JPH086046B2 - Method for producing disazo compound - Google Patents
Method for producing disazo compoundInfo
- Publication number
- JPH086046B2 JPH086046B2 JP9337888A JP9337888A JPH086046B2 JP H086046 B2 JPH086046 B2 JP H086046B2 JP 9337888 A JP9337888 A JP 9337888A JP 9337888 A JP9337888 A JP 9337888A JP H086046 B2 JPH086046 B2 JP H086046B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- parts
- general formula
- acid
- 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 - Lifetime
Links
- -1 disazo compound Chemical class 0.000 title claims description 19
- 238000004519 manufacturing process Methods 0.000 title description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000000047 product Substances 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
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WYRNRZQRKCXPLA-UHFFFAOYSA-N 3-(n-ethylanilino)propanenitrile Chemical compound N#CCCN(CC)C1=CC=CC=C1 WYRNRZQRKCXPLA-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229920006239 diacetate fiber Polymers 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000004744 fabric Substances 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
- 239000002609 medium Substances 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- SQYNKIJPMDEDEG-UHFFFAOYSA-N paraldehyde Chemical compound CC1OC(C)OC(C)O1 SQYNKIJPMDEDEG-UHFFFAOYSA-N 0.000 description 1
- 229960003868 paraldehyde Drugs 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920006304 triacetate fiber Polymers 0.000 description 1
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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/04—Disazo dyes from a coupling component "C" containing a directive amino group
- C09B31/043—Amino-benzenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Photoreceptors In Electrophotography (AREA)
Description
【発明の詳細な説明】 産業上の利用分野 本発明はジスアゾ化合物の製造方法に関する。TECHNICAL FIELD The present invention relates to a method for producing a disazo compound.
従来の技術 ヘテロ環含有ジスアゾ化合物の製造方法に関しては、
特開昭51−41734、特開昭57−125263、特開昭59−19746
4など数多く報告がなされている。しかしながらそれら
のいずれの方法においても目的とするジスアゾ化合物を
高収率、高純度で得る事はでない。又、高収率、高純度
を達成し得る方法として特開昭58−129059の方法が報告
されている。この方法においてはカップラーであるジフ
エニルメタン系アミンを合成する時にホルムアルデヒド
を使用する必要があり人体及び環境への影響を考えると
好ましい方法とは言いがたい。Prior Art Regarding the method for producing a heterocycle-containing disazo compound,
JP-A-51-41734, JP-A-57-125263, JP-A-59-19746
There are many reports such as 4. However, it is not possible to obtain the target disazo compound in high yield and high purity by any of these methods. Further, as a method capable of achieving high yield and high purity, the method disclosed in JP-A-58-129059 has been reported. In this method, formaldehyde must be used when synthesizing a diphenylmethane amine as a coupler, and it is hard to say that it is a preferable method considering the effects on the human body and the environment.
発明が解決しようとする課題 ヘテロ環含有ジスアゾ化合物を製造する方法において
目的物が高収率、高純度で得られかつ人体、環境に悪い
影響を与えるおそれの少ない製造方法の開発が望まれて
いる。DISCLOSURE OF THE INVENTION Problems to be Solved by the Invention In the method for producing a heterocycle-containing disazo compound, it is desired to develop a production method in which the target product can be obtained in high yield and high purity, and the human body and the environment are less likely to have adverse effects. .
課題を解決する為の手段 本発明者らは前記したような課題を解決すべく鋭意研
究を重ねた結果、本発明に至った。即ち本発明は一般式
（II） 〔式（II）においてＤは （X1,X2は夫々独立に水素原子、ハロゲン原子、低級ア
ルキル基、ニトロ基、トリフロロメチル基、低級アルコ
キシカルボニル基、低級アルコキシ基又はヒドロキシ基
を表す）又は を表す。〕 で示されるアミン類をジアゾ化し、一般式（III） 〔式（III）においてR1,R2は夫々独立に水素原子、置
換もしくは非置換のアルキル基、アルケニル基又はアリ
ール基を、Ｚは水素、メチル基又はＣ１〜２のアシルア
ミノ基を表す〕 で示されるジフエニルエタン系アミン類とカップリング
させることを特徴とする一般式（ｌ） 〔式（ｌ）においてD,R1,R2及びＺは前記と同じ意味
を表す〕 で示されるジスアゾ化合物の製造方法を提供するもの
である。Means for Solving the Problems The present inventors have achieved the present invention as a result of earnest researches for solving the above problems. That is, the present invention has the general formula (II) [In the formula (II), D is (X 1 and X 2 each independently represent a hydrogen atom, a halogen atom, a lower alkyl group, a nitro group, a trifluoromethyl group, a lower alkoxycarbonyl group, a lower alkoxy group or a hydroxy group) or Represents ] The amine represented by the general formula (III) [In the formula (III), R 1 and R 2 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, an alkenyl group or an aryl group, and Z is hydrogen, a methyl group or a C 1-2 acylamino group] A general formula (l) characterized by coupling with a diphenylethane amine represented by The present invention provides a process for producing a disazo compound represented by the formula (1), wherein D, R 1 , R 2 and Z have the same meanings as described above.
以下に本発明を詳細に説明する。 Hereinafter, the present invention will be described in detail.
一般式（II） （Ｄは前記と同じ意味を表す） で示されるモノアゾ化合物を例えば硫酸、リン酸、硝酸
等の鉱酸又は酢酸、プロピオン酸等の有機酸と硫酸、リ
ン酸、硝酸等からなる混酸中で通常10℃以下で亜硝酸ソ
ーダ又はニトロシル硫酸を用いて３〜５時間ジアゾ化
し、次いで一般式（III） （R1,R2及びＺは前記と同じ意味を表す）で示される
ジフエニルエタン系アミンと、メタノール、エタノール
等のアルコール類又は酢酸、プロピオン酸等の有機酸を
含んでもよい塩類、硫酸、リン酸等の鉱酸媒体中で例え
ば５℃以下２〜３時間撹拌するというような条件で式
（II）の化合物のジアゾ化物：式（III）の化合物のモ
ル比約1:0.5の割合でカップリングさせる事によって目
的とする式（ｌ） （D,R1,R2及びＺは前記と同じ意味を表す）で示され
るジスアゾ化合物が高収率、高純度で得られる。なお式
（ｌ）の目的化合物はカップリング反応後結晶として沈
澱するのでこれを取して目的物を得ることが出来る。General formula (II) (Where D represents the same meaning as described above), a monoazo compound represented by the following formula is usually used in a mixed acid consisting of a mineral acid such as sulfuric acid, phosphoric acid and nitric acid or an organic acid such as acetic acid and propionic acid and sulfuric acid, phosphoric acid and nitric acid. Diazotization with sodium nitrite or nitrosylsulfuric acid at 10 ° C or lower for 3 to 5 hours, then general formula (III) (R 1 , R 2 and Z have the same meanings as described above) and a salt which may contain an alcohol such as methanol or ethanol or an acetic acid or an organic acid such as propionic acid, sulfuric acid or phosphoric acid. Coupling at a molar ratio of the diazotized compound of the compound of formula (II): the compound of formula (III) of about 1: 0.5 under the conditions of stirring in a mineral acid medium such as 5 ° C. or less for 2-3 hours. Target expression (l) The disazo compound represented by (D, R 1 , R 2 and Z have the same meanings as described above) can be obtained in high yield and high purity. The target compound of formula (1) precipitates as crystals after the coupling reaction, and can be taken to obtain the target product.
猶、一般式（III）で示されるジフエニルエタン系ア
ミンは一般式（IV） （式（IV）においてＺ、R1及びR2は式（III）におけ
るのと同じ意味を表す） で示されるアニリン誘導体とアセトアルデヒド又はパラ
アセトアルデヒドを例えば塩酸、硫酸等鉱酸水溶液媒体
中で反応させる事によって得られる。The diphenylethane amine represented by the general formula (III) has the general formula (IV) (In the formula (IV), Z, R 1 and R 2 have the same meanings as in the formula (III)) and the aniline derivative is reacted with acetaldehyde or paraacetaldehyde in an aqueous medium of mineral acid such as hydrochloric acid or sulfuric acid. Obtained by things.
前記において一般式（II）で示される化合物において
Ｄの具体例としては例えば下記のものがあげられる。Specific examples of D in the compound represented by the general formula (II) are as follows.
又、一般式（III）で示される化合物の具体例として
は下記第１表に示される化合物が挙げられる。 Further, specific examples of the compound represented by the general formula (III) include the compounds shown in Table 1 below.
本発明の方法で得られる一般式（ｌ）で示されるジス
アゾ化合物はポリエステル繊維をはじめとしてポリアク
リロニトリル系繊維、トリアセテート繊維、ジアセテー
ト繊維等の合成乃至半合成繊維あるいはこれらを含有す
る混紡繊維を良好な堅牢度でもってネービー色に染色す
るのに供される。 The disazo compound represented by the general formula (1) obtained by the method of the present invention is preferably a synthetic or semi-synthetic fiber such as polyester fiber, polyacrylonitrile fiber, triacetate fiber, diacetate fiber, or a blended fiber containing these. It is used for dyeing a navy color with excellent fastness.
本発明の製造方法によってホルマリンのような人体、
環境に対してより有害な物質を用いることなく高純度、
高収率でジスアゾ化合物が得られるようになった。A human body such as formalin according to the production method of the present invention,
High purity without using substances that are more harmful to the environment,
The disazo compound can be obtained in high yield.
実施例 次に本発明を実施例により更に具体的に説明する。実
施例中、部及び％とあるものは、夫々重量部及び重量％
を示すものとする。EXAMPLES Next, the present invention will be described more specifically by way of examples. In the examples, parts and% mean parts by weight and% by weight, respectively.
Shall be indicated.
実施例1. 98％硫酸70部に酢酸120部を加えてえられた液に冷却
下０〜５℃で40％ニトロシル硫酸25部を滴下した。更に
下記式 で示される化合物16.1部を添加し−２℃〜５℃で４時間
撹拌しゾアゾ液とした。Example 1. 70 parts of 98% sulfuric acid and 120 parts of acetic acid were added and 25 parts of 40% nitrosylsulfuric acid was added dropwise to the obtained solution at 0 to 5 ° C under cooling. Furthermore, the following formula 16.1 parts of the compound shown in 1) was added, and the mixture was stirred at -2 ° C to 5 ° C for 4 hours to give a zoazo solution.
一方、下記式 で示される化合物11.0部を氷水150部、70％硫酸15部、
スルファミン酸1.5部に溶解させカップラー液を調製し
た。On the other hand, the following formula 11.0 parts of the compound represented by: 150 parts of ice water, 15 parts of 70% sulfuric acid,
A coupler solution was prepared by dissolving it in 1.5 parts of sulfamic acid.
このカップラー液に５℃以下で前記ジアゾ液を滴下し
た。更に２時間撹拌後、過、水洗、乾燥して、下記式
（３） で示されるジスアゾ化合物23.8部（収率94％）を得た。
又、純度は71％であり純度換算収率は66.7％であった。
このジスアゾ化合物のλmax（75％アセトン水溶液中）
は650nmであった。The diazo solution was added dropwise to the coupler solution at 5 ° C or lower. After further stirring for 2 hours, the mixture is washed with water, dried, and dried by the following formula (3). 23.8 parts (yield 94%) of the disazo compound represented by
The purity was 71% and the purity conversion yield was 66.7%.
Λmax of this disazo compound (in 75% acetone solution)
Was 650 nm.
本実施例で得られた染料を用いてポリエステル繊維の
130℃高温染色を行ったところ堅牢度が良好なネービー
色の染布が得られた。Using the dye obtained in this example, polyester fiber
When dyed at 130 ° C at high temperature, a navy-colored dyeing cloth having good fastness was obtained.
猶、本実施例に使用した前記式（２）で示される化合
物は以下の方法により合成した。However, the compound represented by the formula (2) used in this example was synthesized by the following method.
水95部に98％硫酸5.1部を加えて得られた液にＮ−シ
アノエチル−Ｎ−エチルアニリン10.4部、パラアルデヒ
ド2.0部を各々添加する。次いで90〜95℃で８時間撹拌
する事によって式（２）で示される化合物11.0部を得
た。5.1 parts of 98% sulfuric acid was added to 95 parts of water, and 10.4 parts of N-cyanoethyl-N-ethylaniline and 2.0 parts of paraaldehyde were added to the resulting solution. Then, the mixture was stirred at 90 to 95 ° C for 8 hours to obtain 11.0 parts of the compound represented by the formula (2).
比較例1.（特開昭58−129059準拠） 実施例１のうち下記式 の代わりに下記式 で示される化合物10.6部を用いて反応させたところ、式
（３）で示されるジスアゾ化合物23.3部（収率92.1％）
を得た。又、純度は68.9％であり純度換算収率は63.5％
であった。Comparative Example 1 (according to Japanese Patent Laid-Open No. 58-129059) Instead of When reacted with 10.6 parts of the compound represented by the formula, 23.3 parts of the disazo compound represented by the formula (3) (yield 92.1%)
I got The purity is 68.9%, and the purity conversion yield is 63.5%.
Met.
実施例2. 実施例１において式（１）で示される化合物の代りに
下記式（４） で示される化合物15.3部を用いた以外は実施例１と同様
に反応を行い下記式（５） で示される化合物20.9部（収率85.7％）を得た。このジ
スアゾ化合物のλmax（70％アセトン水溶液中）は645nm
であった。Example 2 Instead of the compound represented by the formula (1) in Example 1, the following formula (4) The reaction was performed in the same manner as in Example 1 except that 15.3 parts of the compound represented by 20.9 parts (yield 85.7%) of the compound represented by The λmax of this disazo compound (in 70% acetone solution) is 645 nm.
Met.
実施例３〜19. 実施例１に準じて本発明の化合物の合成した。いずれ
のジスアゾ化合物もポリエステル繊維をネービー色に染
色した。Examples 3 to 19. The compound of the present invention was synthesized according to Example 1. Both disazo compounds dyed polyester fibers in a navy color.
以下に合成した染料の構造式及びそれらのλmaxを示
した。（75％アセトン水溶液中） 発明の効果 人体、環境汚染のおそれの少ない方法により高純度、
高収率でヘテロ環含有ジスアゾ化合物を製造する方法が
確立された。The structural formulas of the synthesized dyes and their λmax are shown below. (In 75% acetone solution) Advantages of the Invention Highly purified by a method with less risk of human body and environmental pollution,
A method for producing a heterocycle-containing disazo compound in high yield has been established.
Claims (1)
ルキル基、ニトロ基、トリフロロメチル基、低級アルコ
キシカルボニル基、低級アルコキシ基又はヒドロキシ基
を表す）又は を表す。〕で示されるアミン類をジアゾ化し、一般式
（III） 〔式（III）においてR1,R2は夫々独立に水素原子、置換
もしくは非置換のアルキル基、アルケニル基又はアリー
ル基を、Ｚは水素原子、メチル基又はＣ１〜２のアシル
アミノ基を表す〕で示されるジフエニルエタン系アミン
類とカップリングさせることを特徴とする一般式（ｌ） 〔式（ｌ）においてD,R1,R2及びＺは前記と同じ意味を
表す〕 で示されるジスアゾ化合物の製造方法。1. General formula (II) [In the formula (II), D is (X 1 and X 2 each independently represent a hydrogen atom, a halogen atom, a lower alkyl group, a nitro group, a trifluoromethyl group, a lower alkoxycarbonyl group, a lower alkoxy group or a hydroxy group) or Represents ] The amines represented by the general formula (III) [In the formula (III), R 1 and R 2 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, an alkenyl group or an aryl group, and Z represents a hydrogen atom, a methyl group or a C 1-2 acylamino group. ] The general formula (l) characterized by coupling with a diphenylethane amine represented by [In the formula (l), D, R 1 , R 2 and Z have the same meanings as described above].
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9337888A JPH086046B2 (en) | 1988-04-18 | 1988-04-18 | Method for producing disazo compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9337888A JPH086046B2 (en) | 1988-04-18 | 1988-04-18 | Method for producing disazo compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01266167A JPH01266167A (en) | 1989-10-24 |
| JPH086046B2 true JPH086046B2 (en) | 1996-01-24 |
Family
ID=14080643
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9337888A Expired - Lifetime JPH086046B2 (en) | 1988-04-18 | 1988-04-18 | Method for producing disazo compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH086046B2 (en) |
-
1988
- 1988-04-18 JP JP9337888A patent/JPH086046B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH01266167A (en) | 1989-10-24 |
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