JPS6157305B2 - - Google Patents
Info
- Publication number
- JPS6157305B2 JPS6157305B2 JP12479678A JP12479678A JPS6157305B2 JP S6157305 B2 JPS6157305 B2 JP S6157305B2 JP 12479678 A JP12479678 A JP 12479678A JP 12479678 A JP12479678 A JP 12479678A JP S6157305 B2 JPS6157305 B2 JP S6157305B2
- Authority
- JP
- Japan
- Prior art keywords
- diazaanthraquinone
- nitro
- water
- amino
- pigments
- 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
- VQAKHHWRJABLOL-UHFFFAOYSA-N benzo[g]quinoxaline-5,10-dione Chemical class C1=CN=C2C(=O)C3=CC=CC=C3C(=O)C2=N1 VQAKHHWRJABLOL-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- NXVAFOXTJCRFRX-UHFFFAOYSA-N 6-nitrobenzo[g]quinoxaline-5,10-dione Chemical compound O=C1C2=NC=CN=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] NXVAFOXTJCRFRX-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- KNIQIOWAIMJMLY-UHFFFAOYSA-N 6-aminobenzo[g]quinoxaline-5,10-dione Chemical compound O=C1C2=NC=CN=C2C(=O)C2=C1C=CC=C2N KNIQIOWAIMJMLY-UHFFFAOYSA-N 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229940015043 glyoxal Drugs 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
- 239000002904 solvent Substances 0.000 description 2
- ZRPCOXOHCANVBO-UHFFFAOYSA-N 2,3,5-triaminonaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(N)=C(N)C(=O)C2=C1N ZRPCOXOHCANVBO-UHFFFAOYSA-N 0.000 description 1
- -1 5-nitro-1,4-diazaanthraquinone Anthraquinone Chemical compound 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- SZRDOCAJXSKODE-UHFFFAOYSA-N benzo[g]cinnoline-5,10-dione Chemical compound N1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=N1 SZRDOCAJXSKODE-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000001053 orange pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
本発明は１・４−ジアザアントラキノン誘導体
に関するものである。
本発明の下記一般式
（式中、Ｘはニトロ基またはアミノ基を表わす。）
で示される５−ニトロ−１・４−ジアザアントラ
キノンおよび５−アミノ−１・４−ジアザアント
ラキノンは染料、顔料等の中間体として価値ある
新規な化合物である。
５−ニトロ−１・４−ジアザアントラキノンは
１・４−ジアザアントラキノンを硫酸、酢酸など
の溶媒中で硝酸でニトロ化することにより得ら
れ、また、５−アミノ−１・４−ジアザアントラ
キノンは５−ニトロ−１・４−ジアザアントラキ
ノンを硫化ソーダ、鉄粉などで還元するか、２・
３・５−トリアミノ−１・４−ナフトキノンとグ
リオキザールを、水、酢酸などの溶媒中で縮合す
ることにより得られる。
５−アミノ−１・４−ジアザアントラキノン
は、それ自体新規な橙色の色素であり、各種合成
繊維、プラスチツクその他の着色剤として有用で
あるばかりでなく、種々の染料、顔料等の中間体
としてきわめて価値のあるものである。
また、５−ニトロ−１・４−ジアザアントラキ
ノンは、５−アミノ−１・４−ジアザアントラキ
ノンの中間体あるいはその他の種々の染料、顔料
等の中間体として価値のあるものである。
次に本発明を実施例によつて更に具体的に説明
する。
実施例 １
ジアザアントラキノン3.8ｇを98％硫酸10ｇに
溶解し、75〜80℃において発煙硝酸（ｄ＝1.52）
2.1ｇと98％硫酸15ｇよりなる混酸を１時間で滴
下し、同温度で更に４時間反応させた。室温まで
冷却後、氷水300ｇ中に排出し、析出物を過し
て水洗および乾燥を行なつた。ベンゼンより再結
晶し、５−ニトロ−１・４−ジアザアントラキノ
ン１ｇを得た。
融点 270℃（分解）
マススペクトル M+＝255
The present invention relates to 1,4-diazaanthraquinone derivatives. The following general formula of the present invention (In the formula, X represents a nitro group or an amino group.)
5-nitro-1,4-diazaanthraquinone and 5-amino-1,4-diazaanthraquinone shown by are novel compounds that are valuable as intermediates for dyes, pigments, etc. 5-nitro-1,4-diazaanthraquinone is obtained by nitrating 1,4-diazaanthraquinone with nitric acid in a solvent such as sulfuric acid or acetic acid, and 5-nitro-1,4-diazaanthraquinone Anthraquinone can be obtained by reducing 5-nitro-1,4-diazaanthraquinone with sodium sulfide, iron powder, etc.
It is obtained by condensing 3,5-triamino-1,4-naphthoquinone and glyoxal in a solvent such as water or acetic acid. 5-Amino-1,4-diazaanthraquinone is itself a novel orange pigment, and is not only useful as a coloring agent for various synthetic fibers, plastics, etc., but also as an intermediate for various dyes, pigments, etc. It is extremely valuable. Furthermore, 5-nitro-1,4-diazaanthraquinone is valuable as an intermediate for 5-amino-1,4-diazaanthraquinone or as an intermediate for various other dyes and pigments. Next, the present invention will be explained in more detail with reference to Examples. Example 1 3.8 g of diazaanthraquinone was dissolved in 10 g of 98% sulfuric acid and dissolved in fuming nitric acid (d=1.52) at 75-80°C.
A mixed acid consisting of 2.1 g and 15 g of 98% sulfuric acid was added dropwise over 1 hour, and the reaction was continued for an additional 4 hours at the same temperature. After cooling to room temperature, it was poured into 300 g of ice water, and the precipitate was filtered, washed with water, and dried. Recrystallization from benzene yielded 1 g of 5-nitro-1,4-diazaanthraquinone. Melting point 270℃ (decomposition) Mass spectrum M + =255
【表】
実施例 ２
硫化ソーダ1.14ｇ、硫黄0.15ｇを水100mlに溶
解後、５−ニトロ−１・４−ジアザアントラキノ
ン１ｇを加え、２時間煮沸した。室温まで冷却後
析出した結晶を過し、水から再結晶し、５−ア
ミノ−１・４−ジアザアントラキノン0.3ｇを得
た。
融点 300℃以上
マススペクトル M+＝225[Table] Example 2 After dissolving 1.14 g of sodium sulfide and 0.15 g of sulfur in 100 ml of water, 1 g of 5-nitro-1,4-diazaanthraquinone was added and boiled for 2 hours. After cooling to room temperature, the precipitated crystals were filtered and recrystallized from water to obtain 0.3 g of 5-amino-1,4-diazaanthraquinone. Melting point 300℃ or higher Mass spectrum M + = 225
【表】
赤外吸収スペクトル（KBr）
νNH＝3500cm-1、3350cm-1
νCO＝1680cm-1、1650cm-1
なお、本品を用いて高温染色法によりポリエス
テル繊維を染色したところ、これを鮮明な橙色に
染めた。
実施例 ３
２・３・５−トリアミノ−１・４−ナフトキノ
ン7.7ｇを水230ml中に分散し、90℃で40％グリオ
キザール水溶液7.7ｇを30分間で加え、同温度で
更に３時間反応させた。
室温まで冷却後、析出した結晶を過し、水洗
および乾燥を行ない、赤色結晶８ｇを得た。この
ものの融点、マススペクトル、赤外吸収スペクト
ルおよび元素分析値は実施例２の化合物のそれと
良く合致した。[Table] Infrared absorption spectrum (KBr) νNH = 3500cm -1 , 3350cm -1 νCO = 1680cm -1 , 1650cm -1 Furthermore, when this product was used to dye polyester fibers using a high-temperature dyeing method, it was clearly Dyed orange. Example 3 7.7 g of 2,3,5-triamino-1,4-naphthoquinone was dispersed in 230 ml of water, and 7.7 g of a 40% glyoxal aqueous solution was added over 30 minutes at 90°C, followed by further reaction at the same temperature for 3 hours. . After cooling to room temperature, the precipitated crystals were filtered, washed with water, and dried to obtain 8 g of red crystals. The melting point, mass spectrum, infrared absorption spectrum and elemental analysis values of this compound matched well with those of the compound of Example 2.
Claims (1)
で示される１・４−ジアザアントラキノン誘導
体。[Claims] 1. General formula (In the formula, X represents a nitro group or an amino group.)
A 1,4-diazaanthraquinone derivative represented by
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12479678A JPS5551071A (en) | 1978-10-11 | 1978-10-11 | Diazaanthraquinone derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12479678A JPS5551071A (en) | 1978-10-11 | 1978-10-11 | Diazaanthraquinone derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5551071A JPS5551071A (en) | 1980-04-14 |
| JPS6157305B2 true JPS6157305B2 (en) | 1986-12-06 |
Family
ID=14894325
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12479678A Granted JPS5551071A (en) | 1978-10-11 | 1978-10-11 | Diazaanthraquinone derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5551071A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3375849B2 (en) * | 1997-05-23 | 2003-02-10 | 京セラミタ株式会社 | Naphthoquinone derivative and electrophotographic photoreceptor using the same |
| WO2005016000A1 (en) * | 2003-08-05 | 2005-02-24 | Avalon Pharmaceuticals | Derivatives of cyclic quinone and uses thereof |
-
1978
- 1978-10-11 JP JP12479678A patent/JPS5551071A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5551071A (en) | 1980-04-14 |
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