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Method of producing epoxy compound, epoxy resin composition and its applications, ultraviolet rays-curable can-coating composition and method of producing coated metal can

a technology of epoxy resin and composition, applied in the direction of synthetic resin layered products, instruments, photomechanical devices, etc., can solve the problems of insufficient adhesion to a raw material and processability, poor surface curability, insufficient film performance, etc., to achieve excellent moisture and heat resistance and transparency.

Inactive Publication Date: 2003-03-27
DAICEL CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it has problems that adhesion to a raw material and processability are insufficient, surface curability is poor due to inhibition of curing by oxygen, and in particular, in the case of using the coating material in the form of a thin film (2 to 8 .mu.m), facilities for nitrogen sealing or the like are necessary.
However, it has problems that because curing rate is slow, film performances, in particular film appearance and retort resistance, are insufficient.
Further, both of the radical polymerization type coating material and cationic polymerization type coating material have the problem that curability is insufficient in low irradiation dose (less than 100 mj / cm.sup.2).
However, this coating composition has problems on hardness in hot water pertaining to retort resistance, film appearance, impact resistance, and the like, due to the above reasons.

Method used

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  • Method of producing epoxy compound, epoxy resin composition and its applications, ultraviolet rays-curable can-coating composition and method of producing coated metal can
  • Method of producing epoxy compound, epoxy resin composition and its applications, ultraviolet rays-curable can-coating composition and method of producing coated metal can
  • Method of producing epoxy compound, epoxy resin composition and its applications, ultraviolet rays-curable can-coating composition and method of producing coated metal can

Examples

Experimental program
Comparison scheme
Effect test

production example 1

[0185] 10% acetaldehyde-ethyl acetate solution containing cobalt acetate was charged in a 300 ml stainless reactor equipped with an air inlet, a perforated plate for dispersing a gas and a cooling jacket at 114 kg / h, and reaction was conducted at 45.degree. C. while blowing compressed air. The resulting reaction solution contained 10.1% of peracetic acid, 2.2% of acetaldehyde monoperacetate and 2.0% of acetic acid. This solution was charged in a distillation column together with sodium polyphosphate, followed by concentration, thereby obtaining a peracetic acid solution. In the solution, a peracetic acid concentration was 29.1% and water content was 0.47%.

example i-1

[0186] Synthesis of Alicyclic Epoxy Compound (A-1)

[0187] 36 g of water, 12.0 g of sodium hydrogensulfate, 500 g of isopropylidene-4,4'-dicyclohexanol (a product of Aldrich Chemical Company Inc.) and 500 g of Solvesso 150 (a product of Exxon Chemical) as a solvent were added to a 1 liter flask with a jacket, which is equipped with a stirrer, a cooling tube, a thermometer and a nitrogen inlet, and dehydration reaction was conducted at 100.degree. C.

[0188] Reaction was completed at the time when water was no longer distilled off. As a result of analysis of the reaction liquid with gas chromatography, 2,2-bis (3',4'-cyclohexenyl)propane was formed in a yield of 96%. The reaction solution obtained was washed with 500 ml of ion-exchanged water using a separatory funnel. An organic layer was then distilled under reduced pressure to obtain 387.0 g of colorless, transparent liquid 2,2-bis(3',-4'-cyclohexenyl)propane. Purity of the liquid obtained was 96.1%.

[0189] 100 g of the 2,2-bis(3'-4'-c...

example i-2

[0191] Synthesis of Alicyclic Epoxy Compound (A-2)

[0192] 300 g of 4,4'-dicyclohexanolmethane, 600 g of toluene, 3 g of paratoluenesulfonic acid were added to a 1 liter flask with a jacket, which is equipped with a stirrer, a cooling tube, a thermometer and a nitrogen inlet, and dehydration reaction was conducted at 110.degree. C.

[0193] Reaction was completed at the time when water was no longer distilled off. As a result of analysis of the reaction liquid with gas chromatography, di(3,4-cyclohexenyl)methane was formed in a yield of 96%. The reaction solution obtained was washed with 500 ml of ion-exchanged water using a separatory funnel. An organic layer was then distilled under reduced pressure to obtain 269 g of colorless, transparent liquid di(3-4-cyclohexenyl)methane.

[0194] 100 g of the di(3-4-cyclohexenyl)methane and 200 g of ethyl acetate were charged in the same type of a 1 liter flask with a jacket as in Example I-1. While blowing nitrogen to a gas phase, 276.2 g of an ethy...

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Abstract

The invention I provides a method of producing an alicyclic epoxy compound having a specific structure, which comprises epoxidizing an alicyclic olefin compound having a specific structure by using an aliphatic percarboxylic acid having low water content. The alicyclic epoxy compound is useful for use in coatings, inks, adhesives, sealants, encapsulants, stabilizers or the like. The invention II provides an epoxy resin composition containing the alicyclic epoxy compound as a main component, and a photosemiconductor device comprising a photosemiconductor element encapsulated with the epoxy resin composition. The epoxy resin composition can be cured by heating, thereby obtaining a cured product having excellent moisture and heat resistance and transparency. The invention III provides: an ultraviolet rays-curable can-coating composition containing the alicyclic epoxy compound as a main component, which can be cured by ultraviolet irradiation, and can form a coating film having excellent film performances such as processability, adhesion, hardness and scratch resistance, particularly film appearance and retort resistance; and a process of producing a coated metal can using the composition.

Description

[0001] Invention I relates to a method of producing an epoxy resin compound. More particularly, it relates to a method of producing an alicyclic epoxy compound having a specific structure by oxidizing an alicyclic olefin compound with an aliphatic percarboxylic acid having low,water content. The alicyclic epoxy compound is useful for use in coatings, inks, adhesives, sealants, encapsulants, stabilizers or the like.[0002] Invention II relates to an epoxy resin composition containing an alicyclic epoxy compound as a main component and applications thereof. More particularly, it relates to an epoxy resin composition which can be cured by heating, thereby obtaining a cured product having good moisture and heat resistance and transparency, and applications thereof for photosemiconductor encapsulation.[0003] Invention III relates to an ultraviolet rays-curable can-coating composition containing an alicyclic epoxy compound as a main component, which can be cured by ultraviolet irradiation,...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07D303/16C07D303/22C08G59/22C08G59/24C08G59/38C09D163/00G03F7/038
CPCC07D303/16C07D303/22C08G59/226C08G59/24C08G59/38C09D163/00G03F7/038Y10T428/31511C07D407/12C07D301/14C08G59/00
Inventor TAKAI, HIDEYUKE
Owner DAICEL CHEM IND LTD
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