JPH0826232B2 - Anthrapyridone-based compound, production method and use thereof - Google Patents
Anthrapyridone-based compound, production method and use thereofInfo
- Publication number
- JPH0826232B2 JPH0826232B2 JP22175587A JP22175587A JPH0826232B2 JP H0826232 B2 JPH0826232 B2 JP H0826232B2 JP 22175587 A JP22175587 A JP 22175587A JP 22175587 A JP22175587 A JP 22175587A JP H0826232 B2 JPH0826232 B2 JP H0826232B2
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- resin
- anthrapyridone
- formula
- resistance
- compound represented
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Description
【発明の詳細な説明】 ＜産業上の利用分野＞ 本発明はアントラピリドン系化合物、その製造方法及
びそれを用いる樹脂用着色剤に関する。DETAILED DESCRIPTION OF THE INVENTION <Field of Industrial Application> The present invention relates to an anthrapyridone compound, a method for producing the same, and a colorant for a resin using the same.
＜従来の技術＞ 従来、アントラピリドン系化合物は、特に合成樹脂用
着色剤として使用されており、具体的には以下の構造式
で示されるアントラピリドン系化合物が知られている。<Prior Art> Conventionally, an anthrapyridone compound has been particularly used as a colorant for a synthetic resin, and specifically, an anthrapyridone compound represented by the following structural formula is known.
しかしながら、これらの着色剤は耐熱性が優れるとい
う特徴を有しているが、これらの着色剤で着色された樹
脂成型品は耐光性、耐ブリード性及び耐溶出性等の性能
が十分でなく、更に改良を要望されていた。However, although these colorants have a characteristic that they are excellent in heat resistance, resin molded products colored with these colorants do not have sufficient performance such as light resistance, bleed resistance and elution resistance, Further improvements were requested.
＜発明が解決しようとする問題点＞ 本発明は、本発明によって得られる特定のアントラピ
リドン系化合物を樹脂の着色剤として使用した場合、着
色剤の耐熱性が優れ、耐光性、耐ブリード性及び耐溶出
性等が良好な着色成型品を与えることを見出し本発明を
完成したものである。 <Problems to be Solved by the Invention> In the present invention, when the specific anthrapyridone compound obtained by the present invention is used as a colorant for a resin, the colorant has excellent heat resistance, light resistance, bleed resistance and The present invention has been completed by finding that a colored molded article having good elution resistance and the like can be provided.
従って、本発明の主要な目的は、かかる優れた性能を
具備する着色剤を提供することにある。Therefore, a main object of the present invention is to provide a colorant having such excellent performance.
＜問題点を解決するための手段＞ 本発明は一般式〔Ｉ〕 （式中、Ａは更に置換されていてもよいベンゼン環の残
基を表し、Ｂは式 で示される環を表し、ｎは１〜２の数を表す。） で示されるアントラピリドン系化合物、その製造方法お
よびそれを含んで成ることを特徴とする樹脂用着色剤を
その要旨とする。<Means for Solving Problems> The present invention has the general formula [I] (In the formula, A represents a residue of a benzene ring which may be further substituted, and B represents the formula. Represents a ring, and n represents a number of 1 to 2. ), An anthrapyridone compound, a method for producing the anthrapyridone compound, and a colorant for a resin containing the same are summarized.
本発明に用いられる前記一般式〔Ｉ〕で表されるアン
トラピリドン系化合物は、以下の方法で製造される。The anthrapyridone compound represented by the general formula [I] used in the present invention is produced by the following method.
すなわち、一般式〔II〕 （式中、Ａは更に置換されていてもよいベンゼン環の残
基を表す） で表されるアントラピリドン系化合物と下記一般式〔II
I〕 （式中、Ｂは式 で示される環を表す） で示されるＮ−メチロール化合物とを、例えば硫酸水溶
液中、０〜50℃の温度で１〜10数時間反応させることに
より製造することができる。ここで、一般式〔II〕で表
されるアントラピリドン系化合物としては、更に具体的
には一般式〔IV〕 （式中、Ｘはハロゲン,R,−NHCOR1,−CONR2R3,−COR4,
−SO2R5又は−SO2NR6R7を表し、ここで、R,R1,R4は低級
アルキル基、R2,R3は水素原子または低級アルキル基、R
5は低級アルキル基又はヒドロキシ低級アルキル基、R6,
R7はそれぞれ独立に水素原子又は低級アルキル基を表
す。又、ｍは１〜２の数を示す） で示されるアントラピリドン系化合物を用いることが好
ましい。こられの化合物は、本発明者らが先に出願した
特願昭61−287093号または特願昭62135695号等の記載に
従って製造される。That is, the general formula [II] (Wherein A represents a residue of a benzene ring which may be further substituted) and an anthrapyridone compound represented by the following general formula [II
I] (Where B is the formula The N-methylol compound represented by the formula (1) is reacted with, for example, an aqueous sulfuric acid solution at a temperature of 0 to 50 ° C. for 1 to 10 hours. Here, as the anthrapyridone-based compound represented by the general formula [II], more specifically, the general formula [IV] (In the formula, X is halogen, R, -NHCOR 1 , -CONR 2 R 3 , -COR 4 ,
Represents --SO 2 R 5 or --SO 2 NR 6 R 7 , wherein R, R 1 and R 4 are lower alkyl groups, R 2 and R 3 are hydrogen atoms or lower alkyl groups, R
5 is a lower alkyl group or a hydroxy lower alkyl group, R 6 ,
R 7's each independently represent a hydrogen atom or a lower alkyl group. Further, it is preferable to use an anthrapyridone compound represented by These compounds can be produced according to the description of Japanese Patent Application No. 61-287093 or Japanese Patent Application No. 62135695 filed by the present inventors.
本発明の主要な目的である樹脂着色として使用し得る
樹脂としては、ポリスチレン、ポリメチルメタクリレー
ト、ポリ塩化ビニル、アクリロニトリル・ブタジエン・
スチレン共重合体（ABS樹脂）、アクリロニトリル・ス
チレン共重合体（AS樹脂）、ポリカーボネート、ポリフ
ェニレンオキサイド、ポリプロピレン、ポリエチレン、
ポリアクリロニトリル、ポリアミド、ポリアセタール、
ポリエチレンテレフタレート若しくはポリブチレンテレ
フタレートなどの熱可塑性樹脂、又はフェノール樹脂、
ユリア樹脂、メラミン樹脂、不飽和ポリエスル樹脂、エ
ポキシ樹脂若しくはジアリルフタレート樹脂の様な熱硬
化性樹脂をあげることができる。Resins that can be used for resin coloring, which is the main object of the present invention, include polystyrene, polymethyl methacrylate, polyvinyl chloride, acrylonitrile butadiene.
Styrene copolymer (ABS resin), acrylonitrile-styrene copolymer (AS resin), polycarbonate, polyphenylene oxide, polypropylene, polyethylene,
Polyacrylonitrile, polyamide, polyacetal,
A thermoplastic resin such as polyethylene terephthalate or polybutylene terephthalate, or a phenol resin,
The thermosetting resin such as urea resin, melamine resin, unsaturated polyester resin, epoxy resin or diallyl phthalate resin can be used.
本発明の着色剤は樹脂と着色剤を適当な方法で混合
し、熱、圧力を加えて射出成形、押出加工、紡糸などの
方法により着色された製品を得ることができる。The colorant of the present invention can be obtained by mixing a resin and a colorant by an appropriate method and applying heat and pressure to obtain a colored product by a method such as injection molding, extrusion, spinning or the like.
樹脂の着色法は公知の方法を用いることができる。例
えば樹脂のペレットまたは粉末を適当なミキサー中で、
粉砕された着色剤と必要に応じて各種の添加剤とともに
混合し、次いでニーダー、ロールミル、バンバリーミキ
サー、押出機等で着色剤を樹脂中に溶解又は分散し着色
することができる。更に必要に応じ、圧縮、射出、押出
し、ブロー等の成型を行い、成型品とすることができ
る。A known method can be used for coloring the resin. For example, resin pellets or powder in a suitable mixer,
It is possible to mix the pulverized colorant with various additives as necessary, and then dissolve or disperse the colorant in the resin with a kneader, roll mill, Banbury mixer, extruder or the like for coloring. If necessary, molding such as compression, injection, extrusion and blow can be performed to obtain a molded product.
また、着色剤を適当な重合触媒を含有するモノマーに
加え、重合によって所望の熱可塑性樹脂又は熱硬化性樹
脂の着色物となし適当な方法で成型することもできる。It is also possible to add a colorant to a monomer containing an appropriate polymerization catalyst to form a desired thermoplastic resin or thermosetting resin colored product by polymerization, and mold it by an appropriate method.
着色剤の添加量は、特に限定はないが経済性等を考慮
すれば樹脂に対して0.01〜５重量％、好ましくは0.01〜
１重量％で用いられる。The amount of the colorant added is not particularly limited, but from the viewpoint of economic efficiency, it is 0.01 to 5% by weight, preferably 0.01 to 5% by weight based on the resin.
Used at 1% by weight.
更に、その他通常の樹脂の着色に使用される染料、顔
料を併用することも可能である。例えば二酸化チタンを
0.1〜１重量％併用することにより不透明の着色成型品
を得ることもできる。Further, it is also possible to use other dyes and pigments which are commonly used for coloring resins. For example, titanium dioxide
An opaque colored molded product can also be obtained by using 0.1 to 1% by weight in combination.
＜発明の効果＞ 本発明によって得られる特定のアントラピリドン系化
合物を樹脂の着色剤として使用した場合、着色剤の耐熱
性が優れ、耐光性、耐ブリード性及び耐溶出性等が良好
な着色成型品を与える。<Effects of the Invention> When a specific anthrapyridone compound obtained by the present invention is used as a colorant for a resin, the colorant is excellent in heat resistance, and has good light resistance, bleeding resistance, elution resistance and the like. Give a gift.
＜実施例＞ 次に、本発明を更に具体的に実施例によって説明する
が、本発明は以下の実施例に限定されるものではない。
例中、部は重量部を表す。<Examples> Next, the present invention will be described more specifically by examples, but the present invention is not limited to the following examples.
In the examples, parts represent parts by weight.
実施例1. 下記構造式 で示されるアントラピリドン化合物3.9部と下記構造式 で示されるＮ−メチロール化合物5.3部とを、90％硫酸5
0g中25〜30℃の温度で７時間反応させ、反応液を水300m
l中へ排出し、生じた沈澱物を濾別し、水で洗浄後乾燥
させることにより下記構造式 で示されるアントラピリドン化合物のケーキ6.7部を得
た。この化合物のλmax（クロロホルム）は522nmであ
り、融点は212〜217℃であった。Example 1. The following structural formula Anthrapyridone compound represented by 3.9 parts and the following structural formula 5.3 parts of N-methylol compound represented by
React in 0g at a temperature of 25-30 ℃ for 7 hours.
The resulting precipitate was filtered out, washed with water and dried to obtain the following structural formula. 6.7 parts of a cake of the anthrapyridone compound represented by The compound had a λmax (chloroform) of 522 nm and a melting point of 212 to 217 ° C.
得られたアントラピリドン化合物0.2部をABS樹脂100
部と混合した後、押出機を用いて205℃で着色を行い、
着色ペレットを得た。0.2 parts of the obtained anthrapyridone compound was added to ABS resin 100
After mixing with the parts, coloring was performed at 205 ° C. using an extruder,
Colored pellets were obtained.
この着色ペレットを射出成形機で230℃×１分サイク
ルで成形し、透明の黄味赤色の板状着色成型品を得た。
得られた板状着色成型品は耐ブリード性が優れており、
さらに耐溶出性耐光性が優れていた。又、270℃×３分
サイクルで射出成型しても板状着色成型品の色相の変化
はわずかであり、耐熱性も良好であった。The colored pellets were molded by an injection molding machine at a cycle of 230 ° C for 1 minute to obtain a transparent yellowish red plate-shaped colored molded product.
The obtained plate-shaped colored molded article has excellent bleed resistance,
Further, elution resistance and light resistance were excellent. Further, even when injection molding was carried out at a cycle of 270 ° C. for 3 minutes, the hue of the plate-shaped colored molded product was slightly changed, and the heat resistance was also good.
実施例２ 実施例１に記載の方法に従って、実施例１に用いたＮ
−メチロール化合物に代え、下記構造式 で示されるＮ−メチロール化合物を用い、同様にして下
記構造式 で示される黄味赤色の色相のアントラピリドン系化合物
を得た。この化合物のλmax（クロロホルム）は522nmで
あり、融点は147〜152℃であった。Example 2 N used in Example 1 according to the method described in Example 1.
-In place of the methylol compound, the following structural formula Using the N-methylol compound represented by To obtain an anthrapyridone compound having a yellowish red hue. The compound had a λmax (chloroform) of 522 nm and a melting point of 147 to 152 ° C.
実施例３ 実施例１に記載の方法に従って、実施例１に用いたア
ントラピリドン系化合物に代え、下記構造式 で示される化合物を用い、同様にして下記構造式 で示されるアントラピリドン系化合物を得た。この化合
物のλmax（クロロホルム）は525nmであり、融点は192
〜197.5℃であった。Example 3 The following structural formula was used instead of the anthrapyridone compound used in Example 1 according to the method described in Example 1. In the same manner, using the compound represented by An anthrapyridone compound represented by This compound has a λmax (chloroform) of 525 nm and a melting point of 192
It was ~ 197.5 ° C.
得られた化合物0.2部を用いて実施例１に記載の方法
に従って成型し、やや青味の板状着色成型品を得た。得
られた板状成型品は耐ブリード性、耐溶出性及び耐光性
が優れていた。また実施例１と同様、耐熱性が優れてい
た。The obtained compound (0.2 part) was molded according to the method described in Example 1 to obtain a slightly bluish plate-shaped colored molded product. The obtained plate-shaped molded product was excellent in bleed resistance, elution resistance and light resistance. Also, as in Example 1, the heat resistance was excellent.
比較例1,2,3 前記公知化合物Ａ〜Ｃを用いて、本発明の化合物との
比較した結果を以下に示す。Comparative Examples 1, 2, 3 The results of comparison with the compound of the present invention using the known compounds A to C are shown below.
比較例１……公知化合物Ａを用いた場合 比較例２……公知化合物Ｂ 〃 比較例３……公知化合物Ｃ 〃 公知化合物それぞれ0.2部を用いて、実施例１に記載
の方法に従ってそれぞれ成型した。Comparative Example 1 ... Using Known Compound A Comparative Example 2 ... Known Compound B 〃 Comparative Example 3 …… Known Compound C 〃 Known compound 0.2 parts each was molded according to the method described in Example 1. .
得られた成型品の品質を本発明のアントラピリドン系
化合物と比較して表−１に示す。The quality of the obtained molded product is shown in Table 1 in comparison with the anthrapyridone compound of the present invention.
表−１から明らかなように、本発明のアントラピリド
ン系化合物は耐熱性が優れているとともに着色された樹
脂成型品は耐光性、耐ブリード性及び耐溶出性のいずれ
もが良好であった。As is clear from Table 1, the anthrapyridone compound of the present invention has excellent heat resistance, and the colored resin molded product has good light resistance, bleed resistance and elution resistance.
☆耐ブリード性 TiO21.0％を含有する軟質PVC板にABS着色成型板を重
ね、100g/cm2の荷重下、80℃で２時間処理し、軟質PVC
板への着色の程度をJIS−Ｌ−0805汚染用グレースケー
ルで判定評価した。 ☆ Bleed resistance A soft PVC board containing 1.0% TiO 2 is overlaid with an ABS colored molded board, and treated at 80 ° C for 2 hours under a load of 100g / cm 2 to create a soft PVC board.
The degree of coloring on the plate was evaluated by a JIS-L-0805 stain gray scale.
☆耐溶出性 ポリオレフィン等衛生協議会の色材の試験法−溶出試
験法に準じて試験、評価した。☆ Elution resistance Tested and evaluated according to the test method for coloring materials of the Hygiene Council such as polyolefin-dissolution test method.
○……溶出なし ×印……（ ）に示す溶媒に溶出した。○: No elution ×: Dissolved in the solvent shown in ().
☆耐光性 JIS−Ｌ−0842に準じ、フェードメーターによる促進
テストを行った。判定は同時照射したブルースケールに
より行った。☆ Light resistance According to JIS-L-0842, an accelerated test was performed using a fade meter. Judgment was performed using a blue scale that was simultaneously irradiated.
☆耐熱性 ABS樹脂から得た着色ペレットを射出成型機で230℃×
１分サイクルで成型したものを標準とし270℃で３分サ
イクルで成型したものの変退色の程度をJIS−Ｌ−0802
変退色用グレーズスケールで判定し、耐熱性を評価し
た。☆ Colored pellets obtained from heat-resistant ABS resin at 230 ° C with an injection molding machine
JIS-L-0802 is used as the standard for the one-minute cycle molding and the degree of discoloration of the three-minute cycle molding at 270 ° C.
The heat resistance was evaluated by judging with a glaze scale for discoloration and fading.
実施例４ 実施例１の記載の方法に従って構造式 で示されるアントラピリドン系化合物を得た。この化合
物のλmax（クロロホルム）は520nmであった。Example 4 Structural formula according to the method described in Example 1 An anthrapyridone compound represented by The λmax (chloroform) of this compound was 520 nm.
ついで得られた化合物0.2部をポリスチレン樹脂100部
と混合した後、押出機を用いて205℃で着色を行い、着
色ペレットを得た。Next, 0.2 parts of the obtained compound was mixed with 100 parts of polystyrene resin, and then colored at 205 ° C. using an extruder to obtain colored pellets.
この着色ペレットを射出型機で220℃×１分サイクル
で成型し、黄味赤色の成型品を得た。得られた成型品は
耐ブリード性、耐溶出性及び耐光性が優れていた。The colored pellets were molded by an injection machine at a cycle of 220 ° C. for 1 minute to obtain a yellowish red molded product. The obtained molded product was excellent in bleed resistance, elution resistance and light resistance.
実施例５ 実施例１の記載の方法に従って構造式 で示されるアントラピリドン化合物を得た。この化合物
のλmax（クロロホルム）は519nmであった。Example 5 Structural formula according to the method described in Example 1 An anthrapyridone compound represented by The λmax (chloroform) of this compound was 519 nm.
次いで得られた化合物0.1部をポリエチレン樹脂100部
と混合した後、押出機を用いて220℃で着色を行い、着
色ペレットを得た。Next, 0.1 parts of the obtained compound was mixed with 100 parts of polyethylene resin, and then colored at 220 ° C. using an extruder to obtain colored pellets.
この着色ペレットを実施例１の記載の方法に従って成
型し、黄味赤色の板状着色成型物を得た。The colored pellets were molded according to the method described in Example 1 to obtain a yellowish red plate-shaped colored molded product.
得られた板状成型品は耐ブリード性、耐光性が優れて
いた。The plate-shaped molded product obtained was excellent in bleed resistance and light resistance.
実施例６〜９ 表−２に示すアントラピリドン系化合物を樹脂用着色
剤として使用して実施例１に記載の方法で成型した。得
られた成型品の耐ブリード性、耐溶出性及び耐光性は優
れていた。又、実施例１同様、耐熱性が優れていた。Examples 6 to 9 The anthrapyridone compounds shown in Table 2 were used as a colorant for resins and molded by the method described in Example 1. The obtained molded product was excellent in bleed resistance, elution resistance and light resistance. Also, as in Example 1, the heat resistance was excellent.
Claims (3)
基を表し、Ｂは式 で示される環を表し、ｎは１〜２の数を表す） で表されるアントラピリドン系化合物。1. A general formula [I] (In the formula, A represents a residue of a benzene ring which may be further substituted, and B represents the formula. The anthrapyridone-based compound represented by the formula (1), wherein n represents a number of 1 to 2).
基を表す） で表されるアントラピリドン系化合物と下記一般式〔II
I〕 （式中、Ｂは式 で示される環を表す） で示されるＮ−メチロール化合物とを反応させることを
特徴とする一般式〔Ｉ〕 （式中、Ａは更に置換されていてもよいベンゼン環の残
基を表し、Ｂは式 で示される環を表し、ｎは１〜２の数を表す） で表されるアントラピリドン系化合物の製造方法。2. General formula [II] (Wherein A represents a residue of a benzene ring which may be further substituted) and an anthrapyridone compound represented by the following general formula [II
I] (Where B is the formula The compound represented by the formula (I) is reacted with an N-methylol compound represented by (In the formula, A represents a residue of a benzene ring which may be further substituted, and B represents the formula. Represents a ring, and n represents a number of 1 to 2).
基を表し、Ｂは式 で示される環を表し、ｎは１〜２の数を表す） で表されるアントラピリドン系化合物を含んで成ること
を特徴とする樹脂用着色剤。3. A general formula [I] (In the formula, A represents a residue of a benzene ring which may be further substituted, and B represents the formula. And an anthrapyridone-based compound represented by the formula: n is a number of 1 to 2).
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22175587A JPH0826232B2 (en) | 1987-09-03 | 1987-09-03 | Anthrapyridone-based compound, production method and use thereof |
| EP87310447A EP0270306B1 (en) | 1986-12-01 | 1987-11-26 | Anthrapyridone compounds, their production process and their use |
| DE8787310447T DE3768922D1 (en) | 1986-12-01 | 1987-11-26 | ANTHRAPYRIDONE COMPOUNDS, THEIR PRODUCTION AND THEIR USE. |
| US07/126,596 US4902798A (en) | 1986-12-01 | 1987-11-30 | Anthrapyridone compounds |
| US08/167,443 US5367075A (en) | 1986-12-01 | 1993-12-14 | Anthrapyridone compounds, their production process and their use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22175587A JPH0826232B2 (en) | 1987-09-03 | 1987-09-03 | Anthrapyridone-based compound, production method and use thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6465174A JPS6465174A (en) | 1989-03-10 |
| JPH0826232B2 true JPH0826232B2 (en) | 1996-03-13 |
Family
ID=16771697
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22175587A Expired - Fee Related JPH0826232B2 (en) | 1986-12-01 | 1987-09-03 | Anthrapyridone-based compound, production method and use thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0826232B2 (en) |
-
1987
- 1987-09-03 JP JP22175587A patent/JPH0826232B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6465174A (en) | 1989-03-10 |
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