WO2018217038A1 - Composition de résine pour outil de meulage et outil de meulage fabriqué à partir de la composition de résine - Google Patents

Composition de résine pour outil de meulage et outil de meulage fabriqué à partir de la composition de résine Download PDF

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Publication number
WO2018217038A1
WO2018217038A1 PCT/KR2018/005914 KR2018005914W WO2018217038A1 WO 2018217038 A1 WO2018217038 A1 WO 2018217038A1 KR 2018005914 W KR2018005914 W KR 2018005914W WO 2018217038 A1 WO2018217038 A1 WO 2018217038A1
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WIPO (PCT)
Prior art keywords
compound
grinding tool
resin composition
group
formula
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PCT/KR2018/005914
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English (en)
Korean (ko)
Inventor
김상우
이승희
안기호
김율리아나
김영대
Original Assignee
주식회사 엘지화학
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Priority claimed from KR1020180058367A external-priority patent/KR102067688B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to US16/473,211 priority Critical patent/US20190351529A1/en
Priority to CN201880008266.7A priority patent/CN110234469B/zh
Priority to EP18806393.7A priority patent/EP3527327B1/fr
Priority to JP2019535382A priority patent/JP6821236B2/ja
Publication of WO2018217038A1 publication Critical patent/WO2018217038A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule

Definitions

  • Resin composition for grinding tool and grinding tool made of said resin composition
  • the present invention relates to a resin composition for grinding tools and a grinding tool made of the resin composition.
  • Grinding tools are tools used to frictionally polish and / or cut articles of various materials such as metals, plastics and ceramics.
  • grinding tools are formed using a composition comprising abrasive particles, fillers and resin binders.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • the present invention is to provide a grinding tool made of the resin composition with improved heat resistance and durability.
  • the grinding tool manufactured from the said resin composition is provided.
  • 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.
  • 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.
  • a resin composition for a grinding tool is provided.
  • 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.
  • 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.
  • 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.
  • the abrasive particles those well known in the art may be applied without particular limitation.
  • the abrasive particles may be metal particles, inorganic particles, metal coated inorganic particles, and the like.
  • 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.
  • 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 ⁇ 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.
  • 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.
  • the content of the abrasive grains is preferably not less than 20 wt. 0/0.
  • the abrasive particles to be added in excess so that the abrasive particles be the durability is easily detached from the grinding tool deteriorated
  • 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.
  • the layer filler may be a metal layer filler, an inorganic layer filler, an organic filler, a composite filler, or the like.
  • 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.
  • 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.
  • 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.
  • the amount of the layer premise is preferably not less than 10 wt. 0/0.
  • the filler comprises less than 60 wt. 0/0.
  • 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.
  • 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.
  • 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.
  • the prepolymer may also exhibit excellent curability, low melting temperature and wide process window, like the resin composition for the grinding tool.
  • the processing temperature of the prepolymer may be in the range of 150 ° C to 350 ° C.
  • the processing temperature means a temperature at which the prepolymer exists in a processable state.
  • a processing temperature may be, for example, a melting temperature (T m ) or a glass transition temperature (T g ).
  • T m melting temperature
  • T g glass transition temperature
  • 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.
  • the curing temperature (Tc) may be higher than the processing silver ( ⁇ ⁇ )
  • 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 ( ⁇ ⁇ ) 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.
  • 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.
  • 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.
  • the curing agent may be a compound represented by the following formula (1):
  • M is a tetravalent radical derived from an aliphatic, cycloaliphatic or aromatic compound
  • ⁇ 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.
  • 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.
  • alkanes, alkenes, or alkynes straight or branched alkanes, alkenes, or alkynes can be exemplified.
  • 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.
  • 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.
  • the number of carbon atoms of the said aromatic compound is also the number containing the carbon atom which exists in the linker.
  • 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.
  • Ri to R 6 are each independently hydrogen, an alkyl group, an alkoxy group, or an aryl group.
  • Ri to R 8 are each independently hydrogen, an alkyl group, an alkoxy group or an aryl group.
  • R i to R i o are each independently hydrogen, an alkyl group, an alkoxy group, or an aryl group
  • Ari and Ar 2 are each independently an arylene group.
  • 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.
  • the alkylene group or alkylidene group may be substituted or unsubstituted.
  • 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.
  • 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.
  • R 1 to R 4 are each independently hydrogen, an alkyl group, or It is an alkoxy group, A is an alkylene 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • X 1 and X 2 may each independently be a divalent radical derived from an aromatic compound.
  • ⁇ ⁇ and X 2 may each independently be a divalent radical derived from an aromatic compound having 6 to 40 carbon atoms.
  • the divalent radical derived from an aromatic compound may be a divalent radical derived from the aromatic compound mentioned above.
  • ⁇ and X 2 may each independently be a divalent radical derived from a compound represented by any one of Formulas 8 to 10 below.
  • R U to R 16 are each independently hydrogen, an alkyl group alkoxy group, an aryl group, a hydroxy group, or a carboxyl group.
  • R11 to 0 are each independently hydrogen, an alkyl group, an alkoxy group, an aryl group, a hydroxy group, or a carboxyl group,
  • 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.
  • 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.
  • the substitution position of the amine group based on the moiety linked to ⁇ 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • an aryl group may mean a monovalent moiety derived from the aforementioned aromatic compound, unless otherwise specified.
  • 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.
  • the alkylene group or alkylidene group may be optionally substituted with one or more substituents.
  • 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.
  • 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.
  • 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.
  • 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.
  • the compound represented by the formula (1) can be formed by dehydration condensation reaction of a dianhydride compound and a diamine compound.
  • 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.
  • the decomposition temperature may be 300 ° C or more, 350 ° C or more, 400 ° C or more or 500 ° C or more.
  • 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.
  • 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.
  • 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.
  • the curing agent is preferably applied at 0.02 moles or more relative to 1 mole of the phthalonitrile compound.
  • the curing agent is preferably applied in an amount of 1.5 mol or less with respect to 1 mol of the Sanghaphthalonitrile compound.
  • 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 ⁇ 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. ,
  • the amount of the resin binder is preferably not less than 10 wt. 0/0.
  • the binder resin is preferably included by 50 wt. 0/0.
  • 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.
  • 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.
  • 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.
  • the grinding tool can be made by injection molding (injection molding process), the transfer, a forming process (transfer molding process).
  • 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.
  • 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.
  • the compound of formula 19 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.
  • ⁇ is about 3.
  • the compound of formula 20 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.
  • NMP N-methyl pyrrolidone
  • ⁇ is about 3.
  • 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.
  • Example 2 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 The molding was fired in an oven at 350 ° C. for 6 hours to prepare a grinding layer specimen for a grinding tool.
  • 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 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.
  • Example 4 Using the resin composition, a grinding layer specimen for a grinding tool was manufactured in the same manner as in Example 1.
  • Example 4 Using the resin composition, a grinding layer specimen for a grinding tool was manufactured in the same manner as in Example 1.
  • Example 4 Using the resin composition, a grinding layer specimen for a grinding tool was manufactured in the same manner as in Example 1.
  • Example 4 Using the resin composition, a grinding layer specimen for a grinding tool was manufactured in the same manner as in Example 1.
  • 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.
  • Example 5 Using the resin composition, a grinding layer specimen for a grinding tool was manufactured in the same manner as in Example 1.
  • Example 5 Using the resin composition, a grinding layer specimen for a grinding tool was manufactured in the same manner as in Example 1.
  • Example 5 Using the resin composition, a grinding layer specimen for a grinding tool was manufactured in the same manner as in Example 1.
  • Example 5 Using the resin composition, a grinding layer specimen for a grinding tool was manufactured in the same manner as in Example 1.
  • 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.
  • 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.
  • the average particle diameter of the diamond particles as abrasive particles 100 ⁇ 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 resin composition is put into a thermoforming mold and the molding temperature is 250 ° C to
  • 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
  • thermogravimetric analysis 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.
  • 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.
  • 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.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

La présente invention concerne une composition de résine pour un outil de meulage et un outil de meulage fabriqué à partir de la composition de résine. La composition de résine pour l'outil de meulage, selon la présente invention, présente une résistance à la chaleur élevée et une excellente aptitude au traitement, permettant ainsi la fourniture de l'outil de meulage ayant une résistance à la chaleur et une durabilité améliorées.
PCT/KR2018/005914 2017-05-24 2018-05-24 Composition de résine pour outil de meulage et outil de meulage fabriqué à partir de la composition de résine WO2018217038A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US16/473,211 US20190351529A1 (en) 2017-05-24 2018-05-24 Resin composition for abrasive tool and abrasive tool made of the resin composition
CN201880008266.7A CN110234469B (zh) 2017-05-24 2018-05-24 用于研磨工具的树脂组合物和由所述树脂组合物制成的研磨工具
EP18806393.7A EP3527327B1 (fr) 2017-05-24 2018-05-24 Composition de résine pour outil abrasif et outil abrasif fabriqué à partir de la composition de résine
JP2019535382A JP6821236B2 (ja) 2017-05-24 2018-05-24 研削工具用樹脂組成物および前記樹脂組成物で製造された研削工具

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR20170064326 2017-05-24
KR10-2017-0064326 2017-05-24
KR1020180058367A KR102067688B1 (ko) 2017-05-24 2018-05-23 연삭 공구용 수지 조성물 및 상기 수지 조성물로 제조된 연삭 공구
KR10-2018-0058367 2018-05-23

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WO2018217038A1 true WO2018217038A1 (fr) 2018-11-29

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US5004801A (en) 1988-11-21 1991-04-02 The United States Of America As Represented By The Secretary Of The Navy Polymer of dithioether-linked phthalonitrile
US5132396A (en) 1990-04-30 1992-07-21 The United States Of America As Represented By The Secretary Of The Navy Phthalonitrile monomers containing imide and/or phenoxy linkages, and polymers thereof
US5139054A (en) 1991-06-28 1992-08-18 Leggett & Platt, Incorporated Spring interior forming and assembling apparatus
US5208318A (en) 1991-03-15 1993-05-04 Keller Teddy M Phosphazene-containing amine as curing agent for phthalonitrile-base polymer
US5237045A (en) 1992-01-09 1993-08-17 The United States Of America As Represented By The Secretary Of The Navy Curing phthalonitrile resins with acid and amine
US5292854A (en) 1989-05-16 1994-03-08 The United States Of America As Represented By The Secretary Of The Navy Synthesis of phthalonitrile resins containing ether and imide linkages with aromatic diamine curing agent
US20090130849A1 (en) * 2007-10-29 2009-05-21 Wai Mun Lee Chemical mechanical polishing and wafer cleaning composition comprising amidoxime compounds and associated method for use
CN101733713A (zh) * 2008-11-26 2010-06-16 绵阳中研磨具有限责任公司 用酞菁树脂生产砂轮的方法
KR20160059444A (ko) * 2014-11-18 2016-05-26 주식회사 엘지화학 프탈로니트릴 수지
KR20160115543A (ko) * 2015-03-27 2016-10-06 주식회사 엘지화학 중합성 조성물

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4244857A (en) * 1979-08-30 1981-01-13 The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration Curing agent for polyepoxides and epoxy resins and composites cured therewith
US4408035A (en) 1981-08-24 1983-10-04 The United States Of America As Represented By The Secretary Of The Navy Phthalonitrile resin from diphthalonitrile monomer and amine
US5003039A (en) 1988-11-18 1991-03-26 The United States Of America As Represented By The Secretary Of The Navy Amino phenyl containing curing agent for high performance phthalonitrile resin
US5350828A (en) 1988-11-21 1994-09-27 The United States Of America As Represented By The Secretary Of The Navy Synthesis and polymerization of dithioether-linked phthalonitrile monomers
US5004801A (en) 1988-11-21 1991-04-02 The United States Of America As Represented By The Secretary Of The Navy Polymer of dithioether-linked phthalonitrile
US5292854A (en) 1989-05-16 1994-03-08 The United States Of America As Represented By The Secretary Of The Navy Synthesis of phthalonitrile resins containing ether and imide linkages with aromatic diamine curing agent
US5003078A (en) 1989-05-16 1991-03-26 The United States Of America As Represented By The Secretary Of The Navy Synthesis of phthalonitrile resins containing ether and imide linkages
US5132396A (en) 1990-04-30 1992-07-21 The United States Of America As Represented By The Secretary Of The Navy Phthalonitrile monomers containing imide and/or phenoxy linkages, and polymers thereof
US5208318A (en) 1991-03-15 1993-05-04 Keller Teddy M Phosphazene-containing amine as curing agent for phthalonitrile-base polymer
US5139054A (en) 1991-06-28 1992-08-18 Leggett & Platt, Incorporated Spring interior forming and assembling apparatus
US5237045A (en) 1992-01-09 1993-08-17 The United States Of America As Represented By The Secretary Of The Navy Curing phthalonitrile resins with acid and amine
US20090130849A1 (en) * 2007-10-29 2009-05-21 Wai Mun Lee Chemical mechanical polishing and wafer cleaning composition comprising amidoxime compounds and associated method for use
CN101733713A (zh) * 2008-11-26 2010-06-16 绵阳中研磨具有限责任公司 用酞菁树脂生产砂轮的方法
KR20160059444A (ko) * 2014-11-18 2016-05-26 주식회사 엘지화학 프탈로니트릴 수지
KR20160115543A (ko) * 2015-03-27 2016-10-06 주식회사 엘지화학 중합성 조성물

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