JPS581148B2 - Verinon Keisenriyouno Seizouhou - Google Patents
Verinon Keisenriyouno SeizouhouInfo
- Publication number
- JPS581148B2 JPS581148B2 JP8378675A JP8378675A JPS581148B2 JP S581148 B2 JPS581148 B2 JP S581148B2 JP 8378675 A JP8378675 A JP 8378675A JP 8378675 A JP8378675 A JP 8378675A JP S581148 B2 JPS581148 B2 JP S581148B2
- Authority
- JP
- Japan
- Prior art keywords
- parts
- naphthalene
- dicarboxylic anhydride
- dinitronaphthalene
- general formula
- 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
- 239000000975 dye Substances 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- RJKGJBPXVHTNJL-UHFFFAOYSA-N 1-nitronaphthalene Chemical class C1=CC=C2C([N+](=O)[O-])=CC=CC2=C1 RJKGJBPXVHTNJL-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 238000000034 method Methods 0.000 description 13
- AVCSMMMOCOTIHF-UHFFFAOYSA-N 1,8-dinitronaphthalene Chemical compound C1=CC([N+]([O-])=O)=C2C([N+](=O)[O-])=CC=CC2=C1 AVCSMMMOCOTIHF-UHFFFAOYSA-N 0.000 description 11
- 239000000843 powder Substances 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 7
- IZJDCINIYIMFGX-UHFFFAOYSA-N benzo[f][2]benzofuran-1,3-dione Chemical compound C1=CC=C2C=C3C(=O)OC(=O)C3=CC2=C1 IZJDCINIYIMFGX-UHFFFAOYSA-N 0.000 description 7
- YFOOEYJGMMJJLS-UHFFFAOYSA-N 1,8-diaminonaphthalene Chemical compound C1=CC(N)=C2C(N)=CC=CC2=C1 YFOOEYJGMMJJLS-UHFFFAOYSA-N 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 6
- 229910052742 iron Inorganic materials 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 150000007524 organic acids Chemical class 0.000 description 5
- 238000006722 reduction reaction Methods 0.000 description 5
- SOOKWSYBWVCXEB-UHFFFAOYSA-N 8-nitronaphthalen-1-amine Chemical compound C1=CC([N+]([O-])=O)=C2C(N)=CC=CC2=C1 SOOKWSYBWVCXEB-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- -1 dinitrate naphthalene Chemical compound 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZUTCJXFCHHDFJS-UHFFFAOYSA-N 1,5-dinitronaphthalene Chemical compound C1=CC=C2C([N+](=O)[O-])=CC=CC2=C1[N+]([O-])=O ZUTCJXFCHHDFJS-UHFFFAOYSA-N 0.000 description 2
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- DHZBEENLJMYSHQ-XCVPVQRUSA-N cantharidin Chemical compound C([C@@H]1O2)C[C@@H]2[C@]2(C)[C@@]1(C)C(=O)OC2=O DHZBEENLJMYSHQ-XCVPVQRUSA-N 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- XNKFCDGEFCOQOM-UHFFFAOYSA-N 1,2-dinitronaphthalene Chemical compound C1=CC=CC2=C([N+]([O-])=O)C([N+](=O)[O-])=CC=C21 XNKFCDGEFCOQOM-UHFFFAOYSA-N 0.000 description 1
- 101100433727 Caenorhabditis elegans got-1.2 gene Proteins 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- XSCFKJGIAYKLRV-UHFFFAOYSA-N n-naphthalen-1-ylnitramide Chemical class C1=CC=C2C(N[N+](=O)[O-])=CC=CC2=C1 XSCFKJGIAYKLRV-UHFFFAOYSA-N 0.000 description 1
- KHARCSTZAGNHOT-UHFFFAOYSA-N naphthalene-2,3-dicarboxylic acid Chemical compound C1=CC=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 KHARCSTZAGNHOT-UHFFFAOYSA-N 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】 本発明はペリノン系染料の改良された製造法に関する。[Detailed description of the invention] The present invention relates to an improved method for producing perinone dyes.
更に詳しくは，本発明は一般式（式中Ａはアミン基ある
いはニトロ基を表わす）にて示される１−ニトロナフタ
リン誘導体と一般（式中Ｘはハロゲン原子、ｎは０〜４
の整数をわす）にて示されるナフタリン−２，３−ジカ
ルボン酸無水物を有機酸中にて、ニトロ基を還元しうる
金属で還元縮合することを特徴とする一般式（式中Ｘは
ハロゲン原子，ｎは０〜４の整数を表わす）にて示され
るペリノン系染料の製造力法に関する。More specifically, the present invention relates to 1-nitronaphthalene derivatives represented by the general formula (wherein A represents an amine group or a nitro group) and the general formula (wherein X is a halogen atom and n is 0 to 4
A general formula characterized by reducing and condensing naphthalene-2,3-dicarboxylic anhydride represented by This invention relates to a method for manufacturing perinone dyes represented by atoms (n represents an integer from 0 to 4).
上記一般式（■）で示されるペリノン系染料は有機系合
成高分子材料の着色剤として価値ある物質であり、本発
明は上記染料を工業的に有利に製造することを目的とし
ている。The perinone dye represented by the above general formula (■) is a valuable substance as a coloring agent for organic synthetic polymer materials, and the object of the present invention is to industrially advantageously produce the above dye.
ペリノン系染料の合成には、公知の方法として，１，８
−ジアミノナフタリンをナフタリン−２，３−ジカルボ
ン酸あるいはその誘導体と、有機溶媒，例えばニトロベ
ンゼン、トリクロルベンゼン，Ｃ−ジクロルベンゼン，
モノクロルベンゼン、ピペリジン，キノリン、ビリジン
、氷酢酸あるいはこれらの溶剤の混合物中で縮合反応を
行なう方法がある。A known method for synthesizing perinone dyes is 1,8
- Diaminonaphthalene with naphthalene-2,3-dicarboxylic acid or its derivative and an organic solvent such as nitrobenzene, trichlorobenzene, C-dichlorobenzene,
There is a method of carrying out the condensation reaction in monochlorobenzene, piperidine, quinoline, pyridine, glacial acetic acid, or a mixture of these solvents.
この場合原料の１，８−ジアミノナフタリンの工業的合
成法としてはナフタリンを混酸中にてジニトロ化するこ
とにより１，８−ジニトロナフタリンおよび１，５−ジ
ニトロナフタリンの混合物を製造し，これを適当な溶剤
によって１，８−ジニトロナフタリンと１，５−ジニト
ロナフタリンを分離し，１，８−ジニトロナフタリンを
還元して、１，８−ジアミノナフタリンをうる方法があ
る（Ｐ．Ｂ．リポート：Ｐ．Ｂ．８１０２７）。In this case, the industrial synthesis method for the raw material 1,8-diaminonaphthalene is to dinitrate naphthalene in a mixed acid to produce a mixture of 1,8-dinitronaphthalene and 1,5-dinitronaphthalene, which is then There is a method of separating 1,8-dinitronaphthalene and 1,5-dinitronaphthalene with a suitable solvent and reducing 1,8-dinitronaphthalene to obtain 1,8-diaminonaphthalene (P.B. Report: P. .B.81027).
この方法によれば分離効率および還元後の分取効率がよ
くないために目的とする１，８−ジアミノナフタリンの
収率は３４％前後になり、著しく低いものである。According to this method, the yield of the target 1,8-diaminonaphthalene is around 34%, which is extremely low because the separation efficiency and the preparative efficiency after reduction are not good.
また混合ジニトロナフタリンを分別することなしに直接
還元した後目的とする１，８−ジアミノナフタリンを分
取した場合の収率は６０％であり，前者に比較して収率
の向上は認められるが工業的な製造方法としては充分で
あるとはいい難い（特開昭４７−２５１５８号）。Furthermore, when mixed dinitronaphthalene is directly reduced without fractionation and the desired 1,8-diaminonaphthalene is fractionated, the yield is 60%, which is an improvement in yield compared to the former. It cannot be said that this method is sufficient as an industrial manufacturing method (Japanese Patent Application Laid-Open No. 47-25158).
本発明者らはかかる従来法の欠点を考慮して鋭意検討し
た結果、１，８−ジニトロナフタリンを原料として，ナ
フタリン−２，３−ジカルボン酸の無水物あるいはその
ハロゲン誘導体を有機酸中にてニトロ基を還元しうる金
属で還元しつつ縮合させて上記一般式（ＩＩＩ）で示さ
れるペリノン系染料を製造する方法を見出した。The inventors of the present invention have conducted intensive studies in consideration of the shortcomings of the conventional method, and have found that using 1,8-dinitronaphthalene as a raw material, naphthalene-2,3-dicarboxylic acid anhydride or its halogen derivative is prepared in an organic acid. We have found a method for producing a perinone dye represented by the above general formula (III) by condensing the nitro group while reducing it with a reducible metal.
この方法は１，８−ジニトロナフタリンを還元して１，
８−ジアミノナフタリンを製造する工程を省略して、１
，８−ジニトロナフタリンから直接目的染料たる一般式
（１）の化合物を製造できることで，アミノ化（還元）
工程による収率の低下を防き，一段階の反応工程をもっ
て，使用する１，８−ジニトロナフタリンを高率で利用
できる利点があり、得られる染料は公知の１，８−ジア
ミノナフタリン法のものと同等であるので経済的に非常
に有利な方法である。This method reduces 1,8-dinitronaphthalene to 1,
By omitting the step of producing 8-diaminonaphthalene, 1
, 8-dinitronaphthalene can directly be used to produce the compound of general formula (1), which is the desired dye, allowing for amination (reduction).
It has the advantage of preventing a decrease in yield due to the process and making it possible to utilize the 1,8-dinitronaphthalene at a high rate through a one-step reaction process, and the dye obtained is a dye obtained by the known 1,8-diaminonaphthalene method. This is an economically very advantageous method.
α−ナフチルアミンを公知の方法でニトロ化して生成す
るニトロ−α−ナフチルアミン異性体混合物より，異性
体を分別して得られる１−ニトロ−８−アミノナフタリ
ンも更に還元することなしに本発明方法に使用できる。1-Nitro-8-aminonaphthalene obtained by separating the isomers from the nitro-α-naphthylamine isomer mixture produced by nitration of α-naphthylamine by a known method is also used in the method of the present invention without further reduction. can.
本発明で使用される一般式（■）で示される化合物は１
，８−ジニトロナフタリンおよび１−ニトロ−８−アミ
ノナフタリンである。The compound represented by the general formula (■) used in the present invention is 1
, 8-dinitronaphthalene and 1-nitro-8-aminonaphthalene.
本発明で使用しうる一般式（ｎ）で示される化合物には
ナフタリン−２，３−ジカルボン酸無水物およびそのハ
ロゲン誘導体があり、そのハロゲン置換基としては例え
ば、クロル原子，ブロム原子が挙げられる。Compounds represented by the general formula (n) that can be used in the present invention include naphthalene-2,3-dicarboxylic anhydride and its halogen derivatives, and examples of the halogen substituents include chlorine atom and bromine atom. .
かかるハロゲン置換ナフタリン−２，３−ジカルボン酸
無水物としては、
モノ−クロル−ナフタリン
−２，３−ジカルボン酸無水物
モノ−ブロム−ナフタリン
−２，３−ジカルボン酸無水物
ジ−クロルーナフタリン
−２，３−ジカルボン酸無水物
ジ−ブロム−ナフタリン
−２，３−ジカルボン酸無水物
トリ−クロル−ナフタリン
−２，３−ジカルボン酸無水物
トリ−ブロム−ナフタリン
−２，３−ジカルボン酸無水物
テトラ−クロルーナフタリン
−２，３−ジカルボン酸無水物
テトラ−ブロム−ナフタリン
−２，３−ジカルボン酸無水物
等が挙げられる。Such halogen-substituted naphthalene-2,3-dicarboxylic anhydride includes mono-chloro-naphthalene-2,3-dicarboxylic anhydride mono-bromo-naphthalene-2,3-dicarboxylic anhydride di-chloro-naphthalene-2,3-dicarboxylic anhydride; 2,3-dicarboxylic anhydride di-bromo-naphthalene-2,3-dicarboxylic anhydride tri-chloro-naphthalene-2,3-dicarboxylic anhydride tri-bromo-naphthalene-2,3-dicarboxylic anhydride Examples include tetra-chloronaphthalene-2,3-dicarboxylic anhydride, tetra-bromo-naphthalene-2,3-dicarboxylic anhydride, and the like.
還元縮合に使用される有機酸としては酢酸、プロピオン
酸等の低級有機酸であり，それぞれ単独に、あるいは混
合して使用できる。The organic acids used in the reduction condensation are lower organic acids such as acetic acid and propionic acid, which can be used alone or in combination.
ニトロ基を還元しうる金属としては，鉄、アルミニウム
等である。Examples of metals that can reduce nitro groups include iron and aluminum.
この場合アルミニウムは鉄と混合して使用する。In this case aluminum is used mixed with iron.
アルミニウムの単独使用は還元反応が行なわれ難いので
アルミニウムを使用する場合には鉄の併用が必要である
。If aluminum is used alone, it is difficult to carry out the reduction reaction, so when aluminum is used, it is necessary to use iron in combination.
この場合鉄の使用量は量的に制限されることはないが通
常有利にはニトロ基１コを還元するに必要な量の１／１
０以上の鉄を併用する。In this case, the amount of iron used is not subject to quantitative restrictions, but is usually advantageously 1/1 of the amount required to reduce one nitro group.
0 or more iron is used together.
反応は１−ニトロナフタリン誘導体と等モル量のナフタ
リン−２，３−ジカルボン酸無水物誘導体を有機酸中に
溶解あるいは懸濁させておき、ニトロ基を還元するに必
要な量の還元剤を添加して，７０℃以上において、還元
縮合を行なう。The reaction is carried out by dissolving or suspending an equimolar amount of a naphthalene-2,3-dicarboxylic anhydride derivative in an organic acid and adding the amount of reducing agent necessary to reduce the nitro group. Then, reductive condensation is carried out at 70°C or higher.
反応終了後析出せる生成物は、目的物と有機酸の金属塩
の一部が混入しているので、水洗し、また一部還元剤か
未反応のまま析出せる生成物に混在する場合には稀礦酸
例えば，硫酸等で加熱処理することにより溶解除去する
。The product that can be precipitated after the reaction is partially contaminated with the target product and the metal salt of the organic acid, so it should be washed with water, and if some of the reducing agent is mixed in the product that can be precipitated without reacting. It is dissolved and removed by heat treatment with a diluted acid such as sulfuric acid.
以下に実施例をもって本発明を説明する。The present invention will be explained below with reference to Examples.
実施例 １
１，８−ジニトロナフタリン２１．８部、ナフタリン−
２，３−ジカルボン酸無水物１９．８部、還元鉄粉３４
部を氷酢酸６７０部中にて，８時間煮沸かきまぜた。Example 1 21.8 parts of 1,8-dinitronaphthalene, naphthalene-
2,3-dicarboxylic anhydride 19.8 parts, reduced iron powder 34
1 part was boiled and stirred in 670 parts of glacial acetic acid for 8 hours.
冷却して，生成物を濾過し、２％硫酸２００部とともに
９０℃にて２時間かきまぜて濾別し，水洗乾燥して，下
記構造の染料２９部を得た。After cooling, the product was filtered, stirred with 200 parts of 2% sulfuric acid at 90° C. for 2 hours, filtered, washed with water and dried to obtain 29 parts of a dye having the following structure.
赤橙色結晶性粉末で融点は３０２．５〜３０３．５℃を
示した。It was a red-orange crystalline powder with a melting point of 302.5-303.5°C.
元素分析値は次のとおりで計算値とほぼ一致した。The elemental analysis values were as follows and almost agreed with the calculated values.
Ｃ％ Ｈ％ Ｎ％
計算値 ８２．５ ３．７５ ８．７５実測
値 ８２．２ ３．５５ ８．８実施例 ２
８−ニトロ−１−ナフチルアミン１８．８部．ナフタリ
ン−２，３−ジカルボン酸無水物１９．８部、氷酢酸６
５０部、還元鉄粉１７部を混合して，実施例１と同様に
反応処理して染料２８．８部を得た。C% H% N% Calculated value 82.5 3.75 8.75 Actual value 82.2 3.55 8.8 Example 2 18.8 parts of 8-nitro-1-naphthylamine. 19.8 parts of naphthalene-2,3-dicarboxylic anhydride, 6 parts of glacial acetic acid
50 parts of reduced iron powder and 17 parts of reduced iron powder were mixed and subjected to reaction treatment in the same manner as in Example 1 to obtain 28.8 parts of dye.
融点は３０３〜３０４℃を示した。The melting point was 303-304°C.
実施例 ３
１，８−ジニトロナフタリン２１．８部、ナフタリン−
２，３−ジカルボン酸無水物１９．８部、氷酢酸６７０
部，還元鉄粉７部、アルミニウム粉８部を混合して１３
時間煮沸して反応させた。Example 3 21.8 parts of 1,8-dinitronaphthalene, naphthalene-
19.8 parts of 2,3-dicarboxylic anhydride, 670 parts of glacial acetic acid
13 parts, 7 parts of reduced iron powder, and 8 parts of aluminum powder were mixed.
The mixture was boiled for an hour to react.
冷却後濾別して８％硫酸２００部と９０℃で加熱処理し
て染料２９部えた。After cooling, the mixture was filtered and heated at 90° C. with 200 parts of 8% sulfuric acid to obtain 29 parts of dye.
融点は３０３〜３０４．５℃を示した。The melting point was 303-304.5°C.
実施例 ４
１，８−ジニトロナフタリン２１．８部、ジブロムナフ
タリン−２，３−ジカルボン酸無水物３７部，氷酢酸７
００部、還元鉄粉３４部を混合して実施例１と同様に反
応処理して，赤褐色結晶性粉末４４部を得た。Example 4 21.8 parts of 1,8-dinitronaphthalene, 37 parts of dibromnaphthalene-2,3-dicarboxylic anhydride, 7 parts of glacial acetic acid
00 parts and 34 parts of reduced iron powder were mixed and reacted in the same manner as in Example 1 to obtain 44 parts of reddish brown crystalline powder.
このもののブロム含有率は下記の如く計算値とほぼ一致
した。The bromine content of this product almost agreed with the calculated value as shown below.
Ｂｒ％
計算値 ３３．５
実測値 ３１．５
実施例 ５
８−ニトロ−１−ナフチルアミン１８．８部，テトラブ
ロムナフタリン−２，３−ジカルボン酸無水物５２部、
氷酢酸７００部、還元鉄粉１７部，アルミニウム粉５．
４部を混合して１３時間煮沸かきまぜて反応させた。Br% Calculated value 33.5 Actual value 31.5 Example 5 18.8 parts of 8-nitro-1-naphthylamine, 52 parts of tetrabromnaphthalene-2,3-dicarboxylic acid anhydride,
700 parts of glacial acetic acid, 17 parts of reduced iron powder, 5. aluminum powder.
4 parts were mixed and reacted by boiling and stirring for 13 hours.
生成物を炉別して，８％硫・酸２５０部と９０℃で１時
間かきまぜてｐ別，水洗乾燥して、赤褐色結晶性粉末６
１部を得た。The product was separated in a furnace, stirred with 250 parts of 8% sulfuric acid at 90°C for 1 hour, separated, washed with water, and dried to give a reddish brown crystalline powder 6.
I got 1 copy.
このもののブロム分析の結果は下記の如くであり計算値
とほぼ一致した。The results of bromine analysis of this product were as shown below, and almost agreed with the calculated values.
Ｂｒ％ 計算値 ５０．３ 実測値 ４９．０Br% Calculated value 50.3 Actual value 49.0
Claims (1)
される１−ニトロナフタリン誘導体と一般式 （式中Ｘはハロゲン原子、ｎは０〜４の整数を表わす）
にて示されるナフタリン−２，３−ジカルボン酸無水物
を有機酸中にて，ニトロ基を還元しうる金属で還元縮合
することを特徴とする一般式 （式中Ｘはハロゲン原子、ｎは０〜４の整数を表わす）
にて示されるペリノン系染料の製造法。[Scope of Claims] 1 A 1-nitronaphthalene derivative represented by the general formula (wherein A represents an amino group or a nitro group) and a 1-nitronaphthalene derivative represented by the general formula (wherein X is a halogen atom and n is an integer from 0 to 4) )
The general formula (wherein X is a halogen atom and n is 0 ~ represents an integer of 4)
The method for producing perinone dyes shown in
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8378675A JPS581148B2 (en) | 1975-07-07 | 1975-07-07 | Verinon Keisenriyouno Seizouhou |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8378675A JPS581148B2 (en) | 1975-07-07 | 1975-07-07 | Verinon Keisenriyouno Seizouhou |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS526731A JPS526731A (en) | 1977-01-19 |
| JPS581148B2 true JPS581148B2 (en) | 1983-01-10 |
Family
ID=13812311
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8378675A Expired JPS581148B2 (en) | 1975-07-07 | 1975-07-07 | Verinon Keisenriyouno Seizouhou |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS581148B2 (en) |
-
1975
- 1975-07-07 JP JP8378675A patent/JPS581148B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS526731A (en) | 1977-01-19 |
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