JPH0445541B2 - - Google Patents
Info
- Publication number
- JPH0445541B2 JPH0445541B2 JP58017207A JP1720783A JPH0445541B2 JP H0445541 B2 JPH0445541 B2 JP H0445541B2 JP 58017207 A JP58017207 A JP 58017207A JP 1720783 A JP1720783 A JP 1720783A JP H0445541 B2 JPH0445541 B2 JP H0445541B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- dye
- dyeing
- water
- 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
- 239000000835 fiber Substances 0.000 claims description 17
- 229920000728 polyester Polymers 0.000 claims description 14
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000005205 alkoxycarbonyloxyalkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims description 3
- 125000005197 alkyl carbonyloxy alkyl group Chemical group 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
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 2
- 239000000975 dye Substances 0.000 description 35
- 238000004043 dyeing Methods 0.000 description 24
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- -1 chloroacetylamino group Chemical group 0.000 description 17
- 239000004744 fabric Substances 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 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 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000000859 sublimation Methods 0.000 description 5
- 230000008022 sublimation Effects 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- XVGHZFWFGXDIOU-UHFFFAOYSA-N 2-aminothiophene-3-carbonitrile Chemical compound NC=1SC=CC=1C#N XVGHZFWFGXDIOU-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-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
- 235000011054 acetic acid Nutrition 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 235000010265 sodium sulphite 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
- 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
- 229920000742 Cotton Polymers 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
- 229920006221 acetate fiber Polymers 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000005236 alkanoylamino group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 1
- 125000004656 alkyl sulfonylamino group Chemical group 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
- 125000006226 butoxyethyl group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 229920006239 diacetate fiber Polymers 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 150000002148 esters Chemical class 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- VATYWCRQDJIRAI-UHFFFAOYSA-N p-aminobenzaldehyde Chemical compound NC1=CC=C(C=O)C=C1 VATYWCRQDJIRAI-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920006304 triacetate fiber Polymers 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
明な青色に染色し、諸堅牢度、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、
下記の一般式〔〕
（式中、Ｘはホルミル基またはチオシアナート
基を表わし、Ｙは水素原子、塩素原子、メチル基
またはアシルアミノ基を表わし、R1およびR2は
水素原子、アルキル基、アルコキシアルキル基、
フエノキシアルキル基、シアノアルキル基、アル
キルカルボニルオキシアルキル基、アルコキシカ
ルボニルアルキル基またはアルコキシカルボニル
オキシアルキル基を表わす。）
で示される新規な水不溶性のジスアゾ染料であ
る。
前記一般式〔〕においてＹ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
セチルアミノ基等の置換されていてもよいアルカ
ノイルアミノ基、メチルスルホニルアミノ基等の
アルキルスルホニルアミノ基などが挙げられ、
R1およびR2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、ペン
チル基、ヘキシル基、ヘプチル基、オクチル基等
のアルキル基；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アル
キル基；フエノキシエチル基等のフエノキシアル
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、
エチルカルボニ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等が挙げられる。
前示一般式〔〕で示されるジスアゾ染料は下
記式〔〕
（式中、Ｘ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〔〕
で示される２−アミノ−３−シアノチオフエンと
カツプリングさせ、得られた下記式〔〕
（式中、Ｘ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、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；ジアセテート繊維、トリアセテート繊維等の
アセテート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〔〕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
〔〕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〔〕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。
ｐ−ホルミルアニリン12.1ｇを７％塩酸150ml
中に溶解し、この溶液を２℃に冷却し、ついで
2N−亜硫酸ソーダ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−シアノ
チオフエン12.4ｇ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時間攪拌
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−
シアノ−５−（ｐ−ホルミルフエニルアゾ）チオ
フエン12.5ｇ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（亜硫酸ソーダ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
分攪拌して、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200
ｇ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時間攪拌し、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615nmであつた。
実施例 ２
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に分散させて染
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630nmであ
つた。
実施例 ３
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に分散させて染
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662nmであ
つた。
実施例 ４
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に分散させて染
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641nmであ
つた。
実施例 ５
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に分散させて染
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625nmであ
つた。
実施例 ６
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 a disazo dye for polyester fibers, and more specifically to a disazo dye that dyes polyester fibers in a bright blue color and has excellent color fastness, temperature stability, and pH stability during dyeing. The disazo dye for polyester fibers of the present invention is
General formula below [] (In the formula, X represents a formyl group or a thiocyanate group, Y represents a hydrogen atom, a chlorine atom, a methyl group, or an acylamino group, and R 1 and R 2 represent a hydrogen atom, an alkyl group, an alkoxyalkyl group,
It represents a phenoxyalkyl group, a cyanoalkyl group, an alkylcarbonyloxyalkyl group, an alkoxycarbonyloxyalkyl group, or an alkoxycarbonyloxyalkyl group. ) is a new water-insoluble disazo dye. The acylamino group represented by Y in the general formula [] includes an acetylamino group, an optionally substituted alkanoylamino group such as a chloroacetylamino group, an alkylsulfonylamino group such as a methylsulfonylamino group, and the like.
R 1 and R 2 are alkyl groups such as methyl group, ethyl group, linear or branched propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group; methoxyethyl group, ethoxyethyl group , lower alkoxyalkyl groups such as butoxyethyl group; phenoxyalkyl groups such as phenoxyethyl group; cyano lower alkyl groups such as cyanomethyl group and cyanoethyl group; acetyloxyethyl group,
Examples include lower alkylcarbonyloxy lower alkyl groups such as ethylcarbonyloxyethyl group; alkoxycarbonyloxy lower alkyl groups such as methoxycarbonyloxyethyl group; alkoxycarbonyl lower alkyl groups such as methoxycarbonylmethyl group and ethoxycarbonylmethyl group. The disazo dye represented by the above general formula [] is the following formula [] (wherein, X is the same as defined above) is diazotized to form the following formula [] The following formula obtained by coupling with 2-amino-3-cyanothiophene represented by [] (wherein, X is the same as defined above) is diazotized to form the following general formula [] (In the formula, Y, R 1 and R 2 are the same as defined above.)
It can be produced by coupling with an aniline represented by: 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. Fibers include blended products and blended woven products of acetate fibers such as diacetate fibers and triacetate fibers and the above polyester fibers. In order to dye polyester fibers using the dye of the present invention, since the dye represented by the general formula [] shown above is insoluble or sparingly soluble in water, naphthalene sulfonic acid and formaldehyde are used as dispersants in a conventional manner. Dyeing or printing may be carried out by preparing a dyeing bath or printing paste in which a condensate, higher alcohol sulfuric ester, higher alkylbenzene sulfonate, etc. are 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 [] used in the method of the present invention may be used in combination with dyes of the same type or dyes of other systems, and among these, the dyes represented by the general formula [] can be used in combination with each other. Depending on the combination, good results such as improved dyeability may be obtained. 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 0.5g of the dye shown in naphthalenesulfonic acid
100 g of polyester fiber was immersed in a dyeing bath containing 1 g of formaldehyde condensate and 2 g of higher alcohol sulfate ester dispersed in water, and heated at 130°C.
After dyeing for 60 minutes, soaping, washing and drying resulted 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 as follows. 12.1g of p-formylaniline and 150ml of 7% hydrochloric acid
This solution was cooled to 2°C and then
50 ml of 2N sodium sulfite 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 12.4 g of 2-amino-3-cyanothiophene dissolved in 200 ml of methanol at 2°C, stirred at the same temperature for 2 hours, and after removing the precipitated monoazo compound, Washed with water and dried. This monoazo compound 2-amino-3-
12.5 g of cyano-5-(p-formylphenylazo)thiophene was added to a mixture of 135 ml of acetic acid and 135 ml of phosphoric acid, and then 3.5 g of nitrosyl sulfate (3.5 g of sodium sulfite was added to 97% sulfuric acid) at 0-5°C.
(Prepared by dissolving 20g of
The mixture was stirred for several minutes to prepare a diazo solution of a monoazo compound. Dissolve 8.7 g of N-(ethyl)-N-(β-cyanoethyl)aniline in 200 ml of methanol and add 200 ml of ice.
g 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 615 nm. Example 2 Structural formula below 0.5g of the dye shown in naphthalenesulfonic acid
A dyeing bath was prepared by dispersing it in water 3 containing 1 g of formaldehyde condensate and 2 g of higher alcohol sulfate. Polyester fibers are dyed in this dye bath.
After immersing 100 g of the fabric and dyeing it at 130°C for 60 minutes, soaping, washing with water, and drying resulted 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 630 nm. Example 3 Structural formula below 0.5g of the dye shown in naphthalenesulfonic acid
A dyeing bath was prepared by dispersing it in water 3 containing 1 g of formaldehyde condensate and 2 g of higher alcohol sulfate. Polyester fibers are dyed in this dye bath.
After immersing 100 g of the fabric and dyeing it at 130°C for 60 minutes, soaping, washing with water, and drying resulted 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 662 nm. Example 4 Structural formula below 0.5g of the dye shown in naphthalenesulfonic acid
A dyeing bath was prepared by dispersing it in water 3 containing 1 g of formaldehyde condensate and 2 g of higher alcohol sulfate. Polyester fibers are dyed in this dye bath.
After immersing 100 g and dyeing at 130°C for 60 minutes, soaping, washing with water and drying, a bright reddish-blue dyed fabric was obtained. 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 641 nm. Example 5 Structural formula below 0.5g of the dye shown in naphthalenesulfonic acid
A dyeing bath was prepared by dispersing it in water 3 containing 1 g of formaldehyde condensate and 2 g of higher alcohol sulfate. Polyester fibers are dyed in this dye bath.
After immersing 100 g and dyeing at 130°C for 60 minutes, soaping, washing with water and drying, a bright reddish-blue dyed fabric was obtained. 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 625 nm. Example 6 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】
Claims (1)
基を表わし、Ｙは水素原子、塩素原子、メチル基
またはアシルアミノ基を表わし、R1およびR2は
水素原子、アルキル基、アルコキシアルキル基、
フエノキシアルキル基、シアノアルキル基、アル
キルカルボニルオキシアルキル基、アルコキシカ
ルボニルアルキル基またはアルコキシカルボニル
オキシアルキル基を表わす。） 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 formyl group or a thiocyanate group, Y represents a hydrogen atom, a chlorine atom, a methyl group, or an acylamino group, and R 1 and R 2 represent a hydrogen atom, an alkyl group, an alkoxyalkyl group,
It represents a phenoxyalkyl group, a cyanoalkyl group, an alkylcarbonyloxyalkyl group, an alkoxycarbonyloxyalkyl group, or an alkoxycarbonyloxyalkyl group. ) Disazo dye for polyester fibers.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58017207A JPS59145253A (en) | 1983-02-04 | 1983-02-04 | Disazo dye for polyester fiber |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58017207A JPS59145253A (en) | 1983-02-04 | 1983-02-04 | Disazo dye for polyester fiber |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59145253A JPS59145253A (en) | 1984-08-20 |
| JPH0445541B2 true JPH0445541B2 (en) | 1992-07-27 |
Family
ID=11937491
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58017207A Granted JPS59145253A (en) | 1983-02-04 | 1983-02-04 | Disazo dye for polyester fiber |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59145253A (en) |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57109860A (en) * | 1980-12-26 | 1982-07-08 | Mitsubishi Chem Ind Ltd | Disazo dye for polyester fiber |
| JPS57111356A (en) * | 1980-12-29 | 1982-07-10 | Mitsubishi Chem Ind Ltd | Disazo dye for polyester fiber |
| JPS57125262A (en) * | 1981-01-27 | 1982-08-04 | Mitsubishi Chem Ind Ltd | Disazo dye for polyester fiber |
| JPS57167355A (en) * | 1981-04-08 | 1982-10-15 | Nippon Kayaku Co Ltd | Disazo compound and method for dyeing or printing hydrophobic fiber by using the same |
| JPS57207649A (en) * | 1981-06-18 | 1982-12-20 | Mitsubishi Chem Ind Ltd | Disazo dye for polyester fiber |
| JPS57212255A (en) * | 1981-06-23 | 1982-12-27 | Mitsubishi Chem Ind Ltd | Disazo dye for polyester fiber |
| JPS585362A (en) * | 1981-07-01 | 1983-01-12 | Mitsubishi Chem Ind Ltd | Disazo dye for polyester fiber |
| JPS585363A (en) * | 1981-07-01 | 1983-01-12 | Mitsubishi Chem Ind Ltd | Diazo dye for polyester fiber |
-
1983
- 1983-02-04 JP JP58017207A patent/JPS59145253A/en active Granted
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57109860A (en) * | 1980-12-26 | 1982-07-08 | Mitsubishi Chem Ind Ltd | Disazo dye for polyester fiber |
| JPS57111356A (en) * | 1980-12-29 | 1982-07-10 | Mitsubishi Chem Ind Ltd | Disazo dye for polyester fiber |
| JPS57125262A (en) * | 1981-01-27 | 1982-08-04 | Mitsubishi Chem Ind Ltd | Disazo dye for polyester fiber |
| JPS57167355A (en) * | 1981-04-08 | 1982-10-15 | Nippon Kayaku Co Ltd | Disazo compound and method for dyeing or printing hydrophobic fiber by using the same |
| JPS57207649A (en) * | 1981-06-18 | 1982-12-20 | Mitsubishi Chem Ind Ltd | Disazo dye for polyester fiber |
| JPS57212255A (en) * | 1981-06-23 | 1982-12-27 | Mitsubishi Chem Ind Ltd | Disazo dye for polyester fiber |
| JPS585362A (en) * | 1981-07-01 | 1983-01-12 | Mitsubishi Chem Ind Ltd | Disazo dye for polyester fiber |
| JPS585363A (en) * | 1981-07-01 | 1983-01-12 | Mitsubishi Chem Ind Ltd | Diazo dye for polyester fiber |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59145253A (en) | 1984-08-20 |
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