NOVEL ORGANOPOLYSILOXANE, THERMOSETTING RESIN ADDITIVE COMPRISING THE SAME, AND THERMOSETTING RESIN COMPOSITION COMPRISING THE SAME

TECHNICAL FIELD

[0001] The present invention relates to a novel organopolysiloxane, a thermosetting resin additive comprising the same, and a thermosetting resin composition comprising the same. Priority is claimed on Japanese Patent Application No. 2012-101221 filed on April 26, 2012, the content of which are incorporated herein by reference.

BACKGROUND ART

[0002] Thermosetting resin compositions such as epoxy resins and the like find application as sealing, adhesive, and other agents used in the manufacture of electrical and electronic parts. However, the use of these compositions is associated with problems, such as low modulus of elasticity, and hence high rigidity, of cured products obtained from these compositions. As a result, stress is prone to be generated in electrical and electronic parts due to expansion and contraction when the aforementioned compositions are used. Therefore, various additives are added to thermosetting resin compositions in order to mitigate the internal stress in the cured body.

[0003] For example, Japanese Unexamined Patent Application Publication Nos. 2006-269730 and 2005-15559 disclose sealing epoxy resin molding materials comprising a silicone-containing polymer having an epoxy group as such additives. However, compatibility of such a silicone-containing polymer having an epoxy group in the resin composition is insufficient, and reactivity with the epoxy resin is low. Thus, there have been problems in that bleeding out occurs when a large amount of the additive is added. Furthermore, there is a problem in that variations in the characteristics of the resin are seen if the content of the epoxy groups is increased in order to enhance compatibility and reactivity.

[0004] As a solution to this problem, using an amino group-containing organopolysiloxane as an additive to a thermosetting resin composition has been proposed. For example, Japanese Unexamined Patent Application Publication No. 2011-152196 discloses an epoxy resin composition for sealing semiconductors comprising a reaction product of a higher fatty acid and a primary amino group-containing polysiloxane as a release agent. Moreover, Japanese Examined Patent Application Publication S62-27095 discloses an epoxy resin composition comprising an organopolysiloxane having a primary amino group-containing organic group.

[0005] However, in cases where these primary amino group-containing organopolysiloxanes are used, there is a problem in that the effects of reducing internal stress in the cured resin are insufficient. Furthermore, there is a problem in that the thermosetting resin gelates prior to molding. [0006] Additionally, organopolysiloxanes having secondary amino groups have been proposed. For example, Japanese Unexamined Patent Application Publication Nos. 2008-285552 and 2008-285553 disclose curable epoxy resin compositions comprising crosslinking silicone particles having aryl groups or aralkyi groups and secondary amino groups, and a mixture of said crosslinking silicone particles and an epoxy resin and an epoxy resin curing agent.

[0007] However, crosslinking silicone particles have fine pores and, thus, there is a problem in that the hygroscopicity of the obtained cured product is high. Additionally, there is a problem in that shrinkage ratio is high when curing the composition.

[0008] An example of a non-crosslinked secondary amino group-containing organopolysiloxane is disclosed in Japanese Unexamined Patent Application Publication No. H03-157453 as a primer composition comprising an organopolysiloxane obtained by a reaction with a silane having an anilino group. However, the ratio of Si0 _4/2 units in this organopolysiloxane is high and, thus, there are problems such as the effects of reducing internal stress in the cured resin being insufficient and the shrinkage ratio being high when curing. Additionally, there is no disclosure of using a mixture of the organopolysiloxane and a thermosetting resin and, thus, compatibility with thermosetting resins and other characteristics are not clearly shown.

PRIOR ART DOCUMENTS

[0009] Patent Document 1 : Japanese Unexamined Patent Application Publication No.

2006-269730A

Patent Document 2: Japanese Unexamined Patent Application Publication No. 2005-015559A Patent Document 3: Japanese Unexamined Patent Application Publication No. 2011-152196A Patent Document 4: Japanese Examined Patent Application Publication No. S62-027095

Patent Document 5: Japanese Unexamined Patent Application Publication No. 2008-285552A Patent Document 6: Japanese Unexamined Patent Application Publication No. 2008-285553A Patent Document 7: Japanese Unexamined Patent Application Publication No. H03-157453A

DISCLOSURE OF INVENTION

Technical Problem

[0010] In light of the problems described above, an object of the present invention is to provide a novel organopolysiloxane having superior compatibility with thermosetting resins and superior reactivity with thermosetting resins, and a thermosetting resin additive comprising the

organopolysiloxane. Another object is to provide a thermosetting resin composition that is free of problems such as bleeding out and the like and that has low curing shrinkage ratio.

Solution To Problem

[0011] As a result of intensive investigation aimed at achieving the above objects, the present inventors arrived at the present invention. That is, the object of the present invention is achieved by an organopolysiloxane represented by the average unit formula:

(R ¹ Si03/ ₂ )a(R ² R ³ Si0 _2/2 ) _b (R ⁴ R ⁵ R ⁶ SiO _1/2 ) _c (Si0 ₄ / ₂ ) _d (wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , and R ⁶ are each identical or differing monovalent hydrocarbon groups, halogen-substituted monovalent hydrocarbon groups, or secondary amino

group-containing organic groups having nitrogen atom-bonded aromatic rings; and from 0.1 to 70 mol% of the total number of moles of the R to R ⁶ moieties is constituted by the secondary amino group-containing organic groups);

"a" to "d" satisfying the following relationships:

0<a, 0<b, 0<c, 0<d≤0.3, 0.01<b/a<10, 0≤c/a≤0.8, and a+b+c+d=1.

[0012] The organopolysiioxane preferably comprises aryl groups having from 6 to 20 carbons at an amount of not less than 5 mol% of the total number of moles of the R ¹ to R ⁶ moieties.

[0013] The organopolysiioxane preferably comprises alkyl groups having from 1 to 20 carbons at an amount of not less than 10 mol% of the total number of moles of the R ¹ to R ⁶ moieties.

[0014] The organopolysiioxane preferably comprises secondary amino group-containing organic groups having nitrogen atom-bonded aromatic rings at an amount of not less than 5 mol% of the total number of moles of the R ¹ to R ⁶ moieties.

[0015] The secondary amino group-containing organic groups having nitrogen atom-bonded aromatic rings are preferably groups represented by the following formula:

-R ⁷ -(NR ⁸ CH ₂ CH ₂ ) _e -NH-R ⁹

(wherein, "e" is an integer not less than 0; R ⁷ is a divalent hydrocarbon group; R ⁸ is a hydrogen atom, a monovalent hydrocarbon group, an acyl groups, or a group represented by the formula: -CH ₂ CH(OH)R ¹⁰ (wherein, R ¹⁰ is a monovalent organic group); and R ⁹ is a monovalent hydrocarbon group or an acyl group; provided that at least one of R ⁸ and R ⁹ is an aryl group and when "e" is 0, R ⁹ is an aryl group).

[0016] A weight average molecular weight of the organopolysiioxane is preferably in a range from 500 to 50,000.

[0017] The present invention is also related to a thermosetting resin additive comprising the organopolysiioxane described above.

[0018] The present invention is also related to a thermosetting resin composition comprising a thermosetting resin, a curing agent, and the thermosetting resin additive described above.

[0019] The thermosetting resin additive is preferably comprised at an amount of from 0.1 to 500 parts by mass per a total 100 parts by mass of the thermosetting resin and the curing agent.

[0020] The thermosetting resin is preferably an epoxy resin.

[0021] The curing agent is preferably a phenolic resin.

[0022] The thermosetting resin composition of the present invention can further comprise an inorganic filler.

Advantageous Effects of Invention

[0023] According to the present invention, an organopolysiioxane having superior compatibility with epoxy resins and similar thermosetting resins and superior reactivity, and a thermosetting resin additive comprising this organopolysiloxane can be provided.

[0024] Additionally, with a thermosetting resin composition comprising the thermosetting resin additive of the present invention, internal stress in cured resin can be mitigated and formability can be improved. Furthermore, warping and similar deformations of the cured resin can be suppressed.

DETAILE DESCRIPTION OF THE INVENTION

[0025] An organopolysiloxane of the present invention is represented by the average unit formula:

(R Si03,2) _a (R ² R ³ Si0 _2/2 ) _b (R R ⁵ R ⁶ Si0 _1/2 ) _c (Si0 ₄ /2)d

. In this formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , and R ⁶ are each identical or differing monovalent hydrocarbon groups, halogen-substituted monovalent hydrocarbon groups, or secondary amino group-containing organic groups having nitrogen atom-bonded aromatic rings; and from 0.1 to 70 mol% of the total number of moles of the R to R ⁶ moieties is constituted by the secondary amino group-containing organic groups; and

"a" to "d" satisfy the following relationships:

0<a, 0<b,

0<c, 0<d<0.3, 0.01≤b/a<10, 0≤c/a≤0.8, and a+b+c+d=1.

[0026] Examples of the R ¹ to R ⁶ monovalent hydrocarbon group moieties in the

organopolysiloxane of the present invention include methyl groups, ethyl groups, propyl groups, butyl groups, pentyl groups, hexyl groups, heptyl groups, and similar alkyl groups; vinyl groups, allyl groups, butenyl groups, pentenyl groups, hexenyl groups, and similar alkenyl groups; phenyl groups, tolyl groups, xylyl groups, naphthyl groups, and similar aryl groups; benzyl groups, phenethyl groups, and similar aralkyl groups; and chloromethyl groups, 3-chloropropyl groups, 3,3,3-trifluoropropyl groups, nonafluorobutyl ethyl groups, and similar substituted alkyl groups.

[0027] The organopolysiloxane of the present invention preferably comprises aryl groups having from 6 to 20 carbons at an amount of not less than 5 mol% and more preferably comprises aryl groups having from 6 to 20 carbons at an amount of from 20 to 70 mol% of the total number of moles of the R ¹ to R ⁶ moieties. Examples of the aryl groups include phenyl, tolyl, xylyl, and naphthyl groups. The aryl groups are preferably phenyl groups or naphthyl groups.

[0028] The organopolysiloxane of the present invention preferably comprises alkyl groups having from 1 to 20 carbons at an amount of not less than 0 mol% and more preferably comprises alkyl groups having from 1 to 20 carbons at an amount from 5 to 80 mol% of the total number of moles of the R ¹ to R ⁶ moieties. Examples of the alkyl groups include methyl groups, ethyl groups, propyl groups, butyl groups, pentyl groups, hexyl groups, heptyl groups, octyl groups, decyl groups, and dodecyl groups. The alkyl groups are preferably methyl groups or ethyl groups.

[0029] The organopolysiloxane of the present invention preferably comprises secondary amino group-containing organic groups having nitrogen atom-bonded aromatic rings at an amount of not less than 5 mol% and more preferably comprises secondary amino group-containing organic groups having nitrogen atom-bonded aromatic rings at an amount from 5 to 40 mol% of the total number of moles of the R to R ⁶ moieties. Because of including the secondary amino group-containing organic groups, the thermosetting resin additive of the present invention has superior compatibility with thermosetting resins even in cases where the R ¹ to R ⁶ moieties do not include aryl groups.

[0030] The secondary amino group-containing organic groups having nitrogen atom-bonded aromatic rings are preferably groups represented by the following formula:

-R ⁷ -(NR ⁸ CH ₂ CH ₂ ) _e -NH-R ⁹

In this formula, "e" is an integer not less than 0; R ⁷ is a divalent hydrocarbon group; R ⁸ is a hydrogen atom, a monovalent hydrocarbon group, an acyl groups, or a group represented by the formula: -CH ₂ CH(OH)R ¹⁰ (wherein, R ¹⁰ is a monovalent organic group); and R ⁹ is a monovalent hydrocarbon group or an acyl group; provided that at least one of R ⁸ and R ⁹ is an aryl group and when "e" is 0, R ⁹ is an aryl group.

Examples of the divalent hydrocarbon group include methylene, ethylene, propylene, butylene, hexene, and similar alkylene groups having from 1 to 10 carbons. Additionally, the monovalent hydrocarbon group is synonymous with the groups recited for the R ¹ to R ⁶ moieties. Examples of the monovalent organic group include the monovalent hydrocarbon group and groups wherein a portion or all of the carbon-bonded hydrogen atoms in the monovalent hydrocarbon group are substituted with cyano groups, epoxy groups, or the like. Additionally, a small amount of silicon-bonded hydrogen atoms, hydroxyl groups, or alkoxy groups may be comprised.

[0031] With the organopolysiloxane of the present invention, a small portion of the R ¹ to R ⁶ moieties may be hydroxyl groups or alkoxy groups having from 1 to 20 carbons. In this case, preferably less than 40 mol% and more preferably less than 10 mol% of the total number of moles of the R to R ⁶ moieties are hydroxyl groups or alkoxy groups.

[0032] In the organopolysiloxane of the present invention, "a" is preferably from 0.10 to 0.95 and more preferably is from 0.20 to 0.90. "b" is preferably from 0.05 to 0.80 and more preferably from 0. 0 to 0.75. b+c is preferably from 0.05 to 0.85 and more preferably from 0.10 to 0.80. Preferably, d=0.

[0033] The organopolysiloxane of the present invention preferably has a weight average molecular weight in a range from 500 to 50,000 and more preferably has a weight average molecular weight in a range from 1 ,000 to 10,000 when measured by gel permeation

chromatography (GPC) in a 1 mass.% toluene solution.

[0034] The organopolysiloxane of the present invention preferably is soluble in toluene at 25°C. Here, "soluble" means that 1 mass.% or more of the organopolysiloxane dissolves in toluene, and "dissolve" means that residue is not visually identifiable after adding 1 g of the organopolysiloxane to 99 g of toluene and stirring for 10 minutes at 25°C. If the organopolysiloxane has a crosslinked or gelled structure or has an excessive amount of siloxane units represented by (Si0 ₄ / ₂ ), the organopolysiloxane will be insoluble in toluene.

Organopolysiloxanes that are insoluble in toluene have problems such as the effects of reducing internal stress in the cured resin being insufficient and the shrinkage ratio being high when curing.

[0035] Preferably, in the organosiloxane of the present invention, contents of potassium and sodium are not greater than 0.1 ppm, content of chlorine is not greater than 5 ppm, and contents of uranium and thorium are not greater than 1 ppb. This is because there is a possibility that the moisture-resistant properties in high-temperature/high-humidity environments of a sealed or bonded semiconductor will be inhibited if the content of chlorine or the contents of sodium and potassium exceed the upper limits described above.

[0036] While the organopolysiloxane of the present invention may be produced according to conventional methods, it may also be produced according to the method described below.

[0037] In the presence of a basic catalyst, react (I) one type or a mixture of two or more types of siloxanes having at least one type of unit selected from the group consisting of (i) a unit represented by the formula: R ¹¹ Si0 ₃ / ₂ (wherein R ¹ is a monovalent hydrocarbon group), (ii) a unit represented by the formula: R ² R ³ Si0 ₂ /2 (wherein R ² and R ³ are identical or different monovalent hydrocarbon groups), (iii) a unit represented by the formula: R ⁴ R ¹⁵ R ⁶ Si0 _1/2 (wherein R ¹⁴ , R ¹⁵ , and R ⁶ are identical or different monovalent hydrocarbon groups), and (iv) a unit represented by the formula: Si0 _4/2 ; or, alternatively, at least one alkoxysilane or a mixture of two or more alkoxysilanes selected from the group consisting of trialkoxy organosilane, dialkoxy diorganosilane, monoalkoxy triorganosilane, and tetraalkoxysilane; and

(II) a secondary amino group-containing alkoxysilane represented by the general formula:

R ¹⁷ R ¹⁸ _f Si(OR ¹⁹ ) ₍₃ _ _f) (wherein R ¹⁷ is a secondary amino group-containing organic group, R ¹⁸ is a monovalent hydrocarbon group, R ²⁰ is an alkyl group, and "f is 0, 1 , or 2), or a partial hydrolysate thereof.

[0038] In the production method described above, the component (I) is the main starting material and is constituted by the one type or the mixture of two or more types of siloxanes having at least one type of unit selected from the group consisting of the units described as (i) to (iv) above or, alternatively, is the one type of alkoxysilane or the mixture of two or more types of alkoxysilanes. Examples of the component (I) include the siloxane consisting only of the unit described in (i), the siloxane consisting only of the unit described in (iii), the siloxane consisting only of the unit described in (iv), a siloxane consisting of the unit described in (i) and the unit described in (ii), a siloxane consisting of the unit described in (i) and the unit described in (iii), a siloxane consisting of the unit described in (i) and the unit described in (iv), a siloxane consisting of the unit described in (i), the unit described in (ii), and the unit described in (iii), a siloxane consisting of the unit described in (i), the unit described in (ii), and the unit described in (iv), and a siloxane consisting of the unit described in (i), the unit described in (ii), the unit described in (iii), and the unit described in (iv); trialkoxy organosilane, dialkoxy diorganosilane, a mixture of trialkoxy organosilane and dialkoxy diorganosilane; a mixture of trialkoxy organosilane, dialkoxy diorganosilane, and alkoxy triorganosilane; and a mixture of trialkoxy organosilane, dialkoxy diorganosilane, monoalkoxy triorganosilane, and tetraalkoxysilane. Note that in the formula, the R ¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , and R ¹⁶ moieties are identical or different monovalent hydrocarbon groups and examples thereof include methyl groups, ethyl groups, propyl groups, butyl groups, pentyl groups, hexyl groups, heptyl groups, and similar alkyl groups; vinyl groups, allyl groups, butenyl groups, pentenyl groups, hexenyl groups, and similar alkenyl groups; phenyl groups, tolyl groups, xylyl groups, naphthyl groups, and similar aryl groups; benzyl groups, phenethyl groups, and similar aralkyl groups; chloromethyl groups, 3-chloropropyl groups, 3,3,3-trifluoropropyl groups, nonafluorobutyl ethyl groups, and similar substituted alkyl groups. In this case, preferably 10 mol% or more and more preferably 30 mol% or more of the R ¹ moieties are phenyl groups. Additionally, examples of the silicon-bonded organic group in the alkoxysilanes are synonymous with the monovalent hydrocarbon groups described above for the R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , and R ¹⁶ moieties, and examples of the alkoxy groups include alkoxy groups having from 1 to 10 carbons.

[0039] The monovalent hydrocarbon groups in the component (II) are synonymous with the groups described for the R ¹¹ to R ¹⁶ moeities of component (I). Examples of the alkyl groups include methyl groups, ethyl groups, propyl groups, butyl groups, pentyl groups, hexyl groups, heptyl groups, octyl groups, decyl groups, and dodecyl groups.

[0040] Examples of the silane or the siloxane in the component (I) include methyl

trimethoxysilane, methyl triethoxysilane, ethyl trimethoxysilane, ethyl triethoxysilane, vinyl trimethoxysilane, phenyltrimethoxysilane, 3,3,3-trifluoropropyl trimethoxysilane, dimethyl dimethoxysilane, methylphenyl dimethoxysilane, methylvinyl dimethoxysilane, diphenyl dimethoxysilane, dimethyl diethoxysilane, methylphenyl diethoxysilane, tetramethoxysilane, tetraethoxysilane, tetrapropoxysilane, dimethoxy diethoxysilane, and hydrolysis/condensation reaction products thereof.

[0041] In the production method described above, the component (I) and the component (II) are reacted using a basic catalyst. The basic catalyst serves a purpose of co-hydrolyzing, co-condensing, and also equilibrating the component (I) and the component (II). Examples thereof include sodium hydroxide, potassium hydroxide, cesium hydroxide, and similar hydroxides of alkali metals; sodium-t-butoxide, potassium-t-butoxide, cesium-t-butoxide, and similar alkoxides of alkali metals; and sodium silanolate compounds, potassium silanolate compounds, cesium silanolate compounds, and similar silanol compounds of alkali metals. The basic catalyst is preferably a potassium or cesium basic catalyst. Additionally, as necessary, water may be added for the purpose of co-hydrolyzing or co-condensing the component (I) and the component (II). After reacting the component (I) and the component (II), the solid content concentration in the reaction system may, as necessary, be adjusted using an organic solvent, and the system may be further reacted.

[0042] In the production method described above, the siloxane bonds are randomly cleaved and re-bonded through the equilibrium reaction. As a result, the obtained epoxy group-containing silicone resin is in an equilibrium condition. If the reaction temperature is low, the equilibrium reaction will not progress sufficiently, and if the reaction temperature is excessively high, the silicon-bonded organic groups will pyrolyze. Therefore, the reaction temperature is preferably from 80°C to 200°C and more preferably from 100°C to 150°C. The equilibrium reaction can be carried out easily at reflux temperature by selecting an organic solvent having a boiling point from 80 to 200°C. Note that, the equilibrium reaction can be stopped by neutralizing the basic catalyst. Preferably, carbonic acid gas, carboxylic acid gas, or a similar weak acid is added to neutralize the basic catalyst. The salt produced as a result of the neutralization can be removed via filtration or water rinsing.

[0043] The present invention also relates to a thermosetting resin additive comprising an organopolysiloxane. The thermosetting resin additive of the present invention is characterized by comprising the organopolysiloxane of the present invention described above as said organopolysiloxane.

[0044] Additionally, the present invention also relates to a thermosetting resin composition comprising a thermosetting resin, a curing agent, and a thermosetting resin additive. The composition of the present invention is characterized by comprising the thermosetting resin additive of the present invention described above as said thermosetting resin additive.

[0045] The thermosetting resin additive comprised in the thermosetting resin composition of the present invention is preferably comprised at an amount of from 0.1 to 500 parts by mass per a total 100 parts by mass of the thermosetting resin and the curing agent.

[0046] Examples of the thermosetting resin comprised in the thermosetting resin composition of the present invention include epoxy resin, cyanate resin, phenolic resin, polyimide resin, and urethane resin. Of these, epoxy resins are preferable.

[0047] Examples of the epoxy resin include biphenyl type epoxy resins, bisphenol-A epoxy resins, bisphenol-F epoxy resins, stilbene epoxy resins, biphenyl-ether epoxy resins, and

biphenyl-sulphone epoxy resins. Of these, from the perspective of formability and

nonflammability, a crystalline epoxy resin is preferably and a biphenyl type epoxy resin is more preferable.

[0048] Examples of the biphenyl type epoxy resin include 4,4'-bis(2,3-epoxypropoxy)biphenyl, 4,4'-bis(2,3-epoxypropoxy)-3,3',5,5'-tetramethyl biphenyl,

4,4'-bis(2,3-epoxypropoxy)-3,3\5,5'-tetraethyl biphenyl, and 4,4'-bis(2,3-epoxypropoxy)-3,3',5,5'-tetrabutyl biphenyl. Such a biphenyl type epoxy resin is available as, for example, YX4000HK, manufactured by Yuka Shell Epoxy Co., Ltd.

[0049] The curing agent comprised in the thermosetting resin composition of the present invention preferably is a phenolic resin. Examples of the phenolic resin include phenol novolac type phenolic resins, cresol novolac type phenolic resins, resole type phenolic resins, triphenyl alkane type epoxy resins, dicyclopentadiene-modified phenolic resins, phenol aralkyl type phenolic resins, biphenol type phenolic resins, and naphthol aralkyl type phenolic resins.

[0050] Of these, from the perspective of nonflammability, a phenol aralkyl type phenolic resin is preferable. Such a phenol aralkyl type phenolic resin is available as, for example, Milex XLC-3L, manufactured by Mitsui Chemicals, Inc.

[0051] A content of the curing agent comprised in the thermosetting resin composition of the present invention is not particularly limited, but is an amount where a molar ratio of the phenolic hydroxyl groups in the phenolic resin to the epoxy groups in the epoxy resin is preferably from 0.5 to 2.5 and more preferably from 0.5 to 1.5. This is because if the curing agent is used in an amount less than the lower limit described above, the curing of the thermosetting resin composition will tend to be insufficient; and, if the content of curing agent exceeds the upper limit described above, strength of a cured product obtained from the composition will tend to decline.

[0052] The thermosetting resin composition of the present invention may further comprise an inorganic filler for the purpose of imparting mechanical strength and heat resistant properties and reducing expansion due to heat in the obtained cured product of the composition. A content of the inorganic filler in the thermosetting resin composition is preferably from 100 to 1 ,200 parts by mass, more preferably from 400 to 1 ,000 parts by mass, and even more preferably from 400 to 800 parts by mass per a total 100 parts by mass of the thermosetting resin and the curing agent. If the content of inorganic filler is less than the lower limit described above, the strength of the obtained cured product will tend to be insufficient.

[0053] Examples of the inorganic filler include fibrous fillers such as glass fiber, asbestos, alumina fiber, ceramic fiber having alumina and silica as components, boron fiber, zirconia fiber, silicon carbide fiber, and metal fiber; particulate fillers such as fused silica, crystalline silica, precipitated silica, fumed silica, baked silica, zinc oxide, baked clay, carbon black, glass beads, alumina, talc, calcium carbonate, clay, aluminum hydroxide, magnesium hydroxide, barium sulfate, titanium dioxide, aluminum nitride, boron nitride, silicon carbide, aluminium oxide, magnesium oxide, titanium oxide, beryllium oxide, kaolin, mica, zirconia, and the like; and mixtures of two or more thereof. The form of the inorganic filler is not particularly limited, and examples thereof include spherical, needle-like, flat, irregularly crushed shape, and the like. Of these, a spherical form is preferable. Particularly, from the perspective of formability and hygroscopicity, spherical fused silica having an average particle size of from 5 to 40 pm is preferable. [0054] Additionally, a silane coupling agent, titanate coupling agent, or similar coupling agent can be used for the purpose of enhancing dispersibility and adhesion of the inorganic filler with respect to the thermosetting resin. Examples of such silane coupling agents include

3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane,

2-(3,4-epoxycyclohexyl)ethyl trimethoxysilane, and similar epoxy group-containing

alkoxysilanes; N-(2-aminoethyl)-3-aminopropyl trimethoxysilane, 3-aminopropyl triethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, and similar amino group-containing alkoxysilanes; and 3-mercaptopropyltrimethoxysilane and similar mercapto group-containing alkoxysilanes.

Examples of the titanate coupling agent include i-propoxytitane tri(i-isostearate). A combination of two or more coupling agents may be used. The method of surface treating and the compounded amount of the coupling agent used in the surface treating are not limited.

[0055] The thermosetting resin composition of the present invention preferably further comprises a curing accelerator for the purpose of accelerating the curing. Examples of the curing accelerator include triphenylphosphine, tributylphosphine, tri(p-methylphenyl)phosphine, tri(nonylphenyl)phosphine, triphenylphosphine-triphenylborate,

tetraphenylphosphine-tetraphenylborate, and similar phosphorous compounds; triethylamine, benzyldimethylamine, a-methylbenzyldimethylamine, 1 ,8-diazabicyclo [5.4.0]undecene-7, and similar tertiary amine compounds; and 2-methylimidazol, 2-phenylimidazol,

2-phenyl-4-methylimidazol, and similar imidazole compounds.

[0056] An amount of the curing accelerator is not particularly limited, but is preferably within a range of 0.001 to 20 parts by mass per 100 parts by mass of the thermosetting resin. This is because if the content of the curing accelerator is less than the lower limit described above, accelerating the reaction of the thermosetting resin with the curing agent will tend to be difficult; and, if the content exceeds the upper limit described above, the strength of the obtained cured product will tend to decline.

[0057] As necessary, the thermosetting resin composition of the present invention may comprise a thermoplastic resin, a thermoplastic elastomer, an organic synthetic rubber, a silicone, or a similar stress relaxing agent; Carnauba wax, higher fatty acids, a synthetic wax, or a similar wax; carbon black or a similar coloring agent; a halogen trapping agent; and the like.

[0058] The method for preparing the thermosetting resin composition of the present invention is not particularly limited, and can be prepared by uniformly mixing the thermosetting resin additive with the thermosetting resin and the curing agent. Additionally, in cases where the inorganic filler is compounded as an optional component, an example of a preparation method is one in which the curing agent, the thermosetting resin additive component, and the other optional components are uniformly mixed after mixing the inorganic filler with the thermosetting resin. In this case, examples of methods include adding and integrally blending the coupling agent with the thermosetting resin and the inorganic filler, or surface treating the inorganic filler with the coupling agent beforehand and then mixing the surface treated inorganic filler with the thermosetting resin. Examples of devices for preparing the thermosetting resin composition of the present invention include single-screw or double-screw continuous kneaders, two-roll mills, Ross mixers, and kneader-mixers.

EXAMPLES

[0059] Hereinafter, examples will be used to describe the present invention in more detail, but the present invention is not limited to these examples. In the examples, the content of the components referred to as "parts" means "parts by mass". Moreover, "Ph" indicates a phenyl group, "Me" indicates a methyl group, and "Vi" indicates a vinyl group.

[0060] Melting point

The melting point of the organopolysiloxane was measured using the MEL-TEMP II,

manufactured by Laboratory Device, Inc.

[0061] Weight average molecular weight

The weight average molecular weight of the organopolysiloxane was measured via gel permeation chromatography (GPC), using a toluene solution having a sample concentration of 1 % and employing the use of an Rl detector; and is expressed as a value obtained by converting the molecular weight using the standard polystyrene calibration curve.

[0062] Viscosity

Viscosity at 25°C was measured using a rotational viscometer VG-DA (manufactured by Shibaura System Co., Ltd.).

[0063] Structure analysis

The structure of the organopolysiloxane was determined via ²⁹ Si-nuclear magnetic resonance spectroscopy (using the JNM-ECA500, manufactured by JEOL Ltd.).

[0064] Evaluation method of formability

(1 ) Spiral flow

Spiral flow was measured at a mold temperature of 175°C and under a molding pressure of 70 kgf/cm ² in accordance with the EMMI standard.

[0065] (2) Evaluation of mold contamination

Five disks having a diameter of 50 mm and a thickness of 2 mm were formed continuously by using a transfer pressing apparatus. Molding conditions were as follows. Mold temperature: 175°C, curing time: 2 minutes, molding pressure: 70 kgf/cm ² . Thereafter, the chrome-plated surface of the mold was checked for cloudiness. The evaluation was recorded as follow; Cases where cloudiness was not observed were indicated by "o", cases where light cloudiness was observed were indicated by "Δ", and cases where the surface of the mold was contaminated were indicated by

[0066] (3) Burr evaluation

Burr length at the time of molding was measured with a burr measurement mold (a groove having a depth of 20 μηι), using a transfer pressing apparatus under the following conditions: mold temperature: 175°C, curing time: 2 minutes, molding pressure: 70 kgf/cm ² . The evaluation was recorded as follow; Cases where the burr length was 2 mm or less were indicated by "o", cases where the burr length was greater than 2 mm and less than or equal to 10 mm were indicated by "Δ", and cases where the burr length was greater than 10 mm were indicated by "x".

[0067] (4) Shrinkage ratio

Four rodlike bodies were molded using a mold having a 1 x10^1/2 inch cavity at 25°C, and using a transfer pressing apparatus under the following conditions: mold temperature: 175°C, curing time: 2 minutes, molding pressure: 70 kgf/cm ² . The bodies were removed from the mold and a length (L _AM ) of the long edge of the samples after being cooled to 25°C and a length (L _PC ) of the long edge of the post-cured samples (180°C, 5 hours) were compared with a length (L ₀ ) of the long edge of the cavity of the mold at 25°C, and the shrinkage ratio(%) was calculated by the following formulae:

Curing shrinkage ratio

Curing shrinkage ratio (PC)=100x(Lp _C -Lo)/L ₀

Note that the shrinkage ratio prior to the post-curing is designated as "Curing shrinkage ratio (AM)" and the post-curing shrinkage ratio is designated as "Curing shrinkage ratio (PC)".

[0068] (5) Moisture absorption

A specimen was cut from the sample formed in said procedure in evaluation (3), post-cured for 5 hours at 180°C, and the weight of the specimen was precisely measured (W ₀ : about 5 g). The specimen was placed in a 50 cc pressure-cooker test (PCT) container along with 40 g of ion exchanged water, and was retained in a pressurized water vapor environment (121°C) for 20 hours. Then, the specimen was removed from the PCT container, water was wiped from the surface, and a weight (W^ thereof was measured. Moisture absorption was calculated according to the following formula:

Moisture Absorption (%): = 00x(W W ₀ )/Wo

[0069] Preparation of the organopolysiloxane

[Practical Example Π

100 g of phenylsilsesquioxane (217 FLAKE RESIN, manufactured by Dow Corning Toray Co., Ltd.) and 184 g of toluene were placed in a 500 ml flask provided with a thermometer, a

Dean-Stark apparatus, and a refluxing cooler and stirred until the system became uniform. 16.3 g of dimethyldimethoxysilane, 22.3 g of phenylaminopropyltrimethoxysilane, 10 g of ion exchanged water, and 0.13 g of cesium hydroxide were added to the system and co-hydrolyzed while applying heat. Then, excess water was removed by distillation and the system was heated to reflux for 4 hours. The system was cooled, and then 1 g of acetic acid was added to neutralize the system. Thereafter, the generated salt was removed by filtration, and then the toluene was removed by heating the filtrate under reduced pressure. Thus, 132 g of a white solid was obtained. The solid was determined via Si-nuclear magnetic resonance spectroscopic analysis to be a phenylamino group-containing organopolysiloxane represented by the average structural formula:

(Me2Si02/2)o.i4(Ph HC3H ₆ Si03/ ₂ )o.o9(PhSi0 ₃ /2)o.77

having a melting point of 70°C and a weight average molecular weight of 2,700.

When 1 g of the obtained organopolysiloxane was added to 99 g of toluene and stirred at 25°C, complete dissolution of the organopolysiloxane in the toluene was observed.

[0070] Practical Example 21

19.4 g of phenyltrimethoxysilane, 25.0 g of phenylaminopropyltrimethoxysilane, 15.2 g of decamethyltetrasiloxane, 67.5 g of toluene, and 0.20 g of cesium hydroxide were placed in a 200 ml flask provided with a thermometer, a Dean-Stark apparatus, and a refluxing cooler and stirred. 7.9 g of water was added to the system and co-hydrolyzed while applying heat. Then, the generated alcohol and excess water were removed by azeotropic dehydration and the system was heated to reflux for 6 hours. The system was cooled, and then 0.4 g of acetic acid was added to neutralize the system. Thereafter, the generated salt was removed by filtration, and then the toluene and the low boiling components were removed by heating the filtrate under reduced pressure. Thus, 36.4 g of a light yellow highly viscous liquid was obtained. The liquid was determined via ²⁹ Si-nuclear magnetic resonance spectroscopic analysis to be a

phenylamino group-containing siloxane compound represented by the average structural formula:

(Me3SiOi/2)o. ₁₅ (lvle2Si02/2)o.i7(P NHC3H ₆ Si03/2)o. ₃ 3(PhSi032)o.35

having a weight average molecular weight of 2,000.

When 1 g of the obtained organopolysiloxane was added to 99 g of toluene and stirred at 25°C, complete dissolution of the organopolysiloxane in the toluene was observed.

Γ007Π I Practical Example 31

50.0 g of phenylaminopropyltrimethoxysilane, 30.4 g of decamethyltetrasiloxane, 50.2 g of toluene, and 0.20 g of cesium hydroxide were placed in a 200 ml flask provided with a thermometer, a Dean-Stark apparatus, and a refluxing cooler and stirred. 7.9 g of water was added and then the system was co-hydrolyzed while applying heat. Then, the generated alcohol and excess water were removed by azeotropic dehydration and the system was heated to reflux for 6 hours. The system was cooled, and then 0.4 g of acetic acid was added to neutralize the system. Thereafter, the generated salt was removed by filtration, and then the toluene and the low boiling components were removed by heating the filtrate under reduced pressure. Thus, 52.9 g of a light yellow liquid was obtained. The liquid was determined via ²⁹ Si-nuclear magnetic resonance spectroscopic analysis to be a phenylamino group-containing siloxane compound represented by the average structural formula:

(Me3Si0 ₁ /2)o.25(Me2Si0 ₂ /2)o 32(Ph HC ₃ H ₆ Si0 ₃ /2)o.43 having a weight average molecular weight of 2,000 and a viscosity of 1 ,910 mPa-s. When 1 g of the obtained organopolysiloxane was added to 99 g of toluene and stirred at 25°C, complete dissolution of the organopolysiloxane in the toluene was observed.

[0072] fPractical Example 41

38.7 g of phenyltrimethoxysilane, 50.0 g of phenylaminopropyltrimethoxysilane, 60.8 g of decamethyltetrasiloxane, 122.5 g of toluene, and 0.25 g of cesium hydroxide were placed in a 300 ml flask provided with a thermometer, a Dean-Stark apparatus, and a refluxing cooler and stirred. 15.9 g of water was added and then the system was co-hydrolyzed while applying heat. Then, the generated alcohol and excess water were removed by azeotropic dehydration and the system was heated to reflux for 6 hours. The system was cooled, and then 0.5 g of acetic acid was added to neutralize the system. Thereafter, the generated salt was removed by filtration, and then the toluene and the low boiling components were removed by heating the filtrate under reduced pressure. Thus, 93.5 g of a light yellow liquid was obtained. The liquid was determined via ²⁹ Si-nuclear magnetic resonance spectroscopic analysis to be a phenylamino group-containing siloxane compound represented by the average structural formula:

(Me ₃ SiOi 2)o.25(Me2SiO _M )o.2e(PhNHC3H _e SiOiV2)o.2 (PhSi03«)o.23

having a weight average molecular weight of 1 ,900 and a viscosity of 2,410 mPa-s.

Whenl g of the obtained organopolysiloxane was added to 99 g of toluene and stirred at 25°C, complete dissolution of the organopolysiloxane in the toluene was observed.

[0073] [Practical Example 51

76.7 g of phenylaminopropyltrimethoxysilane, 106.9 g of trimethyl-terminated

phenylmethylsiloxane (710 FLUID, manufactured by Dow Corning Toray Co., Ltd.), 162.2 g of toluene, and 0.29 g of cesium hydroxide were placed in a 300 ml flask provided with a thermometer, a Dean-Stark apparatus, and a refluxing cooler and stirred. 12.2 g of water was added and then the system was co-hydrolyzed while applying heat. Then, the generated alcohol and excess water were removed by azeotropic dehydration and the system was heated to reflux for 6 hours. The system was cooled, and then 0.6 g of acetic acid was added to neutralize the system. Thereafter, the generated salt was removed by filtration, and then the toluene and the low boiling components were removed by heating the filtrate under reduced pressure. Thus, 157.7 g of a light yellow liquid was obtained. The liquid was determined via ²⁹ Si-nuclear magnetic resonance spectroscopic analysis to be a phenylamino group-containing siloxane compound represented by the average structural formula:

(Me3Si0 ₁ / ₂ )o.o8(PhMeSi02/2)o.65(PhNHC ₃ H ₆ Si03/2)o.27

having a weight average molecular weight of 1 ,800 and a viscosity of 12,000 mPa-s.

Whenl g of the obtained organopolysiloxane was added to 99 g of toluene and stirred at 25°C, complete dissolution of the organopolysiloxane in the toluene was observed.

[0074] fPractical Example 61 59.4 g of phenyltrimethoxysilane, 38.3 g of phenylaminopropyltrimethoxysilane, 13.9 g of

,3-divinyl-l , ,3,3-tetramethyldisiloxane, 80.6 g of toluene, and 0.20 g of cesium hydroxide were placed in a 300 ml flask provided with a thermometer, a Dean-Stark apparatus, and a refluxing cooler and stirred. 18.2 g of water was added and then the system was co-hydrolyzed while applying heat. Then, the generated alcohol and excess water were removed by azeotropic dehydration and the system was heated to reflux for 6 hours. The system was cooled, and then 0.8 g of acetic acid was added to neutralize the system. Thereafter, the generated salt was removed by filtration, and then the toluene and the low boiling components were removed by heating the filtrate under reduced pressure. Thus, 71.3 g of a light yellow highly viscous liquid was obtained. The liquid was determined via ²⁹ Si-nuclear magnetic resonance spectroscopic analysis to be a phenylamino group-containing siloxane compound represented by the average structural formula:

(V ⁱ Me ₂ SiOi 2)o.i2(PhNHC3HeS ^' i03«)o.3i(PhS ^' i03e)o.57

having a weight average molecular weight of 2,500.

When 1 g of the obtained organopolysiloxane was added to 99 g of toluene and stirred at 25°C, complete dissolution of the organopolysiloxane in the toluene was observed.

[0075] fComparative Example 11

59.4 g of phenyltrimethoxysilane, 76.6 g of phenylaminopropyltrimethoxysilane, and 98.8 g of toluene were placed in a 300 ml flask provided with a thermometer, a Dean-Stark apparatus, and a refluxing cooler and stirred. A mixed solution of 14.6 g of water, 14.6 g of methanol, and 0.13 g of a 11 N potassium hydroxide aqueous solution was added to the system and co-hydrolyzed while applying heat. Next, the generated alcohol was removed by distillation and the system was heated to reflux for 4 hours. The system was cooled, and then 0.2 g of acetic acid was added to neutralize the system. Thereafter, the generated salt was removed by filtration, and then the toluene and the low boiling components were removed by heating the filtrate under reduced pressure. Thus, 98.9 g of a light yellow highly viscous liquid was obtained. The siloxane was determined via ²⁹ Si-nuclear magnetic resonance spectroscopic analysis to be a phenylamino group-containing siloxane compound represented by the average structural formula:

(PhNHC3H ₆ Si03/2)o.5o(PhSi0 ₃ /2)o.5o(OMe)o. ₂ 8

having a weight average molecular weight of 2,500.

When 1 g of the obtained organopolysiloxane was added to 99 g of toluene and stirred at 25°C, complete dissolution of the organopolysiloxane in the toluene was observed.

[0076] fComparative Example 21

Aside from using 17.5 g of aminopropylmethyldimethoxysilane in place of the

phenylaminopropyltrimethoxysilane, the product of Comparative Example 2 was synthesized in the same procedure as that of Practical Example 1. Thus, 120 g of a white solid was obtained. The solid was determined via Si-nuclear magnetic resonance spectroscopic analysis to be an amino group-containing siloxane compound represented by the average structural formula: (MezSiOz/^o. iNHzCaHeCCH^SiOz/^Q.ogi SiO^oj?

having a melting point of 65°C and a weight average molecular weight of 2,880.

When 1 g of the obtained organopolysiloxane was added to 99 g of toluene and stirred at 25°C, complete dissolution of the organopolysiloxane in the toluene was observed.

[0077] [Comparative Example 31

35.0 g of a silicone resin (silicon-bonded hydroxyl group content: 4 mass.%) represented by the following average structure formula:

(Me ₃ Si0 _1/2 )o. ₅₃ (Si0 ₄ /2)o.47

was dissolved in 15.0 g of toluene in a 100 ml flask provided with a thermometer, a Dean-Stark apparatus, and a refluxing cooler. Then, 10 g of 3-anilinopropyltrimethoxysilane was uniformly mixed into the system. The generated methanol was removed from the system while applying heat. The system was then heated at a temperature of toluene reflux for 6 hours. Next, the toluene was removed by heating the reaction liquid under reduced pressure. Thus, 40.8 g of a light yellow highly viscous liquid was obtained. The liquid was determined via ²⁹ Si-nuclear magnetic resonance spectroscopic analysis to be a phenylamino group-containing siloxane compound represented by the average structural formula:

(Me3SiO ₁ /2)0.42(Ph HC ₃ H6SiO3/2)0.07(S ^' lO ₄ /2)0.51

having a weight average molecular weight of 5,500.

[0078] [Comparative Example 41 Production of crosslinking silicone-rubber particles:

86.4 parts by mass of a dimethylpolysiloxane capped at both molecular terminals with silanol groups (silanol group content=4.0 mass.%) having a viscosity of 40 mPa-s and represented by the following average structure formula:

HO-[Si(CH ₃ ) ₂ 0] ₁₂ -H

9.1 parts by mass of a methylhydrogenpolysiloxane capped at both molecular terminals with trimethyisiloxy groups (silicon-bonded hydrogen atom content=1.5 mass.%) having a viscosity of 10 mPa-s, and 4.5 parts by mass of 3-anilinopropyltrimethoxysilane were uniformly mixed. Thus, a crosslinkable silicone composition was prepared. 5 parts by mass of a mixture containing this composition and secondary tridecylether and secondary dodecylether of ethylene oxide (7-mol addition) (43 mass.% of dodecyl groups, 57 mass.% of tridecyl groups, and HLB equal to 12.8) was premixed with 97 parts by mass of water. Thereafter, this mixture was emulsified by a colloid mill. Then, the emulsion was diluted with 100 parts by mass of pure water. Thus, a water-based emulsion of a silicone mixture was prepared.

[0079] Next, a water-based emulsion of tin octoate having an average particle size of about 1.2 pm was prepared by emulsifying 1 part by mass of tin octoate (II) with 1 part by mass of a mixture containing secondary tridecylether and secondary dodecylether of ethylene oxide (7-mol addition) (43 mass.% of dodecyl groups, 57 mass.% of tridecyl groups, and HLB equal to 12.8) and 10 parts by mass of pure water. The emulsion was added to the water-based emulsions of silicone composition, respectively and uniformly mixed, and allowed to sit at rest for 1 day and the crosslinkable silicone composition emulsifying in the water was cured. Thus, a uniform aqueous suspension of cross-linked silicone-rubber particles, free of gel-like substance, was prepared. The suspension was dried by using a hot-air dryer and the cross-linked

silicone-rubber particles were collected. Thus, silicone-rubber particles having a

dimethylsiloxane blocks represented by the average structure formula: -[Si(CH ₃ ) ₂ 0]i ₂ - were prepared. The average particle size of the cross-linked silicone-rubber particles was 1.9 Mm, the type A durometer hardness was 67, and the anilino group content was 1.56 mass.%.

Solubility was checked by adding 1 g of the obtained cross-linked silicone-rubber particles to 99 g of toluene and stirring at 25°C. As dissolution could not be visually confirmed even after 10 minutes of stirring, it was determined that the cross-linked silicone-rubber particles were insoluble in toluene.

[0080] Table 1 : Obtained organopolysiloxanes in each examples

[0081] Preparation and evaluation of the thermosetting resin composition

[Practical Example 71

60 parts by mass of a crystalline biphenyl epoxy resin (product name "Epicoat" YX4000H, manufactured by Yuka Shell Epoxy Co., Ltd.; epoxy equivalent weight=190, melting

point=105°C), 40 parts by mass of a phenol aralkyl phenolic resin (Milex XLC-3L, manufactured by Mitsui Chemicals, Inc.; phenolic hydroxyl group equivalent weight=168; an amount where the molar ratio of the phenolic hydroxyl groups in this phenolic resin to the epoxy groups in the epoxy resin is 1.0), 5 parts by mass of the siloxane composition prepared in Practical Example 1 , 600 parts by mass of an amorphous spherical silica having an average particle size of 12 m

(FB-35X, manufactured by Denki Kagaku Kogyo K.K.), 0.4 parts by mass of carbon black, 1 part by mass of 3-Glycidoxypropyltrimethoxysilane, 1 part by mass of Carnauba wax, and 1 part by mass of triphenylphosphine were melted and mixed uniformly using by a heated two-roll mill. Thus, a curable epoxy resin composition was prepared. Spiral flow, burrs, mold contamination, moisture absorption, Curing shrinkage ratio (AM), and Curing shrinkage ratio (PC) were evaluated for this curable epoxy resin composition and a cured body thereof. The results are shown in Table 2.

[0082] [Practical Example 81

Aside from using 5 parts by mass of the siloxane compound prepared in Practical Example 3 in place of the siloxane compound prepared in Practical Example 1 , the curable epoxy resin composition of Practical Example 8 was prepared in the same procedure as that of Practical Example 7. The curable epoxy resin composition and a cured body thereof were evaluated in the same manner as described in Practical Example 7. The results are shown in Table 2.

[0083] [Practical Example 91

Aside from using 5 parts by mass of the siloxane compound prepared in Practical Example 6 in place of the siloxane compound prepared in Practical Example 1 , the curable epoxy resin composition of Practical Example 9 was prepared in the same procedure as that of Practical Example 7. The curable epoxy resin composition and a cured body thereof were evaluated in the same procedure as described in Practical Example 7. The results are shown in Table 2.

[0084] [Practical Example 101

51 parts by mass of an amorphous biphenyl aralkyl epoxy resin (NC-3000, manufactured by Nippon Kayaku Co., Ltd.; epoxy equivalent weight= 275, softening point= 60°C), 39 parts by mass of a biphenyl aralkyl phenolic resin (MEH-7851SS, manufactured by Meiwa Plastics Industries, Ltd.; phenolic hydroxyl group equivalent weight= 207, softening point= 80°C), 5 parts by mass of the siloxane compound prepared in Practical Example 2, 550 parts by mass of an amorphous spherical silica having an average particle size of 12 μιτι (FB-35X, manufactured by Denki Kagaku Kogyo K.K.), 0.4 parts by mass of carbon black, 1 part by mass of 3-Glycidoxypropyltrimethoxysilane, 1 part by mass of Carnauba wax, and 1 part by mass of triphenylphosphine were melted and mixed uniformly using a heated two-roll mill. Thus, a curable epoxy resin composition was prepared. The curable epoxy resin composition and a cured body thereof were evaluated in the same procedure as described in Practical Example 7. The results are shown in Table 2.

[0085] [Comparative Example 51

Aside from using 5 parts by mass of the siloxane compound prepared in Comparative Example 1 in place of the siloxane compound prepared in Practical Example 1 , the curable epoxy resin composition of Comparative Example 5 was prepared in the same manner as that of Practical Example 7. The curable epoxy resin composition and a cured body thereof were evaluated in , the same procedure as described in Practical Example 7. The results are shown in Table 2.

[0086] [Comparative Example 61

Aside from using 5 parts by mass of the siloxane compound prepared in Comparative Example 2 in place of the siloxane compound prepared in Practical Example 1 , the curable epoxy resin composition of Comparative Example 6 was prepared in the same manner as that of Practical Example 7. The curable epoxy resin composition and a cured body thereof were evaluated in the same procedure as described in Practical Example 7. The results are shown in Table 2.

[0087] [Comparative Example 71

Aside from not using the siloxane compound prepared in Practical Example , the curable epoxy resin composition of Comparative Example 7 was prepared in the same manner as that of Practical Example 7. The curable epoxy resin composition and a cured body thereof were evaluated in the same procedure as described in Practical Example 7. The results are shown in Table 2.

[0088] [Comparative Example 81

Aside from not using the siloxane compound prepared in Practical Example 2, the curable epoxy resin composition of Comparative Example 8 was prepared in the same procedure as that of Practical Example 10. The curable epoxy resin composition and a cured body thereof were evaluated in the same manner as described in Practical Example 7. The results are shown in Table 2.

[0089] [Comparative Example 91

Aside from using 5 parts by mass of the siloxane compound prepared in Comparative Example 3 in place of the siloxane compound prepared in Practical Example 1 , the curable epoxy resin composition of Comparative Example 9 was prepared in the same procedure as that of Practical Example 7. The curable epoxy resin composition and a cured body thereof were evaluated in the same procedure as described in Practical Example 7. The results are shown in Table 2.

[0090] [Comparative Example 101

Aside from using 5 parts by mass of the cross-linked silicone-rubber particles prepared in Comparative Example 4 in place of the siloxane compound prepared in Practical Example 2, the curable epoxy resin composition of Comparative Example 10 was prepared in the same manner as that of Practical Example 10. The curable epoxy resin composition and a cured body thereof were evaluated in the same procedure as described in Practical Example 7. The results are shown in Table 2.

[0091] Table 2

[0092] As it is clear from Table 2, in cases where the thermosetting resin compositions of Practical Examples 7 to 10 were cured, formability was superior, and moisture absorption and cure shrinkage were superior. On the other hand, in cases where the thermosetting resin compositions of Comparative Example 5 to 10 were cured, either gelling occurred or moisture absorption and curing shrinkage ratio were inferior.

Industrial Applicability

[0093] By using the thermosetting resin composition of the present invention, a cured body having excellent formability, low moisture absorption, and low curing shrinkage ratio can be formed. Thus, the thermosetting resin composition of the present invention can be suitably used as a sealing agent or adhesive for electric and electronic parts that are sensitive to stress generated when curing or when exposed to thermal shock.