JPS62250060A - Disazo compound and method for dyeing using same - Google Patents
Disazo compound and method for dyeing using sameInfo
- Publication number
- JPS62250060A JPS62250060A JP61094363A JP9436386A JPS62250060A JP S62250060 A JPS62250060 A JP S62250060A JP 61094363 A JP61094363 A JP 61094363A JP 9436386 A JP9436386 A JP 9436386A JP S62250060 A JPS62250060 A JP S62250060A
- Authority
- JP
- Japan
- Prior art keywords
- dye
- formula
- dyeing
- disazo compound
- group
- 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.)
- Granted
Links
- 238000004043 dyeing Methods 0.000 title claims abstract description 32
- -1 Disazo compound Chemical class 0.000 title claims abstract description 27
- 238000000034 method Methods 0.000 title claims description 22
- 239000000835 fiber Substances 0.000 claims abstract description 20
- 239000002253 acid Substances 0.000 claims abstract description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
- 150000001450 anions Chemical class 0.000 claims abstract description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- 125000000542 sulfonic acid group Chemical group 0.000 claims abstract description 4
- 125000001624 naphthyl group Chemical group 0.000 claims abstract 3
- 229920002678 cellulose Polymers 0.000 claims description 14
- 239000001913 cellulose Substances 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 2
- 239000000975 dye Substances 0.000 abstract description 21
- 150000001875 compounds Chemical class 0.000 abstract description 13
- 229920000728 polyester Polymers 0.000 abstract description 12
- 239000000986 disperse dye Substances 0.000 abstract description 9
- 210000001170 unmyelinated nerve fiber Anatomy 0.000 abstract description 7
- 239000012736 aqueous medium Substances 0.000 abstract description 3
- 239000004952 Polyamide Substances 0.000 abstract description 2
- 238000004040 coloring Methods 0.000 abstract description 2
- 229920002647 polyamide Polymers 0.000 abstract description 2
- 210000002268 wool Anatomy 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 229920003043 Cellulose fiber Polymers 0.000 description 11
- 239000004744 fabric Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000985 reactive dye Substances 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 5
- 210000004744 fore-foot Anatomy 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000007513 acids Chemical class 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
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 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 3
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- 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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000049 pigment 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
- 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
- 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
- 238000010521 absorption reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001555 benzenes Chemical group 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 235000009120 camo Nutrition 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
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 210000002683 foot Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 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
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 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
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/34—Material containing ester groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/08—Azo dyes
- C09B62/09—Disazo or polyazo dyes
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、新規な水溶性ジスアゾ化合物及びこれを用い
てセルロース又はセルロース含有繊維類（とくにポリエ
ステル／セルロース混合繊維）を橙色ないしスカーレッ
ト色に染色する方法に関するものである。Detailed Description of the Invention (Industrial Application Field) The present invention is directed to a novel water-soluble disazo compound and a method for dyeing cellulose or cellulose-containing fibers (especially polyester/cellulose mixed fibers) in an orange to scarlet color using the same. It's about how to do it.
（従来の技術）
近年、ポリエステル／セルロース混合繊維（以下、単に
ｌ’−Ｐ／Ｃ繊維」と略記する。）を、分散染料と反応
性染料の併用により一浴一段、１３０℃で染色する方法
が検討されており、かかる方法で橙色ないしスカーレッ
ト色系反応性染料として用いられる化合物としては、例
えば特開昭６０−２０８３６８号、特開昭６０−８６１
６９号及び特開昭６０−２６０６５７号の各公報に、そ
れぞれ遊離酸の形で下記構造式（ａＬ （ｂ）及び〔
Ｃ〕
で示される水溶性モノ及びジスアゾ染料化合物が記載さ
れている。(Prior art) In recent years, a method has been developed in which polyester/cellulose mixed fibers (hereinafter simply referred to as l'-P/C fibers) are dyed in one step at 130°C in one bath using a combination of a disperse dye and a reactive dye. have been studied, and examples of compounds that can be used as orange to scarlet reactive dyes in this method include JP-A-60-208368 and JP-A-60-861.
69 and JP-A-60-260657, the following structural formulas (aL (b) and [
C] Water-soluble mono- and disazo dye compounds are described.
（発明が解決しようとする問題点）
しかしながら、上記構造式Ｃａ）で示される従来の化合
物は、分子中に反応基となる基：分子中のＯＨ基との反
応が効率的であれば工業的有利であるが、例えばＰ／Ｃ
繊維の１３０℃での一浴一段染色法におけるような高温
染色においては、母体構造のセルロースに対する親和性
が少なく、染着性、ビルドアツプ性が劣る、という問題
点があった。また、上記構造式Ｃｂ）で示される従来の
化合物は、分子中に反応基：ＯＯＨ
性は比較的良好である半面、分子中にかかる反経済的に
は極めて不利である、という問題点があった。更に、上
記構造式〔Ｃ〕で示される従来の化合物は、分子中に反
応基が１個しか存在しなくても、染色時のｐＨが７以上
ではセルロースに対し高い反応率を示す好ましいもので
あるが、該ｐＨが７より低い６．５等を示す弱酸性では
反応率が低下して好ましからざるものとなるので、例え
ば前記Ｐ／Ｃ繊維の一浴一段１３０℃以上の高温染色法
ではこれと併用されるポリエステル用分散染料の分解防
止等のために染色時のｐＨとしては上記６，５等の弱酸
性領域がとくに好ましいことからすれば、該従来の化合
物はかかるＰ／Ｃ繊維の一浴一段染色用には明らかに不
適当である、という問題点があった。(Problems to be Solved by the Invention) However, the conventional compound represented by the above structural formula Ca) has a group that becomes a reactive group in the molecule. Although advantageous, e.g. P/C
In high-temperature dyeing such as the one-bath one-stage dyeing method of fibers at 130° C., there is a problem in that the affinity for cellulose, which is a matrix structure, is low and the dyeability and build-up properties are poor. In addition, the conventional compound represented by the above structural formula Cb) has a reactive group in the molecule: OOH property, but while it has relatively good property, it has the problem that it is extremely uneconomical due to the reactive group in the molecule. Ta. Furthermore, the conventional compound represented by the above structural formula [C] is a preferable compound that exhibits a high reaction rate with cellulose at a pH of 7 or higher during dyeing, even if only one reactive group is present in the molecule. However, if the pH is weakly acidic, such as 6.5, which is lower than 7, the reaction rate decreases and becomes undesirable. Considering that the pH at the time of dyeing is particularly preferably in the weakly acidic range of 6 or 5 to prevent the decomposition of the disperse dye for polyester used in combination with P/C fibers, the conventional compound is suitable for use with such P/C fibers. There was a problem in that it was clearly unsuitable for one-step bath dyeing.
本発明は、上記の従来の問題点を解決しうる橙色ないし
スカーレット色系反応性染料として有用で新規な水溶性
ジスアゾ化合物及びそれを用いる染色法の提供を目的と
する。The object of the present invention is to provide a novel water-soluble disazo compound useful as an orange to scarlet reactive dye capable of solving the above-mentioned conventional problems, and a dyeing method using the same.
（問題点を解決するだめの手段）
本発明者らは、かかる目的を達成すべく鋭意研究を進め
た結果、本発明に到達した。すなわち、本発明は、遊離
酸の形で下記一般式（１）（式中、Ｄｚはメチル基、メ
トキシ基若しくはスルホン酸基で置換されていてもよい
ベンゼン環又は前記いずれかの基で置換されていてもよ
いナフタレン環を表わし、Ｒは水素原子、メチル基、カ
ルバモイル基又はカルボキシル基ヲ表わし、Ａ はアニ
オンを表わす。）で示される水溶性ジスアゾ化合物、並
びに、該化合物を用いることを特徴とするセルロース又
はセルロース含有繊維類の染色法を要旨とするものであ
る。かがる本発明の水溶性ジスアゾ化合物において、Ａ
ｅはピリジン核の正電荷とバランスさせるに必要な負電
荷であシ、その具体例としてはＯＨ、Ｃ１：Ｂｒ、Ｆ−
等が挙げられる。(Means for Solving the Problems) The present inventors have conducted intensive research to achieve the above object, and as a result, have arrived at the present invention. That is, the present invention provides compounds of the following general formula (1) (where Dz is a benzene ring optionally substituted with a methyl group, a methoxy group, or a sulfonic acid group, or a benzene ring substituted with any of the above groups) in the form of a free acid. R represents a hydrogen atom, a methyl group, a carbamoyl group, or a carboxyl group, and A represents an anion. The gist of this paper is a method for dyeing cellulose or cellulose-containing fibers. In the water-soluble disazo compound of the present invention, A
e is a negative charge necessary to balance the positive charge of the pyridine nucleus; specific examples thereof are OH, C1:Br, F-
etc.
本発明の前足一般式ＣＩ）で示されるジスアゾ化合物は
、例えば次のようにして製造することができる。すなわ
ち、遊離酸の形で下記一般式（式中、Ｄｚは前足一般式
（１）におけると同一の意義を有する。）で示される色
素１モル割合と、遊離酸の形で下記一般式ＣＩ）
Ｏ
（式中、Ｄｚは前足一般式（１）におけると同一の意義
を有する。）で示される色素１モル割合を縮合させ、遊
離酸の形で下記一般式（ＩＶ）（式中、Ｄｚは前足一般
式ＣＩ）におけると同一の意義を有する。）で示される
ジスアゾ体とする。The disazo compound represented by the general formula CI) of the present invention can be produced, for example, as follows. That is, 1 molar proportion of the dye represented by the following general formula (in the formula, Dz has the same meaning as in the front paw general formula (1)) in the form of a free acid, and the following general formula CI) in the form of a free acid. O (wherein, Dz has the same meaning as in the forefoot general formula (1)) is condensed to form the following general formula (IV) in the form of a free acid: It has the same meaning as in the forepaw general formula CI). ) as a disazo compound.
次いで、このジスアゾ体に、下記一般式（Ｖ）（式中、
Ｒは前足一般式〔１〕におけると同一の意義を有する。Next, the following general formula (V) (wherein,
R has the same meaning as in the forepaw general formula [1].
）で示される化合物を、水媒中、７０℃〜１００℃で反
応せしめ、前足一般式〔１〕で示される本発明の化合物
を得ることができる。) can be reacted in an aqueous medium at 70°C to 100°C to obtain the compound of the present invention represented by the general formula [1].
なお、反応液から目的生成物を取得するには、通常の塩
析法が用いられるが、反応液をそのままスプレー乾燥す
る方法によることもできる。Note that to obtain the desired product from the reaction solution, a normal salting-out method is used, but a method of spray drying the reaction solution as it is can also be used.
（作用）
かくして得られる本発明の橙色ないしスカーレット色系
の水溶性ジスアゾ化合物は、繊維、布を染色するための
染料、紙、合成樹脂の着色用色素、更にインクジェット
式プリンター用などの色素として広く利用することがで
き、なかでも反応性染料としての適性がとくに優れてい
る新規な化合物である。すなわち、本発明の化合物は、
ｐＨ７以上で行われるセルロース繊維の通常の染色法で
セルロースに対し高い反応率を示すばかりでな（、ｐＨ
５，６の弱酸性下１３０℃以上の高温で行われる染色法
でも分解することなくセルロースに対し高い反応率を示
すことから、Ｐ／Ｃ繊維の一浴一段染色法でポリエステ
ル用分散染料と併用するにはとくに好適である。(Function) The orange to scarlet water-soluble disazo compound of the present invention thus obtained is widely used as a dye for dyeing fibers and cloth, a pigment for coloring paper and synthetic resins, and a pigment for inkjet printers. It is a novel compound that is particularly suitable as a reactive dye. That is, the compound of the present invention is
Not only does it show a high reaction rate with cellulose in the usual dyeing method for cellulose fibers carried out at pH 7 or higher (pH
It shows a high reaction rate to cellulose without decomposing even in a dyeing method that is carried out at a high temperature of 130°C or higher under weak acidity of 5 or 6, so it can be used in combination with a disperse dye for polyester in a one-bath one-step dyeing method for P/C fibers. It is particularly suitable for
本発明のジスアゾ化合物を染料として用いる場合には、
対象となる繊維としては、木綿、ビスコースレーヨン、
キュプラアンモニウムレーヨン、麻などのセルロース系
繊維、更にはポリアミド、羊毛、絹等の含窒素繊維が挙
げられるが、セルロース繊維がとくに好ましい。また、
これらの繊維は、例えばポリエステル、トリアセテート
、ポリアクリロニトリルなどとの混合繊維であっても差
し支えない。When using the disazo compound of the present invention as a dye,
Targeted fibers include cotton, viscose rayon,
Examples include cellulose fibers such as cuproammonium rayon and hemp, and nitrogen-containing fibers such as polyamide, wool, and silk, but cellulose fibers are particularly preferred. Also,
These fibers may be mixed fibers with polyester, triacetate, polyacrylonitrile, etc., for example.
本発明のジスアゾ化合物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全染色するに必要な染
料、例えばＣｏ１ｏｕｒ 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。In the fiber dyeing method using the disazo compound of the present invention, dyes necessary for dyeing all of the non-cellulose fibers, such as disperse dyes listed in Co1our Index (3rd edition), are added to the dye bath at the same time. It can be dyed.
本発明のジスアゾ化合物を使用してセルロース系繊維を
染色する場合には、例えば、上記一般式ＣＩ）で示され
るジスアゾ化合物及び染色中に染浴をｐＨ５〜１０に保
持するに必要な緩衝剤（例えば炭酸、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又はカリウム
塩の単一または混合物で通常０．５〜５．０ｆ／ｌ程度
）、そして必要に応じて電解質（塩化ナトリウム又は硫
酸ナトリウム等を通常１〜ｔｓｏｒ／＃程度、特に好ま
しくは４０〜８０ ｔ／ｌ ）を加えた染浴を調製し、
この染浴にセルロース系繊維を投入し、温度１００〜１
５０℃で３０〜５０分間加熱することによって良好な染
色を行うことができる。When dyeing cellulose fibers using the disazo compound of the present invention, for example, a disazo compound represented by the above general formula CI) and a buffer ( For example, acids such as carbonic acid, phosphoric acid, acetic acid, citric acid, sodium salts or potassium salts of these acids, either singly or in mixtures (usually about 0.5 to 5.0 f/l), and if necessary, an electrolyte (chlorinated Prepare a dye bath to which sodium or sodium sulfate or the like is added (usually about 1 to tsor/#, particularly preferably 40 to 80 t/l),
Cellulose fibers are put into this dye bath, and the temperature is 100 to 1.
Good dyeing can be achieved by heating at 50°C for 30 to 50 minutes.
また、セルロース系繊維に他の繊維、例えばポリエステ
ル繊維を混合して製造されている混紡布、混繊編物等を
染色するためには、本発明の前示一般式（１）で示され
るジスアゾ化合物と、上記Ｃｏ１ｏｕｒ Ｉｎｄ’ｅｘ
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。この場合、染浴のｐＨ
を５〜７に保持するのが好ましい。In addition, in order to dye blended fabrics, blended knitted fabrics, etc. produced by mixing cellulose fibers with other fibers such as polyester fibers, a disazo compound represented by the general formula (1) of the present invention may be used. And the above Co1our Ind'ex
By adding the listed disperse dye to the above dye bath, cellulose fibers and polyester fibers can be dyed simultaneously by a one-bath, one-stage method. In this case, the pH of the dyebath
It is preferable to keep it between 5 and 7.
また、上記のような混紡布、混繊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、更には、本発明のジスアゾ化合物によ
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
。In addition, when dyeing blended fabrics, blended knitted fabrics, etc., as described above, a one-bath two-step method is used in which one of the fibers is dyed first, and then the other fiber is dyed in the same bath. Furthermore, a two-bath method may be used in which the dyeing method using the disazo compound of the present invention and the dyeing method for fibers other than cellulose fibers are combined to dye cellulose fibers and other fibers from separate baths. It is also possible to adopt the law.
（実施例）
次に、本発明を実施例により更に具体的に説明するが、
本発明は、以〒の実施例に限定されるものではない。(Example) Next, the present invention will be explained in more detail with reference to Examples.
The present invention is not limited to the following examples.
実施例１
（セルロース繊維の染色例）
遊離酸の形で下記構造式（１−１）
％式％（）
で示されるジスアゾ化合物０．２ｔ、芒硝１６ｔ１緩衝
剤としてＮａ２ＨＰＯ４１２Ｈ２００，４ｔおよびＫＨ
２ＰＯ４０，１ｆを水２００ｍｊｌに加えてｐＨ＝７に
調製した染浴に、未シルケット綿メリヤス１゜２を入れ
、３０分を要して１２０’Ｃまで昇温し、同温度で６０
分間染色した後水洗、ソーピンク、水洗、乾燥を行いス
カーレット色の染色物を得た。本染料の染着率は８６ｑ
６と非常に良好で、得られた染色物は極めて濃厚であり
、また、耐塩素堅牢度及び耐汗−日光堅牢度はいずれも
良好であった。Example 1 (Example of dyeing cellulose fibers) 0.2 t of a disazo compound represented by the following structural formula (1-1) in the form of a free acid, 16 t of sodium sulfate, 4 t of Na2HPO412H200, and KH as a buffering agent.
Add 2PO40.1f to 200mjl of water to adjust the pH to 7. Put 1°2 of unmercerized cotton knitted fabric in the dye bath, raise the temperature to 120'C over 30 minutes, and then dye at the same temperature for 60'C.
After dyeing for a minute, washing with water, sowing pink, washing with water, and drying were performed to obtain a scarlet dyed product. The dyeing rate of this dye is 86q
6, which was very good, and the dyed product obtained was extremely rich, and the chlorine fastness and sweat-sunlight fastness were both good.
（前足構造式（１−１）で示されるジスアゾ化合物の製
造例）
遊離酸の形で下式：
で表わされるモノアゾ色素１モル割合と、遊離酸の形で
下式：
で表わされるモノアゾ色素１モル割合を水媒中、３０〜
４０℃で縮合させ、遊離酸の形で下式：で表わされるジ
スアゾ体を製造した。(Production example of a disazo compound represented by the forefoot structural formula (1-1)) 1 molar proportion of a monoazo dye represented by the following formula in the form of a free acid and 1 monoazo dye represented by the following formula in the form of a free acid The molar ratio in an aqueous medium is 30~
Condensation was carried out at 40° C. to produce a disazo compound represented by the following formula in the form of a free acid.
得られたジスアゾ体５．１２を水３００ｍＪに溶解し、
これにニコチン酸１． Ｏｆを加え、９０℃まで加熱し
ｐＨ６にて１２時間反応させた。次いで、塩化カリウム
で塩析、済過、乾燥して、前足構造式（１−１）で示さ
れる本発明のジスアゾ化合物４．６２を得た。The obtained disazo compound 5.12 was dissolved in 300 mJ of water,
Add 1.0% nicotinic acid to this. Of was added, heated to 90°C, and reacted at pH 6 for 12 hours. Next, the mixture was salted out with potassium chloride, filtered, and dried to obtain the disazo compound 4.62 of the present invention represented by the forefoot structural formula (1-1).
実施例２（Ｐ／Ｃ繊維の一浴一段法による染色例）
実施例１記載の構造式（１−ｔ）で示される本発明のジ
スアゾ化合物０．２１及び下記構造式：で示される公知
のポリエステル用モノアゾ分散染料０．２ｆ、芒硝１２
１、緩衝剤としで鵠ＰＯ４０、０２を及びＮａ２Ｂ４Ｏ
７・１０Ｈ２００，１２ｔを水２００ｍ１に加えてｐＨ
６に調製した染浴に、ポリエステル／木綿＝５０：５０
の混紡布１０ｆを入れ、３０分を要して１３０℃まで昇
温し、同温度で６０分間染色した後、水洗、ソーピンク
、水洗、乾燥を行い、同色性良好なスカーレット色の染
色物を得た。Example 2 (Example of dyeing P/C fiber by one-bath one-step method) Disazo compound 0.21 of the present invention represented by the structural formula (1-t) described in Example 1 and the known disazo compound represented by the following structural formula: Monoazo disperse dye for polyester 0.2f, Glauber's salt 12
1. As a buffer, PO40, 02 and Na2B4O
Add 200,12t of 7・10H to 200ml of water and adjust the pH.
Add polyester/cotton = 50:50 to the dye bath prepared in step 6.
10f of blended fabric was added, the temperature was raised to 130°C over 30 minutes, dyed at the same temperature for 60 minutes, washed with water, soaked pink, washed with water, and dried to obtain a scarlet dyed product with good color consistency. Ta.
その結果、セルロース用反応性染料の本発明のスカーレ
ット色ジスアゾ化合物及びポリエステル用のスカーレッ
ト色分散染料の染着性はいずれも非常に良好で、得られ
た染色物は極めて濃厚かつ同色性良好たスカーレット色
を示し、その耐塩素堅ろう度及び耐汗−日光堅ろう度は
いずれも良好であった。As a result, the dyeing properties of the scarlet-colored disazo compound of the present invention, which is a reactive dye for cellulose, and the scarlet-colored disperse dye for polyester were both very good, and the dyed product obtained was a very deep scarlet color with good color constancy. It exhibited good color and its chlorine fastness and sweat-sunlight fastness were both good.
実施例３
遊離酸の形で各構造式を下記第１表に示す９種の本発明
のジスアゾ化合物を、実施例１の（製造例）に準じて合
成し、得られた各化合物の最大吸収波長λｍａｘ （ｎ
ｍ） （水中）を下記第１表に示した。また、これらの
各ジスアゾ化合物を用い、実施例１の（染色例）と同様
にして綿布を染色したところ、いずれも染着率７０％以
上の良好な染色物が得られた。これらの各染色綿布の色
調を下記第１表に示した。Example 3 Nine types of disazo compounds of the present invention whose structural formulas are shown in Table 1 below in the form of free acids were synthesized according to the (manufacturing example) of Example 1, and the maximum absorption of each compound obtained was Wavelength λmax (n
m) (in water) are shown in Table 1 below. Further, when cotton cloth was dyed using each of these disazo compounds in the same manner as in Example 1 (dying example), good dyed products with a dyeing rate of 70% or more were obtained in all cases. The color tone of each of these dyed cotton fabrics is shown in Table 1 below.
第 １ 表
遊離酸の形で一般式：
％式％）
第 １ 表 つづき
（発明の効果）
以上の結果から明らかなように、本発明の新規な水溶性
ジスアゾ化合物は、反応性染料としての適性がとくに優
れ、ｐＨ７以上での通常の染色法においてセルロースに
対し高い染着率を示して濃厚かつ耐塩素堅ろう度及び耐
汗−日光堅ろう度の良好な橙色〜スカーレット色の染色
物が得られるばかりでなく、Ｐ／Ｃ繊維の弱酸性染浴に
おける一浴一段１３０°Ｃ以上の高温染色法においても
、該ジスアゾ化合物をポリエステル用分散染料と併用す
ることにより、同色性良好で濃厚かつ耐塩素堅ろう度及
び耐汗−日光堅ろう度の良好な橙色〜スカーレット色の
染色物が得られる、という工業的価値ある顕著な効果を
奏するものである。Table 1 General formula in the form of free acid: %Formula %) Table 1 Continued (Effects of the invention) As is clear from the above results, the novel water-soluble disazo compound of the present invention is suitable as a reactive dye. It exhibits a high dyeing rate against cellulose in ordinary dyeing methods at pH 7 or above, and can yield orange to scarlet dyed products that are thick and have good chlorine fastness and sweat-sunlight fastness. In addition, even in high-temperature dyeing methods of 130°C or higher per step in a weakly acidic dyeing bath for P/C fibers, by using the disazo compound in combination with a disperse dye for polyester, it can be dyed with good color consistency, richness, and chlorine resistance. This has a remarkable effect of industrial value in that an orange to scarlet colored dyed product with good heat resistance and sweat resistance and sunlight fastness can be obtained.
Claims (2)
ン酸基で置換されていてもよいベンゼン環又は前記いず
れかの基で置換されていてもよいナフタレン環を表わし
、Ｒは水素原子、メチル基、カルバモイル基又はカルボ
キシル基を表わし、Ａ＾■はアニオンを表わす。）で示
される水溶性ジスアゾ化合物。(1) In the form of a free acid, the general formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼...[I] (In the formula, D_z may be substituted with a methyl group, a methoxy group, or a sulfonic acid group. represents a benzene ring or a naphthalene ring which may be substituted with any of the above groups, R represents a hydrogen atom, methyl group, carbamoyl group or carboxyl group, and A^■ represents an anion). Disazo compound.
ン酸基で置換されていてもよいベンゼン環又は前記いず
れかの基で置換されていてもよいナフタレン環を表わし
、Ｒは水素原子、メチル基、カルバモイル基又はカルボ
キシル基を表わし、Ａ＾■はアニオンを表わす。）で示
される水溶性ジスアゾ化合物を用いることを特徴とする
セルロース又はセルロース含有繊維類の染色法。(2) In the form of a free acid, the general formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼...[I] (In the formula, D_z may be substituted with a methyl group, a methoxy group, or a sulfonic acid group. represents a benzene ring or a naphthalene ring which may be substituted with any of the above groups, R represents a hydrogen atom, methyl group, carbamoyl group or carboxyl group, and A^■ represents an anion). A method for dyeing cellulose or cellulose-containing fibers, characterized by using a disazo compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61094363A JPH0619044B2 (en) | 1986-04-23 | 1986-04-23 | Disazo compound and dyeing method using the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61094363A JPH0619044B2 (en) | 1986-04-23 | 1986-04-23 | Disazo compound and dyeing method using the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62250060A true JPS62250060A (en) | 1987-10-30 |
| JPH0619044B2 JPH0619044B2 (en) | 1994-03-16 |
Family
ID=14108222
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61094363A Expired - Lifetime JPH0619044B2 (en) | 1986-04-23 | 1986-04-23 | Disazo compound and dyeing method using the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0619044B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0468922A2 (en) * | 1990-07-24 | 1992-01-29 | Ciba-Geigy Ag | Use of polyazodyes for dyeing leather |
-
1986
- 1986-04-23 JP JP61094363A patent/JPH0619044B2/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0468922A2 (en) * | 1990-07-24 | 1992-01-29 | Ciba-Geigy Ag | Use of polyazodyes for dyeing leather |
| US5176717A (en) * | 1990-07-24 | 1993-01-05 | Ciba-Geigy Corporation | Use of sulfonated polyazo dyes for dyeing leather in brilliant fast red shades |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0619044B2 (en) | 1994-03-16 |
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