JPH0751678B2 - Water-soluble monoazo dye - Google Patents
Water-soluble monoazo dyeInfo
- Publication number
- JPH0751678B2 JPH0751678B2 JP62117930A JP11793087A JPH0751678B2 JP H0751678 B2 JPH0751678 B2 JP H0751678B2 JP 62117930 A JP62117930 A JP 62117930A JP 11793087 A JP11793087 A JP 11793087A JP H0751678 B2 JPH0751678 B2 JP H0751678B2
- Authority
- JP
- Japan
- Prior art keywords
- dye
- group
- water
- present
- 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.)
- Expired - Lifetime
Links
Description
【発明の詳細な説明】 （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り、詳しくは構造中にビニルス
ルホン型反応基を有し、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。DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a medium-yellow water-soluble monoazo dye having a novel structure, and more particularly to a vinyl sulfone type reactive group in the structure, The present invention relates to a water-soluble monoazo dye suitable for dyeing cellulose or nitrogen-containing fibers.
（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
度も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。(Prior Art) When dyeing fibers containing cellulose or nitrogen-containing fibers, a water-soluble reactive dye is usually used. As the reactive dye, a level dyeing property is excellent and an article to be dyed is also used. It is required to be able to dye deeply and to have various fastnesses of the dyed product. 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.
例えば、特開昭59−96174号には下記構造式〔ア〕、
〔イ〕で示されるナフタレンアゾベンゼン系反応性染料
が示されている。For example, in JP-A-59-96174, the following structural formula [A],
A naphthalene azobenzene-based reactive dye represented by [a] is shown.
しかしながら、前示構造式〔ア〕の反応性染料は均染性
は良好であるものの、例えば、被染物にアイロンをかけ
た際の熱変色性は満足すべきものではない。一方、前示
構造式〔イ〕の反応染料は熱変色性は小さいが、均染性
がやや不十分である上、被染物を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満足すべきもので
はない。 However, although the reactive dye of the structural formula [A] shown above has a good level dyeing property, for example, the thermochromic property when the dyed object is ironed is not satisfactory. On the other hand, the reactive dye of the structural formula (a) shown above has a small thermal discoloration property, but its level dyeing property is somewhat insufficient, and it should be satisfactory in terms of discoloration property against strong alkaline water when dying a dyed object. Not kimono.
（発明が解決しょうとする問題点） 本発明は上記実情に鑑み、反応性染料として用いた場
合、均染性が良好で、熱変色性が小さく、且つ、染色後
にシルケット加工をする際の強アルカリ水に対する変色
性も小さい総合的に優れた黄色系の水溶性色素を提供し
ょうとするものである。(Problems to be solved by the invention) In view of the above situation, the present invention, when used as a reactive dye, has good leveling property, small thermochromic property, and is strong in mercerizing after dyeing. It is an object of the present invention to provide a totally excellent yellow water-soluble dye that has little discoloration to alkaline water.
（問題点を解決するための手段） 本発明者等は、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を用いることにより、本発明の上記
の目的が達成されることを見い出し、本発明を完成する
に至った。(Means for Solving the Problems) As a result of various investigations, the present inventors have found that the use of a novel monoazo compound having a specific structure achieves the above-mentioned object of the present invention. The invention was completed.
すなわち、本発明は遊離酸の形で、下記一般式〔Ｉ〕 〔式中、Ｘは−NHCONH2基を表わし、R1は水素原子また
は低級アルキル基を表わし、R2およびR3は水素原子、低
級アルキル基、低級アルコキシ基またはハロゲン原子を
表わし、Ｙは−CH＝CH2基または−CH2CH2OSO3H基を表わ
し、ｎは１〜３の整数を表わす。〕で示される水溶性モ
ノアゾ色素に存する。That is, the present invention is in the form of a free acid represented by the following general formula [I] [In the formula, X represents a -NHCONH 2 group, R 1 represents a hydrogen atom or a lower alkyl group, R 2 and R 3 represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a halogen atom, and Y represents-. CH = CH 2 group or -CH 2 CH 2 OSO 3 H group, and n represents an integer of 1 to 3. ] It exists in the water-soluble monoazo dye shown by these.
以下、本発明を詳細に説明するに、前示一般式〔Ｉ〕に
おけるR1、R2およびR3が低級アルキル基を表わす場合、
低級アルキル基とは、例えば、メチル基、エチル基、プ
ロピル基等の炭素数１〜４の直鎖または分岐状のアルキ
ル基を意味する。BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail, in which R 1 , R 2 and R 3 in the general formula [I] shown above represent a lower alkyl group,
The lower alkyl group means, for example, a linear or branched alkyl group having 1 to 4 carbon atoms such as a methyl group, an ethyl group and a propyl group.
R2およびR3が低級アルコキシ基の場合は、例えば、メト
キシ基、エトキシ基、プロポキシ基などの炭素数１〜４
の直鎖または分岐状のアルコキシ基が挙げられ、また、
R2およびR3で表わされるハロゲン原子としては、通常、
弗素原子、塩素原子、臭素原子が挙げられる。When R 2 and R 3 are lower alkoxy groups, for example, they have 1 to 4 carbon atoms such as methoxy group, ethoxy group, propoxy group and the like.
A linear or branched alkoxy group of
The halogen atom represented by R 2 and R 3 is usually
A fluorine atom, a chlorine atom, and a bromine atom are mentioned.
本発明の前示一般式〔Ｉ〕で表わされるモノアゾ色素は
例えば、一般式〔II〕 （式中、Ｘは前示一般式〔Ｉ〕におけると同一の意義を
有する。）で示される色素類と下記一般式〔III〕 H2NCH2 nSO3H ……〔III〕 （式中、ｎは前示一般式〔Ｉ〕におけると同一の意義を
有する。）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〕 （式中、Ｘおよびｎは前示一般式〔Ｉ〕におけると同一
の意義を有する。）となし、これに下記一般式〔Ｖ〕 （式中、R1、R2、R3およびＹは前示一般式〔Ｉ〕におけ
ると同一の意義を有する。）で表わされる化合物を水系
媒質中90〜95℃の温度で縮合させることにより容易に製
造される。The monoazo dye represented by the above general formula [I] of the present invention is, for example, the general formula [II] (In the formula, X has the same meaning as in the above-mentioned general formula [I].) And a dye represented by the following general formula [III] H 2 NCH 2 n SO 3 H ... [III] (wherein , N has the same meaning as in the above-mentioned general formula [I].
Condensation at a temperature of ° C (Wherein X and n have the same meaning as in the general formula [I] shown above), and the following general formula [V] (Wherein R 1 , R 2 , R 3 and Y have the same meaning as in the above-mentioned general formula [I]) by condensing in a water-based medium at a temperature of 90 to 95 ° C. Easily manufactured.
（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。(Function) The monoazo dye of the present invention can be widely used as a dye for dyeing fibers, cloths, etc., a dye for coloring papers, synthetic resins, and a dye for inkjet printers. Excellent suitability as a dye.
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。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.
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。In order to dye cellulose or nitrogen-containing fibers with the monoazo dye of the present invention, usually, an acid alkali binder such as sodium bicarbonate, an inorganic alkali such as sodium carbonate, or an organic base such as triethylamine is used. In the presence, it can be stained by a conventional method.
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。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.
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。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.
（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。(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.
実施例１ 構造式 （λmax 405nm）で示されるモノアゾ色素0.3gを水300ml
に溶解し、芒硝20gを加え溶解して調製した染浴に綿布1
5gを浸漬し30分を要して50℃迄昇温した。次いで、炭酸
ソーダ4.5gを添加し50℃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。Example 1 Structural formula (Λ max 405 nm) 0.3 g of monoazo dye, 300 ml of water
1 g of cotton cloth in a dye bath prepared by dissolving and dissolving 20 g of Glauber's salt
5 g was immersed and the temperature was raised to 50 ° C over 30 minutes. Then, 4.5 g of sodium carbonate was added and dyeing was carried out at 50 ° C. for 1 hour, followed by washing with water, soaping, washing with water and drying to obtain a dyed product having a good yellow levelness.
また、この染色物にアイロンをかけても熱変色がなく、
更に、これを３％水酸化ナトリウム水溶液中に浸漬処理
（20℃×５分間）とし、未処理布との色相変化を比較し
たが、その変化は非常に小さかった。In addition, even if you iron this dyed product, there is no heat discoloration,
Further, this was dipped in a 3% aqueous solution of sodium hydroxide (20 ° C. × 5 minutes) and the hue change was compared with that of an untreated cloth, but the change was very small.
なお、ここで用いたモノアゾ色素は下記構造式 で示されるモノアゾ化合物１モル割合と２−アミノエタ
ンスルホン酸１モル割合を水媒体中30〜40℃の温度で、
液性を炭酸ナトリウムでpH 8に保ちつつ10時間撹拌し反
応を行ない、下記構造式 で示される化合物とした後３−（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 5〜６
に保ちつつ10時間撹拌し反応を行った後塩化カリウムで
塩析して製造した。The monoazo dye used here has the following structural formula. 1 mole ratio of the monoazo compound represented by and 1 mole ratio of 2-aminoethanesulfonic acid in an aqueous medium at a temperature of 30 to 40 ° C.
The reaction was carried out by stirring the solution for 10 hours while maintaining the pH at 8 with sodium carbonate. After the compound represented by the formula (3) was prepared, the liquid property was adjusted to pH 5-6 with sodium acetate at a temperature of 90-95 ° C. in a molar ratio of 3- (β-hydroxyethyl) sulfonylaniline sulfate.
The reaction was carried out by stirring for 10 hours while maintaining the above temperature, and then salting out with potassium chloride was performed.
実施例２ 第１表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、均一で濃厚な
染色ができ、得られた染色物にアイロンをかけても熱変
色はなく、強アルカリ処理後の色相変化も小さかった。Example 2 The monoazo dyes of the present invention (shown in the form of free acid) shown in Table 1 were synthesized according to the method of Example 1, and cotton cloth was dyed in the same manner as in Example 1, respectively. A uniform and deep dyeing was possible, no thermal discoloration was observed when the obtained dyed product was ironed, and the change in hue after strong alkaline treatment was small.
（発明の効果） 本発明のモノアゾ色素を用いセルロース、または含窒素
繊維染色した場合、均染性良好で熱やアルカリ水に対す
る変色が小さい堅牢な黄色の染色物を得ることができ
る。 (Effect of the Invention) When the monoazo dye of the present invention is used for dyeing cellulose or nitrogen-containing fibers, it is possible to obtain a fast yellow dyed product having good levelness and little discoloration to heat or alkaline water.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 清水 幸晴 福岡県北九州市八幡西区大字藤田2447番地 の１ 三菱化成工業株式会社黒崎工場内 (56)参考文献 特開 昭59−96174（ＪＰ，Ａ) ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Yukiharu Shimizu 1 2447, Fujita, Hachimansai-ku, Kitakyushu, Fukuoka Prefecture Mitsubishi Kasei Kogyo Co., Ltd. Kurosaki Plant (56) Reference JP-A-59-96174 (JP, A)
Claims (1)
は低級アルキル基を表わし、R2およびR3は水素原子、低
級アルキル基、低級アルコキシ基またはハロゲン原子を
表わし、Ｙは−CH＝CH2基または−CH2CH2OSO3H基を表わ
し、ｎは１〜３の整数を表わす〕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 represents a -NHCONH 2 group, R 1 represents a hydrogen atom or a lower alkyl group, R 2 and R 3 represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a halogen atom, and Y represents-. CH = CH 2 group or -CH 2 CH 2 OSO 3 H group, and n represents an integer of 1 to 3].
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62117930A JPH0751678B2 (en) | 1987-05-14 | 1987-05-14 | Water-soluble monoazo dye |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62117930A JPH0751678B2 (en) | 1987-05-14 | 1987-05-14 | Water-soluble monoazo dye |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63280769A JPS63280769A (en) | 1988-11-17 |
| JPH0751678B2 true JPH0751678B2 (en) | 1995-06-05 |
Family
ID=14723724
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62117930A Expired - Lifetime JPH0751678B2 (en) | 1987-05-14 | 1987-05-14 | Water-soluble monoazo dye |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0751678B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9515304D0 (en) * | 1995-07-26 | 1995-09-20 | Ilford Ag | Azo dyes |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5996174A (en) * | 1982-11-24 | 1984-06-02 | Mitsubishi Chem Ind Ltd | Reactive dye for cellulose fiber |
-
1987
- 1987-05-14 JP JP62117930A patent/JPH0751678B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63280769A (en) | 1988-11-17 |
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