JPH04293969A - Liquid composition of direct dye - Google Patents
Liquid composition of direct dyeInfo
- Publication number
- JPH04293969A JPH04293969A JP8114291A JP8114291A JPH04293969A JP H04293969 A JPH04293969 A JP H04293969A JP 8114291 A JP8114291 A JP 8114291A JP 8114291 A JP8114291 A JP 8114291A JP H04293969 A JPH04293969 A JP H04293969A
- Authority
- JP
- Japan
- Prior art keywords
- liquid composition
- dye
- direct
- lithium hydroxide
- parts
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 26
- 239000007788 liquid Substances 0.000 title claims abstract description 25
- 239000000982 direct dye Substances 0.000 title claims abstract description 10
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims abstract description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 30
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 21
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims abstract description 21
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims abstract description 8
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 8
- 235000021286 stilbenes Nutrition 0.000 claims abstract description 8
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims abstract description 6
- FIXVWFINKCQNFG-UHFFFAOYSA-M sodium;4-[(4-aminophenyl)diazenyl]benzenesulfonate Chemical compound [Na+].C1=CC(N)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 FIXVWFINKCQNFG-UHFFFAOYSA-M 0.000 claims abstract description 4
- 238000006482 condensation reaction Methods 0.000 claims description 8
- 239000000975 dye Substances 0.000 abstract description 15
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract description 10
- 239000004202 carbamide Substances 0.000 abstract description 7
- SDCDTWFAOKXZHD-UHFFFAOYSA-L disodium;5-nitro-2-[2-(4-nitro-2-sulfonatophenyl)ethenyl]benzenesulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1C=CC1=CC=C([N+]([O-])=O)C=C1S([O-])(=O)=O SDCDTWFAOKXZHD-UHFFFAOYSA-L 0.000 abstract description 4
- 238000009833 condensation Methods 0.000 abstract description 2
- 230000005494 condensation Effects 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 238000001556 precipitation Methods 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- -1 4-aminoazobenzenesulfonic acid sodium salt Chemical compound 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 229920003043 Cellulose fiber Polymers 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- JCQLAAMILSTQJX-UHFFFAOYSA-L [Na+].[Na+].C1(=C(C(=CC=C1)S(=O)(=O)[O-])S(=O)(=O)[O-])C=CC1=CC=CC=C1 Chemical compound [Na+].[Na+].C1(=C(C(=CC=C1)S(=O)(=O)[O-])S(=O)(=O)[O-])C=CC1=CC=CC=C1 JCQLAAMILSTQJX-UHFFFAOYSA-L 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Coloring (AREA)
Abstract
Description
【０００１】0001
【産業上の利用分野】本発明は濃厚状態で経時的に安定
な橙色のスチルベン系アゾ直接染料の液状組成物に関す
る。FIELD OF THE INVENTION The present invention relates to a liquid composition of an orange stilbene azo direct dye which is stable over time in a concentrated state.
【０００２】0002
【従来の技術】カラーインデックス（以下Ｃ．Ｉ．と略
する）ダイレクトオレンジ３９に代表されるスチルベン
系アゾ直接染料は、紙、パルプの染色のほかセルロ−ス
繊維類の染色に広く使用されているが、そのダスト発生
の問題および作業能率向上のためから、その液状品が多
用されるようになった。しかしながら、スチルベン系ア
ゾ直接染料はその構造上、濃厚な溶液を得にくいことが
一般的に知られており、貯蔵中の結晶析出や品質劣化等
その経時安定性が悪いと言う問題点がある。又、冬期、
寒冷地においては短期間に染料水溶液が固化するという
問題がある。[Prior Art] Stilbene-based azo direct dyes represented by Color Index (hereinafter abbreviated as C.I.) Direct Orange 39 are widely used for dyeing cellulose fibers as well as paper and pulp. However, due to the problem of dust generation and to improve work efficiency, liquid products have come to be used frequently. However, it is generally known that it is difficult to obtain a concentrated solution of stilbene-based azo direct dyes due to their structure, and there are problems such as crystal precipitation during storage, quality deterioration, and poor stability over time. Also, in winter,
In cold regions, there is a problem that dye aqueous solutions solidify in a short period of time.
【０００３】0003
【発明が解決しようとする課題】Ｃ．Ｉ．ダイレクトオ
レンジ３９につき水性媒質中で十分濃厚でかつ長期間放
置しても粘度上昇、結晶析出等をおこさず又寒冷地にお
いても固化しない安定な液状組成物の開発が望まれてい
る。[Problem to be solved by the invention]C. I. It is desired to develop a stable liquid composition for Direct Orange 39 that is sufficiently thick in an aqueous medium and does not cause viscosity increase or crystal precipitation even when left for a long period of time, and does not solidify even in cold regions.
【０００４】0004
【課題を解決するための手段】本発明者らは前記したよ
うな課題を解決すべく鋭意研究を重ねた結果、本発明に
至ったものである。即ち、本発明は
（１）還元剤の存在下、４，４′−ジニトロ−２，２′
−スチルベンジスルホン酸ナトリウム塩と４−アミノア
ゾベンゼン−４′−スルホン酸ナトリウム塩とを水酸化
リチウムあるいは水酸化リチウムと水酸化ナトリウムの
存在下で縮合反応させることにより得られた色素と尿素
、エチレングリコール及びジエチレングリコールから選
ばれる一種又は二種以上を含有するスチルベン系橙色直
接染料の液状組成物
（２）縮合反応に使用する水酸化ナトリウムと水酸化リ
チウムの使用割合が重量比で５０：５０乃至０：１００
である前項１に記載の液状組成物に関する。[Means for Solving the Problems] The present inventors have conducted intensive research to solve the above-mentioned problems, and as a result, they have arrived at the present invention. That is, the present invention provides (1) in the presence of a reducing agent, 4,4'-dinitro-2,2'
- Pigment obtained by condensation reaction of stilbenedisulfonic acid sodium salt and 4-aminoazobenzene-4'-sulfonic acid sodium salt in the presence of lithium hydroxide or lithium hydroxide and sodium hydroxide, and urea and ethylene glycol Liquid composition of stilbene-based orange direct dye containing one or more selected from diethylene glycol and diethylene glycol (2) The weight ratio of sodium hydroxide and lithium hydroxide used in the condensation reaction is 50:50 to 0: 100
The present invention relates to the liquid composition according to item 1 above.
【０００５】本発明における色素成分は水溶媒中で還元
剤の存在下、４，４′−ジニトロ−２，２′−スチルベ
ンジスルホン酸ナトリウム塩と４−アミノアゾベンゼン
スルホン酸ナトリウム塩とのモル比１：１乃至１：２、
好ましくは１：１．３乃至１：１．６の割合の混合物を
水酸化リチウム又は水酸化リチウムと水酸化ナトリウム
を用いて，還元、縮合することにより得られ、生成物は
下記式（１）、式（２）及び式（３）で表される染料を
含む混合物である。４，４′−ジニトロ−２，２′−ス
チルベンジスルホン酸ナトリウム塩と４−アミノアゾベ
ンゼンスルホン酸ナトリウム塩とをアルカリ剤の存在下
で縮合して得られる染料はＣ．Ｉ．ダイレクトオレンジ
３９として知られているが、その構造については明らか
にされていなかった。The dye component in the present invention is prepared by mixing 4,4'-dinitro-2,2'-stilbenedisulfonic acid sodium salt and 4-aminoazobenzenesulfonic acid sodium salt in a molar ratio of 1 in the presence of a reducing agent in an aqueous solvent. :1 to 1:2,
It is obtained by reducing and condensing a mixture preferably in a ratio of 1:1.3 to 1:1.6 using lithium hydroxide or lithium hydroxide and sodium hydroxide, and the product has the following formula (1). , a mixture containing dyes represented by formula (2) and formula (3). The dye obtained by condensing 4,4'-dinitro-2,2'-stilbenedisulfonic acid sodium salt and 4-aminoazobenzenesulfonic acid sodium salt in the presence of an alkaline agent is C.I. I. It is known as Direct Orange 39, but its structure has not been clarified.
【０００６】[0006]
【化１】[Chemical formula 1]
【０００７】[0007]
【化２】[Chemical 2]
【０００８】[0008]
【化３】
（式（１）、（２）及び（３）においてＭはＮａ又はＬ
ｉを示す。）[Image Omitted] (In formulas (1), (2) and (3), M is Na or L
Indicates i. )
【０００９】本発明においてアルカリ剤存在下における
縮合反応は還元反応と同時に行うが、アルカリ剤の存在
下で縮合反応を行った後で還元反応を行ってもよい。さ
らに還元反応は複数の還元剤を用いて反応を２段階に分
けて行うことにより反応を完結させてもよい。還元剤と
してはメタノ−ル、エタノ−ル等のアルコール類、エチ
レングリコール、ジエチレングリコール、トリエチレン
グリコール、グリセロール、モノエタノ−ルアミン、ジ
エタノ−ルアミンのようなヒドロキシアルキルアミン類
、ブドウ糖が挙げられ、これらは一種又は二種以上を任
意に混合してもちいてもよい。還元剤の使用量は水溶媒
に対して３〜３０％（重量％）の範囲に変えることがで
き、好ましくは４〜７％（重量％）の範囲である。In the present invention, the condensation reaction in the presence of an alkali agent is carried out simultaneously with the reduction reaction, but the reduction reaction may be carried out after the condensation reaction in the presence of an alkali agent. Further, the reduction reaction may be completed by performing the reaction in two stages using a plurality of reducing agents. Examples of reducing agents include alcohols such as methanol and ethanol, hydroxyalkylamines such as ethylene glycol, diethylene glycol, triethylene glycol, glycerol, monoethanolamine and diethanolamine, and glucose. Alternatively, two or more types may be arbitrarily mixed and used. The amount of reducing agent used can vary from 3 to 30% (wt%), preferably from 4 to 7% (wt%) based on the water solvent.
【００１０】アルカリ縮合反応に使用する水酸化ナトリ
ウムと水酸化リチウムの使用割合は重量比で５０：５０
乃至０：１００の比率で変えることができる。水酸化リ
チウムの量、又は水酸化リチウムと水酸化ナトリウムの
合計量の水溶媒に対する使用濃度は２〜８％（重量％）
の範囲で変えることができる。還元剤存在下でのアルカ
リ縮合反応は水溶媒中で通常８０〜１１０℃好ましくは
９０℃〜１００℃の温度で１０〜１５時間で実施し得る
。縮合で使用される水の量は生成物中の染料濃度が約１
０〜５０％（重量％）になるように変えることができる
。縮合反応終了後はｐＨが高いので、必要に応じ例えば
酢酸等によりｐＨ７〜９．５の範囲まで中和して前記し
た式（１）乃至式（３）で表される染料を含む水溶液を
えることが出来る。[0010] The ratio of sodium hydroxide and lithium hydroxide used in the alkaline condensation reaction is 50:50 by weight.
The ratio can be changed from 0:100. The amount of lithium hydroxide or the total amount of lithium hydroxide and sodium hydroxide used in the water solvent is 2-8% (wt%)
can be changed within the range. The alkaline condensation reaction in the presence of a reducing agent can be carried out in an aqueous solvent at a temperature of usually 80 to 110°C, preferably 90 to 100°C, for 10 to 15 hours. The amount of water used in the condensation is such that the dye concentration in the product is approximately 1
It can be changed from 0 to 50% (weight %). After completion of the condensation reaction, the pH is high, so if necessary, neutralize with acetic acid etc. to a pH range of 7 to 9.5 to obtain an aqueous solution containing the dyes represented by the above formulas (1) to (3). I can do it.
【００１１】上記のように調製されたスチルベン系アゾ
直接染料を含有する水溶液に尿素、エチレングリコ−ル
及びジエチレングリコ−ルから選ばれる一種又は二種を
添加し更に必要に応じ水及びその他の添加剤を添加混合
し本発明の液状組成物をえる。上記において尿素、エチ
レングリコ−ル、ジエチレングリコ−ルは単独であるい
はこれらを混合して組成物に１０〜４０％好ましくは２
０〜３０％（重量比）含有するように、又水は組成物中
に１０〜７０％好ましくは３０〜５０％（重量比）含ま
れるように添加される。得られた本発明の液状組成物は
必要によりろ過等により挟雑物を除去してもよい。又そ
の他の添加剤として防黴剤、キレ−ト剤等を添加するこ
とも出来る。One or two selected from urea, ethylene glycol and diethylene glycol are added to the aqueous solution containing the stilbene azo direct dye prepared as described above, and further water and other additives are added as necessary. are added and mixed to obtain the liquid composition of the present invention. In the above, urea, ethylene glycol, and diethylene glycol may be used alone or in combination in the composition in an amount of 10 to 40%, preferably 2.
Water is added in an amount of 0 to 30% (by weight), and water is added to the composition in an amount of 10 to 70%, preferably 30 to 50% (by weight). If necessary, impurities may be removed from the obtained liquid composition of the present invention by filtration or the like. Furthermore, other additives such as antifungal agents and chelating agents may also be added.
【００１２】本発明の液状組成物は常温では６ケ月以上
、又−５℃程度の低温でも３ケ月以上結晶の析出を起こ
さず、長期間にわたる保存安定性に優れている。本発明
の液状組成物は常法により紙の染色又はセルロ−ス繊維
の染色に用いて優れた染色物を与える。例えば紙の染色
においては内添法、サイズプレス法、コ−ト法等が採用
される。本発明の液状組成物は他の染料と配合して使用
することも出来る。例えば、本発明の液状組成物と赤色
直接染料を色素分重量比で５０：５０乃至９９：１の範
囲で混合し必要に応じ尿素をさらに添加することにより
褐色の染色性、保存性に優れた濃厚水溶液を得ることが
できる。[0012] The liquid composition of the present invention does not cause crystal precipitation for more than 6 months at room temperature, and for more than 3 months even at a low temperature of about -5°C, and has excellent long-term storage stability. The liquid composition of the present invention can be used for dyeing paper or cellulose fibers by conventional methods to give excellent dyed products. For example, in paper dyeing, the internal addition method, size press method, coating method, etc. are employed. The liquid composition of the present invention can also be used in combination with other dyes. For example, by mixing the liquid composition of the present invention and a red direct dye in a pigment weight ratio in the range of 50:50 to 99:1 and further adding urea if necessary, excellent brown dyeing properties and storage stability can be obtained. Concentrated aqueous solutions can be obtained.
【００１３】[0013]
【実施例】以下実施例をあげ本発明を更に詳細に説明す
る。[Examples] The present invention will be explained in more detail with reference to Examples below.
【００１４】実施例１
４、４′−ジニトロ−２、２′−スチルベンジスルホン
酸ナトリウム２８８部に水１１００部を加え、９５℃に
昇温して溶解する。これに４−アミノアゾベンゼン−４
′−スルホン酸ナトリウム塩２４５部を加え、更に４８
％水酸化ナトリウム水溶液７３部、水酸化リチウム３７
部、エチレングリコール２７部を続けて加え約１００℃
で１０時間反応させる。次いでブドウ糖３０部を加え８
５〜９０℃で２時間反応させる。次いで、酢酸３７部を
加えｐＨ９〜９．５としたのち、尿素１７４０部を加え
、溶解させる。その後、溶解液を濾過しゴミ等を除去し
、水を加え、全量を５８００部に調整し本発明の液状組
成物を得た。この液状組成物は常温（２０〜２５℃）で
６カ月以上、低温（−５℃）で３カ月以上結晶の析出及
び固化しない優れた貯蔵安定性を示した。Example 1 1100 parts of water was added to 288 parts of sodium 4,4'-dinitro-2,2'-stilbenedisulfonate, and the mixture was heated to 95°C to dissolve. To this, 4-aminoazobenzene-4
Add 245 parts of '-sulfonic acid sodium salt, and add 48 parts of
% sodium hydroxide aqueous solution 73 parts, lithium hydroxide 37 parts
1 part and 27 parts of ethylene glycol were added successively at approximately 100°C.
Let it react for 10 hours. Next, add 30 parts of glucose and
React at 5-90°C for 2 hours. Next, 37 parts of acetic acid was added to adjust the pH to 9 to 9.5, and then 1,740 parts of urea was added and dissolved. Thereafter, the solution was filtered to remove dust and the like, and water was added to adjust the total amount to 5,800 parts to obtain a liquid composition of the present invention. This liquid composition exhibited excellent storage stability without crystal precipitation or solidification for more than 6 months at room temperature (20-25°C) and for more than 3 months at low temperature (-5°C).
【００１５】パルプに対して５％（重量比以下同様）の
上記で得られた液状組成物を染浴に添加し、１５分後サ
イズ剤をパルプに対して１％添加した。更に１０分後硫
酸バンドをパルプに対して３％添加しさらに２０分間染
色することにより、着色度の高い橙色の抄紙を得る事が
出来た。The above-obtained liquid composition was added to the dye bath in an amount of 5% based on the pulp (the same applies below), and after 15 minutes, a sizing agent was added in an amount of 1% based on the pulp. After a further 10 minutes, 3% sulfuric acid was added to the pulp, and the pulp was dyed for another 20 minutes, making it possible to obtain highly colored orange paper.
【００１６】実施例２
実施例１における４８％水酸化ナトリウム７３部の代わ
りに水酸化リチウム７４部を用いるほかは実施例１と同
様な方法により、本発明の液状組成物を得た。この液状
組成物は実施例１と同様にパルプを着色度の高い橙色に
染色でき、又貯蔵安定性に優れていた。Example 2 A liquid composition of the present invention was obtained in the same manner as in Example 1 except that 74 parts of lithium hydroxide was used instead of 73 parts of 48% sodium hydroxide in Example 1. Similar to Example 1, this liquid composition was able to dye pulp in a highly colored orange color and had excellent storage stability.
【００１７】実施例３
実施例１で得た液状組成物１７０部にＣ．Ｉ．ダイレク
トレッド８３：１の本体分７．５％を含有する液状染料
３２部を加え、更に尿素４８部、更に水を加えて、全体
を３１９部に調整し結晶析出のない安定な液状染料を得
た。この液状染料は常温（２０〜２５℃）で６カ月以上
、低温（−５℃）で３カ月以上結晶の析出及び固化しな
い優れた貯蔵安定性を示した。この液状染料でパルプを
染色すると着色度の高い褐色の紙を得ることができた。Example 3 170 parts of the liquid composition obtained in Example 1 was added with C.I. I. Add 32 parts of liquid dye containing 7.5% of Direct Red 83:1, further add 48 parts of urea, and further add water to adjust the total to 319 parts to obtain a stable liquid dye without crystal precipitation. Ta. This liquid dye exhibited excellent storage stability without crystal precipitation or solidification for more than 6 months at room temperature (20-25°C) and for more than 3 months at low temperature (-5°C). When pulp was dyed with this liquid dye, brown paper with a high degree of coloring could be obtained.
【００１８】[0018]
【発明の効果】４，４′−ジニトロ−２，２′−スチル
ベンジスルホン酸ナトリウム塩と４−アミノアゾベンゼ
ンスルホン酸ナトリウム塩とを還元剤とアルカリ剤の存
在下で縮合して得られる直接染料（Ｃ．Ｉ．ダイレクト
オレンジ３９）につき経時安定性に優れた濃厚な液状組
成物が得られた。Effects of the Invention: A direct dye ( A thick liquid composition with excellent stability over time was obtained for C.I. Direct Orange 39).
Claims (2)
，２′−スチルベンジスルホン酸ナトリウム塩と４−ア
ミノアゾベンゼン−４′−スルホン酸ナトリウム塩とを
水酸化リチウムあるいは水酸化リチウムと水酸化ナトリ
ウムの存在下で縮合反応させることにより得られた色素
と尿素、エチレングリコール及びジエチレングリコール
から選ばれる一種又は二種以上を含有するスチルベン系
橙色直接染料の液状組成物Claim 1: 4,4'-dinitro-2 in the presence of a reducing agent.
, 2'-stilbenzene-4'-sulfonic acid sodium salt and 4-aminoazobenzene-4'-sulfonic acid sodium salt in the presence of lithium hydroxide or lithium hydroxide and sodium hydroxide. A liquid composition of a stilbene-based orange direct dye containing one or more selected from , ethylene glycol, and diethylene glycol.
酸化リチウムの使用割合が重量比で５０：５０乃至０：
１００である請求項１に記載の液状組成物Claim 2: The weight ratio of sodium hydroxide and lithium hydroxide used in the condensation reaction is from 50:50 to 0:
100. The liquid composition according to claim 1, wherein
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8114291A JPH04293969A (en) | 1991-03-22 | 1991-03-22 | Liquid composition of direct dye |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8114291A JPH04293969A (en) | 1991-03-22 | 1991-03-22 | Liquid composition of direct dye |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04293969A true JPH04293969A (en) | 1992-10-19 |
Family
ID=13738163
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8114291A Pending JPH04293969A (en) | 1991-03-22 | 1991-03-22 | Liquid composition of direct dye |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04293969A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000037973A1 (en) * | 1998-12-18 | 2000-06-29 | Nippon Kayaku Kabushiki Kaisha | Color polarizer with support for liquid crystal projector and color liquid crystal projector |
| WO2002081580A1 (en) * | 2001-04-04 | 2002-10-17 | Nippon Kayaku Kabushiki Kaisha | Aqueous ink composition, water-soluble dye composition and ink-jet recording method |
| JP2005068416A (en) * | 2003-08-07 | 2005-03-17 | Nippon Kayaku Co Ltd | Aqueous black ink composition and colored material |
-
1991
- 1991-03-22 JP JP8114291A patent/JPH04293969A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000037973A1 (en) * | 1998-12-18 | 2000-06-29 | Nippon Kayaku Kabushiki Kaisha | Color polarizer with support for liquid crystal projector and color liquid crystal projector |
| US6552849B1 (en) | 1998-12-18 | 2003-04-22 | Nippon Kayaku Kabushiki Kaisha | Color polarizer with support for liquid crystal projector and color liquid crystal projector |
| WO2002081580A1 (en) * | 2001-04-04 | 2002-10-17 | Nippon Kayaku Kabushiki Kaisha | Aqueous ink composition, water-soluble dye composition and ink-jet recording method |
| US7056374B2 (en) | 2001-04-04 | 2006-06-06 | Nippon Kayaku Kabushiki Kaisha | Aqueous ink composition, water-soluble dye composition and ink-jet recording method |
| JP2005068416A (en) * | 2003-08-07 | 2005-03-17 | Nippon Kayaku Co Ltd | Aqueous black ink composition and colored material |
| JP4605638B2 (en) * | 2003-08-07 | 2011-01-05 | 日本化薬株式会社 | Aqueous black ink composition and colored body |
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