Process for preparation of alicyclic diepoxy compound, curable epoxy resin compositions, epoxy resin compositions for the encapsulation of electronic components, stabilizers for electrical insulating oils, and casting epoxy resin compositions for electrical insulation

Inactive Publication Date: 2006-01-12
DAICEL CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0033] An object of the present invention (1) is to provide a process for preparation of a less viscous and easily manageable alicyclic d

Problems solved by technology

If they are used under high temperatures and high moistures or under such a condition that a strong acid occurs, cured products thereof may suffer from decrease in physical properties.
Therefore, as the risk that the peroxydate is explosively decomposed is involved, there is a problem in safeness.
In addition, molybdenum chloride (V) used as a catalyst is expensive and strongly poisonous.
However, the cured product composed of the above aromatic epoxy resin for general purpose that is a glycidyl ether-based epoxy resin has the structure of an aromatic nucleus, so it has inferior weatherability outdoors.
Therefore, the glycidyl ether-based epoxy resin is mostly used by being dissolved in a solvent typified by toluene, xylene, methyl ethyl ketone, ethyl acetate, or the like, which causes a problem with workability and environmental safeness.
Since the epoxy compound with an alicyclic skeleton has sufficient performance but slightly lower reactivity when used in the above applications, the cured product thereof may suffer from decrease in physical properties and reactivity.
Furthermore, the foregoing monoepoxidized 4-vinylcyclohexene and limonene diepoxide evaporate at room temperature, which causes a problem with working surroundings.
However, none of those curable resin compositions each including the alicyclic diepoxy compound has displayed satisfactory performance yet.
Therefore, cracks occur in the portion of the resin and cracks and exfoliation occur around a chip, which reduces reliability, resulting in a problem of unusability as a pro

Method used

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  • Process for preparation of alicyclic diepoxy compound, curable epoxy resin compositions, epoxy resin compositions for the encapsulation of electronic components, stabilizers for electrical insulating oils, and casting epoxy resin compositions for electrical insulation
  • Process for preparation of alicyclic diepoxy compound, curable epoxy resin compositions, epoxy resin compositions for the encapsulation of electronic components, stabilizers for electrical insulating oils, and casting epoxy resin compositions for electrical insulation
  • Process for preparation of alicyclic diepoxy compound, curable epoxy resin compositions, epoxy resin compositions for the encapsulation of electronic components, stabilizers for electrical insulating oils, and casting epoxy resin compositions for electrical insulation

Examples

Experimental program
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Effect test

examples

Examples and Comparative Examples for Invention (1)

[0177] The following examples are used for illustrations of the present invention, and they do not restrict the scope at all.

example 1

[0178] In a reactor, 406 g of bicyclohexyl-3,3′-diene, which is an alicyclic olefin compound represented by the above general formula (II), and 1,217 g of ethyl acetate were placed. While nitrogen was flown into a gas phase part and the temperature in the reaction system was controlled at 37.5° C., 457 g of an ethyl acetate solution (water content: 0.41% by weight) containing peracetic acid at 30% by weight was added dropwise for about 3 hours. After the completion of dropwise addition of the peracetic acid solution, the resulting mixture was aged at 40° C. for 1 hour to complete the reaction. The crude liquid at the completion of the reaction was then washed with water at 30° C., and treated at 70° C. / 20 mmHg to remove low-boiling-point compounds. Consequently, 415 g of an epoxy compound was obtained with an yield of 85%.

[0179] The oxirane oxygen content of the epoxy compound obtained was 14.7% by weight (theoretical value: 16.5% by weight).

[0180] In 1HNMR analysis, a peak at abo...

example 2

[0181] 243 g of bicyclohexyl-3,3′-diene, which is an alicyclic olefin compound represented by the above general formula (II), and 730 g of ethyl acetate were placed. While nitrogen was flown into a gas phase part and the temperature in the reaction system was controlled at 37.5° C., 274 g of an ethyl acetate solution (water content: 0.41% by weight) containing peracetic acid at 30% by weight was added dropwise for about 3 hours. After the completion of dropwise addition of peracetic acid solution, the resulting mixture was aged at 40° C. for 1 hour to complete the reaction. The crude liquid at the completion of the reaction was then washed with water at 30° C., and treated at 70° C. / 20 mmHg to remove low-boiling-point compounds. Consequently, 270 g of an epoxy compound was obtained with an yield of 93%.

[0182] The oxirane oxygen content of the epoxy compound obtained was 15.3% by weight.

[0183] In 1HNMR analysis, a peak at about δ4.5 to 5 ppm originating from the inner double bond d...

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Abstract

According to the present invention (1), an alicyclic diepoxy compound represented by the following general formula (I):
can be produced in high purity and high yields at low cost, by epoxidizing the corresponding alicyclic diolefin compound with an organic percarboxylic acid. As the alicyclic diepoxy compound lacks an ester group in the molecule, it will show high reactivity for a cationic catalyst. Besides, when it is used as a curable epoxy resin composition of the present invention (2), it will show an effect of lowering its curing temperature or reducing its curing time. The curable epoxy resin composition has high reactivity for various curing agents, low viscosity, and excellent workability. Moreover, the curable resin composition is also superior in that it has less effect to working surroundings, and a cured product thereof shows useful physical properties for the uses in coatings, ink, adhesives, sealants, encapsulants, and the like. Furthermore, as a resin composition of the present invention (3) shows a low coefficient of water absorption, it is of extremely high quality as an epoxy resin composition for the encapsulation of electronic parts. In addition, a stabilizer for an electrical insulating oil of the present invention (4) (i.e., the alicyclic diepoxy compound or an electrical insulating oil containing such a compound) is low in acid value, and the stabilizer improves the properties of the insulating oil. In addition, a cured product obtained by curing a casting epoxy resin composition for electrical insulation of the present invention (5) has excellent properties such as high bending strength, high Tg, and low permittivity.

Description

TECHNICAL FIELD [0001] The present invention relates to a process for preparation of an alicyclic diepoxy compound in which an unsaturated group-containing compound having a bicyclohexyl-3,3′-diene skeleton is reacted with an organic percarboxylic acid. In addition, the present invention relates to a curable resin composition having such the diepoxy compound as an essential ingredient and to a cured product thereof. The resin composition is useful in various fields including applications such as coatings, ink, adhesives, sealants, and encapsulating materials. Moreover, the present invention relates to an epoxy resin composition for encapsulating electronic parts such as a semiconductor, the epoxy resin composition containing the above alicyclic diepoxy compound as an essential ingredient and showing high moisture-resistance and high fluidity. Moreover, the present invention relates to a stabilizer for an electrical insulating oil and an electrical insulating oil. More particularly, ...

Claims

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Application Information

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IPC IPC(8): C08G59/38C08L63/00C07D301/14C07D303/04C08G59/24
CPCC07D301/14C08G59/24C07D303/04C08G59/027C07D301/19C08G59/20H01B3/40
Inventor MAESHIMA, HISASHITAKAI, HIDEYUKI
Owner DAICEL CHEM IND LTD
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