JP2015227415A - Ordinary-temperature curable epoxy resin composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an ordinary-temperature curable epoxy resin composition capable of hardening quickly not only at ordinary temperature but especially at low temperatures without heating and an adhesive and a repair/reinforcement method of structure using the composition.SOLUTION: An ordinary-temperature curable epoxy resin composition comprises an ingredient (A) an epoxy resin, (B) one or more compounds selected from aliphatic polyamines, alicyclic polyamines and their modified products and (C) a complex of a boron halide and an amine compound, hardens quickly at ordinary temperature, especially in a low-temperature environmental atmosphere, like outdoors in winter, without need of heating, and secures a sufficient usable time. An injection agent, a coating and an adhesion using the composition harden in a low-temperature environmental atmosphere while securing a sufficient usable time. A repair/reinforcement method of a structure using the composition is also provided.

Description

  The present invention relates to a room temperature curable epoxy resin composition. Specifically, the epoxy resin composition is rapidly cured without heating even at room temperature, particularly at a low temperature, without sufficient heating, and sufficient flexibility. The present invention relates to a room temperature curable epoxy resin composition that can ensure a working time.

Conventionally, a two-component curable composition comprising an epoxy resin and a curing agent has been used for various applications. For example, a two-component curable composition comprising an epoxy resin and an amine-based curing agent such as an aliphatic polyamine is advantageous in that it is excellent in room temperature curing, adhesiveness, durability, mechanical properties, etc. Used in repair and reinforcement work for structures such as structures and steel structures.
Specifically, it is used as an injection material for repairing cracks in concrete structures, or as a coating agent or adhesive for reinforcing concrete or steel structures with fiber sheets or reinforcing plates.

Such repair and reinforcement work is carried out regardless of the season or place. Therefore, in order to perform such a construction particularly in winter or at a place where the temperature is low, it is required that the two-component curable composition has good low-temperature curability.
However, when amine compounds such as aliphatic polyamines are used as an epoxy resin curing agent, there is a disadvantage that curing at low temperatures is significantly delayed.

  Some norbornanediamine, 1,3-bis (aminomethyl) cyclohexane (1,3-BAC) or their modified products exhibit curability even at a temperature lower than room temperature, but at low temperatures such as outdoors in winter. Curability in the atmosphere was insufficient.

  By the way, it is generally known that boron halide has a capability of causing cationic polymerization of an epoxy resin compound as a Lewis acid and curing it. However, when boron halide and epoxy resin are mixed, the reaction proceeds immediately and the pot life cannot be ensured. Therefore, boron halide is not suitable as a component for producing an epoxy resin composition used for an injection material, a coating agent, an adhesive or the like as described above.

  Therefore, usually, a boron halide amine complex is mixed with an epoxy resin and used as a one-component heat-curable epoxy resin. For example, a method of curing an epoxy resin using a boron trifluoride-aromatic amine complex has been proposed (Patent Document 1).

  However, these combinations require heating at the time of curing and, of course, do not cure in a low-temperature atmosphere outdoors in winter, so use them as adhesives for repair and reinforcement of structures. I can't.

JP-A-9-52942

  The present invention provides a room temperature curable epoxy resin composition that cures rapidly without heating, not only at room temperature, but also at low temperatures, and that ensures sufficient pot life. It is an object to do.

  In order to solve the above problems, the present invention employs the following configuration. That is, the present invention comprises (A) component: epoxy resin, and (B) component: one or more compounds selected from the group consisting of aliphatic polyamines, alicyclic polyamines, and modified products thereof, and (C) Component: The present invention relates to a room temperature curable epoxy resin composition comprising a boron halide and a complex of an amine compound.

  1st invention for solving the said subject was chosen from the group which consists of the epoxy resin which is (A) component, and the aliphatic polyamine which is (B) component, alicyclic polyamine, and those modified products. It is a room temperature curable epoxy resin composition characterized by containing a compound of a seed or more and a complex of boron halide as component (C) and an amine compound.

  2nd invention for solving the said subject is (C) component with boron trifluoride and 1 or more types of compounds chosen from the group which consists of aliphatic amine, alicyclic amine, and imidazole. The room temperature curable epoxy resin composition of the first invention, which is a complex.

  According to a third invention for solving the above-mentioned problem, the component (C) is composed of boron trifluoride and norbornanediamine, 1,3-xylylenediamine, isophoronediamine, 4,4′-methylenebis (cyclohexylamine), tetra The first compound which is a complex with at least one compound selected from the group consisting of ethylenepentamine, 1,3-bis (aminomethyl) cyclohexane, 2-ethyl-4-methylimidazole, monoethylamine and isopropylamine. It is the room temperature curable epoxy resin composition of the invention.

  4th invention for solving the said subject is 20-200 mass parts of (B) component, and (C) component is 1-100 mass parts with respect to 100 mass parts of (A) component. 1 is a room temperature curable epoxy resin composition according to any one of the first to third inventions.

  5th invention for solving the said subject is the equivalent ratio of the active hydrogen group of (B) component with respect to the epoxy group of (A) component being 0.5-2.0, (A) 100 mass parts of component On the other hand, it is a room temperature curable epoxy resin composition of the said 1st-4th invention whose (C) component is 1-100 mass parts.

  6th invention for solving the said subject is the adhesive agent which consists of the normal temperature curable epoxy resin composition of any one of 1st-5th invention.

  A seventh invention for solving the above-mentioned problems is a structure characterized in that the room temperature curable epoxy resin composition of any one of the first to fifth inventions is used to repair or reinforce a structure. This is a method for repairing and reinforcing objects.

  The room temperature curable epoxy resin composition according to the present invention is one or more selected from the group consisting of (A) component: epoxy resin and (B) component: aliphatic polyamine, alicyclic polyamine, and modified products thereof. And a component containing component (C): a complex of boron halide and an amine compound, it cures at room temperature without heating, and can be heated even in a low-temperature atmosphere such as outdoors in winter. It has an excellent effect that it cures quickly without being required and a sufficient pot life is ensured.

  And, by using the room temperature curable epoxy resin composition according to the present invention, a practical, injectable, coating, and adhesive that cures with sufficient working time even in a low temperature environment atmosphere is provided. It became possible to do.

  In addition, the room temperature curable epoxy resin composition according to the present invention cures while having sufficient pot life even in a low temperature atmosphere such as outdoors in winter. By using as a coating agent or adhesive to reinforce objects and steel structures with fiber sheets and reinforcing plates, it is easy and reliable to repair and reinforce these structures even in low-temperature environments such as outdoors in winter. And it can be done firmly.

  And after performing construction using the room temperature curable epoxy resin composition according to the present invention in a low temperature atmosphere such as outdoors in the winter, due to unexpected earthquakes, etc., concrete structures and steel structures are usually Even when large stress is applied to the extent that deformation causes damage, the presence of a hardened epoxy resin that has been hardened surely and sufficiently by construction makes it difficult for deformation to occur. There is an effect that can be prevented.

  Hereinafter, embodiments for carrying out the present invention will be described in detail. In addition, this invention is not limited only to these illustrations, Of course, a various change can be added in the range which does not deviate from the summary of this invention.

[About component (A)]
The component (A) according to the present invention is a liquid or solid resin having two or more epoxy groups in the molecule.

  Component (A) is, for example, biphenyl type epoxy resin, bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol AD type obtained by reacting bichloro, bisphenol A, bisphenol F, bisphenol AD, bisphenol S, etc. with epichlorohydrin. Epoxy resins, bisphenol S-type epoxy resins, etc., hydrogenated or brominated epoxy resins, glycidyl ester-type epoxy resins, novolac-type epoxy resins, urethane-modified epoxy resins with urethane bonds, metaxylenediamine, hydantoin, etc. And a nitrogen-containing epoxy resin, a polybutadiene or a rubber-modified epoxy resin containing NBR.

  (A) A component is not limited to these, You may use said epoxy resin in combination of 2 or more types.

[About component (B)]
The component (B) used in the present invention is an aliphatic polyamine, an alicyclic polyamine, or a modified product thereof, and is a curing agent for an epoxy resin.

  Examples of the aliphatic polyamine include ethylenediamine, 1,3-trimethylenediamine, 1,4-tetramethylenediamine, 1,3-pentamethylenediamine, 1,5-pentamethylenediamine, and 1,6-hexamethylene. Diamine, 1,2-propylenediamine, 1,2-butylenediamine, 2,3-butylenediamine, 1,3-butylenediamine, 2-methyl-1,5-pentamethylenediamine, 3-methyl-1,5- In addition to aliphatic diamines such as pentamethylenediamine, 2,4,4-trimethyl-1,6-hexamethylenediamine, and 2,2,4-trimethyl-1,6-hexamethylenediamine, diethylenetriamine, triethylenetetramine, tetra Ethylenepentamine, pentaethylenehexamine, 1,3-xylylenediamine 1,4-xylylenediamine, α, α, α ′, α′-tetramethyl-1,3-xylylenediamine, α, α, α ′, α′-tetramethyl-1,4-xylylenediamine , Ω, ω′-diamino-1,4-diethylbenzene, 1,3-bis (1-amino-1-methylethyl) benzene, 1,4-bis (1-amino-1-methylethyl) benzene, 1, Examples thereof include, but are not limited to, 3-bis (α, α-dimethylaminomethyl) benzene.

  Examples of the alicyclic polyamine include 1,3-cyclopentanediamine, 1,4-cyclohexanediamine, 1,3-cyclohexanediamine, and 1-amino-3-aminomethyl-3,5,5-trimethylcyclohexane. 1-amino-1-methyl-4-aminomethylcyclohexane, 1-amino-1-methyl-3-aminomethylcyclohexane, 4,4′-methylenebis (cyclohexylamine), 4,4′-methylenebis (3-methyl) -Cyclohexylamine), methyl-2,3-cyclohexanediamine, methyl-2,4-cyclohexanediamine, methyl-2,6-cyclohexanediamine, 1,3-bis (aminomethyl) cyclohexane, 1,4-bis (amino) Methyl) cyclohexane, isophoronediamine, norbornanedia And the like, such as 2,5-bis (aminomethyl) bicyclo [2.2.1] heptane, 2,6-bis (aminomethyl) bicyclo [2.2.1] heptane, etc. It is not limited to.

  Examples of the modified product of the aliphatic polyamine or alicyclic polyamine (B) include an epoxy adduct reaction product, a Mannich reaction product, a cyanoethylated product, a Michael reaction product, and a ketimine product of the aliphatic polyamine or alicyclic polyamine. However, it is not limited to these.

[About component (C)]
The component (C) used in the present invention is a complex of a boron halide and an amine compound. The epoxy resin as the component (A) and the aliphatic polyamine, the alicyclic polyamine as the component (B), or a modified product thereof. And promotes the curing reaction.

  Examples of the boron halide include boron trifluoride, boron tribromide, and boron trichloride. Among these, boron trifluoride is preferable from the viewpoint of easy handling and availability.

  Examples of the amine compound include aliphatic amines, alicyclic amines, aromatic amines, amines having an ether bond, polyamide amines, polyoxypropylene amines, modified amines, and linear chains containing a plurality of nitrogen atoms. Or cyclic | annular tertiary amine salt, imidazoles, aminosilanes, ammonia, etc. are mentioned.

  Examples of each amine compound include monomethylamine, monoethylamine, n-propylamine, isopropylamine, butylamine, amylamine, hexylamine, n-octylamine, 2-ethylhexylamine, nonylamine, decylamine, laurylamine, pentadecyl. Amine, cetylamine, stearylamine, cyclohexylamine, dimethylamine, diethylamine, dipropylamine, diisopropylamine, dibutylamine, diamylamine, dioctylamine, di (2-ethylhexyl) amine, didecylamine, dilaurylamine, dicetylamine, distearylamine, Methylstearylamine, ethylstearylamine, butylstearylamine, triamylamine, trihexylamine, trioctyl Amines, triallylamine, oleylamine, monoethanolamine, diethanolamine, triethanolamine, benzyldimethylamine, 2- (dimethylaminomethyl) phenol, 2,4,6-tris (dimethylaminomethyl) phenol, the above aliphatic polyamines, etc. Aliphatic amines; mensendiamine, 1,2-diaminocyclohexane, bis (4-amino-3-methylcyclohexyl) methane, bis (4-amino-methylcyclohexyl) methane, polycyclohexylpolyamine, cyclohexylamine, pyridine, above Cycloaliphatic amines such as cycloaliphatic polyamines; 4,4'-diaminodiphenyl sulfone, diaminodiphenyl ether, diaminodiphenyl sulfone, 4,4'-methylenedianiline, benzidine, 4,4'- (O-toluidine), 4,4'-thiodianiline, o-phenylenediamine, dianidine, methylenebis (o-chloroaniline), m-phenylenediamine, 2,4-toluenediamine, diaminoditolylsulfone, 4-methoxy- 6-methyl-m-phenylenediamine, 2,6-diaminopyridine, 4-chloro-o-phenylenediamine, m-aminobenzylamine, bis (3,4-diaminophenyl) sulfone, aniline, laurylaniline, stearylaniline, Aromatic amines such as triphenylamine; 3,9-bis (3-aminopropyl) -2,4,8,10-tetraoxaspiro [5,5] undecane (ATU), morpholine, N-methylmorpholine, Such as polyoxypropylene amine, polyoxyethylene amine, etc. Amines having a ether bond; polyamides obtained by reacting diamine acids with polyamines such as diethylenetriamine and diethylenetetramine, polyamide polyamideamines using polycarboxylic acids other than dimer acids; imidazoles, 2-ethyl-4-methyl Imidazoles such as imidazole, 2-phenylimidazole, 1-benzyl-2-methylimidazole, 2-undecylimidazole; dicyandiamide and derivatives thereof; epoxy-modified amine obtained by reacting an epoxy compound with the above amines, and the above amines Modified amines such as Mannich-modified amine, Michael addition-modified amine, ketimine obtained by reacting with formalin and phenol; 2-ethylhexanoic acid of 2,4,6-tris (dimethylaminomethyl) phenol Compounds such as amine salts such as salts, quaternary ammonium salts such as tetramethylammonium chloride, benzalkonium chloride, DABCO (registered trademark) series, DABCO BL series, 1,8-diazabicyclo [3] manufactured by Sankyo Aero Products 4.0] -7-undecene, 1,5-diazabicyclo [4.3.0] -5-nonene, 1,4-diazabicyclo [2.2.2] Directly containing a plurality of nitrogen atoms such as octane. Chain or cyclic tertiary amine salt; γ-aminopropyltrimethoxysilane, γ-aminopropyltriethoxysilane, γ-aminopropyltriisopropoxysilane, γ-aminopropylmethyldimethoxysilane, γ-aminopropylmethyldiethoxy Silane, N- (β-aminoethyl) aminopropyltrimethoxysilane, N- (β-a Minoethyl) aminopropylmethyldimethoxysilane, N- (β-aminoethyl) aminopropyltriethoxysilane, N- (β-aminoethyl) aminopropylmethyldiethoxysilane, N- (β-aminoethyl) aminopropyltriisopropoxy Aminosilanes such as silane, γ-ureidopropyltrimethoxysilane, N-phenyl-γ-aminopropyltrimethoxysilane, N-benzyl-γ-aminopropyltrimethoxysilane, N-vinylbenzyl-γ-aminopropyltriethoxysilane Ammonia and the like can be mentioned, but not limited thereto.

As an amine compound that forms a complex with boron trifluoride, an aliphatic amine, an alicyclic amine, and an imidazole are more preferable because of a high curing acceleration effect, and since a curing acceleration effect is higher, norbornanediamine, 1 , 3-xylylenediamine, isophoronediamine, 4,4'-methylenebis (cyclohexylamine), tetraethylenepentamine, 1,3-bis (aminomethyl) cyclohexane, 2-ethyl-4-methylimidazole, monoethylamine, isopropyl An amine is more preferable, and 1,3-xylylenediamine, isophoronediamine, 1,3-bis (aminomethyl) cyclohexane and 2-ethyl are preferred because of the ease of handling due to the liquid complex with boron trifluoride. -4-Methylimidazole is most preferred.
In addition, in order to facilitate handling, the component (C) is prepared by mixing with a diluent such as butyl glycidyl ether or the liquid component (A) or component (C) to prepare a solution. You may do it.

[Ratio of (A) component, (B) component, (C) component]
The component (B) and the component (C) may be appropriately selected in order to obtain a desired pot life, and may be used alone or in combination of two or more.

  (B) As a mixing amount of a component, 10-200 mass parts is preferable with respect to 100 mass parts of (A) component, 10-100 mass parts is more preferable, and 10-50 mass parts is the most preferable. When the amount of the component (B) is less than 10 parts by mass, problems such as insufficient curing at low temperatures may occur, and when it exceeds 200 parts by mass, the pot life may not be sufficient. .

  Component (C) is preferably mixed in an amount of 1 to 100 parts by weight, more preferably 1 to 50 parts by weight, even more preferably 2 to 50 parts by weight, based on 100 parts by weight of component (A). 5 to 50 parts by mass is more preferable, 10 to 50 parts by mass is more preferable, and 20 to 50 parts by mass is most preferable. If the amount of component (C) is less than 1 part by mass, problems such as insufficient curing at low temperatures may occur, and if it exceeds 100 parts by mass, the pot life may not be sufficient. .

[Other ingredients]
Moreover, the other well-known arbitrary component may be mix | blended in the resin composition for epoxy resin curing which concerns on this invention. Specifically, fillers such as kaolin, clay, talc, silica sand, silica, titanium oxide, calcium carbonate, carbon black, pigments such as dyes, organic solvents such as alcohols, ketones, aromatic hydrocarbons, mono or Various additives such as a reactive diluent such as di- or triepoxide compound, a silane coupling agent, a pigment dispersant, an antifoaming agent, a titanium coupling agent, an ultraviolet absorber, and an antioxidant may be blended.

  EXAMPLES Hereinafter, although this invention is demonstrated in detail based on an Example, this invention is not limited to an Example.

<Manufacturing of epoxy resin composition and evaluation method of pot life, curing time and fixing time>
The epoxy resin composition shown as an Example and a comparative example below was produced.

Example 1
After charging 7.7 parts by mass of norbornanediamine (NBDA, molecular weight 154.26) into a vessel equipped with a stirrer, 7.0 parts by mass of boron trifluoride tetrahydrofuran complex (molecular weight 139.91) was added dropwise and mixed. After stirring for 1 hour, THF was distilled off under reduced pressure to obtain a complex (BF ₃ · NBDA) of boron trifluoride (BF ₃ ) and norbornanediamine, which is a white solid at room temperature, as component (C).

Next, 7.5 parts by mass of jER828 (product name, manufactured by Mitsubishi Chemical Corporation), which is an epoxy resin of component (A), and 1,6-hexanediol diglycidyl ether (ED503, manufactured by ADEKA Corporation, product name) ) In 2.5 parts by mass, component (B) 1,3-xylylenediamine (MXDA, molecular weight 136.19) in 1.8 parts by mass, and component (C) trifluoride obtained above 1.04 parts by mass of a complex of boron and norbornanediamine (BF ₃ · NBDA) were sequentially mixed to obtain a room temperature curable epoxy resin composition.

  And about the produced normal temperature curable epoxy resin composition, the following items were evaluated.

[Pot life]
The component (B) and the component (C) are sequentially mixed with the component (A). When the mixing of the component (C) is started, the test is started. When the container containing the mixed epoxy resin composition is tilted at each evaluation temperature, the composition stops flowing under its own weight. Time is referred to as “pot life”. The evaluation is carried out in a 23 ° C. atmosphere and a 5 ° C. atmosphere, and the measured pot life is recorded as “23 ° C. pot life” and “5 ° C. pot life”, respectively.

[Curing time]
(B) component and (C) component are sequentially mixed and stirred with (A) component. When the mixing of the component (C) is started, the test is started. From the start of the test, when a metal spoon is used and the epoxy resin composition that has been hardened is pressed firmly, the composition does not deform. The time until is set as “curing time”. The evaluation is performed in a 23 ° C. atmosphere and a 5 ° C. atmosphere, and the measured curing times are recorded as “23 ° C. curing time” and “5 ° C. curing time”, respectively.

(Example 2)
Instead of “7.7 parts by mass of norbornanediamine” in Example 1, “6.8 parts by mass of 1,3-xylylenediamine” was used, and as component (C), a transparent viscous liquid at room temperature. A complex of boron fluoride and 1,3-xylylenediamine (BF ₃ · MXDA) was obtained, and instead of “(C) component 1.04 parts by mass”, “(C) component 0.98 parts by mass” A normal temperature curable epoxy resin composition was obtained by the same method as in Example 1 except that was used, and evaluated by the same method.

(Example 3)
Instead of “7.7 parts by mass of norbornane diamine” in Example 1, “8.5 parts by mass of isophorone diamine (IPDA, molecular weight 170.25)” was used, and as component (C), a transparent viscous liquid was used at room temperature. Obtain a complex of boron trifluoride and isophoronediamine (BF ₃ · IPDA), and use “(C) component 1.11 parts by mass” instead of “(C) component 1.04 parts by mass”. Otherwise, a room temperature curable epoxy resin composition was obtained by the same method as in Example 1, and evaluated by the same method.

Example 4
Instead of “7.7 parts by mass of norbornanediamine” in Example 1, “4,4′-methylenebis (cyclohexylamine) (PACM, molecular weight 210.36) 10.5 parts by mass” was used as the component (C). And obtaining a complex (BF ₃ · PACM) of boron trifluoride and 4,4′-methylenebis (cyclohexylamine), which is a white solid at room temperature, instead of “(C) component 1.04 parts by mass” The normal temperature curable epoxy resin composition was obtained by the same method as in Example 1 except that “1.25 parts by mass of component (C)” was used, and evaluated by the same method.

(Example 5)
In place of “7.7 parts by mass of norbornanediamine” in Example 1, “9.4 parts by mass of tetraethylenepentamine (TEPA, molecular weight 189.3)” was used, and as component (C), yellow viscous at room temperature. A liquid complex of boron trifluoride and tetraethylenepentamine (BF ₃ · TEPA) was obtained, and instead of “(C) component 1.04 parts by mass”, “(C) component 1.16 parts by mass” Except for using “part”, a room temperature curable epoxy resin composition was obtained by the same method as in Example 1 and evaluated by the same method.

(Example 6)
Instead of “7.7 parts by mass of norbornanediamine” in Example 1, “1,3-bis (aminomethyl) cyclohexane (1,3-BAC, molecular weight 142.24) 7.1 parts by mass” was used. C) As a component, a complex solution (BF ₃ .1,3-BAC) of boron trifluoride and 1,3-bis (aminomethyl) cyclohexane, which is a transparent viscous liquid at room temperature, was obtained. A normal temperature curable epoxy resin composition was obtained in the same manner as in Example 1 except that “1.00 part by mass of component (C)” was used instead of “1.04 parts by mass of component”. The method was evaluated.

(Example 7)
In place of “7.7 parts by mass of norbornanediamine” in Example 1, 5.5 parts by mass of “2-ethyl-4-methylimidazole (2E4MZ, molecular weight 110.16)” was used as the component (C) at room temperature. A yellow liquid, a complex of boron trifluoride and 2-ethyl-4-methylimidazole (BF ₃ · 2E4MZ) was obtained, and instead of “(C) component 1.04 parts by mass”, “(C The normal temperature curable epoxy resin composition was obtained in the same manner as in Example 1 except that 0.8) part by mass of component) was used, and evaluated in the same manner.

(Example 8)
As component (C), instead of “complex of boron trifluoride and norbornanediamine”, a commercially available white solid “boron trifluoride monoethylamine (BF ₃ .monoethylamine, molecular weight 112.9)” is used. In the same manner as in Example 1, except that “(C) component 0.82 parts by mass” was used instead of “(C) component 1.04 parts by mass”, the room temperature curable epoxy resin composition was changed. Obtained and evaluated by the same method.

Example 9
As component (C), instead of “complex of boron trifluoride and norbornanediamine”, butyl of “boron trifluoride isopropylamine complex (BF ₃ .isopropyl complex, molecular weight 257.1013)” which is a commercially available brown liquid Except that “glycidyl ether mixture (boron trifluoride isopropylamine complex 60% by mass)” was used, and “(C) component 0.72 parts by mass” was used instead of “(C) component 1.04 parts by mass”. The normal temperature curable epoxy resin composition was obtained by the same method as in Example 1 and evaluated by the same method.

(Example 10)
(B) As the component, instead of “1.8 parts by mass of 1,3-xylylenediamine”, “2.5 parts by mass of norbornanediamine” is used. An epoxy resin composition was obtained and evaluated by the same method.

(Example 11)
(B) In place of “1,3-xylylenediamine 1.8 parts by mass” as the component, “isophoronediamine 2.4 parts by mass” is used in the same manner as in Example 6, except that room temperature curing is performed. An epoxy resin composition was obtained and evaluated by the same method.

(Example 12)
(B) In place of “1,3-xylylenediamine 1.8 parts by mass”, “4,4′-methylenebis (cyclohexylamine) 3.0 parts by mass” is used as the component in Example 6. A normal temperature curable epoxy resin composition was obtained by the same method and evaluated by the same method.

(Example 13)
(B) Instead of “1.8 parts by mass of 1,3-xylylenediamine” as the component, “tetraethylenepentamine 1.5 parts by mass” is used in the same manner as in Example 6 at room temperature. A curable epoxy resin composition was obtained and evaluated by the same method.

(Example 14)
As Example (6), except that “1,3-bis (aminomethyl) cyclohexane 2.0 parts by mass” is used instead of “1,3-xylylenediamine 1.8 parts by mass” as the component (B), A normal temperature curable epoxy resin composition was obtained by the same method and evaluated by the same method.

(Example 15)
A normal temperature curable epoxy resin composition was obtained in the same manner as in Example 6 except that “(C) component 0.10 parts by mass” was used instead of “(C) component 1.0 part by mass”. The same method was used for evaluation.

(Example 16)
A normal temperature curable epoxy resin composition was obtained in the same manner as in Example 6 except that “(C) component 0.20 part by mass” was used instead of “(C) component 1.0 part by mass”. The same method was used for evaluation.

(Example 17)
A normal temperature curable epoxy resin composition was obtained in the same manner as in Example 6 except that “(C) component 0.50 part by mass” was used instead of “(C) component 1.0 part by mass”. The same method was used for evaluation.

(Example 18)
A normal temperature curable epoxy resin composition was obtained in the same manner as in Example 6 except that “(C) component 2.00 parts by mass” was used instead of “(C) component 1.0 part by mass”. The same method was used for evaluation.

(Example 19)
A normal temperature curable epoxy resin composition was obtained in the same manner as in Example 6, except that “(C) component 1.00 part by mass” was used instead of “(C) component 1.0 part by mass”. The same method was used for evaluation.

(Example 20)
In addition to the component (A), component (B) and component (C) of Example 6, in addition to 3 parts by mass of NS # 400: calcium carbonate (manufactured by Nitto Flour Industry Co., Ltd.) A room temperature curable epoxy resin composition was obtained by the same method as in Example 6, and evaluated by the same method.

(Example 21)
In addition to (A) component, (B) component and (C) component of Example 6, JR-600E: Rutile type titanium oxide (manufactured by Teika Co., Ltd.) was added in addition to 3 parts by mass. A room temperature curable epoxy resin composition was obtained by the same method as in Example 6, and evaluated by the same method.

(Example 22)
In addition to the component (A), component (B) and component (C) of Example 6, 0.5 parts by mass of Aerosil # 200: hydrophilic fumed silica (Evonik) was added. The normal temperature curable epoxy resin composition was obtained by the same method as in Example 6 and evaluated by the same method.

(Example 23)
In addition to (A) component, (B) component, and (C) component of Example 6, ASP-170: Kaolin (made by BASF) 3 mass parts was added, and the same as Example 6 Thus, a room temperature curable epoxy resin composition was obtained and evaluated by the same method.

(Example 24)
In the same manner as in Example 6, a room temperature curable epoxy resin composition was obtained.

  And the fixing time was evaluated about the produced normal temperature curable epoxy resin composition.

[Fixed time]
The component (B) and the component (C) are sequentially mixed with the component (A) to obtain an epoxy resin composition. The epoxy resin composition is applied to two test pieces (test body: SPCC-SB steel plate (25 mm × 100 mm × 1.6 mmt)), and the test pieces are crossed so that the adhesive surface area is 25 mm × 25 mm. The time when the test pieces were fixed and stopped moving was defined as “fixing time”, and the fixing time in an atmosphere at 23 ° C. was defined as “23 ° C. fixing time” and The fixing time in a 5 ° C. atmosphere is evaluated as “5 ° C. fixing time”.

(Example 25)
The component (A) in Example 6 was replaced with 10 parts by mass of jER828, and the others were obtained in the same manner as in Example 6 to obtain a room temperature curable epoxy resin composition and evaluated in the same manner.

(Example 26)
A room temperature curable epoxy resin composition was obtained by the same method as in Example 6, and evaluated by the same method.

(Example 27)
The component (A) of Example 6 was replaced with 10 parts by mass of Epicron 830 (DIC Corporation, registered trademark), and the others were obtained in the same manner as in Example 6 to obtain a room temperature curable epoxy resin composition. Evaluation was performed by the method.

(Comparative Example 1)
An epoxy resin composition was obtained by the same method as in Example 1 except that the component (C) in Example 1 was not used, and evaluated by the same method.

(Comparative Example 2)
(B) It replaces with "1,3-xylylenediamine 1.8 mass parts" which is a component, and is the same as Example 6 except using "2-ethyl-4-methylimidazole 0.50 mass part". The epoxy resin composition was obtained by the method and evaluated by the same method.

(Comparative Example 3)
(B) Instead of “1.8 parts by mass of 1,3-xylylenediamine” as the component, Example 6 is used except that “4 parts by mass of 4,4′-diaminodiphenylmethane (DDM)” is used. The epoxy resin composition was obtained by the same method and evaluated by the same method.

(Comparative Example 4)
Example 6 except that “4,4′-diaminodiphenylsulfone (DDS) 3.5 parts by mass” was used instead of “1,3-xylylenediamine 1.8 parts by mass” as the component (B). The epoxy resin composition was obtained by the same method and evaluated by the same method.

(Comparative Example 5)
An epoxy resin composition was obtained by the same method as in Example 6 except that the component (B) in Example 6 was not blended, and the same evaluation was performed.

(Comparative Example 6)
(A) 10 parts by mass of jER828, (B) component of 1.8 parts by mass of 1,3-xylylenediamine, and (C) component is not blended. A resin composition was obtained and subjected to the same evaluation.

(Comparative Example 7)
The same method as Comparative Example 6 except that “2.5 parts by mass of norbornanediamine” is used instead of “1.8 parts by mass of 1,3-xylylenediamine” as the component (B) in Comparative Example 6 The epoxy resin composition was obtained with the same evaluation.

(Comparative Example 8)
The same method as in Comparative Example 6, except that “2.4 parts by mass of isophoronediamine” is used instead of “1.8 parts by mass of 1,3-xylylenediamine” as the component (B) in Comparative Example 1 The epoxy resin composition was obtained with the same evaluation.

(Comparative Example 9)
Other than using “4,4′-methylenebis (cyclohexylamine) 3.0 parts by mass” instead of “1.8 parts by mass of 1,3-xylylenediamine” of the component (B) in Comparative Example 1, An epoxy resin composition was obtained in the same manner as in Comparative Example 6, and the same evaluation was performed.

(Comparative Example 10)
The same as Comparative Example 6 except that “1.5 parts by mass of tetraethylenepentamine” is used instead of “1.8 parts by mass of 1,3-xylylenediamine” as the component (B) of Comparative Example 1 The epoxy resin composition was obtained by the method and the same evaluation was performed.

(Comparative Example 11)
Other than using “1,3-bis (aminomethyl) cyclohexane 2.0 parts by mass” instead of “1.8 parts by mass of 1,3-xylylenediamine” in the component (B) of Comparative Example 1 The epoxy resin composition was obtained by the same method as in Comparative Example 6, and the same evaluation was performed.

(Comparative Example 12)
The component (B) of Comparative Example 1 was replaced by “1.8 parts by mass of 1,3-xylylenediamine”, but “0.50 parts by mass of 2-ethyl-4-methylimidazole” was used. An epoxy resin composition was obtained in the same manner as in Example 6, and the same evaluation was performed.

(Comparative Example 13)
Comparative Example 1 except that instead of “1.8 parts by mass of 1,3-xylylenediamine” as the component (B) of Comparative Example 1, “3.0 parts by mass of 4,4′-diaminodiphenylmethane” was used. The epoxy resin composition was obtained by the same method as 6, and the same evaluation was performed.

(Comparative Example 14)
The component (B) of Comparative Example 1 was replaced with “1.8 parts by mass of 1,3-xylylenediamine”, except that “3.5 parts by mass of 4,4′-diaminodiphenylsulfone” was used. An epoxy resin composition was obtained in the same manner as in Example 6, and the same evaluation was performed.

(Comparative Example 15)
An epoxy resin composition was obtained by the same method as in Example 6 except that the component (C) in Example 6 was not blended, and the same evaluation was performed.

(Comparative Example 16)
A room temperature curable epoxy resin composition was obtained in the same manner as in Example 24 except that the component (C) in Example 24 was not blended, and evaluated in the same manner.

(Comparative Example 17)
A room temperature curable epoxy resin composition was obtained by the same method as in Example 27 except that the component (C) of Example 27 was not blended, and evaluated in the same manner.

(Comparative Example 18)
(A) Component epoxy resin, jER828 10 parts by mass, (B) component 1,3-xylylenediamine 1.8 parts by mass, 1,3-BAC 0.5 parts by mass, C) As a component, using 0.50 part by mass of boron trifluoride tetrahydrofuran complex (BF ₃ · THF complex), a room temperature curable epoxy resin composition was obtained, and a 23 ° C. pot life and a 23 ° C. curing time were obtained. Was evaluated.

  The test results obtained by evaluating the pot life, curing time, and fixing time using the compositions of the Examples and Comparative Examples obtained above are shown below. The room temperature curable epoxy resin composition of the present invention is The effect to play is demonstrated.

<Evaluation 1>
First, using the compositions of Examples 1 to 9 and Comparative Example 1 obtained above, “23 ° C. working time”, “5 ° C. working time”, “23 ° C. curing time”, and “5 ° C.” The “curing time” was evaluated. The results are shown in Table 1.

  As a result of evaluation using each of the above compositions, the epoxy resin composition was divided into “(A) component: epoxy resin” and “(B) component: aliphatic polyamine, alicyclic polyamine and By containing one or more compounds selected from the group consisting of those modified products ”and“ (C) component: a complex of a boron halide and an amine compound ”, three specific components, At 23 ° C., the curing time is 13 minutes to 95 minutes and has an extremely rapid curing time, and the pot life is 12 minutes to 54 minutes, which ensures excellent workability. It became clear that it became possible to obtain a novel room temperature curable epoxy resin composition (Table 1: Examples 1 to 9).

  Further, the epoxy resin composition is selected from the group consisting of “(A) component: epoxy resin” and “(B) component: aliphatic polyamine, alicyclic polyamine, and modified products thereof, as in the present invention. Surprisingly, it is heated at 5 ° C. by including one or more compounds ”and“ (C) component: complex of boron halide and amine compound ”. Without curing, the curing time is 8 hours to 16 hours and the curing time is sufficiently rapid, and the pot life is 3 hours to 7 hours. It has become clear that it has become possible to obtain a novel room temperature curable epoxy resin composition that exhibits the excellent effect of solving the conventional problems of being ensured (Table 1: Examples 1 to 1). Example 9).

  The amine composition is norbornanediamine, 1,3-xylylenediamine, isophoronediamine, 4,4′-methylenebis (cyclohexylamine), tetraethylenepentamine, 1,3-bis (aminomethyl) cyclohexane, 2- Ethyl-4-methylimidazole, isopropylamine or monoethylamine has different properties, but it is a complex of boron halide and amine compound, and as component (C) of the present invention, component (A) and ( As described above, it was confirmed that any of the excellent effects was obtained when used together with the component B).

  On the other hand, the component (C) is not added as in the prior art, and the basic components of the resin composition are “(A) component: epoxy resin” and “(B) component: aliphatic polyamine, alicyclic polyamine, and their components. The epoxy resin composition of Comparative Example 1 consisting of “one or more compounds selected from the group consisting of modified products” has a curing time at 23 ° C. of 230 minutes, which is much longer than that of the present invention, In particular, at 5 ° C., it was not hardened within a practical range of 24 hours or longer (Table 1: Comparative Example 1).

<Evaluation 2>
About each epoxy resin composition in Example 6, Example 10- Example 14 and Comparative Example 2- Comparative Example 5 which were obtained above, "23 degree C pot life", "5 degree C pot time", "23 degree C “Curing time” and “5 ° C. curing time” were evaluated. The results are shown in Table 2.

  As a result of evaluation using each of the above-mentioned compositions, the component (B) is selected from the group consisting of aliphatic polyamines, alicyclic polyamines and their modified products that also have different properties from 1,3-xylylenediamine. Even if it is replaced with norbornanediamine, isophoronediamine, 4,4′-methylenebis (cyclohexylamine), tetraethylenepentamine or 1,3-bis (aminomethyl) cyclohexane, which is one or more of the above compounds, By using it together with “(A) component: epoxy resin” and “(C) component: complex of boron halide and amine compound” and containing each of these three components, at 23 ° C., It has an extremely quick curing time of 11.5 minutes to 29 minutes, and a pot life of 11 minutes to 25 minutes, ensuring sufficient workability. That new cold-curable epoxy resin composition which exhibits the results it became possible to obtain revealed (Table 2: Example 6 and Examples 10 to 14).

  In addition, the component (B) is one or more compounds selected from the group consisting of aliphatic polyamines, alicyclic polyamines, and modified products thereof having characteristics different from those of 1,3-xylylenediamine, Even if it is replaced with norbornanediamine, isophoronediamine, 4,4′-methylenebis (cyclohexylamine), tetraethylenepentamine, or 1,3-bis (aminomethyl) cyclohexane, Surprisingly, by using together with the component C) and containing each of these three components, a curing time of 8 to 11 hours is sufficiently rapid without heating at 5 ° C. The existing problem of having sufficient workability even in low-temperature atmospheres such as outdoors in winter, with a pot life of 2 hours to 5 hours, is solved It exhibits a very excellent effect that, it became possible to obtain a novel cold-curing epoxy resin composition revealed (Table 2: Example 6 and Examples 10 to 14).

  On the other hand, like Comparative Example 2 to Comparative Example 4, like the conventional epoxy resin composition, “(B) component: one selected from the group consisting of aliphatic polyamines, alicyclic polyamines and their modified products” When components other than “the above compound” were used, the curing time at 23 ° C. was 5 to 16 hours, which was much longer than that of the present invention. In particular, at 5 ° C., it was confirmed that the curing time was 24 hours or longer and was not practical (Table 2: Comparative Examples 2 to 4).

  Moreover, when the epoxy resin composition is prepared so as to contain the component (A) and the component (C) but not the component (B), the curing time is 24 hours or more, which is not practical. It was confirmed that it was impossible to solve the problem. (Table 2: Comparative Example 5).

  Furthermore, the following comparative examples were evaluated in order to confirm the degree of contribution to the curing time of “(C) component: complex of boron halide and amine compound” in the room temperature curable epoxy resin composition of the present invention.

<Evaluation 3>
In Evaluation 1, the curing time at 23 ° C. is 230 minutes, which is much longer than that of the present invention, and in particular at 5 ° C., it is 24 hours or longer and does not cure within the practical range. The composition of the comparative example shown does not use the component (C), and is used in combination with the component (A) “(B) component: from the group consisting of aliphatic polyamines, alicyclic polyamines and their modified products. As the “one or more selected compounds”, 1,3-xylylenediamine is used.

  Therefore, the component (A) is used in combination with the component (B) 1,3-xylylenediamine and the component (C) is not used, or the component (A) is used in combination with the component 1,3-xylylenediamine (B). The amine is also one or more compounds selected from the group consisting of aliphatic polyamines, alicyclic polyamines, and modified products thereof, norbornane diamine, isophorone diamine, 4,4′-methylene bis (cyclohexylamine), tetra Ethylenepentamine or 1,3-bis (aminomethyl) cyclohexane, or 2-amine 2-ethyl-4-methylimidazole, 4,4′-diaminodiphenylmethane or 4 as a polyamine (B ′) component other than (B) component , 4′-diaminodiphenylsulfone was prepared, and “23 ° C. curing time” and “5 ° C.” were also used for these compositions. It confirmed the reduction time "(Comparative Example 6 Comparative Example 14). The results are shown in Table 3.

  As a result of evaluation using each of the above compositions, the component (C) was not used, and the component (A) was selected from the group consisting of the aliphatic polyamine, alicyclic polyamine of component (B), and modified products thereof. As one or more compounds, norbornanediamine, 1,3-xylylenediamine, isophoronediamine, 4,4′-methylenebis (cyclohexylamine), tetraethylenepentamine or 1,3-bis (aminomethyl) cyclohexane Or Comparative Example 6 to Comparative Example 14 in which 2-ethyl-4-methylimidazole, 4,4′-diaminodiphenylmethane, or 4,4′-diaminodiphenylsulfone is used in combination as a polyamine (B ′) component other than (B) component In the composition, the curing time at 23 ° C. is 103 minutes to 24 hours or more, which is much longer than that of the present invention. In particular, at 5 ° C., both are 24 hours or longer, and are not cured within the practical range. As in the case of using 1,3-xylylenediamine as the component (B), there is a problem in either case. It could not be solved, and it was shown that it was not practical (Table 3).

<Evaluation 4>
With regard to the component (C) in the present invention, those having different blending amounts were prepared, and the pot life and the curing time were confirmed (Example 6, Examples 15 to 19 and Comparative Example 15). The results are shown in Table 4.

  As a result of evaluation using each of the above compositions, 7.5 parts by mass of jER828 as component (A), 2.5 parts by mass of ED503, and 1.8 of 1,3-xylylenediamine as component (B). In Comparative Example 15 using parts by mass and not adding the component (C), the curing time at 23 ° C. was as long as 230 minutes, and at 5 ° C., it was not cured within a practical range of 24 hours or more. (Table 4: Comparative Example 15).

  However, as in the present invention, when (C) component (complex of boron trifluoride and 1,3-bis (aminomethyl) cyclohexane) is further added to the above component (A) and component (B), 23 Both pot life and curing time at 5 ° C. and 5 ° C. were shortened. Depending on increasing the amount of component (C) added to component (A) and component (B) from 0.1 parts by weight to 5 parts by weight, the pot life of 23 ° C. is 90 minutes to 3.5 minutes. The 23 ° C curing time is shortened from 150 minutes to 4 minutes, the 5 ° C pot life is shortened from 9-15 hours to 14 minutes, and the 5 ° C curing time is shortened from 22 hours to 15 minutes. (Table 4: each example).

  As described above, in the room temperature curable epoxy resin composition of the present invention, according to the increase in the amount of the component (C) to be added to the component (A) and the component (B), the temperature is cured at 23 ° C. and cured at 23 ° C. It was revealed that the time, 5 ° C. pot life and 5 ° C. curing time were all shortened to the practical range (Table 4). And, in using the room temperature curable epoxy resin composition, the (A) component and the (B) component are obtained so as to obtain those having an optimal pot life and curing time not only at room temperature but also in a low temperature atmosphere. It was found that the amount of the component (C) to be added can be increased to reduce the pot life and the curing time (Table 4).

<Evaluation 5>
One or more compounds selected from the group consisting of the epoxy resin as the component (A) of the present invention, the aliphatic polyamine, the alicyclic polyamine as the component (B), and their modified products, and the component (C) The room temperature curable epoxy resin composition characterized by containing a boron halide and a complex of an amine compound, can be used as well and can be cured even if a filler is added. The test which confirms whether it has the property from which the effect which promotes is acquired was performed (Example 20-Example 23). The results are shown in Table 5.

  As an example of a general-purpose filler to be added to the component (A), the component (B) and the component (C), NS # 400: calcium carbonate, JR-600E: rutile titanium oxide, Aerosil # 200: hydrophilic fumed The prepared compositions of Examples 20 to 23 were evaluated using silica and ASP-170: kaolin, respectively.

  As a result of evaluation using each of the above compositions, the epoxy resin as the component (A) of the present invention and the aliphatic polyamine, alicyclic polyamine as the component (B), and modified products thereof are selected. The room temperature curable epoxy resin composition containing one or more kinds of compounds and a complex of boron halide as component (C) and an amine compound is composed of calcium carbonate, rutile titanium oxide, and hydrophilic fumed silica. Even if a general-purpose filler such as kaolin is further added, a practical use time of 23 ° C. for 15 minutes to 18 minutes and a curing temperature of 23 ° C. of 16 minutes to 19 minutes are ensured and curing is possible. It became clear that it has the property from which the effect promoted is acquired (Table 5: Example 20-Example 23).

<Evaluation 6>
One or more compounds selected from the group consisting of the epoxy resin as the component (A) of the present invention, the aliphatic polyamine, the alicyclic polyamine as the component (B), and their modified products, and the component (C) A room temperature curable epoxy resin composition characterized by containing a boron halide and a complex of an amine compound can be practically used as an adhesive at both room temperature and low temperature atmosphere (Example 24 and Comparative Example 16) were evaluated. The results are shown in Table 6.

  The room temperature curable epoxy resin composition of the present invention is composed of 7.5 parts by mass of component (A) jER828, 2.5 parts by mass of ED503, and 1.8 parts by mass of 1,3-xylylenediamine (B). Part (C) was prepared so as to contain 1.0 part by mass of the complex of component (C) boron trifluoride and 1,3-bis (aminomethyl) cyclohexane (Example 24). In addition, as the resin composition to be compared, only the component (A) and the component (B) were used, and a resin composition not containing the component (C) was prepared (Comparative Example 16).

  The resin compositions of the above Examples and Comparative Examples were applied to two test pieces (test body: SPCC-SB steel plate (25 mm × 100 mm × 1.6 mmt), and the test was performed so that the adhesive surface area was 25 mm × 25 mm. The pieces were bonded together in a cross shape, and the time until the test pieces were fixed and stopped moving was measured as “fixing time.” Fixing time at 23 ° C. atmosphere (23 ° C. fixing time) and 5 ° C. atmosphere The fixing time (5 ° C. fixing time) was evaluated.

  As a result of evaluation using each of the above compositions, the room temperature curable resin composition containing the component (A), the component (B) and the component (C) of the present invention has a fixed time of 23 ° C. Was found to be able to exhibit a useful property as an adhesive that can reliably fix the test piece in a short time in a room temperature atmosphere of 2 hours (Table 6: Example 24). Furthermore, as a result of checking the fixing time at 5 ° C., the above-mentioned room temperature curable resin composition of the present invention reliably fixes the test piece in a short time to a practical level even in a low temperature atmosphere of 8 to 16 hours. As a result, it has been revealed that it can exhibit very useful properties as an adhesive (Table 6: Example 24).

  On the other hand, in the conventional resin composition containing no component (C), the 23 ° C. fixing time is 6 hours, which is longer than that of the present invention, and the 5 ° C. fixing time is 48 hours or more, Under a low temperature atmosphere, it was revealed that the test piece could not be fixed within a practical range and could not be used as an adhesive (Comparative Example 16).

<Evaluation 7>
In the room temperature curable epoxy resin composition of the present invention, even if the epoxy resin as the component (A) is replaced with another epoxy resin other than bisphenol A, the pot life is secured and the curing is accelerated. The test which confirms whether it has the property from which the effect which is obtained is obtained was done (Example 25- Example 27 and Comparative Example 17). The results are shown in Table 7.

  The room temperature curable resin composition containing the component (A), the component (B), and the component (C) of the present invention as a result of evaluation using each of the above compositions is the component (A). Even if bisphenol A is used (Example 25 and Example 26) or bisphenol F type epoxy resin is used (Example 27), sufficient pot life is ensured as well. It became clear that it has the property which the effect which accelerates | stimulates hardening is acquired (Table 7).

  On the other hand, a bisphenol F type epoxy resin is used as the component (A), and only the component (B) is blended with the component (A) as in the past, and unlike the present invention, the resin composition does not further blend the component (C). In the product, the pot life was 10 times or more that of the present invention, and the curing time was 11 times or more that of the present invention, indicating that it was not practical (Table 7: Comparative Example 17).

<Evaluation 8>
Component (A) of the present invention: epoxy resin, Component (B): one or more compounds selected from the group consisting of aliphatic polyamines, alicyclic polyamines and modified products thereof, and component (C): halogen Component (C) in a room temperature curable epoxy resin composition characterized by containing a complex of boron halide and an amine compound: In place of a complex of boron halide and an amine compound, boron trifluoride and THF Similarly, in the case of using a complex (BF ₃ · THF complex), a test for confirming whether or not it has the property of ensuring the pot life and promoting the curing was performed ( Comparative Example 18). The results are shown in Table 8.

As in Comparative Example 18, in addition to the components (A) and (B) of the present invention, as the component (C), instead of the complex of boron halide and amine compound in the present invention, boron trifluoride and A complex of THF (BF ₃ · THF complex) was further mixed, and the pot life and the curing time were evaluated. As a result, when the above-mentioned THF complex is mixed with an epoxy resin composed of the component (A) and the component (B), some gelation occurs in 10 seconds after stirring, and it is impossible to secure a pot life that is practically usable. (Table 8).

  The epoxy resin composition comprises (A) component: epoxy resin, and (B) component: one or more compounds selected from the group consisting of aliphatic polyamines, alicyclic polyamines, and modified products thereof, and (C) Ingredient: By containing a complex of boron halide and amine compound, it cures at room temperature without heating, and does not require heating even in a low-temperature atmosphere such as outdoors in winter It is possible to provide a room temperature curable epoxy resin composition that is quickly cured and has a sufficient pot life.

  And, by using a room temperature curable epoxy resin composition characterized by containing each of the above components, a practical, injectable agent that cures with sufficient pot life even in a low temperature environment atmosphere, A coating and an adhesive can be provided.

  Moreover, in order to reinforce the room temperature curable epoxy resin composition characterized by containing each of the above-mentioned components with an injection agent for repairing cracks in a concrete structure, or a concrete structure or steel structure with a fiber sheet or a reinforcing plate By using them as coating agents, adhesives, etc., it becomes possible to repair, reinforce and reinforce these structures easily, reliably and firmly even in a low temperature atmosphere such as outdoors in winter.

  And after construction using a room temperature curable epoxy resin composition characterized by containing each of the above components under a low temperature atmosphere such as outdoors in winter, concrete is usually used due to an unexpected earthquake, etc. Even when a large stress is applied to the structure or steel structure that undergoes deformation and breakage, deformation is less likely to occur due to the presence of a cured epoxy resin that has been hardened reliably and sufficiently by construction. These structures are prevented from collapsing.

Claims (7)

  One or more compounds selected from the group consisting of (A) component epoxy resin, (B) component aliphatic polyamine, alicyclic polyamine and their modified products, and (C) component halogen A room temperature curable epoxy resin composition comprising a complex of boron fluoride and an amine compound.   The room temperature curable property according to claim 1, wherein the component (C) is a complex of boron trifluoride and one or more compounds selected from the group consisting of aliphatic amines, alicyclic amines, and imidazoles. Epoxy resin composition.   Component (C) is boron trifluoride and norbornanediamine, 1,3-xylylenediamine, isophoronediamine, 4,4′-methylenebis (cyclohexylamine), tetraethylenepentamine, 1,3-bis (aminomethyl) The room temperature curable epoxy resin composition according to claim 1, which is a complex with one or more compounds selected from the group consisting of cyclohexane, 2-ethyl-4-methylimidazole, monoethylamine and isopropylamine.   The component (B) is 20 to 200 parts by mass, and the component (C) is 1 to 100 parts by mass with respect to 100 parts by mass of the component (A). Room temperature curable epoxy resin composition.   The equivalent ratio of the active hydrogen group of the component (B) to the epoxy group of the component (A) is 0.5 to 2.0, and the component (C) is 1 to 100 mass with respect to 100 parts by mass of the component (A). The room temperature curable epoxy resin composition according to any one of claims 1 to 4, which is a part.   An adhesive comprising the room temperature curable epoxy resin composition according to any one of claims 1 to 5.   A repair / reinforcement method for a structure comprising repairing / reinforcing a structure using the room temperature curable epoxy resin composition according to any one of claims 1 to 5.