JPH0768459B2 - Dyeing - Google Patents
DyeingInfo
- Publication number
- JPH0768459B2 JPH0768459B2 JP1005911A JP591189A JPH0768459B2 JP H0768459 B2 JPH0768459 B2 JP H0768459B2 JP 1005911 A JP1005911 A JP 1005911A JP 591189 A JP591189 A JP 591189A JP H0768459 B2 JPH0768459 B2 JP H0768459B2
- Authority
- JP
- Japan
- Prior art keywords
- dye
- parts
- groups
- hydroxymethyl
- quinophthalone
- 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
- C09B25/00—Quinophthalones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Indole Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
【発明の詳細な説明】 （産業上の利用分野） 本発明は染料の製造方法に関し、更に詳しく耐熱性、鮮
明性、透明性等に優れた着色物を与える新規な染料の製
造方法に関する。TECHNICAL FIELD The present invention relates to a method for producing a dye, and more particularly to a novel method for producing a dye which gives a colored product excellent in heat resistance, sharpness, transparency and the like.
（従来の技術及びその問題点） 従来、ポリエステル等の合成繊維の着色方法としては、
分散染料による染色方法及び顔料による原液着色方法が
広く利用されている。(Prior art and its problems) Conventionally, as a method for coloring synthetic fibers such as polyester,
A dyeing method using a disperse dye and a stock solution coloring method using a pigment are widely used.
分散染料による染色は、比較的低分子量の染料を用いて
ポリエステル繊維を染色するものであり、美麗な着色繊
維が提供されるが、染料の分子量が小さいことから、耐
昇華性等の耐熱性が不十分であり、熱処理時に種々の問
題が生じる。Dyeing with a disperse dye is for dyeing polyester fibers with a dye having a relatively low molecular weight, and a beautiful colored fiber is provided, but since the molecular weight of the dye is small, heat resistance such as sublimation resistance is low. It is insufficient and causes various problems during heat treatment.
一方、顔料による原液着色方法の場合には、上記の如き
耐熱性の問題は少ないが、顔料の分散性に問題があり、
紡糸時のノズルの目詰りや発色性の問題があり、又、顔
料はポリエステル中に溶解することがないので、着色物
の鮮明性や透明性が不十分であるという問題がある。On the other hand, in the case of the stock solution coloring method using a pigment, the heat resistance problem as described above is small, but there is a problem in the dispersibility of the pigment.
There is a problem of nozzle clogging and color development during spinning, and there is a problem that the clarity and transparency of the colored product are insufficient because the pigment does not dissolve in the polyester.
この様な鮮明性や透明性は原液着色方法に染料を用いれ
ば問題はないが、原液着色時の温度は200乃至300℃或い
はそれ以上の高温になる為、染料が容易に熱分解し、染
料による原液着色方法は困難である。There is no problem if such a sharpness or transparency is obtained by using a dye in the undiluted solution coloring method, but since the temperature during undiluted solution coloring is a high temperature of 200 to 300 ° C or higher, the dye is easily thermally decomposed and the dye The stock solution coloring method is difficult.
以上の如き問題はポリエステルに限定されず、ポリエチ
レン、ポリプロピレン、ポリアミド、ポリカーボネート
等の他の合成樹脂や合成繊維においても同様に生じてい
る。The above-mentioned problems are not limited to polyester, and occur similarly in other synthetic resins and synthetic fibers such as polyethylene, polypropylene, polyamide and polycarbonate.
従って、本発明の目的は、耐熱性、鮮明性、透明性等に
優れた着色物を与える染料を提供することである。Therefore, an object of the present invention is to provide a dye which gives a colored product having excellent heat resistance, vividness and transparency.
（問題点を解決する為の手段） 上記目的は以下の本発明によって達成される。即ち、本
発明は、下記一般式（Ｉ）で表わされるキノフタロン染
料とＮ−ヒドロキシメチルフタルイミドを反応させるこ
とを特徴とする下記一般式（II）で表わされる染料の製
造方法である。(Means for Solving Problems) The above object is achieved by the present invention described below. That is, the present invention is a method for producing a dye represented by the following general formula (II), which comprises reacting a quinophthalone dye represented by the following general formula (I) with N-hydroxymethylphthalimide.
（上記式中におけるＡ環はベンゼン環又はナフタレン環
であり、R1乃至R3は水素原子、ハロゲン原子、低級アル
キル基、低級アルコキシ基、フェニル基、ベンゾイル
基、アシル基、ニトロ基又はアミノ基である。） （作用） 下記一般式（Ｉ）で表わされる染料は従来公知であり、
キノフタロン染料と称され、ポリエステル等の合成繊維
の分散染料として広く使用されている。 (A ring in the above formula is a benzene ring or a naphthalene ring, and R 1 to R 3 are hydrogen atoms, halogen atoms, lower alkyl groups, lower alkoxy groups, phenyl groups, benzoyl groups, acyl groups, nitro groups or amino groups. (Function) The dye represented by the following general formula (I) is conventionally known,
It is called a quinophthalone dye and is widely used as a disperse dye for synthetic fibers such as polyester.
（式中のR1及びR2は前記と同意義を有する。） 上記キノフタロン染料をポリエステル等の合成樹脂の原
液着色方法に使用すると、原液着色時の高温によって、
昇華したり熱分解したりして使用することが出来ない。 (R 1 and R 2 in the formula have the same meanings as described above.) When the above quinophthalone dye is used in a stock solution coloring method for a synthetic resin such as polyester, the high temperature during stock solution coloring causes
It cannot be used due to sublimation or thermal decomposition.
これに対し、該キノフタロン染料にフタルイミドメチル
基又は置換フタルイミドメチル基を結合させることによ
って耐熱性が著しく向上し、原液着色時の高温によって
昇華したり熱分解することが全くなくなり、又、一般の
有機顔料とは異なり、被着色材である合成樹脂中に溶解
するので均一美麗で且つ鮮明性及び透明性に優れた着色
物が提供される。On the other hand, by bonding a phthalimidomethyl group or a substituted phthalimidomethyl group to the quinophthalone dye, the heat resistance is remarkably improved, and there is no sublimation or thermal decomposition due to the high temperature at the time of coloring the undiluted solution. Unlike a pigment, it dissolves in a synthetic resin that is a material to be colored, so that a colored product that is uniformly beautiful and has excellent sharpness and transparency is provided.
（好ましい実施態様） 本発明の染料は前記の公知の一般式（Ｉ）のキノフタロ
ン染料に、Ｎ−ヒドロキシメチルフタルイミドを反応さ
せることによって得られる。(Preferred Embodiment) The dye of the present invention is obtained by reacting the above-mentioned known quinophthalone dye of the general formula (I) with N-hydroxymethylphthalimide.
使用するキノフタロン染料は前記一般式（Ｉ）において
R1及びR2が水素原子ものが好ましいが、これをハロゲン
化したハロゲン化キノフタロン染料等も好ましく使用す
ることが出来、更にR1及び又はR2がメチル基、エチル
基、プロピル基の如き低級アルキル基、メトキシ基、エ
トキシ基、プロポキシ基等の低級アルコキシ基、ニトロ
基等の置換基を有するものであってもよい。The quinophthalone dye used is represented by the above general formula (I).
R 1 and R 2 are preferably hydrogen atoms, but halogenated quinophthalone dyes obtained by halogenating this are also preferably used, and R 1 and / or R 2 is a lower group such as a methyl group, an ethyl group or a propyl group. It may have a lower alkoxy group such as an alkyl group, a methoxy group, an ethoxy group, a propoxy group, or a substituent such as a nitro group.
上記キノフタロン染料に反応させるＮ−ヒドロキシメチ
ルフタルイミドは、フタルイミドにホルマリンを反応さ
せることによって得られる公知の化合物であり、本発明
においてはＮ−ヒドロキシメチルフタルイミドにはその
ベンゼン環に置換基を有さぬもの及び置換基を有するも
のが含まれ、例えば、好ましい具体例としては、 Ｎ−ヒドロキシメチルフタルイミド、 Ｎ−ヒドロキシメチル−４−ニトロフタルイミド、 Ｎ−ヒドロキシメチル−３−ニトロフタルイミド、 Ｎ−ヒドロキシメチル−３−ヒドロキシフタルイミド、 Ｎ−ヒドロキシメチル−３−クロルフタルイミド、 Ｎ−ヒドロキシメチル−４−クロルフタルイミド、 Ｎ−ヒドロキシメチル−3,6−ジクロルフタルイミド、 Ｎ−ヒドロキシメチル−3,4,5,6−テトラクロルフタル
イミド、 Ｎ−ヒドロキシメチル−3,4,5,6−テトラブロムフタル
イミド、 Ｎ−ヒドロキシメチル−３−アミノフタルイミド、 Ｎ−ヒドロキシメチル−４−アミノフタルイミド、 Ｎ−ヒドロキシメチル−３−メトキシフタルイミド、 Ｎ−ヒドロキシメチル−３−メチルフタルイミド、 Ｎ−ヒドロキシメチル−４−メチルフタルイミド、 Ｎ−ヒドロキシメチル−4,5−ジブロムフタルイミド等
が挙げられる。The N-hydroxymethylphthalimide reacted with the quinophthalone dye is a known compound obtained by reacting phthalimide with formalin, and in the present invention, N-hydroxymethylphthalimide has no substituent on its benzene ring. And those having a substituent, for example, as preferable specific examples, N-hydroxymethylphthalimide, N-hydroxymethyl-4-nitrophthalimide, N-hydroxymethyl-3-nitrophthalimide, N-hydroxymethyl- 3-hydroxyphthalimide, N-hydroxymethyl-3-chlorophthalimide, N-hydroxymethyl-4-chlorophthalimide, N-hydroxymethyl-3,6-dichlorophthalimide, N-hydroxymethyl-3,4,5,6 -Tetrachlorphthalimi , N-hydroxymethyl-3,4,5,6-tetrabromophthalimide, N-hydroxymethyl-3-aminophthalimide, N-hydroxymethyl-4-aminophthalimide, N-hydroxymethyl-3-methoxyphthalimide, N- Examples thereof include hydroxymethyl-3-methylphthalimide, N-hydroxymethyl-4-methylphthalimide, N-hydroxymethyl-4,5-dibromophthalimide and the like.
キノフタロン染料とＮ−ヒドロキシメチルフタルイミド
との反応は、両者を脱水縮合によって行うこと出来、脱
水縮合可能な方法はいずれも有効であるが、特に好まし
い方法は両者を濃硫酸（例えば95乃至99％）中に溶解
し、約10乃至100℃程度の温度で１乃至24時間反応させ
ることによって目的物である前記一般式（II）で表わさ
れる染料が得られる（詳細は後述の実施例の参照のこ
と）。The reaction between the quinophthalone dye and N-hydroxymethylphthalimide can be carried out by dehydration condensation of both, and any method capable of dehydration condensation is effective, but a particularly preferable method is to use both with concentrated sulfuric acid (eg 95 to 99%). The target compound, a dye represented by the general formula (II), can be obtained by dissolving it in the reaction mixture and reacting it at a temperature of about 10 to 100 ° C. for 1 to 24 hours (for details, see the examples below). ).
両者の反応はキノフタロン染料１モル当り、Ｎ−ヒドロ
キシメチルフタルイミド１乃至３モルの比率で行うのが
よく、特にキノフタロン染料１モル当りＮ−ヒドロキシ
メチルフタルイミド0.8乃至1.5モルを反応させ、後に生
成物を精製することによってキノフタロン染料１モルに
Ｎ−ヒドロキシメチルフタルイミド１モルが反応した生
成物が得られる。The reaction between the two is preferably carried out at a ratio of 1 to 3 mol of N-hydroxymethylphthalimide per 1 mol of quinophthalone dye, particularly 0.8 to 1.5 mol of N-hydroxymethylphthalimide is reacted per 1 mol of quinophthalone dye, and the product is later produced. The product obtained by reacting 1 mol of quinophthalone dye with 1 mol of N-hydroxymethylphthalimide is obtained by purification.
Ｎ−ヒドロキシメチルフタルイミド基又は置換Ｎ−ヒド
ロキシメチルフタルイミド基の結合位置は明確には確認
されていないが、キノフタロン染料の水酸基のオルト位
置に結合している可能性が高い。Although the bonding position of the N-hydroxymethylphthalimide group or the substituted N-hydroxymethylphthalimide group has not been clearly confirmed, it is highly possible that it is bonded to the ortho position of the hydroxyl group of the quinophthalone dye.
以上の如くして得られた一般式（II）で表わされる本発
明の染料は黄色粉末であり、440乃至450nmの間に最大吸
収波長を有し、約300℃迄の温度に対し、十分な熱安定
性を有している。The dye of the present invention represented by the general formula (II) obtained as described above is a yellow powder, has a maximum absorption wavelength between 440 and 450 nm, and has a sufficient absorption temperature up to about 300 ° C. It has thermal stability.
以上の後き一般式（II）で表わされる染料によって着色
される有機物の代表例は、ポリエステル樹脂、ポリアミ
ド樹脂、ポリプロピレン樹脂、ポリエチレン樹脂、ポリ
スチレン樹脂、ポリ塩化ビニル樹脂、ポリカーボネート
樹脂等の熱可塑性合成樹脂である。特に繊維化されるポ
リエステル樹脂が最も適している。勿論、本発明では、
これらの樹脂に限定されず、塗料、印刷インキ、油等の
他の有機物の着色も機能である。Typical examples of organic substances colored by the dye represented by the general formula (II) are thermoplastic synthetic resins such as polyester resin, polyamide resin, polypropylene resin, polyethylene resin, polystyrene resin, polyvinyl chloride resin, and polycarbonate resin. It is a resin. Particularly, the polyester resin which is made into fiber is most suitable. Of course, in the present invention,
The function is not limited to these resins, and coloring of other organic substances such as paints, printing inks and oils is also a function.
着色方法は特に限定されないが、好ましい方法は原液着
色方法であり、この原液着色方法は、樹脂ペレットに前
記一般式（II）で表わされる染料を樹脂100重量部当り
0.01乃至１重量部の割合で加え、これを溶融混練して押
出成形、射出成形、溶融紡糸する方法及び樹脂を形成す
る単量体中に前記染料を加えて重合と同時に着色を行う
方法であり、その他の従来公知の方法も同様に使用する
ことが出来る。The coloring method is not particularly limited, but a preferred method is a stock solution coloring method. This stock solution coloring method uses resin pellets containing the dye represented by the general formula (II) per 100 parts by weight of the resin.
It is a method of adding 0.01 to 1 part by weight, melt-kneading the mixture, and extrusion-molding, injection-molding, melt-spinning, and a method of adding the above-mentioned dye to a resin-forming monomer to perform polymerization and coloring. Other known methods can be used as well.
（効果） 以上の如き本発明によれば、耐熱性、鮮明性、透明性等
に優れた着色物が容易に提供される。(Effect) According to the present invention as described above, a colored product having excellent heat resistance, sharpness, transparency and the like can be easily provided.
（実施例） 次に実施例及び使用例を挙げて本発明を更に具体的に説
明する。尚、文中、部又は％とあるのは特に断りのない
限り重量基準である。(Examples) Next, the present invention will be described more specifically with reference to Examples and Examples of use. In the text, parts and% are based on weight unless otherwise specified.
実施例１ ３′−ヒドロキシ−キノフタロン28.9部を98％硫酸580
部中に20乃至25℃の温度で攪拌しながら溶解させる。こ
れにＮ−ヒドロキシメチルフタルイミド18.6部を加えて
20乃至25℃の温度で24時間攪拌する。次いで反応物を氷
水6,000部中へ10℃以下の温度で少しずつ加え、析出し
た結晶を濾過し、中性迄水洗した後、90℃で乾燥すると
下記式で示される新規な黄色染料42.6部が得られる。こ
の染料の熱分解点は290℃で、最大吸収波長は443nmであ
る。又、この染料はポリエステル等の合成樹脂を鮮明な
黄色に着色し優れた耐熱性、鮮明性及び透明性を有する
着色物を与える。Example 1 28.9 parts of 3'-hydroxy-quinophthalone was added to 98% sulfuric acid 580
Dissolve in parts with stirring at a temperature of 20 to 25 ° C. Add 18.6 parts of N-hydroxymethylphthalimide to this
Stir for 24 hours at a temperature of 20-25 ° C. Then, the reaction product was gradually added to 6,000 parts of ice water at a temperature of 10 ° C or lower, the precipitated crystals were filtered, washed with water to neutrality, and then dried at 90 ° C to obtain 42.6 parts of a novel yellow dye represented by the following formula. can get. The thermal decomposition point of this dye is 290 ° C, and the maximum absorption wavelength is 443 nm. Further, this dye colors a synthetic resin such as polyester in a bright yellow color to give a colored product having excellent heat resistance, sharpness and transparency.
実施例２ ３′−ヒドロキシ−キノフタロン28.9部を98％硫酸580
部中に25乃至30℃の温度で攪拌しながら溶解させる。こ
れにＮ−ヒドロキシメチル−3,4,5,6−テトラクロルフ
タルイミド33.1部を加えて25乃至30℃の温度で24時間攪
拌する。次いで反応物を氷水6,000部中へ10℃以下の温
度で少しずつ加え、析出した結晶を濾過し、中性迄水洗
した後、90℃で乾燥すると下記式で示される新規な黄色
染料55.7部が得られる。この染料の熱分解点は320℃
で、最大吸収波長は444nmである。 Example 2 28.9 parts of 3'-hydroxy-quinophthalone was added to 98% sulfuric acid 580
Dissolve in parts with stirring at a temperature of 25 to 30 ° C. To this was added 33.1 parts of N-hydroxymethyl-3,4,5,6-tetrachlorophthalimide and the mixture was stirred at a temperature of 25 to 30 ° C. for 24 hours. Then, the reaction product was gradually added to 6,000 parts of ice water at a temperature of 10 ° C or lower, and the precipitated crystals were filtered, washed with water to neutrality, and dried at 90 ° C to obtain 55.7 parts of a novel yellow dye represented by the following formula. can get. The thermal decomposition point of this dye is 320 ℃
And the maximum absorption wavelength is 444 nm.
実施例３ 原料として３′−ヒドロキシ−キノフタロン28.9部とＮ
−ヒドロキシメチル−４−ニトロフタルイミド23.3部
を、溶媒として98％硫酸580部を用い、その他は実施例
１と同様に処理して下記で示される新規な黄色染料46.8
部が得られる。この染料の熱分解点は285℃であり、最
大吸収波長は442nmである。 Example 3 28.9 parts of 3'-hydroxy-quinophthalone and N as raw materials
-Hydroxymethyl-4-nitrophthalimide (23.3 parts), 98% sulfuric acid (580 parts) as a solvent, and the same treatment as in Example 1 except that the novel yellow dye 46.8 shown below was used.
Part is obtained. The thermal decomposition point of this dye is 285 ° C, and the maximum absorption wavelength is 442 nm.
実施例４ 原料として３′−ヒドロキシ−キノフタロン28.9部とＮ
−ヒドロキシメチル−４−メチルフタルイミド20.1部
を、溶媒として98％硫酸580部を用い、その他は実施例
１と同様に処理して下記式で示される新規な黄色染料4
3.9部が得られる。この染料の熱分解点は305℃であり、
最大吸収波長は446nmである。 Example 4 28.9 parts of 3'-hydroxy-quinophthalone and N as raw materials
-Hydroxymethyl-4-methylphthalimide (20.1 parts), 98% sulfuric acid (580 parts) as a solvent, and the other treatments were carried out in the same manner as in Example 1 to obtain a novel yellow dye 4 of the following formula.
3.9 copies will be obtained. The thermal decomposition point of this dye is 305 ℃,
The maximum absorption wavelength is 446 nm.
実施例５ 下記第１表の原料を使用し、他は実施例１乃至４と同様
にして下記第１表の染料を得た。 Example 5 The dyes shown in Table 1 below were obtained in the same manner as in Examples 1 to 4 except that the raw materials shown in Table 1 below were used.
使用例１ 実施例１の染料0.5部とパンソルブH1.0部とを混練した
ものを、ポリ塩化ビニル樹脂コンパウンド50部と混合
し、６インチロールで155乃至160℃で３分間ロール練り
してシートを形成し、このシートを170℃で50Kgの圧力
で厚さ5mmにプレス成形したものは透明な純黄色に着色
されており、この着色シートに白色塩化ビニル樹脂シー
トを50℃で10Kgの圧力で24時間重ねても染料の移行性は
認められなかった。 Use Example 1 A sheet prepared by kneading 0.5 parts of the dyestuff of Example 1 and 1.0 part of Pansolve H with 50 parts of polyvinyl chloride resin compound and rolling with a 6-inch roll at 155 to 160 ° C. for 3 minutes. Is formed, and this sheet is press-molded at a pressure of 50 kg at a temperature of 170 ° C. to a thickness of 5 mm and is colored in transparent pure yellow, and a white vinyl chloride resin sheet is added to this colored sheet at a pressure of 10 kg at 50 ° C. No dye migration was observed even after 24 hours.
使用例２ 実施例２の染料の微粉砕物５部を、1,000部のポリエチ
レンに混合し、250℃で射出成形した成形品は透明で均
一な黄色に着色されていた。USE EXAMPLE 2 5 parts of the finely pulverized product of the dye of Example 2 was mixed with 1,000 parts of polyethylene and injection-molded at 250 ° C. The molded product was transparent and uniformly colored yellow.
使用例３ 実施例３の染料10部、分散剤１部及びエチレングリコー
ル89部をボールミルで磨砕し、この磨砕物15部を、テレ
フタル酸ジメチル１モルとエチレングリコール２モルと
から得られるエステル交換生成物100部に添加し、減圧
下約280℃で４時間加熱重合し、均一美麗に着色された
黄色のポリエステルを得た。この着色ポリエステルを常
法に従って紡糸したところ、紡糸ノズルの目詰まりは全
くなく、透明性及び鮮明性に優れたポリエステル繊維が
得られた。この繊維束を２枚の白色のポリエステルシー
トの間に挟み120℃で20Kgの圧力下で２時間加熱処理し
たが、白色ポリエステルシートへの染料の移行は認めら
れなかった。USE EXAMPLE 3 10 parts of the dyestuff of Example 3, 1 part of a dispersant and 89 parts of ethylene glycol are ground with a ball mill, and 15 parts of this ground product are transesterified from 1 mol of dimethyl terephthalate and 2 mols of ethylene glycol. The product was added to 100 parts and heat-polymerized under reduced pressure at about 280 ° C. for 4 hours to obtain a uniformly and beautifully colored yellow polyester. When this colored polyester was spun according to a conventional method, a spinning nozzle was not clogged at all, and a polyester fiber excellent in transparency and sharpness was obtained. This fiber bundle was sandwiched between two white polyester sheets and heat-treated at 120 ° C. under a pressure of 20 kg for 2 hours, but no dye transfer to the white polyester sheet was observed.
使用例４ 実施例４の染料１部とポリエチレンテレフタレート樹脂
ペレット200部とを混合し、290乃至300℃の温度の乾式
紡糸装置で８分間の滞留時間で３デニールの繊維を紡糸
したところ、紡糸ノズルの目詰まりは全くなく、透明性
及び鮮明性に優れたポリエステル繊維が得られた。この
繊維束を２枚の白色のポリエステルシートの間に挟み12
0℃で20Kgの圧力下で２時間加熱処理したが、白色ポリ
エステルシートへの染料の移行は認められなかった。
尚、他の実施例の染料も上記使用例１乃至４と同様に耐
熱性、鮮明性及び透明性に優れた着色物を与える。USE EXAMPLE 4 1 part of the dyestuff of Example 4 and 200 parts of polyethylene terephthalate resin pellets were mixed and a 3 denier fiber was spun in a dry spinning apparatus at a temperature of 290 to 300 ° C. for a residence time of 8 minutes. No polyester was clogged and a polyester fiber excellent in transparency and sharpness was obtained. Insert this fiber bundle between two white polyester sheets 12
When heat-treated at 0 ° C. under a pressure of 20 kg for 2 hours, transfer of the dye to the white polyester sheet was not observed.
The dyes of the other examples also give colored products excellent in heat resistance, sharpness and transparency as in the above-mentioned Use Examples 1 to 4.
Claims (1)
ン染料とＮ−ヒドロキシメチルフタルイミドを反応させ
ることを特徴とする下記一般式（II）で表わされる染料
の製造方法。 （上記式中におけるＡ環はベンゼン環又はナフタレン環
であり、R1乃至R3は水素原子、ハロゲン原子、低級アル
キル基、低級アルコキシ基、フェニル基、ベンゾイル
基、アシル基、ニトロ基又はアミノ基である。）1. A process for producing a dye represented by the following general formula (II), which comprises reacting a quinophthalone dye represented by the following general formula (I) with N-hydroxymethylphthalimide. (A ring in the above formula is a benzene ring or a naphthalene ring, and R 1 to R 3 are hydrogen atoms, halogen atoms, lower alkyl groups, lower alkoxy groups, phenyl groups, benzoyl groups, acyl groups, nitro groups or amino groups. It is.)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1005911A JPH0768459B2 (en) | 1989-01-17 | 1989-01-17 | Dyeing |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1005911A JPH0768459B2 (en) | 1989-01-17 | 1989-01-17 | Dyeing |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02187470A JPH02187470A (en) | 1990-07-23 |
| JPH0768459B2 true JPH0768459B2 (en) | 1995-07-26 |
Family
ID=11624083
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1005911A Expired - Fee Related JPH0768459B2 (en) | 1989-01-17 | 1989-01-17 | Dyeing |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0768459B2 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5800573A (en) * | 1994-10-06 | 1998-09-01 | Bayer Aktiengesellschaft | Bulk dyeing using quinophthalone dyestuffs |
| JP3608873B2 (en) * | 1995-06-16 | 2005-01-12 | 三井化学株式会社 | Optical recording medium |
| JP5501716B2 (en) * | 2009-09-28 | 2014-05-28 | 株式会社Ａｄｅｋａ | Cyanine compound, optical recording material and color correction material using the compound |
| KR102235984B1 (en) * | 2018-04-04 | 2021-04-02 | 주식회사 엘지화학 | Quinophthalone-based compound, photosensitive resin composition, photoresist, color filter, and display device comprising the same |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5150330A (en) * | 1974-10-28 | 1976-05-01 | Mitsubishi Chem Ind | KINOFUTARONKEIGANRYONO SEIZOHOHO |
-
1989
- 1989-01-17 JP JP1005911A patent/JPH0768459B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02187470A (en) | 1990-07-23 |
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