JPH069893A - Water-soluble monoazo dye - Google Patents
Water-soluble monoazo dyeInfo
- Publication number
- JPH069893A JPH069893A JP16616392A JP16616392A JPH069893A JP H069893 A JPH069893 A JP H069893A JP 16616392 A JP16616392 A JP 16616392A JP 16616392 A JP16616392 A JP 16616392A JP H069893 A JPH069893 A JP H069893A
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- JP
- Japan
- Prior art keywords
- group
- formula
- dye
- compound
- water
- 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.)
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/503—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an esterified or non-esterified hydroxyalkyl sulfonyl or mercaptoalkyl sulfonyl group, a quaternised or non-quaternised aminoalkyl sulfonyl group, a heterylmercapto alkyl sulfonyl group, a vinyl sulfonyl or a substituted vinyl sulfonyl group, or a thiophene-dioxide group
- C09B62/507—Azo dyes
- C09B62/51—Monoazo dyes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は新規な構造を有する中庸
黄色系の水溶性モノアゾ色素に関するものである。詳し
くは、構造中に３個の反応基を有し、特にセルロースま
たは含窒素繊維の染色に適した水溶性モノアゾ色素に関
するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a medium yellow water-soluble monoazo dye having a novel structure. More specifically, the present invention relates to a water-soluble monoazo dye having three reactive groups in its structure, which is particularly suitable for dyeing cellulose or nitrogen-containing fibers.
【０００２】[0002]
【従来の技術】セルロースまたは含窒素繊維を含有する
繊維類を染色する場合、通常、水溶性の反応性染料が用
いられるが、この反応性染料としては、均染性に優れ、
且つ、被染物を濃厚に染色することができ、しかも、染
色物の各種堅牢度の良好なものが要求される。このよう
な反応性染料の特性は染料の基本骨格、置換基、反応基
及びこれらの組合せにより微妙に異なり、従来、種々の
構造の染料が提案されている。2. Description of the Related Art When dyeing fibers containing cellulose or nitrogen-containing fibers, water-soluble reactive dyes are usually used.
In addition, it is required that the dyed product can be dyed deeply and that the dyed product has various fastnesses. The characteristics of such reactive dyes are slightly different depending on the basic skeleton of the dye, the substituents, the reactive groups and combinations thereof, and dyes having various structures have been proposed in the past.
【０００３】公知の中庸黄色染料の例として、特公昭５
８−１８４７４号及び特公昭５８−１８４７１号には下
記の構造〔ア〕及び〔イ〕の反応性染料が示されてい
る。As an example of a known medium yellow dye, Japanese Patent Publication No.
No. 8-18474 and Japanese Patent Publication No. 58-18471 disclose reactive dyes having the following structures [a] and [a].
【０００４】[0004]
【化２】 [Chemical 2]
【０００５】〔ア〕，〔イ〕で示される如くジアゾ成分
はいずれもナフタレン系であるが、これらの染料は均染
性が今一歩不充分であり、またビルドアップ性の点で満
足すべきものではない。As shown in [a] and [a], the diazo components are both naphthalene type, but these dyes are not satisfactory in levelness and are satisfactory in terms of build-up. is not.
【０００６】[0006]
【発明が解決しようとする課題】本発明は、上記実情に
鑑みなされたものであり、塩素堅牢度、耐光堅牢度はも
ちろんのこと均染性が良好で、かつビルドアップ性の優
れた中庸黄色系の水溶性反応染料を提供しようとするも
のである。SUMMARY OF THE INVENTION The present invention has been made in view of the above-mentioned circumstances, and has a good levelness of chlorine as well as fastness to light and light-fastness, and has a good build-up property. It is intended to provide a water-soluble reactive dye of the system.
【０００７】[0007]
【課題を解決するための手段】本発明者等は、上述の如
き特性を有した水溶性反応染料を提供すべく種々検討し
た結果、特定の構造を持つ新規なモノアゾ化合物が、上
記の目的を達成することを見い出し、本発明を完成させ
るに至った。すなわち、本発明の要旨は遊離酸の形で下
記一般式〔Ｉ〕As a result of various investigations by the present inventors to provide a water-soluble reactive dye having the above-mentioned characteristics, a novel monoazo compound having a specific structure has the above-mentioned object. After finding what has been achieved, the present invention has been completed. That is, the gist of the present invention is the following formula [I] in the form of a free acid.
【０００８】[0008]
【化３】 [Chemical 3]
【０００９】〔式中、Ｘは−ＣＨ＝ＣＨ2 または−ＣＨ
2 ＣＨ2 Ｗ（ここでＷはアルカリにより脱離する基を表
わす）を表わし、Ｙはハロゲン原子又は−ＮＲ3 −Ｅ−
ＳＯ 2 Ｘを表わし、Ｅは置換基を有していても良いフェ
ニレン基またはナフチレン基を表し、Ｒ1 は低級アルキ
ル基、−ＮＨＣＯＮＨ2 基又は−ＮＨＣＯＴ（ここでＴ
は低級アルキル基を表わす）を表わし、Ｒ2 は水素原
子、Ｃ1 〜Ｃ2 のアルキル基またはアルコキシ基を表わ
し、Ｒ3 は水素原子またはＣ1 〜Ｃ2 アルキル基を表わ
す〕で示される水溶性モノアゾ色素に存する。[Wherein, X is -CH = CH2Or -CH
2CH2W (where W represents a group capable of leaving by alkali)
Where Y is a halogen atom or —NR3-E-
SO 2Represents X, and E represents a substituent which may have a substituent.
Represents a nylene group or a naphthylene group, R1Is lower archi
Group, -NHCONH2Group or -NHCOT (where T
Represents a lower alkyl group), and R2Is hydrogen
Child, C1~ C2Represents an alkyl group or an alkoxy group of
And R3Is a hydrogen atom or C1~ C2Represents an alkyl group
]] In the water-soluble monoazo dye.
【００１０】本発明を更に詳述する。前示式〔Ｉ〕中、
Ｘは−ＣＨ＝ＣＨ2 または−ＣＨ2 ＣＨ2 Ｗである。ア
ルカリの作用により−ＣＨ2 ＣＨ2 ＷからＷ−Ｈが脱離
して−ＣＨ＝ＣＨ2 となるので−ＣＨ2 ＣＨ2 Ｗと−Ｃ
Ｈ＝ＣＨ2 は均等物である。Ｗで表わされるアルカリの
作用で脱離する基としては、通常、硫酸エステル基、チ
オ硫酸エステル基、リン酸エステル基、酢酸エステル
基、またはハロゲン原子などがあげられ、特に好ましく
は硫酸エステル基があげられる。The present invention will be described in more detail. In the above formula [I],
X is -CH = CH 2 or -CH 2 CH 2 W. Since the -CH = CH 2 -CH 2 CH 2 W from W-H is eliminated by the action of an alkali -CH 2 CH 2 W and -C
H = CH 2 is equivalent. Examples of the group which is eliminated by the action of an alkali represented by W include a sulfate ester group, a thiosulfate ester group, a phosphate ester group, an acetate ester group, or a halogen atom, and a sulfate ester group is particularly preferable. can give.
【００１１】Ｙで表わされるハロゲン原子としては、フ
ッ素原子、塩素原子、臭素原子があげられるが特にフッ
素原子が好ましい。Ｒ1 は低級アルキル基、−ＮＨＣＯ
ＮＨ2 基または−ＮＨＣＯＴ（Ｔは低級アルキル基を表
わす）であるが、特にＲ1 が低級アルキル基、ＮＨＣＯ
ＮＨ2 基である場合には被染物を後シルケット加工する
際の強アルカリ水に対する変色性の点で優れている。Examples of the halogen atom represented by Y include a fluorine atom, a chlorine atom and a bromine atom, and a fluorine atom is particularly preferable. R 1 is a lower alkyl group, -NHCO
NH 2 group or —NHCOT (T represents a lower alkyl group), particularly R 1 is a lower alkyl group, NHCO
When it is an NH 2 group, it is excellent in terms of discoloration with respect to strong alkaline water when the article to be dyed is subjected to post mercerizing.
【００１２】Ｒ2 は、水素原子、Ｃ1 〜Ｃ2 アルキル基
またはＣ1 〜Ｃ2 アルコキシ基を表わす。又、Ｒ3 は水
素原子またはＣ1 〜Ｃ2 アルキル基を表わす。ジアゾ成
分中の−ＳＯ3 Ｈ基、−ＳＯ2 Ｘ基の置換位置はオルト
位、メタ位、パラ位のいずれでもよく、例えば下記の基
等が挙げられる。R 2 represents a hydrogen atom, a C 1 -C 2 alkyl group or a C 1 -C 2 alkoxy group. R 3 represents a hydrogen atom or a C 1 -C 2 alkyl group. -SO 3 H groups in a diazo component, the substitution position of -SO 2 X group ortho, meta, may be any of the para position, for example, groups such as the following may be mentioned.
【００１３】[0013]
【化４】 [Chemical 4]
【００１４】一般式〔Ｉ〕において、Ｅで表されるフェ
ニレンおよびナフチレンとしては、メチル、エチル、メ
トキシ、エトキシ、クロロ、ブロモ及びスルホの群から
選ばれる、１又は２個の置換基により置換されていても
よいフェニレンおよびスルホで置換されていてもよいナ
フチレンが例示され、例えば、下記の構造の基等が挙げ
られる。In the general formula [I], the phenylene and naphthylene represented by E are substituted with 1 or 2 substituents selected from the group consisting of methyl, ethyl, methoxy, ethoxy, chloro, bromo and sulfo. Examples thereof include phenylene which may be substituted and naphthylene which may be substituted with sulfo, and examples thereof include groups having the following structures.
【００１５】[0015]
【化５】 [Chemical 5]
【００１６】[0016]
【化６】 [Chemical 6]
【００１７】（式中、＊で示した結合は、−Ｎ（Ｒ3 ）
−基に通じている結合を意味する。）なお、本願明細書
に於いて、低級アルキル基は、通常Ｃ1 〜Ｃ4 アルキル
基を意味する。(In the formula, the bond indicated by * is -N (R 3 )
-Means a bond leading to a group. In this specification, the lower alkyl group usually means a C 1 -C 4 alkyl group.
【００１８】本発明のモノアゾ色素は、遊離酸の形で、
またはその塩の形で存在するが、塩としては通常アルカ
リ金属およびアルカリ土類金属塩であり、特にリチウム
塩、ナトリウム塩、カリウム塩が好ましい。前記一般式
〔Ｉ〕で表わされるモノアゾ色素は次のようにして製造
することができる。例えば下記一般式〔II〕で示される
色素類と下記一般式〔III 〕で表わされるアミン類を水
性媒質中、３０〜４０℃の温度で縮合させ下記一般式
〔IV〕の化合物を製造する。The monoazo dye of the present invention is in the form of a free acid,
Or, it exists in the form of a salt thereof, and the salt is usually an alkali metal salt or an alkaline earth metal salt, and a lithium salt, a sodium salt and a potassium salt are particularly preferable. The monoazo dye represented by the general formula [I] can be produced as follows. For example, the dyes represented by the following general formula [II] and the amines represented by the following general formula [III] are condensed in an aqueous medium at a temperature of 30 to 40 [deg.] C. to produce a compound of the following general formula [IV].
【００１９】[0019]
【化７】 [Chemical 7]
【００２０】（式〔II〕及び〔IV〕中、Ｒ1 ，Ｒ2 およ
びＸは前示定義と同じであり、Ｙ′はハロゲン原子を表
わす。式〔III 〕及び〔IV〕中、Ｅ，ＸおよびＲ3 は前
示定義と同じである。）前示式〔IV〕で表わされる化合
物は、前示式〔Ｉ〕に於いて、Ｙがハロゲン原子である
モノアゾ色素に相当する。(In the formulas [II] and [IV], R 1 , R 2 and X are the same as defined above, and Y'represents a halogen atom. In formulas [III] and [IV], E, X and R 3 are the same as defined above.) The compound represented by the above formula [IV] corresponds to the monoazo dye in which Y is a halogen atom in the above formula [I].
【００２１】また、前示一般式〔Ｉ〕において、Ｙが−
ＮＲ3 −Ｅ−ＳＯ2 Ｘで表わされるモノアゾ色素は、前
示一般式〔IV〕で表わされるモノアゾ色素と前示一般式
〔III 〕で表わされるアミン類を水性媒質中、９０〜９
５℃の温度で縮合させて製造する。本発明のモノアゾ色
素の特徴は、ジアゾ成分が−ＳＯ3 Ｈ基２個および−Ｓ
Ｏ 2 Ｘ基で置換されているフェニル基であり、かつカッ
プリング成分にハロゲン原子と−ＮＲ3 −Ｅ−ＳＯ2 Ｘ
基、または２つの−ＮＲ3 −Ｅ−ＳＯ2 Ｘ基で置換され
たトリアゾニル基を有することにある。この構造によ
り、ビルドアップ性および均染性が著しく向上する。In the general formula [I] shown above, Y is-
NR3-E-SO2The monoazo dye represented by X is
Shown by the general formula [IV] and the general formula shown above
The amines represented by [III] in an aqueous medium in an amount of 90 to 9
It is produced by condensation at a temperature of 5 ° C. Monoazo color of the present invention
The basic characteristic is that the diazo component is -SO3Two H groups and -S
O 2A phenyl group substituted with an X group, and
Halogen atom and -NR as pulling component3-E-SO2X
Group, or two -NR3-E-SO2Substituted with X group
It has a triazonyl group. With this structure
The build-up property and level dyeing property are remarkably improved.
【００２２】[0022]
【作用】本発明のモノアゾ色素は繊維、布などを染色す
るための染料、紙、合成樹脂を着色するための色素、更
に、インクジェット式プリンター用などの色素として広
く利用することができるが、特に染料としての適性が優
れている。本発明のモノアゾ色素を染料として用いる場
合には、対象となる繊維としては、木綿、ビスコースレ
ーヨン、キュプラアンモニウムレーヨン、麻などのセル
ロース系繊維、更にポリアミド、羊毛、絹等の含窒素繊
維が挙げられるが、セルロース繊維が特に望ましい。ま
た、これらの繊維は、例えばポリエステル、トリアセテ
ート、ポリアクリロニトリルなどの混合繊維として用い
られていても差し支えない。The monoazo dye of the present invention can be widely used as a dye for dyeing fibers and cloths, a dye for coloring paper and synthetic resins, and a dye for ink jet printers. Excellent suitability as a dye. When the monoazo dye of the present invention is used as a dye, target fibers include cellulosic fibers such as cotton, viscose rayon, cupraammonium rayon and hemp, and further nitrogen-containing fibers such as polyamide, wool and silk. However, cellulosic fibers are particularly desirable. Further, these fibers may be used as a mixed fiber of polyester, triacetate, polyacrylonitrile, etc., for example.
【００２３】本発明のモノアゾ色素を用いてセルロース
または含窒素繊維類を染色するには、通常、重炭酸ソー
ダ、炭酸ソーダ等の無機アルカリ、またはトリエチルア
ミン等の有機塩基よりなる酸結合剤を用い、これら酸結
合剤の存在下、常法に従って染色することができる。本
発明の色素を用いる染色法としては、特に浸染法が好適
であり、染色温度は通常、４０〜８０℃程度が好適であ
る。さらに、本発明の色素は、コールドパッドバッチ
法、パッドスチーム法、捺染法などの染色法に適用する
こともできる。In order to dye cellulose or nitrogen-containing fibers with the monoazo dye of the present invention, an acid binder consisting of an inorganic alkali such as sodium bicarbonate and sodium carbonate or an organic base such as triethylamine is usually used. Staining can be carried out in the presence of a binder according to a conventional method. The dyeing method using the dye of the present invention is particularly preferably the dip dyeing method, and the dyeing temperature is usually about 40 to 80 ° C. Furthermore, the dye of the present invention can also be applied to a dyeing method such as a cold pad batch method, a pad steam method, and a printing method.
【００２４】[0024]
【実施例】次に、本発明を実施例により具体的に説明す
るが、本発明はその要旨を超えない限り以下の実施例に
限定されるものではない。なお、ビルドアップ性、均染
性は次のようにして測定した。 〔ビルドアップ性の測定〕得られた染布の表面表射率を
色素計〔日本電色工業（株）製〕で測定し、染着濃度を
求めた。ビルドアップ性については各色素の０．３ｇ使
用した際の染着濃度に対する色素１．２ｇ使用した際の
染着濃度を求め、その相対値で表わした。 〔均染性〕モノアゾ色素０．３ｇを用いて染色した染色
布について、視覚により均一に染色されているか否かを
判定した。EXAMPLES Next, the present invention will be specifically described by way of examples, but the present invention is not limited to the following examples unless it exceeds the gist. The build-up property and level dyeing property were measured as follows. [Measurement of build-up property] The surface emissivity of the obtained dyed cloth was measured with a dye meter [manufactured by Nippon Denshoku Industries Co., Ltd.] to determine the dyeing density. Regarding the build-up property, the dyeing concentration when 1.2 g of the dye was used with respect to the dyeing concentration when 0.3 g of each dye was used was obtained and expressed as a relative value. [Leveling] The dyed cloth dyed with 0.3 g of the monoazo dye was visually judged to be uniformly dyed.
【００２５】実施例１、比較例１ 遊離酸の形で下記構造式〔Ｉ−１〕および〔Ａ−１〕で
示される各モノアゾ色素０．３ｇ又は１．２ｇをそれぞ
れ水３００ｍｌに溶解し、芒硝２０ｇを加え溶解して調
製した染浴に、未シルケット処理の綿布１５ｇを浸漬し
３０分を要して６０℃迄昇温した。次いで、炭酸ソーダ
４．５ｇを添加し６０℃で１時間染色した後、水洗、ソ
ーピング、水洗、乾燥を行ない、黄色の染色物を得た。
ビルドアップ性及び均染性を評価し、結果を表−１に示
した。Example 1, Comparative Example 1 0.3 g or 1.2 g of each monoazo dye represented by the following structural formulas [I-1] and [A-1] in the form of a free acid was dissolved in 300 ml of water, 15 g of unmercerized cotton cloth was immersed in a dye bath prepared by adding 20 g of sodium sulfate and dissolving it, and the temperature was raised to 60 ° C. in 30 minutes. Then, 4.5 g of sodium carbonate was added and dyeing was carried out at 60 ° C. for 1 hour, followed by washing with water, soaping, washing with water and drying to obtain a yellow dyed product.
Build-up properties and level dyeing properties were evaluated, and the results are shown in Table-1.
【００２６】[0026]
【化８】 [Chemical 8]
【００２７】[0027]
【表１】 [Table 1]
【００２８】なお、構造式〔Ｉ−１〕で表わされる本発
明のモノアゾ色素は遊離酸の形で下記構造式〔II−１〕The monoazo dye of the present invention represented by the structural formula [I-1] has the following structural formula [II-1] in the form of a free acid.
【００２９】[0029]
【化９】 [Chemical 9]
【００３０】で示されるモノアゾ化合物１モル割合と４
−（β−ヒドロキシエチル）スルホニルアニリン硫酸エ
ステル１．２モル割合を水媒体中３５℃でｐＨ＝５．０
〜５．５に保持して１０時間反応させ、塩化カリウムで
塩析を行うことにより得た。得られた化合物のλmax は
４１２ｎｍ（水媒体中）であった。 実施例２ 遊離酸の形で、下記構造式〔Ｉ−２〕1 mole ratio of monoazo compound represented by
1.2 mol ratio of-(β-hydroxyethyl) sulfonylaniline sulfuric acid ester was added at pH = 5.0 at 35 ° C in an aqueous medium.
It was obtained by carrying out the reaction for 10 hours while maintaining the pH at -5.5, and salting out with potassium chloride. Λ max of the obtained compound was 412 nm (in an aqueous medium). Example 2 In the form of a free acid, the following structural formula [I-2]
【００３１】[0031]
【化１０】 [Chemical 10]
【００３２】〔λmax ４１２ｎｍ（水媒体中）〕で示さ
れるモノアゾ色素０．３ｇ又は０．６ｇをそれぞれ水３
００ｍｌに溶解し、芒硝２０ｇを加え溶解して調製した
染浴に、綿布１５ｇを浸漬し３０分を要して６０℃迄昇
温した。次いで炭酸ソーダ４．５ｇを添加し６０℃で１
時間染色した後、水洗、ソーピング、水洗、乾燥を行な
い、黄色の均染性良好な染色物を得た。またビルドアッ
プ性も良好であった。0.3 g or 0.6 g of the monoazo dye represented by [λ max 412 nm (in an aqueous medium)] was added to water 3
15 g of cotton cloth was immersed in a dye bath prepared by dissolving 20 g of Glauber's salt in 00 ml and dissolving, and the temperature was raised to 60 ° C. in 30 minutes. Then add 4.5 g of sodium carbonate and add 1 at 60 ° C.
After dyeing for a period of time, washing with water, soaping, washing with water and drying were carried out to obtain a dyed product with good yellow levelness. The build-up property was also good.
【００３３】なお、実施例２の本発明モノアゾ色素は遊
離酸の形で下記構造式〔II−２〕The monoazo dye of the present invention of Example 2 is in the form of a free acid and has the following structural formula [II-2].
【００３４】[0034]
【化１１】 [Chemical 11]
【００３５】で示されるモノアゾ化合物１モル割合と４
−（β−ヒドロキシエチル）スルホニルアニリン硫酸エ
ステル１．２モル割合を水媒体中３５℃で液性を炭酸ナ
トリウムでｐＨ＝５．０〜５．５に保持して１０時間攪
拌し反応を行い、遊離酸の形で下記構造式〔Ｉ−２′〕1 mole ratio of the monoazo compound represented by and 4
-(Β-Hydroxyethyl) sulfonylaniline sulfate 1.2 mol ratio was maintained at 35 ° C in an aqueous medium at pH = 5.0 to 5.5 with sodium carbonate, and stirred for 10 hours for reaction. In the form of the free acid, the following structural formula [I-2 ′]
【００３６】[0036]
【化１２】 [Chemical 12]
【００３７】で示される化合物とした後、更に４−（β
−ヒドロキシエチル）スルホニルアニリン硫酸エステル
１．２モル割合と水媒体中９０〜９５℃の温度で液性を
酢酸ナトリウムでｐＨ＝５．０〜５．５に保持して１０
時間攪拌し反応を行った後、塩化カリウムで塩析して製
造した。 実施例３ 表−２に示す本発明のモノアゾ色素（遊離酸の形で示
す。）を実施例１または実施例２の方法に準じて合成
し、実施例１と同様の方法で綿布を染色したところ、各
々、均染性は著しく良好でビルドアップ性も良好であっ
た。After the compound of formula (4) is prepared, 4- (β
-Hydroxyethyl) sulfonylaniline sulfate 1.2 mol ratio and the liquid property in an aqueous medium at a temperature of 90 to 95 [deg.] C. and pH of 5.0 to 5.5 with sodium acetate.
The mixture was stirred for a reaction to carry out the reaction, and then salted out with potassium chloride for production. Example 3 The monoazo dyes of the present invention (shown in the form of free acid) shown in Table 2 were synthesized according to the method of Example 1 or Example 2, and the cotton cloth was dyed by the same method as in Example 1. However, the level dyeing properties were remarkably good and the build-up properties were also good.
【００３８】[0038]
【表２】 [Table 2]
【００３９】[0039]
【表３】 [Table 3]
【００４０】[0040]
【表４】 [Table 4]
【００４１】[0041]
【表５】 [Table 5]
【００４２】[0042]
【表６】 [Table 6]
【００４３】[0043]
【表７】 [Table 7]
【００４４】[0044]
【発明の効果】本発明のモノアゾ色素は、セルロースま
たは含窒素繊維を染色した場合、塩素堅牢度、耐光堅牢
度に加え、特に、均染性及びビルドアップ性が良好で、
中庸黄色系の水溶性反応染料として極めて有用である。Industrial Applicability The monoazo dye of the present invention, when dyed with cellulose or nitrogen-containing fibers, has good chlorine fastness and light fastness, and particularly good levelness and build-up property.
It is extremely useful as a medium yellow water-soluble reactive dye.
【手続補正書】[Procedure amendment]
【提出日】平成４年１０月１日[Submission date] October 1, 1992
【手続補正１】[Procedure Amendment 1]
【補正対象書類名】明細書[Document name to be amended] Statement
【補正対象項目名】００１３[Correction target item name] 0013
【補正方法】変更[Correction method] Change
【補正内容】[Correction content]
【００１３】[0013]
【化４】 [Chemical 4]
───────────────────────────────────────────────────── フロントページの続き (72)発明者 姫野 清 北九州市八幡西区黒崎城石１番１号 三菱 化成ヘキスト株式会社研究所内 ─────────────────────────────────────────────────── ─── Continuation of front page (72) Inventor Kiyohime Himeno 1-1 Kurosaki Shiroishi, Hachimansai-ku, Kitakyushu City Mitsubishi Kasei Hoechst Co., Ltd.
Claims (1)
（ここでＷはアルカリにより脱離する基を表わす）を表
わし、Ｙはハロゲン原子又は−ＮＲ3 −Ｅ−ＳＯ 2 Ｘを
表わし、Ｅは置換基を有していても良いフェニレン基ま
たはナフチレン基を表し、Ｒ1 は低級アルキル基、−Ｎ
ＨＣＯＮＨ2 基又は−ＮＨＣＯＴ（ここでＴは低級アル
キル基を表わす）を表わし、Ｒ2 は水素原子、Ｃ1 〜Ｃ
2 のアルキル基またはＣ1 〜Ｃ2 アルコキシ基を表わ
し、Ｒ3 は水素原子またはＣ1 〜Ｃ2アルキル基を表わ
す〕で示される水溶性モノアゾ色素。1. The following general formula [I] in the form of a free acid:[In the Formula, X is -CH = CH2Or -CH2CH2W
(Where W represents a group capable of leaving by alkali)
I, Y is a halogen atom or -NR3-E-SO 2X
In the formula, E is a phenylene group which may have a substituent.
Or naphthylene group, R1Is a lower alkyl group, -N
HCONH2Group or -NHCOT (where T is a lower alkyl
Represents a kill group) and R2Is a hydrogen atom, C1~ C
2Alkyl group or C1~ C2Represents an alkoxy group
And R3Is a hydrogen atom or C1~ C2Represents an alkyl group
] A water-soluble monoazo dye represented by
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP04166163A JP3126808B2 (en) | 1992-06-24 | 1992-06-24 | Water-soluble monoazo dye |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP04166163A JP3126808B2 (en) | 1992-06-24 | 1992-06-24 | Water-soluble monoazo dye |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH069893A true JPH069893A (en) | 1994-01-18 |
| JP3126808B2 JP3126808B2 (en) | 2001-01-22 |
Family
ID=15826248
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP04166163A Expired - Fee Related JP3126808B2 (en) | 1992-06-24 | 1992-06-24 | Water-soluble monoazo dye |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3126808B2 (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006103186A2 (en) * | 2005-03-26 | 2006-10-05 | Dystar Textilfarben Gmbh & Co Deutschland Kg | Reactive dyestuffs, method for the production thereof, and use of the same |
| CN106893353A (en) * | 2015-12-17 | 2017-06-27 | 上海安诺其集团股份有限公司 | A kind of application of monoazos |
| CN106893352A (en) * | 2015-12-17 | 2017-06-27 | 上海安诺其集团股份有限公司 | A kind of monoazos |
| CN106892874A (en) * | 2015-12-17 | 2017-06-27 | 江苏安诺其化工有限公司 | The preparation method of monoazos |
| CN106893361A (en) * | 2015-12-17 | 2017-06-27 | 上海安诺其集团股份有限公司 | A kind of dye composite and preparation method thereof |
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1992
- 1992-06-24 JP JP04166163A patent/JP3126808B2/en not_active Expired - Fee Related
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006103186A2 (en) * | 2005-03-26 | 2006-10-05 | Dystar Textilfarben Gmbh & Co Deutschland Kg | Reactive dyestuffs, method for the production thereof, and use of the same |
| WO2006103186A3 (en) * | 2005-03-26 | 2007-09-27 | Dystar Textilfarben Gmbh & Co | Reactive dyestuffs, method for the production thereof, and use of the same |
| CN106893353A (en) * | 2015-12-17 | 2017-06-27 | 上海安诺其集团股份有限公司 | A kind of application of monoazos |
| CN106893352A (en) * | 2015-12-17 | 2017-06-27 | 上海安诺其集团股份有限公司 | A kind of monoazos |
| CN106892874A (en) * | 2015-12-17 | 2017-06-27 | 江苏安诺其化工有限公司 | The preparation method of monoazos |
| CN106893361A (en) * | 2015-12-17 | 2017-06-27 | 上海安诺其集团股份有限公司 | A kind of dye composite and preparation method thereof |
| CN106893352B (en) * | 2015-12-17 | 2018-10-09 | 上海安诺其集团股份有限公司 | A kind of monoazos |
| CN106893361B (en) * | 2015-12-17 | 2018-10-09 | 上海安诺其集团股份有限公司 | A kind of dye composite and preparation method thereof |
| CN106893353B (en) * | 2015-12-17 | 2018-10-09 | 上海安诺其集团股份有限公司 | A kind of application of monoazos |
| CN106892874B (en) * | 2015-12-17 | 2019-06-25 | 江苏安诺其化工有限公司 | The preparation method of monoazos |
| CN116023796A (en) * | 2022-12-30 | 2023-04-28 | 上海雅运新材料有限公司 | Water-soluble dye compound and preparation method and application thereof |
| CN116023796B (en) * | 2022-12-30 | 2024-05-03 | 上海雅运新材料有限公司 | Water-soluble dye compound and preparation method and application thereof |
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| Publication number | Publication date |
|---|---|
| JP3126808B2 (en) | 2001-01-22 |
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