JPS645069B2 - - Google Patents
Info
- Publication number
- JPS645069B2 JPS645069B2 JP55189018A JP18901880A JPS645069B2 JP S645069 B2 JPS645069 B2 JP S645069B2 JP 55189018 A JP55189018 A JP 55189018A JP 18901880 A JP18901880 A JP 18901880A JP S645069 B2 JPS645069 B2 JP S645069B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- alkyl group
- dye
- lower alkyl
- dyeing
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 239000000835 fiber Substances 0.000 claims description 19
- 229920000728 polyester Polymers 0.000 claims description 16
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 10
- 125000005336 allyloxy group Chemical group 0.000 claims description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 3
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 239000000975 dye Substances 0.000 description 45
- 238000004043 dyeing Methods 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 24
- 239000004744 fabric Substances 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- -1 acetoxyethyl group Chemical group 0.000 description 14
- 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 8
- 238000000859 sublimation Methods 0.000 description 8
- 230000008022 sublimation Effects 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 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
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 6
- 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
- 239000000243 solution Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- 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
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 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
- LOGPMRUTGLEHIV-UHFFFAOYSA-N 2-amino-5-phenyl-2-(thiophen-2-yldiazenyl)-3H-thiophene-3-carbonitrile Chemical compound NC1(SC(=CC1C#N)C1=CC=CC=C1)N=NC=1SC=CC1 LOGPMRUTGLEHIV-UHFFFAOYSA-N 0.000 description 1
- XVGHZFWFGXDIOU-UHFFFAOYSA-N 2-aminothiophene-3-carbonitrile Chemical compound NC=1SC=CC=1C#N XVGHZFWFGXDIOU-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#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
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-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
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001412 amines Chemical class 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
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000003086 colorant Substances 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
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 238000002156 mixing Methods 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
- 238000003756 stirring Methods 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
- 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、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〔〕
（式中、X1およびX2は水素原子、ハロゲン原子、
トリフルオロメチル基またはニトロ基を表わし、
Ｙはシアノ基または低級アルコキシカルボニル基
を表わし、Ｚは水素原子、メチル基またはアセチ
ルアミノ基を表わし、R1は低級アルコキシ低級
アルキル基、アリル基、アリルオキシ低級アルキ
ル基、低級アルキルカルボニルオキシ低級アルキ
ル基、低級アルコキシカルボニルオキシ低級アル
キル基、シアノ低級アルキル基、低級アルコキシ
カルボニル低級アルキル基またはアリルオキシカ
ルボニル低級アルキル基を表わし、R2はハロゲ
ン原子もしくはメチル基で置換されていてもよい
アリル基またはアリルオキシ低級アルキル基を表
わす。）で示される新規な水不溶性のジスアゾ染
料である。
前示一般式〔〕において、X1およびX2で表
わされるハロゲン原子としては、フツ素原子、塩
素原子、臭素原子、沃素原子が挙げられ、Ｙで表
わされる低級アルコキシカルボニル基としては、
メトキシカルボニル基、エトキシカルボニル基、
ブトキシカルボニル基等が挙げられ、R1で表わ
される低級アルコキシ低級アルキル基としては、
メトキシエチル基、エトキシエチル基、ブトキシ
エチル基等が挙げられ、アリルオキシ低級アルキ
ル基としては、アリルオキシエチル基等が挙げら
れ、低級アルキルカルボニルオキシ低級アルキル
基としては、アセトキシエチル基等が挙げられ、
低級アルコキシカルボニルオキシ低級アルキル基
としては、メトキシカルボニルオキシエチル基、
エトキシカルボニルオキシエチル基等が挙げら
れ、低級アルコキシカルボニル低級アルキル基と
しては、メトキシカルボニルメチル基、メトキシ
カルボニルエチル基、メトキシカルボニルプロピ
ル基、エトキシカルボニルエチル基、ブトキシカ
ルボニルエチル基等が挙げられ、シアノ低級アル
キル基としては、シアノメチル基、シアノエチル
基等が挙げられ、アリルオキシカルボニル低級ア
ルキル基としては、アリルオキシカルボニルメチ
ル基、アリルオキシカルボニルエチル基、アリル
オキシカルボニルプロピル基等が挙げられ、R2
で表わされるハロゲン原子もしくはメチル基で置
換されていてもよいアリル基としてはアリル基、
２−メチルアリル基、２−クロロアリル基等が挙
げられ、アリルオキシ低級アルキル基としてはア
リルオキシエチ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、X1およびX2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〔〕
（式中、Ｙ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、X1X2およびＹ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、Ｚ、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〔〕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料性
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、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100ml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。このとき温度は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12.4
ｇをメタノール200mlに溶液中に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−シアノ−５−フエニルア
ゾチオフエン）11.4ｇを酢酸114mlおよびリン酸
114ml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分間撹拌してモノアゾ化合物のジアゾ
液を調製した。
Ｎ−アリル−Ｎ−（β−シアノエチル）アニリ
ン9.3ｇ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597nｍ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610nｍ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582nｍ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605nｍ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631nｍであ
つた。
実施例 ６
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660nｍであ
つた。
実施例 ７
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604nｍ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 a disazo dye for polyester fibers, and more specifically, it dyes polyester fibers in a vivid blue color and improves various fastnesses, particularly light fastness,
This invention relates to disazo dyes that have excellent sublimation fastness, water fastness, temperature stability during dyeing, and PH stability. The disazo dye for polyester fibers of the present invention is
General formula below [] (In the formula, X 1 and X 2 are hydrogen atoms, halogen atoms,
represents a trifluoromethyl group or a nitro group,
Y represents a cyano group or a lower alkoxycarbonyl group, Z represents a hydrogen atom, a methyl group or an acetylamino group, and R 1 represents a lower alkoxy lower alkyl group, an allyl group, an allyloxy lower alkyl group, a lower alkylcarbonyloxy lower alkyl group , lower alkoxycarbonyloxy lower alkyl group, cyano lower alkyl group, lower alkoxycarbonyl lower alkyl group or allyloxycarbonyl lower alkyl group, R 2 is an allyl group or allyloxy lower which may be substituted with a halogen atom or a methyl group. Represents an alkyl group. ) is a new water-insoluble disazo dye. In the above general formula [], the halogen atoms represented by X 1 and X 2 include fluorine atom, chlorine atom, bromine atom, and iodine atom, and the lower alkoxycarbonyl group represented by Y includes:
Methoxycarbonyl group, ethoxycarbonyl group,
Examples of the lower alkoxy lower alkyl group represented by R 1 include butoxycarbonyl group, etc.
Examples of the allyloxy lower alkyl group include an allyloxyethyl group; examples of the lower alkylcarbonyloxy lower alkyl group include an acetoxyethyl group;
As the lower alkoxycarbonyloxy lower alkyl group, methoxycarbonyloxyethyl group,
Examples of lower alkoxycarbonyl lower alkyl groups include methoxycarbonylmethyl group, methoxycarbonylethyl group, methoxycarbonylpropyl group, ethoxycarbonylethyl group, butoxycarbonylethyl group, and cyano lower Examples of the alkyl group include a cyanomethyl group and a cyanoethyl group, and examples of the allyloxycarbonyl lower alkyl group include an allyloxycarbonylmethyl group, an allyloxycarbonylethyl group, an allyloxycarbonylpropyl group, and R 2
Examples of the allyl group optionally substituted with a halogen atom or methyl group include an allyl group,
Examples of the allyloxy lower alkyl group include a 2-methylallyl group and a 2-chloroallyl group, and examples of the allyloxy lower alkyl group include an allyloxyethyl group. The disazo dye represented by the above general formula [] is the following formula [] (In the formula, X 1 and X 2 are the same as defined above.) The amines represented by (In the formula, Y is the same as defined above.) Coupled with an aminothiophene represented by the following formula [] (wherein, X 1 X 2 and Y are the same as defined above) is diazotized to form the following general formula [] It can be produced by coupling with an aniline represented by the formula (wherein Z, 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 of fibers and the above-mentioned 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. Good results such as improved dye properties may be obtained by blending. 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 dye bath containing 1 g of formaldehyde condensate and 2 g of higher alcohol sulfate ester dispersed in water, and dyed at 130°C.
After dyeing for 60 minutes, soaping, washing and drying resulted 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 as follows. 9.3 g of aniline was dissolved in 100 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 set not to exceed 5°C. The obtained aniline diazonium salt solution was mixed with 2-amino-3-cyanothiophene 12.4
g was added to 200 ml of methanol at 2° C. and stirred at the same temperature for 2 hours. The precipitated monoazo compound was removed, washed with water, and dried. 11.4 g of this monoazo compound (2-amino-3-cyano-5-phenylazothiophene) was added to 114 ml of acetic acid and phosphoric acid.
Add nitrosyl sulfuric acid (3.5 g of sodium nitrite) to this mixture at 0-5°C.
(prepared by dissolving 97% sulfuric acid in 20 g) was gradually added.
A diazo solution of a monoazo compound was prepared by stirring at the same temperature for 30 minutes. 9.3 g of N-allyl-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 597 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 610 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 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 λmax (acetone) of this product was 582 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 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 605 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 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 631 nm. Example 6 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 660 nm. Example 7 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 604 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)
トリフルオロメチル基またはニトロ基を表わし、
Ｙはシアノ基または低級アルコキシカルボニル基
を表わし、Ｚは水素原子、メチル基またはアセチ
ルアミノ基を表わし、R1は低級アルコキシ低級
アルキル基、アリル基、アリルオキシ低級アルキ
ル基、低級アルキルカルボニルオキシ低級アルキ
ル基、低級アルコキシカルボニルオキシ低級アル
キル基、シアノ低級アルキル基、低級アルコキシ
カルボニル低級アルキル基またはアリルオキシカ
ルボニル低級アルキル基を表わし、R2はハロゲ
ン原子もしくはメチル基で置換されていてもよい
アリル基またはアリルオキシ低級アルキル基を表
わす。）で示されるポリエステル繊維用ジスアゾ
染料。[Claims] 1. General formula (In the formula, X 1 and X 2 are hydrogen atoms, halogen atoms,
represents a trifluoromethyl group or a nitro group,
Y represents a cyano group or a lower alkoxycarbonyl group, Z represents a hydrogen atom, a methyl group or an acetylamino group, and R 1 represents a lower alkoxy lower alkyl group, an allyl group, an allyloxy lower alkyl group, a lower alkylcarbonyloxy lower alkyl group , lower alkoxycarbonyloxy lower alkyl group, cyano lower alkyl group, lower alkoxycarbonyl lower alkyl group or allyloxycarbonyl lower alkyl group, R 2 is an allyl group or allyloxy lower which may be substituted with a halogen atom or a methyl group. Represents an alkyl group. ) Disazo dye for polyester fibers.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55189018A JPS57109860A (en) | 1980-12-26 | 1980-12-26 | Disazo dye for polyester fiber |
| GB8137778A GB2093056B (en) | 1980-12-26 | 1981-12-15 | Disazo dyestuffs and dyeing process |
| 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 |
| CH8258/81A CH647254A5 (en) | 1980-12-26 | 1981-12-23 | DISAZO DYES FOR POLYESTER FIBERS. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55189018A JPS57109860A (en) | 1980-12-26 | 1980-12-26 | Disazo dye for polyester fiber |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57109860A JPS57109860A (en) | 1982-07-08 |
| JPS645069B2 true JPS645069B2 (en) | 1989-01-27 |
Family
ID=16233919
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP55189018A Granted JPS57109860A (en) | 1980-12-26 | 1980-12-26 | Disazo dye for polyester fiber |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57109860A (en) |
Families Citing this family (9)
| 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 |
| JPS59145254A (en) * | 1983-02-04 | 1984-08-20 | Gosei Senriyou Gijutsu Kenkyu Kumiai | Disazo dye for polyester fiber |
| JPS59145253A (en) * | 1983-02-04 | 1984-08-20 | Gosei Senriyou Gijutsu Kenkyu Kumiai | Disazo dye for polyester fiber |
| JPH066674B2 (en) * | 1986-04-21 | 1994-01-26 | 合成染料技術研究組合 | Disazo compound and dyeing method using the same |
| JPH066675B2 (en) * | 1986-04-21 | 1994-01-26 | 合成染料技術研究組合 | Disazo compound and dyeing method using the same |
| GB8704727D0 (en) * | 1987-02-27 | 1987-08-05 | Ici Plc | Aromatic disazo compound |
| JP5713005B2 (en) * | 2010-03-26 | 2015-05-07 | 浩司 瀬川 | Dye for dye-sensitized solar cell and dye-sensitized solar cell |
| WO2012161098A1 (en) | 2011-05-20 | 2012-11-29 | 三菱化学株式会社 | Azo compound and ink containing compound |
| JP6233316B2 (en) | 2012-11-28 | 2017-11-22 | 三菱ケミカル株式会社 | Azo compound, ink containing azo compound, display containing the ink, and electronic paper |
-
1980
- 1980-12-26 JP JP55189018A patent/JPS57109860A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57109860A (en) | 1982-07-08 |
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