JPH0827386A - Production of 4,4'-diamino-1,1'-dianthraquinonyl - Google Patents
Production of 4,4'-diamino-1,1'-dianthraquinonylInfo
- Publication number
- JPH0827386A JPH0827386A JP16717794A JP16717794A JPH0827386A JP H0827386 A JPH0827386 A JP H0827386A JP 16717794 A JP16717794 A JP 16717794A JP 16717794 A JP16717794 A JP 16717794A JP H0827386 A JPH0827386 A JP H0827386A
- Authority
- JP
- Japan
- Prior art keywords
- dianthraquinonyl
- diamino
- water
- sulfuric acid
- desulfonation
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/005—Di-anthraquinonyl and derivative compounds
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、赤色建染染料及び赤色
顔料として有用な４，４’−ジアミノ−１，１’−ジア
ントラキノニルの製造方法に関する。FIELD OF THE INVENTION The present invention relates to a method for producing 4,4'-diamino-1,1'-dianthraquinonyl useful as a red vat dye and a red pigment.
【０００２】[0002]
【従来の技術】４，４’−ジアミノ−１，１’−ジアン
トラキノニル−３，３’−ジスルホン酸類を鉱酸等によ
り脱スルホン化することにより、４，４’−ジアミノ−
１，１’−ジアントラキノニル顔料類を製造する方法は
公知である。例えば、特公昭３８−２５８４２号公報に
は、４，４’−ジアミノ−１，１’−ジアントラキノニ
ル−３，３’−ジスルホン酸類を鉱酸又は酸性を示す塩
とともに加熱反応して脱スルホン化し、その反応溶液を
氷水中に注ぐことにより加水分解して、目的物を得る方
法が記載されている。しかしながら、この特公昭３８−
２５８４２号公報に記載の方法で得られる４，４’−ジ
アミノ−１，１’−ジアントラキノニル顔料類は、極め
て微小な粒子であるため濾過性が非常に悪く、工業的に
不利である。また特開平５−３９４３５号公報では、濾
過性を改善する方法として、脱スルホン化後の反応溶液
を水中に注いで得られる水性懸濁液の温度が、０℃を越
えないように保持する方法が提案されている。しかし、
この方法によっても、やはり濾過性が悪く、濾過に非常
に長時間を要するため、目的物中に不純物が多く残存
し、顔料として要求される鮮明な色に欠けていた。2. Description of the Related Art 4,4'-Diamino-1,1'-dianthraquinonyl-3,3'-disulfonic acid is desulfonated with a mineral acid or the like to give 4,4'-diamino-
Methods for making 1,1'-dianthraquinonyl pigments are known. For example, in Japanese Examined Patent Publication No. 38-25842, 4,4′-diamino-1,1′-dianthraquinonyl-3,3′-disulfonic acids are heated with a mineral acid or a salt showing acidity to desulfone. And then the reaction solution is poured into ice water to be hydrolyzed to obtain the desired product. However, this Japanese Patent Publication 38-
The 4,4′-diamino-1,1′-dianthraquinonyl pigments obtained by the method described in Japanese Patent No. 25842 are extremely fine particles and therefore have very poor filterability, which is industrially disadvantageous. Further, in JP-A-5-39435, as a method of improving the filterability, a method of keeping the temperature of an aqueous suspension obtained by pouring a reaction solution after desulfonation into water so as not to exceed 0 ° C. Is proposed. But,
Even by this method, the filterability is still poor and the filtration requires a very long time, so that a large amount of impurities remain in the target product and the clear color required as a pigment is lacking.
【０００３】また一方、特開昭６３−３１２３６６号公
報では、４，４’−ジアミノ−１，１’−ジアントラキ
ノニル−３，３’−ジスルホン酸を脱スルホン化後、硫
酸塩状で単離し、該硫酸塩を水に加えて加水分解して
４，４’−ジアミノ−１，１’−ジアントラキノニル化
合物を得る方法が記載されている。しかしながら、この
方法においても、硫酸塩状で濾取、単離するに際し、脱
スルホン化後の硫酸濃度及び晶析方法によって濾過性が
著しく変化し、しかもこの段階での濾過性は、最終目的
物である４，４’−ジアミノ−１、１’−ジアントラキ
ノニル顔料の品質に大きく影響する。即ち、硫酸塩の濾
過性が悪いと、不純物が除去されず、こうして得られた
硫酸塩の加水分解で生成した目的物を濾取する際の濾過
性も不良で、不純物が残存し、鮮明な色を有する顔料は
得られない。On the other hand, in JP-A-63-312366, 4,4'-diamino-1,1'-dianthraquinonyl-3,3'-disulfonic acid is desulfonated and then converted into a sulfate salt. Separately, a method of obtaining the 4,4′-diamino-1,1′-dianthraquinonyl compound by adding the sulfate to water and hydrolyzing it is described. However, also in this method, when the sulfate salt is filtered and isolated, the filterability remarkably changes depending on the sulfuric acid concentration after the desulfonation and the crystallization method, and the filterability at this stage is The quality of 4,4'-diamino-1,1'-dianthraquinonyl pigment is significantly affected. That is, if the filterability of the sulfate salt is poor, the impurities are not removed, and the filterability of the target product produced by the hydrolysis of the sulfate salt thus obtained is poor, and the impurities remain and are clear. Colored pigments are not obtained.
【０００４】[0004]
【発明が解決しようとする課題】本発明の目的は、上記
のような問題点を解決し、不純物が効率よく除去され、
鮮明な色を有する４，４’−ジアミノ−１，１’−ジア
ントラキノニルを製造し得る、作業性に優れた工業的に
有利な方法を提供することにある。SUMMARY OF THE INVENTION The object of the present invention is to solve the above problems and to remove impurities efficiently.
An object of the present invention is to provide an industrially advantageous method capable of producing 4,4′-diamino-1,1′-dianthraquinonyl having a bright color and having excellent workability.
【０００５】[0005]
【課題を解決するための手段】本発明者らは、上記の目
的を達成するため鋭意検討した結果、本発明に到達し
た。即ち、本発明は、４，４’−ジアミノ−１，１’−
ジアントラキノニル−３，３’−ジスルホン酸又はその
塩を硫酸を用いて脱スルホン化し、４，４’−ジアミノ
−１，１’−ジアントラキノニルを製造する方法におい
て、脱スルホン化後水で希釈して硫酸濃度を７０〜８０
％とし、７０〜１１０℃に冷却し、その温度で静置して
保温熟成させ、生成した硫酸塩を単離し、該硫酸塩を水
中に注ぐことにより加水分解することを特徴とする、
４，４’−ジアミノ−１，１’−ジアントラキノニルの
製造方法である。The present inventors have arrived at the present invention as a result of extensive studies to achieve the above object. That is, the present invention relates to 4,4′-diamino-1,1′-
In the method for producing 4,4′-diamino-1,1′-dianthraquinonyl by desulfonation of dianthraquinonyl-3,3′-disulfonic acid or a salt thereof with sulfuric acid, after desulfonation, water is used. Dilute sulfuric acid concentration to 70-80
%, Cooled to 70 to 110 ° C., allowed to stand at that temperature for heat retention aging, and the sulfate salt produced is isolated and hydrolyzed by pouring the sulfate salt into water.
This is a method for producing 4,4'-diamino-1,1'-dianthraquinonyl.
【０００６】以下、本発明について詳細に説明する。本
発明で用いる４，４’−ジアミノ−１，１’−ジアント
ラキノニル−３，３’−ジスルホン酸の塩としては、ナ
トリウム、カリウムなどのアルカリ金属、マグネシウ
ム、カルシウム、バリウムなどのアルカリ土類金属、亜
鉛、アルミニウムなどの低毒性の金属などの塩を例示で
きる。Hereinafter, the present invention will be described in detail. The salt of 4,4′-diamino-1,1′-dianthraquinonyl-3,3′-disulfonic acid used in the present invention includes alkali metals such as sodium and potassium, alkaline earth metals such as magnesium, calcium and barium. Examples thereof include salts of metals and low-toxicity metals such as zinc and aluminum.
【０００７】本発明においては、４，４’−ジアミノ−
１，１’−ジアントラキノニル−３，３’−ジスルホン
酸又はその塩を硫酸中にて脱スルホン化する。硫酸濃度
は通常９０％以下、好ましくは７５〜８０％であり、反
応温度は１２０〜２２０℃、好ましくは１４０〜１５０
℃である。In the present invention, 4,4'-diamino-
1,1'-dianthraquinonyl-3,3'-disulfonic acid or its salt is desulfonated in sulfuric acid. The sulfuric acid concentration is usually 90% or less, preferably 75 to 80%, and the reaction temperature is 120 to 220 ° C, preferably 140 to 150.
° C.
【０００８】本発明においては、得られた脱スルホン化
した反応溶液を水で希釈して硫酸濃度を７０〜８０％、
好ましくは７０〜７５％とした後、反応溶液を７０〜１
１０℃に冷却し、この温度に保持して、静置して保温熟
成し、結晶を析出させる。熟成時間は反応のスケールに
よっても異なるが、通常０．５〜２０時間、好ましくは
５〜１５時間である。熟成終了後、必要であれば更に冷
却して４０〜８０℃とし、濾過して硫酸塩を単離する。
脱スルホン化後、水で希釈した後の硫酸濃度、及び自然
冷却し、静置保温する熟成工程が、濾過性を改善させ、
目的物の色相を向上させる上で非常に重要である。即
ち、水で希釈して適切な硫酸濃度に調整することによ
り、不純物を晶析母液に溶解させて、４，４’−ジアミ
ノ−１，１’−ジアントラキノニル硫酸塩（以下、「硫
酸塩」と略す）への不純物の取込みを抑え、また自然冷
却したのち静置保温する熟成工程を設けることで、硫酸
塩の結晶を大きく成長させるという効果を有するものと
推測される。この２つの効果によって、硫酸塩を単離す
る際の濾過性は飛躍的に向上し、不純物は効率よく除去
され、鮮明な色相の目的物が得られる。In the present invention, the resulting desulphonated reaction solution is diluted with water to a sulfuric acid concentration of 70 to 80%,
After preferably 70-75%, the reaction solution is 70-1
The mixture is cooled to 10 ° C., kept at this temperature, and allowed to stand to be heat-aged for aging to precipitate crystals. The aging time varies depending on the scale of the reaction, but is usually 0.5 to 20 hours, preferably 5 to 15 hours. After completion of the aging, if necessary, the mixture is further cooled to 40 to 80 ° C., and the sulfate is isolated by filtration.
After desulfonation, the sulfuric acid concentration after dilution with water, and the aging step of naturally cooling and keeping still temperature improve filterability,
It is very important in improving the hue of the target product. That is, the impurities are dissolved in the crystallization mother liquor by diluting with water and adjusting to an appropriate sulfuric acid concentration, and 4,4′-diamino-1,1′-dianthraquinonyl sulfate (hereinafter, “sulfate It is presumed that it has an effect of largely growing sulfate crystals by suppressing the incorporation of impurities into (), and by providing an aging step of naturally cooling and then keeping the temperature still. By these two effects, the filterability at the time of isolating the sulfate is dramatically improved, the impurities are efficiently removed, and the target product having a clear hue is obtained.
【０００９】本発明においては、単離した硫酸塩は、６
０〜８０％の硫酸にて洗浄した後、水中に注入すること
により加水分解し、これを濾取して、目的物である４，
４’−ジアミノ−１，１’−ジアントラキノニルを得
る。この最終段階での濾過においても濾過性は良好で、
短時間で終了する。In the present invention, the isolated sulfate salt is 6
After washing with 0-80% sulfuric acid, it is hydrolyzed by pouring it into water, and this is collected by filtration to obtain the desired product, 4,
4'-Diamino-1,1'-dianthraquinonyl is obtained. Even in the final stage of filtration, the filterability is good,
Finish in a short time.
【００１０】[0010]
【実施例】以下、実施例により本発明を更に具体的に説
明する。尚、得られた化合物の展色試験は下記の方法で
行う。 １．実施例で得られた化合物４．０ｇに樹脂（ベッコゾ
ールＪ−５２４−ＩＭ−６０：スーパーベッカミンＪ−
８２０−６０＝７０：３０の比で混合したもの（樹脂は
共に第日本インキ（株）製））１３ｇ、溶剤（キシレ
ン：ｎ−ブタノール＝７５：２５の比で混合したもの）
１３ｇを加え、１時間分散させ、再度樹脂５０ｇを追加
後１０分間分散させ、色エナメルを作製する。 ２．１のエナメルを濃度試験用のカード紙（商品名：ブ
ラッシュＴ、中越パルプ工業社製）にアプリケータで均
一の厚みに展色する。 ３．３０分間放置し、１３０℃、２０分間焼き付ける。 ４．比較例１で合成した化合物をスタンダードとし、こ
れを同様に試験用カード紙に焼きつけたものと比較する
ことにより色相を評価する。The present invention will be described in more detail with reference to the following examples. The color development test of the obtained compound is carried out by the following method. 1. 4.0 g of the compound obtained in the example was added to a resin (Beccosol J-524-IM-60: Super Beckamine J-.
820-60 = 70: 30 mixed together (resins are both manufactured by Nippon Ink Co., Ltd.) 13 g, solvent (xylene: n-butanol = 75: 25 mixed together)
13 g is added and dispersed for 1 hour, and 50 g of resin is added again and dispersed for 10 minutes to prepare a colored enamel. The enamel of 2.1 is applied to a card paper for density test (Brand name: Blush T, manufactured by Chuetsu Pulp Industry Co., Ltd.) with an applicator to have a uniform thickness. 3. Leave for 30 minutes and bake at 130 ° C for 20 minutes. 4. The compound synthesized in Comparative Example 1 is used as a standard, and the hue is evaluated by comparing it with that which is similarly burned on a test card paper.
【００１１】実施例１ ９８％硫酸１９１ｇ中に水４９ｇを入れ７８％硫酸を調
整し、この７８％硫酸液を室温とし、４，４’−ジアミ
ノ−１，１’−ジアントラキノニル−３，３’−ジスル
ホン酸ナトリウム３０ｇを、５０℃以下に保持しながら
装入した。装入終了後、１５０℃まで昇温し、同温度で
３時間反応し、脱スルホン化を行った。その後、水２
７．４ｇを加えて硫酸濃度を７０％とし、自然放冷によ
り３０〜４０分かけて１０５℃まで冷却し、攪拌を停止
して静置し、１００〜１０５℃に保持して１０時間熟成
した。その後５０℃まで冷却して吸引濾過し、７０％硫
酸１００ｇにてプレスケーキの洗浄を行った。洗浄後、
プレスケーキを敷水８００部中に装入し、室温にて１時
間攪拌し、吸引濾過、水洗、乾燥して４，４’−ジアミ
ノ−１，１’−ジアントラキノニル１６．５ｇ（収率８
１％）を得た。硫酸塩および最終目的物の濾過性はとも
に非常に良好で、濾過は１分程で終了し、展色試験の結
果、得られた４，４’−ジアミノ−１，１’−ジアント
ラキノニルは、スタンダードに比べて鮮明赤色の色相を
呈した。Example 1 49 g of water was added to 191 g of 98% sulfuric acid to adjust 78% sulfuric acid, and this 78% sulfuric acid solution was brought to room temperature to obtain 4,4'-diamino-1,1'-dianthraquinonyl-3, 30 g of sodium 3'-disulfonate was charged while maintaining the temperature at 50 ° C or lower. After the completion of charging, the temperature was raised to 150 ° C. and the reaction was carried out at the same temperature for 3 hours to carry out desulfonation. Then water 2
7.4 g was added to adjust the sulfuric acid concentration to 70%, and the mixture was naturally cooled to 105 ° C. over 30 to 40 minutes, the stirring was stopped and allowed to stand, and the mixture was kept at 100 to 105 ° C. and aged for 10 hours. . Then, the mixture was cooled to 50 ° C., suction-filtered, and the presscake was washed with 100 g of 70% sulfuric acid. After washing
The press cake is charged in 800 parts of water and stirred at room temperature for 1 hour, suction filtered, washed with water and dried to give 16.5 g of 4,4′-diamino-1,1′-dianthraquinonyl (yield. 8
1%) was obtained. Both the sulfate salt and the final target product had very good filterability, and the filtration was completed in about 1 minute. As a result of the color development test, the 4,4'-diamino-1,1'-dianthraquinonyl obtained was , Showed a brighter red hue than the standard.
【００１２】実施例２ 実験例１と同様に、４，４’−ジアミノ−１，１’−ジ
アントラキノニル−３，３’−ジスルホン酸ナトリウム
の脱スルホン化を行い、脱スルホン化後、水９．６ｇを
加えて硫酸濃度を７５％とし、自然放冷により１時間か
けて８５℃まで冷却し、攪拌を停止して静置し、８０〜
８５℃に保持して５時間熟成した。その後５０℃まで冷
却して吸引濾過し、７５％硫酸１００ｇにてプレスケー
キの洗浄を行った。洗浄後、プレスケーキを敷水８００
部中に装入し、室温にて１時間攪拌し、吸引濾過、水
洗、乾燥して４，４’−ジアミノ−１，１’−ジアント
ラキノニル１３．８ｇ（収率６７％）を得た。硫酸塩お
よび最終目的物の濾過性はともに非常に良好で、濾過は
１分程で終了し、展色試験の結果、得られた４，４’−
ジアミノ−１，１’−ジアントラキノニルは、スタンダ
ードに比べて鮮明赤色の色相を呈した。Example 2 As in Experimental Example 1, sodium 4,4'-diamino-1,1'-dianthraquinonyl-3,3'-disulfonate was desulfonated, and after desulfonation, water was added. 9.6 g was added to adjust the sulfuric acid concentration to 75%, and the mixture was naturally cooled to 85 ° C. over 1 hour.
It was kept at 85 ° C and aged for 5 hours. Then, the mixture was cooled to 50 ° C., suction filtered, and the presscake was washed with 100 g of 75% sulfuric acid. After washing, spread the press cake with water 800
The mixture was charged into a batch, stirred at room temperature for 1 hour, suction filtered, washed with water, and dried to obtain 13.8 g (yield 67%) of 4,4′-diamino-1,1′-dianthraquinonyl. . Both the sulfate and the final target product had very good filterability, and the filtration was completed in about 1 minute.
Diamino-1,1'-dianthraquinonyl exhibited a bright red hue as compared to the standard.
【００１３】比較例１ 実施例１と同様に４，４’−ジアミノ−１，１’−ジア
ントラキノニル−３，３’−ジスルホン酸ナトリウムの
脱スルホン化を行い、脱スルホン化後、水４８ｇを加え
て硫酸濃度を６５％とし、自然放冷により３０〜４０分
かけて１０５℃まで冷却し、攪拌を停止して１００〜１
０５℃に保持して１０時間熟成した。その後５０℃まで
冷却して、吸引濾過し、６５％硫酸１００ｇにてプレス
ケーキの洗浄を行った。洗浄後、プレスケーキを敷水８
０ｇ中に装入、室温にて１時間攪拌し、吸引濾過、水
洗、乾燥して４，４’−ジアノ−１，１’−ジアントラ
キノニル１５．４ｇ（収率７５％）を得た。硫酸塩及び
最終目的物の濾過性はともに不良で、濾過に５分程度要
し、得られた４，４’−ジアミノ−１，１’−ジアント
ラキノニルは青みがかった暗赤色を呈していた。Comparative Example 1 Sodium 4,4'-diamino-1,1'-dianthraquinonyl-3,3'-disulfonate was desulfonated in the same manner as in Example 1, and after desulfonation, 48 g of water was added. Was added to adjust the sulfuric acid concentration to 65%, and the mixture was naturally cooled to 105 ° C. over 30 to 40 minutes.
It was kept at 05 ° C and aged for 10 hours. Then, the mixture was cooled to 50 ° C., suction filtered, and the press cake was washed with 100 g of 65% sulfuric acid. After washing, spread the press cake with water 8
It was charged in 0 g, stirred at room temperature for 1 hour, suction filtered, washed with water, and dried to obtain 15.4 g (yield 75%) of 4,4′-diano-1,1′-dianthraquinonyl. Both the sulfate and the final target product were poor in filterability, and it took about 5 minutes for filtration, and the obtained 4,4′-diamino-1,1′-dianthraquinonyl had a bluish dark red color.
【００１４】比較例２ 実施例１と同様に４，４’−ジアミノ−１，１’−ジア
ントラキノニル−３，３’−ジスルホン酸ナトリウムの
脱スルホン化を行い、脱スルホン化後、水２７．４ｇを
加えて硫酸濃度を７０％とし、その後５０℃まで急冷し
て濾過し、７０％硫酸１００ｇにてプレスケーキの洗浄
を行った。その後、プレスケーキを敷水８００ｇ中に装
入、室温にて１時間攪拌し、濾過、水洗、乾燥して４，
４’−ジアミノ−１，１’−ジアントラキノニル１６．
０ｇ（収率７９％）を得た。硫酸塩及び最終目的物の濾
過性はともに不良で、濾過に２０分程度要し、得られた
４，４’−ジアミノ−１，１’−ジアントラキノニルは
青みがかった暗赤色を呈していた。Comparative Example 2 As in Example 1, sodium 4,4'-diamino-1,1'-dianthraquinonyl-3,3'-disulfonate was desulfonated, and after desulfonation, water 27 was added. 0.4 g was added to adjust the sulfuric acid concentration to 70%, and then the mixture was rapidly cooled to 50 ° C. and filtered, and the presscake was washed with 100 g of 70% sulfuric acid. After that, the press cake is charged into 800 g of spread water, stirred at room temperature for 1 hour, filtered, washed with water, dried, and
4'-diamino-1,1'-dianthraquinonyl 16.
0 g (yield 79%) was obtained. Both the sulfate and the final target product were poor in filterability, and it took about 20 minutes to filter, and the obtained 4,4′-diamino-1,1′-dianthraquinonyl had a bluish dark red color.
【００１５】[0015]
【発明の効果】本発明により、不純物が効率よく除去さ
れ、鮮明な色相を有する、赤色建染染料及び顔料として
有用な４，４’−ジアミノ−１，１’−ジアントラキノ
ニルを製造し得る、作業性に優れた工業的に有利な方法
を提供することができた。INDUSTRIAL APPLICABILITY According to the present invention, 4,4'-diamino-1,1'-dianthraquinonyl useful as a red vat dye and a pigment having a clear hue with impurities efficiently removed can be produced. It was possible to provide an industrially advantageous method with excellent workability.
Claims (1)
トラキノニル−３，３’−ジスルホン酸又はその塩を硫
酸を用いて脱スルホン化し、４，４’−ジアミノ−１，
１’−ジアントラキノニルを製造する方法において、脱
スルホン化後水で希釈して硫酸濃度を７０〜８０％と
し、７０〜１１０℃に冷却し、その温度で静置して保温
熟成させ、生成した硫酸塩を単離し、該硫酸塩を水中に
注ぐことにより加水分解することを特徴とする、４，
４’−ジアミノ−１，１’−ジアントラキノニルの製造
方法。1. 4,4′-Diamino-1,1′-dianthraquinonyl-3,3′-disulfonic acid or a salt thereof is desulfonated with sulfuric acid to obtain 4,4′-diamino-1,
In the method for producing 1'-dianthraquinonyl, after desulfonation, the mixture is diluted with water to a sulfuric acid concentration of 70 to 80%, cooled to 70 to 110 ° C, and allowed to stand at that temperature for heat aging to form the product. The sulfates are isolated and hydrolyzed by pouring the sulfates into water.
Process for producing 4'-diamino-1,1'-dianthraquinonyl.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6167177A JP2987057B2 (en) | 1994-07-19 | 1994-07-19 | Process for producing 4,4'-diamino-1,1'-dianthraquinonyl |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6167177A JP2987057B2 (en) | 1994-07-19 | 1994-07-19 | Process for producing 4,4'-diamino-1,1'-dianthraquinonyl |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0827386A true JPH0827386A (en) | 1996-01-30 |
| JP2987057B2 JP2987057B2 (en) | 1999-12-06 |
Family
ID=15844854
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6167177A Expired - Lifetime JP2987057B2 (en) | 1994-07-19 | 1994-07-19 | Process for producing 4,4'-diamino-1,1'-dianthraquinonyl |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2987057B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5801972B1 (en) * | 2015-01-16 | 2015-10-28 | 大日精化工業株式会社 | Pigment composition and coloring composition using the same |
| JP5801976B1 (en) * | 2015-03-31 | 2015-10-28 | 大日精化工業株式会社 | Method for producing pigment composition |
-
1994
- 1994-07-19 JP JP6167177A patent/JP2987057B2/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5801972B1 (en) * | 2015-01-16 | 2015-10-28 | 大日精化工業株式会社 | Pigment composition and coloring composition using the same |
| JP5801976B1 (en) * | 2015-03-31 | 2015-10-28 | 大日精化工業株式会社 | Method for producing pigment composition |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2987057B2 (en) | 1999-12-06 |
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