JPH07292265A - Thiophene monoazo dye - Google Patents
Thiophene monoazo dyeInfo
- Publication number
- JPH07292265A JPH07292265A JP6110448A JP11044894A JPH07292265A JP H07292265 A JPH07292265 A JP H07292265A JP 6110448 A JP6110448 A JP 6110448A JP 11044894 A JP11044894 A JP 11044894A JP H07292265 A JPH07292265 A JP H07292265A
- Authority
- JP
- Japan
- Prior art keywords
- group
- denier
- monoazo dye
- dye
- fastness
- 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
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 title abstract 2
- 229930192474 thiophene Natural products 0.000 title abstract 2
- 238000004043 dyeing Methods 0.000 claims abstract description 17
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 claims abstract description 15
- 125000005843 halogen group Chemical group 0.000 claims abstract description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 5
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims abstract description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 3
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims abstract description 3
- -1 methoxymethylcarbonylamino group Chemical group 0.000 claims description 10
- 229920001410 Microfiber Polymers 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 3
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 239000000835 fiber Substances 0.000 abstract description 26
- 229920000728 polyester Polymers 0.000 abstract description 16
- 238000005406 washing Methods 0.000 abstract description 10
- 239000000126 substance Substances 0.000 abstract description 7
- 210000004243 sweat Anatomy 0.000 abstract description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract description 2
- 239000000975 dye Substances 0.000 description 23
- 239000004744 fabric Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000986 disperse dye Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000003658 microfiber Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- XIZSUYSWKGAOCN-UHFFFAOYSA-N 2-amino-4-chloro-5-formylthiophene-3-carbonitrile Chemical compound NC=1SC(C=O)=C(Cl)C=1C#N XIZSUYSWKGAOCN-UHFFFAOYSA-N 0.000 description 1
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006126 n-butyl sulfonyl group Chemical group 0.000 description 1
- 125000006124 n-propyl sulfonyl group Chemical group 0.000 description 1
- 125000006252 n-propylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
Landscapes
- Coloring (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、水不溶性の赤紫乃至青
色系のモノアゾ染料に関する。特にポリエステル極細繊
維を洗濯堅牢及びアルカリ汗堅牢度に優れた赤紫色乃至
青色に染色することのできる分散染料に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a water-insoluble reddish purple to blue type monoazo dye. In particular, the present invention relates to a disperse dye capable of dyeing polyester ultrafine fibers in a reddish purple or blue color which is excellent in fastness to washing and alkaline sweat.
【０００２】[0002]
【従来の技術】近年のポリエステルの発展は著しい。ポ
リエステル繊維に種々の研究が加えられ、それを基に様
々の付加価値の高い繊維製品を生み出している。その中
で、ポリエステル繊維の風合をよくする等の目的で繊維
の極細化の研究が進み、１デニール以下、更に０．３デ
ニール以下の繊度の繊維も多量に生産され、特殊の風合
や特性を具えた繊維製品を生み出している。2. Description of the Related Art The recent development of polyester is remarkable. Various researches have been conducted on polyester fibers, and various high value-added textile products have been produced based on the research. Among them, research on ultrafine fiber has been advanced for the purpose of improving the texture of polyester fiber, and a large amount of fibers with a fineness of 1 denier or less, and 0.3 denier or less are produced. We produce textile products with unique characteristics.
【０００３】この一方でこれら極細ポリエステル繊維
は、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新たにおこってい
る。On the other hand, when these ultrafine polyester fibers are dyed with a conventional dye, there is a new problem that the wet fastness such as washing fastness is significantly reduced.
【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
を有する赤紫色乃至青色分散染料を提供することを目的
とするものである。特にポリエステル極細繊維を洗濯堅
牢度に優れ、アルカリ汗堅牢度良好な赤紫色乃至青色に
染色し得る分散染料を提供することを目的とする。SUMMARY OF THE INVENTION It is an object of the present invention to provide a reddish purple to blue disperse dye having good wash fastness, alkaline sweat fastness and light fastness. . In particular, it is an object of the present invention to provide a disperse dye capable of dyeing a polyester ultrafine fiber in reddish purple or blue which has excellent fastness to washing and good fastness to alkaline sweat.
【０００５】[0005]
【課題を解決するための手段】本発明の要旨は、下記一
般式〔Ｉ〕The gist of the present invention is to provide a compound represented by the following general formula [I]
【０００６】[0006]
【化２】 [Chemical 2]
【０００７】〔式中、Ｐはホルミル基、ニトロ基又はシ
アノ基を表わし、Ｑはシアノ基又はニトロ基を表わし、
Ｔはハロゲン原子、メチル基、フェニル基又はメチルス
ルホニル基を表わし、Ｘは水素原子、ハロゲン原子、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。〕にて示されるモ
ノアゾ染料にある。[In the formula, P represents a formyl group, a nitro group or a cyano group, and Q represents a cyano group or a nitro group,
T represents a halogen atom, a methyl group, a phenyl group or a methylsulfonyl group, and X represents a hydrogen atom, a halogen atom, a methyl group or an NHZ group (wherein Z is a C 1 -C 4 alkylsulfonyl group, a phenylsulfonyl group, C 1 to C 4 alkylcarbonyl group, C 1 to C 2 alkoxy represents a C 1 to C 2 alkylcarbonyl group, phenylcarbonyl group or aminocarbonyl group), and Y represents a hydrogen atom or a C 1 to C 2 alkoxy group. In the formula, R represents a phenyl group, a phenoxy group or a benzyl group. ] It is in the monoazo dye shown by.
【０００８】以下本発明を詳細に説明する。前記一般式
〔Ｉ〕に於て、Ｔ及びＸで表わされるハロゲン原子とし
ては、塩素原子または臭素原子が挙げられるが、特に塩
素原子が好ましい。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
ニル基及びｓｅｃ−ブチルスルホニル基で表わされる直
鎖状又は分岐鎖状アルキルスルホニル基が挙げられる。The present invention will be described in detail below. In the general formula [I], examples of the halogen atom represented by T and X include a chlorine atom and a bromine atom, and a chlorine atom is particularly preferable. The C 1 -C 4 alkylsulfonyl group as Z of the NHZ group represented by X includes a methylsulfonyl group, an ethylsulfonyl group, an n-propylsulfonyl group, an i-propylsulfonyl group, an n-butylsulfonyl group and sec-butyl. A straight chain or branched chain alkylsulfonyl group represented by a sulfonyl group can be mentioned.
【０００９】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、及びｉ−ブチルカルボニル基で
表わされるＣ1 〜Ｃ4 直鎖状又は分岐鎖状アルキルカル
ボニル基が挙げられる。中でも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特に好
ましい。As the C 1 -C 4 alkylcarbonyl group, a methylcarbonyl group, an ethylcarbonyl group, n-
Propylcarbonyl group, i-propylcarbonyl group, n
- butyl group, and C 1 -C 4 linear or branched alkyl group include represented by i- butyl group. Of these, a C 1 -C 2 alkylsulfonyl group and a C 1 -C 2 alkylcarbonyl group are particularly preferable.
【００１０】又、ＺとしてのＣ1 〜Ｃ2 アルコキシＣ1
〜Ｃ2 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
チルカルボニル基及びエトキシエチルカルボニル基が挙
げられる。中でも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、
メトキシ基及びエトキシ基が挙げられる。Also, C 1 -C 2 alkoxy C 1 as Z
Examples of the -C 2 alkylcarbonyl group include a methoxymethylcarbonyl group, an ethoxymethylcarbonyl group, a methoxyethylcarbonyl group and an ethoxyethylcarbonyl group. Of these, a methoxymethylcarbonyl group is preferable. As the C 1 -C 2 alkoxy group represented by Y,
A methoxy group and an ethoxy group are mentioned.
【００１１】一般式〔Ｉ〕で示されるモノアゾ染料の中
でも特にＸがＣ1 〜Ｃ2 アルキルカルボニルアミノ基又
はメトキシメチルカルボニルアミノ基、Ｙが水素原子、
Ｒがフェニル基、Ｐがホルミル基、Ｑがシアノ基そして
Ｔがハロゲン原子であるモノアゾ染料が好ましい。前記
一般式〔Ｉ〕で示される染料は、例えば下記一般式〔I
I〕Among the monoazo dyes represented by the general formula [I], X is a C 1 -C 2 alkylcarbonylamino group or a methoxymethylcarbonylamino group, Y is a hydrogen atom,
A monoazo dye in which R is a phenyl group, P is a formyl group, Q is a cyano group, and T is a halogen atom is preferable. The dye represented by the general formula [I] is, for example,
I]
【００１２】[0012]
【化３】 [Chemical 3]
【００１３】（式中、Ｐ，Ｑ及びＴは前記と同様の意義
を有する。）にて示されるアミン類を常法に従ってジア
ゾ化し、次いで下記一般式〔III 〕(Wherein P, Q and T have the same meanings as described above), the amines represented by the general formula [III] below are diazotized by a conventional method.
【００１４】[0014]
【化４】 [Chemical 4]
【００１５】（式中、Ｘ，Ｙ及びＲは前記と同様の意義
を有する。）にて示されるアニリン類とカップリングす
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、混織品
等の混合繊維製品が挙げられる。(Wherein X, Y and R have the same meanings as described above), and can be produced by coupling with an aniline. Fibers that can be dyed with the monoazo dye of the present invention include polyethylene terephthalate, polybutylene terephthalate, polyester fibers made of polycondensates of terephthalic acid and 1,4-bis- (hydroxymethyl) cyclohexane, polyamides such as nylon. Examples include mixed fiber products such as a mixed fiber product of a system fiber or a natural fiber such as cotton, silk and wool and the above polyester fiber, a mixed woven product and the like.
【００１６】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から、１デニール以下のファイ
ンデニールファイバーと呼ばれる繊維、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繊
維まで良好に染色し得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。As the polyester fiber, a fiber capable of satisfactorily dyeing from a regular denier fiber having a normal fineness to a fiber called fine denier fiber having a denier of 1 denier or less, and a fiber called ultra microfiber having a denier of 0.3 denier or less. Can be mentioned. 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.
【００１７】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 an ordinary 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.
【００１８】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.
【００１９】[0019]
【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
【００２０】[0020]
【化５】 [Chemical 5]
【００２１】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青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。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 blue dyed cloth having good homogeneity and same density between 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.
【００２２】尚、洗濯堅牢度は、ＡＡＴＣＣ２Ａ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。２−アミ
ノ−３−シアノ−４−クロル−５−ホルミルチオフエン
１．９ｇを氷酢酸／プロピオン酸（３：１）１５ｇ及び
８５％硫酸５．０ｇの混合物に添加し、これに０〜５℃
でニトロシル硫酸（４３％）３．２ｇを滴下する。次い
で０〜５℃で４時間攪拌する。The washing fastness was determined by determining the degree of stain of nylon cloth by the AATCC2A method. The monoazo dye used in this example was produced by the following method. 1.9 g of 2-amino-3-cyano-4-chloro-5-formylthiophene are added to a mixture of 15 g of glacial acetic acid / propionic acid (3: 1) and 5.0 g of 85% sulfuric acid, to which 0-5 are added. ℃
Then 3.2 g of nitrosylsulfuric acid (43%) is added dropwise. Then, the mixture is stirred at 0 to 5 ° C for 4 hours.
【００２３】残存する亜硝酸を破壊する為尿素を添加
し、これをＮ，Ｎ−ジベンゾイルオキシエチルアミノ−
ｍ−アセトアニリド４．５ｇをメタノール２００ｍｌに
溶解した溶液に０〜５℃で滴下し、２時間攪拌した後濾
別、水洗、乾燥し、目的とする染料を得た。該染料の最
大波長（λmax ：アセトン中）は５９０ｎｍであった。 比較例１ 特開昭６１−２６６４６６号公報 実施例６記載の下記
染料Urea was added to destroy the remaining nitrous acid, and this was added to N, N-dibenzoyloxyethylamino-
4.5 g of m-acetanilide was added dropwise to a solution prepared by dissolving 200 ml of methanol at 0 to 5 ° C., stirred for 2 hours, filtered, washed with water and dried to obtain a target dye. The maximum wavelength of the dye (λ max in acetone) was 590 nm. Comparative Example 1 JP-A No. 61-266466 The following dye described in Example 6
【００２４】[0024]
【化６】 [Chemical 6]
【００２５】についても実施例１に準じて染色評価をし
たところ、洗濯堅牢度は２−３級と劣るものであった。The dyeing evaluation was also carried out in accordance with Example 1, and the fastness to washing was inferior to 2-3 grade.
【００２６】実施例２〜２１ 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+ 以上あった。Examples 2 to 21 The dyes shown in Table 1 were synthesized according to Example 1, and the ultra microfiber woven fabric was dyed in the same manner as in Example 1. As a result, the wash fastness was 4 + or more.
【００２７】[0027]
【表１】 [Table 1]
【００２８】[0028]
【表２】 [Table 2]
【００２９】[0029]
【表３】 [Table 3]
【００３０】[0030]
【表４】 [Table 4]
【００３１】[0031]
【発明の効果】本発明は、諸堅牢性に優れた水不溶性モ
ノアゾ染料を提供するものであり、この染料を用いるこ
とによりポリエステル繊維、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同様に洗濯堅牢度、アル
カリ汗堅牢度及び耐光堅牢度に優れた赤紫色乃至青色に
染色することができる。INDUSTRIAL APPLICABILITY The present invention provides a water-insoluble monoazo dye which is excellent in various fastness properties. By using this dye, polyester fibers, especially ultrafine fibers having a denier of 0.3 denier or less can be obtained with ordinary fineness. Like fibers, it can be dyed in magenta or blue which is excellent in fastness to washing, fastness to alkali sweat and fastness to light.
Claims (3)
し、Ｑはシアノ基又はニトロ基を表わし、Ｔはハロゲン
原子、メチル基、フェニル基又はメチルスルホニル基を
表わし、Ｘは水素原子、ハロゲン原子、メチル基又はＮ
ＨＺ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。〕にて示されるモノアゾ染
料。1. The following general formula [I]: [Wherein P represents a formyl group, a nitro group or a cyano group, Q represents a cyano group or a nitro group, T represents a halogen atom, a methyl group, a phenyl group or a methylsulfonyl group, and X represents a hydrogen atom or a halogen atom. Atom, methyl group or N
HZ group (where Z is a 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, phenylcarbonyl group or amino Represents a carbonyl group), and Y is a hydrogen atom or C 1 -C 2
It represents an alkoxy group, and R represents a phenyl group, a phenoxy group or a benzyl group. ] The monoazo dye shown by these.
アルキルカルボニルアミノ基又はメトキシメチルカルボ
ニルアミノ基、Ｙが水素原子、Ｒがフェニル基、Ｐがホ
ルミル基、Ｑがシアノ基であり、Ｔがハロゲン原子であ
るモノアゾ染料。2. In the general formula [I], X is C 1 to C 2
A monoazo dye in which an alkylcarbonylamino group or a methoxymethylcarbonylamino group, Y is a hydrogen atom, R is a phenyl group, P is a formyl group, Q is a cyano group, and T is a halogen atom.
いる０．３デニール以下の極細繊維の染色法。3. A method for dyeing ultrafine fibers having a denier of 0.3 or less using the monoazo dye according to claim 1.
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6110448A JPH07292265A (en) | 1994-04-26 | 1994-04-26 | Thiophene monoazo dye |
| TW084101806A TW324021B (en) | 1994-03-08 | 1995-02-27 | Mono-azo dyestuff |
| EP95103258A EP0671440B1 (en) | 1994-03-08 | 1995-03-07 | Monoazo dyes |
| DE69510971T DE69510971T2 (en) | 1994-03-08 | 1995-03-07 | Monoazo dyes |
| ES95103258T ES2136754T3 (en) | 1994-03-08 | 1995-03-07 | MONOAZOIC DYES. |
| US08/399,660 US5527888A (en) | 1994-03-08 | 1995-03-07 | Thiophene-type monoazo dyes |
| KR1019950004740A KR100347978B1 (en) | 1994-03-08 | 1995-03-08 | Monoazo dyes |
| US08/594,487 US5608042A (en) | 1994-03-08 | 1996-01-31 | Benzothiazolemonoazo dyes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6110448A JPH07292265A (en) | 1994-04-26 | 1994-04-26 | Thiophene monoazo dye |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH07292265A true JPH07292265A (en) | 1995-11-07 |
Family
ID=14535981
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6110448A Pending JPH07292265A (en) | 1994-03-08 | 1994-04-26 | Thiophene monoazo dye |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH07292265A (en) |
-
1994
- 1994-04-26 JP JP6110448A patent/JPH07292265A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR100847236B1 (en) | Azo dyes, dye mixtures, methods for their preparation and dyeing or printing of hydrophobic fiber materials using them | |
| KR100347978B1 (en) | Monoazo dyes | |
| JPS6229463B2 (en) | ||
| JPH0860004A (en) | Monoazo dye, production thereof and method of using the same | |
| JP2001123083A (en) | Blue monoazo disperse dye | |
| JP3300158B2 (en) | Monoazo dye | |
| JPH07292265A (en) | Thiophene monoazo dye | |
| JPH07304973A (en) | Benzisothiazole monoazo dye | |
| JPH07292266A (en) | Monoazo dye | |
| JPS5853022B2 (en) | Manufacturing method of dispersible monoazo dye | |
| JPH0635550B2 (en) | Monoazo dye | |
| JPH07304974A (en) | Azo dye | |
| JPH07242834A (en) | Monoazo dye | |
| JP3335467B2 (en) | Monoazo dyes for polyester fiber dyeing | |
| JPH0134265B2 (en) | ||
| JPH0632989A (en) | Monoazo disperse dye and its mixture | |
| US3985726A (en) | Benzisothiazole and indazole azo compounds | |
| JPH07331099A (en) | Azo dye | |
| JPH045699B2 (en) | ||
| JP3006618B2 (en) | Monoazo dye | |
| JPS61281156A (en) | Water-insoluble monoazo compound and dyeing method using same | |
| JPS6232148A (en) | monoazo dye | |
| JPS58101157A (en) | Monoazo dye for synthetic fiber | |
| JPH07292267A (en) | Nitrobenzothiazole monoazo dye | |
| JPH0376349B2 (en) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20040629 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20041124 |