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High-purity alicyclic epoxy compound, process for producing the same, curable epoxy resin composition, cured article thereof, and use

An epoxy compound and alicyclic technology, applied in the direction of organic chemistry, can solve problems such as the hue cannot meet the requirements, and the solvent is difficult to remove.

Inactive Publication Date: 2007-03-21
DAICEL CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the synthesis of epoxy compound (I), the solvent is difficult to remove
So, still have the high molecular weight part that elution time is shorter than the elution time of alicyclic epoxy compound (I) in GPC analysis detection, and have retention time than alicyclic epoxy compound (I) in gas chromatography detection Impurities and reaction intermediates with short retention time of I) lead to epoxy compound (I) in terms of hue (APHA) which cannot meet the requirements and are not enough to be applied to transparent materials that require heat resistance, including display materials such as liquid crystals

Method used

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  • High-purity alicyclic epoxy compound, process for producing the same, curable epoxy resin composition, cured article thereof, and use
  • High-purity alicyclic epoxy compound, process for producing the same, curable epoxy resin composition, cured article thereof, and use
  • High-purity alicyclic epoxy compound, process for producing the same, curable epoxy resin composition, cured article thereof, and use

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Embodiment

[0226]Although the present invention will be described more fully hereinafter with reference to Examples and Application Examples, the present invention is not intended to be limited by them. "%" used in the examples means "% by weight" unless otherwise specified.

[0227]

[0228] In the pretreatment, 0.04 g of the alicyclic epoxy compound (I) was dissolved in 2 g of tetrahydrofuran (THF) and filtered using a filter [DISMIC 13JP050AN manufactured by Toyo Roshi Kaisha, Ltd.] with a pore diameter of 0.50 μm. The THF solution of the obtained alicyclic epoxy compound (I) was analyzed by GPC to give the peak area ratio of each component, indicating the concentration of each component. The respective concentrations of the components eluting earlier than the alicyclic epoxy compound (I) were added to determine the concentration of the high molecular weight component.

[0229] Instrument: HLC-80020GPC [manufactured by TOSO CORPORATION]

[0230] Detector: Differential refractomete...

preparation Embodiment 1

[0259] Add the 10% acetaldehyde-ethyl acetate solution that contains cobalt acetate with the rate of 114kg / hour in the 300ml stainless steel reactor that is equipped with air inlet, gas dispersion perforated plate and condensing jacket, inject compressed air into reactor simultaneously and The reaction was carried out at 45°C. The reaction solution contained 10.1% peracetic acid, 2.2% acetaldehyde-ethyl acetate and 2.0% acetic acid. The solution was placed together with sodium polyphosphate in a distillation column and concentrated to obtain a peracetic acid solution. The peracetic acid solution contained 29.1% peracetic acid and 0.47% water.

Embodiment 1

[0261] Add 36 g of water, 12.0 g of sodium bisulfate, 500 g of isopropylidene-4', 4-dicyclohexanol (by ALDRICH Manufactured) and 500 g of Solvesso 150 (manufactured by Exxon Chemical) as a solution, dehydration reaction was carried out at 100°C. The reaction was completed when the water was completely distilled off. The reaction solution was analyzed by gas chromatography, and the yield of 2,2-bis(3',4'-cyclohexenyl)propane was 96%. After the resulting reaction solution was washed in 500 ml of ion-exchanged water using a separatory funnel, the organic layer was distilled under reduced pressure to obtain 387.0 g of 2,2-bis(3',4'-cyclohexenyl)propane, which was a colorless and transparent liquid. The purity is 96.1%. To the aforementioned 1 L jacketed flask was added 100 g of the 2,2 bis(3',4'-cyclohexenyl)propane and 300 g of ethyl acetate. Then, 307.2 g of a substantially water-free ethyl acetate solution of peracetic acid (concentration of peracetic acid: 29.1%, water cont...

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Abstract

A high-purity alicyclic epoxy compound which is obtained by epoxidizing an alicyclic olefin compound with an aliphatic peroxycarboxylic acid containing substantially no water, subsequently subjecting the resultant compound to desolvation to produce an alicyclic epoxy compound represented by the general formula (I): (I) and purifying the epoxy compound by distillation and in which the concentration of high-molecular components having a shorter elution time than the alicyclic epoxy compound as determined by GPC analysis is 5.5% or lower in terms of areal ratio, the concentration of impurities having a shorter retention time than the alicyclic epoxy compound as determined by GC analysis is 19.5% or lower in terms of areal ratio, the concentration of intermediates is 4.5% or lower in terms of areal ratio, and the hue (APHA) is 60 or less; a process for efficiently producing the epoxy compound using a less toxic solvent; and a curable resin composition containing the compound.

Description

technical field [0001] The present invention relates to a high-purity alicyclic epoxy compound obtained by oxidation of an alicyclic olefin compound with an aliphatic percarboxylic acid substantially free of water followed by purification; a process for the preparation of the compound; a curable epoxy resin Compositions; cured products thereof; and various applications of the high-purity cycloaliphatic epoxy compounds. Specifically, the present invention relates to a high-purity cycloaliphatic epoxy compound with reduced concentration of impurities or reaction intermediates and improved color hue; a method for purifying the compound product by distillation; a method comprising said high-purity cycloaliphatic epoxy compound; A curable epoxy resin composition of an oxygen compound; a cured product thereof; and various applications of the high-purity cycloaliphatic epoxy compound. The high-purity cycloaliphatic epoxy compound is used in applications that require heat resistance ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D301/14C07D303/04C07D303/34C08G59/24
CPCC07D303/04C07D303/34C07D407/12
Inventor 北尾久平高井英行
Owner DAICEL CHEM IND LTD