JPH0798907B2 - Azo compound and its manufacturing method - Google Patents
Azo compound and its manufacturing methodInfo
- Publication number
- JPH0798907B2 JPH0798907B2 JP1124055A JP12405589A JPH0798907B2 JP H0798907 B2 JPH0798907 B2 JP H0798907B2 JP 1124055 A JP1124055 A JP 1124055A JP 12405589 A JP12405589 A JP 12405589A JP H0798907 B2 JPH0798907 B2 JP H0798907B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- nitro group
- hydrogen atom
- azo
- formula
- 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 - Fee Related
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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/103—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group of the naphthalene series
Description
【発明の詳細な説明】 産業上の利用分野 本発明は新規なアゾ化合物、それを含む着色剤およびそ
の製造法に関する。更に詳しくは優れた耐熱性や堅牢性
を持つ不溶性アゾ顔料、その製造法およびその使用法に
関する。TECHNICAL FIELD The present invention relates to a novel azo compound, a colorant containing the same, and a method for producing the same. More specifically, it relates to an insoluble azo pigment having excellent heat resistance and fastness, a method for producing the same, and a method for using the same.
従来の技術 アゾ顔料はジアゾ化合物とカプラーとのカップリング反
応で合成される。それらに使われるカプラーの中で特に
重要なのは３−ヒドロキシ−２−ナフトエ酸あるいはそ
の誘導体である。2. Description of the Related Art Azo pigments are synthesized by a coupling reaction between a diazo compound and a coupler. Particularly important among the couplers used in them are 3-hydroxy-2-naphthoic acid or its derivatives.
３−ヒドロキシ−２−ナフトエ酸から合成されるブリリ
アント・カーミン6B（PigmentRed57）やウォチャングレ
ッド（PigmentRed48）は最も重要な赤色溶性アゾ顔料で
ある。これらはCa、Ba、Mnなどの不溶性金属レーキの形
で使用されているが金属塩であるから本質的に酸、アル
カリに対し不安定である。Brilliant carmine 6B (PigmentRed57) and Watchengred (PigmentRed48), which are synthesized from 3-hydroxy-2-naphthoic acid, are the most important red-soluble azo pigments. These are used in the form of insoluble metal lakes such as Ca, Ba and Mn, but are essentially unstable to acids and alkalis because they are metal salts.
一方、３−ヒドロキシ−２−ナフトエ酸とアニリン類と
の縮合で合成される３−ヒドロキシ−２−ナフトアニリ
ド（ナフトールAS）をカプラーとして不溶性アゾ顔料が
合成される。このいわゆるナフトール顔料は溶解性や堅
牢性を改善する目的で開発されており、一般的に耐光
性、耐候性、耐薬品性、耐溶剤性などの性質においてア
ゾレーキ顔料に優る。On the other hand, an insoluble azo pigment is synthesized using 3-hydroxy-2-naphthanilide (naphthol AS), which is synthesized by condensation of 3-hydroxy-2-naphthoic acid and anilines, as a coupler. This so-called naphthol pigment has been developed for the purpose of improving solubility and fastness, and is generally superior to azo lake pigments in properties such as light resistance, weather resistance, chemical resistance and solvent resistance.
この様に３−ヒドロキシ−２−ナフトエ酸から誘導され
るアゾ化合物は古くから重要な顔料として知られている
が、その異性体である６−ヒドロキシ−２−ナフトエ酸
から誘導されるアゾ顔料およびその特性については殆ん
ど知られていない。Thus, the azo compound derived from 3-hydroxy-2-naphthoic acid has been known as an important pigment for a long time, and the azo pigment derived from its isomer, 6-hydroxy-2-naphthoic acid, and Little is known about its properties.
本発明が解決しようとする課題 ナフトール顔料は優秀な顔料であるが、色材に対してま
すます多様な性能が要求される現代においてはナフトー
ル顔料もまた十分に要求に対応できる性能を持つとは言
い難い。本発明の目的はアゾ色素の基本骨格として、３
−ヒドロキシ−２−ナフトエ酸の異性体であるところの
６−ヒドロキシ−２−ナフトエ酸を用い、耐熱、耐水、
耐溶剤、耐薬品性等の諸特性において優れた有用な新規
アゾ化合物およびそれを含む着色剤を提供することにあ
る。Problems to be Solved by the Present Invention Although naphthol pigments are excellent pigments, it is said that naphthol pigments also have the ability to sufficiently meet the demands in today's world when increasingly diverse performances are required for coloring materials. Hard to say. The object of the present invention is to provide the basic skeleton of an azo dye with 3
Using 6-hydroxy-2-naphthoic acid, which is an isomer of -hydroxy-2-naphthoic acid,
It is intended to provide a useful new azo compound excellent in various properties such as solvent resistance and chemical resistance, and a colorant containing the same.
６−ヒドロキシ−２−ナフトエ酸は近年芳香族ポリエス
テルの要素のひとつとして注目を集めている素材で、そ
の誘導体、特に芳香核上に置換基としてニトロ基を有す
るアニリンのジアゾニウム化合物と６−ヒドロキシ−２
−ナフトエ酸誘導体とをカップリングして得られるアゾ
化合物は全く新規であり、かつ、３−ヒドロキシ−２−
ナフトエ酸から誘導されるアゾ化合物に比べ優れた耐
熱、耐水および耐溶剤性を有することが判明した。6-Hydroxy-2-naphthoic acid has recently attracted attention as one of the elements of aromatic polyesters, and its derivatives, especially diazonium compounds of aniline having a nitro group as a substituent on the aromatic nucleus and 6-hydroxy- Two
-The azo compound obtained by coupling with a naphthoic acid derivative is completely novel, and 3-hydroxy-2-
It was found to have excellent heat resistance, water resistance and solvent resistance as compared with azo compounds derived from naphthoic acid.
課題を解決するための手段 本発明は下記一般式〔Ｉ〕で表されるアゾ化合物、 〔式中、R1、R2、R3、R4、R5およびR6はそれぞれ独立し
て水素原子、アルキル基、アルコキシ基、ニトロ基また
はハロゲン原子を示す（但し、R1、R2およびR3のうち少
なくとも一つはニトロ基である）。〕、それを含む着色
剤およびそのアゾ化合物の製法を提供する。Means for Solving the Problems The present invention provides an azo compound represented by the following general formula [I], [In the formula, R 1 , R 2 , R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom, an alkyl group, an alkoxy group, a nitro group or a halogen atom (provided that R 1 , R 2 And at least one of R 3 is a nitro group). ], And a method for producing a colorant containing the same and an azo compound thereof.
本発明のアゾ化合物は新規化合物であり、この化合物を
構成するベンゼン環あるいはナフタレン環にはどのよう
な置換基がどの位置に付いてもよいが、これを顔料とし
て用いるときはカップリング成分として、６−ヒドロキ
シ−２−ナフトアニリドを用い、ジアゾ成分として、ニ
トロ基を置換基として有するアニリン類のジアゾニウム
塩を用て得られるアゾ化合物が好適である。この様な構
成により、耐熱、耐薬品、耐水および耐溶剤性等に優れ
たアゾ顔料を得ることが可能となる。The azo compound of the present invention is a novel compound, and the benzene ring or naphthalene ring constituting this compound may have any substituent at any position, but when it is used as a pigment, as a coupling component, An azo compound obtained by using 6-hydroxy-2-naphthanilide and a diazonium salt of an aniline having a nitro group as a substituent as a diazo component is suitable. With such a constitution, it becomes possible to obtain an azo pigment having excellent heat resistance, chemical resistance, water resistance and solvent resistance.
さらに本発明の特徴は、色彩的性質や堅牢性からみてR1
からR6までの置換基はそれぞれ独立して水素原子、アル
キル基、アルコキシ基、ニトロ基またはハロゲン原子が
好ましい。Furthermore, the feature of the present invention is that R 1
It is preferable that the substituents from R to R 6 are each independently a hydrogen atom, an alkyl group, an alkoxy group, a nitro group or a halogen atom.
アルキル基としては低級アルキル基、例えばメチル、エ
チル、ｎ−プロピル、イソプロピル、ｎ−ブチル、ｔ−
ブチル等、特にメチル基が好ましい。The alkyl group is a lower alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, t-
Butyl and the like, especially a methyl group is preferable.
アルコキシ基としては低級アルキル基を有するアルコキ
シ基、特にメトキシまたはエトキシ基が好ましい。As the alkoxy group, an alkoxy group having a lower alkyl group, particularly a methoxy or ethoxy group is preferable.
ハロゲン原子としてはフッ素、塩素、臭素、または沃素
が好ましい。The halogen atom is preferably fluorine, chlorine, bromine or iodine.
R2またはR3のいずれかがニトロ基である化合物が特に耐
熱耐薬品性等の理由で好ましい。A compound in which either R 2 or R 3 is a nitro group is particularly preferable for reasons such as heat resistance and chemical resistance.
R4、R5およびR6は全て水素である化合物が色の鮮明さの
点で好結果が得られる傾向がある。Compounds in which R 4 , R 5 and R 6 are all hydrogen tend to give good results in terms of color vividness.
特に好ましい例はR1とR4が水素原子、メチル基またはメ
トキシ基、R2が水素原子、メチル基またはニトロ基、R3
が水素原子またはニトロ基（特にR2がニトロ基でないと
きはR3はニトロ基）、R5とR6が水素原子である化合物で
ある。Particularly preferred examples are R 1 and R 4 are hydrogen atom, methyl group or methoxy group, R 2 is hydrogen atom, methyl group or nitro group, R 3
Is a hydrogen atom or a nitro group (especially when R 2 is not a nitro group, R 3 is a nitro group), and R 5 and R 6 are hydrogen atoms.
本発明化合物は着色剤、特に塗料、印刷インキ、クレヨ
ン、プラスチック練込み用着色剤として有用である。こ
れらの用法は、従来のアゾ系顔料と全く同様である。但
し本発明化合物は耐熱、耐薬品、耐水、耐溶剤性が従来
のアゾ系顔料、特に３−ヒドロキシ−２−ナフトアニリ
ドから誘導されたものより優れているのでその適用範囲
が広い。特にプラスチック練込み用着色剤は、プラスチ
ックを溶融状態にして着色剤を練込むため、プラスチッ
クの融点以上での高い耐熱性が要求されるが、本発明化
合物は耐熱性に優れており、特にその様な目的の着色剤
として好適である。同様に熱硬化型塗料用着色剤として
も有用である。また耐水、耐溶剤性に優れているため、
塗料、印刷インキ等に有用である。The compound of the present invention is useful as a colorant, particularly as a colorant for paints, printing inks, crayons, and plastics. These usages are exactly the same as those of conventional azo pigments. However, since the compound of the present invention is superior in heat resistance, chemical resistance, water resistance and solvent resistance to conventional azo pigments, especially those derived from 3-hydroxy-2-naphthanilide, its application range is wide. Particularly, the plastic kneading colorant is required to have high heat resistance above the melting point of the plastic because the colorant is kneaded in the plastic in a molten state, but the compound of the present invention is excellent in heat resistance, and particularly It is suitable as a colorant for such purposes. Similarly, it is also useful as a colorant for thermosetting paints. Also, because it is excellent in water resistance and solvent resistance,
It is useful for paints and printing inks.
本発明のアゾ化合物は、従来、３−ヒドロキシ−２−ナ
フトエ酸等から誘導される公知のアゾ化合物と同様の方
法により合成し得る。例えば一般式〔II〕 〔式中R1、R2、およびR3はそれぞれ独立して水素原子、
アルキル基、アルコキシ基、ニトロ基またはハロゲン原
子を示す（但しそのうちいずれかはニトロ基であ
る）。〕 で示される化合物をジアゾ化し、得られたジアゾニウム
化合物を一般式〔III〕： 〔式中R4、R5およびR6はそれぞれ独立して水素原子、ア
ルキル基、アルコキシ基、ニトロ基またはハロゲン原子
を示す〕 で示される化合物とカップリングすることにより製造さ
れる。The azo compound of the present invention can be synthesized by the same method as a known azo compound derived from 3-hydroxy-2-naphthoic acid or the like. For example, the general formula [II] [Wherein R 1 , R 2 , and R 3 are each independently a hydrogen atom,
An alkyl group, an alkoxy group, a nitro group or a halogen atom is shown (however, one of them is a nitro group). ] The compound represented by the formula is diazotized, and the obtained diazonium compound is represented by the general formula [III]: [Wherein R 4 , R 5 and R 6 each independently represents a hydrogen atom, an alkyl group, an alkoxy group, a nitro group or a halogen atom].
ジウゾ化反応は例えば、一般式〔II〕で示されるアニリ
ン類塩酸水溶液に氷冷下、攪拌しながら亜硝酸ナトリウ
ム水溶液を加えて行なわれる。このように調製されたジ
アゾニウム塩水溶液をヒドロキシナフトアニリド類〔II
I〕のアルカリ水溶液に加えてカップリングが行なわれ
る。反応温度は０〜40℃が好ましい。温度が高ければ反
応は速いが、ジアゾニウム塩の分解も速まるので10〜30
℃が特に好ましい。カップリング反応の最適pHはケース
バイケースであるがヒドロキシナフトアニリド類を溶か
すアルカリ量は最少にとどめることが好ましい。The diazotization reaction is carried out, for example, by adding an aqueous sodium nitrite solution to the aniline hydrochloric acid aqueous solution represented by the general formula [II] under ice-cooling and stirring. The diazonium salt aqueous solution thus prepared was treated with hydroxynaphthoanilides [II
Coupling is performed in addition to the alkaline aqueous solution of [I]. The reaction temperature is preferably 0 to 40 ° C. If the temperature is high, the reaction will be fast, but the decomposition of the diazonium salt will also be fast, so 10-30
C is especially preferred. The optimum pH of the coupling reaction is on a case-by-case basis, but it is preferable to minimize the amount of alkali that dissolves hydroxynaphthoanilides.
一般式〔III〕で示されるヒドロキシナフトアニリド類
は、例えば６−アセトキシ−２−ナフトエ酸を一般式
〔IV〕 〔式中R4、R5およびR6はそれぞれ独立して水素原子、ア
ルキル基、アルコキシ基、ニトロ基またはハロゲン原子
を示す。〕 で式される化合物と縮合し、次いでアセトキシ基を加水
分解して得てもよい。Hydroxynaphthoanilides represented by the general formula [III] include, for example, 6-acetoxy-2-naphthoic acid represented by the general formula [IV] [In the formula, R 4 , R 5 and R 6 each independently represent a hydrogen atom, an alkyl group, an alkoxy group, a nitro group or a halogen atom. ] It may be obtained by condensing with a compound represented by the following formula and then hydrolyzing the acetoxy group.
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、部は重量部を示す。本発明はこれら実施例にの
み限定されるものではない。Next, the present invention will be described more specifically by way of examples. In the examples, “part” means “part by weight”. The invention is not limited to these examples.
実施例１ ６−アセトキシ−２−ナフトエ酸の合成： ６−ヒドロキシ−２−ナフトエ酸を15倍量の酢酸に100
℃で溶解し、酸触媒の存在下1.2当量の無水酢酸を加え
る。冷却後６−アセトキシ−２−ナフトエ酸の結晶を濾
取する。Example 1 Synthesis of 6-acetoxy-2-naphthoic acid: 6-hydroxy-2-naphthoic acid in 15 volumes of acetic acid 100
Dissolve at ° C and add 1.2 equivalents of acetic anhydride in the presence of acid catalyst. After cooling, crystals of 6-acetoxy-2-naphthoic acid are collected by filtration.
６−ヒドロキシ−２−ナフトアニリド： ６−アセトキシ−２−ナフトエ酸69部をキシレン414部
に分散し、ジメチルホルムアミド0.4部を加える。よく
攪拌しながら塩化チオニル53部を滴下し、３時間反応さ
せる。その後、過剰の塩化チオニルを留去し、これにア
ニリン33部を加え、110℃で２時間反応させる。冷却後
６−アセトキシ−２−ナフトアニリドの結晶を濾取す
る。これをアルカリ水に加えて加水分解したのち、硫酸
で酸析する。結晶を濾過、水洗、乾燥して６−ヒドロキ
シ−２−ナフトアニリドを得る。6-Hydroxy-2-naphthanilide: 69 parts of 6-acetoxy-2-naphthoic acid are dispersed in 414 parts of xylene and 0.4 part of dimethylformamide is added. While stirring well, 53 parts of thionyl chloride is added dropwise and the reaction is carried out for 3 hours. Then, excess thionyl chloride is distilled off, 33 parts of aniline is added thereto, and the mixture is reacted at 110 ° C. for 2 hours. After cooling, crystals of 6-acetoxy-2-naphthanilide are collected by filtration. This is added to alkaline water for hydrolysis and then acidified with sulfuric acid. The crystals are filtered, washed with water and dried to obtain 6-hydroxy-2-naphthanilide.
２−ヒドロキシ−６−ナフトアニリド−１−アゾ（２′
−メチル−５′−ニトロベンゼン）の合成： ４−ニトロ−２−トルイジン7.6部に35％塩酸17.7部を
加え良く混連した。これに水500部を加えて溶解し、０
℃に保ちながら亜硝酸ナトリウム3.5部を水20部に溶解
した溶液を滴下してジアゾ化を行なった。他方、６−ヒ
ドロキシ−２−ナフトアニリド14部を水酸化ナトリウム
６部を含む水1000部に加熱溶解し、冷却後17℃に保っ
た。これに上述のジアゾ溶液を約15分で滴下してカップ
リング反応を行なった。２時間攪拌後、10％酢酸水溶液
を用いてpHを7.0−7.2に調整した。次いで70℃に昇温し
て30分攪拌したのち反応物を濾過した。ケーキを水洗、
乾燥すると鮮やかなオレンジ色の下記構造式のアゾ化合
物:2−ヒドロキシ−６−ナフトアニリド−１−アゾ−
（２′−メチル−５′−ニトロベンゼン）が得られた。2-hydroxy-6-naphthanilide-1-azo (2 '
-Methyl-5'-nitrobenzene): 4-Nitro-2-toluidine (7.6 parts) and 35% hydrochloric acid (17.7 parts) were added and mixed well. To this, add 500 parts of water and dissolve,
While keeping at ℃, a solution of 3.5 parts of sodium nitrite dissolved in 20 parts of water was added dropwise to carry out diazotization. On the other hand, 14 parts of 6-hydroxy-2-naphthanilide was dissolved by heating in 1000 parts of water containing 6 parts of sodium hydroxide, and the mixture was cooled and kept at 17 ° C. The above-mentioned diazo solution was added dropwise thereto for about 15 minutes to carry out a coupling reaction. After stirring for 2 hours, the pH was adjusted to 7.0-7.2 using a 10% aqueous acetic acid solution. Then, the temperature was raised to 70 ° C., the mixture was stirred for 30 minutes, and then the reaction product was filtered. Wash the cake with water,
A vivid orange azo compound of the following structural formula: 2-hydroxy-6-naphthanilide-1-azo-
(2'-methyl-5'-nitrobenzene) was obtained.
このアゾ化合物の耐水性、耐薬品性、耐溶剤性などの諸
性質はきわめて良好であった。その分解点は281℃であ
った。赤外線吸収スペクトル（KBr錠剤法）を第１図に
示す。また、JISK−5101に従って印刷インキを作り、展
色した試験片の色彩的データは、最大吸収波長611nm、
明度（Ｙ）14.6％、刺激純度（Pe）80.4％であった。 Various properties such as water resistance, chemical resistance, and solvent resistance of this azo compound were extremely good. The decomposition point was 281 ° C. The infrared absorption spectrum (KBr tablet method) is shown in FIG. Also, printing ink was made according to JIS K-5101, and the color data of the developed test piece has a maximum absorption wavelength of 611 nm,
The brightness (Y) was 14.6% and the excitation purity (Pe) was 80.4%.
実施例２〜４ 第１表に挙げたアミン類と６−ヒドロキシ−２−ナフト
アニリド類を用いて実施例１と同様の操作により第１表
に示す各種のアゾ化合物を得た。これらのアゾ化合物の
耐水性、耐薬品性、耐溶剤性などの諸性質並びに色彩的
データを実施例１の結果とともに第１表に示す。Examples 2 to 4 Various azo compounds shown in Table 1 were obtained by the same procedure as in Example 1 using the amines and 6-hydroxy-2-naphthanilides listed in Table 1. Various properties of these azo compounds such as water resistance, chemical resistance, solvent resistance and color data are shown in Table 1 together with the results of Example 1.
耐水性、耐薬品性、耐溶剤性は次のようにして評価し
た。Water resistance, chemical resistance, and solvent resistance were evaluated as follows.
耐水性：試料1gを水20gに加え、超音波で20分間分散さ
せる。煮沸１分後、冷却濾過する。濾液を観察する。Water resistance: Add 1 g of sample to 20 g of water and disperse ultrasonically for 20 minutes. After 1 minute of boiling, the mixture is cooled and filtered. Observe the filtrate.
耐薬品性、耐溶剤性：試料1gを試験液20mlに加え、超音
波で５分間分散させる。濾過後、濾液を観察する。Chemical resistance, solvent resistance: Add 1 g of the sample to 20 ml of the test liquid and disperse with ultrasonic waves for 5 minutes. After filtration, observe the filtrate.
評価:A＝全く着色が認められないもの、Ｂ＝着色が極め
て僅かであるもの、Ｃ＝着色が少しあるもの、Ｄ＝着色
があるもの、Ｅ＝着色が著しいもの。Evaluation: A = no coloration at all, B = very little coloration, C = some coloration, D = coloration, E = significant coloration.
参考例１〜４ 対応する番号の実施例中のカプラー骨格を６−ヒドロキ
シ−２−ナフトエ酸から３−ヒドロキシ−２−ナフトエ
酸にかえて、おのおの実施例１と同様の操作により第２
表に示す公知のアゾ顔料を得た。Reference Examples 1 to 4 The coupler skeleton in the correspondingly numbered Examples was changed from 6-hydroxy-2-naphthoic acid to 3-hydroxy-2-naphthoic acid, and the second procedure was carried out in the same manner as in Example 1.
The known azo pigments shown in the table were obtained.
第１表と第２表を比較して分かるように本発明のアゾ化
合物はそれらの構造異性体であるところの公知のアゾ顔
料と比べて耐水性、耐薬品性、耐溶剤性、耐熱性などの
物理化学的性質に優れた性能を示した。As can be seen by comparing Tables 1 and 2, the azo compound of the present invention has water resistance, chemical resistance, solvent resistance, heat resistance, etc. as compared with known azo pigments which are structural isomers thereof. It showed excellent performance in physicochemical properties.
発明の効果 このようにして製造された本発明のアゾ化合物はオレン
ジ色から鮮やかな赤色までの様々な美しい色を有し、顔
料として印刷インキ、クレヨン、塗料、プラスチックの
着色などに広く使用することができる。本発明のアゾ化
合物は常温では水に全く溶けず、アルカリ水あるいは酸
性水に対しても強い堅牢性を示す。また、アセトン、キ
シレン、メタノールなどの有機溶剤に対しても優れた堅
牢性を示す。これらの性質は印刷インキ、塗料などの着
色剤に適す。更に本発明のアゾ化合物は構造異性体の関
係にある公知のアゾ顔料と比べてより高い分解点を持
つ。この性質は特に焼付け塗料やポリオレフィンのよう
な熱可塑性樹脂の着色に有利である。 EFFECTS OF THE INVENTION The azo compound of the present invention thus produced has various beautiful colors from orange to bright red and can be widely used as a pigment for printing inks, crayons, paints, coloring of plastics and the like. You can The azo compound of the present invention does not dissolve in water at room temperature at all, and exhibits strong fastness to alkaline water or acidic water. It also exhibits excellent fastness to organic solvents such as acetone, xylene, and methanol. These properties are suitable for colorants such as printing inks and paints. Further, the azo compound of the present invention has a higher decomposition point than known azo pigments having a structural isomer relationship. This property is particularly advantageous for coloring a baking paint or a thermoplastic resin such as polyolefin.
第１図は実施例１の化合物の赤外線吸収スペクトルを示
す。FIG. 1 shows the infrared absorption spectrum of the compound of Example 1.
Claims (6)
て水素原子、アルキル基、アルコキシ基、ニトロ基また
はハロゲン原子を示す（但し、R1、R2およびR3のうち少
なくとも一つはニトロ基である）。〕1. An azo compound represented by the following general formula [I]. [In the formula, R 1 , R 2 , R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom, an alkyl group, an alkoxy group, a nitro group or a halogen atom (provided that R 1 , R 2 And at least one of R 3 is a nitro group). ]
基、R2が水素原子、メチル基またはニトロ基、R3が水素
原子またはニトロ基（但し、R2がニトロ基でないときは
ニトロ基）、R5とR6が水素原子である請求項１に記載の
アゾ化合物。2. General formula [I]: In, R 1 and R 4 are a hydrogen atom, a methyl group or a methoxy group, R 2 is a hydrogen atom, a methyl group or a nitro group, R 3 is a hydrogen atom or a nitro group (however, when R 2 is not a nitro group ), R 5 and R 6 are hydrogen atoms, the azo compound according to claim 1.
ルキル基、アルコキシ基、ニトロ基またはハロゲン原子
を示す（但しそのうちのいずれかはニトロ基であ
る）。〕 で示される化合物をアゾ化し、得られたジアゾニウム化
合物を一般式〔III〕： 〔式中R4、R5およびR6はそれぞれ独立して水素原子、ア
ルキル基、アルコキシ基、ニトロ基またはハロゲン原子
を示す。〕 で示される化合物とカップリングすることを特徴とする
請求項１に記載のアゾ化合物の製法。3. A general formula [II]: [In the formula, R 1 , R 2 and R 3 each independently represent a hydrogen atom, an alkyl group, an alkoxy group, a nitro group or a halogen atom (provided that any one of them is a nitro group). ] The diazonium compound obtained by azotization of the compound represented by the following general formula [III]: [In the formula, R 4 , R 5 and R 6 each independently represent a hydrogen atom, an alkyl group, an alkoxy group, a nitro group or a halogen atom. ] The method for producing an azo compound according to claim 1, which comprises coupling with a compound represented by:
アルキル基、アルコキシ基、ニトロ基またはハロゲン原
子を示す。〕 の化合物が６−アセトキシ−２−ナフトエ酸を一般式
〔IV〕： 〔式中R4、R5およびR6はそれぞれ独立して水素原子、ア
ルキル基、アルコキシ基、ニトロ基またはハロゲン原子
を示す。〕 で示される化合物と縮合し、次いでアセトキシ基を加水
分解して得られるものである請求項３に記載の製法。4. A general formula [III]: [In the formula, R 4 , R 5 and R 6 are each independently a hydrogen atom,
It represents an alkyl group, an alkoxy group, a nitro group or a halogen atom. ] The compound of 6-acetoxy-2-naphthoic acid is represented by the general formula [IV]: [In the formula, R 4 , R 5 and R 6 each independently represent a hydrogen atom, an alkyl group, an alkoxy group, a nitro group or a halogen atom. ] The manufacturing method of Claim 3 which is obtained by condensing with the compound shown by these, and then hydrolyzing an acetoxy group.
キ、塗料または高分子材料用練込み着色剤。6. A kneading colorant for a printing ink, paint or polymer material, which comprises the compound according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1124055A JPH0798907B2 (en) | 1989-05-17 | 1989-05-17 | Azo compound and its manufacturing method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1124055A JPH0798907B2 (en) | 1989-05-17 | 1989-05-17 | Azo compound and its manufacturing method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02302471A JPH02302471A (en) | 1990-12-14 |
| JPH0798907B2 true JPH0798907B2 (en) | 1995-10-25 |
Family
ID=14875855
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1124055A Expired - Fee Related JPH0798907B2 (en) | 1989-05-17 | 1989-05-17 | Azo compound and its manufacturing method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0798907B2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6084101A (en) * | 1996-10-11 | 2000-07-04 | Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo | Naphtol derivative and process for producing the same |
| WO2000023526A1 (en) | 1998-10-16 | 2000-04-27 | Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo | Toning agent |
| JP5300321B2 (en) * | 2008-05-22 | 2013-09-25 | キヤノン株式会社 | Monoazo pigment, electrophotographic photosensitive member, process cartridge, and electrophotographic apparatus |
-
1989
- 1989-05-17 JP JP1124055A patent/JPH0798907B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02302471A (en) | 1990-12-14 |
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