JPS59213765A - Monoazo dye for polyester fiber - Google Patents
Monoazo dye for polyester fiberInfo
- Publication number
- JPS59213765A JPS59213765A JP8727683A JP8727683A JPS59213765A JP S59213765 A JPS59213765 A JP S59213765A JP 8727683 A JP8727683 A JP 8727683A JP 8727683 A JP8727683 A JP 8727683A JP S59213765 A JPS59213765 A JP S59213765A
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- group
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- formula
- fastness
- phenyl
- Prior art date
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Abstract
Description
【発明の詳細な説明】
本発明はポリエステル繊維用モノアゾ染料に関するもの
でアシ、詳しくはポリエステル繊維を諸竪牢度、特に耐
光竪牢度、耐昇華竪牢度に優れた赤色ないし青色に染色
し、かつ耐熱性およびアルカリ防抜染性に優れたモノア
ゾ染料に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a monoazo dye for polyester fibers, and more specifically, it dyes polyester fibers in red to blue colors that are excellent in various degrees of rigidity, particularly light resistance and sublimation resistance. The present invention relates to a monoazo dye having excellent heat resistance and alkali discharge printing resistance.
最近、ポリエステル繊維の新しい染色加工法として、ア
ルカリ防抜染加工が多〈実施されるようになった。アル
カリ防抜染の原理は、染色布の所定部分の染料をアルカ
リによって加水分解し、ポリエステル繊維に対する親和
性を失わせしめることである。Recently, as a new dyeing process for polyester fibers, alkali-resistant discharge printing has become popular. The principle of alkali-proof discharge printing is to hydrolyze the dye in a predetermined portion of the dyed fabric with an alkali, causing it to lose its affinity for polyester fibers.
特に最近はアルカリ防抜染性を高め、地染め布の防抜染
性が良好でアシ、アルカリ剤及び可溶化抜染促進剤の使
用量が少量で差し色染料損傷の少ない染料が強く望まれ
ている。Particularly recently, there has been a strong demand for dyes that have improved alkali discharge resistance, good resistance to discharge printing of ground-dyed fabrics, use of small amounts of reeds, alkaline agents, and solubilizing discharge printing accelerators, and less damage to the accent color dye.
従って、この目的に使用する染料は、骨格中比較的多く
保有している。そのため、アルカリ防抜染性は高まるが
、耐洗濯堅牢度、耐汗堅牢度および耐水堅牢度等の湿潤
堅牢度や、さらには耐熱性が劣るという欠点があった。Therefore, the dye used for this purpose is retained in a relatively large amount in the skeleton. Therefore, although the alkali discharge printing resistance is improved, there is a drawback that the wet fastness such as washing fastness, sweat fastness and water fastness, and further heat resistance are poor.
本発明は、良好なアルカリ防抜染性を有し、かつ良好な
湿潤堅牢度および耐熱性を有する染料の開発を目的とし
、鋭意検討した所、この相反する原理的矛盾を解決し1
本発明を完成した。The purpose of the present invention is to develop a dye that has good alkali discharge resistance, wet fastness, and heat resistance, and after intensive studies, we have resolved these contradictory principles.
The invention has been completed.
すなわち1本発明に係る染料は、下記一般式[1)
(式中、Xは水素原子、塩素原子、低級アルキル基また
はフェニル基を表わし、Yは水素原子、メチル基、塩素
原子、またはアセチルアミノ基’e!わし、Z (d、
= ) ロ基マタU No(、R”) 0=OH−基
を表わし、Rtはシアノ基、01〜輌アルコキシカルボ
ニル基、フェニル基、フェニルスルホニル基、ベンゾイ
ル基を表わし、RはC3〜0.oアルキル基を表わす)
で示されるポリエステル繊維用モノアゾ染料をその要旨
とするものである。That is, the dye according to the present invention has the following general formula [1] (wherein, X represents a hydrogen atom, a chlorine atom, a lower alkyl group, or a phenyl group, and Y represents a hydrogen atom, a methyl group, a chlorine atom, or an acetylamino Base 'e! I, Z (d,
=) RO group U No(,R'') 0=OH- group, Rt represents a cyano group, 01~alkoxycarbonyl group, phenyl group, phenylsulfonyl group, benzoyl group, R represents C3~0. o represents an alkyl group)
The gist is the monoazo dye for polyester fibers shown in the following.
前足一般式[”Dで示される染料はたとえば。For example, dyes represented by the forepaw general formula [D].
下記一般式[1[]
(式中、X、Zは前記定義と同じ)で示されるアニリン
類をジアゾ化し、下記一般式〔l)(式中Yは前記定義
に同じ)で示されるアミン類とカップリングさせること
によシ製造される。Anilines represented by the following general formula [1[] (wherein, X and Z are the same as defined above) are diazotized to produce amines represented by the following general formula [l] (wherein Y is the same as defined above). It is manufactured by coupling with.
xで示される低級アルキル基としてはメチル基、エチル
基、グルビル基、ブチル基等が挙げられ、R′で示され
る01〜01oアルコキシカルボニル基としては、メト
キシカルボニル基、エトキシカルボニル基、プロポキシ
カルボニル基、ブトキシカルボニル基、ペントキシカル
ボニル基。Examples of the lower alkyl group represented by x include methyl group, ethyl group, gluvyl group, butyl group, etc., and examples of the 01-01o alkoxycarbonyl group represented by R' include methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group. , butoxycarbonyl group, pentoxycarbonyl group.
ヘキンキシカルボニル基、ヘプチ四キシカルボデパ
二ル基、オクチロキシカルボニル基、fカッキシカルボ
ニル基等が挙げられ、Rで示されるアルコキシ基として
は、メチル基、エチル基、プロピル基、イソプロピル基
、ブチル基、イソブチル基、アミル基、ヘキシル基、ヘ
プチル基。Examples of the alkoxy group represented by R include hequinoxycarbonyl group, heptytetraxycarbodepanyl group, octyloxycarbonyl group, fcoxycarbonyl group, and examples of the alkoxy group represented by R include methyl group, ethyl group, propyl group, isopropyl group, and butyl group. group, isobutyl group, amyl group, hexyl group, heptyl group.
オクチル基、2−エチルヘキシル基、デシル基等があげ
られる。Examples include octyl group, 2-ethylhexyl group, and decyl group.
前記一般式CDにおいて、Xが水素原子または塩素原子
、特に、水素原子であ勺、Yが水素原子、メチル基また
は塩素原子、特に、水素原子でI、zがニトロ基または
H3迦=CH−基。In the general formula CD, X is a hydrogen atom or a chlorine atom, especially a hydrogen atom, Y is a hydrogen atom, a methyl group or a chlorine atom, especially a hydrogen atom, and z is a nitro group or a H3=CH- Base.
特に、ニトロ基であシ、RがC3〜c、oフルキル基、
特に、C8〜C6のアルキル基であるものが好ましい。In particular, a nitro group, R is a C3-c, o-furkyl group,
Particularly preferred are C8 to C6 alkyl groups.
本発明のモノアゾ染料によシ染色し得る繊維類としては
、ポリエチレンテレフタレート、テレフタル酸と/、ク
ービス−(ヒドロキシメチル)シクロヘキサンとの重縮
金物などによるポリエステル繊維、あるいは木綿、絹、
羊毛などの天然繊維と上記ポリエステル繊維との混紡品
、混繊品が挙げられる。Examples of fibers that can be dyed with the monoazo dye of the present invention include polyester fibers made of polyethylene terephthalate, polycondensed metals of terephthalic acid and/or cubis-(hydroxymethyl)cyclohexane, cotton, silk, etc.
Examples include blended products and mixed fiber products of natural fibers such as wool and the above-mentioned polyester fibers.
本発明の染料を用いてポリエステル繊維全染色するには
、常法によp、ナフクレンスルホン酸とホルムアルデヒ
ドとの縮合物、高級アルコール硫酸エステル、高級アル
キルベンゼンスルホン酸塩等の分散剤を使用し、前足一
般式CI〕で示される染料を水性媒体中に分散させて染
色浴または捺染糊1に調製し、浸染または捺染を行なえ
ばよい。たとえば、浸染を行なう場合には。In order to fully dye polyester fibers using the dye of the present invention, a dispersant such as p, a condensate of napucrene sulfonic acid and formaldehyde, a higher alcohol sulfate, a higher alkylbenzene sulfonate, etc. is used in a conventional manner. A dye represented by general formula CI] may be dispersed in an aqueous medium to prepare a dyeing bath or printing paste 1, and then dyeing or printing may be carried out. For example, when performing dyeing.
高温染色法、キャリヤー染色法、ザーモゾル染色法など
の通常の染色処理法ti用することによシ、ポリエステ
ル繊維ないしはその混紡、混繊品にW早変のすぐれた染
色を施こすことができる。また、場合によシ、染色浴に
蟻酸、酢酸。By using conventional dyeing methods such as high-temperature dyeing, carrier dyeing, thermosol dyeing, etc., it is possible to dye polyester fibers or their blends and blended fibers with excellent W change speed. Also, if necessary, formic acid or acetic acid may be added to the dye bath.
燐酸あるいは硫酸アンモニタムなどの酸性物質を添加し
ておくことによシ、さらに好結果が得られることがある
。Even better results may be obtained by adding an acidic substance such as phosphoric acid or ammonium sulfate.
不発明のモノアゾ染料は同系統の染料あるいは他系統の
染料と併用してもよく、特に前足一般式CI]で示され
る染料相互の配合によフ染色性の向上等、好結果が得ら
れることがある。The uninvented monoazo dye may be used in combination with dyes of the same type or dyes of other types, and in particular, good results such as improved dyeability can be obtained by combining the dyes represented by the general formula CI]. There is.
本発明の染料は、カップラー窒素置換基に。The dyes of the invention have a coupler nitrogen substituent.
シアノエチル基とアルコキシカルボニルオキシ基が導入
されているため、驚くべきことに極めて良好なアルカリ
抜染性全盲し、かつ優秀な湿潤堅牢度を示す実用性の高
い染料である。Because it contains a cyanoethyl group and an alkoxycarbonyloxy group, it is surprisingly a highly practical dye that exhibits extremely good alkaline discharge printability and excellent wet fastness.
なお、同様の置換基金有する染料が、特公昭y3−it
Jii号公報に記載されているが。In addition, dyes with similar replacement funds are
Although it is described in the Jii issue.
これらはいずれもベンゼン系のジアゾ成分を有する染料
であシ、アルカリ抜染適性に今一つ不元である。All of these dyes have a benzene-based diazo component, and are not suitable for alkaline discharge printing.
次に本発明を実施例及び比較例にょシ更に具体的に説明
するが、本願発明はこれら実施例に限定されるものでは
ない。Next, the present invention will be explained in more detail with reference to Examples and Comparative Examples, but the present invention is not limited to these Examples.
実施例/
下記構造式
で表わされるモノアゾ染料θ、!Jをす7タレンスルホ
ン酸−ホルムアルデヒド縮合物/、θ1および高級アル
コール硫酸エステル2gを含む水3tに分散させて染色
液ft調製した。Example/ Monoazo dye θ represented by the following structural formula,! A staining solution ft was prepared by dispersing J in 3 t of water containing 7 talenesulfonic acid-formaldehyde condensate/, θ1 and 2 g of higher alcohol sulfate.
この染色浴にポリエステル布/θ01!’r浸漬し、7
30℃で60分間染色し念後、ソーピンク、水洗、およ
び乾燥を行なった之ころ、耐光堅牢度、耐昇華堅牢度お
よび湿潤堅牢度の良好なボルドー色に染色されたポリエ
ステル布が得られた。Polyester cloth/θ01 in this dye bath! 'r dipped, 7
After dyeing at 30° C. for 60 minutes, washing with water and drying, a polyester cloth dyed in a burgundy color with good light fastness, sublimation fastness and wet fastness was obtained.
本実施例で使用した染料は、!−二トローλ−アミノチ
アゾールを硫酸中で、ニトロシル硫酸音用いてジアゾ化
し、N−シアノエチル−N−n−ブトキシカルボニルオ
キシエチルアニリン、tJyをメタノール/θO−に溶
解した溶液中に0〜3’Qで添加し析出結晶茫ろ別、水
洗及び乾燥を行うことによ)得られた(理論収率9/%
)。不品のλmaX (アセトン)はjar nmであ
った。The dye used in this example is! - Dizotyl λ-aminothiazole was diazotized in sulfuric acid using nitrosyl sulfate, and N-cyanoethyl-N-n-butoxycarbonyloxyethylaniline, tJy, was added to a solution of 0-3' in methanol/θO-. (Theoretical yield: 9/%)
). The λmaX (acetone) of the rejected product was jar nm.
実施例λ
下記構造式
で示される染料o、、t g yl(ナフタレンスルホ
ン酸−ホルムアルデヒド縮合物θ39と混合し、ペイン
トシェーカーで微粉砕し、微粒子化染料を得た。下記の
組成からなる元糊と十分混合し。Example λ Dye o, t g yl represented by the following structural formula (mixed with naphthalene sulfonic acid-formaldehyde condensate θ39 and finely pulverized with a paint shaker to obtain a finely divided dye. A base paste consisting of the following composition Mix thoroughly.
元糊組成
カルボキシメチルセルロース系糊剤 301
1酒石酸 θ0.2J
芳香族キーヤリヤー θ、31/
水 ≦7.!J色
糊100gを得た。Original glue composition Carboxymethylcellulose based glue 301
1 Tartaric acid θ0.2J Aromatic key carrier θ, 31/
Water ≦7. ! 100 g of J color glue was obtained.
この色糊盆ポリエステル繊維上に印捺し。This color glue tray is printed on polyester fiber.
700℃にて中間乾燥を行ない、ついで720℃の過熱
水蒸気中にて7分間保持し発色させた後、ソーピンク、
水洗および乾燥を行なったところ、耐光堅牢度、耐昇華
堅牢度および湿潤堅牢度の良好な赤味青色に捺染された
ポリエステル布が得られた。After performing intermediate drying at 700°C, and then holding in superheated steam at 720°C for 7 minutes to develop color, it became So Pink,
After washing with water and drying, a reddish-blue printed polyester cloth with good light fastness, sublimation fastness, and wet fastness was obtained.
本実施例で使用した染料のλmax (アセトン)は!
7 e nmであった。What is the λmax (acetone) of the dye used in this example?
It was 7 e nm.
実施例3
実施例イと同様の方法によシ、下記第1表に示した染料
を用いてポリエステルミR維を染色し、第1表に示す色
調の染色物を得た。Example 3 In the same manner as in Example A, polyester MiR fibers were dyed using the dyes shown in Table 1 below to obtain dyed products having the colors shown in Table 1.
なお、以下特に表示のないアルキル基はノルマルを示す
。In addition, the alkyl group which is not specifically indicated below shows normal.
比較例/〜3
次に本発明染料と、構造の類イリする公知染料との比較
実験を行い結果を第2表に示す。Comparative Examples/~3 Next, a comparative experiment was conducted between the dye of the present invention and a known dye having a similar structure, and the results are shown in Table 2.
*:公知染料/ 米国特許第2??/9’12号明細書
記載**:公知染料2 特開昭Δ゛6−1.0jj♂号
公報記載*林:公知染料3 特開昭j7−/6062号
公報記載第λ表から明らかなように5本発明の染料は。*: Known dye/U.S. Patent No. 2? ? /9'12 specification **: Known dye 2 As described in JP-A-6-1.0jj♂ *Hayashi: Known dye 3 As is clear from the λ table described in JP-A-7-6062 The dye of the present invention is as follows.
良好なアルカリ抜染性?有するとともに、湿潤堅牢度、
耐熱性等を有する極めて高い実用的価値のある染料であ
る。Good alkaline discharge printability? as well as wet fastness,
It is a dye with extremely high practical value due to its heat resistance.
尚、@コ表において、各特性の評価0よ下記の方法によ
シ行なった。In addition, in the @ table, the evaluation of each property was determined by the following method.
+l) アルカリ抜染性
あらかじめ試験すべき染料で染色した染色布に、炭酸ン
ーダとポリエチレングリコール(平均分子量aoo)’
@含む抜染wJt塗布し、温度/♂O℃で7分間過熱水
蒸気中で処理した後に、還元洗浄して得られた染布の抜
染部分の白度を汚染用グレースケチルで判定した。+l) Alkaline discharge dyeing property A dyed cloth dyed with the dye to be tested in advance is coated with carbonate powder and polyethylene glycol (average molecular weight aoo)'
The whiteness of the discharge-printed portion of the dyed fabric obtained by applying @containing discharge printing wJt and treating it in superheated steam for 7 minutes at a temperature of ♂O ℃ was determined using gray ketyl for contamination.
]2) ボリウレタ/加工法
一ハイドランF−,2gK”(商品名、大日本インキ化
学社製)の1%溶液を使用して730℃で2分間キユア
リングする。] 2) Polyurethane/Processing method - Curing at 730° C. for 2 minutes using a 1% solution of “Hydran F-, 2gK” (trade name, manufactured by Dainippon Ink Chemical Co., Ltd.).
(3)洗濯堅牢度
ポリウレタン加工を施した染色布にマルチファイバーを
添付し、AATCO法洗濯IA号に準じて洗濯試験を行
ない、マルチファイバーのナイロン繊維の汚染をグレー
スケールにて判定した。(3) Washing fastness A multi-fiber was attached to a dyed cloth treated with polyurethane, and a washing test was conducted according to AATCO washing method No. IA, and contamination of the nylon fibers of the multi-fiber was determined on a gray scale.
(4)汗堅早変
ポリウレタン加工?施した染色布iJ工8L−Or4#
A法に準じ、但し添付布はナイロン布とシルク布全使
用した方法により試験上行ない、シルク布の汚染度をグ
レースケールにて判定した。(4) Polyurethane treatment that changes sweat hardness quickly? Dyed cloth iJ 8L-Or4#
The test was carried out in accordance with Method A, except that both nylon cloth and silk cloth were used as the attached cloths, and the degree of contamination of the silk cloth was determined on a gray scale.
(0)水堅牢度
ポリウレタン加工を施した染色布i JISL−〇、l
f′4t6五法に準じ、但しナイロン布の代わシシルク
布を添付した方法によシ試験全行ない、シルク布の汚染
度をグレースケールにて判定した。(0) Water fastness: Dyed fabric treated with polyurethane JISL-〇, l
All tests were conducted in accordance with the f'4t6 method except that a silk cloth was attached instead of the nylon cloth, and the degree of contamination of the silk cloth was determined on a gray scale.
(6)耐熱性
染料ケーキ全ナフタレンスルホン酸−ホルムアルデヒド
縮合物と混合し、/ 30 ’Oで7時間熱処理した後
の染料の残存率で判定した。(6) Heat-resistant dye cake Mixed with total naphthalene sulfonic acid-formaldehyde condensate and heat-treated at /30'O for 7 hours, and then judged by the residual rate of the dye.
出願人 合成染料技術研究組合 代理人 弁理士 長谷用 − ほか/名Applicant: Synthetic Dye Technology Research Association Agent Patent Attorney Hase - Others/names
Claims (1)
たはフェニル基を表わし、Yは水素原子、メチル基、塩
素原子、またはアセチC8〜0.oのアルコキシカルボ
ニル基、フェニル基、フェニルスルホニル基、ヘンソイ
ル基ヲ表わし、RはC3〜C8oのアルキル基を表わす
)で示されるポリエステル繊維用モノアゾ染料(1) General formula (wherein, X represents a hydrogen atom, a chlorine atom, a lower alkyl group, or a phenyl group, and Y represents a hydrogen atom, a methyl group, a chlorine atom, or an acetic acid C8-0.o alkoxycarbonyl group, A monoazo dye for polyester fibers represented by a phenyl group, a phenylsulfonyl group, or a hensoyyl group, and R represents a C3 to C8o alkyl group
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP8727683A JPS59213765A (en) | 1983-05-18 | 1983-05-18 | Monoazo dye for polyester fiber |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP8727683A JPS59213765A (en) | 1983-05-18 | 1983-05-18 | Monoazo dye for polyester fiber |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS59213765A true JPS59213765A (en) | 1984-12-03 |
JPH0372103B2 JPH0372103B2 (en) | 1991-11-15 |
Family
ID=13910246
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP8727683A Granted JPS59213765A (en) | 1983-05-18 | 1983-05-18 | Monoazo dye for polyester fiber |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS59213765A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4642339A (en) * | 1983-03-18 | 1987-02-10 | Research Association Of Synthetic Dyestuffs | Thiazoleazophenylaminoethyl carbonyloxy-C8 -C10 -alkyl compounds useful as dyes for polyester fibers |
WO2009019206A3 (en) * | 2007-08-09 | 2009-06-04 | Dystar Textilfarben Gmbh & Co | 1,3-thiazolyl azo dyes, their preparation and use |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS56143247A (en) * | 1980-03-13 | 1981-11-07 | Sandoz Ag | 4-chlorothiazolyl containing compound |
-
1983
- 1983-05-18 JP JP8727683A patent/JPS59213765A/en active Granted
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS56143247A (en) * | 1980-03-13 | 1981-11-07 | Sandoz Ag | 4-chlorothiazolyl containing compound |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4642339A (en) * | 1983-03-18 | 1987-02-10 | Research Association Of Synthetic Dyestuffs | Thiazoleazophenylaminoethyl carbonyloxy-C8 -C10 -alkyl compounds useful as dyes for polyester fibers |
WO2009019206A3 (en) * | 2007-08-09 | 2009-06-04 | Dystar Textilfarben Gmbh & Co | 1,3-thiazolyl azo dyes, their preparation and use |
JP2010535877A (en) * | 2007-08-09 | 2010-11-25 | ダイスター・テクスティルファルベン・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング・ウント・コンパニー・ドイッチュラント・コマンデイトゲゼルシャフト | 1,3-thiazolylazo dyes, their preparation and use |
US7892295B2 (en) | 2007-08-09 | 2011-02-22 | Dystar Colours Deutschland Gmbh | 1.3-thiazolyl azo dyes, their preparation and use |
Also Published As
Publication number | Publication date |
---|---|
JPH0372103B2 (en) | 1991-11-15 |
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