JPH0578590B2 - - Google Patents
Info
- Publication number
- JPH0578590B2 JPH0578590B2 JP59085509A JP8550984A JPH0578590B2 JP H0578590 B2 JPH0578590 B2 JP H0578590B2 JP 59085509 A JP59085509 A JP 59085509A JP 8550984 A JP8550984 A JP 8550984A JP H0578590 B2 JPH0578590 B2 JP H0578590B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- fibers
- dye
- dyeing
- hydrogen atom
- 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
- 239000000985 reactive dye Substances 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims 1
- 239000000835 fiber Substances 0.000 description 24
- 238000004043 dyeing Methods 0.000 description 21
- 239000000975 dye Substances 0.000 description 18
- 229920003043 Cellulose fiber Polymers 0.000 description 16
- 229920000728 polyester Polymers 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- 239000004744 fabric Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 239000000986 disperse dye Substances 0.000 description 6
- -1 β-cyanoethylamino Chemical group 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- BVCXXRGKINNOEO-UHFFFAOYSA-N 2-(4-aminophenyl)sulfonylethanol;sulfuric acid Chemical compound OS(O)(=O)=O.NC1=CC=C(S(=O)(=O)CCO)C=C1 BVCXXRGKINNOEO-UHFFFAOYSA-N 0.000 description 1
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 1
- GGZZISOUXJHYOY-UHFFFAOYSA-N 8-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(N)=CC=CC2=C1O GGZZISOUXJHYOY-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 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 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Description
発明の目的
(イ) 産業上の利用分野
本発明は新規な反応性染料に関するものであ
る。
(ロ) 従来の技術
従来、セルロース繊維を染色する場合には、反
応性染料を使用し、炭酸ナトリウム、炭酸カリウ
ム、水酸化ナトリウム等の酸結合剤および塩化ナ
トリウム、硫酸ナトリウム等の電解質の存在下
に、PH10以上で、温度100℃以下の条件下で行う
方法が採用されている。
(ハ) 発明が解決しようとする問題点
ところが、近年セルロース繊維とその他の繊
維、特にポリエステル繊維との混紡布等の需要が
増大し、この様なセルロース／ポリエステル混合
繊維（以下単にＣ／Ｐ繊維と記す）を染色するた
めには、セルロース繊維に対する染料および染色
条件とポリエステル繊維に対する染料および染色
条件とをそれぞれに適用する必要があつた。それ
はポリエステル繊維を染色するための染料および
染色条件がセルロース繊維に対するそれと、大き
く相違するからであつた、すなわちポリエステル
繊維を染色するためには、分散染料を使用し、温
度約130℃で染色する必要があつたためである。
たとえば、上記Ｃ／Ｐ繊維を同一の工程で染色
するとすれば、反応性染料と分散染料との組合せ
で二つの異なる染料を使用し染色を行わせること
となり、これにはいくつかの問題があつた。例え
ば反応性染料をセルロース繊維側に充分染着させ
るためには酸結合剤によりPHを10以上とすること
が必要となり、酸結合剤の存在は分散染料の分解
を促進し分散染料のポリエステル繊維への染着が
不充分となる、一方、分散染料をポリエステル繊
維側に染着させるためには高温条件（通常130℃）
を必要とするが、上記高PH下における高温下では
反応性染料の加水分解を促進し、セルロース繊維
への染着が著しく阻害されることとなる。したが
つてこの様なＣ／Ｐ繊維を染色する場合には、セ
ルロースまたはポリエステルの一方の繊維を染色
した後、別浴により他の一方の繊維を染色する二
浴法が一般的に行われることとなるのである。
本発明は、分散染料によりポリエステル繊維を
染色する際の、PHおよび染色条件下でセルロース
繊維を染色することができる新規な反応性染料の
提供をその目的とするものである。
発明の構成
(イ) 問題点を解決するための手段
すなわち、本発明は
一般式〔〕
Object of the Invention (a) Industrial Application Field The present invention relates to a novel reactive dye. (b) Conventional technology Conventionally, when dyeing cellulose fibers, reactive dyes are used in the presence of acid binders such as sodium carbonate, potassium carbonate, and sodium hydroxide, and electrolytes such as sodium chloride and sodium sulfate. For this purpose, a method is adopted in which the pH is 10 or higher and the temperature is 100℃ or lower. (c) Problems to be solved by the invention However, in recent years, demand for blended fabrics of cellulose fibers and other fibers, especially polyester fibers, etc. has increased, and such cellulose/polyester blended fibers (hereinafter simply referred to as C/P fibers) ), it was necessary to apply dyes and dyeing conditions to cellulose fibers and dyes and dyeing conditions to polyester fibers, respectively. This is because the dyes and dyeing conditions for dyeing polyester fibers are significantly different from those for cellulose fibers. In other words, to dye polyester fibers, it is necessary to use disperse dyes and dye at a temperature of approximately 130°C. This is because it was hot. For example, if the above-mentioned C/P fibers were to be dyed in the same process, two different dyes would be used in combination, a reactive dye and a disperse dye, which would pose several problems. Ta. For example, in order to fully dye the reactive dyes on the cellulose fiber side, it is necessary to use an acid binder to raise the pH to 10 or more. On the other hand, high temperature conditions (usually 130℃) are required to dye the disperse dye on the polyester fiber side.
However, at high temperatures under the above-mentioned high pH conditions, hydrolysis of the reactive dye is promoted, and dyeing of cellulose fibers is significantly inhibited. Therefore, when dyeing such C/P fibers, a two-bath method is generally used in which one fiber, cellulose or polyester, is dyed and then the other fiber is dyed in a separate bath. It becomes. An object of the present invention is to provide a novel reactive dye that can dye cellulose fibers under the pH and dyeing conditions when dyeing polyester fibers with disperse dyes. Structure of the invention (a) Means for solving the problem That is, the present invention has the general formula []
【化】
（式中、Ｍは水素原子またはアルカリ金属を表
わし、R1は水素原子を表わし、R2は低級アルコ
キシ基またはスルホン酸基を表わし、R3は水素
原子、アセチルアミノ基またはスルホン酸基を表
わし、R4およびR5は水素原子、メチル基、メト
キシ基またはスルホン酸基を表わし、Ｚは塩素原
子、フツ素原子、脂肪族または芳香族のアミノ残
基、メトキシ基またはフエノキシ基を表わし、ｍ
は１，２または３を表わし、ｎは０または１を表
わし、そしてベンゼン環ＡおよびＢはナフタレン
環を表わしても良い。）
で示される反応性染料、
を要旨とするものである。
本発明の一般式〔〕で表わされる反応性染料
において、Ｍで表わされるアルカリ金属として
は、ナトリウム、カリウム等が挙げられ、R2で
表わされる低級アルコキシ基としては、炭素数１
〜４のアルコキシ基が挙げられ、Ｚで表わされる
脂肪族または芳香族のアミノ残基としてはアミ
ノ、C1〜4のアルキルアミノ、エタノールアミノ、
β−シアノエチルアミノ、β−スルホエチルアミ
ノ、グリシン残基、アニリノおよびスルホ、クロ
ロ、低級アルキル、低級アルコキシ、ニトロ、カ
ルボキシ等で置換されたアニリノ基が挙げられ
る。
前示一般式〔〕で表わされる反応性染料は次
のようにして製造することができる。
たとえば一般式〔〕、〔〕[Chemical Formula] (In the formula, M represents a hydrogen atom or an alkali metal, R 1 represents a hydrogen atom, R 2 represents a lower alkoxy group or a sulfonic acid group, and R 3 represents a hydrogen atom, an acetylamino group or a sulfonic acid group. R 4 and R 5 represent a hydrogen atom, a methyl group, a methoxy group, or a sulfonic acid group, and Z represents a chlorine atom, a fluorine atom, an aliphatic or aromatic amino residue, a methoxy group, or a phenoxy group. Representation, m
represents 1, 2 or 3, n represents 0 or 1, and the benzene rings A and B may represent a naphthalene ring. ) Reactive dyes shown in the following are the main points. In the reactive dye represented by the general formula [] of the present invention, examples of the alkali metal represented by M include sodium, potassium, etc., and the lower alkoxy group represented by R 2 has a carbon number of 1
-4 alkoxy groups, and the aliphatic or aromatic amino residues represented by Z include amino, C1-4 alkylamino, ethanolamino,
Examples include β-cyanoethylamino, β-sulfoethylamino, glycine residues, anilino and anilino groups substituted with sulfo, chloro, lower alkyl, lower alkoxy, nitro, carboxy, and the like. The reactive dye represented by the general formula [] can be produced as follows. For example, general formula [], []
【式】【formula】
【式】
（式中、Ｍ，R1，R2，R3，ｍそしてベンゼン
環ＡおよびＢは前記定義に同じ）
で示される化合物を通常のジアゾ化およびカツプ
リングを行い下記一般式〔〕[Formula] (In the formula, M, R 1 , R 2 , R 3 , m and benzene rings A and B are the same as defined above.) A compound represented by the formula is subjected to conventional diazotization and coupling to form the following general formula []
【化】
（式中、Ｍ，R1，R2，R3，ｍそしてベンゼン
環ＡおよびＢは前記定義に同じ）
で示されるモノアゾ体とする。
一方、下記式〔〕、〔〕、〔〕It is a monoazo compound represented by the following formula: (wherein M, R 1 , R 2 , R 3 , m and benzene rings A and B are the same as defined above). On the other hand, the following formulas [], [], []
【化】[ka]
【化】[ka]
【化】
（式中、Ｍ，R4，R5，Ｚおよびｎは前記定義
に同じ）
で示される化合物を水性媒質中、任意の順序で縮
合させ下記一般式〔〕[Chemical Formula] (wherein M, R 4 , R 5 , Z and n are the same as defined above) are condensed in an arbitrary order in an aqueous medium to form the following general formula []
【化】
（式中、Ｍ，R4，R5，Ｚおよびｎは前記定義
に同じ）
で示される化合物を製造する。
次いで該一般式〔〕で示される化合物に前記
〔〕のモノアゾ体を、通常の方法でジアゾ化し
たジアゾニウム化合物をカツプリングさせること
により前示一般式〔〕の反応性染料を製造する
ことができる。
(ロ) 作 用
本発明の反応性染料で染色し得る繊維としては
木綿、ビスコースレーヨン、キユプラアンモニウ
ムレーヨン、麻などのセルロース系繊維を挙げる
ことができる。またセルロース系繊維を含有する
ポリエステル、トリアセテート、ポリアクリロニ
トリル、ポリアミド、羊毛、絹などの混合繊維中
の該セルロース系繊維はもちろん良好に染色する
ことができる。
本発明の反応性染料を使用する繊維の染色方法
においては、セルロース系以外の繊維を染色する
に必要な染料、例えばColour Index（第３版）に
記載されている分散染料などを同時に染浴に加え
て染色することができる。
本発明の反応性染料を使用してセルロース系繊
維を染色する場合には、たとえば上記一般式
〔〕で示される反応性染料、および染色中に、
染浴をPH５〜10に保持するに必要な緩衝剤（たと
えば炭酸、リン酸、酢酸、クエン酸等の酸とそれ
らの酸のナトリウム塩またはカリウム塩の単一ま
たは混合物で通常0.5〜5.0ｇ／程度））そして
必要に応じて電解質（塩化ナトリウムまたは硫酸
ナトリウム等を通常１〜150ｇ／程度）を加え
た染浴を調整し、この染浴にセルロース系繊維を
投入し、温度100〜150℃で30〜50分間加熱するこ
とによつて良好な染色を行うことができる。
また、セルロース系繊維に他の繊維たとえばポ
リエステル繊維を加えて製造される混紡布、混織
編物等を染色するためには、本発明の上記一般式
〔〕で示される反応性染料と、上記Colour
Index所載の分散染料とを上記染浴に添加するこ
とにより、セルロース系繊維とポリエステル繊維
とを一浴一段法により同時に染色することができ
る。
また、上記のような混紡布、混織編物等を染色
する場合に、従来採用されているようにどちらか
一方の繊維を染色した後に同浴で他方の繊維を染
色する一浴二段法を適用してもよく、さらには、
本発明の反応性染料による染色法とセルロース系
繊維以外の繊維に対する染色法とを組合せて、
別々の浴からセルロース系繊維とその他の繊維と
を染色する二浴法を採用することも可能である。
以下、本発明の方法を実施例によつて具体的に
説明するが、本発明は、以下の実施例に限定され
るものではない。
(ハ) 実施例および効果
実施例 １
遊離酸の形で下記構造式A compound represented by the formula (wherein M, R 4 , R 5 , Z and n are the same as defined above) is produced. Next, the reactive dye of the general formula [] can be produced by coupling the monoazo form of the above [] to the compound of the general formula [] with a diazonium compound obtained by diazotizing it by a conventional method. (b) Function Examples of fibers that can be dyed with the reactive dye of the present invention include cellulose fibers such as cotton, viscose rayon, cuprammonium rayon, and hemp. Furthermore, cellulose fibers in mixed fibers such as polyester, triacetate, polyacrylonitrile, polyamide, wool, silk, etc. containing cellulose fibers can of course be dyed well. In the fiber dyeing method using the reactive dye of the present invention, dyes necessary for dyeing non-cellulose fibers, such as disperse dyes listed in the Color Index (3rd edition), are added to the dye bath at the same time. In addition, it can be dyed. When dyeing cellulose fibers using the reactive dye of the present invention, for example, the reactive dye represented by the above general formula [ ] and during dyeing,
Buffers necessary to maintain the dye bath at pH 5-10 (for example, acids such as carbonic acid, phosphoric acid, acetic acid, citric acid, and sodium salts or potassium salts of these acids, singly or in mixtures, usually 0.5-5.0 g/ )) Then, if necessary, prepare a dye bath to which electrolytes (usually about 1 to 150 g of sodium chloride or sodium sulfate, etc.) are added, add cellulose fibers to this dye bath, and dye at a temperature of 100 to 150 degrees Celsius. Good dyeing can be achieved by heating for 30-50 minutes. In addition, in order to dye blended fabrics, blended knitted fabrics, etc. produced by adding other fibers such as polyester fibers to cellulose fibers, a reactive dye represented by the above general formula [] of the present invention and the above Color
By adding the disperse dye listed in the Index to the above dye bath, cellulose fibers and polyester fibers can be dyed simultaneously by a one-bath, one-stage method. In addition, when dyeing blended fabrics, blended knitted fabrics, etc., as described above, the conventional one-bath two-step method of dyeing one fiber and then dyeing the other fiber in the same bath is used. May be applied, and furthermore,
By combining the dyeing method using the reactive dye of the present invention and the dyeing method for fibers other than cellulose fibers,
It is also possible to employ a two-bath method in which cellulosic fibers and other fibers are dyed from separate baths. EXAMPLES Hereinafter, the method of the present invention will be specifically explained with reference to Examples, but the present invention is not limited to the following Examples. (c) Examples and effect examples 1 The following structural formula in the form of free acid
【化】
｛λmax518nm（水）｝
で示される反応性染料0.29ｇ、芒硝16ｇ、緩衝剤
としてNa2HPO4・12H2O0.4ｇおよびKH2PO40.1
ｇを水200mlに加えてPH＝７に調製した染浴に、
未シルケツト綿メリヤス10ｇを入れ30分を要して
120℃迄昇温し、同温度で60分間染色した後、水
洗、ソーピング、水洗および乾燥を行い、鮮明赤
色の染色物を得た。本染料の染着度は非常に良好
で、得られた染色物は極めて濃厚であり、耐光堅
牢度、耐塩素堅牢度および耐汗−日光堅牢度はい
ずれも良好であつた。
なお、本実施例で使用した反応性染料は、２−
ナフチルアミン−４，８−ジスルホン酸30.3ｇを
１−アミノベンゼン−２−スルホン酸17.3ｇと常
法でジアゾ化およびカツプリングして下式[Chemical] {λmax518nm (water)} 0.29g of reactive dye, 16g of mirabilite, 0.4g of Na 2 HPO 4・12H 2 O and 0.1 KH 2 PO 4 as buffering agents.
Add g to 200 ml of water to adjust the pH to 7,
Add 10g of unmercered cotton knitted fabric and leave for 30 minutes.
After raising the temperature to 120°C and dyeing at the same temperature for 60 minutes, washing with water, soaping, washing with water and drying were performed to obtain a bright red dyed product. The degree of dyeing of this dye was very good, and the dyed product obtained was extremely deep, and the light fastness, chlorine fastness, and sweat-sunlight fastness were all good. The reactive dye used in this example was 2-
30.3 g of naphthylamine-4,8-disulfonic acid was diazotized and coupled with 17.3 g of 1-aminobenzene-2-sulfonic acid using the following formula.
【化】
で表わされるモノアゾ化合物を製造した。一方２
−アミノ−５−ヒドロキシナフタリン−７−スル
ホン酸23.9ｇと塩化シアヌル18.5ｇを５℃以下で
縮合させた後、４−（β−ヒドロキシエチル）ス
ルホニルアニリン硫酸エステル28.1ｇを30〜35℃
で縮合させ下記式A monoazo compound represented by the following formula was produced. On the other hand 2
- After condensing 23.9 g of amino-5-hydroxynaphthalene-7-sulfonic acid and 18.5 g of cyanuric chloride at 5°C or lower, 28.1 g of 4-(β-hydroxyethyl)sulfonylaniline sulfate was added at 30 to 35°C.
Condensate with the following formula
【化】
の化合物を製造し、該反応液中に上記モノアゾ化
合物を常法でジアゾ化したジアゾ液を加え、カツ
プリングさせた後塩化カリウムで塩析することに
より上記ジスアゾ反応性染料を製造した。
実施例 ２
実施例１に準じた方法で下記一般式The above-mentioned disazo-reactive dye was produced by producing a compound of formula [Image Omitted], adding a diazo solution obtained by diazotizing the above-mentioned monoazo compound in a conventional manner to the reaction solution, coupling, and salting out with potassium chloride. Example 2 The following general formula was prepared in the same manner as in Example 1.
【化】
で表わされるジスアゾ反応性染料により綿布を染
色し、結果を第１表に示した。Cotton cloth was dyed with a disazo-reactive dye represented by the following formula, and the results are shown in Table 1.
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
Claims (1)
わし、R1は水素原子を表わし、R2は低級アルコ
キシ基またはスルホン酸基を表わし、R3は水素
原子、アセチルアミノ基またはスルホン酸基を表
わし、R4およびR5は水素原子、メチル基、メト
キシ基またはスルホン酸基を表わし、Ｚは塩素原
子、フツ素原子、脂肪族または芳香族のアミノ残
基、メトキシ基またはフエノキシ基を表わし、ｍ
は１，２または３を表わし、ｎは０または１を表
わし、そしてベンゼン環ＡおよびＢはナフタレン
環を表わしても良い。） で示される反応性染料。[Claims] 1 General formula [] [Chemical formula] (wherein M represents a hydrogen atom or an alkali metal, R 1 represents a hydrogen atom, R 2 represents a lower alkoxy group or a sulfonic acid group, and R 3 represents a hydrogen atom, an acetylamino group or a sulfonic acid group, R 4 and R 5 represent a hydrogen atom, a methyl group, a methoxy group or a sulfonic acid group, and Z represents a chlorine atom, a fluorine atom, an aliphatic or aromatic group represents an amino residue, methoxy group or phenoxy group, m
represents 1, 2 or 3, n represents 0 or 1, and the benzene rings A and B may represent a naphthalene ring. ) reactive dyes.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8550984A JPS60229957A (en) | 1984-04-27 | 1984-04-27 | Reactive dye |
| GB08509081A GB2160883B (en) | 1984-04-09 | 1985-04-09 | Reactive azo dyes |
| US06/721,514 US4645832A (en) | 1984-04-09 | 1985-04-09 | Cellulose fiber-reactive disazo or trisazo dyes having a triazine ring substituted by A(B-sulfatoethyl) sulfonylanilino group |
| CH1515/85A CH663215A5 (en) | 1984-04-09 | 1985-04-09 | REACTIVE AZO DYES. |
| DE3512690A DE3512690C2 (en) | 1984-04-09 | 1985-04-09 | Reactive azo dyes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8550984A JPS60229957A (en) | 1984-04-27 | 1984-04-27 | Reactive dye |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60229957A JPS60229957A (en) | 1985-11-15 |
| JPH0578590B2 true JPH0578590B2 (en) | 1993-10-29 |
Family
ID=13860898
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8550984A Granted JPS60229957A (en) | 1984-04-09 | 1984-04-27 | Reactive dye |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60229957A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61200174A (en) * | 1985-02-28 | 1986-09-04 | Mitsubishi Chem Ind Ltd | Disazo compound |
| US5075428A (en) * | 1988-07-30 | 1991-12-24 | Bayer Aktiengesellschaft | 2,4-diamino-6-fluorotriazine disazo reactive dyestuffs |
| JP2650360B2 (en) * | 1988-10-14 | 1997-09-03 | 住友化学工業株式会社 | Disazo compound and dyeing or printing method using the same |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5512187A (en) * | 1978-07-06 | 1980-01-28 | Ciba Geigy Ag | Reactive dye* prepatation and application thereof |
-
1984
- 1984-04-27 JP JP8550984A patent/JPS60229957A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5512187A (en) * | 1978-07-06 | 1980-01-28 | Ciba Geigy Ag | Reactive dye* prepatation and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60229957A (en) | 1985-11-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |