WO2018217038A1

WO2018217038A1 - Resin composition for grinding tool and grinding tool manufactured from the resin composition

Info

Publication number: WO2018217038A1
Application number: PCT/KR2018/005914
Authority: WO
Inventors: 김상우; 이승희; 안기호; 김율리아나; 김영대
Original assignee: 주식회사 엘지화학
Priority date: 2017-05-24
Filing date: 2018-05-24
Publication date: 2018-11-29

Abstract

The present invention relates to a resin composition for a grinding tool and a grinding tool manufactured from the resin composition. The resin composition for the grinding tool, according to the present invention, has high heat resistance and excellent processability, thereby enabling the provision of the grinding tool having improved heat resistance and durability.

Description

[Name of invention]

Resin composition for grinding tool and grinding tool made of said resin composition

Technical Field

Cross Citation with Related Applications

This application claims the benefit of priority based on Korean Patent Application No. 10-2017-0064326 dated May 24, 2017 and Korean Patent Application No. 10-2018-0058367 dated May 23, 2018. All content disclosed in the documents is included as part of this specification. The present invention relates to a resin composition for grinding tools and a grinding tool made of the resin composition.

[Technique to become background of invention]

Grinding tools are tools used to frictionally polish and / or cut articles of various materials such as metals, plastics and ceramics. Generally, grinding tools are formed using a composition comprising abrasive particles, fillers and resin binders.

On the other hand, in the grinding process for any abrasive article, the temperature of the grinding zone rises rapidly due to the friction between the grinding tool and the article. If the article to be ground is a hard colorant which is difficult to grind, for example hard metal or hard ceramic, very high temperature frictional heat is generated.

This increase in temperature in the grinding zone acts as a major factor causing thermal breakage and shortening of the life of the grinding tool. For example, the resin binder is thermally decomposed by friction in the grinding process and is bound by the resin binder. Existing abrasive particles and layering agent may be eliminated from the grinding tool.

In order to minimize thermal breakage of the grinding tool, polyimide resins, epoxy resins, phenol resins, amino resins and the like, which are known to be excellent in heat resistance, have been applied as the resin binder.

By the way, the polyimide resin exhibits high heat resistance, but has a disadvantage in that its production cost is high and its manufacturing process is very complicated, resulting in low productivity. And the above Epoxy resins, phenol resins, and the like have limitations that make it difficult to ensure sufficient heat resistance and durability.

[Content of invention]

Problem to be solved

The present invention is to provide a resin composition for a grinding tool that enables the provision of a grinding tool having excellent heat resistance and durability in an easy processing process. In addition, the present invention is to provide a grinding tool made of the resin composition with improved heat resistance and durability.

[Measures of problem]

According to the invention,

Abrasive particles,

Layer agent and

Cured resin binder from a composition containing a phthalonitrile compound

Including, a resin composition for a grinding tool is provided.

Moreover, according to this invention, the grinding tool manufactured from the said resin composition is provided. Hereinafter, a resin composition for a grinding tool and a grinding tool made of the resin composition according to embodiments of the present invention will be described in detail.

Prior to this, the terminology is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention unless expressly stated otherwise. As used herein, the singular forms “a”, “an” and “the” include plural forms as well, unless the phrases clearly indicate the opposite.

As used herein, the meaning of ¹ to ¹ embodies a particular characteristic, region, integer, step, operation, element, and / or component, and other specific characteristics, region, integer, step, operation, element, component, and / or group. It does not exclude the presence or addition of. I. Resin Compositions for Grinding Tools

According to one embodiment of the invention,

Abrasive particles,

Fillers and

Cured resin binder from a composition containing a phthalonitrile compound

Including, a resin composition for a grinding tool is provided. As a result of continuous research by the inventors, when a cured resin binder is applied from a composition containing a phthalonitrile compound to a resin composition for a grinding tool including abrasive particles and fillers, the grinding tool has excellent heat resistance and durability through an easy processing process. It was confirmed that it can provide.

In particular, the resin composition for the grinding tool provided through the present invention can minimize thermal decomposition or thermal breakage of the grinding tool due to frictional heat by including the resin binder, thereby improving durability and life of the grinding tool. Hereinafter, the components that may be included in the resin composition for the grinding tool will be described in more detail. The resin composition for grinding tools contains abrasive particles.

The abrasive particles are particles that act to polish and / or cut the surface of the article by friction with the article to be ground.

As the abrasive particles, those well known in the art may be applied without particular limitation. For example, the abrasive particles may be metal particles, inorganic particles, metal coated inorganic particles, and the like.

Specifically, the abrasive particles are one or more selected from the group consisting of natural diamond, synthetic diamond, boron nitride, cubic boron nitride (CBN), alumina, silica, silicon carbide, alumina-zirconia, titanium diboride, and boron carbide. It may be a particle, but is not limited thereto.

The type and particle diameter of the abrasive particles may be appropriately selected depending on the material or form of the object to be ground. For example, the average particle diameter of the abrasive particles is 0.1 fM Or at least 0.5 im, at least 1 mi at black, at least 10 IM, at least 50 rn at black; And 2000 μιη or less, or 1500 or less, or 1000 [M or less, black may be 750 or less.

The shape of the abrasive particles is not particularly limited, and may be applied in various forms such as granules, spheres, rods, polygons, pyramids, and the like.

The content of the abrasive particles may vary depending on the type of the object to be ground, and preferably 20 to 60% by weight of the total weight of the resin composition for the grinding tool. Specifically, the abrasive particles is 20 parts by weight ^_0/0 or more of the total weight of the resin for the grinding tool composition, or 25 wt. ^_0/0 or more, or 30 wt. ^_0/0 or more, or 35 weight ^_0/0 above, black is 40 weight ^_0/0 or more; And 60 parts by weight ^_0/0 or less, the black can be included more than 55 weight ^_0/0 or less, or 50 wt. ^_0/0.

In order that the grinding operation can not be expressed sufficiently layer, the content of the abrasive grains is preferably not less than 20 wt. ^_0/0. Where, however, the abrasive particles to be added in excess, so that the abrasive particles be the durability is easily detached from the grinding tool deteriorated, it is preferred that the abrasive particles comprise less than 60 wt. ^_0/0. In addition, the said resin composition for grinding tools contains a layer agent. .

The layer agent is added to reinforce physical properties such as the stiffness, compressive strength, bending coefficient, abrasion resistance, thermal conductivity, malleability, grinding, adhesion, and lubrication characteristics of the grinding tool.

As the filler, those well known in the art may be applied without particular limitation. For example, the layer filler may be a metal layer filler, an inorganic layer filler, an organic filler, a composite filler, or the like. ^'

Specifically, the layering agent is copper, tungsten, iron oxide, copper-tin alloy, silicon carbide, alumina, calcite, limestone, marble, limestone, creolite, silica, silicate, metal carbonate, metal sulfate, metal sulfite, metal oxide Sodium chloride, magnesium chloride, iron disulfide, molybdenum disulfide, antimony trisulfide, graphite, glass fiber, molybdenum disulfide, antimony trisulfide, tungsten sulfide, silane coupling agent, titanate coupling agent, zirconate coupling agent, One or more layering agents selected from the group consisting of zircoaluminate coupling agents and carbon fibers May be, but is not limited thereto.

The type and particle size of the filler may be determined in consideration of physical properties of the grinding tool to be reinforced, dispersibility of the filler, and the like.

The form of the layering agent is not particularly limited, and may be applied in various forms such as liquid, granules, spheres, rods, polygons, pyramids, fibers, and the like.

Then, the content of the layer may be a premise may be determined in consideration of the type and physical properties to the reinforcement of the grinding target goods, preferably 10 to 60 parts by weight ^_0/0 of the total weight of the resin composition for the polishing tools. Specifically, the filler is 10 parts by weight ^_0/0 or more of the total weight of the resin composition for the polishing tools, or 15 parts by weight ^_0/0 or more, or 20 wt. ^_0/0 or more; And 60 parts by weight ^_0/0 or less, or 50 wt. ^_0/0 or less, the black is 40 wt% or less, and black may be included more than 30 parts by weight ^_0/0 or less, or 25 wt. ^_0/0.

In order to ensure that the reinforcing effect by the layer assumptions can be expressed sufficiently layer, the amount of the layer premise is preferably not less than 10 wt. ^_0/0. However, Hida preferred that the filler, so that the durability may be lowered, etc. When added in excess polishing efficiency may be degraded, or the layer is easily detached from the premise grinding tool, wherein the filler comprises less than 60 wt. ^_0/0. On the other hand, the resin composition for grinding tools includes a resin binder cured from a composition containing a phthalonitrile compound.

The resin binder is added to impart molding processability to the resin composition for the grinding tool and to stably fix the abrasive particles and the layer filler to the grinding tool. The resin composition for the grinding tool is processed in a state in which the abrasive particles and the filler are dispersed in a matrix of the resin binder.

The resin binder enables the provision of the grinding tool in an easy process equivalent to that of a conventional thermosetting or thermoplastic resin binder, without requiring a complicated processing process as compared with a conventional polyimide resin having high heat resistance.

The resin binder is a compound cured from a composition containing a phthalonitrile compound, and may be a mixture of a phthalonitrile compound and a curing agent or a prepolymer formed by reaction of the mixture.

Here, the prepolymer refers to the resin composition for the grinding tool. The reaction between the phthalonitrile compound and the curing agent occurs to some extent (for example, the so-called polymerization of the A or B stage stage) or the state of the polymerization completely, and exhibits proper fluidity, for example, It may mean a state that can be processed into a grinding tool material as described later.

In addition, the prepolymer corresponds to a state in which the polymerization of the phthalonitrile compound and the curing agent is somewhat advanced, and the melt viscosity measured at a temperature within a range of about 150 ^° C. to 250 ^° C. is 100 cP to 50,000 cP, 100 cP. It may mean a state in the range of 10,000 to 10,000 cP, or 100 cP to 5000 cP. Thus, the prepolymer may also exhibit excellent curability, low melting temperature and wide process window, like the resin composition for the grinding tool. For example, the processing temperature of the prepolymer may be in the range of 150 ^° C to 350 ^° C. In this case, the processing temperature means a temperature at which the prepolymer exists in a processable state. Such a processing temperature may be, for example, a melting temperature (T _m ) or a glass transition temperature (T _g ). In this case the absolute value of the process window of the prepolymer, i.e. the difference (T _c -T _p ) between the processing temperature (T _p ) and the curing temperature (T _c ) of the prepolymer, is 3 (rc or more, 5 (rc or more) or It may be greater than or equal to loo ^° C. In one example, the curing temperature (Tc) may be higher than the processing silver (Τ _ρ ) This range can be achieved by using a prepolymer, for example to prepare a grinding tool as described below. The upper limit of the process window is not particularly limited, but for example, the difference between the processing temperature (Τ _ρ ) and the degree of hardening silver (T _c ) (T _c -T _p ) may be advantageous. ) May be 400 ^° C or less or 300 ^° c or less. Meanwhile, the kind of phthalonitrile compound that can be applied to the resin binder is not particularly limited, but may be cured with the phthalonitrile compound, for example. 2 or more, or 2 to 20, 2 to 16, or 2 to 12, and 2 black phthalonitrile structure that can form a phthalonitrile resin through reaction with the agent Compounds containing from 8 to 8, or from 2 to 4 can be used.

There are various compounds known to be suitable for the formation of the phthalonitrile resin, and in the present invention, all such known compounds may be used. Examples of compounds in one example include US Pat. No. 4,408,035, US Pat. 5,003,039, U.S. Patent 5,003,078, U.S. Patent 5,004,8, U.S. Patent 5,132,396, U.S. Patent 5,139,054, U.S. Patent 5,208,318, U.S. Patent 5,237,045, U.S. Patent 5,292,854 or U.S. Patent Compounds known in US Pat. No. 5,350,828 and the like can be exemplified, and various compounds known in the art can be included in the examples in addition to those described above. The resin binder may be one in which the composition containing the phthalonitrile compound is cured by at least one curing agent selected from the group consisting of an amine compound, a hydroxy compound, and an imide compound. The amine compound, hydroxy compound and imide compound mean a compound having at least one amino group, hydroxy group or imide group in each molecule.

Preferably, the curing agent may be a compound represented by the following formula (1):

[Formula 1]

In Chemical Formula 1,

M is a tetravalent radical derived from an aliphatic, cycloaliphatic or aromatic compound,

Χΐ and X ² are each independently a divalent radical derived from an alkylene group, an alkylidene group or an aromatic compound,

eta is a number of 1 or more.

The imide-based compound represented by Chemical Formula 1 may include an imide structure in a molecule, so that the resin binder may have excellent heat resistance, but may adversely affect physical properties even when the resin composition for the grinding tool is processed or cured at a high temperature. Do not cause defects such as voids. In Formula 1, M is tetravalent from an aliphatic, alicyclic or aromatic compound. It may be a radical. Wherein, in the aliphatic, alicyclic or aromatic compound,

Radicals formed by leaving four hydrogen atoms may have a structure in which each carbon atom of the carbonyl group of Formula 1 is connected.

Specifically, as the aliphatic compound, straight or branched alkanes, alkenes, or alkynes can be exemplified. As the aliphatic compound, alkanes, alkenes, or alkynes 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 may be used. The alkanes, alkenes, or alkynes may be optionally substituted by one or more substituents.

Examples of the alicyclic compound include hydrocarbon compounds having a non-aromatic ring structure having 3 to 20 carbon atoms, 3 to 16 carbon atoms, 3 to 12 carbon atoms, 3 to 8 carbon atoms, or 3 to 4 carbon atoms. Such an alicyclic hydrocarbon compound may include at least one hetero atom such as oxygen or nitrogen as a ring constituent atom, and may be optionally substituted with one or more substituents if necessary. Examples of the aromatic compound include benzene, a compound containing benzene, or a derivative of any one of the above. The compound containing benzene may mean a compound having a structure in which two or more benzene rings are condensed while sharing one or two carbon atoms, or are directly connected or connected by an appropriate linker. . Examples of linkers applied to linking the two benzene rings include an alkylene group, an alkylidene group, -0-, -S-, -C (= 0)-, -s (= o)-, and -s (= o) _2- , -C (= 0) -0-U-0- C (O)-, -L ² -C (= 0) -0-L ^3- , -L ⁴ -0-C (= 0 ) -L ^5- , or -ΙΛΑ ^ -ΙΛΑ ^ -ΙΛ and the like can be exemplified. L ⁱ to L ⁸ in the above examples are each independently a single bond, -0-, an alkylene group, or an alkylidene group; Ari and Ar ² may each independently be an arylene group. The aromatic compound may include, for example, 6 to 30, 6 to 28, 6 to 27, 6 to 25, 6 to 20 or 6 to 12 carbon atoms. It may be substituted by one or more substituents if necessary. When the compound contains the above-mentioned linker, the number of carbon atoms of the said aromatic compound is also the number containing the carbon atom which exists in the linker. Specifically, for example, in Formula 1, M is a tetravalent radical derived from alkanes, alkenes, or alkynes, or represented by any one of the following Formulas 2 to 7. It may be a tetravalent radical derived from a compound.

[Formula 2]

In Formula 2, Ri to R ⁶ are each independently hydrogen, an alkyl group, an alkoxy group, or an aryl group.

[Formula 3]

In Formula 3, Ri to R ⁸ are each independently hydrogen, an alkyl group, an alkoxy group or an aryl group.

[Formula 4]

In Chemical Formula 4,

R ⁱ to R ⁱ o are each independently hydrogen, an alkyl group, an alkoxy group, or an aryl group, and X is a single bond, an alkylene group, an alkylidene group, -0-, -S-, -c (= o)- , -s (= o)-, -s (= o) ₂ -,-C (= 0) -0-U-0-C (= 0)-, -L ² -C (= 0) -0- L ^3- , -L ⁴ -0-C (= 0) -L ^5- , or -L ^ A ^ -I -A ^ -L ^8- ; Li to L ⁸ are each independently a single bond, -0-, an alkylene group, or an alkylidene group; Ari and Ar ² are each independently an arylene group. In the present specification, ¹ single bond ¹ means a case where an atom is not present in the portion. Therefore, when X in Formula 4 is a single bond, it means a case where no atom is present in the moiety represented by X. In this case, the benzene rings on both sides of X may be directly connected to form a biphenyl structure.

In Chemical Formula 4, -C (= 0) -0-U-0-C (= 0)-, -L ² -C (= 0) -0-L ^3- , or -L ⁴ -0 in X. L ¹ to L ⁵ in —C (= 0) -L ⁵ -may each independently be an alkylene group or an alkylifene group having 1 to 12 carbon atoms, 1 to 8 carbon atoms, or 1 to 4 carbon atoms; The alkylene group or alkylidene group may be substituted or unsubstituted.

In addition, in X in Formula 4,--ΙΛΑ ^ -ΙΛΑ ^ -ΙΛ, wherein L ⁶ and L ⁸ may be -0-; 1 may be an alkylene group or an alkylidene group having 1 to 12 carbon atoms, 1 to 8 carbon atoms, or 1 to 4 carbon atoms; The alkylene group or alkylidene group may be substituted or unsubstituted. Ar ⁱ and Ar ² may be a phenylene group, in which case L ⁶ and L ⁸ may be linked to the ortho, meta or para position of the phenylene, respectively.

5]

In Chemical Formula 5

R ⁱ to R ⁴ are each independently hydrogen, an alkyl group, or an alkoxy group, and two of R ^] to R ⁴ may be linked to each other to form an alkylene group,

A is an alkylene group or alkenylene group, wherein the alkylene group or alkenylene group of A may contain one or more oxygen atoms as a hetero atom.

In Formula 6, R ¹ to R ⁴ are each independently hydrogen, an alkyl group, or It is an alkoxy group, A is an alkylene group.

[Formula 7]

It is an alkoxy group. The tetravalent radical derived from the compound represented by Formulas 2 to 7 is formed by directly leaving R ¹ to R ^{10, which} is a substituent of Formulas 2 to 7, or black is a substituent which may be present in R ¹ to R ⁱ o. The hydrogen atom belonging to the alkyl group, the alkoxy group, the aryl group, the alkylene group, or the alkenylene group may be separated and formed.

For example, when the tetravalent radical is derived from the compound of Formula 3, at least one, at least two, at least three or four of R ⁱ to R 6 of Formula 3 form a radical, or black is R ¹ The radicals may be formed by leaving the hydrogen atoms of the alkyl group, alkoxy group, or aryl group present in R ⁶ to R ⁶ . Forming a radical in the above may mean that the site is connected to the carbon atom of the carbonyl group of Formula 1 as described above.

In addition, when the tetravalent radical is derived from a compound of Formula 4, R ⁱ to R ⁱ o in Formula 4 each independently represent a hydrogen, an alkyl group, an alkoxy group or an aryl group, at least one, at least two, at least three More than 4 or 4 may form a radical linked to the formula (1) Each of which does not form the radical may be a hydrogen, an alkyl group or an alkoxy group, or may be a hydrogen or an alkyl group. In one example, in Formula 4, any two of R7 to R9 and any two of R2 to R4 may form the radical, and the other substituents are each independently hydrogen, an alkyl group, an alkoxy group, or an aryl group, or a hydrogen, alkyl group, or It may be an alkoxy group or hydrogen or an alkyl group. More specifically, for example, the compound represented by Chemical Formula 2 may be banzen or 1,2,4,5-tetraalkylbenzene, and the like, but is not limited thereto.

The compound represented by Formula 4 may be a biphenyl, or a compound represented by any one of Formulas A to F, but is not limited thereto.

Formula F]

Compound represented by the formula (5) is cyclonucleic acid and the like

8 cycloalkanes substituted with one or more alkyl groups It may be a compound represented by a cycloalkene having 4 to 8 carbon atoms such as cyclonucleene, or the formula of any one of the following formulas G to I, but is not limited thereto.

I]

The compound represented by Chemical Formula 6 may be represented by Chemical Formula J, or a compound _ in which at least one of hydrogen of the compound represented by Chemical Formula J is substituted with an alkyl group may be exemplified, but is not limited thereto.

Meanwhile, in Chemical Formula 1, X ¹ and X ² may each independently be a divalent radical derived from an aromatic compound. For example, Χ ^ΐ and X ² may each independently be a divalent radical derived from an aromatic compound having 6 to 40 carbon atoms. Here, the divalent radical derived from an aromatic compound may be a divalent radical derived from the aromatic compound mentioned above.

Specifically, for example, χι and X ² may each independently be a divalent radical derived from a compound represented by any one of Formulas 8 to 10 below.

In Formula 8, R ^U to R ¹⁶ are each independently hydrogen, an alkyl group alkoxy group, an aryl group, a hydroxy group, or a carboxyl group.

In Chemical Formula 9,

R11 to 0 are each independently hydrogen, an alkyl group, an alkoxy group, an aryl group, a hydroxy group, or a carboxyl group,

X ¹ is a single bond, an alkylene group, an alkylidene group, -0-, -S-, -C (= 0)-, -NR ^21- , -S (= 0)-, -S (= 0) _2- , -L ⁹ -Ar ³ -U ⁰ -or L ^U -Ar ^ -A -L ^13- ; R ²¹ is hydrogen, an alkyl group, an alkoxy group, or an aryl group; U to are each independently a single bond, -0-, an alkylene group, or an alkylidene group; Ar ³ to Ar ⁵ are each independently an arylene group.

[Formula 1 is _.

In Formula 10, R ^U to R ^2Q are each independently hydrogen, an alkyl group alkoxy group, an aryl group, a hydroxy group, or a carboxyl group. The divalent radical derived from the compound represented by the formulas (8) to (10) is an alkyl group which is formed by directly leaving R ¹¹ to R ^{20, which} is a substituent of the formulas (8) to (10), or a substituent which may be present in R ¹¹ to R ² o. The hydrogen atom belonging to the alkoxy group, the aryl group, the alkylene group or the alkenylene group may be formed by leaving.

For example, when the divalent radical is derived from the compound represented by the formula (8), for example phenylene, the substitution position of the amine group based on the moiety linked to Ν in X ^I of formula (1) is represented by ortho ( ortho, meta or para position, and the substitution position of the amine group based on the site linked to N in X ² of Formula 1 is also ortho, meta or para (para) location.

In addition, when the divalent radical is derived from the compound represented by Formula ⁹ , any one of R ⁷ to R ⁹ of Formula 9 and R ² to R ⁴ of Formula 9 is connected to the nitrogen atom of Formula 1 To form radicals. Other substituents other than the substituents forming the radicals may each independently be hydrogen, an alkyl group, an alkoxy group or an aryl group, a hydrogen, an alkyl group or an alkoxy group, or may be a hydrogen or an alkyl group. More specifically, for example, the compound represented by Formula 8 may be exemplified by benzene which may be substituted with at least one hydroxy group or carboxyl group, but is not limited thereto.

The compound represented by Formula 9 may be biphenyl which may be substituted with at least one hydroxy group or carboxyl group, a compound which may be substituted with at least one hydroxy group or carboxyl group and represented by any one of Formulas A to F, or Compounds which may be substituted with at least one hydroxy group or carboxyl group and represented by K or M may be exemplified, but are not limited thereto.

[Formula K]

The compound represented by Chemical Formula 10 may be represented by Chemical Formula N, or a compound in which at least one of hydrogen of the compound represented by Chemical Formula N is substituted with a hydroxy group or a carboxyl group may be exemplified, but is not limited thereto.

In the present specification, the alkyl group has 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms, or 1 carbon unless otherwise specified. It may be an alkyl group of 4 to. The alkyl group may be linear, branched, or cyclic and may be substituted by one or more substituents if necessary.

In the present specification, unless otherwise specified, the alkoxy group may be an alkoxy 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. The alkoxy group may be linear, branched, or cyclic and may be substituted by one or more substituents if necessary. In the present specification, an aryl group may mean a monovalent moiety derived from the aforementioned aromatic compound, unless otherwise specified.

In the present specification, an alkylene group or an alkylidene group is an alkylene group or an alkylidene 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, unless otherwise specified. Can mean. The alkylene group or alkylidene group may be linear, branched, or cyclic. In addition, the alkylene group or alkylidene group may be optionally substituted with one or more substituents.

In the present specification, as the substituent which may be optionally substituted with an aliphatic compound, an alicyclic compound, an aromatic compound, an alkyl group, an alkoxy group, an aryl group, an alkylene group, or an alkylidene group, halogen, glyc, such as chlorine or fluorine Epoxy groups, such as a cylyl group, an epoxy alkyl group, a glycidoxy alkyl group, or an alicyclic epoxy group, an acryloyl group, a methacryloyl group, an isocyanate group, a thiol group, an alkyl group, an alkoxy group, an aryl group, etc. can be illustrated, but this is limited to this. It doesn't happen. Meanwhile, in Chemical Formula 1, n means the number of imide repeating units and is one or more. Specifically, n is one or more, or two or more; And 200 or less, or 150 or less, black is 100 or less, black is 80 or less, or 70 or less, or 60 or less, black is 50 or less, black is 40 or less, or 30 or less, or 20 or less, black is 10 or less, or May be 5 or less.

In particular, the curing agent may be more preferably applied in that the compound in the formula (1) wherein n is a number of 2 or more, preferably in the range of 2 to 200 to enable the expression of high thermal stability and heat resistance. Meanwhile, the compound represented by Chemical Formula 1 may be synthesized according to a known method for synthesizing an organic compound, and the specific manner thereof is not particularly limited. For example, the compound represented by the formula (1) can be formed by dehydration condensation reaction of a dianhydride compound and a diamine compound.

In addition, the compound represented by the formula (1) has a high boiling point, does not volatilize or decompose at high temperatures, thereby maintaining a stable curability of the resin composition for the grinding tool, adversely affects the physical properties during high temperature processing or curing process It does not form a viable void.

According to one embodiment, the compound represented by Formula 1, the decomposition temperature may be 300 ^° C or more, 350 ^° C or more, 400 ^° C or more or 500 ^° C or more. In this case, the decomposition silver may mean a temperature at which the decomposition rate of the compound represented by Chemical Formula 1 is maintained in a range of 10% or less, 5% or less, or 1% or less. The upper limit of the decomposition temperature is not particularly limited, but may be, for example, about 1,000 ^° C. or less.

In addition, the compound represented by the formula (1) is melted by the process window (ie, the resin composition for the grinding tool) of the resin composition for the grinding tool by the selection of X ¹ or X ² which is M or a linker of the core. It is possible to easily control the difference between the temperature and the curing temperature, it can act as a curing agent of various physical properties. As described above, the resin binder is a composition containing the phthalonitrile compound is cured by the curing agent, the curing agent may be applied in a ratio of 0.02 mol to 1.5 mol relative to 1 mol of the phthalonitrile compound. In order for the phthalonitrile compound to be sufficiently cured to form a resin binder, the curing agent is preferably applied at 0.02 moles or more relative to 1 mole of the phthalonitrile compound. However, since the process window of the resin composition for the grinding tool including the resin binder may be narrowed when an excessive amount of the curing agent is applied, the curing agent is preferably applied in an amount of 1.5 mol or less with respect to 1 mol of the Sanghaphthalonitrile compound. And, the content of the resin binder is the content of the abrasive particles and the layering agent, It may vary depending on the type of the object to be ground, preferably, may be 10 to 50% by weight of the total weight of the resin composition for the grinding tool 공구 Specifically, the resin binder 10 weight of the total weight of the resin composition for the grinding tool ^0.0 / or more, or 15 wt. ^_0/0 above, black is 20 parts by weight ^_0/0 or more; And 50 parts by weight ^_0/0 or less, or 45 weight ^_0/0 or less, the black can be included more than 40 parts by weight ^_0/0. ,

In order to be able to be so while the grinding tool can exhibit a heat resistance aiming, wherein the abrasive particles and filler is sufficiently bonded to the floor grinding tools, the amount of the resin binder is preferably not less than 10 wt. ^_0/0. However, since the resin-bonded grinding efficiency it can be lowered if I is added in an excessive amount, the binder resin is preferably included by 50 wt. ^_0/0.

II. Grinding tools

According to another embodiment of the invention, there is provided a grinding tool made of the resin composition described above.

The grinding tool is a tool used for polishing and / or cutting articles of various materials such as metal, plastic, ceramic, etc. by friction, and is formed using the resin composition described above.

In particular, as the grinding tool is manufactured by the resin composition for the grinding tool described above, the thermal decomposition black of the grinding tool due to frictional heat in the grinding process may minimize thermal damage, thereby exhibiting improved durability and lifespan.

The grinding tool may be manufactured by a method well known in the art using the above-described resin composition for grinding tools.

For example, the grinding tool may be manufactured by a compression molding process in which the resin composition is placed in an arbitrary mold, compressed at a constant pressure, and then heated. In addition, the grinding tool can be made by injection molding (injection molding process), the ^transfer, a forming process (transfer molding process). 【Effects of the Invention】

The resin composition for grinding tools according to the present invention has a high heat resistance and excellent workability, thereby enabling the provision of a grinding tool showing improved heat resistance and durability.

[Brief Description of Drawings]

1 is ⁱ H-NMR spectrum of Compound (PN1) according to Preparation Example 1 of the present invention.

2 is ⁱ H-NMR spectrum of Compound (PN2) according to Preparation Example 2 of the present invention.

3 is a 1 H-NMR spectrum of the compound (CA1) according to the present invention.

4 is an H-NMR spectrum of the compound (CA2) according to the present invention.

5 is an H-NMR spectrum of the compound (CA3) according to the present invention.

[Specific contents to carry out invention]

Hereinafter, preferred embodiments will be presented to aid in understanding the invention. However, the following examples are only intended to illustrate the invention, not limited to the invention only. Preparation Example 1 Synthesis of Phtharonitrile Compound (PN1)

Compound (PN1) of formula 11 was synthesized in the following manner.

32.7 g and 120 g of DMF (dimethyl formamide)

Into a 3-neck RBF (3 neck round bottom flask) was dissolved by stirring at room temperature. Subsequently, 51.9 g of the compound represented by the following Chemical Formula 13 was added, and 50 g of DMF was added, followed by stirring to dissolve. Subsequently, 62.2 g of potassium carbonate and 50 g of DMF were added together, and the temperature was raised to 85 ^° C. while stirring. After reacting for about 5 hours in this state, it was cooled to room temperature. The reacted reaction solution was dissolved in 0.2 N hydrochloric acid. Pour into aqueous solution to neutralize precipitate and wash with water after filtration. Thereafter, the filtered reaction product was dried in a vacuum oven at 100 ^° C. for 1 day, and after removing water and residual solvent, the compound of formula 11 (PN1) was obtained in a yield of about 80% by weight. The result of H-NMR analysis of the obtained compound of Formula 11 (PN1) is shown in FIG. 1.

[Formula 11]

[Formula 12]

[Formula 13]

Preparation Example 2 Synthesis of Phtharonitrile Compound (PN2)

Compound (PN2) of Formula 14 was synthesized in the following manner.

28.0 g of 4,4'-bis (hydroxyphenyl) methane and 150 mL of dimethyl formamide (DMF) were added to a 500 mL 3-neck RBF (3 neck round bottom flask) and dissolved at room temperature. Then 48.5 g of 4-nitrophthalonitrile was added to the mixture, and 50 g of DMF was added, followed by stirring to dissolve. Subsequently, 58.1 g of potassium carbonate and 50 g of DMF were added together, and the temperature was raised to 85 ^° C while stirring. After reacting for about 5 hours, the mixture was cooled to room temperature. The corner reaction solution was poured into a 0.2 N aqueous hydrochloric acid solution to neutralize precipitate, and washed with water after filtering. Thereafter, the filtered reaction product was dried in a vacuum oven at 100 ^° C. for 1 day, and after removing water and residual solvent, the target compound (PN2) was obtained in a yield of about 83% by weight. ^I H-NMR analysis of the obtained compound of Formula 14 (PN2) is shown in FIG. 2. 14]

Preparation Example 3 Synthesis of Curing Agent (CAl)

Compound (CA1) of Formula 17 was synthesized by dehydration of diamine and dianhydride. 24 g of 4,4'-oxydianiline ^ -oxydianiline and 40 g of NMP (N-methyl-pyrrolidone) were added to a 3-neck RBF (3 neck round bottom flask), and stirred at room temperature to dissolve. The water was cooled in a water bath, and 8.7 g of the compound of Formula 18 was slowly added in three portions and 40 g of NMP was added thereto. When all of the added compound was dissolved, 16 g of toluene was added to the reaction solution for azeotrope. The Dean-Stark unit and the ripple force condenser were installed, and toluene was added to the Dean-Stark unit. 42 mL of pyridine was added as a dehydration condensation catalyst, and the temperature was raised to 170 ^° C. and stirred for 3 hours. The water generated as the imide ring was formed was further stirred for 2 hours while being removed by the Dean-Stark apparatus: and the residual toluene and pyridine were removed. The reaction product was cooled to room temperature and precipitated and recovered in methanol. The recovered precipitate was extracted with methanol to remove residual banung water and dried in a vacuum oven to give the compound (CA1) of the formula 17 in a yield of about 85 wt. ^_0/0. The X-NMR analysis result of the obtained compound of formula 17 (CA1) is shown in FIG. 3.

[Formula 17]

Preparation Example 4 Synthesis of Curing Agent (CA2)

The compound of formula 19 (CA2) was synthesized by dehydration condensation of diamine and dianhydride. 24 g of 4,4'-oxydianiline (4,4'-oxydianiline) and 50 g of NMP (N-methyl pyrrolidone) were added to a 3-neck RBF (3 neck round bottom flask), and stirred at room temperature to dissolve. I was. The above was cooled by a water bath, and 19.5 g of the compound of Formula 18 was slowly added in three portions and added with 100 g of NMP. When all the added compound was dissolved, 30 g of toluene was added to the reaction solution for azeotrope reaction. The Dean-Stark unit and the reflux condenser were installed and filled with toluene in the Dean-Stark unit. 6.3 mL of pyridine was added as a dehydration condensation catalyst, and the temperature was raised to 170 ^° C. and stirred for 3 hours. Water generated while forming the imide ring was further stirred for 2 hours while the Dean-Stark apparatus was removed, and residual toluene and pyridine were removed. The reaction product was cooled to room temperature and recovered by precipitation in methanol. The recovered precipitate was extracted with methanol to remove residual coagulum and dried in a vacuum oven to yield compound (CA2) of formula 19 in a yield of about 85% by weight. 1H-NMR analysis of the obtained compound of formula 19 (CA2) is shown in FIG. 4.

[Formula 19]

In Formula 19, η is about 3.

[Formula 18]

Preparation Example 5 Synthesis of Curing Agent (CA3)

The compound of formula 20 (CA3) was synthesized by dehydration of diamine and dianhydride. 8.1 g of m-phenylene diamine and 50 g of N-methyl pyrrolidone (NMP) were added to a 3-neck RBF (3 neck round bottom flask), and stirred at room temperature to dissolve. The above was observed with a water bath, and 26 g of the compound represented by Chemical Formula 21 was gradually divided into three portions and added with 60 g of NMP. When all of the added compound was dissolved, 23 g of toluene was added to the reaction solution for azeotrope reaction. The Dean Stark unit and the reflux condenser were installed and filled with toluene in the Dean Stark unit. 5.2 mL of pyridine was added as a dehydration condensation catalyst, and the temperature was raised to 17 CTC and stirred for 3 hours. The product generated while forming the imide ring was further stirred for 2 hours while the Dean Stark apparatus was removed, and the residual toluene and pyridine were removed. The reaction product was cooled to room temperature and recovered by precipitation in methanol. The recovered precipitate was extracted with Soxhlet with methanol to remove residual semicouns and dried in a vacuum oven to yield compound (CA3) of formula 21 in a yield of about 93% by weight. H-NMR analysis of the compound of Formula 21 (CA3) is shown in FIG. 5.

In Formula 20, ^η is about 3.

[Formula 21]

Example 1

A resin binder in which the curing agent (CA1) of Preparation Example 4 was mixed at a ratio of 0.2 mol to 1 mol of the phthalonitrile compound (PN1) of Preparation Example 1 was prepared.

Diamond abrasive grain particles having an average particle size of 25 to 100 parts by weight ^_0/0, 50 parts by weight of copper ⁰ / a filler., And common summing the resin binder 25% by weight to prepare a resin composition for polishing tools.

In the resin composition into a mold and cured for 20 minutes at 10 minutes at 250 ^° C with a force of 30 MPa in the hot press, 300 ^° C to obtain a molded article.

The molding was fired in an oven at 350 ^° C. for 6 hours to prepare a grinding layer specimen for a grinding tool. Example 2

A resin binder was prepared in which the curing agent (CA2) of Preparation Example 5 was mixed at a ratio of 0.2 mol to 1 mol of the phthalonitrile compound (PN1) of Preparation Example 1.

The combined copper and 50% weight average particle size of the diamond particles 25 to 100 parts by weight ^_0/0, the filler in the abrasive grain, and 25% by weight of the binder resin to prepare a resin composition for a common grinding tool.

A grinding tool for the grinding layer with the specimen of Example 1, the same ^"method by using the above resin composition was prepared. Example 3

A resin binder was prepared in which the curing agent (CA3) of Preparation Example 6 was mixed at a ratio of 0.2 mol to 1 mol of the phthalonitrile compound (PN1) of Preparation Example 1.

Having an average particle size of 100 to 25 parts by weight abrasive particles of diamond particles ^_0/0, 50 parts by weight of copper ^_0/0 to layer premise, and common summing the resin binder 25% by weight of a resin for the grinding tool The composition was prepared.

Using the resin composition, a grinding layer specimen for a grinding tool was manufactured in the same manner as in Example 1. Example 4

A resin binder was prepared in which the curing agent (CA1) of Preparation Example 4 was mixed at a ratio of 0.2 mol to 1 mol of the phthalonitrile compound (PN2) of Preparation Example 2.

The average particle size of 100 / diamond particles as abrasive particles 25 parts by weight ^_0/0, 50 parts by weight of copper ^_0/0 to layer premise, and common summing the resin binder 25% by weight to prepare a resin composition for polishing tools. ^'

Using the resin composition, a grinding layer specimen for a grinding tool was manufactured in the same manner as in Example 1. Example 5

A resin binder was prepared in which the curing agent (CA2) of Preparation Example 5 was mixed at a ratio of 0.2 mol to 1 mol of the phthalonitrile compound (PN2) of Preparation Example 2.

Having an average particle size of 100 to 25 parts by weight abrasive particles of diamond particles ^_0/0, 50 parts by weight of copper ^_0/0 to layer premise, and common summing the resin binder 25% by weight to prepare a resin composition for polishing tools.

Using the resin composition, a grinding layer specimen for a grinding tool was manufactured in the same manner as in Example 1. Example 6

A resin binder was prepared in which the curing agent (CA3) of Preparation Example 6 was mixed at a ratio of 0.2 mol to 1 mol of the phthalonitium compound (PN2) of Preparation Example 2.

Abrasive particles 100 of the diamond particles 25 parts by weight ⁰ / average particle diameter., 50 parts by weight of copper ^_0/0 to layer premise, and common summing the resin binder 25% by weight to prepare a resin composition for polishing tools.

Using the resin composition, a grinding layer specimen for a grinding tool was manufactured in the same manner as in Example 1. Comparative Example 1

The average particle diameter of the diamond particles as abrasive particles 100皿25 weight ^_0/0, by adding the copper traces 50 weight ^_0/0, and a phenol resin 25 wt% of a filler, to prepare a resin composition for polishing tools.

The resin composition was put into a mold and cured at 150 ^° C. for 30 minutes with a force of 30 MPa in a hot press to obtain a molding.

The molded product was fired in an oven at 210 ^° C. for 6 hours to prepare a grinding layer specimen for a grinding tool. Comparative Example 2

The combined 25% by weight, average particle diameter of the diamond particles 100 with abrasive particles, 50 parts by weight of copper ^_0/0, and a polyimide resin of 25% by weight filler in common to prepare a resin composition for polishing tools.

The resin composition is put into a thermoforming mold and the molding temperature is 250 ^° C to

Pressing and depressurizing were repeated under the conditions of molding pressure of 30 MPa while gradually decreasing the temperature to 350 ^° C., and heating and pressure molding were performed for 3 hours to obtain a molded product. The molded material was heat-treated at 350 ^° C. for 3 hours to prepare a grinding layer specimen for a grinding tool. Test Example 1 NMR Analysis

PN1 to PN2 and CA1 to CA3 compounds obtained in Preparation Examples 1 to 5 were subjected to H-NMR analysis according to the manufacturer's manual using Agilent's 500 MHz NMR equipment. Samples for NMR measurements were prepared by dissolving the compound of interest in dimethyl sulfoxide (dSO) -d6. H-NMR analysis results for each compound are shown in FIGS. 1 to 5. Test Example 2 Evaluation of Thermal Stability

The thermogravimetric analysis (TGA) evaluated the thermal stability (degree of pyrolysis) of the grinding layer specimens for the grinding tool, and the results are shown in Table 1 below. Specifically, TGA was performed using the TGA e850 instrument of Mettler-Toledo, and the analysis was performed in an atmosphere of N ₂ flow while raising the temperature at a rate of 10 TV minutes from about 25 ^° C to 800 ^° C for the test specimens. It was. Test Example 3. Evaluation of Heat Resistance

Heat resistance of the resin binder for the grinding tool was evaluated by heat deflection temperature (HDT) measurement, and the results are shown in Table 1 below.

Specifically, the heat resistance was measured according to the test method of ASTM D648-16 (Method B) standard. Test Example 4 Evaluation of Machining Process

In the above examples and comparative examples, it was evaluated whether or not the complexity of the processing process in the production of the grinding layer specimen for the grinding tool using each resin composition.

Table 1

According to Test Examples 1 to 4, the resin composition according to Examples 1 to 6 was prepared by a method similar to the process of Comparative Example 1 to which phenol resin was applied, and was higher than that of Comparative Example 2 to which polyimide resin was applied. Productivity was shown. In addition, the grinding layer specimens for the grinding tools according to Examples 1 to 6 had relatively high thermal stability as a result of TGA measurement and higher heat resistance as a result of HDT measurement than the specimen of Comparative Example 1.

Claims

[Claim]

[Claim 1]

Abrasive particles,

Fillers and

A resin composition for a grinding tool comprising a resin binder cured from a composition containing a phthalonitrile compound.

[Claim 2]

The method of claim 1,

The resin binder is a resin composition for a grinding tool, wherein the composition containing the phthalonitrile compound is cured by at least one curing agent selected from the group consisting of an amine compound, a hydroxy compound and an imide compound.

[Claim 3]

The method of claim 2,

The hardener is a compound represented by the following formula (1), the composition for grinding tools:

[Formula 1]

In Chemical Formula 1,

M is a tetravalent radical derived from an aliphatic, alicyclic or aromatic compound, χι and X ² are each independently a divalent radical derived from an alkylene group, an alkylidene group or an aromatic compound,

eta is a number of 1 or more.

[Claim 4]

The method of claim 3, wherein

The curing agent is a resin composition for a grinding tool, wherein n is a compound in the range of 2 to 200 in the formula (1).

[Claim 5]

The method of claim 1,

The abrasive particles are at least one particle selected from the group consisting of natural diamond, synthetic diamond, boron nitride, cubic boron nitride (CBN), alumina, silica, silicon carbide, alumina-zirconia, titanium diboride, and boron carbide, Resin composition for grinding tools.

[Claim 6]

The method of claim 1 wherein.

The layering agent is copper, tungsten, iron oxide, copper-tin alloy, silicon carbide, alumina, calcite, marl, marble, limestone, creolite, silica, silicate, metal carbonate, metal sulfate, metal sulfite, metal oxide, sodium chloride Magnesium Chloride, Iron Disulfide, Molybdenum Disulfide, Antimony Trisulfide, Absolutely, Glass Fiber, Molybdenum Disulfide, Antimony Trisulfide, Tungsten Sulphide, Silane Coupling Agent, Titanate Coupling Agent, Zirconate Coupling Agent, Zircoalumi A resin composition for a grinding tool, which is at least one layering agent selected from the group consisting of a nate coupling agent, and carbon fiber.

[Claim 7] ■

The method of claim 1,

20 to 60% by weight of the abrasive particles,

The filler of 10 to 60 parts by weight ^_0/0, and

10 to 50% by weight of the resin binder

Resin comprising a resin for a grinding tool. [Claim 8]

A grinding tool made of the resin composition of claim 1.