JPH032910B2 - - Google Patents
Info
- Publication number
- JPH032910B2 JPH032910B2 JP56010690A JP1069081A JPH032910B2 JP H032910 B2 JPH032910 B2 JP H032910B2 JP 56010690 A JP56010690 A JP 56010690A JP 1069081 A JP1069081 A JP 1069081A JP H032910 B2 JPH032910 B2 JP H032910B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- dye
- lower alkyl
- dyeing
- 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.)
- Expired - Lifetime
Links
- -1 tetrahydrofurfuryl group Chemical group 0.000 claims description 25
- 239000000835 fiber Substances 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 229920000728 polyester Polymers 0.000 claims description 16
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000004442 acylamino group Chemical group 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 239000000975 dye Substances 0.000 description 36
- 238000004043 dyeing Methods 0.000 description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 239000004744 fabric Substances 0.000 description 14
- 238000000034 method Methods 0.000 description 9
- 238000000859 sublimation Methods 0.000 description 8
- 230000008022 sublimation Effects 0.000 description 8
- 238000001035 drying Methods 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- AHSWGWIUVXBWEE-UHFFFAOYSA-N (diazonioamino)benzene Chemical class N#[N+]NC1=CC=CC=C1 AHSWGWIUVXBWEE-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- WYRNRZQRKCXPLA-UHFFFAOYSA-N 3-(n-ethylanilino)propanenitrile Chemical compound N#CCCN(CC)C1=CC=CC=C1 WYRNRZQRKCXPLA-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000006226 butoxyethyl group Chemical group 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007796 conventional method Methods 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
- 239000002270 dispersing agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000006627 ethoxycarbonylamino group Chemical group 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 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
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- DGGJQLCAYQCPDD-UHFFFAOYSA-N methyl 2-aminothiophene-3-carboxylate Chemical compound COC(=O)C=1C=CSC=1N DGGJQLCAYQCPDD-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- GLQWRXYOTXRDNH-UHFFFAOYSA-N thiophen-2-amine Chemical compound NC1=CC=CS1 GLQWRXYOTXRDNH-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Landscapes
- Coloring (AREA)
Description
本発明はポリエステル繊維用ジスアゾ染料に関
するものであり、詳しくはポリエステル繊維を鮮
明な赤味青色から青色に染色し、諸堅牢度、特に
耐光堅牢度、耐昇華堅牢度、水堅牢度、また染色
時の温度安定性およびPH安定性にすぐれたジスア
ゾ染料に関するものである。
本発明のポリエステル繊維用ジスアゾ染料は、
下記一般式〔Ｉ〕
（式中、Ｘは水素原子、塩素原子、臭素原子、メ
チル基またはアシルアミノ基を表わし、Ｙは水素
原子、メチル基またはメトキシ基を表わし、R1
およびR2は水素原子；非置換の低級アルキル
基；シアノ基、ヒドロキシル基、低級アルコキシ
基、低級アルコキシカルボニルオキシ基、低級ア
ルキルカルボニルオキシ基、低級アルコキシカル
ボニル基、フエノキシ基、クロル低級アルキルカ
ルボニルオキシ基もしくはアリルオキシカルボニ
ル基で置換された低級アルキル基；シクロヘキシ
ル基またはベンジル基を表わし、R3は低級アル
キル基、アルケニル基またはテトラヒドロフルフ
リル基を表わす。）で示される。
前示一般式〔Ｉ〕においてＸで表わされるアシ
ルアミノ基としてはアセチルアミノ基、クロロア
セチルアミノ基、ベンゾイルアミノ基、メチルス
ルホニルアミノ基、クロロプロピオニルアミノ
基、エトキシカルボニルアミノ基、エチルアミノ
カルボニルアミノ基等が挙げられる。R1および
R2としては水素原子；メチル基、エチル基、直
鎖状または分岐鎖状のプロピル基、ブチル基等の
非置換の低級アルキル基；メトキシエチル基、エ
トキシエチル基、ブトキシエチル基等の低級アル
コキシ低級アルキル基；フエノキシエチル基等の
フエノキシ低級アルキル基；ヒドロキシエチル
基、ヒドロキシプロピル基、ヒドロキシブチル
基、ヒドロキシヘキシル基、２−ヒドロキシ−３
−メトキシプロピル基等のヒドロキシアルキル
基、シアノメチル基、シアノエチル基等のシアノ
低級アルキル基；アセチルオキシエチル基等の低
級アルキルカルボニルオキシ低級アルキル基；メ
トキシカルボニルオキシエチル基等の低級アルコ
キシカルボニルオキシ低級アルキル基；メトキシ
カルボニルメチル基、エトキシカルボニルメチル
基等のアルコキシカルボニル低級アルキル基；ク
ロロプロピオニルオキシエチル基等のクロル低級
アルキルカルボニルオキシ低級アルキル基；アリ
ルオキシカルボニルエチル基、アリルオキシカル
ボニルメチル基等のアリルオキシカルボニル低級
アルキル基；シクロヘキシル基；ベンジル基等が
挙げられる。
R3で表わされる低級アルキル基としてはメチ
ル基、エチル基、直鎖状または分岐鎖状のプロピ
ル基、ブチル基等が挙げられ、アルケニル基とし
てはアリル基、２−メチルアリル基、クロチル基
等が挙げられる。
前示一般式〔Ｉ〕で示されるジスアゾ染料はア
ニリンをジアゾ化し下記式〔〕
（式中、R3は前記定義に同じ。）で示されるアミ
ノチオフエン類とカツプリングさせ、得られた下
記式〔〕
（式中、R3は前記定義に同じ。）で示されるモノ
アゾ化合物をジアゾ化し、下記一般式〔〕
（式中、Ｘ、Ｙ、R1およびR2は前記定義に同
じ。）で示されるアニリン類とカツプリングさせ
ることによつて製造することができる。
本発明のジスアゾ染料により染色しうる繊維と
しては、ポリエ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、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、混織品が挙げ
られる。
本発明の染料を用いてポリエステル繊維を染色
するには、前示一般式〔Ｉ〕で示される染料が水
に不溶ないし難溶であるので、常法により、分散
剤として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エステル、高
級アルキルベンゼンスルホン酸塩などを使用して
水性媒質中に分散させた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。例えば浸
染の場合、高温染色法、キヤリヤー染色法、サー
モゾル染色法などの通常の染色処理法を適用すれ
ば、ポリエステル繊維ないしは、その混紡品に堅
牢度のすぐれた染色を施すことができる。その
際、場合により、染色浴にギ酸、酢酸、リン酸あ
るいは硫酸アンモニウムなどのような酸性物質を
添加すれば、さらに好結果が得られる。
また、本発明方法に使用される前示一般式
〔Ｉ〕で示される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、このうち前示一般
式〔Ｉ〕で示される染料相互の配合により染色性
の向上等、好結果が得られる場合がある。
次に、本発明を実施例によつて更に具体的に説
明するが、本発明はその要旨を超えない限り以下
の実施例に限定されるものではない。
実施例 １
下記構造式
で示される染料0.5gをナフタレンスルホン酸−ホ
ルムアルデヒド縮合物1gおよび高級アルコール
硫酸エステル2gを含む水３に分散させた染色
浴にポリエステル繊維100gを浸漬し、130℃で60
分間染色した後、ソーピング、水洗および乾燥を
行なつたところ、鮮明な赤味青色の染布が得られ
た。得られた染布の耐光堅牢度、昇華堅牢度およ
び水堅牢度、ならびに上記染料の染色時の温度安
定性およびPH安定性は良好であつた。
本実施例で使用した染料は下記のようにして製
造した。
アニリン9.3gを７％塩酸150ml中に溶解し、こ
の溶液を２℃に冷却し、ついで2N−亜硝酸ソー
ダ50mlを加えた。この時、温度は５℃を超えない
ようにした。得られたアニリンのジアゾニウム塩
溶液を２−アミノ−３−メトキシカルボニルチオ
フエン15.7gをメタノール200mlに溶解した溶液中
に２℃にて添加して同温度で２時間撹拌し、析出
したモノアゾ化合物を取後、水洗して乾燥し
た。このモノアゾ化合物（２−アミノ−３−メト
キシカルボニル−５−（３−フエニルアゾ）チオ
フエン）13.5gを酢酸135mlおよびりん酸135mlの
混合物中に加え、ついでこの混合物中に０〜５℃
でニトロシル硫酸（亜硝酸ソーダ3.5gを97％硫酸
20gに溶解して調製）を徐々に加え、同温度で30
分撹拌して、モノアゾ化合物のジアゾ液を調製し
た。
Ｎ−（エチル）−Ｎ−（β−シアノエチル）アニ
リン8.7gをメタノール200mlに溶解し、氷200gと
水100ml中に添加した。これにさきに調製したジ
アゾ液を加え、０〜５℃で２時間撹拌し、析出し
たジスアゾ染料を取後、水洗して乾燥した。本
品のλmax（アセトン）は585nmであつた。
実施例 ２
下記構造式
で示される染料0.5gを用いて実施例１に記載した
方法により染色浴を調製した。この染色浴にポリ
エステル繊維100gを浸漬し、130℃で60分間染色
した後、ソーピング、水洗および乾燥を行なつた
ところ、鮮明な青色の染布が得られた。
得られた染布の耐光堅牢度、昇華堅牢度および
水堅牢度ならびに上記染料の染色時の温度安定
性、PH安定性は良好であつた。
本実施例で使用した染料は実施例１に準じて製
造した。本品のλmax（アセトン）は600nmであ
つた。
実施例 ３
下記構造式
で示される染料0.5gを用いて実施例１に記載した
方法により染色浴を調製した。この染色浴にポリ
エステル繊維100gを浸漬し、130℃で60分間染色
した後、ソーピング、水洗および乾燥を行なつた
ところ、鮮明な赤味青色の染布が得られた。
得られた染布の耐光堅牢度、昇華堅牢度および
水堅牢度ならびに上記染料の染色時の温度安定
性、PH安定性は良好であつた。
本実施例で使用した染料は実施例１に準じて製
造した。本品のλmax（アセトン）は585nmであ
つた。
実施例 ４
下記構造式
で示される染料0.5gを用いて実施例１に記載した
方法により染色浴を調製した。この染色浴にポリ
エステル繊維100gを浸漬し、130℃で60分間染色
した後、ソーピング、水洗および乾燥を行なつた
ところ、鮮明な青色の染布が得られた。
得られた染布の耐光堅牢度、昇華堅牢度および
水堅牢度ならびに上記染料の染色時の温度安定
性、PH安定性は良好であつた。
本実施例で使用した染料は実施例１に準じて製
造した。本品のλnax（アセトン）は625nmであつ
た。
実施例 ５
下記構造式
で示される染料0.5gを用いて実施例１に記載した
方法により染色浴を調製した。この染色浴にポリ
エステル繊維100gを浸漬し、130℃で60分間染色
した後、ソーピング、水洗および乾燥を行なつた
ところ、鮮明な青色の染布が得られた。
得られた染布の耐光堅牢度、昇華堅牢度および
水堅牢度ならびに上記染料の染色時の温度安定
性、PH安定性は良好であつた。
本実施例で使用した染料は実施例１に準じて製
造した。本品のλnax（アセトン）は620nmであつ
た。
実施例 ６
下記構造式
で示される染料0.5gを用いて実施例１に記載した
方法により染色浴を調製した。この染色浴にポリ
エステル繊維100gを浸漬し、130℃で60分間染色
した後、ソーピング、水洗および乾燥を行なつた
ところ、鮮明な赤味青色の染布が得られた。
得られた染布の耐光堅牢度、昇華堅牢度および
水堅牢度ならびに上記染料の染色時の温度安定
性、PH安定性は良好であつた。
本実施例で使用した染料は実施例１に準じて製
造した。本品のλnax（アセトン）は595nmであつ
た。
実施例 ７
下記構造式
で示される染料0.5gを用いて実施例１に記載した
方法により染色浴を調製した。この染色浴にポリ
エステル繊維100gを浸漬し、130℃で60分間染色
した後、ソーピング、水洗および乾燥を行なつた
ところ、鮮明な赤味青色の染布が得られた。
得られた染布の耐光堅牢度、昇華堅牢度および
水堅牢度ならびに上記染料の染色時の温度安定
性、PH安定性は良好であつた。
本実施例で使用した染料は実施例１に準じて製
造した。本品のλnax（アセトン）は585nmであつ
た。
実施例 ８
実施例１と同様の方法により下記表−１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。
The present invention relates to disazo dyes for polyester fibers, and more specifically, it dyes polyester fibers from vivid reddish blue to blue, and improves various fastnesses, particularly light fastness, sublimation fastness, water fastness, and dyeing process. This invention relates to a disazo dye with excellent temperature stability and PH stability. The disazo dye for polyester fibers of the present invention is
General formula [I] below (In the formula, X represents a hydrogen atom, chlorine atom, bromine atom, methyl group or acylamino group, Y represents a hydrogen atom, methyl group or methoxy group, and R 1
and R 2 is a hydrogen atom; unsubstituted lower alkyl group; cyano group, hydroxyl group, lower alkoxy group, lower alkoxycarbonyloxy group, lower alkylcarbonyloxy group, lower alkoxycarbonyl group, phenoxy group, chlorolower alkylcarbonyloxy group or a lower alkyl group substituted with an allyloxycarbonyl group; a cyclohexyl group or a benzyl group, and R 3 represents a lower alkyl group, an alkenyl group, or a tetrahydrofurfuryl group. ). Examples of the acylamino group represented by X in the general formula [I] include acetylamino group, chloroacetylamino group, benzoylamino group, methylsulfonylamino group, chloropropionylamino group, ethoxycarbonylamino group, ethylaminocarbonylamino group, etc. can be mentioned. R 1 and
R 2 is a hydrogen atom; an unsubstituted lower alkyl group such as a methyl group, an ethyl group, a linear or branched propyl group, a butyl group; a lower alkoxy group such as a methoxyethyl group, an ethoxyethyl group, a butoxyethyl group, etc. Lower alkyl group; phenoxy lower alkyl group such as phenoxyethyl group; hydroxyethyl group, hydroxypropyl group, hydroxybutyl group, hydroxyhexyl group, 2-hydroxy-3
-Hydroxyalkyl groups such as methoxypropyl groups; cyano lower alkyl groups such as cyanomethyl groups and cyanoethyl groups; lower alkylcarbonyloxy lower alkyl groups such as acetyloxyethyl groups; lower alkoxycarbonyloxy lower alkyl groups such as methoxycarbonyloxyethyl groups. ; Alkoxycarbonyl lower alkyl groups such as methoxycarbonylmethyl group and ethoxycarbonylmethyl group; Chlor lower alkylcarbonyloxy lower alkyl group such as chloropropionyloxyethyl group; Allyloxycarbonyl group such as allyloxycarbonylethyl group and allyloxycarbonylmethyl group Examples include lower alkyl group; cyclohexyl group; benzyl group. Examples of the lower alkyl group represented by R 3 include methyl group, ethyl group, linear or branched propyl group, butyl group, etc., and alkenyl groups include allyl group, 2-methylallyl group, crotyl group, etc. Can be mentioned. The disazo dye represented by the above general formula [I] can be obtained by diazotizing aniline to form the following formula [] (In the formula, R 3 is the same as defined above.) Coupled with an aminothiophene represented by the following formula [] (In the formula, R 3 is the same as defined above.) is diazotized, and the following general formula [] It can be produced by coupling with an aniline represented by the formula (wherein, X, Y, R 1 and R 2 are the same as defined above). Fibers that can be dyed with the disazo dye of the present invention include polyester fibers made of polyethylene terephthalate, polycondensates of terephthalic acid and 1,4-bis(hydroxymethyl)cyclohexane, and natural fibers such as cotton, silk, and wool. Examples include blended products and blended products with the above-mentioned polyester fibers. In order to dye polyester fibers using the dye of the present invention, naphthalene sulfonic acid and formaldehyde are used as dispersants by a conventional method, since the dye represented by the general formula [I] shown above is insoluble or sparingly soluble in water. Dyeing or printing may be carried out by preparing a dyeing bath or printing paste in which a condensate of , higher alcohol sulfuric ester, higher alkylbenzene sulfonate, etc. is dispersed in an aqueous medium. For example, in the case of dip dyeing, polyester fibers or their blends can be dyed with excellent fastness by applying ordinary dyeing methods such as high temperature dyeing, carrier dyeing, and thermosol dyeing. In this case, even better results can be obtained if an acidic substance such as formic acid, acetic acid, phosphoric acid or ammonium sulfate is added to the dyeing bath. Furthermore, the dye represented by the general formula [I] used in the method of the present invention may be used in combination with dyes of the same type or dyes of other types, and among these, the dye represented by the general formula [I] Good results, such as improved dyeing properties, may be obtained by combining them with each other. Next, the present invention will be explained in more detail with reference to examples, but the present invention is not limited to the following examples unless it exceeds the gist thereof. Example 1 The following structural formula 100 g of polyester fiber was immersed in a dyeing bath in which 0.5 g of the dye represented by was dispersed in 3 water containing 1 g of naphthalene sulfonic acid-formaldehyde condensate and 2 g of higher alcohol sulfate.
After dyeing for a few minutes, soaping, washing and drying yielded a vivid reddish-blue dyed fabric. The light fastness, sublimation fastness and water fastness of the obtained dyed fabric, as well as the temperature stability and PH stability during dyeing of the above dye, were good. The dye used in this example was produced as follows. 9.3 g of aniline was dissolved in 150 ml of 7% hydrochloric acid, the solution was cooled to 2 DEG C., and then 50 ml of 2N sodium nitrite was added. At this time, the temperature was kept not to exceed 5°C. The obtained aniline diazonium salt solution was added to a solution of 15.7 g of 2-amino-3-methoxycarbonylthiophene dissolved in 200 ml of methanol at 2°C and stirred at the same temperature for 2 hours to remove the precipitated monoazo compound. After taking it, it was washed with water and dried. 13.5 g of this monoazo compound (2-amino-3-methoxycarbonyl-5-(3-phenylazo)thiophene) was added to a mixture of 135 ml of acetic acid and 135 ml of phosphoric acid, and then added to the mixture at 0-5°C.
Nitrosyl sulfate (3.5 g of sodium nitrite in 97% sulfuric acid)
(Prepared by dissolving 20g of
The mixture was stirred for several minutes to prepare a diazo solution of a monoazo compound. 8.7 g of N-(ethyl)-N-(β-cyanoethyl)aniline was dissolved in 200 ml of methanol and added to 200 g of ice and 100 ml of water. The diazo solution prepared earlier was added to this, and the mixture was stirred at 0 to 5°C for 2 hours, and the precipitated disazo dye was removed, washed with water, and dried. The λmax (acetone) of this product was 585 nm. Example 2 Structural formula below A dyeing bath was prepared by the method described in Example 1 using 0.5 g of the dye shown. 100 g of polyester fibers were immersed in this dyeing bath and dyed at 130° C. for 60 minutes, followed by soaping, washing with water, and drying, resulting in a vivid blue dyed fabric. The light fastness, sublimation fastness and water fastness of the obtained dyed fabric, as well as the temperature stability and PH stability during dyeing of the above dye, were good. The dye used in this example was produced according to Example 1. The λmax (acetone) of this product was 600 nm. Example 3 Structural formula below A dyeing bath was prepared by the method described in Example 1 using 0.5 g of the dye shown. 100 g of polyester fibers were immersed in this dyeing bath and dyed at 130°C for 60 minutes, followed by soaping, washing with water, and drying, resulting in a dyed fabric with a vivid reddish blue color. The light fastness, sublimation fastness and water fastness of the obtained dyed fabric, as well as the temperature stability and PH stability during dyeing of the above dye, were good. The dye used in this example was produced according to Example 1. The λmax (acetone) of this product was 585 nm. Example 4 Structural formula below A dyeing bath was prepared by the method described in Example 1 using 0.5 g of the dye shown. 100 g of polyester fibers were immersed in this dyeing bath and dyed at 130° C. for 60 minutes, followed by soaping, washing with water, and drying, resulting in a vivid blue dyed fabric. The light fastness, sublimation fastness and water fastness of the obtained dyed fabric, as well as the temperature stability and PH stability during dyeing of the above dye, were good. The dye used in this example was produced according to Example 1. The λ nax (acetone) of this product was 625 nm. Example 5 Structural formula below A dyeing bath was prepared by the method described in Example 1 using 0.5 g of the dye shown. 100 g of polyester fibers were immersed in this dyeing bath and dyed at 130° C. for 60 minutes, followed by soaping, washing with water, and drying, resulting in a vivid blue dyed fabric. The light fastness, sublimation fastness and water fastness of the obtained dyed fabric, as well as the temperature stability and PH stability during dyeing of the above dye, were good. The dye used in this example was produced according to Example 1. The λ nax (acetone) of this product was 620 nm. Example 6 Structural formula below A dyeing bath was prepared by the method described in Example 1 using 0.5 g of the dye shown. 100 g of polyester fibers were immersed in this dyeing bath and dyed at 130° C. for 60 minutes, followed by soaping, washing with water, and drying, resulting in a vivid reddish-blue dyed fabric. The light fastness, sublimation fastness and water fastness of the obtained dyed fabric, as well as the temperature stability and PH stability during dyeing of the above dye, were good. The dye used in this example was produced according to Example 1. The λ nax (acetone) of this product was 595 nm. Example 7 Structural formula below A dyeing bath was prepared by the method described in Example 1 using 0.5 g of the dye shown. 100 g of polyester fibers were immersed in this dyeing bath and dyed at 130° C. for 60 minutes, followed by soaping, washing with water, and drying, resulting in a vivid reddish-blue dyed fabric. The light fastness, sublimation fastness and water fastness of the obtained dyed fabric, as well as the temperature stability and PH stability during dyeing of the above dye, were good. The dye used in this example was produced according to Example 1. The λ nax (acetone) of this product was 585 nm. Example 8 Polyester fibers were dyed using the dyes shown in Table 1 below in the same manner as in Example 1 to obtain dyed products having the colors shown in the table.
【表】【table】
【表】【table】
Claims (1)
チル基またはアシルアミノ基を表わし、Ｙは水素
原子、メチル基またはメトキシ基を表わし、R1
およびR2は水素原子；非置換の低級アルキル
基；シアノ基、ヒドロキシル基、低級アルコキシ
基、低級アルコキシカルボニルオキシ基、低級ア
ルキルカルボニルオキシ基、低級アルコキシカル
ボニル基、フエノキシ基、クロル低級アルキルカ
ルボニルオキシ基もしくはアリルオキシカルボニ
ル基で置換された低級アルキル基；シクロヘキシ
ル基またはベンジル基を表わし、R3は低級アル
キル基、アルケニル基またはテトラヒドロフルフ
リル基を表わす。）で示されるポリエステル繊維
用ジスアゾ染料。[Claims] 1. General formula (In the formula, X represents a hydrogen atom, chlorine atom, bromine atom, methyl group or acylamino group, Y represents a hydrogen atom, methyl group or methoxy group, and R 1
and R 2 is a hydrogen atom; unsubstituted lower alkyl group; cyano group, hydroxyl group, lower alkoxy group, lower alkoxycarbonyloxy group, lower alkylcarbonyloxy group, lower alkoxycarbonyl group, phenoxy group, chlorolower alkylcarbonyloxy group or a lower alkyl group substituted with an allyloxycarbonyl group; a cyclohexyl group or a benzyl group, and R 3 represents a lower alkyl group, an alkenyl group, or a tetrahydrofurfuryl group. ) Disazo dye for polyester fibers.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1069081A JPS57125262A (en) | 1981-01-27 | 1981-01-27 | Disazo dye for polyester fiber |
| GB8137778A GB2093056B (en) | 1980-12-26 | 1981-12-15 | Disazo dyestuffs and dyeing process |
| CH8258/81A CH647254A5 (en) | 1980-12-26 | 1981-12-23 | DISAZO DYES FOR POLYESTER FIBERS. |
| US06/334,005 US4621136A (en) | 1980-12-26 | 1981-12-23 | Phenyl azo cyanothienyl azo anilino dyestuffs |
| DE19813151114 DE3151114A1 (en) | 1980-12-26 | 1981-12-23 | DISAZO DYES FOR POLYESTER FIBERS |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1069081A JPS57125262A (en) | 1981-01-27 | 1981-01-27 | Disazo dye for polyester fiber |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57125262A JPS57125262A (en) | 1982-08-04 |
| JPH032910B2 true JPH032910B2 (en) | 1991-01-17 |
Family
ID=11757270
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1069081A Granted JPS57125262A (en) | 1980-12-26 | 1981-01-27 | Disazo dye for polyester fiber |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57125262A (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59142255A (en) * | 1983-02-03 | 1984-08-15 | Mitsubishi Chem Ind Ltd | Disazo dye for cellulose-containing fiber |
| JPS59145253A (en) * | 1983-02-04 | 1984-08-20 | Gosei Senriyou Gijutsu Kenkyu Kumiai | Disazo dye for polyester fiber |
| JPS59145254A (en) * | 1983-02-04 | 1984-08-20 | Gosei Senriyou Gijutsu Kenkyu Kumiai | Disazo dye for polyester fiber |
| KR20140026499A (en) | 2011-05-20 | 2014-03-05 | 미쓰비시 가가꾸 가부시키가이샤 | Azo compound and ink containing compound |
| CN104822780B (en) | 2012-11-28 | 2017-09-01 | 三菱化学株式会社 | Azo, the ink comprising Azo, the display comprising the ink and Electronic Paper |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2438496A1 (en) * | 1974-08-10 | 1976-02-26 | Bayer Ag | DISAZO DYES |
-
1981
- 1981-01-27 JP JP1069081A patent/JPS57125262A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2438496A1 (en) * | 1974-08-10 | 1976-02-26 | Bayer Ag | DISAZO DYES |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57125262A (en) | 1982-08-04 |
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