JPH07207170A - Dye composition for dying synthetic leather, dying method using the same and dyed product - Google Patents
Dye composition for dying synthetic leather, dying method using the same and dyed productInfo
- Publication number
- JPH07207170A JPH07207170A JP6022082A JP2208294A JPH07207170A JP H07207170 A JPH07207170 A JP H07207170A JP 6022082 A JP6022082 A JP 6022082A JP 2208294 A JP2208294 A JP 2208294A JP H07207170 A JPH07207170 A JP H07207170A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- dye
- artificial leather
- cobalt complex
- dyeing
- 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.)
- Pending
Links
Landscapes
- Coloring (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明はポリアミド系人工皮革を
染色するための染料組成物及びそれを用いて人工皮革を
染色する方法、並びにその染色物に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a dye composition for dyeing a polyamide artificial leather, a method for dyeing artificial leather using the same, and a dyed product thereof.
【０００２】[0002]
【従来の技術】従来、ポリアミド系人工皮革を黄色系、
赤色系、青色系のいわゆる三原色染料による染色を行う
場合、移染性の良好ないわゆる均染型酸性染料を用いて
染色を得ることが知られているが、概して湿潤堅牢度が
劣る欠点を有する。近来、スポーツ衣料マーケットの拡
大に伴い、人工皮革の鮮明緑色の中高濃度染色物の湿潤
堅牢度に対する要望は高くなっている。2. Description of the Related Art Conventionally, a polyamide-based artificial leather is yellow-based,
When dyeing with a red or blue so-called three-primary color dye, it is known to obtain a dye using a so-called level dyeing type acid dye having good dye transferability, but generally has the disadvantage of poor wet fastness. . Recently, with the expansion of the sports clothing market, the demand for the wet fastness of bright green medium-high density dyeing of artificial leather is increasing.
【０００３】例えば、特公平５−65627 号公報には、ポ
リアミド系人工皮革を緑色に染色する方法として、その
実施例６にはキノン系酸性染料を用いて人工皮革を染色
する方法が示されているが、この場合においても、特に
高濃度染色物を得ようとする場合、湿潤堅牢度等に問題
が生ずる結果となり、この改善が要請されていた。For example, Japanese Examined Patent Publication (Kokoku) No. 5-65627 discloses a method for dyeing a polyamide artificial leather with a green color, and Example 6 thereof shows a method for dyeing an artificial leather with a quinone acid dye. However, even in this case, especially when an attempt is made to obtain a high-density dyed product, problems such as wet fastness result, and this improvement has been demanded.
【０００４】[0004]
【発明が解決しようとする課題】本発明者らは、従来の
染色法の欠点を克服し、人工皮革を鮮明かつ高濃度の緑
色に均一に染色し、かつ良好な湿潤堅牢度を付与するこ
とのできる染料組成物及び染色法について鋭意研究し、
特定の染料母体構造を有するアゾ染料の混合コバルト錯
塩染料を用いることにより、好適な人工皮革の緑色染色
物が得られることを見出し、本発明を完成するに至っ
た。DISCLOSURE OF THE INVENTION The present inventors have overcome the drawbacks of the conventional dyeing methods, uniformly dyeing artificial leather in a clear and high-concentration green color, and imparting good wet fastness. Diligently researched dye compositions and dyeing methods,
The inventors have found that a suitable green dyed product of artificial leather can be obtained by using a mixed cobalt complex salt dye of an azo dye having a specific dye base structure, and have completed the present invention.
【０００５】[0005]
【課題を解決するための手段】本発明は、人工皮革を染
色するための染料組成物であって、該組成物が遊離酸の
形で下記一般式（１）The present invention provides a dye composition for dyeing artificial leather, the composition being in the form of a free acid, represented by the following general formula (1):
【０００６】[0006]
【化−７】 [Chemical-7]
【０００７】（式中、Ａは、ハロゲン原子、低級アルキ
ル基又は置換もしくは未置換のスルホンアミド基を有し
ていてもよいベンゼン環を、Ｂは、ハロゲン原子、低級
アルキル基又は低級アルコキシ基を有していてもよいベ
ンゼン環を表わす）で示されるアゾ化合物と遊離酸の形
で下記一般式（２）(In the formula, A is a halogen atom, a lower alkyl group or a benzene ring which may have a substituted or unsubstituted sulfonamide group, and B is a halogen atom, a lower alkyl group or a lower alkoxy group. Which represents a benzene ring which may be present) and a free acid in the form of the following general formula (2)
【０００８】[0008]
【化−８】 [Chemical-8]
【０００９】（式中、Ｒ1 及びＲ2 はそれぞれ独立に水
素原子又は低級アルキル基を表わす）で示されるアゾ化
合物との混合コバルト錯塩染料を含有することを特徴と
する人工皮革を緑色に染色するための染料組成物であ
る。An artificial leather characterized by containing a mixed cobalt complex salt dye with an azo compound represented by the formula (wherein R 1 and R 2 independently represent a hydrogen atom or a lower alkyl group) is dyed green. It is a dye composition for
【００１０】本発明の特徴は、特定構造のアゾ化合物の
２分子にコバルト１原子が錯結合してなる混合コバルト
錯塩染料を用いて、人工皮革を染色するための染料組成
物として用いることにより、従来の問題点を改善し得る
ことを見出した点にある。本発明に用いられる混合コバ
ルト錯塩染料の一部は、例えば米国特許２７７６９５６
号明細書に記載されており、同明細書に記載の方法に準
じて製造することができる。例えば、式（１）のアゾ化
合物と式（２）のアゾ化合物を１：０．５〜２の範囲で
混合し、これら合計のアゾ化合物２モルに対してコバル
ト化合物１〜１．５モル比で反応させることによって得
られる。反応生成物には、通常式（１）のアゾ化合物及
び式（２）のアゾ化合物との非対称型コバルト錯塩染料
以外に、式（１）のアゾ化合物の対称型２：１コバルト
錯塩染料及び式（２）のアゾ化合物の対称型２：１コバ
ルト錯塩染料が含まれることがある。A feature of the present invention is to use a mixed cobalt complex salt dye in which one atom of cobalt is complex-bonded to two molecules of an azo compound having a specific structure, and to use it as a dye composition for dyeing artificial leather. The point is that the conventional problems can be improved. Some of the mixed cobalt complex salt dyes used in the present invention are disclosed, for example, in US Pat.
It can be manufactured according to the method described in the specification. For example, the azo compound of the formula (1) and the azo compound of the formula (2) are mixed in the range of 1: 0.5 to 2, and the cobalt compound is 1 to 1.5 mol ratio based on 2 mol of the total azo compound. It is obtained by reacting with. In addition to the asymmetric cobalt complex salt dyes with the azo compound of the formula (1) and the azo compound of the formula (2), the reaction product includes a symmetrical 2: 1 cobalt complex dye of the azo compound of the formula (1) and the formula The symmetrical 2: 1 cobalt complex salt dye of the azo compound of (2) may be contained.
【００１１】これらの反応生成物の組成比は、反応の条
件、即ちｐＨ、温度、原料アゾ化合物の仕込みモル比、
コバルト化剤（例えば、２価の硫酸コバルト、酢酸コバ
ルト、塩化コバルト、酒石酸コバルト等）の種類、中和
剤（例えば、苛性ソーダ、炭酸ソーダ、重炭酸ソーダ、
アンモニア、酢酸ソーダ、アルカノールアミン等）の種
類、攪拌速度、反応系の濃度、無機塩の濃度等々により
種々に変化させることができ、また、食塩等の無機塩の
添加による結晶化、分離によってもその組成比を変える
ことができる。The composition ratios of these reaction products are the reaction conditions, that is, pH, temperature, the molar ratio of the starting azo compound charged,
Type of cobalting agent (for example, divalent cobalt sulfate, cobalt acetate, cobalt chloride, cobalt tartrate, etc.), neutralizing agent (for example, caustic soda, sodium carbonate, sodium bicarbonate,
Ammonia, sodium acetate, alkanolamine, etc.), stirring speed, concentration of reaction system, concentration of inorganic salt, etc., and can be changed by crystallization and separation by addition of inorganic salt such as salt. The composition ratio can be changed.
【００１２】本発明者らは、人工皮革を染色するための
染料組成物であって、該組成物が式（１）のアゾ化合物
の対称型２：１コバルト錯塩染料１〜５０重量％：式
（２）のアゾ化合物の対称型２：１コバルト錯塩染料１
〜５０重量％：式（１）及び式（２）の非対称型コバル
ト錯塩染料２０〜９８重量％から成る混合コバルト錯塩
染料が、人工皮革の高濃度鮮明にしてかつ均一染色に適
し、特に従来の問題とされていた湿潤堅牢度に優れた染
色物が得られることを見出した。また、特に好ましい混
合コバルト錯塩染料の組成は、式（１）のアゾ化合物の
対称型２：１コバルト錯塩染料２〜２５重量％：式
（２）のアゾ化合物の対称型２：１コバルト錯塩染料２
〜２５重量％：式（１）及び式（２）の非対称型コバル
ト錯塩染料４０〜９８重量％から成る混合コバルト錯塩
染料であり、特に好ましい緑色の均一染色物を得ること
ができる。The present inventors have proposed a dye composition for dyeing artificial leather, wherein the composition is a symmetrical 2: 1 cobalt complex salt dye of an azo compound of the formula (1): 1 to 50% by weight: Symmetrical 2: 1 cobalt complex salt dye 1 of azo compound of (2)
˜50% by weight: A mixed cobalt complex salt dye consisting of 20 to 98% by weight of the asymmetric cobalt complex salt dyes of the formulas (1) and (2) is suitable for high density and sharp dyeing of artificial leather. It has been found that a dyed product excellent in wet fastness, which has been a problem, can be obtained. A particularly preferred composition of the mixed cobalt complex dye is a symmetrical 2: 1 cobalt complex dye of the azo compound of the formula (1) 2 to 25% by weight: a symmetrical 2: 1 cobalt complex dye of the azo compound of the formula (2) Two
-25% by weight: A mixed cobalt complex salt dye consisting of 40 to 98% by weight of the asymmetric cobalt complex salt dye of the formula (1) and the formula (2), and a particularly preferable green uniform dyeing product can be obtained.
【００１３】従来の緑色染色物を得るために、通常用い
られる黄色染料と青色染料を混合して染色する方法で
は、本発明の対象とする人工皮革の染色の場合、不均染
となり、適当でない。また、例えば後述する式（５）の
青色染料と式（６）黄色染料を混合した場合にも均一な
染色物が得られない。これに反し、本発明の染料組成物
を用いれば、均一な染色物が得られる点、極めて有用で
ある。The conventional method of mixing a yellow dye and a blue dye for dyeing to obtain a green dyed product is not suitable for dyeing artificial leather, which is the object of the present invention, because it causes uneven dyeing. . Further, for example, when a blue dye of the formula (5) described later and a yellow dye of the formula (6) are mixed, a uniform dyed product cannot be obtained. On the contrary, the use of the dye composition of the present invention is extremely useful in that a uniform dyed product can be obtained.
【００１４】本発明にいう式（１）のアゾ化合物及び式
（２）のアゾ化合物の非対称型コバルト錯塩染料は、下
記一般式（３）The asymmetric cobalt complex salt dye of the azo compound of the formula (1) and the azo compound of the formula (2) referred to in the present invention is represented by the following general formula (3).
【００１５】[0015]
【化−９】 [Chemical-9]
【００１６】（式中、Ｒ1 及びＲ2 は前記の意味を表
し、Ｍはアルカリ金属、アンモニウム又は有機アミン塩
を表わす）で示される。(Wherein R 1 and R 2 are as defined above, and M is an alkali metal, ammonium or organic amine salt).
【００１７】本発明にいう前記式（１）で示されるアゾ
化合物としては、具体的には次のようなアゾ化合物が挙
げられる。Specific examples of the azo compound represented by the above formula (1) in the present invention include the following azo compounds.
【００１８】[0018]
【化−１０】 [Chemical-10]
【００１９】本発明にいう前記式（２）で示されるアゾ
化合物としては、具体的には次のようなアゾ化合物が挙
げられる。Specific examples of the azo compound represented by the above formula (2) in the present invention include the following azo compounds.
【００２０】[0020]
【化−１１】 [Chemical-11]
【００２１】本発明に用いられる式（１）のアゾ化合物
及び式（２）のアゾ化合物の非対称型コバルト錯塩染料
は、具体的には例えば、下記一般式（４）The asymmetric cobalt complex salt dye of the azo compound of the formula (1) and the azo compound of the formula (2) used in the present invention is specifically, for example, the following general formula (4).
【００２２】[0022]
【化−１２】 [Chemical-12]
【００２３】（式中、Ｘは水素原子又は塩素原子を表
し、Ｍはアルカリ金属、アンモニウム又は有機アミン塩
を表わす）で示される。(Wherein, X represents a hydrogen atom or a chlorine atom, and M represents an alkali metal, ammonium or organic amine salt).
【００２４】また、式（２）のアゾ化合物の対称型２：
１コバルト錯塩染料は、具体的には例えば、下記式
（５）Further, the symmetric type 2 of the azo compound of the formula (2):
The 1-cobalt complex salt dye is specifically, for example, represented by the following formula (5):
【００２５】[0025]
【化−１３】 [Chemical-13]
【００２６】（式中、Ｍはアルカリ金属、アンモニウム
又は有機アミン塩を表わす）で示される。(In the formula, M represents an alkali metal, ammonium or organic amine salt).
【００２７】更に、式（１）のアゾ化合物の対称型２：
１コバルト錯塩染料は、具体的には例えば、下記式
（６）Further, the symmetric type 2: of the azo compound of the formula (1):
The 1-cobalt complex salt dye is specifically, for example, the following formula (6)
【００２８】[0028]
【化−１４】 [Chemical-14]
【００２９】（式中、Ｘは水素原子又は塩素原子を表
し、Ｍはアルカリ金属、アンモニウム又は有機アミン塩
を表わす）で示される。(Wherein X represents a hydrogen atom or a chlorine atom, and M represents an alkali metal, ammonium or organic amine salt).
【００３０】本発明の対象とする人工皮革とは、ポリア
ミド系極細繊維（例えば、単繊度が約０．５デニール以
下、とりわけ約０．０２デニール以下の極細乃至超極細
ポリアミド系繊維）と多孔質ポリウレタン（例えば、ポ
リエステルポリオール型ポリウレタン、ポリエーテルポ
リオール型ポリウレタン）とからなる人工皮革であり、
具体的には、通常基体層としてウレタン等の弾性ポリマ
ーを含浸したポリアミド系繊維結合体（不織布）を用
い、表面層にポリウレタンを付与して仕上げたスムース
調、エナメル調、或いは基体表面層に繊維立毛層を形成
させて仕上げた繊維質スェード調の人工皮革が好ましく
あげられる。The artificial leathers to which the present invention is applied include polyamide ultrafine fibers (for example, ultrafine or ultrafine polyamide fibers having a fineness of about 0.5 denier or less, especially about 0.02 denier or less) and a porous material. An artificial leather made of polyurethane (for example, polyester polyol type polyurethane, polyether polyol type polyurethane),
Specifically, a polyamide-based fiber conjugate (nonwoven fabric) usually impregnated with an elastic polymer such as urethane is used as the base layer, and polyurethane is applied to the surface layer to finish it in a smooth tone, an enamel tone, or a fiber for the substrate surface layer. A fibrous suede-like artificial leather finished by forming a napped layer is preferred.
【００３１】本発明は、これらの人工皮革を前記した特
定のコバルト錯塩染料（単独又は混合）を用いて染色す
ることを特徴とする人工皮革の染色方法を包含する。ま
た、本発明は、本発明に用いられる錯塩染料以外の他の
黄色系、赤色系、青色系のいわゆる三原色染料等々と併
用して人工皮革を湿潤堅牢に染色する方法をも包含す
る。The present invention includes a method for dyeing artificial leather, which is characterized in that these artificial leathers are dyed with the above-mentioned specific cobalt complex salt dye (single or mixed). The present invention also includes a method of dyeing artificial leather in a wet and fast manner in combination with a yellow, red or blue so-called three primary color dye other than the complex salt dye used in the present invention.
【００３２】本発明のコバルト錯塩染料による人工皮革
の染色は、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高濃度、鮮明であり、均
一であって高い湿潤堅牢度を維持する。The artificial leather dyeing with the cobalt complex dye of the present invention can be dyed from a weakly alkaline to weakly acidic bath, but especially when applied from a bath containing neutral or slightly acidic such as acetic acid or ammonium sulfate. And good results are obtained. The dyeings thus obtained have high densities, are brilliant, uniform and maintain high wet fastnesses.
【００３３】[0033]
【発明の効果】本発明によれば、人工皮革を高濃度でか
つ鮮明な緑色に染色し、特に優れた湿潤堅牢度を有す
る。Industrial Applicability According to the present invention, artificial leather is dyed in a high density and in a bright green color and has particularly excellent wet fastness.
【００３４】[0034]
【実施例】以下の錯塩染料の合成例及びそれを用いた染
色方法について、実施例によって具体的に説明する。な
お、実施例中、部は重量部を表わす。EXAMPLES The following synthetic examples of complex salt dyes and dyeing methods using the same will be specifically described by way of examples. In the examples, “part” means “part by weight”.
【００３５】実施例１（合成例） 前記式（２）−１のアゾ化合物４０．１部（０．１モ
ル）と、式（１）−１のアゾ化合物３７．６部（０．１
モル）を水３０００部と水酸化ナトリウム１０部の溶液
に加え、８０℃に昇温し、硫酸コバルト２８．１部
（０．１モル）の水溶液を加え、ソーダ灰６部を加え
る。反応が終了すれば塩析し、濾別、乾燥する。得られ
たコバルト化物は、ＬＣ分析(254nm検出) の結果 式（２）−１のアゾ化合物の対称型コバルト錯体 １０重量％ 式（１）−１のアゾ化合物の対称型コバルト錯体 ５重量％ 式（１）及び式（２）の非対称型コバルト錯体 ８５重量％ の組成を有していた。Example 1 (Synthesis Example) 40.1 parts (0.1 mol) of the azo compound of formula (2) -1 and 37.6 parts (0.1 mol) of the azo compound of formula (1) -1.
Mol) to a solution of 3000 parts of water and 10 parts of sodium hydroxide, the temperature is raised to 80 ° C., an aqueous solution of 28.1 parts (0.1 mol) of cobalt sulfate is added, and 6 parts of soda ash is added. When the reaction is completed, salting out is carried out, followed by filtration and drying. The obtained cobalt compound was analyzed by LC (254 nm detection). As a result, a symmetrical cobalt complex of the azo compound of the formula (2) -1 10% by weight A symmetrical cobalt complex of the azo compound of the formula (1) -1 5% by weight It had a composition of 85% by weight of the asymmetric cobalt complex of formula (1) and formula (2).
【００３６】なお、非対称型コバルト錯体染料は、極大
吸収波長 625 nm 、452 nm（ｐＨ＝７の緩衝液中）であ
り、水に溶解して鮮明緑色を呈する。The asymmetric cobalt complex dye has maximum absorption wavelengths of 625 nm and 452 nm (in a buffer solution of pH = 7) and exhibits a bright green color when dissolved in water.
【００３７】実施例２（染色法） 上記の方法によって得られた染料０．１部を水１００部
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２．０部を投
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、鮮明な緑色を呈し、湿潤堅
牢度等の諸堅牢度も極めて良好であった。Example 2 (Dyeing method) 0.1 part of the dye obtained by the above method was dissolved in 100 parts of water and put in a dyeing pot of a mini color dyeing tester,
2.0 parts of a suede-like polyamide artificial leather was put into this 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.
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 vivid green color and had very good fastnesses such as wet fastness.
【００３８】実施例３〜１０ 実施例１と同様にして下記表−１に示す混合コバルト錯
塩染料を得、その染料を用いて実施例２と同様にして人
工皮革を染色した場合の染色色相を右欄に示した。Examples 3 to 10 The mixed cobalt complex salt dyes shown in Table 1 below were obtained in the same manner as in Example 1, and the dyed hue when artificial leather was dyed in the same manner as in Example 2 using the dyes. Shown in the right column.
【００３９】[0039]
【表−１】 [Table-1]
【００４０】比較例１〜３ 実施例２と同様のして下記表−２に記載の市販の染料を
用いて同様にスエード調のポリアミド系人工皮革を染色
した。なお、染色濃度は長波長側と短波長側の極大吸光
度の合計がほぼ等しくなる様に調整した。染色物の試験
は、ＪＩＳ Ｌ ０８４６−Ａ法に従って水堅牢度試験
を行った。結果を表−２に示した。Comparative Examples 1 to 3 In the same manner as in Example 2, commercially available dyes shown in Table 2 below were used to dye similarly suede polyamide artificial leather. The dyeing concentration was adjusted so that the sums of the maximum absorbances on the long wavelength side and the short wavelength side were almost equal. The dyed product was tested for water fastness according to JIS L 0846-A method. The results are shown in Table-2.
【００４１】表−２に示すように、本発明にかかる混合
コバルト錯塩染料は、比較対象のキノン系酸性染料又は
ジスアゾ系酸性染料に比較して、ポリアミド汚染におい
て著しく優れている。As shown in Table 2, the mixed cobalt complex dye according to the present invention is remarkably excellent in polyamide contamination as compared with the quinone acid dye or the disazo acid dye to be compared.
【００４２】[0042]
【表−２】 [Table-2]
Claims (7)
あって、該組成物が遊離酸の形で下記一般式（１） 【化−１】 （式中、Ａは、ハロゲン原子、低級アルキル基又は置換
もしくは未置換のスルホンアミド基を有していてもよい
ベンゼン環を、Ｂは、ハロゲン原子、低級アルキル基又
は低級アルコキシ基を有していてもよいベンゼン環を表
わす）で示されるアゾ化合物と遊離酸の形で下記一般式
（２） 【化−２】 （式中、Ｒ1 及びＲ2 はそれぞれ独立に水素原子又は低
級アルキル基を表わす）で示されるアゾ化合物との混合
コバルト錯塩染料を含有することを特徴とする人工皮革
を染色するための染料組成物。1. A dye composition for dyeing artificial leather, the composition being in the form of a free acid, represented by the following general formula (1): (In the formula, A is a halogen atom, a lower alkyl group or a benzene ring which may have a substituted or unsubstituted sulfonamide group, and B is a halogen atom, a lower alkyl group or a lower alkoxy group. Which represents an optionally substituted benzene ring) and the free acid in the form of the following general formula (2) A dye composition for dyeing artificial leather, which contains a mixed cobalt complex dye with an azo compound represented by the formula (wherein R 1 and R 2 each independently represent a hydrogen atom or a lower alkyl group). object.
（３） 【化−３】 （式中、Ｒ1 及びＲ2 は請求項１に記載の意味を表し、
Ｍはアルカリ金属、アンモニウム又は有機アミン塩を表
わす）で示される請求項１に記載の人工皮革を染色する
ための染料組成物。2. A mixed cobalt complex dye is represented by the following general formula (3): (In the formula, R 1 and R 2 have the meanings defined in claim 1,
The dye composition for dyeing artificial leather according to claim 1, wherein M represents an alkali metal, ammonium or an organic amine salt.
あって、該組成物が遊離酸の形で下記一般式（１） 【化−４】 （式中、Ａは、ハロゲン原子、低級アルキル基又は置換
もしくは未置換のスルホンアミド基を有していてもよい
ベンゼン環を、Ｂは、ハロゲン原子、低級アルキル基又
は低級アルコキシ基を有していてもよいベンゼン環を表
わす）で示されるアゾ化合物と遊離酸の形で下記一般式
（２） 【化−５】 （式中、Ｒ1 及びＲ2 はそれぞれ独立に水素原子又は低
級アルキル基を表わす）で示されるアゾ化合物との混合
コバルト錯塩染料であって、式（１）のアゾ化合物の対
称型２：１コバルト錯塩染料１〜５０重量％：式（２）
のアゾ化合物の対称型２：１コバルト錯塩染料１〜５０
重量％：式（１）及び式（２）の非対称型コバルト錯塩
染料２０〜９８重量％から成ることを特徴とする人工皮
革を染色するための染料組成物。3. A dye composition for dyeing artificial leather, the composition being in the form of a free acid represented by the following general formula (1): (In the formula, A is a halogen atom, a lower alkyl group or a benzene ring which may have a substituted or unsubstituted sulfonamide group, and B is a halogen atom, a lower alkyl group or a lower alkoxy group. Which may be a benzene ring) and a free acid in the form of the following general formula (2): A mixed cobalt complex dye with an azo compound represented by the formula (wherein R 1 and R 2 each independently represent a hydrogen atom or a lower alkyl group), wherein the azo compound of the formula (1) has a symmetrical type of 2: 1. Cobalt complex salt dye 1 to 50% by weight: Formula (2)
Azo compound symmetric type 2: 1 cobalt complex salt dyes 1 to 50
% By weight: 20 to 98% by weight of the asymmetric cobalt complex dyes of the formulas (1) and (2), a dye composition for dyeing artificial leather.
錯塩染料が、下記式（４） 【化−６】 （式中、Ｘは水素原子又は塩素原子を表し、Ｍはアルカ
リ金属、アンモニウム又は有機アミン塩を表わす）で示
される請求項１〜請求項３のいずれかに記載の人工皮革
を染色するための染料組成物。4. An asymmetric cobalt complex salt dye of formula (1) and formula (2) is represented by the following formula (4): (In the formula, X represents a hydrogen atom or a chlorine atom, and M represents an alkali metal, ammonium or an organic amine salt) for dyeing the artificial leather according to any one of claims 1 to 3. Dye composition.
染料組成物を含有する染浴から人工皮革を染色すること
を特徴とする人工皮革の染色方法。5. A method for dyeing artificial leather, which comprises dyeing the artificial leather from a dyebath containing the dye composition according to any one of claims 1 to 4.
孔質ポリウレタンとからなる人工皮革である請求項５に
記載の人工皮革の染色方法。6. The method for dyeing artificial leather according to claim 5, wherein the artificial leather is an artificial leather composed of a polyamide ultrafine fiber and a porous polyurethane.
の染色方法で染色された人工皮革。7. An artificial leather dyed by the dyeing method according to claim 5 or 6.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6022082A JPH07207170A (en) | 1994-01-21 | 1994-01-21 | Dye composition for dying synthetic leather, dying method using the same and dyed product |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6022082A JPH07207170A (en) | 1994-01-21 | 1994-01-21 | Dye composition for dying synthetic leather, dying method using the same and dyed product |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH07207170A true JPH07207170A (en) | 1995-08-08 |
Family
ID=12072964
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6022082A Pending JPH07207170A (en) | 1994-01-21 | 1994-01-21 | Dye composition for dying synthetic leather, dying method using the same and dyed product |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH07207170A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107043553A (en) * | 2016-12-14 | 2017-08-15 | 恒升化工有限公司 | A kind of preparation method of acid dyes |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2776956A (en) * | 1957-01-08 | Soinhi | ||
| JPS50108321A (en) * | 1974-01-30 | 1975-08-26 |
-
1994
- 1994-01-21 JP JP6022082A patent/JPH07207170A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2776956A (en) * | 1957-01-08 | Soinhi | ||
| JPS50108321A (en) * | 1974-01-30 | 1975-08-26 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107043553A (en) * | 2016-12-14 | 2017-08-15 | 恒升化工有限公司 | A kind of preparation method of acid dyes |
| CN107043553B (en) * | 2016-12-14 | 2019-04-23 | 恒升化工有限公司 | A kind of preparation method of acid dyes |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3970946B2 (en) | Azo dye mixtures, azo dyes, their production and their use | |
| JP4624554B2 (en) | Triphendioxazine dyes for organic substrate dyeing | |
| JPS5842661A (en) | Water-soluble azo compound, manufacture and use thereof as dye | |
| DE4209261A1 (en) | ANIONIC DISORGAN BINDINGS | |
| TWI667293B (en) | Trisazo acid dyes, a process for preparing the same, use thereof, a process for dyeing or printing a substrate and a colour-containing substrate by using the same, and dye composition having the same | |
| TWI422647B (en) | Acid dyes | |
| JPH0197282A (en) | Method for dyeing or printing natural or synthetic polyamide fiber material using reactive dye | |
| GB2148921A (en) | New formazan reactive dyes | |
| JPS5930970A (en) | Dyeing of different dyeing fiber | |
| US2576037A (en) | Sulfonyl fluorides of amino azo dyestuffs | |
| WO1999048987A1 (en) | Reactive black dye compositions for cellulose fibers | |
| EP1760117A2 (en) | Reactive dyestuff compositions and their use | |
| JPH07207170A (en) | Dye composition for dying synthetic leather, dying method using the same and dyed product | |
| CA2560958A1 (en) | Monoazo dyes | |
| JPS6245792A (en) | Dyeing of polyester fiber having fine denier | |
| JPS5974163A (en) | Disazo compound and dyeing therewith | |
| JPH1046045A (en) | Three-color dyeing or three-color printing | |
| JP2868143B2 (en) | Cobalt-containing azo dye composition and dyeing method using the same | |
| JP3580564B2 (en) | Cobalt-containing azo compound, its use and production method | |
| JPH07179783A (en) | Tricolor dyeing or printing method | |
| KR0148686B1 (en) | Watersoluble phthalocyanine compounds, process for their preparation and their use | |
| JPS59170143A (en) | Monoazo dye for polyester fiber | |
| ITRM950196A1 (en) | DYE COMPLEXES OF POLYAZOIC COMPOUNDS, THEIR PRODUCTION AND THEIR USE AS DYES. | |
| JPH0358388B2 (en) | ||
| KR0131760B1 (en) | Phthalocyanine compound, rrocess for dyeing or printing of organic substructure by using the smae |