JP2014160160A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2014160160A5 JP2014160160A5 JP2013030652A JP2013030652A JP2014160160A5 JP 2014160160 A5 JP2014160160 A5 JP 2014160160A5 JP 2013030652 A JP2013030652 A JP 2013030652A JP 2013030652 A JP2013030652 A JP 2013030652A JP 2014160160 A5 JP2014160160 A5 JP 2014160160A5
- Authority
- JP
- Japan
- Prior art keywords
- color filter
- group
- carbon atoms
- colorant
- parts
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 claims description 7
- 239000000049 pigment Substances 0.000 claims description 6
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 4
- 239000003086 colorant Substances 0.000 claims 5
- 125000004432 carbon atoms Chemical group C* 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 238000004040 coloring Methods 0.000 claims 3
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 2
- FXXSGZBPAJRJHH-ZOZQPSRMSA-N (4E)-4-[[2-chloro-5-(trifluoromethyl)phenyl]hydrazinylidene]-N-[2,5-dichloro-4-[[(4Z)-4-[[2-chloro-5-(trifluoromethyl)phenyl]hydrazinylidene]-3-oxonaphthalene-2-carbonyl]amino]phenyl]-3-oxonaphthalene-2-carboxamide Chemical compound FC(F)(F)C1=CC=C(Cl)C(N\N=C\2C3=CC=CC=C3C=C(C/2=O)C(=O)NC=2C(=CC(NC(=O)C=3C(C(=N\NC=4C(=CC=C(C=4)C(F)(F)F)Cl)/C4=CC=CC=C4C=3)=O)=C(Cl)C=2)Cl)=C1 FXXSGZBPAJRJHH-ZOZQPSRMSA-N 0.000 claims 1
- JNNHVXMCVRYTTN-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-3,6-dione Chemical compound C1=CC(Cl)=CC=C1C(NC1=O)=C2C1=C(C=1C=CC(Cl)=CC=1)NC2=O JNNHVXMCVRYTTN-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 239000011230 binding agent Substances 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000000178 monomer Substances 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical class C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 claims 1
- 239000011347 resin Substances 0.000 claims 1
- 229920005989 resin Polymers 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 239000000758 substrate Substances 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 239000000243 solution Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- -1 azo compound Chemical class 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000002194 synthesizing Effects 0.000 description 2
- INCJNDAQNPWMPZ-UHFFFAOYSA-N 3-amino-4-methoxybenzamide Chemical compound COC1=CC=C(C(N)=O)C=C1N INCJNDAQNPWMPZ-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N P-Phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Description
（１）アゾ化合物ａの合成
水１５００部に４−メトキシ−３−アミノ−安息香酸アミド６２部を加えた後、３５％塩酸１４７部を加え、−２〜０℃になるよう冷却した。この溶液に２５％亜硝酸ナトリウム水溶液１０４部を加えた後、０〜５℃に保持しながら、３０分間攪拌し、ジアゾニウム溶液を調整した。別途、２，３−ヒドロキシナフトエ酸７０部と、２５％水酸化ナトリウム溶液１５８部、水１５００部からなるカップラー溶液を調整した。調整したジアゾニウム溶液とカップラー溶液を、同時にｐＨ５．４の酢酸バッファー溶液３０００部に１０分間で滴下した。滴下終了後、室温で３０分間攪拌した後、さらに、８０℃に保持しながら攪拌し、析出した反応物をろ取し、熱湯で洗浄後、乾燥してアゾ化合物ａを１３２部（収率：９８．０％）得た。
(1) Synthesis of azo compound a After adding 62 parts of 4-methoxy-3-amino-benzoic acid amide to 1500 parts of water, 147 parts of 35% hydrochloric acid was added and cooled to −2 to 0 ° C. After adding 104 parts of 25% aqueous sodium nitrite solution to this solution, the mixture was stirred for 30 minutes while maintaining at 0 to 5 ° C. to prepare a diazonium solution. Separately, a coupler solution consisting of 70 parts of 2,3-hydroxynaphthoic acid, 158 parts of 25% sodium hydroxide solution and 1500 parts of water was prepared. The adjusted diazonium solution and coupler solution were simultaneously added dropwise to 3000 parts of an acetic acid buffer solution having a pH of 5.4 over 10 minutes. After completion of the dropwise addition, the mixture was stirred at room temperature for 30 minutes, and further stirred while maintaining at 80 ° C. The precipitated reaction product was collected by filtration, washed with hot water, and dried to obtain 132 parts of azo compound a (yield: 98.0%).
（１）アゾ顔料１の合成
Ｏ−キシレン９００部に、アゾ化合物ａ１２２部、およびＮ，Ｎ−ジメチルホルムアミド１０部を加え、８５℃に加熱後、塩化チオニル４２部を３０分間で滴下した。滴下終了後、２時間還流した。別途調製した１，４−フェニレンジアミン１７部とＯ−キシレン１５００部を８５℃に加熱した溶液に、上記反応溶液を１時間かけて滴下し、４時間加熱還流した。この反応液を９５℃に冷却後、２８％アンモニア水溶液２０部および水２０部を加え、９５〜１００℃にて３０分間攪拌後、析出した反応物をろ取し、Ｏ−キシレン、メタノール、および熱湯で洗浄後、乾燥してアゾ顔料１を９９部（収率：７８．９％）得た。ＴＯＦ−ＭＳによる質量分析の結果、および元素分析の結果から、アゾ顔料１であることを同定した。表２に、元素分析の結果を示す。
(1) Synthesis of azo pigment 1 122 parts of azo compound a and 10 parts of N, N-dimethylformamide were added to 900 parts of O-xylene. After heating to 85 ° C., 42 parts of thionyl chloride was added dropwise over 30 minutes. After completion of dropping, the mixture was refluxed for 2 hours. The above reaction solution was added dropwise to a solution prepared by separately heating 17 parts of 1,4-phenylenediamine and 1500 parts of O-xylene at 85 ° C. over 1 hour and refluxed for 4 hours. After cooling this reaction liquid to 95 ° C, 20 parts of 28% aqueous ammonia solution and 20 parts of water were added and stirred at 95-100 ° C for 30 minutes. The precipitated reaction product was collected by filtration, and O-xylene, methanol, and After washing with hot water and drying, 99 parts of azo pigment 1 (yield: 78.9%) were obtained. From the results of mass spectrometry by TOF-MS and the results of elemental analysis, it was identified as azo pigment 1. Table 2 shows the results of elemental analysis.
Claims (6)
一般式（１）
［一般式（１）中、ＲaおよびＲbは、それぞれ独立して、水素原子、炭素数１〜４のアルキル基または置換基を有しても良いフェニル基を表す。Ｒcは、炭素数１〜４のアルキル基を表す。ＸおよびＹは、それぞれ独立して、水素原子、ハロゲン原子、シアノ基、ニトロ基、炭素数１〜４のアルキル基、炭素数１〜４のアルコキシル基またはトリフルオロメチル基を表す。］ A color filter colorant comprising an azo pigment represented by the following general formula (1).
General formula (1)
[In General Formula (1), R a and R b each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group which may have a substituent. R c represents an alkyl group having 1 to 4 carbon atoms. X and Y each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, or a trifluoromethyl group. ]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2013030652A JP6179121B2 (en) | 2013-02-20 | 2013-02-20 | Colorant for color filter, coloring composition, and color filter |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2013030652A JP6179121B2 (en) | 2013-02-20 | 2013-02-20 | Colorant for color filter, coloring composition, and color filter |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017035845A Division JP6172488B1 (en) | 2017-02-28 | 2017-02-28 | Colorant for color filter, coloring composition, and color filter |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014160160A JP2014160160A (en) | 2014-09-04 |
| JP2014160160A5 true JP2014160160A5 (en) | 2016-02-04 |
| JP6179121B2 JP6179121B2 (en) | 2017-08-16 |
Family
ID=51611888
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013030652A Active JP6179121B2 (en) | 2013-02-20 | 2013-02-20 | Colorant for color filter, coloring composition, and color filter |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP6179121B2 (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107743487B (en) * | 2015-06-17 | 2021-08-20 | 株式会社Lg化学 | Xanthene compound and photosensitive resin composition containing same |
| KR102131481B1 (en) * | 2016-07-26 | 2020-07-07 | 주식회사 엘지화학 | Photosensitive resin composition and color filter comprising same |
| JP6368844B1 (en) | 2017-08-25 | 2018-08-01 | 東洋インキＳｃホールディングス株式会社 | Azo pigment, colorant for color filter, contact composition and color filter |
| JP6973270B2 (en) * | 2018-04-25 | 2021-11-24 | 東洋インキＳｃホールディングス株式会社 | Color filter coating composition and color filter |
| JP6969489B2 (en) * | 2018-04-27 | 2021-11-24 | 東洋インキＳｃホールディングス株式会社 | Red coloring composition for organic EL display device, color filter, and organic EL display device |
| CN110511593B (en) | 2018-05-21 | 2022-07-08 | 东洋油墨Sc控股株式会社 | Azo pigment, color filter, colorant and coloring composition for the same, and display device and image pickup element comprising the same |
| JP6973297B2 (en) * | 2018-05-29 | 2021-11-24 | 東洋インキＳｃホールディングス株式会社 | Coloring compositions and color filters for color filters |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH519561A (en) * | 1969-07-08 | 1972-02-29 | Ciba Geigy Ag | Process for the production of new disazo pigments |
| JPS4914528A (en) * | 1972-05-22 | 1974-02-08 | ||
| EP0442846A3 (en) * | 1990-02-15 | 1992-09-16 | Ciba-Geigy Ag | Disazo compounds with long-chain alkylester- or alkylamide moieties |
| TW445284B (en) * | 1997-03-19 | 2001-07-11 | Ueno Seiyaku Oyo Kenkyujo Kk | Condensed azo compounds and their preparation |
| DE10032019A1 (en) * | 2000-07-01 | 2002-01-10 | Clariant Gmbh | Process for the preparation of disazo condensation pigments in microreactors |
| JP2002372618A (en) * | 2001-06-14 | 2002-12-26 | Fujifilm Arch Co Ltd | Red hardening composition for color filter and color filter using the same |
| JP2009237462A (en) * | 2008-03-28 | 2009-10-15 | Dic Corp | Red pigment for color filter, red color composition using the same, and the color filter |
| JP2010015063A (en) * | 2008-07-04 | 2010-01-21 | Fujifilm Corp | Colored photosensitive resin composition, color filter and method for manufacturing color filter |
| JP5544128B2 (en) * | 2008-09-02 | 2014-07-09 | 富士フイルム株式会社 | Azo compound, azo pigment, pigment dispersion, coloring composition, and ink jet recording ink |
| JP5460204B2 (en) * | 2009-09-24 | 2014-04-02 | 株式会社Ｄｎｐファインケミカル | Photosensitive red composition for color filter and color filter using the same |
| JP5622379B2 (en) * | 2009-11-06 | 2014-11-12 | 富士フイルム株式会社 | Azo compound, pigment composition, method for producing pigment composition, ink for inkjet recording, coloring composition for color filter, and color filter |
| JP5747289B2 (en) * | 2011-03-30 | 2015-07-15 | 東洋インキＳｃホールディングス株式会社 | Method for producing azo pigment |
-
2013
- 2013-02-20 JP JP2013030652A patent/JP6179121B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2014160160A5 (en) | ||
| JP2017058652A5 (en) | ||
| JP2010519356A5 (en) | ||
| JP2016118619A5 (en) | ||
| JP2015512381A5 (en) | ||
| JPS58157863A (en) | Production of monoazo dye | |
| JP2017111398A5 (en) | ||
| WO2016068151A1 (en) | Azo compound production method | |
| JPS5817771B2 (en) | Disazo pigment no. | |
| JP6251197B2 (en) | Process for preparing substituted phenylpropanones | |
| JP2011032210A5 (en) | ||
| JP6211711B2 (en) | Azo dye composition and method for producing the same | |
| JP2021147490A5 (en) | ||
| TWI784111B (en) | porphyrazine compound | |
| CN103087544A (en) | P-phenylenediamine bisazo organic pigment and preparation method thereof | |
| JP2012526870A5 (en) | ||
| JPS6253023B2 (en) | ||
| CN100366617C (en) | Benzoxazole azo-compound for generating carrier | |
| JPS61221266A (en) | Azo dyes | |
| JPH0240267B2 (en) | AZOGANRYOOYOBISONOSEIZOHOHO | |
| JP2017057160A (en) | Benzotriazole compound and method for producing the same | |
| JPH0232301B2 (en) | JISUAZOSENRYONOSEIZOHO | |
| JP4364663B2 (en) | Process for producing ureido derivatives of hydroxynaphthalenecarboxylic acids | |
| JP4518819B2 (en) | Azo compounds | |
| JP4441312B2 (en) | Azo compounds |