JPS58171450A - Monoazo dye for polyester fiber - Google Patents

Monoazo dye for polyester fiber

Info

Publication number
JPS58171450A
JPS58171450A JP57054501A JP5450182A JPS58171450A JP S58171450 A JPS58171450 A JP S58171450A JP 57054501 A JP57054501 A JP 57054501A JP 5450182 A JP5450182 A JP 5450182A JP S58171450 A JPS58171450 A JP S58171450A
Authority
JP
Japan
Prior art keywords
dye
formula
methoxy
compound
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.)
Pending
Application number
JP57054501A
Other languages
Japanese (ja)
Inventor
Toshio Niwa
俊夫 丹羽
Kiyoshi Himeno
清 姫野
Junji Yoshihara
潤二 吉原
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 JP57054501A priority Critical patent/JPS58171450A/en
Publication of JPS58171450A publication Critical patent/JPS58171450A/en
Pending legal-status Critical Current

Links

Abstract

NEW MATERIAL:The compound of formula I (Z is H or Cl; X is H, Cl, methyl or methoxy; Y is methyl, OH or methoxy; R is lower alkyl). EXAMPLE:The compound of formula II. USE:A dye having excellent resistance to alkali discharging, and capable of dyeing a polyester fiber such as polyethylene terrephthalate fiber or its blend with cotton, silk, wool, etc., in reddish blue - greenish blue color having excellent fastness to light, sublimation and water. PROCESS:The objective compound is prepared by diazotizing the amine of formula III and coupling with the compound of formula IV [e.g. N,N-bis(ethoxycarbonyloxyethyl)-2-methoxy-5-methylaniline].

Description

【発明の詳細な説明】 本発明はポリエステル繊維用モノアゾ染料に関するもの
であり、詳しくはポリエステル繊維を諸堅牢変1%に耐
光竪牢度、耐昇華堅牢度、水竪牢度にすCれた赤味背色
から緑味青色に染色するアルカリ防抜染性にすぐれたモ
ノアゾ染料に関するものである。
DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a monoazo dye for polyester fibers, and more specifically, the present invention relates to a monoazo dye for polyester fibers. This invention relates to a monoazo dye with excellent alkali discharge resistance that dyes from a reddish background color to a greenish blue color.

本発明に係る染料は、下記一般式(1)(式中、2は水
素原子または塩素原子を表わし、Xは水素原子、塩素原
子、メチル基またはメトキシ基を表わし、Yはメチル基
、ヒドロキシル基またはメトキシ基を表わし、lは低級
アルキル基を表わす。)で示されるポリエステに繊維用
水不溶性モノアゾ染料である。
The dye according to the present invention has the following general formula (1) (wherein 2 represents a hydrogen atom or a chlorine atom, X represents a hydrogen atom, a chlorine atom, a methyl group, or a methoxy group, and Y represents a methyl group or a hydroxyl group. or a methoxy group, and l represents a lower alkyl group) is a water-insoluble monoazo dye for polyester fibers.

前示一般式(1)で示されるモノアゾ染料は下記式(1
) (式中、2は前記定義に同じ)で示されるアミン類をジ
アゾ化し、下記式(1) で示される化合物とカップリングさせることにより、製
造することができる。〔l3式で示されるカップリング
成分としては。
The monoazo dye represented by the general formula (1) shown above is represented by the following formula (1).
) (wherein 2 is the same as defined above) can be produced by diazotizing an amine represented by the formula (2) and coupling it with a compound represented by the following formula (1). [As a coupling component represented by the formula l3.

N、N−ビス(エトキシカルボニルオキシエチル)−コ
ーメトキシー3−メチルアニリン N、N−ヒス(エトキシカルボニルオキシエチル)−一
、j−ジメトキシアニリン N、N−ビス(エトキシカルボニルオキシエチル)−一
、!−ジメチルアニリン N、N−ビス(エトキシカルボニルオキシエチル゛)−
一−ヒドロキシー!−クロロアニリンN、N−ビス(エ
トキシカルボニルオキシエテル)−2−メトキシ−!−
クロロアニIJ 7N、N−ビス(エトキシカルボニル
オキシエチル)−1−メトキシアニリン 等が挙げられる。
N,N-bis(ethoxycarbonyloxyethyl)-comethoxy-3-methylaniline N,N-his(ethoxycarbonyloxyethyl)-1,j-dimethoxyaniline N,N-bis(ethoxycarbonyloxyethyl)-1,! -dimethylaniline N,N-bis(ethoxycarbonyloxyethyl)-
-Hydroxy! -Chloroaniline N,N-bis(ethoxycarbonyloxyether)-2-methoxy-! −
Examples include Chloroani IJ 7N, N-bis(ethoxycarbonyloxyethyl)-1-methoxyaniline, and the like.

本発明のモノアゾ染料により染色し得る繊維類としては
、ポリエチレンテレフタレート、テレフタルIll/、
$−ビス−(ヒドロキシメチル)シクロヘキサンとの重
゛縮合物などよりな庫−ポリ混繊品が挙げられる。
Fibers that can be dyed with the monoazo dye of the present invention include polyethylene terephthalate, terephthal Ill/,
Examples include polycondensate products such as polycondensates with $-bis-(hydroxymethyl)cyclohexane.

本発明の染料を用いてポリエステル酸mを染色するKは
、常法により、ナフタレンスルホン酸とホルムアルデヒ
ドとの縮合物、高級アルコール硫酸ニスデル、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、#示一
般式〔1〕で示される染料を水性媒体中に分散させて染
色浴または捺染糊を調製し、浸染または捺染な行なえば
よい、たとえば、浸染を行なう場合には、高温、染色法
、キャリヤー染色法、サーモゾル染色法などの通常の染
色処理法を適用することにより、、ポリエステル繊維な
いしはその混紡、混繊品に堅牢度のすぐれた染色を施こ
すことができる。また、場合により、染色浴に蟻酸、酢
酸、燐酸あるいは硫酸アンモニウムなどの酸性物質を添
加しておくことKより、さらに好結果が得られることが
ある。
K, which dyes polyester acid m using the dye of the present invention, is dyed using a dispersant such as a condensate of naphthalene sulfonic acid and formaldehyde, higher alcohol Nisdel sulfate, or higher alkylbenzene sulfonate. Dyeing or printing may be carried out by dispersing the dye represented by the general formula [1] in an aqueous medium to prepare a dyeing bath or printing paste.For example, in the case of dyeing, high temperature, dyeing method, carrier dyeing By applying ordinary dyeing methods such as dyeing methods and thermosol dyeing methods, it is possible to dye polyester fibers or their blends and mixed fiber products with excellent fastness. In some cases, even better results may be obtained by adding an acidic substance such as formic acid, acetic acid, phosphoric acid or ammonium sulfate to the dyeing bath.

本発明のモノアゾ染料は同系統の染料あるいは他系統の
染料と併用してもよく、特に岐示一般式白〕で示される
染料相互の配合により染色性の向上等、好結果が得られ
ることがある。
The monoazo dye of the present invention may be used in combination with dyes of the same type or dyes of other types, and in particular, good results such as improved dyeability can be obtained by combining the dyes represented by the general formula ``White'' with each other. be.

次に本発明を実権例により更に具体的に説明する。Next, the present invention will be explained in more detail with reference to actual examples.

実施例1 下記構造式 て示される染料Q!fをナフタレンスルホン酸−ホルム
アルデヒド縮合、物/)およヒ高級アルコール硫酸エス
テルコtを含む水JjK分・散させて染色浴を調製した
。この染色浴にポリエステル繊維100fを浸漬し、/
30C−’C40分間染色した後、ソーピンク、水洗、
乾燥を行なったとこう、鮮明な青色の染布が得られた。
Example 1 Dye Q! represented by the following structural formula. A dyeing bath was prepared by dispersing f in water containing naphthalene sulfonic acid-formaldehyde condensation, product/) and higher alcohol sulfate ester. 100f of polyester fibers are immersed in this dyeing bath,
30C-'C After dyeing for 40 minutes, so pink, washed with water,
After drying, a vivid blue dyed fabric was obtained.

得られた染布の耐光堅牢度、耐昇華堅牢I!および水堅
牢度は良好であった。
The light fastness and sublimation fastness of the dyed fabric obtained are I! and water fastness was good.

本実輪例で使用した染料は下記のようにして製造した。The dye used in this fruit ring example was produced as follows.

−一アミノーl−ニトロテアソール17fをリン酸1l
−1酢酸ltwtK溶解し、−3℃でダコ憾ニトロシル
硫酸を用いてジアゾ化し、得られたジアゾニウム塩溶液
をN、N−ビス(エトキシカルボニルオキシエチル)−
コーメトキシー5−メチルアニリン2ユl?をメタノー
ル2!0w5tlC溶解した溶液中に0℃で添加し、析
出した染料を濾取、水洗乾燥した0本品のλwax  
(アセトン)は40711rm  であった。
-17f of monoamino-l-nitrotheasole in 1l of phosphoric acid
-1 acetic acid ltwtK was dissolved and diazotized using nitrosyl sulfuric acid at -3°C, and the resulting diazonium salt solution was N,N-bis(ethoxycarbonyloxyethyl)-
Comethoxy 5-methylaniline 2 liters? was added to a solution of 2!0w5tlC in methanol at 0°C, the precipitated dye was collected by filtration, washed with water and dried.
(acetone) was 40711 rm.

実権例コ で示される染料anfPをナフタレンスルホン酸−ホル
ムアルデヒド縮合物JtThよび水ダtと混合し、サン
ドグラインダーで10時間磨砕して得た染料分散液およ
びキャリヤー(メイプリンター!−一!(商標)、明成
化学■製)JPを捺桑糊90fK混入し色糊を調製した
A dye dispersion obtained by mixing the dye anfP shown in Example 1 with naphthalene sulfonic acid-formaldehyde condensate JtTh and water dat and grinding the mixture with a sand grinder for 10 hours and a carrier (May Printer!-1! (trademark) ), Meisei Kagaku ■) JP was mixed with 90 fK of mulberry paste to prepare colored paste.

この色糊をポリエステル繊維材料に印捺し、l0DCで
2分間中間乾燥後、ttocで7分間蒸熱し、染料を固
着させ、ンーピング、水洗および乾燥処理を行なったと
ころ、耐光竪牢変および耐昇華堅牢度の良好な鮮明な青
色の染布が得られた。
This color paste was printed on a polyester fiber material, and after intermediate drying at 10DC for 2 minutes, it was steamed at TTOC for 7 minutes to fix the dye, and after being subjected to looming, water washing and drying treatment, it was found to be light resistant and sublimation resistant. A dyed cloth of clear blue color with good strength was obtained.

本品のλ1x(アセトン)はA / ! amであった
The λ1x (acetone) of this product is A/! It was am.

実施例J 下記構造式 で示される染料を使用し、実施例1と同様にポリエステ
ル繊維を染色したところ、鮮明な青色の染布か得られた
。得られた染布の耐光堅牢喫、耐昇華堅牢度、水堅牢度
は良好であった。
Example J When a polyester fiber was dyed in the same manner as in Example 1 using a dye represented by the following structural formula, a vivid blue dyed fabric was obtained. The dyed fabric obtained had good light fastness, sublimation fastness, and water fastness.

本実施例で使用した染料は実施例1に準じて製造した1
本品のλm&X (アセトン)はgosam  であっ
た。
The dye used in this example was 1 produced according to Example 1.
The λm&X (acetone) of this product was gosam.

実施例亭 実施例1と同様の方法により下記表に示した染料を用い
てポリエステル繊維を染色し、同表に示す色調の染色物
を得た。
EXAMPLE-TEI Polyester fibers were dyed using the dyes shown in the table below in the same manner as in Example 1 to obtain dyed products having the colors shown in the table.

Claims (1)

【特許請求の範囲】[Claims] (1)一般式 (式中、2は水素原子または塩素原子を表わし、Xは水
素原子、塩素原子、メチル基またはメトキシ基を表わし
、Yはメチル基、ヒドロキシル基またはメトキシ基を表
わし、11低級アルキル基を表わす、)で示されるポリ
エステル繊維用モノアゾ染料。
(1) General formula (wherein 2 represents a hydrogen atom or a chlorine atom, X represents a hydrogen atom, a chlorine atom, a methyl group or a methoxy group, Y represents a methyl group, a hydroxyl group or a methoxy group, 11 lower A monoazo dye for polyester fibers represented by ), which represents an alkyl group.
JP57054501A 1982-04-01 1982-04-01 Monoazo dye for polyester fiber Pending JPS58171450A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP57054501A JPS58171450A (en) 1982-04-01 1982-04-01 Monoazo dye for polyester fiber

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP57054501A JPS58171450A (en) 1982-04-01 1982-04-01 Monoazo dye for polyester fiber

Publications (1)

Publication Number Publication Date
JPS58171450A true JPS58171450A (en) 1983-10-08

Family

ID=12972374

Family Applications (1)

Application Number Title Priority Date Filing Date
JP57054501A Pending JPS58171450A (en) 1982-04-01 1982-04-01 Monoazo dye for polyester fiber

Country Status (1)

Country Link
JP (1) JPS58171450A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61246259A (en) * 1985-04-25 1986-11-01 Gosei Senriyou Gijutsu Kenkyu Kumiai Monoazo compound and dyeing method using same
KR19980072793A (en) * 1997-03-07 1998-11-05 성재갑 Heteroazo dye composition for dyeing

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61246259A (en) * 1985-04-25 1986-11-01 Gosei Senriyou Gijutsu Kenkyu Kumiai Monoazo compound and dyeing method using same
KR19980072793A (en) * 1997-03-07 1998-11-05 성재갑 Heteroazo dye composition for dyeing

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