JPS6125018B2 - - Google Patents
Info
- Publication number
- JPS6125018B2 JPS6125018B2 JP3725676A JP3725676A JPS6125018B2 JP S6125018 B2 JPS6125018 B2 JP S6125018B2 JP 3725676 A JP3725676 A JP 3725676A JP 3725676 A JP3725676 A JP 3725676A JP S6125018 B2 JPS6125018 B2 JP S6125018B2
- Authority
- JP
- Japan
- Prior art keywords
- cyclodextrin
- clathrate
- diamine
- molecule
- compound
- 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
- 229920000858 Cyclodextrin Polymers 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 36
- 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 claims description 35
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 16
- 239000001116 FEMA 4028 Substances 0.000 claims description 12
- 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 claims description 12
- 235000011175 beta-cyclodextrine Nutrition 0.000 claims description 12
- 229960004853 betadex Drugs 0.000 claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- IYWCBYFJFZCCGV-UHFFFAOYSA-N formamide;hydrate Chemical compound O.NC=O IYWCBYFJFZCCGV-UHFFFAOYSA-N 0.000 claims 1
- 150000004985 diamines Chemical class 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000004952 Polyamide Substances 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- IZRWZLBCZMYWIG-UHFFFAOYSA-N 1,2-dinitro-3-phenylbenzene Chemical group [O-][N+](=O)C1=CC=CC(C=2C=CC=CC=2)=C1[N+]([O-])=O IZRWZLBCZMYWIG-UHFFFAOYSA-N 0.000 description 1
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 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
- 150000001412 amines Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009472 formulation 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
- 238000010438 heat treatment Methods 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000006864 oxidative decomposition reaction Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
本発明は新規なシクロデキストリン包接化合物
に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel cyclodextrin clathrate compounds.
従来有機及び無機の化合物と尿素、チオ尿素、
フエノール類、ジニトロジフエニル等の化合物と
が包接化合物を形成することが知られている。し
かしこの種の包接化合物はすべて包接格子をつく
る分子である化合物の分子が複数個集合して包接
格子を形成するものばかりであり、包接格子をつ
くる分子の単分子中に他の化合物を包接するいわ
ゆる単分子包接化合物ではない。 Conventional organic and inorganic compounds and urea, thiourea,
It is known that compounds such as phenols and dinitrodiphenyl form clathrate compounds. However, all of these types of clathrate compounds are molecules that form an inclusion lattice by aggregation of multiple molecules of the compound that make up the inclusion lattice. It is not a so-called monomolecular clathrate that includes compounds.
一方、１分子中に他の化合物をその空孔内に包
接できる化合物としてシクロデキストリンが知ら
れており、炭化水素、ヨウ素、アルコール等との
包接化合物が得られているが、シクロデキストリ
ンとジアミンとの包接化合物については未だ知ら
れていない。 On the other hand, cyclodextrin is known as a compound that can include other compounds in its pores in one molecule, and inclusion compounds with hydrocarbons, iodine, alcohol, etc. have been obtained, but cyclodextrin Inclusion compounds with diamines are not yet known.
本発明者は合成が容易であり、しかも溶解性に
優れかつ親水性に富むポリアミドについて多角的
に検討を行なつてきたところ、ポリアミド重合体
のアミン原料として包接化合物を使用することに
着目し、本発明を完成したものである。 The present inventor has conducted multifaceted studies on polyamides that are easy to synthesize, have excellent solubility, and is highly hydrophilic, and has focused on the use of clathrate compounds as amine raw materials for polyamide polymers. , has completed the present invention.
すなわち本発明の目的は有用なシクロデキスト
リン包接化合物およびその製造方法を提供するこ
とである。 That is, an object of the present invention is to provide a useful cyclodextrin clathrate compound and a method for producing the same.
本発明の有用なシクロデキストリン包接化合物
は、包接格子をつくる分子がシクロデキストリン
であり、包接されるジアミン分子がヘキサメチレ
ンジアミン又はｐ−キシリレンジアミンであるシ
クロデキストリン包接化合物である。本発明のシ
クロデキストリン包接化合物において包接格子を
つくる分子であるシクロデキストリンはｄ−グル
コースが６〜８個環状にα−１，４結合によつて
つながつた次式により示される化合物である。 A cyclodextrin clathrate compound useful in the present invention is a cyclodextrin clathrate compound in which the molecule forming the inclusion lattice is cyclodextrin, and the diamine molecule to be included is hexamethylene diamine or p-xylylene diamine. Cyclodextrin, which is a molecule forming an inclusion lattice in the cyclodextrin clathrate compound of the present invention, is a compound represented by the following formula in which 6 to 8 d-glucoses are connected in a ring through α-1,4 bonds.
前式においてｎ＝４をα−シクロデキストリ
ン、ｎ＝５をβ−シクロデキストリン、ｎ＝６を
γ−シクロデキストリンと称するが、これらα−
体、β−体及びγ−体では分子内部の空洞の径が
異なる。シクロデキストリンを第１図に示す分子
摸型図で表した場合、径γはα−体で６Å、β−
体で７〜８Å、γ−体では９〜10Åであるので、
どの型のシクロデキストリンを用いるかは包接さ
れるジアミンの分子構造で異なつてくるが、一般
にはβ−シクロデキストリンが用いられる。 In the above formula, n = 4 is referred to as α-cyclodextrin, n = 5 is referred to as β-cyclodextrin, and n = 6 is referred to as γ-cyclodextrin.
The diameter of the cavity inside the molecule differs between the molecule, the β-form, and the γ-form. When cyclodextrin is represented in the molecular model diagram shown in Figure 1, the diameter γ is 6 Å for the α-form, and the diameter for the β-form is 6 Å.
Since it is 7 to 8 Å in the body and 9 to 10 Å in the γ-body,
The type of cyclodextrin used depends on the molecular structure of the diamine to be included, but β-cyclodextrin is generally used.
シクロデキストリンとジアミンとの包接化合物
の製造はシクロデキストリンに直接ジアミンを包
接することにより行なわれる。包接は一般には液
体触体中で行なわれ、たとえばシクロデキストリ
ンの水溶液にジアミンを添加することにより行な
われる。この際シクロデキストリンの空洞内部が
親油性であるためにジアミンとは容易に包接化合
物を形成する。包接温度は臨界的ではないが30〜
40℃が特に望ましい。これより低温では反応温度
が遅く、一方沸騰水中では生成した包接化合物が
解難し、冷却の際に再び包接体となるので高温で
反応を行なう意味はない。反応後、反応温度を室
温に冷却することにより包接化合物が白色の沈殿
として析出する。液体媒体は水の外に有機溶媒も
使用され、例えばジメチルアセトアミド、ヘキサ
メチルホスホリツクトリアミド中ではシクロデキ
ストリンとジアミンとの包接化合物は溶解した状
態で得られ、一方ジメチルホルムアミド中ではゲ
ルとなるがこれをアセトンと混合することにより
沈殿となるので単離することができる。 An inclusion compound of cyclodextrin and diamine is produced by directly including diamine in cyclodextrin. Inclusion is generally carried out in a liquid medium, for example by adding the diamine to an aqueous solution of cyclodextrin. At this time, since the inside of the cavity of cyclodextrin is lipophilic, it easily forms an inclusion compound with diamine. The clathration temperature is not critical but is 30~
A temperature of 40°C is particularly desirable. If the temperature is lower than this, the reaction temperature will be slow, while in boiling water the clathrate formed will dissolve and become an clathrate again upon cooling, so there is no point in carrying out the reaction at a high temperature. After the reaction, the clathrate is precipitated as a white precipitate by cooling the reaction temperature to room temperature. In addition to water, organic solvents are also used as liquid media; for example, in dimethylacetamide and hexamethylphosphoric triamide, the clathrate compound of cyclodextrin and diamine is obtained in a dissolved state, while in dimethylformamide, it becomes a gel. By mixing this with acetone, it becomes a precipitate, which can be isolated.
シクロデキストリンに対するジアミンの添加量
は目的とする包接化合物がシクロデキストリン１
分子の空洞内にジアミン１分子を包接した化合物
である点からシクロデキストリン１モルに対して
ジアミン１モル以上の割合が望ましい。 The amount of diamine added to cyclodextrin is determined when the target inclusion compound is cyclodextrin 1.
Since it is a compound in which one molecule of diamine is included in the cavity of the molecule, a ratio of 1 mole or more of diamine to 1 mole of cyclodextrin is desirable.
液体媒体の種類、シクロデキストリンに対する
ジアミンの添加量の変化にかゝわらず、いずれの
場合にも単離、精製後の生成物はシクロデキスト
リン１分子中にジアミン１分子を含む包接化合物
であることを元素分析、NMR、IR等から確認し
た。 Regardless of the type of liquid medium or the amount of diamine added to cyclodextrin, the product after isolation and purification is an inclusion compound containing one molecule of diamine in one molecule of cyclodextrin. This was confirmed by elemental analysis, NMR, IR, etc.
本発明のシクロデキストリン包接化合物は、こ
れとアジピン酸、テレフタレル酸又はイソフタル
酸等の二塩基性カルボン酸若しくはその反応性酸
誘導体とを重縮合することにより、ポリアミドの
ジアミン成分であるヘキサメチレンジアミン又は
ｐ−キシリレンジアミンがシクロデキストリンに
より包接されたポリアミドが得られ、このポリア
ミドは溶解性及び親水性に優れ、その溶液から繊
維、フイルム等を成形することができる（本発明
の同日出願である特公昭60−14766号公報参照）。
更に本発明のシクロデキストリン包接化合物は分
子内に多数の水酸基を有するので、この水酸基を
利用して種々の化学試剤と反応させて有用を材料
に転換することが可能である。又包接化反応自体
を応用してジアミンの単離、精製を行うことがで
きる。更にジアミンをシクロデキストリンで包接
することにより、ジアミンの酸化反応を防止でき
るので、本発明の包接化合物はジアミンの酸化分
解等に対する高い安定性が要求される医薬品、化
粧品、食品等の分野で、製品の製剤面、使用面で
安全面を増す目的で使用される。 The cyclodextrin clathrate compound of the present invention is produced by polycondensing the cyclodextrin clathrate compound with a dibasic carboxylic acid such as adipic acid, terephthalic acid, or isophthalic acid, or a reactive acid derivative thereof. Alternatively, a polyamide in which p-xylylenediamine is clathrated with cyclodextrin can be obtained, and this polyamide has excellent solubility and hydrophilicity, and fibers, films, etc. can be formed from the solution. (Refer to a certain Special Publication No. 14766).
Furthermore, since the cyclodextrin clathrate compound of the present invention has a large number of hydroxyl groups in its molecule, it can be converted into useful materials by reacting with various chemical reagents using these hydroxyl groups. Furthermore, diamines can be isolated and purified by applying the clathration reaction itself. Furthermore, by including diamine with cyclodextrin, the oxidation reaction of diamine can be prevented, so the clathrate compound of the present invention can be used in fields such as pharmaceuticals, cosmetics, and foods, where high stability against oxidative decomposition of diamine is required. Used to increase safety in product formulation and use.
次に本発明を実施例について具体的に説明する
が、本発明はこれによりなんら限定されるもので
はない。 Next, the present invention will be specifically explained with reference to Examples, but the present invention is not limited thereto in any way.
実施例 １
ヘキサメチレンジアミンの水溶液に当量のβ−
シクロデキストリンを２％濃度で加え、30〜40℃
に加温しながら撹拌すると均一な溶液となつた。
このまゝ反応混液を室温に放置すると次第に白色
の沈殿が生成した。この沈殿を別しアセトンで
よく洗浄後乾燥した。生成物がヘキサメチレンジ
アミン１分子を空洞内に含むβ−シクロデキスト
リン１分子との包接化合物であることを元素分
析、IR及びNMRスペクトルから確認した。Example 1 An equivalent amount of β- to an aqueous solution of hexamethylene diamine
Add cyclodextrin at 2% concentration, 30-40℃
When stirred while heating, a homogeneous solution was obtained.
When the reaction mixture was left at room temperature, a white precipitate gradually formed. This precipitate was separated, thoroughly washed with acetone, and then dried. It was confirmed from elemental analysis, IR and NMR spectra that the product was an inclusion compound with one molecule of β-cyclodextrin containing one molecule of hexamethylene diamine in the cavity.
元素分析の結果はＣ：46.10％、Ｈ：6.90％、
Ｎ：2.18％であり、１対１の包接化合物としての
計算値Ｃ：46.08％、Ｈ：6.88％、Ｎ：2.24％と略
一致する。 The results of elemental analysis are C: 46.10%, H: 6.90%,
N: 2.18%, which is approximately in agreement with the calculated values for a one-to-one clathrate compound: C: 46.08%, H: 6.88%, and N: 2.24%.
生成物のIRスペクトルを第２図に示すが、
3500cm-1に−OH、−NHの伸縮振動、1050cm-1に
ホルマール結合による吸収が認められる。 The IR spectrum of the product is shown in Figure 2.
Stretching vibrations of -OH and -NH are observed at 3500 cm -1 and absorption due to formal bonding is observed at 1050 cm -1 .
一方NMRスペクトルでは第３図に示すように
β−シクロデキストリンによる遮蔽効果により特
性吸収があまり明らかにでないがβ−シクロデキ
ストリンの−CH2−が3.9ppm、−CH−が
4.7ppm、−OHが5.2ppmに現われ、また包接ヘキ
サメチレンジアミンの吸収が2.3ppmに現われ
る。 On the other hand, in the NMR spectrum, as shown in Figure 3, the characteristic absorption is not very clear due to the shielding effect of β-cyclodextrin, but -CH 2 - of β-cyclodextrin is 3.9 ppm, and -CH- is
4.7ppm, -OH appears at 5.2ppm, and absorption of clathrate hexamethylenediamine appears at 2.3ppm.
実施例 ２
ｐ−キシリレンジアミンと当量のβ−シクロデ
キストリンとをジメチルホルムアミド中に添加
し、30〜40℃で撹拌すると、系はゲル化した。こ
のゲルを大量のアセトン中に投じて白色沈殿を回
収し、十分なアセトンで洗浄した後乾燥した。Example 2 p-xylylenediamine and an equivalent amount of β-cyclodextrin were added into dimethylformamide and stirred at 30-40°C, and the system gelled. This gel was poured into a large amount of acetone to collect a white precipitate, washed with sufficient acetone, and then dried.
生成物がｐ−キシリレンジアミン１分子を空洞
内に含むβ−シクロデキストリン１分子との包接
化合物であることをNMRで確認したが、この化
合物には融点がなく、300℃付近で分解した。 It was confirmed by NMR that the product was an inclusion compound with one molecule of β-cyclodextrin containing one molecule of p-xylylenediamine in the cavity, but this compound had no melting point and decomposed at around 300℃. .
この生成物のNMRスペクトルを第４図に示す
が、β−シクロデキストリンの−CH2−が
3.9ppm、−CH−が4.7ppm、−OHが5.2ppmに現
われ、また包接ｐ−キシリレンジアミンの吸収が
2.3ppmに現われている。 The NMR spectrum of this product is shown in Figure 4, where -CH 2 - of β-cyclodextrin is
3.9ppm, -CH- appears at 4.7ppm, -OH appears at 5.2ppm, and absorption of clathrate p-xylylenediamine occurs.
Appears at 2.3ppm.
第１図はシクロデキストリン分子の摸型図、第
２図はヘキサメチレンジアミンのβ−シクロデキ
ストリン包接化合物のIRスペクトル、第３図は
同じくNMRスペクトル、第４図はｐ−キシリレ
ンジアミンのβ−シクロデキストリン包接化合物
のNMRスペクトルである。
Figure 1 is a schematic diagram of a cyclodextrin molecule, Figure 2 is the IR spectrum of the β-cyclodextrin clathrate of hexamethylene diamine, Figure 3 is the NMR spectrum, and Figure 4 is the β-cyclodextrin clathrate of hexamethylene diamine. - NMR spectrum of cyclodextrin clathrate.
Claims (1)
であり包接される分子がヘキサメチレンジアミン
又はｐ−キシリレンジアミンであるシクロデキス
トリン包接化合物。 ２ シクロデキストリンがβ−シクロデキストリ
ンである特許請求の範囲第１項記載の包接化合
物。 ３ シクロデキストリンにヘキサメチレンジアミ
ン又はｐ−キシリレンジアミンを包接させること
を特徴とするシクロデキストリン包接化合物の製
造方法。 ４ シクロデキストリンがβ−シクロデキストリ
ンである特許請求の範囲第３項に記載の包接化合
物の製造方法。 ５ 包接温度が30〜40℃である特許請求の範囲第
３項又は第４項記載の包接化合物の製造方法。 ６ 包接を水又はジメチルホルムアミドで行う特
許請求の範囲第３項ないし第５項のいずれかに記
載の包接化合物の製造方法。[Scope of Claims] 1. A cyclodextrin clathrate compound in which the molecule forming the clathrate lattice is cyclodextrin and the molecule to be included is hexamethylene diamine or p-xylylene diamine. 2. The clathrate compound according to claim 1, wherein the cyclodextrin is β-cyclodextrin. 3. A method for producing a cyclodextrin clathrate compound, which comprises clasping hexamethylene diamine or p-xylylene diamine with cyclodextrin. 4. The method for producing an clathrate compound according to claim 3, wherein the cyclodextrin is β-cyclodextrin. 5. The method for producing an clathrate compound according to claim 3 or 4, wherein the clathrate temperature is 30 to 40°C. 6. A method for producing an clathrate compound according to any one of claims 3 to 5, wherein clathration is carried out with water or dimethylformamide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3725676A JPS52121084A (en) | 1976-04-05 | 1976-04-05 | Cyclodextrin inclusion compound and process for preparting the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3725676A JPS52121084A (en) | 1976-04-05 | 1976-04-05 | Cyclodextrin inclusion compound and process for preparting the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS52121084A JPS52121084A (en) | 1977-10-12 |
| JPS6125018B2 true JPS6125018B2 (en) | 1986-06-13 |
Family
ID=12492556
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3725676A Granted JPS52121084A (en) | 1976-04-05 | 1976-04-05 | Cyclodextrin inclusion compound and process for preparting the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS52121084A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5208316A (en) * | 1990-10-01 | 1993-05-04 | Toppan Printing Co., Ltd. | Cyclodextrin polymer and cyclodextrin membrane prepared using said polymer |
-
1976
- 1976-04-05 JP JP3725676A patent/JPS52121084A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS52121084A (en) | 1977-10-12 |
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