KR20160043030A - Novel organopolysiloxane, surface treatment agent comprising the same, resin composition comprising the same, and gelatinous product or cured product thereof - Google Patents

Abstract

The present invention relates to an organopolysiloxane represented by the following formula, use thereof as a surface treating agent, and a resin composition comprising the organopolysiloxane and a functional filler:
R ⁶ ₃ Si-R ⁵ - [SiR ⁴ ₂ O] _n -Si R ³ _(3-a) - [R ² -R ¹ ] _a
In the above formulas,
R ¹ is a monovalent hydrocarbon group having a plurality of aromatic rings and having at least 10 carbon atoms;
R ² is a direct bond to a divalent hydrocarbon group or silicon (Si) atom which may contain a heteroatom;
R ³ and R ⁴ are each independently selected from monovalent hydrocarbon groups;
R ⁵ is a divalent hydrocarbon group which may contain a hetero atom, or an oxygen atom;
R ⁶ is a group independently selected from an alkyl group, an alkenyl group, an aryl group, and an alkoxy group;
n is an integer from 0 to 200;
a is an integer of 1 to 3;

Description

TECHNICAL FIELD [0001] The present invention relates to a novel organopolysiloxane, a surface treatment agent containing the same, a resin composition containing the same, and a gel or a cured product of the organopolysiloxane,

The present invention relates to a novel organopolysiloxane, a surface treatment agent containing the same, and a resin composition containing the same, and more particularly to a thermally conductive silicone composition. Priority is claimed on Japanese Patent Application No. 2013-168660, filed August 14, 2013, the contents of which are incorporated herein by reference.

A functional filler selected from a thermally conductive filler, a fluorescent filler, an electrically conductive filler, a dielectric filler, an insulating filler, a light-diffusing filler, a translucent filler, a colorable filler, and a reinforcing filler, Grease, gel, rubber-like cured product, coating agent, phase-change material and the like. Particularly, in recent years, high density and increased integration of printed circuit boards and hybrid ICs on which transistors, ICs, memory elements and other electronic components are mounted have been achieved. Thus, various types of thermally conductive silicone compositions are used to effectively dissipate heat. Thermally conductive silicone greases, thermally conductive silicone gel compositions, thermally conductive silicone rubber compositions, and the like are known as such thermally conductive silicone compositions.

An example of a composition that has been proposed as such a thermally conductive silicone composition is a thermally conductive silicone composition using a silicone oil as the primary agent and containing an inorganic filler such as zinc oxide or alumina powder Japanese Unexamined Patent Application Publication No. S51-55870 and Japanese Unexamined Patent Application Publication No. S61-157587), organopolysiloxanes, alkoxy groups bonded to silicon atoms, or acyloxy groups (Japanese Unexamined Patent Application Publication No. 2000-256558) comprising an organopolysiloxane, a thermally conductive filler, and a curing agent having an alkoxy group bonded to a silicon atom (Japanese Unexamined Patent Application Publication No. 2000-256558), and an organopolysiloxane, a curing agent, A thermally conductive silicone composition comprising a thermally conductive filler surface-treated with an alkylene organosiloxane (see Japanese Unexamined Patent Application, Include Application Publication No. 2001-139815 No.).

Japanese Unexamined Patent Application Publication No. S50-105573 Japanese Unexamined Patent Application Publication No. S51-55870 Japanese Unexamined Patent Application Publication No. S61-157587 Japanese Unexamined Patent Application Publication No. 2000-256558 Japanese Unexamined Patent Application Publication No. 2001-139815

In resin compositions comprising functional fillers, and in particular in thermally conductive silicone compositions, the components proposed as surface treatment agents are often compounds having hydrolysable groups, such as alkoxysilyl groups. These hydrolyzable groups are somewhat effective for metal oxides having hydroxyl groups on the surface, such as alumina, but they are ineffective for functional fillers that do not have hydroxyl groups on their surfaces, such as boron nitride or graphite, and these functional fillers- , And thermally conductive fillers are used at a high concentration, the viscosity of the resulting composition is remarkably increased, resulting in a problem that handling workability is considerably lowered. Therefore, as the surface treating agent using known organopolysiloxanes, there is a problem that the resin composition can not be filled with various functional fillers at a high concentration, the performance of the composition to be produced is insufficient, and that the composition achieves both excellent handling workability and performance There is a problem that it can not be done.

The present invention was conceived at least to solve the problems described above, and the present invention provides novel organopolysiloxanes having excellent handling workability or dispersion stability. The problem of increased viscosity or poor dispersion does not occur even when various functional fillers are filled in the surface treatment agent containing the novel organopolysiloxane, in particular, the functional resin composition. The concepts of the present invention are embodied in typical novel organopolysiloxane and / or thermally conductive silicone compositions having good handling performance and high thermal conductivity. These properties may also appear when they contain a large amount of thermally conductive filler.

In one aspect, there is provided an organopolysiloxane represented by formula (I).

Formula I

R ¹ is a monovalent hydrocarbon group having a plurality of aromatic rings and having at least 10 carbon atoms;

R ² is a direct bond to a divalent hydrocarbon group or silicon (Si) atom which may contain a heteroatom;

R ³ and R ⁴ are each independently selected from monovalent hydrocarbon groups;

R ⁵ is a divalent hydrocarbon group which may contain a hetero atom, or an oxygen atom;

R ⁶ is a group independently selected from an alkyl group, an alkenyl group, an aryl group, and an alkoxy group;

n is an integer from 0 to 200;

a is an integer of 1 to 3;

The present invention also relates to a surface treatment agent comprising the organopolysiloxane described above.

The surface treatment agent of the present invention can be suitably used for the surface treatment of various functional fillers and can be suitably used for the surface treatment of various functional fillers and is suitably used for the surface treatment of various functional fillers such as thermally conductive fillers, fluorescent fillers, electrically conductive fillers, dielectric fillers, insulative fillers, light-diffusing fillers, And a reinforcing filler. ≪ Desc / Clms Page number 2 >

The surface treatment agent containing the organopolysiloxane of the present invention can be used in the form of an inorganic filler, an organic filler, a nanocrystal structure, and a quantum dot, and fillers that can be partially or wholly covered with a silica layer ≪ / RTI > may be used for the surface treatment of one type or two or more types of fillers. These surface treatment agents can be used in the synthesis process of various functional fillers.

The present invention also relates to a resin composition comprising the above-described organopolysiloxane and a filler surface-treated with the organopolysiloxane. These resin compositions may be curable resin compositions or thermoplastic resin compositions, and may also be non-curable or thick-walled resin compositions.

The resin composition of the present invention can be used for various applications depending on the type of the functional filler and the resin. In particular, the resin composition is used for a purpose selected from a thermally conductive material, an electrically conductive material, a semiconductor sealing material, an optical material, a functional coating material, Can be used.

The resin composition of the present invention particularly preferably has a viscosity, curability, or phase changeability. Thickening refers to the fact that the initial viscosity is not significantly changed but the total viscosity is increased by heating under desired use conditions or by using a thickening agent to form a gel or viscous liquid or paste form. Examples include grease compositions and the like. The term " hardenability " refers to a property of curing the composition due to heating or the like, and examples thereof include not only the hard coat resin composition and the semiconductor encapsulating resin composition but also a resin composition which can be formed into a sheet, a resin composition which is cured into a gel- And a semi-curable resin composition which forms a soft rubber having plasticity. The phase change refers to the property that a functional filler is filled in a heat-softening resin having a softening point such as a wax, wherein the phase varies depending on the operating temperature of the exothermic electronic part and the like, have.

In particular, the present invention relates to a thermally conductive silicone composition comprising an organopolysiloxane (A) and a thermally conductive filler (B) as described above.

The silicone composition of the present invention may further comprise at least one type of organopolysiloxane (C) in addition to the organopolysiloxane of formula (1) described above.

The thermally conductive filler (B) described above is preferably selected from the group consisting of pure metals, alloys, metal oxides, metal hydroxides, metal nitrides, metal carbides, metal silicides, carbon, soft magnetic alloys, At least one type of powder and / or fiber selected from the group consisting of

The above-described pure metal may be bismuth, lead, tin, antimony, indium, cadmium, zinc, silver, copper, nickel, aluminum, iron or metal silicon; or

The alloy consists of two or more types of metal selected from the group consisting of bismuth, lead, tin, antimony, indium, cadmium, zinc, silver, copper, nickel, aluminum, iron or metal silicon; or

Wherein the metal oxide is alumina, zinc oxide, silicon oxide, magnesium oxide, beryllium oxide, chromium oxide, or titanium oxide; or

The metal hydroxide is magnesium hydroxide, aluminum hydroxide, barium hydroxide, or calcium hydroxide; or

Wherein the metal nitride is boron nitride, aluminum nitride, or silicon nitride; or

Wherein the metal carbide is silicon carbide, boron carbide, or titanium carbide; or

The metal suicide may be magnesium silicide, titanium silicide, zirconium silicide, tantalum silicide, niobium silicide, chromium silicide, tungsten silicide, or molybdenum silicide; or

The carbon may be diamond, graphite, fullerene, carbon nanotubes, graphene, activated carbon, or amorphous carbon black; or

The soft magnetic alloy may be selected from the group consisting of Fe-Si alloy, Fe-Al alloy, Fe-Si-Al alloy, Fe-Si-Cr alloy, Fe-Ni alloy, Fe- Co alloy, Fe-Si-Al-Cr alloy, Fe-Si-B alloy, or Fe-Si-Co-B alloy; or

The ferrite is Mn-Zn ferrite, Mn-Mg-Zn ferrite, Mg-Cu-Zn ferrite, Ni-Zn ferrite, Ni-Cu-Zn ferrite or Cu-Zn ferrite.

The thermally conductive filler (B) described above is particularly preferably a plate-shaped boron nitride powder (B1) having an average particle size of 0.1 to 30 mu m, a granular boron nitride powder (B2) having an average particle size of 0.1 to 50 mu m, , Spherical and / or pulverized aluminum oxide powder (B3) having an average particle size of 0.01 to 50 mu m, graphite (B4) having an average particle size of 0.01 to 50 mu m, or two or more types thereof / RTI >

The content of the component (B) is preferably 100 to 3,500 parts by mass per 100 parts by mass of the components (A) and (C).

The organopolysiloxane of component (C) preferably has hydrolyzable functional groups bonded to silicon atoms in the molecule.

The component (C) is an organopolysiloxane having a monovalent hydrocarbon group having an aliphatic unsaturated bond to a silicon atom in the molecule and an organopolysiloxane having a hydrogen atom bonded to a silicon atom in the molecule, and the component (C) Further comprises a catalyst for thickening or curing these organopolysiloxanes as a result of the hydrosilylation reaction.

Further, the component (C) is an organopolysiloxane having a monovalent hydrocarbon group having a hydrolyzable functional group bonded to a silicon atom in the molecule and having an aliphatic unsaturated bond to a silicon atom, and a hydrogen atom bonded to a silicon atom in the molecule , Wherein component (C) preferably further comprises a catalyst for thickening or curing these organopolysiloxanes by hydrosilylation reaction.

The present invention also relates to a gelatinous product or a cured product formed by thickening or curing the above-described silicone composition containing a catalyst for thickening or curing the composition as a result of the hydrosilylation reaction. will be.

The novel organopolysiloxane of the present invention is useful as a surface treatment agent for various functional fillers and has an advantage that various functional fillers can be blended into a resin composition in a large amount without deteriorating handling workability or dispersion stability. In particular, the novel organopolysiloxanes of the present invention are useful in the surface treatment of thermally conductive fillers, and the thermally conductive silicone composition of the present invention is characterized in that the composition comprises a large amount of thermally conductive filler to obtain a silicone composition having a high thermal conductivity Even if included, it demonstrates good handling workability without increased composition viscosity. In the case of the curable composition, a uniform cured product can be obtained.

First, the novel organopolysiloxane of the present invention will be described in detail. In the composition, the organopolysiloxane will be treated as "component (A) ".

The organopolysiloxane of the present invention is represented by formula (1)

Formula 1

In Formula 1, R ¹ is a monovalent hydrocarbon group having a plurality of aromatic rings and having at least 10 carbon atoms, which may contain an oxygen atom or a sulfur atom. Further, a plurality of aromatic rings may be condensed, and the aromatic rings are preferably condensed. More preferably, R < ¹ > is a monovalent hydrocarbon group having a plurality of aromatic rings and having at least 10 to at most 40 carbon atoms. Examples of such monovalent hydrocarbon groups having a plurality of aromatic rings and having at least 10 carbon atoms include naphthyl group, alkylnaphthyl group, anthracenyl group, biphenyl group, phenylnaphthyl group, phenyl anthracenyl group, A thiophene group, a thienyl group, a thienyl group, a thienyl group, a thienyl group, a thienyl group, a thienyl group, a thienyl group, a thienyl group, Naphthyl group, naphthyl group, naphthyl group, naphthyl group, naphthyl group, naphthyl group, naphthyl group, naphthyl group, alkylnaphthyl group, phenoxyphenyl group and phenylcarbonyloxyphenyl group. Preferably, R ¹ is 1-naphthyl group, 2-naphthyl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, p- , Or p-ethylnaphthyl group. R ¹ is particularly preferably a 1-naphthyl group or a 2-naphthyl group.

R ² is a direct bond to a divalent hydrocarbon group or silicon (Si) atom which may contain a heteroatom and is, for example, an unsaturated hydrocarbon group such as an alkenyl group, acryloxy Group or a group formed by the reaction of a functional group having a methacryloxy group at the terminal thereof or a group formed by the reaction of a halogen atom, a hydrolyzable functional group such as an alkoxy group or an acyloxy group, and a silanol group Lt; / RTI > Such a structure is a divalent linking group represented by the following structural formula or a direct bond of a Si atom.

In the above structural formulas, "CO" is a carbonyl group represented by -C (= O) - and R ⁷ is each independently a substituted or unsubstituted, linear or branched alkylene group having 2 to 22 carbon atoms Or an alkenylene group, or an arylene group having 6 to 22 carbon atoms. R ⁸ is the same group as R ⁷ or is a group selected from divalent groups represented by the following formulas.

Specifically, R ² is preferably a methylene group, an ethylene group, a methylmethylene group, a propylene group, a methylethylene group, a butylene group, a phenylene group, a methylene phenyl methyl group, an ethylene phenetyl group, Group, a propylene ether group, a butylene ether group, a phenyl ether group, a phenylcarbonyl group, a carbonyl ether group, an oxycarbonyl group, a methylene carbonyl group, an ethylene carbonyl group, a propylene carbonyl group and the like It is the selected group. R ² is particularly preferably a methylene group, an ethylene group, a methylmethylene group, a propylene group, a methylethylene group, an oxygen atom, an oxymethylene group, or an oxyethylene group from the viewpoints of ease of raw material availability and ease of synthesis.

R ³ and R ⁴ are each independently selected from monovalent hydrocarbon groups and preferably monovalent hydrocarbon groups having from 1 to 10 carbon atoms, with no aliphatic unsaturation. Examples include straight chain alkyl groups such as methyl group, ethyl group, propyl group, butyl group, hexyl group, and decyl group; Branched alkyl groups such as isopropyl group, tertiary butyl group, and isobutyl group; Cyclic alkyl groups such as cyclohexyl group; Aryl groups such as phenyl group, tolyl group, and xylyl group; And aralkyl groups such as benzyl group and phenethyl group. R ³ and R ⁴ are preferably an alkyl group having 1 to 4 carbon atoms or a phenyl group, particularly preferably a methyl group, an ethyl group or a phenyl group.

R ⁵ is a divalent hydrocarbon group which may contain a hetero atom, or an oxygen atom, which may contain an oxygen atom or a sulfur atom. R ⁵ is preferably a divalent hydrocarbon group having 1 to 20 carbon atoms, an oxygen atom, or a divalent hydrocarbon group containing 1 or 2 oxygen atoms and having 1 to 20 carbon atoms, A divalent linking group represented by a structural formula or an oxygen atom (-O-). In the following formulas, CO, R ⁷ , and R ⁸ are the same group as described above.

Specifically, R ⁵ is preferably a methylene group, an ethylene group, a methylmethylene group, a propylene group, a methylethylene group, a butylene group, a phenylene group, a methylene phenyl methyl group, an ethylene phenetyl group, Group, propylene ether group, butylene ether group, phenyl ether group, phenylcarbonyl group, carbonyl ether group, oxycarbonyl group, methylene carbonyl group, ethylene carbonyl group, propylene carbonyl group, ethylene carboxypropyl group, (Methyl) ethylene carboxypropylene group, and the like. R ⁵ is particularly preferably a methylene group, an ethylene group, a methylmethylene group, a propylene group, a methylethylene group, an oxygen atom, an oxymethylene group, an oxyethylene group, an ethylene carboxyl group, Or a (methyl) ethylene carboxypropylene group.

R ⁶ is a group independently selected from an alkyl group, an alkenyl group, an aryl group, and an alkoxy group each having 1 to 20 carbon atoms. Examples of R ⁶ include linear alkyl groups such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group , Tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group, and eecodecyl group; Branched alkyl groups such as 2-methylundecyl group and 1-hexylheptyl group; Cyclic alkyl groups such as cyclododecyl group; Aralkyl groups such as 2- (2,4,6-trimethylphenyl) propyl group; Hydrocarbon groups having unsaturated bonds, such as vinyl group, allyl group, butenyl group, hexenyl group, and octenyl group; Aryl groups such as phenyl group, tolyl group, and xylyl group; And aralkyl groups such as benzyl group and phenethyl group.

n is an integer of 0 to 200, a is an integer of 1 to 3, and p is an integer of 0 to 10.

Since the organopolysiloxane (A) contained as a component of the present invention has a functional group having two or more aromatic rings, the compatibility with a filler having a plate-like structure or a polycyclic aromatic filler is high. When this is used for producing a composite material such as a surface treatment agent, a base oil and the like, for example, a grease, a compound, or a gel, compatibility can be improved and viscosity increase can be suppressed.

The following compounds are examples of such organopolysiloxanes. Here, Me is a CH ₃ group.

The method for producing the organopolysiloxane (A) used in the present invention is not particularly limited, but the organopolysiloxane can be prepared by the following method.

Wherein the organopolysiloxane has the following formula:

Wherein R ¹ , R ² , R ³ , and R ⁴ are the same groups as described above, n, a, and b are the same numbers as described above. The organopolysiloxanes (a-1) and

(B-1) having a plurality of aliphatic double bonds in the molecule and containing from 10 to 40 carbon atoms, which may contain an oxygen atom or a sulfur atom, is subjected to an addition reaction by hydrosilylation reaction . ≪ / RTI >

Alternatively, the organopolysiloxane may have the formula:

Bonded hydrogen atom-containing polysiloxane represented by the formula (a) in which R ³ , R ⁴ , R ⁵ , and R ⁶ are the same groups as described above, and n and a are the same numbers as described above -2) and

A monovalent hydrocarbon compound or organosilicon compound (b-2) having at least one aliphatic double bond in the molecule and containing a functional group having a plurality of aromatic rings and containing an oxygen atom or a sulfur atom and having 10 or more carbon atoms, Can be obtained by performing an addition reaction by a hydrosilylation reaction.

As yet another method that does not employ a hydrosilylation reaction, the organopolysiloxane is represented by the following formula:

(Wherein R ³ , R ⁴ , R ⁵ , and R ⁶ are the same groups as described above.) N and a are the same numbers as described above) and silicon-bonded hydrogen atom-containing polysiloxane

R _b SiX _(4-b)

(Wherein R is a monovalent hydrocarbon group containing a functional group having a plurality of aromatic rings and having at least 10 carbon atoms and X is a halogen atom or a hydrolyzable functional group such as an alkoxy group or an acyloxy group , and b is an integer of 1 to 4) by performing a substitution reaction.

A functional group having a plurality of aromatic rings, which is a feature of the present invention, is contained in the raw material (a-1) or the raw material (b-2).

The following compounds are examples of the silicon-bonded hydrogen atom-containing organopolysiloxane (a-1) containing a functional group having a plurality of aromatic rings.

Examples of the hydrocarbon compound or organosilicon compound (b-1) having at least one aliphatic double bond in the molecule and having no plural aromatic functional groups include ethylene, acetylene, 1-propene, 1-butene, Hexene, octene, octene, 1-decene, 1-dodecene, 1-tetradecene, 1-hexadecene, Vinyltrimethoxysilane, vinyltrimethoxysilane, vinyltrimethoxysilane, vinyltrimethoxysilane, vinyltrimethoxysilane, vinyltrimethoxysilane, vinyltrimethoxysilane, vinyltrimethoxysilane, vinyltrimethoxysilane, vinyltrimethoxysilane, vinyltrimethoxysilane, Vinyltriethoxysilane, vinyltriethoxysilane, vinyltriethoxysilane, vinyltriethoxysilane, vinyltriisopropoxysilane, vinyltriacetoxysilane, vinylmethyldiacetoxysilane, vinyltris (methyl ethyl ketone, Aminooxy) silane, vinyltriisopropenoxysilane, vinylphen (Trimethylsiloxy) silane, vinyl heptamethyltrisiloxane, allyltrimethylsilane, allyltrimethoxysilane, allyltrimethoxysilane, allyltrimethoxysilane, allyltrimethoxysilane, allyltrimethoxysilane, allyltrimethoxysilane, (Trimethylsiloxy) silane, 5-hexenyl trimethoxysilane, 5-hexenylmethyldimethoxysilane, 5-hexenyldimethylmethoxysilane, 5-hexenyltriethoxysilane, 5-hexenylmethyldiethoxysilane, 5-hexenyldimethylethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyldimethylmethoxysilane , 3-methacryloxypropyltriethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, and 3-acryloxypropylmethyldimethoxysilane.

Examples of the silicon-bonded hydrogen atom-containing organopolysiloxane (a-2) having no functional group having a plurality of aromatic rings include pentamethyldisiloxane, ethyltetramethyldisiloxane, n-propyltetramethyldisiloxane, Propyltetramethyldisiloxane, n-butyltetramethyldisiloxane, n-butyltetramethyldisiloxane, n-hexyltetramethyldisiloxane, n-octyltetramethyldisiloxane, n-decyltetramethyldisiloxane, n-dodecyl Tetramethyldisiloxane, n-tetradodecyltetramethyldisiloxane, n-hexadecyltetramethyldisiloxane, and n-octadecyltetramethyldisiloxane.

Examples of raw materials for the hydrocarbon compound or organic silicon compound (b-2) having at least one aliphatic double bond and a functional group having a plurality of aromatic rings include vinyl naphthalene, vinyl anthracene, vinyl phenanthrene, vinyl pyrene, , Vinylphenylphenylene, vinylphenylnaphthalene, vinylphenyl anthracene, vinylphenylphenanthrene, vinylphenylpyrene, vinylphenylterphenyl, phenoxystyrene, phenylcarbonylstyrene, phenylcarboxystyrene, phenoxycarbonylstyrene, allylnaphthalene, allyl (Allylphenoxy) benzene, allyl (phenylcarbonyl) benzene, allylphenoxybenzene, allylphenoxyphenyl, allylphenanthrene, allylphenanthrene, allylphenanthrene, allylpyrene, allylbiphenyl, allylterphenyl, allylphenylnaphthalene, allylphenylanthracene, Benzene, allylphenoxybenzene, allyl (phenylcarbonyl) benzene, allyl (phenylcarboxy) benzene, and allyl (phenoxycarbonyl) benzene.

More specific examples are 1-vinylnaphthylene, 2-vinylnaphthylene, 1 -vinylanthracene, 2-vinylanthracene, 9-vinylanthracene, 1-vinylphenanthrene, Vinylphenylene, 1,2-vinylphenanthrene, 1,2-vinylphenylbenzene, 1,3-vinylphenylbenzene, 1,4-vinylphenylbenzene, Benzene, 1,3-vinyl (1-naphthyl) benzene, 1,3-vinyl (2-naphthyl) benzene, Vinylnaphthalene, 4-vinyl-1,1 '- (4'-phenyl) biphenylene, 1-allylnaphthalene, 2-allyl Naphthalene, 1-allylanthracene, 2-allylanthracene, 9-allylanthracene, 1-allylphenanthrene, 2-allylphenanthrene, 3-allylphenanthrene, (1-naphthyl) benzene, 1,2-allyl (2-naphthyl) benzene, 1,3 - allyl (1-naphthyl) benzene, (1-naphthyl) benzene, 1,4-allyl (2-naphthyl) benzene, 1-allyl-4-naphthylnaphthalene, 4 Vinyl-3- (phenyloxy) benzene, 1-vinyl-2- (phenyl) (Phenylcarbonyl) benzene, 1-vinyl-2- (phenoxycarbonyl) benzene, 1-allyl-4- (Phenyloxy) benzene, 1-allyl-3- (phenyloxy) benzene, 1- Carboxy) benzene, and 1-allyl-2- (phenoxycarbonyl) benzene.

The hydrosilylation reaction is usually carried out using a metal complex catalyst, but is not particularly limited in the production process of the present invention. The catalyst used in the production method of the present invention is a catalyst in which a silicon-bonded hydrogen atom in the raw material (a-1) or (a-2) is added to an aliphatic double bond in the component (b-1) For example, a Group VIII transition metal catalyst of the periodic table, preferably a platinum catalyst. Specific examples include platinum chloride, an alcohol solution of platinum chloride, platinum olefin complexes, platinum alkenylsiloxane complexes, and platinum carbonyl complexes.

In the production process of the present invention, the molar ratio of the component (a-1) and the component (b-1) or the component (a-2) It is preferable that the reaction is carried out in an amount of 0.5 to 1.5 mol in the amount of the component (b-1) or the component (b-2) per 1 mol of the component (a-2), and the reaction is carried out in an amount of 0.95 to 1.1 mol Is particularly preferable.

In addition, the use of an organic solvent is optional in the production process of the present invention. Examples of such organic solvents include aromatic, such as benzene, toluene, and xylene; Aliphatic, such as pentane, hexane, heptane, octane, and decane; Ethers such as tetrahydrofuran, diethyl ether, and dibutyl ether; Ketones such as acetone and methyl ethyl ketone; And esters, such as ethyl acetate and butyl acetate.

In addition, the reaction temperature is not particularly limited in the production method of the present invention, and the reaction can be carried out at room temperature or under heating. When the reaction is carried out under heating, the reaction temperature is preferably 50 to 200 占 폚. Further, the progress of the reaction can be determined by analyzing the reaction solution by methods such as gas chromatography analysis, infrared spectroscopy analysis, or nuclear magnetic resonance analysis, and determining the ratio of the respective raw materials in the reaction system and the silicon- The content of the group can be obtained and tracked. After completion of the reaction, the target organopolysiloxane can be obtained by removing unreacted components, an organic solvent, and the like.

One method for producing the organopolysiloxane of the present invention is a method of reacting a siloxane (c) having a hydroxyl group at one end with an organosilicon compound (d) having a plurality of aromatic functional groups and having a single hydrolysable group to be.

The following compound is an example of a siloxane (c) having a hydroxyl group at one end:

These polysiloxanes having a hydroxyl group at one end can be obtained according to a known production method (Japanese Unexamined Patent Application Publication No. H8-113649 and Japanese Patent No. 2826939).

Further, examples of the organosilicon compound (d) having a substituent group having a plurality of aromatic functional groups and having a single hydrolyzable group include 1-naphthylchlorodimethylsilane, 1-naphthyldimethylmethoxysilane, 1-naphthyldimethyl Anthracenyldimethylmethoxysilane, 1-anthracenyldimethylmethoxysilane, 2-anthracenyldimethylmethoxysilane, 1-anthracenyldimethylmethoxysilane, 1-anthanecyldimethylsiloxane, (Dimethylmethoxysilyl) benzene, 1,4-phenyl (dimethylmethoxysilyl) benzene, 1,4- (1'-naphthyl) (Phenyldimethylsilyl) benzene, 4,4'-dimethylmethoxysilyl (phenyl) -1,1'-biphenylene, 1,4-chlorodimethylsilyl (phenyloxy) benzene, 1,2- (Phenyloxy) benzene, 1,3-dimethylmethoxysilyl (phenyloxy) benzene, 1,4-dimethylmethoxysilyl (phenylcarbonyl) benzene, 1,3-dimethylmethoxysilyl Nylcarboxy) benzene, and 1,2-dimethylmethoxysilyl (phenoxycarbonyl) benzene.

These organosilicon compounds can be synthesized, for example, according to the method described in Journal of Organometallic Chemistry (1998), 550 (1-2), 283-300.

When the organopolysiloxane of the present invention has at least one condensation-reactive functional group (for example, an alkoxy group) or a hydrosilylation-reactive functional group (for example, an alkenyl group) in the molecule, the organopolysiloxane But may be used as all or part of the main preparation of various functional resin compositions. For example, the curable silicone resin composition can be obtained by reacting the above-described organopolysiloxane having at least one condensation reactive functional group or hydrosilylation reactive functional group in the molecule, reactive silicone functioning as a crosslinking agent, and various functional fillers and curing reaction catalysts described below And then the surface of the functional filler is treated in the in-situ reaction system (integral blending method), and then the entire composition can be cured. In particular, the organopolysiloxane of the present invention has excellent blending stability for a silicone resin composition (hereinafter simply referred to as "silicone composition") such that the organopolysiloxane exhibits excellent properties of the functional filler in the cured product There is an advantage in that even when a large amount of these functional fillers are added, it is possible to provide a cured product or a non-curable composition which is uniform in its entirety and excellent in a desired function.

The organopolysiloxane of the present invention can be modified to have excellent thermal stability and to be provided with surface hydrophobicity, micro-dispersibility, and dispersion stability of the microparticles or microparticles having a highly micronized structure. Particularly, when used for the surface treatment of various functional fillers, there is no reduction in handling workability such as rapid thickening even when the filler is filled in the resin composition at a high concentration. Therefore, by using the organopolysiloxane of the present invention for the surface treatment agent, it is possible to fill the resin composition with various functional fillers which can not be added at high concentration or can not be stably dispersed by a commonly known surface treatment at a high concentration, A resin composition having high performance and excellent handling workability can be obtained. The use of the surface treatment agent of the organopolysiloxane of the present invention will be described below.

The surface treatment agent of the present invention comprises the above-described organopolysiloxane, and particularly preferably at least 50 mass% of the organopolysiloxane described above as a main preparation. Meanwhile, the surface treatment agent of the present invention can be used after dilution with a commonly known solvent or the like, and other additives such as an antioxidant, an antioxidant, a pigment, a dye, etc. can be used without departing from the object of the present invention Organosilicon compounds such as silane coupling agents or silylating agents, organic titanate compounds, organoaluminate compounds, organotin compounds, waxes, fatty acids, fatty acid esters, fatty acid salts or silanol condensation catalysts, A tin compound may be added to the surface treatment agent of the present invention. Examples of other surface treating compounds contained in the surface treatment agent of the present invention include silane compounds such as methyl (trimethoxy) silane, ethyl (trimethoxy) silane, hexyl (trimethoxy) silane, decyl (Trimethoxy) silane, 3 - glycidoxypropyl (trimethoxy) silane, 3 - methacryloxypropyltrimethoxysilane, 2 - [(3,4) - epoxycyclohexyl] (Trimethoxy) silane, 3-methacryloxypropyl (trimethoxy) silane, 3-acryloxypropyl (trimethoxy) silane and 1- (trimethoxy) 3,3,3-trimethylsiloxane . The present invention may also include other reactive silicone compounds within the range that does not inhibit the effects of the present invention.

The surface treatment agent of the present invention may be useful for treating various substrate surfaces, and the substrate to be treated is not particularly limited. Examples of substrates that can be surface-treated in addition to the various functional fillers described below include glass, for example, soda glass, heat ray reflecting glass, automotive glass, marine glass, aircraft glass, Glass, glass containers, and glassware; Metal sheets, such as copper, iron, stainless steel, aluminum, and zinc; Paper, for example, high-grade paper and straw paper; Synthetic resin films, for example, polyester resins, polycarbonate resins, polystyrene resins, and acrylic resins; Fibers or fabrics such as natural and synthetic fibers; A plastic substrate made of the above-mentioned synthetic resin; And various other materials such as ceramics and ceramics.

Further, the surface treatment agent of the present invention is useful as a surface treatment agent for various functional fillers, and can improve the surface properties of various functional fillers such as hydrophobicity, cohesiveness, fluidity, and dispersibility and compatibility in polymers, particularly curable resins . Although these functional fillers are not particularly limited, the surface treatment agent of the present invention can be selected from thermally conductive fillers, fluorescent fillers, electrically conductive fillers, dielectric fillers, insulating fillers, light-diffusing fillers, translucent fillers, The surface treatment agent can be used particularly suitably for the surface treatment of one type or two or more types of fillers, and even when the resin composition is filled with the filler at a high concentration, the surface treatment agent can achieve a desired function, It has an advantage that it can be improved without lowering the viscosity. At this time, the shape of the functional filler (spherical shape, rod shape, needle shape, plate shape, irregular shape, abundant shape, cocoon-shaped shape, etc.), particle size (aerosol shape, Crystal, porosity, non-porosity, etc.) is not limited, but the average primary particle size is preferably in the range of 1 nm to 100 탆. The shape of the functional filler and the average primary particle size can be appropriately selected according to the intended use and function, and it is also included in the preferred mode of the present invention to use a functional filler having a plurality of average primary particle sizes or the like to improve the filling rate do.

Examples of a method of treating the surface of such a functional filler include a method of spraying a surface treatment agent or a solution thereof (including a dispersion such as an organic solvent) at room temperature to 200 DEG C while stirring the functional filler using a stirrer, and then drying the mixture ; A method of mixing the functional filler and the surface treatment agent or a solution thereof in an agitator (including a grinder such as a bore mill or a jet mill, an ultrasonic dispersing apparatus, etc.), and then drying the mixture; And a treatment method of blending the treatment agent in a solvent, dispersing the functional filler to adsorb it on the surface, and then drying and baking the substrate. Another example is a method in which a functional filler and a surface treatment agent are added to a resin to which a functional filler is to be blended, and then the mixture is treated in situ (an integral blending method). The amount of the surface treatment agent to be added when treating the surface of the functional filler is preferably 0.1 to 50 parts by mass, particularly preferably 0.1 to 25 parts by mass, per 100 parts by mass of the functional filler.

In particular, the filler to be suitably treated by the surface treatment agent of the present invention may be one type selected from inorganic fillers, organic fillers, nanocrystal structures, quantum dots, and fillers in which some or all of their surfaces are covered by a silica layer or There are two or more types of fillers. They are well known as raw materials for thermally conductive materials, electrically conductive materials, semiconductor sealing materials, optical materials, functional paints, cosmetics and the like, and the surface treatment agents of the present invention are suitable for surface treatment of these fillers. However, when the metal oxide fine particles having a particle size of 1 to 500 nm or a part or all of the surface of the metal oxide fine particles are used as a surface treatment agent for fine particles coated with a silica layer, the fine dispersibility and dispersion stability in the hydrophobic curable resin and the silicone resin Can be remarkably improved and the function of the resulting curable resin can be improved.

The filler to be suitably treated by the surface treatment agent of the present invention is preferably an inorganic filler, particularly preferably a thermally conductive filler described below, but the present invention is not limited to this case.

The fluorescent filler is an inorganic particle, a nanocrystal structure, a quantum dot, or the like that emits fluorescence of a wavelength longer than the wavelength of the excitation light when the ultraviolet or visible excitation light is incident on the fine particles. Particularly, fine particles having an excitation band at a wavelength of 300 to 500 nm and an emission peak at a wavelength of 380 to 780 nm, particularly blue light (wavelength: 440 to 480 nm), green light (wavelength: 500 to 540 nm), yellow light To 595 nm), or red light (wavelength: 600 to 700 nm). Examples of phosphor particulates typically available on the market are garnet, other oxides, nitrides, oxynitrides, sulfides, oxides, rare earth sulfides, or Y ₃ Al ₅ O ₁₂ : Ce, (Y, Rare earth aluminic acid chloride or halophosphoric acid chloride which is mainly activated by a lanthanide element such as Ce represented by ₃ Al ₅ O ₁₂ : Ce, Y ₃ (Al, Ga) ₅ O ₁₂ : Ce or the like. Specific examples of these phosphor fine particles are inorganic phosphor fine particles disclosed in, for example, Japanese Unexamined Patent Application Publication No. 2012-052018.

The phosphor particles treated with the surface treatment agent of the present invention typically have an average particle size in the range of from 0.1 to 300 mu m and can be treated as a mixture of glass powders, for example, glass beads. In addition, the surface treatment agent may be used for treatment of a mixture containing a plurality of phosphor particles in accordance with a wavelength range of excitation light or light emission. For example, when white light is obtained by irradiating excitation light in an ultraviolet range, it may be preferable to surface-treat a mixture of fluorescent fine particles emitting blue, green, yellow and red fluorescence.

The nanocrystal structure - in particular, the semiconductor nanocrystal structure - can control the emission wavelength depending on the size of the nanocrystals and particles due to the quantum containment effect, and in particular, semiconductor nanocrystals, called quantum dots, Emitting semiconductor, for example, as an LED, in particular, as a light-emitting material or a fluorescent material, from the viewpoint that the wavelength of luminescence light emission can be controlled over the entire visible spectrum by controlling the particle size. It is useful as a radiator or wavelength conversion material to be converted. Such a nanocrystal structure consists of Si nanocrystals, II-VI compound semiconductor nanocrystals, III-V compound semiconductor nanocrystals, IV-VI compound semiconductor nanocrystals, and mixtures thereof. Particularly, II-VI group semiconductor nanocrystals typified by CdSe semiconductor, III-V group compound semiconductor nanocrystals typified by GaN semiconductor, and IV-VI group compound semiconductor nanocrystals represented by SbTe semiconductor are used. Such semiconductor nanocrystals can be obtained by gas-phase growth at a high temperature or can be colloidal-phase semiconductor nanocrystals synthesized by organic chemical methods (including vapor-phase processes). The nanocrystals may also have a core-shell structure.

The average particle size of the nanocrystal structure used in the light-emitting semiconductor, particularly the quantum dot, is in the range of about 0.1 nm to several tens nm and is selected according to the emission wavelength. By surface-treating these nanocrystals with the surface-treating agent of the present invention, it is possible to orient or bind the organopolysiloxane on the surface of the nanocrystals to prevent agglomeration of the organopolysiloxane, and to improve the fine dispersibility and dispersion stability, Properties and light extraction efficiency can be further improved.

The electrically conductive filler is a component used to provide electrical conductivity to the composition, examples being various types of carbon black; Metal powders such as silver, copper, iron and aluminum; Metal oxides such as zinc oxide and tin oxide; And an electrically conductive coated filler in which a core material, for example, barium sulfate or titanium oxide, is coated by these materials. In addition, various other surfactants can be blended into the composition as a conductivity-imparting agent, and they can be used in combination. Some of these are components that also function as thermally conductive fillers.

The dielectric filler is a ferroelectric filler, a dielectric filler, or a combination of the two, and the filler may provide a relatively high dielectric constant to allow the composition to store charge. Examples of these dielectric fillers are lead zirconate titanate, barium titanate, calcium methaniobate, bismuth methabite, methanoborate, methaniobasilan, strontium methaniobate, lead methaniobate, , Barium strontium titanate, barium sodium niobate, barium potassium niobate, barium rubidium niobate, titanium oxide, tantalum oxide, hafnium oxide, niobium oxide, aluminum oxide, and stearate. In particular, the treatment with barium titanate and titanium oxide is suitable from the viewpoint of improving the dielectric constant, but the present invention is not limited to such a case.

The insulating filler provides electrical insulation to the composition, and in addition to the thermally conductive filler described below, fumed silica, precipitated silica, fused silica, and the like can be used. Some or all of these are components that also function as reinforcing fillers.

The light-diffusing filler provides light diffusing properties to the composition, and in addition to calcium carbonate and barium sulfate, for example, crosslinked polymethyl methacrylate resin particles, silicone resin particles, polyorganosilsesquioxane particles, silica particles, Quartz particles, silica fibers, quartz fibers, and glass fibers. These light-diffusing fillers can be used in glass substitute applications, for example in light-diffusing plates in the field of liquid crystal displays, optical elements of optical lenses and optical waveguides, street lamp covers, and laminated glass for automotive and building materials, as well as cosmetics May be suitably used for spherical silicone particles intended to be used for wrinkle hiding (soft focus).

The translucent filler is composed of fine particles having a high refractive index and negligibly small light scattering property, and these fillers can provide a high refractive index and a high transparency to the composition. The surface treatment agent of the present invention can be suitably used for surface treatment of metal oxide fine particles used in an optical material. The average particle size of the metal oxide fine particles used as the translucent filler is in the range of 1 to 500 nm, particularly preferably 1 to 100 nm, and the range of 1 to 20 nm is more preferable in view of the transparency of the optical material containing the fine particles desirable. Further, for the purpose of improving the optical, electromagnetic, and mechanical properties of the optical material, these metal oxide fine particles may be nanocrystalline particles having a crystal diameter of 10 to 100 nm, and the nanocrystalline particles are also preferable. The translucent filler treated with the surface treatment agent of the present invention also has an excellent heat resistance when used in an optical semiconductor device or the like and has an advantage that the device is resistant to yellowing, discoloration and the like.

Examples of the metal oxide fine particles include barium titanate, zirconium oxide, aluminum oxide (alumina), silicon oxide (silica), titanium oxide, strontium titanate, barium zirconate titanate, cerium oxide, cobalt oxide, indium tin oxide, , Tin oxide, niobium oxide, and iron oxide. In particular, a metal oxide containing at least one type of metal element selected from titanium, zirconium and barium is preferable in terms of optical properties and electrical properties. Some of these are components that also function as thermally conductive fillers, dielectric fillers, or reinforcing fillers.

Particularly, zirconium oxide has a relatively high refractive index (refractive index: 2.2) and is therefore useful for optical material applications requiring high refractive index and high transparency. Likewise, barium titanate has a high dielectric constant and refractive index, and is useful for imparting optical and electromagnetic performance to organic materials. The surface treatment agent of the present invention can finely and stably disperse fine metal oxide particles in the hydrophobic curable resin as a result of the surface treatment of fine metal oxide particles such as barium titanate, thereby enabling more stable mass mixing than untreated fine particles. As a result, there is an advantage that the optical properties (in particular, high refractive index) and the electromagnetic properties of the resin composition obtained can be remarkably improved.

The reinforcing filler is a component to provide the high mechanical strength required depending on the application of the composition. Examples of such reinforcing fillers include fumed silica, precipitated silica, fused silica, and aerosol titanium oxide. These reinforcing fillers may have a surface hydrophobized with a polyorganosiloxane other than the organopolysiloxane of the present invention, hexamethyldisiloxane, or the like. In particular, from the viewpoint of improving the mechanical strength, it is preferable to use a reinforcing filler having a specific surface area of at least 130 cm ² / g as measured by the BET method.

Further, the surface treatment agent of the present invention is a commonly known reinforcing filler, and can be used for treatment of the substrate used in the functional resin composition. Examples include talc, clay, mica powder, glass powder (glass beads), glass frit, glass fabric, glass tape, glass mat, or a material whose surface is partially or wholly covered by a silica layer.

The surface treatment agent of the present invention is particularly useful when used in the surface treatment of a swellable layered clay material-particularly, a nano clay material-blended for the purpose of improving the mechanical properties, gas permeability or water vapor permeability of a functional resin composition, And the mechanical properties, gas permeability or water vapor permeability of the functional resin composition can be improved without deteriorating the blending ratio or dispersion stability of the functional resin composition. Herein, "nano-clay" refers to natural or synthetic, modified or unmodified ionic phyllosilicates having a predominantly stratified structure, examples being smectite clay minerals such as montmorillonite, especially sodium montmorillonite-bentonite; Hectorite; Saponite; Steven site; And smectite and hectorite clays containing filo silicates such as beidellite. Since the layered structure of the nanoclay has diffusion only in a one-dimensional direction in the nanometer range, delamination or expansion tends to occur easily, and when it is incorporated into the resin composition, it is separated from each other. Each release layer preferably has a thickness of less than 25 ANGSTROM (approximately 2.5 nm), more preferably less than 10 ANGSTROM (approximately 1 nm), most preferably 5 to 8 ANGSTROM (approximately 0.5 to 0.8 nm) (Aspect ratio) (length / width).

The surface treatment agent of the present invention may further be used in a synthetic or post-treatment step of a member in which the above-described functional filler or a part or all of its surface is covered with a silica layer. The method of use in the synthesis step or the post-treatment step is not particularly limited, but an example of a solid-phase method is a method in which the functional filler described above or a part or all of the surface of the functional filler described above is subjected to surface treatment with a silica layer Is treated with the surface treatment agent of the present invention and then the substrate is dispersed or finely pulverized using mechanical force or ultrasonic waves. Apparatuses known in the art for dispersing or grinding can be used without limitation.

The coating of the functional filler described above with the silica layer can be carried out by a conventionally known method. Examples of the method that can be used include a method of dispersing these fine members in an appropriate solvent and then adding an aqueous solution of sodium silicate under acidic conditions, a method of adding a silicate solution, or a method of adding a hydrolyzable 4-functional silane to an acidic or basic catalyst Lt; RTI ID = 0.0 > hydrolysis < / RTI >

On the other hand, the surface treatment of the present invention can also be used for the synthesis of functional fillers produced by the liquid phase method. When the surface treatment agent of the present invention is used in the liquid phase synthesis method, the particle surface of the resulting functional filler is partially or wholly covered with the organopolysiloxane of the present invention in the particle formation step. Accordingly, not only is there a merit that the material can be finely and uniformly dispersed in the redispersion step, but also the surface characteristics of the fine member produced by selecting the refractive index of the organosilicon compound or the type of the reactive functional group used are designed There is an advantage to be able to do. Further, by performing the liquid phase synthesis in the state in which the surface treatment agent of the present invention is carried out, it is possible to obtain a metal nanoparticle surface-treated at the time of synthesis, semiconductor nanoparticles, core-shell nanoparticles, doped nanoparticles, - plate and the like can be synthesized by an integrated process.

When the filler surface-treated with the organopolysiloxane and organopolysiloxane of the present invention is blended with various resin compositions, a large amount of various functional fillers are blended into the resin composition without deteriorating handling workability or dispersion stability of various functional fillers And has the advantage that a resin composition in which these functional fillers are stably packed at a high concentration can be obtained. These resin compositions are described below.

The resin part constituting the resin composition is not particularly limited as long as it can mix the organopolysiloxane of the present invention without deteriorating its practicality and is capable of containing or dispersing various functional fillers, Has a thickening, hardening or phase change property.

Herein, the thickening property does not significantly change the initial viscosity but exhibits a property of forming a gel or viscous liquid or paste form by heating under desired use conditions or increasing the total viscosity by using a thickener, and examples thereof include a grease composition and the like .

The curing property indicates that the composition is cured by heating or the like, and examples thereof include not only a hard coat resin composition and a semiconductor encapsulating resin composition but also a resin composition which can be formed into a sheet form, a resin composition which is cured into a gel state with flexibility, And a semi-curable resin composition for forming a soft rubber having plasticity.

The phase changeability is a function of filling the heat-softening resin having a softening point such as wax with a functional filler. The phase exhibits properties that vary depending on the operating temperature of the exothermic electronic part, for example, a so-called phase change material.

Such a resin component is not particularly limited, and examples thereof include hydrocarbon resins such as polyethylene, polypropylene, polymethylpentene, polybutene, crystalline polybutadiene, polystyrene, and styrene-butadiene resin; Vinyl resins such as polyvinyl chloride and polyvinyl acetate; Acrylic resins such as polymethylmethacrylate; Polyvinylidene chloride; Polytetrafluoroethylene; An ethylene-polytetrafluoroethylene resin; Ethylene-vinyl acetate resin; Acrylonitrile-styrene (AS) resins; Acrylonitrile-butadiene-styrene (ABS) resins; Acrylonitrile-acrylate-styrene (AAS) resins; Acrylonitrile-polyethylenechloride-styrene (ACS) resin; Polyacetals having ionomers and linear structures (engineering plastics); Polyamide (nylon); Polycarbonate; Polyphenylene oxide; Polyethylene terephthalate; Polybutylene terephthalate; Polyacrylates; Polysulfone; Polyethersulfone; Polyimide; Polyamide imide; Polyether ether ketone; Polyphenylene sulfite unsaturated polyester; Phenolic resin; Epoxy resin; A modified melamine resin; Fluorine resin; Silicone resin; Cellulose resins such as celluloid, cellophane, and cellulose acetate; Resin derived from natural rubber, for example, ebonite; And resins derived from proteins, such as gelatin.

The resin used in the present invention is preferably a thermosetting resin such as wax, an epoxy resin, a phenol resin, a silicone resin, a melamine resin, a urea resin, an unsaturated polyester resin, a diallyl terephthalate resin, (Meth) acrylic ester resin, benzocyclobutene resin, fluororesin, polyurethane resin, polycarbonate resin, norbornene resin, polyolefin resin, and polystyrene resin, which are selected from the group consisting of a resin, a polyimide resin, a polyamide resin, And at least one type of resin. The resin composition of the present invention is particularly preferably a silicone composition.

These resin compositions may be a curable resin composition or a thermoplastic resin composition, and may be an uncured or thickened resin composition. Further, when the resin is a heat-softening resin, it may be a phase-change material. The resin composition of the present invention can be used for various applications depending on the type of the functional filler and the resin, but in particular, the resin composition is used for a purpose selected from a thermally conductive material, an electrically conductive material, a semiconductor sealing material, an optical material, a functional coating material, Can be used.

In particular, surface-treated fillers by the organosilicon compounds and organosilicon compounds of the present invention are preferably blended into a silicone composition. Particularly, when used on the surface of the thermally conductive filler, even when the composition is filled with the thermally conductive filler at a high concentration to realize a high thermal conductivity, the handling workability is good without any increase in the viscosity of the composition. In the case of the curable composition, a uniform cured product can be obtained. The surface treatment and thermally conductive silicone composition of the thermally conductive filler which is the most suitable use of the organosilicon compound of the present invention will be described below.

The thermally conductive silicone composition of the present invention comprises the above-described organosilicon compound (A) and the thermally conductive filler (B), and the surface treatment of the thermally conductive filler using the organosilicon compound (A) Lt; / RTI >

Component (B) is a thermally conductive filler for providing thermal conductivity to the composition of the present invention and is preferably a thermally conductive filler for providing thermal conductivity to the composition of the present invention, preferably a pure metal, alloy, metal oxide, metal hydroxide, metal nitride, metal carbide, And ferrite. ≪ RTI ID = 0.0 > [0002] < / RTI > The component particularly preferably contains a thermally conductive material having a carbon system or a monofilamental appearance that does not contain a hydroxyl group on the surface and is expected to interact with an aromatic group. The powders and / or fibers used may be treated with various surface treating agents known as coupling agents.

Examples of pure metals include bismuth, lead, tin, antimony, indium, cadmium, zinc, silver, copper, nickel, aluminum, iron and metal silicon. Examples of alloys include alloys of two or more types of metals selected from the group including bismuth, lead, tin, antimony, indium, cadmium, zinc, silver, aluminum, iron and metal silicon. Examples of metal oxides include alumina, zinc oxide, silicon oxide, magnesium oxide, beryllium oxide, chromium oxide, and titanium oxide. Examples of metal hydroxides include magnesium hydroxide, aluminum hydroxide, barium hydroxide, and calcium hydroxide. Examples of metal nitrides include boron nitride, aluminum nitride, and silicon nitride. Examples of the metal carbide include silicon carbide, boron carbide, and titanium carbide. Examples of the metal silicide include magnesium silicide, titanium silicide, zirconium silicide, tantalum silicide, niobium silicide, chromium silicide, tungsten silicide, and molybdenum silicide. Examples of carbon include diamond, graphite, fullerene, carbon nanotubes, graphene, activated carbon, and amorphous carbon black. Examples of soft magnetic alloys include Fe-Si alloys, Fe-Al alloys, Fe-Si-Al alloys, Fe-Si-Cr alloys, Fe-Ni alloys, Fe-Ni-Co alloys, Fe- Co alloy, Fe-Si-Al-Cr alloy, Fe-Si-B alloy, and Fe-Si-Co-B alloy. Examples of the ferrite include Mn-Zn ferrite, Mn-Mg-Zn ferrite, Mg-Cu-Zn ferrite, Ni-Zn ferrite, Ni-Cu-Zn ferrite and Cu-Zn ferrite. Component (B) is preferably at least one type of powder and / or fiber selected from these components.

The thermally conductive filler (B) described above is particularly preferably (B1) a platelet boron nitride powder having an average particle size of 0.1 to 30 μm, (B2) a granular boron nitride powder having an average particle size of 0.1 to 50 μm , (B3) spherical and / or crushed aluminum oxide powder having an average particle size of 0.01 to 50 mu m, (B4) spherical and / or crushed graphite having an average particle size of 0.01 to 50 mu m, It is a mixture of the above types.

Examples of the shape of the component (B) include a spherical shape, a needle shape, a disk shape, a rod shape, a flat shape, an amorphous shape and a fibrous shape.

Examples of the surface treating agent for treating the powder and / or the fiber of the component (B) include a surfactant, a silane coupling agent, an aluminum coupling agent, and a silicone surface treatment agent.

In the present composition, the content of the component (B) is not particularly limited, but in order to form a silicone composition having excellent thermal conductivity, the content is preferably at least 30% by volume, more preferably 30 to 90% Still more preferably in the range of 60 to 90% by volume, particularly preferably in the range of 80 to 90% by volume. Likewise, in order to form a silicone composition having excellent thermal conductivity, the content of the component (B) is preferably at least 50% by mass, more preferably 70 to 98% by mass, particularly preferably 90% To 97% by mass.

Specifically, the content of the component (B) is preferably within a range of 100 to 3,500 parts by mass, more preferably within a range of 100 to 2,500 parts by mass, particularly preferably within a range of 100 to 2,500 parts by mass, relative to 100 parts by mass of the total of the components (A) Preferably in the range of 100 to 2,500 parts by mass. This is because, when the content of the component (B) is lower than the lower limit of the above-described range, the resulting silicone composition tends to become insufficient in thermal conductivity, while if the content exceeds the upper limit of the above- The viscosity of the composition is so high that the component (B) can not be uniformly dispersed into the resulting silicone composition or the handling workability thereof tends to be significantly lowered.

The organopolysiloxane of the component (C) is not particularly limited, but a hydrolyzable group bonded to a silicon atom in the molecule, for example, an alkoxy group, an alkoxyalkoxy group, an alkoxyoxy group, an acyloxy group or a trialkoxysilylalkyl group, Can be used as the organopolysiloxane.

The organopolysiloxane of component (C) is an organopolysiloxane having a monovalent hydrocarbon group having an aliphatic unsaturated bond to a silicon atom in the molecule and an organopolysiloxane having a hydrogen atom bonded to the silicon atom in the molecule, Organopolysiloxanes having a hydrolysable group bonded to a silicon atom may further be used.

In the organopolysiloxane having at least one monovalent hydrocarbon group having an aliphatic unsaturated bond to a silicon atom in the molecule, the monovalent hydrocarbon group having an aliphatic unsaturated bond is preferably a straight chain alkenyl group, particularly preferably a vinyl group , An allyl group, or a hexenyl group. Examples of the group bonded to the silicon atom other than the monovalent hydrocarbon group having an aliphatic unsaturated bond are monovalent hydrocarbon groups having no aliphatic unsaturated bond, and this group is preferably an alkyl group or an aryl group, more preferably 1 To 4 carbon atoms, and particularly preferably a methyl group or an ethyl group. The viscosity of such an organopolysiloxane at 25 캜 is not particularly limited, but is preferably in the range of 20 to 100,000 mPa s, more preferably in the range of 50 to 100,000 mPa 쨌 s, Is in the range of 50,000 mPa 占 퐏, particularly preferably in the range of 100 to 50,000 mPa 占 퐏. The molecular structure of such an organopolysiloxane is not particularly limited and may be, for example, a linear chain, a branched chain, a straight chain having some branches, a cyclic or a dendrimer (dendrimer type). Examples of such organopolysiloxanes include homopolymers having these molecular structures, copolymers composed of these molecular structures, or mixtures thereof.

Examples of such organopolysiloxanes include dimethylpolysiloxanes capped with dimethylvinylsiloxy groups at both ends of the molecule, dimethylpolysiloxanes capped with methylphenylvinylsiloxy groups at both ends of the molecule, dimethylsiloxane capped with dimethylvinylsiloxy groups at both ends of the molecule Siloxane-methylphenylsiloxane copolymers, dimethylsiloxane-methylvinylsiloxane copolymers capped with dimethylvinylsiloxy groups at both ends of the molecule, dimethylsiloxane-methylvinylsiloxane copolymers capped with trimethylsiloxy groups at both ends of the molecule, Methyl (3,3,3-trifluoropropyl) polysiloxane capped with a dimethylvinylsiloxy group at the end, a dimethylsiloxane-methylvinylsiloxane copolymer capped with a silanol group at both ends of the molecule, a silanol Dimethylsiloxane-methylvinylsiloxane-methylphenylsiloxane copolymers capped in groups, _{Learning: (CH 3) 3 SiO 1} /2 siloxane unit which is represented by the _{formula: (CH 3) 2 (CH} 2 = CH) siloxane units of the formula represented by SiO _1/2 CH ₃ SiO _3/2 represented by siloxane unit, and the _{formula: (CH 3) 2 SiO 2} /2 consisting of siloxane units represented by the organosiloxane copolymer, capped with silanol groups on the dimethyl polysiloxane, the molecular both ends capped with silanol groups at both ends of a molecule Dimethylpolysiloxane capped with trimethoxysiloxy groups at both ends of the molecule, dimethylsiloxane-methylphenylsiloxane copolymer capped with trimethoxysilyl groups at both ends of the molecule, methyldimethylsiloxane-methylphenylsiloxane copolymer at both ends of the molecule, Dimethylpolysiloxanes capped with trimethoxysilyl groups, dimethylpolysiloxanes capped with trimethoxysilyl groups, dimethylpolysiloxanes capped with trimethoxysilyl groups, dimethylpolysiloxanes capped with trimethoxysilyl groups, And mixtures thereof.

In the organopolysiloxane having at least one hydrogen atom bonded to silicon atoms in the molecule, examples of groups bonded to silicon atom bonds other than hydrogen atoms are monovalent hydrocarbon groups having no aliphatic unsaturated bond as described above, Preferably an alkyl group or an aryl group, more preferably an alkyl group having 1 to 4 carbon atoms, particularly preferably a methyl group or an ethyl group. The viscosity of such an organopolysiloxane at 25 캜 is not particularly limited, but is preferably in the range of 1 to 100,000 mPa 占 퐏, and particularly preferably in the range of 1 to 5,000 mPa 占 퐏. The molecular structure of such an organopolysiloxane is not particularly limited and may be, for example, a linear chain, a branched chain, a straight chain having some branches, a cyclic or a dendrimer (dendrimer type). Examples of such organopolysiloxanes include homopolymers having these molecular structures, copolymers composed of these molecular structures, and mixtures thereof.

In the organopolysiloxane having a hydrolyzable group bonded to a silicon atom in the molecule, the hydrolyzable group is preferably an alkoxy group, an alkoxyalkoxy group, an alkenoxy group, an acyloxy group, a silanol group, or a trialkoxysilylalkyl group to be.

Examples of such organopolysiloxanes include dimethylpolysiloxane capped with trimethoxysiloxy group (trimethylsiloxy group) at one end of the molecule, dimethylpolysiloxane capped with trimethoxysiloxy group (dimethylvinylsiloxy group) at one end of the molecule A dimethylsiloxane-methylphenylsiloxane copolymer capped with trimethoxysiloxy group (dimethylvinylsiloxy group) at one end of the molecule, a dimethylsiloxane-methylphenylsiloxane copolymer capped with trimethoxysiloxy group (dimethylvinylsiloxy group) at one end of the molecule Dimethylpolysiloxanes, dimethylpolysiloxanes capped with trimethoxysiloxy groups at both ends of the molecule, dimethylsiloxane-methylmethoxysiloxane copolymers capped with trimethylsiloxy groups at both ends of the molecule, capping with trimethylsiloxy groups at both ends of the molecule ≪ / RTI > dimethylsiloxane-methylethoxysiloxane copolymer at both ends of the molecule, trimethoxysiloxane (3-trimethoxysilylpropyl) -dimethylsiloxane copolymer capped with dimethyl (5-trimethoxysilylhexyl) groups at both ends of the molecule, a dimethylpolysiloxane capped with silanol groups at both ends of the molecule Dimethylpolysiloxanes, dimethylsiloxane-methylphenylsiloxane copolymers capped with silanol groups at both ends of the molecule, dimethylpolysiloxanes capped with methyldimethoxysiloxy groups at both ends of the molecule, capped with triethoxysiloxy groups at both ends of the molecule Dimethylpolysiloxanes, dimethylpolysiloxanes capped with trimethoxysilylethyl groups at both ends of the molecule, and mixtures of two or more of these components.

The method for producing the present composition is not particularly limited. For example, a production process [1] in which component (A) is mixed with component (B), component (C) is added in small amounts thereto, and the resulting composition is mixed can be used, or alternatively, (A) may be premixed with the component (C), and a small amount of the component (B) may be added thereto [2]. However, the production method [1] is particularly preferable. Various devices can be used as a mixing device, but a rotating / revolution mixing device (Awatori Neritaro series manufactured by Thinky Corp., UM-118 manufactured by UNIX Corp., UFO series manufactured by EME Corp., , A speed mixer manufactured by House-Child Corp., and the like) is preferable from the viewpoint of mixing efficiency.

The present invention is described in detail below based on examples, but the present invention is not limited to the examples. Note that the physical properties in the examples are values measured at 25 占 폚. The degree of polymerization in the formula is the average degree of polymerization.

[Example 1]

Synthesis of 1 - ((2-naphthyl) ethyl) -3- (n-octyl) -1,1 ', 3 ", 3" -tetramethyldioxolane

First, 103 g of ion-exchanged water and 48 g of concentrated hydrochloric acid were charged in a 200 ml four-necked flask equipped with a stirrer, a thermometer, a cooling tube and a dropping funnel in a nitrogen atmosphere, stirred and cooled to 10 캜 or lower. Then, 30.4 g (0.222 mol) of 1,1,3,3-tetramethyldioxolane was charged to the flask. Next, 82.0 g (0.387 mol) of n-octyldimethylchlorosilane was added dropwise into the mixture with water-cooling or air-cooling so that the temperature of the reaction solution did not exceed 10 캜. After completion of the dropwise addition, the mixture was stirred at 10 DEG C or lower for 2 hours. The reaction mixture was analyzed by gas chromatography (GLC), and it was estimated that the peak related to n-octyldimethylchlorosilane disappeared to complete the reaction. The reaction mixture was allowed to stand and the upper layer was subjected to mixing / washing liquid separation three times with 100 ml of ion exchange water, twice with 100 ml of a saturated aqueous sodium hydrogen carbonate solution and three times with 100 ml of a saturated sodium chloride aqueous solution. The mixture was dehydrated with anhydrous sodium sulphate and distilled under reduced pressure to give 62 g (yield: 65%) of a fraction of 61 to 65 ° C / 1 hPa. When this oil is analyzed by nuclear magnetic resonance (NMR) and infrared spectroscopy (IR), the fraction is 3- (n-octyl) -1,1 ', 3', 3 " Containing organopolysiloxane which is a silicon-bonded hydrogen atom-containing organopolysiloxane represented by tetramethyldiloxane. The purity of this siloxane according to GLC was 99.5%.

Further, a complex of 23.4 g of 2-vinylnaphthalene (purity: 93.9%, 0.142 mol), 22 g of toluene, and platinum and 1,3-divinyltetramethyldisiloxane was stirred in a nitrogen atmosphere with a stirrer, a thermometer, And a dropping funnel, and the mixture was mixed so that the amount of platinum metal was 5 ppm relative to the total mass of the reaction mixture, and the mixture was heated to 40 캜. Subsequently, 35.3 g (0.143 mol) of the above-described 3- (n-octyl) -1, ', 1 ", 3', 3" -tetramethyldisiloxane was added to the reaction solution Was added dropwise to the mixture while cooling with air. After completion of the dropwise addition, the mixture was stirred at 60 DEG C for 2 hours. IR analysis of the reaction mixture showed that the SiH peak originating from 3- (n-octyl) -1, ', 1 ", 3', 3" -tetramethyldisiloxane vinyltrimethoxysilane disappeared, . The reaction mixture was heated to 90 ° C / 1 hPa under reduced pressure to remove the solvent, low-boiling unreacted product, and the like, and 55.0 g of a reaction product (yield: 94%) was obtained. When these fractions were analyzed by NMR and IR, it was found that 1 - ((2-naphthyl) ethyl) -3- (n-octyl) -1,1 ' Lt; / RTI > is an organopolysiloxane.

[Example 2]

Synthesis of 1 - ((2-naphthyl) ethyl) -3 ', 3 ", 5', 5" -tetramethyl-3,5-dicylar-

The title compound was synthesized by replacing n-octyldimethylchlorosilane with (2-naphthyl) ethyldimethylchlorosilane and 2-vinylnaphthalene with 1,5-hexadiene in the same manner as in Example 1 , 40.3 g of material (yield: 69%) were obtained. When these fractions were analyzed by NMR and IR, it was found that 1 - ((2-naphthyl) ethyl) -3 ', 3' ', 5', 5 '' - tetramethyl-3,5- It was confirmed that it was an organopolysiloxane represented by Sen.

[Example 3]

Synthesis of α, ω-trimethylsilyl ((2-naphthyl) ethyl) -polydimethylsiloxane (polymerization degree: 25)

First, 2.41 g of 2-vinylnaphthalene (purity: 93.9%, 0.142 mol), 10 g of toluene, and a complex of platinum and 1,3-divinyltetramethyldisiloxane were stirred in a nitrogen atmosphere with a stirrer, a thermometer, Was added to a 100 ml four-necked flask equipped with a dropping funnel and mixed so that the amount of platinum metal was 5 ppm relative to the total mass of the reaction mixture, and the mixture was heated to 40 캜. Then, 27.5 g of?,? - trimethylsilylhydrogen-polymethylsiloxane (polymerization degree: 25, SiH = 0.55%) was added dropwise to the mixture with water or air cooling so that the temperature of the reaction solution did not exceed 50 ° C. After completion of the dropwise addition, the mixture was stirred at 60 DEG C or lower for 2 hours. The reaction mixture was analyzed by IR. As a result, it was estimated that the SiH peak originating from?,? - trimethylsilylhydrogen-polydimethylsiloxane disappeared and the reaction was terminated. The reaction mixture was heated to 90 ° C / 1 hPa under reduced pressure to remove the solvent, low-boiling unreacted products, and the like, and 28.9 g of reaction product (yield: 96%) was obtained. When this fraction was analyzed by NMR and IR, the fraction was found to be?,? -Trimethylsilyl ((2-naphthyl) ethyl) -polydimethylsiloxane (degree of polymerization: 25).

[Example 4]

Synthesis of α, ω-trimethylsilyl (1-naphthyl) -polydimethylsiloxane (polymerization degree: 50)

First, 50.05 g of?,? - trimethylsilylhydroxyl-polydimethylsiloxane (polymerization degree: 50, SiOH = 0.45%), 50 g of toluene and 1.7 g of diethylamine (0.023 mol) , A cooling tube and a dropping funnel, and 2.91 g (0.013 mol) of 1-naphthyldimethylchlorosilane were added at room temperature. After completion of the addition, the system was heated at 60 < 0 > C for 8 hours. The mixture was then cooled to room temperature. After removing the resulting salt by filtration, the filtrate was heated to 90 ° C / 1 hPa under reduced pressure to remove the solvent, low-boiling unreacted product and the like, and 51.0 g of reaction product (yield: 97%) was obtained. When this fraction was analyzed by NMR and IR, the fraction proved to be?,? -Trimethylsilyl (1-naphthyl) -polydimethylsiloxane (degree of polymerization: 50).

The thermally conductive silicone composition of the present invention is described in more detail below. In addition, the viscosity and thermal conductivity of the thermally conductive silicone composition were measured as follows.

(Viscosity of thermally conductive silicone composition)

The viscosity of the thermally conductive silicone composition at 25 캜 was measured using a TA Instruments rheometer (AR550). As a geometry, a parallel plate having a diameter of 20 mm was used. The gap was 200 mu m and the shear rate was 10.0 (l / s). A small viscosity value means that the viscosity of the thermally conductive silicone composition is small, thus indicating excellent handling workability.

(Thermal conductivity)

The thermal resistance at 25 占 폚 of the thermally conductive silicone grease composition having an area of 1 cm 占 1 cm and a thickness of 200 占 퐉 and 500 占 퐉 was measured with a C-Therm TCi thermal conductivity measuring apparatus manufactured by C-Therm Corp. , And the thermal conductivity was measured from this value.

[Example 5]

First, the _{formula: (nC 8 H 17) (} CH 3) 2 SiOSi (CH 3) 2 C 2 H 4 Np ( Here, Np is a 2-naphthyl group), a 10.3 mass obtained in Example 1 indicated by the parts of 79.6 parts by mass of spherical alumina powder having an average particle size of 12 占 퐉, 4.4 parts by mass of boron nitride having an average particle size of 20 占 퐉 and 8.8 parts by mass of boron nitride having an average particle size of 0.8 占 퐉, Filled into a container to prepare a thermally conductive silicone grease having a filler content of 70% by volume. This was mixed for 30 seconds using an AR-100 rotation / revolving mixer manufactured by Thinky Corp., and the mixture was scratched and mixed again for 30 seconds. The viscosity (shear rate 10.0 (l / s)) of this thermally conductive silicone grease was 100 Pa · s and the thermal conductivity was 4.5 W / m · K.

[Examples 6 to 11]

The thermally conductive silicone composition was prepared by changing the composition shown in Table 1 using the organopolysiloxane (1) and / or the organopolysiloxane (2) shown in Table 1 instead of the material obtained in Example 1 as the organopolysiloxane ≪ / RTI > was prepared using the same method as in Example 5. The viscosity (shear rate: 10.0 (1 / s)) and the thermal conductivity of this thermally conductive silicone composition are shown in Table 1. By using the organopolysiloxane of the present invention in part or all of the treating agent, it was possible to obtain a composition exhibiting a high thermal conductivity in the form of a paste having a practical level of viscosity and excellent uniformity.

[Comparative Examples 1 and 2]

The thermally conductive silicone composition was prepared by the same method as in Example 5 except that the organopolysiloxane shown in Table 2 was used instead of the material obtained in Example 1 as the organopolysiloxane and the composition shown in Table 2 was changed to ≪ / RTI > The viscosity (shear rate: 10.0 (1 / s)) and the thermal conductivity of this thermally conductive silicone composition are shown in Table 2. When the organopolysiloxane of this comparative example was used, the resulting composition did not form a uniform paste and its thermal conductivity could not be determined.

(**) The sample could not be measured because it did not form a uniform paste.

In the table, organopolysiloxane

(CH ₃ ) ₂ C ₂ H ₄ Np (wherein Np is a 2-naphthyl group) (* 1) (CH ₂ ═CHC ₄ H ₈ ) (CH ₃ ) ₂ SiOSi

(CH ₃ ) ₃ SiO ((CH ₃ ) ₂ SiO) _n Si (OCH ₃ ) ₃ (n (average) = 20)

(CH ₃ ) ₃ SiO ((CH ₃ ) ₂ SiO) _n Si (CH ₃ ) ₂ C ₂ H ₄ Np (n = 25)

(CH ₃ ) ₃ SiO (CH ₃ ) ₂ SiO) _n Si (CH ₃ ) ₂ C ₂ H ₄ Np (n (average) = 50)

_{(* 5) (CH 3)} 3 SiO ((CH 3) 2 SiO) n Si (CH 3) 2 Np (n ( average) = 25)

(6) (MeO) ₃ SiC ₃ H ₆ (CH ₃ ) ₂ SiOSi (CH ₃ ) ₂ C ₂ H ₄ Np (where Np is a 2-naphthyl group and Me is a methyl group)

(* 7) C ₈ H ₁₇ (CH ₃ ) ₂ SiOSi (CH ₃ ) ₂ (C ₈ H ₁₇ )

(CH ₃ ) ₃ SiO ((CH ₃ ) ₂ SiO) _n Si (CH ₃ ) ₃ (n (average) = 45)

(* 9) NpC ₂ H ₄ (CH ₃ ) ₂ SiOSi (CH ₃ ) ₂ C ₂ H ₄ Np (Np is a 2-naphthyl group)

In the table,

(* a) Spherical alumina powder having an average particle size of 12 mu m

(* b) Granular boron nitride having an average particle size of 20 mu m

(* c) Plate-type boron nitride having an average particle size of 0.8 mu m

(* d) Graphite having an average particle size of 20 mu m

[Example 12]

First, 6.0 parts by mass of an organopolysiloxane represented by the formula: (CH ₂ ═CHC ₄ H ₈ ) (CH ₃ ) ₂ SiOSi (CH ₃ ) ₂ C ₂ H ₄ Np (where Np is a 2-naphthyl group) 8.1 parts by mass of an organopolysiloxane represented by the formula CH ₂ CH (CH ₂ ) ₂ SiO ((CH ₃ ) ₂ SiO) _n Si (CH ₃ ) ₂ CH ₂ ═CH (n (average = 300) : 2.1 mass expressed by (CH ₃ ) ₃ SiO ((CH ₃ ) HSiO) _n ((CH ₃ ) ₂ SiO) _m Si (CH ₃ ) ₃ , 25.6 parts by weight of boron nitride having an average particle size of 20 mu m, 0.09 parts by weight of tetravinyltetramethylcyclotetrasiloxane, and 1,3-divinyltetramethyldisiloxane having a platinum content of 0.5% by weight 0.9 parts by mass of platinum complex was placed in a 100 ml vessel, which was mixed for 30 seconds using an AR-100 rotary / air mixer manufactured by Thinky Corp., and the mixture was scraped off and mixed again for 30 seconds . This composition was heated for 15 minutes at 150 DEG C to conduct the hydrosilylation reaction, thereby producing a thermally conductive silicone cured product (thickness: 1 mm and 2 mm). The thermal conductivity of this thermally conductive cured product was 5.5 W / m K.

[Comparative Example 3]

The thermally conductive silicone cured product can be obtained by reacting ((CH ₂ ═CHC ₄ H ₈ ) (CH ₃ ) ₂ SiOSi (CH ₃ ) ₂ C ₂ H ₄ NP (wherein Np is a 2-naphthyl group) instead of the organopolysiloxane Was prepared in the same manner as in Example 12 except that (C ₈ H ₁₇ ) (CH ₃ ) ₂ SiOSi (CH ₃ ) ₂ (C ₈ H ₁₇ ) was used. : 100 (l / s)) was 350, and since the viscosity was too high, it was difficult to obtain a uniform cured product.

Claims (17)

An organopolysiloxane represented by the following formula (1).
Formula 1

In Formula 1,
R ¹ is a monovalent hydrocarbon group having a plurality of aromatic rings and having at least 10 carbon atoms;
R ² is a direct bond to a divalent hydrocarbon group or silicon (Si) atom which may contain a heteroatom;
R ³ and R ⁴ are each independently selected from monovalent hydrocarbon groups;
R ⁵ is a divalent hydrocarbon group which may contain a hetero atom, or an oxygen atom;
R ⁶ is a group independently selected from an alkyl group, an alkenyl group, an aryl group, and an alkoxy group;
n is an integer from 0 to 200;
a is an integer of 1 to 3; A surface treatment agent comprising the organopolysiloxane of claim 1. 3. The method of claim 2, wherein the surface treatment of at least one type of filler selected from a thermally conductive filler, a fluorescent filler, an electrically conductive filler, a dielectric filler, an insulating filler, a light-diffusing filler, a translucent filler, a colorable filler, For use as a surface treatment agent. The method of claim 2, wherein the surface treatment agent is applied to at least one type of filler selected from inorganic fillers, organic fillers, nanocrystal structures, and quantum dots, wherein some or all of the surface of the filler A surface treatment agent which can be coated with a silica layer. A resin composition comprising the organopolysiloxane of claim 1 and a filler surface-treated with the organopolysiloxane of claim 1. 6. The resin composition according to claim 5 for use in applications selected from thermally conductive materials, electrically conductive materials, semiconductor encapsulating materials, optical materials, functional paints, and cosmetics. The resin composition according to claim 5 or 6, wherein the resin composition has a viscosity, curability, or phase changeability. A thermally conductive silicone composition comprising an organopolysiloxane (A) of Formula (1) and a thermally conductive filler (B). 9. The thermally conductive silicone composition of claim 8, further comprising at least one type of organopolysiloxane (C) other than the organopolysiloxane of formula (I). The method of claim 8 or 9, wherein the thermally conductive filler (B) is selected from the group consisting of pure metals, alloys, metal oxides, metal hydroxides, metal nitrides, metal carbides, metal suicides, carbon, soft magnetic alloys ), And ferrite. The thermally conductive silicone composition according to claim 1, wherein the thermally conductive silicone composition is at least one type of powder and / or fiber. The method of claim 10, wherein the pure metal is bismuth, lead, tin, antimony, indium, cadmium, zinc, silver, copper, nickel, aluminum, iron or metal silicon; or
The alloy consists of two or more types of metals selected from the group consisting of bismuth, lead, tin, antimony, indium, cadmium, zinc, silver, copper, nickel, aluminum, iron or metal silicon; or
Wherein the metal oxide is alumina, zinc oxide, silicon oxide, magnesium oxide, beryllium oxide, chromium oxide, or titanium oxide; or
The metal hydroxide is magnesium hydroxide, aluminum hydroxide, barium hydroxide, or calcium hydroxide; or
The metal nitride is boron nitride, aluminum nitride, or silicon nitride; or
The metal carbide is silicon carbide, boron carbide, or titanium carbide; or
Wherein the metal silicide is magnesium magnesium silicate, titanium silicide, zirconium silicide, tantalum silicide, niobium silicide, chromium silicide, tungsten silicide, or molybdenum silicide; or
The carbon is diamond, graphite, fullerene, carbon nanotubes, graphene, activated carbon, or amorphous carbon black; or
Wherein the soft magnetic alloy is selected from the group consisting of Fe-Si alloys, Fe-Al alloys, Fe-Si-Al alloys, Fe-Si-Cr alloys, Fe- Ni alloys, Fe- Co alloy, Fe-Si-Al-Cr alloy, Fe-Si-B alloy, or Fe-Si-Co-B alloy; or
Wherein the ferrite is Mn-Zn ferrite, Mn-Mg-Zn ferrite, Mg-Cu-Zn ferrite, Ni-Zn ferrite, Ni-Cu-Zn ferrite or Cu-Zn ferrite. 12. The method according to any one of claims 8 to 11, wherein the thermally conductive filler (B) is a platelet boron nitride powder (B1) having an average particle size of 0.1 to 30 mu m, an average particle size of 0.1 to 50 mu m Granular boron nitride powder (B2), spherical and / or pulverized aluminum oxide powder (B3) having an average particle size of 0.01 to 50 mu m, (B4) graphite having an average particle size of 0.01 to 50 mu m, Or mixtures of two or more of these types. 13. The thermally conductive silicone composition according to any one of claims 9 to 12, wherein the content of the component (B) is 100 to 3500 parts by mass per 100 parts by mass of the total of the component (A) and the component (C). 14. The thermally conductive silicone composition according to any one of claims 9 to 13, wherein the organopolysiloxane of component (C) has hydrolyzable functional groups bonded to silicon atoms in the molecule. The method according to any one of claims 9 to 14, wherein the component (C) is an organopolysiloxane having a monovalent hydrocarbon group having an aliphatic unsaturated bond to a silicon atom in the molecule, and an organopolysiloxane having a monovalent hydrocarbon group Wherein the component (C) further comprises a catalyst for thickening or curing the organopolysiloxane by a hydrosilylation reaction, wherein the organopolysiloxane has a hydrogen atom. 16. The method according to any one of claims 9 to 15, wherein the component (C) is an organosiloxane having a monovalent hydrocarbon group having a hydrolyzable functional group bonded to a silicon atom in the molecule and having an aliphatic unsaturated bond to a silicon atom Polysiloxane, and an organopolysiloxane having a hydrogen atom bonded to a silicon atom in the molecule, wherein the component (C) is selected from the group consisting of a thermally oxidized organopolysiloxane Conductive silicone composition. A gelatinous product or a cured product formed by thickening or curing the silicone composition of claim 15 or 16.