JPS5851026B2 - naphtoyl range benzimidazole - Google Patents
naphtoyl range benzimidazoleInfo
- Publication number
- JPS5851026B2 JPS5851026B2 JP10046175A JP10046175A JPS5851026B2 JP S5851026 B2 JPS5851026 B2 JP S5851026B2 JP 10046175 A JP10046175 A JP 10046175A JP 10046175 A JP10046175 A JP 10046175A JP S5851026 B2 JPS5851026 B2 JP S5851026B2
- Authority
- JP
- Japan
- Prior art keywords
- parts
- acid
- nitro
- orthonitroaniline
- naphtoyl
- 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
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 title 1
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical class NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 claims description 6
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- 239000000843 powder Substances 0.000 description 13
- 229960000583 acetic acid Drugs 0.000 description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- 239000004793 Polystyrene Substances 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- OLAPPGSPBNVTRF-UHFFFAOYSA-N naphthalene-1,4,5,8-tetracarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1C(O)=O OLAPPGSPBNVTRF-UHFFFAOYSA-N 0.000 description 6
- 229920002223 polystyrene Polymers 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 238000006482 condensation reaction Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- DLURHXYXQYMPLT-UHFFFAOYSA-N 2-nitro-p-toluidine Chemical compound CC1=CC=C(N)C([N+]([O-])=O)=C1 DLURHXYXQYMPLT-UHFFFAOYSA-N 0.000 description 2
- PBGKNXWGYQPUJK-UHFFFAOYSA-N 4-chloro-2-nitroaniline Chemical compound NC1=CC=C(Cl)C=C1[N+]([O-])=O PBGKNXWGYQPUJK-UHFFFAOYSA-N 0.000 description 2
- ISFYBUAVOZFROB-UHFFFAOYSA-N 4-ethoxy-2-nitroaniline Chemical compound CCOC1=CC=C(N)C([N+]([O-])=O)=C1 ISFYBUAVOZFROB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- -1 carbon atom orthonitroaniline derivatives Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 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 2
- 239000007858 starting material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- FCMRHMPITHLLLA-UHFFFAOYSA-N 2-methyl-6-nitroaniline Chemical compound CC1=CC=CC([N+]([O-])=O)=C1N FCMRHMPITHLLLA-UHFFFAOYSA-N 0.000 description 1
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
- QFMJFXFXQAFGBO-UHFFFAOYSA-N 4-methoxy-2-nitroaniline Chemical compound COC1=CC=C(N)C([N+]([O-])=O)=C1 QFMJFXFXQAFGBO-UHFFFAOYSA-N 0.000 description 1
- FQPPKORVTBLTBX-UHFFFAOYSA-N 5-iodo-2-nitroaniline Chemical compound NC1=CC(I)=CC=C1[N+]([O-])=O FQPPKORVTBLTBX-UHFFFAOYSA-N 0.000 description 1
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
本発明はナフトレンジベンツイミダゾール系染料の改良
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 naphthrene dibenzimidazole dyes.
更に詳細には、本発明は１・４・５・８−ナフタリンテ
トラカルボン酸またはその無水物と、一般式
（式中Ｒは水素、
ハロゲン、炭素原子数２以下の※
アルキル基または炭素原子数２以下のアルコキシ基を表
わす）にて表わされるオルトニトロアニリン誘導体を、
有機酸中にて、ニトロ基を還元しうる金属で還元縮合す
ることからなる一般式（式中Ｒは前述したとおりである
）にて表わされるシスおよび／またはトランス異性体の
ナフトイレンジベンツイミダゾール系染料の製造法にあ
る。More specifically, the present invention relates to 1,4,5,8-naphthalenetetracarboxylic acid or its anhydride, and the general formula (wherein R is hydrogen, halogen, an alkyl group having 2 or less carbon atoms, or a carbon atom orthonitroaniline derivatives represented by (representing 2 or less alkoxy groups),
Cis and/or trans isomer naphthoylene dibenzimidazole represented by the general formula (in the formula, R is as described above) consisting of reductive condensation of a nitro group with a reducible metal in an organic acid. It is in the manufacturing method of dyes.
ナフトイレンジベンツイミダゾール系染料の合成には公
知の方法として、■・４・５・８−ナフタリンテトラカ
ルボン酸またはその無水物と、オルトジアミノベンゼン
誘導体を、酢酸中にて反応させる方法がある。A known method for synthesizing naphthoylene dibenzimidazole dyes is a method in which 4-4-5-8-naphthalenetetracarboxylic acid or its anhydride is reacted with an orthodiaminobenzene derivative in acetic acid.
この場合の出発物質の一つであるオルトジアミノベンゼ
ン誘導体は、オルトニトロアニリン誘導体を還元するこ
とにて得られる。An orthodiaminobenzene derivative, which is one of the starting materials in this case, can be obtained by reducing an orthonitroaniline derivative.
この方法は作業工程も長く、各工程での損失も避けられ
ず、収率低下をもたらし、経済的に満足できる方法とは
いえない。This method requires long working steps, and losses are inevitable in each step, leading to a decrease in yield, and it cannot be said to be an economically satisfactory method.
本発明の方法によれば、上述したオルトジアミノベンゼ
ン誘導体を使用せずに、その原料であるオルトニトロア
ニリン誘導体を直接出発物質と使用でき、これを原料と
して還元および縮合を一段階で行なうことができ、上記
公知の方法と比較して作業工程が短縮される上に、製造
装置も簡略化され、原料損失も少なく、経済的に非常に
有利な方法である。According to the method of the present invention, the raw material, orthonitroaniline derivative, can be used directly as a starting material without using the above-mentioned orthodiaminobenzene derivative, and reduction and condensation can be carried out in one step using this raw material. Compared to the above-mentioned known methods, the working steps are shortened, the manufacturing equipment is simplified, and there is less loss of raw materials, making it an economically very advantageous method.
本発明で使用されるオルトアニリン誘導体としては例え
ばオルトニトロアニリン自体；３−二トロー４−アニン
ジン、３−ニトロ−４−フェネチジン等のアルコキシ−
オルトニトロアニリン；３ニトロ−２−アミノトルエン
、３−ニトロ−４アミノ−トルエン、３−ニトロ−４−
アミノエチルベンゼン等のアルキル−オルトニトロアニ
リン；２−ニトロ−４−クロルアニリン、２−ニトロ−
５−クロルアニリン、２〜ニトロ−４−フロムアニリン
、２−ニトロ−５−ヨードアニリン等のハロゲン化オル
トニトロアニリンがある。Examples of orthoaniline derivatives used in the present invention include orthonitroaniline itself; alkoxy derivatives such as 3-nitro-4-anidine and 3-nitro-4-phenetidine
Orthonitroaniline; 3-nitro-2-aminotoluene, 3-nitro-4-amino-toluene, 3-nitro-4-
Alkyl-orthonitroaniline such as aminoethylbenzene; 2-nitro-4-chloroaniline, 2-nitro-
There are halogenated orthonitroanilines such as 5-chloroaniline, 2-nitro-4-fromaniline, and 2-nitro-5-iodoaniline.
反応に使用しうる有機酸としては例えば濃度８０％以上
の酢酸またはプロピオン酸がある、中でも酢酸が好まし
い。Examples of organic acids that can be used in the reaction include acetic acid or propionic acid with a concentration of 80% or more, with acetic acid being preferred.
ニトロ基の還元に使用しうる金属としては還元鉄がある
。Reduced iron is a metal that can be used to reduce the nitro group.
還元縮合反応は一工程で進行させることができる。The reduction condensation reaction can proceed in one step.
即ち例えば１・４・５・８−ナフタリンテトラカルボン
酸あるいはその無水物１モルとオルトニトロアニリン誘
導体２モルとを、有機酸中で、ニトロ基を還元するのに
必要な理論量ないし僅かに過剰な量の還元鉄粉を加え、
８０℃以上の温度で攪拌しながら、還元を行なうと、縮
合反応も同時に進行する。That is, for example, 1 mole of 1,4,5,8-naphthalenetetracarboxylic acid or its anhydride and 2 moles of an orthonitroaniline derivative are mixed in an organic acid in a stoichiometric amount to a slight excess necessary for reducing the nitro group. Add a suitable amount of reduced iron powder,
When the reduction is carried out while stirring at a temperature of 80° C. or higher, the condensation reaction also proceeds at the same time.
アミノ基が消失したとき、生成した染料を取出し、稀薄
な無機酸で熱処理することにより残存還元鉄を溶出させ
る。When the amino groups disappear, the resulting dye is taken out and heat treated with dilute inorganic acid to elute the remaining reduced iron.
か（して得られたナフトイレンジベンツイミダゾール系
染料は前述した如（シス異性体とトランス異性体の混合
物である。The naphthoylene dibenzimidazole dye obtained as described above is a mixture of cis and trans isomers.
この混合物はこのままで、あるいは所望により公知の方
法例えばアルコール性苛性カリ溶液により各異性体を分
離することができる。This mixture can be used as it is, or if desired, the isomers can be separated by a known method such as an alcoholic potassium hydroxide solution.
かくして得られた本発明による染料は微粒子化、例えば
硫酸に溶解させ、次いで多量の氷水中に投入して再沈殿
させ、戸数して微粒子化したものは、建染染料あるいは
顔料として有機高分子材料の橙色から赤褐色乃至ボルド
色の赤色系の着色剤と有用性を有する。The thus obtained dye according to the present invention is made into fine particles, for example, dissolved in sulfuric acid, and then poured into a large amount of ice water to be reprecipitated. It is useful as a red coloring agent ranging from orange to reddish brown to bold.
以下実施例を挙げて本発明を説明する。The present invention will be explained below with reference to Examples.
文中部とあるのは重量部である。The text section indicates the weight section.
実施例 １
１・４・５・８−ナフタリンテトラカルボン酸３０部、
オルトニトロアニリン２８部を、氷酢酸６００部中に入
れ、還元鉄粉３５部を加えて、煮沸攪拌した。Example 1 30 parts of 1,4,5,8-naphthalenetetracarboxylic acid,
28 parts of orthonitroaniline was placed in 600 parts of glacial acetic acid, 35 parts of reduced iron powder was added, and the mixture was boiled and stirred.
この時の温度は１１５〜１１７℃を示した。The temperature at this time was 115-117°C.
２時間後更に内温を１２０℃に上昇させた。Two hours later, the internal temperature was further raised to 120°C.
このとき内圧が若干加わった。この状態で５時間攪拌し
て冷却し、内温９０℃になったとき濾過した。At this time, some internal pressure was added. The mixture was stirred in this state for 5 hours, cooled, and filtered when the internal temperature reached 90°C.
形成された生成物を３％塩酸２００部と共に９０°Ｃに
加熱して濾過、湯洗して乾燥した。The product formed was heated to 90° C. with 200 parts of 3% hydrochloric acid, filtered, washed with hot water and dried.
得られた生成物はスカレートの粉末３８．７部であった
。The product obtained was 38.7 parts of scalate powder.
これはシス体とトランス体の混合物で、構造はＣ１■、
７１１１０と同一であった。This is a mixture of cis and trans forms, and the structure is C1■,
It was the same as 71110.
このものはポリスチロールをスカーレットに着色した。This one is polystyrene colored scarlet.
実施例 ２
８５％酢酸６００部中に、１・４・５・８−ナフタリン
テトラカルボン酸３０部、４−クロル２−ニトロアニリ
ン３５部と還元鉄粉３５部を加え、２時間煮沸攪拌した
。Example 2 30 parts of 1,4,5,8-naphthalenetetracarboxylic acid, 35 parts of 4-chloro2-nitroaniline, and 35 parts of reduced iron powder were added to 600 parts of 85% acetic acid, and the mixture was boiled and stirred for 2 hours.
次いで内温を１２０℃に上昇させた、このとき内圧が若
干加わった。Next, the internal temperature was raised to 120°C, at which time internal pressure was slightly added.
この状態で５時間攪拌し、冷却して内温９０℃に戸別し
、生成物を５％硫酸２００部と共に９０℃に加熱して沢
過し、湯洗して乾燥した。The mixture was stirred in this state for 5 hours, cooled to an internal temperature of 90° C., heated to 90° C. with 200 parts of 5% sulfuric acid, filtered, washed with hot water, and dried.
かくして赤褐色粉末４５部を得た。Thus, 45 parts of reddish brown powder was obtained.
このものはＣ，Ｉ。７１１１５と同一であった。This one is C,I. It was the same as 71115.
ポリスチロールを赤褐色に着色した。The polystyrene was colored reddish brown.
実施例 ３
９０％酢酸６００部中に１・４・５・８−ナフタリンテ
トラカルボン酸３０部、４−メチル−２ニトロアニリン
３０部、還元鉄粉３５部を加えて２時間攪拌し、以下実
施例１と同様に処理した。Example 3 30 parts of 1,4,5,8-naphthalenetetracarboxylic acid, 30 parts of 4-methyl-2-nitroaniline, and 35 parts of reduced iron powder were added to 600 parts of 90% acetic acid, stirred for 2 hours, and carried out below. It was treated in the same manner as in Example 1.
暗褐色粉末４１．５部を得た。41.5 parts of dark brown powder were obtained.
このものはポリスチロールを赤褐色に着色した。This product colored polystyrene reddish brown.
実施例 ４
氷酢酸６００部中に１・４・５・８−ナフタリンテトラ
カルボン酸３０部、４−メトキシ−２ニトロアニリン３
４部、還元鉄粉３５部を加えて以下実施例１と同様に処
理した。Example 4 30 parts of 1,4,5,8-naphthalenetetracarboxylic acid, 3 parts of 4-methoxy-2-nitroaniline in 600 parts of glacial acetic acid
4 parts and 35 parts of reduced iron powder were added, and the following treatment was carried out in the same manner as in Example 1.
得られたものは暗褐色の粉末４４部を得た。The result was 44 parts of a dark brown powder.
このものはポリスチロールを赤褐色に着色した。This product colored polystyrene reddish brown.
実施例 ５
氷酢酸６００部中に、４−エトキシ−２−ニトロアニリ
ン３６部、■・４・５・８−ナフタリンテトラカルボン
酸３０部、還元鉄粉３５部を加えて、実施例１と同様に
処理した。Example 5 The same procedure as in Example 1 was carried out by adding 36 parts of 4-ethoxy-2-nitroaniline, 30 parts of 4-5-8-naphthalene tetracarboxylic acid, and 35 parts of reduced iron powder to 600 parts of glacial acetic acid. processed.
かくして暗赤褐色粉末４６部を得た。46 parts of a dark reddish-brown powder were thus obtained.
構造はＣ１１，７１１２０と同一であった。The structure was identical to C11,71120.
このものはポリスチロールを赤褐色に着色した。This product colored polystyrene reddish brown.
実施例 ６
８０％酢酸６００部中に、４−エトキシ−２ニトロアニ
リン３６部、■・４・５・８−ナフタリンテトラカルボ
ン酸二無水物２７部、還元鉄粉３５部を加えて、実施例
１と同様に還元縮合反応を行ない、処理した。Example 6 36 parts of 4-ethoxy-2-nitroaniline, 27 parts of 4-4-5-8-naphthalene tetracarboxylic dianhydride, and 35 parts of reduced iron powder were added to 600 parts of 80% acetic acid. A reduction condensation reaction was carried out in the same manner as in 1.
か（して暗赤褐色の粉末４７部を得た。(47 parts of a dark reddish brown powder was obtained.
構造はＣ６■、７１１２０と同一であった。The structure was the same as C6■, 71120.
このものはポリスチロールを赤褐色に着色した。This product colored polystyrene reddish brown.
実施例 ７
実施例１において酢酸の代りにプロピオン酸６００部を
使用して実施例１と同様に反応および処理を行なった。Example 7 The reaction and treatment were carried out in the same manner as in Example 1 except that 600 parts of propionic acid was used instead of acetic acid.
Claims (1)
その無水物と、一般式 （式中Ｒは水素、ハロゲン、炭素原子数２以下のアルキ
ル基または炭素原子数２以下のアルコキシ基を表わす）
にて表わされるオルトニトロアニリン誘導体を、有機酸
中にて、ニトロ基を還元シうる金属で還元縮合すること
を特徴とする一般式（式中Ｒは前述したとおりである）
で表わされるナフトレンジベンツイミダゾール系染料の
製造法。[Scope of Claims] 11,4,5,8-naphthalenetetracarboxylic acid or its anhydride; (represents an alkoxy group)
A general formula characterized in that an orthonitroaniline derivative represented by is reductively condensed with a metal capable of reducing a nitro group in an organic acid (in the formula, R is as described above)
A method for producing a naphthrene dibenzimidazole dye represented by
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10046175A JPS5851026B2 (en) | 1975-08-18 | 1975-08-18 | naphtoyl range benzimidazole |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10046175A JPS5851026B2 (en) | 1975-08-18 | 1975-08-18 | naphtoyl range benzimidazole |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5224225A JPS5224225A (en) | 1977-02-23 |
| JPS5851026B2 true JPS5851026B2 (en) | 1983-11-14 |
Family
ID=14274537
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10046175A Expired JPS5851026B2 (en) | 1975-08-18 | 1975-08-18 | naphtoyl range benzimidazole |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5851026B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070134572A1 (en) * | 2005-12-12 | 2007-06-14 | Xerox Corporation | Photoconductive members |
| CN102634226A (en) * | 2011-02-11 | 2012-08-15 | 张争鸣 | Preparation method for vat scarlet |
-
1975
- 1975-08-18 JP JP10046175A patent/JPS5851026B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5224225A (en) | 1977-02-23 |
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