JPH0529375B2 - - Google Patents
Info
- Publication number
- JPH0529375B2 JPH0529375B2 JP20248888A JP20248888A JPH0529375B2 JP H0529375 B2 JPH0529375 B2 JP H0529375B2 JP 20248888 A JP20248888 A JP 20248888A JP 20248888 A JP20248888 A JP 20248888A JP H0529375 B2 JPH0529375 B2 JP H0529375B2
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- arene
- alkyl group
- formula
- producing
- 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 - Lifetime
Links
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000002202 Polyethylene glycol Substances 0.000 claims description 4
- VTJUKNSKBAOEHE-UHFFFAOYSA-N calixarene Chemical class COC(=O)COC1=C(CC=2C(=C(CC=3C(=C(C4)C=C(C=3)C(C)(C)C)OCC(=O)OC)C=C(C=2)C(C)(C)C)OCC(=O)OC)C=C(C(C)(C)C)C=C1CC1=C(OCC(=O)OC)C4=CC(C(C)(C)C)=C1 VTJUKNSKBAOEHE-UHFFFAOYSA-N 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229920001223 polyethylene glycol Polymers 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000003444 phase transfer catalyst Substances 0.000 claims description 3
- 150000001339 alkali metal compounds Chemical class 0.000 claims description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000002334 glycols Chemical class 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 150000003242 quaternary ammonium salts Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- UOEYZAXKBKAKRO-UHFFFAOYSA-N 5,11,17,23,29,35-hexa-tert-butylcalix[6]arene-37,38,39,40,41,42-hexol Chemical compound C1C(C=2O)=CC(C(C)(C)C)=CC=2CC(C=2O)=CC(C(C)(C)C)=CC=2CC(C=2O)=CC(C(C)(C)C)=CC=2CC(C=2O)=CC(C(C)(C)C)=CC=2CC(C=2O)=CC(C(C)(C)C)=CC=2CC2=CC(C(C)(C)C)=CC1=C2O UOEYZAXKBKAKRO-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 2
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 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
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
- C08G65/3311—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing a hydroxy group
- C08G65/3314—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing a hydroxy group cyclic
- C08G65/3315—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing a hydroxy group cyclic aromatic
- C08G65/3317—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing a hydroxy group cyclic aromatic phenolic
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polyethers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、カリウム、ルビジウム、セシウムの
ようなアルカリ金属に対して捕捉能力を有し且つ
有機合成反応における触媒として有用なカリツク
スアレーン誘導体の製造方法に関するものであ
る。Detailed Description of the Invention (Field of Industrial Application) The present invention is directed to the use of calyxarene derivatives that have the ability to capture alkali metals such as potassium, rubidium, and cesium and are useful as catalysts in organic synthesis reactions. This relates to a manufacturing method.
（従来の技術）
従来、カリツクスアレーン誘導体の製造方法と
しては、ベンゼン溶液中で、カリウム−ｔ−ブト
キシドを触媒として用いてｐ−ｔ−ブチルカリツ
クス〔ｎ〕アレーンにポリエチレングリコールモ
ノメチルエーテルのｐ−トルエンスルホネートを
反応させる方法が知られている（例えば、船田
等、中本義章、石田真一郎：Polimer
Preprints、Japan、Vo134、No.３、368頁（1985）
参照）。(Prior Art) Conventionally, as a method for producing calixarene derivatives, pt-butyl calix[n]arene is converted into p-p of polyethylene glycol monomethyl ether in a benzene solution using potassium-t-butoxide as a catalyst. - A method of reacting toluenesulfonate is known (for example, Funada et al., Yoshiaki Nakamoto, Shinichiro Ishida: Polymer
Preprints, Japan, Vo134, No. 3, 368 pages (1985)
reference).
（発明が解決しようとする課題）
しかしながら、上記の従来方法で用いられるカ
リウム−ｔ−ブトキシドは非常に吸湿性が大きい
ため、反応を行うには特別の乾燥した室を必要と
する。また、カリウム−ｔ−ブトキシドは皮膚や
粘膜を腐食させるだけでなく、高温で酸素や空気
に晒すと発火に危険性さえある。このように上記
方法は危険度が高い問題があつた。(Problems to be Solved by the Invention) However, the potassium t-butoxide used in the above-mentioned conventional method is highly hygroscopic and requires a special dry chamber to carry out the reaction. Moreover, potassium t-butoxide not only corrodes the skin and mucous membranes, but also poses a risk of ignition when exposed to oxygen or air at high temperatures. As described above, the above method has a problem of high risk.
本発明は、このような問題を解消することを目
的として開発された製造方法である。 The present invention is a manufacturing method developed with the aim of solving such problems.
（課題を解決するための手段）
上記目的達成のため、相間移動触媒を用いれば
極めて安全（低温、常圧下）に、しかも高収率で
目的とするカリツクスアレーン誘導体を製造でき
ることを見出し本発明を完成した。(Means for Solving the Problems) In order to achieve the above object, it has been discovered that the desired calixarene derivative can be produced extremely safely (at low temperatures and under normal pressure) and in high yield by using a phase transfer catalyst, and the present invention is presented. completed.
即ち、本発明に係るカリツクスアレーン誘導体
の製造方法は、次の一般式［１］
（式中、Ｒは水素又はアルキル基を、ｎは４〜
８の整数を夫々示す。）
で表される化合物を、水酸化リチウム、水酸化ナ
トリウム、水酸化カリウム、炭酸ナトリウム、炭
酸カリウムのような室温で取扱いの容易なアルカ
リ金属化合物と塩化ベンジルトリメチルアンモニ
ウム、塩化ベンジルトリエチルアンモニウム、塩
化テトラ−ｎ−ブチルアンモニウム、臭化テトラ
−ｎ−ブチルアンモニウムなどのような四級アン
モニウム塩との存在下、塩化メチレン中40℃で一
般式［２］
Ｘ−（CH2CH2Ｏ）nR′ ……［２］
（式中、R′は水素又はアルキル基を示し、ｍ
は１〜20の数である。Ｘはアリールスルホニル基
を示す。 That is, the method for producing calixarene derivatives according to the present invention is carried out by the following general formula [1] (In the formula, R is hydrogen or an alkyl group, and n is 4 to
Each represents an integer of 8. ) are combined with alkali metal compounds that can be easily handled at room temperature such as lithium hydroxide, sodium hydroxide, potassium hydroxide, sodium carbonate, and potassium carbonate, and benzyltrimethylammonium chloride, benzyltriethylammonium chloride, and tetrachloride. - General formula [ 2] ...[2] (In the formula, R' represents hydrogen or an alkyl group, m
is a number from 1 to 20. X represents an arylsulfonyl group.
で表される化合物と反応させることを特徴とす
る。It is characterized by reacting with a compound represented by:
本発明の反応成分である上記一般式［１］で示
されるものとしては、例えば、ｐ−ｔ−ブチルカ
リツクス〔６〕アレーン、ｐ−ｔ−ブチルカリツ
クス〔８〕アレーン、ｐ−ｔ−ブチルカリツクス
〔４〕アレーン、ｐ−ｔ−オクチルカリツクス
〔４〕アレーン、ｐ−ｔ−オクチルカリツクス
〔６〕アレーン、ｐ−ｔ−オクチルカリツクス
〔８〕アレーンなどが挙げられる。 Examples of the reaction components of the present invention represented by the general formula [1] include pt-butylcalix[6]arene, pt-butylcalix[8]arene, and pt-butylcalix[8]arene. Examples include butylcalyx[4]arene, pt-octylcalyx[4]arene, pt-octylcalyx[6]arene, pt-octylcalyx[8]arene, and the like.
また、上記一般式［２］で示されるものとし
て、例えば、トリエチレングリコールモノメチル
エーテルのｐ−トルエンスルホネート、ポリエチ
レングリコールモノメチルエーテルのｐ−トルエ
ンスルホネートなどが挙げられる。 Examples of the compound represented by the general formula [2] include p-toluenesulfonate of triethylene glycol monomethyl ether and p-toluenesulfonate of polyethylene glycol monomethyl ether.
（作用）
本発明方法は、上記した通り低温で且つ安全に
反応を行うことができるため、有利な方法であ
る。尚、この反応は室温付近の温度で行うことが
できるが、塩化メチレンの沸点（40℃）付近の温
度で行うと収率が向上するので好ましい。(Function) As described above, the method of the present invention is an advantageous method because the reaction can be carried out safely at low temperatures. Although this reaction can be carried out at a temperature near room temperature, it is preferable to carry it out at a temperature near the boiling point of methylene chloride (40°C) because the yield will improve.
（実施例） 以下、本発明の実施例を説明する。(Example) Examples of the present invention will be described below.
実施例
クロロホルム及びメタノール含有ｐ−ｔ−ブチ
ルカリツクス〔６〕アレーンを2.0ｇ（0.00173モ
ル）、トリエチレングリコールモノメチルエーテ
ルのｐ−トルエンスルホネート9.89ｇ（0.0311モ
ル）、水酸化カリウム3.65ｇ（0.065モル）、及び
触媒として、塩化ベンジルトリメチルアンモニウ
ム1.0ｇを20mlの塩化メチレンに溶解、分散させ、
40℃で24時間かきまぜた。Example 2.0 g (0.00173 mol) of p-t-butyl calix[6]arene containing chloroform and methanol, 9.89 g (0.0311 mol) of p-toluene sulfonate of triethylene glycol monomethyl ether, 3.65 g (0.065 mol) of potassium hydroxide ), and as a catalyst, 1.0 g of benzyltrimethylammonium chloride was dissolved and dispersed in 20 ml of methylene chloride,
Stir at 40°C for 24 hours.
その後、反応混合物を水に注ぎ、生成物を塩化
メチレンで抽出した。その抽出液を無水硫酸マグ
ネシウムで乾燥させた後、塩化メチレンを留去す
ると、粘性のある液体が得られた。これを放置す
ると結晶が析出した。エタノールで再結晶すると
無色立方晶が3.0ｇ（収率94％）得られた。この
物質の融点は123〜124℃である。 Afterwards, the reaction mixture was poured into water and the product was extracted with methylene chloride. After drying the extract over anhydrous magnesium sulfate, methylene chloride was distilled off to obtain a viscous liquid. When this was left to stand, crystals precipitated. Recrystallization from ethanol gave 3.0 g (yield 94%) of colorless cubic crystals. The melting point of this material is 123-124°C.
また、この物質は、赤外スペクトル（KBr）
分析及び元素分析のデータから下記構造式を持つ
と思われる。 This substance also has an infrared spectrum (KBr)
Based on the analysis and elemental analysis data, it seems to have the following structural formula.
赤外スペクトル；2950，2920，2850，1600，
1580，1480，1460，1110cm-1
元素分析；Ｃ，69.94％、Ｈ，9.34％
（C108H168O24に対する理論値Ｃ，70.10％、
Ｈ，9.15％）
実施例
クロロホルム及びメタノール含有ｐ−ｔ−ブチ
ルカリツクス〔６〕アレーン2.0ｇ（0.00173モ
ル）、ポリエチレングリコールモノメチルエーテ
ルのｐ−トルエンスルホネート（平均分子量440）
13.7ｇ（0.0311モル）、水酸化カリウム3.65ｇ及び
触媒として塩化ベンジルトリエチルアンモニウム
1.0ｇを20mlの塩化メチレン溶解分散させ、実施
例に記載した方法で反応を行い、処理した。そ
の結果、粘性のある液体が５ｇ得られた。 Infrared spectrum; 2950, 2920, 2850, 1600,
1580, 1480, 1460, 1110 cm -1 Elemental analysis; C, 69.94%, H, 9.34% (theoretical value C for C 108 H 168 O 24 , 70.10%,
H, 9.15%) Example 2.0 g (0.00173 mol) of p-t-butyl calix[6]arene containing chloroform and methanol, p-toluenesulfonate of polyethylene glycol monomethyl ether (average molecular weight 440)
13.7g (0.0311 mol), potassium hydroxide 3.65g and benzyltriethylammonium chloride as catalyst
1.0 g was dissolved and dispersed in 20 ml of methylene chloride, and the reaction was carried out by the method described in the Examples. As a result, 5 g of viscous liquid was obtained.
また、この物質は、赤外スペクトル（液膜）分
析のデータから下記構造式を持つと思われる。 Furthermore, this substance appears to have the following structural formula based on data from infrared spectrum (liquid film) analysis.
赤外スペクトル；2950，2900，2850，1600，
1470，1130cm-1
（発明の効果）
以上のように本発明にれば、反応は低温で起こ
り、また操作が簡単なため、危険もなく、安全に
反応を終えることができる。また、生成物は高収
率で得ることができる。 Infrared spectrum; 2950, 2900, 2850, 1600,
1470, 1130 cm -1 (Effects of the Invention) As described above, according to the present invention, the reaction occurs at a low temperature and the operation is simple, so the reaction can be completed safely without any danger. Also, the product can be obtained in high yield.
Claims (1)
８の整数を夫々示す。） で表されるカリツクス〔ｎ〕アレーンを、アルカ
リ金属化合物及び相間移動触媒の存在下、有機溶
媒中、一般式 Ｘ−（CH2CH2Ｏ）nR′ （式中、R′は水素又はアルキル基を示し、ｍ
は１〜20の数である。Ｘはアリールスルホニル基
を示す。） で表されるポリエチレングリコール誘導体と反応
させ、一般式 （式中Ｒ及びR′は水素又はアルキル基を、ｎ
は４〜８の整数を、ｍは１〜20の数を夫々示す。）
で表されるカリツクスアレーン誘導体を製造する
ことを特徴とするカリツクスアレーン誘導体の製
造方法。 ２ 相間移動触媒が四級アンモニウム塩であるこ
とを特徴とする請求項１記載のカリツクスアレー
ン誘導体の製造方法。[Claims] 1. General formula (In the formula, R is hydrogen or an alkyl group, and n is 4 to
Each represents an integer of 8. ) in an organic solvent in the presence of an alkali metal compound and a phase transfer catalyst, a calix [ n ]arene represented by the general formula Indicates an alkyl group, m
is a number from 1 to 20. X represents an arylsulfonyl group. ) is reacted with a polyethylene glycol derivative represented by the general formula (In the formula, R and R' represent hydrogen or an alkyl group, n
represents an integer from 4 to 8, and m represents a number from 1 to 20, respectively. )
1. A method for producing a calyxarene derivative, which comprises producing a calyxarene derivative represented by: 2. The method for producing a calixarene derivative according to claim 1, wherein the phase transfer catalyst is a quaternary ammonium salt.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20248888A JPH0253749A (en) | 1988-08-12 | 1988-08-12 | Production of calixarene derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20248888A JPH0253749A (en) | 1988-08-12 | 1988-08-12 | Production of calixarene derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0253749A JPH0253749A (en) | 1990-02-22 |
| JPH0529375B2 true JPH0529375B2 (en) | 1993-04-30 |
Family
ID=16458332
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20248888A Granted JPH0253749A (en) | 1988-08-12 | 1988-08-12 | Production of calixarene derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0253749A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7122708B1 (en) * | 2000-05-12 | 2006-10-17 | Basf Aktiengesellschaft | High-functionality polyether polyols and preparation thereof |
| JP5008199B2 (en) * | 2008-02-06 | 2012-08-22 | 日立化成工業株式会社 | Epoxy resin curing agent, epoxy resin composition, and electronic component device |
| CN103052670B (en) * | 2010-07-30 | 2016-03-02 | 三菱瓦斯化学株式会社 | Compound, radiation sensitive composition and resist pattern forming method |
-
1988
- 1988-08-12 JP JP20248888A patent/JPH0253749A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0253749A (en) | 1990-02-22 |
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