JPS6187760A - Method for improving solubility of methyl orange dye in solvent - Google Patents
Method for improving solubility of methyl orange dye in solventInfo
- Publication number
- JPS6187760A JPS6187760A JP13606184A JP13606184A JPS6187760A JP S6187760 A JPS6187760 A JP S6187760A JP 13606184 A JP13606184 A JP 13606184A JP 13606184 A JP13606184 A JP 13606184A JP S6187760 A JPS6187760 A JP S6187760A
- Authority
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- Japan
- Prior art keywords
- methyl orange
- orange
- chloroform
- complex
- cyclodextrin
- Prior art date
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Abstract
Description
【発明の詳細な説明】
本発明は、メチルオレンジ色素の溶剤溶解性改善方法に
関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for improving the solvent solubility of methyl orange dye.
メチルオレンジは下記構造式
で示される、親水性のアゾ色素で、酸塩基指示薬として
最も広（使われているものの一つである。Methyl orange is a hydrophilic azo dye shown by the structural formula below, and is one of the most widely used acid-base indicators.
しかしながら、その有機溶剤に対する溶解性は。However, its solubility in organic solvents.
アルコール、ピリジン等に若干量溶ける程度で。It is only slightly soluble in alcohol, pyridine, etc.
その他の有機溶剤、特にクロロホルム、エチルエーテル
、ベンゼン、クロルベンゼン等の非極性溶剤には殆んど
溶解しなり為、その分、使用範囲が限られている。即ち
、メチルオレンジの溶剤溶解性が改善されれば１例えば
非水滴定等に更にその用途が広がり、また、それによシ
非水滴定自体もその応用範囲が広がることになる。It is hardly soluble in other organic solvents, especially non-polar solvents such as chloroform, ethyl ether, benzene, and chlorobenzene, and its range of use is therefore limited. That is, if the solvent solubility of methyl orange is improved, its uses will be further expanded to, for example, non-aqueous titration, and the scope of application of non-aqueous titration itself will also be expanded accordingly.
力）かる状況に鑑み１本発明者らは、メチルオレンジの
有機溶剤に対する溶解性を改善するべく鋭意研究を重ね
た結果、特定の修飾シクロデキストリンでこれを包接す
るととｌこより、その目的を達成し得ることを見出し１
本発明を完成するに到った。In view of the above situation, the present inventors have conducted intensive research to improve the solubility of methyl orange in organic solvents, and have found that by including it with a specific modified cyclodextrin, this objective can be achieved. Find out what can be achieved 1
The present invention has now been completed.
即ち１本発明は、一般式
％式％
〔式中１．β−ＣＤはβ−シクロデキス） ＩＪン残基
Ｈ
Ｒ１、Ｒ２は炭素数６以上のアルキル基を表わす。）を
表わす。〕で示される修飾シフロブキスＩ−１ンを用い
ることを特徴とするメチルオレンジの有機溶剤に対する
溶解性改善方法、及び一般式〔■〕で示される修飾シク
ロデキストリノとメチルオレンジとによ多形成される錯
体の発明である。That is, 1 the present invention is based on the general formula % [in the formula 1. (β-CD is β-cyclodex) IJn residue HR R1 and R2 represent an alkyl group having 6 or more carbon atoms. ). ] A method for improving the solubility of methyl orange in organic solvents, which is characterized by using modified cyclodextrino represented by the general formula [■] and methyl orange. This is an invention of a complex.
本発明によれば、メチルオレンジの有機溶剤に対する溶
解性が著しく改善され、これまで殆んど不溶であったク
ロロホルムのような非極性溶剤にも容易に相当量が溶け
ｓ ａｈ塩基の濃度に応答して発色又は変色し得る。従
って、これによジメチルオレンジの応用範囲は極めて広
いものになることが期待できる。According to the present invention, the solubility of methyl orange in organic solvents has been significantly improved, and a considerable amount of methyl orange is easily dissolved in nonpolar solvents such as chloroform, in which it was almost insoluble until now, and responds to the concentration of sah base. may develop or change color. Therefore, it is expected that the range of applications of dimethyl orange will be extremely wide.
本発明の方法によりメチルオレンジがクロロホルム等の
有機溶剤に可溶化される理由は必ずしも明らかではない
が、大凡次の如く考えられる。即ち、一般式ＣＩ）で示
される脂溶性修飾シクロデキストリン（この内、Ｘ＝−
８−Ｒ” のものを（Ｉａ工Ｘ＝−Ｎ−Ｒ” のも
のを（Ｉ ｂ〕とする。）は、例、ｔｔｆジシクロへキ
シル１８−クラウン−６にみられるような金属イオン、
ｖ・強力に配位するような基はなく、主に、疎水性相互
作用を周込た包接作用によって、可溶化を促していると
考えられる。例えばＣＩ＆）の換金についていえば、下
記、（ａ）又は（ａ′）で示すような二つの包接が考え
られる。The reason why methyl orange is solubilized in organic solvents such as chloroform by the method of the present invention is not necessarily clear, but it is thought to be roughly as follows. That is, a lipophilic modified cyclodextrin represented by the general formula CI) (wherein, X=-
8-R'' (Ia engineering
v. There is no group that strongly coordinates, and it is thought that solubilization is promoted mainly by inclusion action involving hydrophobic interactions. For example, regarding the conversion of CI&) into cash, there are two possible inclusions as shown in (a) or (a') below.
（ａ）はメチルオレンジの極性基をＣＩ＆） の極性
のある水酸基によって安定化を与え、メチルオレンジ分
子を（Ｉａ）の分子が包み込むような形で可溶化される
。（ａ′）はクラウンエーテルの場合にやや近い形であ
るが、スルホキシド基の酸素がナトリウム金属と配位し
、その対アニオンとしてメチルオレンジ分子が包接され
ると共にクロロホルム中に可溶化される。どちらの形で
クロロホルム中に可溶化しているかは現時点では不明で
あるが、いずれにしても（ａ） 、 （ａ’）のいずれ
かの形をとっているものと考えられる。一方、 （Ｉ
ｂ〕 の場合には、 （Ｉａ） がメチルオレンジ
と１：ｌで錯体を形成しているのに対し、１：２の錯体
を形成していると考えられ、下記、（ｂ）のような形で
可溶化されると考えられる。In (a), the polar group of methyl orange is stabilized by the polar hydroxyl group of CI&), and the methyl orange molecule is solubilized in such a manner that the molecule of (Ia) is wrapped around it. (a') is somewhat similar to the case of crown ether, but the oxygen of the sulfoxide group coordinates with sodium metal, and the methyl orange molecule is included as a counter anion and is solubilized in chloroform. It is currently unknown in which form it is solubilized in chloroform, but in any case it is thought to be in either form (a) or (a'). On the other hand, (I
b] In the case of (Ia), it is thought that it forms a 1:2 complex with methyl orange, whereas it forms a 1:2 complex, and as shown in (b) below. It is thought to be solubilized in the form of
（ｂ）
一つの（Ｉｂ）の空孔に包接され、外に出ているメチル
オレンジの極性部分を安°定化させるために。(b) In order to stabilize the polar part of methyl orange that is included in one (Ib) vacancy and is exposed to the outside.
もう一つの（Ｉｂ） 分子の水酸基を用いてｌ：２錯体
を形成している。（Ｉａｌの（ａ）の場合との違いは明
確には判らないが、極性基の安定化のうけ方に違いがあ
るものと考えられる。A 1:2 complex is formed using the hydroxyl group of another (Ib) molecule. (The difference between Ial and case (a) is not clearly understood, but it is thought that there is a difference in the way the polar group is stabilized.
以下１本発明の詳細な説明する。The present invention will be explained in detail below.
本発明に用いられる一般式ＣＩＩで示される修飾シクロ
デキストリン誘導体に於て、Ｘで表わされＨ
６以上のアルキル基であることが望ましく１通常は−Ｃ
ａＨｕ −−ＣａＨｎ −−Ｃ，。Ｈｔ＋ 、 −Ｃ＞
＊Ｈｔｓ −−Ｃ＋ｎＨｔ。In the modified cyclodextrin derivative represented by the general formula CII used in the present invention, it is preferable that H represented by X is an alkyl group of 6 or more.
aHu --CaHn --C,. Ht+, -C>
*Hts --C+nHt.
等がより好ましく用いられる。etc. are more preferably used.
本発明で用すられる一般式ＣＩ］で示される修飾シフロ
ブキス２）は自体公知の製法（Ｊ、Ａｍ。The modified sifurobukis 2) represented by the general formula CI used in the present invention can be produced by a method known per se (J, Am.
Ｃｈｅｍ、 Ｓｏｃ、、 １０２ 、７６２ （１９８
０）； Ｔｅｔｒａｈｅｄｒｏｎ。Chem, Soc, 102, 762 (198
0); Tetrahedron.
Ｖｏｌ、 ３９． Ｎｏ、９．１４１７ （１９８３）
等） ニヨ？）、 例ＪＬば下記の合成経路に従って容
易に合成することができる。Vol, 39. No. 9.1417 (1983)
etc.) Niyo? ), Example JL can be easily synthesized according to the following synthetic route.
一般式〔Ｉａで示される修飾シクロデキストリンを用１
／−ａｒメチルオレンジを包接し、有！Ｈ溶剤に可溶化
させる方法を述べると、一般式ＣＩ）に於て。Using a modified cyclodextrin represented by the general formula [Ia]
/-ar includes methyl orange, yes! The method of solubilizing it in a H solvent is described in general formula CI).
Ｘ＝−８−Ｒ’の場合、即ち（Ｉａ）を周込た場合にハ
、メチルオレンジ１モルｌζ対し、 （Ｉａ） ４１モ
ルで、充分であるが１通常はｌ乃至数倍モル用いらし１
例えば、メチルオレンジを適当量、クロロホルムに懸濁
し、これに（Ｉａ）をメチルオレンジと等モル乃至それ
以上の量加えて３０分以上撹拌すレバ、橙黄色澄明なメ
チルオレンジのクロロホルム溶液が容易に得られる。ま
た、 （Ｉａ〕の適当濃度のクロロホルム溶液にメチ
ルオレンジを過剰モル加え、３０分以上撹拌した後不耐
分（固体のメチルオレンジ）を−去すれば、同様に、橙
黄色澄明ナメチルオレンジのクロロホルム溶液が得られ
。When X = -8-R', that is, when (Ia) is incorporated, 41 mol of (Ia) is sufficient for 1 mol ζ of methyl orange, but usually 1 to several times the mol is used. 1
For example, by suspending an appropriate amount of methyl orange in chloroform, adding (Ia) in an amount equal to or more than the methyl orange, and stirring for 30 minutes or more, a clear orange-yellow chloroform solution of methyl orange can be easily obtained. can get. Similarly, if an excess molar amount of methyl orange is added to a chloroform solution of (Ia) at an appropriate concentration, and after stirring for 30 minutes or more, the intolerant portion (solid methyl orange) is removed, an orange-yellow clear solution of methyl orange can be obtained. A chloroform solution is obtained.
この溶液を濃縮乾固することによシ、修飾シクロデキス
トリンＣＩａ）−メチルオレンジ錯体（修６シクロデキ
ストリン包接メチルオレンジ）の橙色固体が得られる。By concentrating this solution to dryness, an orange solid of modified cyclodextrin CIa)-methyl orange complex (modified cyclodextrin clathrate methyl orange) is obtained.
この錯体は再びクロロホルムに可溶で、＃縮前のクロロ
ホルム溶液と同一のＵＶスペクトルを与える。尚、乾燥
メチルオレンジの粉末をクロロホルムに懸濁し、振とう
してもクロロホルムは全く着色しない。This complex is again soluble in chloroform and gives the same UV spectrum as the chloroform solution before condensation. Note that even if dried methyl orange powder is suspended in chloroform and shaken, chloroform does not color at all.
また、一般式ＣＩ〕に於て、Ｘ＝−Ｎ−Ｒ” の場合
、即ち〔Ｉｂ〕を用いた場合には、メチルオレンジ１モ
ルに対し、（Ｉｂ：ｌは２モル必要であり１通常２乃至
数倍モル用いられ１例えば、メチルオレンジを適当量、
クロロホルムに懸濁し、これに［：Ｉｂ：ｌ ラメチル
オレンジの２倍モル乃至それ以上の量加えて３０分以上
撹拌すれば、橙黄色澄明なメチルオレンジのクロロホル
ム溶液が得られる。In addition, in the general formula CI], when X = -N-R'', that is, when [Ib] is used, (Ib:l is required to be 2 moles and 1 is usually 1 mole per mole of methyl orange. For example, an appropriate amount of methyl orange is used,
By suspending the suspension in chloroform, adding twice or more moles of [:Ib:l methyl orange] and stirring for 30 minutes or more, a clear orange-yellow chloroform solution of methyl orange can be obtained.
また、 （Ｉｂ）の適当濃度のクロロホルム溶液にメ
チルオレンジを過剰モル加え、３０分以上撹拌した後不
醪分を炉去すれば、同様に、橙黄色澄明なメチルオレン
ジのクロロホルム溶液が得られ、この溶液を濃縮乾固す
れば、修飾シクロデキスト１１／ＣＩｂ）−メチルオレ
ンジ錯体の橙色固体が得られる。この錯体はクロロホル
ム番こ可溶であシ、濃縮前のクロロホルム溶液ト同一の
ＵＶスペクトルを与える。In addition, by adding an excess molar amount of methyl orange to a chloroform solution of (Ib) at an appropriate concentration, stirring for 30 minutes or more, and then removing the insoluble matter in an oven, a clear orange-yellow chloroform solution of methyl orange can be similarly obtained, When this solution is concentrated to dryness, an orange solid of modified cyclodext 11/CIb)-methyl orange complex is obtained. This complex is soluble in chloroform and gives the same UV spectrum as the chloroform solution before concentration.
以上述べた如く１本発明は、従来有機溶剤に難溶であっ
たメチルオレンジ色素を特定の修飾シクロデキストリン
で包接することによシ、これを可溶化させる方法を提供
するものであり、非水滴定等の分析の分野を始めとして
斯業に貢献するところ大なるものである。As described above, the present invention provides a method for solubilizing methyl orange dye, which has conventionally been poorly soluble in organic solvents, by including it with a specific modified cyclodextrin. His contributions to this industry are significant, including in the field of analysis such as titration.
以下に実施例を挙げて本発明を更に詳細に説明する。The present invention will be explained in more detail with reference to Examples below.
実施例１゜
試験管にメチルオレンジ５０ｑを秤量シ、ヘプタキス（
６−ドデシルスルフィニル−６−デオキシ）−β−シク
ロデキストリンの各濃度のクロロホルム溶液５ ａｔを
加えた。室温で約３０分間部とうした後、不溶分を済過
して除き、クロロホルムで５倍に希釈して夫々４２０ｎ
ｍ （メチルオレンジの極大吸収波長）に於ける吸光度
を測定した。Example 1 Weighed 50q of methyl orange in a test tube, and added heptakis (
5 at of a chloroform solution of each concentration of 6-dodecylsulfinyl-6-deoxy)-β-cyclodextrin was added. After stirring at room temperature for about 30 minutes, insoluble matter was removed, diluted 5 times with chloroform, and 420 nm each was diluted with chloroform.
The absorbance at m (maximum absorption wavelength of methyl orange) was measured.
結果を第１図に示す。第１図より明らかな如く。The results are shown in Figure 1. As is clear from Figure 1.
修飾シクロデキストリン［Ｉａ、ｌを周込る本発明の方
法によりメチルオレンジはクロロホルムに容易に可溶化
され、溶液の濃度に応じて着色度が強（なる。また、こ
の場合、ヘプタキス（６−ドデシルスルフィニル−６−
デオキシ）−β−シクロデキヌ） ＩＩンはメチルオレ
ンジを１：１のモル比で可溶化していることが判る。By the method of the present invention incorporating modified cyclodextrin [Ia, l, methyl orange is easily solubilized in chloroform, and the degree of coloring becomes strong depending on the concentration of the solution. Sulfinyl-6-
It can be seen that methyl orange is solubilized by (deoxy)-β-cyclodequine in a molar ratio of 1:1.
実施例２゜
実施例１．に於て、ヘプタキス（６−ドデシルスルフィ
ニル−６−デオキシ）−β−シクロデキストＩＩンの代
りに、ヘプタキス（６−ドデシルアミノ−６−デオキシ
）゛−β−シクロデキストリンを用い、実施例１． と
同様に処理して、第２図に示すような結果を得た。第２
図より明らかなように、修飾シクロデキヌ） ＩＩン［
：Ｉｂ）を用いる本発明の方法に於てもメチルオレンジ
はクロロホルムに容易に可溶化され、溶液の濃度に応じ
て１着色度が強くなっている。尚、この場合は、ヘプタ
キス（６−ドデシルアミノ−６−デオキシ）−β−シク
ロデキスｌ−ＩＪンはメチルオレンジを２＝１のモル比
で可溶化していることが判る。Example 2゜Example 1. In Example 1, heptakis(6-dodecylsulfinyl-6-deoxy)-β-cyclodextrin was replaced with heptakis(6-dodecylsulfinyl-6-deoxy)-β-cyclodextrin, and Example 1. The same procedure as above was carried out, and the results shown in FIG. 2 were obtained. Second
As is clear from the figure, modified cyclodequine) IIine [
Even in the method of the present invention using Ib), methyl orange is easily solubilized in chloroform, and the degree of coloring becomes stronger depending on the concentration of the solution. In this case, it can be seen that heptakis(6-dodecylamino-6-deoxy)-β-cyclodextyl-IJ solubilizes methyl orange at a molar ratio of 2=1.
実施例３゜
りａａホルム５ｎｍｌにメチルオレンジ６５５ ｍ９（
２ｍ ｍｏｌ ）を懸濁し、これにヘプタホス（６−ド
デシルスルフィニル−６−デオキシ）−β−７クロデキ
ストＩＩン６ ｊｉ （２，４ｍｍｏｌ ）を加エテ６
０分撹拌すると、橙黄色澄明なメチルオレンジのクロロ
ホルム溶液が得られた。Example 3 Add 655 m9 of methyl orange to 5 nm of aa form (
Heptafos(6-dodecylsulfinyl-6-deoxy)-β-7 clodext II (2.4 mmol) was added to the suspension.
After stirring for 0 minutes, a clear orange-yellow chloroform solution of methyl orange was obtained.
実施例４゜
実施例３．に於て、ヘプタキス（６−ドデシルスルフィ
ニル−６−デオキシ）−β−シクロデキス） ＩＪン６
ｇの代りに、ヘプタキス（６−デシルスルフィニル−６
−デオキシ）−β−シクロデキスＩ−ＩＩン５．６ｇを
用いて実施例３． と同様に処理し、同様の結果を得た
。Example 4゜Example 3. In , heptakis(6-dodecylsulfinyl-6-deoxy)-β-cyclodex) IJn6
g instead of heptakis (6-decylsulfinyl-6
Example 3 using 5.6 g of -deoxy)-β-cyclodex I-II. was processed in the same manner as above, and similar results were obtained.
実施例５、
実施例３．に於て、ヘプタキス（６−ドデシルスルフィ
ニル−６−デオキシ）−β−シクロデキストリン６Ｉの
代りに、ヘプタキス（６−デシルアミノ−６−デオキシ
）−β−シクロデキストリン１０．６ｇを用いて実施例
３． と同様に処理し。Example 5, Example 3. In Example 3, 10.6 g of heptakis (6-decylamino-6-deoxy)-β-cyclodextrin was used in place of heptakis (6-dodecylsulfinyl-6-deoxy)-β-cyclodextrin 6I. Process in the same way.
同様な結果を得た。Similar results were obtained.
実施例６゜
ヘプタキス（６−ドデシルスルフィニル−６−デオキシ
）−β−シクロデキストリンの２．２ ｍ Ｍクロロホ
ルム溶液５ ｍｌにメチルオレンジ７４０〜を加え３０
分間間部うした。振とり後、過剰のメチルオレンジを炉
去し、 Ｐ’Ｍ−を濃縮乾固して錯体の橙色固体３２ｍ
９を得た。本固体はクロロホルムに澄明に爵けて橙黄色
溶液となり、ＵＶ測定を行なうと、４２０ｎｍに極大吸
収波長を示した。Example 6 To 5 ml of a 2.2 mM chloroform solution of heptakis(6-dodecylsulfinyl-6-deoxy)-β-cyclodextrin was added methyl orange 740 to 30
It was a while ago. After shaking, excess methyl orange was removed in an oven, and P'M- was concentrated to dryness to give 32 m of an orange solid complex.
I got a 9. This solid was dissolved in chloroform to become a clear orange-yellow solution, and when UV measurement was performed, it showed a maximum absorption wavelength at 420 nm.
本錯体の溶剤溶解性を表１に示す。Table 1 shows the solvent solubility of this complex.
実施例７゜
ヘプタキス（６−オクチルスルフィニル−６−デオキシ
）−β−シクロデキストリンの２．０ｍＭクロロホルム
溶液５ｍｌにメチルオレンジ７００〜を加え、以下実施
例６． と同様にして、錯体２５ダを得た。本錯体の溶
剤溶解性を表１に示す。Example 7 Methyl Orange 700~ was added to 5 ml of a 2.0 mM chloroform solution of heptakis(6-octylsulfinyl-6-deoxy)-β-cyclodextrin, and the following Example 6. In the same manner as above, a complex of 25 da was obtained. Table 1 shows the solvent solubility of this complex.
表 １ 本発明に係る錯体の溶剤溶解性 但し、＋））：可溶、廿：殆ど可溶、＋：倣溶。Table 1 Solvent solubility of the complex according to the invention However, +)): soluble, 廿: almost soluble, +: imitatively soluble.
−二不溶 を夫々示す。- Indicates two insoluble properties.
実施例８゜
ヘプタキス（６−ドデシルアミノ−６−デオキシ）−β
−シクロデキストリンの２．５ ｍ Ｍクロロホルム溶
液５ ｍｌにメチルオレンジ３００〜ヲ加工。Example 8゜Heptakis(6-dodecylamino-6-deoxy)-β
- Process methyl orange 300 to 5 ml of a 2.5 mM chloroform solution of cyclodextrin.
以下実施例６． と同様にして、橙色の錯体３２ｍ９を
得た。本錯体の溶解性はクロロホルムに可溶ｃ＋＋＋）
で、ベンゼンに殆ど可溶（丑）であった。Example 6 below. In the same manner as above, an orange complex 32m9 was obtained. The solubility of this complex is soluble in chloroform (c+++)
It was almost soluble in benzene.
第１図は実施例１． に関するもの、第２図は実施例２
．に関するもので、どちらも本発明に係る修飾シフロブ
キス） ＩＪン誘導体を用いてメチルオレンジをクロロ
ホルムに可溶化させた際の修飾シフロブキス） ＩＩン
濃度と、４２０ｎｍ（メチルオレンジの極大吸収波長）
に於ける吸光度との関係を示したもので、横軸は修飾シ
フロブキス） ＩＪン濃度（×１０５ｍ０ｌ／ｌ）を、
縦軸は４２０ ｎｍに於ける吸光度Ｃ０Ｄ）を夫々表わ
す。
特許出願人 和光純薬工業株式会社
第 １ 田
濃 度 （Ｘ １０”ｍｏｌｈ）
昭和５２年／／月 ２日FIG. 1 shows Example 1. Fig. 2 shows Example 2.
．． (Modified Schiflovkis, both of which are related to the present invention) Modified Schiflobkis when methyl orange is solubilized in chloroform using an IJ derivative) II concentration and 420 nm (maximum absorption wavelength of methyl orange)
The graph shows the relationship between the absorbance at
The vertical axis represents the absorbance (C0D) at 420 nm. Patent Applicant Wako Pure Chemical Industries, Ltd. No. 1 Concentration (X 10”molh) Month 2, 1978
Claims (2)
＿４〔 I 〕〔式中、β−ＣＤはβ−シクロデキストリ
ン残基を表わし、Ｘは▲数式、化学式、表等があります
▼又は▲数式、化学式、表等があります▼（但し、 Ｒ＾１、Ｒ＾２は炭素数６以上のアルキル基を表わす。 ）を表わす。〕で示される修飾シクロデキストリンを用
いることを特徴とする、メチルオレンジの有機溶剤に対
する溶解性改善方法。(1) General formula β-CD(CH_2X)_7(OH)_1
＿４〔I〕[In the formula, β-CD represents a β-cyclodextrin residue, and , R^2 represents an alkyl group having 6 or more carbon atoms. ] A method for improving the solubility of methyl orange in an organic solvent, the method comprising using a modified cyclodextrin shown in the following.
＿４〔 I 〕〔式中、β−ＣＤはβ−シクロデキストリ
ン残基を表わし、Ｘは▲数式、化学式、表等があります
▼又は▲数式、化学式、表等があります▼（但し、 Ｒ＾１、Ｒ＾２は炭素数６以上のアルキル基を表わす。 ）を表わす。〕で示される修飾シクロデキストリンとメ
チルオレンジとにより形成される錯体。(2) General formula β-CD(CH_2X)_7(OH)_1
＿４〔I〕[In the formula, β-CD represents a β-cyclodextrin residue, and , R^2 represents an alkyl group having 6 or more carbon atoms. ] A complex formed by a modified cyclodextrin and methyl orange.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13606184A JPS6187760A (en) | 1984-06-30 | 1984-06-30 | Method for improving solubility of methyl orange dye in solvent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13606184A JPS6187760A (en) | 1984-06-30 | 1984-06-30 | Method for improving solubility of methyl orange dye in solvent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6187760A true JPS6187760A (en) | 1986-05-06 |
Family
ID=15166285
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13606184A Pending JPS6187760A (en) | 1984-06-30 | 1984-06-30 | Method for improving solubility of methyl orange dye in solvent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6187760A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62100557A (en) * | 1985-10-25 | 1987-05-11 | Mitsubishi Electric Corp | Improvement of light fastness of dye |
| JPS63144329A (en) * | 1986-12-09 | 1988-06-16 | Agency Of Ind Science & Technol | Organic hyper thin film of inclusion compound of dye and cyclodextrin derivative and its production |
-
1984
- 1984-06-30 JP JP13606184A patent/JPS6187760A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62100557A (en) * | 1985-10-25 | 1987-05-11 | Mitsubishi Electric Corp | Improvement of light fastness of dye |
| JPS63144329A (en) * | 1986-12-09 | 1988-06-16 | Agency Of Ind Science & Technol | Organic hyper thin film of inclusion compound of dye and cyclodextrin derivative and its production |
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