JPH0794617B2 - Aqueous liquid composition - Google Patents
Aqueous liquid compositionInfo
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- JPH0794617B2 JPH0794617B2 JP62173946A JP17394687A JPH0794617B2 JP H0794617 B2 JPH0794617 B2 JP H0794617B2 JP 62173946 A JP62173946 A JP 62173946A JP 17394687 A JP17394687 A JP 17394687A JP H0794617 B2 JPH0794617 B2 JP H0794617B2
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- dye
- liquid composition
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- formula
- aqueous liquid
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Description
【発明の詳細な説明】 産業上の利用分野 本発明は染料の液状組成物に関する。更に詳しくは反応
性染料の貯蔵安定性良好な濃厚水性液状組成物に関す
る。FIELD OF THE INVENTION The present invention relates to liquid compositions of dyes. More specifically, it relates to a concentrated aqueous liquid composition having good storage stability of a reactive dye.
従来の技術 従来反応性染料においては他の種属の染料と同様粉塵が
立たない、計量、運搬、溶解等における取り扱いが容易
である等の理由でその濃厚水性液状品が多用されてい
る。そしてそのような液状品の貯蔵安定性をより向上さ
せるために脱塩処理を施したり、ε−カプロラクタム、
ポリビニルピロリドン等の助剤を添加するということが
行われている。遊離酸として 式（Ia） （式（Ia）においてＲは−NHC2H4SO3Hを表す） で表される反応性染料においてそのナトリウム塩あるい
はカリウム塩である染料の液状組成物は脱塩処理を施し
たり前記したような助剤を加えるだけでは低温乃至室温
での長期間貯蔵における結晶析出防止、液状品そのもの
の凍結防止等の品質目標が達成できない。殊に染料濃度
が高い場合においてはその困難性が大きい。2. Description of the Related Art Conventional reactive dyes are often used as concentrated dyes because they are free from dust as in the case of dyes of other species and are easy to handle in measurement, transportation, dissolution and the like. Then, a desalting treatment is performed to further improve the storage stability of such a liquid product, ε-caprolactam,
It is practiced to add an auxiliary agent such as polyvinylpyrrolidone. Formula (Ia) as free acid (Wherein R represents —NHC 2 H 4 SO 3 H in the formula (Ia)), the liquid composition of the dye which is the sodium salt or potassium salt of the reactive dye represented by the formula (Ia) is desalted or treated as described above. It is not possible to achieve quality goals such as prevention of crystal precipitation during long-term storage at low temperature to room temperature and prevention of freezing of the liquid product by simply adding such auxiliary agents. Especially when the dye concentration is high, the difficulty is great.
発明が解決しようとする問題点 前記式（Ia）で示される反応性染料につき低温乃至室温
（凡そ−10℃乃至30℃）において長期間保存しても染料
液自体の凍結や染料の決勝析出を起こさない濃厚水性液
状組成物が求められている。Problems to be Solved by the Invention Even when the reactive dye represented by the formula (Ia) is stored at a low temperature to room temperature (about -10 ° C to 30 ° C) for a long period of time, the dye solution itself is frozen and the final deposition of the dye is prevented. There is a need for a concentrated aqueous liquid composition that does not occur.
問題点を解決する為の手段 本発明者らは前記したような問題点を解決すべく鋭意研
究を重ねた結果本発明に至った。即ち本発明は式（Ｉ） （式（Ｉ）中Ｒは−NHC2H4SO3Mを、Ｍはそれぞれ独立し
てLi 、Na 、Ｋ 又は NH（C2H4OH）３を表す。但し
Ｍのうち少なくとも１個のＭはLi 又は NH（C2H4OH）
３を表すものとする。） で表される反応性染料の濃厚水性液状組成物を提供す
る。Means for Solving the Problems The inventors of the present invention have diligently studied to solve the above problems.
As a result of repeated research, the present invention has been achieved. That is, the present invention has the formula (I)(R in formula (I) is -NHC2HFourSO3M and M are independent
Li , Na , K Or NH (C2HFourOH)ThreeRepresents However
At least one of M is Li Or NH (C2HFourOH)
ThreeShall be represented. ) Provides a concentrated aqueous liquid composition of a reactive dye represented by
It
本発明の液状組成物につき説明する。The liquid composition of the present invention will be described.
本発明において対象とされる式（Ia）で示される反応性
染料はそれ自体公知の染料であり、例えば次式（ａ） で示されるモノアゾ色素母体とタウリンと塩化シアヌー
ルとを任意の順序で縮合することによってえられる。The reactive dye represented by the formula (Ia) which is an object of the present invention is a dye known per se, for example, the following formula (a) It can be obtained by condensing a monoazo dye matrix represented by, taurine, and cyanuric chloride in any order.
本発明の水性液状組成物においては式（Ｉ）で示される
反応性染料の３又は４個のスルホン酸基の少なくとも１
個が−SO3Li基又は−SO3NH（C2H4OH）３基を形成してい
るものであるが、このような塩を形成せしめる方法とし
ては例えば式（Ia）の反応性染料を合成するにあたっ
て、溶解剤、中和剤として通常に用いられるソーダ灰、
重曹、カセイソーダ、カセイカリ等の代りにその一部又
は全部を水酸化リチウム又はトリエタノールアミンにお
き代えることにより３又は４個のスルホン酸基のうちの
少なくとも１個のスルホン酸基を−SO3Li基又は−SO3NH
（C2H4OH）３基に変えられる。この際式（Ia）の反応性
染料１モルに対して１〜10モルより好ましくは２〜４モ
ルの水酸化リチウム又はトリエタノールアミンが用いら
れる。即ち前記したような量の水酸化リチウム又はトリ
エタノールアミンが式（ａ）のアゾ色素合成時あるいは
該アゾとタウリンと塩化シアヌールとの縮合時（１次縮
合及び２次縮合）に分割して加えることも出来るし全量
を１時に加えることも出来る。In the aqueous liquid composition of the present invention, at least 1 of 3 or 4 sulfonic acid groups of the reactive dye represented by the formula (I) is used.
Individual group forms a —SO 3 Li group or a —SO 3 NH (C 2 H 4 OH) 3 group. As a method for forming such a salt, for example, a reactive dye of the formula (Ia) is used. When synthesizing, soda ash, which is usually used as a dissolving agent and a neutralizing agent,
At least one of the 3 or 4 sulfonic acid groups is replaced with -SO 3 Li by substituting lithium hydroxide or triethanolamine for a part or all of it in place of baking soda, caustic soda, caustic potash and the like. Group or --SO 3 NH
Can be converted to (C 2 H 4 OH) 3 groups. In this case, 1 to 10 mol, preferably 2 to 4 mol of lithium hydroxide or triethanolamine is used per 1 mol of the reactive dye of the formula (Ia). That is, the above-mentioned amount of lithium hydroxide or triethanolamine is dividedly added during the synthesis of the azo dye of the formula (a) or during the condensation of the azo, taurine and cyanuric chloride (primary condensation and secondary condensation). You can also add the whole amount at 1 o'clock.
このようにしてえられた反応液を蒸発濃縮するか、より
好ましくは逆浸透法によって脱塩濃縮することによって
本発明の濃厚水溶液状組成物がえられる。逆浸透法にお
ける過材としてはポリベンツイミダゾロン、セルロー
スアセテート、部分けん化セルロースアセテート等が用
いられる。このようにしてえられた本発明の液状組成物
は通常20〜40％の染料分を含有するものであり必要に応
じて水を加えて濃度が調整される。The concentrated aqueous composition of the present invention can be obtained by evaporating and concentrating the reaction solution thus obtained, or more preferably desalting and concentrating by the reverse osmosis method. Polybenzimidazolone, cellulose acetate, partially saponified cellulose acetate, and the like are used as an overactive material in the reverse osmosis method. The liquid composition of the present invention thus obtained usually contains a dye content of 20 to 40%, and the concentration is adjusted by adding water if necessary.
なお本発明の濃厚水性液状組成物にポリアクリル酸ナト
リウム、ε−カプロラクタム等を加えたり、該液状組成
物のpHを6.0〜8.5に調製することが経時安定性を一層向
上させる手段として必要に応じて採用される。It should be noted that sodium polyacrylate, ε-caprolactam or the like may be added to the concentrated aqueous liquid composition of the present invention, or the pH of the liquid composition may be adjusted to 6.0 to 8.5 as a means for further improving the stability over time. Will be adopted.
本発明の水性液状組成物は低温あるいは室温における長
期の保存にも安定で組成物が凍結を起こしたり結晶の析
出を起こしたりしないものであり、通常の染色法に従い
木綿、レーヨン又はこれらを含有する混紡繊維の染色に
供される。The aqueous liquid composition of the present invention is stable even at long-term storage at low temperature or room temperature and does not cause freezing or precipitation of crystals, and contains cotton, rayon or these according to a usual dyeing method. Used for dyeing mixed fiber.
実施例 本発明は実施例によって更に詳細に説明する。実施例中
部は重量部を、％は重量％を意味する。Examples The present invention will be described in more detail by examples. In the examples, "part" means "part by weight" and "%" means "% by weight".
実施例１ ２−ナフチルアミン−3,6,8−トリスルホン酸の２ナト
リウム塩のフリー酸換算104部をジアゾ化し、48部の重
曹の存在下で38.7部のｍ−アミノフェニル尿素とカップ
リングしモノアゾ色素ベースを得た。これを塩化シアヌ
ル47.3部と０〜５℃で12部のトリエタノールアミンを用
いpH6〜７に保ちながら一時縮合を行った。モノアゾ色
素ベースの残存を認めなくなった時点で33.6部のタウリ
ンを加え、84部のトリエタノールアミンでpH6.7〜7.3に
中和しながら徐々に昇温させ、50℃を保つことによって
２次縮合を完結させた。Example 1 104 parts by weight of 2-naphthylamine-3,6,8-trisulfonic acid disodium salt in terms of free acid was diazotized and coupled with 38.7 parts of m-aminophenylurea in the presence of 48 parts of sodium bicarbonate. A monoazo dye base was obtained. This was temporarily condensed with 47.3 parts of cyanuric chloride and 12 parts of triethanolamine at 0 to 5 ° C while maintaining the pH at 6 to 7. When the remaining monoazo dye base is no longer observed, add 33.6 parts of taurine and gradually warm it while neutralizing it to pH 6.7-7.3 with 84 parts of triethanolamine, and maintain the temperature at 50 ° C to carry out the secondary condensation. Was completed.
この反応液につき逆浸透装置にて脱塩濃縮処理を行い濃
縮された水性液状組成物をえた。（550g） なお逆浸透装置にはポリベンツイミダゾロン膜（帝人エ
ンニアリング社製）を用い膜面積200cm2、25〜35Kg/cm2
の圧力で処理を行った。The reaction solution was desalted and concentrated by a reverse osmosis apparatus to obtain a concentrated aqueous liquid composition. (550g) Incidentally, a polybenzimidazolone membrane (manufactured by Teijin Enniaring Co., Ltd.) was used for the reverse osmosis device, and the membrane area was 200 cm 2 , 25 to 35 kg / cm 2.
The treatment was carried out at a pressure of.
この液状組成物中の染料構造を分析した結果式（II）で
示される染料において４個のＭのうち１個は NH（C2H4
OH）3,3個はNa である染料であった。染料濃度は30％
でありNaCl 0.2％,Na2SO4 0.05％を含有していた。As a result of analyzing the dye structure in this liquid composition, the formula (II)
In the dyes shown, one of the four M is NH (C2HFour
OH)3, 3 are Na Was a dye. Dye concentration is 30%
And NaCl 0.2%, Na2SOFour It contained 0.05%.
実施例２ ２−ナフチルアミン−3,6,8−トリスルホン酸の２ナト
リウム塩のフリー酸換算104部をジアゾ化し、トリエタ
ノールアミン63部を用いながら38.7部のｍ−アミノフェ
ニル尿素とカップリングを行いモノアゾ色素ベースを得
た。このものに塩化シアヌル47.3部を加え０〜５℃で40
部のトリエタノールアミンを用いpH6〜７に保ちながら
１次縮合を行った。続いて実施例１と同様にして２次縮
合を行い、得られた反応液につき実施例と同様にして逆
浸透法により脱塩・濃縮処理を施し濃縮された液状組成
物を得た。（450g）この液状組成物中に含まれる染料は
式（II）の染料において４個のＭのうち、２個はHN
（CH2CH2OH）3,2個はNa である染料であった。又染
料濃度は36％であった。 Example 2 2-Naphthyl 2-naphthylamine-3,6,8-trisulfonic acid
Diazotized 104 parts of free acid equivalent of the selenium salt,
38.7 parts of m-aminophen using 63 parts of nolamine
Coupling with nilurea yields a monoazo dye base
It was Add 47.3 parts of cyanuric chloride to this and add 40 at 0-5 ° C.
While keeping the pH 6 to 7 with some triethanolamine
Primary condensation was performed. Then, in the same manner as in Example 1, secondary compression is performed.
The reaction mixture obtained was mixed in the same manner as in the Example.
Liquid composition concentrated by desalting and concentration by permeation method
I got a thing. (450g) The dye contained in this liquid composition is
Of the four M's in the dye of formula (II), two are HN
(CH2CH2OH)3, 2 are Na Was a dye. Matazome
The material concentration was 36%.
実施例３ 実施例１に準じてモノアゾ色素ベースを合成し、続いて
10％のLiOH水溶液を使用して塩化シアヌル47.3部との１
次縮合を０〜５℃,pH6〜７で行った。続いて33.6部のタ
ウリンを加え、同じく10％のLiOH水溶液を用いてpH6.8
〜7.5に中和しながら徐々に昇温させ、50℃に保ち２次
縮合を完結した。この反応液につき逆浸透法による脱
塩、濃縮を施して濃縮された水性液状組成物を得た。
（450g）この液状組成物につき分析したところ式（II）
の染料において４個のＭのうち２個がLi で２個がNa
である染料が含有されていた。又染料の含有率は35％で
あった。Example 3 A monoazo dye base was synthesized according to Example 1, followed by
1 with 47.3 parts cyanuric chloride using 10% LiOH aqueous solution
Subcondensation was carried out at 0-5 ° C, pH 6-7. Then 33.6 copies
Urine was added and the pH was adjusted to 6.8 using 10% LiOH aqueous solution.
Secondary temperature is gradually raised while neutralizing to ~ 7.5
The condensation is complete. This reaction solution was removed by reverse osmosis.
Salt and concentration were performed to obtain a concentrated aqueous liquid composition.
(450 g) When this liquid composition was analyzed, the formula (II)
2 of 4 M in the dye And 2 are Na
Contained a dye. The dye content is 35%
there were.
実施例４ 実施例１の２−ナフチルアミン−3,6,8−トリスルホン
酸２ナトリウム塩の代りに２カリウム塩を用い、実施例
１に準じて染料合成・脱塩・濃縮を行ない濃縮された水
性液状組成物を得た。（550g）この組成物には式（II）
の染料において４個のＭのうち１個がNa 及びNH （C2
H4OH）3,2個がＫ である染料が含有されていた。（染
料の含有率30％） 実施例５ ２−ナフチルアミン−3,6,8−トリスルホン酸２カリウ
ム塩のフリー酸換算104部をジアゾ化し、48部の重曹存
在下で38.7部のｍ−アミノフェニル尿素とカップリング
し、モノアゾ色素ベースを得た。これを塩化シアヌル4
7.3部と０〜５℃で40部のトリエタノールアミンを用
い、pH6〜7.5に保ちながら１次縮合を行った。続いてタ
ウリン33.6部を加え、120部の10％LiOHを用いてpH7〜7.
5に中和しながら徐々に昇温させ50℃を保つことによっ
て２次縮合を完結させた。更に、反応液を脱塩・濃縮し
濃縮された水性液状組成物を得た。（540g）この組成物
には式（II）の染料において４個のＭのうち１個がN
a ,Li及びHN （C2H4OH）３で２個がＫ である染料が
含有されていた。（染料の含有率30％） 比較例 本発明によって得られた水性液状組成物の低温に於ける
安定製を測定するためにそれらの組成物を水で希釈して
染料濃度20％の溶液を作成して下記の安定性試験を行っ
た。Example 4 2-naphthylamine-3,6,8-trisulfone of Example 1
Example using dipotassium salt instead of acid disodium salt
Concentrated water obtained by performing dye synthesis, desalting, and concentration according to 1.
A liquid composition was obtained. (550g) This composition has formula (II)
Of the four M's in the dye And NH (C2
HFourOH)3, 2 are K Contained a dye. (Dyeing
Content 30%) Example 5 2-Naphthylamine-3,6,8-trisulfonic acid 2 Kaliu
Diazotized 104 parts of free acid equivalent of sodium salt and 48 parts of baking soda
Coupling with 38.7 parts of m-aminophenylurea
Then, a monoazo dye base was obtained. This is cyanuric chloride 4
Use 7.3 parts and 40 parts triethanolamine at 0-5 ° C
The primary condensation was carried out while maintaining the pH at 6 to 7.5. Then,
Add 33.6 parts of urin and use 120 parts of 10% LiOH to pH 7-7.
By neutralizing the temperature to 5 and gradually raising the temperature to 50 ° C,
To complete the secondary condensation. Furthermore, the reaction solution is desalted and concentrated.
A concentrated aqueous liquid composition was obtained. (540g) This composition
In the dye of formula (II), one of the four M is N
a , Li and HN (C2HFourOH)ThreeAnd two are K The dye is
It was contained. (Dye content 30%) Comparative Example At low temperature of the aqueous liquid composition obtained by the present invention
Dilute those compositions with water to measure stability
Prepare a solution with 20% dye concentration and perform the stability test below.
It was
下記の染料（IV、Ｖ及びVI）の合成反応液を全て逆浸透
法によって脱塩・濃縮し無機塩含有量は最終調整液中で
0.5％以下となる様にした。比較の対象としては下記式
（IV），（Ｖ），（VI）の構造を有する染料の溶液を用
いた。All reaction solutions of the following dyes (IV, V and VI) were desalted and concentrated by the reverse osmosis method, and the inorganic salt content was adjusted in the final adjustment solution.
It was set to 0.5% or less. For comparison, solutions of dyes having the structures of the following formulas (IV), (V) and (VI) were used.
また、各染料溶液を20％濃度に調整するにあたり、ポリ
アクリル酸ナトリウムを対液１％添加した。 Further, when adjusting the concentration of each dye solution to 20%, 1% of sodium polyacrylate was added to the liquid.
表中○は完溶状態、△はわずかに結晶の析出が認められ
る状態、×はほぼ全体に結晶が析出又は凍結した状態を
示す。 In the table, ◯ indicates a completely dissolved state, Δ indicates a state in which slight crystal precipitation is observed, and x indicates a state in which crystals are almost entirely precipitated or frozen.
又、実施例４の液状組成物から20％濃度液を調製する際
にε−カプロラクタムを10％添加した調製液を作成した
ところ、30日後まで完溶状態であった。（−５℃保管） 応用例 実施例１で得られた本発明の液状組成物から調製された
染料分20％を含む液状組成物を用いて下記組成の色湖を
作成し木綿布に印捺し、102℃,10分間スチーミングを行
い黄色の捺染染色物を得た。Further, when a 20% concentration liquid was prepared from the liquid composition of Example 4, a preparation liquid containing 10% ε-caprolactam was prepared, and it was in a completely dissolved state until 30 days later. (Storage at −5 ° C.) Application Example Using the liquid composition prepared from the liquid composition of the present invention obtained in Example 1 and containing 20% of dye, a colored lake having the following composition was prepared and printed on a cotton cloth. Steaming was carried out at 102 ° C. for 10 minutes to obtain a yellow print dyed product.
実施例１の本発明の液状組成物から 調製された液状組成物 10部 ５％アルギン酸ナトリウム水溶液 50部 重曹 ２部 尿素 ５部 水 33部 発明の効果 長期の保存にも安定な式（１）で示される反応性染料の
濃厚水性液状組成物が得られた。Liquid composition prepared from the liquid composition of the present invention in Example 1 10 parts 5% sodium alginate aqueous solution 50 parts Baking soda 2 parts Urea 5 parts Water 33 parts Effect of the invention With formula (1) stable for long-term storage A concentrated aqueous liquid composition of the indicated reactive dye was obtained.
Claims (1)
してLi 、Na 、Ｋ 又は NH（C2H4OH）３を表す。但
しＭのうち少なくとも１個のＭはLi 又は NH（C2H4O
H）３を表すものとする。） で表される反応性染料の濃厚水性液状組成物。1. A formula (I)(R in formula (I) is -NHC2HFourSO3M and M are independent
Then Li , Na , K Or NH (C2HFourOH)ThreeRepresents However
At least one of M is Li Or NH (C2HFourO
H)ThreeShall be represented. ) A concentrated aqueous liquid composition of a reactive dye represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62173946A JPH0794617B2 (en) | 1987-07-14 | 1987-07-14 | Aqueous liquid composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62173946A JPH0794617B2 (en) | 1987-07-14 | 1987-07-14 | Aqueous liquid composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6420268A JPS6420268A (en) | 1989-01-24 |
| JPH0794617B2 true JPH0794617B2 (en) | 1995-10-11 |
Family
ID=15969998
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62173946A Expired - Lifetime JPH0794617B2 (en) | 1987-07-14 | 1987-07-14 | Aqueous liquid composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0794617B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013022044A1 (en) | 2011-08-09 | 2013-02-14 | 日本化薬株式会社 | Gray ink composition for ink jet printing and method for printing fibers using same |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013035951A (en) * | 2011-08-09 | 2013-02-21 | Nippon Kayaku Co Ltd | Golden yellow ink composition for inkjet printing and method for printing fiber using the same |
| JP5943568B2 (en) * | 2011-08-09 | 2016-07-05 | 日本化薬株式会社 | Black ink composition for ink jet printing and fiber printing method using the same |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CH660493A5 (en) * | 1984-12-07 | 1987-04-30 | Ciba Geigy Ag | METHOD FOR PRODUCING CONCENTRATED LOW-SALT AQUEOUS SOLUTIONS OF AMINOTRIAZINYL REACTIVE DYES. |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013022044A1 (en) | 2011-08-09 | 2013-02-14 | 日本化薬株式会社 | Gray ink composition for ink jet printing and method for printing fibers using same |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6420268A (en) | 1989-01-24 |
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