JPS58191754A - Reactive dye for cellulosic fiber - Google Patents

Reactive dye for cellulosic fiber

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Publication number
JPS58191754A
JPS58191754A JP57075855A JP7585582A JPS58191754A JP S58191754 A JPS58191754 A JP S58191754A JP 57075855 A JP57075855 A JP 57075855A JP 7585582 A JP7585582 A JP 7585582A JP S58191754 A JPS58191754 A JP S58191754A
Authority
JP
Japan
Prior art keywords
formula
methyl
compound
group
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.)
Granted
Application number
JP57075855A
Other languages
Japanese (ja)
Other versions
JPH0643562B2 (en
Inventor
Toshio Niwa
俊夫 丹羽
Yoshiaki Kato
美明 加藤
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Mitsubishi Kasei Corp
Original Assignee
Mitsubishi Kasei Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Mitsubishi Kasei Corp filed Critical Mitsubishi Kasei Corp
Priority to JP57075855A priority Critical patent/JPH0643562B2/en
Publication of JPS58191754A publication Critical patent/JPS58191754A/en
Publication of JPH0643562B2 publication Critical patent/JPH0643562B2/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Abstract

NEW MATERIAL:A compound of formula I (R<1> is H, methyl; ethyl; R<2> is H, methyl, methoxy, sulfonic acid, X is H, methyl, methoxy, ethoxy; Y is H, methyl acetylamino, chlorine; X is aliphatic or aromatic residue bearing 1-2 sulfonic groups). EXAMPLE:The compound of formula II. USE:It dyes cellulosic fiber such as cotton, linen or viscose rayon and its blend fabrics thereof with synthetic fiber such as polyester yellow with high fastness to sweat, sun light and chlorine. PREPARATION:For example, the condensation reaction between a pigment of formula III and an amine of the formula: Z-H is conducted in an aqueous medium at 30-40 deg.C to give a compound of formula IV and the product is subjected to condensation reaction with a compound of formula V in an aqueous medium at 90-95 deg.C.

Description

【発明の詳細な説明】 本発明はセルロース繊維類用反応性染料に係るものであ
る。
DETAILED DESCRIPTION OF THE INVENTION The present invention relates to reactive dyes for cellulose fibers.

詳しくは1本発明はセルロース系繊維、特に天然または
再生セルロース繊維を堅牢かつ濃厚な黄色に染色するビ
ニルスルホニル型反応性染料に関するものである。
Specifically, the present invention relates to vinylsulfonyl-type reactive dyes for dyeing cellulosic fibers, particularly natural or regenerated cellulose fibers, in a fast and deep yellow color.

本発明のセルロース繊維類用反応性染料は一般式〔1〕 (式中、R1は水素、メチル基ま九はエテル基を宍わし
R2およびpmは水素、メチル基、メトチル基、アセチ
ルアミノ基または塩素を表わし、2はスルホン酸基をl
ケまたはコケ有する脂肪族または芳香族のアミノ残基を
費わす。)で示されるビニルスルホニル型反応性染料で
ある。
The reactive dye for cellulose fibers of the present invention has the general formula [1] (wherein R1 is hydrogen, a methyl group or an ether group, and R2 and pm are hydrogen, a methyl group, a methyl group, an acetylamino group, or 2 represents chlorine, and 2 represents a sulfonic acid group.
It contains aliphatic or aromatic amino residues with moss or moss. ) is a vinylsulfonyl-type reactive dye.

本発明の前足一般式(13で懺わされる染料は、例えば
一般式〔■〕 ! (式中、R1,XおよびYは前足一般式〔l〕ににおけ
ると同一の意義を有する。)で示される色素類と下6己
一般式 (式中、2は前足一般式(13におけると同一の意義を
有する。)で示されるアミン類を水系媒質中30〜μ0
Cで縮合させ下記一般式〔■〕(式中、R1、z 、 
Y オヨび2は前足一般式〔I〕におけると同一の意義
を有する。)で示される化合物となしこれに下記一般式
CI!/380、OH,OH,0日0.H (式中、R1およびHaは前足一般式〔1〕におけると
同一の意義を有する。)で示される化合物を水系媒質中
りθ〜ワjCで縮合させることにより容易に製造される
The dye coated with the forepaw general formula (13) of the present invention is, for example, the general formula [■]! (wherein, R1, X and Y have the same meanings as in the forepaw general formula [l]). The dyes shown and the amines represented by the general formula (wherein 2 has the same meaning as in the general formula (13)) were mixed in an aqueous medium at 30 to μ0
C and condensed to form the following general formula [■] (wherein, R1, z,
Y Oyobi 2 has the same meaning as in the foreleg general formula [I]. ) and the following general formula CI! /380, OH, OH, 0 days 0. It is easily produced by condensing a compound represented by H (wherein R1 and Ha have the same meanings as in the general formula [1]) in an aqueous medium at θ to wajC.

本発明の反応性染料により染色し得るセルロース繊維類
としては木綿、麻等の天然繊維、ビスコースレーヨン等
の再生−m i タu セルロース繊維とポリエステル
線維、ポリアクリロニトリル繊維等の合成繊維との混紡
品などが挙げられる。
Examples of cellulose fibers that can be dyed with the reactive dye of the present invention include natural fibers such as cotton and linen, and recycled blends of cellulose fibers and synthetic fibers such as polyester fibers and polyacrylonitrile fibers. Examples include products.

本発明の反応性染料を用いてセルロース繊維類を染色す
るには、酸結合剤例えば重脚酸ソーダ、炭酸ソーダ等の
無機アルカリを九はトリエチルアミン等の有機塩基の存
在下通常行なわれる方法で染色することができる。例え
に浸染法で染色する場合には食塩または芒硝等の無機塩
及び酸結合剤の存在下@Q〜60Cの温度条件下で通常
の方法によシ染色することができる。
In order to dye cellulose fibers using the reactive dye of the present invention, dyeing is carried out by a conventional method in the presence of an acid binder such as an inorganic alkali such as dibasic acid or sodium carbonate, or an organic base such as triethylamine. can do. For example, in the case of dyeing by dip dyeing, dyeing can be carried out by a conventional method in the presence of an inorganic salt such as common salt or mirabilite and an acid binder at a temperature of Q to 60C.

さらに捺染法で染色する場合にも通常用いられる方法例
えばアルギン酸ソーダ、尿素、還元防止剤、酸結合剤を
用いて行う方法で染色することができる。またパツドノ
(フチ法、パッドスチーム法などビニルスルホニル型水
溶性反応性染料に用いられる各種の染色法が適用できる
Furthermore, when dyeing by a textile printing method, dyeing can be carried out by a commonly used method, such as a method using sodium alginate, urea, a reduction inhibitor, and an acid binder. In addition, various dyeing methods used for vinylsulfonyl-type water-soluble reactive dyes, such as the padding method and the pad steam method, can be applied.

なお1本願発明の染料は非常に高い染着率を有しており
染色後の廃水処理の点において4有利である。一方堅牢
度面も非常に良好で近年問題となっている塩素堅牢度は
従来の黄色染料に比べ驚異的に高いレベルにあり、複合
堅牢度として問題になる汗−日光堅牢度も高く黄色系染
料としては非常に高い実用価値を有している。
Note that the dye of the present invention has a very high dyeing rate and is advantageous in terms of waste water treatment after dyeing. On the other hand, the fastness is also very good, and the fastness to chlorine, which has become a problem in recent years, is at an amazingly high level compared to conventional yellow dyes.The fastness to sweat and sunlight, which is a problem in terms of composite fastness, is also high and yellow dyes. It has extremely high practical value.

以下、本発明の方法を実施例によって具体的に説明する
が1本発明はその要旨を超えない限りこれらの実施例に
限定されるものではない。
Hereinafter, the method of the present invention will be specifically explained with reference to Examples, but the present invention is not limited to these Examples unless the gist thereof is exceeded.

実施例1 構造式 %式%) で示される染料0.3 fを水zoomに溶解し、芒硝
コθfを加え溶解して調製した染浴に綿布iztを浸漬
し30分を要してtoC迄昇温した。次いで炭酸ソーダ
a、r tを添加しjOCで/時間染色した後水洗、ン
ーピング、水洗、乾燥を行ない、黄色の染色物を得た。
Example 1 A cotton fabric izt was immersed in a dye bath prepared by dissolving 0.3 f of the dye represented by the structural formula (% formula %) in water zoom, and adding and dissolving mirabilite θf, and it took 30 minutes to reach toC. The temperature rose. Next, sodium carbonate a and rt were added and dyed with jOC for an hour, followed by washing with water, nooping, washing with water, and drying to obtain a yellow dyed product.

本染料の染着度は非常に高く得られ友染色物は極めて濃
厚であり耐場素堅牢ft1r級(J工8θ//4tK準
処し有効塩素20 ppm )と非常にすぐれ耐光堅牢
度、汗−日f堅牢度も良好であった。
The degree of dyeing of this dye is very high, and the dyed product is very thick, and has very good field fastness, FT1R class (20 ppm of available chlorine, subject to J-Tech 8θ//4tK), light fastness, and sweat-fastness. The weather fastness was also good.

なお、本実施例で使用した染料は 式 で示され!1モル割合と3−アミノベンゼンスルホン酸
1モル割合な水媒中30〜uOCで液性を炭酸ナトリウ
ムで中性に保ちつつ3時間攪拌し式 の染料とした後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モル割合ト水媒中9θ〜?j
17で液性を酢酸す) IJウムでpHす〜6に保ちつ
つ70時間攪拌した後塩化カリウムで塩析して得た。
The dye used in this example is shown by the formula! 1 molar ratio of 3-aminobenzenesulfonic acid and 1 molar ratio of 3-aminobenzenesulfonic acid in an aqueous medium with 30~uOC, stirring for 3 hours while keeping the liquid neutral with sodium carbonate to obtain a dye of the formula 3-(β-hydroxyethyl). 1 molar proportion of sulfonylaniline sulfate 9θ in aqueous medium? j
After stirring for 70 hours while keeping the pH at ~6 with IJum, the solution was salted out with potassium chloride.

実施例− 構造式 で示される染料を用いて下記の処決で綿布を捺染した。Example- Structural formula A cotton fabric was printed using the dye shown in the following procedure.

染 料                  コ、θを
尿  素                 to、θ
Vアルギン酸ソーダ         3.θ23−二
トロベンゼンスルホン酸ソーダ    θ、jfヘキサ
メタリン酸ソーダ         θ、jf重炭酸ソ
ーダ           1.O9水       
   残部 100、Of すなわち、上記組成の捺染糊を綿布に印捺しlθCで中
間乾燥後100Cで蒸熱処理次いで水洗、ソーピング、
水洗、乾燥を行なった。
Dye ko, θ to urea to, θ
V Sodium Alginate 3. θ23-Sodium nitrobenzenesulfonate θ, jf Sodium hexametaphosphate θ, jf Sodium bicarbonate 1. O9 water
The remaining portion was 100%. That is, the printing paste having the above composition was printed on a cotton cloth, and after intermediate drying at lθC, it was steamed at 100C, followed by washing with water, soaping,
Washed with water and dried.

ぞの結釆耐光堅牢度、湿潤堅牢1の良好な濃厚黄色の染
色物を得た、また本染色物の塩素堅牢度Viり縁(JI
B ogre寥に準拠し有効塩素λθppm )と非常
にすぐれていた。
A deep yellow dyed product with good light fastness and wet fastness of 1 was obtained, and the chlorine fastness of this dyed product was
The effective chlorine (λθppm) was very excellent in accordance with Bogre's standard.

なお1本実施例で使用した染料は 式 で示される染料1モル割合と愼−アミノベンゼンスルホ
ン酸7モル割合を水媒中30〜弘OCで液性を炭酸ナト
リウムで中性に保ちつつ3時間攪拌し式 の染料とした後 式 で示されるアミンlモル割合と水媒中90〜9すCで液
性を酢酸ナトリウムでpHす〜6に保ちつつ70時間攪
拌した稜均化カリウムで塩析して得た。
Note that the dye used in this example was a mixture of 1 mole of the dye shown by the formula and 7 moles of Shin-aminobenzenesulfonic acid in an aqueous medium of 30 to 50% OC for 3 hours while keeping the liquid property neutral with sodium carbonate. Stir to make a dye, then salt out with ridge-equalized potassium, which is stirred for 70 hours while keeping the pH at ~6 with sodium acetate at 90 to 9 C in an aqueous medium with the amine l molar ratio shown in the formula. I got it.

実施例3 実施例1に準じた方法で下配一般式 で示される染料を用いて綿布を染色した結果は下表の通
りである。
Example 3 The results of dyeing cotton cloth using the dye represented by the general formula below in the same manner as in Example 1 are shown in the table below.

Claims (1)

【特許請求の範囲】[Claims] (1)一般式 (式中、R1は水素、メチル基またはエチル基を表わし
R2およびR8は水素、メチル基、メトキシ基またはス
ルホン酸基を表わし、Xは水素、メチル基、メトキシ基
を九はエトキシ基を表わし、Yは水素、メチル基、アセ
チルアミノ基または塩素を表わし、2はスルホン酸基を
lケま九はコケ有する脂肪族または芳香族のアミノ残基
を表わす。) で示されるセルロース繊維類用反応性染料。
(1) General formula (wherein R1 represents hydrogen, methyl group or ethyl group; R2 and R8 represent hydrogen, methyl group, methoxy group or sulfonic acid group; X represents hydrogen, methyl group, methoxy group; 2 represents an ethoxy group, Y represents hydrogen, methyl group, acetylamino group, or chlorine, 2 represents a sulfonic acid group, and 9 represents an aliphatic or aromatic amino residue having moss.) Reactive dye for textiles.
JP57075855A 1982-05-06 1982-05-06 Reactive dyes for cellulose fibers Expired - Lifetime JPH0643562B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP57075855A JPH0643562B2 (en) 1982-05-06 1982-05-06 Reactive dyes for cellulose fibers

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP57075855A JPH0643562B2 (en) 1982-05-06 1982-05-06 Reactive dyes for cellulose fibers

Publications (2)

Publication Number Publication Date
JPS58191754A true JPS58191754A (en) 1983-11-09
JPH0643562B2 JPH0643562B2 (en) 1994-06-08

Family

ID=13588254

Family Applications (1)

Application Number Title Priority Date Filing Date
JP57075855A Expired - Lifetime JPH0643562B2 (en) 1982-05-06 1982-05-06 Reactive dyes for cellulose fibers

Country Status (1)

Country Link
JP (1) JPH0643562B2 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106049101A (en) * 2016-06-12 2016-10-26 青岛大学 Method for performing normal-temperature rapid dip dyeing on seaweed non-woven fabric and enhancing ultraviolet resistance

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106049101A (en) * 2016-06-12 2016-10-26 青岛大学 Method for performing normal-temperature rapid dip dyeing on seaweed non-woven fabric and enhancing ultraviolet resistance

Also Published As

Publication number Publication date
JPH0643562B2 (en) 1994-06-08

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