JPH0643408B2 - Glycidyl compound incorporation complex - Google Patents
Glycidyl compound incorporation complexInfo
- Publication number
- JPH0643408B2 JPH0643408B2 JP23068785A JP23068785A JPH0643408B2 JP H0643408 B2 JPH0643408 B2 JP H0643408B2 JP 23068785 A JP23068785 A JP 23068785A JP 23068785 A JP23068785 A JP 23068785A JP H0643408 B2 JPH0643408 B2 JP H0643408B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- compound
- glycidyl
- complex
- formula
- 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 - Fee Related
Links
- -1 Glycidyl compound Chemical class 0.000 title claims description 17
- 238000010348 incorporation Methods 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 25
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- WXTPRAZNOXQAFY-UHFFFAOYSA-N 1,1,6,6-tetraphenylhexa-2,4-diyne-1,6-diol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C#CC#CC(O)(C=1C=CC=CC=1)C1=CC=CC=C1 WXTPRAZNOXQAFY-UHFFFAOYSA-N 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 239000013078 crystal Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- YLNSNVGRSIOCEU-UHFFFAOYSA-N oxiran-2-ylmethyl butanoate Chemical compound CCCC(=O)OCC1CO1 YLNSNVGRSIOCEU-UHFFFAOYSA-N 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- VVHFXJOCUKBZFS-UHFFFAOYSA-N 2-(chloromethyl)-2-methyloxirane Chemical compound ClCC1(C)CO1 VVHFXJOCUKBZFS-UHFFFAOYSA-N 0.000 description 1
- KDSVXIGJVLFKOE-UHFFFAOYSA-N 2-(ethylsulfanylmethyl)oxirane Chemical compound CCSCC1CO1 KDSVXIGJVLFKOE-UHFFFAOYSA-N 0.000 description 1
- QYYCPWLLBSSFBW-UHFFFAOYSA-N 2-(naphthalen-1-yloxymethyl)oxirane Chemical compound C=1C=CC2=CC=CC=C2C=1OCC1CO1 QYYCPWLLBSSFBW-UHFFFAOYSA-N 0.000 description 1
- CKZJQEQANLYJAG-UHFFFAOYSA-N 2-phenyl-2-[(2-phenyloxiran-2-yl)methoxymethyl]oxirane Chemical compound C1OC1(C=1C=CC=CC=1)COCC1(C=2C=CC=CC=2)CO1 CKZJQEQANLYJAG-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- URYGFDRDSYOMTO-UHFFFAOYSA-N oxiran-2-ylmethyl 2-naphthalen-1-yloxyacetate Chemical compound C=1C=CC2=CC=CC=C2C=1OCC(=O)OCC1CO1 URYGFDRDSYOMTO-UHFFFAOYSA-N 0.000 description 1
- JUVGLPRIQOJMIR-UHFFFAOYSA-N oxiran-2-ylmethyl 3-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1C=CC(=O)OCC1CO1 JUVGLPRIQOJMIR-UHFFFAOYSA-N 0.000 description 1
- XRQKARZTFMEBBY-UHFFFAOYSA-N oxiran-2-ylmethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1CO1 XRQKARZTFMEBBY-UHFFFAOYSA-N 0.000 description 1
- YEARBAZDKOUUAM-UHFFFAOYSA-N oxiran-2-ylmethyl naphthalene-1-carboxylate Chemical compound C=1C=CC2=CC=CC=C2C=1C(=O)OCC1CO1 YEARBAZDKOUUAM-UHFFFAOYSA-N 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- QNAJAJLBHMMOJB-UHFFFAOYSA-N oxiran-2-ylmethyl propanoate Chemical compound CCC(=O)OCC1CO1 QNAJAJLBHMMOJB-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
Landscapes
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】 （発明の技術分野） 本発明はグリシジル化合物を取り込んで生成する、安定
であると共に容易にグリシジル化合物を放出できるグリ
シジル化合物取り込み錯体（いわゆる包接化合物）に関
する。TECHNICAL FIELD OF THE INVENTION The present invention relates to a glycidyl compound-incorporating complex (so-called clathrate compound), which is formed by incorporating a glycidyl compound, is stable and can easily release the glycidyl compound.
（従来技術） 有機化合物間の取り込み錯体は既にいくつか知られてお
り、これらの錯体については取り込まれた化合物（ゲス
ト(guest)化合物）の反応性が自由な時の状態の反応性
と異なることに興味がもたれている。また一方、化合物
の精製単離を目的としてこの種の錯体を利用しようとす
る試みもある。(Prior Art) Several incorporation complexes between organic compounds are already known, and the reactivity of the incorporated compound (guest compound) is different from the reactivity of the complex when it is free. Interested in. On the other hand, there are also attempts to utilize this type of complex for the purpose of purifying and isolating the compound.
本発明者らは1,1,6,6−テトラフェニルヘキサ−2,4−ジ
イン−1,6−ジオールをホスト(host)化合物として種々
の化合物と結晶性の錯体を形成させたことを既に報告し
た(Tetrahedron Lett.1968,3695、1981,22,3865、J.Chem.
Soc.Jpn 1983,239)。しかしながら、上記ホスト化合物
とグリシジル化合物との組合せによる取込み錯体につい
ては全く知られていない。グリシジル化合物は有機合成
化学上重要な中間体であり、また高分子合成化学におい
ても重要なモノマーである。これらのグリシジル化合物
は種類によっては高純度で得ることは必ずしも容易では
ない。またグリシジル化合物の重合反応における取込み
錯体の効果も新規なポリマーを製造する上で非常に関心
がもたれるところである。The present inventors have already shown that 1,1,6,6-tetraphenylhexa-2,4-diyne-1,6-diol was used as a host compound to form a crystalline complex with various compounds. Reported (Tetrahedron Lett. 1968, 3695, 1981, 22, 3865, J. Chem.
Soc. Jpn 1983, 239). However, an incorporation complex obtained by combining the host compound and the glycidyl compound is not known at all. Glycidyl compounds are important intermediates in synthetic organic chemistry and also important monomers in synthetic polymer chemistry. It is not always easy to obtain these glycidyl compounds with high purity depending on the kind. The effect of the incorporation complex on the polymerization reaction of the glycidyl compound is also of great interest in producing a new polymer.
（発明の目的） 本発明は有機合成化学上各種の応用が考えられる、特に
高純度の中間体もしくは重合用モノマーとしてのグリシ
ジル化合物を得るための、または新しい反応性を示す中
間体もしくは重合用モノマーとしての新規なグリシジル
化合物取り込み錯体を提供することを目的とする。(Object of the invention) The present invention is considered to have various applications in synthetic organic chemistry, particularly for obtaining a glycidyl compound as a high-purity intermediate or a monomer for polymerization, or an intermediate or a monomer for polymerization showing a new reactivity. An object of the present invention is to provide a novel glycidyl compound-incorporated complex as.
（発明の構成） 本発明は、下記一般式（Ｉ）で示されるグリシジル化合
物 （但し、（Ｉ）式において、Ｒは水素原子又はメチル基
を表わす。Ｘはヒドロキシ基，アルコキシ基，アシル
基，アシルオキシ基，アルコキシカルボニル基，フェノ
キシ基，Ｏ−メチルフェノキシ基，ナフトキシ基，シア
ノ基及びアルキルチオ基から選ばれる基又はハロゲン原
子を表わす。）と下記一般式（II）で示される1,1,6,6
−テトラフェニルヘキサ−2,4−ジイン−1,6−ジオール
もしくはその誘導体 （但し、（II）式において、Ｘはアルキル基，アリール
基，アラルキル基，アルコキシ基及びアルキルチオ基か
ら選ばれる基か水素原子又はハロゲン原子を表わす。ｎ
は１〜５の整数である。） とによって形成されてなるグリシジル化合物取り込み錯
体である。(Structure of the Invention) The present invention provides a glycidyl compound represented by the following general formula (I). (In the formula (I), R represents a hydrogen atom or a methyl group. X represents a hydroxy group, an alkoxy group, an acyl group, an acyloxy group, an alkoxycarbonyl group, a phenoxy group, an O-methylphenoxy group, a naphthoxy group, a cyano group. And a group selected from an alkylthio group or a halogen atom) and 1,1,6,6 represented by the following general formula (II)
-Tetraphenylhexa-2,4-diyne-1,6-diol or its derivative (However, in the formula (II), X represents a group selected from an alkyl group, an aryl group, an aralkyl group, an alkoxy group and an alkylthio group, a hydrogen atom or a halogen atom.
Is an integer of 1 to 5. ) And a glycidyl compound incorporation complex formed by
本発明においてゲスト化合物となるグリシジル化合物と
しては、グリシドール，エピクロルヒドリン，エピブロ
モヒドリン，β−メチルエピクロルヒドリン，アリルグ
リシジルエーテル，ブチルグリシジルエーテル，フェニ
ルグリシジルエーテル，Ｏ−メチルフェニルグリシジル
エーテル，ナフチルグリシジルエーテル，酢酸グリシジ
ル，プロピオン酸グリシジル，酪酸グリシジル，安息香
酸グリシジル，ケイ皮酸グリシジル，アクリル酸グリシ
ジル，メタクリル酸グリシジル，ナフトエ酸グリシジ
ル，ナフトキシ酢酸グリシジル，エチルグリシジルチオ
エーテル，ω−エポキシ酪酸エチルなどが挙げられる。Examples of the glycidyl compound serving as a guest compound in the present invention include glycidol, epichlorohydrin, epibromohydrin, β-methylepichlorohydrin, allyl glycidyl ether, butyl glycidyl ether, phenyl glycidyl ether, O-methylphenyl glycidyl ether, naphthyl glycidyl ether, acetic acid. Examples thereof include glycidyl, glycidyl propionate, glycidyl butyrate, glycidyl benzoate, glycidyl cinnamate, glycidyl acrylate, glycidyl methacrylate, glycidyl naphthoate, glycidyl naphthoxyacetate, ethyl glycidyl thioether, and ethyl ω-epoxybutyrate.
本発明においてホスト化合物となる（II）式化合物は既
に知られており、前駆体である下記（III）式化合物を
酸化カップリング、例えば塩化第一銅−ピリジン触媒の
存在下アセトン溶液中で空気酸化することによって容易
に製造できる。The formula (II) compound serving as a host compound in the present invention is already known, and the following formula (III) compound which is a precursor is oxidatively coupled, for example, air in an acetone solution in the presence of a cuprous chloride-pyridine catalyst. It can be easily produced by oxidation.
また上記（III）式化合物は対応するケトンとアセチレ
ンからエチニル化反応によって製造される。 Further, the above formula (III) compound is produced from a corresponding ketone and acetylene by an ethynylation reaction.
上記（II）式化合物の具体的な例としては、1,1,6,6−
テトラフェニルヘキサ−2,4−ジイン−1,6−ジオール 1,1,6,6−テトラ（ｐ−クロロフェニル）ヘキサ−2,4−
ジイン−1,6−ジオール 1,1,6,6−テトラ（ｐ−フルオロフェニル）ヘキサ−2,4
−ジイン−1,6−ジオール 1,1,6,6−テトラ（ｐ−メチルフェニル）ヘキサ−2,4−
ジイン−1,6−ジオール 1,1,6,6−テトラ（ｏ−クロロフェニル）ヘキサ−2,4−
ジイン−1,6−ジオール 1,1,6,6−テトラ（2,4−ジクロロフェニル）ヘキサ−2,
4−ジイン−1,6−ジオール 1,1,6,6−テトラ（3,5−ジクロロフェニル）ヘキサ−2,
4−ジイン−1,6−ジオール 1,1,6,6−テトラ（ｐ−ブトキシフェニル）ヘキサ−2,4
−ジイン−1,6−ジオール 1,1,6,6−テトラ（ｐ−エチルチオフェニル）ヘキサ−
2,4−ジイン−1,6−ジオール などが挙げられる。Specific examples of the formula (II) compound include 1,1,6,6-
Tetraphenylhexa-2,4-diyne-1,6-diol 1,1,6,6-tetra (p-chlorophenyl) hexa-2,4-
Diyne-1,6-diol 1,1,6,6-tetra (p-fluorophenyl) hexa-2,4
-Diyne-1,6-diol 1,1,6,6-tetra (p-methylphenyl) hexa-2,4-
Diyne-1,6-diol 1,1,6,6-tetra (o-chlorophenyl) hexa-2,4-
Diyne-1,6-diol 1,1,6,6-tetra (2,4-dichlorophenyl) hexa-2,
4-diyne-1,6-diol 1,1,6,6-tetra (3,5-dichlorophenyl) hexa-2,
4-diyne-1,6-diol 1,1,6,6-tetra (p-butoxyphenyl) hexa-2,4
-Diyne-1,6-diol 1,1,6,6-tetra (p-ethylthiophenyl) hexa-
2,4-diyne-1,6-diol and the like can be mentioned.
本発明において（Ｉ）式化合物と（II）式化合物から錯
体を形成させるには、これら両者を直接混合してもよい
し、溶媒を用いて反応させてもよい。溶媒としては脂肪
族炭化水素類，芳香族炭化水素類，エーテル類の単独も
しくはこれらの混合物が適当である。反応温度や反応時
間は上記（Ｉ）式，（II）式の化合物の組合わせによっ
て異なるが、通常室温乃至溶媒の還流温度の範囲が適当
である。反応時間は錯体形成による沈澱によって容易に
定められる。In the present invention, in order to form a complex from the compound of formula (I) and the compound of formula (II), they may be mixed directly or may be reacted using a solvent. Suitable solvents are aliphatic hydrocarbons, aromatic hydrocarbons and ethers, either alone or as a mixture thereof. The reaction temperature and the reaction time vary depending on the combination of the compounds of the above formulas (I) and (II), but usually a range of room temperature to the reflux temperature of the solvent is suitable. The reaction time is easily determined by precipitation due to complex formation.
錯体は使用する（Ｉ）式化合物と（II）式化合物の組合
わせによって異なるが、通常（Ｉ）式化合物と（II）式
化合物のモル比が３：１〜１：３の割合の化合物として
生成する。The complex varies depending on the combination of the formula compound (I) and the formula compound (II) used, but is usually a compound having a molar ratio of the formula compound (I) and the formula compound (II) of 3: 1 to 1: 3. To generate.
得られた錯体は固態結晶であり、これを再結晶によって
精製することが可能である。またこの錯体を加熱蒸溜、
極性溶媒による置換、クロマトグラフィーなどの手段に
よって分解させて特異な性質を有するグリシジル化合物
を取り出すこともできる。The obtained complex is a solid crystal and can be purified by recrystallization. Also, this complex is heated and distilled,
It is also possible to take out a glycidyl compound having a unique property by decomposing it by means such as substitution with a polar solvent or chromatography.
（発明の効果） 本発明の錯体は新規な化合物であり、安定性に優れると
共に通常の手段によって特異な性質をもった有用なグリ
シジル化合物を極めて容易に放出することができる。(Effects of the Invention) The complex of the present invention is a novel compound, which is extremely stable and can release a useful glycidyl compound having a unique property by an ordinary means very easily.
（実施例） 実施例１ 1,1,6,6−テトラフェニルヘキサー2,4−ジイン1,6−ジ
オール2.0gを酪酸グリシジル20mlに加熱溶解させ、その
後室温で12時間放置したところ無色プリズム状結晶2.1g
が析出した。この結晶は融点92〜99℃で原料化合物のモ
ル比が１：１の錯体であることが確められた。(Example) Example 1 2.0 g of 1,1,6,6-tetraphenylhexa-2,4-diyne-1,6-diol was dissolved in 20 ml of glycidyl butyrate by heating and then left standing at room temperature for 12 hours to give colorless prisms. 2.1 g of crystals
Was deposited. It was confirmed that this crystal was a complex having a melting point of 92 to 99 ° C. and a molar ratio of raw material compounds of 1: 1.
実施例２ 酪酸グリシジルの代りにフェニルグリシジルエーテル20
mlを用いた以外は実施例１と同様にして無色針状結晶2.
0gを得た。この結晶は融点86〜91℃で原料化合物のモル
比が１：１の錯体であることが確められた。Example 2 Phenylglycidyl ether 20 instead of glycidyl butyrate
Colorless needle crystals in the same manner as in Example 1 except that ml was used 2.
I got 0g. It was confirmed that this crystal was a complex having a melting point of 86 to 91 ° C. and a molar ratio of raw material compounds of 1: 1.
上記実施例１〜２によって得られた錯体の赤外線吸収ス
ペクトルを第１図〜第２図に示した。The infrared absorption spectra of the complexes obtained in Examples 1 and 2 are shown in FIGS. 1 and 2.
第１図は実施例１よって得られた錯体の赤外線吸収スペ
クトルであり、第２図は実施例２によって得られた錯体
の赤外線吸収スペクトルである。FIG. 1 is an infrared absorption spectrum of the complex obtained in Example 1, and FIG. 2 is an infrared absorption spectrum of the complex obtained in Example 2.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.5 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ｃ０７Ｄ 303/12 ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 5 Identification code Internal reference number FI technical display area C07D 303/12
Claims (1)
合物と一般式（II）で示される１，１，６，６−テトラ
フェニルヘキサ−２，４−ジイン−１，６−ジオールも
しくはその誘導体とによって形成されてなるグリシジル
化合物取り込み錯体。 （但し、（Ｉ）式において、Ｒは水素原子又はメチル基
を表わす。Ｘはヒドロキシ基，アルコキシ基，アシル
基，アシルオキシ基，アルコキシカルボニル基，フェノ
キシ基，Ｏ−メチルフェノキシ基，ナフトキシ基，シア
ノ基及びアルキルチオ基から選ばれる基又はハロゲン原
子を表わす。） （但し（II）式において、Ｘはアルキル基，アリール
基，アラルキル基，アルコキシ基及びアルキルチオ基か
ら選ばれる基か水素原子又はハロゲン原子を表わす。ｎ
は１〜５の整数である。）1. A glycidyl compound represented by the following general formula (I) and 1,1,6,6-tetraphenylhexa-2,4-diyne-1,6-diol represented by the general formula (II) or a compound thereof. A glycidyl compound-incorporating complex formed with a derivative. (In the formula (I), R represents a hydrogen atom or a methyl group. X represents a hydroxy group, an alkoxy group, an acyl group, an acyloxy group, an alkoxycarbonyl group, a phenoxy group, an O-methylphenoxy group, a naphthoxy group, a cyano group. Represents a group or a halogen atom selected from a group and an alkylthio group.) (In the formula (II), X represents a group selected from an alkyl group, an aryl group, an aralkyl group, an alkoxy group and an alkylthio group, a hydrogen atom or a halogen atom.
Is an integer of 1 to 5. )
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23068785A JPH0643408B2 (en) | 1985-10-16 | 1985-10-16 | Glycidyl compound incorporation complex |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23068785A JPH0643408B2 (en) | 1985-10-16 | 1985-10-16 | Glycidyl compound incorporation complex |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6289674A JPS6289674A (en) | 1987-04-24 |
| JPH0643408B2 true JPH0643408B2 (en) | 1994-06-08 |
Family
ID=16911735
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP23068785A Expired - Fee Related JPH0643408B2 (en) | 1985-10-16 | 1985-10-16 | Glycidyl compound incorporation complex |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0643408B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04117856U (en) * | 1991-04-05 | 1992-10-21 | 新日本製鐵株式会社 | Levitation support device |
| EP0589044B1 (en) * | 1991-12-12 | 1996-10-23 | Nippon Soda Co., Ltd. | Novel inclusion compound comprising tetrakisphenol as host |
-
1985
- 1985-10-16 JP JP23068785A patent/JPH0643408B2/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| 日本化学学会誌、１９８３年２号，２３９−２４２頁 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6289674A (en) | 1987-04-24 |
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| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |