JP2565703B2 - Reactive dye composition - Google Patents
Reactive dye compositionInfo
- Publication number
- JP2565703B2 JP2565703B2 JP62045958A JP4595887A JP2565703B2 JP 2565703 B2 JP2565703 B2 JP 2565703B2 JP 62045958 A JP62045958 A JP 62045958A JP 4595887 A JP4595887 A JP 4595887A JP 2565703 B2 JP2565703 B2 JP 2565703B2
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- dye
- formula
- parts
- dye composition
- water
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- 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.)
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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、特にセルロース系繊維の染色に有用な反応
染料組成物に関する。TECHNICAL FIELD The present invention relates to a reactive dye composition particularly useful for dyeing cellulosic fibers.
〈従来技術〉 特公昭58-18472号公報に遊離酸の形で下式 で示されるモノアゾ染料が知られている。この染料は、
堅牢度が優れカラーイールドが高く、染色の再現性が良
い等の種々の特長を有しているため、特にセルロース系
繊維の染色に多用されている。<Prior Art> Japanese Patent Publication No. 58-18472 discloses the following formula in the form of free acid. A monoazo dye represented by is known. This dye is
Since it has various features such as excellent fastness, high color yield, and good dyeing reproducibility, it is widely used especially for dyeing cellulose fibers.
〈発明が解決しようとする問題点〉 しかしながら、染色業界の要望事項はさらに高度化し
ている。<Problems to be Solved by the Invention> However, the requirements of the dyeing industry are becoming more sophisticated.
例えば、染料溶解時に冷水で簡単に溶解できる、或い
は濃厚状態でもアルカリ浴安定性は良い等である。For example, when the dye is dissolved, it can be easily dissolved with cold water, or the stability of the alkaline bath is good even in a concentrated state.
又、最近、粉塵の発生がない、自動調液装置による計
量に適している等の利点から、液状反応染料が好まれる
傾向にある。Further, recently, liquid reactive dyes have tended to be preferred because of advantages such as generation of dust and suitability for measurement by an automatic liquid preparation device.
上式で示される染料は、その液状組成物の低温貯蔵安
定性の観点から溶解度の一層の改良が望まれている。From the viewpoint of low temperature storage stability of the liquid composition of the dye represented by the above formula, further improvement in solubility is desired.
〈問題を解決するための手段〉 本発明者は上記した問題を解決すべく鋭意検討の結
果、特定の組合せを含む染料組成物がこれらの問題を解
決することを見出し本発明を完成するに至った。<Means for Solving the Problems> As a result of intensive studies to solve the above problems, the present inventor has found that a dye composition containing a specific combination solves these problems, and has completed the present invention. It was
すなわち、本発明は、遊離酸の形で下記一般式（Ｉ） （式中、Ｚは−CH＝CH2又は−CH2CH2OSO3Ｈを表わ
す。） で示されるモノアゾ化合物50〜95重量％、及び遊離酸の
形で下記一般式（II） （式中、Ｚは前記の意味を有する。） で示されるモノアゾ化合物50〜５重量％から成る混合物
を含有してなる反応染料組成物を提供する。That is, the present invention provides a compound represented by the following general formula (I) in the form of a free acid. (In the formula, Z represents —CH═CH 2 or —CH 2 CH 2 OSO 3 H.) 50 to 95% by weight of a monoazo compound represented by the following general formula (II) in the form of a free acid. (In the formula, Z has the above meaning.) A reactive dye composition comprising a mixture of 50 to 5% by weight of a monoazo compound represented by
本発明の反応染料組成物は、それぞれ単独に式（Ｉ）
及び式（II）の化合物を常法により合成した後で所定の
混合割合となるように粉体配合するか合成時に２種の反
応基成分を所定の割合で混合使用することにより製造す
ることができる。本発明の染料組成物は、式（Ｉ）及び
式（II）で示される化合物以外の他の染料、染色助剤、
増量剤などを含有することができる。The reactive dye compositions of the present invention are of the formula (I)
And the compound of the formula (II) can be prepared by synthesizing by a conventional method and then powder blending so as to have a predetermined mixing ratio, or by mixing and using two kinds of reactive group components at a predetermined ratio at the time of synthesis. it can. The dye composition of the present invention comprises a dye other than the compounds represented by formula (I) and formula (II), a dyeing aid,
A filler or the like can be contained.
このようにして得られる本発明の染料組成物は、それ
ぞれ式（Ｉ）及び式（II）の染料単品よりも溶解度が大
幅に向上し、その結果、冷水にも簡単に溶解し、染料溶
解時の作業性を向上することができる。The thus-obtained dye composition of the present invention has a significantly improved solubility as compared with the dyes of the formula (I) and the formula (II) alone, and as a result, the dye composition easily dissolves in cold water. The workability of can be improved.
又、コールドパッドバッチ染色ではパディングの為に
調製される染料溶液には通常あらかじめアルカリが添加
されるので、染料は常温で繊維にパッドされるまで、調
製された染浴のなかで析出凝集或いはゲル化等の性状変
化を起こすことなく安定な状態で保持されることが必要
である。特に、濃度の高い染色物を得る時に問題となる
が、アルカリ浴での溶解度の高い本発明組成物はこの点
においても問題はなく、工業時に有利に用いられる。Also, in cold pad batch dyeing, an alkali is usually added to the dye solution prepared for padding in advance, so the dye is precipitated and aggregated or gelled in the prepared dyeing bath until it is padded on the fiber at room temperature. It is necessary to maintain a stable state without causing property changes such as aging. In particular, this is a problem when obtaining a dyed product having a high concentration, but the composition of the present invention having a high solubility in an alkaline bath has no problem in this respect as well, and is advantageously used in industry.
さらに、本発明組成物は容易に液状品とすることがで
き、式（Ｉ）及び式（II）の染料単独の液状品に比べ、
低温貯蔵安定性が優れている。Furthermore, the composition of the present invention can be easily made into a liquid product, and compared with a liquid product containing only the dye of the formula (I) and the formula (II),
Excellent low temperature storage stability.
以下、実施例により本発明を更に詳細に説明する。実
施例中、部は重量部を表わす。Hereinafter, the present invention will be described in more detail with reference to Examples. In the examples, "part" means "part by weight".
実施例１ ２−アミノナフタレン−3,6,8−トリスルホン酸54部
を水500部に分散させ、塩酸15部を加えた後、亜硝酸ソ
ーダ10部を水30部に溶解した液を30分で加え、５〜10℃
で１時間攪拌する。過剰の亜硝酸をスルファミン酸で消
去した後、このジアゾニウム塩をｍ−アミノフエニル尿
素26部を水150部に分散したスラリー液に加える。Example 1 54 parts of 2-aminonaphthalene-3,6,8-trisulfonic acid was dispersed in 500 parts of water, 15 parts of hydrochloric acid was added, and then 10 parts of sodium nitrite was dissolved in 30 parts of water to obtain 30 parts. Add in minutes, 5-10 ℃
Stir for 1 hour. After removing excess nitrous acid with sulfamic acid, the diazonium salt is added to a slurry liquid in which 26 parts of m-aminophenylurea is dispersed in 150 parts of water.
さらに２時間攪拌してカップリングを終了させる。 Stir for another 2 hours to complete the coupling.
次いで、塩化シアヌル25部を加え、５時間攪拌する。 Then, 25 parts of cyanuric chloride is added and stirred for 5 hours.
次いで、ｍ−アミノフエニルウルファートエチルスル
ホン35部とｐ−アミノフエニルスルファートエチルスル
ホン４部を加え、45〜50℃に昇温し、同温度で７時間攪
拌する。反応終了後、塩化ナトリウムで塩析し、結晶を
析出させ、吸引過により結晶を別した後、60℃で乾
燥する。Then, 35 parts of m-aminophenyl sulfoethyl ethyl sulfone and 4 parts of p-aminophenyl sulfate ethyl sulfone are added, the temperature is raised to 45 to 50 ° C., and the mixture is stirred at the same temperature for 7 hours. After completion of the reaction, salting out is carried out with sodium chloride to precipitate crystals, and the crystals are separated by suction and dried at 60 ° C.
この様にして得られた染料組成物は、染料分として、
下式（１）の染料成分を90重量％ 及び下式（２）の染料成分を10重量％ を含んでおり、極めて良好な溶解度を有していた。The dye composition thus obtained, as a dye component,
90% by weight of the dye component of formula (1) below And 10% by weight of the dye component of the following formula (2) And had a very good solubility.
実施例２ ｍ−アミノフエニルスルファートエチルスルホンを31
部、ｐ−アミノフエニルスルファートエチルスルホンを
８部用いる以外は実施例１と同様にして、溶解度の優れ
ている反応染料組成物〔染料分として、式（１）の染料
成分を80重量％、式（２）の染料成分を20重量％含む〕
を得た。Example 2 31 m-aminophenyl sulfate ethyl sulfone
Parts, a reactive dye composition having excellent solubility in the same manner as in Example 1 except that 8 parts of p-aminophenylsulfatoethyl sulfone is used [80% by weight of the dye component of the formula (1) as a dye component]. , Containing 20% by weight of the dye component of formula (2)]
I got
実施例３ 実施例１でｐ−アミノフエニルスルファートエチルス
ルホンの代りにｍ−アミノフエニルスルファートエステ
ルスルホンを用いて合成した染料70部と、実施例１でｍ
−アミノフエニルスルファートエチルスルホンの代りに
ｐ−アミノフエニルスルファートエチルスルホンを用い
て合成した染料30部を配合機で混合した染料組成物は、
極めて良好な溶解度を有していた。Example 3 70 parts of a dye synthesized by using m-aminophenyl sulfate ester sulfone in place of p-aminophenyl sulfate ethyl sulfone in Example 1 and m in Example 1
A dye composition prepared by mixing 30 parts of a dye synthesized by using p-aminophenylsulfatoethylsulfone in place of aminophenylsulfatoethylsulfone in a blender is
It had a very good solubility.
実施例４ 試料所定量を上皿天秤で秤量し100mlビーカーに入
れ、85℃の水100mlをビーカーに加え、83℃の恒温槽に
入れた。ビーカーの内温が80℃にっているのを確認して
からプロペラ式攪拌機を廻し２分間攪拌した。このよう
にして得られた試料溶液を20℃±１℃の恒温槽に入れ、
４時間放置する。試溶液をブフナーロート上の東洋濾紙
No.5A（直径11cm）一枚で吸引濾した。濾紙上の溶液が
完全に吸引されてから濾紙の残渣の有無を観察した。濾
紙を取り出し風乾した。Example 4 A predetermined amount of a sample was weighed with a precision balance and placed in a 100 ml beaker. 100 ml of water at 85 ° C was added to the beaker and placed in a thermostat at 83 ° C. After confirming that the internal temperature of the beaker was 80 ° C., the propeller stirrer was turned to stir for 2 minutes. The sample solution thus obtained was placed in a thermostat at 20 ° C ± 1 ° C,
Leave for 4 hours. Toyo filter paper on Buchner funnel
A single No. 5A (diameter 11 cm) was used for suction filtration. After the solution on the filter paper was completely sucked, the presence or absence of residue on the filter paper was observed. The filter paper was removed and air dried.
判定表示（絶対値） 吸引濾過直後に濾紙上の残渣の有無を観察し、濾紙上
に残渣の認められない界量（g/l）およびその時の温度
と放置時間を表示する。その結果を表１に示す。Judgment display (absolute value) Immediately after suction filtration, observe the presence or absence of residue on the filter paper, and display the amount of boundary (g / l) where no residue is found on the filter paper, and the temperature and standing time at that time. Table 1 shows the results.
中性溶解度 実施例５ 所定量の染料を約50mlの熱湯に完全に溶解し、冷却後
水を加えて80mlに調整したものを染料液とした。無水芒
硝15gを約70mlの熱湯に完全に溶解し、これにNaOH（40
°Be）13mlを加え、20〜30℃まで冷却後、水を加えて全
量を100mlに調整してアルカリ液とした。染料液中にア
ルカリ液20mlを添加してよく攪拌し、液温を25〜27℃に
保って放置した。アルカリ添加後10分毎に濾紙（東洋濾
紙NO.2）に染料液を滴下した。Neutral solubility Example 5 A predetermined amount of dye was completely dissolved in about 50 ml of boiling water, and after cooling, water was added to adjust to 80 ml to prepare a dye solution. 15 g of anhydrous Glauber's salt was completely dissolved in about 70 ml of boiling water, and NaOH (40
(BeBe) 13 ml was added, and after cooling to 20 to 30 ° C., water was added to adjust the total amount to 100 ml to prepare an alkaline solution. 20 ml of an alkaline solution was added to the dye solution and well stirred, and the solution temperature was kept at 25 to 27 ° C. and allowed to stand. The dye solution was added dropwise to the filter paper (Toyo Filter Paper No. 2) every 10 minutes after the addition of the alkali.
判定 濾紙上に作った染液のスポットを観察し、凝集物、ゲル
状物の有無を調べ、凝集物またはゲル状物を認めた時間
を表示する。Judgment The spots of the dyeing solution made on the filter paper are observed and checked for the presence of aggregates or gels, and the time when the aggregates or gels are recognized is displayed.
その結果を表２に示す。Table 2 shows the results.
実施例６ 化合物（１）および化合物（２）を各配合比で配合し
た染料5gを上皿天秤で秤量し、約50mlの熱湯に完全に溶
解し、イオン交換水を加えて１に調製する。この染料
液60mlおよび20％硫酸ナトリウム溶液25mlをステンレス
ポットに採取し、浴比が1:20になるように染浴を水で調
整する。被染物（未シルケット綿ニット）を上記ステン
レスポットに入れ、染色機にセット、20分後に20％炭酸
ナトリウム溶液10mlを加え60分間染色する。染色終了
後、染色物を取り出し充分水洗を行った後、1g/lのアデ
カノールTS800コンクを含むソーピング浴にて95℃で10
分間ソーピングを行う。次いで充分に水洗を行い、乾燥
する。 Example 6 5 g of the dye in which the compound (1) and the compound (2) were blended at respective compounding ratios were weighed with a precision balance, completely dissolved in about 50 ml of boiling water, and ion-exchanged water was added to prepare 1. 60 ml of this dye solution and 25 ml of 20% sodium sulfate solution are collected in a stainless steel pot, and the dye bath is adjusted with water so that the bath ratio is 1:20. Put the dyed product (unmercury cotton knit) in the stainless pot, set it in the dyeing machine, and after 20 minutes, add 10 ml of 20% sodium carbonate solution and dye for 60 minutes. After dyeing, take out the dyed product, wash it thoroughly with water, and then use a soaping bath containing 1 g / l of ADEKA NOL TS800 CONK at 95 ° C for 10 days.
Soap for minutes. Then, it is thoroughly washed with water and dried.
判定 得られた染色物の表面濃度（K/S値）をSICOMUC −20
〔（株）住化分析センター製測色システム）により測定
し、標準品に対するカラーイールドを次式により算出す
る。Judgment The surface density (K / S value) of the obtained dyed product is calculated by SICOMUC -20
[Measurement using a color measurement system manufactured by Sumika Chemical Analysis Service, Ltd.]
Then, calculate the color yield for the standard product by the following formula.
You.
（ここでの標準品は供試化合物（１）とする。） その結果を表３に示す。 (The standard product here is the test compound (1).) The results are shown in Table 3.
Claims (1)
す。） で示されるモノアゾ化合物50〜95重量％、及び遊離酸の
形で下記一般式（II） （式中、Ｚは前記の意味を有する。） で示されるモノアゾ化合物50〜５重量％から成る混合物
を含有してなる反応染料組成物。1. The following general formula (I) in the form of a free acid. (In the formula, Z represents —CH═CH 2 or —CH 2 CH 2 OSO 3 H.) 50 to 95% by weight of a monoazo compound represented by the following general formula (II) in the form of a free acid. (In the formula, Z has the above meaning.) A reactive dye composition comprising a mixture of 50 to 5% by weight of a monoazo compound represented by the formula:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62045958A JP2565703B2 (en) | 1987-02-27 | 1987-02-27 | Reactive dye composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62045958A JP2565703B2 (en) | 1987-02-27 | 1987-02-27 | Reactive dye composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63213573A JPS63213573A (en) | 1988-09-06 |
| JP2565703B2 true JP2565703B2 (en) | 1996-12-18 |
Family
ID=12733773
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62045958A Expired - Fee Related JP2565703B2 (en) | 1987-02-27 | 1987-02-27 | Reactive dye composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2565703B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2250297B (en) * | 1990-11-27 | 1994-04-20 | Sumitomo Chemical Co | Fiber reactive yellow dye composition |
| CN104341795B (en) * | 2014-10-21 | 2017-10-27 | 泰兴锦云染料有限公司 | A kind of reactive yellow dyes of high washing fastness and preparation method thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5615481A (en) * | 1979-07-11 | 1981-02-14 | Sumitomo Chemical Co | Dyeing of cellulosic fiber |
-
1987
- 1987-02-27 JP JP62045958A patent/JP2565703B2/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5615481A (en) * | 1979-07-11 | 1981-02-14 | Sumitomo Chemical Co | Dyeing of cellulosic fiber |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63213573A (en) | 1988-09-06 |
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