JPS58103560A - Monoazo dye for synthetic fiber - Google Patents

Monoazo dye for synthetic fiber

Info

Publication number
JPS58103560A
JPS58103560A JP20118381A JP20118381A JPS58103560A JP S58103560 A JPS58103560 A JP S58103560A JP 20118381 A JP20118381 A JP 20118381A JP 20118381 A JP20118381 A JP 20118381A JP S58103560 A JPS58103560 A JP S58103560A
Authority
JP
Japan
Prior art keywords
group
monoazo dye
dyeing
dye
synthetic fiber
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
JP20118381A
Other languages
Japanese (ja)
Other versions
JPH0124180B2 (en
Inventor
Toshio Niwa
俊夫 丹羽
Kiyoshi Himeno
清 姫野
Hiroshi Takimoto
滝本 浩
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.)
GOSEI SENRIYOU GIJUTSU KENKYU KUMIAI
Original Assignee
GOSEI SENRIYOU GIJUTSU KENKYU KUMIAI
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 GOSEI SENRIYOU GIJUTSU KENKYU KUMIAI filed Critical GOSEI SENRIYOU GIJUTSU KENKYU KUMIAI
Priority to JP20118381A priority Critical patent/JPS58103560A/en
Publication of JPS58103560A publication Critical patent/JPS58103560A/en
Publication of JPH0124180B2 publication Critical patent/JPH0124180B2/ja
Granted legal-status Critical Current

Links

Abstract

NEW MATERIAL:An azo compd. of formulaI(where R' is a 5-8C alkyl group or a 5-8C alkoxyethyl group; R<2> is a cyanoalkyl (1-3C) group, a 1-4C alkoxycarbonylmethyl group or a 1-4C alkoxyethoxycarbonylmethyl group; X is H, methyl group, acetylamino group or Cl). USE:The monoazo dye is used for dip dyeing and printing of polyester fiber, etc. in bright blue to green colors. PREPARATION:Diazonium salt of 2-amino-3,5-dinitrothiophene is coupled with aniline of formula II (e.g. N-hexyl-N-(beta-cyanoethyl)-m-toluidine).

Description

【発明の詳細な説明】 本発明は合成繊維用モノアゾ染料に関するものである※
詳しくは、本発明は、合成繊維類性れ、かつ鮮明な青色
ないし緑色−染色するアゾ染料に関するものである〇 以下に本発明の詳細な説明する。
[Detailed Description of the Invention] The present invention relates to a monoazo dye for synthetic fibers*
Specifically, the present invention relates to an azo dye that dyes synthetic fibers with a vivid blue to green color.The present invention will be described in detail below.

本発明に係号染料は、下記一般式(13(式中、Iは0
.、、アルキル基または0.、、、アルツキクエテル基
を表わし、IはシアノO3−1アル午ルa、’J−4フ
ルコキシカルボニルメチル基tえハ’s−iアルコキシ
エトキシカルボニルメチル基を表わし、Iは水素原子、
メチル基、アセチルア宿〕基または塩素原子を表わす口
)で示されh**fNkoy′*″71°  え 前示一般式〔1〕に示される染料は壷−ア擢ノー J、
!−シェド薗チオフェンのジアゾニウム塩を下記一般式
(13 X (式中W、!およびIは前記定義に同じ)で示されるア
ニリン類とカップリングさせることによ*S+を造され
る・ 曽示一般式(1)で示されるアニリン類の具体例として
は菖−へキシル−1−(l−シアノエチル)−4−)ル
イジン、舅−へ中シルー菖−(r−シアツブ閤ビル)ア
ニリン、J ” 741 ?ルアミノ−夏−へ命シルー
1−シアノメチル7品リン、夏−(/−へキシルオキシ
エチル)−舅−(l−シアノエチル)−US−)ルイジ
ン、舅−オクチル−■−(メト命ジカルボニル/?ル)
アニリン、1−へブチル−罵−(ブトキシカルボニルメ
チル)−重一トルイシン、J−アセチルアンノー夏−へ
キシル−菖−(工1?’/カルボニルメチル)アニリン
、菫−へキシル−夏−(β−メトキシエトキシ)カルボ
具ルメチルー朧−トルイジン、葺−(J−エテルヘキシ
#)−1−(/−エトキシエトキシ)カルボ具ルメチル
アニリン、M−(β−へブチルオキシzfル)−M−(
メトキシカルボニル/?ル)−膳−トルイジン等が挙げ
られる・ 本発明の染料によ)染色し得る合成繊維類としては、ポ
リエステル、ポリエステルエーテル、ボリア々ド、ポリ
フレ1フ60合成高分子物質よシなる繊維、トリアセテ
ート、ジアセテート勢O牛合成高分子物質よ〕なる繊維
、あるいはこれらO合成繊維相互の混紡品まえは木綿、
絹、羊(S勢の天然繊維との混紡品が挙げられるが、4
1にポリエチレンテレフタレート、テレフタル酸と1.
参−ビス−(ヒト四キシメチル)シフ買へ命サンとの重
縮合物勢のポリエステルよシなる繊維が好ましい◎ 本発明の染料によ)前記合成繊111kmを染色するK
は、前示一般式[1]で示される染料を常法にヨ〕す7
タレンスルホン酸とホルムアルデヒド゛とO縮合物、高
級アルコ−kll@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、水性媒質中に分散させ
て染色浴まえは捺染湖をIII製し、浸染まえは捺染を
行なえばよい・たとえば浸染を行なう鳩舎には、高温染
色法、キャリヤー染色法、ナー七ゾル染色法などの通常
の染色処理法を適用するととによ)、前記舎成繊艙類K
li率度のすぐれた染色を施ζすことができる。まえ鳩
舎によ〉染色浴に蟻酸、酢酸、リン酸あるいは硫酸7ノ
4二りムなどの酸性物質を添加しておくことくよp、さ
らに好結果が得られゐこと7fihゐ・ 次に本発明を実施例によ如さらに^体的に説明する・ 実施例I 下記構造式 で表わされゐ篭ノアゾ染料0.1 jをす7タレンスル
ホン駿−ホルムアルデヒド縮合物/lおよび高級アルー
−ル硫酸エステkJllを含む水JtK分散させて染色
浴を調製し九〇 この染色浴にポリエステル繊維1009を浸漬し、/J
O℃で60分間染色した後、ソーピング、水洗および乾
燥を行なう木ところ、耐光塵牢度および昇華騒牢度の良
好な鮮明實色に染色されえポリエステル布がllれた。
The dye related to the present invention has the following general formula (13 (wherein I is 0
.. , , alkyl group or 0. , , represents an alkoxy ether group, I represents a cyano O3-1 a, 'J-4 flukoxycarbonylmethyl group, and an alkoxyethoxycarbonylmethyl group, I represents a hydrogen atom,
A dye represented by a methyl group, an acetyl group, or a chlorine atom) and represented by the general formula [1] shown above is a dye represented by the above general formula [1].
! - *S+ is produced by coupling a diazonium salt of thiophene with an aniline represented by the following general formula (13 Specific examples of the anilines represented by the formula (1) include iris-hexyl-1-(l-cyanoethyl)-4-)luidine, iris-henakasilu-(r-cyanoethyl)aniline, and J'' 741 ?Ruamino-Natsu-Heme Sil-1-Cyanomethyl 7 items Phosphorus, Natsu-(/-hexyloxyethyl)-(l-cyanoethyl)-US-) Luidine, Sho-octyl-■-(metho-octyl-) carbonyl/?ru)
Aniline, 1-hebutyl-(butoxycarbonylmethyl)-toluicine, J-acetyl-hexyl-(1?'/carbonylmethyl)aniline, violet-hexyl-( β-methoxyethoxy)carboxylmethyl-oboro-toluidine, Fuki-(J-ethoxyethoxy#)-1-(/-ethoxyethoxy)carboxylmethylaniline, M-(β-hebutyloxyzfl)-M-(
Methoxycarbonyl/? Synthetic fibers that can be dyed with the dye of the present invention include fibers such as polyester, polyester ether, boriad, Polyfre 1F 60 synthetic polymer materials, and triacetate. , diacetate synthetic polymer material], or a blend of these synthetic fibers; cotton;
Silk, sheep (blended products with S type natural fibers are included, but 4
Polyethylene terephthalate, terephthalic acid and 1.
It is preferable to use a polyester fiber made of a polycondensate with bis-bis-(human tetraoxymethyl) Schiffer.
The dye represented by the general formula [1] shown above is used in a conventional manner7.
Using a dispersant such as talenesulfonic acid, formaldehyde and O condensate, higher alcohol kll@ester, higher alkylbenzene sulfonate, etc., it is dispersed in an aqueous medium to prepare a printing lake before dyeing. (For example, for pigeon houses that are dyed by dip dyeing, ordinary dyeing methods such as high-temperature dyeing, carrier dyeing, and nanosol dyeing can be applied.) K
Dyeing with excellent li ratio can be applied. For even better results, add an acidic substance such as formic acid, acetic acid, phosphoric acid or sulfuric acid to the dyeing bath in the pigeon coop. The invention will be explained more specifically with reference to examples. Example I A noazo dye represented by the following structural formula, 0.1 j, 7-talenesulfone-formaldehyde condensate/l, and a higher allyl. A dyeing bath was prepared by dispersing water JtK containing sulfuric acid ester KJll, and polyester fiber 1009 was immersed in this dyeing bath, /J
After dyeing at 0.degree. C. for 60 minutes, soaping, rinsing and drying the fabric, the polyester fabric was dyed in a bright true color with good light resistance and sublimation resistance.

本実施例で使用した染料は1−ア建ノーJ、j−m −
)ルイ5ジンとカップリングして製造しぇ・本品OJm
亀X(アセトン)は43亭n鳳で6つぇ。
The dyes used in this example were 1-a-denoJ, j-m-
) Manufactured by coupling with Louis 5 Gin - This product OJm
Turtle X (acetone) is 43 Tei n Otori and there are 6 of them.

実施例− 下記構造式 で表わされるモノ7ノ染料0.1 jをす7タレンスル
ホン讃−ホルムアルデヒド縮合物/、zlおよび高級ア
ルコールamエステル/It含む水Stは分散させ、こ
れにメチルナフタレy系中ヤリキー1177を加えて染
色浴を調製し九〇この染色浴にポリエステル繊1114
100gを浸漬し、100℃でto分間染色した後、ソ
ーピンク、水洗および乾燥を行なったとζろ、耐光胆牢
度および昇華竪牢度の良好な鮮明青色に染色されたポリ
エステル布が得られた。
Example - Mono-7 dye represented by the following structural formula 0.1j was dispersed in water containing 7talenesulfone-formaldehyde condensate/, zl and higher alcohol am ester/It, and dissolved in methylnaphthalene system. Prepare a dyeing bath by adding Yariky 1177 and add polyester fiber 1114 to this dyeing bath.
After immersing 100 g of the fabric and dyeing it at 100° C. for up to minutes, washing it with water and drying it, a polyester cloth dyed in vivid blue with good color resistance, light resistance, and sublimation stiffness was obtained.

本実f1例で使用した象科はコーア々ノーJ、j扁−エ
トキシカルボニルメチルアニリンとカップリングして製
造した。本品のλwax (アセトン)はA J J 
!1111でありN。
The polyester used in this Example F1 was produced by coupling it with Co-A-N-ethoxycarbonylmethylaniline. The λwax (acetone) of this product is A J J
! 1111 and N.

実施例J 下記構造式 で表わされるモノアゾ染料0.j jlを用い、実施例
1と同じ方法に従ってポリエステル繊維の染色を行なつ
えところ竪牢度が良好でかつ鮮明な青色に染色されたポ
リエステル布が得られた。
Example J Monoazo dye represented by the following structural formula 0. Polyester fibers were dyed using JJL in the same manner as in Example 1, and a polyester cloth having good firmness and being dyed in a clear blue color was obtained.

本実施例で使用した染料はコ、−アミノ−J、1−ジニ
ト交チオフエ°ンを常法に従ってジアゾ化t、、m−(
/−へブチルオキシエチル)−夏一メトキシカルボニル
メチルーm−トルイジンとカップリングさせて製造し九
〇 本品のλwax (アセトン)は、baonnであった
・ 実施例ダ〜/1 下記表−7に示すモノアゾ染料を用いて、実施例Iの方
法に従ってポリエステル繊維の染色を行なったところ同
表に示す色調Ω染布が得られ九〇
The dye used in this example was diazotized t,, m-(
/-hebutyloxyethyl)-Natsuichi methoxycarbonylmethyl-m-toluidine was produced by coupling with m-toluidine, and the λwax (acetone) of the 90 products was baonn.Example D~/1 Table 7 below Polyester fibers were dyed according to the method of Example I using the monoazo dye shown in Table 1, and a dyed fabric with the color tone Ω shown in the table was obtained.

Claims (1)

【特許請求の範囲】[Claims] (1)  一般式 (式中、!llはo11アル中ル基を良はONアル=キ
シエチル基t−表わし、tはシアノ01−47を表わし
、Xは水素原子、メチル基、アセチルア建)基または塩
素原子を表わす・)で示されゐ合威繊#IAJli帛毫
ノアゾ染料
(1) General formula (in the formula, !ll represents an o11 alkyl group, Ryo represents an ON alkoxyethyl group, t represents a cyano01-47, and X represents a hydrogen atom, a methyl group, an acetyl group) group, or #IAJli textile noazo dye indicated by ) representing a chlorine atom
JP20118381A 1981-12-14 1981-12-14 Monoazo dye for synthetic fiber Granted JPS58103560A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP20118381A JPS58103560A (en) 1981-12-14 1981-12-14 Monoazo dye for synthetic fiber

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP20118381A JPS58103560A (en) 1981-12-14 1981-12-14 Monoazo dye for synthetic fiber

Publications (2)

Publication Number Publication Date
JPS58103560A true JPS58103560A (en) 1983-06-20
JPH0124180B2 JPH0124180B2 (en) 1989-05-10

Family

ID=16436718

Family Applications (1)

Application Number Title Priority Date Filing Date
JP20118381A Granted JPS58103560A (en) 1981-12-14 1981-12-14 Monoazo dye for synthetic fiber

Country Status (1)

Country Link
JP (1) JPS58103560A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103602095A (en) * 2013-09-10 2014-02-26 江苏亚邦染料股份有限公司 Monoazo-type disperse dyes, preparation method thereof and applications thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103602095A (en) * 2013-09-10 2014-02-26 江苏亚邦染料股份有限公司 Monoazo-type disperse dyes, preparation method thereof and applications thereof
CN103602095B (en) * 2013-09-10 2016-04-20 江苏亚邦染料股份有限公司 One class Monoazo type dispersed dye, preparation method and application

Also Published As

Publication number Publication date
JPH0124180B2 (en) 1989-05-10

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