JPH093021A - Fine powdery hydrazine compound - Google Patents

Abstract

PURPOSE: To obtain the subject compound having a specific average particle diameter, excellent in dispersibility in organic solvents, water and resin raw materials without deteriorating the heat resistance, moisture resistance, water resistance, electric insulation, etc., of epoxy resins, large in the curing speed, and useful as a curing agent for the epoxy resins. CONSTITUTION: A hydrazide compound having one or more hydrazide groups in the molecule e.g. a compound of formula I [R is H, an alkyl, a (substituted) aryl, hydrazino], a compound of formula II [A is a (substituted)alkylene, a (substituted)arylene, oxo; (n) is 0,1]}. The hydrazide compound has an average particle diameter of 0.5-20μm, especially 1-5μm, and preferably surface-coated with a coupling agent such as a silane, titanate, aluminum or phosphorus coupling agent.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a finely divided hydrazide compound. The finely powdered hydrazide compound of the present invention can be suitably used as a curing agent for producing an epoxy resin for a sealing material or a sealing material for electronic parts such as liquid crystal display devices.

[0002]

2. Description of the Related Art Epoxy resins are usually produced by adding a curing agent to a raw material such as bisphenol A or epichlorohydrin, or by adding the curing agent and then heating to about 100 to 200 ° C. Examples of the curing agent include aliphatic amines such as diethylenetriamine and triethylenetetramine, modified amines obtained by adding epoxy resin, acrylonitrile, ethylene oxide and the like to the aliphatic amines, aromatic compounds such as metaphenylenediamine, diaminodiphenylmethane and diaminodiphenylsulfone. Group polyamines, phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methylnadic acid anhydride, pyromellitic anhydride, HET acid anhydride, acid anhydrides such as dodecenyl succinic anhydride, adipic acid dihydrazide, dodecane diacid dihydrazide, etc. Dibasic acid dihydrazide and the like are used.

Of these curing agents, amines and acid anhydrides have been widely used since they give epoxy resins excellent in electric insulation, heat resistance, moisture resistance, water resistance, and dimensional stability. It has drawbacks such as short pot life, high curing temperature, and long curing time. On the other hand, dibasic acid dihydrazide is used in an increasing amount because it is superior in storage stability to amines and acid anhydrides. However, the epoxy resin obtained has heat resistance, moisture resistance and water resistance. , Electrical insulation is not enough,
There is no problem when it is used in the field of adhesives and paints, but it is not problematic when it is used in the field of encapsulants and shields of electronic parts such as liquid crystal display devices that require high reliability. Appropriate. Further, dibasic acid dihydrazide has a characteristic that it is difficult to dissolve or disperse in water or various organic solvents, especially water. Such characteristics are not suitable under the present circumstances where the awareness of environmental protection is increasing and the solvent used in the production of synthetic resin is being replaced by water from organic solvent.

On the other hand, JP-A-2-223954 discloses a resin composition containing an epoxy resin and a dibasic acid dihydrazide, and a dibasic acid dihydrazide having an average particle size of 10 μm or less is advantageous in terms of thermosetting property. Is also disclosed. However, the resin composition described in this publication is used for the purpose of forming a circuit of a printed wiring board by a photoresist method, and therefore, in addition to epoxy resin and dibasic acid dihydrazide, general epoxy resin Contains an ethylenic photopolymerizable monomer and a photopolymerization initiator which are not contained. Therefore, the curing reaction of the resin composition cannot be treated in the same manner as that of a general epoxy resin.

[0005]

As a result of intensive studies to solve the above-mentioned problems of the prior art, the present inventor crushed dibasic acid dihydrazide into a fine powder having an average particle diameter in a specific range, and pulverized it with an epoxy resin. When used as a curing agent for resins, not only the curing reaction itself can be carried out at a lower temperature in a short time, but also the drawbacks of conventional dibasic acid dihydrazides,
That is, the heat resistance, moisture resistance, water resistance of the obtained epoxy resin,
Disadvantages such as a decrease in electrical insulation is eliminated, and in addition, fine powder having an average particle diameter in the specific range is also excellent in dispersibility in an organic solvent or water, easy to uniformly disperse with a resin raw material, and in an aqueous system. The present invention has been completed by finding out that it can be preferably used for the production of the synthetic resin.

That is, the present invention relates to a hydrazide compound having at least one hydrazide group in one molecule and having an average particle diameter of 0.5 to 20 μm.

The finely divided hydrazide compound of the present invention has an average particle size of 0.5 to 20 μm, preferably 1 to 5 μm. If it is less than 0.5 μm, the storage stability may be lowered, and further, the aggregation of particles may make handling of the product difficult, which is not preferable. On the other hand, when it exceeds 20 μm, for example, when the finely powdered hydrazide compound of the present invention is used as a curing agent for an epoxy resin, the heat resistance, moisture resistance, water resistance, electrical insulation and the like of the resulting epoxy resin are deteriorated, which is preferable. Absent.

The finely divided hydrazide compound of the present invention can be produced by treating a powder of a hydrazide compound having at least one hydrazide group in its molecule (hereinafter simply referred to as "hydrazide compound") with a high-pressure grinder.

The hydrazide compound is not particularly limited and may be a known compound. Specifically, for example, the general formula

[0010]

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[Wherein R represents a hydrogen atom, an alkyl group, an aryl group which may have a substituent or a group —NHNH ₂ ]. ] A monohydrazide compound represented by the general formula

[0012]

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[In the formula, A represents an alkylene group which may have a substituent, an arylene group which may have a substituent or an oxo group. n represents 0 or 1. ] The dihydrazide compound etc. which are represented by these can be mentioned.

In the above general formula (1), the alkyl group represented by R is, for example, a methyl group, an ethyl group or n.
-A carbon number of 1 to 1 such as -propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group and n-undecyl group.
Twelve linear alkyl groups can be mentioned. Examples of the aryl group include a phenyl group, a biphenyl group, a naphthyl group, an anthryl group, a phenanthryl group and the like, and among these, a phenyl group and a naphthyl group are preferable. Examples of the substituent of the aryl group include a hydroxyl group, a halogen atom such as fluorine, chlorine and bromine, a carboxy group, a methyl group, an ethyl group, an n-propyl group and i.
Examples thereof include linear or branched alkyl groups having 1 to 4 carbon atoms such as so-propyl group, n-butyl group, tert-butyl group, and iso-butyl group, and among these, a hydroxyl group and a carboxy group. Etc. are preferred.

Specific examples of the monohydrazide compound of the above general formula (1) include carbohydrazide, lauric acid hydrazide, salicylic acid hydrazide, form hydrazide, acetohydrazide, propionic acid hydrazide, p.
-Hydroxybenzoic acid hydrazide, naphthoic acid hydrazide, 2-hydroxy-3-naphthoic acid hydrazide and the like can be mentioned.

In the general formula (2), examples of the alkylene group represented by A include a methylene group, an ethylene group, an n-propylene group, an n-butylene group, an n-pentylene group, an n-hexylene group and an n-hexene group. Examples thereof include linear alkylene groups having 1 to 12 carbon atoms such as heptylene group, n-octylene group, n-nonylene group, n-decylene group, and n-undecylene group. As the substituent of the alkylene group,
For example, a hydroxyl group etc. can be mentioned. Examples of the arylene group include a phenylene group, a biphenylene group, a naphthylene group, an anthrylene group, and a phenanthrylene group. Among these, a phenylene group and a naphthylene group are preferable. As the substituent of the arylene group,
The same substituents as those described above for the aryl group can be used.

Specific examples of the dihydrazide compound represented by the general formula (2) include oxalic acid dihydrazide, malonic acid dihydrazide, succinic acid dihydrazide, adipic acid dihydrazide, azelaic acid dihydrazide, sebacic acid dihydrazide, dodecane-2-acid dihydrazide. Examples thereof include maleic acid dihydrazide, fumaric acid dihydrazide, diglycolic acid dihydrazide, tartaric acid dihydrazide, malic acid dihydrazide, isophthalic acid dihydrazide, terephthalic acid dihydrazide, and dibasic acid dihydrazide such as 2,6-naphthoic acid dihydrazide.

Examples of hydrazide compounds other than the above include polyacrylic acid hydrazide, dibasic acid dihydrazide compounds described in Japanese Patent Publication No. 2-4607, and 2,4-dihydrazino-6-methylamino-sym-triazine. You can

The high-pressure pulverizer for finely pulverizing the above various hydrazide compounds into those having an average particle size specified in the present invention is a pulverized product by introducing a high-pressure gas (for example, air, nitrogen, etc.) into the device. There is no particular limitation as long as it is a device that performs the above. For example, high-pressure air is jetted into the device from at least one direction, preferably two or more directions, on the side surface of the device to generate an air flow to pulverize powder, An example is a system that collects fine powder that floats above the device. More specifically, for example, a counter jet mill (trade name, manufactured by Alpine, Netherlands), a cross jet mill (trade name, manufactured by Kurimoto Iron Works Co., Ltd.), a jet atomizer (trade name, Seishin Industry Co., Ltd.) Manufactured) and the like.

The finely powdered hydrazide compound of the present invention may be surface-treated with a coupling agent. By performing the surface treatment, the curing time can be further shortened when used as a curing agent or curing accelerator for synthetic resin, for example.

The coupling agent used in the present invention may be a known one, for example, a silane coupling agent,
Examples thereof include titanate-based coupling agents, aluminum-based coupling agents, phosphorus-based coupling agents, and the like.

Specific examples of the silane coupling agent include, for example, γ-aminopropyltriethoxysilane,
N-β- (aminoethyl) -γ-aminopropyltriethoxysilane, N-β- (aminoethyl) -γ-aminopropyltrimethoxysilane, N-β- (aminoethyl) -γ-aminopropylmethyldimethoxysilane , N
-Phenyl-γ-aminopropyltrimethoxysilane,
Aminosilane coupling agents such as γ-ureidopropyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, β- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, γ-glycidyloxypropyltrimethoxysilane, Epoxysilane coupling agents such as γ-glycidoxypropylmethyldiethoxysilane, vinylsilane coupling agents such as vinyltrichlorosilane, vinyltrimethoxysilane, vinyltriethoxysilane and vinyltris (β-methoxyethoxy) silane, γ -Mercaptosilane-based coupling agents such as mercaptopropyltrimethoxysilane, acrylsilane-based coupling agents such as γ-methacryloyloxypropyltrimethoxysilane, methyltrimethoxysilane, methyltriethoxysilane General formula RSi (OR ') ₃ such as orchid, γ-chloropropyltrimethoxysilane and trifluoromethyltrimethoxysilane [wherein R is a carbon number 1 which may be substituted by one or two or more halogen atoms]
A linear or branched alkyl group of about 4 to R '
Represents a linear or branched alkyl group having about 1 to 4 carbon atoms. And the like.

Specific examples of titanate coupling agents include, for example, isopropyltriisostearoyl titanate, isopropyl tris-isodecylbenzenesulfonyl titanate, isopropyl tris-n-decylbenzenesulfonyl titanate, isopropyl tris (dioctylpyrophosphate) titanate, Tetraisopropyl-bis (dioctylphosphite) titanate,
Tetraoctyl-bis (ditridecylphosphite) titanate, tetra (2,2-diallyloxymethyl-1)
-Butyl) -bis (di-tridecyl phosphite) titanate, bis (dioctyl pyrophosphate) oxyacetate titanate, bis (dioctyl pyrophosphate) ethylene titanate, isopropyl trioctanoyl titanate, isopropyl dimethacryl isostearoyl titanate, isopropyl isostearoyl Examples thereof include diacrylic titanate, isopropyl tri (dioctyl phosphate) titanate, isopropyl tricumyl phenyl titanate, isopropyl tri (N-aminoethyl aminoethyl) titanate, dicumyl phenyloxyacetate titanate and diisostearoyl ethylene titanate.

Specific examples of the aluminum-based coupling agent include aluminum monoacetylacetonate-bis (ethylacetoacetate), aluminum tris (acetylacetate), acetoalkoxyaluminum diisopropylate and the like.

The phosphorus-based coupling agent is, for example,
Acryloyloxyethyl phthaloxyethyl diethyl phosphate, di (methacryloyloxyethyl phthaloxyethyl) diethylpyrophosphate, di (methacryloyloxyethyl phthaloxyethyl) methyl phosphite, di (methacryloyloxyethyl phthaloxyethyl) phosphate, di (acryloyloxy) Ethylphthaloxyethyl) pyrophosphate, di (methacryloyloxyethylphthaloxyethyl) phosphite, methacryloyloxyethyl maleoxyethyl diethyl phosphate, di (acryloyloxyethyl maleoxyethyl) diethylpyrophosphate, di (methacryloyloxyethyl maleoxyethyl) ) Ethyl phosphite, di (acryloyloxyethyl maleoxyethyl) phosphate Di (methacryloyloxyethyl maleoxyethyl) pyrophosphate, di (acryloyloxyethyl maleoxyethyl) phosphite, methacryloyloxyethyl succinoxyethyl diethyl phosphate, di (methacryloyloxyethyl succinoxyethyl) dimethylpyrophosphate, di ( Methacryloyloxyethyl succinoxyethyl) ethyl phosphite, di (methacryloyloxyethyl succinoxyethyl) phosphate, di (methacryloyloxyethyl succinoxyethyl) pyrophosphate, di (methacryloyloxyethyl succinoxyethyl)
Examples thereof include phosphite, di (N-acrylaminomethyl) phosphite, di (N-acrylaminomethyl) pyrophosphate, and di (N-acrylaminomethyl) phosphate.

Among the above coupling agents, silane coupling agents, aluminum coupling agents and the like are preferable.

Such coupling agents may be used alone or in combination of two or more.

For surface treatment using a coupling agent, known methods such as wet method and dry method can be employed.

The treatment by the wet method is usually carried out by mixing the finely divided hydrazide compound of the present invention with a solution or dispersion of a coupling agent, separating the treated finely divided hydrazide compound from this mixture, and drying. Done. Coupling agents are water, acetic acid water, methanol, ethanol,
It is soluble or dispersible in organic solvents such as cellosolve, alkylamine, and alkylolamine, or a mixed solvent thereof. The concentration of the coupling agent at this time is not particularly limited,
It can be appropriately selected from a wide range, but usually 0.1 to 5% by weight
The amount may be about 0.5 to 2% by weight.
For separation of the treated fine powder hydrazide compound, known methods such as filtration, centrifugation, decantation and the like can be adopted. When the finely powdered hydrazide compound treated by drying aggregates, it may be pulverized according to a known method. Further, the finely divided hydrazide compound dispersion may be mixed with the coupling agent solution or dispersion, and the treated finely divided hydrazide compound may be collected and dried. As the solvent for dispersing the fine powder hydrazide compound, the same solvent as described above can be used.
The wet method can be carried out with heating or heating, if necessary. The standard of the temperature at that time is about 30 to 100 ° C.

In the dry method, the coupling agent or the solution or dispersion thereof is added to the powder of the finely powdered hydrazide compound, with stirring and / or preheating, if necessary, and mixed (preferably mixed under heating). Is the way. For stirring and mixing, an ordinary blender, preferably a blender having a shearing force such as a Henschel mixer or a super mixer is used. The solution and dispersion of the coupling agent may be the same as those used in the wet method. The preheating and heating may be performed in a temperature range up to a temperature at which decomposition or deterioration of the fine powder hydrazide compound does not occur.

In both the wet method and the dry method, the amount of the coupling agent used may be appropriately selected from a wide range depending on the type of the coupling agent, the stability with time of the fine powder hydrazide compound, etc. It may be about 0.01 to 10 parts by weight, preferably about 0.1 to 5 parts by weight, based on 100 parts by weight of the fine powder hydrazide compound. When a solution or dispersion liquid of the coupling agent is used, the amount of the solution or dispersion liquid may be adjusted so that the mixing ratio is as described above.

The finely powdered hydrazide compound of the present invention can be used, for example, as a curing agent or curing accelerator for synthetic resins. When the finely powdered hydrazide compound of the present invention is used for curing synthetic resin, a known curing agent and / or curing accelerator can be used in combination as long as the effect thereof is not impaired. Among the finely divided hydrazide compounds of the present invention, the finely divided monohydrazide compound is, for example, as a curing accelerator for synthetic resin, and the finely divided dihydrazide compound is, for example,
It can be suitably used as a curing agent for synthetic resins.
The fine powdery monohydrazide compound and the fine powdery dihydrazide compound can be used in combination.

The synthetic resin to which the fine powder hydrazide compound of the present invention can be applied is not particularly limited and may be a known one, for example, epoxy resin, xylene resin, guanamine resin, diallyl phthalate resin, vinyl ester resin,
Examples thereof include thermosetting resins such as phenolic resins, unsaturated polyester resins, furan resins, polyimides, polyurethanes, maleic acid resins, melamine resins and urea resins, and thermoplastic resins such as acrylic resins and acetoacetylated polyvinyl alcohol. Of these, epoxy resins and acrylic resins are particularly preferable.

Any known epoxy resin may be used,
For example, bisphenol A type epoxy resin, bisphenol F type epoxy resin, phenol novolac type epoxy resin, cresol novolac type epoxy resin, glycidyl amine type epoxy resin, alicyclic epoxy resin, urethane modified epoxy resin, brominated bisphenol A type epoxy resin , Heterocyclic epoxy resins and the like. The curing accelerator of the present invention can be applied to various commercially available epoxy resins.

Any known acrylic resin may be used,
Specific examples thereof include those containing at least one selected from the following non-functional monomers, monofunctional monomers and polyfunctional monomers. Specific examples of the non-functional monomer include, for example, methyl methacrylate,
Ethyl methacrylate, propyl methacrylate, n-butyl methacrylate, isobutyl methacrylate, tert-butyl methacrylate, 2-ethylhexyl methacrylate, octyl methacrylate, isodecyl methacrylate,
Lauryl methacrylate, lauryl methacrylate-tridecyl, tridecyl methacrylate, cetyl methacrylate-
Stearyl, stearyl methacrylate, cyclohexyl methacrylate, benzyl methacrylate and the like can be mentioned. Specific examples of the monofunctional monomer include, for example,
Methacrylic acid, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, dimethylaminoethyl methacrylate, diethylaminoethyl methacrylate, tert-butylaminoethyl methacrylate, glycidyl methacrylate, tetrahydrofurfuryl methacrylate, etc. may be mentioned. it can. Specific examples of the polyfunctional monomer include ethylene dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, decaethylene glycol dimethacrylate, and pentadecaethylene glycol dimethacrylate. , Pentamethacrylate ethylene glycol dimethacrylate, 1,3-butylene dimethacrylate, allyl methacrylate, trimethylolpropane trimethacrylate, pentaerythritol tetramethacrylate, diethylene glycol phthalate diethylene glycol and the like. Further, for example, a copolymerization monomer such as acrylamide, acrylonitrile, acryloylmorpholine, and acryloguanamine may be contained. Further, it can be applied to a commercially available acrylic resin.

In the above synthetic resin, if necessary, known inorganic fillers such as fused silica, crystalline silica, aluminum hydroxide, alumina, white carbon and carbon black, potassium titanate whiskers, calcium silicate whiskers, Inorganic whiskers such as aluminum borate whiskers, magnesium borate whiskers, and zinc silicate whiskers, various rubbers and the like may be contained. Further, if necessary, known plastic additives such as an antioxidant, an ultraviolet absorber, an antistatic agent, a flame retardant, a colorant, and an antifungal agent may be contained. In curing the thermosetting resin using the fine powder hydrazide compound of the present invention, known methods can be adopted. For example, the liquid thermosetting resin component before curing may be mixed with the finely powdered hydrazide compound of the present invention and, if necessary, a known curing agent, curing accelerator, and other additives, and heated. . The curing reaction can be carried out in any of an aqueous system, an organic solvent system or an emulsion system. When using the finely powdered dihydrazide compound of the present invention as a curing agent, the amount of the curing agent is not particularly limited and can be appropriately selected from a wide range, but usually about 1 to 50 parts by weight with respect to 100 parts by weight of the resin solid content,
The amount is preferably about 5 to 10 parts by weight. Further, when the fine powdery monohydrazide compound of the present invention is used as a curing accelerator, the compounding amount of the curing accelerator is not particularly limited and can be appropriately selected from a wide range, but is usually 0.01 to 10 relative to the resin solid content. The amount may be about part by weight, preferably about 0.1 to 1 part by weight. Also, the curing temperature and time are not limited, but the curing reaction can be completed under a relatively low temperature of usually 100 to 120 ° C. in a short time of about 5 to 30 minutes. In addition, of course, the curing reaction can be performed at a temperature higher than 120 ° C. When the fine powdery monohydrazide compound of the present invention is used as a curing accelerator, the curing reaction proceeds even at a lower temperature of around 90 ° C.
It takes about 30 minutes to finish.

Crosslinking of the thermoplastic resin can also be carried out in the same manner as in the case of the thermosetting resin, except that the crosslinking temperature is room temperature and the use of a curing agent is not essential.

[0038]

INDUSTRIAL APPLICABILITY The fine powder hydrazide compound of the present invention, when used as a curing agent for an epoxy resin, can give an epoxy resin excellent in heat resistance, moisture resistance, water resistance, electrical insulation, etc. The epoxy resin can be suitably used not only as a main component of paints and adhesives, molded products, but also as a sealing material and a sealing material for electronic parts such as liquid crystal display devices.

The differential hydrazide compound of the present invention is
It has excellent dispersibility in organic solvents and water, is easy to uniformly disperse with the resin raw material, and can be suitably used for producing synthetic resins in an aqueous system.

As described above, the finely powdered dihydrazide compound of the present invention can be used not only as a curing agent and a curing accelerator for synthetic resins, but also as an intermediate for the production of various pharmaceuticals and agricultural chemicals.

[0041]

EXAMPLES The present invention will be specifically described below with reference to Examples and Test Examples.

Example 1 Adipic acid dihydrazide was crushed with a high-pressure crusher (trade name: Jet Ohmizer, manufactured by Seishin Industry Co., Ltd.),
Finely powdered adipic acid dihydrazide having an average particle diameter of 2.0 μm was produced.

Test Example 1 To 100 parts by weight of an epoxy resin (trade name: Epotote YD-128, manufactured by Yuka Shell Epoxy Co., Ltd.) was added 30 parts by weight of the finely powdered adipic acid dihydrazide of Example 1 to obtain 12 parts.
The gel time was measured by heating to 0 ° C. For comparison, an undiluted product of adipic acid dihydrazide was used and the gel time was measured in the same manner as above. The results are shown in Table 1.

[0044]

[Table 1]

Example 2 100 g of adipic acid dihydrazide of Example 1 was added to 500 ml of methanol, and 0.5 g of an aluminum coupling agent (trade name: AL-M, manufactured by Ajinomoto Co., Inc.) was added and mixed well. , Methanol was removed, and surface-treated adipic acid dihydrazide was produced.

Examples 3 to 5 Isophthalic dihydrazide (Example 3), dodecane diacid dihydrazide (Example 4) or 2,6-naphthoic acid dihydrazide (Example 5) is used as the dihydrazide compound instead of adipic acid dihydrazide. Except for this, the same operation as in Example 1 was carried out to produce a fine powdery dihydrazide compound having an average particle diameter of 2.0 to 4.0 μm.

The obtained finely powdered dihydrazide compound was treated in the same manner as in Example 2 to produce a surface-treated dihydrazide compound.

Test Example 2 Test Example 1 except that the fine powdery dihydrazide compound of Examples 2 to 5 (however, the fine powdery adipic acid dihydrazide is that of Example 1) and the surface-treated dihydrazide compound were used in place of the fine powdery adipic acid dihydrazide. The gel time was measured in the same manner as in. For comparison, gel time was also measured for undiluted products of each dihydrazide compound. Table 2 shows the results
Shown in

[0049]

[Table 2]

It can be seen from Tables 1 and 2 that the curing time can be significantly shortened by using the dihydrazide compound of the present invention as a curing agent.

Test Example 3 From the epoxy resin obtained in Test Example 1, a size of 20 mm ×
A test piece of 10 mm x 10 mm is cut out and 80 ° C x 96
After being stored under the condition of% RH for 2000 hours, the appearance of the test piece was observed. The results are shown in Table 3.

[0052]

[Table 3]

From Table 3, it is clear that the epoxy resin cured by using the fine powdery dihydrazide compound of the present invention is excellent in heat resistance and moisture resistance.

Claims (4)

[Claims] 1. A hydrazide compound having at least one hydrazide group in one molecule and having an average particle diameter of 0.5 to 20 μm. 2. The average particle diameter is 1 to 5 μm.
The finely powdered hydrazide compound described in. 3. The finely powdered hydrazide compound according to claim 1, wherein the hydrazide compound is a dibasic acid dihydrazide. 4. The finely powdered hydrazide compound according to claim 1, which is surface-treated with a coupling agent.