JPH1067855A - Organic-group-modified silicate and thermosetting resin composite containing the same as the component - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain an org.-group-modified silicate which is suitable for producing a thermosetting resin composite having excellent resistances to heat and environmental conditions, high mechanical strengths, and good toughness, thermal impact resistance, and moldability by subjecting a system comprising an alkoxysilane and a silicon compd. having a specific functional group and SiH groups to reaction. SOLUTION: This silicate is obtd. by subjecting a system comprising an alkoxysilane and a silicon compd. having at least one specific functional group and at least two SiH groups in the molecule to reaction. The specific functional group is pref. a carboxyl, acid anhydride, epoxy, amino, or hydroxyl group, esp. pref. an epoxy group. Tetraethyl silicate is esp. pref. as the alkoxysilane. A pref. silicon compd. is an epoxidized polymethylhydrogensiloxane deriv.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION The present invention relates to a thermosetting resin which is blended with a thermosetting resin and then reacted with the resin to provide excellent heat resistance, environmental resistance, high mechanical strength such as bending characteristics, and good high toughness. The present invention relates to an organic group-modified silicate from which a thermosetting resin composite material having thermal shock resistance and moldability can be obtained, and a thermosetting resin composite material containing the silicate as a component.

[0002]

2. Description of the Related Art Inorganic fillers such as silica are used in resin compositions used as sealants for electronic components such as ICs to improve strength, impact resistance, heat resistance, moldability, etc., and reduce costs. It is widely used as a filler for such reasons. However, organic resin and inorganic filler have low affinity and are difficult to disperse.Because each is present independently, when external force such as thermal stress is applied, it is the most mechanically weak part. There is a problem that destruction occurs from an interface between a certain resin and an inorganic filler, and it is not possible to sufficiently improve the characteristics. Conventionally, as a method of solving this problem, a method of compounding a coupling agent has been performed, but the coupling agent reacts with an inorganic filler having a hydroxyl group if conditions are selected,
At present, it is difficult to set the conditions and it is not possible to sufficiently improve the characteristics. In addition, many of these silica particles contain impurities such as chlorine, sodium, uranium and thorium, and these are generally known to cause wiring corrosion and soft errors, respectively. Even if such silica is subjected to a coupling treatment, physical properties cannot be improved as long as impurities are mixed.

On the other hand, when synthesizing spherical silica particles by the sol-gel method, silica particles having a specific organic modifying group are prepared by adding alkoxysilane having an organic functional group, and this improves the properties of a resin product as a filler. This is already disclosed in Japanese Examined Patent Publication No. 6-17476. However, the mixing ratio of ethyl silicate used as a raw material for the sol-gel method is as high as 97% or more and is close to an inorganic material. The effect of improving the affinity of the resin composition is insufficient, and the resulting resin composition also has unsatisfactory mechanical properties such as bending properties.

[0004] It is also disclosed in Japanese Patent Application Laid-Open No. H05-260, that a silicon-based hybrid material can be obtained by mixing an alkoxysilane, a silicon compound having at least two SiH groups, and an organic compound having at least two alkenyl groups.
No. 86192, which is disclosed in Japanese Unexamined Patent Publication No. 86192, since it contains two or more alkenyl groups and the like, organic and inorganic are sequentially cross-linked to form an organic-inorganic hybrid material. The molding processability is inferior to that of the conductive resin, and the strength is also unsatisfactory. As described above, an organic material capable of obtaining a thermosetting resin composite material having excellent heat resistance, environmental resistance, high mechanical strength such as bending characteristics, and good high toughness, thermal shock resistance, and moldability. Group-modified silicate has not been developed yet.

[0005]

DISCLOSURE OF THE INVENTION The present invention has been made to solve a problem which has been difficult with a conventional inorganic filler. Thermosetting resin composite material with good interfacial strength, excellent heat resistance and environmental resistance, high mechanical strength such as bending properties, and good high toughness, thermal shock resistance, and moldability. The present invention relates to an organic group-modified silicate and a thermosetting resin composite material containing the silicate as a component.

[0006]

Means for Solving the Problems In view of such circumstances, the present inventors have conducted intensive studies and as a result, have found that they contain an alkoxysilane (a) and at least one specific functional group,
By reacting a system comprising a silicon compound (b) having at least two SiH groups in the molecule, an organic group-modified silicate having a specific functional group can be obtained. It has been found that the resin itself has flexibility and good affinity with the resin, and when used as a component of the thermosetting resin composition, the characteristics of the resin product are remarkably improved, and the present invention has been completed.

[0007]

BEST MODE FOR CARRYING OUT THE INVENTION The alkoxysilanes having no functional group other than the alkoxy group used as the component (a) in the present invention have a high heat resistance when the organic group-modified silicate obtained in the present invention is blended in a resin. It is a component for imparting flame resistance and high strength, and is not particularly limited, and various components can be used, but an alkoxysilane represented by the formula (2) or a hydrolytic condensate thereof is preferable. Can be used. RnSi (OR ') _4-n (2) R is a monovalent organic group having 1 to 50 carbon atoms and may be the same or different. R 'is a monovalent hydrocarbon group such as methyl, ethyl and n-propyl. n is an integer selected from 0, 1, 2, and 3.

More specifically, tetraalkoxysilanes such as orthomethyl silicate, orthoethyl silicate and ortho n-propyl silicate and their partially hydrolyzed condensates, methyltrimethoxysilane, methyltriethoxysilane, phenyltrimethoxysilane Trialkoxysilanes such as silanes and partial hydrolysis condensates thereof, dimethyldimethoxysilane, phenylmethyldimethoxysilane, dialkoxysilanes such as diphenyldimethoxysilane, trimethylmethoxysilane, phenyldimethylmethoxysilane, triphenylmethoxysilane, etc. Monoalkoxysilane and the like. Among them, tetraethyl silicate is preferable, but these alkoxysilanes may be used alone or in combination of two or more.

The silicon compound used as the component (b) in the present invention contains at least one specific functional group,
And a silicon compound having at least two SiH groups, which imparts toughness and moldability in a thermosetting composite material obtained by blending the organic group-modified silicate of the present invention with a thermosetting resin and reacting the same. It is. Specific functional groups include carboxyl groups, acid anhydride groups, epoxy groups,
An amino group or a hydroxyl group is preferred, and an epoxy group is particularly preferred. The component (b) is not particularly limited, but if specifically exemplified.

[0010] And the like. In the formula, R represents one or more substituents selected from a methyl group, a phenyl group, and an alkyl group having 2 to 24 carbon atoms, preferably a methyl group, and l, m, and n represent 1 To 400. X is an organic chain containing at least one specific functional group selected from a carboxyl group, an acid anhydride group, an epoxy group, an amino group, and a hydroxyl group.

Also, In the formula, R represents a methyl group, a phenyl group, a carbon number of 2 to 24,
Represents one or more substituents selected from the alkyl groups of the above, preferably a methyl group, and l is 0 to 10
0 m is an integer from 1 to 400 n is an integer from 2 to 400. X is an organic chain containing at least one specific functional group selected from a carboxyl group, an acid anhydride group, an epoxy group, an amino group, and a hydroxyl group.

[0012] And the like, and a branched organic functional group-containing silicon compound. In the formula, R represents one or more substituents selected from a methyl group, a phenyl group and an alkyl group having 2 to 24 carbon atoms, preferably a methyl group, and n represents 0, 1,
Integer selected from 2,3. X is an organic chain containing at least one specific functional group selected from a carboxyl group, an acid anhydride group, an epoxy group, an amino group, or a hydroxyl group.

The method for introducing the functional group into the silicon compound is not particularly limited. For example, at least one specific group selected from a carboxyl group, an acid anhydride group, an epoxy group, an amino group, or a hydroxyl group. An organic compound having a functional group and containing an alkenyl group in the molecule;
A method of introducing a functional group by mixing a silicon compound having two SiH groups and causing a hydrosilylation reaction between the alkenyl group and the SiH group. in this case,
Preferably, the reaction conditions are such that at least two or more SiH groups remain after the reaction.

The mixing ratio of the components (a) and (b) used in the present invention is a very important index for controlling the characteristics of the obtained organic group-modified silicate. The weight ratio of (a) and (b) is preferably from 95: 5 to 70:30, more preferably from 95: 5 to 80:20, even more preferably from 90:10 to 80:20. If the compounding ratio of (a) is less than 5%, the number of functional groups is small, so that there is a tendency that sufficient organic group modification cannot be performed, and the obtained organic group-modified silicate tends not to have sufficient flexibility. On the other hand, if it is larger than 30%, the resulting organic group-modified silicate tends to be too soft, resulting in insufficient strength.

A catalyst may be used for the hydrolysis / condensation reaction of the alkoxysilyl group and the SiH group. As a catalyst,
There is no particular limitation, and known silanol condensation catalysts such as inorganic acids such as hydrochloric acid and sulfuric acid, tin carboxylate salts such as dibutyltin dilaurate and dibutyltin maleate, and inorganic bases such as sodium hydroxide and calcium hydroxide. Is mentioned. These catalysts may be used alone or in combination of two or more.

In order to obtain desired characteristics, the organic group-modified silicate of the present invention is prepared by converting the basic components of the alkoxysilanes (a), the functional group-containing silicon compound (b), the catalyst, water and the like into a homogeneous system as much as possible. It is desirable to make the reaction under close conditions. When the reaction is carried out in a heterogeneous state of the reaction system, the concentration of each component is locally increased, and partial gelation occurs, often resulting in only a heterogeneous material. Therefore, a solvent can be used as needed for the improvement of the uniformity of the above components, and further for controlling the reaction temperature.
There is no particular limitation.

As an example of a method for obtaining the thermosetting resin composite material of the present invention, first, under a temperature condition of 50 to 100 ° C.,
A solution of the silicon compound (b) is added dropwise to the alkoxysilanes (a) with a catalyst, if necessary, over a period of about 1 hour with good stirring, and further reacted for 1 to 3 hours to produce an organic group-modified silicate containing a functional group. I do. Next, to the obtained silicate containing a specific functional group, a solution of an organic solvent in which a thermosetting resin having two or more functional groups capable of reacting with this functional group is added, and the mixture is stirred and mixed. Is removed under reduced pressure and then heat-treated to obtain a thermosetting resin composite material. The heat treatment conditions are 70 ° C. to 180 ° C.
For 1 to 5 hours.

As the thermosetting resin used as the component (c) of the present invention, known thermosetting resins can be used as long as they have two or more functional groups in the molecule that can react with the functional groups of the organic group-modified silicate. Can be used. Examples of the functional group capable of reacting with the functional group of the organic group-modified silicate include a hydroxyl group, an amino group, an epoxy group, a carboxyl group, a mercapto group, and an isocyanate group, and among them, those having an epoxy group, a hydroxyl group, or an amino group preferable. Specific examples include a phenol resin, a urea resin, a melamine resin, and an epoxy resin.

The functional group equivalent of the organic group modified silicate and the thermosetting resin (b) / functional group equivalent of the organic group modified silicate in the thermosetting resin capable of reacting with the functional group of the organic group modified silicate (a) ) Is preferably within the range of 0.1 ≦ functional group equivalent (b) / functional group equivalent (a) ≦ 10, particularly 0.2 ≦ functional group equivalent (b) / functional group equivalent (a) ≦ 7. More preferably, 0.5 ≦ functional group equivalent (b) / functional group equivalent (a) ≦ 5, and still more preferably, 1 ≦ functional group equivalent (b) /
Functional group equivalent (a) ≦ 4, most preferably 1.5 ≦ functional group equivalent (b) / functional group equivalent (a) ≦ 3.

When the functional group equivalent ratio is less than 0.1, the ratio of the thermosetting resin becomes low, so that the fluidity and moldability tend to decrease. The dispersibility of the silicate powder tends to decrease because the amount of thermosetting resin having no bond tends to increase,
Various properties of a cured product obtained by crosslinking the resin composition tend to decrease. When the thus obtained thermosetting resin composite material of the present invention is blended with a conventionally known epoxy resin, a resin composition for a phenolic resin-based molding material, and the like, and cured, the composition has strength and impact resistance. Significant improvements in heat resistance, heat resistance, moldability, etc. can be achieved. The following can be considered as a reason for this.

That is, the thermosetting resin composite material of the present invention comprises:
Because the thermosetting resin itself is fixed to the silicate, the silicate is dispersed more evenly in advance than the conventional thermosetting resin composition when blended into the composition. Can be easily increased. Further, in the conventional thermosetting resin, the organic resin and the inorganic filler are hardly dispersed because of their low affinity, and since each is present independently, an external force such as thermal stress is applied. In this case, destruction occurs at the interface between the resin and the inorganic filler, which is the weakest part mechanically, and the properties cannot be sufficiently improved, but the novel thermosetting resin composite material of the present invention has a silicate surface. Since the thermosetting resin itself is immobilized, the interface between the silicate and the thermosetting resin is strong, and the affinity between the two is good, so that the thermosetting resin composite material of the present invention is used. It is considered that various properties of the thermosetting resin composition used were improved.

[0022]

The present invention will be described below with reference to examples. <Containing a specific functional group and having at least two S
Synthesis of iH group-containing silicon compound>

(Silicon Compound 1) A polymethyl hydrogen siloxane (SH1107 manufactured by Dow Corning Toray Silicone Co., Ltd.) is placed in a flask whose inside is replaced with nitrogen.
100.7 g and 100 ml of dry toluene were charged. Then, with stirring, The flask was immersed in an oil bath at 70 ° C., allyl glycidyl ether 11.2g and chloroplatinic acid catalyst solution (the _{H 2 PtCl 6 · 6H 2 O} 1.0g those that have been dissolved in isopropanol 9 g) and 300μl 100m of toluene
1 was added dropwise over about 1 hour. About one more
The reaction was carried out at 70 ° C. for a time to obtain a solution of silicon compound 1 containing a functional group.

(Silicon Compound 2) A polymethyl hydrogen siloxane (SH1107 manufactured by Dow Corning Toray Silicone Co., Ltd.) is placed in a flask whose inside is replaced with nitrogen.
220.3 g and 100 ml of dry 1,4-dioxane were charged. Then, with stirring, The flask was immersed in an oil bath at 70 ° C., allyl glycidyl ether 9.2g and chloroplatinic acid catalyst solution (the _{H 2 PtCl 6 · 6H 2 O} 1.0g those that have been dissolved in isopropanol 9 g) and 300μl A solution dissolved in 100 ml of toluene was added dropwise over about 1 hour.
The reaction was further performed at 70 ° C. for about 1 hour to obtain a solution of silicon compound 1 containing a functional group.

(Silicon compound 3) A polymethyl hydrogen siloxane (SH1107 manufactured by Dow Corning Toray Silicone Co., Ltd.) is placed in a flask whose inside is replaced with nitrogen.
118.2 g and dry 1,4-dioxane 100 ml were charged. Then, with stirring, The flask was immersed in an oil bath at 70 ° C., allyl glycidyl ether 41.3g and chloroplatinic acid catalyst solution (the _{H 2 PtCl 6 · 6H 2 O} 1.0g those that have been dissolved in isopropanol 9 g) and 300μl A solution dissolved in 100 ml of toluene was added dropwise over about 1 hour. The reaction was further performed at 70 ° C. for about 1 hour to obtain a solution of silicon compound 1 containing a functional group.

(Silicon Compound 4) A polymethyl hydrogen siloxane (SH1107, manufactured by Dow Corning Toray Silicone Co., Ltd.) is placed in a flask in which the system is purged with nitrogen.
32.3 g and 100 ml of dry 1,4-dioxane were charged. Then, with stirring, The flask was immersed in an oil bath at 70 ° C., allyl glycidyl ether 10.8g and chloroplatinic acid catalyst solution (the _{H 2 PtCl 6 · 6H 2 O} 1.0g those that have been dissolved in isopropanol 9 g) and 300μl A solution dissolved in 100 ml of toluene was added dropwise over about 1 hour.
The reaction was further performed at 70 ° C. for about 1 hour to obtain a solution of silicon compound 1 containing a functional group.

(Silicon compound 5) A polymethyl hydrogen siloxane (SH1107 manufactured by Dow Corning Toray Silicone Co., Ltd.) is placed in a flask in which the system is replaced with nitrogen.
289.8 g and 100 ml of dry 1,4-dioxane were charged. Then, with stirring, The flask was immersed in an oil bath at 70 ° C., allyl glycidyl ether 8.6g and chloroplatinic acid catalyst solution (the _{H 2 PtCl 6 · 6H 2 O} 1.0g those that have been dissolved in isopropanol 9 g) and 300μl A solution dissolved in 100 ml of toluene was added dropwise over about 1 hour.
The reaction was further performed at 70 ° C. for about 1 hour to obtain a solution of silicon compound 1 containing a functional group.

<Thermosetting Composite Material 1> With the inside of the system replaced with nitrogen, 1006 g of ethyl silicate was added dropwise to the solution of silicon compound 1 in an oil bath heated to 70 ° C., and the mixture was stirred at 0.5 N HCl aqueous solution (30 ml) in 1,4-
The solution dissolved in 10 ml of dioxane was stirred for about 1 hour.
The dripping was completed over time. Thereafter, the reaction was further continued for about 1 hour, and the solvent was removed under reduced pressure to prepare an organic group-modified silicate. 450 g of the above organic group-modified silicate, phenol novolak resin (PR-5 manufactured by Sumitomo Durez Co., Ltd.)
1470; 50 g of OH equivalent 105) and 1 g of triphenylphosphine as a catalyst were added, and then charged into a small Henschel mixer, and further reacted at a temperature of 80 ° C to 150 ° C for 1 to 3 hours while stirring at 500 to 700 rpm. The thermosetting resin composite material of the present invention was obtained. The obtained thermosetting resin composite material is subjected to infrared absorption spectrum and solid-state NMR.
As a result, it was confirmed that the hydroxyl group of the phenol resin was reacted with the epoxy group of the organic group-modified silicate. Here, when the functional group equivalent of the hydroxyl group of this thermosetting resin composite material was examined, it was 1086.3.

<Thermosetting Composite Material 2> With the inside of the system replaced with nitrogen, 600 g of ethyl silicate was dropped into the solution of silicon compound 2 and stirred in an oil bath heated to 70 ° C. The dropwise addition was completed over about 1 hour while stirring a solution of 30 ml of an aqueous HCl solution in 10 ml of 1,4-dioxane. Thereafter, the reaction was further continued for about 1 hour, and the solvent was removed under reduced pressure to prepare an organic group-modified silicate. 450 g of the above organic group-modified silicate, phenol novolak resin (PR-51 manufactured by Sumitomo Durez Co., Ltd.)
470; 50 g of OH equivalent 105), and 1 g of triphenylphosphine as a catalyst, and then charged into a small Henschel mixer, and further reacted at a temperature of 80 ° C to 150 ° C for 1 to 3 hours while stirring at 500 to 700 rpm. The thermosetting resin composite material of the present invention was obtained. The obtained thermosetting resin composite material is subjected to infrared absorption spectrum and solid-state NMR.
As a result, it was confirmed that the hydroxyl group of the phenol resin was reacted with the epoxy group of the organic group-modified silicate. Here, when the functional group equivalent of the hydroxyl group of this thermosetting resin composite material was examined, it was 1073.8.

<Thermosetting Composite Material 3> 507.2 g of ethyl silicate was added dropwise to the solution of silicon compound 3 in an oil bath heated to 70 ° C. while the inside of the system was replaced with nitrogen. 30 ml of a 5N HCl aqueous solution was added to 1,4
Dropping was completed over about 1 hour while stirring the solution dissolved in 10 ml of dioxane. Thereafter, the reaction was further continued for about 1 hour, and the solvent was removed under reduced pressure to prepare an organic group-modified silicate. After mixing 450 g of the above-mentioned organic group-modified silicate, 50 g of phenol novolak resin (PR-51470, manufactured by Sumitomo Durez Co., Ltd .; OH equivalent: 105), and 1 g of triphenylphosphine as a catalyst, the mixture was charged into a small Henschel mixer and charged at 500 to 700 rpm. The mixture was further reacted at a temperature of 80 ° C. to 150 ° C. for 1 to 3 hours while stirring to obtain a thermosetting resin composite material of the present invention. The obtained thermosetting resin composite material was subjected to infrared absorption spectrum, solid NM
As a result of checking with R, it was confirmed that the hydroxyl group of the phenol resin and the epoxy group of the organic group-modified silicate reacted. Here, when the functional group equivalent of the hydroxyl group of this thermosetting resin composite material was examined, it was 1306.5.

<Thermosetting Composite Material 4> ((a) / {(a) + (b)})
When the weight ratio of is less than 0.05) In a state where the inside of the system is replaced with nitrogen, 1034 g of ethyl silicate is added dropwise to the solution of silicon compound 4 in an oil bath heated to 70 ° C., and the mixture is stirred at 0.5 N HCl aqueous solution 3
Dropping was completed in about 1 hour while stirring a solution of 0 ml in 10 ml of 1,4-dioxane. afterwards,
The reaction was further continued for about 1 hour, and the solvent was removed under reduced pressure to produce an organic group-modified silicate. 450 g of the above organic group-modified silicate, phenol novolak resin (PR-51470, manufactured by Sumitomo Durez Co., Ltd .; OH equivalent: 105) 50
g, 1 g of triphenylphosphine as a catalyst, and then charged into a small Henschel mixer,
While stirring at 0 rpm, the temperature is further increased to 80 ° C to 150 ° C.
For 1 to 3 hours to obtain a thermosetting resin composite material of the present invention. The obtained thermosetting resin composite material was checked by infrared absorption spectrum and solid-state NMR. As a result, it was confirmed that the hydroxyl group of the phenol resin and the epoxy group of the organic group-modified silicate reacted. Here, when the functional group equivalent of the hydroxyl group of this thermosetting resin composite material was examined, 1083.
It was 6.

<Thermosetting Composite Material 5> ((a) / {(a) + (b)})
When the weight ratio of is not less than 0.3) 557.1 g of ethyl silicate was added dropwise to the solution of the silicon compound 3 in an oil bath heated to 70 ° C. while the atmosphere in the system was replaced with nitrogen, and the mixture was stirred. The dropwise addition was completed over about 1 hour while stirring a solution of 30 ml of a 0.5N HCl aqueous solution in 10 ml of 1,4-dioxane. Thereafter, the reaction was further continued for about 1 hour, and the solvent was removed under reduced pressure to prepare an organic group-modified silicate. 450 g of the above organic group-modified silicate, phenol novolak resin (PR-51470, manufactured by Sumitomo Durez Co., Ltd .; OH equivalent: 105) 50
g, 1 g of triphenylphosphine as a catalyst, and then charged into a small Henschel mixer,
While stirring at 0 rpm, the temperature is further increased to 80 ° C to 150 ° C.
For 1 to 3 hours to obtain a thermosetting resin composite material of the present invention. The obtained thermosetting resin composite material was checked by infrared absorption spectrum and solid-state NMR. As a result, it was confirmed that the hydroxyl group of the phenol resin and the epoxy group of the organic group-modified silicate reacted. Here, when the functional group equivalent of the hydroxyl group of this thermosetting resin composite material was examined, it was 1070.
It was 0.

<< Examples 1-3 and Comparative Examples 1-4 >>
The mixing raw materials shown in Table 3 were mixed, kneaded and pulverized to obtain an epoxy resin molding material, and the molding material was subjected to transfer molding to obtain a molded product. The evaluation results of the molded products are also
The results are shown in Table 3. In addition, the characteristic evaluation of the obtained molded article was performed by the following method. (1) Heat cycle: A copper plate of 25 × 25 × 3 mm is embedded in the bottom of a molded product of 30 × 25 × 5 mm, and the temperature is -40 ° C.
And + 200 ° C. for about 30 minutes, and after 100 cycles, resin cracks were examined. (2) Flexural strength: measured according to JIS K6911. (3) Spiral flow: Measured at about 175 ° C. and 70 kg / cm 2 using a mold conforming to the EMMI standard. (4) Molded appearance (the molded article surface was visually judged. A circle indicates that the surface of the molded article is smooth, and a cross indicates that the irregularity occurs.)

[0034]

[Table 1]

[0035]

[Table 2]

[0036]

[Table 3]

[0037]

According to the present invention, by blending and reacting with a resin, excellent heat resistance and combustion resistance, high mechanical strength such as bending characteristics, good high toughness, thermal shock resistance, and moldability are obtained. And an organic group-modified silicate from which a thermosetting resin composite material having the following is obtained, and a thermosetting composite material containing the silicate as a component.

Claims (7)

[Claims] 1. A reaction system comprising an alkoxysilane (a) and a silicon compound (b) containing at least one specific functional group and having at least two SiH groups in a molecule. An organic group-modified silicate, characterized in that: 2. The organic group-modified silicate according to claim 1, wherein the specific functional group is a carboxyl group, an acid anhydride group, an epoxy group, an amino group, or a hydroxyl group. 3. The method according to claim 1, wherein the reaction is an alkoxysilyl group,
The organic group-modified silicate according to claim 1 or 2, which is a hydrolysis and condensation reaction of an iH group. 4. The organic group-modified silicate according to claim 1, wherein the alkoxysilane (a) is tetraethyl silicate. 5. A silicon compound (b) containing a specific functional group and having at least two SiH groups in a molecule.
5. The organic group-modified silicate according to claim 1, wherein is a polymethylhydrogensiloxane derivative containing an epoxy group. 6. The weight ratio of (a) to (b) is 95: 5 to 5.
6. The organic group-modified silicate according to claim 1, wherein the ratio is 70:30. 7. A method of mixing and reacting a thermosetting resin (c) having two or more functional groups capable of reacting with the organic group-modified silicate according to claim 1, 2, 3, 4, 5, or 6. A thermosetting resin composite material obtained.