JPH06306146A - Maleimide resin composition and composite material produced therefrom - Google Patents

Abstract

PURPOSE:To provide a maleimide resin compsn. from which a cured resin article can be produced by a simple, easy, and rapid work. CONSTITUTION:A maleimide resin compsn. contains a linear polymer obtd. by copolymerizing a diepoxy compd. with a dihydric phenol compd. in the presence of a silicon compd. having or generating a silanolic hydroxyl group and an organometallic compd., a maleimide compd., a di- or polyamine compd., a silicon compd. having or generating a silanolic hydroxyl group, and an organometallic compd. The compsn., when it is cured, exhibits a very high toughness and characteristics inherent in a maleimide resin and, when combined with a substrate sheet, gives a composite material having excellent characteristics.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an artificial satellite structure, an aviation mechanism structure, a radar dome structure, an antenna structure, leisure products such as golf shafts, tennis rackets, fishing rods, and the like.
The present invention relates to a maleimide resin composition that can be widely used as materials for printed circuit boards, resin-encapsulated semiconductor components, electrical equipment insulating members, building members, and the like, and composite materials using the same.

[0002]

2. Description of the Related Art It has been conventionally known that maleimide compounds (maleimide resins) are excellent in various properties such as heat resistance. When addition polymerization is carried out using a compound having an amino group as a curing agent, volatile components are not generated, so these components do not remain as bubbles in the molecular structure, and a very dense resin cured product is obtained. Obtainable.

However, since the reaction between the maleimide compound and the compound having an amino group generally requires a high temperature condition of about 150 ° C. or higher and a long time, energy saving and workability are serious problems in forming a resin cured product by the above compound. Has become.

By the way, there is a demand for a lightweight material having high rigidity and high strength as various structural materials for artificial satellites, aircrafts, electric appliances and the like. For example, application of a composite material using carbon fiber, boron fiber, silicon carbide fiber, glass fiber or the like as a reinforcing base material and a maleimide resin, specifically, a maleimide resin composition containing a curing agent as a matrix has been attempted. ing. In such a composite material, a fibrous sheet-like base material formed by arranging carbon fibers or boron fibers in one direction and a matrix (maleimide resin) are combined and laminated, and the matrix is cured and molded. It has been proposed to exhibit excellent properties such as high strength and high elasticity. However, in this composite material, the direction other than the fiber arrangement direction of the sheet-shaped substrate, that is, the direction perpendicular to the fiber orientation, and the impact resistance, crack resistance, and other strength between the layers of the sheet-shaped substrate are remarkably increased. There is a problem that performance degradation is caused.

[0005]

SUMMARY OF THE INVENTION The present invention has been made in view of the above circumstances, and the first purpose thereof is to provide excellent properties as a maleimide resin in terms of heat resistance, mechanical properties, electrical properties, and the like. It is an object of the present invention to provide a maleimide resin composition in which a cured resin product can be obtained by a simple and quick operation.

A second object of the present invention is a composite material using a maleimide resin composition as a matrix, which has excellent heat resistance due to the characteristics of the maleimide resin.
It has mechanical strength and electrical characteristics, as well as crack resistance,
It is an object of the present invention to provide a composite material which is also excellent in impact resistance and which can be simply produced by a rapid matrix hardening operation.

[0007]

The first object of the present invention is to provide (a) a bifunctional epoxy compound and a bifunctional phenol compound having a silanol group or a silanol group. A linear polymer synthesized by polymerizing in the presence of a silicon compound and an organometallic compound, and (b) a maleimide compound,
(C) a difunctional or polyfunctional amine compound,
This is achieved by a maleimide resin composition containing (d) a silicon compound having a silanol-containing hydroxyl group or generating a silanol-containing hydroxyl group, and (e) an organometallic compound.

According to the maleimide resin composition of the present invention,
Generally, by performing a molding process including a treatment such as heating and light irradiation, the double bond of the maleimide compound (maleimide resin) (b) corresponding to the resin main component is converted into the double bond corresponding to the curing agent. The functional or polyfunctional amine compound (c) is added, the polymerization reaction of the maleimide compound (b) proceeds, and a cured product having a three-dimensional molecular structure is obtained.

In such a maleimide resin composition, in the addition polymerization reaction of the maleimide compound (b) and the amine compound (c), that is, in the curing reaction, a silicon compound (d) which has a silanol hydroxyl group or produces a silanol hydroxyl group and Since a binary curing catalyst composed of the organometallic compound (e) is present, this polymerization reaction is accelerated. Furthermore, by adjusting the combination of the compounds used for the curing catalyst and the amount of the compounds mixed, it becomes possible to easily variably adjust the progress state of the polymerization reaction, for example, the conditions such as the curing reaction rate. Therefore, the curing time can be shortened and the curing temperature can be lowered, and excellent curing characteristics can be imparted.

Further, in the maleimide resin composition of the present invention, the characteristics as a maleimide resin are sufficiently ensured with respect to heat resistance, mechanical properties, electrical properties and the like during curing.

However, in general, in a maleimide resin composition,
When a bifunctional or polyfunctional amine compound is used as a curing agent, the resin cured product formed is composed of a maleimide resin and an amine compound due to the fact that the amine compound has many reaction points. The cross-linking density of the three-dimensional molecular structure (cross-linking structure) may become high, resulting in excessive rigidity and impaired flexibility. In this case, the use of the maleimide resin composition may be limited. On the other hand, in the maleimide resin composition of the present invention, in addition to the composition system of components (b) to (e) described above, component (a), that is, a bifunctional epoxy compound and a bifunctional phenol compound. A polymer having a linear molecular structure synthesized from is blended. In the resin cured product obtained from such a maleimide resin composition, the above linear polymer is incorporated into its three-dimensional molecular structure. Therefore, in this resin cured product, the rigidity and the flexibility are maintained in a good balance, and the toughness is remarkably improved.

On the other hand, the second object of the present invention is achieved by a composite material obtained by coating or impregnating a base material with the above-mentioned maleimide resin composition and curing the same. In such a composite material, since the maleimide resin composition is applied as the matrix resin, the curing time of the matrix can be shortened, the curing temperature can be lowered, and the workability of curing can be improved. Further, the characteristics as a maleimide resin-based material are ensured with respect to heat resistance, mechanical strength, electrical properties, corrosion resistance including chemical resistance, and the like. Furthermore, crack resistance and impact resistance are further improved, and toughness is remarkably improved.

The maleimide resin composition of the present invention will be described in detail below. The maleimide resin composition of the present invention comprises the above-mentioned component (a), that is, a bifunctional epoxy compound and a bifunctional phenol compound, which has a silanol-containing hydroxyl group or produces a silanol-containing hydroxyl group and a silicon compound and an organic compound. It is most characteristic in that it contains a linear polymer synthesized in the presence of a metal compound. A cured product formed from such a resin composition becomes stronger due to the action of such a linear polymer.

Examples of the bifunctional epoxy compound used for the synthesis of the linear polymer, that is, the compound having two epoxy groups include, for example, bisphenol A type epoxy resin, bisphenol S type epoxy resin, and bisphenol F type epoxy resin. Examples thereof include resins and bisphenol K type epoxy resins. Examples of the bifunctional phenol compound used in the synthesis of the linear polymer, that is, the compound having two phenolic hydroxyl groups include, for example, bisphenol A, bisphenol S, bisphenol F, bisphenol K and other bisphenol compounds. Is mentioned.
The mixing ratio of these epoxy compound and phenol compound is set according to the molecular weight of the polymer to be synthesized.

The silicon compound having a silanol group hydroxyl group or generating a silanol group hydroxyl group and the organometallic compound used in the synthesis of the linear polymer correspond to a catalyst in the polymerization reaction of the epoxy compound and the phenol compound.

Specific examples of the silanol-containing silicon compound having a hydroxyl group, that is, the compound having a hydroxyl group directly bonded to a silicon atom, include diphenylmethylsilanol, phenylvinylsilanediol, tri (paramethoxyphenyl) silanol, and triacetylsilanol. , Diphenylethylsilanol, diphenylpropylsilanol,
Tri (paranitrophenyl) silanol, phenyldivinylsilanol, 2-butenyldiphenylsilanol, 2-
Pentenyldiphenylsilanol, phenyldipropylsilanol, paramethylbenzyldimethylsilanol,
Examples thereof include triethylsilanol, trimethylsilanol, tripropylsilanol, tributylsilanol, triisobutylsilanol and the like.

Examples of the silicon compound which produces a silanol hydroxyl group include compounds having a hydrolyzable group directly bonded to a silicon atom, or compounds which produce a silanol hydroxyl group by photolysis.

Of these, specific examples of the compound having a hydrolyzable group include triphenylmethoxysilane, diphenyldimethoxysilane, triphenylethoxysilane, diphenylmethylmethoxysilane, phenylvinylmethylmethoxysilane and diphenyldiethoxysilane. , Tri (paramethoxyphenyl) methoxysilane,
Triacetylmethoxysilane, diphenyldiethoxysilane, diphenylpropylethoxysilane, diphenylpropionylmethoxysilane, diphenylmethyltriphenylacetoxysilane, tri (paranitrophenyl)
Methoxysilane, triacetylmethoxysilane, phenyldivinylmethoxysilane, 2-butynyldiphenylmethoxysilane, di (2-pentenyl) phenylethoxysilane, phenyldipropylmethoxysilane, tri (paramethoxyphenyl) ethoxysilane, paramethylbenzyltri Methoxysilane, trifluoroacetyltrimethoxysilane, di (parachlorophenyl) diethoxysilane, triethylmethoxysilane, trimethylmethoxysilane, tripropylmethoxysilane, tributylethoxysilane, triisobutylacetoxysilane, compounds shown below (SI-1 ), (SI-2) and the like.

[0019]

[Chemical 1]

Specific examples of the silicon compound which produces a silanol hydroxyl group upon irradiation with light include a peroxysilane compound, a compound having an α-ketosilyl group, and a compound in which an o-nitrobenzyloxy group is directly bonded to a silicon atom. To be

In the synthesis of the linear polymer, the compounding amount of the silicon compound is appropriately set according to the molecular weight of the polymer to be synthesized. Examples of the organometallic compound include those in which various organic groups are directly bonded to metals such as aluminum, titanium, chromium, zirconium, copper, iron, manganese, nickel, vanadium, and cobalt, and complexes of the above metals. Compounds.

Of these, organoaluminum compounds are particularly useful, and are compounds having an alkoxy group or a phenoxy group bonded to an aluminum atom, an acyloxy ligand, a β-diketonato ligand, an o-carbonylphenolate at an aluminum atom. A complex compound to which a ligand or the like is bound is desirable.

Here, the alkoxy group preferably has 1 to 10 carbon atoms and includes methoxy, isopropoxy, butoxy, pentoxy and the like. Examples of the phenoxy group include phenoxy, o-methylphenoxy, o-methoxyphenoxy, p-nitrophenoxy,
2,6-dimethylphenoxy and the like can be mentioned.

Examples of the acyloxy ligand include acetato, propionato, isopropionato, butyrato, stearate, ethylacetoacetato, propylacetoacetato, butylacetoacetato, diethylmalato, dipivaloylmethanato and the like. To be

Examples of the β-diketonato ligand include acetylacetonato, trifluoroacetylacetonate, hexafluoroacetylacetonate, and the following (Li
-1) to (Li-3) and the like.

[0026]

[Chemical 2]

Examples of the o-carbonylphenolate ligand include salicylaldehyde. Specific examples of the above organoaluminum compound include:
Trismethoxyaluminum, trisethoxyaluminum, trisisopropoxyaluminum, trisphenoxyaluminum, trisparamethylphenoxyaluminum, isopropoxydiethoxyaluminum, trisbutoxyaluminum, trisacetoxyaluminum, trisstearatoaluminum, trisbutyratoaluminum, trispropionato. Aluminum, trisisopropionato aluminum, trisacetylacetonato aluminum, tristrifluoroacetylacetonato aluminum, trishexafluoroacetylacetonato aluminum, trisethylacetoacetato aluminum, trissartylaldehdato aluminum, trisdiethylmalolato aluminum, trispropyl Acetoacetate Aluminum, tris butyl acetoacetate Tato aluminum, tris dipivaloylmethanate aluminum, diacetylacetonatobis dipivaloylmethanate aluminum, and the following compound (Al-1) ~ (Al
-10) and the like.

[0028]

[Chemical 3]

[0029]

[Chemical 4]

These organoaluminum compounds may be used alone or in a mixture of two or more. In the synthesis of the linear polymer, the compounding amount of the organometallic compound is appropriately set according to the molecular weight of the polymer to be synthesized.

Specifically, the above-mentioned linear polymer is synthesized by charging the above-mentioned components in a suitable solvent and subjecting them to a treatment such as heating or exposure under a suitable temperature and pressure condition. You can The type of solvent used here, other synthesis conditions, and the like can also be appropriately selected according to the molecular weight of the polymer to be synthesized.

The linear polymer is a compound having a linear molecular structure and having a low molecular weight (oligomer) and a compound having a relatively high molecular weight (polymer).
Is included. The molecular weight is appropriately set depending on the use of the finally obtained maleimide resin cured product, but is preferably in the range of about 1,000 to 30,000.

In the maleimide resin composition of the present invention,
The blending amount of the linear polymer which is the component (a) is as follows.
The total amount of (c), (d) and (e) is 100 parts by weight, preferably 0.5 to 300 parts by weight, particularly preferably 5 to 150 parts by weight. If the blending amount is less than 0.5 parts by weight, the crack resistance and impact resistance of the cured product may be impaired, and if it exceeds 300 parts by weight, the viscosity of the solution of the composition increases, The workability of curing may deteriorate.

The maleimide compound (b) corresponding to the resin main component in the maleimide resin composition of the present invention is not particularly limited as long as it is a compound having at least one maleimide group, but it can be synthesized, for example, as follows. That is, first, maleic anhydride, a compound having an amino group, and optionally other acid anhydrides are reacted to generate an amic acid, and then the amic acid is converted to a lower acid anhydride such as acetic anhydride, sodium acetate. Etc. to obtain a ring by dehydration. Specific examples of the compound having at least one maleimide group include N, N'-phenylene bismaleimide, N, N'-hexamethylene bismaleimide,
N, N'-methylene-di-p-phenylene bismaleimide, N,
N'-oxy-di-p-phenylene bismaleimide, N, N'-
4,4'-benzophenone-bismaleimide, N, N'-diphenylsulfone bismaleimide, N, N '-(3,3'-dimethyl)-
Methylene-di-p-phenylene bismaleimide, N, N'-4,
4'-dihexahexylmethane-bismaleimide, N, N'-m
(Or p) -xylylene-bismaleimide, N, N '-(3,
3'-Diethyl) -methylene-di-p-phenylene bismaleimide, N, N'-metatoluylene-di-maleimide, maleimide compound obtained by reaction of mixed polyamine which is a reaction product of aniline and formalin with maleic anhydride , Monomaleimide compounds such as N-allyl-maleimide and N-phenylmaleimide. These maleimide compounds may be used alone or in a mixture of two or more.

Examples of the difunctional or polyfunctional amine compound (c) corresponding to the curing agent in the maleimide resin composition of the present invention include, for example, phenylenediamine, diaminodiphenylmethane, diaminodiphenyl ether, diaminodiphenyl sulfone, diaminodiphenyl sulfide. , Aromatic amine compounds consisting of halogen-substituted or alkyl-substituted compounds of these compounds, amine compounds obtained by reacting aniline or aniline derivatives with aldehydes, aminophenol derivatives having a hydroxyl group and an amino group in one molecule, and the like. To be Further, a compound having a secondary amino group in which one of the active hydrogens of the amino group is substituted with an alkyl group or an aryl group can be mentioned. These amine compounds are used alone or in a mixture of two or more.

The compounding amount of the amine compound (c) in the maleimide resin composition can be set within the stoichiometric range depending on its kind. In the maleimide resin composition of the present invention, the silicon compound (d) having a silanol-containing hydroxyl group corresponding to the curing catalyst or generating a silanol-containing hydroxyl group, and the organometallic compound (e) are the above-mentioned components (a). Compounds similar to those that can be used in the synthesis of linear polymers apply.

In the maleimide resin composition, the compounding amount of the silicon compound (d) is preferably about 0.001 to 0.001.
30% by weight, particularly preferably 0.1 to 10% by weight. If the blending amount is less than 0.001% by weight, sufficient curing-accelerated curing may not be obtained,
If it exceeds the weight%, the compatibility with other components may be deteriorated at the preparation stage of the composition.

In the maleimide resin composition, the organometallic compound (e), especially the organoaluminum compound, may be used alone or in a mixture of two or more kinds. The blending amount of the organoaluminum compound is preferably about 0.001 to 1 by weight ratio with respect to the maleimide compound (b).
0%, particularly preferably 0.1 to 5%. If the blending amount is less than 0.001% by weight, sufficient curing characteristics cannot be obtained, and if it exceeds 10% by weight, not only the cost becomes high, but also the cured product formed, particularly the composite material. This is not preferable because the electrical characteristics of are deteriorated.

In order to further improve the mechanical strength of the cured product, the maleimide resin composition of the present invention contains fine particles or short fibers in addition to the components (a) to (e) described above. It is desirable to mix them.

A wide variety of inorganic materials, organic materials, polymer materials, and metal materials are used for the powder and granules. Specific examples thereof include silica, alumina, talc, calcium carbonate, clay, aluminum hydroxide, barium sulfate, titanium dioxide, silicon nitride, silicon carbide, boron nitride, graphite, polyimide, polysulfone, and phenoxy resin.

On the other hand, the short fiber is not particularly limited as long as it is used as a reinforcing material of a resin material. Specific examples include glass fibers, alumina fibers, boron fibers, silicon carbide fibers, metal whiskers, carbon fibers, polyamide fibers, polybenzimidazole fibers, and the like.

When powders or short fibers are blended in the maleimide resin composition, the blending amount thereof is preferably about 3 parts with respect to 100 parts by weight of the total amount of the maleimide compound, the curing agent and the curing catalyst. ˜300 parts by weight, particularly preferably about 10 to 250 parts by weight. If the amount is less than 3 parts by weight, the mechanical strength of the cured product may not be sufficiently improved. On the other hand, if it exceeds 300 parts by weight, it becomes difficult to uniformly mix the resin component with the powder and / or the short fibers, and the workability of curing may be deteriorated.

The maleimide resin composition of the present invention comprises the components (a) to (e) and, if necessary, powders, short fibers,
Other additives may be dispersed or dissolved in an appropriate diluent to prepare a solution (varnish).

Next, the composite material of the present invention will be described in detail. In the composite material of the present invention, a sheet-shaped substrate is preferably used as the substrate. This sheet-shaped substrate is not particularly limited as long as it can be used as a reinforcing substrate for improving the mechanical strength of the matrix in a general composite material. Preferably, for example, a sheet made of a fibrous material made of an inorganic material or an organic material such as carbon fiber, glass fiber, boron fiber, nitride compound fiber, aromatic polyamide fiber and the like can be mentioned. Preferred is a sheet-like base material formed by arranging a bundle of fibers of the above-mentioned material in one direction.

When the sheet-like base material is used, the composite material of the present invention can be produced more specifically as follows. That is, first, a solution of a maleimide resin composition containing the components (a) to (e) described above is applied or impregnated as a matrix resin to a sheet-like base material as described above, and a slight heating is applied. Make prepreg. Next, several sheets of the prepregized sheets (prepregs) are laminated so that the carbon fibers in each sheet have an appropriate arrangement direction of the carbon fibers, and are cured to obtain a composite material.

The means for curing the prepreg as described above can be appropriately selected depending on the kind of the compound contained in the maleimide resin composition. For example, the prepreg is heated and / or irradiated with light. Can be done by applying. In particular, when the maleimide resin composition contains a silicon compound or the like that decomposes by light irradiation to generate a silanol group, the prepreg is cured by irradiating the prepreg with light such as ultraviolet light. However, in this case, the strength of the composite material to be produced, particularly the strength of the matrix may become insufficient, so it is preferable to subject the prepreg to heat treatment in addition to light irradiation.

Further, in the above-mentioned prepreg lamination, the characteristics of the composite material to be produced can be changed by adjusting the relationship in the arrangement direction of the fibers constituting each sheet.

The composite material of the present invention can also be prepared as follows when using substrates having different forms. For example, a sheet tape such as glass fiber or mica is wound around the electric conductor in advance, and then the tape is impregnated with the maleimide resin composition in a vacuum tank. Next, the resin composition is cured by heating to obtain a composite material having excellent electrical and mechanical performance. In addition, for manufacturing the composite material, a method of manufacturing various structures, parts, electrical appliances and the like can be applied. In this case, the maleimide resin composition is molded by a method such as transfer molding, injection molding or casting to obtain a composite material having a desired shape.

When the composite material of the present invention is produced, the maleimide resin composition contains the components (a) to (a) as described above.
In addition to (e), it is particularly preferable to add fine particulate powder or short fibers. In this case, the maleimide resin composition can be impregnated or applied to the base material without increasing the viscosity, so that the workability is improved.

Further, in the above composite material, the powdery particles are
When the base material is a sheet-like base material using a fibrous material, the base material is filled around the fibers constituting the base material and further in the gaps between the fibers. As a result, the strength of the composite material, for example, the strength in the direction orthogonal to the fiber orientation on the sheet surface is improved. In particular, when an external force is applied to the composite material, the energy is dispersed and propagates in the composite material due to the presence of the powder and granular material, and thus it is estimated that the occurrence of cracks in the composite material is prevented. Has been done.

Short fibers are also considered to improve the strength of the composite material produced in the same manner as above. In particular, when a composite material is prepared by coating or impregnating a sheet-shaped substrate with a maleimide resin composition, and then heating and curing the same, the strength between layers is improved due to the presence of short fibers. As a result, delamination is prevented.

It should be noted that the particle size of the powder or granules used for producing such a composite material is not particularly limited when the fibrous material is used as a sheet-like substrate to which the maleimide resin composition is applied or impregnated. It is desirable for the body to be smaller than the fiber diameter so that the interstices between the fibers are highly filled.

[0053]

EXAMPLES The present invention will be described in detail below with reference to examples. These examples are described for the purpose of facilitating the understanding of the present invention, and do not limit the present invention in particular. Synthesis Example 1: Synthesis of linear polymer Epicoat 828 (manufactured by Shell Chemical Co., Ltd.) as a bifunctional epoxy compound and a bifunctional phenol compound
4,4'-dihydroxydiphenyl sulfone (bisphenol S: manufactured by Wako Pure Chemical Industries, Ltd.), triphenylsilanol (TPS: manufactured by Toshiba Silicone Co., Ltd.) as a silicon compound, and trisacetylacetonato aluminum (Alacac: Wako Pure Chemical Industries, Ltd.) as an organic metal compound. (Manufactured by Yakusha Co., Ltd.) with the composition shown in Table 1 below, and the epoxy compound and the phenol compound are reacted under the conditions shown in the same table to obtain linear polymers (I-1) to
(I-3) was synthesized. The molecular weight of the obtained polymer is also shown in Table 1 below.

[0054]

[Table 1] Example 1 N, N'-methylene-di-p-phenylene bismaleimide (BMI: synthetic) was used as a maleimide compound, and diaminodiphenylmethane (DAM: was used as a difunctional amine compound).
The linear polymer (I manufactured by Kanto Chemical Co., Inc.) obtained in Synthesis Example 1 was used.
-1) to (I-3), triphenylsilanol (TPS) as a silicon compound, and triacetylacetonatoaluminum (Alac) as an organometallic compound.
ac) was mixed in the diluent methyl ethyl ketone (MEK) with the composition shown in Table 2 below to give a maleimide resin composition (M
-1) to (M-6) were prepared.

On the other hand, a bundle (3000 pieces) of carbon fibers (pitch-based carbon fibers) having a diameter of 7 μm was arranged in a sheet shape in one direction to prepare a sheet-shaped base material. The tensile elastic modulus of this sheet-shaped substrate was 49 ton / mm ² .

Next, the sheet-shaped substrate is coated or impregnated with each of the maleimide resin compositions (M-1) to (M-6) prepared as described above, air-dried, and then at a temperature of about 45.
It was heated at 0 ° C to form a prepreg. Next, this prepreg is cut into a predetermined shape, and the prepreg 23 after cutting is cut.
The arrangement direction of the carbon fibers in one prepreg and the arrangement direction of the carbon fibers in the prepregs laminated on the upper layer and / or the lower layer of the prepreg are 9
The layers were alternately laminated so as to form 0 degree. After covering the upper surface and the lower surface of this laminate with a release sheet, the laminate was sandwiched between a set of stainless steel plates having a thickness of 2 mm and further housed in a vacuum forming bag. Subsequently, this bag was introduced into an autoclave and heated under the conditions shown in Table 2 below to cure the maleimide resin composition in the laminate housed in the bag, and to prepare a composite material having a thickness of about 1.6 mm. Got

Regarding the composite material produced in this way,
Tensile strength was measured according to ASTM D3030, and fracture toughness value was measured according to the double torsion method. The results are also shown in Table 2. Comparative Example 1 A maleimide resin composition (C-1) containing no linear polymer was prepared by mixing each component with the composition shown in Table 2 below in a diluent methyl ethyl ketone (MEK).

Then, according to the same method and conditions as in Example 1, the sheet-shaped substrate and the maleimide resin composition (C-
A composite material was prepared using 1). The tensile strength and fracture toughness of this composite material were measured in the same manner as in Example 1. The results are also shown in Table 2.

[0059]

[Table 2]

From the results shown in Table 2, which corresponds to the present invention,
Maleimide resin composition (M-1) each containing a linear polymer
To (M-6), both of the mechanical strength and toughness of the composite material produced by using the resin composition (C-1) containing no polymer. It turned out to be excellent.

[0061]

As described in detail above, according to the present invention,
Provided is a maleimide resin composition in which excellent properties as a maleimide resin are secured in terms of heat resistance, mechanical properties, electrical properties, etc., and a resin cured product can be obtained by a simple and quick operation. Further, the maleimide resin composition exhibits excellent toughness when cured.

Furthermore, according to the present invention, by using the above maleimide resin composition, a rapid matrix hardening operation results in excellent heat resistance due to the characteristics of the maleimide resin.
It has mechanical strength and electrical characteristics, as well as crack resistance,
It is possible to manufacture a composite material which has excellent impact resistance and is extremely tough.

Claims (2)

[Claims] 1. Synthesized by polymerizing (a) a bifunctional epoxy compound and a bifunctional phenol compound in the presence of a silicon compound having a silanol-containing hydroxyl group or a silanol-containing hydroxyl group or an organometallic compound. (B) a maleimide compound, (c) a bifunctional or polyfunctional amine compound, and (d) a silicon compound having a silanol group or forming a silanol group. e) A maleimide resin composition containing an organometallic compound. 2. A composite material obtained by coating or impregnating a base material with the maleimide resin composition according to claim 1 and curing the base material.