JPS62250059A - Disazo compound and method for dyeing using same - Google Patents
Disazo compound and method for dyeing using sameInfo
- Publication number
- JPS62250059A JPS62250059A JP61094362A JP9436286A JPS62250059A JP S62250059 A JPS62250059 A JP S62250059A JP 61094362 A JP61094362 A JP 61094362A JP 9436286 A JP9436286 A JP 9436286A JP S62250059 A JPS62250059 A JP S62250059A
- Authority
- JP
- Japan
- Prior art keywords
- group
- dye
- formula
- dyeing
- disazo compound
- 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 29
- 238000000034 method Methods 0.000 title claims description 22
- 239000000835 fiber Substances 0.000 claims abstract description 19
- 239000002253 acid Substances 0.000 claims abstract description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 7
- 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
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims abstract description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims abstract description 4
- 229920002678 cellulose Polymers 0.000 claims description 14
- 239000001913 cellulose Substances 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 239000000975 dye Substances 0.000 abstract description 24
- 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 6
- 239000012736 aqueous medium Substances 0.000 abstract description 3
- 238000004040 coloring Methods 0.000 abstract description 2
- 229920003002 synthetic resin Polymers 0.000 abstract description 2
- 239000000057 synthetic resin Substances 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- 239000000123 paper Substances 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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 239000004744 fabric Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000985 reactive dye Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 210000004744 fore-foot Anatomy 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- 238000005406 washing Methods 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
- 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 210000002683 foot Anatomy 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 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 2
- 239000010446 mirabilite Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 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 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
- 239000004952 Polyamide Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000000872 buffer Substances 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
- 230000000694 effects Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011487 hemp 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
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 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
- 229920002647 polyamide Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000001694 spray drying Methods 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
Landscapes
- Coloring (AREA)
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（例えば、とく
にポリエステル／セルロース混合繊維等）を黄色に染色
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 (for example, especially polyester/cellulose mixed fibers, etc.) yellow. 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
「Ｐ／Ｃ繊維」と略記する。）を、分散染料と反応性染
料の併用によシー浴一段、１３０℃で染色する方法が検
討されており、かかる方法で黄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６０−８６１６
８号公報及び特開昭６０−２６０６５７号公報にはそれ
ぞれ遊離酸の形で下記構造式（ａ）及び（ｂ〕で示され
る水溶性染料化合物が記載されている。(Prior Art) In recent years, a method of dyeing polyester/cellulose mixed fibers (hereinafter simply referred to as "P/C fibers") using a combination of disperse dyes and reactive dyes in a sea bath at 130°C has been developed. Compounds that can be used as yellow reactive dyes in this method include, for example, Japanese Patent Application Laid-Open No. 60-8616.
No. 8 and Japanese Unexamined Patent Publication No. 60-260657 respectively describe water-soluble dye compounds represented by the following structural formulas (a) and (b) in the form of free acids.
（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（ａ）で示される従来の化合
物には、
させることによりセルロースに対して高反応、性を示す
ようにしたものである点で、経済的 ゝ見地からは不利
である、
■ 塩素濃度２０〜４０ｐｐｍ程度における塩素堅ろう
度が不充分で、より高い塩素堅ろう度が要望される、
等の問題点があった。また、上記構造式〔ｂ〕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よシ
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ｐ
Ｈ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 (a) is economically disadvantageous in that it exhibits high reactivity and properties towards cellulose by There were problems such as: (1) the chlorine fastness was insufficient at a chlorine concentration of about 20 to 40 ppm, and a higher chlorine fastness was desired; In addition, the conventional compound represented by the above structural formula [b] is a preferable compound that exhibits a high reaction rate with cellulose at a pH of 7 or higher during dyeing, even if there is only one reactive group 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. In order to prevent the decomposition of polyester disperse dyes used in conjunction with this, P during dyeing is
Considering that H is particularly preferably in the weakly acidic range such as 6 and 5, the conventional compounds are clearly unsuitable for one-bath one-step dyeing of such P/C fibers. Ta.
本発明は、上記の従来の問題点を解決しうる黄色系反応
性染料として有用で新規な水溶性ジスアゾ系化合物及び
それを用いる染色法の提供を目的とする。The present invention aims to provide a novel water-soluble disazo compound useful as a yellow 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、Ｘは水素原子、メチ
・ル基、メトキシ基。(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 a free acid having the following general formula (1) (wherein, X is a hydrogen atom, a methyl group, or a methoxy group).
アセチルアミノ基、ベンゾイルアミノ基又はカルバモイ
ルアミノ基を表わし、Ｙは水素原子。It represents an acetylamino group, a benzoylamino group or a carbamoylamino group, and Y is a hydrogen atom.
メチル基、エチル基、メトキシ基又はエトキシ基を表わ
し、Ｒは水素原子、メチル基、カルバモイル基、カルボ
キシル基を表わし、Ａｅはアニオンを表わし、ｍは２又
は３の整数を表わす。）で示される水溶性ジスアゾ系化
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。かかる本発明の水溶性ジスアゾ系化合物
において、Ａｏはピリジン核の窒素原子の正電荷とバラ
ンスさせるに必要な負電荷であり、その具体例としては
ＯＨ、Ｃ４−、Ｂｒ−、Ｆ−等が挙げられる。It represents a methyl group, an ethyl group, a methoxy group, or an ethoxy group, R represents a hydrogen atom, a methyl group, a carbamoyl group, or a carboxyl group, Ae represents an anion, and m represents an integer of 2 or 3. ), and a method for dyeing cellulose or cellulose-containing fibers □, which is characterized by using the water-soluble disazo compound. In the water-soluble disazo compound of the present invention, Ao is a negative charge necessary to balance the positive charge of the nitrogen atom of the pyridine nucleus, and specific examples thereof include OH, C4-, Br-, F-, etc. It will be done.
本発明の前足一般式（１）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％
（式中、Ｘ１Ｙ及びｍ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〕（式中、Ｘ１Ｙ及びｍ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ＩＪ）で示されるジスアゾ体とする。次いで、この
ジスアゾ体に、下−記一般式（Ｖ）
店ＲＣＶ〕
（式中、Ｒは前足一般式（１）におけると同一の意義を
有する。）で示される化合物を、水媒中、７０℃〜１０
０℃で反応せしめ、前足一般式ＣＩ）で示される本発明
の化合物を得ることができる。The disazo compound represented by the forefoot general formula (1) of the present invention can be produced, for example, as follows. That is, the 1 molar proportion of the dye represented by the following general formula % formula % (in the formula, X1Y and m have the same meaning as in the front foot general formula (1)) in the form of free acid, and One molar proportion of the dye represented by the following general formula CI] (wherein X1Y and m have the same meanings as in the front paw general formula [1]) is condensed to form a free acid in the following general formula IJ). It is the disazo compound shown. Next, a compound represented by the following general formula (V) (wherein R has the same meaning as in the forefoot general formula (1)) was added to this disazo compound in an aqueous medium for 70 min. °C~10
By reacting at 0° C., compounds of the invention of the general formula CI) can be obtained.
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黄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
。(Function) The yellow water-soluble disazo compound of the present invention thus obtained can be 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.
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（、ｐＨ５，６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。That is, the compound of the present invention not only shows a high reactivity with cellulose in the usual dyeing method for cellulose fibers carried out at pH 7 or higher (130
Since it exhibits a high reaction rate with cellulose without being decomposed even in a dyeing method carried out at a high temperature of .degree. C. or higher, it is particularly suitable for use in combination with a disperse dye for polyester in a one-bath one-step dyeing method for P/C fibers.
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を染色するに必要な染
料１９例えばＣｏ１ｏｕｒ Ｉｎｄθ・Ｘ（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 method for dyeing fibers using the disazo compound of the present invention, dyes necessary for dyeing non-cellulose fibers, such as disperse dyes described in Co1our Indθ・X (3rd edition), are simultaneously added to the dye bath. In addition, 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（１）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す） ＩＪウム塩又は
カリウム塩の単一または混合物で通常０．５〜５．０ｔ
／ｌ程度）、そして必要に応じて電解質（塩化ナトリウ
ムまたは硫酸す） ＩＪウム等を通常１〜１５ｏｆ／ｌ
程度、特に好ましくは４０〜８ｏり／Ｊ）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
１００〜１５０℃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, use the disazo compound represented by the above general formula (1) and the dye bath during dyeing to a pH of 5 to 10.
(For example, acids such as carbonic acid, phosphoric acid, acetic acid, citric acid, etc. and their acid salts) IJum salt or potassium salt, singly or as a mixture, usually 0.5 to 5.0 t
/l), and if necessary, an electrolyte (sodium chloride or sulfuric acid), usually 1 to 15 of/l.
A good dyeing process can be achieved by preparing a dye bath to which the dyestuff is added (especially preferably 40 to 8 o/J), adding cellulose fibers to this dye bath, and heating at a temperature of 100 to 150°C for 30 to 50 minutes. It can be carried out.
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、本発明の前足一般式ＣＩ）で示され
るジスアゾ化合物と、上記Ｃｏ１ｏｕｒ 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。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. that are manufactured by mixing cellulose fibers with other fibers, such as polyester fibers, a disazo compound represented by the forefoot general formula CI) of the present invention, Co1our Index above
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、以下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％（１１）
で示される本発明のジスアゾ化合物０２ｖ１芒硝１６ｆ
１緩衝剤としテＮａ２ＨＰｏ４１２Ｈ２ｏｏ、４２及び
ＫＨ２ＰＯ４０，１ｆを水２００ ｍｌ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１０ｆを
入れ、３０分を要して１２０℃まで昇温し、同温度で６
０分間染色した後水洗、ソーピング、水洗、乾燥を行い
、黄色の染色物を得た。本染料の染着率は８５係と非常
に良好で、得られた染色物は極めて濃厚であり、その耐
光堅ろう度は５級、耐塩素堅ろう度は４−５級（ＪＩＳ
Ｌ０８８４．塩素濃度２０ ｐｐｍ）といずれも良好
であった。Example 1 (Example of dyeing cellulose fiber) Disazo compound 02v1 Glauber's salt 16f of the present invention represented by the following structural formula (1-1) % formula % (11) in the form of free acid
1 As a buffer, add Na2HPo412H2oo,42 and KH2PO40,1f to 200 ml of water to adjust pH=
Put 10 f of unmercerized cotton stockinette into the dye bath prepared in step 7, heat it up to 120°C over 30 minutes, and dye it at the same temperature for 6
After dyeing for 0 minutes, washing with water, soaping, washing with water, and drying were performed to obtain a yellow dyed product. The dyeing rate of this dye is very good at 85 modulus, and the dyed product obtained is extremely rich, its light fastness is grade 5, and its chlorine fastness is grade 4-5 (JIS
L0884. The chlorine concentration was 20 ppm), which was 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 the 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４．７７を水３００ｍｌ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、濾過、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４．５ｇを得た。The obtained disazo compound 4.77 was dissolved in 300 ml 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 4.5 g of the disazo compound 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（１−１）で示される本発明のジ
スアゾ化合物０．２ Ｆ及び下記構造式：で示される公
知のポリエステル用キノフタロン系分散染料０．２ｆ、
芒硝１２ｆ１緩衝剤としてＫＨ２ＰＯ４０，０２Ｆ及び
Ｎａ２Ｂ４Ｏ７・１ｏＨ２０ｏ、１２ｙを水２００ｒＪ
に加えてｐＨ６に調製した染浴に、ポリエステル／木綿
＝５０：５０の混紡布］、 ＯＳ’を入れ、３０分を要
して１３ｏ′Ｃ″ｉ！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
良好な黄色の染色物を得た。Example 2 (Example of dyeing P/C fiber by one-bath one-step method) Disazo compound 0.2F of the present invention represented by the structural formula (1-1) described in Example 1 and a known known compound represented by the following structural formula: Quinophthalone disperse dye for polyester 0.2f,
KH2PO40,02F and Na2B4O7.1oH20o,12y as a buffering agent of Glauber's salt 12f1 in water 200rJ
In addition, a blended fabric of polyester/cotton = 50:50] and OS' were added to a dye bath adjusted to pH 6, and the temperature was raised to 13o'C''i! over 30 minutes, and then at the same temperature for 60 minutes. After dyeing, washing with water, sowing pink, washing with water, and drying were performed to obtain a yellow dyed product with good color constancy.
その結果、セルロース用反応性染料の本発明の黄色ジス
アゾ化合物及びポリエステル用の黄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
かつ同色性良好な黄色を示し、その耐光堅ろう度、耐塩
素堅ろう度はいずれも良好であった。As a result, the dyeing properties of the yellow disazo compound of the present invention, which is a reactive dye for cellulose, and the yellow disperse dye for polyester were both very good, and the dyed products obtained exhibited an extremely deep yellow color with good isochromaticity. The light fastness and chlorine 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８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（ｎｍ
） （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多以上
の良好な染色物が得られ、それらの耐塩素堅ろう度は４
−５級といずれも良好であった。これらの各染色布の色
調を下記第１表に示した。Example 3 Eight 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 (nm
) (in water) are shown in Table 1 below. In addition, 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, and their chlorine resistance was degree is 4
-5 grade and all were good. The color tone of each of these dyed fabrics is shown in Table 1 below.
（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光堅ろう度１、耐
塩素堅ろう度のいずれも良好な黄色の染色物が得られる
ばかシでなく、Ｐ／Ｃ繊維の弱酸性染浴における一浴一
段１３０℃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顕著な効果を奏するものである
。(Effects of the Invention) As is clear from the above results, the novel water-soluble disazo compound of the present invention has particularly excellent suitability as a reactive dye, and has a high dyeability against cellulose in a normal dyeing method at pH 7 or higher. It is not only possible to obtain a yellow dyed product that shows a high adhesion rate and has a good light fastness of 1 and chlorine fastness, but it is also possible to obtain a dyed product of 130°C or higher per bath in a weakly acidic dyeing bath for P/C fibers. Even in the high-temperature dyeing method, by using the disazo compound together with a disperse dye for polyester,
It has good color constancy, is thick, and exhibits remarkable durability.
Claims (2)
ルアミノ基、ベンゾイルアミノ基又はカルバモイルアミ
ノ基を表わし、Ｙは水素原子、メチル基、エチル基、メ
トキシ基又はエトキシ基を表わし、Ｒは水素原子、メチ
ル基、カルバモイル基、カルボキシル基を表わし、Ａ＾
■はアニオンを表わし、ｍは２又は３の整数を表わす。 ）で示される水溶性ジスアゾ系化合物。(1) In the form of free acid, the following general formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼... [I] (In the formula, X is a hydrogen atom, methyl group, methoxy group, acetylamino group, benzoyl represents an amino group or a carbamoylamino group, Y represents a hydrogen atom, methyl group, ethyl group, methoxy group or ethoxy group, R represents a hydrogen atom, methyl group, carbamoyl group, or carboxyl group, A^
(2) represents an anion, and m represents an integer of 2 or 3. ) A water-soluble disazo compound.
ルアミノ基、ベンゾイルアミノ基又はカルバモイルアミ
ノ基を表わし、Ｙは水素原子、メチル基、エチル基、メ
トキシ基又はエトキシ基を表わし、Ｒは水素原子、メチ
ル基、カルバモイル基、カルボキシル基を表わし、Ａ＾
■はアニオンを表わし、ｍは２又は３の整数を表わす。 ）で示される水溶性ジスアゾ系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 free acid, the following general formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼... [I] (In the formula, X is a hydrogen atom, methyl group, methoxy group, acetylamino group, benzoyl represents an amino group or a carbamoylamino group, Y represents a hydrogen atom, methyl group, ethyl group, methoxy group or ethoxy group, R represents a hydrogen atom, methyl group, carbamoyl group, or carboxyl group, A^
(2) represents an anion, and m represents an integer of 2 or 3. 1. A method for dyeing cellulose or cellulose-containing fibers, characterized by using a water-soluble disazo compound shown in ).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61094362A JPH0619043B2 (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 |
|---|---|---|---|
| JP61094362A JPH0619043B2 (en) | 1986-04-23 | 1986-04-23 | Disazo compound and dyeing method using the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62250059A true JPS62250059A (en) | 1987-10-30 |
| JPH0619043B2 JPH0619043B2 (en) | 1994-03-16 |
Family
ID=14108191
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61094362A Expired - Lifetime JPH0619043B2 (en) | 1986-04-23 | 1986-04-23 | Disazo compound and dyeing method using the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0619043B2 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5328995A (en) * | 1990-07-02 | 1994-07-12 | Ciba-Geigy Corporation | Azo dyes containing triazine middle components and a 1,4-phenylene-2,5-disubstituted coupling component |
| EP0714955A1 (en) * | 1994-12-02 | 1996-06-05 | Ciba-Geigy Ag | Azodyestuffs, process for their preparation and the use thereof |
| WO2002092698A1 (en) * | 2001-05-11 | 2002-11-21 | Nippon Kayaku Kabushiki Kaisha | Disazo compound, reactive dye composition, and methods of dyeing cellulose or cellulose-containing fiber |
| WO2006103414A3 (en) * | 2005-03-31 | 2007-06-07 | Fujifilm Imaging Colorants Ltd | Disazodyes for ink-jet printing |
-
1986
- 1986-04-23 JP JP61094362A patent/JPH0619043B2/en not_active Expired - Lifetime
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5328995A (en) * | 1990-07-02 | 1994-07-12 | Ciba-Geigy Corporation | Azo dyes containing triazine middle components and a 1,4-phenylene-2,5-disubstituted coupling component |
| EP0714955A1 (en) * | 1994-12-02 | 1996-06-05 | Ciba-Geigy Ag | Azodyestuffs, process for their preparation and the use thereof |
| WO2002092698A1 (en) * | 2001-05-11 | 2002-11-21 | Nippon Kayaku Kabushiki Kaisha | Disazo compound, reactive dye composition, and methods of dyeing cellulose or cellulose-containing fiber |
| US7029503B2 (en) | 2001-05-11 | 2006-04-18 | Nippon Kayaku Kabushiki Kaisha | Disazo compound, reactive dye composition, and method of dyeing cellulose or cellulose-containing fibers |
| KR100790467B1 (en) * | 2001-05-11 | 2008-01-02 | 니폰 가야꾸 가부시끼가이샤 | Disazo compound, reactive dye composition, and method of dyeing cellulose or cellulose-containing fibers |
| WO2006103414A3 (en) * | 2005-03-31 | 2007-06-07 | Fujifilm Imaging Colorants Ltd | Disazodyes for ink-jet printing |
| US7704309B2 (en) | 2005-03-31 | 2010-04-27 | Fujifilm Imaging Colorants Limited | Disazodyes for ink-jet printing |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0619043B2 (en) | 1994-03-16 |
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