JPH07304974A - Azo dye - Google Patents
Azo dyeInfo
- Publication number
- JPH07304974A JPH07304974A JP6120560A JP12056094A JPH07304974A JP H07304974 A JPH07304974 A JP H07304974A JP 6120560 A JP6120560 A JP 6120560A JP 12056094 A JP12056094 A JP 12056094A JP H07304974 A JPH07304974 A JP H07304974A
- Authority
- JP
- Japan
- Prior art keywords
- group
- dye
- alkyl
- denier
- alkoxy
- 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
Links
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
- D06P1/18—Azo dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/40—Preparation of azo dyes from other azo compounds by substituting hetero atoms by radicals containing other hetero atoms
- C09B43/42—Preparation of azo dyes from other azo compounds by substituting hetero atoms by radicals containing other hetero atoms by substituting radicals containing hetero atoms for —CN radicals
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/52—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing synthetic macromolecular substances
- D06P1/56—Condensation products or precondensation products prepared with aldehydes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
- D06P3/54—Polyesters using dispersed dyestuffs
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、水不溶性の赤色乃至青
色系モノアゾ染料に関する。本発明は、特にポリエステ
ル極細繊維の染色に適した水不溶性のモノアゾ染料に関
する。又、本発明は０．３デニール以下のポリエステル
極細繊維を選択堅牢度及びアルカリ汗堅牢度に優れた赤
色乃至青色に染色することのできる水不溶性染料に関す
る。FIELD OF THE INVENTION The present invention relates to a water-insoluble red to blue monoazo dye. The present invention relates to a water-insoluble monoazo dye which is particularly suitable for dyeing polyester microfibers. The present invention also relates to a water-insoluble dye capable of dyeing a polyester ultrafine fiber having a denier of 0.3 denier or less with red or blue color having excellent selective fastness and fastness to alkaline sweat.
【０００２】[0002]
【従来の技術】近年、ポリエステル繊維の極細繊維の開
発が進み、０．３デニール以下といった極めて繊度の小
さい繊維も生産されている。ポリエステル繊維はその付
加価値を高めるため、種々の研究が進んでいるが、その
中で特に従来にない風合をもったポリエステル繊維製品
を製造する等の目的で繊維の極細化の研究が進んでい
る。2. Description of the Related Art In recent years, development of ultrafine fibers of polyester fibers has progressed, and fibers having an extremely small fineness of 0.3 denier or less have been produced. Various studies are underway to increase the added value of polyester fibers, but among them, research on ultrafine fibers has been advanced for the purpose of producing polyester fiber products with a texture that has never been seen before. There is.
【０００３】この極細繊維は様々の特性を備えた製品を
生み出しているが、一方において従来の染料で染色した
場合、洗濯堅牢度等の湿潤堅牢度が大幅に低下するとい
う問題が生じている。These ultrafine fibers have produced products having various characteristics, but on the other hand, when dyed with a conventional dye, there arises a problem that the wet fastness such as washing fastness is significantly lowered.
【０００４】[0004]
【発明が解決しようとする課題】本発明は良好な洗濯堅
牢度を有し、しかもアルカリ汗堅牢度及び耐光堅牢度を
有する赤色乃至青色系分散染料を提供することを目的と
するものである。SUMMARY OF THE INVENTION It is an object of the present invention to provide a red to blue disperse dye having good washing fastness, alkaline sweat fastness and light fastness.
【０００５】[0005]
【課題を解決するための手段】本発明は、下記一般式
〔Ｉ〕The present invention has the following general formula [I]:
【０００６】[0006]
【化２】 [Chemical 2]
【０００７】（式中、Ａはハロゲン原子、シアノ基、ニ
トロ基、Ｃ1 〜Ｃ2 アルキル基、Ｃ1〜Ｃ4 アルキルス
ルホニル基又はフェニルアゾ基を表わし、Ｘは水素原
子、ハロゲン原子、水酸基、メチル基又はＮＨＺ基（こ
こでＺはＣ1 〜Ｃ4 アルキルスルホニル基、フェニルス
ルホニル基、Ｃ1 〜Ｃ4 アルキルカルボニル基、Ｃ1 〜
Ｃ2 アルコキシＣ1 〜Ｃ2 アルキルカルボニル基、フェ
ニルカルボニル基又はアミノカルボニル基を表わす。）
を表わし、Ｙは水素原子、Ｃ1 〜Ｃ2 アルキル基又はＣ
1 〜Ｃ2 アルコキシ基を表わし、Ｒはフェニル基、フェ
ノキシ基又はベンジル基を表わす。）で示されるモノア
ゾ染料を要旨とするものである。(In the formula, A represents a halogen atom, a cyano group, a nitro group, a C 1 -C 2 alkyl group, a C 1 -C 4 alkylsulfonyl group or a phenylazo group, and X represents a hydrogen atom, a halogen atom, a hydroxyl group, Methyl group or NHZ group (where Z is a C 1 -C 4 alkylsulfonyl group, phenylsulfonyl group, C 1 -C 4 alkylcarbonyl group, C 1
C 2 alkoxy represents a C 1 -C 2 alkylcarbonyl group, a phenylcarbonyl group or an aminocarbonyl group. )
Represents a hydrogen atom, a C 1 -C 2 alkyl group or C
Represents 1 -C 2 alkoxy group, R represents a phenyl group, a phenoxy group or a benzyl group. ) Is the gist of a monoazo dye represented by.
【０００８】以下、本発明を詳細に説明する。前記一般
式〔Ｉ〕において、Ａ、Ｘ及びＹで表わされるハロゲン
原子としては塩素原子又は臭素原子が挙げられる。又Ａ
で表わされるＣ1 〜Ｃ4 アルキルスルホニル基としては
メチルスルホニル基、エチルスルホニル基、プロピルス
ルホニル基、ブチルスルホニル基が挙げられるが特にメ
チルスルホニル基が好ましい。又、Ａ及びＹで表わされ
るＣ1 〜Ｃ2 アルキル基としては、メチル基又はエチル
基が挙げられるが、特にメチル基が好ましい。The present invention will be described in detail below. In the general formula [I], the halogen atom represented by A, X and Y includes a chlorine atom or a bromine atom. See A
Examples of the C 1 -C 4 alkylsulfonyl group represented by include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, and a butylsulfonyl group, and a methylsulfonyl group is particularly preferable. Examples of the C 1 -C 2 alkyl group represented by A and Y include a methyl group and an ethyl group, and a methyl group is particularly preferable.
【０００９】又、Ｘで表わされるＮＨＺ基のＺとしての
Ｃ1 〜Ｃ4 アルキルスルホニル基としては、メチルスル
ホニル基、エチルスルホニル基、ｎ−プロピルスルホニ
ル基、ｉ−プロピルスルホニル基、ｎ−ブチルスルホニ
ル基、ｓｅｃ−ブチルスルホニル基等のＣ1 〜Ｃ4 の直
鎖状又は分岐鎖状のアルキルスルホニル基が挙げられ
る。又、Ｃ1 〜Ｃ4 アルキルカルボニル基としては、メ
チルカルボニル基、エチルカルボニル基、ｎ−プロピル
カルボニル基、ｉ−プロピルカルボニル基、ｎ−ブチル
カルボニル基、ｉ−ブチルカルボニル基等の直鎖状又は
分岐鎖状のアルキルカルボニル基が挙げられる。The C 1 -C 4 alkylsulfonyl group as Z of the NHZ group represented by X is a methylsulfonyl group, ethylsulfonyl group, n-propylsulfonyl group, i-propylsulfonyl group, n-butylsulfonyl group. Group, and a C 1 to C 4 straight-chain or branched-chain alkylsulfonyl group such as a sec-butylsulfonyl group. The C 1 -C 4 alkylcarbonyl group may be a linear group such as methylcarbonyl group, ethylcarbonyl group, n-propylcarbonyl group, i-propylcarbonyl group, n-butylcarbonyl group, i-butylcarbonyl group or the like. A branched alkylcarbonyl group can be mentioned.
【００１０】特に好ましくはＣ1 〜Ｃ2 アルキルスルホ
ニル基及びＣ1 〜Ｃ2 アルキルカルボニル基が挙げられ
る。又、Ｚで表わされるＣ1 〜Ｃ2 アルコキシＣ1 〜Ｃ
2 アルキルカルボニル基としてはメトキシメチルカルボ
ニル基、エトキシメチルカルボニル基、メトキシエチル
カルボニル基、又は、エトキシエチルカルボニル基が挙
げられるが、特にメトキシメチルカルボニル基が好まし
い。Ｙで表わされるＣ1 〜Ｃ2 アルコキシ基としてはメ
トキシ基又はエトキシ基が挙げられる。Particularly preferably, a C 1 -C 2 alkylsulfonyl group and a C 1 -C 2 alkylcarbonyl group are mentioned. In addition, C 1 -C 2 alkoxy C 1 -C represented by Z
Examples of the 2- alkylcarbonyl group include a methoxymethylcarbonyl group, an ethoxymethylcarbonyl group, a methoxyethylcarbonyl group, and an ethoxyethylcarbonyl group, and a methoxymethylcarbonyl group is particularly preferable. Examples of the C 1 -C 2 alkoxy group represented by Y include a methoxy group and an ethoxy group.
【００１１】一般式〔Ｉ〕で示されるモノアゾ染料にお
いて、Ａがハロゲン原子、メチル基、ニトロ基又はフェ
ニルアゾ基を表わし、Ｘがメチル基、Ｃ1 〜Ｃ2 アルキ
ルカルボニルアミノ基、メトキシメチルカルボニルアミ
ノ基又はＣ1 〜Ｃ2 アルキルスルホニルアミノ基、Ｙが
水素原子、そしてＲがフェニル基である染料が特に好ま
しい。前記一般式〔Ｉ〕で示されるモノアゾ染料は例え
ば下記一般式〔II〕In the monoazo dye represented by the general formula [I], A represents a halogen atom, a methyl group, a nitro group or a phenylazo group, and X represents a methyl group, a C 1 -C 2 alkylcarbonylamino group or methoxymethylcarbonylamino. Particularly preferred are dyes having a radical or a C 1 -C 2 alkylsulphonylamino group, Y is a hydrogen atom and R is a phenyl group. The monoazo dye represented by the general formula [I] is, for example, the following general formula [II]
【００１２】[0012]
【化３】 [Chemical 3]
【００１３】（式中、Ａは前記定義と同じ意味を表わ
す。）で示されるアミン類を常法によってジアゾ化し、
次いで下記一般式〔III 〕(Wherein A represents the same meaning as defined above), the amines represented by the formula are diazotized by a conventional method,
Then the following general formula [III]
【００１４】[0014]
【化４】 [Chemical 4]
【００１５】（式中、Ｘ、ＹおよびＲは前記定義と同じ
意味を表わす。）で示されるアニリン類とカップリング
することにより下記一般式〔IV〕(Wherein X, Y and R have the same meanings as defined above) by coupling with an aniline represented by the following general formula [IV]
【００１６】[0016]
【化５】 [Chemical 5]
【００１７】で示される化合物を合成し、これを乾燥す
る。次いで、一般式〔IV〕で示される化合物を公知の方
法、例えば、特公昭４５−７８５号公報記載の方法に従
い臭素原子をシアノ基に置換することにより製造するこ
とができる。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、ポリブチ
レンテレフタレート、テレフタル酸と１，４−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
よりなるポリエステル繊維、ナイロン等のポリアミド系
繊維あるいは木綿、絹、羊毛などの天然繊維と上記ポリ
エステル繊維との混紡品、混編織品等の混合繊維製品が
挙げられる。The compound of formula (1) is synthesized and dried. Then, the compound represented by the general formula [IV] can be produced by substituting a bromine atom with a cyano group according to a known method, for example, the method described in JP-B-45-785. Fibers that can be dyed with the monoazo dye of the present invention include polyethylene terephthalate, polybutylene terephthalate, terephthalic acid and 1,4-bis-
Polyester fibers composed of a polycondensate with (hydroxymethyl) cyclohexane, polyamide fibers such as nylon, or natural fibers such as cotton, silk, and wool, and mixed fiber products of the above polyester fibers such as mixed knitted woven products Can be mentioned.
【００１８】ポリエステル繊維としては通常の繊度のレ
ギュラーデニール繊維、１デニール以下のファインデニ
ール繊維、更に、０．３デニール以下のウルトラマイク
ロファイバーと呼ばれる極細繊維も良好に染色できる繊
維として挙げられる。本発明の染料を用いて染色を実施
するにあたっては、常法により、分散剤を使用し、前記
一般式〔Ｉ〕で示されるモノアゾ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
を行なえばよい。Examples of the polyester fibers include regular denier fibers having a normal fineness, fine denier fibers having a denier of 1 denier or less, and ultrafine fibers having an denier of 0.3 denier or less, which are called ultramicrofibers, can be well dyed. In carrying out dyeing with the dye of the present invention, a dispersant is used by a conventional method to disperse the monoazo dye represented by the general formula [I] in an aqueous medium to prepare a dyeing bath or a printing paste. However, it may be dyed or printed.
【００１９】例えば、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
いしはその混紡品、混織品に堅牢度のすぐれた染色を施
すことができる。また、場合により、染色浴に酸性物質
を添加しておくことにより、さらに好結果が得られるこ
とがある。For example, in the case of dyeing, by applying a usual dyeing treatment method such as a high temperature dyeing method, a carrier dyeing method and a thermosol dyeing method, the polyester fiber or its blended fabric and blended fabric have excellent fastness. Can be dyed. Further, depending on the case, better results may be obtained by adding an acidic substance to the dyeing bath.
【００２０】本発明のモノアゾ染料を用いて上記の浸染
または捺染により得られた染布は、洗濯堅牢度に優れ、
また、耐アルカリ汗堅牢度、耐光堅牢度、耐昇華堅牢
度、及び耐水堅牢度等の諸堅牢度に優れたものである。
更に、この染布に後加工を施した場合でも、本発明では
湿潤堅牢度が大幅に低下すると言うことはない。なお、
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い。The dyed cloth obtained by the above-mentioned dip dyeing or printing using the monoazo dye of the present invention has excellent fastness to washing,
Further, it is excellent in various fastnesses such as alkali sweat fastness, light fastness, sublimation fastness, and water fastness.
Further, even when the dyed cloth is post-processed, the wet fastness is not significantly lowered in the present invention. In addition,
The monoazo dye of the present invention may be used in combination with a dye of the same system or a dye of another system.
【００２１】[0021]
【実施例】次に、本発明を実施例により更に具体的に説
明するが、本発明は、その要旨を越えない限り以下の実
施例に限定されるものではない。 実施例１EXAMPLES Next, the present invention will be described more specifically by way of examples, but the present invention is not limited to the following examples unless it exceeds the gist. Example 1
【００２２】[0022]
【化６】 [Chemical 6]
【００２３】上記構造式で表わされるモノアゾ染料０．
０２５ｇを、ナフタレンスルホン酸−ホルムアルデヒド
縮合物０．０２５ｇ及び高級アルコール硫酸エステル
０．０２５ｇを含む水２００ｍｌ中に分散させ染色浴を
調製した。この染色浴に、繊径が２デニールと０．０１
デニールのポリエステル繊維の交織布１０ｇを浸漬し、
１３５℃で３０分間染色した後、ソーピング、水洗およ
び乾燥を行なったところ、異デニール間で同色性と同濃
度性の良好な鮮明な赤色の染布が得られた。なお、上記
の染料にて染色された上記、交織布の洗濯堅牢度は４+
級と優れたものであった。尚、洗濯堅牢度は、ＡＡＴＣ
Ｃ２Ａ法でのナイロン布の汚染度を判定した。尚、本実
施例で使用したモノアゾ染料は以下の方法に依り製造し
た。即ち、次の構造式Monoazo dye represented by the above structural formula:
025 g was dispersed in 200 ml of water containing 0.025 g of a naphthalenesulfonic acid-formaldehyde condensate and 0.025 g of a higher alcohol sulfate ester to prepare a dye bath. In this dyeing bath, the fiber diameter is 2 denier and 0.01
Immerse 10 g of denier polyester fiber interwoven cloth,
After dyeing at 135 ° C. for 30 minutes, soaping, washing with water and drying were carried out, and a clear red dyed cloth having good color and density with different denier was obtained. In addition, the washing fastness of the above-mentioned woven cloth dyed with the above dye is 4 +
It was a class and excellent. In addition, wash fastness is AATC
The stain degree of the nylon cloth by the C2A method was judged. The monoazo dye used in this example was produced by the following method. That is, the following structural formula
【００２４】[0024]
【化７】 [Chemical 7]
【００２５】で示される化合物を特公昭４５−７８５号
公報記載の方法に従って臭素原子をシアノ置換すること
により得た。該染料の最大吸収波長（λmax ：アセトン
中）は５９１ｎｍであった。 比較例１ ＵＳＰ．３９６２２０９号米国特許明細書コラム３９に
記載の下記構造式The compound of formula (1) was obtained by substituting the bromine atom with cyano according to the method described in JP-B-45-785. The maximum absorption wavelength (λ max : in acetone) of the dye was 591 nm. Comparative Example 1 USP. No. 3962209 The following structural formula described in US Pat.
【００２６】[0026]
【化８】 [Chemical 8]
【００２７】で示される染料を用いて実施例１に準じて
染色評価をしたところ、洗濯堅牢度は２級と劣るもので
あった。 実施例２〜４０ 実施例１に準じて表−１に記載の各染料を合成し、実施
例１と同様にしてウルトラマイクロファイバー交織布を
染色した。その結果、洗濯堅牢度は４+ 級以上あった。When the dyeing evaluation was carried out in accordance with Example 1 using the dye represented by the formula (1), the washing fastness was inferior to the second grade. Examples 2 to 40 The dyes shown in Table-1 were synthesized according to Example 1, and the ultra microfiber mixed woven fabric was dyed in the same manner as in Example 1. As a result, the washing fastness was 4 + or higher.
【００２８】[0028]
【表１】 [Table 1]
【００２９】[0029]
【表２】 [Table 2]
【００３０】[0030]
【表３】 [Table 3]
【００３１】[0031]
【表４】 [Table 4]
【００３２】[0032]
【発明の効果】本発明によればポリエステル繊維を諸堅
牢度に優れた赤色乃至青色に染色することのできる水不
溶性染料を提供することができる。更に本発明に係る染
料はポリエステル極細繊維、特に０．３デニール以下の
超極細繊維を通常の繊度の繊維と全く同様に洗濯堅牢度
及びアルカリ汗堅牢度に優れた赤色乃至青色に染色する
ことができるものである。According to the present invention, it is possible to provide a water-insoluble dye capable of dyeing polyester fibers in red or blue with excellent fastness. Further, the dye according to the present invention is capable of dyeing polyester ultrafine fibers, especially ultrafine fibers having a denier of 0.3 denier or less, in red to blue excellent in washing fastness and alkaline sweat fastness just like fibers of ordinary fineness. It is possible.
Claims (3)
〜Ｃ2 アルキル基、Ｃ1〜Ｃ4 アルキルスルホニル基又
はフェニルアゾ基を表わし、Ｘは水素原子、ハロゲン原
子、水酸基、メチル基又はＮＨＺ基（ここでＺはＣ1 〜
Ｃ4 アルキルスルホニル基、フェニルスルホニル基、Ｃ
1 〜Ｃ4 アルキルカルボニル基、Ｃ1 〜Ｃ2 アルコキシ
Ｃ1 〜Ｃ2 アルキルカルボニル基、フェニルカルボニル
基又はアミノカルボニル基を表わす。）を表わし、Ｙは
水素原子、Ｃ1 〜Ｃ2 アルキル基又はＣ1 〜Ｃ2 アルコ
キシ基を表わし、Ｒはフェニル基、フェノキシ基又はベ
ンジル基を表わす。）にて示されるアゾ染料。1. The following general formula [I]: (In the formula, A is a halogen atom, a nitro group, a cyano group, C 1
To C 2 alkyl group, C 1 to C 4 alkylsulfonyl group or phenylazo group, X is a hydrogen atom, a halogen atom, a hydroxyl group, a methyl group or an NHZ group (where Z is C 1 to C 1
C 4 alkylsulfonyl group, phenylsulfonyl group, C
1 -C 4 alkylcarbonyl group, C 1 -C 2 alkoxy C 1 -C 2 alkylcarbonyl group, a phenylcarbonyl group or an aminocarbonyl group. ), Y represents a hydrogen atom, a C 1 -C 2 alkyl group or a C 1 -C 2 alkoxy group, and R represents a phenyl group, a phenoxy group or a benzyl group. ) Azo dyes represented by.
ン原子、メチル基、ニトロ基又はフェニルアゾ基であ
り、Ｘがメチル基、Ｃ1 〜Ｃ2 アルキルスルホニルアミ
ノ基、メトキシメチルカルボニルアミノ基、Ｃ1 〜Ｃ2
アルキルカルボニルアミノ基であり、Ｙが水素原子であ
り、Ｒがフェニル基であるアゾ染料。2. In the general formula [I], A is a halogen atom, a methyl group, a nitro group or a phenylazo group, X is a methyl group, a C 1 -C 2 alkylsulfonylamino group, a methoxymethylcarbonylamino group, C 1 to C 2
An azo dye which is an alkylcarbonylamino group, Y is a hydrogen atom and R is a phenyl group.
０．３デニール以下のポリエステル極細繊維の染色法。3. A method for dyeing polyester ultrafine fibers having a denier of 0.3 or less using the azo dye according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6120560A JPH07304974A (en) | 1994-05-10 | 1994-05-10 | Azo dye |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6120560A JPH07304974A (en) | 1994-05-10 | 1994-05-10 | Azo dye |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH07304974A true JPH07304974A (en) | 1995-11-21 |
Family
ID=14789338
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6120560A Pending JPH07304974A (en) | 1994-05-10 | 1994-05-10 | Azo dye |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH07304974A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007040079A1 (en) * | 2005-09-30 | 2007-04-12 | Yamamoto Chemicals, Inc. | Novel azo compound |
| CN106543771A (en) * | 2016-10-11 | 2017-03-29 | 扬州日兴生物科技股份有限公司 | The special compounding dispersive red dye of dacron ultrafine fiber |
-
1994
- 1994-05-10 JP JP6120560A patent/JPH07304974A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007040079A1 (en) * | 2005-09-30 | 2007-04-12 | Yamamoto Chemicals, Inc. | Novel azo compound |
| JP5172345B2 (en) * | 2005-09-30 | 2013-03-27 | 山本化成株式会社 | New azo compounds |
| CN106543771A (en) * | 2016-10-11 | 2017-03-29 | 扬州日兴生物科技股份有限公司 | The special compounding dispersive red dye of dacron ultrafine fiber |
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