JPWO2012165222A1 - 染料系偏光素子及び偏光板 - Google Patents
染料系偏光素子及び偏光板 Download PDFInfo
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- JPWO2012165222A1 JPWO2012165222A1 JP2013517982A JP2013517982A JPWO2012165222A1 JP WO2012165222 A1 JPWO2012165222 A1 JP WO2012165222A1 JP 2013517982 A JP2013517982 A JP 2013517982A JP 2013517982 A JP2013517982 A JP 2013517982A JP WO2012165222 A1 JPWO2012165222 A1 JP WO2012165222A1
- Authority
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- Prior art keywords
- dye
- formula
- film
- polarizing element
- polyvinyl alcohol
- 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.)
- Granted
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- 239000000975 dye Substances 0.000 claims abstract description 91
- 239000011347 resin Substances 0.000 claims abstract description 46
- 229920005989 resin Polymers 0.000 claims abstract description 46
- 239000004372 Polyvinyl alcohol Substances 0.000 claims abstract description 33
- 229920002451 polyvinyl alcohol Polymers 0.000 claims abstract description 33
- -1 azo compound Chemical class 0.000 claims abstract description 30
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 239000011241 protective layer Substances 0.000 claims description 12
- 230000010287 polarization Effects 0.000 abstract description 22
- 239000000126 substance Substances 0.000 abstract description 13
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 abstract description 12
- 239000001045 blue dye Substances 0.000 abstract description 9
- 239000002994 raw material Substances 0.000 abstract description 7
- 238000000034 method Methods 0.000 description 39
- 239000000243 solution Substances 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000003431 cross linking reagent Substances 0.000 description 18
- 239000000853 adhesive Substances 0.000 description 16
- 230000008569 process Effects 0.000 description 16
- 230000001070 adhesive effect Effects 0.000 description 14
- 238000004043 dyeing Methods 0.000 description 14
- 239000000049 pigment Substances 0.000 description 14
- 238000002834 transmittance Methods 0.000 description 14
- 238000001035 drying Methods 0.000 description 12
- 238000005406 washing Methods 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 11
- 239000004327 boric acid Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 9
- 238000004140 cleaning Methods 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- 229920002554 vinyl polymer Polymers 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- 239000004973 liquid crystal related substance Substances 0.000 description 8
- 238000004078 waterproofing Methods 0.000 description 8
- 206010042674 Swelling Diseases 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 230000008961 swelling Effects 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 230000001681 protective effect Effects 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 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 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000012790 adhesive layer Substances 0.000 description 4
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N alpha-ketodiacetal Natural products O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 4
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000013053 water resistant agent Substances 0.000 description 4
- 229920002284 Cellulose triacetate Polymers 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 150000001299 aldehydes Chemical group 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000002346 layers by function Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229920002689 polyvinyl acetate Polymers 0.000 description 3
- 239000011118 polyvinyl acetate Substances 0.000 description 3
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 2
- IVIDDMGBRCPGLJ-UHFFFAOYSA-N 2,3-bis(oxiran-2-ylmethoxy)propan-1-ol Chemical compound C1OC1COC(CO)COCC1CO1 IVIDDMGBRCPGLJ-UHFFFAOYSA-N 0.000 description 2
- WHQOKFZWSDOTQP-UHFFFAOYSA-N 2,3-dihydroxypropyl 4-aminobenzoate Chemical compound NC1=CC=C(C(=O)OCC(O)CO)C=C1 WHQOKFZWSDOTQP-UHFFFAOYSA-N 0.000 description 2
- CUGZWHZWSVUSBE-UHFFFAOYSA-N 2-(oxiran-2-ylmethoxy)ethanol Chemical compound OCCOCC1CO1 CUGZWHZWSVUSBE-UHFFFAOYSA-N 0.000 description 2
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 2
- MKTOIPPVFPJEQO-UHFFFAOYSA-N 4-(3-carboxypropanoylperoxy)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)OOC(=O)CCC(O)=O MKTOIPPVFPJEQO-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 241000694440 Colpidium aqueous Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 238000010306 acid treatment Methods 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000000987 azo dye Substances 0.000 description 2
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 2
- 229910021538 borax Inorganic materials 0.000 description 2
- 150000001639 boron compounds Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 231100000481 chemical toxicant Toxicity 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 229910000365 copper sulfate Inorganic materials 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 229940015043 glyoxal Drugs 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 229920001477 hydrophilic polymer Polymers 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920001228 polyisocyanate Polymers 0.000 description 2
- 239000005056 polyisocyanate Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000005185 salting out Methods 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000004328 sodium tetraborate Substances 0.000 description 2
- 235000010339 sodium tetraborate Nutrition 0.000 description 2
- 235000019832 sodium triphosphate Nutrition 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 239000003440 toxic substance Substances 0.000 description 2
- WYXIGTJNYDDFFH-UHFFFAOYSA-Q triazanium;borate Chemical compound [NH4+].[NH4+].[NH4+].[O-]B([O-])[O-] WYXIGTJNYDDFFH-UHFFFAOYSA-Q 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- KLBVIRPOVIVOLL-UHFFFAOYSA-N 3-hydroxy-4-[[4-[4-[[2-hydroxy-3-[(2-methoxyphenyl)carbamoyl]naphthalen-1-yl]diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-N-(2-methoxyphenyl)naphthalene-2-carboxamide Chemical compound COc1ccccc1NC(=O)c1cc2ccccc2c(N=Nc2ccc(cc2OC)-c2ccc(N=Nc3c(O)c(cc4ccccc34)C(=O)Nc3ccccc3OC)c(OC)c2)c1O KLBVIRPOVIVOLL-UHFFFAOYSA-N 0.000 description 1
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- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- PTIWCWYYGIRDIZ-UHFFFAOYSA-K Durazol blue 4R Chemical compound [Na+].[Na+].[Na+].COc1cc(N=Nc2cc(cc3cc(cc(O)c23)S([O-])(=O)=O)S([O-])(=O)=O)c(C)cc1N=Nc1c(O)c2ccc(Nc3ccccc3)cc2cc1S([O-])(=O)=O PTIWCWYYGIRDIZ-UHFFFAOYSA-K 0.000 description 1
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- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
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- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
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- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
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- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate 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
- 239000007787 solid Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- OLSOUGWNONTDCK-UHFFFAOYSA-J tetrasodium 5-amino-3-[[4-[4-[(8-amino-1-hydroxy-3,6-disulfonatonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-4-hydroxynaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(N=NC3=CC=C(C=C3OC)C=3C=C(C(=CC=3)N=NC=3C(=CC4=CC(=CC(N)=C4C=3O)S([O-])(=O)=O)S([O-])(=O)=O)OC)=C(O)C2=C1N OLSOUGWNONTDCK-UHFFFAOYSA-J 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
Classifications
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/08—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of polarising materials
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/06—Disazo dyes from a coupling component "C" containing a directive hydroxyl group
- C09B31/068—Naphthols
- C09B31/072—Naphthols containing acid groups, e.g. —CO2H, —SO3H, —PO3H2, —OSO3H, —OPO2H2; Salts thereof
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- C—CHEMISTRY; METALLURGY
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- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/08—Disazo dyes from a coupling component "C" containing directive hydroxyl and amino groups
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/04—Azo compounds in general
- C09B45/08—Copper compounds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/24—Disazo or polyazo compounds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/24—Disazo or polyazo compounds
- C09B45/26—Disazo or polyazo compounds containing chromium
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/24—Disazo or polyazo compounds
- C09B45/28—Disazo or polyazo compounds containing copper
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- C—CHEMISTRY; METALLURGY
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- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0055—Mixtures of two or more disazo dyes
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
- G02B5/3025—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state
- G02B5/3033—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
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- Chemical & Material Sciences (AREA)
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- Optics & Photonics (AREA)
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- Nonlinear Science (AREA)
- Mathematical Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Polarising Elements (AREA)
Abstract
Description
従来、製紙材料およびセルロース系繊維を堅牢な青色に染める染料としては、C.I.Direct Blue15、200、202、203などが知られており、製紙業界および染色業界において多用されている。しかしながら、これらの染料に共通する欠点としては、これらの染料を原料として使用する際の共通の問題点として、主原料として使用されているジアニシジンが特定化学物質第一類に該当する毒性化学物質であり、かつ、色素そのものもジアニシジン系色素であるので、ジアニシジンの使用に当っては、労働安全衛生法を厳守することが必須であり、極めて厳重な防護設備の下で作業する必要があり、安全衛生管理及び生産効率の向上に関して大きな制約要因となっている。
一方、ジアニシジン以外の青色染料としては、例えばC.I. Direct Blue67、78、106、108等があるが、いずれもジアニシジン系青色染料に比べて明らかに染着性不良の欠点を有している。即ちジアニシジンを使用しなくては堅牢で染着性の良い青色染料を容易に得ることが難しく、この為ジアニシジンが特定化学物質第一類に該当する毒性化学物質であり、作業者への曝露を避ける為の防護設備に多くの経費をかけてもなおこれを使用する青色染料が広く製造され、使用されている状況にある。従って、ジアニシジンの様な特定化学物質に該当する原料を使用しないで、堅牢で染着性の良い青色染料を得ることは、染料業界、製紙業界だけでなく、偏光板の開発にとって永年強く望まれていた。特に、偏光素子の開発においては、高い偏光特性を有することが前提としてあり、それに加え、偏光機能と色と耐久性とを兼ね備えることが非常に困難であった。
(3)二色性色素を含有し、3倍以上延伸してなるポリビニルアルコール樹脂又はその誘導体のフィルムからなる偏光素子であって、該二色性色素の少なくとも一つである上記式(1)で示されるアゾ化合物又はその塩と、該二色性色素の少なくとも一つである式(2)で示されるアゾ化合物又はその塩の含有量の比が、9:1〜10:0であることを特徴とする該偏光素子の製造方法に関する。
本発明の偏光素子は、ポリビニルアルコール樹脂又はその誘導体に二色性色素を含有し、3倍以上延伸してなるフィルムであって、該二色性色素の少なくとも一つが前記式(1)で表される色素である。 式(1)で表される色素は、偏光特性が良好であるが、不純物として含まれる式(2)で表される色素は、フィルム中に含有されると偏光特性が大きく低下する。そのため、式(2)で表される色素は、式(1)の化合物及び式(2)の化合物の総量中に10%以内、好ましくは5%以内、より好ましくは3%以内、さらに好ましくは1%以内であることが好ましい。
<色素溶液の作製>
2−アミノナフタリン−4,8−ジスルホン酸(慣用名:C酸) 32.5部を水145部に溶かし35%塩酸26部を含む水140部中に加え15〜20℃で亜硝酸ソーダ6.9部を加えて1時間かけてジアゾ化する。次いでパラクレシジン13.7部、35%塩酸17.5部とからなる水溶液を加え、酢酸ソーダでpH3.0〜3.5を保ちながら、20℃で4時間かけて斑点テストでパラクレシジンが認められなくなるまでカップリングする。次いでこのアミノアゾ化合物に35%塩酸21.4部を加え、10℃で亜硝酸ソーダ6.9部を加えて15〜20℃で2〜3時間を要して2次ジアゾ化を行う。次いでこれをフェニルJ酸31.5部、水125部、ソーダ灰11部とからなる水溶液中に加え、更にソーダ灰溶液を注加しながら、pH8.5〜9.5を保ち、20℃で3時間かけて斑点テストでジアゾ化物が認められなくなるまで2次カップリングを行い、ジスアゾ化合物を得た。ついで、硫酸銅25部の水溶液にモノエタノールアミン30.5部を加えてつくった銅錯塩を加え95℃で10時間かけて薄層クロマト上で未反応物を認められなくなるまで銅化反応を行い、本願の式(1)で示される色素が20重量%含有した溶液を作製した。
<偏光素子の作製>
ケン化度が99%以上の膜厚75μmのポリビニルアルコール系樹脂フィルム(クラレ社製 VFシリーズ)を40℃の温水に2分浸漬し膨潤処理をした。膨潤処理したフィルムを、式(1)で表される色素の20重量%水溶液に25重量%のサヌキ塩にて塩析し、60℃にて乾燥させた色素粉体(HPLC純度98.2%)を0.05重量%、トリポリ燐酸ナトリウム0.1重量%を含有した45℃の水溶液に浸漬し、染料の吸着を行った。染料が吸着されたフィルムを水にて洗浄し、洗浄の後、2重量%のホウ酸を含有した40℃の水溶液で1分間ホウ酸処理を行った。ホウ酸処理して得られたフィルムを、5.0倍に延伸しながらホウ酸3.0重量%を含有した55℃の水溶液中で5分間処理を行った。そのホウ酸処理して得られたフィルムの緊張状態を保ちつつ、30℃の水で15秒間洗浄を行った。処理して得られたフィルムを直ちに70℃で9分間乾燥処理を行い膜厚28μmの偏光素子を得た。
実施例1で用いた式(1)で表される色素が含有した20重量%溶液を25重量%のサヌキ塩にて塩析し、乾燥する際の温度を90℃にて乾燥させた色素粉体(HPLC純度87.9%)を用いた以外は同様に偏光素子の作製を行った。乾燥させた色素粉体には、式(2)で表される色素が7.5%含有していた。また、得られた偏光素子を溶解し、HPLC測定を行ったところ、フィルム中の式(1)に示される色素の純度は88.7%であった。
Claims (3)
- 請求項1に記載の偏光素子の片面、もしくは両面に保護層が設けられている偏光板。
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PCT/JP2012/063047 WO2012165222A1 (ja) | 2011-05-30 | 2012-05-22 | 染料系偏光素子及び偏光板 |
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CN (1) | CN103502852B (ja) |
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WO2014162633A1 (ja) * | 2013-04-03 | 2014-10-09 | 日本化薬株式会社 | 無彩色な偏光素子、及び偏光板 |
CN105190378B (zh) * | 2013-04-03 | 2018-02-16 | 日本化药株式会社 | 具有高透射率的无彩色的染料系偏振元件和偏振片 |
JP6769711B2 (ja) * | 2013-09-27 | 2020-10-14 | 日本化薬株式会社 | 染料系偏光素子、または、染料系偏光板 |
KR101740639B1 (ko) * | 2016-04-01 | 2017-05-26 | 에스케이씨하스디스플레이필름(유) | 흡수염료를 포함하는 액정표시장치 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS57145155A (en) * | 1981-03-04 | 1982-09-08 | Nippon Kayaku Co Ltd | Copper-containing azo compound and dyeing method using the same |
JPS62190272A (ja) * | 1986-02-17 | 1987-08-20 | Canon Inc | 記録液 |
JPH03769A (ja) * | 1989-05-29 | 1991-01-07 | Nippon Kayaku Co Ltd | アゾ化合物及びそれを用いる染色法 |
JPH0553014A (ja) * | 1991-08-29 | 1993-03-05 | Sumitomo Chem Co Ltd | 染料系偏光膜 |
JPH0553015A (ja) * | 1991-08-29 | 1993-03-05 | Sumitomo Chem Co Ltd | 染料系の偏光膜 |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3236238A1 (de) * | 1982-09-30 | 1984-05-24 | Sandoz-Patent-GmbH, 7850 Lörrach | Metallkomplexe sulfogruppenhaltiger disazoverbindungen, verfahren zur herstellung und verwendung |
JPS60156759A (ja) | 1984-01-25 | 1985-08-16 | Nippon Kayaku Co Ltd | 水溶性ジスアゾ化合物 |
CA2076560A1 (en) * | 1991-08-29 | 1993-03-01 | Kazuya Ogino | Dye-containing polarizing film |
JPH0718192A (ja) * | 1993-07-02 | 1995-01-20 | Nippon Kayaku Co Ltd | 含銅アゾ化合物及びそれを用いて染色する方法 |
JPH11218611A (ja) | 1998-01-30 | 1999-08-10 | Nippon Kayaku Co Ltd | 染料系偏光膜 |
JP4049229B2 (ja) | 1998-01-30 | 2008-02-20 | 日本化薬株式会社 | 新規偏光膜 |
JP4162334B2 (ja) | 1999-07-26 | 2008-10-08 | 日本化薬株式会社 | 染料系偏光膜 |
JP4162336B2 (ja) | 1999-08-20 | 2008-10-08 | 日本化薬株式会社 | 染料系偏光膜 |
JP2001027708A (ja) | 1999-07-14 | 2001-01-30 | Nippon Kayaku Co Ltd | 液晶プロジェクター用偏光板及びカラー液晶プロジェクタ |
JP4371345B2 (ja) | 2001-03-30 | 2009-11-25 | 日本化薬株式会社 | 染料系偏光膜 |
JP4033443B2 (ja) | 2002-01-22 | 2008-01-16 | 日本化薬株式会社 | 染料系偏光膜及び偏光板 |
JP4270486B2 (ja) | 2002-08-09 | 2009-06-03 | 日本化薬株式会社 | トリスアゾ化合物、水性インク組成物及び着色体 |
WO2004092282A1 (ja) | 2003-04-16 | 2004-10-28 | Nippon Kayaku Kabushiki Kaisha | アゾ化合物及びその塩 |
KR20060109439A (ko) * | 2003-10-27 | 2006-10-20 | 클라리언트 파이넌스 (비브이아이)리미티드 | 음이온성 디스아조 또는 테트라아조 염료의 저장안정성농축 수용액 |
WO2005113684A1 (en) * | 2004-05-19 | 2005-12-01 | Clariant Finance (Bvi) Limited | Stable liquid formulations of anionic dyes |
WO2006076063A1 (en) * | 2005-01-10 | 2006-07-20 | Lanxess Corporation | Improved lightfast, trichromatic black dye mixtures |
KR100544327B1 (ko) * | 2005-08-02 | 2006-01-23 | 신화오플라주식회사 | 유기발광다이오드 디스플레이용 염료계 원편광판 |
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- 2012-05-22 CA CA 2837270 patent/CA2837270A1/en not_active Abandoned
- 2012-05-22 KR KR20137025338A patent/KR20140031861A/ko active Search and Examination
- 2012-05-22 EP EP12793233.3A patent/EP2717074B8/en not_active Not-in-force
- 2012-05-22 WO PCT/JP2012/063047 patent/WO2012165222A1/ja active Application Filing
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- 2012-05-22 CN CN201280021655.6A patent/CN103502852B/zh active Active
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Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS57145155A (en) * | 1981-03-04 | 1982-09-08 | Nippon Kayaku Co Ltd | Copper-containing azo compound and dyeing method using the same |
JPS62190272A (ja) * | 1986-02-17 | 1987-08-20 | Canon Inc | 記録液 |
JPH03769A (ja) * | 1989-05-29 | 1991-01-07 | Nippon Kayaku Co Ltd | アゾ化合物及びそれを用いる染色法 |
JPH0553014A (ja) * | 1991-08-29 | 1993-03-05 | Sumitomo Chem Co Ltd | 染料系偏光膜 |
JPH0553015A (ja) * | 1991-08-29 | 1993-03-05 | Sumitomo Chem Co Ltd | 染料系の偏光膜 |
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EP2717074A4 (en) | 2014-12-03 |
CA2837270A1 (en) | 2012-12-06 |
JP5998129B2 (ja) | 2016-09-28 |
WO2012165222A1 (ja) | 2012-12-06 |
CN103502852B (zh) | 2016-08-17 |
CN103502852A (zh) | 2014-01-08 |
TW201300465A (zh) | 2013-01-01 |
HK1192778A1 (zh) | 2014-08-29 |
EP2717074B8 (en) | 2019-05-22 |
US20140087201A1 (en) | 2014-03-27 |
EP2717074A1 (en) | 2014-04-09 |
TWI487749B (zh) | 2015-06-11 |
KR20140031861A (ko) | 2014-03-13 |
EP2717074B1 (en) | 2019-02-27 |
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