CN104160305B - Dyestuff system polarization element and polaroid - Google Patents
Dyestuff system polarization element and polaroid Download PDFInfo
- Publication number
- CN104160305B CN104160305B CN201380009089.1A CN201380009089A CN104160305B CN 104160305 B CN104160305 B CN 104160305B CN 201380009089 A CN201380009089 A CN 201380009089A CN 104160305 B CN104160305 B CN 104160305B
- Authority
- CN
- China
- Prior art keywords
- polarization element
- polaroid
- film
- formula
- dyestuff
- 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.)
- Active
Links
- 230000010287 polarization Effects 0.000 title claims abstract description 78
- 239000000975 dye Substances 0.000 title description 61
- 229920005989 resin Polymers 0.000 claims abstract description 44
- 239000011347 resin Substances 0.000 claims abstract description 44
- 229920002451 polyvinyl alcohol Polymers 0.000 claims abstract description 38
- 239000004372 Polyvinyl alcohol Substances 0.000 claims abstract description 35
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 239000002253 acid Substances 0.000 claims abstract description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- 239000004973 liquid crystal related substance Substances 0.000 claims description 13
- 230000001681 protective effect Effects 0.000 claims description 13
- 238000000034 method Methods 0.000 description 47
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 42
- 239000003795 chemical substances by application Substances 0.000 description 27
- 230000008569 process Effects 0.000 description 27
- 239000000126 substance Substances 0.000 description 23
- 230000000052 comparative effect Effects 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- 238000004132 cross linking Methods 0.000 description 19
- 238000004519 manufacturing process Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000010410 layer Substances 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- 238000010521 absorption reaction Methods 0.000 description 10
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 10
- 239000004327 boric acid Substances 0.000 description 10
- 238000004140 cleaning Methods 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 238000001035 drying Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- -1 alkylamine salt Chemical class 0.000 description 9
- 238000004043 dyeing Methods 0.000 description 9
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 7
- 206010042674 Swelling Diseases 0.000 description 7
- 239000000049 pigment Substances 0.000 description 7
- 238000012545 processing Methods 0.000 description 7
- 230000008961 swelling Effects 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 229910052740 iodine Inorganic materials 0.000 description 6
- 239000011630 iodine Substances 0.000 description 6
- 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 5
- 239000002585 base Substances 0.000 description 5
- 239000002346 layers by function Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 229920002284 Cellulose triacetate Polymers 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 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 4
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N alpha-ketodiacetal Natural products O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 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
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 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
- 229960004050 aminobenzoic acid Drugs 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000007767 bonding agent Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 238000007127 saponification reaction Methods 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
- 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
- STOOUUMSJPLRNI-UHFFFAOYSA-N 5-amino-4-hydroxy-3-[[4-[4-[(4-hydroxyphenyl)diazenyl]phenyl]phenyl]diazenyl]-6-[(4-nitrophenyl)diazenyl]naphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC2=CC(S(O)(=O)=O)=C(N=NC=3C=CC(=CC=3)C=3C=CC(=CC=3)N=NC=3C=CC(O)=CC=3)C(O)=C2C(N)=C1N=NC1=CC=C([N+]([O-])=O)C=C1 STOOUUMSJPLRNI-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229920001744 Polyaldehyde Polymers 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
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- 229920006387 Vinylite Polymers 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 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
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical group 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
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 238000012937 correction Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 229940015043 glyoxal Drugs 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Natural products OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 238000003475 lamination Methods 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 description 2
- 210000000713 mesentery Anatomy 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 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
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 229910000349 titanium oxysulfate Inorganic materials 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
- 229920002554 vinyl polymer Polymers 0.000 description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- 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 description 1
- FDGAEAYZQQCBRN-UHFFFAOYSA-N 3-amino-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1N FDGAEAYZQQCBRN-UHFFFAOYSA-N 0.000 description 1
- XKFIFYROMAAUDL-UHFFFAOYSA-N 3-amino-4-methylbenzoic acid Chemical group CC1=CC=C(C(O)=O)C=C1N XKFIFYROMAAUDL-UHFFFAOYSA-N 0.000 description 1
- MDIOOMYYSWKVTE-UHFFFAOYSA-N 4-amino-3-chloro-5-methoxybenzoic acid Chemical group COC1=CC(C(O)=O)=CC(Cl)=C1N MDIOOMYYSWKVTE-UHFFFAOYSA-N 0.000 description 1
- DFFMMDIDNCWQIV-UHFFFAOYSA-N 4-amino-3-methoxybenzenesulfonic acid Chemical group COC1=CC(S(O)(=O)=O)=CC=C1N DFFMMDIDNCWQIV-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical class OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 229920000856 Amylose Polymers 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 238000006424 Flood reaction Methods 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 229940081735 acetylcellulose Drugs 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000012461 cellulose resin Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- HGAZMNJKRQFZKS-UHFFFAOYSA-N chloroethene;ethenyl acetate Chemical compound ClC=C.CC(=O)OC=C HGAZMNJKRQFZKS-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 229920005994 diacetyl cellulose Polymers 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- PBOIUUROGJVVNC-UHFFFAOYSA-L disodium 2-hydroxy-5-[[4-[[2-methoxy-4-[(3-sulfonatophenyl)diazenyl]phenyl]carbamoylamino]phenyl]diazenyl]benzoate Chemical compound [Na+].[Na+].COc1cc(ccc1NC(=O)Nc1ccc(cc1)N=Nc1ccc(O)c(c1)C([O-])=O)N=Nc1cccc(c1)S([O-])(=O)=O PBOIUUROGJVVNC-UHFFFAOYSA-L 0.000 description 1
- DSARWKALPGYFTA-UHFFFAOYSA-L disodium 4-hydroxy-7-[(5-hydroxy-6-phenyldiazenyl-7-sulfonatonaphthalen-2-yl)carbamoylamino]-3-phenyldiazenylnaphthalene-2-sulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC2=CC(NC(=O)NC=3C=C4C=C(C(N=NC=5C=CC=CC=5)=C(O)C4=CC=3)S([O-])(=O)=O)=CC=C2C(O)=C1N=NC1=CC=CC=C1 DSARWKALPGYFTA-UHFFFAOYSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 210000004379 membrane Anatomy 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 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
- 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
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 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
- FIXVWFINKCQNFG-UHFFFAOYSA-M sodium;4-[(4-aminophenyl)diazenyl]benzenesulfonate Chemical compound [Na+].C1=CC(N)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 FIXVWFINKCQNFG-UHFFFAOYSA-M 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 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
- 150000003752 zinc compounds Chemical class 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
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/02—Disazo dyes
- C09B33/04—Disazo dyes in which the coupling component is a dihydroxy or polyhydroxy compound
- C09B33/048—Disazo dyes in which the coupling component is a dihydroxy or polyhydroxy compound the coupling component being a bis-naphthol
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polarising Elements (AREA)
- Liquid Crystal (AREA)
Abstract
Problem of the present invention is to develop a kind ofly to be had good polarized light property and also has the polarization element of high-durability.The present invention relates to a kind of polarization element, it is characterized in that, it is by containing polyvinyl alcohol resin or derivatives thereof and dichroic dye and the polarization element that forms of the film stretched, the azo-compound represented by formula (1) that at least one of this dichroic dye is free acid form or its salt.(in formula, A represents the phenyl with at least 1 carboxyl alternatively base.)
Description
Technical field
The present invention relates to dyestuff system polarization element and the polaroid employing this polarization element.
Background technology
Polarization element is normally by making to be adsorbed on polyvinyl alcohol resin film as the iodine of dichromatism pigment or dichroic dye and carrying out orientation to manufacture.By adhesive layer, the diaphragm formed by triacetyl cellulose etc. is fitted at least one side of this polarization element to make polaroid, thus in liquid crystal indicator etc.Use iodine to be called as iodine system polaroid as the polaroid of dichromatism pigment, in addition, use dichroic dye to be called as dyestuff system polaroid as the polaroid of dichromatism pigment.Among them, if compare with the iodine system polaroid with identical degree of polarization, then dyestuff system polaroid has low, that namely contrast the is low problem of transmitance, but it has following characteristics: have high-fire resistance, high wet heat durability, high stability, and, have developed the dyestuff with various color, high color selective can be obtained by carrying out cooperation.
In addition, in recent years, on optical applications, the intensity of light source improves increasingly, has because this high light and the thermal conductance that produces together with it cause the problem of polaroid generation variable color.In addition, particularly for the polaroid for liquid crystal displays such as digital signage, these digital signage are contemplated in outdoor application, also require degree of polarization and its photostability, and its improvement requires high.
Prior art document
Patent documentation
Patent documentation 1: No. 3769140th, Japanese patent gazette
Patent documentation 2: Japanese Unexamined Patent Publication 2003-313451
Patent documentation 3: Japanese Patent Publication 64-5623
Patent documentation 4: No. 2004-075719, Japanese Unexamined Patent Publication
Non-patent literature
Non-patent literature 1: Machine (functional pigmented application) the 1st printing of property pigment ying can issue version, and Co., Ltd. C MC publishes, and enters Jiang Zhenghao chief editor, P98-100
Non-patent literature 2: dyestuff chemistry; Thin Tian Fengzhu; Skill report hall
Summary of the invention
The problem that invention will solve
Patent documentation 1 and Patent Document 2 discloses the patent relating to the sunproof polaroid of requirement and the dyestuff for polaroid.In the embodiment 5 of patent documentation 3, disclose two J acid aminoazo-compound diazotising obtained.
But, although disclose the such technology of patent documentation 1, patent documentation 2, do not meet the requirement in market, and although the permanance of dyestuff dyestuff disclosed in patent documentation 3 is higher, polarized light property is low.Thus, people require to develop to have good polarized light property and the polarization element also with high-durability.
The present inventor conducts in-depth research to solve above-mentioned problem, a kind of polarization element of result new discovery, this polarization element has good polarized light property and also has high-durability, this polarization element by containing polyvinyl alcohol resin or derivatives thereof and dichroic dye and the film stretched form, it is characterized in that, azo-compound represented by formula (1) of at least one of this dichroic dye or its salt.
For solving the scheme of problem
That is, the present invention relates to following content.
(1) a kind of polarization element, it is by containing polyvinyl alcohol resin or derivatives thereof and dichroic dye and the polarization element that forms of the film stretched, the azo-compound represented by formula (1) that at least one of this dichroic dye is free acid form or its salt;
(in formula, A represents the phenyl with at least 1 carboxyl alternatively base.)
(2) polaroid, the one side of its polarization element described in (1) or be two-sidedly provided with protective seam;
(3) liquid crystal indicator, it the has polarization element described in (1) or the polaroid described in (2);
(4) spreadlight lens, it the has polarization element described in (1) or the polaroid described in (2).
The effect of invention
Polarization element containing polyvinyl alcohol resin or derivatives thereof and dichroic dye of the present invention or polaroid have high-durability and good polarized light property.
Embodiment
Below, the present invention is described in detail.
The present invention relates to a kind of polarization element, it is by containing polyvinyl alcohol resin or derivatives thereof and dichroic dye and the polarization element that forms of the film stretched, it is characterized in that, the azo-compound represented by formula (1) that at least one of this dichroic dye is free acid form or its salt, the feature of this polarization element is, it has good polarized light property and also has high-durability.By making polyvinyl alcohol mesentery contain at least one of the dyestuff represented by formula (1) and stretch, forming film, above-mentioned feature can be realized thus.
(in formula, A represents the phenyl with at least 1 carboxyl alternatively base.)
Next, the concrete example of the azo-compound represented by above-mentioned formula (1) used in the present invention is enumerated below.It should be noted that, the sulfo group in formula, carboxyl and hydroxyl represent with the form of free acid.
Synthetic method
Azo-compound represented by formula (1) or its salt according to the method for making of the common azo dyes recorded in non-patent literature 2, easily can manufacture by carrying out coupling.As concrete manufacture method, such as, the amino-compound that formula (20) represents is utilized known method diazotising, N is coupled at 10 DEG C ~ 20 DEG C alkali, two (1-hydroxyl-3-sulfo group-6-naphthyl) amine of N-(trivial name: two J acid) and obtain two azo-compounds, obtains the solution of the compound containing formula (1).
(in formula, Rx or Ry represent respectively hydrogen atom, carbon number be 1 to 4 low alkyl group, carbon number be 1 to 4 lower alkoxy, hydroxyl, carboxyl, nitro or halogen atom.)
Next by this solution evaporate to dryness or filtration drying of saltouing, pulverize, obtain the compound of the formula (1) of the application of powdered.The compound of the formula (1) so obtained uses with the form of sodium salt usually, also can use with the form of lithium salts, sylvite, ammonium salt, alkylamine salt etc.
The dyestuff of formula (1) carries out the correction of tone and the raising of polarizing properties by share with other organic pigment.As the organic pigment in this case used, as long as there is the pigment of absorption characteristic and polarized light property Gao Zeke thinks any dyestuff in the wavelength region may that the absorbing wavelength region from the pigment used in the present invention is different, dichroic dye is not particularly limited, as long as hydrophilic macromolecule can be dyeed, the dichroic dyes such as azo system, anthraquinone system, quinophthalone system can be enumerated, the pigment recorded with color index can be exemplified in addition.Such as C.I. directly yellow 12, C.I. directly yellow 28, C.I. Direct Yellow 44, C.I. direct orange 26, C.I. direct orange 39, C.I. direct orange 107, C.I. directly red 2, C.I. directly red 31, C.I. directly red 79, C.I. directly red 81, C.I. directly red 247, C.I. direct green 80, C.I. direct green 59 can be enumerated; And Japanese Unexamined Patent Publication 2001-33627, Japanese Unexamined Patent Publication 2002-296417, Japanese Unexamined Patent Publication 2003-215338, WO2004/092282, Japanese Unexamined Patent Publication 2001-056412, Japanese Unexamined Patent Publication 2001-027708, Japanese Unexamined Patent Publication 11-218611, Japanese Unexamined Patent Publication 11-218610, Japanese Laid-Open Patent Publication 60-156759, organic dyestuff etc. described in non-patent literature 1.These organic dyestuff, except using with the form of free acid, can also use with the form of the salt of alkali metal salt (such as Na salt, K salt, Li salt), ammonium salt or amine.Wherein, dichroic dye is not limited thereto, and also can use known dichroic dye, but preferred azo based dye.Except these shown dichroic dyes, also can share other organic dyestuff as required.
For object polarization element, be the difference of muted color polarization element, the colored polarization element of liquid crystal projection apparatus or other colored polarization element according to it, the kind of the organic dyestuff coordinated separately is also different.Its blending ratio is not particularly limited, combined amount can be set arbitrarily according to the expectation of light source, permanance, required tone etc.
The dyestuff of formula (1) is infiltrated up in the film of polyvinyl alcohol resin or derivatives thereof.The manufacture method of the polyvinyl alcohol resin forming polarization element is not particularly limited, such as, can by vinylite saponification.As vinylite, except as except the polyvinyl acetate of leifa, can also enumerate vinyl acetate and can with the multipolymer etc. of other monomer of its copolymerization.As other monomer with vinyl acetate copolymerization, such as unsaturated carboxylic acid class, olefines, vinyl ethers or unsaturated sulfonic acid class etc. can be enumerated.The saponification degree of polyvinyl alcohol resin is usually preferably 85 % by mole ~ 100 % by mole, is more preferably more than 95 % by mole.This polyvinyl alcohol resin can be modified further, such as, also can use polyvinyl formal or Pioloform, polyvinyl acetal etc. through aldehydes modification.In addition, the degree of polymerization of polyvinyl alcohol resin is usually preferably 1,000 ~ 10,000, is more preferably 1,500 ~ 6,000.The derivant of the polyvinyl alcohol resin that can use in the present invention can enumerate the resin etc. implementing above-mentioned modification.
Film polyvinyl alcohol resin or derivatives thereof (hereinafter both being called polyvinyl alcohol resin in the lump) film forming obtained uses as base film (former anti-Off ィ Le system).The film build method of polyvinyl alcohol resin is not particularly limited, known method can be utilized to carry out film forming.In this case, polyvinyl alcohol resin film can contain glycerine, ethylene glycol, propylene glycol or low molecular poly etc. as plastifier.Plasticising dosage is preferably 5 % by weight ~ 20 % by weight, is more preferably 8 % by weight ~ 15 % by weight.The thickness of the base film formed by polyvinyl alcohol resin is not particularly limited, such as, is preferably 5 μm ~ 150 μm, is more preferably 10 μm ~ 100 μm.
First swelling operation is implemented to above-mentioned polyvinyl alcohol resin film.Swelling operation is carried out by being flooded in the solution of 20 DEG C ~ 50 DEG C by polyvinyl alcohol resin film for 30 seconds ~ 10 minutes.Solution is preferably water.When the time manufacturing polarization element will be shortened, due to also can be swelling when the dyeing process of dyestuff, thus also swelling operation can be omitted.
Dyeing process is implemented after swelling operation.Dyeing process is by making polyvinyl alcohol resin film immersion in containing the solution of dichroic dye and making dyestuff infiltrate.Solution temperature in this operation is preferably 5 DEG C ~ 60 DEG C, is more preferably 20 DEG C ~ 50 DEG C, is particularly preferably 35 DEG C ~ 50 DEG C.The dipping time in the solution can appropriateness regulate, and preferably regulates at 30 seconds ~ 20 minutes, is more preferably 1 minute ~ 10 minutes.For colouring method, be preferably immersed in this solution, but also by this solution is applied to polyvinyl alcohol resin film to carry out.
Solution containing dichroic dye can contain sodium chloride, sodium sulphate, anhydrous sodium sulfate, sodium tripolyphosphate etc. as dyeing assistant.Their content can according to depending on time of dyeing, temperature is adjusted to arbitrary concentration, be preferably 0 % by weight ~ 5 % by weight with respective content meter, be more preferably 0.1 % by weight ~ 2 % by weight.
The method of infiltrating as making dyestuff, is undertaken by being immersed in the solution containing dichroic dye, also it can be made to contain the method for dyestuff for the stage of carrying out processing and forming at the base film (former anti-) to polyvinyl alcohol resin film.
After dyeing process, matting (hereinafter referred to matting 1) can be carried out before entering ensuing operation.Matting 1 is carry out the operation of cleaning for the dye solvent being attached to polyvinyl alcohol resin film surface in dyeing process.By carrying out matting 1, dyestuff can be suppressed to transfer in the liquid next carrying out processing.Usually water is used in matting 1.
Cleaning method is preferably immersed in this solution, also can by this solution is applied to polyvinyl alcohol resin film to clean.The time of cleaning is not particularly limited, is preferably 1 second ~ 300 seconds, is more preferably 1 second ~ 60 seconds.The temperature of the solvent in matting 1 needs for the temperature of dissolving does not occur hydrophilic macromolecule.Usually cleaning treatment is carried out at 5 DEG C ~ 40 DEG C.
After dyeing process or matting 1, the operation made it containing crosslinking chemical and/or resistance to hydrated agent can be carried out.As crosslinking chemical, such as, can use the boron compounds such as boric acid, borax or ammonium borate; The polyaldehyde such as glyoxal or glutaraldehyde; The multicomponent isocyanate based compounds such as biuret form, isocyanuric acid ester type or end-sealed type; The titanium sub-group compounds etc. such as titanyl sulfate, can use diglycidyl ether of ethylene glycol, polyamideepichlorohydrin etc. in addition.As resistance to hydrated agent, succinic acid peroxide, ammonium persulfate, Calcium perchlorate, benzoin ethyl ether, ethylene glycol diglycidylether, glycerin diglycidyl ether, ammonium chloride or magnesium chloride etc. can be enumerated, preferably use boric acid.The crosslinking chemical of more than the above at least one illustrated and/or resistance to hydrated agent is used to carry out the operation made it containing crosslinking chemical and/or resistance to hydrated agent.Be preferably water as solvent now, but be not limited to water.Make it in the operation containing crosslinking chemical and/or resistance to hydrated agent, for the crosslinking chemical in solvent and/or resistance to hydrated agent containing concentration, for boric acid, be preferably 0.1 % by weight ~ 6.0 % by weight relative to the concentration of solvent, be more preferably 1.0 % by weight ~ 4.0 % by weight.Solvent temperature in this operation is preferably 5 DEG C ~ 70 DEG C, is more preferably 5 DEG C ~ 50 DEG C.For the method made containing crosslinking chemical and/or resistance to hydrated agent in polyvinyl alcohol resin film, be preferably immersed in this solution, also by the coating of this solution or polyvinyl alcohol resin film can be applied to.Processing time in this operation is preferably 30 seconds ~ 6 minutes, is more preferably 1 minute ~ 5 minutes.Wherein, make it containing crosslinking chemical and/or resistance to hydrated agent non-essential, when wanting the shortening time, when crosslinking Treatment or resistance to hydration process need not be carried out, also can omit this treatment process.
After having carried out dyeing process, matting 1 or having made it the operation containing crosslinking chemical and/or resistance to hydrated agent, carry out stretching process.Stretching process refers to the operation of polyvinyl alcohol mesentery being carried out to unilateral stretching.Drawing process can be any one of wet type pulling method or dry stretch process.
When dry stretch process, when stretching heating medium is normal temperature ~ 180 DEG C, air dielectric, be preferably stretch under the condition of normal temperature ~ 180 DEG C in the temperature of air dielectric.In addition, for humidity, preferably process in the atmosphere of 20%RH ~ 95%RH.As heating means, can enumerate such as between roller region stretch (ロ ー Le Inter ゾ ー Application extend (rollzone-drawing)) method, roller adds hot-drawing method, pressurization stretches (calendering is stretched) method, infrared heating pulling method etc., but is not limited to this drawing process.Stretching process can be 1 section of stretching, also can be stretched by the multistage of more than 2 sections and carry out.
When wet type pulling method, stretch in water, water-miscible organic solvent or its mixed solution.Stretch processing is carried out while being preferably immersed in the solution containing crosslinking chemical and/or resistance to hydrated agent.As crosslinking chemical, the boron compounds such as such as boric acid, borax or ammonium borate can be used; The polyaldehyde such as glyoxal or glutaraldehyde; The multicomponent isocyanate based compounds such as biuret form, isocyanuric acid ester type or end-sealed type; The titanium sub-group compounds etc. such as titanyl sulfate, can use diglycidyl ether of ethylene glycol, polyamideepichlorohydrin etc. in addition.As resistance to hydrated agent, succinic acid peroxide, ammonium persulfate, Calcium perchlorate, benzoin ethyl ether, ethylene glycol diglycidylether, glycerin diglycidyl ether, ammonium chloride or magnesium chloride etc. can be enumerated.Can stretch in the solution containing the crosslinking chemical more than at least one illustrated above and/or resistance to hydrated agent.Crosslinking chemical preferred boric acid.The concentration of the crosslinking chemical in stretching process and/or resistance to hydrated agent is such as preferably 0.5 % by weight ~ 15 % by weight, is more preferably 2.0 % by weight ~ 8.0 % by weight.Stretching ratio is preferably 2 ~ 8 times, is more preferably 5 ~ 7 times.For draft temperature, preferably carry out processing, being more preferably 45 DEG C ~ 58 DEG C at 40 DEG C ~ 60 DEG C.Stretching time is generally 30 seconds ~ 20 minutes, is more preferably 2 minutes ~ 5 minutes.Wet type stretching process can carry out 1 section of stretching, is also undertaken by the multistage stretching of more than 2 sections.
After carrying out stretching process, sometimes have the precipitation of crosslinking chemical and/or resistance to hydrated agent on film surface or have the attachment of foreign matter, thus can carry out the matting (hereinafter referred to matting 2) that film surface is cleaned.Scavenging period is preferably 1 second ~ 5 minutes.Cleaning method is preferably immersed in cleaning solution, also by being applied by solution or being applied to polyvinyl alcohol resin film to clean.1 section of cleaning treatment can be carried out, also can carry out the multistage process of more than 2 sections.The solution temperature of matting is not particularly limited, is generally 5 DEG C ~ 50 DEG C, is preferably 10 DEG C ~ 40 DEG C.
As solvent used in treatment process hereto, such as water can be enumerated; Dimethyl sulfoxide (DMSO); 1-METHYLPYRROLIDONE; The alcohols such as methyl alcohol, ethanol, propyl alcohol, isopropyl alcohol, glycerine, ethylene glycol, propylene glycol, diglycol, triethylene glycol, tetraethylene glycol or trimethylolpropane; The amine such as ethylenediamine or diethylene triamine equal solvent, but be not limited to these.In addition the potpourri of these solvents of more than a kind can also be used.Most preferred solvent is water.
The drying process of film is carried out after stretching process or matting 2.Dry process is undertaken by natural drying, in order to improve drying efficiency further, can utilize based on roller compression or utilize air knife or suction roll etc. carry out the moisture removing on surface and/or carry out air-supply drying.As dry treatment temperature, preferably carry out drying process at 20 DEG C ~ 100 DEG C, more preferably carry out drying process at 60 DEG C ~ 100 DEG C.The dry processing time can apply 30 seconds ~ 20 minutes, is preferably 5 minutes ~ 10 minutes.
The polyvinyl alcohol resin film polarization element utilizing above method can obtain permanance of the present invention to be improved.Even if the film of the absorption dichroic dye in polarization element is not polyvinyl alcohol resin, but the film obtained by amylose system resin, starch-series resin, cellulose-based resin, polyacrylate system resin etc., also can by containing dichroic dye, carry out stretching, carry out shearing orientation etc. and make hydrophilic resin carry out orientation to produce same polarization element, but the polarization element film formed by polyvinyl alcohol resin film is the most suitable.
By obtained polarization element one side or two-sided protective clear layer is set, obtained polaroid.Polymkeric substance can be utilized to make coating layer when protective clear layer is set or make the laminate layers of film.As forming the transparent polymer of protective clear layer or film, preferred mechanical intensity is high, the transparent polymer of good thermal stability or film.Material as protective clear layer use can enumerate acetyl cellulose resins or its film of such as triacetyl cellulose or diacetyl cellulose and so on; Acrylic resin or its film; Corvic or its film; Nylon resin or its film; Vibrin or its film; Polyarylate resin or its film; Norborene and so on take cyclic olefin as cyclic polyolefin resin or its film of monomer; Tygon, polypropylene; Ring system or there is polyolefin or its multipolymer of norborene skeleton; Main chain or side chain are resin or polymkeric substance or its film etc. of acid imide and/or acid amides.In addition, as protective clear layer, the resin with liquid crystal liquid crystal property or its film also can be set.The thickness of diaphragm is such as 0.5 μm ~ about 200 μm.By by resin of the same race or not of the same race wherein or film at one side or two-sidedly arrange more than 1 layer, make polaroid.
Above, in order to protective clear layer and polarization element be fitted, cementing agent (then drug) is needed.Be not particularly limited as cementing agent, preferably polyethylene alcohol system cementing agent.As polyethenol series cementing agent, such as GohsenolNH-26 (synthesis society of Japan manufactures), ExcevalRS-2117 (manufacture of KURARAY society) etc. can be enumerated, but be not limited to this.Crosslinking chemical and/or resistance to hydrated agent can be added in a binder.In polyethenol series cementing agent, use maleic anhydride-isobutylene copolymers, the cementing agent being mixed with crosslinking chemical can be used as required.As maleic anhydride-isobutylene copolymers, such as Isobam#18 (manufacture of KURARAY society), Isobam#04 (manufacture of KURARAY society), ammonia modification Isobam#104 (manufacture of KURARAY society), ammonia modification Isobam#110 (manufacture of KURARAY society), imidizate Isobam#304 (manufacture of KURARAY society), imidizate Isobam#310 (manufacture of KURARAY society) etc. can be enumerated.Water-soluble polynary epoxy compound can be used in crosslinking chemical now.As water-soluble polynary epoxy compound, such as DenacolEX-521 (manufacture of NagaseChemteX society), Tetrad-C (テ ト ラ ッ ト-C, Mitsui gas chemistry society manufactures) etc. can be enumerated.In addition, as the cementing agent beyond polyvinyl alcohol resin, the known cementing agent of carbamate system, acrylic acid series, epoxy and so on can also be used.In addition, for improving the cohesive force of cementing agent or improving the object of water tolerance, also can contain the additives such as zinc compound, chloride, iodide with the concentration of 0.1 % by weight ~ 10 about % by weight simultaneously.Additive is not also limited.After utilizing cementing agent laminating protective clear layer, by carrying out drying or thermal treatment at suitable temperature, obtain polaroid.
When the polaroid obtained according to circumstances such as conforms to the display device such as liquid crystal, organic electroluminescent, also can arrange for the layer or the film that improve angle of visibility, improve the various functional layer of contrast, there is brightness raising property as the protective seam of non-exposed surface or the surface of film afterwards.In order to make polaroid and these films or display device fit, preferably use bonding agent (adhesion drug).
This polaroid can opposite side surface, namely in the exposed surface of protective seam or film, there is anti-reflecting layer or the known various functional layer such as antiglare layer, hard conating.Have various functional layer, preferred coating process to make this, also can fitting by cementing agent or bonding agent, this has the film of function.In addition, various functional layer can be layer for control phase difference or film.
Utilize said method, polarization element of the present invention and polaroid can be obtained.The display screen employing polarization element of the present invention or polaroid be reliability high, there is high-contrast and there is the display screen of high color reprodubility for a long time.
The polarization element of the present invention so obtained arranges protective seam or functional layer and support etc. as required with the form of the polaroid with diaphragm, is used to liquid crystal projection apparatus, counter, clock and watch, notebook computer, word processor, liquid crystal TV set, spreadlight lens, polaroid glasses, auto navigation and indoor and outdoor tester or display etc.
Embodiment
Illustrate in greater detail the present invention below by embodiment, but the present invention is not limited thereto.It should be noted that, the evaluation of the transmitance shown in embodiment, degree of polarization is carried out as follows.In addition, hereinafter " part " refers to " weight portion ".
Each transmitance uses spectrophotometer (society of Hitachi manufactures " U-4100 ") to measure.
When using spectrophotometer (society of Hitachi manufactures " U-4100 ") to measure transmitance, the emitting side of light arrange be 43% based on JIS-Z8701 (illuminant-C 2 ° of visuals field) depending on the transmitance after sensitivity correction and degree of polarization be 99.99% iodine system polaroid (Polatechno society manufactures SKN-18043P), be incident to mensuration sample to enable absolute polarized light.The protective seam of iodine system polaroid is now the triacetyl cellulose without ultraviolet absorption ability.
To the incident definitely polarized light of polaroid of the present invention, the direction of vibration of this absolute polarized light orthogonal with the absorption direction of principal axis of polaroid of the present invention (the absorption axle of this absolute polarizer is parallel with the absorption axle of polaroid of the present invention) is measured, obtained absolute parallel transmitance is set to Ky; The direction of vibration of this absolute polarized light parallel with the absorption direction of principal axis of polaroid of the present invention (the absorption axle of this absolute polarizer is orthogonal with the absorption axle of polaroid of the present invention) is measured, obtained absolute orthogonal transmitance is set to Kz.
By absolute parallel transmitance Ky and absolute orthogonal transmitance Kz, obtain singleton transmittance Ts by following calculating formula (i).
Ts=(Ky+Kz)/2 formula (i)
By absolute parallel transmitance Ky and absolute orthogonal transmitance Kz, obtain degree of polarization ρ by following calculating formula (ii).
ρ=(Ky-Kz)/(Ky+Kz) formula (ii)
Embodiment A-1
The making > of < dyestuff
PABA is dissolved in 145 parts, water, joins in 140 parts, the water containing 35 % by weight hydrochloric acid 26 parts, add sodium nitrite 6.9 parts at 15 DEG C ~ 20 DEG C and carry out 1 hour diazotising.Next joined by N, in the aqueous solution that two (1-hydroxyl-3-sulfo group-6-naphthyl) amine of N-(trivial name: two J acid) 31.5 parts, 125 parts, water, 11 parts, sodium carbonate are formed, add soda ash solution further, keep pH8.5 ~ 9.5 simultaneously, utilize within 3 hours, carry out coupling at 20 DEG C, till confirming less than two azo-compounds in spot test, obtain two azo-compounds.Add in obtained solution into Zan qi salt (サ ヌ キ salt (Sanukisalt)), carry out saltouing, filtering, at 60 DEG C of evaporates to dryness, make the dyestuff represented by formula (4) of the application.
The making > of < polarization element
Be more than 99% by saponification degree, thickness is that the polyvinyl alcohol resin film (KURARAY society manufactures VF series) of 75 μm floods 2 minutes in the warm water of 40 DEG C, carry out swelling treatment.By the film immersion after swelling treatment in 45 DEG C of aqueous solution of the dyestuff 0.05 % by weight represented by the formula (4) containing the application, sodium tripolyphosphate 0.1 % by weight, carry out the absorption of dyestuff.To the film water cleaning of dyestuff be adsorbed, and after cleaning, utilize 40 DEG C of aqueous solution of the boric acid containing 2 % by weight to carry out boric acid process in 1 minute.The film obtained carrying out boric acid process stretches with 5.0 times, carries out process in 5 minutes in 55 DEG C of aqueous solution containing boric acid 3.0 % by weight simultaneously.This film carrying out boric acid process and obtain utilizes the water of 30 DEG C to carry out cleaning in 15 seconds when keeping tense situation.Carrying out dry process in 9 minutes at 70 DEG C immediately by processing the film obtained, making the polarization element that thickness is 28 μm, as mensuration sample.
Embodiment A-2
In embodiment A-1,4-amino-benzoic acid is replaced with 3-amino-4-methyl benzoic acid 16.2 parts, make the dyestuff represented by the application's formula (10), similarly make polarization element in addition, as mensuration sample.
Embodiment A-3
In embodiment A-1,4-amino-benzoic acid is replaced with 17.9 parts, 3-amino-4-methoxyl benzoic acid, make the dyestuff represented by the application's formula (16), similarly make polarization element in addition, as mensuration sample.
Embodiment A-4
In embodiment A-1,4-amino-benzoic acid is replaced with 3-methoxyl-4-amino-5-chlorobenzoic acid 19.8 weight portion, make the dyestuff represented by the application's formula (19), similarly make polarization element in addition, as mensuration sample.
Comparative examples A-1
Dyestuff represented by the application's formula (2) used in embodiment A-1 is replaced with two azo dyess of the C.I.Direct81 shown in non-patent literature 1, similarly make polarization element in addition, as mensuration sample.
Comparative examples A-2
Dyestuff represented by the application's formula (2) used in embodiment A-1 is replaced with two azo dyess shown in embodiment 1 of Japanese Patent Publication 7-92531, similarly make polarization element in addition, as mensuration sample.
Comparative examples A-3
Dyestuff represented by the application's formula (2) used in embodiment A-1 is replaced with two azo dyess shown in embodiment No.16 of Japanese Laid-Open Patent Publication 63-189803, similarly make polarization element in addition, as mensuration sample.
Comparative examples A-4
Dyestuff represented by the application's formula (2) used in embodiment A-1 is replaced with the dyestuff shown in compound example numbering 8 of No. 2985408, Jap.P., similarly make polarization element in addition, as mensuration sample.
Comparative examples A-5
In embodiment A-1,3-amino-4-methoxyl benzoic acid is replaced with 3-methoxyl-4-aminobenzenesulfonic acid, make two azo dyess with two J acid represented by following formula (21), similarly make polarization element in addition, as mensuration sample.
For obtained polarization element, use spectrophotometer U-4100 at 380nm ~ 780nm with 1nm measuring space Ky and Kz.In the degree of polarization ρ calculated by obtained Ky, Kz, the wavelength with most high-polarization is set to λ max.By when making the simple substance transmitance Ts at λ max place be about 40.5% ~ 41.5%, the degree of polarization ρ max at λ max place is shown in table 1.
[table 1]
| λmax | Ts max | ρ max | |
| Embodiment A-1 | 557 | 41.08 | 99.94 |
| Embodiment A-2 | 563 | 40.91 | 99.90 |
| Embodiment A-3 | 568 | 41.12 | 99.85 |
| Embodiment A-4 | 565 | 40.95 | 99.88 |
| Comparative examples A-1 | 519 | 41.13 | 99.95 |
| Comparative examples A-2 | 589 | 41.41 | 94.82 |
| Comparative examples A-3 | 578 | 40.81 | 99.77 |
| Comparative examples A-4 | 620 | 40.60 | 94.68 |
| Comparative examples A-5 | 552 | 41.48 | 93.65 |
Compare the degree of polarization ρ max at the λ max place of obtained polarization element, result is known: embodiment A-1 ~ A-4 has equal above degree of polarization compared with Comparative examples A-1 ~ A-5.Particularly, if compare with the Comparative examples A-5 with two same J acid, the known polarization element obtaining degree of polarization high about 6% ~ 7%.
Embodiment B-3
< light fastness test >
Use polyethenol series cementing agent, the tri acetyl cellulose membrane (Fujiphoto society manufactures TD-80U, hereinafter referred to as TAC) being 80 μm by the polarization element obtained in embodiment A-3 and the thickness having carried out alkali treatment carries out lamination according to the formation of polarization element/tack coat/TAC, and lamination obtains polaroid.
Obtained polaroid is cut into 40mm × 40mm, fit in the transparency glass plate of 1mm by bonding agent PTR-3000 (Japanese chemical drug society manufactures) according to the formation of polarization element/tack coat/TAC/ bonding coat/transparency glass plate, make light fastness test and evaluate sample.
In light fastness test, (SugaSeikiCo., Ltd. manufacture to utilize xenon arc testing machine; SX-75), carry out the light exposure experiment of 70 hours from polarization element side under the condition of 100W, blackboard temperature 89 DEG C, ambient humidity 30%, confirm that the change of Ky, Kz of front and back is penetrated in illumination, and calculate the contrast C R calculated by following formula (iii), compare the permanance for light.
CR=Ky/Kz formula (iii)
Comparative example B-1
The polarization element A-3 used in Embodiment B-3 is replaced with the polarization element obtained in comparative example B-1, similarly carries out the endurancing for light in addition.
Comparative example B-2
The polarization element A-3 used in Embodiment B-3 is replaced with the polarization element obtained in comparative example B-2, similarly carries out the endurancing for light in addition.
Comparative example B-3
The polarization element A-3 used in Embodiment B-3 is replaced with the polarization element obtained in comparative example B-3, similarly carries out the endurancing for light in addition.
Ky, Kz, the CR at the λ max place before the long duration test of the polaroid obtained in Embodiment B-1, comparative example B-1 ~ comparative example B-3 and after light fastness test are shown in table 2.
[table 2]
As shown in Table 2, the dyestuff of the application is compared with comparative example B-1 ~ comparative example B-3, and the photostability for light improves tremendously, suppressed more than 2 times of the reduction of contrast.
From table 1 and table 2: about the dyestuff of the application, polarity is high as shown in Table 1, the polarization element with the equal above degree of polarization with the polaroid dyestuff used in the past can be obtained; In addition as shown in Table 2, obtain the contrast being not less than existing polaroid reduce few, for the high polaroid of the photostability of light.Also known thus, the polaroid of the present embodiment has high polarizing coefficient and high temperature and the long-time photostability exposed is also excellent.By polarization element of the present invention or polaroid are used in liquid crystal projection apparatus, counter, clock and watch, notebook computer, word processor, liquid crystal TV set, spreadlight lens, polaroid glasses, auto navigation and indoor and outdoor tester or display etc., even if do not use the dyestuff belonging to particular chemicals of dianisidine and so on can obtain having the liquid crystal display and lens etc. of high stability yet.
Claims (4)
1. a polarization element, it is by containing polyvinyl alcohol resin or derivatives thereof and dichroic dye and the polarization element that forms of the film stretched, it is characterized in that, the azo-compound represented by formula (1) that at least one of this dichroic dye is free acid form or its salt
In formula, A represents the phenyl with at least 1 carboxyl alternatively base.
2. a polaroid, its one side at polarization element according to claim 1 or be two-sidedly provided with protective seam.
3. a liquid crystal indicator, it has polarization element according to claim 1 or polaroid according to claim 2.
4. a spreadlight lens, it has polarization element according to claim 1 or polaroid according to claim 2.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2012-041024 | 2012-02-28 | ||
| JP2012041024 | 2012-02-28 | ||
| PCT/JP2013/053921 WO2013129170A1 (en) | 2012-02-28 | 2013-02-19 | Dye-based polarizing element, and polarizing plate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104160305A CN104160305A (en) | 2014-11-19 |
| CN104160305B true CN104160305B (en) | 2016-04-13 |
Family
ID=49082370
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201380009089.1A Active CN104160305B (en) | 2012-02-28 | 2013-02-19 | Dyestuff system polarization element and polaroid |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JP5989082B2 (en) |
| KR (1) | KR101949190B1 (en) |
| CN (1) | CN104160305B (en) |
| HK (1) | HK1202930A1 (en) |
| TW (1) | TWI569047B (en) |
| WO (1) | WO2013129170A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105143935B (en) * | 2013-06-03 | 2017-12-08 | 日本化药株式会社 | Display device polarizer or polarizer with blue light emitting device |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB662253A (en) * | 1948-07-16 | 1951-12-05 | Ciba Ltd | Manufacture of new tetrakisazo-dyestuffs |
| US2583519A (en) * | 1944-12-19 | 1952-01-22 | Ciba Ltd | Azo-dyestuffs |
| GB901748A (en) * | 1957-11-06 | 1962-07-25 | Durand & Huguenin Ag | Metallisable azo-dyestuffs and process for their manufacture |
| US4859039A (en) * | 1984-11-16 | 1989-08-22 | Sumitomo Chemical Company, Limited | Light-polarizing film |
| CN101398501A (en) * | 2007-09-28 | 2009-04-01 | 日东电工株式会社 | Polarizing plate, method for producing same, optical film, and image display device |
| CN101836140A (en) * | 2007-10-24 | 2010-09-15 | 日东电工株式会社 | Polarizing plate, optical film and image display device |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH078376B2 (en) | 1987-06-26 | 1995-02-01 | 株式会社神戸製鋼所 | Extrusion press shearing device |
| JPH0718192A (en) * | 1993-07-02 | 1995-01-20 | Nippon Kayaku Co Ltd | Copper-containing azo compound and method for dyeing using the same |
| JP3680323B2 (en) * | 1993-10-14 | 2005-08-10 | 住友化学株式会社 | Dye-type polarizing film |
| JP3769140B2 (en) | 1998-03-20 | 2006-04-19 | 住友化学株式会社 | Polarized film |
| JP2003313451A (en) | 2002-04-26 | 2003-11-06 | Sumitomo Chem Co Ltd | Azo compound or its salt, and their application to polarizing film |
| JP4270486B2 (en) | 2002-08-09 | 2009-06-03 | 日本化薬株式会社 | Trisazo compound, water-based ink composition, and colored body |
| JP4828932B2 (en) * | 2005-12-22 | 2011-11-30 | 伊藤光学工業株式会社 | Mold and method for polarizing plastic lens |
| CN102066497B (en) * | 2008-06-17 | 2014-02-26 | 日本化药株式会社 | Azo compound and salts thereof, as well as dye-based polarization films and polarizing plates comprising the same |
| WO2012137736A1 (en) * | 2011-04-07 | 2012-10-11 | 日本化薬株式会社 | Water-soluble azo dye, dye composition containing same, and dyeing method using same |
-
2013
- 2013-02-19 KR KR1020147020318A patent/KR101949190B1/en active IP Right Grant
- 2013-02-19 CN CN201380009089.1A patent/CN104160305B/en active Active
- 2013-02-19 WO PCT/JP2013/053921 patent/WO2013129170A1/en active Application Filing
- 2013-02-19 JP JP2014502139A patent/JP5989082B2/en active Active
- 2013-02-26 TW TW102106784A patent/TWI569047B/en active
-
2015
- 2015-04-08 HK HK15103420.7A patent/HK1202930A1/en not_active IP Right Cessation
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2583519A (en) * | 1944-12-19 | 1952-01-22 | Ciba Ltd | Azo-dyestuffs |
| GB662253A (en) * | 1948-07-16 | 1951-12-05 | Ciba Ltd | Manufacture of new tetrakisazo-dyestuffs |
| GB901748A (en) * | 1957-11-06 | 1962-07-25 | Durand & Huguenin Ag | Metallisable azo-dyestuffs and process for their manufacture |
| US4859039A (en) * | 1984-11-16 | 1989-08-22 | Sumitomo Chemical Company, Limited | Light-polarizing film |
| CN101398501A (en) * | 2007-09-28 | 2009-04-01 | 日东电工株式会社 | Polarizing plate, method for producing same, optical film, and image display device |
| CN101836140A (en) * | 2007-10-24 | 2010-09-15 | 日东电工株式会社 | Polarizing plate, optical film and image display device |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2013129170A1 (en) | 2013-09-06 |
| JP5989082B2 (en) | 2016-09-07 |
| TW201344257A (en) | 2013-11-01 |
| JPWO2013129170A1 (en) | 2015-07-30 |
| KR20140138603A (en) | 2014-12-04 |
| HK1202930A1 (en) | 2015-10-09 |
| TWI569047B (en) | 2017-02-01 |
| CN104160305A (en) | 2014-11-19 |
| KR101949190B1 (en) | 2019-02-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104115042B (en) | Dyestuff system polarization element and polaroid | |
| CN103347959B (en) | Azo-compound, dye type polarizing film and polarization plates | |
| CN105190378A (en) | Achromatic dye-based highly-transmissive polarization element, and polarization plate | |
| TWI518139B (en) | Dye-based polarizer and polarizing plate | |
| CN105247392A (en) | Achromatic dye-based polarization element, and polarization plate | |
| WO2013154139A1 (en) | Polarizing element, and polarizer | |
| CN105190377A (en) | Achromatic polarization element, and polarization plate | |
| CN103502852B (en) | Dyestuff system polarization element and polaroid | |
| TW202014392A (en) | Polarization element and polarizing plate and optical member using the same | |
| JP6111193B2 (en) | Dye-type polarizing element and polarizing plate | |
| CN104160305B (en) | Dyestuff system polarization element and polaroid | |
| CN104105988B (en) | Dyestuff is polarization element and polarizer | |
| CN103620453A (en) | Polarizing element and polarizing plate |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| REG | Reference to a national code |
Ref country code: HK Ref legal event code: DE Ref document number: 1202930 Country of ref document: HK |
|
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| REG | Reference to a national code |
Ref country code: HK Ref legal event code: GR Ref document number: 1202930 Country of ref document: HK |