JPH05339237A - Pyridone-based compound - Google Patents
Pyridone-based compoundInfo
- Publication number
- JPH05339237A JPH05339237A JP14282792A JP14282792A JPH05339237A JP H05339237 A JPH05339237 A JP H05339237A JP 14282792 A JP14282792 A JP 14282792A JP 14282792 A JP14282792 A JP 14282792A JP H05339237 A JPH05339237 A JP H05339237A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- pyridone
- improved
- azo
- 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.)
- Granted
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
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
- C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
- C09B29/3626—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O)
- C09B29/363—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O) from diazotized amino carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は色素製造の中間体として
有用なピリドン系化合物に関する。FIELD OF THE INVENTION The present invention relates to a pyridone compound useful as an intermediate in the production of dyes.
【０００２】[0002]
【従来の技術】ピリドン系化合物は、アゾ色素製造の際
のカップラー成分として重要であり、色素製造の中間体
として広く用いられている。一般にピリドンアゾ系色素
は、イエロー色素としては吸収波長が短く、マゼンタ、
シアン色素と組み合わせて使用する際、ブラックの濃度
が不十分であるという問題がある。カップラー成分であ
るピリドン系化合物にトリフルオロメチル基を導入する
ことによりアゾ色素の深色化が可能と予想されるが、ト
リフルオロメチル基を含むピリドン系化合物は知られて
いない。BACKGROUND OF THE INVENTION Pyridone compounds are important as coupler components in the production of azo dyes and are widely used as intermediates in the production of dyes. In general, pyridone azo dye has a short absorption wavelength as a yellow dye,
When used in combination with a cyan dye, there is a problem that the density of black is insufficient. By introducing a trifluoromethyl group into the pyridone compound that is the coupler component, it is expected that the azo dye can be bathochromatized, but a pyridone compound containing a trifluoromethyl group has not been known.
【０００３】[0003]
【発明が解決しようとする課題】本発明はアゾ色素製造
の中間体として有用なトリフルオロメチル基を含んだピ
リドン系化合物を提供することを目的とする。SUMMARY OF THE INVENTION It is an object of the present invention to provide a pyridone compound containing a trifluoromethyl group, which is useful as an intermediate for producing an azo dye.
【０００４】[0004]
【課題を解決するための手段】本発明は前記請求項１に
おいて、一般式（Ｉ）で示されるピリドン系化合物をそ
の要旨とする。以下本発明を詳細に説明する。本発明の
前記一般式（Ｉ）で示されるピリドン系化合物を具体的
に説明すると、式中Ｒで表わされる非置換のアルキル基
としては、炭素数１〜１０の直鎖状もしくは分岐鎖状の
アルキル基があげられる。The gist of the present invention is the pyridone compound represented by formula (I) in claim 1. The present invention will be described in detail below. The pyridone compound represented by the general formula (I) of the present invention will be specifically described. In the formula, the unsubstituted alkyl group represented by R is a linear or branched chain having 1 to 10 carbon atoms. An alkyl group is mentioned.
【０００５】本発明のピリドン系化合物の具体例として
は、前記一般式（Ｉ）においてＲで示される基が後記第
１表に示されるものがあげられる。Specific examples of the pyridone compound of the present invention include those in which the group represented by R in the general formula (I) is shown in Table 1 below.
【０００６】[0006]
【表１】 [Table 1]
【０００７】本発明の前記一般式（Ｉ）で示されるピリ
ドン系化合物は、例えば下記の方法に従って製造するこ
とができる。即ち、トリフルオロアセト酢酸エチルエス
テルと、シアノ酢酸メチルエステルと、下記一般式（I
I） Ｒ−ＮＨ2 （II） （式中Ｒは前記一般式（Ｉ）と同じ意味を表わす）で示
されるアミン類とを混合し、加熱下で反応させることに
より製造することができる。反応温度としては６０〜９
０℃が適当である。反応終了後の目的物の取り出し方法
としては、反応液を３％塩酸水溶液に排出し、析出した
結晶をろ過し、水洗後乾燥すれば良い。The pyridone compound represented by the general formula (I) of the present invention can be produced, for example, according to the following method. That is, trifluoroacetoacetic acid ethyl ester, cyanoacetic acid methyl ester, and the following general formula (I
I) R-NH 2 (II ) ( wherein R is the formula (I) mixing the amine represented by the representative) the same meaning as can be produced by reacting under heating. The reaction temperature is 60 to 9
0 ° C is suitable. After the completion of the reaction, the desired product can be taken out by discharging the reaction solution into a 3% aqueous hydrochloric acid solution, filtering the precipitated crystals, washing with water and drying.
【０００８】[0008]
【発明の効果】本発明のピリドン系化合物は新規なピリ
ドンアゾ系色素の中間体として有用であり、この化合物
をカップラーとして製造されるアゾ色素は下記一般式
（III)INDUSTRIAL APPLICABILITY The pyridone compound of the present invention is useful as an intermediate for a novel pyridone azo dye, and the azo dye produced using this compound as a coupler has the following general formula (III):
【０００９】[0009]
【化２】 [Chemical 2]
【００１０】で示されるピリドン系化合物から製造され
るアゾ色素に比べて最大吸収波長が長波長化しており、
適当なマゼンタ色およびシアン色を組み合わせることに
より得られるブラックの色濃度が向上するという効果が
あり、又、溶解度が向上し、感熱転写記録用色素として
用いた場合、記録濃度が向上するという効果がある。The maximum absorption wavelength is longer than that of the azo dye produced from the pyridone compound represented by
There is an effect that the color density of black obtained by combining appropriate magenta color and cyan color is improved, and also that the solubility is improved and, when it is used as a dye for thermal transfer recording, the effect that the recording density is improved. is there.
【００１１】[0011]
【実施例】以下の実施例により本発明を具体的に説明す
るが、かかる実施例は本発明を限定するものではない。The present invention will be described in detail with reference to the following examples, but the examples do not limit the present invention.
【００１２】実施例１ トリフルオロアセト酢酸エチルエステル２４．９ｇ、シ
アノ酢酸メチルエステル１３．５ｇ及びメチルアミン水
溶液（４０％）２１．１ｇを混合し、６０〜７０℃に昇
温し６０〜７０℃で８時間攪拌した。上記の反応液を室
温まで冷却後、水３０４ml、濃塩酸２８mlの混合液中に
添加し室温で１時間攪拌した。析出した結晶を吸引ろ取
後乾燥し、前記一般式（Ｉ）においてＲがメチル基であ
るピリドン系化合物２７．１ｇを得た。Example 1 24.9 g of trifluoroacetoacetic acid ethyl ester, 13.5 g of cyanoacetic acid methyl ester and 21.1 g of methylamine aqueous solution (40%) were mixed, and the temperature was raised to 60 to 70 ° C. and 60 to 70 ° C. It was stirred for 8 hours. After the above reaction solution was cooled to room temperature, it was added to a mixed solution of 304 ml of water and 28 ml of concentrated hydrochloric acid and stirred at room temperature for 1 hour. The precipitated crystals were collected by suction filtration and dried to obtain 27.1 g of the pyridone compound in which R in the general formula (I) was a methyl group.
【００１３】本品は融点２０４．５〜２０６．０℃の白
色結晶であった。本品の他の物性値を以下に示す。 マススペクトル：ｍ／ｚ ２１８（Ｍ+ ） 元素分析：Ｃ8 Ｈ5 Ｎ2 Ｏ2 Ｆ3 計算値 Ｃ ４４．０５ Ｈ ２．３１ Ｎ １
２．８４ 実測値 Ｃ ４３．８２ Ｈ ２．２８ Ｎ １
２．８２The product was white crystals having a melting point of 204.5 to 206.0 ° C. Other physical properties of this product are shown below. Mass spectrum: m / z 218 (M + ) Elemental analysis: C 8 H 5 N 2 O 2 F 3 calculated value C 44.05 H 2.31 N 1
2.84 Found C 43.82 H 2.28 N 1
2.82
【００１４】実施例２ トリフルオロアセト酢酸エチルエステル２４．９ｇ、シ
アノ酢酸メチルエステル１３．５ｇ及びエチルアミン水
溶液（７０％）１７．６ｇを混合し、７０〜８０℃に昇
温し、７０〜８０℃で８時間攪拌した。上記の反応液を
室温まで冷却後、水３０４ml、濃塩酸２８mlの混合液中
に添加し室温で１時間攪拌した。析出した結晶を吸引ろ
取後乾燥し、前記一般式（Ｉ）においてＲがエチル基で
あるピリドン系化合物２４．４ｇを得た。Example 2 Trifluoroacetoacetic acid ethyl ester (24.9 g), cyanoacetic acid methyl ester (13.5 g) and ethylamine aqueous solution (70%) (17.6 g) were mixed, and the mixture was heated to 70-80 ° C and 70-80 ° C. It was stirred for 8 hours. After the above reaction solution was cooled to room temperature, it was added to a mixed solution of 304 ml of water and 28 ml of concentrated hydrochloric acid and stirred at room temperature for 1 hour. The precipitated crystals were collected by suction filtration and dried to obtain 24.4 g of the pyridone compound in which R in the general formula (I) was an ethyl group.
【００１５】本品は融点２２４．５〜２２６．５℃の白
色結晶であった。本品の他の物性値を以下に示す。 マススペクトル：ｍ／ｚ ２３２（Ｍ+ ） 元素分析：Ｃ9 Ｈ7 Ｎ2 Ｏ2 Ｆ3 計算値 Ｃ ４６．５６ Ｈ ３．０４ Ｎ １
２．０７ 実測値 Ｃ ４６．２８ Ｈ ３．００ Ｎ １
１．９８The product was white crystals having a melting point of 224.5 to 226.5 ° C. Other physical properties of this product are shown below. Mass spectrum: m / z 232 (M + ) Elemental analysis: C 9 H 7 N 2 O 2 F 3 calculated value C 46.56 H 3.04 N 1
2.07 measured value C 46.28 H 3.00 N 1
1.98
【００１６】参考例１ アゾ色素の合成 ｍ−フルオロアニリン８．１ｇを水１９０ml及び濃塩酸
９mlと混合し、これに０〜５℃で亜硝酸ナトリウム５．
６ｇの水溶液を添加し、０〜５℃で１時間攪拌した。こ
れにスルファミン酸１．１ｇを添加して攪拌した後、前
記実施例１で得られたピリドン系化合物２０ｇのメタノ
ール溶液を０〜５℃で添加し、水酸化ナトリウム水溶液
により反応溶液のｐＨを５〜６に調整した。これを０〜
５℃で２時間攪拌後、析出した結晶を吸引ろ取し乾燥し
て、カラムクロマトグラフィーにより精製し、次の式Reference Example 1 Synthesis of Azo Dye 8.1 g of m-fluoroaniline was mixed with 190 ml of water and 9 ml of concentrated hydrochloric acid, and this was mixed with sodium nitrite at 0-5 ° C.
6 g of an aqueous solution was added, and the mixture was stirred at 0 to 5 ° C for 1 hour. After 1.1 g of sulfamic acid was added and stirred, a methanol solution of 20 g of the pyridone compound obtained in Example 1 was added at 0 to 5 ° C., and the pH of the reaction solution was adjusted to 5 with an aqueous sodium hydroxide solution. Adjusted to ~ 6. 0 to this
After stirring at 5 ° C for 2 hours, the precipitated crystals were collected by suction filtration, dried, and purified by column chromatography to give the following formula
【００１７】[0017]
【化３】 [Chemical 3]
【００１８】で表わされるピリドンアゾ系色素１４．５
ｇを得た。本品は融点１２０．５〜１２１．３℃の黄色
結晶であり、アセトン中の吸収スペクトル測定結果はλ
max ４３２ｎｍ、εmax ４．５×１０4 であり、本色素
は鮮明な黄色を示した。Pyridone azo dye 14.5 represented by
g was obtained. This product is a yellow crystal with a melting point of 120.5-121.3 ° C, and the absorption spectrum measurement result in acetone is λ.
max 432 nm and ε max 4.5 × 10 4 , and this dye showed a vivid yellow color.
Claims (1)
化合物。 【化１】 （式中、Ｒはアルキル基を表わす）1. A pyridone compound represented by the following general formula (I): [Chemical 1] (In the formula, R represents an alkyl group)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14282792A JP3243837B2 (en) | 1992-06-03 | 1992-06-03 | Pyridone compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14282792A JP3243837B2 (en) | 1992-06-03 | 1992-06-03 | Pyridone compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05339237A true JPH05339237A (en) | 1993-12-21 |
| JP3243837B2 JP3243837B2 (en) | 2002-01-07 |
Family
ID=15324545
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14282792A Expired - Fee Related JP3243837B2 (en) | 1992-06-03 | 1992-06-03 | Pyridone compounds |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3243837B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6086637A (en) * | 1996-11-23 | 2000-07-11 | Basf Aktiengesellschaft | Trifluormethylpyridone based indolenine methine dyes |
-
1992
- 1992-06-03 JP JP14282792A patent/JP3243837B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6086637A (en) * | 1996-11-23 | 2000-07-11 | Basf Aktiengesellschaft | Trifluormethylpyridone based indolenine methine dyes |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3243837B2 (en) | 2002-01-07 |
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