JPH0619041B2 - Reactive monoazo dye - Google Patents
Reactive monoazo dyeInfo
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- JPH0619041B2 JPH0619041B2 JP61105163A JP10516386A JPH0619041B2 JP H0619041 B2 JPH0619041 B2 JP H0619041B2 JP 61105163 A JP61105163 A JP 61105163A JP 10516386 A JP10516386 A JP 10516386A JP H0619041 B2 JPH0619041 B2 JP H0619041B2
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Description
【発明の詳細な説明】 (a) 発明の目的 (イ)（産業上の利用分野） 本発明は反応型モノアゾ染料に関するものであり、詳し
くは、ヒドロキシル基、アミノ基またはアニオン性基含
有繊維類を赤色に染色することができるモノアゾ染料に
関するものである。DETAILED DESCRIPTION OF THE INVENTION (a) Purpose of the Invention (a) (Field of Industrial Application) The present invention relates to a reactive monoazo dye, and more specifically, a fiber containing a hydroxyl group, an amino group or an anionic group. The present invention relates to a monoazo dye capable of dyeing red.
(ロ)（従来の技術） 従来、ヒドロキシル基含有繊維及びアミノ基含有繊維を
染色する場合は、一SO3Na基を有するアニオン性水溶性
染料が使用されており、そして、アニオン性基含有繊維
を染色する場合は、４級化窒素原子を有するカチオン性
水溶性染料が使用されている。(B) (Prior Art) Conventionally, when dyeing a hydroxyl group-containing fiber and an amino group-containing fiber, an anionic water-soluble dye having one SO 3 Na group has been used, and an anionic group-containing fiber. In the case of dyeing, a cationic water-soluble dye having a quaternized nitrogen atom is used.
従つて、ヒドロキシル基含有繊維及びアミノ基含有繊維
と、アニオン性基含有繊維との混合繊維を染色する場合
は、上記アニオン性水溶性染料とカチオン性水溶性染料
との二種類の染料を用いなければならないが、各々染色
条件が異なるので、ヒドロキシル基含有繊維及びアミノ
基含有繊維と、アニオン性基含有繊維とを同時には、染
色することができないことや、また、これらの繊維を順
次、染色した場合でも、アニオン性水溶性染料とカチオ
ン性水溶性染料とによりコンプレツクスが形成され染着
不良となること等の問題があつた。Therefore, when dyeing a mixed fiber of a hydroxyl group-containing fiber and an amino group-containing fiber and an anionic group-containing fiber, two types of dyes, an anionic water-soluble dye and a cationic water-soluble dye, must be used. However, since the dyeing conditions are different, it is not possible to dye the hydroxyl group-containing fiber and the amino group-containing fiber and the anionic group-containing fiber at the same time, and these fibers are sequentially dyed. Even in this case, there is a problem that a complex is formed by the anionic water-soluble dye and the cationic water-soluble dye, resulting in poor dyeing.
(ハ)（発明が解決しようとする問題点） 本発明は、ヒドロキシル基含有繊維及びアミノ基含有繊
維と、アニオン性基含有繊維との混合繊維を染色する場
合に、１種類の染料を用いて、ヒドロキシル基含有繊維
及びアミノ基含有繊維と、アニオン性基含有繊維を同時
に染色することができるモノアゾ染料を目的とする。(C) (Problems to be Solved by the Invention) The present invention uses one kind of dye when dyeing a mixed fiber of a hydroxyl group-containing fiber and an amino group-containing fiber and an anionic group-containing fiber. A monoazo dye capable of simultaneously dyeing a hydroxyl group-containing fiber and an amino group-containing fiber, and an anionic group-containing fiber.
(b) 発明の構成 (イ)（問題点を解決する為の手段） 本発明は下記一般式〔1〕 （式中、Ｘは水素またはハロゲン原子を表わし、Ｙはハ
ロゲン原子を表わし、Ｚは 基または 基を表わし、そのうちR1は水素原子、またはアルキル基
を表わし、R2はアルキレン基を表わし、R3はアルキル基
を表わし、そしてＡ はアニオンを表わす。）で示され
る反応型モノアゾ染料を要旨とするものである。(b) Structure of the Invention (a) (Means for Solving Problems) The present invention has the following general formula [1](In the formula, X represents hydrogen or a halogen atom, and Y represents
Represents a logen atom, and Z isBase orRepresents a group of which R1Is a hydrogen atom or an alkyl group
Represents R2Represents an alkylene group, R3Is an alkyl group
And A Represents an anion. ) Indicated by
The subject is reactive monoazo dyes.
以下、本発明を詳細に説明する。Hereinafter, the present invention will be described in detail.
前示一般式〔1〕で示される本発明のモノアゾ染料にお
いて、ＸおよびＹで表わされるハロゲン原子としては、
例えば、塩素原子、臭素原子またはフツ素原子等が挙げ
られ、特に塩素原子が好ましい。R1およびR3で表わされ
るアルキル基としては、例えばメチル基、エチル基また
はプロピル基などの低級アルキル基が挙げられる。また
R2で表わされるアルキレン基としては例えばエチル基、
プロピレン基などの低級アルキレン基が挙げられる。更
に、Ａ で表わされるアニオンとしては通常、ハロゲン
アニオン、メチル硫酸アニオン、エチル硫酸アニオン、
トシル硫酸アニオン等のアニオンが挙げられる。In the monoazo dye of the present invention represented by the general formula [1] shown above,
And as the halogen atom represented by X and Y,
Examples include chlorine atom, bromine atom, and fluorine atom.
In particular, a chlorine atom is preferable. R1And R3Represented by
Examples of the alkyl group include a methyl group, an ethyl group and
Is a lower alkyl group such as a propyl group. Also
R2As the alkylene group represented by, for example, an ethyl group,
Examples include lower alkylene groups such as propylene group. Change
To A The anion represented by is usually halogen.
Anion, methylsulfate anion, ethylsulfate anion,
Anions such as tosylsulfate anion are mentioned.
前示一般式〔1〕で示されるモノアゾ染料を合成するに
は、例えば、下記一般式 （式中、ＸおよびＹは前記定義に同じ。）で示されるア
ミン類を常法に従つて、ジアゾ化し、次いで、下記一般
式〔III〕 （式中、Ｚは前記定義に同じ。）で示されるカツプリン
グ成分とカツプリングさせることにより容易に製造する
ことができる。To synthesize the monoazo dye represented by the general formula [1] shown above, for example, the following general formula (In the formula, X and Y are the same as defined above.) The amines represented by the following general formula [III] are diazotized by a conventional method. (In the formula, Z is the same as the above definition.) It can be easily produced by coupling with a coupling component.
なお、前示一般式〔III〕のカツプリング成分は通常、
下記の一般式〔IV〕 （式中、Ｚ′は 基または 基を表わし、R1、R2またはR3は前記定義に同じ。） で示されるピリジン系化合物を一般式〔V〕 R3−Ａ……〔V〕 （R3およびＡは前記定義に同じである。）で示されるア
ルキル化剤により、例えば有機溶媒中、室温〜５０℃の
温度で０．５〜５時間反応させることにより製造するこ
とができる。このアルキル化反応において用いられる有
機溶媒としては、例えばアセトン、メチルエチルケト
ン、ジオキサン、テトラハイドロフラン、トルエン、ク
ロロベンゼン、ジクロロベンゼン、ニトロベンゼンなど
が挙げられる。The coupling component of the general formula [III] shown above is usually
The following general formula [IV] (In the formula, Z ′ is Base or Represents a group, and R 1 , R 2 or R 3 has the same meaning as defined above. ) Is treated with an alkylating agent represented by the general formula [V] R 3 -A ... [V] (R 3 and A are as defined above), for example, in an organic solvent at room temperature. It can be produced by reacting at a temperature of -50 ° C for 0.5-5 hours. Examples of the organic solvent used in this alkylation reaction include acetone, methyl ethyl ketone, dioxane, tetrahydrofuran, toluene, chlorobenzene, dichlorobenzene, and nitrobenzene.
また前示一般式〔V〕のアルキル化剤としては、通常、
ジメチル硫酸、ジエチル硫酸、臭化メチル、臭化エチ
ル、沃化メチル、沃化エチル、ｐ−トルエンスルホン酸
メチルエステル、りん酸トリエチルエステル等が挙げら
れ、この使用量は、例えば、前示一般式〔IV〕のピリジ
ン系化合物に対して１．０〜１．１倍モルである。The alkylating agent of the general formula [V] shown above is usually
Dimethylsulfate, diethylsulfate, methyl bromide, ethyl bromide, methyl iodide, ethyl iodide, p-toluenesulfonic acid methyl ester, phosphoric acid triethyl ester and the like can be mentioned. The amount is 1.0 to 1.1 times the mol of the pyridine compound of [IV].
本発明の反応型モノアゾ染料の場合には、ヒドロキシ基
含有繊維、アミノ基含有繊維及びアニオン性基含有繊維
の混紡品、混織品及び混編品を同時に一浴で染色するこ
とができる。In the case of the reactive type monoazo dye of the present invention, a mixed spinning product, a mixed woven product and a mixed knitted product of a hydroxy group-containing fiber, an amino group containing fiber and an anionic group containing fiber can be dyed simultaneously in one bath.
本発明の染料を適用可能なヒドロキシル基含有繊維とし
ては、木綿、麻等の天然繊維、ビスコース・レーヨン、
銅アンモニアレーヨン等の半合成繊維などの織編物が挙
げられ、アミノ基含有繊維としては、羊毛、絹、合成ポ
リアミドおよびポリウレタン繊維などの織編物が挙げら
れ、また、アニオン性基含有繊維としては、アクリル繊
維およびカチオン可染ポリエステル繊維の織編物が挙げ
られる。As the hydroxyl group-containing fiber to which the dye of the present invention can be applied, cotton, natural fiber such as hemp, viscose rayon,
Examples include woven and knitted materials such as semi-synthetic fibers such as cuprammonium rayon, and amino group-containing fibers include woven and knitted materials such as wool, silk, synthetic polyamide and polyurethane fibers, and the anionic group-containing fibers include Examples include woven and knitted products of acrylic fibers and cationic dyeable polyester fibers.
本発明のモノアゾ染料は、水溶液の状態で浸染染色法に
おける染浴、及び、パデイング染色法におけるパデイン
グ浴として、また、糊剤との併用により捺染色糊とし
て、各々の染色法に使用することができる。The monoazo dye of the present invention can be used in each dyeing method in the state of an aqueous solution as a dyeing bath in a dip dyeing method, and as a padding bath in a padding dyeing method, and as a printing dye paste in combination with a sizing agent. it can.
ヒドロキシル基含有繊維またはアミノ基含有繊維とアク
リル繊維との混合繊維をパデイング染色または捺染する
際には、通常、尿素あるいは平均分子量２００〜５００
程度の範囲のポリエチレングリコール、ポリプロピレン
グリコール等、両末端の水酸基がジメチル化、ジアセチ
ル化された染料と反応しない多価アルコール類、更には
染料とヒドロキシル基またはアミノ基との反応を促進さ
せる目的で酸結合剤を配合するのが望ましい。When padding dyeing or printing a fiber containing a hydroxyl group-containing fiber or a fiber containing an amino group and an acrylic fiber, urea or an average molecular weight of 200 to 500 is usually used.
Polyhydric alcohols such as polyethylene glycol, polypropylene glycol, etc., having hydroxyl groups at both ends that are not dimethylated or diacetylated, and acid for the purpose of accelerating the reaction between the dye and the hydroxyl group or amino group. It is desirable to incorporate a binder.
この酸結合剤は、通常、トリクロロ酢酸ナトリウムのよ
うな水の存在下において加熱するとアルカリを発生する
アルカリ前駆化合物が望ましい。The acid binder is usually an alkali precursor compound that generates alkali when heated in the presence of water such as sodium trichloroacetate.
また、尿素あるいは多価アルコール類の使用量は、通
常、パデイング浴または捺染色糊に対して３〜８重量％
の範囲が挙げられ、またトリクロロ酢酸ナトリウムの使
用量は、本発明のモノアゾ染料の場合には、モノフロロ
トリアジンを有しており反応性が高いので、通常、０．
３〜０．５重量％と少量でよい。Further, the amount of urea or polyhydric alcohol used is usually 3 to 8% by weight based on the padding bath or the printing dye paste.
In the case of the monoazo dye of the present invention, the amount of sodium trichloroacetate used is usually 0, since it has monofluorotriazine and is highly reactive.
A small amount of 3 to 0.5% by weight is sufficient.
染色時における染料の固着条件は例えば、浸染染色法で
は、９５〜１３０℃で３０〜６０分間程度、パデイング
染色または捺染法では、乾燥後１００〜１３０℃の飽和
蒸気で５〜１０分間、１６０〜２２０℃の熱風または加
熱蒸気で３０秒〜１０分間である。The dye fixation conditions at the time of dyeing are, for example, 95 to 130 ° C. for about 30 to 60 minutes in the dip dyeing method, and 5 to 10 minutes in saturated vapor at 100 to 130 ° C. after drying for padding dyeing or printing method. It is 30 seconds to 10 minutes with hot air or heated steam at 220 ° C.
固着後の染色物は常法に従つて、界面活性剤を含む熱水
で洗浄することにより、鮮明でかつ均一に染色された堅
牢度の良好な染色物を得ることができる。The dyed product after fixing is washed with hot water containing a surfactant according to a conventional method, whereby a dyed product which is dyed clearly and uniformly and has good fastness can be obtained.
（実施例） 以下、本発明を実施例によつて更に詳細に説明するが、
本発明は以下の実施例に限定されるものではない。(Examples) Hereinafter, the present invention will be described in more detail with reference to Examples.
The present invention is not limited to the examples below.
実施例１ 上記組成のパテイング浴を調製し、アクリル／木綿（混
合比５０／５０）混紡布に含浸させ、絞り率６０％に絞
り、８０℃で３分間中間乾燥した後、加熱蒸気を用い、
１７０℃で７分間処理をした。このものを水洗した後、
２ｇ／のアニオン界面活性剤（花王石鹸(株)製商標ス
コアロール＋４００）を含有する洗浄液を用いて浴比
１：３０で９０℃で２０分間ソーピングをした。Example 1 A putting bath having the above composition was prepared, impregnated with an acrylic / cotton (mixing ratio 50/50) blended cloth, squeezed to a squeezing ratio of 60%, intermediately dried at 80 ° C. for 3 minutes, and then heated steam was used.
It was treated at 170 ° C. for 7 minutes. After washing this thing with water,
Soaping was carried out at 90 ° C. for 20 minutes at a bath ratio of 1:30 using a cleaning solution containing 2 g / anionic surfactant (Scoreroll + 400 manufactured by Kao Soap Co., Ltd.).
このようにして、各種堅牢度が良好で、しかも、アクリ
ル／木綿混紡布の全面が均一に染色された赤色の染色物
を得た。In this way, a red dyed product was obtained which had various fastnesses and the entire surface of the acrylic / cotton blended fabric was dyed uniformly.
なお、本実施例で使用した染料は下記構造式 で示されるピリジン系化合物４．８ｇとジメチル硫酸
１．４ｇとを、ジオキサン１００ml中で５０℃で３時間
反応させた後、冷水２００mlに放出することにより、カ
ツプリング溶液を調整した。The dye used in this example has the following structural formula. A coupling solution was prepared by reacting 4.8 g of the pyridine-based compound shown in (4) with 1.4 g of dimethylsulfate in 100 ml of dioxane at 50 ° C. for 3 hours and then releasing the mixture into 200 ml of cold water.
一方、４，６−ジクロロベンゾチアゾール２．２ｇを酢
酸１５mlとリン酸１５mlの混合液中に加え、０〜３℃で
４７％ニトロシル硫酸３．６ｇを添加し２時間撹拌し、
ジアゾ化を行なつた。この得られたジアゾ液を前記カツ
プリング溶液に、０℃以下、pH２〜４の範囲にコントロ
ールしながら徐々に加え、２時間撹拌しカツプリング反
応を行なつた後、析出した結晶を別、水洗、乾燥して
赤色結晶５．１ｇを得た。On the other hand, 2.2 g of 4,6-dichlorobenzothiazole was added to a mixed solution of 15 ml of acetic acid and 15 ml of phosphoric acid, 3.6 g of 47% nitrosyl sulfuric acid was added at 0 to 3 ° C., and the mixture was stirred for 2 hours,
Diazotization was performed. The resulting diazo solution was gradually added to the coupling solution while controlling the temperature to 0 ° C. or less and the pH to a range of 2 to 4, and the coupling reaction was carried out by stirring for 2 hours, and then the precipitated crystals were separated, washed with water and dried. Then, 5.1 g of red crystals were obtained.
また、本品のλmax （５０％ＤＭＦ水溶液）は５０６ｎ
ｍであつた。The λmax (50% DMF aqueous solution) of this product is 506n.
It was m.
実施例２ で示される混合物（ca１：１） 上記組成のパデイング浴を調製し、アクリル／６−ナイ
ロン（混合比８０／２０）混紡布に含浸し、絞り率５０
％に絞つた後、１００℃で７分間蒸熱固着した。このも
のを実施例１に記載の方法に従つて処理したところ、堅
牢度が良好で、しかも、アクリル／ナイロン混紡布の全
面が均一に染色された鮮明な赤色の染色物を得た。Example 2 Mixture shown by (ca1: 1) A padding bath having the above composition was prepared and impregnated with an acrylic / 6-nylon (mixing ratio 80/20) mixed spinning cloth, and the drawing ratio was 50.
After squeezing to 100%, steam fixation was performed at 100 ° C. for 7 minutes. When this product was treated according to the method described in Example 1, a fast red dyeing product which had good fastness and in which the entire surface of the acrylic / nylon blended fabric was dyed uniformly was obtained.
なお、本実施例で使用した染料は、実施例１に記載の方
法に準じて合成した。また本混合物のλmax （５０％Ｄ
ＭＦ水溶液）は５０６ｎｍであつた。The dye used in this example was synthesized according to the method described in Example 1. Also, the λmax of this mixture (50% D
MF aqueous solution) was 506 nm.
実施例３ 上記構造式で示されるモノアゾ染料の１wt％水溶液（pH
７．５）でアクリル／ウール（混合比５０／５０）混織
品を９８℃で１時間処理した後、熱水で洗浄することに
より、堅牢度が優れ、しかも、均一ないらつきのない赤
色の染色物を得た。Example 3 1 wt% aqueous solution of monoazo dye represented by the above structural formula (pH
7.5) Acrylic / wool (mixing ratio 50/50) mixed woven material is treated at 98 ° C for 1 hour, and then washed with hot water to give a red dyeing which has excellent fastness and is uniform and has no unevenness. I got a thing.
本実施例に使用した染料は実施例１に記載の方法に準じ
て合成した。The dye used in this example was synthesized according to the method described in Example 1.
また、本品のλmax （５０％ＤＭＦ水溶液）は５０７ｎ
ｍであつた。In addition, λmax (50% DMF aqueous solution) of this product is 507n.
It was m.
実施例４ 実施例１において、染布をアクリル／ウール（混合比５
０／５０）を混紡布にかえた以外は実施例１に記載の方
法に従つて染色したところ、堅牢度が優れ、しかも、全
面が均一に染色された赤色の染色物が得られた。Example 4 In Example 1, the dyed cloth was made of acrylic / wool (mixing ratio 5
(0/50) was changed to a blended fabric, and dyeing was carried out according to the method described in Example 1. As a result, a red dyed product having excellent fastness and having the entire surface uniformly dyed was obtained.
実施例５ 実施例１において、染布を木綿布にかえた以外は実施例
１に記載の方法に従つて染色したところ、堅牢度が優
れ、しかも、全面が均一に染色された赤色の染色物が得
られた。Example 5 A red dyed product which was dyed in accordance with the method described in Example 1 except that the dyeing fabric was changed to a cotton fabric in Example 1 and which had excellent fastness and was uniformly dyed on the entire surface. was gotten.
実施例６ 実施例３において、染布をカチオン可染ポリエステル／
ウール（混合比５０／５０）混紡布にかえた以外は実施
例１に記載の方法に従つて染色したところ、堅牢度が優
れ、しかも、全面が均一に染色された赤色の染色物が得
られた。Example 6 In Example 3, the dyed cloth is a cationic dyeable polyester /
Dyeing was carried out according to the method described in Example 1 except that a wool (mixing ratio 50/50) blended fabric was used. As a result, a red dyed product having excellent fastness and uniformly dyed over the entire surface was obtained. It was
実施例７ 第１表に記載したモノアゾ染料を使用し、実施例１に記
載の方法に従つてパデイング染色を行なつたところ、均
一に染色された赤色の染色物を得た。Example 7 Using the monoazo dyes shown in Table 1, padding dyeing was carried out according to the method described in Example 1 to obtain a uniformly dyed red dyed product.
また、これらのモノアゾ染料のλmax（５０％ＤＭＦ水
溶液）は第１表に示す通りであつた。Further, λmax (50% DMF aqueous solution) of these monoazo dyes is as shown in Table 1.
(c)（発明の効果） 本発明の反応型モノアゾ染料によれば、例えば、木綿ま
たはウール、ナイロンとアクリルとの混合繊維など、ヒ
ドロキシル基含有繊維及びアミノ基含有繊維と、アニオ
ン性基含有繊維との混合繊維を同時に染色することがで
きる。しかも、両繊維に対する染色性が良好であるた
め、むらのない均一な染色物を得ることができる。ま
た、これら染色物の各種堅牢度（特に湿潤堅牢度）も良
好である。したがつて、本発明の染料は実用的価値の高
い優れたものである。 (c) (Effect of the Invention) According to the reactive monoazo dye of the present invention, for example, fibers containing hydroxyl groups and fibers containing amino groups, and fibers containing anionic groups, such as cotton or wool, a mixed fiber of nylon and acrylic, etc. The mixed fiber with can be dyed at the same time. Moreover, since the dyeability of both fibers is good, it is possible to obtain a uniform dyed product without unevenness. Further, various fastnesses (especially wet fastness) of these dyed products are also good. Therefore, the dye of the present invention is excellent in practical value.
Claims (1)
ロゲン原子を表わし、Ｚは 基または 基を表わし、そのうちR1は水素原子またはアルキル基を
表わし、R2はアルキレン基を表わし、R3はアルキル基を
表わし、そしてＡ はアニオンを表わす。）で示される
反応型モノアゾ染料。1. The following general formula [I](In the formula, X represents hydrogen or a halogen atom, and Y represents
Represents a logen atom, and Z isBase orRepresents a group of which R1Is a hydrogen atom or an alkyl group
Represent, R2Represents an alkylene group, R3Is an alkyl group
Representation, and A Represents an anion. )
Reactive monoazo dye.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61105163A JPH0619041B2 (en) | 1986-05-08 | 1986-05-08 | Reactive monoazo dye |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61105163A JPH0619041B2 (en) | 1986-05-08 | 1986-05-08 | Reactive monoazo dye |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62263262A JPS62263262A (en) | 1987-11-16 |
| JPH0619041B2 true JPH0619041B2 (en) | 1994-03-16 |
Family
ID=14400025
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61105163A Expired - Lifetime JPH0619041B2 (en) | 1986-05-08 | 1986-05-08 | Reactive monoazo dye |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0619041B2 (en) |
-
1986
- 1986-05-08 JP JP61105163A patent/JPH0619041B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62263262A (en) | 1987-11-16 |
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