JP2868143B2 - Cobalt-containing azo dye composition and dyeing method using the same - Google Patents
Cobalt-containing azo dye composition and dyeing method using the sameInfo
- Publication number
- JP2868143B2 JP2868143B2 JP5300899A JP30089993A JP2868143B2 JP 2868143 B2 JP2868143 B2 JP 2868143B2 JP 5300899 A JP5300899 A JP 5300899A JP 30089993 A JP30089993 A JP 30089993A JP 2868143 B2 JP2868143 B2 JP 2868143B2
- Authority
- JP
- Japan
- Prior art keywords
- cobalt
- group
- dyeing
- azo dye
- monoazo compound
- 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
Landscapes
- Coloring (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明は、コバルト含有アゾ染料
組成物及びそれを用いるポリアミド繊維材料の染色方法
に関する。The present invention relates to a cobalt-containing azo dye composition and a method for dyeing a polyamide fiber material using the same.
【０００２】[0002]
【従来の技術】従来、モノアゾ染料のクロム又はコバル
ト錯塩は、合成又は天然のポリアミド繊維・材料に対し
て優れた染色性を有し、例えば、色相、鮮明度、湿潤堅
牢度、耐光堅牢度等に優れることから広く使用されてい
る。例えば特公昭42-5340 号公報、特公昭46-2428 号公
報、特開昭58-5365 号公報、特開昭60-88186号公報、特
開昭62-225563 号公報等には種々のクロム又はコバルト
錯塩モノアゾ染料が記載されている。2. Description of the Related Art Hitherto, chromium or cobalt complex salts of monoazo dyes have excellent dyeing properties on synthetic or natural polyamide fibers and materials, for example, hue, sharpness, wet fastness, light fastness and the like. Widely used because it is excellent. For example, JP-B-42-5340, JP-B-46-2428, JP-A-58-5365, JP-A-60-88186, JP-A-62-225563, etc. disclose various chromium or Cobalt complex monoazo dyes are described.
【０００３】[0003]
【発明が解決しようとする課題】しかし、近年加工が盛
んになったポリアミド系人工皮革の染色においては、鮮
明なネイビーブルー色乃至はルビン色に高濃度に染色す
る染料は少なく、特にカラーバリューが高く、諸堅牢度
のすぐれた鮮明な青色乃至紫色系染料が強く要望されて
いた。本発明者らは、特定の構造を有するコバルト含有
アゾ染料混合組成物を用いることにより、これらの要望
を満たすことを見出し、本発明を完成した。However, in the dyeing of polyamide-based artificial leather, which has been actively processed in recent years, there are few dyes that can be dyed at a high density in a clear navy blue or rubin color, and the color value is particularly low. There has been a strong demand for vivid blue to purple dyes that are high and have excellent fastnesses. The present inventors have found that these requirements are satisfied by using a cobalt-containing azo dye mixture composition having a specific structure, and have completed the present invention.
【０００４】[0004]
【課題を解決するための手段】本発明は、一般式（１）According to the present invention, there is provided a compound represented by the general formula (1):
【０００５】[0005]
【化４】 Embedded image
【０００６】（式中、Ｘ、Ｙはそれぞれ独立に水素原
子、ニトロ基、クロル原子、メチル基、エチル基、スル
ファモイル基、メトキシ基又はエトキシ基を示す。Ｒ
1 、Ｒ2 はそれぞれ独立に炭素数１〜４の低級アルキル
基を示し、Ｒは水素原子またはメチル基を示す。）で表
わされるモノアゾ化合物の１：２−コバルト錯体アゾ染
料２０〜８０重量部と、一般式（２）又は一般式（３）(Wherein, X and Y each independently represent a hydrogen atom, a nitro group, a chloro atom, a methyl group, an ethyl group, a sulfamoyl group, a methoxy group or an ethoxy group.
1 and R 2 each independently represent a lower alkyl group having 1 to 4 carbon atoms, and R represents a hydrogen atom or a methyl group. 20) to 80 parts by weight of a 1: 2-cobalt complex azo dye of a monoazo compound represented by the following formula (2) or (3):
【０００７】[0007]
【化５】 Embedded image
【０００８】[0008]
【化６】 Embedded image
【０００９】（上記式中、Ｑ、Ｚはそれぞれ独立に水素
原子、ニトロ基、クロル原子、メチル基、エチル基、ス
ルファモイル基、メトキシ基又はエトキシ基を示す。Ｒ
3 は、炭素数１〜４の低級アルキル基を示す。）で表わ
されるモノアゾ化合物の１：２−コバルト錯体アゾ染料
８０〜２０重量部とからなることを特徴とするコバルト
含有アゾ染料組成物である。(In the above formula, Q and Z each independently represent a hydrogen atom, a nitro group, a chloro atom, a methyl group, an ethyl group, a sulfamoyl group, a methoxy group or an ethoxy group.
3 represents a lower alkyl group having 1 to 4 carbon atoms. (1) Cobalt-containing azo dye composition comprising 80 to 20 parts by weight of a 1: 2-cobalt complex azo dye of a monoazo compound represented by the following formula:
【００１０】一般式（１）で示されるモノアゾ化合物
は、例えば、３−（ジメチルアミノ）フェノール、３−
（ジエチルアミノ）フェノール、３−（ジブチルアミ
ノ）フェノール、３−（ジプロピルアミノ）フェノー
ル、３−（ジエチルアミノ）フェノール、３−（ジメチ
ルアミノ）−４−メチルフェノール、３−（ジエチルア
ミノ）−４−メチルフェノール、３−（ジブチルアミ
ノ）−４−メチルフェノールと、ジアゾ化された２−ア
ミノ−フェノール、２−アミノ−４−ニトロフェノー
ル、２−アミノ−５−ニトロフェノール、２−アミノ−
４−クロルフェノール、２−アミノ−４−メチルフェノ
ール、２−アミノ−４−メトキシフェノール、２−アミ
ノ−４−クロル−６−ニトロ−フェノール、２−アミノ
−４−ニトロ−６−クロル−フェノール、２−アミノ−
４−メチル−６−ニトロ−フェノールなどとを弱酸性、
中性または弱アルカリ性の媒質中でカップリング反応さ
せることによって容易に得られる。The monoazo compound represented by the general formula (1) is, for example, 3- (dimethylamino) phenol, 3- (dimethylamino) phenol,
(Diethylamino) phenol, 3- (dibutylamino) phenol, 3- (dipropylamino) phenol, 3- (diethylamino) phenol, 3- (dimethylamino) -4-methylphenol, 3- (diethylamino) -4-methyl Phenol, 3- (dibutylamino) -4-methylphenol and diazotized 2-amino-phenol, 2-amino-4-nitrophenol, 2-amino-5-nitrophenol, 2-amino-
4-chlorophenol, 2-amino-4-methylphenol, 2-amino-4-methoxyphenol, 2-amino-4-chloro-6-nitro-phenol, 2-amino-4-nitro-6-chloro-phenol , 2-amino-
Weakly acidic with 4-methyl-6-nitro-phenol and the like;
It is easily obtained by performing a coupling reaction in a neutral or weakly alkaline medium.
【００１１】前記一般式（２）又は（３）で示されるモ
ノアゾ化合物は、例えば、６−アミノ−Ｎ−メチル−２
−ナフタレンスルホンアミド、６−アミノ−Ｎ−エチル
−２−ナフタレンスルホンアミド、６−アミノ−Ｎ−プ
ロピル−２−ナフタレンスルホンアミド、６−アミノ−
Ｎ−ブチル−２−ナフタレンスルホンアミド、６−ヒド
ロキシ−Ｎ−メチル−２−ナフタレンスルホンアミド、
６−ヒドロキシ−Ｎ−エチル−２−ナフタレンスルホン
アミド、６−ヒドロキシ−Ｎ−プロピル−２−ナフタレ
ンスルホンアミド、６−ヒドロキシ−Ｎ−ブチル−２−
ナフタレンスルホンアミドと、ジアゾ化された２−アミ
ノ−フェノール、２−アミノ−４−ニトロフェノール、
２−アミノ−５−ニトロフェノール、２−アミノ−４−
クロルフェノール、２−アミノ−４−メチルフェノー
ル、２−アミノ−４−メトキシフェノール、２−アミノ
−４−クロル−６−ニトロ−フェノール、２−アミノ−
４−クロル−５−ニトロフェノール、２−アミノ−４−
ニトロ−６−クロルフェノール、２−アミノ−４−メチ
ル−６−ニトロ−フェノール２−アミノ−４，６ジニト
ロフェノールとをカップリング反応させることにより容
易に製造することができる。The monoazo compound represented by the general formula (2) or (3) is, for example, 6-amino-N-methyl-2
-Naphthalenesulfonamide, 6-amino-N-ethyl-2-naphthalenesulfonamide, 6-amino-N-propyl-2-naphthalenesulfonamide, 6-amino-
N-butyl-2-naphthalenesulfonamide, 6-hydroxy-N-methyl-2-naphthalenesulfonamide,
6-hydroxy-N-ethyl-2-naphthalenesulfonamide, 6-hydroxy-N-propyl-2-naphthalenesulfonamide, 6-hydroxy-N-butyl-2-
Naphthalenesulfonamide, diazotized 2-amino-phenol, 2-amino-4-nitrophenol,
2-amino-5-nitrophenol, 2-amino-4-
Chlorophenol, 2-amino-4-methylphenol, 2-amino-4-methoxyphenol, 2-amino-4-chloro-6-nitro-phenol, 2-amino-
4-chloro-5-nitrophenol, 2-amino-4-
Nitro-6-chlorophenol and 2-amino-4-methyl-6-nitro-phenol can be easily produced by a coupling reaction with 2-amino-4,6 dinitrophenol.
【００１２】本発明者らは、モノアゾ化合物２分子にコ
バルト１原子が錯結合しているいわゆる対称型コバルト
錯塩染料、すなわち一般式（１）の１：２コバルト錯塩
染料と一般式（２）又は一般式（３）の１：２コバルト
錯塩染料とを所定の割合で混合して得られる混合染料組
成物が、ポリアミド繊維、特にポリアミド系人工皮革の
染色に用いて、色相、染色性、諸堅牢度等において極め
て好ましい性能をもたらすことを見出し、本発明を完成
するに至った。The present inventors have proposed a so-called symmetrical cobalt complex dye in which one molecule of cobalt is complex-bonded to two molecules of a monoazo compound, that is, a 1: 2 cobalt complex dye of the general formula (1) and a compound of the general formula (2) or (2). A mixed dye composition obtained by mixing a 1: 2 cobalt complex salt dye of the general formula (3) at a predetermined ratio is used for dyeing polyamide fibers, particularly polyamide-based artificial leather, to obtain a hue, dyeability, and various fastnesses. The inventors have found that the present invention provides extremely favorable performance in terms of degree and the like, and have completed the present invention.
【００１３】本発明の目的とするコバルト含有アゾ染料
組成物製造方法としては、前記一般式に示したモノアゾ
化合物にコバルト付与剤を反応させる公知の方法が適用
され、例えばこれらのモノアゾ化合物を、水又はメタノ
ール、アセトン、グリコール類等の水性媒質中、モノア
ゾ化合物ベースに対して、０．５１〜０．６モル比のコ
バルト付与剤を用い、温度７０〜１１０℃、好ましくは
９０〜９５℃で行われる。As a method for producing the cobalt-containing azo dye composition of the present invention, a known method of reacting a monoazo compound represented by the above general formula with a cobalt imparting agent is applied. Alternatively, in an aqueous medium such as methanol, acetone, or glycols, a cobalt-imparting agent is used in a molar ratio of 0.51 to 0.6 with respect to the monoazo compound base at a temperature of 70 to 110 ° C, preferably 90 to 95 ° C. Will be
【００１４】ここで、コバルト付与剤としては、例え
ば、硫酸コバルト、酒石酸コバルト、酢酸コバルト等が
用いられる。この際、コバルト化の触媒として、アルカ
ノールアミン等の有機アミン類、苛性ソーダ、ソーダ灰
等のアルカリ剤を用いることが出来る。かくして得られ
た一般式（１）で示されるモノアゾ化合物の１：２コバ
ルト錯塩染料と、一般式（２）又は一般式（３）の１：
２コバルト錯塩染料とを所定の割合で混合することによ
って本発明の混合染料組成物が得られる。その混合割合
は、一般式（１）で示されるモノアゾ化合物の１：２コ
バルト錯塩染料が２０〜８０重量部、好ましくは３０〜
７０重量部、及び一般式（２）又は一般式（３）の１：
２コバルト錯塩染料が８０〜２０重量部、好ましくは７
０〜３０重量部である。Here, as the cobalt imparting agent, for example, cobalt sulfate, cobalt tartrate, cobalt acetate and the like are used. At this time, an organic amine such as alkanolamine and an alkaline agent such as caustic soda and soda ash can be used as a catalyst for cobaltation. The thus obtained 1: 2 cobalt complex salt dye of the monoazo compound represented by the general formula (1) and 1: 2 of the general formula (2) or (3).
The mixed dye composition of the present invention can be obtained by mixing the 2 cobalt complex dye with a predetermined ratio. The mixing ratio is such that the 1: 2 cobalt complex salt dye of the monoazo compound represented by the general formula (1) is 20 to 80 parts by weight, preferably 30 to 80 parts by weight.
70 parts by weight, and 1 of the general formula (2) or the general formula (3):
80 to 20 parts by weight, preferably 7,
0 to 30 parts by weight.
【００１５】本発明の目的とするコバルト含有アゾ染料
組成物の他の製造方法としては、一般式（１）で示され
るモノアゾ化合物、一般式（２）又は（３）で示される
モノアゾ化合物の前駆体にコバルト付与剤を反応させる
ことによっても得られる。例えば少なくとも一種のジア
ゾ成分のジアゾ化物と、少なくとも２種のカップリング
成分の混合物とを反応させて得られる少なくとも２種の
金属を含まないモノアゾ化合物の混合物にコバルト付与
剤を作用させて、同時的に本発明の目的とするコバルト
含有アゾ染料の混合染料組成物を製造することもでき
る。As another method for producing the cobalt-containing azo dye composition of the present invention, a monoazo compound represented by the general formula (1) or a precursor of the monoazo compound represented by the general formula (2) or (3) is used. It can also be obtained by reacting a body with a cobalt imparting agent. For example, by reacting a mixture of at least one diazo component of a diazo component and a mixture of at least two types of metal-free monoazo compounds obtained by reacting a mixture of at least two types of coupling components with a cobalt imparting agent, In addition, a mixed dye composition of a cobalt-containing azo dye aimed at by the present invention can also be produced.
【００１６】なお、この場合に一般式（１）で示される
モノアゾ化合物と一般式（２）又は（３）で示されるモ
ノアゾ化合物（モノアゾ化合物２分子）にコバルト１原
子が錯結合している、いわゆる非対称型コバルト錯塩染
料が混入生成することがあるが、かかる混合染料組成物
でもポリアミド繊維の染色に好ましい結果をもたらすこ
とがあり、本発明に含まれる。In this case, one atom of cobalt is complex-bonded to the monoazo compound represented by the general formula (1) and the monoazo compound (two molecules of the monoazo compound) represented by the general formula (2) or (3). A so-called asymmetric type cobalt complex dye may be mixed and formed, but such a mixed dye composition may bring about a favorable result for dyeing polyamide fibers and is included in the present invention.
【００１７】本発明のコバルト含有アゾ染料組成物の取
り出しは、通常の方法によって塩析、濾過、乾燥し、或
いは水溶液のまま、スプレイ乾燥し、又は必要により濃
縮し、有機溶媒を加え、濃厚水溶液の形で染色に供する
こともできる。本発明のコバルト含有アゾ染料組成物
は、その合成および沈澱生成の後に乾燥しないで湿った
ペーストの形で次の処理に使用するのが有利である。The cobalt-containing azo dye composition of the present invention is taken out by salting out, filtration, drying, or spray drying as it is in an aqueous solution, or concentrating as necessary, adding an organic solvent, and adding an organic solvent to the concentrated aqueous solution. Can also be used for dyeing. The cobalt-containing azo dye compositions of the present invention are advantageously used in the subsequent processing in the form of a wet paste without drying after their synthesis and precipitation.
【００１８】本発明のコバルト含有アゾ染料組成物は、
非常に多くの種類の物質を染色および捺染するのに適し
ている。特にこの化合物は動物性物質、例えば絹、皮革
特に羊毛の染色に適しているが、ポリアミド、ポリウレ
タン等から作られた合成繊維材料の染色および捺染にも
適している。特にポリアミド系合成皮革、スゥエード材
料に対してカラーバリューが高く、諸堅牢度のすぐれた
鮮明な青色乃至紫色に染色するのに適する。The cobalt-containing azo dye composition of the present invention comprises
Suitable for dyeing and printing numerous types of materials. In particular, the compounds are suitable for dyeing animal substances, such as silk, leather, especially wool, but also for dyeing and printing synthetic fiber materials made from polyamides, polyurethanes and the like. In particular, it has a high color value with respect to polyamide-based synthetic leather and suede materials, and is suitable for dyeing in a clear blue or purple color with excellent fastness.
【００１９】本発明のコバルト含有アゾ染料組成物は、
弱アルカリ性〜弱酸性の浴から染色することができる
が、特に中性または僅かに酸性例えば酢酸若しくは硫安
を含んでいる浴から適用して好結果が得られる。こうし
て得られた染色物は均一であって日光、洗濯等に対して
良好な堅牢度を示すが特にその鮮明度およびビルドアッ
プ性において優れている。The cobalt-containing azo dye composition of the present invention comprises
Dyeings can be carried out from weakly alkaline to slightly acidic baths, but are particularly successful with application from neutral or slightly acidic baths containing, for example, acetic acid or ammonium sulphate. The dyed product thus obtained is uniform and shows good fastness to sunlight, washing and the like, but is particularly excellent in its sharpness and build-up property.
【００２０】[0020]
【発明の効果】本発明のコバルト含有アゾ染料組成物
は、好ましい青色色相を有し、特に動物性物質、例えば
絹、皮革、特に羊毛の染色に適しているが、ポリアミ
ド、ポリウレタンおよびポリアクリロニトリルから作ら
れた合成繊維材料の染色および捺染にも適している。ま
た、ポリアミド系人工皮革又はポリアミド系合成皮革、
特にスゥエード調の材料に対してカラーバリューが高
く、諸堅牢度のすぐれた鮮明な青色乃至紫色に染色す
る。The cobalt-containing azo dye compositions according to the invention have a favorable blue hue and are particularly suitable for dyeing animal substances, such as silk, leather, especially wool, but are particularly suitable for dyeing polyamides, polyurethanes and polyacrylonitriles. It is also suitable for dyeing and printing of synthetic fiber materials made. In addition, polyamide-based artificial leather or polyamide-based synthetic leather,
In particular, it has a high color value with respect to a suede-like material and is dyed in a clear blue or purple color having excellent fastnesses.
【００２１】[0021]
【実施例】以下、実施例によって本発明を具体的に説明
する。なお、実施例中、部は重量部を表わす。The present invention will be specifically described below with reference to examples. In the examples, parts represent parts by weight.
【００２２】実施例１ ２−アミノ−５−ニトロフェノールのジアゾ化物に、６
−アミノ−Ｎ−メチル−２−ナフタレンスルホンアミド
を通常の方法によってカップリングさせて得られるモノ
アゾ化合物（Ａ）にコバルト付与剤を作用させて得られ
る１：２−コバルト錯体アゾ染料５０部と２−アミノ−
５−ニトロフェノールのジアゾ化物に、３−（ジエチル
アミノ）フェノールをカップリングさせて得られるモノ
アゾ化合物（Ｂ）にコバルト付与剤を作用させて得られ
る１：２−コバルト錯体アゾ染料５０部とを混合して染
料組成物を得た。Example 1 2-amino-5-nitrophenol diazotized
50 parts of a 1: 2-cobalt complex azo dye obtained by reacting a monoazo compound (A) obtained by coupling -amino-N-methyl-2-naphthalenesulfonamide by a conventional method with a cobalt-imparting agent; -Amino-
A diazotized product of 5-nitrophenol is mixed with 50 parts of a 1: 2-cobalt complex azo dye obtained by reacting a monoazo compound (B) obtained by coupling 3- (diethylamino) phenol with a cobalt imparting agent. Thus, a dye composition was obtained.
【００２３】得られた混合染料組成物０．１ｇを水１０
０ｇに溶解し、ミニカラー染色試験機の染色ポットに入
れ、これにスエード調のポリアミド系人工皮革２．０ｇ
を投入して蓋をした。この染色ポットを内温４０℃のミ
ニカラー染色機に挿入し、９０℃まで５０分間で昇温し
た。９０℃で３０分間保温したのち、染色ポットを取り
出し冷却する。被染物を取り出し、常法に従って洗浄し
た。かくして得られた染色物は、鮮明なネイビーブルー
色を呈し、諸堅牢度も良好であった。0.1 g of the obtained mixed dye composition was added to 10 parts of water.
0 g, and put in a dye pot of a mini-color dyeing tester, and add 2.0 g of suede-like artificial polyamide leather.
And put on the lid. This dyeing pot was inserted into a mini-color dyeing machine having an internal temperature of 40 ° C., and the temperature was raised to 90 ° C. in 50 minutes. After keeping the temperature at 90 ° C. for 30 minutes, the dyeing pot is taken out and cooled. The material to be dyed was taken out and washed according to a conventional method. The dyed product thus obtained exhibited a clear navy blue color and good fastnesses.
【００２４】実施例２ 実施例１に記載の方法によって得られたモノアゾ化合物
（Ａ）とモノアゾ化合物（Ｂ）の混合物に、通常の方法
によってコバルト付与剤を作用させてコバルト化を完了
させる。Example 2 A mixture of the monoazo compound (A) and the monoazo compound (B) obtained by the method described in Example 1 is allowed to act with a cobalt-imparting agent by a conventional method to complete the cobaltation.
【００２５】得られた染料組成物は、モノアゾ化合物
（Ａ）の対称型１：２コバルト染料及びモノアゾ化合物
（Ｂ）の対称型１：２コバルト染料を等量含有し、さら
にモノアゾ化合物（Ａ）とモノアゾ化合物（Ｂ）各１分
子に対してコバルト１分子が配位したいわゆる非対称型
１：２コバルト染料が相当量含まれた混合染料組成物で
あった。The obtained dye composition contains an equal amount of the symmetrical 1: 2 cobalt dye of the monoazo compound (A) and the symmetrical 1: 2 cobalt dye of the monoazo compound (B), and further contains the monoazo compound (A). And a monoazo compound (B), a mixed dye composition containing a considerable amount of a so-called asymmetric 1: 2 cobalt dye in which one molecule of cobalt is coordinated with one molecule of each.
【００２６】上記の方法によって得られた混合染料組成
物０．１ｇを水１００ｇに溶解し、ミニカラー染色試験
機の染色ポットに入れ、これにスエード調のポリアミド
系人工皮革２．０ｇを投入して蓋をした。この染色ポッ
トを内温４０℃のミニカラー染色機に挿入し、９０℃ま
で５０分間で昇温した。９０℃で３０分間保温したの
ち、染色ポットを取り出し冷却する。被染物を取り出
し、常法に従って洗浄した。かくして得られた染色物
は、鮮明なネイビーブルー色を呈し、諸堅牢度も良好で
あった。0.1 g of the mixed dye composition obtained by the above method is dissolved in 100 g of water, put into a dyeing pot of a mini-color dyeing tester, and 2.0 g of suede-like polyamide artificial leather is put therein. With a lid. This dyeing pot was inserted into a mini-color dyeing machine having an internal temperature of 40 ° C., and the temperature was raised to 90 ° C. in 50 minutes. After keeping the temperature at 90 ° C. for 30 minutes, the dyeing pot is taken out and cooled. The material to be dyed was taken out and washed according to a conventional method. The dyed product thus obtained exhibited a clear navy blue color and good fastnesses.
【００２７】実施例３ ２−アミノ−５−ニトロフェノールのジアゾ化物に、６
−ヒドロキシ−Ｎ−メチル−２−ナフタレンスルホンア
ミドとを通常の方法によってカップリングさせてモノア
ゾ化合物（Ｃ）を得、通常の方法によってコバルト付与
剤を作用させて１：２−コバルト錯体アゾ染料を得た。
一方、実施例１で得られたモノアゾ染料（Ｂ）に、通常
の方法によってコバルト付与剤を作用させて１：２−コ
バルト錯体アゾ染料を得、これらのコバルト錯体アゾ染
料を等量混合して混合染料組成物を得た。Example 3 The diazotized product of 2-amino-5-nitrophenol was added with 6
-Hydroxy-N-methyl-2-naphthalenesulfonamide is coupled by a conventional method to obtain a monoazo compound (C), and a 1: 2-cobalt complex azo dye is reacted by a conventional method with a cobalt imparting agent. Obtained.
On the other hand, the monoazo dye (B) obtained in Example 1 was reacted with a cobalt imparting agent by a usual method to obtain a 1: 2-cobalt complex azo dye, and these cobalt complex azo dyes were mixed in equal amounts. A mixed dye composition was obtained.
【００２８】この染料混合物０．１ｇを水１００ｇに溶
解し、ミニカラー染色試験機の染色ポットに入れ、これ
にスエード調のポリアミド系人工皮革２．０ｇを投入し
て蓋をした。この染色ポットを内温４０℃のミニカラー
染色機に挿入し、９０℃まで５０分間で昇温した。９０
℃で３０分間保温したのち、染色ポットを取り出し冷却
する。被染物を取り出し、常法に従って洗浄した。かく
して得られた染色物は、鮮明なバイオレット色を呈し、
諸堅牢度も良好であった。0.1 g of this dye mixture was dissolved in 100 g of water, put into a dyeing pot of a mini-color dyeing tester, and 2.0 g of suede-like artificial polyamide leather was put into the pot and the lid was closed. This dyeing pot was inserted into a mini-color dyeing machine having an internal temperature of 40 ° C., and the temperature was raised to 90 ° C. in 50 minutes. 90
After keeping the temperature at 30 ° C for 30 minutes, the dyeing pot is taken out and cooled. The material to be dyed was taken out and washed according to a conventional method. The dyed material thus obtained has a clear violet color,
Various fastnesses were also good.
【００２９】実施例４ 実施例３で得られたモノアゾ化合物（Ｃ）と実施例１で
得られたモノアゾ化合物（Ｂ）との略等量混合物にコバ
ルト付与剤を作用させてコバルト化を完了させた。得ら
れた染料は、モノアゾ化合物（Ｂ）の対称型１：２コバ
ルト染料及びモノアゾ化合物（Ｃ）の対称型１：２コバ
ルト染料を等量含有し、さらにモノアゾ化合物（Ｂ）と
モノアゾ化合物（Ｃ）各１分子に対してコバルト１分子
が配位したいわゆる非対称型１：２コバルト染料が相当
量含まれた混合染料組成物であった。Example 4 A cobalt-imparting agent is allowed to act on a substantially equivalent mixture of the monoazo compound (C) obtained in Example 3 and the monoazo compound (B) obtained in Example 1 to complete the cobaltation. Was. The resulting dye contains equal amounts of the symmetrical 1: 2 cobalt dye of the monoazo compound (B) and the symmetrical 1: 2 cobalt dye of the monoazo compound (C), and the monoazo compound (B) and the monoazo compound (C) A) A mixed dye composition containing a considerable amount of a so-called asymmetric 1: 2 cobalt dye in which one molecule of cobalt is coordinated for each one molecule.
【００３０】この染料混合物０．１ｇを水１００ｇに溶
解し、ミニカラー染色試験機の染色ポットに入れ、これ
にスエード調のポリアミド系人工皮革２．０ｇを投入し
て蓋をした。この染色ポットを内温４０℃のミニカラー
染色機に挿入し、９０℃まで５０分間で昇温した。９０
℃で３０分間保温したのち、染色ポットを取り出し冷却
する。被染物を取り出し、常法に従って洗浄した。かく
して得られた染色物は、鮮明なバイオレット色を呈し、
諸堅牢度も良好であった。0.1 g of this dye mixture was dissolved in 100 g of water, placed in a dyeing pot of a mini-color dyeing tester, and 2.0 g of suede-like artificial polyamide leather was put into the pot and the lid was closed. This dyeing pot was inserted into a mini-color dyeing machine having an internal temperature of 40 ° C., and the temperature was raised to 90 ° C. in 50 minutes. 90
After keeping the temperature at 30 ° C for 30 minutes, the dyeing pot is taken out and cooled. The material to be dyed was taken out and washed according to a conventional method. The dyed material thus obtained has a clear violet color,
Various fastnesses were also good.
フロントページの続き (58)調査した分野(Int.Cl.6，ＤＢ名) C09B 67/22 C09B 45/02 - 45/22 D06P 1/10 D06P 3/24 D06P 3/32 ＣＡ（ＳＴＮ)Continued on the front page (58) Fields surveyed (Int.Cl. 6 , DB name) C09B 67/22 C09B 45/02-45/22 D06P 1/10 D06P 3/24 D06P 3/32 CA (STN)
Claims (3)
クロル原子、メチル基、エチル基、スルファモイル基、
メトキシ基又はエトキシ基を示す。Ｒ1 、Ｒ2 はそれぞ
れ独立に炭素数１〜４の低級アルキル基を示し、Ｒは水
素原子またはメチル基を示す。）で表わされるモノアゾ
化合物の１：２−コバルト錯体アゾ染料２０〜８０重量
部と、一般式（２）又は一般式（３） 【化２】 【化３】 （上記式中、Ｑ、Ｚはそれぞれ独立に水素原子、ニトロ
基、クロル原子、メチル基、エチル基、スルファモイル
基、メトキシ基又はエトキシ基を示す。Ｒ3 は、炭素数
１〜４の低級アルキル基を示す。）で表わされるモノア
ゾ化合物の１：２−コバルト錯体アゾ染料８０〜２０重
量部とからなることを特徴とするコバルト含有アゾ染料
組成物。1. A compound of the general formula (1) (Wherein X and Y each independently represent a hydrogen atom, a nitro group,
Chlorine atom, methyl group, ethyl group, sulfamoyl group,
Indicates a methoxy group or an ethoxy group. R 1 and R 2 each independently represent a lower alkyl group having 1 to 4 carbon atoms, and R represents a hydrogen atom or a methyl group. 20 to 80 parts by weight of a 1: 2-cobalt complex azo dye of a monoazo compound represented by the following formula (2) or (3): Embedded image (In the above formula, Q and Z each independently represent a hydrogen atom, a nitro group, a chloro atom, a methyl group, an ethyl group, a sulfamoyl group, a methoxy group or an ethoxy group. R 3 is lower alkyl having 1 to 4 carbon atoms. A azo dye composition comprising a monoazo compound represented by the formula: 80 to 20 parts by weight of a monoazo compound represented by the formula:
成物を用いることを特徴とする合成又は天然のポリアミ
ド繊維材料の染色方法。2. A method for dyeing a synthetic or natural polyamide fiber material, comprising using the cobalt-containing azo dye composition according to claim 1.
人工皮革である請求項２に記載の染色方法。3. The dyeing method according to claim 2, wherein the synthetic polyamide fiber material is a polyamide artificial leather.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5300899A JP2868143B2 (en) | 1993-11-05 | 1993-11-05 | Cobalt-containing azo dye composition and dyeing method using the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5300899A JP2868143B2 (en) | 1993-11-05 | 1993-11-05 | Cobalt-containing azo dye composition and dyeing method using the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH07126547A JPH07126547A (en) | 1995-05-16 |
| JP2868143B2 true JP2868143B2 (en) | 1999-03-10 |
Family
ID=17890471
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5300899A Expired - Fee Related JP2868143B2 (en) | 1993-11-05 | 1993-11-05 | Cobalt-containing azo dye composition and dyeing method using the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2868143B2 (en) |
-
1993
- 1993-11-05 JP JP5300899A patent/JP2868143B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH07126547A (en) | 1995-05-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3970946B2 (en) | Azo dye mixtures, azo dyes, their production and their use | |
| JPS5823416B2 (en) | Production method of chromium mixed complex salt dye | |
| JP2868143B2 (en) | Cobalt-containing azo dye composition and dyeing method using the same | |
| JP3580564B2 (en) | Cobalt-containing azo compound, its use and production method | |
| JPH06287460A (en) | 1:2 chrome complex dye | |
| CA1085386A (en) | Water-soluble brown l:2-chromium-mixed complex dyestuffs, process for their manufacture and their use for the dyeing of natural or synthetic polyamide fibers | |
| US4113719A (en) | 1:2-Cobalt-complex azo dyestuffs having an acetoacetylamino diphenylamino coupler | |
| JP2927568B2 (en) | Azo dyes, their preparation and use | |
| JP3090487B2 (en) | New azo black dye | |
| KR0148686B1 (en) | Watersoluble phthalocyanine compounds, process for their preparation and their use | |
| JP2729402B2 (en) | Water-soluble trisazo dye | |
| JPS62250059A (en) | Disazo compound and method for dyeing using same | |
| JP3205576B2 (en) | New cationic dye | |
| JPS5840358A (en) | Asymmetrical 1:2 chromium complex dye | |
| JPH07207170A (en) | Dye composition for dying synthetic leather, dying method using the same and dyed product | |
| US4145339A (en) | Water-soluble 1:2-cobalt complex dyestuffs of an azomethine and of an azo compound | |
| JPH0751678B2 (en) | Water-soluble monoazo dye | |
| JPH035427B2 (en) | ||
| JPS63132969A (en) | Benzothiazole-based monoazo dye | |
| JPH06157928A (en) | Azo dye, its preparation and its application | |
| JPH06104776B2 (en) | Monoazo compound and monoazo dye | |
| JP2556692B2 (en) | Method for dyeing hydrophobic fiber using pyridone monoazo compound | |
| JPS6051505B2 (en) | Water-soluble monoazo dye | |
| JPS61141765A (en) | Monoazo dye | |
| JPH0358388B2 (en) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20081225 Year of fee payment: 10 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20081225 Year of fee payment: 10 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20091225 Year of fee payment: 11 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20091225 Year of fee payment: 11 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20101225 Year of fee payment: 12 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20101225 Year of fee payment: 12 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20111225 Year of fee payment: 13 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20121225 Year of fee payment: 14 |
|
| LAPS | Cancellation because of no payment of annual fees |