of azo dyes from other azo compounds by acylation of amino groups with monocarboxylic acids, carbamic esters or halides, mono- isocyanates, or haloformic acid esters
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
-
- 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
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Chemical & Material Sciences (AREA)
- Nonlinear Science (AREA)
- Organic Chemistry (AREA)
- Mathematical Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Polarising Elements (AREA)
- Liquid Crystal (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2015102406 | 2015-05-20 | ||
| JP2015102398 | 2015-05-20 | ||
| JP2015102406 | 2015-05-20 | ||
| JP2015102398 | 2015-05-20 | ||
| PCT/JP2016/064987 WO2016186195A1 (ja) | 2015-05-20 | 2016-05-20 | アゾ化合物及びそれらを含有する染料系偏光膜並びに偏光板 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPWO2016186195A1 JPWO2016186195A1 (ja) | 2018-03-08 |
| JP6824160B2 true JP6824160B2 (ja) | 2021-02-03 |
Family
ID=57320459
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017519412A Active JP6824160B2 (ja) | 2015-05-20 | 2016-05-20 | アゾ化合物及びそれらを含有する染料系偏光膜並びに偏光板 |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JP6824160B2 (zh) |
| KR (1) | KR102581552B1 (zh) |
| CN (1) | CN107614625B (zh) |
| HK (1) | HK1243448A1 (zh) |
| TW (1) | TWI715584B (zh) |
| WO (1) | WO2016186195A1 (zh) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018181470A1 (ja) * | 2017-03-31 | 2018-10-04 | 日本化薬株式会社 | アゾ化合物又はその塩、並びにこれを含有する染料系偏光膜、染料系偏光板、及び液晶表示装置 |
| WO2021153374A1 (ja) * | 2020-01-29 | 2021-08-05 | 日本化薬株式会社 | アゾ化合物又はその塩、並びにこれを含有する染料系偏光膜、染料系偏光板、及び表示装置 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2519651A (en) * | 1945-07-26 | 1950-08-22 | Ciba Ltd | Polyazo dyestuffs |
| JPH08240715A (ja) * | 1995-03-03 | 1996-09-17 | Sumitomo Chem Co Ltd | 偏光フィルムの製造法 |
| US5667719A (en) * | 1995-06-02 | 1997-09-16 | Hoechst Celanese Corp. | High extinction polarizer films comprising liquid crystal polymeric moieties |
| JP3769140B2 (ja) * | 1998-03-20 | 2006-04-19 | 住友化学株式会社 | 偏光フィルム |
| JP4162334B2 (ja) | 1999-07-26 | 2008-10-08 | 日本化薬株式会社 | 染料系偏光膜 |
| JP4078476B2 (ja) * | 1999-12-24 | 2008-04-23 | 住友化学株式会社 | アゾ化合物又はその塩及びそれらを含有する染料系偏光膜 |
| TW555812B (en) * | 1999-12-24 | 2003-10-01 | Sumitomo Chemical Co | Azo-compounds and dye polarizing films containing them |
| AU2003252356A1 (en) * | 2002-08-05 | 2004-02-23 | Nippon Kayaku Kabushiki Kaisha | Trisazo compounds, water-base ink compositions, and colored articles |
| JP5204944B2 (ja) * | 2004-06-07 | 2013-06-05 | 富士フイルム株式会社 | 黒インク組成物、およびインクジェット記録方法。 |
| JP4736424B2 (ja) * | 2004-12-27 | 2011-07-27 | 住友化学株式会社 | アゾ化合物又はその塩、及び該化合物又はその塩を含有する偏光膜 |
| WO2007023733A1 (ja) * | 2005-08-22 | 2007-03-01 | Sumitomo Chemical Company, Limited | アゾ化合物及び該化合物を含有する偏光膜 |
| JP5017961B2 (ja) * | 2005-08-22 | 2012-09-05 | 住友化学株式会社 | アゾ化合物及び該化合物を含有する偏光膜 |
| JP2009132794A (ja) * | 2007-11-30 | 2009-06-18 | Nippon Kayaku Co Ltd | アゾ化合物、インク組成物、記録方法及び着色体 |
| JP2009155364A (ja) * | 2007-12-25 | 2009-07-16 | Sumitomo Chemical Co Ltd | アゾ化合物及び該アゾ化合物を含有する偏光膜 |
| KR101793761B1 (ko) * | 2010-03-30 | 2017-11-03 | 닛뽄 가야쿠 가부시키가이샤 | 수용성 아조 화합물 또는 그 염, 잉크 조성물 및 착색체 |
| US20140218797A1 (en) * | 2011-09-09 | 2014-08-07 | Polatechno Co., Ltd. | Polarizing Element And Polarizing Plate |
| KR102129135B1 (ko) * | 2012-02-28 | 2020-07-01 | 스미또모 가가꾸 가부시키가이샤 | 편광막, 원편광판 및 이들의 제조 방법 |
| JP2014148592A (ja) * | 2013-01-31 | 2014-08-21 | Ricoh Co Ltd | インクジェットインクセット、画像形成方法、画像形成装置 |
| JP6592443B2 (ja) * | 2014-08-08 | 2019-10-16 | 日本化薬株式会社 | 水溶性アゾ化合物又はその塩、インク組成物及び着色体 |
-
2016
- 2016-05-20 TW TW105115803A patent/TWI715584B/zh active
- 2016-05-20 KR KR1020177033440A patent/KR102581552B1/ko active IP Right Grant
- 2016-05-20 WO PCT/JP2016/064987 patent/WO2016186195A1/ja active Application Filing
- 2016-05-20 CN CN201680029276.XA patent/CN107614625B/zh active Active
- 2016-05-20 JP JP2017519412A patent/JP6824160B2/ja active Active
-
2018
- 2018-03-02 HK HK18103062.7A patent/HK1243448A1/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPWO2016186195A1 (ja) | 2018-03-08 |
| TW201704360A (zh) | 2017-02-01 |
| WO2016186195A1 (ja) | 2016-11-24 |
| CN107614625A (zh) | 2018-01-19 |
| CN107614625B (zh) | 2019-11-12 |
| KR102581552B1 (ko) | 2023-09-21 |
| TWI715584B (zh) | 2021-01-11 |
| KR20180006925A (ko) | 2018-01-19 |
| HK1243448A1 (zh) | 2018-07-13 |
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