JPS6221828B2 - - Google Patents
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- Publication number
- JPS6221828B2 JPS6221828B2 JP54079310A JP7931079A JPS6221828B2 JP S6221828 B2 JPS6221828 B2 JP S6221828B2 JP 54079310 A JP54079310 A JP 54079310A JP 7931079 A JP7931079 A JP 7931079A JP S6221828 B2 JPS6221828 B2 JP S6221828B2
- Authority
- JP
- Japan
- Prior art keywords
- parts
- concentrated solution
- water
- weight
- present
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
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- Luminescent Compositions (AREA)
Description
本発明は、
一般式（）
（式中、Ｍは水素またはアルカリ金属原子、
X1、X2は−SO3Mまたは−SO2NH2を表わす。）
で示されるビストリアジニルアミノスチルベン
誘導体、
ジエチレングリコールおよび／またはトリエ
チレングリコール40−70重量％（対濃厚溶液組
成物）
水５−25重量％（対濃厚溶液組成物）
よりなることを特徴とする螢光性物質の濃厚溶液
組成物に関する。
本発明の目的とするところは、一般式（）で
示される螢光性物質の安定な高濃度溶液を提供す
ることにある。
従来、螢光性物質の多くは、微粉末の形で製造
販売されている。しかしながら、この微粉末染料
は、これを取扱う場合、種々の欠点を有する。た
とえば、乾燥、粉砕、配合、詰め換えの工程を必
要とし、また前記工程および使用の際の秤量、溶
解等の工程において常に不快な粉塵の発生をとも
ない、損失も少なくない。
このようなことから、螢光性物質を濃厚溶液化
する試みも種々行なわれており、一部実用化もな
されている。しかしながら、従来知られている一
般式（）の化合物の濃厚溶液は、決して安定性
が充分でなく、長期間の保存において螢光性物質
の結晶が析出したり、増白性が低下したり又、多
くの場合高価なトリエタノールアミン等を用いて
アミン塩化することが必要であり、製造コスト上
からも有利とは言えなかつた。
本発明者らは、一般式（）で示される螢光性
物質の濃厚溶液について、安定で工業的に安価な
ものを得るべく検討した結果、前記本発明に到達
した。
本発明は、溶解剤として水の他、ジエチレング
リコールおよび／またはトリエチレングリコール
を、それぞれ特定の割合で使用する点が特徴であ
り、得られた濃厚溶液は三ケ月間貯蔵しても結晶
が析出することもなく安定であり、また増白性が
低下したりすることもない。更に悪臭などもなく
工業的に安価に製造できる。
本発明の組成物は任意の方法で製造することが
できる。たとえば、一般式（）のビストリアジ
ニルアミノスチルベン誘導体の縮合反応後、塩析
または酸析し、過してウエツトケーキとし、こ
れを溶解剤に加熱溶解し、必要により水量を蒸
発、蒸発等により調整し、不溶解分を去して濃
厚溶液とするか、あるいは縮合反応後、必要によ
り蒸発、蒸留等により水量を調整した後、溶解剤
を添加し、不溶解分を去して濃厚溶液とするこ
とができる。
本発明の組成物には、他に公知の溶解剤、たと
えば尿素などを適宜併用してもさしつかえない。
本発明において、組成物の水の割合は５重量％
以上の水分を含有することが必要である。また25
重量％以上では安定性不良となるため好ましくな
い。特に好ましい水の割合は５−20重量％であ
る。溶解剤の組成物に対する割合は、40−70重量
％であることが必要である。40重量％未満では安
定な濃厚溶液組成物が得られない。また70重量％
を越える場合は、安定で濃厚な溶液が得られな
い。
次に、本発明の螢光性物質について、公知の
種々の溶解剤を使用して安定性比較試験を行なつ
た結果を示す。表−１より本発明の濃厚溶液組成
物はきわめて安定性良好であることがわかる。
The present invention is based on the general formula () (In the formula, M is hydrogen or an alkali metal atom,
X 1 and X 2 represent -SO 3 M or -SO 2 NH 2 . ), characterized by consisting of diethylene glycol and/or triethylene glycol 40-70% by weight (based on the concentrated solution composition) and water 5-25% by weight (based on the concentrated solution composition) The present invention relates to concentrated solution compositions of fluorescent substances. An object of the present invention is to provide a stable, highly concentrated solution of a fluorescent substance represented by the general formula (). Conventionally, many fluorescent substances have been manufactured and sold in the form of fine powder. However, this fine powder dye has various disadvantages when handling it. For example, it requires the steps of drying, crushing, blending, and refilling, and in the steps of weighing, dissolving, etc. during use, unpleasant dust is always generated, resulting in considerable losses. For this reason, various attempts have been made to turn fluorescent substances into concentrated solutions, and some have even been put into practical use. However, the conventionally known concentrated solutions of the compound of general formula () are never sufficiently stable, and when stored for a long period of time, crystals of fluorescent substances may precipitate, whitening properties may decrease, or However, in many cases, it is necessary to convert the amine into a salt using expensive triethanolamine or the like, and it cannot be said to be advantageous in terms of production cost. The present inventors have arrived at the present invention as a result of studies to obtain a stable and industrially inexpensive concentrated solution of a fluorescent substance represented by the general formula (). The present invention is characterized in that, in addition to water, diethylene glycol and/or triethylene glycol are used in specific proportions as a solubilizing agent, and crystals do not precipitate even if the resulting concentrated solution is stored for three months. It is stable and does not cause any decrease in whitening properties. Furthermore, there is no bad odor and it can be produced industrially at low cost. The composition of the present invention can be manufactured by any method. For example, after a condensation reaction of a bistriazinylaminostilbene derivative of the general formula (), salting out or acid precipitation is performed, a wet cake is obtained, which is heated and dissolved in a dissolving agent, and the amount of water is adjusted by evaporation, evaporation, etc. if necessary. Then, remove the insoluble matter to make a concentrated solution, or after the condensation reaction, adjust the amount of water by evaporation, distillation, etc. if necessary, then add a solubilizer and remove the insoluble matter to make a concentrated solution. be able to. The composition of the present invention may also contain other known solubilizing agents, such as urea, as appropriate. In the present invention, the proportion of water in the composition is 5% by weight.
It is necessary to contain more than the above amount of water. 25 again
If it is more than % by weight, it is not preferable because it will result in poor stability. A particularly preferred proportion of water is 5-20% by weight. The proportion of solubilizer to the composition should be 40-70% by weight. If the amount is less than 40% by weight, a stable concentrated solution composition cannot be obtained. Also 70% by weight
If it exceeds 20%, a stable and concentrated solution cannot be obtained. Next, the results of a comparative stability test on the fluorescent substance of the present invention using various known solubilizing agents will be shown. Table 1 shows that the concentrated solution composition of the present invention has extremely good stability.
【表】【table】
【表】
次に実施例をあげて本発明を説明する。文中部
とあるのは重量部を意味する。
実施例 １
塩化シアヌル369部、４・4′−ジアミノスチル
ベン２・2′−ジスルホン酸ソーダ414部、メタニ
ル酸ソーダ390部、ジエタノールアミン210部とか
ら公知の方法により縮合し、反応の各段階におい
て生成する酸をソーダ灰により中和して得られる
下記式(1)の化合物
を含む反応液を塩化ナトリウムで塩析し、得られ
たウエツトケーキ82部（化合物(1)を32部含む）
に、ジエチレングリコール46部を加え、80−90℃
に加熱してケーキを溶解する。
減圧で水24部を除去した後、90−95℃で不溶物
質を別する。螢光性物質32部、ジエチレングリ
コール46部、水20部、塩化ナトリウム２部からな
る濃厚溶液が得られた。この濃厚溶液は、３ケ月
以上安定で、結晶の析出および吸光値の低下は認
められなかつた。
実施例 ２
実施例１において、メタニル酸ソーダ390部に
代えてメタニル酸カリウム422部を使用して得ら
れた下記式(2)の化合物
32部を含む反応液300部を58部まで濃縮する。水
20部を含むスラリーが得られる。これにトリエチ
レングリコール46部を加え、螢光性物質を溶解し
た後、不溶物質を別する。螢光性物質32部、ト
リエチレングリコール46部、水20部および塩化ナ
トリウム２部とからなる濃厚溶液が得られた。
この濃厚溶液は３ケ月以上安定であり、結晶の
析出および吸光値の低下は認められなかつた。
実施例 ３
実施例１でメタニル酸ソーダ390部に換え、ｐ
−スルホンアミドアニリン344部を使用して得ら
れた下記式(3)の化合物
32部を含む反応液300部を塩化ナトリウムで塩析
し、得られたウエツトケーキ85部にジエチレング
リコール50部を加え、80−90℃でケーキを溶解す
る。減圧で水31部を除去した後、90−95℃で不溶
の結晶を別する。螢光性物質32部、ジエチレン
グリコール50部、水16部および塩化ナトリウム２
部からなる濃厚溶液が得られた。
この濃厚溶液は、３ケ月以上安定で、結晶の析
出および吸光値の低下は認められなかつた。[Table] Next, the present invention will be explained with reference to Examples. The text middle part means the weight part. Example 1 369 parts of cyanuric chloride, 414 parts of sodium 4,4'-diaminostilbene 2,2'-disulfonate, 390 parts of sodium methanilate, and 210 parts of diethanolamine were condensed by a known method, and the product was produced at each stage of the reaction. Compound of the following formula (1) obtained by neutralizing the acid with soda ash 82 parts of the obtained wet cake (containing 32 parts of compound (1)) were salted out with sodium chloride.
Add 46 parts of diethylene glycol to 80-90℃
Heat to dissolve the cake. After removing 24 parts of water under reduced pressure, the insoluble material is separated off at 90-95°C. A concentrated solution was obtained consisting of 32 parts of fluorescent substance, 46 parts of diethylene glycol, 20 parts of water and 2 parts of sodium chloride. This concentrated solution was stable for more than 3 months, and no crystal precipitation or decrease in absorbance value was observed. Example 2 Compound of the following formula (2) obtained by using 422 parts of potassium methanate in place of 390 parts of sodium methanate in Example 1 Concentrate 300 parts of the reaction solution containing 32 parts to 58 parts. water
A slurry containing 20 parts is obtained. 46 parts of triethylene glycol is added to this to dissolve the fluorescent substance, and then the insoluble substances are separated. A concentrated solution was obtained consisting of 32 parts of fluorescent substance, 46 parts of triethylene glycol, 20 parts of water and 2 parts of sodium chloride. This concentrated solution was stable for more than 3 months, and neither crystal precipitation nor decrease in absorbance value was observed. Example 3 In Example 1, 390 parts of sodium methanate was replaced with p.
-Compound of the following formula (3) obtained using 344 parts of sulfonamide aniline 300 parts of the reaction solution containing 32 parts was salted out with sodium chloride, 50 parts of diethylene glycol was added to 85 parts of the resulting wet cake, and the cake was dissolved at 80-90°C. After removing 31 parts of water under reduced pressure, the insoluble crystals are separated at 90-95°C. 32 parts of fluorescent substance, 50 parts of diethylene glycol, 16 parts of water and 2 parts of sodium chloride
A concentrated solution consisting of 50% was obtained. This concentrated solution was stable for more than 3 months, and no crystal precipitation or decrease in absorbance value was observed.
Claims (1)
X1、X2は−SO3Mまたは−SO2NH2を表わす。） で示されるビストリアジニルアミノスチルベン
誘導体、 ジエチレングリコールおよび／またはトリエ
チレングリコール40−70重量％（対濃厚溶液組
成物）、 水５−25重量％（対濃厚溶液組成物）よりな
ることを特徴とする螢光性物質の濃厚溶液組成
物。[Claims] 1 General formula () (In the formula, M is hydrogen or an alkali metal atom,
X 1 and X 2 represent -SO 3 M or -SO 2 NH 2 . ), characterized by comprising 40-70% by weight of diethylene glycol and/or triethylene glycol (based on the concentrated solution composition) and 5-25% by weight of water (based on the concentrated solution composition) A concentrated solution composition of a fluorescent substance.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7931079A JPS562354A (en) | 1979-06-22 | 1979-06-22 | Concentrated solution of fluorescent material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7931079A JPS562354A (en) | 1979-06-22 | 1979-06-22 | Concentrated solution of fluorescent material |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS562354A JPS562354A (en) | 1981-01-12 |
| JPS6221828B2 true JPS6221828B2 (en) | 1987-05-14 |
Family
ID=13686275
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7931079A Granted JPS562354A (en) | 1979-06-22 | 1979-06-22 | Concentrated solution of fluorescent material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS562354A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61290499A (en) * | 1985-06-18 | 1986-12-20 | 日本電気株式会社 | Enunciation speed varying voice synthesizer |
-
1979
- 1979-06-22 JP JP7931079A patent/JPS562354A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS562354A (en) | 1981-01-12 |
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