CN116745335A

CN116745335A - Curable composition

Info

Publication number: CN116745335A
Application number: CN202280012095.1A
Authority: CN
Inventors: 金度延; 孙昊延; 姜杨求; 田信姬; 李哈娜; 李政玹
Original assignee: LG Chem Ltd
Current assignee: LG Chem Ltd
Priority date: 2021-09-30
Filing date: 2022-09-20
Publication date: 2023-09-12

Abstract

The present application can provide a curable composition or a thermal interface material or the like that exhibits low adhesion to a predetermined adherend while having low density and exhibiting high thermal conductivity, and provide such a curable composition or thermal interface material or the like: which ensures excellent flame retardant characteristics without using a halogen flame retardant or a phosphorus-based flame retardant, or minimizing the use ratio thereof and exhibits a release characteristic and thixotropic property suitable for a process.

Description

Curable composition

Technical Field

Cross Reference to Related Applications

The present application claims the benefit of priority based on korean patent application No. 10-2021-0129972, 9 and 30, 2021 and korean patent application No. 10-2022-0117998, 9 and 19, 2022, the disclosures of which are incorporated herein by reference in their entireties.

Technical Field

The present application relates to curable compositions, thermal Interface Materials (TIMs) and uses thereof.

Background

As the number of electrical or electronic devices, such as batteries, requiring thermal management increases, the importance of heat dissipating materials, such as Thermal Interface Materials (TIMs), increases. Various types of heat dissipating materials are known. As one of conventional heat dissipation materials, a material in which a resin binder is filled with a filler having heat dissipation characteristics is known (for example, patent document 1).

In such a heat dissipating material, a silicone resin, a polyolefin resin, an acrylic resin, an epoxy resin, or the like is generally used as a resin binder.

The heat dissipating material is basically required to have excellent heat conductivity, and further functions are required according to the use. For example, depending on the application, the heat dissipating material may need to exhibit low adhesion to a particular adherend as well as high thermal conductivity.

For example, when it is necessary to replace a portion of the product that is in contact with the heat sink material, or when it is necessary to change the position of the heat sink material in the process, etc., the heat sink material needs to exhibit low adhesion.

Among known heat dissipating materials, materials exhibiting low adhesion include materials that employ silicone resins as a resin binder. However, silicone resins are relatively expensive. In addition, the silicone resin contains components that cause contact failure or the like when applied to electronic/electric products, so that use is limited.

Even the polyurethane material applied in patent document 1 can form a heat dissipating material having high thermal conductivity, and has other various advantages, but is a material exhibiting high adhesion to most adherends.

Methods of reducing the adhesive force of materials exhibiting high adhesive force include a method of blending components called so-called plasticizers. However, plasticizers formulated in large amounts for the purpose of controlling adhesion have problems of damaging the inherent advantages of the material itself or eluting out during the course of use, etc.

Meanwhile, the heat dissipation material may require flame retardant characteristics to ensure safety against fire generated in electrical products, electronic products, or batteries, etc. Methods of ensuring flame retardant properties include methods of blending components known as so-called flame retardants.

The flame retardant should have good mixing characteristics with respect to the raw materials and the additional additives, not affect the mechanical properties of the final product, and minimize the generation of toxic gases in consideration of the use environment.

As the flame retardant, a halogen-containing flame retardant (so-called halogen flame retardant, for example, bromine-based flame retardant) can be used. The halogen element-containing flame retardant can ensure excellent flame retardant properties, but has such a problem that: dioxins, which are environmentally hazardous substances, are of course corrosive when burned, so that they may affect the mechanical properties of the final product and be harmful to the human body.

In addition, there are cases where a flame retardant containing phosphorus (P) element (so-called phosphorus-based flame retardant) is used as the flame retardant. The flame retardant containing a phosphorus element can ensure excellent flame retardant properties while being less toxic than the flame retardant containing a halogen element, but is known to be expensive and to have a problem of weakening heat radiation properties.

[ Prior Art literature ]

(patent document 1) Korean patent laid-open No. 10-2016-0105354

Disclosure of Invention

Technical problem

The present application is directed to curable compositions, thermal Interface Materials (TIMs), and uses thereof. The thermal interface material may be a thermal interface material formed by curing a curable composition. An object of the present application is to provide a curable composition or a thermal interface material or the like which exhibits low adhesion to a predetermined adherend while having low density and exhibiting high thermal conductivity.

The present application is also intended to ensure excellent flame retardant characteristics without using a halogen flame retardant or a phosphorus-based flame retardant or minimizing the use ratio thereof, and to exhibit a release characteristic (ejection properties) and thixotropic properties suitable for the process.

It is an object of the present application to provide a product comprising a curable composition, a cured product of a curable composition, or a thermal interface material.

Technical proposal

In the physical characteristics mentioned in the present application, if the measured temperature affects the physical characteristics, the relevant physical characteristics are physical characteristics measured at room temperature unless otherwise specified.

The term room temperature as used in the present application is a natural temperature without warming or cooling, which may mean any temperature, for example, in the range of 10 ℃ to 30 ℃, such as a temperature of about 15 ℃ or higher, about 18 ℃ or higher, about 20 ℃ or higher, about 23 ℃ or higher, about 27 ℃ or lower, or 25 ℃. In this specification, unless otherwise indicated, temperature is in degrees celsius (°c).

In the physical properties mentioned in the present application, if the measured pressure affects the physical properties, the relevant physical properties are physical properties measured at normal pressure unless otherwise specified.

The term normal pressure as used in the present application is a natural pressure under no pressurization or depressurization, which means an atmospheric pressure in the range of about 700mmHg to 800mmHg as the normal pressure.

The term "a to b" as used in the present application means "within the range of a to b, including both a and b". For example, the fact that a to b parts by weight are contained has the same meaning as that contained in the range of a to b parts by weight.

The term relative humidity as used in the present application is expressed as a percentage (%) of the ratio of the amount of water vapor contained in a unit volume of current air to the maximum saturated vapor pressure that can be contained per unit volume of the air, which can be expressed in RH%.

The term weight average molecular weight (M _w ) GPC (gel permeation chromatography) measurement can be used, which can be specifically measured according to the following physical property measurement method. Furthermore, the term polydispersity index (PDI) as used in the present application is obtained by mixing the weight average molecular weight (M _w ) Divided by the number average molecular weight (M _n ) And the value (M _w /M _n ) Which means the molecular weight distribution of the polymer. Number average molecular weight (M _n ) GPC (gel permeation chromatography) may also be used for measurement.

The term excellent thermal conductivity as used in the present application may mean that in a state where the curable composition is made into a cured product (sample) having a diameter of 2cm or more and a thickness of 5mm, the measured thermal conductivity is about 2.0W/mK or more, 2.1W/mK or more, 2.2W/mK or more, 2.3W/mK or more, 2.4W/mK or more, 2.5W/mK or more, 2.6W/mK or more, 2.7W/mK or more, 2.8W/mK or more, 2.9W/mK or more, or about 3.0W/mK or more, as measured in the thickness direction of the sample according to ASTM D5470 standard or ISO 22007-2 standard.

The term low specific gravity or low-specific gravity as used in the present application may mean a case where the specific gravity measured at room temperature is 3 or less for a curable composition, a cured product of the curable composition, a filler, or the like.

The term high specific gravity or high-specific gravity as used in the present application may mean a case where the specific gravity measured at room temperature is greater than 3 for the curable composition, the cured product of the curable composition, the filler, or the like.

The term excellent flame retardancy as used in the present application may mean a case where the result of evaluation according to the following physical property measurement method (UL 94V) is V-0 grade or more.

Unless otherwise indicated, the term viscosity as used in the present application may be a value measured at 25 ℃, which may be specifically measured according to the following physical property measurement method.

The term substantially free of a particular material as used in the present application is intended to have a meaning that does not allow for the intended inclusion of the particular material. However, in the case where the specific material is naturally contained, unless otherwise specified, the specific material may be considered to be substantially not contained if contained in an amount of 0.1% by weight or less, 0.05% by weight or less, or 0.01% by weight or less with respect to the total weight.

The term substitution as used in the present application means that a hydrogen atom bonded to a carbon atom of a compound becomes an additional substituent, wherein if the position to be substituted is a position where the hydrogen atom is replaced, i.e., a position where a substituent can be substituted, the position to be substituted is not particularly limited, and when two or more substituents are substituted, the substituents may be the same as or different from each other.

The term halogen or halogen element used in the present application means an element of group 17 of the periodic table of elements, and in the present application, it may mean a group consisting of chlorine (Cl), iodine (I), bromine (Br) and fluorine (F) in the element of group 17.

The term substituent as used in the present application means an atom or group of atoms that replaces one or more hydrogen atoms on the parent chain of a hydrocarbon. In addition, substituents are described below, but are not limited thereto, and unless otherwise indicated herein, substituents may or may not be further substituted with substituents described below.

Unless otherwise described, the term alkyl or alkylene as used in the present application may be a linear or branched alkyl or alkylene having from 1 to 20 carbon atoms, or from 1 to 16 carbon atoms, or from 1 to 12 carbon atoms, or from 1 to 8 carbon atoms, or from 1 to 6 carbon atoms, or a cyclic alkyl or alkylene having from 3 to 20 carbon atoms, or from 3 to 16 carbon atoms, or from 3 to 12 carbon atoms, or from 3 to 8 carbon atoms, or from 3 to 6 carbon atoms. Here, the cyclic alkyl or alkylene group also includes an alkyl or alkylene group having only a ring structure, and an alkyl or alkylene group having a ring structure. For example, both cyclohexyl and methylcyclohexyl correspond to cyclic alkyl groups. Further, for example, an alkyl group or an alkylene group may be specifically exemplified by methyl (methylene), ethyl (ethylene), n-propyl (n-propylene), isopropyl (isopropylene), n-butyl (n-butylene), isobutyl (isobutylene), t-butyl (t-butylene), sec-butyl (sec-butylene), 1-methyl-butyl (1-methyl-butylene), 1-ethyl-butyl (1-ethyl-butylene), n-pentyl (n-pentylene), isopentyl (isopentylene), neopentyl (neopentyl), t-pentyl (t-pentylene), n-hexyl (n-hexyl), 1-methylpentyl (1-methylpentylene), 2-methylpentyl (2-methylpentylene), 4-methyl-2-pentyl (4-methyl-2-pentylene), 3-dimethylbutyl (3, 3-dimethylbutyl), 2-ethylbutyl (2-ethylbutylene), n-heptyl (n-heptyl), 1-methylhexyl (1-methylhexyl), n-octyl (n-octyl), t-octyl (n-octyl), 1-methylheptyl (1-methylheptyl), 2-ethylhexyl (2-ethylheptyl), 2-propylpentyl (2-propylpentylene), n-nonyl (n-nonylene), 2-dimethylheptyl (2, 2-dimethylheptyl), 1-ethylpropyl (1-ethylpropyl), 1-dimethylpropyl (1, 1-dimethylpropyl), isohexyl (isohexyl), 2-methylpentyl (2-methylpentylene), 4-methylhexyl (4-methylhexyl) and 5-methylhexyl (5-methylhexyl) and the like, but are not limited thereto. Further, the cycloalkyl group or the cycloalkylene group may be specifically exemplified by cyclopropyl (cyclopropyl group), cyclobutyl (cyclobutyl group), cyclopentyl (cyclopentyl group), 3-methylcyclopentyl (3-methylcyclopentyl group), 2, 3-dimethylcyclopentyl group (2, 3-dimethylcyclopentyl group), cyclohexyl (cyclohexyl group), 3-methylcyclohexyl (3-methylcyclohexyl group), 4-methylcyclohexyl (4-methylcyclohexyl group), 2, 3-dimethylcyclohexyl group (2, 3-dimethylcyclohexyl group), 3,4, 5-trimethylcyclohexyl group (3, 4, 5-trimethylcyclohexyl group), 4-tert-butylcyclohexyl group (4-tert-butylcyclohexyl group), cycloheptyl group (cycloheptylene group), cyclooctyl group (cyclooctyl group) and the like, but is not limited thereto.

Unless otherwise described, the term alkenyl or alkenylene as used in the present application may be a linear or branched acyclic alkenyl or alkenylene having 2 to 20 carbon atoms, or 2 to 16 carbon atoms, or 2 to 12 carbon atoms, or 2 to 8 carbon atoms, or 2 to 6 carbon atoms, or a cyclic alkenyl or alkenylene having 3 to 20 carbon atoms, or 3 to 16 carbon atoms, or 3 to 12 carbon atoms, or 3 to 8 carbon atoms, or 3 to 6 carbon atoms. Here, when an alkenyl group or alkenylene group having a ring structure is included, it corresponds to a cyclic alkenyl group or alkenylene group. Further, for example, it can be exemplified by vinyl (vinylidene), n-propenyl (n-propenyl), isopropenyl (isopropenyl), n-butenyl (n-butenylene), isobutenyl (isobutylene), t-butenyl (t-butenylene), sec-butenyl (sec-butenylene), 1-methyl-butenyl (1-methyl-butenylene), 1-ethyl-butenyl (1-ethyl-butenylene), n-pentenyl (n-pentenylene), isopentenyl (isopentenyl), neoprene (neoprenylene), t-pentenyl (t-pentenylene), n-hexenyl (n-hexenyl), 1-methylpentenyl (1-methylpentenyl), 2-methylpentenyl (2-methylpentenyl), 4-methyl-2-pentenyl (4-methyl-2-pentenylene), 3-dimethylbutenyl (3, 3-dimethylbutenyl), 2-ethylbutenyl (2-ethylbutenylene), n-heptenyl (n-heptylene), 1-methylhexenyl (n-heptenyl), 1-methylpentenyl (n-heptenyl), n-octenyl (n-octenyl), 2-ethylhexyl alkenyl (2-ethylhexyl enyl), 2-propylpentenyl (2-propylpentenylene), n-nonenyl (n-nonenyl), 2-dimethylheptenyl (2, 2-dimethylheptenyl), 1-ethylpropenyl (1-ethylpropenyl), 1-dimethylpropenyl (1, 1-dimethylpropenyl), isohexenyl (isohexenyl), 2-methylpentenyl (2-methylpentenyl), 4-methylhexenyl (4-methylhexenyl), 5-methylhexenyl (5-methylhexenyl), and the like, but are not limited thereto. Further, the cycloalkenyl group or the cycloalkenyl group may be specifically exemplified by a cyclopropenyl group (cyclopropenyl group), a cyclobutenyl group (cyclobutenyl group), a cyclopentenyl group (cyclopentenyl group), a 3-methylcyclopentenyl group (3-methylcyclopentenylene group), a 2, 3-dimethylcyclopentenyl group (2, 3-dimethylcyclopentenyl group), a cyclohexenyl group (cyclohexenylene group), a 3-methylcyclohexenyl group (3-methylcyclohexenyl group), a 4-methylcyclohexenyl group (4-methylcyclohexenyl group), a 2, 3-dimethylcyclohexenyl group (2, 3-dimethylcyclohexenylene group), a 3,4, 5-trimethylcyclohexenyl group (3, 4, 5-trimethylcyclohexenyl group), a 4-t-butylcyclohexenyl group (4-t-butylcyclohexenylene group), a cycloheptenyl group (cycloheptenyl group), a cyclooctenyl group (cyclooctenyl group) and the like, but is not limited thereto.

Unless otherwise described, the term alkynyl or alkynylene as used in the present application may be a linear or branched acyclic alkynyl or alkynylene having 2 to 20 carbon atoms, or 2 to 16 carbon atoms, or 2 to 12 carbon atoms, or 2 to 8 carbon atoms, or 2 to 6 carbon atoms, or may be a cyclic alkynyl or alkynylene having 3 to 20 carbon atoms, or 3 to 16 carbon atoms, or 3 to 12 carbon atoms, or 3 to 8 carbon atoms, or 3 to 6 carbon atoms. Here, when an alkynyl group or an alkynylene group having a ring structure is included, it corresponds to a cyclic alkynyl group or an alkynylene group. Further, for example, it can be exemplified by ethynyl (ethynylene), n-propynyl (n-propynylene), i-propynyl (i-propynylene), n-butynyl (n-butynylene), i-butynyl (i-butynylene), t-butynyl (t-butynylene), s-butynyl (s-butynylene), 1-methyl-butynyl (1-methyl-butynylene), 1-ethyl-butynyl (1-ethyl-butynylene), n-pentynyl (n-pentyne), i-pentynyl (i-pentyne), neopentynyl (neopentynylene), t-pentyne (t-pentyne), n-hexynyl (n-hexynylene), 1-methylpentynyl (1-methylpentynylene), 2-methylpentynyl (2-methylpentynylene), 4-methyl-2-pentynyl (4-methyl-2-pentyne), 3-dimethylbutynyl (3, 3-dimethylbutynyl), 2-ethylbutynyl (2-ethylheptynyl), n-heptynyl (n-heptynyl), 1-methylpentynyl (n-heptynyl), n-heptynyl (n-heptynyl) (1-methylpentynyl), 2-ethylhexyl group (2-ethylhexyl group), 2-propylpentyl group (2-propylpentyl group), n-nonyl group (n-nonyl group), 2-dimethylheptyl group (2, 2-dimethylheptyl group), 1-ethylpropynyl group (1-ethylpropynyl group), 1-dimethylpropynyl group (1, 1-dimethylpropynyl group), isohexynyl group (isohexynyl group), 2-methylpentanynyl group (2-methylpentanynyl group), 4-methylhexynyl group (4-methylhexynyl group), 5-methylhexynyl group (5-methylhexynyl group), and the like, but are not limited thereto. Further, the cycloalkynyl group or the cycloalkynylene group may be specifically exemplified by a cyclopropynyl group (cyclopropynyl group), a cyclobutynyl group (cyclobutynyl group), a cyclopentynyl group (cyclopentynyl group), a 3-methylcyclopentynyl group (3-methylcyclopentynyl group), a 2, 3-dimethylcyclopentynyl group (2, 3-dimethylcyclopentynyl group), a cyclohexenyl group (cyclohexenyl group), a 3-methylcyclohexynyl group (3-methylcyclohexynyl group), a 4-methylcyclohexynyl group (4-methylcyclohexynyl group), a 2, 3-dimethylcyclohexenyl group (2, 3-dimethylcyclohexenyl group), a 3,4, 5-trimethylcyclohexenyl group (3, 4, 5-trimethylcyclohexenyl group), a 4-tert-butylcyclohexenyl group, a cycloheptynyl group (cycloheptynyl group), a cyclooctynyl group (cyclooctynyl group) and the like, but is not limited thereto.

Alkyl, alkylene, alkenyl, alkenylene, alkynyl and alkynylene groups may also be optionally substituted with one or more substituents. In this case, the substituent may be one or more selected from: halogen (chlorine (Cl), iodine (I), bromine (Br), fluorine (F)), aryl, heteroaryl, epoxy, alkoxy, cyano, carboxyl, acryl, methacryl, acryloyloxy, methacryloyloxy, carbonyl, and hydroxyl, but are not limited thereto.

The term aryl as used in the present application means an aromatic ring in which one hydrogen is removed from the aromatic hydrocarbon ring, wherein the aromatic hydrocarbon ring may comprise a single ring or multiple rings. Unless otherwise described, the aryl group does not have a particularly limited number of carbon atoms, but may be an aryl group having 6 to 30 carbon atoms, or 6 to 26 carbon atoms, or 6 to 22 carbon atoms, or 6 to 20 carbon atoms, or 6 to 18 carbon atoms, or 6 to 15 carbon atoms. Furthermore, the term arylene as used in the present application means that the aryl group has two bonding positions, i.e., a divalent group. The description of aryl groups as described above may be applied, except that arylene groups are each divalent groups. The aryl group may be exemplified by, for example, phenyl, phenethyl, phenylpropyl, benzyl, tolyl, xylyl, naphthyl, or the like, but is not limited thereto.

The term heteroaryl as used in the present application is an aromatic ring comprising one or more heteroatoms other than carbon, which may in particular comprise one or more heteroatoms selected from nitrogen (N), oxygen (O), sulfur (S), selenium (Se) and tellurium (Te). In this case, atoms constituting the ring structure of the heteroaryl group may be referred to as ring atoms. Furthermore, heteroaryl groups may include single or multiple rings. Unless otherwise described, the heteroaryl group does not have a particularly limited number of carbon atoms, but may be a heteroaryl group having 2 to 30 carbon atoms, or 2 to 26 carbon atoms, or 2 to 22 carbon atoms, or 2 to 20 carbon atoms, or 2 to 18 carbon atoms, or 2 to 15 carbon atoms. In another example, the heteroaryl group does not have a particularly limited number of ring atoms, but may be a heteroaryl group having 5 to 30, 5 to 25, 5 to 20, 5 to 15, 5 to 10, or 5 to 8 ring atoms. Heteroaryl groups may be exemplified by, for example, thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, dibenzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzosilol, phenanthroline, isoxazolyl, thiadiazolyl, phenothiazinyl, phenazinyl, and condensed structures thereof, and the like, but are not limited thereto.

Furthermore, the term heteroarylene as used in the present application means that the heteroaryl group has two bonding positions, i.e. a divalent group. The description of heteroaryl groups as described above may be applied, except that each heteroaryl group is a divalent group.

Aryl or heteroaryl groups may also be optionally substituted with one or more substituents. In this case, the substituent may be one or more selected from: halogen (chlorine (Cl), iodine (I), bromine (Br), fluorine (F)), aryl, heteroaryl, epoxy, alkoxy, cyano, carboxyl, acryl, methacryl, acryloyloxy, methacryloyloxy, carbonyl, and hydroxyl, but are not limited thereto.

The present application relates to curable compositions. The term curable composition as used in the present application means a composition prepared by curing reactionA composition to be cured. In the present application, whether curing is properly completed by the curing reaction can be determined by FT-IR (fourier transform infrared), DSC (differential thermal analysis) and DMA (dynamic mechanical analysis) measurements. For example, when the main resin is a polyol resin and the curing agent is an isocyanate compound, it can be determined by the following facts: based on the measurement of 2250cm by FT-IR analysis ^-1 The conversion of the nearby NCO peaks is 80% or greater. Further, in particular, when the main resin is a polyol resin and the curing agent is an isocyanate compound, it can be determined by the fact that: 2250cm as determined by FT-IR analysis based on 24 hours cure at room temperature and normal humidity ^-1 The NCO peak conversion in the vicinity was 80% or more. In the present application, curing may be the same as attempting to cause the curing reaction to proceed and curing to have been properly completed as above.

The curable composition according to one example of the present application may be a resin composition. The term resin composition as used in the present application means a composition comprising a component known in the art as a resin, or a composition not comprising a resin but comprising a component capable of forming a resin by a curing reaction or the like. Thus, in the present application, the term resin or the scope of the resin component includes not only components commonly referred to as resins, but also components capable of forming resins by curing and/or polymerization reactions.

Curable compositions according to one example of the application may be cured to form a Thermal Interface Material (TIM). Thus, in the present application, the cured product of the curable composition and the thermal interface material may refer to the same object.

The curable composition according to one example of the present application may be a one-part or two-part composition. The term one-component composition as used in the present application means a curable composition in which components involved in curing are contained in a state in which they are in physical contact with each other. Furthermore, the term two-component composition as used in the present application may mean a curable composition in which at least some of the components involved in curing are physically separated into separate and contained components.

The curable composition according to one example of the present application may be a room temperature curable type, a thermosetting type, an energy ray curable type, and/or a moisture curable type. The term room temperature curable as used herein refers to curable compositions in which the curing reaction can be initiated and/or carried out at room temperature. Furthermore, the term thermosetting as used in the present application refers to curable compositions in which the curing reaction can be initiated and/or carried out by the application of heat. Further, the term energy ray curable type as used in the present application means a curable composition in which a curing reaction can be initiated and/or performed by irradiation with energy rays (e.g., ultraviolet rays or electron beams, etc.). Furthermore, the term moisture curable as used in the present application refers to curable compositions in which the curing reaction can be initiated and/or carried out in the presence of moisture.

The curable composition according to one example of the application may be solvent-based or solvent-free. Solvent-free formulations may be suitable when considering the aspect of application efficiency or load on the environment, etc.

The curable composition according to one example of the present application may be a polyurethane composition. In this case, the curable composition may comprise polyurethane, or may comprise components capable of forming polyurethane. For example, the thermal interface material, which is the cured product of the curable composition, may comprise polyurethane. In one example, the polyurethane may be formed by the reaction of components in the main part and the curative part, which is described below.

The curable composition or cured product thereof according to one example of the present application may have at least one of the following physical properties. The physical properties described below are independent of each other, and one physical property is not prioritized over another physical property, and at least one, or two or more of the physical properties described below may be satisfied. The physical properties described below are caused by a combination of components contained in the curable composition or a cured product thereof.

The curable composition or the cured product thereof according to one example of the present application may exhibit low adhesion to a specific adherend, or form a cured product capable of exhibiting low adhesion. Such a curable composition may be a polyurethane composition. Polyurethane is known as an adhesive material capable of exhibiting excellent adhesion to various adherends. Therefore, as a method for making the polyurethane composition exhibit low adhesion to an adherend, a method of introducing an adhesion-reducing component such as a plasticizer is generally used. When such components of plasticizer and the like are applied, the adhesion of polyurethane material may be lowered, but there may be a problem that: the relevant components deteriorate other physical properties that can be ensured in the polyurethane or they elute from the polyurethane material during the course of its use. However, in the present application, for the polyurethane material, low adhesion can be achieved while minimizing the use amount of an adhesion-reducing component such as a plasticizer. Thus, in the present application, such a material can be provided: which solves the problem of high adhesion which is not required according to the use while using a polyurethane material.

The adhesion force of the curable composition or the cured product thereof according to one example of the present application to aluminum may be 1N/mm ² Or smaller. In another example, the upper limit of the adhesion of the curable composition or cured product to aluminum may also be 0.1N/mm ² 、0.099N/mm ² 、0.098N/mm ² 、0.097N/mm ² 、0.096N/mm ² 、0.095N/mm ² 、0.094N/mm ² 、0.093N/mm ² 、0.092N/mm ² 、0.091N/mm ² Or 0.09N/mm ² . The adhesion of the curable composition or cured product thereof to aluminum may be less than or equal to any of the upper limits described above. In the present application, the lower limit of the adhesion force to aluminum is not particularly limited. In one example, the adhesion to aluminum may be 0N/mm ² Or greater, or greater than 0N/mm ² . The curable composition may be a curable composition that has substantially no measure of adhesion to aluminum, or may be a curable composition capable of forming a cured product that has substantially no measure of adhesion to aluminum. Accordingly, the adhesion to aluminum may be less than or equal to any of the above upper limits, while being 0N/mm ² Or greater, or greater than 0N/mm ² . The adhesion of the curable composition or cured product thereof to aluminum can be measured in the manner described in the examples herein.

The adhesive force of the curable composition or the cured product thereof according to an example of the present application to the polyester may be 100gf/cm or less. In another example, the upper limit of the adhesion of the curable composition or cured product to the polyester may also be 99.9gf/cm, 99.8gf/cm, 99.7gf/cm, 99.6gf/cm, 99.5gf/cm, 99.4gf/cm, 99.3gf/cm, 99.2gf/cm, 99.1gf/cm, or 99gf/cm. The adhesion of the curable composition or cured product thereof to the polyester may be equal to or less than any of the upper limits described above. In the present application, the lower limit of the adhesive force of the polyester is not particularly limited. In one example, the lower limit of the adhesion of the curable composition or cured product to the polyester may also be about 0gf/cm, 2gf/cm, 4gf/cm, 6gf/cm, 8gf/cm, 10gf/cm, 12gf/cm, 14gf/cm, 16gf/cm, 18gf/cm, or 20 gf/cm. The curable composition or cured product thereof may exhibit substantially no adhesion to the polyester. The adhesion of the curable composition or the cured product thereof to the polyester may also be within the range of any one of the lower limits to any one of the upper limits described above. Adhesion of the curable composition or cured product thereof to the polyester may be measured in the manner described in the examples herein.

The curable composition according to one example of the present application or a cured product thereof may exhibit excellent thermal conductivity characteristics. For example, the lower limit of the thermal conductivity of the curable composition or cured product thereof may also be about 2.0W/mK, 2.1W/mK, 2.2W/mK, 2.3W/mK, 2.4W/mK, 2.5W/mK, 2.6W/mK, 2.7W/mK, 2.8W/mK, 2.9W/mK, or 3W/mK. The thermal conductivity may be greater than or equal to any of the lower limits described above. The upper limit of the thermal conductivity is not particularly limited. For example, the upper limit of the thermal conductivity of the curable composition or cured product thereof may also be about 10W/mK, 9W/mK, 8W/mK, 7W/mK, 6W/mK, 5W/mK, or 4W/mK. The thermal conductivity may be within the range of any one of the above lower limits to any one of the above upper limits. The thermal conductivity of such a curable composition or a cured product thereof can be measured by the method disclosed in examples to be described below.

The curable composition according to one example of the application or the cured product thereof may also exhibit an appropriate hardness. For example, if the hardness of the curable composition or its cured product is too high, there may be a problem due to excessive brittleness. Further, by adjusting the hardness of the curable composition or a cured product thereof according to the purpose of application, impact resistance and vibration resistance can be ensured, and durability of the product can be ensured. The upper limit of the hardness expressed in shore OO type of the curable composition or cured product thereof may be 100, 98, 96, 94, 92 or 90. The shore OO type hardness may be less than or equal to any of the upper limits described above. The lower limit of the shore OO type hardness may be 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, or 80. The shore OO type hardness may be greater than or equal to any of the lower limits described above. The shore OO type hardness may also be in the range of any of the upper limits described above to any of the lower limits described above. The hardness of such a curable composition or a cured product thereof can be measured by the method disclosed in examples to be described below.

The curable composition according to one example of the application or the cured product thereof may also exhibit suitable flexibility. For example, when the flexibility of the curable composition or its cured product is adjusted to a desired level, the application uses can be greatly expanded. For example, the upper limit of the radius of curvature of the curable composition or cured product thereof may be about 20mm, 19mm, 18mm, 17mm, 16mm, 15mm, 14mm, 13mm, 12mm, 11mm, 10mm, or 9 mm. The radius of curvature may be less than or equal to any of the upper limits described above. The lower limit of the radius of curvature may be, for example, about 1mm, 2mm, 3mm, 4mm, 5mm, 6mm, or 7 mm. The radius of curvature may be greater than or equal to any of the lower limits described above. The radius of curvature may also be within the range of any of the upper limits to any of the lower limits. The radius of curvature of such a curable composition or cured product thereof can be measured by the method disclosed in examples to be described below.

The curable composition according to one example of the present application or a cured product thereof may have insulating properties. That is, the curable composition may have insulating properties and/or form a cured product having insulating properties. For example, in the curable composition or cured product thereof, the lower limit of the dielectric breakdown voltage measured according to ASTM D149 may be about 3kV/mm, 5kV/mm, 7kV/mm, 10kV/mm, 15kV/mm, or 20 kV/mm. The dielectric breakdown voltage may be greater than or equal to any of the lower limits described above. The higher the value of the dielectric breakdown voltage, the more excellent the insulating property appears to be, and thus the upper limit is not particularly limited, but the upper limit of the dielectric breakdown voltage may be around 50kV/mm, 45kV/mm, 40kV/mm, 35kV/mm, or 30kV/mm in view of the composition of the curable composition or the like. The dielectric breakdown voltage may be less than or equal to any of the upper limits described above. Such dielectric breakdown voltage may be controlled by adjusting the insulating properties of the curable composition, which may be achieved, for example, by applying an insulating filler in the composition. In general, among the fillers, ceramic fillers are known as components capable of ensuring insulation properties. Further, if the cured product of the curable composition can secure the electrical insulation characteristics as above, stability can be secured while maintaining performance with respect to various materials (e.g., a case or a battery cell included in a battery module).

The curable composition or the cured product thereof according to one example of the present application may have flame retardancy. The curable composition or cured product thereof may exhibit a V-0 rating in the UL 94V test (vertical burn test). Thus, stability against fires and other accidents that are of concern depending on the application of the curable composition can be ensured. In addition, in general, in order to ensure flame retardancy, it is generally ensured by a halogen-containing flame retardant, a phosphorus-containing flame retardant, and a combination thereof. However, in the case of a flame retardant containing substantially no halogen element and a flame retardant containing phosphorus (P) element, the curable composition or cured product thereof may have a V-0 grade result as measured according to the UL 94V test by an appropriate combination of the polyol component and filler component described below.

In the curable composition or the cured product thereof according to one example of the present application, the combined content of the halogen element and the phosphorus element may be 0.3% by weight or less with respect to the total content of the curable composition or the cured product. The upper limit of the combined content of the halogen element and the phosphorus element may be 0.29 wt%, 0.28 wt%, 0.27 wt%, 0.26 wt%, 0.25 wt%, 0.24 wt%, 0.23 wt%, 0.22 wt%, 0.21 wt%, or 0.2 wt% with respect to the total content of the curable composition or the cured product. The combined content of the halogen element and the phosphorus element may be less than or equal to any one of the upper limits described above. The lower limit of the combined content of the halogen element and the phosphorus element is not particularly limited, but may be 0 wt% (excluding), or more than 0 wt% with respect to the total content of the curable composition or the cured product. By the combined content of the halogen element and the phosphorus element, it can be determined that the curable composition or the cured product thereof contains substantially no halogen element-containing flame retardant and no phosphorus element-containing flame retardant. The combined content of the halogen element and the phosphorus element may be greater than or equal to any of the lower limits described above. The combined content of the halogen element and the phosphorus element may be within a range from any one of the upper limits to any one of the lower limits.

The halogen element content, the phosphorus element content, and the combined content of the halogen element and the phosphorus element in the curable composition or the cured product according to an example of the present application can be measured by ICP analysis. As the ICP analysis method used in the present application, ICP-OES (inductively coupled plasma-optical emission spectrometer), ICP-AES (inductively coupled plasma-atomic emission spectrometer), ICP-MS (inductively coupled plasma mass spectrometer), ICP-AAS (inductively coupled plasma-atomic absorption spectrometer) or the like can be used as appropriate, and in view of a measurement target, ICP-OES can be preferably used for analysis, and in particular, measurement can be performed in the manner described in the embodiments of the present specification. The halogen element content, the phosphorus element content, and the combined content of the halogen element and the phosphorus element can be measured by the methods disclosed in examples to be described below.

In the curable composition or cured product according to an example of the present application, the halogen element content may be 0.3% by weight or less relative to the total content of the curable composition or cured product. The upper limit of the halogen element content may be 0.29 wt%, 0.28 wt%, 0.27 wt%, 0.26 wt%, 0.25 wt%, 0.24 wt%, 0.23 wt%, 0.22 wt%, 0.21 wt%, or 0.2 wt% with respect to the total content of the curable composition or cured product. The halogen element content may be less than or equal to any of the upper limits mentioned above. The lower limit of the halogen element content is not particularly limited, but may be 0 wt% (excluding), or more than 0 wt% with respect to the total content of the curable composition or cured product. The curable composition or cured product thereof may be determined by the halogen element content to be substantially free of halogen element-containing flame retardants. The halogen content may be greater than or equal to any of the lower limits described above. The halogen content may also be within the range of any of the upper limits described above to any of the lower limits described above.

In the curable composition or the cured product thereof according to one example of the present application, the phosphorus element content may be 0.3% by weight or less relative to the total content of the curable composition or the cured product. The upper limit of the phosphorus element content may be 0.29 wt%, 0.28 wt%, 0.27 wt%, 0.26 wt%, 0.25 wt%, 0.24 wt%, 0.23 wt%, 0.22 wt%, 0.21 wt%, or 0.2 wt% with respect to the total content of the curable composition or cured product. The phosphorus element content may be less than or equal to any of the upper limits mentioned above. The lower limit of the content of the phosphorus element is not particularly limited, but may be 0% by weight (excluding), or more than 0% by weight with respect to the total content of the curable composition or cured product. The curable composition or cured product thereof may be determined by the phosphorus element content to be substantially free of phosphorus element-containing flame retardants. The phosphorus content may be greater than or equal to any of the lower limits described above. The phosphorus content may also be within the range of any of the upper limits to any of the lower limits.

In the curable composition or the cured product thereof according to one example of the present application, the combined content of the halogen-containing flame retardant and the phosphorus-containing flame retardant may be 1% by weight or less relative to the total content of the curable composition or the cured material. The upper limit of the combined content of the halogen element-containing flame retardant and the phosphorus element-containing flame retardant may be 0.9 wt%, 0.8 wt%, 0.7 wt%, 0.6 wt%, 0.5 wt%, 0.4 wt%, 0.3 wt%, 0.2 wt%, 0.1 wt%, 0.01 wt%, or 0.001 wt%. The combined content of the halogen element-containing flame retardant and the phosphorus element-containing flame retardant may be less than or equal to any of the upper limits described above. The lower limit of the combined content of the halogen element-containing flame retardant and the phosphorus element-containing flame retardant is not particularly limited, but may be 0% by weight (excluding), or more than 0% by weight with respect to the total content of the curable composition or cured product. The combined content of the halogen element-containing flame retardant and the phosphorus element-containing flame retardant may be greater than or equal to any of the lower limits described above. The combined content of the halogen element-containing flame retardant and the phosphorus element-containing flame retardant may also be in the range of any one of the upper limits to any one of the lower limits.

In the curable composition or the cured product thereof according to one example of the present application, the content of the halogen-containing flame retardant may be 1% by weight or less relative to the total content of the curable composition or the cured product. The upper limit of the content of the halogen-containing flame retardant is 0.9 wt%, 0.8 wt%, 0.7 wt%, 0.6 wt%, 0.5 wt%, 0.4 wt%, 0.3 wt%, 0.2 wt%, 0.1 wt%, 0.01 wt%, or 0.001 wt% with respect to the total content of the curable composition or cured product. The content of the halogen-containing flame retardant may be less than or equal to any of the upper limits mentioned above. The lower limit of the content of the halogen-containing flame retardant is not particularly limited, but may be 0% by weight (excluding), or more than 0% by weight with respect to the total content of the curable composition or cured product. The content of the halogen-containing flame retardant may be greater than or equal to any of the lower limits mentioned above. The content of the halogen-containing flame retardant may also be in the range of any one of the above upper limits to any one of the above lower limits.

In the curable composition or the cured product thereof according to one example of the present application, the content of the flame retardant containing a phosphorus element may be 1% by weight or less relative to the total content of the curable composition or the cured product. The upper limit of the content of the flame retardant containing a phosphorus element may be 0.9 wt%, 0.8 wt%, 0.7 wt%, 0.6 wt%, 0.5 wt%, 0.4 wt%, 0.3 wt%, 0.2 wt%, 0.1 wt%, 0.01 wt%, or 0.001 wt% with respect to the total content of the curable composition or cured product. The content of the phosphorus-containing flame retardant may be less than or equal to any of the upper limits mentioned above. The lower limit of the content of the flame retardant containing a phosphorus element is not particularly limited, but may be 0% by weight (excluding), or more than 0% by weight with respect to the total content of the curable composition or cured product. The content of the phosphorus-containing flame retardant may be greater than or equal to any of the lower limits described above. The content of the phosphorus-containing flame retardant may also be in the range of any one of the upper limits to any one of the lower limits.

The specific gravity of the curable composition or the cured product thereof according to one example of the present application may be 3 or less. The upper limit of the specific gravity may be 2.99, 2.98, 2.97 or 2.96. The upper limit of the specific gravity may be less than or equal to any one of the upper limits described above. Such specific gravity may be achieved by applying a filler having a low specific gravity and/or applying a surface treated filler. In addition, the lower limit of the specific gravity is not particularly limited, since the lower the specific gravity is, the more advantageous the weight of the application product is reduced. For example, the specific gravity may be about 1.5 or greater, or 2 or greater. The specific gravity may be greater than or equal to any of the lower limits described above. The specific gravity may also be within a range from any one of the upper limits to any one of the lower limits.

As described above, the curable composition or the cured product thereof according to one example of the present application may be used as a thermal interface material or the like, and for example, heat generated when a battery is rapidly charged may be rapidly dissipated to reduce the risk of fire or the like. However, in order to achieve heat dissipation performance, a heat conductive filler having a high specific gravity is generally excessively applied thereto, but in this case, the weight of the battery increases, and the weight of a product to which the battery is ultimately applied also increases. In particular, when applied to an electric vehicle, it may be detrimental to the fuel efficiency of the vehicle. Therefore, in order for the curable composition or the cured product thereof to have a low specific gravity, the content of the filler having a high specific gravity as described above should be reduced. However, when the high specific gravity filler is reduced, the heat radiation performance is lowered, making it difficult to prevent fire or the like due to accumulated heat. That is, the low specific gravity and the high thermal conductivity are in a trade-off relationship with each other.

The curable composition or the cured product thereof according to one example of the present application can simultaneously ensure low specific gravity characteristics and heat dissipation characteristics even in the above trade-off relationship by an appropriate combination of filler components to be described below.

The curable composition according to one example of the present application may have a low shrinkage during or after curing. By so doing, peeling or void generation and the like that may occur during the application process can be prevented. The shrinkage may be appropriately adjusted within a range capable of exhibiting the above-described effects, and may be, for example, less than 5%, less than 3%, or less than about 1%. Since the shrinkage ratio is more advantageous as the value decreases, the lower limit is not particularly limited.

The curable composition or cured product thereof according to one example of the present application may have a low Coefficient of Thermal Expansion (CTE). By so doing, peeling or void generation and the like that may occur during the application or use process can be prevented. The coefficient of thermal expansion may be appropriately adjusted within a range capable of exhibiting the above-described effects, and may be, for example, less than 300ppm/K, less than 250ppm/K, less than 200ppm/K, less than 150ppm/K, or less than about 100ppm/K. The lower limit is not particularly limited since the lower the value of the thermal expansion coefficient is, the more advantageous it may be.

In the curable composition or the cured product thereof according to an example of the present application, the 5% weight loss temperature in thermogravimetric analysis (TGA) may be 400 ℃ or more, or the 800 ℃ remaining amount may be 70% by weight or more. Stability at high temperatures can be further improved by such characteristics. In another example, the 800 ℃ residual amount may be about 75 wt% or greater, about 80 wt% or greater, about 85 wt% or greater, or about 90 wt% or greater. In another example, the 800 ℃ residual amount may be about 99 wt% or less. Heat of the bodyThe re-analysis (TGA) can be performed at 60cm ³ Nitrogen per minute (N) ₂ ) The heating rate of 20 ℃ for 20 ℃ in the atmosphere is measured in the range of 25 ℃ to 800 ℃. Thermogravimetric analysis (TGA) results may also be achieved by compositional control of the curable composition. For example, the 800 ℃ residual amount is generally affected by the type or ratio of filler contained in the curable composition, and when an excessive amount of filler is contained, the residual amount increases.

The curable composition according to one example of the application may comprise a polyol component. The polyol component may include the polyol in an amount of 55 wt% or more, 60 wt% or more, 65 wt% or more, 70 wt% or more, 75 wt% or more, 80 wt% or more, 85 wt% or more, 90 wt% or more, 95 wt% or more, 99 wt% or more, or 100 wt% relative to the total weight.

The term polyol as used in the present application may mean a compound in which the lower limit of the number of hydroxyl groups is around 2 or 3 per molecule. The upper limit of the number of hydroxyl groups of the polyol is not particularly limited, but may be about 10, 9, 8, 7, 6, 5, 4 or 3 hydroxyl groups per molecule. The number of hydroxyl groups of the polyol may be less than or equal to any of the upper limits described above. The number of hydroxyl groups contained in the polyol may be within a range from any one of the lower limits to any one of the upper limits. The number of hydroxyl groups contained in the polyol may be determined by ¹ H NMR is determined, but the number of hydroxyl groups may be based on 1 ¹ Peaks present in the region of 3ppm to 4ppm in H NMR were determined. Further, the polyol may be named according to the number of hydroxyl groups, and may be referred to as, for example, a difunctional polyol (having two hydroxyl groups) or the like.

The curable composition according to one example of the present application may contain a polyol component in a range of 1 part by weight or more to 80 parts by weight or less with respect to 100 parts by weight of a filler component to be described below. The upper limit of the content of the polyol component may be about 60 parts by weight, 50 parts by weight, 40 parts by weight, 30 parts by weight, 20 parts by weight or 15 parts by weight with respect to 100 parts by weight of the filler component, and the lower limit of the content of the polyol component may be about 2 parts by weight, 3 parts by weight, 4 parts by weight, 5 parts by weight, 6 parts by weight, 7 parts by weight, 8 parts by weight, 9 parts by weight or 10 parts by weight with respect to 100 parts by weight of the filler component. The content of the polyol component may also be greater than or equal to any of the above-mentioned lower limits, less than or equal to any of the above-mentioned upper limits, or within the range of any of the above-mentioned lower limits to any of the above-mentioned upper limits. By controlling the content ratio of the polyol component and the filler component as described above, compounding characteristics can be exhibited, viscosity and thixotropy suitable for the process can be ensured, and a cured product having excellent thermal conductivity can be formed.

In the curable composition according to one example of the present application, the polyol component may include a first polyol that is a difunctional polyol and a second polyol having 3 or more functionalities. By containing the first polyol and the second polyol as the polyol components at the same time, the curable composition can ensure viscosity and thixotropic properties suitable for the process, can be cured more densely at the time of curing to ensure excellent curing characteristics, and can exhibit low adhesion to a specific adherend, or can form a cured product capable of exhibiting low adhesion.

In the curable composition according to one example of the present application, the polyol component is not particularly limited if it is used in the art, but, for example, it may include polyester polyols, polyether polyols, polycarbonate polyols, polyester polycarbonate polyols, polyolefin polyols, conjugated diene polymer-based polyols, castor oil-based polyols, silicone-based polyols, vinyl polymer-based polyols, and the like, depending on the skeleton structure. These may be used in a single type, and may be used in a combination of 2 or more types.

In the curable composition according to one example of the present application, the first polyol or the second polyol of the polyol component may be an oil modified polyol or a non-oil modified polyol.

The term oil modified polyol as used in the present application means that it contains a polyol having 3 or more carbon atoms at the endLinear or branched hydrocarbyl polyols. Thus, polyols that do not contain linear or branched hydrocarbyl groups having 3 or more carbon atoms at the terminal end may be referred to herein as non-oil modified polyols. That is, the first polyol or the second polyol of the polyol component may contain a branched hydrocarbon chain having 3 or more carbon atoms at the terminal end. Can pass through ¹ H NMR determination of whether the first polyol or the second polyol comprises a hydrocarbon group, wherein based on ¹ The presence and amount of hydrocarbon groups can be determined by the presence of peaks in the region of 4ppm to 5ppm in H NMR. When the oil-modified polyol is applied and formed into a polyurethane material, a low adhesion to a specific material can be ensured while minimizing the use amount of an adhesion-reducing component such as a plasticizer, and excellent compounding characteristics can be provided.

The lower limit of the number of carbon atoms of the linear or branched hydrocarbon group contained in the terminal of the oil-modified polyol may be around 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16 or 17. The number of carbon atoms may be greater than or equal to any of the lower limits described above. The upper limit of the number of carbon atoms may be about 50, 49, 48, 47, 46, 45, 44, 43, 42, 41, 40, 39, 38, 37, 36, 35, 34, 33, 32, 31, 30, 29, 28, 27, 26, 25, 24, 23, 22, 21, 20, 19, 18, 17, 16, 15, 14, 13, 12, 11, 10, 9, or 8. The number of carbon atoms may be less than or equal to any of the upper limits described above. The number of carbon atoms may be within a range from any one of the lower limits to any one of the upper limits.

The linear or branched hydrocarbyl groups may or may not contain double bonds. Where a double bond is included, such a double bond may be a conjugated double bond or a cis double bond.

Specific types of hydrocarbyl groups may be exemplified by alkyl, alkenyl, or alkynyl groups. In one example, the hydrocarbyl group may be attached to the polyol compound through a carbonyl or carbonyloxy group, and in this case, the hydrocarbyl group may be an alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, alkylcarbonyloxy, alkenylcarbonyloxy, or alkynylcarbonyloxy group. Here, the number of carbon atoms of the alkyl group, alkenyl group or alkynyl group may be larger than or equal to any of the above-mentioned lower limits of the number of carbon atoms of the linear or branched hydrocarbon group, smaller than or equal to any of the above-mentioned upper limits of the linear or branched hydrocarbon group, or within a range from any of the above-mentioned lower limits of the number of carbon atoms of the linear or branched hydrocarbon group to any of the above-mentioned upper limits of the linear or branched hydrocarbon group.

Alkyl, alkenyl or alkynyl groups may be linear or branched and may be optionally substituted with one substituent. When a substituent is present, the type of substituent is not particularly limited, and for example, a halogen atom such as fluorine (F) may be exemplified as a substituent.

In one example, a hydrocarbyl group may be included in a substituent of formula 1 below.

[ 1]

In formula 1, R is a linear or branched hydrocarbyl group.

In formula 1, the symbol means that the relevant moiety is linked to the polyol. Thus, the oxygen atom in the substituent of formula 1 may be attached to the polyol.

The specific type of hydrocarbyl group that is R in formula 1 is as described above. Accordingly, the content regarding the number of carbon atoms, the type, the form, and the substituents of the above-described hydrocarbon groups can be applied in the same manner as above.

The number of hydrocarbon groups contained in the oil-modified polyol is not particularly limited. For example, the lower limit of the number of hydrocarbon groups contained in the oil-modified polyol may be 1 or 2 per molecule of compound. The upper limit of the number of hydrocarbon groups contained in the oil-modified polyol may also be 10, 9, 8, 7, 6, 5, 4, 3 or 2 per molecule of compound. The number of hydrocarbon groups may also be greater than or equal to any of the above-mentioned lower limits, less than or equal to any of the above-mentioned upper limits, or within the range of any of the above-mentioned lower limits to any of the above-mentioned upper limits.

If the oil modified polyol contains hydroxyl groups and hydrocarbon groups, it may have various forms.

In one example, the oil modified polyol may be a compound in the form of a hydrocarbon compound, such as an alkane, alkene, or alkyne, with at least some of the hydrogen atoms of the compound being substituted with hydroxyl and/or hydrocarbyl groups. The number of carbon atoms in a hydrocarbon compound such as an alkane, alkene, or alkyne can be, for example, 1 to 20, 1 to 16, 1 to 8, or 4 to 6. Such hydrocarbon compounds, e.g., alkanes, alkenes, or alkynes, may be linear, branched, or cyclic. In addition, the hydroxyl and/or hydrocarbyl groups in the alkane, alkene, or alkyne may be substituted on the same carbon atom, or may also be substituted on different carbon atoms.

In another example, the oil modified polyol may have a polyester backbone or a polyether backbone. In this case, the oil modified polyol may be an oligomer compound or a polymer compound.

In one example, the oil modified polyol having a polyester skeleton is a so-called polyester polyol, and may be a polyol having a structure in which a hydrocarbon group is attached to such a polyester polyol.

Further, the oil-modified polyol having a polyether skeleton is a so-called polyether polyol, and may be a polyol having a structure in which a hydrocarbon group is attached to such a polyether polyol.

In one example, the polyester backbone may be a so-called polycaprolactone backbone and the polyether backbone may be a so-called polyalkylene backbone.

In one example, the polyester backbone may be a backbone having a repeating unit represented by the following formula 2.

[ 2]

In formula 2, X ₁ And X ₂ Each independently is a single bond or an oxygen atom, L ₁ Can be alkylene or alkylidene, and n is any number.

In the present application, the term single bond means a case where no atom is present at the relevant position.

In formula 2, in one example, the alkylene group may be an alkylene group having 2 to 20 carbon atoms, 4 to 16 carbon atoms, 4 to 12 carbon atoms, or 4 to 8 carbon atoms, which may be linear or branched.

In formula 2, in one example, the alkylidene group may be an alkylidene group having 1 to 20 carbon atoms, 4 to 16 carbon atoms, 4 to 12 carbon atoms, or 4 to 8 carbon atoms, which may be linear or branched.

In the present application, both alkylene and alkylidene refer to divalent substituents formed by leaving two hydrogen atoms in an alkane. Alkylene and alkylidene groups differ from each other in that: alkylene is a divalent substituent formed by leaving two hydrogen atoms from different carbon atoms of an alkane, while alkylidene is a divalent substituent formed by leaving two hydrogen atoms from one carbon atom of an alkane.

In one example, the polyester backbone may be a polycaprolactone backbone, and in this case, L of formula 2 above ₁ May be a linear alkylene group having 5 carbon atoms or a linear alkylidene group having 5 carbon atoms.

In formula 2, n is an arbitrary number indicating the number of repeating units. The lower limit of n above may be, for example, around 1, 2, 3, 4 or 4.5, and the upper limit may be around 25, 20, 15, 10 or 5. The above n may be greater than or equal to any of the above lower limits, less than or equal to any of the above upper limits, or within the range of any of the above lower limits to any of the above upper limits.

The backbone of formula 2 may be a so-called carboxylic polyol backbone or a caprolactone polyol backbone. Such backbones may be formed in a known manner, for example, backbones of carboxylic acid polyols may be formed by reacting components comprising carboxylic acids and polyols (e.g., diols or triols, etc.), and backbones of caprolactone polyols may be formed by reacting components comprising caprolactone and polyols (e.g., diols or triols, etc.). The carboxylic acid may be a dicarboxylic acid.

In the oil modified polyol having the skeleton of formula 2, a hydroxyl group or the above hydrocarbon group may be present at the end of the skeleton of formula 2.

In this case, the skeleton of the above formula 2 may be represented by the following formula 3.

[ 3]

In formula 3, X ₁ 、X ₂ 、L ₁ And n is as defined in formula 2, and R ₁ Can be a hydroxyl group or a substituent of formula 4 below.

[ 4]

In formula 4, X ₃ Is a single bond or an oxygen atom, and R is the same as R of formula 1 above.

R in formula 3 ₁ When hydroxyl is, X ₁ Can be a single bond, and X ₂ May be an oxygen atom; when R is ₁ In the case of the substituent of formula 4, X ₁ And X ₃ Either one of them may be a single bond, and the other may be an oxygen atom.

In the oil-modified polyol, the lower limit of the number of skeletons of the above formula 2 or formula 3 may be about 1 or 2, and the upper limit may be about 10, 9, 8, 7, 6, 5, 4, 3, or 2. The number of skeletons may be greater than or equal to any of the above-described lower limits, less than or equal to any of the above-described upper limits, or within a range from any of the above-described lower limits to any of the above-described upper limits.

The oil modified polyol having a polyester backbone may have a linear or branched structure.

Here, the linear structure is a structure in which a main chain including the skeleton of the above formula 2 or formula 3 is present and no other polymer chain is attached to the main chain, and the branched structure may be in a form in which a chain including the skeleton of the above formula 2 or formula 3 is bonded as a side chain to the main chain including the skeleton of the above formula 2 or formula 3. Here, in the branched structure, the number of chains including the skeleton of the above formula 2 or formula 3 attached as side chains may be, for example, 1 to 5, 1 to 4, 1 to 3, 1 to 2, or 1.

In one example, the oil modified polyol having a polyester backbone may be a compound in the form of a hydrocarbon compound, such as an alkane, alkene, or alkyne, with at least some of the hydrogen atoms replaced with hydroxyl groups and/or the backbone of formula 3 above. The number of carbon atoms in a hydrocarbon compound such as an alkane, alkene, or alkyne can be, for example, 1 to 20, 1 to 16, 1 to 8, or 4 to 6.

Such hydrocarbon compounds, e.g., alkanes, alkenes, or alkynes, may be linear, branched, or cyclic. In addition, the hydroxyl groups and/or the backbone of formula 3 may be substituted on the same carbon atom in an alkane, alkene, or alkyne, or may also be substituted on different carbon atoms.

In one example, the polyether backbone may be a backbone having repeating units of formula 5 below.

[ 5]

In formula 5, X ₄ And X ₅ Each independently is a single bond or an oxygen atom, L ₂ Can be alkylene or alkylidene, and m is any number.

In formula 5, in one example, the alkylene group may be an alkylene group having 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, which may be linear or branched.

In formula 5, in one example, the alkylidene group may be an alkylene 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, which may be linear or branched.

The meaning of alkylene and alkylidene is as described above.

In formula 5, m is an arbitrary number representing the number of repeating units, which may be a number in the range of 1 to 25, for example.

In the oil-modified polyol having the skeleton of formula 5, a hydroxyl group or the above hydrocarbon group may be present at the end of the skeleton of formula 5 above.

In this case, the skeleton of formula 5 may be represented by formula 6 below.

[ 6]

In formula 6, X ₄ 、X ₅ 、L ₂ And m is as defined in formula 5, and R ₂ Can be a hydroxyl group or a substituent of formula 7 below.

[ 7]

In formula 7, X ₆ Is a single bond or an oxygen atom, and R is the same as R in formula 1 above.

R in formula 6 ₂ When hydroxyl is, X ₄ Is a single bond, and when R ₂ In the case of the substituent of formula 7, X ₄ And X ₆ Either one of them is a single bond, and the other is an oxygen atom.

The oil modified polyol may comprise one or more, or two or more backbones of formula 5 or formula 6 above. The backbone of formula 5 or formula 6 above may be included in the polyol compound in an amount of 10 or less, 9 or less, 8 or less, 7 or less, 6 or less, 5 or less, 4 or less, 3 or less, or 2 or less.

The oil modified polyol having a polyether backbone may have a linear or branched structure.

Here, the linear structure may be a structure in which a main chain including the skeleton of the above formula 5 or formula 6 is present and no other polymer chain is connected to the main chain, and the branched structure may be in the form of a chain including the skeleton of the above formula 5 or formula 6 as a side chain bonded to the main chain including the skeleton of the above formula 5 or formula 6. Here, in the branched structure, the number of chains including the skeleton of the above formula 5 or formula 6 attached as side chains may be, for example, 1 to 5, 1 to 4, 1 to 3, 1 to 2, or 1.

In one example, the oil modified polyol having a polyether backbone may be a compound in the form of a hydrocarbon compound, such as an alkane, alkene, or alkyne, with at least some of the hydrogen atoms replaced with hydroxyl groups and/or the backbone of formula 5 above. The number of carbon atoms in a hydrocarbon compound such as an alkane, alkene, or alkyne can be, for example, 1 to 20, 1 to 16, 1 to 8, or 4 to 6.

Such hydrocarbon compounds, e.g., alkanes, alkenes, or alkynes, may be linear, branched, or cyclic. In addition, the hydroxyl groups and/or the backbone of formula 5 may be substituted on the same carbon atom in an alkane, alkene, or alkyne, or may also be substituted on different carbon atoms.

When the above oil-modified polyol is an oligomer compound or a polymer compound, the relevant compound may have a molecular weight at an appropriate level.

For example, the lower limit of the weight average molecular weight of the oligomer or polymer oil-modified polyol may be about 100g/mol, 200g/mol, 300g/mol, 400g/mol, 500g/mol, 600g/mol, or 700g/mol, and the upper limit may also be about 5,000g/mol, 4,500g/mol, 4,000g/mol, 3,500g/mol, 3,000g/mol, 2,500g/mol, 2,000g/mol, 1,500g/mol, 1,000g/mol, or 900 g/mol. The weight average molecular weight may also be greater than or equal to any of the above lower limits, less than or equal to any of the above upper limits, or within the range of any of the above lower limits to any of the above upper limits.

By applying the oil-modified polyol as described above, desired physical properties can be more effectively ensured. Further, by applying the above-described oil-modified polyol as the first polyol, desired physical properties can be ensured more effectively.

The oil modified polyol may be synthesized by known synthetic methods. That is, the polyol may be prepared by reacting a compound capable of introducing a hydrocarbon group corresponding to the oil modifying moiety with a known polyol or alcohol compound. Herein, a polyol is as defined in the present application, and an alcohol compound means a compound containing one hydroxyl group per molecule. Here, the compound capable of introducing a hydrocarbon group may be exemplified by saturated or unsaturated fatty acids, and specifically, may be exemplified by butyric acid, caproic acid, 2-ethylhexanoic acid, caprylic acid, isononanoic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, linoleic acid, oleic acid, or the like, but is not limited thereto.

In addition, the type of the polyol or alcohol compound to be reacted with the saturated or unsaturated fatty acid is not particularly limited, and for example, a general polyol of an appropriate type to be described below may be applied, but is not limited thereto.

The non-oil modified polyol may have various forms.

In one example, the non-oil modified polyol may be a polyester polyol. As polyester polyols, for example, so-called carboxylic acid polyols or caprolactone polyols can be used.

In one example, the polyester polyol may be a backbone having repeating units of formula 8 below.

[ 8]

In formula 8, X ₇ And X ₈ Each independently is a single bond or an oxygen atom, L ₃ Can be alkylene or alkylidene, and p is any number.

In formula 8, in one example, the alkylidene group may be an alkylene group having 1 to 20 carbon atoms, 4 to 16 carbon atoms, 4 to 12 carbon atoms, or 4 to 8 carbon atoms, which may be linear or branched.

In formula 8, in one example, the alkylene group may be an alkylene group having 2 to 20 carbon atoms, 4 to 16 carbon atoms, 4 to 12 carbon atoms, or 4 to 8 carbon atoms, which may be linear or branched.

When the polyester polyol is a polycaprolactone polyol, L of formula 8 above ₃ May be a linear alkylene group having 5 carbon atoms.

Further, in the above formula 8, p is an arbitrary number indicating the number of repeating units, which may be a number in the range of 1 to 25, for example.

The polyester polyol having the skeleton of the above formula 8 may be a so-called carboxylic acid polyol or caprolactone polyol. Such polyol compounds may be formed by known methods, for example, carboxylic acid polyols may be formed by reacting components comprising carboxylic acids and polyols (e.g., diols or triols, etc.), and caprolactone polyols may be formed by reacting components comprising caprolactone and polyols (e.g., diols or triols, etc.). The carboxylic acid may be a dicarboxylic acid.

In the polyol compound having the skeleton of the above formula 8, a hydroxyl group may be present at the end of the skeleton of the above formula 8 or at another position of the polyester polyol.

When the non-oil modified polyol comprises backbones of formula 8 above, the lower limit of the number of relevant backbones may be around 1 or 2, and the upper limit may also be around 10, 9, 8, 7, or 6, 5, 4, 3, 2, or 1. The number of skeletons is greater than or equal to any of the above-mentioned lower limits, less than or equal to any of the above-mentioned upper limits, or within the range of any of the above-mentioned lower limits to any of the above-mentioned upper limits.

The non-oil modified polyol having a polyester backbone may have a linear or branched structure.

Here, the linear structure may be a structure in which a main chain including the skeleton of the above formula 8 is present and no other polymer chain is attached to the main chain, and the branched structure may be in the form of a chain including the skeleton of the above formula 8 as a side chain bonded to the main chain including the skeleton of the above formula 8. In the branched structure, the number of chains including the skeleton of the above formula 8 attached as side chains may be, for example, 1 to 5, 1 to 4, 1 to 3, 1 to 2, or 1.

In another example, as the non-oil modified polyol, a polyol having the following may also be used: polycaprolactone polyol units or alkylene glycol units; polyol units and dicarboxylic acid units. Such polyols may be the above polycaprolactone polyols or alkylene glycols, or mixtures of polyols and dicarboxylic acids, or may be the reaction products thereof. That is, the polycaprolactone polyol unit, the alkylene glycol unit, the polyol unit, and the dicarboxylic acid unit may be units derived from polycaprolactone polyol, alkylene glycol polyol, and dicarboxylic acid, respectively. At this time, the alkylene glycol may be exemplified by a glycol compound having 1 to 20 carbon atoms, 4 to 16 carbon atoms, or 4 to 12 carbon atoms, such as 3-methyl-1, 5-pentanediol, 1, 9-nonanediol, or 1, 6-hexanediol. Further, the polyol unit may be exemplified by an alkane having 1 to 20 carbon atoms, 4 to 16 carbon atoms, or 4 to 12 carbon atoms substituted with 3 to 10, 3 to 9, 3 to 8, 3 to 7, 3 to 6, 3 to 5, or 3 to 4 hydroxyl groups, such as trimethylolpropane. Further, the dicarboxylic acid may be exemplified by adipic acid, terephthalic acid, isophthalic acid, sebacic acid, or the like. Such polyol compounds are known by the product names P-510, P-1010, P-2010, P-3010, P-4010, P-5010, P-6010, F-510, F-1010, F-2010, F-3010, P-2011, P-520, P-2020, P-1012, P-2012, P-630, P-2030, P-2050, or N-2010 of Kuraray, for example.

When the above-mentioned non-oil-modified polyol is an oligomer compound or a polymer compound, the compound may have a molecular weight at an appropriate level.

For example, the weight average molecular weight of the oligomer or polymer non-oil modified polyol may have a lower limit of about 100g/mol, 200g/mol, 300g/mol, 400g/mol, 500g/mol, 600g/mol, or 700g/mol, and an upper limit of about 5,000g/mol, 4,500g/mol, 4,000g/mol, 3,500g/mol, 3,000g/mol, 2,500g/mol, 2,000g/mol, 1,500g/mol, 1,000g/mol, or 900 g/mol. The weight average molecular weight may also be greater than or equal to any of the above lower limits, less than or equal to any of the above upper limits, or within the range of any of the above lower limits to any of the above upper limits.

By applying the non-oil modified polyol as described above, desired physical properties can be more effectively ensured. Further, by using the above-described oil-modified polyol as the first polyol and using the above-described non-oil-modified polyol as the second polyol, desired physical properties can be ensured more effectively.

In the curable composition according to one example of the present application, the first polyol or the second polyol of the polyol component may be a polyester polyol having a polyester skeleton. The polyester polyol may be an oil modified polyol or a non-oil modified polyol as described above. Since the polyol component contains the first polyol as the polyester oil-modified polyol having a polyester skeleton and the second polyol as the non-oil-modified polyester polyol having a polyester skeleton, desired physical properties can be more effectively ensured.

In the curable composition according to one example of the present application, the first polyol of the polyol component may be an oligomer compound or a polymer compound, and may have an appropriate level of molecular weight. The first polyol may have a weight average molecular weight with a lower limit of about 100g/mol, 200g/mol, 300g/mol, 400g/mol, 500g/mol, 600g/mol, or 700g/mol, and an upper limit of about 2,000g/mol, 1,500g/mol, 1,000g/mol, or 900 g/mol. The weight average molecular weight may also be greater than or equal to any of the above lower limits, less than or equal to any of the above upper limits, or within the range of any of the above lower limits to any of the above upper limits.

In the curable composition according to one example of the present application, the second polyol of the polyol component may be an oligomer compound or a polymer compound, and may have an appropriate level of molecular weight. The second polyol may have a weight average molecular weight of about 500g/mol, 600g/mol, or 700g/mol, and may also have a lower limit of about 5,000g/mol, 4,500g/mol, 4,000g/mol, or 3,500g/mol, 3,000g/mol, 2,500g/mol, 2,000g/mol, 1,500g/mol, 1,000g/mol, or 900 g/mol. The weight average molecular weight may also be greater than or equal to any of the above lower limits, less than or equal to any of the above upper limits, or within the range of any of the above lower limits to any of the above upper limits.

In the curable composition according to one example of the present application, by controlling the weight average molecular weights of the first polyol and the second polyol in the polyol component within the above range, it is possible to ensure viscosity and thixotropic properties suitable for the process.

In the curable composition according to one example of the present application, the polyol component may include the first polyol in an amount of greater than 80 wt% relative to the total weight of the polyol component. The lower limit of the content of the first polyol in the polyol component may be about 81 wt%, 82 wt%, 83 wt%, 84 wt%, 85 wt%, 86 wt%, 87 wt%, 88 wt%, 89 wt%, or 90 wt%, and the upper limit may be about 97 wt%, 96 wt%, 95 wt%, 94 wt%, 93 wt%, 92 wt%, or 91 wt%, with respect to the total weight of the polyol component. The first polyol in the polyol component may also be present in an amount greater than or equal to any of the lower limits set forth above, less than or equal to any of the upper limits set forth above, or within the range of any of the lower limits set forth above to any of the upper limits set forth above.

By controlling the content of the first polyol as above, it can have excellent compounding characteristics in combination with a filler component to be described below; viscosity and thixotropy suitable for the process can be ensured; can be cured more densely upon curing to ensure excellent curing characteristics; and may exhibit low adhesion to a specific adherend; or a cured product capable of exhibiting low adhesion may be formed.

In the curable composition according to one embodiment of the present application, the first polyol (P _A ) With a second polyol (P) _B ) Weight ratio (P) _A /P _B ) May be 5 or greater. Weight ratio (P) _A /P _B ) The lower limit of (2) may be about 5.5, 6, 6.5, 7, 7.5, 8, 8.5, or 9, and the upper limit may be about 20, 18, 16, 14, 12, or 10. Weight ratio (P) _A /P _B ) It may be greater than or equal to any of the above lower limits, less than or equal to any of the above upper limits, or within the range of any of the above lower limits to any of the above upper limits.

By controlling the first polyol (P _A ) With a second polyol (P) _B ) Weight ratio (P) _A /P _B ) Which may have excellent compounding characteristics in combination with filler components to be described below; viscosity and thixotropy suitable for the process can be ensured; can be cured more densely upon curing to ensure excellent curing characteristics; and may exhibit low adhesion to a specific adherend;or a cured product capable of exhibiting low adhesion may be formed. In particular, due to the polyol component of the curable composition controlling the first polyol (P _A ) With a second polyol (P) _B ) Weight ratio (P) _A /P _B ) It may thus exhibit low adhesion to both PET and aluminum, or may form a cured product capable of exhibiting low adhesion.

In the curable composition according to one example of the present application, the first polyol may have an OH% in the range of 3 or more to 20 or less. The lower limit of OH% of the first polyol may be 3.5, 4, 4.5, 5, 5.5, 6, 6.5, 7 or 7.5 and the upper limit may be 18, 16, 14, 12 or 10. The OH% of the first polyol may also be greater than or equal to any of the lower limits, less than or equal to any of the upper limits, or within the range of any of the lower limits to any of the upper limits. Further, when the OH% of the first polyol satisfies the above range, the cured product of the curable composition having an appropriate hardness other than brittleness can be ensured.

The term OH% of the polyol as used in the present application may mean a percentage of the weight of hydroxyl groups (-OH) contained in the polyol corresponding to 1mol with respect to the weight of the polyol corresponding to 1 mol.

In the curable composition according to one example of the present application, the second polyol may have an OH% in the range of 0.5 or more to 5 or less. The lower limit of OH% of the second polyol may be 0.75, 0.8, 0.85, 0.9, 0.95, 1, 1.25, 1.5, 1.75, 2, 2.25, or 2.5, and the upper limit may be 4.5, 4, 3.5, or 3. The OH% of the second polyol may also be greater than or equal to any of the lower limits, less than or equal to any of the upper limits, or within the range of any of the lower limits to any of the upper limits. Further, when the OH% of the first polyol satisfies the above range, the cured product of the curable composition having an appropriate hardness other than brittleness can be ensured.

In the curable composition according to one example of the present application, the polyol component may further include additional polyols different from the first polyol and the second polyol. The additional polyol may be an oil modified polyol or a non-oil modified polyol as described above, or a mixture thereof.

The curable composition according to one example of the application may comprise a filler component. By combining the polyol component and filler component described above, the curable composition can ensure viscosity and thixotropic properties suitable for the process.

The curable composition according to one example of the application was at 2.4 seconds ^-1 The viscosity at 25 ℃ measured at shear rate conditions of (c) may be 400kcP or less. The upper limit of the viscosity of the curable composition may be about 390kcP, 380kcP, 370kcP, 360kcP, 350kcP, 340kcP, 330kcP, 320kcP, 310kcP, or 300kcP, and the lower limit may be about 100kcP, 105kcP, or 110kcP, 115kcP, 120kcP, 125kcP, 130kcP, or 135 kcP. The viscosity of the curable composition may also be greater than or equal to any of the lower limits, less than or equal to any of the upper limits, or within the range of any of the lower limits to any of the upper limits.

The thixotropic index (t.i.) of the curable composition according to one example of the present application may be 5 or less according to the following general equation 1. The upper limit of the thixotropic index of the curable composition may be about 4.9, 4.8, 4.7, 4.6, 4.5, 4.4, 4.3, 4.2, 4.1 or 4, and the lower limit may be about 1.5, 1.6, 1.7, 1.8, 1.9, 2.0, 2.1, 2.2, 2.3, 2.4, 2.5, 2.6 or 2.7. The thixotropic index of the curable composition may also be greater than or equal to any of the lower limits, less than or equal to any of the upper limits, or within the range of any of the lower limits to any of the upper limits.

[ general equation 1]

Thixotropic index (t.i.) =v ₁ /V ₂

In general equation 1, V ₁ At 25℃and 0.24 seconds for a curable composition ^-1 Viscosity measured under the conditions of (2) and V ₂ At 25℃and 2.4 seconds for a curable composition ^-1 Viscosity measured under the conditions of (2).

The curable composition according to one example of the present application may include a filler component in a range of 70 wt% or more to 98 wt% or less with respect to the total weight. The lower limit of the content of the filler component may be about 72 wt%, 74 wt%, 76 wt%, 78 wt%, 80 wt%, 82 wt%, 84 wt% or 86 wt% with respect to the total weight of the curable composition, and the upper limit of the content of the filler component may be 97 wt%, 96 wt%, 95 wt%, 94 wt%, 93 wt%, 92 wt% or 91 wt% with respect to the total weight of the curable composition. The filler component may also be present in an amount greater than or equal to any of the above-mentioned lower limits, less than or equal to any of the above-mentioned upper limits, or within the range of any of the above-mentioned lower limits to any of the above-mentioned upper limits. By controlling the content of the filler component as above, a cured product having excellent thermal conductivity while having viscosity and thixotropy suitable for the process can be formed.

In the curable composition according to one example of the present application, the filler component may include a filler. If the filler is used in the art, the type, shape, size, and the like of the filler are not particularly limited. Further, the filler component may comprise one, or two or more fillers. Furthermore, even if the same type of filler is used, the filler component may be a mixture of fillers having different shapes or sphericities, or a mixture of fillers having different average particle diameters. For example, the filler component may be a mixture of aluminum hydroxide and aluminum oxide (alumina), and the shape and average particle diameter of the aluminum hydroxide and aluminum oxide may be different from each other.

In the present application, the particle average particle diameter of the filler is the D50 particle diameter of the filler, which is the particle diameter measured by Marvern's MASTER SIZER3000 apparatus according to ISO-13320 standard. Distilled water was used as a solvent in the measurement. The incident laser light is scattered by the filler dispersed in the solvent, and the values of the intensity and directivity of the scattered laser light are changed according to the size of the filler, which is analyzed by the Mie (Mie) theory, whereby the D50 particle diameter can be obtained. By the above analysis, the distribution can be obtained by converting into a diameter of a sphere having the same volume as the dispersed filler, and the particle diameter can be evaluated by obtaining a D50 value as a median value of the distribution.

In the present application, a spherical shape of the filler may mean a sphericity of about 0.9 or more, and an aspherical shape may mean a sphericity of less than about 0.9. Sphericity may be determined by analysis of the particle shape of the filler. Specifically, sphericity of a filler as a three-dimensional particle may be defined as a ratio (S '/S) of a surface area (S) of the particle to a surface area (S') of a sphere having the same volume of the particle. For actual particles, circularity is generally used. After obtaining a two-dimensional image of an actual grain, the circularity is expressed as a ratio of a boundary (P) of the image and a boundary of a circle having the same image and the same area (a), and is obtained by the following equation.

< circularity equation >

Circularity=4pi a/P ²

The circularity is represented by a value ranging from 0 to 1, where the value of a perfect circle is 1, and the more irregular the particle shape, the smaller the value thereof is 1. In the present application, the sphericity value may be measured as an average value of circularities measured by a particle shape analysis apparatus (FPIA-3000) of Marvern.

In the curable composition according to one example of the present application, the filler component may include a first filler having a specific gravity of 3 or less and a second filler having a specific gravity of greater than 3. In the present application, the specific gravity of the filler may be based on a value measured by a density measurement method of JIS Z2512 (2012). The curable composition can ensure both low specific gravity characteristics and heat dissipation characteristics by including the first filler and the second filler. The lower limit of the specific gravity of the first filler is not particularly limited, but may be about 0.5, 0.6 or 0.7, and the specific gravity of the first filler may be in the range of 3 or less to any one of the above lower limits. Further, the upper limit of the specific gravity of the second filler is not particularly limited, but may be around 30, 28, 26, 24, 22 or 20, and the specific gravity of the second filler may be in the range of 3 or more to any one of the upper limits described above. Further, the specific gravity of the second filler may be in the range of 3.1 or more to any one of the upper limits described above.

In the curable composition according to one example of the present application, the filler component may include the first filler in a range of 10 wt% or more to 80 wt% with respect to the total weight of the curable composition. The upper limit of the content of the first filler may be about 75 wt%, 70 wt%, 65 wt%, 60 wt%, 55 wt% or 50 wt% with respect to the total weight of the curable composition, and the lower limit of the content of the first filler may be about 11 wt%, 12 wt%, 13 wt%, 14 wt%, 15 wt% or 16 wt% with respect to the total weight of the curable composition. The content of the first filler may also be greater than or equal to any of the above-mentioned lower limits, less than or equal to any of the above-mentioned upper limits, or within the range of any of the above-mentioned lower limits to any of the above-mentioned upper limits. By controlling the content of the first filler as above, both the low specific gravity property and the heat dissipation property can be ensured, and the rapid increase of the adhesive force can be prevented even in the thermal shock test according to the Mil-Std-883 method 1010 or the JEDEC JESD 22-A104. Further, by controlling the content of the first filler as above, even when the flame retardant containing halogen element and the flame retardant containing phosphorus (P) element are not substantially contained, the V-0 grade can be ensured according to the result of UL 94V test measurement.

In the curable composition according to one example of the present application, the first filler may be a metal hydroxide. The type of the metal hydroxide is not particularly limited, but may include one or more selected from aluminum hydroxide and magnesium hydroxide.

In the curable composition according to one example of the present application, for example, the first filler may have an average particle diameter of 60 μm or less while being a metal hydroxide. The lower limit of the average particle diameter of the first filler is not particularly limited, but may be 0.1 μm, 0.5 μm or 1 μm. The average particle diameter of the first filler may be in the range of 60 μm or less to any one of the lower limits described above. By controlling the average particle diameter of the first filler within the above range, both the low specific gravity property and the heat dissipation property can be ensured, and the release property and the thixotropy suitable for the process can be exhibited.

In the curable composition according to one example of the present application, the first filler may contain one kind of filler, or two or more kinds of filler having an average particle diameter of 60 μm or less. For example, the first filler may contain a metal hydroxide having an average particle diameter of about 1 μm, or may contain a filler having an average particle diameter of about 1 μm and a metal hydroxide having an average particle diameter of about 50 μm.

In the curable composition according to one example of the present application, the first filler may contain a first metal hydroxide (O) having an average particle diameter in the range of any one of the lower limits of the particle average particle diameter of the first filler to 10 μm or less ₁ ) A second metal hydroxide (O) having an average particle diameter of 60 μm or less and more than 10 μm ₂ ). Since the first filler contains the first metal hydroxide and the second metal hydroxide, both of the low specific gravity property and the heat dissipation property can be ensured, and the release property and the thixotropy suitable for the process can be exhibited.

In the curable composition according to one embodiment of the present application, the first metal hydroxide (O ₁ ) With a second metal hydroxide (O) ₂ ) Weight ratio (O) ₁ /O ₂ ) May be in the range of 0.1 to 2. Weight ratio (O) ₁ /O ₂ ) The upper limit of (2) may be about 1.8, 1.6, 1.4, 1.2 or 1, and the weight ratio (O) ₁ /O ₂ ) The lower limit of (2) may be about 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, or 0.8. Weight ratio (O) ₁ /O ₂ ) It may be greater than or equal to any of the above lower limits, less than or equal to any of the above upper limits, or within the range of any of the above lower limits to any of the above upper limits. When the first filler satisfies the above range of the first metal hydroxide (O ₁ ) With a second metal hydroxide (O) ₂ ) Weight ratio (O) ₁ /O ₂ ) When the low specific gravity property and the heat dissipation property can be simultaneously ensured, and the release property and the thixotropy suitable for the process can be exhibited.

In the curable composition according to one embodiment of the present application, the average particle diameter (D ₁ ) With the average particle diameter (D) of the second metal hydroxide ₂ ) Ratio (D) ₁ /D ₂ ) May be in the range of 0.005 to 0.1. Average particle diameter ratio (D) ₁ /D ₂ ) The upper limit of (C) may be about 0.09, 0.08, 0.07 or 0.06, and the average particle diameter ratio (D ₁ /D ₂ ) The lower limit of (2) may be about 0.01, 0.015 or 0.02. Average particle diameter ratio (D) ₁ /D ₂ ) It may be greater than or equal to any of the above lower limits, less than or equal to any of the above upper limits, or within the range of any of the above lower limits to any of the above upper limits. When the average particle diameter ratio (D ₁ /D ₂ ) When the above range is satisfied, both the low specific gravity characteristic and the heat dissipation characteristic can be ensured, and the release characteristic and the thixotropic property suitable for the process can be exhibited.

In the curable composition according to one example of the present application, in some cases, the first filler may contain one kind of filler having an average particle diameter of more than 60 μm to 200 μm while being a metal hydroxide, or two or more kinds of filler. Further, the first filler may contain one kind of filler having an average particle diameter of 0.1 μm or more and 60 μm or less while being a metal hydroxide, or two or more kinds of filler. Further, the first filler may contain a filler having an average particle diameter of more than 60 μm to 200 μm while being a metal hydroxide, and a filler having an average particle diameter of 0.1 μm or more to 60 μm or less by mixing them in an appropriate ratio.

In the curable composition according to one example of the present application, the filler component may include the second filler in a range of 50 parts by weight to 800 parts by weight with respect to 100 parts by weight of the first filler. The upper limit of the content of the second filler may be about 750 parts by weight, 700 parts by weight, 650 parts by weight, 600 parts by weight, 550 parts by weight, or 500 parts by weight with respect to 100 parts by weight of the first filler, and the lower limit of the content of the second filler may be about 55 parts by weight, 60 parts by weight, 65 parts by weight, 70 parts by weight, 75 parts by weight, or 80 parts by weight with respect to 100 parts by weight of the first filler. The second filler may also be present in an amount greater than any of the above lower limits, less than or equal to any of the above upper limits, or within the range of any of the above lower limits to any of the above upper limits. By controlling the content of the second filler as above, both the low specific gravity characteristic and the heat dissipation characteristic can be ensured.

In the curable composition according to one example of the present application, the second filler may include one or more selected from aluminum oxide, magnesium oxide, beryllium oxide, titanium oxide, silicon nitride, aluminum nitride, silicon carbide, copper, silver, iron, and titanium.

In the curable composition according to one example of the present application, the second filler may contain a filler 2A having an average particle diameter of 65 μm or more while being limited to the above type. The upper limit of the average particle diameter of the filler 2A is not particularly limited, but may be about 200 μm, 180 μm, 160 μm, 140 μm, 120 μm, 100 μm or 80 μm. The average particle diameter of the filler 2A may be in the range of 65 μm or more to any one of the upper limits mentioned above. Since the second filler contains the filler 2A having an average particle diameter in the above range, both the low specific gravity characteristic and the heat radiation characteristic can be ensured, and the release characteristic suitable for the process can be exhibited.

In the curable composition according to one example of the present application, when the average particle diameter of the first filler is 60 μm or less as described above and the second filler contains the filler 2A, more excellent low specific gravity characteristics and heat dissipation characteristics can be ensured at the same time, and the release characteristics and thixotropic properties suitable for the process can be exhibited.

In the curable composition according to one example of the present application, the second filler may further contain a filler 2B having an average particle diameter of less than 65 μm to 10 μm or more. Since the second filler further contains the filler 2B, excellent heat radiation characteristics can be ensured.

In the curable composition according to one example of the present application, the second filler may contain filler 2A and filler 2B, wherein filler 2A (X _2A ) With filler 2B (X) _2B ) Weight ratio (X) _2A /X _2B ) May be in the range of 1 to 10. Weight ratio (X) _2A /X _2B ) The upper limit of (2) may be about 9, 8, 7 or 6, and the weight ratio (X _2A /X _2B ) The lower limit of (2), 3, 4 or 5. Weight ratio (X) _2A /X _2B ) It may be larger than or equal to any one of the above lower limits, smaller than or equal to any one of the above upper limits, or within a range from any one of the above lower limits to any one of the above upper limits. When the second filler satisfies the above range of filler 2A (X _2A ) With filler 2B (X) _2B ) Weight ratio (X) _2A /X _2B ) When the low specific gravity property and the heat dissipation property can be simultaneously ensured, and the release property and the thixotropy suitable for the process can be exhibited.

In the curable composition according to one example of the present application, the second filler may contain filler 2A and filler 2B, wherein the average particle diameter (D _2A ) Average particle diameter (D) with filler 2B _2B ) Ratio (D) _2A /D _2B ) May be in the range of 1 to 10. Average particle diameter ratio (D) _2A /D _2B ) The upper limit of (C) may be about 9, 8, 7, 6, 5 or 4, and the average particle diameter ratio (D _2A /D _2B ) The lower limit of (2) may be about 1.5, 2, 2.5 or 3. When the average particle diameter ratio (D _2A /D _2B ) When the low specific gravity property and the heat dissipation property can be simultaneously ensured, and the release property and the thixotropy suitable for the process can be exhibited.

In the curable composition according to one example of the present application, in some cases, the second filler may contain a filler 2C having an average particle diameter of less than 10 μm while being limited to the above type. The lower limit of the average particle diameter of the filler 2C is not particularly limited, but may be about 0.01 μm, 0.05 μm, 0.1 μm, 0.5 μm or 1 μm. The average particle diameter of the filler 2C may be in the range of less than 10 μm to any one of the lower limits.

In the curable composition according to one example of the present application, one or more from the group consisting of the first filler and the second filler may be a thermally conductive filler. The heat conductive filler may mean such a filler: the lower limit of the own thermal conductivity is about 0.1W/mK, 0.5W/mK, 1W/mK, 5W/mK, 10W/mK or 15W/mK, or the upper limit of the own thermal conductivity is not particularly limited, but is about 400W/mK, 380W/mK, 350W/mK, 320W/mK or 300W/mK, and the own thermal conductivity is within a range from any one of the above lower limits to any one of the above upper limits. At this time, the self thermal conductivity of the filler may be measured according to ASTM E1461.

The lower limit of the thermal conductivity of the first filler may be about 0.1W/mK, 0.5W/mK, 1W/mK, 5W/mK, 10W/mK or 15W/mK, or the upper limit of the thermal conductivity itself is not particularly limited, but may be about 400W/mK, 380W/mK, 350W/mK, 320W/mK or 300W/mK. The thermal conductivity of the first filler may also be greater than or equal to any of the above-mentioned lower limits, less than or equal to any of the above-mentioned upper limits, or within the range of any of the above-mentioned lower limits to any of the above-mentioned upper limits.

The lower limit of the thermal conductivity of the second filler may be about 1W/mK, 5W/mK, 10W/mK or 15W/mK, or the upper limit of the thermal conductivity itself is not particularly limited, but may be about 400W/mK, 380W/mK, 350W/mK, 320W/mK or 300W/mK. The thermal conductivity of the first filler may also be greater than or equal to any of the above-mentioned lower limits, less than or equal to any of the above-mentioned upper limits, or within the range of any of the above-mentioned lower limits to any of the above-mentioned upper limits.

In the curable composition according to one example of the present application, the filler component may further include a third filler different from the first filler and the second filler. The third filler may be a thermally conductive filler. Further, the type of the third filler is not particularly limited, but may include one or more selected from the group consisting of: metal oxide fillers such as aluminum oxide (alumina), magnesium oxide, beryllium oxide, or titanium oxide; metal hydroxide fillers, such as aluminum hydroxide or magnesium hydroxide; nitride fillers such as boron nitride, silicon nitride, or aluminum nitride; carbide fillers such as silicon carbide; metal fillers, such as copper, silver, iron, aluminum or nickel; and (3) a metal alloy filler. Further, if the third filler is used in the art, the shape and size of the third filler and the like are not particularly limited.

The curable composition according to one embodiment of the present application may further contain one, or two or more additives exemplified below, if necessary to ensure additional physical properties. However, if the additive is generally available in the art, the additive is sufficient and is not necessarily limited to the additives exemplified below.

The curable composition according to one example of the present application may further comprise a plasticizer. The type of plasticizer is not particularly limited, but for example, one or more may be selected from phthalic acid compounds, phosphoric acid compounds, adipic acid compounds, sebacic acid compounds, citric acid compounds, glycolic acid compounds, trimellitic acid compounds, polyester compounds, epoxidized soybean oil, chlorinated paraffin, chlorinated fatty acid esters, fatty acid compounds, compounds having a saturated aliphatic chain substituted with a sulfonic acid group to which a phenyl group is coupled (e.g., mesoll of LANXESS), and vegetable oils, and one or more may be used.

As the phthalic acid compound, one or more of dimethyl phthalate, diethyl phthalate, dibutyl phthalate, dihexyl phthalate, di-n-octyl phthalate, di-2-ethylhexyl phthalate, diisooctyl phthalate, dioctyl phthalate, dinonyl phthalate, diisononyl phthalate, didecyl phthalate, dilauryl phthalate, ditridecyl phthalate, dibenzyl phthalate, dicyclohexyl phthalate, butyl benzyl phthalate, octyl decyl phthalate, butyl octyl phthalate, octyl benzyl phthalate, n-hexyl n-decyl phthalate, n-octyl phthalate and n-decyl phthalate may be used. As the phosphoric acid compound, one or more of tricresyl phosphate, trioctyl phosphate, triphenyl phosphate, octyldiphenyl phosphate, cresyl diphenyl phosphate, and trichloroethyl phosphate may be used. As the adipic acid compound, one or more of dibutoxyethoxyethyl adipate (DBEEA), dioctyl adipate, diisooctyl adipate, di-n-octyl adipate, didecyl adipate, diisononyl adipate (DINA), diisodecyl adipate (DIDP), n-octyl n-decyl adipate, n-heptyl adipate, and n-nonyl adipate may be used. As the sebacic acid compound, one or more of dibutyl sebacate, dioctyl sebacate, diisooctyl sebacate, and butyl benzyl can be used. As the citric acid compound, one or more of triethyl citrate, acetyl triethyl citrate, tributyl citrate, acetyl tributyl citrate, and acetyl trioctyl citrate may be used. As the glycolic acid compound, one or more of methylphthalylethyl glycolate, ethylphthalylethyl glycolate, and butylphthalylethyl glycolate may be used. As the trimellitic acid compound, one or more of trioctyl trimellitate and tri-n-octyl n-decyl trimellitate may be used. The polyester compound may be the reaction product of a diol selected from the group consisting of butanediol, ethylene glycol, 1, 2-propanediol, 1, 3-propanediol, polyethylene glycol, glycerol, a diacid (selected from the group consisting of adipic acid, succinic acid and succinic anhydride) and a hydroxy acid (e.g., hydroxystearic acid).

The curable composition according to one example of the present application may contain the plasticizer in an amount of 0.1 parts by weight or more and 2 parts by weight or less with respect to 100 parts by weight of the filler component. The upper limit of the plasticizer content may be about 1.9 parts by weight, 1.8 parts by weight, 1.7 parts by weight, 1.6 parts by weight, or 1.5 parts by weight with respect to 100 parts by weight of the filler component, and the lower limit of the plasticizer content may be about 0.2 parts by weight, 0.3 parts by weight, 0.4 parts by weight, 0.5 parts by weight, 0.6 parts by weight, or 0.7 parts by weight with respect to 100 parts by weight of the filler component. The plasticizer may be contained in an amount of not less than any of the above-mentioned lower limits, not less than any of the above-mentioned upper limits, or within a range from any of the above-mentioned lower limits to any of the above-mentioned upper limits.

The curable composition according to one embodiment of the present application may further comprise a dispersant. As the dispersant, for example, polyamidoamine and its salts, polycarboxylic acid and its salts, modified polyurethane, modified polyester, modified poly (meth) acrylate, (meth) acrylic acid copolymer, naphthalene sulfonic acid formaldehyde condensate, polyoxyethylene alkyl phosphate, polyoxyethylene alkyl amine, pigment derivative, and the like can be used, but any dispersant known in the art can be used without limitation.

Further, the curable composition according to one example of the present application may contain a viscosity modifier, such as a thixotropic agent, a diluent, or a coupling agent, etc., for controlling the viscosity, such as increasing or decreasing the viscosity, or for controlling the viscosity according to a shear force, if necessary. Thixotropic agents can adjust viscosity according to shear forces. Useful thixotropic agents may be exemplified by fumed silica and the like. Diluents are commonly used to reduce viscosity and if they can exhibit such an effect, various types of diluents known in the art can be used without limitation. In the case of the coupling agent, for example, the coupling agent may be used to improve the dispersibility of the filler component (e.g., alumina, etc.), and if it can exhibit the above effect, various types of coupling agents known in the art may be used without limitation.

The curable composition according to one embodiment of the present application may further comprise a curing agent moiety that reacts with the polyol. Hereinafter, a composition including a curable composition as a main part and simultaneously including a curing agent part will be referred to as a two-component curable composition and will be described.

A two-part curable composition according to one example of the application may comprise a main part and a hardener part. The main portion comprises a polyol component and a first filler component, and the curative portion comprises an isocyanate component and a second filler component.

In the two-component curable composition according to one example of the present application, the curable composition according to one example of the present application as described above may be applied to the main part. That is, the content of the polyol component of the curable composition according to one example of the present application described above may be referred to, and the content of the filler component of the curable composition may be referred to as the first filler component of the two-component curable composition.

In a two-part curable composition according to one example of the application, at least some of the components involved in curing are physically separated and contained. The two-part curable composition or cured product thereof may have at least one of the following physical properties. The physical properties described below are independent of each other, and either physical property is not preferred over the other physical property, and at least one, or two or more of the physical properties described below may be satisfied. The physical properties described below are caused by a combination of the components contained in the curable composition or the cured product thereof.

The two-part curable composition or the cured product thereof according to one example of the present application may exhibit low adhesion to a specific adherend, or form a cured product capable of exhibiting low adhesion. Such a curable composition may be a polyurethane composition. Polyurethane is known as an adhesive material capable of exhibiting excellent adhesion to various adherends. Therefore, as a method for making the polyurethane composition exhibit low adhesion to an adherend, a method of introducing an adhesion-reducing component such as a plasticizer is generally used. When such components of plasticizer and the like are applied, the adhesion of polyurethane material may be lowered, but there may be a problem that: the relevant components deteriorate other physical properties that can be ensured in the polyurethane or they elute from the polyurethane material during the course of its use. However, in the present application, for the polyurethane material, low adhesion can be achieved while minimizing the use amount of an adhesion-reducing component such as a plasticizer. Thus, in the present application, such a material can be provided: which solves the problem of high adhesion which is not required according to the use while using a polyurethane material.

The adhesion force of the two-part curable composition or the cured product thereof according to one example of the present application to aluminum may be 1N/mm ² Or smaller. In another example, the upper limit of the adhesion of the curable composition or cured product to aluminum may also be 0.1N/mm ² 、0.099N/mm ² 、0.098N/mm ² 、0.097N/mm ² 、0.096N/mm ² 、0.095N/mm ² 、0.094N/mm ² 、0.093N/mm ² 、0.092N/mm ² 、0.091N/mm ² Or 0.09N/mm ² . Curable composition or compositionThe adhesion of the cured product to aluminum may be less than or equal to any of the upper limits described above. In the present application, the lower limit of the adhesion force to aluminum is not particularly limited. In one example, the adhesion to aluminum may be 0N/mm ² Or greater, or greater than 0N/mm ² . The curable composition may be a curable composition that has substantially no measure of adhesion to aluminum, or may be a curable composition capable of forming a cured product that has substantially no measure of adhesion to aluminum. Accordingly, the adhesion to aluminum may be less than or equal to any of the above upper limits, while being 0N/mm ² Or greater, or greater than 0N/mm ² . The adhesion of the curable composition or cured product thereof to aluminum can be measured in the manner described in the examples herein.

The adhesion force of the two-part curable composition or the cured product thereof according to one example of the present application to the polyester may be 100gf/cm or less. In another example, the upper limit of the adhesion of the curable composition or cured product to the polyester may also be 99.9gf/cm, 99.8gf/cm, 99.7gf/cm, 99.6gf/cm, 99.5gf/cm, 99.4gf/cm, 99.3gf/cm, 99.2gf/cm, 99.1gf/cm, or 99gf/cm. The adhesion of the curable composition or cured product thereof to the polyester may be equal to or less than any of the upper limits described above. In the present application, the lower limit of the adhesive force of the polyester is not particularly limited. In one example, the lower limit of the adhesion of the curable composition or cured product to the polyester may also be about 0gf/cm, 2gf/cm, 4gf/cm, 6gf/cm, 8gf/cm, 10gf/cm, 12gf/cm, 14gf/cm, 16gf/cm, 18gf/cm, or 20 gf/cm. The curable composition or cured product thereof may exhibit substantially no adhesion to the polyester. The adhesion of the curable composition or the cured product thereof to the polyester may also be within the range of any one of the lower limits to any one of the upper limits described above. Adhesion of the curable composition or cured product thereof to the polyester may be measured in the manner described in the examples herein.

The two-part curable composition or the cured product thereof according to one example of the present application may exhibit excellent thermal conductivity characteristics. For example, the lower limit of the thermal conductivity of the curable composition or cured product thereof may be about 2.0W/mK, 2.1W/mK, 2.2W/mK, 2.3W/mK, 2.4W/mK, 2.5W/mK, 2.6W/mK, 2.7W/mK, 2.8W/mK, 2.9W/mK or 3W/mK. The thermal conductivity may be greater than or equal to any of the lower limits described above. The upper limit of the thermal conductivity is not particularly limited. For example, the upper limit of the thermal conductivity of the curable composition or the cured product thereof may be about 10W/mK, 9W/mK, 8W/mK, 7W/mK, 6W/mK, 5W/mK or 4W/mK. The thermal conductivity may be within the range of any one of the above lower limits to any one of the above upper limits. The thermal conductivity of such a curable composition or a cured product thereof can be measured by the method disclosed in examples to be described below.

The two-part curable composition or cured product thereof according to one example of the present application may also exhibit an appropriate hardness. For example, if the hardness of the curable composition or its cured product is too high, there may be a problem due to excessive brittleness. Further, by adjusting the hardness of the curable composition or a cured product thereof according to the purpose of application, impact resistance and vibration resistance can be ensured, and durability of the product can be ensured. The upper limit of the hardness expressed in shore OO type of the curable composition or cured product thereof may be 100, 98, 96, 94, 92 or 90. The shore OO type hardness may be less than or equal to any of the upper limits described above. The lower limit of the shore OO type hardness may be 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, or 80. The shore OO type hardness may be greater than or equal to any of the lower limits described above. The shore OO hardness may be within a range from any one of the upper limits to any one of the lower limits. The hardness of such a curable composition or a cured product thereof can be measured by the method disclosed in examples to be described below.

The two-part curable composition or cured product thereof according to one example of the present application may also exhibit suitable flexibility. For example, when the flexibility of the curable composition or its cured product is adjusted to a desired level, the application uses can be greatly expanded. For example, the upper limit of the radius of curvature of the curable composition or cured product thereof may be about 20mm, 19mm, 18mm, 17mm, 16mm, 15mm, 14mm, 13mm, 12mm, 11mm, 10mm or 9 mm. The radius of curvature may be less than or equal to any of the upper limits described above. The lower limit of the radius of curvature may be, for example, about 1mm, 2mm, 3mm, 4mm, 5mm, 6mm or 7 mm. The radius of curvature may be greater than or equal to any of the lower limits described above. The radius of curvature may be within a range from any one of the upper limits to any one of the lower limits. The radius of curvature of such a curable composition or cured product thereof can be measured by the method disclosed in examples to be described below.

The two-part curable composition or the cured product thereof according to one example of the present application may have insulating properties. That is, the curable composition may have insulating properties and/or form a cured product having insulating properties. For example, in the curable composition or cured product thereof, the lower limit of the dielectric breakdown voltage measured according to ASTM D149 may be about 3kV/mm, 5kV/mm, 7kV/mm, 10kV/mm, 15kV/mm, or 20 kV/mm. The dielectric breakdown voltage may be greater than or equal to any of the lower limits described above. The higher the value of the dielectric breakdown voltage, the more excellent the insulating property seems to be, and thus the upper limit is not particularly limited, but the upper limit of the dielectric breakdown voltage may be around 50kV/mm, 45kV/mm, 40kV/mm, 35kV/mm or 30kV/mm in view of the composition of the curable composition or the like. The dielectric breakdown voltage may be less than or equal to any of the upper limits described above. Such dielectric breakdown voltage may be controlled by adjusting the insulating properties of the curable composition, which may be achieved, for example, by applying an insulating filler in the composition. In general, among the fillers, ceramic fillers are known as components capable of ensuring insulation properties. Further, if the cured product of the curable composition can secure the electrical insulation characteristics as above, stability can be secured while maintaining performance with respect to various materials (e.g., a case or a battery cell included in a battery module).

The two-part curable composition or the cured product thereof according to one example of the present application may have flame retardancy. The curable composition or cured product thereof may exhibit a V-0 rating in the UL 94V test (vertical burn test). Thus, stability against fires and other accidents that are of concern depending on the application of the curable composition can be ensured. In addition, in general, in order to ensure flame retardancy, it is generally ensured by a halogen-containing flame retardant, a phosphorus-containing flame retardant, and a combination thereof. However, in the case of a flame retardant containing substantially no halogen element and a flame retardant containing phosphorus (P) element, the curable composition or cured product thereof may have a V-0 grade result as measured according to the UL 94V test by an appropriate combination of the polyol component and filler component described below.

In the two-component curable composition or the cured product thereof according to one example of the present application, the combined content of the halogen element and the phosphorus element may be 0.3% by weight or less with respect to the total content of the curable composition or the cured product. The upper limit of the combined content of the halogen element and the phosphorus element may be 0.29 wt%, 0.28 wt%, 0.27 wt%, 0.26 wt%, 0.25 wt%, 0.24 wt%, 0.23 wt%, 0.22 wt%, 0.21 wt% or 0.2 wt% with respect to the total content of the curable composition or cured product. The combined content of the halogen element and the phosphorus element may be less than or equal to any one of the upper limits described above. The lower limit of the combined content of the halogen element and the phosphorus element is not particularly limited, but may be 0 wt% (excluding), or more than 0 wt% with respect to the total content of the curable composition or the cured product. By the combined content of the halogen element and the phosphorus element, it can be determined that the curable composition or the cured product thereof contains substantially no halogen element-containing flame retardant and no phosphorus element-containing flame retardant. The combined content of the halogen element and the phosphorus element may be greater than or equal to any of the lower limits described above. The combined content of the halogen element and the phosphorus element may be within a range from any one of the upper limits to any one of the lower limits.

The halogen element content, the phosphorus element content, and the combined content of the halogen element and the phosphorus element in the two-component curable composition or cured product according to an example of the present application can be measured by ICP analysis. In the two-component curable composition or cured product according to one example of the present application, the halogen element content may be 0.3% by weight or less relative to the total content of the curable composition or cured product. The upper limit of the halogen element content may be 0.29 wt%, 0.28 wt%, 0.27 wt%, 0.26 wt%, 0.25 wt%, 0.24 wt%, 0.23 wt%, 0.22 wt%, 0.21 wt% or 0.2 wt% with respect to the total content of the curable composition or cured product. The halogen element content may be less than or equal to any of the upper limits mentioned above. The lower limit of the halogen element content is not particularly limited, but may be 0 wt% (excluding), or more than 0 wt% with respect to the total content of the curable composition or cured product. The curable composition or cured product thereof may be determined by the halogen element content to be substantially free of halogen element-containing flame retardants. The halogen content may be greater than or equal to any of the lower limits described above. The halogen content may also be within the range of any one of the above upper limits to any one of the above lower limits.

In the two-component curable composition or the cured product thereof according to one example of the present application, the phosphorus element content may be 0.3% by weight or less relative to the total content of the curable composition or the cured product. The upper limit of the phosphorus element content may be 0.29 wt%, 0.28 wt%, 0.27 wt%, 0.26 wt%, 0.25 wt%, 0.24 wt%, 0.23 wt%, 0.22 wt%, 0.21 wt% or 0.2 wt% with respect to the total content of the curable composition or cured product. The phosphorus element content may be less than or equal to any of the upper limits mentioned above. The lower limit of the content of the phosphorus element is not particularly limited, but may be 0% by weight (excluding), or more than 0% by weight with respect to the total content of the curable composition or cured product. The curable composition or cured product thereof may be determined by the phosphorus element content to be substantially free of phosphorus element-containing flame retardants. The phosphorus content may be greater than or equal to any of the lower limits described above. The phosphorus content may also be within the range of any one of the upper limits to any one of the lower limits.

In the two-component curable composition or the cured product thereof according to one example of the present application, the combined content of the halogen-containing flame retardant and the phosphorus-containing flame retardant may be 1% by weight or less relative to the total content of the curable composition or the cured material. The upper limit of the combined content of the halogen element-containing flame retardant and the phosphorus element-containing flame retardant may be 0.9 wt%, 0.8 wt%, 0.7 wt%, 0.6 wt%, 0.5 wt%, 0.4 wt%, 0.3 wt%, 0.2 wt%, 0.1 wt%, 0.01 wt% or 0.001 wt%. The combined content of the halogen element-containing flame retardant and the phosphorus element-containing flame retardant may be less than or equal to any of the upper limits described above. The lower limit of the combined content of the halogen element-containing flame retardant and the phosphorus element-containing flame retardant is not particularly limited, but may be 0% by weight (excluding), or more than 0% by weight with respect to the total content of the curable composition or cured product. The combined content of the halogen element-containing flame retardant and the phosphorus element-containing flame retardant may be greater than or equal to any of the lower limits described above. The combined content of the halogen element-containing flame retardant and the phosphorus element-containing flame retardant may also be in the range of any one of the upper limits to any one of the lower limits.

In the two-component curable composition or the cured product thereof according to one example of the present application, the content of the halogen-containing flame retardant may be 1% by weight or less relative to the total content of the curable composition or the cured product. The upper limit of the content of the halogen-containing flame retardant is 0.9 wt%, 0.8 wt%, 0.7 wt%, 0.6 wt%, 0.5 wt%, 0.4 wt%, 0.3 wt%, 0.2 wt%, 0.1 wt%, 0.01 wt% or 0.001 wt% with respect to the total content of the curable composition or cured product. The content of the halogen-containing flame retardant may be less than or equal to any of the upper limits mentioned above. The lower limit of the content of the halogen-containing flame retardant is not particularly limited, but may be 0% by weight (excluding), or more than 0% by weight with respect to the total content of the curable composition or cured product. The content of the halogen-containing flame retardant may be greater than or equal to any of the lower limits mentioned above. The content of the halogen-containing flame retardant may be within a range from any one of the upper limits to any one of the lower limits.

In the two-component curable composition or the cured product thereof according to one example of the present application, the content of the flame retardant containing a phosphorus element may be 1% by weight or less relative to the total content of the curable composition or the cured product. The upper limit of the content of the flame retardant containing a phosphorus element may be 0.9 wt%, 0.8 wt%, 0.7 wt%, 0.6 wt%, 0.5 wt%, 0.4 wt%, 0.3 wt%, 0.2 wt%, 0.1 wt%, 0.01 wt% or 0.001 wt% with respect to the total content of the curable composition or cured product. The content of the phosphorus-containing flame retardant may be less than or equal to any of the upper limits mentioned above. The lower limit of the content of the flame retardant containing a phosphorus element is not particularly limited, but may be 0% by weight (excluding), or more than 0% by weight with respect to the total content of the curable composition or cured product. The content of the phosphorus-containing flame retardant may be greater than or equal to any of the lower limits described above. The content of the phosphorus-containing flame retardant may be within a range from any one of the upper limits to any one of the lower limits.

The two-part curable composition or the cured product thereof according to one example of the present application may have a specific gravity of 3 or less. The upper limit of the specific gravity may be 2.99, 2.98, 2.97 or 2.96. The upper limit of the specific gravity may be less than or equal to any one of the upper limits described above. Such specific gravity may be achieved by applying a filler having a low specific gravity and/or applying a surface treated filler. In addition, the lower limit of the specific gravity is not particularly limited, since the lower the specific gravity is, the more advantageous the weight of the application product is reduced. For example, the specific gravity may be about 1.5 or greater, or 2 or greater. The specific gravity may be greater than or equal to any of the lower limits described above. The specific gravity may be within a range from any one of the upper limits to any one of the lower limits.

As described above, the two-part curable composition or the cured product thereof according to one example of the present application can be used as a thermal interface material or the like, and for example, heat generated when a battery is rapidly charged can be rapidly dissipated to reduce the risk of fire or the like. However, in order to achieve heat dissipation performance, a heat conductive filler having a high specific gravity is generally excessively applied thereto, but in this case, the weight of the battery increases, and the weight of a product to which the battery is ultimately applied also increases. In particular, when applied to an electric vehicle, it may be detrimental to the fuel efficiency of the vehicle. Therefore, in order for the curable composition or the cured product thereof to have a low specific gravity, the content of the filler having a high specific gravity as described above should be reduced. However, when the high specific gravity filler is reduced, the heat radiation performance is lowered, making it difficult to prevent fire or the like due to accumulated heat. That is, the low specific gravity and the high thermal conductivity are in a trade-off relationship with each other.

The two-component curable composition or the cured product thereof according to one example of the present application can simultaneously ensure low specific gravity characteristics and heat dissipation characteristics even in the above trade-off relationship by an appropriate combination of filler components to be described below.

The two-part curable composition or cured product thereof according to one example of the present application may have a low Coefficient of Thermal Expansion (CTE). By so doing, peeling or void generation and the like that may occur during the application or use process can be prevented. The coefficient of thermal expansion may be appropriately adjusted within a range capable of exhibiting the above-described effects, and may be, for example, less than 300ppm/K, less than 250ppm/K, less than 200ppm/K, less than 150ppm/K, or less than about 100ppm/K. The lower limit is not particularly limited since the lower the value of the thermal expansion coefficient is, the more advantageous it may be.

In the two-part curable composition or the cured product thereof according to one example of the present application, the 5% weight loss temperature in thermogravimetric analysis (TGA) may be 400 ℃ or more, or the 800 ℃ remaining amount may be 70% by weight or more. Stability at high temperatures can be further improved by such characteristics. In another example, the 800 ℃ residual amount may be about 75 wt% or greater, about 80 wt% or greater, about 85 wt% or greater, or about 90 wt% or greater. In another example, the 800 ℃ residual amount may be about 99 wt% or less. Thermogravimetric analysis (TGA) can be at 60cm ³ Nitrogen per minute (N) ₂ ) The heating rate of 20 ℃ for 20 ℃ in the atmosphere is measured in the range of 25 ℃ to 800 ℃. Thermogravimetric analysis (TGA) results may also be achieved by compositional control of the curable composition. For example, the 800 ℃ residual amount is generally affected by the type or ratio of filler contained in the curable composition, and when an excessive amount of filler is contained, the residual amount increases.

In the two-part curable composition according to an example of the present application, the isocyanate component included in the curing agent part may include the isocyanate compound in an amount of 55 wt% or more, 60 wt% or more, 65 wt% or more, 70 wt% or more, 75 wt% or more, 80 wt% or more, 85 wt% or more, 90 wt% or more, 95 wt% or more, 99 wt% or more, or 100 wt% with respect to the total weight.

The term isocyanate compound as used in the present application may mean a compound in which the lower limit of the number of isocyanate groups is about 1 or 2 per molecule. The upper limit of the amount of isocyanate in the isocyanate is not particularly limited, but may be about 10, 9, 8, 7, 6, 5, 4 or 3 isocyanate groups per molecule. The number of isocyanate groups contained in the isocyanate compound may be greater than or equal to any of the above-mentioned lower limits, less than or equal to any of the above-mentioned upper limits, or within a range from any of the above-mentioned lower limits to any of the above-mentioned upper limits. In the present application, when the isocyanate compound has one isocyanate group per molecule, the isocyanate compound may be referred to as a monofunctional isocyanate compound. Further, when the isocyanate compound has two or more isocyanate groups per molecule, the isocyanate compound may be referred to as a polyisocyanate compound. From the standpoint of reacting with the polyol component in the main part to form a polyurethane resin, it may be appropriate that the isocyanate compound is a polyisocyanate compound. Further, the isocyanate compound may be named according to the number of isocyanate groups, and may be referred to as, for example, a difunctional isocyanate compound or a diisocyanate compound (having two isocyanate groups) or the like.

In the two-component curable composition according to one example of the present application, the type of isocyanate compound is not particularly limited, but a non-aromatic polyisocyanate containing no aromatic group may be used to ensure desired physical properties. Further, in the two-component curable composition according to one example of the present application, when considering the combination of the polyol components contained in the main composition, in order to ensure desired physical properties, it may be more suitable to use, among the non-aromatic polyisocyanates containing no aromatic groups, a non-aromatic polyisocyanate having 3 or more isocyanate groups as the isocyanate compound.

As the polyisocyanate compound, for example, aliphatic polyisocyanates such as hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, lysine diisocyanate, norbornane diisocyanate methyl, ethylene diisocyanate, propylene diisocyanate, or tetramethylene diisocyanate; alicyclic polyisocyanates such as trans-cyclohexane-1, 4-diisocyanate, isophorone diisocyanate, bis (isocyanatomethyl) cyclohexane diisocyanate or dicyclohexylmethane diisocyanate; or one or more of the foregoing carbodiimide-modified polyisocyanates or isocyanurate-modified polyisocyanates; etc. In addition, as the polyisocyanate, an addition reaction product of the diisocyanate and a polyol (for example, trimethylolpropane or the like) as described above can also be used. In addition, as the polyisocyanate compound, for example, a trimer of the above diisocyanate may also be used. Furthermore, mixtures of two or more of the above listed compounds may be used.

In the two-part curable composition according to one example of the present application, the curative part may include an isocyanate component in a range of 1 to 10% by weight relative to the total weight of the curative part. The upper limit of the content of the isocyanate component may also be about 9 wt%, 8 wt%, 7 wt% or 6 wt% and the lower limit of the content of the isocyanate component may be about 1.5 wt%, 2 wt%, 2.5 wt%, 3 wt% or 3.5 wt% with respect to the total weight of the curing agent portion. The isocyanate component may also be present in an amount greater than or equal to any of the above lower limits, less than or equal to any of the above upper limits, or within the range of any of the above lower limits to any of the above upper limits.

In a two-part curable composition according to one example of the application, the curative portion may comprise a second filler component. The hardener part can ensure a viscosity and thixotropic properties suitable for the process by means of the combination of the abovementioned isocyanate component and the second filler component.

In the two-part curable composition according to one example of the application, the curative part is at 2.4 seconds ^-1 The viscosity at 25 ℃ measured at shear rate conditions of (c) may be 390kcP or less. The upper limit of the viscosity of the curative portion may be about 380kcP, 370kcP, 360kcP, 350kcP, 340kcP, 330kcP, 320kcP, 310kcP, or 300kcP, and the lower limit may be about 90kcP, 100kcP, 105kcP, 110kcP, 115kcP, 120kcP, 125kcP, 130kcP, or 135 kcP. The viscosity of the curative portion may also be greater than or equal to any of the above lower limits, less than or equal to any of the above upper limits, or within the range of any of the above lower limits to any of the above upper limits.

In the two-part curable composition according to one example of the present application, the thixotropic index (t.i.) of the curing agent part according to the following general equation 2 may be 10 or less. The upper limit of the thixotropic index of the curative portion may be around 9, 8 or 7, and the lower limit of the thixotropic index of the curative portion may be around 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7 or 2.8. The thixotropic index of the curative portion may also be greater than or equal to any of the lower limits, less than or equal to any of the upper limits, or within the range of any of the lower limits to any of the upper limits.

[ general equation 2]

Thixotropic index (t.i.) =v ₃ /V ₄

In general equation 2, V ₃ At 25℃and 0.24 seconds for the hardener part ^-1 Viscosity measured below and V ₄ At 25℃for 2.4 seconds for the hardener part ^-1 Viscosity measured as follows.

In the two-part curable composition according to one example of the present application, the curing agent part may contain the second filler component in the range of 1,000 parts by weight or more and 3,000 parts by weight or less with respect to 100 parts by weight of the isocyanate component. The lower limit of the content of the second filler component may be about 1,100 parts by weight, 1,200 parts by weight, 1,300 parts by weight, 1,400 parts by weight, 1,500 parts by weight, 1,600 parts by weight, or 1,700 parts by weight with respect to 100 parts by weight of the isocyanate component. The upper limit of the content of the second filler component may be about 2,900 parts by weight, 2,800 parts by weight, 2,700 parts by weight, 2,600 parts by weight, 2,500 parts by weight, or 2,400 parts by weight with respect to 100 parts by weight of the isocyanate component. The content of the second filler component may also be greater than or equal to any of the above-mentioned lower limits, less than or equal to any of the above-mentioned upper limits, or within the range of any of the above-mentioned lower limits to any of the above-mentioned upper limits. By controlling the content of the second filler component as described above, a cured product having excellent thermal conductivity while having viscosity and thixotropy suitable for the process can be formed.

In a two-part curable composition according to one example of the application, the second filler component of the curative portion may comprise a filler. If the filler is used in the art, the type, shape, size, and the like of the filler are not particularly limited. Further, the filler component may contain one, or two or more fillers. Furthermore, even if the same type of filler is used, the filler component may be a mixture of fillers having different shapes or sphericities, or a mixture of fillers having different average particle diameters.

In the two-part curable composition according to one example of the present application, the second filler component of the curative portion may comprise a second filler having a specific gravity greater than 3. The upper limit of the specific gravity of the second filler is not particularly limited, but may be about 30, 28, 26, 24, 22 or 20. Further, the specific gravity of the second filler may be in a range of more than 3 to any one of the upper limits. Further, the specific gravity of the second filler may be in the range of 3.1 or more to any one of the upper limits described above.

In the two-part curable composition according to one example of the present application, the second filler component of the curing agent part may contain a first filler having a specific gravity of 3 or less, if necessary. The lower limit of the specific gravity of the first filler is not particularly limited, but may be about 0.5, 0.6 or 0.7, and the specific gravity of the first filler may be in the range of 3 or less to any one of the above lower limits.

In a two-part curable composition according to one example of the application, the second filler component of the curative portion may comprise one or more thermally conductive fillers. Further, the type of filler included in the second filler component may include one or more selected from the group consisting of: metal oxide fillers such as aluminum oxide (alumina), magnesium oxide, beryllium oxide, or titanium oxide; metal hydroxide fillers, such as aluminum hydroxide or magnesium hydroxide; nitride fillers such as boron nitride, silicon nitride, or aluminum nitride; carbide fillers such as silicon carbide; metal fillers, such as copper, silver, iron, aluminum or nickel; and (3) a metal alloy filler. Further, if the third filler is used in the art, the shape and size of the third filler and the like are not particularly limited.

In the two-part curable composition according to one example of the present application, the curing agent part may further contain one, or two or more additives exemplified below, if necessary to ensure additional physical properties. However, if the additive is generally available in the art, the additive is sufficient and is not necessarily limited to the additives exemplified below.

In the two-part curable composition according to one example of the present application, the curative part may further comprise a plasticizer. The type of plasticizer is not particularly limited, but for example, one or more may be selected from phthalic acid compounds, phosphoric acid compounds, adipic acid compounds, sebacic acid compounds, citric acid compounds, glycolic acid compounds, trimellitic acid compounds, polyester compounds, epoxidized soybean oil, chlorinated paraffin, chlorinated fatty acid esters, fatty acid compounds, compounds having a saturated aliphatic chain substituted with a sulfonic acid group to which a phenyl group is coupled (e.g., mesoll of LANXESS), and vegetable oils, and one or more may be used.

In the two-part curable composition according to one example of the present application, the curing agent part may contain the plasticizer in an amount of 50 parts by weight or more and 200 parts by weight or less with respect to 100 parts by weight of the isocyanate component. The upper limit of the content of the plasticizer may be 190 parts by weight, 180 parts by weight, 170 parts by weight, 160 parts by weight, 150 parts by weight, 140 parts by weight, 130 parts by weight or 120 parts by weight or so with respect to 100 parts by weight of the isocyanate component, and the lower limit of the content of the plasticizer may be 70 parts by weight, 80 parts by weight or 90 parts by weight or so with respect to 60 parts by weight of the isocyanate component. The plasticizer may be contained in an amount of not less than any of the above-mentioned lower limits, not less than any of the above-mentioned upper limits, or within a range from any of the above-mentioned lower limits to any of the above-mentioned upper limits.

In the two-part curable composition according to one example of the present application, the curing agent part may further contain a dispersing agent. As the dispersant, for example, polyamidoamine and its salts, polycarboxylic acid and its salts, modified polyurethane, modified polyester, modified poly (meth) acrylate, (meth) acrylic acid copolymer, naphthalene sulfonic acid formaldehyde condensate, polyoxyethylene alkyl phosphate, polyoxyethylene alkyl amine, pigment derivative, and the like can be used, but any dispersant known in the art can be used without limitation.

In the two-part curable composition according to one example of the present application, the curing agent part may contain a viscosity regulator, such as a thixotropic agent, a diluent, or a coupling agent, etc., if necessary, for controlling the viscosity, such as increasing or decreasing the viscosity, or for controlling the viscosity according to a shear force. Thixotropic agents can adjust viscosity according to shear forces. Useful thixotropic agents may be exemplified by fumed silica and the like. Diluents are commonly used to reduce viscosity and if they can exhibit such an effect, various types of diluents known in the art can be used without limitation. In the case of the coupling agent, for example, the coupling agent may be used to improve the dispersibility of the filler component (e.g., alumina, etc.), and if it can exhibit the above effect, various types of coupling agents known in the art may be used without limitation.

In the two-part curable composition according to one example of the present application, the combined content of the first filler component of the main part and the second filler component of the curing agent part may be contained in a range of 70 wt% or more to 98 wt% or less with respect to the total weight of the two-part curable composition. The lower limit of the combined content of the first filler component and the second filler component may be about 72 wt%, 74 wt%, 76 wt%, 78 wt%, 80 wt%, 82 wt%, 84 wt% or 86 wt% with respect to the total weight of the two-component curable composition, and the upper limit of the combined content of the first filler component and the second filler component may be 97 wt%, 96 wt%, 95 wt%, 94 wt%, 93 wt%, 92 wt% or 91 wt% with respect to the total weight of the two-component curable composition. The combined content of the first filler component and the second filler component may also be greater than any of the lower limits, less than or equal to any of the upper limits, or within the range of any of the lower limits to any of the upper limits. By controlling the combined content of the first filler component and the second filler component as described above, a cured product having excellent thermal conductivity while having viscosity and thixotropy suitable for the process can be formed.

In the two-part curable composition according to one example of the present application, one or more selected from the first filler component of the main part and the second filler component of the curing agent part may include a first filler having a specific gravity of 3 or less. The lower limit of the specific gravity of the first filler is not particularly limited, but may be about 0.5, 0.6 or 0.7, and the specific gravity of the first filler may be in the range of 3 or less to any one of the above lower limits.

In the two-component curable composition according to one example of the present application, the first filler may be included in a range of 5 wt% or more and 60 wt% or less with respect to the total weight of the two-component curable composition. The upper limit of the content of the first filler may be 59 wt%, 58 wt%, 57 wt%, 56 wt%, 55 wt%, 54 wt%, 53 wt%, 52 wt%, 51 wt%, 50 wt%, 49 wt%, 48 wt%, 47 wt%, 46 wt%, 45 wt% or 44 wt% relative to the total weight of the two-part curable composition, and the lower limit of the content of the first filler may be 5.2 wt%, 5.4 wt%, 5.6 wt%, 5.8 wt%, 6 wt%, 6.2 wt%, 6.4 wt%, 6.6 wt%, 6.8 wt%, 7 wt%, 7.2 wt% or 7.4 wt%. The content of the first filler may be greater than or equal to any of the above-mentioned lower limits, less than or equal to any of the above-mentioned upper limits, or within a range from any of the above-mentioned lower limits to any of the above-mentioned upper limits. By controlling the content of the first filler as described above and combining the above polyol and isocyanate compound, etc., it is possible to ensure a V-0 grade according to the result of UL 94V test measurement even when the flame retardant containing halogen element and the flame retardant containing phosphorus (P) element are not substantially contained. Further, when the content of the first filler does not reach the above range, it may be difficult to ensure flame retardancy without using a halogen-containing flame retardant and a phosphorus (P) -containing flame retardant. Further, by controlling the content of the first filler and combining the above polyol and isocyanate compound as above, it is possible to simultaneously secure a low specific gravity characteristic and a heat dissipation characteristic, and to prevent a rapid increase in adhesive force even in a thermal shock test according to the Mil-Std-883 method 1010 or JEDEC JESD 22-A104.

In the two-part curable composition according to one example of the present application, one or more selected from the first filler component of the main part and the second filler component of the curing agent part may contain a second filler having a specific gravity of greater than 3. The upper limit of the specific gravity of the second filler is not particularly limited, but may be about 30, 28, 26, 24, 22 or 20, and the specific gravity of the second filler may be in a range of more than 3 to any one of the upper limits. Further, the specific gravity of the second filler may be in the range of 3.1 or more to any one of the upper limits described above.

A two-part curable composition according to one example of the application may include a first filler and a second filler. The two-part curable composition may include the second filler in a range of 100 parts by weight to 2,000 parts by weight with respect to 100 parts by weight of the first filler. The lower limit of the content of the second filler may be about 105 parts by weight, 110 parts by weight, 115 parts by weight, 120 parts by weight, or 125 parts by weight with respect to 100 parts by weight of the first filler, and the upper limit of the content of the second filler may be about 1,900 parts by weight, 1,800 parts by weight, 1,700 parts by weight, 1,600 parts by weight, 1,500 parts by weight, 1,400 parts by weight, or 1,300 parts by weight. The content of the second filler may be greater than any of the above lower limits, less than or equal to any of the above upper limits, or within the range of any of the above lower limits to any of the above upper limits. By controlling the content of the second filler as described above, both the low specific gravity characteristic and the heat dissipation characteristic can be ensured.

In the two-part curable composition according to one example of the present application, the main part (V _A ) And a curing agent part (V _B ) Volume ratio (V) _A /V _B ) May be in the range of 0.5 or more to 2 or less. Volume ratio (V) _A /V _B ) The upper limit of (2) may be about 1.8, 1.6, 1.4 or 1.2, and the volume ratio (V _A /V _B ) The lower limit of (2) may be about 0.6, 0.7, 0.8, 0.9 or 1. Volume ratio (V) _A /V _B ) It may be larger than or equal to any one of the above lower limits, smaller than or equal to any one of the above upper limits, or within a range from any one of the above lower limits to any one of the above upper limits.

An apparatus according to one example of the application includes a heat generating element and a heat carrier in thermal contact with the heat generating element, wherein the heat carrier may comprise a cured product of a curable composition. In addition, the heat carrier of the device may comprise a cured product of a two-part curable composition comprising a major part and a curative part. That is, the heat carrier of the device may comprise one or more selected from the group consisting of a curable composition and a cured product of a two-component curable composition comprising a major portion and a curative portion. The term thermal contact as used in the present application means that the cured product of the curable composition is in direct physical contact with the heat generating element to dissipate heat generated by the heat generating element, or even if the cured product of the curable composition is not in direct contact with the heat generating element (i.e., there is a separate layer between the cured product of the curable composition and the heat generating element), it dissipates heat generated by the heat generating element.

Devices according to one example of the present application include, for example, various electrical and electronic products such as irons, washing machines, dryers, laundry managers, electric shavers, microwave ovens, electric cookers, refrigerators, dishwashers, air conditioners, fans, humidifiers, air purifiers, mobile phones, radio, televisions, radios, computers and notebook computers, or batteries such as secondary batteries, wherein the cured product of the curable composition may dissipate heat generated in the device. In particular, in an electric vehicle battery manufactured by combining battery cells together to form one battery module and combining several battery modules together to form a battery pack, the curable composition of the present application may be used as a material for connecting the battery modules. When the curable composition of the present application is used as a material for connecting battery modules, it may function to dissipate heat generated from the battery cells and fix the battery cells from external impact and vibration.

In an apparatus according to one example of the application, heat generated by the heat generating element may be dissipated through the heat carrier and the heat may be transferred to the cooling area. The cooling region may be in thermal contact with the heat carrier and may have a temperature lower than the temperature of the heat generating element. The cooling region may mean a region having a temperature lower than that of the heating element by a medium such as cooling water, or may mean an air region having a temperature lower than that of the heating element, or the like.

Advantageous effects

The present application can provide a curable composition or a thermal interface material that exhibits low adhesion to a predetermined adherend while having low density and exhibiting high thermal conductivity.

The present application can also provide a curable composition or thermal interface material that ensures excellent flame retardant properties and exhibits release properties and thixotropic properties suitable for a process without using a halogen flame retardant or a phosphorus-based flame retardant or minimizing the use ratio thereof.

The present application may also provide a product comprising the curable composition, a cured product of the curable composition, or a thermal interface material.

Detailed Description

Hereinafter, the present application will be described by way of examples and comparative examples, but the scope of the present application is not limited by what is provided below.

Preparation example 1.

The polyol (A) of the following formula A is prepared in the following manner.

[ A ]

In formula a, n and m are each greater than 0, and the sum (n+m) is about 4.8.

Polycaprolactone polyol (Perston, capa 3031) and isononanoic acid as the saturated fatty acid were mixed in a weight ratio of 1:0.53 (Capa 3031: isononanoic acid). Subsequently, a catalyst (tin (II) 2-ethylhexanoate (Sigma-Aldrich)) was added thereto in an amount of 0.1 parts by weight with respect to 100 parts by weight of the mixture, and maintained while stirring at 150 ℃ for 30 minutes under an inert gas purge. Subsequently, a small amount of xylene (azeotropic solution) was added, the temperature was raised to 200 ℃, and the mixture was allowed to react for 3 hours or more, then the pressure was reduced to 80 torr or less, and xylene and unreacted substances were removed. After cooling, the reaction was filtered to obtain the desired product (compound of formula a) having a weight average molecular weight of about 876g/mol and being a difunctional polyol.

In the following examples and comparative examples, the first filler component contained in the main part may be represented by the filler component (F1), and the second filler component contained in the curing agent part may be represented by the filler component (F2). Further, the mixture of the main part and the curing agent part is represented by a final curable composition, and the filler component (f1+f2) contained in the final curable composition includes a first filler component and a second filler component.

Example 1.

Main part preparation

Polyol component (P), filler component (F1) and plasticizer (Pc, AEKYUNG Petrochemical co., ltd., diisononyl adipate) were mixed in a weight ratio of 9.8:89.1:1.1 (P: F1: pc) to prepare a main part (V _A )。

Polyol component (P) was a mixture of polyol (A) of preparation example 1 above and a trifunctional polyester polyol (supplier: kuraray, product name: F-2010, weight average molecular weight: 2,000 g/mol) mixed in a weight ratio of 9:1 (A: F-2010).

The filler component (F1) was a mixture of spherical alumina (F11) having an average particle diameter of about 70 μm, spherical alumina (F12) having an average particle diameter of about 20 μm, and aluminum hydroxide (F13) having an average particle diameter of about 1 μm, in a weight ratio of 70:12:18 (F11:F12:F 13).

Preparation of the curing agent part

Isocyanate component (H, vencorex, tolonate HDT-LV 2), filler component (F2) and plasticizer (Pc, AEKYUNG Petrochemical Co., ltd., diisononyl adipate) were mixed in a weight ratio of 3.9:91.7:4.4 (H: F2: pc) to prepare a curing agent part (V) _B ). Tolonate HDT-LV2 corresponds to hexamethylene diisocyanate trimer.

The filler component (F2) was a mixture of spherical alumina (F21) having an average particle diameter of about 70 μm, spherical alumina (F22) having an average particle diameter of about 20 μm and alumina (F23) having an average particle diameter of about 1 μm in a weight ratio of 60:10:30 (F21: F22: F23).

Preparation of the final curable composition

The main part (V) _A ) And a curing agent part (V _B ) At 1:1 (V _A :V _B ) Is added to a static mixer and mixed to prepare the final curable composition. The curable composition comprises about 89% by weight of filler component (f1+f2) relative to the total weight, and about 7.4% by weight of aluminum hydroxide relative to the total weight of the curable composition. Further, the curable composition contains about 1,107 parts by weight of alumina relative to 100 parts by weight of aluminum hydroxide. Further, it was found that the combined content of the halogen element and the phosphorus (P) element measured by ICP (inductively coupled plasma) according to the following physical property measurement method was 0.2% by weight or less with respect to the total weight of the curable composition.

Example 2.

Main part preparation

The same polyol component (P) as that of example 1 was used.

The filler component (F1) was a mixture of spherical alumina (F11) having an average particle diameter of about 70 μm, spherical alumina (F12) having an average particle diameter of about 20 μm, and aluminum hydroxide (F13) having an average particle diameter of about 1 μm, in a weight ratio of 45:30:25 (F11:F12:F13).

Preparation of the curing agent part

Isocyanate component (H, vencorex, tolonate HDT-LV 2), filler component (F2) and plasticizer (Pc, AEKYUNG Petrochemical Co., ltd., diisononyl adipate) were mixed in a weight ratio of 3.9:91.7:4.4 (H: F2: pc) to prepare a curing agent part (V) _B )。

The filler component (F2) was a mixture of spherical alumina (F21) having an average particle diameter of about 70 μm, spherical alumina (F22) having an average particle diameter of about 20 μm and alumina (F23) having an average particle diameter of about 1 μm in a weight ratio of 40:30:30 (F21: F22: F23).

Preparation of the final curable composition

The main part (V) _A ) And a curing agent part (V _B ) At 1:1 (V _A :V _B ) Is added to a static mixer and mixed to prepare the final curable composition. The curable composition comprises about 89% by weight of filler component (f1+f2) relative to the total weight, and about 8.4% by weight of aluminum hydroxide relative to the total weight of the curable composition. Further, the curable composition contains about 977 parts by weight of alumina relative to 100 parts by weight of aluminum hydroxide. Further, it was found that the combined content of the halogen element and the phosphorus (P) element measured by ICP (inductively coupled plasma) according to the following physical property measurement method was 0.2% by weight or less with respect to the total weight of the curable composition.

Example 3.

Main part preparation

Polyol component (P), filler component (F1) and plasticizer (Pc, AEKYUNG Petrochemical co., ltd., diisononyl adipate) were mixed in a weight ratio of 11.6:87.5:0.9 (P: F1: pc) to prepare a main part (V _A )。

The same polyol component (P) as that of example 1 was used.

The filler component (F1) was a mixture of spherical alumina (F11) having an average particle diameter of about 70 μm, aluminum hydroxide (F14) having an average particle diameter of about 50 μm, and aluminum hydroxide (F13) having an average particle diameter of about 1 μm, in a weight ratio of 45:30:25 (F11: F14: F13).

Preparation of the curing agent part

Isocyanate component (H, vencorex, tolonate HDT-LV 2), filler component (F2) and plasticizer (Pc, AEKYUNG Petrochemical Co., ltd., diisononyl adipate) were mixed in a weight ratio of 4:91.7:4.3 (H: F2: pc) to prepare a hardener part (V) _B )。

Preparation of the final curable composition

The main part (V) _A ) And a curing agent part (V _B ) At 1:1 (V _A :V _B ) Is added to a static mixer and mixed to prepare the final curable composition. The curable composition comprises about 89% by weight of filler component (f1+f2) relative to the total weight, and about 20.7% by weight of aluminum hydroxide relative to the total weight of the curable composition. Further, the curable composition contains about 332 parts by weight of alumina relative to 100 parts by weight of aluminum hydroxide. Further, it was found that the combined content of the halogen element and the phosphorus (P) element measured by ICP (inductively coupled plasma) according to the following physical property measurement method was 0.2% by weight or less with respect to the total weight of the curable composition.

Example 4.

Main part preparation

Polyol component (P), filler component (F1) and plasticizer (Pc, AEKYUNG Petrochemical co., ltd., diisononyl adipate) were mixed in a weight ratio of 11.0:88.2:0.8 (P: F1: pc) to prepare a main part (V _A )。

The same polyol component (P) as that of example 1 was used.

The filler component (F1) was a mixture of spherical alumina (F11) having an average particle diameter of about 70 μm, aluminum hydroxide (F15) having an average particle diameter of about 17 μm, and aluminum hydroxide (F13) having an average particle diameter of about 1 μm, in a weight ratio of 60:20:20 (F11: F15: F13).

Preparation of the curing agent part

Isocyanate component (H, vencore x, tolonate HDT-LV 2), filler component (F2) and plasticizer (Pc, AEKYUNG Petrochemical co., ltd., diisononyl adipate) were mixed in a weight ratio of 5.2:89.9:4.9 (H: F2: pc) to prepare a hardener part (V _B )。

The filler component (F2) was a mixture of spherical alumina (F21) having an average particle diameter of about 70 μm, aluminum hydroxide (F24) having an average particle diameter of about 17 μm, and aluminum hydroxide (F25) having an average particle diameter of about 1 μm, in a weight ratio of 60:20:20 (F21: F24: F25).

Preparation of the final curable composition

The main part (V) _A ) And a curing agent part (V _B ) At 1:1 (V _A :V _B ) Is added to a static mixer and mixed to prepare the final curable composition. The curable composition comprises about 88 wt.% or so of filler component (f1+f2) relative to the total weight, and about 35.4 wt.% of aluminum hydroxide relative to the total weight of the curable composition. Further, the curable composition contains about 150 parts by weight of alumina relative to 100 parts by weight of aluminum hydroxide. Further, it was found that the combined content of the halogen element and the phosphorus (P) element measured by ICP (inductively coupled plasma) according to the following physical property measurement method was 0.2% by weight or less with respect to the total weight of the curable composition.

Example 5.

Main part preparation

Polyol component (P), filler component (F1) and plasticizer (Pc, AEKYUNG Petrochemical co., ltd., diisononyl adipate) were mixed in a weight ratio of 11.6:87.7:0.7 (P: F1: pc) to prepare a main part (V _A )。

The same polyol component (P) as that of example 1 was used.

The filler component (F1) was a mixture of spherical alumina (F11) having an average particle diameter of about 70 μm, aluminum hydroxide (F15) having an average particle diameter of about 17 μm, and aluminum hydroxide (F13) having an average particle diameter of about 1 μm, in a weight ratio of 50:30:20 (F11: F15: F13).

Preparation of the curing agent part

Isocyanate component (H, vencore x, tolonate HDT-LV 2), filler component (F2) and plasticizer (Pc, AEKYUNG Petrochemical co., ltd., diisononyl adipate) were mixed in a weight ratio of 5.5:89.4:5.1 (H: F2: pc) to prepare a hardener part (V _B )。

The filler component (F2) was a mixture of spherical alumina (F21) having an average particle diameter of about 70 μm, aluminum hydroxide (F24) having an average particle diameter of about 17 μm, and aluminum hydroxide (F25) having an average particle diameter of about 1 μm, in a weight ratio of 50:30:20 (F21: F24: F25).

Preparation of the final curable composition

The main part (V) _A ) And a curing agent part (V _B ) At 1:1 (V _A :V _B ) Is added to a static mixer and mixed to prepare the final curable composition. The curable composition comprises about 88 wt.% or so of filler component (f1+f2) relative to the total weight, and about 43.9 wt.% of aluminum hydroxide relative to the total weight of the curable composition. Further, the curable composition contains about 100 parts by weight of alumina relative to 100 parts by weight of aluminum hydroxide. Further, it was found that the combined content of the halogen element and the phosphorus (P) element measured by ICP (inductively coupled plasma) according to the following physical property measurement method was 0.2% by weight or less with respect to the total weight of the curable composition.

Comparative example 1.

Main part preparation

Polyol component (P), filler component (F1), plasticizer (Pc, AEKYUNG Petrochemical Co., ltd., diisononyl adipate) and phosphorus (P) element-containing solid flame retardant (SF, CHEMPIA, X-GUARD FR-119L) were mixed in a weight ratio of 8.5:88.9:1.2:1.4 (P: F1: pc: SF) to prepare a main part (V) _A )。

The same polyol component (P) as that of example 1 was used.

The filler component (F1) was a mixture of spherical alumina (F11) having an average particle diameter of about 70 μm, spherical alumina (F12) having an average particle diameter of about 20 μm and alumina (F16) having an average particle diameter of about 1 μm in a weight ratio of 60:20:20 (F11:F12:F16).

Preparation of the curing agent part

A solid flame retardant comprising an isocyanate component (H, vencorex, tolonate HDT-LV 2), a filler component (F2), a plasticizer (Pc, AEKYUNG Petrochemical Co., ltd., diisononyl adipate) and a phosphorus (P) element(SF, CHEMPIA, X-GUARD FR-119L) was mixed in a weight ratio of 3.8:90.2:4.4:1.6 (H: F2: pc: SF) to prepare a hardener part (V) _B )。

The filler component (F2) was a mixture of spherical alumina (F21) having an average particle diameter of about 70 μm, spherical alumina (F22) having an average particle diameter of about 20 μm and alumina (F23) having an average particle diameter of about 1 μm in a weight ratio of 60:20:20 (F21: F22: F23).

Preparation of the final curable composition

The main part (V) _A ) And a curing agent part (V _B ) At 1:1 (V _A :V _B ) Is added to a static mixer and mixed to prepare the final curable composition. The curable composition comprises about 88 wt.% or so of filler component (f1+f2) relative to the total weight. In addition, the curable composition includes about 1.52 wt% of a solid flame retardant containing phosphorus (P) element relative to the total weight. In this regard, it was found that the combined content of the halogen element and the phosphorus (P) element, as measured by ICP (inductively coupled plasma) according to the following physical property measurement method, was about 0.35% by weight or more relative to the total weight of the curable composition.

Comparative example 2.

Main part preparation

The same polyol component (P) as that of example 1 was used.

The filler component (F1) was a mixture of spherical alumina (F11) having an average particle diameter of about 70 μm, spherical alumina (F12) having an average particle diameter of about 20 μm, and aluminum hydroxide (F13) having an average particle diameter of about 1 μm, in a weight ratio of 67:22:11 (F11:F12:F 13).

Preparation of the curing agent part

The isocyanate component (H, vencorex, tolonate HDT-LV 2), the filler component (F2) and the plasticizer (Pc, AEKYU)NG Petrochemical co., ltd., diisononyl adipate) was mixed in a weight ratio of 3.9:91.7:4.4 (H: F2: pc) to prepare a hardener part (V _B )。

Preparation of the final curable composition

The main part (V) _A ) And a curing agent part (V _B ) At 1:1 (V _A :V _B ) Is added to a static mixer and mixed to prepare the final curable composition. The curable composition comprises about 89% by weight of filler component (f1+f2) relative to the total weight, and about 4.6% by weight of aluminum hydroxide relative to the total weight of the curable composition. Further, the curable composition contains about 1,848 parts by weight of alumina relative to 100 parts by weight of aluminum hydroxide. Further, it was found that the combined content of the halogen element and the phosphorus (P) element measured by ICP (inductively coupled plasma) according to the following physical property measurement method was 0.2% by weight or less with respect to the total weight of the curable composition.

Comparative example 3.

Main part preparation

Polyol component (P), filler component (F1) and plasticizer (Pc, AEKYUNG Petrochemical co., ltd., diisononyl adipate) were mixed in a weight ratio of 11.7:87.1:1.2 (P: F1: pc) to prepare a main part (V _A )。

As polyol component (P), polyol (A) of preparation example 1 was used.

Preparation of the curing agent part

The isocyanate component (H, vencorex, tolonate HDT-LV 2), filler component (F2) and plasticizer (Pc, AEKYUNG Petrochemical co., ltd., diisononyl adipate) were mixed in a weight ratio of 4.2:91.6:4.2 (H: F2: pc) to prepare a hardener part (V _B )。

Preparation of the final curable composition

The main part (V) _A ) And a curing agent part (V _B ) At 1:1 (V _A :V _B ) Is added to a static mixer and mixed to prepare the final curable composition. The curable composition comprises about 88 wt.% or so of filler component (f1+f2) relative to the total weight, and about 20 wt.% of aluminum hydroxide relative to the total weight of the curable composition. Further, the curable composition contains about 341 parts by weight of alumina relative to 100 parts by weight of aluminum hydroxide. Further, it was found that the combined content of the halogen element and the phosphorus (P) element measured by ICP (inductively coupled plasma) according to the following physical property measurement method was 0.2% by weight or less with respect to the total weight of the curable composition.

Comparative example 4.

Main part preparation

Polyol component (P), filler component (F1) and plasticizer (Pc, AEKYUNG Petrochemical co., ltd., diisononyl adipate) were mixed in a weight ratio of 12.3:87.1:0.6 (P: F1: pc) to prepare a main part (V _A )。

Polyol component (P) was a mixture of polyol (A) of preparation example 1 above and a trifunctional polyester polyol (supplier: kuraray, product name: F-2010, weight average molecular weight: 2,000 g/mol) mixed in a weight ratio of 8:2 (A: F-2010).

Preparation of the curing agent part

Isocyanate component (H, vencorex, tolonate HDT-LV 2), filler component (F2) and plasticizer (Pc, AEKYUNG Petrochemical Co., ltd., diisononyl adipate) were mixed in a weight ratio of 3.8:91.7:4.5 (H: F2: pc) to prepare a curing agent part (V) _B )。

Preparation of the final curable composition

Comparative example 5.

Main part preparation

As polyol component (P), a trifunctional polyester polyol (supplier: kuraray, product name: F-2010, weight average molecular weight: 2,000 g/mol) was used.

Preparation of the curing agent part

Preparation of the final curable composition

The physical properties presented in examples and comparative examples were evaluated in the following manner.

< method for measuring physical Properties >

1. Viscosity and thixotropic index (T.I.)

[ method of measuring viscosity ]

The shear rate was set to 2.4 seconds by a viscometer (manufacturer: brookfield, model name: DV3 THB-CP) and spindle CPA-52Z ^-1 And rotate itAfter 180 seconds, the viscosities of the main part and the hardener part of the examples and comparative examples were measured as final viscosity measurements. The viscosity was measured at 25 ℃.

Specifically, the plate is mounted on the plate connection of the viscometer and adjusted by a control rod to form a constant gap between the spindle and the plate. The plates were separated, and a measurement target of about 0.5mL was applied to the center of the separated plates. The plate to which the measurement target was applied was again mounted on the plate connecting portion of the viscometer, and after waiting until the torque value became 0, the shear rate was set to 2.4 seconds ^-1 And rotated for 180 seconds to measure the viscosity, and the final viscosity value was measured as the viscosity of the measurement target. Here, the measurement target means a main portion or a curing agent portion.

[ thixotropic index measurement method ]

For the measurement target, the viscosity was measured in the same manner as the above viscosity measurement method, but the shear rates were set to 0.24 seconds, respectively ^-1 And 2.4 seconds ^-1 To measure viscosity, and then thixotropic index (t.i.) was measured according to the following equation.

[ thixotropic index calculation equation ]

Thixotropic index (t.i.) =v ₁ /V ₂

In the above calculation equation, V ₁ At 25℃and 0.24 seconds for the measurement target ^-1 Viscosity measured under the conditions of (2) and V ₂ At 25℃for 2.4 seconds for the measurement target ^-1 Viscosity measured under the conditions of (2).

2. Specific gravity

Each of the final curable compositions prepared in examples and comparative examples was cured at about 25 ℃ for about 24 hours to form a cured product, which was cut into pieces to prepare samples, and then the specific gravity of the samples was measured at 25 ℃ using a specific gravity bottle. The specific gravity is based on the density of water measured at 1atm and 4 ℃ (1 g/cm ³ ) Measured and having dimensionless units.

3. Thermal conductivity

Thermal conductivity was measured using the hot disk method (hot disk method). Specifically, each of the final curable compositions prepared in examples and comparative examples was cured in a disc mold having a diameter of about 4cm and a thickness of about 5mm at about 25 ℃ for 24 hours to obtain a cured product sample, and the thermal conductivity was measured in the thickness direction of the sample according to the ISO 22007-2 standard using a thermal constant analyzer. As specified in the above standard (ISO 22007-2), a hot plate device is such that: it can determine the thermal conductivity by measuring the temperature change (resistance change) when heating a sensor in which the nickel wire has a double helix structure, and measuring the thermal conductivity according to such a standard.

4. Flame retardancy

Each of the final curable compositions prepared in examples and comparative examples was cured at about 25 ℃ for about 24 hours to form a cured product having a width of 13mm, a length of 125mm and a thickness of 2mm, and measured from the formed cured product according to UL94V measurement standards. If the result measured according to the UL94V measurement standard is of the V-0 class, it is evaluated as passing, and in the case of other classes, it is evaluated as NG.

5. Measurement of adhesion to polyester

Samples prepared by attaching a PET (polyethylene terephthalate) film and an aluminum plate as an adherend were evaluated. As the PET film, a film having a width of about 10mm and a length of about 200mm was used, and as the aluminum plate, a plate having a width and a length of about 100mm each was used. The final curable compositions according to examples or comparative examples were each applied on the entire surface of an aluminum plate (application such that the thickness after curing was about 2mm or so), and a PET film in a state of being closely attached to a curable composition layer was held at about 25 ℃ for about 24 hours to prepare a sample. At this time, the entire width of the PET film and a length portion of around 100mm were attached to the aluminum plate by the curable composition. In this sample, the adhesion to polyester was measured while the PET film was peeled from the aluminum plate in the longitudinal direction in a state where the aluminum plate was fixed thereto. The peeling was performed at a peeling speed of about 0.5 mm/min and a peeling angle of about 180 degrees until the PET film was completely peeled off.

6. Measurement of adhesion to aluminum

The final curable compositions according to examples or comparative examples were each coated on the center of aluminum substrates having horizontal and vertical lengths of 2cm and 7cm, respectively, to have a width of 2cm and a length of around 2cm, and aluminum substrates having horizontal and vertical lengths of 2cm and 7cm, respectively, were attached again on the coating layers, and the curable compositions were cured by maintaining the state. Curing is carried out at about 25℃for about 24 hours. Here, two aluminum substrates are attached to form an angle of 90 degrees to each other. Hereinafter, in the case of fixing the upper aluminum substrate, the lower aluminum substrate was pressed at a speed of 0.5 mm/min to measure force while separating the lower aluminum substrate, and the adhesive force to aluminum was obtained by dividing the maximum force measured in this process by the area of the test piece.

7. Shore OO hardness

For the cured product of each final curable composition according to examples or comparative examples, the shore OO hardness was measured according to ASTM D2240 standard. The measurement was performed using an ASKER durometer apparatus in which the initial hardness was measured by applying a load of 1kg or more (about 1.5 kg) to the surface of the cured product in the form of a film, and the hardness was evaluated by determining a stable measurement value after 15 seconds. The cured product is formed by maintaining the final curable composition at about 25 ℃ for about 24 hours.

8. Radius of curvature

The radius of curvature of the cured product of each final curable composition according to examples or comparative examples was evaluated as a cured product having a width of 1cm, a length of 10cm and a thickness of 2 mm. When the cured body is attached to a cylinder having a plurality of radii and is bent in the longitudinal direction, the radius of curvature is the smallest radius of the cylinder where no crack occurs in the cured body. The cured product is formed by maintaining the final curable composition at about 25 ℃ for about 24 hours.

9. Module workability

The final curable compositions according to examples or comparative examples were each applied on an aluminum plate to have a square shape of 8cm in width, 8cm in length and about 2mm in thickness. The applied curable composition is maintained at about 25 ℃ for about 24 hours and cured. Subsequently, when the formed cured product was removed from the aluminum plate, the module workability was evaluated according to the following [ module workability evaluation criteria ].

[ Module processability evaluation criterion ]

By: when the cured product was peeled off in the form of a sheet without leaving a residue on the aluminum plate

NG: when the cured product cannot be peeled off from the aluminum plate or remains even after peeling off

10. Measurement of average particle diameter of particles

The particle average particle size of the filler is the D50 particle size of the filler, which is the particle size measured by a Marvern MASTERSIZER3000 apparatus according to the ISO-13320 standard. Distilled water was used as a solvent in the measurement. The incident laser light is scattered by the filler dispersed in the solvent, and the values of the intensity and directivity of the scattered laser light are changed according to the size of the filler, which is analyzed by the mie theory, whereby the D50 particle diameter can be obtained. By the above analysis, the distribution can be obtained by converting into a diameter of a sphere having the same volume as the dispersed filler, and the particle diameter can be evaluated by obtaining a D50 value as a median value of the distribution.

11. Measurement of weight average molecular weight

The weight average molecular weight (Mw) was measured using GPC (gel permeation chromatography). Specifically, the weight average molecular weight (Mw) can be measured by: the sample to be analyzed was added to a 5mL vial, diluted with THF (tetrahydrofuran) solvent to a concentration of about 1mg/mL, and then the standard sample for calibration and the analysis sample were filtered through a syringe filter (pore diameter: 0.45 μm). ChemStation of Agilent technologies was used as an analytical procedure and the weight average molecular weight (Mw) could be obtained by comparing the elution time of the sample with a calibration curve.

< GPC measurement conditions >

Instrument: agilent technologies series 1200

Column: TL mix. A & B using Agilent technologies

Solvent: THF (tetrahydrofuran)

Column temperature: 35 DEG C

Sample concentration: 1mg/mL,200 μl injection

Standard sample: using polystyrene (MP: 3900000, 723000, 316500, 52200, 31400, 7200, 3940, 485)

12. Measurement of halogen element and phosphorus element

Samples of each of the final curable compositions prepared in the above examples and comparative examples were placed in vials weighing 0.1g, and 1mL of nitric acid was added thereto. In the following, a small amount of hydrogen peroxide was added to the vial and heated on a hot plate to dissolve the sample. When the sample was completely dissolved and had a transparent color, an analysis sample was prepared by adding three stages of ultrapure water thereto so that the total volume was 10 mL. In the analysis sample, the contents of halogen element and phosphorus element were measured by ICP-OES (inductively coupled plasma-optical emission spectrometry) analysis under the following conditions. The contents of the halogen element and the phosphorus element measured according to the analysis may be measured each, and the combined contents of the halogen element and the phosphorus element may be measured by adding them.

[ ICP-OES analysis conditions ]

RF power: 1,300W

Torch height: 15.0mm

Plasma gas flow rate: 15.00L/min

Sample gas flow rate: 0.8L/min

Auxiliary gas flow rate: 0.2L/min

Pump speed: 1.5 mL/min

Internal standard substance: yttrium (Y) or scandium (Sc)

The results of the test data measured in the above examples and comparative examples are summarized in tables 1 and 2 below.

TABLE 1

TABLE 2

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Referring to table 1 above, it can be considered that in examples 1 to 5, the main part and the curing agent part have appropriate viscosity and thixotropic index. Referring to table 2 above, it can be determined that examples 1 to 5 have low specific gravity characteristics and excellent thermal conductivity, and it can be considered that excellent flame retardancy is ensured without adding phosphorus or halogen-series flame retardants. Further, it is considered that in examples 1 to 5, the adhesion to polyester and the adhesion to aluminum are low adhesion suitable for the purpose of the present application. Further, it was confirmed that examples 1 to 5 had surface hardness suitable for the purpose of the present application, were flexible, and had excellent workability.

On the other hand, referring to table 2 above, comparative example 1 is shown to have a relatively high specific gravity and poor flame retardancy. Further, although excessive aluminum oxide was used, comparative example 1 exhibited relatively low thermal conductivity due to the deterioration of heat dissipation characteristics by the use of the phosphorus-based flame retardant.

Further, referring to table 2, it is shown that comparative example 2 has no flame retardancy, since the jig is partially burned when measured according to UL94V measurement standard, because the content of aluminum hydroxide is small compared to the total composition. In the examples, aluminum hydroxide within the range specified in the present application was contained, and in particular, when example 1 and comparative example 2 were compared, the difference in flame retardant characteristics was remarkable. This can be considered to indicate that the content of aluminum hydroxide is of great importance. Further, in comparative example 2, it is considered that adhesion force unsuitable for the purpose of the present application is generated between PET and aluminum plate due to imbalance in the bonding between the filler component and the polyol and isocyanate components in the composition.

Referring to table 2, comparative examples 3 and 4 do not incorporate the polyol component as shown in the present application, and thus it can be considered that the adhesion to aluminum or PET is not suitable for the purpose of the present application. Further, referring to table 1, comparative example 4 did not incorporate the polyol component as shown in the present application, so that the main part and the curing agent part had high viscosity, and thus were unsuitable for the process.

Referring to tables 1 and 2, in comparative example 5, the main part and the curing agent part have high viscosity to such an extent that they cannot be compounded, and thus physical properties cannot be measured.

Claims

1. A curable composition comprising:

a polyol component; and

a filler component, and the curable composition forms

A cured product exhibiting flame retardancy of V-0 grade or more while having a specific gravity of 3 or less, a thermal conductivity of 2W/mK or more, and a combined content of halogen element and phosphorus element of 0.3 wt% or less.

2. The curable composition of claim 1 forming an adhesion to aluminum of 0.1N/mm ² Or less and has an adhesion to polyester of 100gf/cm or less.

3. The curable composition of claim 1 wherein the temperature is 25 ℃ for 2.4 seconds ^-1 The viscosity measured at a shear rate of 400kcP or less.

4. The curable composition of claim 1 wherein the polyol component comprises a first polyol that is a difunctional polyol and a second polyol that is a polyol having a trifunctional or higher functionality.

5. The curable composition of claim 4 wherein the first polyol or the second polyol comprises a branched hydrocarbon chain having 3 or more carbon atoms at the terminus.

6. The curable composition of claim 4 wherein the first polyol or the second polyol is a polyol having: polycaprolactone polyol units or alkylene glycol units; polyol unit and dicarboxylic acid unit, and

The polyol unit is a unit derived from a polyol which is an alkane having 1 to 20 carbon atoms substituted with 3 to 10 hydroxyl groups.

7. The curable composition of claim 4 wherein the first polyol and the second polyol are polyester polyols.

8. The curable composition of claim 4 wherein the polyol component comprises greater than 80 weight percent of the first polyol relative to the total weight of the polyol component.

9. The curable composition of claim 4, wherein the first polyol (P _A ) And the second polyol (P _B ) Weight ratio (P) _A /P _B ) 5 or more.

10. The curable composition of claim 4 wherein the first polyol has a weight average molecular weight of 100g/mol to 2,000g/mol and the second polyol has a weight average molecular weight of 500g/mol to 5,000g/mol.

11. The curable composition of claim 1 comprising 70 weight percent or greater of the filler component relative to the total weight.

12. The curable composition of claim 1 wherein the filler component comprises a first filler having a specific gravity of 3 or less and a second filler having a specific gravity greater than 3.

13. The curable composition of claim 11 wherein the first filler is a metal hydroxide.

14. The curable composition of claim 11 comprising 10 weight percent or greater of the first filler relative to the total weight.

15. The curable composition of claim 11, wherein the second filler comprises one or more selected from the group consisting of: aluminum oxide, magnesium oxide, beryllium oxide, titanium oxide, silicon nitride, aluminum nitride, silicon carbide, copper, silver, iron, and titanium.

16. The curable composition of claim 11, wherein the filler component comprises the second filler in a range of 50 to 800 parts by weight relative to 100 parts by weight of the first filler.

17. A two-part curable composition comprising:

a major portion comprising a polyol component and a first filler component; and

a curative portion comprising an isocyanate component and a second filler component, and the two-part curable composition forms

Exhibits flame retardancy of V-0 grade or more and has a combined content of halogen element and phosphorus element of 0.3 wt% or less and has a content of 0.1N/mm ² Or a cured product of less adhesion to aluminum.

18. The curable composition of claim 17, wherein one or more selected from the first filler component and the second filler component comprises a first filler having a specific gravity of 3 or less, and

comprising 5% by weight or more of said first filler relative to the total weight.

19. The curable composition of claim 17 wherein the isocyanate component is a non-aromatic isocyanate compound.

20. An apparatus comprising a heat generating element and a heat carrier in thermal contact with the heat generating element, wherein

The heat carrier comprises one or more selected from the group consisting of a cured product of the curable composition of claim 1 and a cured product of the two-part curable composition of claim 17.