JPS5857461B2 - Method for producing cyanotriphenodioxazine dye - Google Patents
Method for producing cyanotriphenodioxazine dyeInfo
- Publication number
- JPS5857461B2 JPS5857461B2 JP9055476A JP9055476A JPS5857461B2 JP S5857461 B2 JPS5857461 B2 JP S5857461B2 JP 9055476 A JP9055476 A JP 9055476A JP 9055476 A JP9055476 A JP 9055476A JP S5857461 B2 JPS5857461 B2 JP S5857461B2
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- group
- cyanide
- producing
- dye
- 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
- 238000004519 manufacturing process Methods 0.000 title description 2
- JIIVFISVEDAQRR-UHFFFAOYSA-N [1,4]benzoxazino[2,3-b]phenoxazine-1-carbonitrile Chemical compound O1C2=CC3=NC4=CC=CC=C4OC3=CC2=NC2=C1C=CC=C2C#N JIIVFISVEDAQRR-UHFFFAOYSA-N 0.000 title 1
- -1 cyanide compound Chemical class 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 19
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 7
- 239000000975 dye Substances 0.000 description 5
- 238000004809 thin layer chromatography Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical group CN1CCCC1=O SECXISVLQFMRJM-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
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- ICAIHGOJRDCMHE-UHFFFAOYSA-O ammonium cyanide Chemical compound [NH4+].N#[C-] ICAIHGOJRDCMHE-UHFFFAOYSA-O 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 125000004806 1-methylethylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
- KQMCGGGTJKNIMC-UHFFFAOYSA-N 2-hydroxy-3-propyl-2h-furan-5-one Chemical compound CCCC1=CC(=O)OC1O KQMCGGGTJKNIMC-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000279 calcium ferrocyanide Substances 0.000 description 1
- 235000012251 calcium ferrocyanide Nutrition 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- 229940076286 cupric acetate Drugs 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- UMTFPTCPRUEQHM-UHFFFAOYSA-N dicyanolead Chemical compound N#C[Pb]C#N UMTFPTCPRUEQHM-UHFFFAOYSA-N 0.000 description 1
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000000276 potassium ferrocyanide Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- LFAGQMCIGQNPJG-UHFFFAOYSA-N silver cyanide Chemical compound [Ag+].N#[C-] LFAGQMCIGQNPJG-UHFFFAOYSA-N 0.000 description 1
- 229940098221 silver cyanide Drugs 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- XOGGUFAVLNCTRS-UHFFFAOYSA-N tetrapotassium;iron(2+);hexacyanide Chemical compound [K+].[K+].[K+].[K+].[Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] XOGGUFAVLNCTRS-UHFFFAOYSA-N 0.000 description 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Coloring (AREA)
Description
【発明の詳細な説明】
本発明は新規なジオキサジン系染料の製造方法に係るも
のである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel method for producing dioxazine dyes.
更に詳しくは、本発明は次の一般式（Ｉ）（式中、Ｘは
ハロゲン原子を、Ｒは低級アルキル基、低級アルコキシ
アルキル基を、Ｒ′は低級アルキレン基を示す）で表わ
されるシアノ基を含有するトリフエツジオキサジン系染
料を工業的有利＊＊に製造することを目的とするもので
ある。More specifically, the present invention relates to a cyano group represented by the following general formula (I) (wherein, X represents a halogen atom, R represents a lower alkyl group or lower alkoxyalkyl group, and R' represents a lower alkylene group). The purpose of this invention is to industrially advantageously produce triphatedioxazine dyes containing the following.
しかしてこの目的は、本発明方法に従って、の一般式（
ＩＩ）
次
（式中、Ｘ、Ｒ２Ｒ′は前売一般式（Ｉ）におけると同
一の意義を有する。However, the purpose of this is that according to the method of the invention, the general formula (
II) The following formula (wherein, X and R2R' have the same meanings as in General Formula (I)).
）で表わされる化合物を有機媒体中において金属シアン
化合物と反応させることにより達成される。) in an organic medium with a metal cyanide.
本発明を更に詳細に説明するに、一般式（Ｉ）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、Ｒとしてはメチル基、エチル基、プロピル
基、ブチル基のような低級アルキル基、β−メトキシエ
チル基、β−エトキシエチル基、β−プロポキシエチル
基、β−ブトキシエチル基のような低級アルコキシアル
キル基が挙げられる。To explain the present invention in more detail, X in the general formula (I) includes a halogen atom such as a chlorine atom and a bromine atom, and R includes a methyl group, an ethyl group, a propyl group, and a butyl group. and lower alkoxyalkyl groups such as β-methoxyethyl group, β-ethoxyethyl group, β-propoxyethyl group, and β-butoxyethyl group.
Ｒ′としては、メチレン基、エチレン基、トリメチレン
基、３−メチルトリメチレン基、１−メチルエチレン基
のような低級アルキレン基が挙げられる。Examples of R' include lower alkylene groups such as methylene, ethylene, trimethylene, 3-methyltrimethylene, and 1-methylethylene.
本発明は具体的には次のようにして行なわれる。Specifically, the present invention is carried out as follows.
つまり前売一般式（ＩＩ）で表わされる化合物を金属シ
アン化物、特にシアン化第−銅またはそれを生成する化
合物とともに溶媒に溶解または懸濁し加熱する。That is, the compound represented by the general formula (II) is dissolved or suspended in a solvent together with a metal cyanide, particularly cupric cyanide, or a compound producing it, and heated.
反応の進行の様子は薄層クロマトグラフィーによって観
察することができるが、通常前売一般式（Ｉ）における
Ｘで表わされるハロゲン原子がシアノ基で置換された目
的化合物と同時にハロゲン原子が水素で置換された化合
物が副生じてくることが観察される。The progress of the reaction can be observed by thin layer chromatography, but it is common to obtain a target compound in which the halogen atom represented by It is observed that some compounds are produced as by-products.
加熱を適当な段階で停止させ、冷却後、水を加えて析出
した反応生成物を済取する。Heating is stopped at an appropriate stage, and after cooling, water is added to collect the precipitated reaction product.
シアン化第−銅のような加剰のシアン化金属またはハロ
ゲン化金属は公知の方法に従い、シアン化アンモニウム
またはアルカリ金属を用いて水溶性金属塩に変えること
により、または、第一銅塩をたとえば塩化第二鉄によっ
て水溶性第二銅塩に酸化することにより、生成した目的
物から分離することができる。Excess metal cyanides or metal halides, such as cupric cyanide, can be removed by converting them into water-soluble metal salts using ammonium cyanide or alkali metals, or by converting cuprous salts into water-soluble metal salts, such as by converting cuprous salts into water-soluble metal salts using ammonium cyanide or alkali metals, according to known methods. By oxidizing it to a water-soluble cupric salt with ferric chloride, it can be separated from the target product produced.
反応生成物は通常目的化合物である前売一般式（Ｉ）で
表わされる化合物の他に、ハロゲン原子が水素原子で置
換された下記一般式％式％（）
（（ＩＩＩ） 、 （ＩＶ） 、 （Ｖ）の式中のＲ，
Ｋ及び（１）の式中のＸは前売一般式（１）におけると
同一の意義を有する。In addition to the compound represented by the general formula (I), which is the target compound, the reaction product is usually a compound represented by the following general formula (%) ((III), (IV), () in which the halogen atom is replaced with a hydrogen atom. R in the formula V),
K and X in the formula (1) have the same meanings as in the general formula (1).
）で表わされる化合物の混合物として得られる。) is obtained as a mixture of compounds represented by
これらの混合物から目的の化合物を得るためには薄層ク
ロマトグラフィーあるいはカラムクロマトグラフィーな
どの手段を用いることができる。In order to obtain the target compound from these mixtures, means such as thin layer chromatography or column chromatography can be used.
反応の溶媒としては、特に極性の非プロトン性溶媒、例
えば、ジメチルホルムアミド、Ｎ−メチルピロリ下ン、
ホルムアミド、ジメチルアセトアミド、ピリジン、キノ
リン、アセトニトリル、ベンゾニトリル、リン酸−トリ
ス−ジメチルアミド、ジメチルスルホキシド、スルホラ
ン等が適している。As solvent for the reaction, in particular polar aprotic solvents such as dimethylformamide, N-methylpyrrolidine,
Formamide, dimethylacetamide, pyridine, quinoline, acetonitrile, benzonitrile, phosphoric acid-tris-dimethylamide, dimethylsulfoxide, sulfolane and the like are suitable.
特に有利な溶媒はＮ−メチルピロリドンである。A particularly preferred solvent is N-methylpyrrolidone.
金属シアン化物としては、シアン化第−銅のほか、シア
ン化銀、シアン化鉛、フェロシアン化カリウム、フェロ
シアン化カルシウム、フェロシアン化銅、シアン化亜鉛
か好適である。Suitable metal cyanides include cupric cyanide, silver cyanide, lead cyanide, potassium ferrocyanide, calcium ferrocyanide, copper ferrocyanide, and zinc cyanide.
これらのうち、シアン化第−銅がその高い反応性によっ
て特に優れている。Among these, cupric cyanide is particularly outstanding due to its high reactivity.
☆☆ これはそのま
ま反応に用いられるが、反応媒質中でそれを生成する手
段を用いてもよく、たとえば反応媒質にシアン化アルカ
リと適当な第二銅塩、−たとえば硫酸第二銅または酢酸
第二銅を添加しても良い。☆☆ It can be used as is in the reaction, but means for producing it in the reaction medium may also be used, for example by adding an alkali cyanide and a suitable cupric salt, such as cupric sulfate or cupric acetate, to the reaction medium. Copper may also be added.
反応において、反応温度は広範囲に変えることができる
が、有機溶媒及び一般式（ＩＩ）で表わされる出発化合
物の構造に関係する。In the reaction, the reaction temperature can vary within a wide range, but is dependent on the organic solvent and the structure of the starting compound of general formula (II).
一般に温度は２０〜２５０°Ｃ１好ましくは１３０〜２
１０℃である。Generally the temperature is 20-250°C, preferably 130-2
The temperature is 10°C.
本発明方法によって得られる一般式（１）で表わされる
化合物は、それ自体新規なトリフエツジオキサジン系染
料であり、ポリエチレンテレフタレーート、セルロース
アセテートに対して優れた親和性を有し、耐光性の優れ
た非常に鮮明な赤色色調の染色物を与える。The compound represented by the general formula (1) obtained by the method of the present invention is itself a novel triphatedioxazine dye, has excellent affinity for polyethylene terephthalate and cellulose acetate, and has excellent light resistance. Gives dyeings with excellent and very vivid red tones.
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Ｆの実施例に制御約されるもの
ではない。The present invention will be explained in detail below using examples, but the present invention is not limited to the following examples unless the gist of the invention is exceeded.
実施例 １ 下記構造式 で表わされる化合物２ｇ、 シアン化第−銅６ｇを メチルピロリ １７４０ｍ１中に加え還流丁３時 間反応させた。Example 1 Structural formula below 2g of the compound represented by 6g of cupric cyanide Methyl pylori In addition to 1740 m1, 3 o'clock reflux It was allowed to react for a while.
冷却後、反応液を水中に注ぎ析出物を済取した。After cooling, the reaction solution was poured into water to collect the precipitate.
このものを塩化第二鉄１８ｇ、濃塩酸９０１ｒＬｌを水
５００ｒＩＬｌに加えた溶液中６０℃で１時間攪拌した
。This product was stirred at 60° C. for 1 hour in a solution of 18 g of ferric chloride and 901 rLl of concentrated hydrochloric acid in 500 rLl of water.
冷却後、吸引済過し、得られた′ケーキを水で洗浄し、
乾燥することにより原料化合物（１−Ａ）及び下記構造
式（１−Ｂ）。After cooling, suction and filtration were performed, and the resulting cake was washed with water.
By drying, the raw material compound (1-A) and the following structural formula (1-B) are obtained.
（１−Ｃ） 、 （１−Ｄ） 、 （１−Ｅ） 、 （
１−Ｆ）で表わされる化合物の混合物を得た。(1-C), (1-D), (1-E), (
A mixture of compounds represented by 1-F) was obtained.
これらの化合物の構造は混合物から薄層クロマトグラフ
ィーで各々の成分を分取した後、元素分析及びマススペ
クトロメトリーにより確認した。The structures of these compounds were confirmed by elemental analysis and mass spectrometry after separating each component from the mixture by thin layer chromatography.
（１−Ｂ） 、 （１−Ｃ） 、 （１−Ｄ） 。(1-B), (1-C), (1-D).
（１−Ｅ） 、 （１−Ｆ）の化合物は各々単独である
いは混合物のままで、ポリエステル繊維を堅牢度・の優
れた鮮明な赤色〜紫色に染めた。The compounds (1-E) and (1-F) were used alone or as a mixture to dye polyester fibers in bright red to purple colors with excellent fastness.
実施例 ２
下記構造式
で表わされる化合物２ ｆｌ ｓシアン化第−銅６ｇを
Ｎ−メチルピロリドン４０−中に加え還流下１時間反応
させた。Example 2 Compound 2 fl s 6 g of cupric cyanide represented by the following structural formula was added to 40 mm of N-methylpyrrolidone and reacted under reflux for 1 hour.
冷却後、実施例１と同様の方法で処理して原料化合物（
２−Ａ）及び下記構造式％式％）
（２）
で表わされる化合物の混合物を得た。After cooling, the raw material compound (
A mixture of compounds represented by 2-A) and the following structural formula (%) (2) was obtained.
これらの化合物の構造は混合物から薄層クロマトグラフ
ィーで各々の成分を分取した後、元素分析及びマススペ
クトロメトリーにより確認した。The structures of these compounds were confirmed by elemental analysis and mass spectrometry after separating each component from the mixture by thin layer chromatography.
（２−Ｂ） 、 （２−Ｃ） 、 （２−Ｄ） 。(2-B), (2-C), (2-D).
（２−Ｅ） 、 （２−Ｆ）の化合物は各々単独である
いは混合物のままで、ポリエステル繊維を堅牢度の優れ
た鮮明な赤色〜紫色に染めた。The compounds (2-E) and (2-F) were used alone or as a mixture to dye polyester fibers in bright red to purple colors with excellent fastness.
Claims (1)
キル基、Ｃ２〜６アルコキシアルキル基をＲ′は低級ア
ルキレン基を示す。 ）で表わされる化合物を、有機媒体中において金属シア
ン化合物と反応させることを特徴とする下記一般式（Ｉ
） （式中、Ｘ、Ｒ，Ｒ′は前売一般式（ＩＩ）におけると
同一の意義を有する。 ）で表わされるシアノ基を含有するトリフエツジオキサ
ジン系染料の製造方法。[Scope of Claims] 1 The following general formula (II) (wherein, X represents a chlorine atom or a bromine atom, R represents a C1-4 alkyl group or a C2-6 alkoxyalkyl group, and R' represents a lower alkylene group. ) is reacted with a metal cyanide compound in an organic medium.
) (wherein, X, R, and R' have the same meanings as in the general formula (II)).
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9055476A JPS5857461B2 (en) | 1976-07-29 | 1976-07-29 | Method for producing cyanotriphenodioxazine dye |
| CH918477A CH631732A5 (en) | 1976-07-27 | 1977-07-25 | METHOD FOR PRODUCING NEW CYANOTRIPHENODIOXAZINE COMPOUNDS AND THEIR USE. |
| DE19772733539 DE2733539A1 (en) | 1976-07-27 | 1977-07-25 | TRIPHENODIOXAZINE COMPOUNDS, THEIR PRODUCTION AND USE |
| US05/818,841 US4116623A (en) | 1976-07-27 | 1977-07-25 | Cyanotriphenodioxazine compound |
| FR7722922A FR2359842A1 (en) | 1976-07-27 | 1977-07-26 | DERIVATIVES OF CYANOTRIPHENODIOXAZINE, THEIR PRODUCTION PROCESSES AND DYES THEREOF |
| GB31609/77A GB1567810A (en) | 1976-07-27 | 1977-07-27 | Cyanotriphenodioxazine compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9055476A JPS5857461B2 (en) | 1976-07-29 | 1976-07-29 | Method for producing cyanotriphenodioxazine dye |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5316038A JPS5316038A (en) | 1978-02-14 |
| JPS5857461B2 true JPS5857461B2 (en) | 1983-12-20 |
Family
ID=14001618
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9055476A Expired JPS5857461B2 (en) | 1976-07-27 | 1976-07-29 | Method for producing cyanotriphenodioxazine dye |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5857461B2 (en) |
-
1976
- 1976-07-29 JP JP9055476A patent/JPS5857461B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5316038A (en) | 1978-02-14 |
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