JPH0261988B2 - - Google Patents
Info
- Publication number
- JPH0261988B2 JPH0261988B2 JP1753583A JP1753583A JPH0261988B2 JP H0261988 B2 JPH0261988 B2 JP H0261988B2 JP 1753583 A JP1753583 A JP 1753583A JP 1753583 A JP1753583 A JP 1753583A JP H0261988 B2 JPH0261988 B2 JP H0261988B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- acid
- parts
- compound
- 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 disazo compound Chemical class 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 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 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QEAYLNJEDDOYNQ-UHFFFAOYSA-N 6-anilino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C2C(O)=CC(S(O)(=O)=O)=CC2=CC=C1NC1=CC=CC=C1 QEAYLNJEDDOYNQ-UHFFFAOYSA-N 0.000 description 5
- 239000007853 buffer solution Substances 0.000 description 5
- 235000002639 sodium chloride Nutrition 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000000975 dye Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 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 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 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
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 235000010288 sodium nitrite Nutrition 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
- 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
- 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 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000003916 acid precipitation Methods 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
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 229920001577 copolymer Polymers 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
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000004042 decolorization Methods 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
- 238000001035 drying Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000000203 mixture 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
- 229920005615 natural polymer Polymers 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002964 rayon 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
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1753583A JPS59145255A (ja) | 1983-02-07 | 1983-02-07 | 水溶性ジスアゾ化合物 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1753583A JPS59145255A (ja) | 1983-02-07 | 1983-02-07 | 水溶性ジスアゾ化合物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59145255A JPS59145255A (ja) | 1984-08-20 |
| JPH0261988B2 true JPH0261988B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1990-12-21 |
Family
ID=11946612
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1753583A Granted JPS59145255A (ja) | 1983-02-07 | 1983-02-07 | 水溶性ジスアゾ化合物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59145255A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017146212A1 (ja) | 2016-02-26 | 2017-08-31 | 日本化薬株式会社 | アゾ化合物又はその塩及びこれを含有する偏光膜 |
| JPWO2019117123A1 (ja) * | 2017-12-13 | 2021-01-07 | 日本化薬株式会社 | 可視域および赤外域用偏光素子、および、偏光板 |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0374655B1 (de) * | 1988-12-23 | 1993-09-15 | Bayer Ag | Lichtpolarisierende Filme oder Folien enthaltende Stilbenfarbstoffe |
| 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 |
| SG74532A1 (en) | 1994-09-16 | 2000-08-22 | Sumitomo Chemical Co | Tetrakisazo compound and a polarizing film containing the same |
| 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 |
| CN1175289C (zh) | 1999-07-14 | 2004-11-10 | 日本化药株式会社 | 聚乙烯醇型偏振膜，聚乙烯醇型偏振板以及具有该偏振板的彩色液晶投影仪 |
| KR100357909B1 (ko) * | 2000-05-23 | 2002-10-25 | 신화오플라주식회사 | 디스아조 화합물 제조 방법 |
| US7317499B2 (en) | 2002-08-22 | 2008-01-08 | Nitto Denko Corporation | Multilayer plate and display panel with anisotropic crystal film and conducting protective layer |
| EP1712595B1 (en) | 2004-02-04 | 2009-04-29 | Nippon Kayaku Kabushiki Kaisha | Azo compound and polarizing film and polarizing plate each containing the same |
| EP1816170A4 (en) | 2004-11-24 | 2009-10-14 | Nippon Kayaku Kk | AZO COMPOUNDS AND POLYMERIZING FILMS OR PLATES CONTAINING THE SAME |
| KR20100028525A (ko) * | 2007-07-09 | 2010-03-12 | 미쓰비시 가가꾸 가부시키가이샤 | 이방성 막용 화합물 |
| JP6107352B2 (ja) * | 2013-04-12 | 2017-04-05 | 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 |
| WO2022196784A1 (ja) | 2021-03-18 | 2022-09-22 | 日本化薬株式会社 | 光学積層体、それを用いたアイウェア |
| JPWO2022270446A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2021-06-24 | 2022-12-29 |
-
1983
- 1983-02-07 JP JP1753583A patent/JPS59145255A/ja active Granted
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017146212A1 (ja) | 2016-02-26 | 2017-08-31 | 日本化薬株式会社 | アゾ化合物又はその塩及びこれを含有する偏光膜 |
| JPWO2019117123A1 (ja) * | 2017-12-13 | 2021-01-07 | 日本化薬株式会社 | 可視域および赤外域用偏光素子、および、偏光板 |
| JP2023040123A (ja) * | 2017-12-13 | 2023-03-22 | 日本化薬株式会社 | 可視域および赤外域用偏光素子、および、偏光板 |
| JP2023052132A (ja) * | 2017-12-13 | 2023-04-11 | 日本化薬株式会社 | 可視域および赤外域用偏光素子、および、偏光板 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59145255A (ja) | 1984-08-20 |
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