JPS6049024A - Curing of epoxy resin - Google Patents

Abstract

PURPOSE:To obtain a cured epoxy resin having excellent heat resistance, by mixing a polyepoxy resin with 2,4-diamino-6-[2'-alkylimidazolyl(1)']ethyl-S-triazine, etc. as a hardener and a specific polymerizable monomer, etc., and heating the mixture. CONSTITUTION:A polyepoxy compound having one or more epoxy groups in a molecule is mixed with (B) a hardener comprising 2,4-diamino-6-[2'-alkylimidazolyl(1)']ethyl-S-triazine or an isocyanuric acid adduct of 2,4-diamino-6-[2'-alkylimidazolyl(1)']ethyl-S-triazine, (C) a polymerizable monomer comprising 2,4-diamino-6-vinyl-S-triazine and (D) a polymerization initiator, and the mixture is heated to obtain the objective opoxy resin. Preferably, the amount of the component B is 3-10pts.wt. per 100pts.wt. of the component A, that of the component C is 5-100mol% of the component A, and that of the component D is 0.5-1.0% of the component C.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for curing an epoxy compound having an average of more than one epoxy group in the molecule, and its purpose is to cure a polyepoxy compound and a curing agent mixed together. It has a long bottle life at room temperature, can be used as a one-component epoxy resin that quickly cures when heated to the desired temperature, and the cured resin has excellent heat resistance. The purpose is to grant the following.

The method of the present invention can be applied to electronic component sealing materials, insulating materials, adhesives, etc., and can exhibit significant f# effects.

When curing polyepoxy compounds, it is known that blending -1 midazole compounds results in a one-component composition with good workability and a resin with considerable heat resistance. In the manufacturing of
As density increases, improvements in workability, heat resistance, etc. are required.

In light of this fact, the name of the unexploded town, etc., was determined after intensive study on a one-component epoxy resin with high heat resistance. As a curing agent, 2,4-diamino-6-(2'-alkylimidazolyl(1)')ethyl-8-to'Jacine formula shown by the following formula (wherein formula 1 is an argyl group and R' is hydrogen 2,4-diamino-6-(2'-
Alkylimidazolyl(1)')ethyl-8-)! J azine isocyanuric acid adduct (wherein t and R' are the same as above) and 2,4-
The desired objective was achieved by adding a combination of diamino-6-pinyl-8-) riazine and a conjugating monomer with a conjugating agent initiator.

The reason why the epoxy resin cured product produced by the Himi method has excellent heat resistance is that when the polyepoxy compound and imidazole compound are heated, they undergo anionic polymerization to create a three-dimensional network structure, and vinyl triazine initiates polymerization. When heated in the presence of the epoxy resin, it radically polymerizes to form a linear polymer with high heat resistance.
The rigid chains of riazine intersect and form
This is thought to be due to the formation of a penetrated network structure.

The use of a specific imidazole compound in the method of the present invention is essential in order to achieve both workability such as shelf life and fluidity of the liquid composition, and heat resistance for the resin.〇Curing agent used in the present invention 2,4-diamino-6
-(2'-alkylimidazolyl(1)')enalu 1
3-) Riazine can be synthesized by the method described in Japanese Patent Publication No. 47-36391, and a representative example thereof is 2,4-diamino-6-(2'-methylimidazolyl(1)')ethyl -S-triazine, 2,4-diamino-6-(2'-ethyl 4'-methylimidazolyl (X
)' ) Ethyl-8-)riazine, 2,4-diamino-
6-(2'-cundecylimidazolyl (1)') ether-8-) liazine, etc., and the saponifying agent 2,4-diamino-6-(2'-argylimidazolyl (1)') ethyl-8 -) Addition of riazine inocyanuric acid v! J can be produced by the method described in Japanese Patent Publication No. 56-19514, and a typical example thereof is 2゜4-diamino-
6-(2'-Methylimidazolyl(1)') Engineering f-ruz-yazine isocyanuric acid adduct, 2,4-diamino-6-(2'-ethyl-4'-methylimidazolyl(1)') and ethyl-S-triazine cyanuric adducts. The appropriate amount of these grading agents to be used is 3 to 10 parts per 100 parts of the polyepoxy compound.

Also, 2,4-diamino-6-vinyl-
B-) To riazine: 5 to 5 to t polyepoxy compound
It can be blended in a range of 100%.

As polymerization initiators for 2.4-diamino-6-vinyl-S-triazine, commonly known organic peroxides, inorganic peroxides, azoisobutylnitrile, etc. are used, and among these, those that change less over time Dicumyl peroxide is particularly suitable because it is easy to handle.

The appropriate amount of the polymerization initiator to be used is 0.5 to 1.096 to 2,4-diamino-6-vinyl-S-triazine.

In carrying out the present invention, in addition to the above-mentioned main components, inorganic fillers such as calcium carbonate, talc, alumina, and silica, and coloring agents such as pigments and dyes may be added.

In the method of the present invention, in addition to forming a one-component composition in which each component is uniformly mixed in advance, it is also possible to mix a curing agent or a polymerization initiator immediately before the reaction. The curing reaction can be completed by heating to a temperature of about 90-150°C for several hours.

The present invention will be explained in detail below using Examples and Reference Examples.

Disaster'AMi 11y+J 1゜Digrindyl ether to bisphenol [Product name [Ebomitsuku n-14DJ (Mikata Petrochemical EvoA-n)] 1[
]]Og;, 2,4-di-γmino-6(2'-methylimidazolyl(1)')ethyl-s-triazine 5g, 2
．． 1-Diamino-6-pinyl S-tosu 7973.15
g5 Dicumyl peroxide [Product name: Percmil D
-4DJ (Japan Oil) M), 10.1g (0.5% molar ratio to vinyltriazine) and dried iJ4 wall agent [trade name [Erosil No.'500J (Japan Aerosil)]
An epoxy resin composition was prepared by uniformly mixing 1 g in fractions in a three-roll mill.

The viscosity of ice crystals at 25'C is 3,200 cps.

The rate of increase in viscosity after being left at a temperature of 40'G for one week was 22'3.
．． ,． The gel time when heated at a temperature of 150°C is 2 minutes 10 seconds, and the cured product heated at a temperature of 90°C for 4 hours and further 4 hours at 150°C has a glass transition point of 166 'C, heat/deformation temperature [(, T engineering 5K-7207
)1/) Songs that fall at 1'C and 25'C have an intensity (J I
5K-7205) 7.7Kg/LIIIl, 150'
Reference Example The same treatment as in the above example was carried out without adding 2,4-diamino-6-pinyl-8-) riazine and dicumyl peroxide. As a result, the uncured epoxy resin composition had a viscosity increase rate of 179 μm and a gel time of 2 minutes and 35 seconds at 25'C, and the cured product had a glass transition point of f24'c. 1ro 1'C
One song has a strength of 4"g/haz (25'C), 0.7
Kg/u&(150'C) Teat7IC0 Example 2 In Example 1, the curing agent 2.4-diamino-6=(2
Except that '-methylimidazolyl(1)') ethyl-s-triazine was changed to 2,4-diamino-6-(2'-methylimidazolyl(1)M ether-f3-) riazine in cyanuric acid adduct ( The same bolts were used) were treated with exactly the same formulation, and the properties were examined under the same conditions.
The uncured epoxy resin composition has a viscosity of 3.500 cps.
(25℃), viscosity +4 rate 5%, gel time 1 minute 20
The cured product has a glass transition point of 170, a thermal deformation temperature of 166'O%, a bending bow, and a Li degree of 9.71 (g
/ll, 11 (25'C), 2.1Kg/m (150'
C)' was shown.

patent applicant Shikoku Kasei Koso Co., Ltd.

Claims (1)

[Claims] 2,4-diamino-6 as a curing agent for polyepoxy compounds having an average of more than one epoxy group in the molecule.
-[2'-alkylimidazolyl(1)')ethyl-
s-triazine or 2,4-diamino-6-(2'-alnolimidazolyl(1)') ether-S-toV azineisoanuric acid adduct and 2,4-diamino-6-pinyl-8-) liazine and an epoxy resin curing method, which comprises mixing and heating a polymerization initiator for the 1j polymerizable monomer.