CN100471915C - 多偶氮化合物及含有所述化合物的偏振膜 - Google Patents
多偶氮化合物及含有所述化合物的偏振膜 Download PDFInfo
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- CN100471915C CN100471915C CNB200410092555XA CN200410092555A CN100471915C CN 100471915 C CN100471915 C CN 100471915C CN B200410092555X A CNB200410092555X A CN B200410092555XA CN 200410092555 A CN200410092555 A CN 200410092555A CN 100471915 C CN100471915 C CN 100471915C
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- naphthyl
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 58
- -1 Poly-azo compound Chemical class 0.000 title claims description 34
- 230000010287 polarization Effects 0.000 title description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052802 copper Inorganic materials 0.000 claims abstract description 8
- 239000010949 copper Substances 0.000 claims abstract description 8
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 239000011248 coating agent Substances 0.000 claims description 65
- 238000000576 coating method Methods 0.000 claims description 65
- 239000000975 dye Substances 0.000 claims description 33
- 239000011159 matrix material Substances 0.000 claims description 18
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 12
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 229920005989 resin Polymers 0.000 claims description 8
- 239000011347 resin Substances 0.000 claims description 8
- 239000004973 liquid crystal related substance Substances 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 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 claims description 3
- 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 claims description 3
- 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 claims description 3
- 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 claims description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract description 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract description 4
- 229910052742 iron Inorganic materials 0.000 abstract description 4
- 229910052759 nickel Inorganic materials 0.000 abstract description 4
- 229910052725 zinc Inorganic materials 0.000 abstract description 4
- 239000011701 zinc Substances 0.000 abstract description 4
- 125000003277 amino group Chemical group 0.000 abstract 1
- 239000012528 membrane Substances 0.000 abstract 1
- 125000000542 sulfonic acid group Chemical group 0.000 abstract 1
- 238000000034 method Methods 0.000 description 13
- 230000000176 photostabilization Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 4
- 239000004327 boric acid Substances 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
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- 235000010288 sodium nitrite Nutrition 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 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
- 238000002835 absorbance Methods 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 150000002169 ethanolamines Chemical class 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 238000009434 installation Methods 0.000 description 2
- 229910003002 lithium salt Inorganic materials 0.000 description 2
- 159000000002 lithium salts Chemical class 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 150000004291 polyenes Chemical class 0.000 description 2
- 229920002689 polyvinyl acetate Polymers 0.000 description 2
- 239000011118 polyvinyl acetate Substances 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 208000005156 Dehydration Diseases 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 229920002978 Vinylon Polymers 0.000 description 1
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229920006317 cationic polymer Polymers 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
- 229940005991 chloric acid Drugs 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- NWFNSTOSIVLCJA-UHFFFAOYSA-L copper;diacetate;hydrate Chemical compound O.[Cu+2].CC([O-])=O.CC([O-])=O NWFNSTOSIVLCJA-UHFFFAOYSA-L 0.000 description 1
- UGWKCNDTYUOTQZ-UHFFFAOYSA-N copper;sulfuric acid Chemical compound [Cu].OS(O)(=O)=O UGWKCNDTYUOTQZ-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- HQRPHMAXFVUBJX-UHFFFAOYSA-M lithium;hydrogen carbonate Chemical compound [Li+].OC([O-])=O HQRPHMAXFVUBJX-UHFFFAOYSA-M 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000010129 solution processing Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/36—Trisazo dyes of the type
- C09B35/362—D is benzene
-
- 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
-
- 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
- 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
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- 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
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- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
- C09K2323/03—Viewing layer characterised by chemical composition
- C09K2323/031—Polarizer or dye
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- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F21—LIGHTING
- F21V—FUNCTIONAL FEATURES OR DETAILS OF LIGHTING DEVICES OR SYSTEMS THEREOF; STRUCTURAL COMBINATIONS OF LIGHTING DEVICES WITH OTHER ARTICLES, NOT OTHERWISE PROVIDED FOR
- F21V9/00—Elements for modifying spectral properties, polarisation or intensity of the light emitted, e.g. filters
- F21V9/14—Elements for modifying spectral properties, polarisation or intensity of the light emitted, e.g. filters for producing polarised light
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- General Physics & Mathematics (AREA)
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Abstract
多偶氮化合物,其选自式(I)化合物和式(II)化合物,(其中,Me代表铜、镍、锌或者铁,A代表含有1-3个磺酸基,并进一步任选含有烷基或者烷氧基的萘基,R1和R2各自独立地代表氢原子、烷基或者烷氧基,和R3代表氨基或者羟基)。
Description
技术领域
本发明涉及一种多偶氮化合物,及含有所述化合物的偏振膜。
背景技术
近来,存在进一步提高偏振膜的偏振度的需求.此外,装配在汽车上如汽车导航和相似装置的显示器,在太阳光的辐射的环境中使用,并且液晶显示器如液晶投影仪、投影电视及相似装置在大量的光的辐射环境中使用,因此,对于这些应用来说,需要一种即使长期在高温环境中,在大量光的辐射下,显示出极少偏振膜吸光度降低,也就是说,具有极好的耐光性的偏振膜。
作为偏振膜,已知的有在偏振膜基质中含有覆盖所需波长的染料作为偏振元件的膜,如通过拉伸定向的基于聚乙烯醇的膜,或者通过聚氯乙烯膜脱氢氯酸或者聚乙烯醇膜脱水等方法定向得到聚烯的基于聚烯的膜。
作为偏振膜的特定的偏振元件,已知的是含有下式(B)化合物作为有效成分的染料,然而,含有上述染料的偏振膜的偏振度是98%,并且耐光性不足(JP-A No.5-295281,实施例63).
发明内容
本发明的一个目的是提供一种用作具有极好偏振度的偏振膜的染料的多偶氮化合物,并且该化合物进一步赋予偏振膜极好的耐光性。
也就是说,本发明提供以下[1]-[8]。
[1]多偶氮化合物,选自式(I)化合物和式(II)化合物,
(其中,Me代表铜、镍、锌或者铁,A代表含有1-3个磺酸基的萘基,进一步任选含有烷基或者烷氧基,R1和R2各自独立地代表氢原子、烷基或者烷氧基,和R3代表氨基或者羟基)。
[2]根据[1]所述的多偶氮化合物,其中R1代表氢原子、甲基或者甲氧基。
[3]根据[1]所述的多偶氮化合物,其中R2代表氢原子、甲基或者甲氧基。
[4]偏振膜,其包含用于偏振膜的含有根据[1]-[3]任一项的多偶氮化合物的染料,和偏振膜基质.
[5]根据[4]所述的偏振膜,其中用于偏振膜的染料还进一步含有不同于多偶氮化合物的有机染料。
[6]根据[5]的偏振膜,其中所述有机染料是选自由以下颜色索引属名代表的有机染料的至少一种:
C.I.直接黄12,
C.I.直接黄28,
C.I.直接黄44,
C.I.直接橙26,
C.I.直接橙39,
C.I.直接橙107,
C.I.直接红2,
C.I.直接红31,
C.I.直接红79,
C.I.直接红81,
C.I.直接红117,
C.I.直接红247。
[7]根据[4]-[6]任一项的偏振膜,其中偏振膜基质是由聚乙烯醇树脂形成的基质。
[8]含有根据[7]的偏振膜的液晶显示器.
具体实施方式
本发明的多偶氮化合物选自式(I)化合物和式(II)化合物的至少一种。
此处,本发明的多偶氮化合物包括多偶氮化合物本身及其盐。
在上式中,Me代表选自铜、镍、锌和铁的过渡金属,A代表含有1-3个磺酸基,并进一步任选含有烷基或者烷氧基的萘基,R1和R2各自独立地代表氢原子、烷基或者烷氧基,和R3代表氨基或者羟基。
作为本发明的多偶氮化合物(此后,在某些情况下通称为本发明化合物),优选式(I)的化合物,因为其能赋予偏振膜极好的耐光性。
在(I)和式(II)中,Me代表选自铜、镍、锌和铁的过渡金属,其中优选的是铜。
A代表含有1-3个磺酸基,并进一步任选含有烷基或者烷氧基的萘基。
此处,作为烷基,可列出例如,甲基、乙基、丙基等,其中优选的是甲基。作为烷氧基,可列出例如,甲氧基、乙氧基、丙氧基等,其中优选的是甲氧基。
可列作A的是,例如,含有一个磺酸基的萘基如5-磺基-2-萘基、6-磺基-2-萘基、7-磺基-2-萘基、8-磺基-2-萘基、4-磺基-1-萘基、5-磺基-1-萘基、6-磺基-1-萘基、7-磺基-1-萘基等;具有两个磺酸基的萘基如1,5-磺基-2-萘基、6,8-磺基-2-萘基、4,8-磺基-2-萘基、5,7-磺基-2-萘基、3,6-磺基-2-萘基、3,6-磺基-1-萘基、4,6-磺基-1-萘基等;1,5,7-磺基-2-萘基、3,6,8-磺基-2-萘基、4,6,8-磺基-2-萘基等。
从染色的角度,优选A是含有2-3个磺酸基的萘基,特别优选的是1,5-磺基-2-萘基、6,8-磺基-2-萘基、4,8-磺基-2-萘基、5,7-磺基-2-萘基和3,6-磺基-2-萘基。
R1和R2各自独立地代表氢原子、烷基或者烷氧基。作为烷基和烷氧基,列出与上文描述的相同的基团.
R1优选代表氢原子、甲基或甲氧基,R2优选代表氢原子、甲基或甲氧基。
R3代表氨基或者羟基.R3的键合位置是苯甲酰氨基的邻位或者对位,优选在苯甲酰氨基的对位。
作为制备本化合物的方法,在此例举下述及相似的方法。
首先,式(III)的双偶氮化合物
(其中,A、R1和R2具有与上文描述的相同的基团)在酸性含水介质中,在0-40℃下与亚硝酸钠反应,进行重氮化作用。
所得到的重氮化合物可与式(IV)的化合物在0-40℃、pH值6-11的条件下在含水介质中反应,以得到本发明的式(II)化合物。
(其中,R3具有与上文中描述的相同的基团.)
作为本发明的式(II)化合物的钠盐,例举下述的(II-1)-(II-7)。
其次,作为制备本发明式(I)化合物的方法,例如例举这样的方法,其中式(I)中的Me是铜、铜盐如硫酸铜、氯化铜、醋酸铜等时,优选硫酸铜加入含有上述式(II)化合物的水溶液中,并将混合物加热到70-100℃,或者例举其它的方法.向铜盐可以根据需要进一步加入,锂盐如碳酸锂、碳酸氢锂等,钠盐如碳酸钠、碳酸氢钠等,钾盐如碳酸钾、碳酸氢钾等,胺如氨、单乙醇胺、二乙醇胺、单丙醇胺、嘧啶等。
当式(I)化合物的Me是铜,并且是钠盐时,可例举(I-1)-(I-7)
作为本化合物,可列举碱金属盐如锂盐、钠盐、钾盐等;有机胺盐如乙醇胺盐、烷基胺盐等;铵盐基等。其中,优选的是钠盐,因为其易于包含在偏振膜基质中。
本化合物通常产生具有在约550-680nm波长下为约90%或更高的极好偏振度的偏振膜。
本发明的偏振膜是包含用于含有本发明化合物的偏振膜的染料和偏振膜基质的偏振膜.所述用于偏振膜的染料可以由本发明化合物单独组成,但是,其含有本发明化合物和其它有机染料以便即使不在550-680nm波长范围内也能提高偏振性能。此处,所述的有机染料通常是不同于本发明化合物的高二向色性的染料,优选具有极好耐光性的染料。
作为具体的有机染料,例举由下述颜色索引属名代表的染料。所述有机染料可单独或者作为两种或更多种的混合物使用。
C.I.直接黄12,
C.I.直接黄28,
C.I.直接黄44,
C.I.直接橙26,
C.I.直接橙39,
C.I.直接橙107,
C.I.直接红2,
C.I.直接红31,
C.I.直接红79,
C.I.直接红81,
C.I.直接红117,
C.I.直接红247。
作为偏振膜基质,可提及例如,由基于聚乙烯醇的树脂、聚醋酸乙烯酯树脂、乙烯/醋酸乙烯酯(EVA)树脂、聚酰胺树脂、聚酯树脂等形成的基质.此处,基于聚乙烯醇的树脂包括作为聚乙酸乙烯酯部分或完全皂化的物质的聚乙烯醇;乙酸乙烯酯和其它可共聚单体(例如,烯烃如乙烯和丙稀、不饱和羧酸如丁烯酸、丙烯酸、甲基丙烯酸、马来酸等,不饱和磺酸、乙烯醚等)的共聚物的皂化物,例如皂化EVA树脂等;通过用醛改性聚乙烯醇获得的聚乙烯缩甲醛和聚乙烯缩乙醛,等等。作为偏振膜基质,从染料的吸收性能和定向性能来说,适合使用由基于聚乙烯醇的树脂制成的膜,特别是聚乙烯醇膜本身。
作为制备偏振膜的方法,例举以下方法。首先,将用于偏振膜的染料以约0.0001-10重量%的浓度溶解在水中以制备染料浴。如果需要,可以使用染料助剂,例如在染料浴中使用0.1-10重量%的芒硝的方法是适合的。
将偏振膜基质浸入制备的染料浴中,并进行染色。优选的染色温度是40-80℃。染料的定向通过在染色之前拉伸偏振膜基质或者染色的偏振膜基质来进行.作为拉伸方法,例如可以采用湿法、干法等。
可进行后处理如硼酸处理等以提高偏振膜的光束透射率、偏振度和光耐性。虽然可根据所采用的偏振膜基质和染料的种类而变化,但所述的硼酸处理在30-80℃范围内,优选50-80℃,利用1-15重量%、优选5-10%重量的硼酸水溶液来进行。此外,如果需要,可联合采用固定处理和含有阳离子聚合物的水溶液处理。
本发明的偏振膜含有用于含有多偶氮化合物或其盐的偏振膜的染料,和偏振膜基质,本发明的偏振膜具有极好的耐光性,即使长期在高温环境中,在大量光的辐射下,偏振膜的吸光度也并不降低。本发明的偏振膜至少在550-680nm范围内显示出极好的偏振吸光度。
由于其极好的性能,本发明的偏振膜能适用于大量光的液晶显示器,例如汽车导航、液晶投影仪、投影电视等。
实施例
本发明将基于实施例进一步的详细说明,但无需说明的是,本发明的范围不受实施例的任何限制.除非另外说明,实施例和对比实施例中的%和份数指的是重量百分数和重量份数。
实施例1
(本发明化合物的制备实施例)
向1500份水中加入170份式(III-1)的双偶氮化合物和30份亚硝酸钠,
此后,在20-30℃下向其中加入120份35%的盐酸,并搅拌混合物2小时,导致重氮化。过量的亚硝酸钠通过加入氨基磺酸除去,以得到双偶氮液体。
此后,将上述双偶氮液体在1个小时的时间内加入到含有式(IV-1)化合物的液体中,
并通过加入碳酸钠水溶液保持pH值为7。添加完毕后,再搅拌混合物1小时,以得到通式(II-1)的多偶氮化合物。在含水介质中,该双偶氮化合物的λmax为565nm。
将25份式(II-1)的化合物加入到500份水中,并向其中加入6份无水硫酸铜和8份单乙醇胺,加热混合物到95℃反应12小时。此后,将混合物冷却到30℃,然后加入35%的盐酸以控制pH值到7,此后,利用氯化钠盐析,并过滤沉淀的晶体,得到式(I-1)的多偶氮化合物。在含水介质中,该双偶氮化合物的λmax为598nm。
(偏振膜的制备实施例)
将厚度为75微米的聚乙烯醇膜[Kuraray Vinylon # 7500,由Kuraray Co.,Ltd.生产]沿径向轴拉伸五倍,得到偏振膜基质。在保持其拉紧状态下,将该聚乙烯醇膜浸入70℃水溶液中,该溶液含有0.025%由上述(本发明化合物的制备实施例)得到的多偶氮化合物(1)和0.2%的芒硝(染料助剂)。此后,将其浸入78℃的7.5%的硼酸水溶液中5分钟,此后,取出并用20℃的水洗涤20秒,在50℃下干燥以得到偏振膜.所得到的偏振膜的λmax(沿拉伸方向透射的波长是最小的,也适用于下文的描述)是610nm.测量该偏振膜在610nm处的偏振度,发现43%单体透射率(single body transmittance)下的偏振度是99.8%。
当所得到的偏振膜在100℃下,在照度为405mW/cm2(红光)的高压水银灯下辐射120小时时,ΔA(%)的值为94(%),显示出高温下长时间暴露具有极好的耐光性.ΔA(%)定义如下:
ΔA(%)=(A(120)/A(0))×100
当用A(0)表示在0小时时的吸光度值,和A(120)表示120小时后的吸光度值的时候,越大的ΔA意味着越好的耐光性。
对比实施例1
利用上述的式(B)(在专利文献1的实施例63中描述的化合物)代替用于含有(I-1)多偶氮化合物的偏振膜的染料,以与实施例1中相同的方法得到偏振膜.测量所得到的偏振膜的偏振度,发现43%单体透射率下的偏振度是98%,显示出比本发明的偏振膜差的性能。此外,当制备了偏振膜并以与实施例1中相同的方式,在100℃下,在照度为405mW/cm2(红光)的高压水银灯下辐射120小时时,ΔA(%)的值为81(%),显示出比本发明的偏振膜差的耐光性。
Claims (8)
2.根据权利要求1的多偶氮化合物,其中R1代表氢原子、甲基或者甲氧基。
3.根据权利要求1的多偶氮化合物,其中R2代表氢原子、甲基或者甲氧基。
4.一种偏振膜,其包含含有根据权利要求1的多偶氮化合物的用于偏振膜的染料,和偏振膜基质。
5.根据权利要求4的偏振膜,其中用于偏振膜的染料还进一步含有不同于多偶氮化合物的有机染料。
6.根据权利要求5的偏振膜,其中所述有机染料是选自由以下颜色索引属名代表的有机染料的至少一种:
C.I.直接黄12,
C.I.直接黄28,
C.I.直接黄44,
C.I.直接橙26,
C.I.直接橙39,
C.I.直接橙107,
C.I.直接红2,
C.I.直接红31,
C.I.直接红79,
C.I.直接红81,
C.I.直接红117,
C.I.直接红247。
7.根据权利要求4的偏振膜,其中偏振膜基质是由聚乙烯醇树脂形成的基质。
8.一种含有根据权利要求7的偏振膜的液晶显示器。
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