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Diolefin compound, epoxy resin, curable resin composition and cured product

A technology of epoxy resin and curing resin, applied in the direction of organic chemistry, etc., can solve the problems of unoptimized operation, small molecular weight, high cost, etc., and achieve the effect of excellent mechanical properties and low colorability

Inactive Publication Date: 2011-11-09
NIPPON KAYAKU CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are not many types of alicyclic epoxy compounds available, and most of the raw materials before epoxidation are relatively expensive compounds
In addition, epoxides of dicyclopentadiene, etc. are cheap, but they have low polarity and small molecular weight, so they have sublimation properties, which are not only unfavorable in terms of work, but also have a high density of functional groups between molecules, resulting in a cured product with poor toughness. thing

Method used

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  • Diolefin compound, epoxy resin, curable resin composition and cured product
  • Diolefin compound, epoxy resin, curable resin composition and cured product
  • Diolefin compound, epoxy resin, curable resin composition and cured product

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0134] Into the flask with stirrer, reflux condenser, and stirring device, add 150 parts of water, 55.1 parts of 3-cyclohexene formaldehyde, 62.6 parts of trimethylolpropane, and 7.3 parts of concentrated hydrochloric acid while purging nitrogen gas , and reacted at 60 °C for 10 hours. After completion of the reaction, 100 parts of water and 30 parts of 3% sodium hydroxide aqueous solution were added, and then neutralized with disodium hydrogen phosphate. 200 parts of methyl isobutyl ketone was added thereto, and after washing three times with 100 parts of water, the solvent and the like were removed to obtain the following formula (4)

[0135]

[0136] 101 parts of the diene compound (D-1) of the present invention represented.

[0137] The obtained compound was in a liquid form, and its purity was 94% as measured by GC, and 98% was confirmed as a result of GPC analysis. The viscosity is 21000mPa·s (25°C, E-type viscometer).

Embodiment 2

[0139] In the flask with stirrer, reflux condenser, stirring device, Dean-Stark (Dean-Stark) tube, add 150 parts of toluene, 55.1 parts of 3-cyclohexene formaldehyde, two 62.6 parts of trimethylolpropane and 1.5 parts of p-toluenesulfonic acid were reacted for 10 hours while removing water under reflux conditions. After completion of the reaction, 3 parts of sodium tripolyphosphate was added, stirred at 100° C. for 30 minutes, filtered, 200 parts of toluene and 100 parts of 10% by weight disodium hydrogen phosphate aqueous solution were added, washed with water, and washed with water three times with 100 parts of water. 200 parts of methyl isobutyl ketone was added thereto, washed with 100 parts of water three times, and then the solvent and the like were removed to obtain 108 parts of the diene compound (D-2) of the present invention represented by the above formula (4).

[0140] The obtained compound was in a liquid form, and its purity as measured by GC was 93%, and as a re...

Embodiment 3

[0142] Add 15 parts of water, 0.95 parts of 12-phosphotungstic acid, 0.78 parts of disodium hydrogen phosphate, dihardened tallow alkyl dimethyl After 2.7 parts of ammonium acetate (Lion Akuke system, 50% by weight hexane solution) and generate tungstic acid series catalyst, add 120 parts of toluene, 108 parts of compound (D-2) of the formula (4) that embodiment 2 obtains, carry out again By stirring, a solution in an emulsion state was obtained. The temperature of this solution was raised to 50 degreeC, 55 parts of 35% hydrogen peroxide aqueous solutions were added, stirring vigorously, and it stirred at 50 degreeC for 13 hours as it was. The progress of the reaction was confirmed by GC. After the reaction, the conversion rate of the substrate was >99%, and the raw material peak disappeared.

[0143] Then, after neutralizing with a 1% aqueous sodium hydroxide solution, 25 parts of a 20% aqueous sodium thiosulfate solution was added, stirred for 30 minutes, and then left to s...

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Abstract

The invention aims to provide a novel alicyclic epoxy resin having no ester bond in each molecule, and a precursor of the alicyclic epoxy resin. The precursor is a diolefin compound represented by formula (1) (wherein each of the plurality of R's independently represents a hydrogen atom or an alkyl group having 1-6 carbon atoms), and the epoxy resin is obtained by epoxidizing the diolefin compound.

Description

technical field [0001] The present invention relates to novel diene compounds and epoxy resins suitable for use as electrical and electronic materials. Background technique [0002] Epoxy resin is cured with various curing agents, and generally becomes a cured product with excellent mechanical properties, water resistance, chemical resistance, heat resistance, electrical properties, etc., and is used in adhesives, coatings, laminates, molding materials, casting materials, solder resist, etc. In recent years, especially in the field of semiconductor-related materials, electronic devices with light, thin, short, and small keywords such as mobile phones with cameras, ultra-thin LCD TVs and plasma TVs, and light notebook computers are flooded. , Therefore, very high characteristics are also required for packaging materials represented by epoxy resins. In particular, the structure of cutting-edge packaging is complicated, and the number of items that are difficult to seal unles...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D319/06C07D407/14C08G59/26
CPCC08L63/00C07D407/04C07D319/06C08G59/26
Inventor 中西政隆洼木健一宫川直房川田义浩佐佐木智江青木静铃木瑞观枪田正人小柳敬夫
Owner NIPPON KAYAKU CO LTD
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