JPH0450944B2 - - Google Patents
Info
- Publication number
- JPH0450944B2 JPH0450944B2 JP1022884A JP1022884A JPH0450944B2 JP H0450944 B2 JPH0450944 B2 JP H0450944B2 JP 1022884 A JP1022884 A JP 1022884A JP 1022884 A JP1022884 A JP 1022884A JP H0450944 B2 JPH0450944 B2 JP H0450944B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- acid
- parts
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 N-methyl-N-acetylamino group Chemical group 0.000 claims description 63
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 4
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 3
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 28
- 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 17
- HBZVNWNSRNTWPS-UHFFFAOYSA-N 6-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(N)=CC=C21 HBZVNWNSRNTWPS-UHFFFAOYSA-N 0.000 description 13
- 239000004372 Polyvinyl alcohol Substances 0.000 description 12
- 229920002451 polyvinyl alcohol Polymers 0.000 description 12
- 235000002639 sodium chloride Nutrition 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000010287 polarization Effects 0.000 description 3
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical group CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- QEZZCWMQXHXAFG-UHFFFAOYSA-N 8-aminonaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(N)=CC=CC2=C1 QEZZCWMQXHXAFG-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 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
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000005185 salting out Methods 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 229910052979 sodium sulfide Inorganic materials 0.000 description 2
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- XPKFTIYOZUJAGA-UHFFFAOYSA-N 2,5-diethoxyaniline Chemical compound CCOC1=CC=C(OCC)C(N)=C1 XPKFTIYOZUJAGA-UHFFFAOYSA-N 0.000 description 1
- TUOWYJFPLMIKCX-UHFFFAOYSA-N 2-ethoxynaphthalen-1-amine Chemical compound C1=CC=CC2=C(N)C(OCC)=CC=C21 TUOWYJFPLMIKCX-UHFFFAOYSA-N 0.000 description 1
- FAOJNWOJCPKVTM-UHFFFAOYSA-N 2-methoxynaphthalen-1-amine Chemical compound C1=CC=CC2=C(N)C(OC)=CC=C21 FAOJNWOJCPKVTM-UHFFFAOYSA-N 0.000 description 1
- ZCNCWYFISJTFHB-UHFFFAOYSA-N 4-hydroxy-7-(methylamino)naphthalene-2-sulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(NC)=CC=C21 ZCNCWYFISJTFHB-UHFFFAOYSA-N 0.000 description 1
- YGNDWDUEMICDLW-UHFFFAOYSA-N 7-anilino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C=1C=C2C(O)=CC(S(O)(=O)=O)=CC2=CC=1NC1=CC=CC=C1 YGNDWDUEMICDLW-UHFFFAOYSA-N 0.000 description 1
- ZLHGMJOGMLVDFS-UHFFFAOYSA-N 7-benzamido-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C=1C=C2C(O)=CC(S(O)(=O)=O)=CC2=CC=1NC(=O)C1=CC=CC=C1 ZLHGMJOGMLVDFS-UHFFFAOYSA-N 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- OVBJJZOQPCKUOR-UHFFFAOYSA-L EDTA disodium salt dihydrate Chemical compound O.O.[Na+].[Na+].[O-]C(=O)C[NH+](CC([O-])=O)CC[NH+](CC([O-])=O)CC([O-])=O OVBJJZOQPCKUOR-UHFFFAOYSA-L 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- SJWQCBCAGCEWCV-UHFFFAOYSA-N n-(3-amino-4-methoxyphenyl)acetamide Chemical compound COC1=CC=C(NC(C)=O)C=C1N SJWQCBCAGCEWCV-UHFFFAOYSA-N 0.000 description 1
- PEMGGJDINLGTON-UHFFFAOYSA-N n-(3-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(N)=C1 PEMGGJDINLGTON-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1022884A JPS60156759A (ja) | 1984-01-25 | 1984-01-25 | 水溶性ジスアゾ化合物 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1022884A JPS60156759A (ja) | 1984-01-25 | 1984-01-25 | 水溶性ジスアゾ化合物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60156759A JPS60156759A (ja) | 1985-08-16 |
| JPH0450944B2 true JPH0450944B2 (enExample) | 1992-08-17 |
Family
ID=11744420
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1022884A Granted JPS60156759A (ja) | 1984-01-25 | 1984-01-25 | 水溶性ジスアゾ化合物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60156759A (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0374655B1 (de) * | 1988-12-23 | 1993-09-15 | Bayer Ag | Lichtpolarisierende Filme oder Folien enthaltende Stilbenfarbstoffe |
| US5272259A (en) * | 1988-12-23 | 1993-12-21 | Bayer Aktiengesellschaft | Stilbene dyestuffs and light-polarizing films or sheets containing stilbene |
| ES2104881T3 (es) * | 1991-09-26 | 1997-10-16 | Ciba Geigy Ag | Procedimiento para teñir papel con colorantes diazoicos. |
| US5423100A (en) * | 1992-08-26 | 1995-06-13 | Mitsui Toatsu Chemicals, Inc. | Water-soluble azo compounds and polarizing films using the compounds |
| US5639809A (en) | 1994-06-22 | 1997-06-17 | Mitsui Toatsu Chemicals, Inc. | Azo compounds and polarizing films using the compounds |
| WO2000037973A1 (fr) * | 1998-12-18 | 2000-06-29 | Nippon Kayaku Kabushiki Kaisha | Polariseur de couleur a support pour projecteur a cristaux liquides et projecteur associe |
| DE60020976T2 (de) | 1999-07-14 | 2005-12-29 | Nippon Kayaku K.K. | Farbstoff-polarisator |
| WO2004092282A1 (ja) | 2003-04-16 | 2004-10-28 | Nippon Kayaku Kabushiki Kaisha | アゾ化合物及びその塩 |
| CA2553415A1 (en) | 2004-02-04 | 2005-08-18 | Nippon Kayaku Kabushiki Kaisha | Azo compound and polarizing film and polarizing plate each containing the same |
| CA2586123A1 (en) | 2004-11-24 | 2006-06-01 | Nippon Kayaku Kabushiki Kaisha | Azo compounds and dye-type polarizing films or plates containing the same |
| WO2007138980A1 (ja) | 2006-06-01 | 2007-12-06 | Nippon Kayaku Kabushiki Kaisha | アゾ化合物及びその塩並びにそれらを含有する染料系偏光膜 |
| CN101466798B (zh) | 2006-06-13 | 2013-01-16 | 日本化药株式会社 | 偶氮化合物和包含它的染料偏振膜 |
| CN101479347B (zh) | 2006-06-22 | 2013-08-07 | 日本化药株式会社 | 偶氮化合物和含有该偶氮化合物的染料偏振膜 |
| CN101688065B (zh) * | 2007-07-09 | 2014-03-12 | 三菱化学株式会社 | 各向异性膜用化合物 |
| TWI406907B (zh) | 2007-11-02 | 2013-09-01 | Nippon Kayaku Kk | 偶氮化合物及含有彼等之染料系偏光膜 |
| CN102037082B (zh) | 2008-05-20 | 2014-05-28 | 日本化药株式会社 | 偶氮化合物及包含所述偶氮化合物的染料基偏振膜和偏振片 |
| US8477268B2 (en) | 2008-06-17 | 2013-07-02 | Nippon Kayaku Kabushiki Kaisha | Azo compound and salts thereof, as well as dye-based polarization films and polarizing plates comprising the same |
| KR20140031861A (ko) | 2011-05-30 | 2014-03-13 | 니폰 가야꾸 가부시끼가이샤 | 염료계 편광소자 및 편광판 |
| US20140085721A1 (en) | 2011-05-30 | 2014-03-27 | Polatechno Co., Ltd. | Dye-Based Polarizing Element And Polarizing Plate |
| US20140126054A1 (en) | 2011-05-31 | 2014-05-08 | Polatechno Co., Ltd. | Dye-Based Polarizing Element And Polarizing Plate |
| JP6317334B2 (ja) | 2013-04-03 | 2018-04-25 | 日本化薬株式会社 | 無彩色な染料系偏光素子、及び偏光板 |
| TWI643908B (zh) | 2013-04-03 | 2018-12-11 | 日本化藥公司 | 具有高透過率之無彩色之染料系偏光元件及偏光板 |
| EP2983019A4 (en) | 2013-04-03 | 2016-11-02 | Nippon Kayaku Kk | ACHROMATIC POLARIZING ELEMENT, AND POLARIZING PLATE |
| JP6064759B2 (ja) * | 2013-04-12 | 2017-01-25 | 三菱化学株式会社 | 異方性色素膜用色素、該色素を含む組成物、異方性色素膜及び偏光素子 |
| WO2016186183A1 (ja) | 2015-05-20 | 2016-11-24 | 日本化薬株式会社 | 染料系偏光素子、並びにこれを用いた偏光板及び液晶表示装置 |
| CN109154691B (zh) | 2016-05-16 | 2020-05-12 | 日本宝来科技有限公司 | 偏振构件和具有该偏振构件的平视显示装置 |
| JP7035018B2 (ja) | 2017-03-31 | 2022-03-14 | 日本化薬株式会社 | アゾ化合物又はその塩、並びにこれを含有する染料系偏光膜、染料系偏光板、及び液晶表示装置 |
-
1984
- 1984-01-25 JP JP1022884A patent/JPS60156759A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60156759A (ja) | 1985-08-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0450944B2 (enExample) | ||
| JP3205096B2 (ja) | 水溶性アゾ染料及び該染料を用いた偏光フィルム | |
| JPH0312606A (ja) | 水溶性アゾ染料及びこれを含有する偏光膜 | |
| JP4078476B2 (ja) | アゾ化合物又はその塩及びそれらを含有する染料系偏光膜 | |
| JP2001033627A (ja) | 染料系偏光膜 | |
| EP0727465B1 (en) | An azo compound and a polarizing film containing the same | |
| EP0584962B1 (en) | Water-soluble azo compounds and polarizing films using the compounds | |
| JPH0261988B2 (enExample) | ||
| JP4815721B2 (ja) | ポリアゾ化合物又はその塩及びそれらを含有する染料系偏光膜 | |
| EP0688830B1 (en) | Azo compounds and polarizing films using the compounds | |
| JPH0813932B2 (ja) | 水溶性アゾ染料及びこれを含有する偏光膜 | |
| JP3270536B2 (ja) | 水溶性アゾ染料及び該染料を用いた偏光フィルム | |
| US3859271A (en) | Reactive yellow ' -sulfatoethylsulfonyl phenylazo-4-(1-substituted phenyl-3-methyl-5-amino)-pyrazole dyes | |
| JP3617540B2 (ja) | アゾ化合物及び該化合物を用いた偏光フィルム | |
| JP2657416B2 (ja) | 偏光板 | |
| JPH05295282A (ja) | 水溶性アゾ染料及び該染料を用いた偏光フィルム | |
| JPH09302250A (ja) | アゾ化合物及びそれを含有する染料系偏光膜 | |
| EP0621317B1 (en) | Azo compound and polarizing film using it | |
| US4297278A (en) | Pentakis-and heptakis-azoxy dyestuffs | |
| JP3852966B2 (ja) | アゾ化合物及び該化合物を用いた偏光フィルム | |
| JP3803394B2 (ja) | アゾ化合物及び該化合物を用いた偏光フィルム | |
| JP3263121B2 (ja) | 水溶性アゾ染料及び該染料を用いた偏光フィルム | |
| JP2001002631A (ja) | ジスアゾ化合物及びそれを含有する染料系偏光膜 | |
| JP2003301120A (ja) | 新規なアゾ染料 | |
| US2420630A (en) | Disazo dye compounds |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |