JPS6179573A - Abrasive resinoid composition - Google Patents

Abstract

PURPOSE:To reduce rank odors in time of grinding as well as to improve grindability and wheel characteristics ever so better, by using a specific composition. CONSTITUTION:An abrasive resinoid composition contains a dicyclopentadienyl denaturation unsaturated ester compound obtainable by reacting dicy clopentadienyl alpha,beta-unsaturated dibasic acid monoester and polyhydric alcohol and/or diglycidienyl ester compound as well as natural and/or artificial abrasives. In addition, this resinoid composition contains a polymatic monomer, water, an isocyanurate derivative and/or a thermoplastic polymer.

Description

Detailed Description of the Invention (Field of Industrial Application) ``The present invention relates to a polishing resin composition, and more specifically, to a polishing resin composition that does not corrode the polishing machine or the workpiece, and has excellent grinding properties and grinding wheel properties. The present invention relates to a polishing resin composition for a grindstone.

(Prior Art) In a grinding wheel, it is said that the influence of the binder on the performance of the grinding wheel is extremely large.

As a binder, feldspar and other inorganic clays (
Inorganic substances such as vitrified keroseki), a type of cement called magnesha oxychloride (magnesia grindstone), and synthetic resins (resinoid grindstones) such as phenolic resin called Bakelite, epoxy resin, and polyvinyl alcohol CPVA) are known. .

Compared to resinoid grinding wheels, magnesha grinding wheels have the advantage of being less affected by heat generation during grinding (and have excellent grinding properties), but the chloride in the binder makes it difficult for the grinding machine and the workpiece (especially metal) It has the disadvantage of being easily corroded.

On the other hand, among resinoid whetstones, those that use unsaturated polyester resin as a binder have superior grinding performance and productivity (work efficiency and working time) compared to those that use phenolic resin as a binder. It is attracting attention as a useful whetstone because it does not corrode the grinder or the workpiece due to chloride.

(Problems to be Solved by the Invention) However, grinding wheels using unsaturated polyester resin as a binder have the drawbacks of generating a significant odor during grinding and deteriorating the characteristics of the grinding wheel, which are major obstacles to industrial use. It becomes.

In order to improve these drawbacks, for example, we focused on the excellent grinding properties of inorganic oxychloride grinding wheels and the small effect of grinding heat, and used a hydrous polyester resin, which is an unsaturated polyester resin containing water, as a binder. (Japanese Patent Laid-Open No. 56-33234).

However, this method has the disadvantage that dimensional changes are likely to occur, and hardness and mechanical strength are significantly reduced when sieving is performed to adjust particle size and pores.

The purpose of the present invention is to eliminate the drawbacks of the above-mentioned prior art,
It is an object of the present invention to provide a polishing resin composition that does not corrode a polishing machine or a workpiece, has extremely little odor during grinding, and has excellent grindability and grindstone properties.

(Means for solving the problem) In order to achieve the above object, the present inventors focused on the excellent grindability of unsaturated polyester resin and the excellent adhesiveness of dicyclopentadiene-modified unsaturated ester compound. However, as a result of intensive research, we have arrived at the present invention.

The present invention provides (A) dicyclopentagenyl α.

A dicyclopentadiene-modified unsaturated ester compound obtained by reacting a β-unsaturated dibasic acid monoester with a polyhydric alcohol and/or a diglycidyl ether compound, and (B) a natural and/or artificial abrasive material The present invention relates to a polishing resin composition comprising:

Furthermore, in addition to the components (A) and (B), the resin composition of the present invention further includes (C) a polymerizable monomer, (D) water, and (E)
It is preferable that the DIIJ chain contains an isocyanurate derivative and/or (F) a thermoplastic polymer having an unsaturated bond.

Dicyclopentagenyl α used in the present invention.

The β-unsaturated dibasic acid monoester is produced by a known method, for example, by reacting dicyclopentadiene with an α,β-unsaturated dibasic acid or its anhydride.

If an anhydride is used, additional water must be added. Hydroxylhydricyclopentadiene and an α,β-unsaturated dibasic acid or anhydride thereof may be reacted.

Dicyclopentadiene is a compound represented by the following formula obtained by trimerizing cyclopentadiene by Diels-Alder reaction.

The purity of dicyclopentadiene is preferably in the range of 75 to 100%, more preferably in the range of 85 to 100%. If the purity is less than 75%, there is a tendency for synthesis mesothelium burrs to occur and the resin to be colored.

Examples of the α,β-unsaturated dibasic acid or its anhydride include maleic acid, maleic anhydride, fumaric acid, itaconic acid, and citraconic acid.

It is preferable that the α,β-unsaturated dibasic acid or its anhydride and dicyclopentadiene are reacted in equimolar amounts.

Note that some dicyclopentadiene dimerate or sifumarate may be generated when obtaining this compound, but
This does not affect the effects of the present invention in any way.

Examples of polyhydric alcohols include propylene glycol, ethylene glycol, diethylene glycol, triethylene glycol, dipropylene glycol, butylene glycol, dihydric alcohols such as hydrogenated bisphenol A1, trimethylolpropane monoallyl ether, glycerin, diglycerin, and pentyl alcohol. erythrit,
Alcohols of three or more alcoholic beverages such as trimethylolpropane are used, and monohydric alcohols such as benzyl alcohol and trimethylolpropane diallyl ether may be used in combination.

In the present invention, in order to produce a dicyclopentadiene-modified unsaturated ester compound, dicyclopentadienyl α
, a β-unsaturated monoester and a polyhydric alcohol may be subjected to a condensation reaction by a conventional method.

At this time, a saturated acid may be used if necessary. Examples of saturated acids include phthalic acid, isophthalic acid, terephthalic acid,
Succinic acid, adipic acid, sepatic acid, tetrahydrophthalic acid, 5-methyl-4-cyclohexene-1,2-dicarboxylic acid, 3,6-nindomethylene-tetrahydrophthalic acid, etc., anhydrides or halogen-substituted products of these acids Polybasic acids such as trimellitic acid and pyromellitic acid, benzoic acid, etc. can also be used.

Further, the dicyclopentadiene-modified unsaturated ester compound used in the present invention includes the dicyclopentadienyl α,
It can also be obtained by reacting a β-unsaturated dibasic acid monoester with a diglycidyl ether compound.

Examples of diglycidyl ether compounds include bisphenol epoxy resins obtained by reacting bisphenol with epichlorohydrin in the presence of an alkali. An example of this is expressed by the following general formula.

(In the formula, X is an integer of 0 to 15) Commercially available products include, for example, Epikot 828, Epicoat 1001, and Epicoat 10 manufactured by Shell Chemical Co., Ltd.
04, Asahi Kasei Kogyo Co., Ltd. AER-664HSAER-33
1, AER-337, Dow Chemical Company F! D, E, R3
There are 30, D, E, R660, D, E, R664, etc.

Further, a compound in which some of the hydrogen atoms are replaced with halogen (for example, bromine) may be used. Commercially available examples include Tobu Kasei Co., Ltd. Evototo YDB-340, YDB-
400 etc. These may be used alone or in a mixture of two or more.

Further, as the diglycidyl ether compound, a novolak epoxy resin can also be used, and for example, the general formula ) is used.

Commercially available products include those manufactured by Dow Chemical Company,
E, N, 43 i, D, E, N, 438,
Epicor 152, Epicor 154 manufactured by Shell Chemical Co., Ltd.
, EPN113B manufactured by Ciba Corporation, etc. These may be used alone or in a mixture of two or more. In addition to bisphenol epoxy resins and novolac epoxy resins, alicyclic epoxy resins and the like can also be used, and these can also be used in combination. In the present invention, a polyhydric alcohol and a diglycidyl ether compound may be used together.

In the present invention, when producing a dicyclopentadiene-modified unsaturated ester compound, a conventional method is used, for example, dicyclopentadienyl α. While stirring β-unsaturated dibasic acid monoester (1.0 mol) and diglycidyl ether compound (0.5 mol) in a nitrogen gas stream,
React at 10-140°C for 3-5 hours.

At this time, quaternary ammonium salts such as laurylpyridium chloride and trimethylbenzyl chloride, and tertiary amines such as dimethylaniline can also be used as reaction accelerators. In addition, when using a polyhydric alcohol, for example, dicyclopentadienyl α,β-unsaturated dihydrochloric acid monoester (1.0 mol) and the polyhydric alcohol (0.5 mol) are stirred in a nitrogen gas stream. 7 at 180-200℃ while
Allow to react for ~10 hours.

Further, when a dicyclopentadiene-modified unsaturated ester compound is used in the resin composition of the present invention, it can be reacted with a metal salt such as magnesium oxide and molded in a thickened state. In this case, it is necessary to provide the unsaturated ester with an acid group capable of reacting with the metal salt. As a method for imparting acid groups, for example, 0.5 to 00 g equivalent of unsaturated basic acid is reacted with 1 equivalent of bisphenol epoxy resin, and 1 mole of polybasic acid is reacted with 1 equivalent of residual epoxy group. be. Polybasic acids include maleic acid, fumaric acid, adipic acid, phthalic acid, trimellitic acid,
Pyromellitic acid and the like are used.

The polybasic acid may be saturated or unsaturated, and the acid may be anhydrous.

The acid value of the dicyclopentadiene-modified unsaturated ester used in the present invention is 50 or less, preferably 15 or less.

In order to prevent gelation due to polymerization during the reaction, it is preferable to use a polymerization inhibitor such as hydroquinone, ditertiary butylcatechol, or hydroquinone monomethyl ether.

In addition, during this esterification reaction, ammonium salts such as trimethylbenzylammonium chloride and pyridinium chloride, tertiary amines such as triethylamine and dimethylaniline, ferric chloride, lithium hydroxide, lithium chloride, and stannic chloride are esterified. Catalysts can also be used to shorten the reaction time.

In the resin composition of the present invention, a polymerizable monomer can be blended as necessary. As a polymerizable monomer, 2
For example, styrene, p-methylstyrene, vinyltoluene, chlorostyrene, divinylbenzene, vinyltoluene, methyl methacrylate, ethyl acrylate, vinyl acetate, etc. are used. Styrene has excellent curability and workability, and p-methylstyrene has less odor during curing than styrene.
It is also preferable because it improves heat resistance (particularly strength retention rate when heated).

There is no particular restriction on the blending ratio of the polymerizable monomer, but from the viewpoint of mechanical properties and particle size adjustment work (sieving), dicyclopentadiene-modified unsaturated ester compound <A)
Preferably, the amount of the polymerizable monomer is 20 to 55 parts by weight relative to 80 to 45 parts by weight.

The natural or artificial abrasive material used in the present invention is an inorganic non-metal with a high hardness used in work or process of mechanically scraping, grinding, or polishing metal, wood, ceramic, plastic, etc. It refers to materials (natural or man-made minerals), and has a grinding action (ejecting shavings that are almost the same as the workpiece, giving the workpiece its shape and dimensions) or a polishing action (finishing and polishing the machined surface). Refers to a natural or artificially created object that has a Examples include diamonds, corundum, emery,
Natural abrasives such as garnet, silica (flint), Tripoli-1 diatomaceous earth, floating stone powder, dolomite (fired product), artificial diamond, silicon carbide, fused alumina, boron nitride, boron carbide, artificial emery, fused zirconia, alumina, Examples include artificial abrasives such as iron oxide, chromium oxide, and cerium oxide.

In the resin composition of the present invention, water (D
C may be blended.・Water is added to reduce the odor characteristic of unsaturated ester compounds generated during grinding.
The effect becomes even greater when used in combination with an isosymanurate derivative (E) having an unsaturated bond in the side chain described later.

The mixing ratio of water <D) is 5 to 150 parts by weight per 100 parts by weight of a mixture of 80 to 45 parts by weight of the dicyclopentadiene-modified unsaturated ester compound (A) and 20 to 55 parts by weight of the polymerizable monomer. parts by weight are preferred, and 10 to 80 parts by weight are particularly preferred. If the amount of water is too large, dimensional changes are likely to occur due to oral administration, and mechanical properties etc. tend to deteriorate.

The resin composition of the present invention may further contain an isocyanurate derivative (E) having an unsaturated bond in its side chain, if desired.

This isocyanurate derivative having an unsaturated bond in the side chain is an isocyanurate derivative represented by the general formula % (in which A, m and n are integers of 1 or 2, and may be the same or different). It is obtained by carrying out an esterification reaction between some or all of the hydroxyl groups of a nurate and an unsaturated basic acid having one or more unsaturated bonds between carbons or a lower alkyl ester thereof. be.

The esterification reaction between the above-mentioned isocyanurate and the above-mentioned unsaturated basic acid or its lower alkyl ester is carried out by a known method.

Although this esterification reaction can be carried out without using a solvent, it is preferable to use a solvent such as toluene or benzene. Preferably, a catalyst such as para-toluenesulfonic acid or concentrated sulfuric acid is used. The reaction temperature is preferably in the range of 60 to 130°C.

By changing the molar ratio of the isocyanurate derivative to the isocyanuric acid alkyl ester, the number of hydroxyl groups in the isocyanurate that undergoes an esterification reaction with the unsaturated basic acid can be changed. For example, when 3 moles of the above unsaturated basic acid or its lower alkyl ester are reacted with 1 mole of the above isocyanurate, all of the hydroxyl groups of the isocyanurate are reacted with the above unsaturated basic acid or its lower alkyl ester. esterified. On the other hand, when one mole of the unsaturated basic acid or its lower alkyl ester is reacted with one mole of the isocyanurate, on average one hydroxyl group of the isocyanurate is reacted with the unsaturated basic acid or its lower alkyl ester.
Esterified with basic acids or their lower alkyl esters.

Usually, the amount of the unsaturated basic acid or lower alkyl ester thereof is 0.1 mole of the isocyanurate.
It is used in a range of 5 to 5 moles. The number of esterified hydroxyl groups in the isocyanurate can also be changed by changing the reaction time.

Isocyanurate derivatives are usually obtained not as a single compound but as a mixture, but in the present invention they may be used in the form of a mixture.

Examples of unsaturated basic acids having one or more carbon-carbon unsaturated bonds used in the present invention include acrylic acid, methacrylic acid, crotonic acid, isocrotonic acid, tiglic acid, angelic acid, undecylenic acid, Examples include oleic acid, linoleic acid, lylunic acid, and the like.

Un14! has one or more unsaturated bonds between carbon and carbon!
! As the lower alkyl of the basic acid, lower alkyl esters of the above-mentioned unsaturated basic acids are used, such as ethyl acrylate, butyl acrylate, methyl methacrylate, methyl oleate, and the like.

Unsaturated - having one or more unsaturated bonds between carbon and carbon
The basic acid or its lower alkyl ester may be used alone or in combination of two or more.

A typical example of an isocyanurate derivative having an unsaturated bond in the side chain is tris(2-hydroxyethyl).
There are acrylic esters and methacrylic esters of isocyanuric acid, which have a structure represented by the general formula % (wherein R4 means hydrogen or a methyl group and may be the same or different), Commercially available from Hitachi Chemical Co., Ltd. (for example, FA-7
31A, FA-731M).

Isocyanuride-BJ conductor (E
) is not particularly limited, but dicyclopentadiene-modified unsaturated ester compound (A) 80-4
It is preferably 5 to 60 parts by weight per 100 parts by weight of a mixture of 5 parts by weight and 20 to 55 parts by weight of the polymerizable monomer.

In the resin composition of the present invention, the isocyanurate (8M) conductor having an unsaturated bond in its side chain can be added with or without melting.

The resin composition of the present invention may further contain a thermoplastic polymer (F) if desired, and such thermoplastic polymers include, for example, vinyl polymers such as polystyrene and polymethyl methacrylate, and saturated Examples include polyester resin. This thermoplastic polymer is blended to prevent cranking during molding, to provide smoothness, and to prevent the grindstone from softening due to heat during grinding.

The blending ratio of the thermoplastic polymer (F) is 1:1 of a mixture of 100 to 45 parts by weight of the dicyclopentadiene-modified unsaturated ester compound (A) and 0 to 55 parts by weight of the polymerizable monomer (B).
00 parts by weight, preferably 5 to 60 parts by weight.

The resin composition of the present invention may further contain a polymerization inhibitor such as hydroquinone, P-benzoquinone, t-butylcatechol, di-t-4-methylphenol, mono-t-butylhydroquinone, anisole, etc. .

To cure the resin composition of the present invention, an organic peroxide such as methyl ethyl ketone peroxide, cyclohexanone peroxide, cumene hydroperoxide, acetylacetone peroxide, t-butyl peroxybenzoate, benzoyl peroxide, dicumyl peroxide, etc. may be used as a curing agent and heated to a temperature of about room temperature to 120°C. At this time, octenoic acid, if necessary,
Naphthenic metal soaps, such as cobalt naphthenate,
One or a combination of two or more of cobalt octenoate, lead naphthenate, manganese naphthenate, etc. may be used as the curing accelerator. Furthermore, dimethylaniline, dimethylaniline, quaternary ammonium salt, acetylacetone, etc. may be used as a curing accelerator.

In addition, the resin composition of the present invention may contain fillers, if necessary.
A colorant, a thickener, and a reinforcing base material may also be included. Examples of fillers include extender pigments such as calcium carbonate, talc, barium sulfate, clay, silica powder, silica, and silica sand, and metals such as cryolite powder, fluorite powder, iron powder, aluminum powder, copper powder, and stainless steel powder. Powder, glass powder, etc. are used.

These may be used alone or in a mixture of two or more. As the coloring material, the organic pigments, inorganic pigments, dyes, or processed products thereof used in -i are used, and metal powders such as aluminum powder, copper powder, copper alloy powder, and stainless steel powder are also used. These may be used alone or in a mixture of two or more. As the thickener, metal hydroxides and oxides are used, and group (I) oxides and hydroxides are particularly preferred, such as magnesia oxide, magnesium hydroxide, calcium oxide, calcium hydroxide, etc. .

Also, isocyanates such as diphenylmethane diisocyanate and tolylene diisocyanate, and amine compounds such as dimethylaniline may be used. The three strong base materials are, for example, glass chopped strands, glass mats, glass cloth, glass rovings, asbestos, cotton cloth, etc., and inorganic or organic fibers such as nylon filaments, polypropylene filaments, carbon filaments, metal filaments, etc. It will be done. The resin composition of the present invention may also contain lightweight aggregates such as alumina hollow bodies, shirasu balloons, fly ash, and carbon balloons.

(Effects of the Invention) The resin composition of the present invention does not corrode the grinding machine or the workpiece, which are the drawbacks of Magnesia grindstones, and has an extremely low odor caused by heat generation during grinding (the characteristic odor of unsaturated polyester resin). It has excellent grinding properties such as grindability, bending strength, and hardness.

(Example of the invention) Hereinafter, the present invention will be explained in detail with reference to Examples.

The parts below mean parts by weight.

Example 1 - 2 moles of dicyclopentadiene, 2 moles of water, and 2 moles of % water maleic acid were charged into a Lof flask and reacted for 2 hours at 120°C in a nitrogen gas stream to give an acid value of 226.
dicyclopentadienyl monomaleate was obtained.

To this dicyclopentagenyl monomaleate, 1.05 mol of propylene glycol and 0.0 mol of hydroquinone were added.
01% by weight and heated at 180°C in a nitrogen gas stream.
The mixture was stirred and mixed, and the mixture was heated and condensed.

To 70 parts of the obtained dicyclopentadiene-modified unsaturated ester compound having an acid value of 20, 40 parts of styrene and 0.03 part of hydroquinone were added and melted to obtain a composition (a).

To 100 parts of this composition (a), 0.5% by weight of cobalt naphthenate (metal content 6%) (weight% based on the composition, the same applies hereinafter), 0.1% by weight of dimethylaniline, and Permec N (manufactured by NOF Corporation) , 55% methyl ethyl ketone peroxide) was added to serve as a binder.

Next, 100 parts of binder and abrasive WA#600 (
400 parts of fused alumina (manufactured by Nagoya Kenkarazai Co., Ltd.) and 80 parts of calcium carbonate NS-200 (Nitto Senkasha!!) were weighed and combined for about 15 minutes using an RFJM machine to form the resin composition of the present invention. I got it.

After passing through a further 42 meshes, cold press molding was performed using a compression molding machine (gauge pressure: 150
kg/rnrd for 10 minutes) and cured under curing conditions of 25°C/12 hours and 120°C/6 hours.

The formulation of the resin composition and the characteristics of the grinding wheel are shown in Table 1.
The table shows excellent odor test and grinding ratio, and bending strength.
It can be seen that the elastic modulus and hardness are also good.

Example 2 2 moles of dicyclopenc diene, 2 moles of water, and 2 moles of maleic anhydride were charged into 124 flasks, and reacted in a nitrogen gas stream at 120°C for 2 hours to give an acid value of 226.
dicyclopentadienyl monomaleate was obtained.

This dicyclopentadienyl monomaleate was added with Epicoat #828 (manufactured by Shell Chemical Co., Ltd., 1t18 per epoxy).
B) 1 mol, 0.1% by weight of trimethylbenzylammonium chloride and 0.1 part of hydroquinone were added and reacted at 130°C for 5 hours.

Composition (b) was obtained by adding and dissolving 40 parts of styrene and 0.03 part of hydroquinone to 60 parts of the obtained dicyclopentadiene-modified unsaturated ester compound having an acid value of 3.8.

To 100 parts of this combination t[(b), 0.5% by weight of cobalt naphthenate (metal content 6%), 0.1% of dimethylaniline, and 1.0% of Vermec N (manufactured by NOF Corporation, 55% methyl ethyl ketone peroxide) % by weight was added as a binder.

Next, 100 parts of binder and abrasive WA#600 (
400 parts of fused alumina (manufactured by Nagoya Kenkizai Co., Ltd.) and 80 parts of calcium carbonate NS-200 (manufactured by Nitto Funka Co., Ltd.) were weighed and mixed for about 15 minutes using a pickling machine to prepare the resin composition of the present invention. Obtained.

Furthermore, after passing through a sieve of 42 mesh, cold press molding was performed using a compression molding machine (gauge pressure: 15
0 kg/mm for 10 minutes) and cured under curing conditions of 25°C/12 hours and 120°C/6 hours.

Table 1 shows the formulation of the resin composition and the characteristics of the grinding wheel. 1st
The table shows excellent odor test and grinding ratio, and bending strength.
It can be seen that the elastic modulus and hardness are also good.

Example 3 2.0 moles of hydroxylated dicyclopentadiene and 2 moles of maleic anhydride were charged into 114 flasks and reacted in a nitrogen gas stream at 120°C for 2 hours to produce dicyclopentadiene with an acid value of 226. Lumono”?Reatewo got it.

To this zinc copentagenyl monomaleate, Epicoat 982B (manufactured by Shell Chemical Co., Ltd., epoxy tel.
8B) 0.85 mol, Epicoat #1001 (Shell Chemical Co., Ltd., epoxy equivalent weight 475) 0.2 mol, ゛・
4,′・゛.

Torino, 0.1% by weight of tilbenzylammonium chloride and 0.01 part of hydroquinone were added and heated to 120°C.
The reaction was carried out for 5 hours. Composition (c) was obtained by adding and dissolving 40 parts of styrene and 0.03 parts of hydroquinone to 70 parts of the dicyclopentadiene-modified unsaturated ester compound of the obtained acid fil[i8.

Cobalt naphthenate (
A mixture was prepared by adding 0.5% by weight of metal (6%), 0.1% by weight of dimethylaniline, and 1.0% by weight of Permec N (manufactured by NOF Corporation, 55% methyl ethyl ketone peroxide). .

Next, 100 parts of binder and abrasive WA#600 (
(manufactured by Nagoya Abrasives Co., Ltd.) 400 parts and calcium carbonate N,
80 parts of S-200 (manufactured by Nitto Funka Co., Ltd.) was weighed and mixed for about 15 minutes using a seeder to obtain a resin composition of the present invention.

After passing through a further 42 mesh sieve, cold press molding was performed using a compression molding machine (gauge pressure: 150
kg/mm for 10 minutes) and cured under curing conditions of 25°C/12 hours and 120°C/6 hours.

Table 1 shows the formulation of the resin composition and the characteristics of the grinding wheel. 1st
The table shows excellent odor test and grinding ratio, and bending strength.
It can be seen that the elastic modulus and hardness are also good.

Example 4 To 100 parts of the composition (a) obtained in Example 1, 0.5% by weight of cobalt naphthenate (metal content 6%), 0.1ffi1% of dimethylaniline, and Permec N (manufactured by NOF Corporation,
559i methyl ethyl ketone peroxide) was added to serve as a binder.

Next, 100 parts of binder and abrasive WA#600 (
Nagoya vf-polishing material? 1J) 40ON, 30 g of water, and 80 parts of calcium carbonate NS-200 (manufactured by Nitto Funka Co., Ltd.) were weighed and combined for about 15 minutes using a cicada to obtain a resin composition of the present invention.

After passing through a further 42 meshes, cold press molding was performed using a compression molding machine (gauge pressure: 15
0 kg/mrr? , 10 minutes) and cured under curing conditions of 25°C/12 hours and 120°C/6 hours.

Table 1 shows the formulation of the resin composition and the characteristics of the grinding wheel. 1st
The table shows excellent odor test and grinding ratio, and bending strength.
It can be seen that the elastic modulus and hardness are also good.
Example 5 To 109 parts of the composition (a) obtained in Example 1, 0.5% by weight of cobalt naphthenate (metal content 6%), 0.1% by weight of dimethylaniline and Permec N (manufactured by NOF Corporation, 55
% methyl ethyl ketone peroxide) was added as a binder.

Next, add 100 parts of binder in a mortar. Acrylic ethyl tris(2-hydroxyethyl)isocyanuric acid (Hitachi Chemical Co., Ltd., FA-, 73!A) 30 parts, abrasive W
Weighed 400 parts of A#600 (manufactured by Nagoya Abrasives Co., Ltd.) and 80 parts of carbonic acid, Lucium NS-200 (manufactured by Nitto Funka Co., Ltd.), and [i? The mixture was combined using Mta for about 20 minutes to obtain a resin composition according to the present invention.

After passing through a further sieve of 42 sieves, cold blur molding was performed using a compression molding machine (gauge pressure: 150
kg/mn (10 minutes) and cured under the curing conditions of 25° C./12 hours and 120° C./6 hours.

Table 1 shows the formulation of the resin composition and the characteristics of the grinding wheel. 1st
The table shows excellent odor test and grinding ratio, and bending strength.
It can be seen that the elastic modulus and hardness are also good.

Example 6 Composition obtained in Example 1+! J(a), 100 parts, 0.5% by weight of cobalt naphthenate (6% gold mud), 0.1% by weight of dimethylaniline, and 1.0% by weight of Permec N (manufactured by NOF Corporation, 55% methyl ethyl ketone peroxide). was added to serve as a binder.

Next, in a mortar were placed 100 parts of a binder, 30 parts of acrylic ester of tris(2-humanicoxyethyl)isocyanuric acid (Hitachi Chemical Co., Ltd. !FA-, 7.31 A), polystyrene 101, and abrasive WA#600 ( 400 copies of Nagoya VR Masha! and Calcium Carbonate NS-200
Weigh out 80 copies (manufactured by Nichizuka Mikasha) and check the results. Rm for about 20 minutes to obtain a resin composition of the present invention.

After passing through a further 42 mesh sieve, cold press molding was performed using a compression molding machine (gauge pressure: 150
kg/mn (10 minutes) and cured under the curing conditions of 25°C/12 hours and 120°C/6 hours.

Table 1 shows the formulation of the resin composition and the characteristics of the grinding wheel. 1st
It can be seen from the table that it has excellent odor test and grinding ratio, and also has good bending strength, elastic modulus, and hardness.

It is also seen that by adding polystyrene, which is a thermoplastic polymer, a molded grindstone having the smoothest surface among the examples can be obtained.

Comparative Example 1 0.7 mol of maleic anhydride, 0.3 mol of isophthalic acid, 0.5 mol of propylene glycol, 0.61 mol of neobenthyl glycol, and 0.01% by weight of hydroquinone were placed in 17!4 Lof flasks. The mixture was stirred and mixed at 210° C. in a nitrogen gas stream, and condensed by heating. To 70 parts of the obtained unsaturated ester having an acid value of 20, 30 parts of styrene and 0.03 parts of hydroquinone were added and melted to obtain a resin (d).

To 100 parts of this composition (d), 0.5% by weight of cobalt naphthenate (metal content 6%) and 1.0% by weight of Vermec N (manufactured by NOF Corporation, 55% methyl ethyl ketone peroxide) were added. In addition, it was used as a binder.

Next, add 100 parts of binder and abrasive WA#6'0 in a mortar.
0 (Nagoya Abrasives Co., Ltd.) and 80 parts of calcium carbonate NS-200 (Nitto Funka Co., Ltd.) were weighed, and ti?
The mixture was combined for about 15 minutes using an Fi machine to obtain a resin composition.

Furthermore, 42 meshes were sieved and then cold press molded using a compression molding machine (gauge pressure: 15
0 kg'/mrrr for 10 minutes) and cured under curing conditions of 25°C/12 hours and 120°C/6 hours.

Table 1 shows the formulation of the resin composition and the characteristics of the grinding wheel. 1st
From the table, it can be seen that the bending strength, elastic modulus, and hardness were significantly lower than those of Examples 1 to 6, and a strong odor was felt.

Comparative Example 2 2.0 mol of methacrylic acid, epoxy resin Epicor 1-8
28 (manufactured by Shell Chemical Co., Ltd., epoxy equivalent: 189) 1 mol, hydroquinone 0.01 per the total amount of the above components
% by weight and 0.1% by weight of trimethylbenzylammonium chloride were charged into a separable flask.
The reaction was heated at 20° C. for 7 hours. Composition (e) was obtained by adding and dissolving 40 parts of styrene and 0.03 part of hydroquinone to 60 parts of the obtained unsaturated ester having an acid value of 9.

Cobalt naphthenate (
Metal content 6%) 0.5% by weight and Permec N (manufactured by NOF Corporation, 55% methyl ethyl ketone peroxide) 1.
0% by weight was added to serve as a binder.

Next, 100 parts of binder and abrasive WA#600 (
400 parts of Nagoya Abrasives Co., Ltd.'jA) and 80 parts of calcium carbonate NS-200 (Nitto Soka Co., Ltd. 3!) were weighed out and mixed for about 15 minutes using a sowing machine to obtain a resin composition.

After passing through a further 42 meshes, cold press molding was performed using a compression molding machine with a gauge pressure of 2150.
kg,/mm for 10 minutes) and cured under curing conditions of 25°C/12 hours and 120°C/6 hours.

(The formulation of the grease-resistant composition and the grinding wheel properties are shown in Table 1. From Table 1, the bending strength, elastic modulus, and hardness are significantly lower than those of Examples 1 to 6, and a strong odor is felt. I understand.

Margin below Table 1 Table 1 (continued)

Claims (1)

[Claims] 1. (A) Dicyclopentadiene-modified product obtained by reacting dicyclopentadienyl α,β-unsaturated dibasic acid monoester with a polyhydric alcohol and/or a diglycidyl ether compound Unsaturated ester compounds and (
B) An abrasive resin composition containing a natural and/or artificial abrasive material. 2. In addition to the components (A) and (B), (C) a polymerizable monomer, (D) water, (E) an isocyanurate derivative having an unsaturated bond in the side chain, and/or (F) heat. The polishing resin composition according to claim 1, which contains a plastic polymer.