JPH0759672B2 - Monoazo acid dye - Google Patents
Monoazo acid dyeInfo
- Publication number
- JPH0759672B2 JPH0759672B2 JP25251386A JP25251386A JPH0759672B2 JP H0759672 B2 JPH0759672 B2 JP H0759672B2 JP 25251386 A JP25251386 A JP 25251386A JP 25251386 A JP25251386 A JP 25251386A JP H0759672 B2 JPH0759672 B2 JP H0759672B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- monoazo
- anhydride
- dye
- acid dye
- 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 - Fee Related
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Description
【発明の詳細な説明】 「産業上の利用分野」 本発明はモノアゾ酸性染料に関するものである。詳しく
はカップリング成分としてガンマ酸誘導体を有する下記
（１）式の化合物またはその塩からなるモノアゾ染料に
関するものである。The present invention relates to a monoazo acid dye. More specifically, it relates to a monoazo dye comprising a compound represented by the following formula (1) having a gamma acid derivative as a coupling component or a salt thereof.
（式中R1、R2はC5〜C9のアルキル基又はCH3を意味し、R
1、R2の何れか１つはC5〜C9のアルキル基である。） 「従来の技術」と「本発明が解決しようとする問題点」 従来からこの種染料としては下記構造の染料が知られて
いる。 (In the formula, R 1 and R 2 mean a C 5 to C 9 alkyl group or CH 3 ,
Any one of 1 and R 2 is a C 5 to C 9 alkyl group. ) "Prior art" and "Problems to be solved by the present invention" Conventionally, as this type of dye, a dye having the following structure is known.
これ等の内（Ａ）は溶解度はよいが、ホルマリンによる
変色があり、（Ｂ）はホルマリンによる変色はないが、
溶解度が悪くアルカリ汗に対する堅牢度が劣るという欠
点をもつている。本発明者等は、これ等の欠点を改善す
べく努力した結果、本発明のモノアゾ酸性染料を見出し
た。 Of these, (A) has good solubility but has discoloration due to formalin, and (B) has no discoloration due to formalin,
It has the drawback of poor solubility and poor fastness to alkaline sweat. As a result of efforts made by the present inventors to ameliorate these drawbacks, the present inventors have found the monoazo acid dye of the present invention.
「問題点を解決するための手段」と「作用」 即ち本発明は前記一般式（１）で表わされる化合物又は
その塩からなるモノアゾ酸性染料に係るものである。前
述既知化合物（Ａ）又は（Ｂ）におけるアセチル基をC5
〜C9のアルキル基をもつたアシル基とした化合物が、元
の化合物（Ａ）、（Ｂ）よりは湿潤堅牢度が向上するこ
とは考えられるが、本発明の化合物の溶解度が次記する
如く、既知化合物に比較して格段に向上することは考え
らえないことである。"Means for Solving Problems" and "Action" That is, the present invention relates to a monoazo acid dye comprising the compound represented by the general formula (1) or a salt thereof. The acetyl group in the aforementioned known compound (A) or (B) is replaced with C 5
It is considered that the compound having an acyl group having a C 9 alkyl group has an improved wet fastness than the original compounds (A) and (B), but the solubility of the compound of the present invention will be described below. As described above, it is unlikely that the compound will be remarkably improved as compared with the known compound.
本発明品と（Ａ）、（Ｂ）との堅牢度の比較は第１表に
示す。Table 1 shows a comparison of the fastness between the product of the present invention and (A) and (B).
本発明の染料は、１、４−ジアミノベンゼン−３−スル
ホン酸を無水カプロン酸、無水エナント酸、無水カプリ
ル酸、無水ペラルゴン酸、無水カプリン酸又はそれ等の
酸のハロゲン化物でアシル化し、得られたアシル化物を
ジアゾ化し、アセチルガンマ酸とカプリングさせるか、
１、４−ジアミノベンゼン−３−スルホン酸を無水酢酸
でアセチル化し、得られたアシル化物をジアゾ化し、ガ
ンマ酸を無水カプロン酸、無水エナント酸、無水カプリ
ル酸、無水ペラルゴン酸、無水カプリン酸又はそれ等の
酸のハロゲン化物でアシル化したものとをカップリング
させて得られる。 The dye of the present invention is obtained by acylating 1,4-diaminobenzene-3-sulfonic acid with caproic anhydride, enanthic anhydride, caprylic anhydride, pelargonic anhydride, capric anhydride, or a halide of such an acid. Diazotize the acylated product and couple it with acetyl gamma acid,
1,4-Diaminobenzene-3-sulfonic acid is acetylated with acetic anhydride, the obtained acylated product is diazotized, and gamma acid is converted into caproic anhydride, enanthic anhydride, caprylic anhydride, pelargonic anhydride, capric anhydride or It can be obtained by coupling with those acylated with an acid halide.
以下、実施例について之を説明する。Hereinafter, examples will be described.
実施例 1. ４−カプロイルアミノ−２−スルホフェエルアゾ−２′
−アセチルアミノ−８′−ヒドロキシナフタリン−６′
−スルホン酸ジナトリウム塩の合成 ４−アミノカプロイルアニリド−３−スルホン酸286g
（１モル）を水5500mlに加える。40％（Volume）塩酸22
8ml（2.5モル）を10分を要して加える。氷片3000gを加
え、温度を０〜５℃とし、次いで亜硝酸ナトリウム69g
（１モル）を40％の水溶液として、撹拌下に30分を要し
て滴下する。次いで苛性ソーダ64g（1.6モル）を30％水
溶液として撹拌下に15分かけて滴下してpH6.0に調整す
る。一方、アセチルガンマ酸295g（1.05モル）を水3000
mlに加え溶解し希硫酸でpH6に調整しておく。この溶液
をジアゾニウム塩の溶液中に撹拌下に加え、反応温度を
35℃に上昇させ20時間撹拌し、次いで70℃に昇温し染料
を溶解し、ソーダ灰80g（0.75モル）を10分で加えpH7.0
に調整した。この温度で食塩700gを加え塩折し35℃まで
冷却し過、食塩水で洗浄し、乾燥した。Example 1. 4-caproylamino-2-sulfoferreazo-2 '
-Acetylamino-8'-hydroxynaphthalene-6 '
-Synthesis of sulfonic acid disodium salt 4-aminocaproylanilide-3-sulfonic acid 286 g
(1 mol) is added to 5500 ml of water. 40% (Volume) Hydrochloric acid 22
Add 8 ml (2.5 mol) over 10 minutes. Add 3000g of ice chips and bring the temperature to 0-5 ° C, then 69g of sodium nitrite
(1 mol) as a 40% aqueous solution is added dropwise with stirring over 30 minutes. Next, 64 g (1.6 mol) of caustic soda was added dropwise as a 30% aqueous solution over 15 minutes with stirring to adjust the pH to 6.0. On the other hand, 295 g of acetyl gamma acid (1.05 mol) was added to 3000 of water.
Add to ml to dissolve and adjust to pH 6 with diluted sulfuric acid. This solution was added to the solution of the diazonium salt with stirring and the reaction temperature was adjusted.
The temperature was raised to 35 ° C and stirred for 20 hours, then the temperature was raised to 70 ° C to dissolve the dye, 80 g (0.75 mol) of soda ash was added in 10 minutes, and the pH was adjusted to 7.0.
Adjusted to. 700 g of sodium chloride was added at this temperature, and the mixture was salt-broken, cooled to 35 ° C., washed with brine and dried.
収量 750g このものの水溶液は500〜520nmで強い吸収を示した。ま
た、羊毛及びナイロンを酸性溶より堅牢な赤色に染色し
た。Yield 750g This aqueous solution showed strong absorption at 500-520nm. In addition, wool and nylon were dyed in a red color which is more robust than acidic solution.
実施例 2. ４−アセチルアミノ−２−スルホフェニルアゾ−２′−
カプロイルアミノ−８′−ヒドロキシナフタリン−６′
−スルホ酸ジナトリウム塩の合成 実施例１の４−アミノカプロイルアニリド−３−スルホ
ン酸の代りに４−アミノアセトアニリド−３−スルホン
酸の当量を用い、アセチルガンマ酸の代りにカプロイル
ガンマ酸を当量用いて実施例１と同様にして得た。この
ものは羊毛及びナイロンを酸性溶より堅牢な赤色に染色
した。Example 2. 4-Acetylamino-2-sulfophenylazo-2'-
Caproylamino-8'-hydroxynaphthalene-6 '
-Synthesis of sulfonic acid disodium salt Similar to Example 1 using 4-aminocaproylanilide-3-sulphonic acid in Example 1 instead of 4-aminoacetanilide-3-sulphonic acid in equivalent amount and replacing acetylgamma acid with equivalent amount of caproylgamma acid. I got it. This dyed wool and nylon a red color that is more robust than acidic solutions.
実施例 3. ４−エナンチルアミノ−２−スルホフェニルアゾ−２′
−アセチルアミノ−８′−ヒドロキシナフタレン−６′
−スルホン酸ジナトリウム塩の合成 実施例１の４−アミノカプロイルアニリド−３−スルホ
ン酸の代りに４−エナンチルアニリド−３−スルホン酸
の当量を用い、実施例１と同様にして得た。このものは
羊毛及びナイロンを酸性溶より堅牢な赤色に染色した。Example 3. 4-Enanthylamino-2-sulfophenylazo-2 '
-Acetylamino-8'-hydroxynaphthalene-6 '
-Synthesis of sulfonic acid disodium salt The procedure of Example 1 was repeated, except that 4-aminocaproylanilide-3-sulfonic acid of Example 1 was replaced with 4-enanthylanilide-3-sulfonic acid equivalent. This dyed wool and nylon a red color that is more robust than acidic solutions.
「発明の効果」 本発明のモノアゾ酸性染料は、既知の同種構造のモノア
ゾ酸性染料における最良の汗堅牢度、洗たく堅牢度、ホ
ルマリン感受性を備え、しかも、前記既知のモノアゾ酸
性染料にはみられない優れた溶解性を発揮するものであ
る。"Effect of the Invention" The monoazo acid dye of the present invention has the best sweat fastness, wash fastness, and formalin sensitivity among known monoazo acid dyes of the same structure, and is not found in the known monoazo acid dyes. It exhibits excellent solubility.
Claims (1)
塩からなるモノアゾ酸性染料。 （式中R1、R2はC5〜C9のアルキル基又はCH3を意味し
R1、R2の何れか１つはC5〜C9のアルキル基である。）1. A monoazo acid dye comprising a compound represented by the following formula (1) or a salt thereof. (Wherein R 1 and R 2 represent a C 5 to C 9 alkyl group or CH 3
Any one of R 1 and R 2 is a C 5 to C 9 alkyl group. )
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25251386A JPH0759672B2 (en) | 1986-10-23 | 1986-10-23 | Monoazo acid dye |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25251386A JPH0759672B2 (en) | 1986-10-23 | 1986-10-23 | Monoazo acid dye |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63108070A JPS63108070A (en) | 1988-05-12 |
| JPH0759672B2 true JPH0759672B2 (en) | 1995-06-28 |
Family
ID=17238414
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP25251386A Expired - Fee Related JPH0759672B2 (en) | 1986-10-23 | 1986-10-23 | Monoazo acid dye |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0759672B2 (en) |
-
1986
- 1986-10-23 JP JP25251386A patent/JPH0759672B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63108070A (en) | 1988-05-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |