JPS593491B2 - Method for manufacturing triphenodioxazine dye - Google Patents
Method for manufacturing triphenodioxazine dyeInfo
- Publication number
- JPS593491B2 JPS593491B2 JP10127676A JP10127676A JPS593491B2 JP S593491 B2 JPS593491 B2 JP S593491B2 JP 10127676 A JP10127676 A JP 10127676A JP 10127676 A JP10127676 A JP 10127676A JP S593491 B2 JPS593491 B2 JP S593491B2
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- formula
- manufacturing
- triphenodioxazine
- group
- 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
- AHWXCYJGJOLNFA-UHFFFAOYSA-N [1,4]benzoxazino[2,3-b]phenoxazine Chemical compound O1C2=CC=CC=C2N=C2C1=CC1=NC3=CC=CC=C3OC1=C2 AHWXCYJGJOLNFA-UHFFFAOYSA-N 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 238000000034 method Methods 0.000 title description 2
- 238000007363 ring formation reaction Methods 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 239000000047 product Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-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
- 125000003545 alkoxy group Chemical group 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- -1 polyethylene terephthalate Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 150000005109 triphenodioxazines Chemical class 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 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
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000212749 Zesius chrysomallus Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Landscapes
- Coloring (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Description
【発明の詳細な説明】
本発明は下記一般式（Ｉ）
（式中、Ｘは塩素原子又は臭素原子、Ｙは（０Ｒ′）Ｎ
ＯＲ基、Ｒ′はＣ，〜４アルキレン基、ＲはＣ，〜４ア
ルキル基を示し、ｎは１又は２である。Detailed Description of the Invention The present invention is based on the following general formula (I) (wherein, X is a chlorine atom or a bromine atom, and Y is (0R')N
OR group, R' represents a C,~4 alkylene group, R represents a C,~4 alkyl group, and n is 1 or 2.
（式中、Ｘ，Ｒ，Ｒ′，ｎは前示一般式（１）における
と同一の意義を有する。）で表わされるトリフエノジオ
キサジン系染料が良好な収率で得られる。A triphenodioxazine dye represented by the formula (wherein X, R, R', and n have the same meanings as in the general formula (1) above) can be obtained in a good yield.
しかしながら、参考までに説明すれ（人前記一般式（１
）において、Ｙが水素原子の場合、閉環反応は一般に、
酸性縮合剤を必要とする。酸性縮合剤は目的の閉環反応
を促進すると同時に、一般式（１）におけるアルコキシ
基のエーテル結炙で表わされる化合物を有機媒体中にお
いて、閉環反応を行なうことを特徴とする下記一般式（
）（式中、Ｘ，Ｒ，Ｒ／及びｎは前示一般式（Ｉ）にお
けると同一の意義を有する。）で表わされるトリフエノ
ジオキサジン系染料の製造方法に係るものである。However, for reference, let me explain (the above general formula (1)
), when Y is a hydrogen atom, the ring-closing reaction is generally
Requires acidic condensing agent. The acidic condensing agent promotes the desired ring-closing reaction and at the same time carries out the ring-closing reaction of the compound represented by the ether linkage of the alkoxy group in the general formula (1) in an organic medium.
) (wherein, X, R, R/ and n have the same meanings as in the general formula (I) above).
本発明を詳細に説明するに、一般式（１）におけるｘと
しては、塩素原子、臭素原子のようなハロゲン原子が挙
げられる。To explain the present invention in detail, x in the general formula (1) includes halogen atoms such as chlorine atom and bromine atom.
又、（０Ｒ′）ＮＯＲで表わされるアルコキシ基の具体
例としては、０ＣＨ２ＣＨ２０ＣＨ２ＣＨ２０Ｃ４Ｈ９
（ｎ）などが挙げられるＯ本発明は次のようにして行な
われる。Further, as a specific example of the alkoxy group represented by (0R')NOR, 0CH2CH20CH2CH20C4H9
(n) etc. The present invention is carried out as follows.
即ち、一般式（１）で表わされる化合物を有機醇媒中で
１０００Ｃ以上、好ましくは１３０〜２５０℃で酸性縮
合剤の存在下あるいは非存在下に加熱することにより閉
環反応を行なう。この場合、本発明のように前記一般式
（１）において、Ｙが（０Ｒ′）。０Ｒ基の場合には、
酸性縮合剤の非存在下でも閉環反応は容易に進行し、下
記一般式（川）反応に用いられる適当な有機溶媒として
は、場合によつてはハロゲン化及び（または）ニトロ化
されているベンゼン系芳香族炭化水素、例えばトルエン
、キシレン、モノクロロベンゼン、ｏ−ジクロロベンゼ
ン、トリクロロベンゼン、ニトロベンゼン、ｏ−ニトロ
トルエン、ナフタレン、α−クロロナフタレン、α−メ
チルナフタレンなどが挙げられる。That is, the ring-closing reaction is carried out by heating the compound represented by the general formula (1) in an organic solvent at 1000C or higher, preferably 130 to 250C, in the presence or absence of an acidic condensing agent. In this case, as in the present invention, Y in the general formula (1) is (0R'). In the case of 0R group,
The ring-closing reaction proceeds easily even in the absence of an acidic condensing agent, and suitable organic solvents for use in the reaction of the following general formula include benzene, which may be halogenated and/or nitrated as the case may be. Examples of aromatic hydrocarbons include toluene, xylene, monochlorobenzene, o-dichlorobenzene, trichlorobenzene, nitrobenzene, o-nitrotoluene, naphthalene, α-chloronaphthalene, and α-methylnaphthalene.
又これ等の他、キノリン、ピコリン、Ｎ，Ｎ−ジメチル
ホルムアミド、ジメチルスルホキシド、Ｎ−メチルピロ
リドン、スルホランなども用いることができる。酸性縮
合剤としては、カルボン酸およびスルホン酸の酸塩化物
、例えばベンゾイルクロライド、ベンゼンスルホニルク
ロライド、ｐ−トルエンスルホニルクロライドの他、チ
オニルクロライド、五塩化リン、塩酸、臭化水素酸、無
水酢酸、ｐトルエンスルホン酸、または金属塩化物、例
えば塩化アルミニウムまたは塩化亜鉛などが挙げられる
。In addition to these, quinoline, picoline, N,N-dimethylformamide, dimethylsulfoxide, N-methylpyrrolidone, sulfolane, etc. can also be used. Examples of acidic condensing agents include acid chlorides of carboxylic acids and sulfonic acids, such as benzoyl chloride, benzenesulfonyl chloride, p-toluenesulfonyl chloride, as well as thionyl chloride, phosphorus pentachloride, hydrochloric acid, hydrobromic acid, acetic anhydride, and p-toluenesulfonyl chloride. Examples include toluenesulfonic acid, or metal chlorides such as aluminum chloride or zinc chloride.
反応の進行の様子は、例えば薄層クロマトグラフイ一な
どにより追跡することができる。The progress of the reaction can be monitored by, for example, thin layer chromatography.
閉環反応終了後、冷却することにより一般に目的の反応
生成物は結晶として析出してくるので、そのものを涙取
すれば良い。目的物が反応洛媒に対して大きな醇解度を
持つ場合には、例えばメタノールのような目的物に対す
る溶解力の小さな洛媒を加え、目的物を析出させること
により淵取することができる。After the completion of the ring-closing reaction, the desired reaction product generally precipitates as crystals by cooling, so it is sufficient to collect the crystals. When the target product has a high solubility in the reaction medium, the target product can be separated out by adding a solvent such as methanol that has a low dissolving power to the target product.
本発明方法によつて得られるトリフエノジオキサジン系
染料はそれ自身新規な染料であり、ポリエチレンテレフ
タレート、セルロースアセテートに対して優れた親和性
を有し、耐光堅牢度の優れた非常に鮮明な赤色色調の染
色物を与える。The triphenodioxazine dye obtained by the method of the present invention is itself a new dye, and has an excellent affinity for polyethylene terephthalate and cellulose acetate, and is a very vivid red color with excellent light fastness. Gives tonal dyeing.
なお、前記一般式（１）で表わされる化合物は、テトラ
ハロゲノｐ−ベンゾキノン類と下記一般式（ｌ）（式中
、Ｒ，Ｒ′，Ｙ，ｎは前示一般式（１）におけると同一
の意義を有する。）で表わされるアニリン類を縮合させ
ることによつて得られる。The compound represented by the above general formula (1) is a tetrahalogeno p-benzoquinone and the following general formula (l) (wherein R, R', Y, and n are the same as in the above general formula (1)). It can be obtained by condensing anilines represented by
以下本発明を実施例により詳細に説明するが、本発明は
その要旨を超えない限り、以下の実施例に制約されるも
のではない。EXAMPLES The present invention will be explained in detail below with reference to examples, but the present invention is not limited to the following examples unless it exceeds the gist thereof.
実施例 １
下記構造式
で表わされる化合物２ｇをニトロベンゼン２０ｍ１中で
環流下１０時間反応し、冷却後析出物を濾取し、下記構
造式で表わされるジオキサジン系化合物の純品１．０ｇ
を得た。Example 1 2 g of the compound represented by the following structural formula was reacted in 20 ml of nitrobenzene under reflux for 10 hours, and after cooling, the precipitate was collected by filtration to obtain 1.0 g of a pure dioxazine compound represented by the following structural formula.
I got it.
本品は融点２９６〜２９８℃の赤褐色結晶で、元素分析
結果は次のとおり計算値と良く合致した。This product is a reddish-brown crystal with a melting point of 296-298°C, and the elemental analysis results agreed well with the calculated values as shown below.
／く実施例 ２
下記構造式
イ
ｏし、下記構造式
タ本品は融点２４１〜２４３℃の赤褐色結晶で元素分析
結果は次のとおり計算値と良く合致した。Example 2 The product has the following structural formula (i) and the following structural formula (t).This product is a reddish-brown crystal with a melting point of 241 to 243°C, and the elemental analysis results were in good agreement with the calculated values as shown below.
ネ参考例下記構造式
た結果（担体・・・シリカゲル、展開溶媒・・・ベンゼ
ン：酢酸エチル＝３：１）、３，１０−ジアルコキシ−
６，１３−ジハロゲノトリフエノジオキサジン類に特有
の蛍光性の赤色の多くのスポツトが表われた。Reference example The following structural formula results (support: silica gel, developing solvent: benzene:ethyl acetate = 3:1), 3,10-dialkoxy-
Many fluorescent red spots characteristic of 6,13-dihalogenotriphenodioxazines appeared.
又このものを濃硫酸に牌解したところ、トリフエノジオ
キサジン類に特有の青色に呈色した。これらのことより
得られた赤褐色結晶は、トリフエノジオキサジン系化合
物の混合物であることが明らかである。When this product was dissolved in concentrated sulfuric acid, it developed a blue color characteristic of triphenodioxazines. It is clear from these results that the reddish brown crystals obtained are a mixture of triphenodioxazine compounds.
又このもののマススペクトルを測定した結果、ｍ／ｅ−
JモV４，７７２，７７０，７３０，７２８，７２６，７
２４，７２２，６８６，６８４，６８２，６８０，６７
８，６７６，６７４にピークが検出された。Also, as a result of measuring the mass spectrum of this material, m/e-
Jmo V4,772,770,730,728,726,7
24,722,686,684,682,680,67
A peak was detected at 8,676,674.
Claims (1)
は塩素原子又は臭素原子、Ｙは（ＯＲ′）＿ｎＯＲ基、
Ｒ′はＣ＿１〜＿４アルキレン基、ＲはＣ＿１〜＿４ア
ルキル基を示し、ｎは１又は２である。 ）で表わされる化合物を有機媒体中において、閉環反応
を行なうことを特徴とする下記一般式（II）▲数式、化
学式、表等があります▼（II）（式中、Ｘ、Ｒ、Ｒ′及
びｎは前示一般式（ I ）におけると同一の意義を有す
る。 ）で表わされるトリフェノジオキサジン系染料の製造方
法。[Claims] 1 The following general formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula,
is a chlorine atom or a bromine atom, Y is a (OR')_nOR group,
R' represents a C_1-_4 alkylene group, R represents a C_1-_4 alkyl group, and n is 1 or 2. ) The following general formula (II) is characterized by carrying out a ring-closing reaction in an organic medium. There are mathematical formulas, chemical formulas, tables, etc. (II) (wherein, n has the same meaning as in the general formula (I).) A method for producing a triphenodioxazine dye represented by the formula (I).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10127676A JPS593491B2 (en) | 1976-08-25 | 1976-08-25 | Method for manufacturing triphenodioxazine dye |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10127676A JPS593491B2 (en) | 1976-08-25 | 1976-08-25 | Method for manufacturing triphenodioxazine dye |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5326826A JPS5326826A (en) | 1978-03-13 |
| JPS593491B2 true JPS593491B2 (en) | 1984-01-24 |
Family
ID=14296344
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10127676A Expired JPS593491B2 (en) | 1976-08-25 | 1976-08-25 | Method for manufacturing triphenodioxazine dye |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS593491B2 (en) |
-
1976
- 1976-08-25 JP JP10127676A patent/JPS593491B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5326826A (en) | 1978-03-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Grayshan et al. | Heterocyclic derivalives of naphthalene‐1, 8‐dicar boxylie anhydride. Part III. Benzo [k, l] thioxanthene‐3, 4‐dicarboximides | |
| CN112174989B (en) | A kind of preparation method of crisborole | |
| US4401585A (en) | Bis(p-alkylphenylethynyl)anthracene | |
| JPS61127766A (en) | Hetero-polycyclic aromatic compound | |
| CN106478626A (en) | One class quinacridone derivative and preparation method and application | |
| JPH05209132A (en) | Tryptanthrine derivative | |
| JPH01160957A (en) | Bis(indoryl)ethylene | |
| JPS593491B2 (en) | Method for manufacturing triphenodioxazine dye | |
| Huntress et al. | The Synthesis of Aminobenzoyleneureas and of Dihydroxyquinoxalines Isomeric with “Luminol” | |
| US3936477A (en) | Blue anthraquinoid disperse dyes, their production and use | |
| US4011224A (en) | Process for the preparation of 7-oxo-7H-dibenzo-[d e,h]-quinolin-2-ol | |
| JPS5851024B2 (en) | Yushiyokukagobutsunoseizouhou | |
| US4011227A (en) | O-(3-hydroxy-1-isoquinolinyl)-benzoic acid | |
| US4219651A (en) | Benzimidazo-[1,2-a]-quinolines | |
| JP3000110B2 (en) | Tetrahydroquinacridine derivative and method for producing the same | |
| US5401846A (en) | Preparation of 5-halo-2-(1-anthraquinonylamino)-benzoic acids and 4'-halo-2,1(N)-anthraquinonyl-1',2'(N)-benzacridones | |
| JPS609503B2 (en) | Tetrachlornaphthalic acid imide derivative and its production method | |
| JPS606377B2 (en) | Method for producing heterocyclic dyes | |
| JPH041160A (en) | 3-aminophenol derivative and production thereof | |
| JPH02204473A (en) | Preparation of 1-amino-2-bromo-4-hydroxy-anthraquinone | |
| JPS594411B2 (en) | naphthalic acid derivatives | |
| JPS5941466B2 (en) | Manufacturing method of azamethine dye | |
| JPH04164037A (en) | Production of acetylene derivative | |
| JPS5838468B2 (en) | Kinophthalon Keikagobutsu no Seizouhou | |
| JPS5851025B2 (en) | Kinophthalonkeikagobutsunoseizouhouhou |