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 (en, 2012) | 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 (en, 2012) |
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 |
| US6552849B1 (en) | 1998-12-18 | 2003-04-22 | Nippon Kayaku Kabushiki Kaisha | Color polarizer with support for liquid crystal projector and color liquid crystal projector |
| WO2001006281A1 (fr) | 1999-07-14 | 2001-01-25 | Nippon Kayaku Kabushiki Kaisha | Polariseur renfermant une teinture |
| JP4452237B2 (ja) | 2003-04-16 | 2010-04-21 | 日本化薬株式会社 | アゾ化合物及びその塩 |
| JP4662853B2 (ja) | 2004-02-04 | 2011-03-30 | 日本化薬株式会社 | アゾ化合物、それを含有する偏光膜及び偏光板 |
| EP1816170A4 (en) | 2004-11-24 | 2009-10-14 | Nippon Kayaku Kk | AZO COMPOUNDS AND POLYMERIZING FILMS OR PLATES CONTAINING THE SAME |
| CA2652747C (en) | 2006-06-01 | 2013-08-06 | Nippon Kayaku Kabushiki Kaisha | Azo compound and salt thereof, and dye-containing polarizing film comprising the compound or salt |
| WO2007145210A1 (ja) | 2006-06-13 | 2007-12-21 | Nippon Kayaku Kabushiki Kaisha | アゾ化合物及びそれらを含有する染料系偏光膜 |
| CN103224713B (zh) | 2006-06-22 | 2015-03-18 | 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 |
| JP5374940B2 (ja) * | 2007-07-09 | 2013-12-25 | 三菱化学株式会社 | 異方性膜用化合物 |
| 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 |
| WO2009142193A1 (ja) | 2008-05-20 | 2009-11-26 | 日本化薬株式会社 | アゾ化合物及びそれらを含有する染料系偏光膜並びに偏光板 |
| JP5366947B2 (ja) | 2008-06-17 | 2013-12-11 | 日本化薬株式会社 | 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並びに偏光板 |
| CN103502852B (zh) | 2011-05-30 | 2016-08-17 | 日本化药株式会社 | 染料系偏光元件和偏振片 |
| CN103547949B (zh) | 2011-05-30 | 2017-07-21 | 日本化药株式会社 | 染料系偏光元件和偏振片 |
| WO2012165224A1 (ja) | 2011-05-31 | 2012-12-06 | 日本化薬株式会社 | 染料系偏光素子及び偏光板 |
| CN105190377B (zh) | 2013-04-03 | 2017-09-19 | 日本化药株式会社 | 无彩色的偏振元件以及偏振片 |
| US10215902B2 (en) | 2013-04-03 | 2019-02-26 | Nippon Kayaku Kabushiki Kaisha | Achromatic dye-based polarization element, and polarization plate |
| 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 |
| 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 |
| CN107003466B (zh) | 2015-05-20 | 2018-12-14 | 日本化药株式会社 | 染料系偏振元件以及使用了该染料系偏振元件的偏振片和液晶显示装置 |
| US10585281B2 (en) | 2016-05-16 | 2020-03-10 | Polatechno Co., Ltd. | Polarizing member and head-up display device comprising same |
| CN110249008B (zh) | 2017-03-31 | 2021-06-11 | 日本化药株式会社 | 偶氮化合物或其盐以及含有它们的染料系偏光膜、染料系偏光板及液晶显示装置 |
-
1984
- 1984-01-25 JP JP1022884A patent/JPS60156759A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60156759A (ja) | 1985-08-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |