JPS6057899B2 - Anion exchanger having inclusion effect and method for producing the same - Google Patents
Anion exchanger having inclusion effect and method for producing the sameInfo
- Publication number
- JPS6057899B2 JPS6057899B2 JP57147185A JP14718582A JPS6057899B2 JP S6057899 B2 JPS6057899 B2 JP S6057899B2 JP 57147185 A JP57147185 A JP 57147185A JP 14718582 A JP14718582 A JP 14718582A JP S6057899 B2 JPS6057899 B2 JP S6057899B2
- Authority
- JP
- Japan
- Prior art keywords
- resin
- polycyclodextrin
- anion exchanger
- producing
- cyclodextrin
- 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
Links
- 230000000694 effects Effects 0.000 title claims description 10
- 150000001450 anions Chemical class 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 239000011347 resin Substances 0.000 claims description 23
- 229920005989 resin Polymers 0.000 claims description 23
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 6
- 125000005265 dialkylamine group Chemical group 0.000 claims description 4
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 229920000858 Cyclodextrin Polymers 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000011324 bead Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000001116 FEMA 4028 Substances 0.000 description 4
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 4
- 229960004853 betadex Drugs 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 235000011175 beta-cyclodextrine Nutrition 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- -1 cyclic oligosaccharide Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 150000003459 sulfonic acid esters Chemical class 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- AAHFRWRQQDVWPX-UHFFFAOYSA-N prop-2-ene-1-sulfonyl chloride Chemical compound ClS(=O)(=O)CC=C AAHFRWRQQDVWPX-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 description 1
- 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 1
- 101001061465 Syntrichia ruralis Probable 1-Cys peroxiredoxin Proteins 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 description 1
- 229940043377 alpha-cyclodextrin Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 230000009881 electrostatic interaction Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 description 1
- 229940080345 gamma-cyclodextrin Drugs 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
Landscapes
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
Description
【発明の詳細な説明】
本発明は包接作用を有する陰イオン交換体及びその製造
方法に関し、さらに詳しくは、ポリシクロデキストリン
樹脂にスルホニルクロリド誘導体を反応させて得られる
生成物にジアルキルアミンを反応させることによる包接
作用を有する陰イオン交換体及びその製造方法に関する
ものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an anion exchanger having an inclusion effect and a method for producing the same, and more specifically to a product obtained by reacting a polycyclodextrin resin with a sulfonyl chloride derivative and a dialkylamine. The present invention relates to an anion exchanger having an clathration effect due to the clathration effect, and a method for producing the same.
シクロデキストリンは６個以上のグルコースがａ−１・
４−結合した環状のオリゴ糖であり、その分子内に筒
状の空洞を有しており、その中に種々の物質を取り込む
ことによつて包接化合物を形成する。この包接化合物を
形成するためには被包接物質の分子の形と大きさがシク
ロデキストリンの空洞に適合していなければならず、適
合の度合により被包接物質とシクロデキストリンとの間
に働く親和力に差が生じるために、その差を利用するこ
とによつて種々の物質の分離や分割を行うことが可能で
あり、シクロデキストリンを架橋高分子化して不溶性の
樹脂とし、それをカラムクロマトグラフィーの充填剤と
して利用する試みが行われている。ところで、シクロデ
キストリンの包接化合物形成作用は主として包接される
物質の大きさと形に依存するため、シクロデキストリン
を高分子化することにより得られるポリシクロデキスト
リン樹脂を用いて物質の分離を行う場合には、大きさと
形の類似したものほど分離が困難となる。Cyclodextrin has six or more glucose molecules a-1,
It is a 4-linked cyclic oligosaccharide that has a cylindrical cavity within its molecule, and forms clathrate compounds by incorporating various substances into the cavity. In order to form this clathrate, the shape and size of the molecule of the clathrate must fit into the cavity of the cyclodextrin, and depending on the degree of compatibility, there is a gap between the clathrate and the cyclodextrin. Because there are differences in the working affinity, it is possible to separate and divide various substances by utilizing these differences. Attempts are being made to use it as a filler in graphics. By the way, the clathrate compound forming effect of cyclodextrin mainly depends on the size and shape of the substance to be included, so when separating substances using polycyclodextrin resin obtained by polymerizing cyclodextrin, The more similar the sizes and shapes, the more difficult it is to separate them.
従つて、このような場合には単に包接の効果だけでは分
離には不十分であり、さらに何らかの分離に有効な効果
を導入する必要がある。本発明者らはこのような実情に
鑑み、ポリシクロデキストリン樹脂の改良に関して鋭意
研究を重ねた結果、ポリシクロデキストリン樹脂にジア
ルキルアミノ基を導入することによつて、ポリシクロデ
キストリン樹脂が単に包接作用を有するだけでなく、陰
イオン交換体としての作用を有するた・め、物質の大き
さと形だけでなく、静電的相互作用の効果が加わり、従
つて電荷分布の差による物質分離の機能を付与できるこ
とを見い出し、この知見に基づいて本発明をなすに至つ
た。Therefore, in such cases, the mere effect of inclusion is not sufficient for separation, and it is necessary to introduce some effect that is effective for separation. In view of these circumstances, the present inventors have conducted extensive research into improving polycyclodextrin resins, and have found that by introducing dialkylamino groups into polycyclodextrin resins, polycyclodextrin resins can be simply clathrated. Because it not only has the function of an anion exchanger, but also the size and shape of the substance, the effect of electrostatic interaction is added, and therefore the function of substance separation due to the difference in charge distribution. The present invention has been completed based on this finding.
すなわち本発明は、ポリシクロデキストリン樹」旨番こ
アノレキノレもしくはアリノレスノレホニノレクロリド
を反応させてスルホン酸エステルとし、それにジアルキ
ルアミンを反応させることによるジアルキルアミノ基を
有するポリシクロデキストリン樹脂の陰イオン交換体及
びその製造方法を提供するものである。That is, the present invention provides an anion of a polycyclodextrin resin having a dialkylamino group by reacting a polycyclodextrin resin or an allinoresnorefoniole chloride to form a sulfonic acid ester, and reacting the sulfonic acid ester with a dialkylamine. The present invention provides an exchanger and a method for manufacturing the same.
本発明において用いるポリシクロデキストリンは、α−
シクロデキストリン、β−シクロデキストリン、γ−シ
クロデキストリン及びこれらの混合物を架橋して高分子
とするか、もしくは、高分子に結合させたものであり、
ジアルキルアミノ基を導入するための反応条件に耐えう
るものはすべて用いることができる。The polycyclodextrin used in the present invention is α-
Cyclodextrin, β-cyclodextrin, γ-cyclodextrin, and mixtures thereof are crosslinked into polymers or bonded to polymers,
Any material that can withstand the reaction conditions for introducing a dialkylamino group can be used.
特にエピクロルヒドリンもしくはジエポキシ化合物によ
り架橋高分子化したポリシクロデキストリン樹脂は、熱
とアルカリに対する耐性が大きいだけでなく、スルホニ
ルクロリドと反応するための水酸基を多数有しているた
め好適である。ポリシクロデキストリン樹脂のスルホン
酸エステルを合成するためには、無水ピリジン中に分散
させたポリシクロデキストリン樹脂にアルキルスルホニ
ルクロリドもしくはアリルスルホニルクロリドを加える
。In particular, polycyclodextrin resin crosslinked with epichlorohydrin or a diepoxy compound is suitable because it not only has high resistance to heat and alkali but also has a large number of hydroxyl groups for reacting with sulfonyl chloride. To synthesize the sulfonic acid ester of polycyclodextrin resin, alkylsulfonyl chloride or allylsulfonyl chloride is added to polycyclodextrin resin dispersed in anhydrous pyridine.
使用する樹脂の形状としては、固体のポリシクロデキス
トリン樹脂を粉砕したもの及びビーズ状の樹脂があるが
、強度の点でビーズ状てあるものが好まれる。また使用
に先だつて十分脱水しておくことが必要である。ポリシ
クロデキストリン樹脂１重量部に対し無水ピリジン３〜
１鍾量部の範囲で加え、０．１〜１濾量部の範囲でアル
キルスルホニルクロリドもしくはアリルスルホニルクロ
リドを加える。混合物は攪拌しつつ室温〜７０℃の範囲
で反応を行わせる。反応時間は温．度により異なるが５
〜５叫間が適当である。反応終了後エステル化された樹
脂をアセトン及び水で十分洗浄した後、アセトンで脱水
し乾燥させる。得られた樹脂１重量部に対し３〜ｌ鍾量
部のジアルキルアミンを加え、攪拌しつつ還流するか、
も！しくはオートクレーブ中にて６０〜１００℃に保つ
。反応時間は５〜２４時間の範囲が適当である。生成物
はアセトンで洗浄した後、希塩酸水溶液にて十分洗浄し
乾燥させることにより、ジアルキルアミノ基を有するポ
リシクロデキストリン樹脂が塩酸（塩として得られる。
この樹脂を水酸化ナトリウム水溶液、次いで脱イオン水
で洗浄することによつて塩素イオンを除去することによ
り、陰イオン交換体として使用することができる。本発
明の特徴は、ポリシクロデキストリン樹脂にジアルキル
アミノ基を導入することにより、包接作用を有する陰イ
オン交換体が得られることであり、得られた樹脂は、イ
オン交換体、分離剤、及び吸着剤として使用できる。The shape of the resin used includes pulverized solid polycyclodextrin resin and bead-shaped resin, but bead-shaped resin is preferred from the viewpoint of strength. It is also necessary to thoroughly dehydrate the product before use. 3 to 3 parts of anhydrous pyridine per 1 part by weight of polycyclodextrin resin
1 part by weight is added, and alkylsulfonyl chloride or allylsulfonyl chloride is added in a range from 0.1 to 1 part by weight. The mixture is stirred and reacted at a temperature ranging from room temperature to 70°C. The reaction time is warm. It varies depending on the degree, but 5
~5 shouts is appropriate. After the reaction is completed, the esterified resin is thoroughly washed with acetone and water, and then dehydrated with acetone and dried. Add 3 to 1 parts of dialkylamine to 1 part by weight of the obtained resin and reflux while stirring, or
too! Alternatively, keep it at 60-100°C in an autoclave. The reaction time is suitably in the range of 5 to 24 hours. The product is washed with acetone and then sufficiently washed with a dilute aqueous hydrochloric acid solution and dried to obtain a polycyclodextrin resin having a dialkylamino group in the form of hydrochloric acid (salt).
This resin can be used as an anion exchanger by removing chloride ions by washing with an aqueous sodium hydroxide solution and then with deionized water. A feature of the present invention is that an anion exchanger having an inclusion effect can be obtained by introducing a dialkylamino group into a polycyclodextrin resin, and the obtained resin can be used as an ion exchanger, a separating agent, and Can be used as an adsorbent.
次に参考例及び実施例によつて本発明をさらに詳細に説
明する。Next, the present invention will be explained in further detail by reference examples and examples.
参考例
粉末状のβ−シクロデキストリン２５ｆに水１２．５ノ
ｍｌを加えて混練し、３０％水酸化ナトリウム水溶液３
７．５ｍ１及び水素化ホウ素ナトリウム１００ｍ９を加
えて均一な溶液とし、５０℃に保つて２００ｒ′Ｐｍの
速度でかきまぜつつ７．５ｍ１のエピクロルヒドリンを
滴下し、３紛間攪拌した後、泡を消すために３紛間．５
０℃に保つた。Reference Example 12.5 nm of water was added to 25f of powdered β-cyclodextrin and kneaded to form a 30% aqueous sodium hydroxide solution 3.
Add 7.5 ml and 100 m9 of sodium borohydride to make a homogeneous solution, keep it at 50°C, and add 7.5 ml of epichlorohydrin dropwise while stirring at a speed of 200 r'Pm. After stirring for 3 times, to eliminate bubbles. 3 conflicts. 5
It was kept at 0°C.
得られたシロツプ状の液体に流動パラフィン３７５ｍ１
を加えて５０℃に保ちつつ１０００ｒｐｍで５分間攪拌
して均一に分散させた後、エピク的レヒドリン２５ｍ１
を加えてさらに２時間５０℃に保つて攪拌した。得られ
たビーズをろ過して分離し、ヘキサン１００ｍ１で３回
、次いでアセトン１００ｍ１で３回洗浄した後、洗浄液
のＰＨが中性になるまで蒸留水で洗浄し、さらに蒸留水
１ｅに１日浸して水溶性成分を除去した。これを５０％
アセトン水で洗浄した後、３００ｍ１のアセトンに１日
浸して脱水し、７０℃にて１日乾燥させ、さらに真空デ
シケ−ター中で五酸化リンにより１日乾燥させた。かく
して得られたポリーβ−シクロデキストリンビーズ２９
ｙをふるいにかけることにより５０〜２００メッシュの
ビーズが２６ｆ得られた。実施例参考例により得られた
ポリーβ−シクロデキストリンビーズ１０ｙをピリジン
３０ｍ１中に分散させ、ベンゼン５ｍＬを加え加熱して
も約５ｍ１を溜去し、冷却した後、ｐ−トルエンスルホ
ニルクロリド１０ｙを加え室温にて３Ｃ＠攪拌した後４
（代）にて５時間攪拌を続けた。Add 375ml of liquid paraffin to the resulting syrupy liquid.
was added and stirred at 1000 rpm for 5 minutes while maintaining the temperature at 50°C to uniformly disperse the mixture, and then added 25 ml of epic rehydrin.
was added, and the mixture was further stirred at 50°C for 2 hours. The obtained beads were separated by filtration, washed 3 times with 100 ml of hexane, then 3 times with 100 ml of acetone, washed with distilled water until the pH of the washing solution became neutral, and further soaked in distilled water 1e for 1 day. water-soluble components were removed. 50% of this
After washing with acetone water, it was immersed in 300 ml of acetone for 1 day to dehydrate it, dried at 70°C for 1 day, and further dried with phosphorus pentoxide in a vacuum desiccator for 1 day. Poly β-cyclodextrin beads 29 thus obtained
26f of beads of 50-200 mesh were obtained by sieving the y. Example 10y of poly-β-cyclodextrin beads obtained in the reference example were dispersed in 30ml of pyridine, 5ml of benzene was added and heated, but about 5ml was distilled off, and after cooling, 10y of p-toluenesulfonyl chloride was added. 3C @ after stirring at room temperature 4
Stirring was continued for 5 hours.
生成分はアセトン、水の順で十分洗浄し、アセトンに浸
して脱水した後、五酸化リンを用いて減圧乾燥させたと
ころ１５クのビーズが得られた。これにベンゼン３０ｍ
ｔを加えて加熱し、約１０ｍ１を溜去した後、ジエチル
アミン２５ｆを加えて２ｃｔｆ間還流させた。得られた
ビーズをアセトン、水の順で洗浄し、希硫酸で中和した
後、水洗及びアセトンで脱水し、減圧乾燥させたところ
、ジエチルアミノ基を有するポリーβ−シクロデキスト
リンビーズの１２．７ｙが塩酸塩として得られた。得ら
れたビーズ１０ｆをとり、１Ｎ水酸化ナトリウム水溶液
で洗浄し、さらに脱イオン水で十分洗浄した後、１．２
Ｎ塩酸を用いて滴定を行つたところ、１３．２モルのジ
メチルアミノ基を有していた。The product was thoroughly washed in the order of acetone and water, immersed in acetone for dehydration, and dried under reduced pressure using phosphorus pentoxide, yielding 15 beads. This and 30m of benzene
After adding t and heating and distilling off about 10ml, 25f of diethylamine was added and refluxed for 2ctf. The obtained beads were washed in the order of acetone and water, neutralized with dilute sulfuric acid, washed with water and dehydrated with acetone, and dried under reduced pressure. Obtained as hydrochloride. The obtained beads 10f were taken and washed with a 1N aqueous sodium hydroxide solution, and then thoroughly washed with deionized water.
Titration using N-hydrochloric acid revealed that it had 13.2 moles of dimethylamino groups.
Claims (1)
樹脂からなる、包接作用を有する陰イオン交換体。 ２ ポリシクロデキストリン樹脂に一般式Ｒ−ＳＯ＿２
Ｃｌで表わされるスルホニルクロリドを反応させ、その
生成物にジアルキルアミンを反応させることを特徴とす
る包接作用を有する陰イオン交換体の製造方法。[Scope of Claims] 1. An anion exchanger having an inclusion effect, which is made of a polycyclodextrin resin having a dialkylamino group. 2 Polycyclodextrin resin with general formula R-SO_2
1. A method for producing an anion exchanger having inclusion action, which comprises reacting a sulfonyl chloride represented by Cl and reacting the product with a dialkylamine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57147185A JPS6057899B2 (en) | 1982-08-25 | 1982-08-25 | Anion exchanger having inclusion effect and method for producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57147185A JPS6057899B2 (en) | 1982-08-25 | 1982-08-25 | Anion exchanger having inclusion effect and method for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5936549A JPS5936549A (en) | 1984-02-28 |
| JPS6057899B2 true JPS6057899B2 (en) | 1985-12-17 |
Family
ID=15424484
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57147185A Expired JPS6057899B2 (en) | 1982-08-25 | 1982-08-25 | Anion exchanger having inclusion effect and method for producing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6057899B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3434547B2 (en) * | 1993-11-15 | 2003-08-11 | 株式会社東芝 | Optical function organic thin film element |
| JP5130454B2 (en) * | 2006-10-10 | 2013-01-30 | 地方独立行政法人青森県産業技術センター | Iodine adsorption and recovery method |
-
1982
- 1982-08-25 JP JP57147185A patent/JPS6057899B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5936549A (en) | 1984-02-28 |
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