KR20220043775A - Resin Composition - Google Patents

Abstract

The present application provides a resin composition which has excellent flowability, permeability, low-viscosity properties, and storage stability, does not have powder contamination on a surface after curing, can be lightweight, and has excellent thermal conductivity per unit volume, and various uses of the resin composition.

Description

Resin Composition

This application relates to a resin composition and its use.

Heat dissipation materials are used in various fields. Taking a vehicle as an example, a heat-dissipating material may be used to treat heat generated from a battery module built in an electric vehicle capable of charging and discharging, an on-board charger (OBC) for charging the battery, and the like.

In addition, heat dissipation material is applied to parts that consume a lot of power, such as other LED modules, and generate a lot of heat, so that the lifespan of the LED module can be improved.

A heat-dissipating material may require very low viscosity characteristics and excellent permeability depending on the application. For example, a heat dissipation material used for potting a product having a narrow gap such as OBC or including a small device requires low viscosity for efficient potting.

In addition, when the heat dissipation material is used in a place requiring weight reduction or miniaturization, such as automobiles, it has as low a viscosity as possible, has excellent heat conduction properties per volume, and flowability and permeability are also required.

Heat dissipation materials are often prepared by blending a thermally conductive filler with a curable resin component.

However, in the case of mixing a large amount of thermally conductive filler in order to ensure high thermal conductivity, it is not easy to secure the flowability, permeability, low viscosity, and low specific gravity characteristics as described above.

In addition, when a heat dissipation material is constructed using a material having a low viscosity, a phenomenon in which powder is attached to the surface after curing of the heat dissipation material occurs, and this phenomenon adversely affects the performance of precise electric or electronic products.

In addition, although fillers having a relatively low specific gravity while having thermal conductivity are known, many of these fillers have high reactivity, contain water, and/or easily contain water. Therefore, in a state in which the curable resin component and the thermally conductive filler are blended, a change in viscosity and/or hardness may occur severely over time, and this phenomenon deteriorates the storage stability of the heat dissipation material.

In addition, thixotropic properties may be required for the heat dissipation material depending on the application. Thixotropy is a property in which the viscosity of a material changes with shear force, and the viscosity decreases as shear force acts.

However, it is a difficult problem to satisfy all of the above-described physical properties for a heat dissipation material (especially a heat dissipation material containing a large amount of filler to realize high thermal conductivity).

This application relates to a resin composition and its use.

In the present application, excellent flowability, permeability, thixotropy and low viscosity properties are secured when a large amount of a filler that is high in reactivity, contains water and/or easily contains water is secured, and the properties are changed over time. An object of the present invention is to provide a resin composition that is stably maintained as designed to ensure excellent storage stability.

In addition, in the present application, it is also another object of the present application to provide a resin composition that does not cause powder to stick on the surface after curing, can be lightweight, and has excellent thermal conductivity per unit volume.

The present application also aims to provide various uses of the resin composition.

Among the physical properties mentioned in this specification, the physical properties in which the measured temperature affects the physical properties are those measured at room temperature unless otherwise specified.

As used herein, the term room temperature refers to a natural temperature that is not heated or reduced, for example, any temperature within the range of about 10° C. to 30° C., for example, about 15° C., about 18° C., about 20° C., It means a temperature of about 23 ℃ or about 25 ℃. In addition, unless otherwise specified in this specification, the unit of temperature is °C.

As used herein, the term alkenyl group, unless otherwise specified, has 2 to 20 carbon atoms, 2 to 16 carbon atoms, 2 to 12 carbon atoms, 2 to 8 carbon atoms, or 2 to 4 carbon atoms straight chain, branched chain, or cyclic alkenyl group. may mean

In the present specification, the term alkyl group or alkoxy group, unless otherwise specified, is a straight chain, branched chain, or cyclic alkyl group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms, or 1 to 4 carbon atoms. Or it may mean an alkoxy group.

In the present specification, unless otherwise specified, the term aryl group refers to a compound containing a benzene structure, a compound containing a structure in which two or more benzenes are connected by a linker, or two benzenes each having one or two carbon atoms. It may mean a monovalent moiety derived from a compound comprising a covalently condensed or bonded structure or a derivative of any one of the above-mentioned compounds. The range of the aryl group as used herein may include a functional group commonly referred to as an aryl group, as well as a so-called aralkyl group or an arylalkyl group. The aryl group may be, for example, an aryl group having 6 to 25 carbon atoms, 6 to 21 carbon atoms, 6 to 18 carbon atoms, or 6 to 12 carbon atoms. Examples of the aryl group include a phenyl group, a dichlorophenyl group, a chlorophenyl group, a phenylethyl group, a phenylpropyl group, a benzyl group, a tolyl group, a xylyl group, or a naphthyl group.

The alkenyl group, alkoxy group, alkyl group, or aryl group may be optionally substituted with one or more substituents. In this case, the substituent includes a halogen such as chlorine or fluorine, an epoxy group such as a glycidyl group, an epoxyalkyl group, a glycidoxyalkyl group or an alicyclic epoxy group, an acryloyl group, a methacryloyl group, an isocyanate group, a thiol group, or a monovalent hydrocarbon Groups and the like may be exemplified, but are not limited thereto.

In the present specification, the term M unit usually refers to a so-called monofunctional siloxane unit that is sometimes expressed as (R ₃ SiO _1/2 ), and the term D unit is usually expressed as (R ₂ SiO _2/2 ). means a so-called difunctional siloxane unit with, the term T unit means a so-called trifunctional siloxane unit, which is sometimes represented by (RSiO _3/2 ), and the term Q unit is usually represented by (SiO _4/2 ) may mean so-called tetrafunctional siloxane units in some cases. In the formula of each siloxane unit, R is a functional group bonded to silicon (Si), and may be, for example, hydrogen, an alkyl group, an alkenyl group, an aryl group, an alkoxy group, or an epoxy group.

The resin composition of the present application may include at least a curable resin component and a filler.

The resin composition of the present application may be a so-called addition-curable silicone resin composition. Such a resin composition includes, as the curable resin component, an alkenyl group-containing polyorganosiloxane component and/or a silicon-bonded hydrogen-containing polyorganosiloxane component. This type of resin composition is cured by reaction (hydrosilylation reaction product) of an alkenyl group of the polyorganosiloxane component containing an alkenyl group with hydrogen of the polyorganosiloxane component containing silicon-bonded hydrogen.

Accordingly, in this case, the curable resin component may be a curable polyorganosiloxane component.

In one example, the resin composition may be a one-component resin composition, a main or curing agent part of a two-component resin composition, or a main part and a curing agent part of a two-component resin composition, or a mixture thereof. The one-component resin composition is a resin composition in which the curable components are stored in a mixed state, and the two-component resin composition is a resin composition in which the curable components are stored separately as a main part and a curing agent part. In the case of a two-component resin composition, the main agent and the curing agent composition are mixed under conditions in which curing can occur at the time of use.

In one example, the resin composition may be a two-component resin composition. In a two-component resin composition, the main part and the curing agent part are physically separated from each other, and components of the composition are included in each of the main part and the curing agent part.

In such a two-component resin composition, the main agent and curing agent parts are mixed under conditions in which curing can occur at the time of use.

When the addition curable silicone resin composition is composed of a two-component type, the main part usually includes an alkenyl group-containing polyorganosiloxane component and a catalyst, the curing agent part includes a silicon-bonded hydrogen-containing polyorganosiloxane component, and the curing agent part includes the catalyst not included. The curing agent part may include an alkenyl group-containing polyorganosiloxane component along with a silicon-bonded hydrogen-containing polyorganosiloxane component.

The term polyorganosiloxane component may mean a mixture of polyorganosiloxanes and/or a mixture of polyorganosiloxanes and siloxane monomers. In a specific example, the polyorganosiloxane component may be a result of a polymerization reaction performed to obtain a specific target polyorganosiloxane. That is, when the monomers are mixed and polymerized to obtain the desired polyorganosiloxane, a plurality of polymer components (polyorganosiloxanes) are generated while the monomer is polymerized, and depending on the polymerization efficiency, some oligomeric components or monomer components may also exist after polymerization. can Accordingly, in the present application, the term polyorganosiloxane component refers to a result of the polymerization reaction as described above, a product obtained by removing the oligomeric component and/or monomer component by purification after the polymerization reaction, or a mixture of two or more types of the polymerization reaction product or purified product. can mean

The resin composition of the present application may include, as a curable resin component, an alkenyl group-containing polyorganosiloxane component and a silicon-bonded hydrogen-containing polyorganosiloxane component. In the case of a two-component resin composition, the alkenyl group-containing polyorganosiloxane component may be included in the main part, and the silicon-bonded hydrogen-containing polyorganosiloxane component may be included in the curing agent part. In addition, the curing agent part may further include an alkenyl group-containing polyorganosiloxane component that is the same as or different from that included in the main part.

As the alkenyl group-containing polyorganosiloxane component, a known polyorganosiloxane component may be used without any particular limitation. In one example, as the polyorganosiloxane component, a polyorganosiloxane component including a straight-chain polyorganosiloxane may be used.

The straight-chain polyorganosiloxane is a polyorganosiloxane having a structure in which both ends of a chain structure composed of D units are blocked by M units.

In the above structure, various types of units may be used as the D unit. For example, as the D unit, a so-called dialkylsiloxane unit (a bifunctional siloxane unit in which R is an alkyl group in the R ₂ SiO _2/2 structure), a diarylsiloxane unit (in the R ₂ SiO _2/2 structure, R is A bifunctional siloxane unit in which all are aryl groups), a dialkenylsiloxane unit (a bifunctional siloxane unit in which R is all alkenyl groups in the R ₂ SiO _2/2 structure), and an alkylarylsiloxane unit (one R in the R ₂ SiO _2/2 structure) A difunctional siloxane unit in which this alkyl group and another R is an aryl group), an alkylalkenylsiloxane unit (a bifunctional siloxane unit in which one R is an alkyl group and the other R is an alkenyl group in the R ₂ SiO _2/2 structure) and arylal At least one unit selected from the group consisting of a kenyl siloxane unit (a bifunctional siloxane unit in which one R is an alkenyl group and the other R is an aryl group in the R ₂ SiO _2/2 structure) may be applied.

Suitable D units include, among the above, a dialkylsiloxane unit (a bifunctional siloxane unit in which R is all alkyl groups in the R ₂ SiO _2/2 structure) and/or an alkylalkenylsiloxane unit (one of the above in the R ₂ SiO _2/2 structure) a difunctional siloxane unit wherein R is an alkyl group and other R is an alkenyl group).

In the structure of the straight-chain polyorganosiloxane, as M units at both ends of the chain structure consisting of D units, for example, an alkenyldialkylsiloxane unit (R ₃ In the SiO _1/2 structure, one of R is an alkenyl group, and the remaining monofunctional siloxane units in which two are alkyl groups) and/or trialkylsiloxane units (monofunctional siloxane units in which R is all alkyl groups in the R ₃ SiO _1/2 structure) and the like may be exemplified. For example, in the case of a structure in which both ends are terminated with alkenyl groups, as the M unit, an alkenyldialkyl siloxane unit may be used.

In one example, as the polyorganosiloxane having an alkenyl group, the D unit of the main chain structure of the straight-chain polyorganosiloxane is a dialkylsiloxane unit (a bifunctional siloxane unit in which R is all alkyl groups in the R ₂ SiO _2/2 structure) and / or an alkylalkenylsiloxane unit (a bifunctional siloxane unit in which one R is an alkyl group and the other R is an alkenyl group in the R ₂ SiO _2/2 structure), and M units at both ends are an alkenyldialkylsiloxane unit (R ₃ Polyorganosiloxane, which is a monofunctional siloxane unit in which one of R is an alkenyl group and the other two are alkyl groups in the SiO _1/2 structure) may be used.

When more than one type of D unit is used as the D unit of the main chain, the main chain may be in the form of a main chain of a random copolymer, a block copolymer, or a gradient copolymer.

The alkenyl group-containing polyorganosiloxane component may be represented by an average unit formula of the following Chemical Formula 1 in one example. In the present specification, the term average unit formula is a unit formula expressed by converting the ratio of the number of moles of all siloxane units (M, D, T and Q units) present in the polyorganosiloxane component to when the total number of moles of all the siloxane units is 1. .

[Formula 1]

(R ¹ R ² ₂ SiO _1/2 ) _a (R ² ₃ SiO _1/2 ) _b (R ² ₂ SiO _2/2 ) _c (R ¹ R ² SiO _2/2 ) _d

In Formula 1, R ¹ is an alkenyl group, R ² is an alkyl group or an aryl group, a+b is a number within the range of 0.001 to 0.1, and c+d is a number within the range of 0.8 to 0.999. Also, in Formula 1, b/a may be a number within the range of 0 to 1000, and d/c may be a number within the range of 0 to 2.

In Formula 1, a+b+c+d is 1.

In Formula 1, a+b is 0.003 or more, 0.005 or more, 0.007 or more, 0.009 or more, 0.011 or more, 0.013 or more, 0.015 or more, 0.017 or more, or 0.019 or more, or 0.08 or less, 0.06 or less, 0.04 or less, 0.03 or less, or It may be about 0.025 or less.

In Formula 1, c + d may be 0.82 or more, 0.84 or more, 0.86 or more, 0.88 or more, 0.9 or more, 0.92 or more, 0.94 or more, 0.96 or more, or 0.98 or more, or 0.995 or less, 0.99 or less, or 0.985 or less.

The alkenyl group-containing polyorganosiloxane component may be a component including the polyorganosiloxane of Formula 2 below. For example, the component may include polyorganosiloxane represented by the following formula (2) while being represented by the average unit formula of formula (1).

[Formula 2]

In Formula 2, R ₁ is an alkenyl group, R ₂ is an alkyl group or an aryl group, and n is a number within the range of 10 to 200.

In Formula 2, n is 20 or more, 40 or more, 50 or more, 60 or more, 70 or more, 80 or more, or 85 or more, or 190 or less, 180 or less, 170 or less, 160 or less, 150 or less, 140 or less, 130 or less in another example. , 120 or less, 110 or less, 100 or less, or 95 or less.

The alkenyl group-containing polyorganosiloxane component may include an alkenyl group in an amount of about 0.01 to 10 mmol/g. In another example, the ratio of the alkenyl group is about 0.05 mmol/g or more, 0.1 mmol/g or more, 0.15 mmol/g or more, 0.2 mmol/g or more, or 0.25 mmol/g or more, or 9.5 mmol/g or less, 9 mmol/g or less. g or less, 8.5 mmol/g or less, 8 mmol/g or less, 7.5 mmol/g or less, 7 mmol/g or less, 6.5 mmol/g or less, 6 mmol/g or less, 5.5 mmol/g or less, 5 mmol/g or less , 4.5 mmol/g or less, 4 mmol/g or less, 3.5 mmol/g or less, 3 mmol/g or less, 2.5 mmol/g or less, 2 mmol/g or less, 1.5 mmol/g or less, 1 mmol/g or less, 0.8 It may be about mmol/g or less, 0.6 mmol/g or less, 0.4 mmol/g or less, or 0.35 mmol/g or less.

The content of the alkenyl group and the silicon-bonded hydrogen content of the polyorganosiloxane component mentioned in the present specification is a value obtained through ¹ H NMR and/or ²⁹ Si NMR analysis described in Examples to be described later for the polyorganosiloxane component. . This method is different from the value theoretically obtained through the chemical formula of the polyorganosiloxane included in the polyorganosiloxane component. That is, since there are various types of polyorganosiloxanes that belong to the same category of chemical formula but may have different detailed structures within the polyorganosiloxane component, in this way the exact ratio of the curable functional groups (alkenyl groups and silicon bonds) The exact ratio between hydrogens) cannot be confirmed.

The ratio plays an important role such as desired flowability, permeability, thixotropy, low viscosity characteristics, low specific gravity characteristics, light weight, storage stability and/or properties capable ^of preventing powder contamination after curing, which is It should be determined based on H NMR and/or ²⁹ Si NMR analysis results.

The content of all alkenyl groups, the content of silicon-bonded hydrogen, the ratio of alkenyl groups and/or the ratio of alkenyl groups and silicon-bonded hydrogen, etc. mentioned in this specification are the desired flowability, permeability, thixotropy, low viscosity characteristics, low specific gravity It is adjusted in consideration of properties, lightness, storage stability and/or properties that can prevent powder contamination after curing.

The alkenyl group-containing polyorganosiloxane component may have a weight average molecular weight of 30000 or less in one example. In the present application, the term weight average molecular weight is a molecular weight obtained by the method of Examples to be described later using GPC (Gel Permeation Chromatograph), and the unit is g/mol. Unless otherwise specified, in the present specification, the molecular weight of the polyorganosiloxane component means the weight average molecular weight of the polyorganosiloxane component.

The molecular weight (Mw) is 28000 or less, 26000 or less, 24000 or less, 22000 or less, 20000 or less, 18000 or less, 16000 or less, or 14000 or less, or 500 or more, 1000 or more, 5000 or more, 10000 or more, 11000 or more, 12000 or less in another example. or more or 13000 or more.

In addition, the alkenyl-containing polyorganosiloxane component may have a molecular weight distribution in the range of 1.3 to 3. The molecular weight distribution is a value obtained by dividing the weight average molecular weight (Mw) of the polyorganosiloxane component by the number average molecular weight (Mn). The molecular weight distribution may be about 1.5 or more, 1.7 or more, or 1.9 or more, or about 2.8 or less, 2.6 or less, 2.4 or less, 2.2 or less, or 2.0 or less.

When a polyorganosiloxane component having such molecular weight characteristics is used, a resin composition suitable for the purpose can be more efficiently provided.

As the polyorganosiloxane component having silicon-bonded hydrogen, a known material may be used without any particular limitation. For example, as the polyorganosiloxane component, a linear polyorganosiloxane, that is, a component including a polyorganosiloxane having a structure in which both ends of a chain structure consisting of D units are blocked by M units may be used.

In the above structure, various types of units may be used as the D unit. For example, as the D unit, a so-called dialkylsiloxane unit (a bifunctional siloxane unit in which R is an alkyl group in the R ₂ SiO _2/2 structure), a diarylsiloxane unit (in the R ₂ SiO _2/2 structure, R is A bifunctional siloxane unit in which all are aryl groups), a dihydrogensiloxane unit (a bifunctional siloxane unit in which R is all hydrogen in the R ₂ SiO _2/2 structure), and an alkylarylsiloxane unit (one R in the R ₂ SiO _2/2 structure) This alkyl group and the other R is an aryl group), an alkylhydrogensiloxane unit (a bifunctional siloxane unit in which one R is an alkyl group and the other R is hydrogen in the R ₂ SiO _2/2 structure) and arylhydrogen At least one unit selected from the group consisting of a siloxane unit (a bifunctional siloxane unit in which one R is hydrogen and the other R is an aryl group in the R ₂ SiO _2/2 structure) may be applied.

Suitable D units include, among others, a dialkylsiloxane unit (a bifunctional siloxane unit in which R is all alkyl groups in the R ₂ SiO _2/2 structure) and/or an alkylhydrogensiloxane unit (one R in the R ₂ SiO _2/2 structure) A difunctional siloxane unit in which this alkyl group and other R is hydrogen) can be exemplified.

In the structure of the straight-chain polyorganosiloxane, as M units at both ends of the chain structure consisting of D units, for example, a hydrogen dialkylsiloxane unit (R ₃ SiO _1/2 structure in which one of R is hydrogen, and the remaining monofunctional siloxane units in which two are alkyl groups) and/or trialkylsiloxane units (monofunctional siloxane units in which R is all alkyl groups in the R ₃ SiO _1/2 structure) and the like may be exemplified. For example, as the M unit in the case of a structure in which both ends are terminated with silicon-bonded hydrogen, a hydrogendialkyl siloxane unit may be used.

The silicon-bonded hydrogen-containing polyorganosiloxane component may be represented by an average unit formula of the following Chemical Formula 3 in one example.

[Formula 3]

(HR ² ₂ SiO _1/2 ) _e (R ² ₃ SiO _1/2 ) _f (R ² ₂ SiO _2/2 ) _g (HR ² SiO _2/2 ) _h

In Formula 3, R ² is an alkyl group or an aryl group, e is a number in the range of 0 to 0.01, f is a number in the range of 0.001 to 0.1, g is a number in the range of 0.05 to 0.95, and h is 0.05 to 0.95 is a number within the range of

In Formula 3, e+g+f+h is 1.

In Formula 3, e may be 0.0001 or more, 0.0005 or more, 0.001 or more, 0.002 or more, 0.003 or more, 0.004 or more, or 0.0045 or more, or 0.008 or less, 0.006 or less, 0.004 or less, 0.002 or less, or 0.001 or less in another example.

In Formula 3, f in another example may be 0.003 or more, 0.005 or more, 0.007 or more, 0.01 or more, 0.15 or more, 0.2 or more, 0.25 or more, 0.3 or more, or 0.35 or more, or 0.08 or less, 0.06 or less, 0.04 or less, or 0.03 or less. .

In Formula 3, g is 0.1 or more, 0.15 or more, 0.2 or more, 0.25 or more, 0.3 or more, 0.35 or more, 0.4 or more, 0.45 or more, 0.5 or more, 0.55 or more, 0.6 or more, 0.65 or more, 0.7 or more, or 0.75 or more, or , 0.9 or less, 0.85 or less, 0.8 or less, 0.75 or less, 0.7 or less, 0.65 or less, 0.6 or less, or 0.55 or less.

In Formula 3, h is 0.1 or more, 0.15 or more, 0.2 or more, 0.25 or more, 0.3 or more, 0.35 or more, or 0.4 or more, or 0.9 or less, 0.85 or less, 0.8 or less, 0.75 or less, 0.7 or less, 0.65 or less, 0.6 or less , 0.55 or less, 0.5 or less, or about 0.45 or less.

The silicon-bonded hydrogen-containing polyorganosiloxane component may contain about 0.1 to 20 mmol/g of silicon-bonded hydrogen. The content of silicon-bonded hydrogen is, in another example, 0.3 mmol/g or more, 0.5 mmol/g or more, 0.7 mmol/g or more, 0.9 mmol/g or more, 1.1 mmol/g or more, 1.3 mmol/g or more, 1.5 mmol/g g or more, 1.7 mmol/g or more, 1.9 mmol/g or more, 2.1 mmol/g or more, 2.3 mmol/g or more, 2.5 mmol/g or more, 2.7 mmol/g or more, 2.9 mmol/g or more, 3.1 mmol/g or more , 3.3 mmol/g or more, 3.5 mmol/g or more, 3.7 mmol/g or more, 3.9 mmol/g or more, or 4.1 mmol/g or more, or 15 mmol/g or less, 10 mmol/g or less, 9 mmol/g or less, 8 mmol/g or less, 7 mmol/g or less, 6 mmol/g or less, 5 mmol/g or less, 4 mmol/g or less, 3 mmol/g or less, 2 mmol/g or less, or 1 mmol/g or less. .

When the silicon-bonded hydrogen-containing polyorganosiloxane component includes both the polyorganosiloxanes of Formulas 4 and 5 as described below, the hydrogen content ratio of the silicon-bonded hydrogen-containing polyorganosiloxane is 0.1 mmol/g or more, 0.3 mmol /g or more, 0.5 mmol/g or more, 0.7 mmol/g or more, 0.9 mmol/g or more, 1.1 mmol/g or more, 1.3 mmol/g or more, 1.5 mmol/g or more, 1.7 mmol/g or more, 1.9 mmol/g or more, 2.1 mmol/g or more, 2.3 mmol/g or more, 2.5 mmol/g or more, 2.7 mmol/g or more, 2.9 mmol/g or more, 3.1 mmol/g or more, 3.3 mmol/g or more, or 3.5 mmol/g or more; , 15 mmol/g or less, 10 mmol/g or less, 9 mmol/g or less, 8 mmol/g or less, 7 mmol/g or less, 6 mmol/g or less, 5 mmol/g or less, or 4 mmol/g or less there is.

If the silicon-bonded hydrogen-containing polyorganosiloxane component includes only the polyorganosiloxane of Formula 5 among the polyorganosiloxanes of Formulas 4 and 5 as described below, the hydrogen content ratio of the silicon-bonded hydrogen-containing polyorganosiloxane is 0.1 mmol/ g or more, 0.3 mmol/g or more, 0.5 mmol/g or more, 0.7 mmol/g or more, 0.9 mmol/g or more, 1.1 mmol/g or more, 1.3 mmol/g or more, 1.5 mmol/g or more, 1.7 mmol/g or more or 1.9 mmol/g or more, 15 mmol/g or less, 10 mmol/g or less, 9 mmol/g or less, 8 mmol/g or less, 7 mmol/g or less, 6 mmol/g or less, 5 mmol/g or less, It may be about 4 mmol/g or less, 3 mmol/g or less, or 2 mmol/g or less.

The silicon-bonded hydrogen-containing polyorganosiloxane component may include polyorganosiloxanes represented by Chemical Formulas 4 and/or 5 below. In the above, the polyorganosiloxane of Formula 4 and the polyorganosiloxane of Formula 5 are referred to as polyorganosiloxane for convenience, but may substantially each be a polyorganosiloxane component. That is, the polyorganosiloxane of Formula 4 is a result of polymerization to form the polyorganosiloxane of Formula 4, and the polyorganosiloxane of Formula 5 may be a result of polymerization to form the polyorganosiloxane of Formula 5 . The silicon-bonded hydrogen-containing polyorganosiloxane component including the polyorganosiloxane of Formulas 4 and/or 5 may or may not have the average unit of Formula 3 above.

[Formula 4]

In Formula 4, R ₃ is an alkyl group or an aryl group, and m is a number within the range of 10 to 1,000,

In Formula 4, m is 20 or more, 30 or more, 40 or more, 50 or more, 60 or more, 70 or more, 80 or more, 90 or more, 100 or more, 110 or more, 120 or more, 130 or more, or 140 or more, or 900 or less in another example. , 800 or less, 700 or less, 600 or less, 500 or less, 400 or less, 300 or less, or 200 or less.

The polyorganosiloxane of Formula 4 (a polyorganosiloxane component including the polyorganosiloxane of Formula 4) may contain about 0.01 to 5 mmol/g of silicon-bonded hydrogen. The content of silicon-bonded hydrogen is, in another example, 0.05 mmol/g or more, 0.07 mmol/g or more, 0.09 mmol/g or more, 0.1 mmol/g or more, 0.15 mmol/g or more, 0.2 mmol/g or more, 0.25 mmol/g or more g or more, 0.3 mmol/g or more, 0.5 mmol/g or more, 0.7 mmol/g or more, 0.9 mmol/g or more, 1.5 mmol/g or more, 2 mmol/g or more, or 2.5 mmol/g or more, or 5 mmol/g Hereinafter, it may be about 4 mmol/g or less or 3 mmol/g or less.

In addition, when the polyorganosiloxane of Formula 2 is included in the alkenyl-containing polyorganosiloxane component, the ratio (m/n) of n of Formula 2 and m of Formula 4 is in the range of about 0.5 to 5 can tomorrow In another example, the ratio (m/n) may be 0.7 or more, 0.9 or more, 1.1 or more, 1.3 or more, 1.5 or more, or 1.6 or more, or 4.5 or less, 4 or less, 3.5 or less, 3 or less, 2.5 or less, or 2 or less.

The total number of alkenyl groups included in the alkenyl group-containing polyorganosiloxane component of the total number of moles (H4) of silicon-bonded hydrogen included in the polyorganosiloxane of Formula 4 (polyorganosiloxane component including the polyorganosiloxane of Formula 4) The ratio (H4/Ak) of the number of moles (Ak) may be in the range of about 0.3 to 10. In another example, the ratio (H4) is 0.5 or more, 0.7 or more, 0.9 or more, 1.5 or more, 2 or more, 2.5 or more, 3 or more, or 3.5 or more, or 9.5 or less, 9 or less, 8.5 or less, 8 or less, 7.5 or less, 7 or less, 6.5 or less, 6 or less, 5.5 or less, 5 or less, 4.5 or less, or 4 or less, 3.5 or less, 3 or less, 2.5 or less, 2 or less, or 1.5 or less.

The silicon-bonded hydrogen-containing polyorganosiloxane component may include the polyorganosiloxane represented by the following formula (5) either alone or together with the polyorganosiloxane of the formula (4).

[Formula 5]

In Formula 5, R ₁ is hydrogen, an alkyl group, or an aryl group, R ₂ is an alkyl group or an aryl group, p is a number within the range of 1 to 60, and q is a number within the range of 5 to 80.

In Formula 5, p is 3 or more, 5 or more, 7 or more, 9 or more, 15 or more, 20 or more, 25 or more, or 30 or more, or 55 or less, 50 or less, 45 or less, 40 or less, 35 or less, 30 or less in another example. , 28 or less or 26 or less.

In Formula 5, q is 7 or more, 9 or more, 11 or more, 13 or more, 15 or more, 17 or more, or 19 or more, or 75 or less, 70 or less, 65 or less, 60 or less, 55 or less, 50 or less, 45 or less in another example. , 40 or less, 35 or less, 30 or less, 25 or less, 20 or less, or 15 or less.

A ratio (p/q) of p and q in Formula 5 may be in the range of 0.5 to 10. In another example, the ratio (p/q) is 0.7 or more, 0.9 or more, 1.1 or more, 1.3 or more, 1.5 or more, 1.7 or more, 1.9 or more, 2.1 or more, or 2.3 or more, or 9 or less, 8 or less, 7 or less, 6 or less , 5 or less, 4 or less, 3 or less, 2 or less, or 1.5 or less.

When the silicon-bonded hydrogen-containing polyorganosiloxane component simultaneously includes the polyorganosiloxanes of Chemical Formulas 4 and 5, the ranges of p and q may be further controlled.

For example, when the silicon-bonded hydrogen-containing polyorganosiloxane component simultaneously includes the polyorganosiloxane of Formula 4 and the polyorganosiloxane of Formula 5, p in Formula 5 may be 28.5 or more, and q may be 17 or less .

In this case, p in another example may be 29 or more, 29.5 or more, 30 or more, 30.5 or more, 31 or more, or 31.5 or more, or 60 or less, 55 or less, 50 or less, 45 or less, 40 or less, or 35 or less.

In addition, in the above case, q may be 5 or more, 7 or more, 9 or more, or 11 or more, or about 15 or less or 13 or less in another example.

In addition, in the above case, the ratio of p and q (p/q) may be in the range of 1.95 to 10. In another example, the ratio (p/q) may be 2.1 or more or 2.3 or more, or 9 or less, 8 or less, 7 or less, 6 or less, 5 or less, 4 or less, or 3 or less.

In addition, as described below, if the silicon-bonded hydrogen-containing polyorganosiloxane component includes only the polyorganosiloxane of Formula 5 among the polyorganosiloxanes of Formulas 4 and 5, p in Formula 5 is 28 or less, and q is 17.5 or more can

In this case, p may be 3 or more, 5 or more, 7 or more, 9 or more, 15 or more, 20 or more, 22 or more, or 24 or more, or about 27 or less, 26 or less, or 25.5 or less in another example.

In addition, in this case, q is 18 or more, 19 or more, or 20 or more, or 75 or less, 70 or less, 65 or less, 60 or less, 55 or less, 50 or less, 45 or less, 40 or less, 35 or less, 30 or less, 25 or less in another example. It may be less than or about 23 or less.

In this case, the ratio (p/q) of p and q in Formula 5 may be in the range of 0.5 to 5. In another example, the ratio (p/q) may be 0.7 or more, 0.9 or more, or 1.1 or more, or 4 or less, 3 or less, 2 or less, 1.5 or less, or about 1.3 or less.

On the other hand, when the silicon-bonded hydrogen-containing polyorganosiloxane component simultaneously includes the polyorganosiloxanes of Chemical Formulas 4 and 5, the ratio of silicon-bonded hydrogen may be controlled.

For example, in the above case, the ratio of silicon-bonded hydrogen of the polyorganosiloxane of Formula 4 (polyorganosiloxane component including the polyorganosiloxane of Formula 4) is in the above range, and the polyorganosiloxane of Formula 5 ( The silicon-bonded hydrogen content ratio of the polyorganosiloxane component including the polyorganosiloxane of Formula 5) may be in the range of 2.5 to 10 mmol/g.

In this case, the silicon-bonded hydrogen content ratio of the polyorganosiloxane of Formula 5 (polyorganosiloxane component including the polyorganosiloxane of Formula 5) is 3 mmol/g or more, 3.5 mmol/g or more, or 4 mmol/g in another example. g or more, 9 mmol/g or less, 8 mmol/g or less, 7 mmol/g or less, 6 mmol/g or less, or 5 mmol/g or less.

In addition, in the above case, the total number of moles (H4) of silicon-bonded hydrogen contained in the polyorganosiloxane of Formula 4 (polyorganosiloxane component including the polyorganosiloxane of Formula 4) and the polyorganosiloxane of Formula 5 (Formula 5) The ratio (H5/H4) of the total number of moles (H5) of silicon-bonded hydrogens in the polyorganosiloxane component including the polyorganosiloxane of 5) may be in the range of 0.5 to 20 in one example. The ratio (H5/H4) is 1 or more, 1.5 or more, 2 or more, 3 or more, 4 or more, 5 or more, 6 or more, 7 or more, 8 or more, or 8.5 or more, or 18 or less, 16 or less, 14 or less in another example. , 12 or less, 10 or less, 8 or less, 6 or less, 4 or less, or 3 or less.

In addition, as described below, if the silicon-bonded hydrogen-containing polyorganosiloxane component includes only the polyorganosiloxane of Formula 5 among the polyorganosiloxanes of Formulas 4 and 5, the polyorganosiloxane of Formula 5 (polyorganosiloxane of Formula 5) The silicon-bonded hydrogen content ratio of the polyorganosiloxane component comprising

In another example, the ratio is 0.3 mmol/g or more, 0.5 mmol/g or more, 0.7 mmol/g or more, 0.9 mmol/g or more, 1.1 mmol/g or more, 1.3 mmol/g or more, 1.5 mmol/g or more, 1.7 mmol It may be about /g or more, or 1.9 mmol/g or more, or 4 mmol/g or less, 3 mmol/g or less, or 2 mmol/g or less.

By including the polyorganosiloxane component as described above with the alkenyl group-containing polyorganosiloxane component, while maintaining low viscosity, excellent flowability and permeability, etc., there is no powder sticking after curing, and a resin composition excellent in other physical properties such as thixotropy can do.

The ratio (H/Ak) of the total number of moles (Ak) of the alkenyl groups of the alkenyl group-containing polyorganosiloxane component and the total number of moles (H) of the silicon-bonded hydrogens of the silicon-bonded polyorganosiloxane component in the resin composition is 0.1 to 20 It can be adjusted within the range.

The ratio (H/Ak) is, in another example, 0.5 or more, 1 or more, 1.5 or more, 2 or more, 2.5 or more, 3 or more, 3.5 or more, 4 or more, 4.5 or more, 5 or more, 5.5 or more, 6 or more, 6.5 or more , 7 or more, 7.5 or more, 8 or more, 8.5 or more, 9 or more, 9.5 or more, 10 or more, 10.5 or more, 11 or more, 11.5 or more, 12 or more, or 12.5 or more, or 18 or less, 16 or less, 14 or less, 12 or less, It may be less than or equal to 10, or less than or equal to 8, or less than or equal to 7.5.

In addition, as described above, when the silicon-bonded hydrogen-containing polyorganosiloxane component includes both the polyorganosiloxanes of Formulas 4 and 5, and when only the polyorganosiloxane of Formula 5 is included, the ratio may be controlled differently. can

For example, when the silicon-bonded hydrogen-containing polyorganosiloxane component includes both the polyorganosiloxanes of Chemical Formulas 4 and 5, the ratio (H/Ak) may be in the range of 5 to 20. The ratio (H/Ak) is, in another example, 5.5 or more, 6 or more, 6.5 or more, 7 or more, 7.5 or more, 8 or more, 8.5 or more, 9 or more, 9.5 or more, or 10 or more, 10.5 or more, 11 or more, 11.5 or more , 12 or more, or 12.5 or more, or 18 or less, 16 or less, 14 or less, 13 or less, 13.5 or less, or about 12 or less.

In addition, as described above, when the silicon-bonded hydrogen-containing polyorganosiloxane component includes only the polyorganosiloxane of Formula 5 among the polyorganosiloxanes of Formulas 4 and 5, the ratio (H/Ak) is in the range of 0.1 to 15 can tomorrow In this case, the ratio (H/Ak) is, in another example, 0.5 or more, 1 or more, 1.5 or more, 2 or more, 2.5 or more, 3 or more, 3.5 or more, 4 or more, 4.5 or more, 5 or more, 5.5 or more, 6 or more or 6.5 or more, or 14 or less, 12 or less, 10 or less, or 8 or less, or 7 or less.

The resin composition further contains a filler. The filler may be a thermally conductive filler.

The thermally conductive filler may mean a filler in which the resin composition is cured to exhibit thermal conductivity of about 1 W/mK or more, 1.1 W/mK or more, 1.2 W/mK or more, or 1.25 W/mK or more. At this time, the thermal conductivity is a value measured in the manner described in the Examples of the present specification. The thermal conductivity is 10 W/mK or less, 9 W/mK or less, 8 W/mK or less, 7 W/mK or less, 6 W/mK or less, 5 W/mK or less, 4 W/mK or less, 3 It may be about W/mK or less, 2.5 W/mK or less, or 2 W/mK or less.

The type of the thermally conductive filler is not particularly limited, aluminum hydroxide (Al(OH) ₃ ), magnesium hydroxide (Mg(OH) ₂ ), calcium hydroxide (Ca(OH) ₂ ), hydromagnesite (Mg ₅ (CO ₃ ) ₄ (OH) ₂ 4H ₂ O), magnesia, alumina, aluminum nitride (AlN), boron nitride (BN), silicon nitride, SiC, ZnO, and/or inorganic fillers such as BeO, etc. may be exemplified. , but is not limited thereto.

In the above, the shape of the filler is not particularly limited, and, for example, spherical, needle-shaped, plate-shaped and other amorphous fillers may be used.

In one example, the filler may have an average particle diameter in the range of 0.001 μm to 100 μm. The average particle diameter is the D50 particle diameter measured by the method described in Examples to be described later. The average particle diameter of the filler is 0.005 μm or more, 0.01 μm or more, 0.05 μm or more, 0.1 μm or more, 0.5 μm or more, 0.8 μm or more, 1 μm or more, 5 μm or more, 10 μm or more, 15 μm or more, 20 μm or more, 25 μm or more in another example. , 30 μm or more, 35 μm or more, 40 μm or more, or 45 μm or more, 95 μm or less, 90 μm or less, 85 μm or less, 80 μm or less, 75 μm or less, 70 μm or less, 65 μm or less, 60 μm or less, 55 μm or less, 50 μm or less, 45 μm or less, 40 μm or less, 35 μm or less, 30 μm or less, 25 μm or less, 20 μm or less, 15 μm or less, 10 μm or less, or 5 μm or less.

A mixture of two or more fillers having at least different average particle diameters may be used as the filler in order to secure appropriate filling properties and secure target properties. For example, as the filler, a first filler having an average particle diameter of 20 μm or more and a second filler having an average particle diameter of less than 20 μm within the aforementioned range may be used.

The average particle diameter of the first filler is, in another example, 25 μm or more, 30 μm or more, 35 μm or more, 40 μm or more, or 45 μm or more, or 100 μm or less, 95 μm or less, 90 μm or less, 85 μm or less, 80 μm or less, 75 μm or less. It may be about 70 μm or less, 65 μm or less, 60 μm or less, or 55 μm or less.

In addition, the average particle diameter of the second filler is, in another example, 0.001 μm or more, 0.005 μm or more, 0.01 μm or more, 0.05 μm or more, 0.1 μm or more, 0.5 μm or more, or 0.8 μm or more, 18 μm or less, 15 μm or less, 10 μm It may be about 5 μm or less or 3 μm or less.

When the first and second fillers are simultaneously applied, the ratio (D1/D2) of the average particle diameter (D1) of the first filler to the average particle diameter (D2) of the second filler is 2 to 100 can be within the scope of tomorrow. The ratio (D1/D2) is 5 or more, 10 or more, 15 or more, 20 or more, 25 or more, 30 or more, 35 or more, 40 or more, or 45 or more, or 95 or less, 90 or less, 85 or less, 80 or less in another example. , 75 or less, 70 or less, 65 or less, 60 or less, or 55 or less.

When the first and second fillers are simultaneously applied, the ratio (W1/W2) of the used weight (W1) of the first filler based on the used weight (W2) of the second filler is 0.5 to 100 May be within range tomorrow. In another example, the ratio (W1/W2) is 1 or more, 1.5 or more, or 2 or more, or 95 or less, 90 or less, 85 or less, 80 or less, 75 or less, 70 or less, 65 or less, 60 or less, 55 or 50 or less, 45 or less, 40 or less, 35 or less, 30 or less, 25 or less, 20 or less, 15 or less, 10 or less, 5 or less, 4 or less, 3 or less, or 2.5 or less.

If necessary, the filler may be surface-treated with a silane compound. In this case, the filler may include a silane compound on the surface.

As the silane compound, a kind suitable for the purpose of the present application may be selected and used, and examples thereof include a compound of the following formula (6).

[Formula 6]

In Formula 6, R ₁ to R ₄ are each independently hydrogen, an alkyl group, and an alkoxy group, and at least one of R ₁ to R ₄ may be an alkyl group having 1 to 18 carbon atoms.

The alkyl group or alkoxy group of Formula 6 may be straight-chain, branched-chain or cyclic, suitably straight-chain, and optionally substituted with one or more substituents.

In one example, at least one, one to three, one to two, or any one of R ₁ to R ₄ in Formula 6 may be an alkyl group having 1 to 18 carbon atoms, and the carbon number of the alkyl group is 2 or more, 3 or more, 4 or more, 5 or more, 6 or more, 7 or more, 8 or more, 9 or more, or 10 or more, or 17 or less, 16 or less, 15 or less, 14 or less, 13 or less, 12 or less, 11 or less, 10 or less , 9 or less, 8 or less, 7 or less, or 6 or less.

In Formula 6, the functional group other than the alkyl group having 1 to 18 carbon atoms among R ₁ to R ₄ may be an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.

In one example, in Formula 6, any one or two of R ₁ to R ₄ may be an alkyl group having 1 to 18 carbon atoms, and the remainder may be an alkoxy group having 1 to 4 carbon atoms. In this case, the number of carbon atoms in the alkyl group is 2 or more, 3 or more, 4 or more, 5 or more, 6 or more, 7 or more, 8 or more, 9 or more, or 10 or more, or 17 or less, 16 or less, 15 or less, 14 or less, 13 or less, 12 or less, 11 or less, 10 or less, 9 or less, 8 or less, 7 or less, or 6 or less.

In the filler, the silane compound may be included in an amount within the range of 0.5 to 5 parts by weight based on 100 parts by weight of the filler. The content is 0.7 parts by weight or more, 0.9 parts by weight or more, 1.1 parts by weight or more, about 1.3 parts by weight or more, about 1.5 parts by weight or more, about 1.7 parts by weight or more, or about 1.9 parts by weight or more, or 4.5 parts by weight or less degree, about 4 parts by weight or less, about 3.5 parts by weight or less, about 3 parts by weight or less, about 2.5 parts by weight or less, about 2 parts by weight or less, about 1.8 parts by weight or less, or about 1.6 parts by weight or less.

By blending such a filler with the curable resin component, when the filler is a highly reactive filler, contains water, or easily contains water, even when such a filler is contained in excess, the desired storage Stability and thixotropy can be effectively secured.

A method of surface-treating the filler with the silane compound is not limited as long as it is a known method. For example, the surface treatment may be performed by contacting the filler with the silane compound under appropriate conditions to induce a reaction between the silane compound and the filler.

For example, the surface treatment is possible by dispersing the filler and the silane compound in an appropriate solvent and mixing and/or maintaining the filler at an appropriate temperature.

The content of the filler in the resin composition is adjusted according to the purpose. For example, in the resin composition, the filler may be included in a proportion of 60 to 95% by weight based on the total weight of the polyorganosiloxane component and the filler. In another example, the ratio may be about 65 wt% or more, 70 wt% or more, 75 wt% or more, or 80 wt% or more, or 90 wt% or less or 85 wt% or less.

The content of the filler may be the content in the resin composition when the resin composition is a one-component type, and may be the content in the main part or the curing agent part in the case of the two-component type, or the content in the mixture of the main material and the curing agent part there is.

The resin composition may include other necessary components in addition to the above components.

In one example, the resin composition of the present application may further include a silane additive. When the filler is surface-treated, the silane additive is a silane compound excluding the silane compound subjected to the surface treatment. The specific type of the additive is not particularly limited, and for example, tetraalkoxy silane, alkyl trialkoxy silane, dialkyl dialkoxy silane, alkoxy trialkyl silane, and the like may be exemplified. In this case, specific types of the alkoxy group and the alkyl group are as described in the introduction of the present specification.

The silane additive may be used in an amount of about 0.5 to 20 parts by weight based on 100 parts by weight of the alkenyl group-containing polyorganosiloxane component. In another example, the ratio is 0.7 parts by weight or more, 0.9 parts by weight or more, 1 part by weight or more, 1.1 parts by weight or more, 1.3 parts by weight or more, 1.5 parts by weight or more, 1.7 parts by weight or more, or 1.9 parts by weight or more, or 18 parts by weight or more. or less, 16 parts by weight or less, 14 parts by weight or less, 12 parts by weight or less, 10 parts by weight or less, 8 parts by weight or less, 6 parts by weight or less, 4 parts by weight or less, or 3 parts by weight or less.

The resin composition may further include a catalyst, for example, an addition reaction catalyst. The type of catalyst is not particularly limited, but, for example, a platinum-based catalyst may be used, and a known or commercially available platinum-based catalyst may be used.

The content of the catalyst is not particularly limited, and may be included in a catalytic amount depending on the composition of the curable polyorganosiloxane component.

In addition to the above components, the resin composition may further include additional additives, for example, pigments or dyes, dispersants, thixotropic agents, flame retardants, and the like, if necessary.

The resin composition, as described above, may be a one-component composition, a main component or a curing agent part of a two-component composition, or a mixture of a main component and a curing agent part of the two-component composition.

In the case of a mixture of the main component and the curing agent part of the one-component or two-component composition, the resin composition may include the aforementioned components simultaneously.

In addition, when the resin composition is a main part of a two-part composition, the main part includes the alkenyl group-containing polyorganosiloxane component as a curable polyorganosiloxane component, and may further include the catalyst and filler. In addition, when the above-mentioned silane additive is also included, it may be included in the main part.

In addition, when the resin composition is a curing agent part of a two-component composition, the curing agent part includes the silicon-bonded hydrogen-containing polyorganosiloxane component as a curable polyorganosiloxane component, and further includes the filler, and does not include a catalyst it may not be If necessary, the curing agent part may also contain an alkenyl group-containing polyorganosiloxane component.

In each of the above cases, specific types of polyorganosiloxane components, fillers, catalysts, etc. and their blending ratios are as described above.

In one example, when the resin composition is a two-component resin composition, the resin composition includes a physically separated main part and a curing agent part, and the main part includes an alkenyl group-containing polyorganosiloxane component and a filler, and the curing agent The part may include a silicon-bonded hydrogen containing polyorganosiloxane component and a filler.

In this case, the main part may include a catalyst and the curing agent part may not include a catalyst.

In this case, specific types of polyorganosiloxane components, fillers, catalysts, etc. and their blending ratios are the same as described above.

The resin composition of the present application is suitably used for a variety of uses, and in particular, as a heat dissipation material, it may be suitably used.

Accordingly, the resin composition may be applied to various uses requiring a heat dissipation material, and the scope of the use is not particularly limited.

For example, as a battery-related technology, the resin composition may be applied as a heat dissipation material such as a battery module or a battery pack or a heat dissipation material of an On Board Charger (OBC) for a vehicle. Accordingly, the present application also relates to a battery module, battery pack, or on-board charger (OBC) including the resin composition or a cured product thereof as a heat dissipation material. In the battery module, battery pack, or on-board charger, the application position or application method of the resin composition or the cured product is not particularly limited, and a known method may be applied. In addition, the resin composition of the present application is not limited to the above uses, and can be effectively applied to various uses requiring excellent heat dissipation properties, storage stability and adhesion.

In another example related to the present application, the present application may relate to an electronic device or device having a cured product of the resin composition.

The type of electronic equipment or device is not particularly limited, and for example, an AVN (audio video navigation) for a vehicle or an OBC (On Board Charger) module for an electric vehicle, an LED module or an IC chip, and a computer or mobile device including the same are exemplified. can

The cured product of the resin composition may dissipate heat within the equipment or device, and may provide durability against impact, insulation, and the like.

The present application may provide a resin composition and uses thereof.

In the present application, excellent flowability, permeability, thixotropy and low viscosity characteristics are secured when a large amount of a filler that is high in reactivity, contains moisture and/or easily contains moisture is secured, and the characteristics are changed over time. It is also possible to provide a resin composition that is stably maintained as designed to ensure excellent storage stability.

In addition, in the present application, it is possible to provide a resin composition that does not cause powder to stick on the surface after curing, can reduce weight, and has excellent thermal conductivity per unit volume.

The present application may also provide various uses of the resin composition.

Hereinafter, the present application will be described in detail through Examples, but the scope of the present application is not limited by the Examples below.

1. Viscosity

The viscosity of the main agent, the curing agent, or the resin composition was measured using an Advanced Rheometic Expansion System (Model Name: ARES, Manufacturer: Rheometic Scientific (UK)). An 8 mm plate was used for the measurement, the temperature condition was set to room temperature (about 25° C.), and the gap was set to 0.7 mm. The viscosity was measured while changing the shear rate from 0.01/s to 10.0/s. For the viscosity, the value at a shear rate of 2.5/s was described as a representative value, and the ratio (I1/I2) of the viscosity (I1) at the shear rate of 0.25/s to the viscosity (I2) at the shear rate of 2.5/s (I1/I2) was thixotropic. It was described as an index.

2. Hardness

The main agent and the curing agent prepared in Examples or Comparative Examples were mixed in a volume ratio of 1:1, and after curing in the form of a film having a thickness of about 5 mm, the hardness of the film surface was measured according to ASTM D 2240 standard. For hardness measurement, an ASKER Durometer instrument was used. The initial hardness was measured by applying a load of about 1.5 kg to the surface of the sample in a flat state, and the hardness was evaluated by confirming the measured value as a stabilized measurement value after 15 seconds. Shore OO hardness was measured.

3. Thermal Conductivity

The main agent and the curing agent prepared in Examples or Comparative Examples were mixed in a volume ratio of 1:1, and after curing to form a film having a thickness of about 5 mm, thermal conductivity in the thickness direction of the film was measured. Thermal conductivity was measured using a hot disk measuring device according to the standard of ISO22007-2, which measures the temperature change while heating a sensor having a nickel wire double spiral structure.

4. ^One H NMR analysis

¹ H NMR analysis of the polyorganosiloxane was performed in a known manner. The analysis was performed at room temperature using an NMR spectrometer including a Varian Unity Inova (500 MHz) spectrometer with a triple resonance 5 mm probe. The polyorganosiloxane to be analyzed was diluted to a concentration of about 10 mg/ml in a solvent for NMR measurement (CDCl ₃ ), and chemical shift was expressed in ppm.

5. ²⁹ Si NMR analysis

²⁹ Si NMR analysis of the polyorganosiloxane was carried out in a known manner. In the ²⁹ Si NMR analysis, chemical shift was expressed using TMS (dilute tetramethylsilane in CDCl ₃ ) as a reference compound.

6. Gel Permeation Chromatograph (GPC)

The number average molecular weight (Mn) and molecular weight distribution of the polyorganosiloxane were measured using gel permeation chromatography (GPC). Put the polyorganosiloxane to be analyzed in a 5 mL vial, and dilute it in THF (tetrahydro furan) to a concentration of about 5 mg/mL. After that, the standard sample for calibration and the sample to be analyzed were filtered through a syringe filter (pore size: 0.45 μm) and then measured. For the analysis program, ChemStation of Agilent Technologies was used, and the weight average molecular weight (Mw) and number average molecular weight (Mn) were obtained by comparing the elution time of the sample with the calibration curve, and the molecular weight distribution (PDI) was obtained by the ratio (Mw/Mn). ) was calculated. The measurement conditions of GPC are as follows.

<GPC measurement conditions>

Instrument: 1200 series from Agilent technologies

Column: Using 2 PLgel mixed B from Polymer laboratories

Solvent: THF

Column temperature: 40℃

Sample concentration: 5 mg/mL, 10 μL injection

Standard Sample: Polystyrene (Mp: 3900000, 723000, 316500, 52200, 31400, 7200, 3940, 485)

Preparation Example 1: Preparation of surface-treated filler (A)

A surface-treated filler (A) was prepared by surface-treating aluminum hydroxide having a D50 particle diameter of about 50 μm with decyltriethoxysilane.

The D50 particle diameter is the particle diameter (median diameter) at 50% cumulative by volume of the particle size distribution, and the particle size distribution is obtained based on the volume, and the particle at the point where the cumulative value is 50% in the cumulative curve with 100% of the total volume. is the diameter The D50 particle size was measured using a MASTERSIZER 3000 equipment from Marven in accordance with ISO-13320. Ethanol was used as a solvent for the measurement.

The surface treatment was performed by mixing the decyltriethoxysilane and the filler in a weight ratio of 1.5:100 (decyltriethoxysilane:filler) in ethanol or methylethylketone as a solvent, and then maintaining the temperature of the mixture at about 60°C. under the condition, the reaction was carried out for 1 hour.

Preparation Example 2: Preparation of surface-treated filler (B)

A surface-treated filler (B) was prepared by surface-treating aluminum hydroxide having a D50 particle diameter of about 1 μm with hexyltriethoxysilane. The method for measuring the D50 particle size is the same as in Preparation Example 1. The surface treatment was performed by mixing the hexyltriethoxysilane and the filler in a weight ratio of 1:100 (hexyltriethoxysilane:filler) in ethanol or methylethylketone as a solvent, and then maintaining the temperature of the mixture at about 60°C. under the condition, the reaction was carried out for 1 hour.

Example 1.

Manufacturing of subject parts

11.9 g of a polyorganosiloxane component (DSVP-100, manufactured by Wonik Cube) comprising a polyorganosiloxane of the following formula A, a platinum catalyst (1,3-divinyl-1,1,3,3-tetramethyl-disiloxane-platinum) (0)-complex) 0.1 g, inhibitor (Inhibitor600, manufacturer: Evonik) 0.3 g, TEOS (Tetraethoxy silane) 0.3 g, D50 aluminum hydroxide with a particle size of about 50 μm, 25.2 g, and D50 hydroxide with a particle size of about 1 μm A main part was prepared by mixing 10.8 g of aluminum and 0.01 g of a pigment.

The meaning and measurement method of the D50 particle size are the same as those described in Preparation Example 1.

The area ratio (Si-CH ₃ /Si-Vinyl) of the Si-Vinyl peak and the Si-CH ₃ peak in ¹ H NMR analysis measured in the manner described above for the polyorganosiloxane component was about 92.65, and the vinyl confirmed therefrom The content of groups was about 0.290 mmol/g.

In addition, the number average molecular weight (Mn) measured by GPC of the polyorganosiloxane component was about 7020 g/mol, and the weight average molecular weight (Mw) was about 13700 g/mol, so the molecular weight distribution (PDI=Mw/ Mn) was about 1.95.

The ingredients are put in a paste mixer, and the heat generated after mixing and dispersing at 600 rpm and 500 rpm for rotation is confirmed, and defoamed for 4 minutes at 600 rpm and 200 rpm for rotation in a vacuum. The subject part was prepared.

[Formula A]

In Formula A, m is a number on the order of 91.

Preparation of hardener parts

7.5 g of a polyorganosiloxane component (XL-11, manufacturer: AB specialty silicones) comprising a polyorganosiloxane of the following formula B, a polyorganosiloxane component (CE-4, manufacturer: AB) comprising a polyorganosiloxane of the following formula C 4.5 g of specialty silicones), 25.2 g of aluminum hydroxide with a D50 particle diameter of about 50 μm as applied to manufacture the main part, and 10.8 g of aluminum hydroxide with a D50 particle diameter of about 1 μm as applied when manufacturing the main part The curing agent part was prepared by mixing. The ingredients are put in a paste mixer, and the heat generated after mixing and dispersing for about 3 minutes at 600 rpm in the process and 500 rpm in rotation is checked, and the heat generated in a vacuum is defoamed at 600 rpm in rotation and 200 rpm in the rotation for 4 minutes. A curing agent part was prepared.

As a result of the ²⁹ Si NMR analysis performed on the polyorganosiloxane component comprising the polyorganosiloxane of Formula B, M units at both ends in the structure of Formula B ((CH ₃ ) ₃ SiO _1/2 units) The molar ratio of D units without hydrogen (CH ₃ ) ₂ SiO _2/2 units is about 68.8 mol %, and the molar ratio of D units without hydrogen (H(CH ₃ )SiO _2/2 units) is about 68.8 mol %. ) was about 26.9 mol%. In addition, the ratio of the Si-H peak to the Si-CH ₃ peak (Si-CH ₃ /Si-H) confirmed by 1H NMR analysis was about 9.61, and the content of silicon-bonded hydrogen confirmed through this was about 4.14 mmol/ it was g.

The ratio of the Si-H peak to the Si-CH ₃ peak (Si-CH ₃ /Si-H) confirmed by 1H NMR analysis performed on the polyorganosiloxane of Formula C was about 648, and the silicon atom bonding confirmed through this The content of hydrogen atoms was about 2.9 mmol/g.

[Formula B]

In formula (B), p is a number on the order of 32, and q is a number on the order of 12.5.

[Formula C]

In formula (C), n is a number on the order of 150.

Example 2.

When preparing the main material and curing agent parts, use the filler (A) of Preparation Example 1 instead of aluminum hydroxide having a D50 particle diameter of about 50 μm, and the filler (B) of Preparation Example 2 instead of aluminum hydroxide having a D50 particle diameter of about 1 μm Except for using a curing agent part was prepared in the same manner as in Example 1.

Example 3.

Manufacturing of subject parts

11.9 g of polyorganosiloxane component (DSVP-100, manufactured by Wonik Cube Co., Ltd.) containing the polyorganosiloxane of formula A, platinum catalyst (1,3-divinyl-1,1,3,3-tetramethyl-disiloxane-platinum ( 0)-complex) 0.1 g, inhibitor (Inhibitor600, manufacturer: Evonik) 0.3 g, TEOS (Tetraethoxy silane) 0.5 g, D50 aluminum hydroxide with a particle diameter of about 50 μm 25.2 g and D50 aluminum hydroxide with a particle diameter of about 1 μm A main part was prepared in the same manner as in Example 1, except that 10.8 g and 0.01 g of the pigment were mixed.

Preparation of hardener parts

12 g of a polyorganosiloxane component (XL-17, manufacturer: AB specialty silicones) containing a polyorganosiloxane of the following formula (D), 25.2 g of aluminum hydroxide having a D50 particle diameter of about 50 μm as applied during the manufacture of the main part, and A curing agent part was prepared by mixing 10.8 g of aluminum hydroxide having a D50 particle diameter of about 1 μm as applied during the manufacture of the part. The mixing method is the same as in Example 1.

As a result of ²⁹ Si NMR and 1H NMR analysis performed on the polyorganosiloxane component comprising the polyorganosiloxane of formula D, the content of silicon-bonded hydrogen was about 1.95 mmol/g.

[Formula D]

In formula (D), p is a number on the order of 25, and q is a number on the order of 21.

The results of evaluating the viscosity, thermal conductivity, and hardness for the Examples and Comparative Examples, respectively, are summarized in Table 1 below. In Table 1 below, the mixing viscosity is a viscosity measured immediately after mixing the main part and the curing agent part in a volume ratio of 1:1.

Example One 2 3 subject part Viscosity (kcP) (2.5/s) 4.52 3.9 3.51 hardener part Viscosity (kcP) (2.5/s) 1.31 1.79 2.48 resin composition Viscosity (kcP) (2.5/s) 3.19 3.77 4.16 thixotropic index 2.23 3.03 3.87 Thermal Conductivity (W/mK) 1.29 1.15 1.22 Hardness (shore OO) 70 69 79

In order to confirm the storage stability of each of the main part and the curing agent part of the example, the viscosity by shear rate was measured immediately after production (0d), after 3 days (3d), after 10 days (10d), and after 17 days (17d). ) were evaluated and summarized in Table 2 below. In the table below, the unit of each viscosity is kcP.

Example 1 Example 2 Example 3 topic hardener topic hardener topic hardener 0d 0.25/s 6.23 3.90 7.10 5.23 6.74 8.02 2.5/s 3.90 2.39 4.52 1.31 3.40 2.48 3d 0.25/s 4.80 3.54 5.90 4.27 3.07 5.23 2.5/s 3.48 2.03 4.10 1.23 2.82 2.10 10d 0.25/s 4.42 3.32 5.40 3.60 2.30 4.50 2.5/s 3.12 1.98 3.98 1.10 2.27 2.01 17d 0.25/s 3.88 2.70 4.08 3.21 2.41 3.94 2.5/s 2.69 1.80 3.68 1.12 2.52 1.91

From Tables 1 and 2, it can be seen that the main part, curing agent part, and resin composition of Examples respectively exhibit appropriate viscosity and thixotropy, ensure thermal conductivity and hardness, and ensure storage stability because there is no increase in viscosity over time. .

Claims (14)

an alkenyl group-containing polyorganosiloxane component including a polyorganosiloxane represented by the following formula (2);
a silicon-bonded hydrogen-containing polyorganosiloxane component comprising at least one polyorganosiloxane selected from the group consisting of a polyorganosiloxane of the following formula (4) and a polyorganosiloxane of the following formula (5); and
A resin composition comprising a filler:
[Formula 2]

In Formula 2, R ₁ is an alkenyl group, R ₂ is an alkyl group or an aryl group, and n is a number within the range of 10 to 200:
[Formula 4]

In Formula 4, R ₃ is an alkyl group or an aryl group, and m is a number within the range of 10 to 1,000:
[Formula 5]

In Formula 5, R ₁ is hydrogen, an alkyl group, or an aryl group, R ₂ is an alkyl group or an aryl group, p is a number within the range of 1 to 60, and q is a number within the range of 5 to 80. The resin composition according to claim 1, wherein the alkenyl group-containing polyorganosiloxane component has a weight average molecular weight of 30000 g/mol or less and a molecular weight distribution within the range of 1.3 to 3. The resin composition according to claim 1, wherein the alkenyl group-containing polyorganosiloxane component contains an alkenyl group in a ratio of 0.01 to 10 mmol/g. The resin composition according to claim 1, wherein the silicon-bonded hydrogen-containing polyorganosiloxane component simultaneously includes the polyorganosiloxane of Formula 4 and the polyorganosiloxane of Formula 5. The resin composition according to claim 4, wherein in Formula 5, p is 28.5 or more, and q is 17 or less. The method according to claim 4, wherein the silicon-bonded hydrogen content of the polyorganosiloxane of the formula (4) is within the range of 0.01 to 5 mmol/g, and the silicon-bonded hydrogen content of the polyorganosiloxane of the formula (5) is 2.5 to 10 mmol/g a resin composition within the range. The resin composition according to claim 1, wherein the silicon-bonded hydrogen-containing polyorganosiloxane component comprises only the polyorganosiloxane represented by Formula 5 among the polyorganosiloxane represented by Formula 4 and the polyorganosiloxane represented by Formula 5. The resin composition according to claim 7, wherein in Formula 5, p is 28 or less, and q is 17.5 or more. The resin composition according to claim 7, wherein the silicon-bonded hydrogen content of the polyorganosiloxane of formula (5) is in the range of 0.1 to 5 mmol/g. The ratio (H/Ak) of the number of moles (Ak) of alkenyl groups in the alkenyl group-containing polyorganosiloxane component to the number of moles (H) of silicon-bonded hydrogen in the silicon-bonded polyorganosiloxane component is in the range of 0.1 to 20. The resin composition within. The resin composition according to claim 1, wherein the filler comprises a compound of the following formula (6) on the surface:
[Formula 6]

In Formula 6, R ₁ to R ₄ are each independently hydrogen, an alkyl group having 4 to 16 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms, and at least one of R ₁ to R ₄ is an alkyl group having 4 to 16 carbon atoms. The resin composition of claim 11, wherein the compound of Formula 6 is included in an amount of 0.5 to 3 parts by weight based on 100 parts by weight of the filler. The resin composition according to claim 1, wherein the filler is included in an amount of 60 to 95% by weight based on the total weight of the polyorganosiloxane component and the filler. A two-component resin composition comprising a main part and a curing agent part,
The main part includes an alkenyl group-containing polyorganosiloxane component and a filler including a polyorganosiloxane of the following formula (2),
The curing agent part is a two-component resin composition comprising a silicon-bonded hydrogen-containing polyorganosiloxane component and a filler including at least one polyorganosiloxane selected from the group consisting of a polyorganosiloxane of the following formula (4) and a polyorganosiloxane of the following formula (5) :
[Formula 2]

In Formula 2, R ₁ is an alkenyl group, R ₂ is an alkyl group or an aryl group, and n is a number within the range of 10 to 200:
[Formula 4]

In Formula 4, R ₃ is an alkyl group or an aryl group, and m is a number within the range of 10 to 1,000:
[Formula 5]

In Formula 5, R ₁ is hydrogen, an alkyl group, or an aryl group, R ₂ is an alkyl group or an aryl group, p is a number within the range of 1 to 60, and q is a number within the range of 5 to 80.