A cyclic molecule having an active hydrogen group-containing side chain, and a curable composition containing the cyclic molecule.

Abstract

A ring molecule having an active-hydrogen-group-containing side chain according to the present invention has a side chain at an end of which an active hydrogen group has been introduced using a polymerizable ring compound, wherein the contained amount of impurities caused by the polymerizable ring compound is not more than 10 mass%.　The present invention makes it possible to provide a raw material for a resin, particularly a resin useful for polishing pads, which provides a high degree of wear resistance and flatness (edge roll-off prevention) for a polishing target member, and which exhibits excellent mechanical properties.

Description

[Technical Field]

[0001] The present invention relates to a cyclic molecule having a side chain with an active hydrogen group introduced at its terminus, which can be suitably used as a raw material for resins such as polyurethane. [Background technology]

[0002] In the semiconductor and optical materials fields, a high degree of smoothness is sometimes required, necessitating polishing. Specifically, polishing is typically performed using the CMP (Chemical Mechanical Polishing) method, which involves supplying a slurry (polishing solution) in which abrasive particles are dispersed in an alkaline or acidic solution to the workpiece.

[0003] In this context, a technology has been disclosed in which polyurethane resin is used as an abrasive component, such as an abrasive pad, when flattening the workpiece with an abrasive (see Patent Document 1).

[0004] In the aforementioned CMP method, the polishing characteristics of the polishing pad require excellent flatness of the workpiece and a high polishing rate (polishing speed). Furthermore, improved wear resistance is desired to increase productivity, but the technology disclosed in Patent Document 1 is insufficient, and further improvements in these performance aspects are required.

[0005] Meanwhile, in recent years, polyrotaxanes have attracted attention as a novel type of compound. These polyrotaxanes are functional materials that have a composite molecular structure consisting of an axial molecule and multiple cyclic molecules that enclose the axial molecule. Due to their properties, these polyrotaxanes are used in various fields, including semiconductors and optical materials.

[0006] Therefore, the present inventors disclose that by using this polyrotaxane as a raw material for the polyurethane resin used in the polishing pad described above, a polishing pad can be made that exhibits excellent polishing properties (see Patent Document 2). [Prior art documents] [Patent Documents]

[0007] [Patent Document 1] Japanese Patent Publication No. 2007-77207 [Patent Document 2] International Publication No. 2018 / 092826 [Overview of the Initiative] [Problems that the invention aims to solve]

[0008] However, in recent years, there has been a demand for polishing pads with even greater performance, particularly in terms of flatness (prevention of edge sagging) and wear resistance of the workpiece to be polished, as well as excellent mechanical properties. The technology described in Patent Document 2, which uses polyrotaxane as a raw material for polyurethane resin, had room for improvement.

[0009] Therefore, the object of the present invention is to provide a resin raw material (for example, polyurethane resin) that exhibits excellent flatness (prevention of edge sagging) of a workpiece when polished using an abrasive pad made of the resulting resin, high wear resistance of the resulting resin, and excellent mechanical properties, and in particular a resin raw material useful for abrasive pads. [Means for solving the problem]

[0010] The inventors diligently conducted research to solve the above problems. As a result of their research aimed at overcoming the above problems, the inventors found that by using a polymerizable cyclic compound to form a cyclic molecule having a side chain into which an active hydrogen group has been introduced at the terminal (hereinafter also referred to as "cyclic molecule having an active hydrogen group-containing side chain" or "component (A)") as a raw material for a resin such as polyurethane, the resulting resin has relatively good wear resistance and mechanical properties, and furthermore, a polishing pad made of the said resin has a certain degree of flatness of the material to be polished.

[0011] However, even when using the cyclic molecule having the active hydrogen group-containing side chain, it sometimes did not possess sufficient properties. As a result of further investigation by the present inventors, it was discovered that by reducing the content of impurities caused by the polymerizable cyclic compound in the cyclic molecule having the active hydrogen group-containing side chain to 10% by mass or less, when used as a raw material for resin, the resulting resin has higher wear resistance and superior mechanical properties, and the polishing pad made from this resin exhibits superior flatness of the workpiece and a higher polishing rate, thus completing the present invention.

[0012] In other words, according to the first invention, A cyclic molecule having a side chain into which an active hydrogen group is introduced at the terminal using a polymerizable cyclic compound, wherein the content of impurities due to the polymerizable cyclic compound is 10% by mass or less. The second aspect of the present invention is a curable composition comprising a cyclic molecule having an active hydrogen group-containing side chain, which is the first aspect of the present invention, and a polymerizable monomer having a polymerizable functional group that can polymerize with the active hydrogen group of the cyclic molecule having an active hydrogen group-containing side chain (hereinafter also simply referred to as "polymerizable monomer" or "component (B)"). The third invention relates to a cured body obtained by curing the curable composition of the second invention, and a polishing pad made of the cured body. The fourth aspect of the present invention is a method for producing a cyclic molecule having an active hydrogen group-containing side chain.

[0013] More specifically, the present invention relates to the following [1] to [9]. [1] A cyclic molecule having a side chain into which an active hydrogen group is introduced at the terminal using a polymerizable cyclic compound, wherein the content of impurities due to the polymerizable cyclic compound is 10% by mass or less, and the cyclic molecule having an active hydrogen group-containing side chain. [2] A cyclic molecule having an active hydrogen group-containing side chain as described in [1] above, wherein the impurities resulting from the polymerizable cyclic compound include a compound obtained by ring-opening the polymerizable cyclic compound. [3] The cyclic molecule is cyclodextrin, the polymerizable cyclic compound is at least one selected from cyclic lactones and cyclic lactams, and the molecular weight of the side chain having an active hydrogen group introduced at the terminal is 300 or more in terms of number average molecular weight. The cyclic molecule having an active hydrogen group-containing side chain according to [1] or [2] above. [4] The cyclic molecule having an active hydrogen group-containing side chain according to any one of [1] to [3] above, wherein the active hydrogen group is any group selected from a hydroxyl group and an amino group. [5] A curable composition comprising the cyclic molecule having an active hydrogen group-containing side chain according to any one of [1] to [4] above, and a polymerizable monomer having a polymerizable functional group capable of polymerizing with the active hydrogen group of the cyclic molecule having the active hydrogen group-containing side chain. [6] The curable composition according to [5] above, further comprising micro hollow particles. [(7)] A cured body obtained by curing the curable composition according to [5] or [6] above. [(8)] A polishing pad comprising the cured body according to [7] above. [9] In a reaction system comprising a polymerizable cyclic compound and a cyclic molecule capable of reacting with the polymerizable cyclic compound, the water content in the reaction system is 10,000 ppm or less, and the polymerizable cyclic compound is ring-opening polymerized to introduce a side chain into the cyclic molecule. A method for producing a cyclic molecule having an active hydrogen group-containing side chain, characterized in that. [Advantages of the Invention]

[0014] The cyclic molecule having an active hydrogen group-containing side chain of the present invention has a resin obtained from the cyclic molecule having the active hydrogen group-containing side chain as a raw material, which has high wear resistance and exhibits excellent mechanical properties. Furthermore, the polishing pad made of the resin has excellent flatness of the polished member and a large polishing rate.

[0015] Or, the cyclic molecule having an active hydrogen group-containing side chain of the present invention can be used not only as a raw material for the resin used in the polishing pad, but also as a raw material for various high-functional resins, and can be usefully used as various high-functional materials or their raw materials. [Embodiments for Carrying Out the Invention]

[0016] The cyclic molecule having an active hydrogen group-containing side chain of the present invention is a cyclic molecule having a side chain with an active hydrogen group introduced at the terminal using a polymerizable cyclic compound, and the content of impurities derived from the polymerizable cyclic compound is 10% by mass or less. It is a cyclic molecule having an active hydrogen group-containing side chain.

[0017] The cyclic molecule having an active hydrogen group-containing side chain of the present invention can be obtained, for example, as described later, by reacting a polymerizable cyclic compound with a cyclic molecule. During the reaction, a side chain derived from the polymerizable cyclic compound is introduced into the cyclic molecule, and an active hydrogen group derived from the polymerizable cyclic compound is introduced into the side chain. Therefore, the cyclic molecule ((A) component) having an active hydrogen group-containing side chain of the present invention can also be referred to as a cyclic molecule into which a side chain with an active hydrogen group introduced at the terminal is introduced using a polymerizable cyclic compound. The active hydrogen group is, for example, a hydroxyl group, an amino group, a thiol group, etc., as described later. The following will be described in detail.

[0018] <Cyclic molecule ((A) component) having an active hydrogen group-containing side chain> The cyclic molecule used as a raw material for forming the (A) component of the present invention is not particularly limited as long as it is a cyclic molecule into which a side chain with an active hydrogen group introduced at the terminal can be introduced using a polymerizable cyclic compound. As the cyclic molecule, a cyclic molecule having a reactive functional group is preferable as described later. Further, the cyclic molecule having an active hydrogen group-containing side chain, which is the (A) component, is preferably composed of only a cyclic molecule and three or more side chains having an active hydrogen group at the terminal introduced into the cyclic molecule. Such an (A) component is unlikely to have a high molecular weight like the polyrotaxane used in the prior art and tends to have excellent handling properties. For example, such cyclic molecules include cyclodextrin, crown ether, benzocrown, dibenzocrown, dicyclohexanocrown, cyclobis(paraquat-1,4-phenylene), dimethoxypyraarene, calixarene, and phenanthroline. Among these, cyclodextrin and calixresorcinarene are preferred, with cyclodextrin being the most preferred.

[0019] The cyclodextrins include α-isomers (ring diameter 0.45-0.6 nm), β-isomers (ring diameter 0.6-0.8 nm), and γ-isomers (ring diameter 0.8-0.95 nm). Mixtures of these can also be used. In the present invention, α-cyclodextrin and β-cyclodextrin are particularly preferred, with β-cyclodextrin being the most preferred in terms of cost and physical properties. The calixresorcinarene is a cyclic molecule obtained by cyclic condensation reaction of resorcinol with various aldehydes. The resorcinol is not limited to resorcinol alone, but may also be a resorcinol derivative such as 2-nitroresorcinol. The aldehyde can be any known aldehyde without any limitations, such as aliphatic aldehydes such as n-butanal, isobutanal, and heptanal, or aromatic aldehydes such as benzaldehyde, vanillin, and 4-nitrobenzaldehyde. Two or more of these may be used in mixture. Among these, heptanal, benzaldehyde, and vanillin are preferably used. Furthermore, in the present invention, the calixresorcinarene is preferably a tetramer, but is not limited thereto.

[0020] The side chain to which the aforementioned active hydrogen group has been introduced at its terminus can be introduced, for example, by utilizing the reactive functional group possessed by a cyclic molecule and reacting it with this reactive functional group.

[0021] Examples of the reactive functional group include hydroxyl groups and amino groups, with hydroxyl groups being preferred. For example, β-cyclodextrin has 21 OH groups (hydroxyl groups) as reactive functional groups, and side chains are introduced by reacting with these OH groups. Therefore, a maximum of 21 side chains can be introduced to one β-cyclodextrin. In the present invention, in order to fully exhibit the function of the side chains described above, it is preferable that at least three side chains with active hydrogen groups introduced at their ends are introduced. Preferably, it is a cyclic molecule with five or more side chains with active hydrogen groups introduced at their ends, more preferably a cyclic molecule with seven or more side chains with active hydrogen groups introduced at their ends, and most preferably a cyclic molecule with eight or more side chains with active hydrogen groups introduced at their ends. There is no particular upper limit, but if the number of introduced side chains is too large, the viscosity of the cyclic molecule having active hydrogen group-containing side chains may increase, potentially reducing its handling properties. For this reason, it is particularly preferable that the number of introduced side chains be in the range of 8 to 18.

[0022] Next, in the present invention, a side chain in which an active hydrogen group is introduced at the terminal using a polymerizable cyclic compound (hereinafter also referred to as an "active hydrogen group-containing side chain"), that is, a side chain possessed by a cyclic molecule, will be described.

[0023] The active hydrogen group-containing side chain is not particularly limited, but it is preferably formed by repeating organic chains with 3 to 20 carbon atoms. The number-average molecular weight of such an active hydrogen group-containing side chain is preferably in the range of 300 to 10000, more preferably 350 to 5000, particularly preferably 400 to 5000, and most preferably in the range of 400 to 1500. Being within this range makes it easier to adjust the hardness and physical properties of the resulting cured product. The number-average molecular weight of this active hydrogen group-containing side chain can be adjusted by the amount of polymerizable cyclic compound used when introducing the active hydrogen group-containing side chain, and can be calculated, 1 This can be determined from 1H-NMR measurements.

[0024] By setting the lower limit of the number-average molecular weight of the active hydrogen group-containing side chain as described above, excellent mechanical properties are exhibited, and when a cured body obtained by curing the curable composition of the present invention is used in a polishing pad, the polishing rate tends to improve. Furthermore, compatibility with component (B) also tends to improve. On the other hand, by setting the upper limit of the number-average molecular weight of the side chain as described above, the hardness of the cured body does not decrease, and the wear resistance does not tend to decrease.

[0025] The impurities resulting from the polymerizable cyclic compound are compounds derived from the polymerizable cyclic compound that were not incorporated into the cyclic molecule when the side chain was introduced into the cyclic molecule using the polymerizable cyclic compound described later. Impurities originating from polymerizable cyclic compounds are specifically compounds in which the polymerizable cyclic compound has opened its ring (compounds that have opened their ring and polymerized solely from polymerizable cyclic compounds), or unreacted polymerizable cyclic compounds. Typically, impurities originating from polymerizable cyclic compounds include compounds in which the polymerizable cyclic compound has opened its ring, and often consist solely of compounds in which the polymerizable cyclic compound has opened its ring. If these polymerizable cyclic compounds contain a large amount of impurities in cyclic molecules having active hydrogen group-containing side chains, the crosslinking density decreases when cured products are made using these molecules, resulting in a decrease in resin properties. Therefore, the content of impurities caused by polymerizable cyclic compounds in cyclic molecules having active hydrogen group-containing side chains should be 10% by mass or less, preferably 5% by mass or less, more preferably 3% by mass or less, and even more preferably 1% by mass or less. The above-mentioned content of impurities caused by polymerizable cyclic compounds is expressed as the content (mass%) relative to the total amount (100% by mass) of cyclic molecules having active hydrogen group-containing side chains.

[0026] By setting the upper limit of the content of impurities caused by the polymerizable cyclic compound as described above, excellent mechanical properties can be achieved, and when a cured body of the curable composition of the present invention is used as a polishing pad, excellent polishing properties can be achieved. If the impurities caused by the polymerizable cyclic compound are outside the above range, the resin properties tend to deteriorate, and the polishing properties also tend to deteriorate.

[0027] The amount of impurities caused by the polymerizable cyclic compound can be determined by isolation, but it can also be determined by measuring the area value using gel permeation chromatography (hereinafter abbreviated as "GPC method").

[0028] The molecular weight used in the GPC method for calculating impurities is the molecular weight on a polyethylene oxide basis, calculated based on the elution time of a polyethylene oxide standard with a known average molecular weight. Impurities originating from polymerizable cyclic compounds typically result in smaller molecular weight peaks than cyclic molecules with active hydrogen group-containing side chains. Therefore, when the area occupied by cyclic molecules with active hydrogen group-containing side chains in the GPC method is denoted as area-pro, and the area occupied by impurities originating from polymerizable cyclic compounds is denoted as area-bypro, the content (mass%) of impurities originating from polymerizable cyclic compounds relative to cyclic molecules with active hydrogen group-containing side chains can be calculated as [100 / (area-pro+area-bypro)]×area-bypro(mass%).

[0029] Furthermore, it is preferable that component (A) has a certain viscosity range. This makes it possible to have excellent handling properties. A preferred viscosity range is 500 mPa·s to 50,000 mPa·s at 60 degrees, more preferably 500 mPa·s to 10,000 mPa·s, and most preferably 1,000 mPa·s to 6,000 mPa·s. These can be determined, for example, by a rotational viscometer.

[0030] Furthermore, if the molecular weight of component (A) is too large, it tends to become difficult to handle and its compatibility deteriorates when mixed with other components, such as component (B). From this viewpoint, the weight-average molecular weight Mw of component (A) is preferably in the range of 1,500 to 100,000, particularly 2,000 to 30,000, especially 2,500 to 10,000, and most preferably in the range of 3,000 to 8,000. In addition, in order to exhibit stable physical properties, it is preferable that the degree of dispersion be 1.2 or less. Note that the weight-average molecular weight Mw and the degree of dispersion are values ​​measured by the GPC measurement method described in the examples below. Also, as mentioned above, if the molecular weight of the cyclic molecule having an active hydrogen group-containing side chain (A) is too large, it tends to deteriorate in handling and compatibility, so it is preferable that the cyclic molecule having an active hydrogen group-containing side chain (A) does not form a complex with other molecules.

[0031] In the present invention, the active hydrogen group-containing side chain may be linear or branched.

[0032] The method for introducing the active hydrogen group-containing side chain can appropriately incorporate methods and compounds disclosed in International Publication No. 2015 / 159875, such as ring-opening polymerization, cationic polymerization, and anionic polymerization. By using the above method, a side chain of an appropriate size can be introduced by reacting an appropriately selected compound with the reactive functional group of the cyclic molecule.

[0033] The polymerizable cyclic compound used in this invention is not limited to any compound that can be introduced into a cyclic molecule by ring-opening polymerization. Specific examples of such polymerizable cyclic compounds include cyclic ethers, cyclic siloxanes, cyclic lactones, cyclic lactams, cyclic acetals, cyclic amines, cyclic carbonates, cyclic iminoethers, and cyclic thiocarbonates.

[0034] Among the polymerizable cyclic compounds, cyclic ethers, cyclic lactones, and cyclic lactams are preferred from the viewpoint of high reactivity and ease of molecular weight adjustment.

[0035] When polymerizable cyclic compounds such as the aforementioned cyclic lactones and cyclic ethers are introduced by ring-opening polymerization, a hydroxyl group is introduced at the end of the side chain, and when polymerizable cyclic lactams are introduced by ring-opening polymerization, an amino group is introduced at the end of the side chain.

[0036] The following are examples of cyclic ethers, cyclic lactones, cyclic lactams, and cyclic carbonates that are preferably used.

[0037] Cyclic ether; Ethylene oxide, 1,2-propylene oxide, epichlorohydrin, epibromohydrin, 1,2-butylene oxide, 2,3-butylene oxide, isobutylene oxide, oxetane, 3-methyloxetane, 3,3-dimethyloxetane, tetrahydrofuran, 2-methyltetrahydrofuran, 3-methyltetrahydrofuran, etc. Cyclic lactone; Four-membered ring lactones; β-propiolactone, β-methylpropiolactone, L-serine-β-lactone, etc. Five-membered ring lactones; γ-butyrolactone, γ-hexanolactone, γ-heptanolactone, γ-octanolactone, γ-decanolactone, γ-dodecanolactone, α-hexyl-γ-butyrolactone, α-heptyl-γ-butyrolactone, α-hydroxy-γ-butyrolactone, γ-methyl-γ-decanolactone, α-methylene-γ-butyrolactone, α,α-dimethyl-γ-butyrolactone, D-erythronolactone, α-methyl Tyl-γ-butyrolactone, γ-nonanolactone, DL-pantractone, γ-phenyl-γ-butyrolactone, γ-undecanolactone, γ-valerolactone, 2,2-pentamethylene-1,3-dioxolan-4-one, α-bromo-γ-butyrolactone, γ-crotonolactone, α-methylene-γ-butyrolactone, α-methacryloyloxy-γ-butyrolactone, β-methacryloyloxy-γ-butyrolactone, etc. Six-membered ring lactones; δ-valerolactone, δ-hexanolactone, δ-octanolactone, δ-nonanolactone, δ-decanolactone, δ-undecanolactone, δ-dodecanolactone, δ-tridecanolactone, δ-tetradecanolactone, DL-mevalonolactone, 4-hydroxy-1-cyclohexanecarboxylic acid δ-lactone, monomethyl-δ-valerolactone, monoethyl-δ-valerolactone, monohexyl-δ-valerolactone, 1,4-dioxan-2-one, 1,5-dioxepant-2-one, etc. 7-membered ring lactones; ε-caprolactone, monomethyl-ε-caprolactone, monoethyl-ε-caprolactone, monohexyl-ε-caprolactone, dimethyl-ε-caprolactone, di-n-propyl-ε-caprolactone, di-n-hexyl-ε-caprolactone, trimethyl-ε-caprolactone, triethyl-ε-caprolactone, tri-n-ε-caprolactone, ε-caprolactone, 5-nonyl-oxepan-2-one, 4,4,6-trimethyl-oxepan-2-one, 4,6,6-trimethyl-oxepan-2-one, 5-hydroxymethyl-oxepan-2-one, etc. 8-membered ring lactones; ζ-enanthractones, etc. Other lactones; lactone, lactide, dilactide, tetramethylglycoside, 1,5-dioxepant-2-one, t-butylcaprolactone, etc. cyclic lactam; 4-membered ring lactams; such as 4-benzoyloxy-2-azetidinone. Five-membered ring lactams; γ-butyrolactam, 2-azabicyclo(2,2,1)hepta-5-en-3-one, 5-methyl-2-pyrrolidone, etc. Six-membered ring lactams; ethyl 2-piperidone-3-carboxylate, etc. 7-membered ring lactams; ε-caprolactam, DL-α-amino-ε-caprolactam, etc. 8-membered ring lactams; ω-heptalactams, etc. Cyclic carbonate; Ethylene carbonate, propylene carbonate, 1,2-butyleneglycerol 1,2-carbonate carbonate, 4-(methoxymethyl)-1,3-dioxolan-2-one, (chloromethyl)ethylene carbonate, vinylene carbonate, 4,5-dimethyl-1,3-dioxolan-2-one, 4-chloromethyl-5-methyl-1,3-dioxolan-2-one, 4-vinyl-1,3-dioxolan-2-one, 4,5-diphenyl-1,3-dioxolan-2-one, 4,4-dimethyl-5-methylene-1,3-dioxolan-2-one, 1,3-dioxan-2-one, 5-methyl-5-propyl-1,3-dioxolan-2-one, 5,5-diethyl-1,3-dioxolan-2-one The polymerizable cyclic compounds described above can be used individually or in combination of two or more.

[0038] In the present invention, the polymerizable cyclic compound preferred is at least one selected from cyclic lactones and cyclic lactams, and the polymerizable cyclic compound more preferably is a cyclic lactone. Particularly preferred cyclic lactones include ε-caprolactone, α-acetyl-γ-butyrolactone, α-methyl-γ-butyrolactone, γ-valerolactone, and γ-butyrolactone, while particularly preferred cyclic lactams are ε-caprolactam, γ-butyrolactam, and DL-α-amino-ε-caprolactam. Among these, the most preferred are ε-caprolactone and ε-caprolactam.

[0039] Furthermore, when introducing side chains by ring-opening polymerization of cyclic compounds, the reactive functional groups (e.g., hydroxyl groups) of the cyclic molecule may be unreactive, and it may be difficult to directly react large polymerizable cyclic compounds, especially due to steric hindrance. In such cases, it is preferable to first react a low-molecular-weight compound such as propylene oxide with the reactive functional groups of the cyclic molecule to perform hydroxypropylation or the like, thereby introducing highly reactive functional groups beforehand, for example, before reacting the aforementioned cyclic lactones or cyclic lactams. Subsequently, the side chains can be introduced by ring-opening polymerization using the polymerizable cyclic compound. In this case, the hydroxypropylated portion can also be considered a side chain.

[0040] The method for producing component (A) of the present invention is not particularly limited, and any known method may be used, however, it is preferable to control the amount of water in the reaction system. If water is present in the reaction system, impurities caused by polymerizable cyclic compounds may be generated, which may reduce the resin properties when a cured product is made. Specifically, a preferred method for producing component (A) is to introduce a side chain into the cyclic molecule by ring-opening polymerization of the polymerizable cyclic compound in a reaction system containing a polymerizable cyclic compound and a cyclic molecule that can react with the polymerizable cyclic compound, with the water content in the reaction system being 10,000 ppm or less. Here, the cyclic molecule that can react with the polymerizable cyclic compound is a cyclic molecule having the reactive functional group described above. Thus, it is preferable to perform ring-opening polymerization with a water content of 10,000 ppm or less in the reaction system between the cyclic molecule and the polymerizable cyclic compound, preferably 5,000 ppm or less, more preferably 3,000 ppm or less, and even more preferably 1,000 ppm or less. The water content in the reaction system can be measured by the Karl Fischer method described in the examples below.

[0041] Furthermore, any known catalyst can be used without limitation for the ring-opening polymerization described above. For example, organotitanium compounds such as tetramethyl titanate, tetraethyl titanate, tetrapropyl titanate, and tetrabutyl titanate; organotin compounds such as 2-ethylhexanate, dibutyltin dilaurate, tin octoate, dibutyltin oxide, and dibutyltin acetate; stannous halogen compounds such as stannous chloride, stannous bromide, and stannous iodide; and various metal acetylacetonate compounds and metal salts of organic carboxylic acids can be used. However, if a certain amount of the catalyst remains after the introduction of the side chain, it may act as a catalyst when curing the curable composition containing components (A) and (B), potentially leading to excessively fast curing and poor curing. Therefore, the amount of remaining catalyst is preferably 5000 ppm or less relative to component (A), calculated on a scale of the various metals used as catalysts. More preferably, it is 1000 ppm or less, and most preferably 600 ppm or less. Of the remaining catalyst amount, for example, the amount of remaining tin can be measured by ICP emission as described in the examples below. On the other hand, if there is too little catalyst, the reaction may be too slow. Therefore, when using catalyst, the amount of catalyst is preferably 50 ppm or more, and more preferably 100 ppm or more, relative to component (A), in terms of the various metals used in the catalyst. Furthermore, in the ring-opening polymerization described above, the catalysts mentioned above or the organic solvents described below can be used, and the reaction can also be carried out without a solvent. Preferred organic solvents when using organic solvents include, but are not limited to, DMSO, DMF, THF, toluene, xylene, chlorobenzene, and chloroform. In the ring-opening polymerization used in this invention, it is preferable to carry it out without solvents for convenience and cost reasons. By carrying out the aforementioned ring-opening polymerization without solvents, the amount of metal catalyst required can be reduced, eliminating not only solvent costs and solvent removal time, but also costs for removing catalysts such as tin, which is extremely useful for industrial production. Furthermore, the preferred reaction temperature for the ring-opening polymerization described above is preferably 80°C or higher and less than 200°C, more preferably 100°C or higher and less than 180°C, and most preferably 110°C or higher and less than 150°C. This allows for stable production even with a small amount of metal catalyst. Furthermore, while the preferred reaction time for the ring-opening polymerization described above varies depending on the catalyst and reaction temperature, prolonged heating is undesirable as it may broaden the distribution of the degree of polymerization. Therefore, the preferred reaction time is 1 to 120 hours, more preferably 3 to 72 hours, and most preferably 3 to 48 hours.

[0042] In this invention, the reaction in which a functional group of a side chain is reacted with another compound to introduce a structure derived from that other compound is sometimes referred to as "modification." The compound used for modification can be any compound that is capable of reacting with the functional group of the side chain. By selecting such a compound, it is possible to introduce various polymerizable functional groups into the side chain, for example.

[0043] As can be understood from the above explanation, the side chains introduced into cyclic molecules can have various functional groups introduced to their ends in a variety of ways. (Preferred composition of component (A)) In the present invention, the most preferably used component (A) is one in which α-cyclodextrin or β-cyclodextrin is used as the cyclic molecule and ε-caprolactone is used as the polymerizable cyclic compound, and a hydroxyl group, which is an active hydrogen group, is introduced at the end of the side chain of the cyclic molecule. In this case, the hydroxyl group of α-cyclodextrin or β-cyclodextrin may be hydroxypropylated, and then a polycaprolactone chain derived from ε-caprolactone may be introduced by ring-opening polymerization.

[0044] Furthermore, the molecular weight and modification rate of the side chain are preferably as described above. The introduced side chain can have active hydrogen at all ends, or it can be modified into an unreactive group in order to achieve the desired number of moles of active hydrogen.

[0045] Examples of the active hydrogen groups include hydroxyl groups, amino groups, and thiol groups. In particular, in the present invention, the preferred active hydrogen group is at least one active hydrogen group selected from the group consisting of hydroxyl groups and amino groups, with the most preferred being the hydroxyl group.

[0046] <(B) A polymerizable monomer having polymerizable functional groups that can polymerize with the active hydrogen groups of component (A)> In the present invention, component (B) can be any known polymerizable monomer having a polymerizable functional group that can polymerize with the active hydrogen group of component (A), without any limitations. And, of course, it is a polymerizable monomer other than component (A). For example, polymerizable monomers described in International Publication No. 2015 / 068798 can be cited.

[0047] If the active hydrogen group of component (A) has polymerizable functional groups selected from hydroxyl groups, thiol groups, and amino groups (in this invention, an amino group refers to both a primary amino group (-NH2) and a secondary amino group (-NHR; R is a substituent, for example, an alkyl group)), then component (B) can be an isocyanate compound having at least two isocyanate groups in the (B1) molecule (hereinafter also referred to as "(B1) isocyanate compound" or "(B1) component").

[0048] Furthermore, if the active hydrogen group of component (A) is a hydroxyl group or an amino group, component (B) can also be an epoxy group-containing monomer having an epoxy group (hereinafter also referred to as "(B2) epoxy group-containing monomer" or "(B2) component").

[0049] The curable composition of the present invention may contain other components as long as they do not impair the effects of the present invention, as long as they contain components (A) and (B). For example, the curable composition may contain other polymerizable monomers different from component (B) that do not polymerize with component (A) (hereinafter also referred to as "other polymerizable monomers"). Specifically, by including other polymerizable monomers that do not polymerize with component (A) but polymerize with component (B) in the curable composition which contains component (A) and component (B) that can polymerize with component (A), copolymerization can be performed between component (A), component (B), and the other polymerizable monomers. That is, the curable composition may contain not only components (A) and (B), but also other polymerizable monomers that can copolymerize with component (B) (hereinafter also referred to as "component (C)").

[0050] Examples of these (C) components include (C1) thiol compounds having at least one group selected from a hydroxyl group and a thiol group (hereinafter also referred to as "(C1)(thiol compound)" or "(C1) component"), and (C2) amino group-containing monomers having an amino group (hereinafter also referred to as "(C2) amino group-containing monomer" or "(C2) component".

[0051] The above example will be explained in more detail. Specifically, for example, in the case of a curable composition in which a (B1) iso(thio)cyanate compound is used as component (B), and further comprises the (C1) (thio)ol compound and / or the (C2) amino group-containing monomer, a cured product can be obtained by copolymerizing components (A), (B1), (C1), and / or (C2). Naturally, in this case, the curable composition may also further contain component (B2).

[0052] The following provides a detailed explanation of components (B) and (C) individually.

[0053] <(B1) Iso(thio)cyanate compounds; (B1) component> (B1) An iso(thio)cyanate compound is a compound having at least two groups selected from the group consisting of isocyanate groups and isothiocyanate groups. Of course, a compound having both an isocyanate group and an isothiocyanate group is also selected. Among these, compounds having 2 to 6 iso(thio)cyanate groups in the molecule are preferred, compounds having 2 to 4 are more preferred, and compounds having 2 to 3 are even more preferred.

[0054] Furthermore, the (B1) iso(thio)cyanate compound may also be a (B12) urethane prepolymer (hereinafter also referred to as "(B12) component") produced by the reaction of a (B13) bifunctional iso(thio)cyanate compound (hereinafter also referred to as "(B13) component") having a total of two groups selected from the group consisting of isocyanate groups and isothiocyanate groups in the molecule, and a (C12) bifunctional active hydrogen-containing compound (hereinafter also referred to as "(C12) component") having two active hydrogen-containing groups in the molecule. The (B12) urethane prepolymer corresponding to component (B1) can be any commonly used one containing two or more unreacted isocyanate groups or isothiocyanate groups, and can be used in the present invention without any limitations, and is preferably a (B12) urethane prepolymer containing two or more isocyanate groups.

[0055] The active hydrogen-containing group in the (C12) component is selected from a hydroxyl group, a thiol group, or an amino group. The specific (C12) component used is one of the examples provided below in the (C1) (thiol) compounds or (C2) amino group-containing monomers.

[0056] The (B1) iso(thio)cyanate compounds can be broadly classified into aliphatic isocyanates, alicyclic isocyanates, aromatic isocyanates, isothiocyanates, other isocyanates, and (B12) urethane prepolymers. Furthermore, the (B1) component may use one type of compound or multiple types of compounds. When multiple types of compounds are used, the standard mass is the total amount of the multiple types of compounds. Specific examples of these (B1) components are as follows.

[0057] Aliphatic isocyanates; (B1) component Ethylene diisocyanate, trimethylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate, octamethylene diisocyanate, nonamethylene diisocyanate, 2,2'-dimethylpentane diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, decamethylene diisocyanate, butene diisocyanate, 1,3-butadiene-1,4-diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, 1,6,11-trimethylundecamethylene diisocyanate, 1,3,6-trimethylhexamethylene Difunctional isocyanates such as ethylene diisocyanate, 1,8-diisocyanate-4-isocyanate methyl octane, 2,5,7-trimethyl-1,8-diisocyanate-5-isocyanate methyl octane, bis(isocyanate ethyl) carbonate, bis(isocyanate ethyl) ether, 1,4-butylene glycol dipropyl ether-ω,ω'-diisocyanate, lysine diisocyanate methyl ester, and 2,4,4-trimethylhexamethylene diisocyanate (corresponding to component (B13) that constitutes the (B12) urethane prepolymer detailed below).

[0058] Alicyclic isocyanates; (B1) component Isophorone diisocyanate, (bicyclo[2.2.1]heptane-2,5-diyl)bismethylene diisocyanate, (bicyclo[2.2.1]heptane-2,6-diyl)bismethylene diisocyanate, 2β,5α-bis(isocyanate)norbornane, 2β,5β-bis(isocyanate)norbornane, 2β,6α-bis(isocyanate)norbornane, 2β,6β-bis(isocyanate)norbornane, 2,6-di(isocyanatemethyl)furan, bis( Isocyanate methyl)cyclohexane, dicyclohexylmethane-4,4'-diisocyanate, 4,4-isopropylidenebis(cyclohexyl isocyanate), cyclohexane diisocyanate, methylcyclohexane diisocyanate, dicyclohexyldimethylmethane diisocyanate, 2,2'-dimethyldicyclohexylmethane diisocyanate, bis(4-isocyanate-n-butylidene)pentaerythritol, diisocyanate dimer acid, 2,5- Bis(isocyanate methyl)-bicyclo[2,2,1]-heptane, 2,6-bis(isocyanate methyl)-bicyclo[2,2,1]-heptane, 3,8-bis(isocyanate methyl)tricyclodecane, 3,9-bis(isocyanate methyl)tricyclodecane, 4,8-bis(isocyanate methyl)tricyclodecane, 4,9-bis(isocyanate methyl)tricyclodecane, 1,5-diisocyanate todecalin, 2,7-diisocyanate todecalin, 1,4- Diisocyanate todecalin, 2,6-diisocyanate todecalin, bicyclo[4.3.0]nonane-3,7-diisocyanate, bicyclo[4.3.0]nonane-4,8-diisocyanate, bicyclo[2.2.1]heptane-2,5-diisocyanate and bicyclo[2.2.1]heptane-2,6-diisocyanate, bicyclo[2,2,2]octane-2,5-diisocyanate, bicyclo[2,2,2]octane-2,6-diisocyanate, tricyclo[5.2.1.0 2.6 ] Decane-3,8-diisocyanate, tricyclo[5.2.1.0 2.6 ] A bifunctional isocyanate such as decane-4,9-diisocyanate (corresponding to component (B13) that constitutes the (B12) urethane prepolymer, as detailed below).

[0059] 2-Isocyanatemethyl-3-(3-isocyanatetopropyl)-5-isocyanatemethyl-bicyclo[2,2,1]-heptane, 2-Isocyanatemethyl-3-(3-isocyanatetopropyl)-6-isocyanatemethyl-bicyclo[2,2,1]-heptane, 2-Isocyanatemethyl-2-(3-isocyanatetopropyl)-5-isocyanatemethyl-bicyclo[2,2,1]-heptane, 2-Isocyanatemethyl-2-(3-isocyanatetopropyl)-6-isocyanatemethyl-bicyclo[2,2,1]-heptane, 2-Isocyanatemethyl-3-(3-isocyanatepropyl Polyfunctional isocyanates such as tris(isocyanate)-5-(2-isocyanate ethyl)-bicyclo[2,2,1]-heptane, 2-isocyanate methyl-3-(3-isocyanate propyl)-6-(2-isocyanate ethyl)-bicyclo[2,1,1]-heptane, 2-isocyanate methyl-2-(3-isocyanate propyl)-5-(2-isocyanate ethyl)-bicyclo[2,2,1]-heptane, 2-isocyanate methyl-2-(3-isocyanate propyl)-6-(2-isocyanate ethyl)-bicyclo[2,2,1]-heptane, and 1,3,5-tris(isocyanate methyl)cyclohexane.

[0060] Aromatic isocyanate; (B1) component Xylylene diisocyanate (o-, m-, p-), tetrachloro-m-xylylene diisocyanate, methylenediphenyl-4,4'-diisocyanate, 4-chlor-m-xylylene diisocyanate, 4,5-dichlor-m-xylylene diisocyanate, 2,3,5,6-tetrabrom-p-xylylene diisocyanate, 4-methyl-m-xylylene diisocyanate, 4-ethyl-m-xylylene diisocyanate, bis(isocyanate ethyl)benzene, bis(isocyanate propyl)benzene, 1,3-bis(α, α-dimethylisocyanate methyl)benzene, 1,4-bis(α,α-dimethylisocyanate methyl)benzene, α,α,α',α'-tetramethylxylylene diisocyanate, bis(isocyanate butyl)benzene, bis(isocyanate methyl)naphthalene, bis(isocyanate methyl)diphenyl ether, bis(isocyanate ethyl)phthalate, 2,6-di(isocyanate methyl)furan, phenylenediisocyanate (o-,m-,p-), tolylene diisocyanate, ethylphenylenediisocyanate, Sopropylphenylenediisocyanate, dimethylphenylenediisocyanate, diethylphenylenediisocyanate, diisopropylphenylenediisocyanate, trimethylbenzene triisocyanate, benzene triisocyanate, 1,3,5-triisocyanate methylbenzene, 1,5-naphthalenediisocyanate, methylnaphthalenediisocyanate, biphenyl diisocyanate, 2,4-tolylenediisocyanate, 2,6-tolylenediisocyanate, 4,4'-diphenylmethane diisocyanate, 2,2' -Diphenylmethane diisocyanate, 2,4'-Diphenylmethane diisocyanate, 3,3'-Dimethyldiphenylmethane-4,4'-Diisocyanate, Bibenzyl-4,4'-Diisocyanate, Bis(isocyanate phenyl)ethylene, 3,3'-Dimethoxybiphenyl-4,4'-Diisocyanate, Phenyl isocyanate methyl isocyanate, Phenyl isocyanate ethyl isocyanate, Tetrahydronaphthylene diisocyanate, Hexahydrobenzene diisocyanate, Hexahydrodiphenylmethane-4,Difunctional isocyanates such as 4'-diisocyanate, diphenyl ether diisocyanate, ethylene glycol-diphenyl ether diisocyanate, 1,3-propylene glycol-diphenyl ether diisocyanate, benzophenone diisocyanate, diethylene glycol-diphenyl ether diisocyanate, dibenzofrandiisocyanate, carbazole diisocyanate, ethylcarbazole diisocyanate, dichlorocarbazole diisocyanate, 2,4-tolylene diisocyanate, and 2,6-tolylene diisocyanate (corresponding to component (B13) that constitutes the urethane prepolymer (B12) detailed below).

[0061] Polyfunctional isocyanate compounds such as methylylene triisocyanate, triphenylmethane triisocyanate, polymeric MDI, naphthalene triisocyanate, diphenylmethane-2,4,4'-triisocyanate, 3-methyldiphenylmethane-4,4',6-triisocyanate, and 4-methyl-diphenylmethane-2,3,4',5,6-pentaiisocyanate.

[0062] Isothiocyanate; (B1) component difunctional isothiocyanates such as p-phenylenediisothiocyanate, xylylene-1,4-diisothiocyanate, and ethylidine diisothiocyanate (corresponding to component (B13) that constitutes the urethane prepolymer (B12) described in detail below).

[0063] Other isocyanates: (B1) component Other isocyanates include polyfunctional isocyanates having a burette structure, uretdione structure, or isocyanurate structure (for example, Japanese Patent Publication No. 2004-534870 discloses a method for modifying the burette structure, uretdione structure, or isocyanurate structure of aliphatic polyisocyanates) using diisocyanates such as hexamethylene diisocyanate and tolylene diisocyanate as the main raw material, and polyfunctional isocyanates formed as adducts with three or more functional polyols such as trimethylolpropane (disclosed in textbooks such as "Polyurethane Resin Handbook" edited by Keiji Iwata, Nikkan Kogyo Shimbun (1987)).

[0064] (B12) Urethane prepolymer; component (B1) having iso(thio)cyanate groups at both ends. In the present invention, a (B12) urethane prepolymer, produced by the reaction of the (B13) component with a (C12) bifunctional active hydrogen-containing compound having two active hydrogen-containing groups in the molecule (described later), can also be used as the (B1) component.

[0065] (B12) The urethane prepolymer is not particularly limited, but as component (B13), it is particularly preferable to use the monomers exemplified below. Specifically, it is preferable to use 1,5-naphthalene diisocyanate, xylene diisocyanate (o-,m-,p-), 2,4-tole diisocyanate, 2,6-tole diisocyanate, phenylene diisocyanate (o-,m-,p-), 2,2'-diphenylmethane diisocyanate, 2,4'-diphenylmethane diisocyanate, 4,4'-diphenylmethane diisocyanate, isophorone diisocyanate, 1,3-bis(isocyanate methyl)cyclohexane, dicyclohexylmethane-4,4'-diisocyanate, and (bicyclo[2.2.1]heptane-2,5(2,6)-diyl)bismethylene diisocyanate. It is preferable to react these with a (C12)2 functional active hydrogen-containing compound to obtain a (B12) component having either an isocyanate group or an isothiocyanate group at both ends.

[0066] Furthermore, in order for the final resin to exhibit particularly excellent properties, it is preferable to produce the (B12) urethane prepolymer using at least one (C12) bifunctional active hydrogen-containing compound having a molecular weight (number average molecular weight) of 300 to 2000. The active hydrogen-containing group refers to a hydroxyl group, a thiol group, or an amino group. Among these, considering reactivity, it is preferable that the active hydrogen-containing group in the (C12) bifunctional active hydrogen-containing compound be a hydroxyl group.

[0067] (C12) bifunctional active hydrogen-containing compounds with a molecular weight (number average molecular weight) of 300 to 2000 can be used in combination of different types and molecular weights. Furthermore, in order to adjust the hardness and strength of the final resin, when forming the (B12) urethane prepolymer, a combination of the (C12) component with a molecular weight (number average molecular weight) of 300 to 2000 and the (C12) component with a molecular weight (number average molecular weight) of 90 to 300 can be used. In this case, depending on the type of (C12) component and the (B13) bifunctional iso(thio)cyanate compound component used, and the amount used, it is preferable that when the (C12) component with a molecular weight of 300 to 2000 is used, the (C12) component with a molecular weight of 90 to 300 is used in a ratio of 0 to 50 parts by mass. Moreover, it is preferable that the (C12) component with a molecular weight of 90 to 300 is used in a ratio of 1 to 40 parts by mass. When using the curable composition of the present invention as an abrasive pad, it is preferable to use the (B12) urethane prepolymer described above. More preferably, it is preferable to use a (B12) urethane prepolymer synthesized by combining a (C12) component having a molecular weight (number average molecular weight) of 300 to 2000 and a (C12) component having a molecular weight (number average molecular weight) of 90 to 300. Furthermore, the ratio of the (C12) component with a molecular weight (number average molecular weight) of 300 to 2000 to the (C12) component with a molecular weight (number average molecular weight) of 90 to 300 is preferably such that, when the total mass parts of the (C12) component with a molecular weight (number average molecular weight) of 300 to 2000 and the (C12) component with a molecular weight (number average molecular weight) of 90 to 300 is 100 parts by mass, the (C12) component with a molecular weight (number average molecular weight) of 300 to 2000 is 60 to 95 parts by mass, and more preferably 70 to 95 parts by mass.

[0068] Furthermore, the (B12) urethane prepolymer must have isocyanate groups and / or isothiocyanate groups at both ends of the molecule. Therefore, it is preferable to manufacture the (B12) urethane prepolymer in such a way that the total number of moles (n5) of isocyanate groups and / or isothiocyanate groups in the (B13) bifunctional iso(thio)cyanate compound and the total number of moles (n6) of active hydrogen-containing groups (hydroxyl groups, thiol groups, or amino groups) in the (C12) bifunctional active hydrogen-containing compound are within the range of 1 < (n5) / (n6) ≤ 2.3. When using two or more components whose molecular ends are (B13), the number of moles (n5) of the isocyanate groups and / or isothiocyanate groups is, of course, the total number of moles of isocyanate groups and / or isothiocyanate groups in the (B13) component. Furthermore, the number of moles of active hydrogen-containing groups (n6) in two or more (C12) bifunctional active hydrogen-containing compounds is, of course, the total number of moles of active hydrogen from the active hydrogen-containing groups. Even if the active hydrogen-containing group is a primary amino group, the primary amino group is considered to be 1 mole. In other words, a considerable amount of energy is required for a second amino group (-NH) to react with a primary amino group (even with a primary amino group, the second -NH is difficult to react). Therefore, in this invention, even if a (C12) bifunctional active hydrogen-containing compound having a primary amino group is used, the primary amino group can be calculated as 1 mole.

[0069] The isocyanate equivalent (total amount of isocyanate equivalent and / or isothiocyanate equivalent) of the (B12) urethane prepolymer can be determined by quantifying the isocyanate groups and / or isothiocyanate groups present in the (B12) urethane prepolymer in accordance with JIS K 7301. The isocyanate groups and / or isothiocyanate groups can be quantified by the following back titration method. First, the obtained (B12) urethane prepolymer is dissolved in a dry solvent. Next, a known amount of di-n-butylamine, which is clearly in excess of the amount of isocyanate groups and / or isothiocyanate groups present in the (B12) urethane prepolymer, is added to the dry solvent to react all the isocyanate groups and / or isothiocyanate groups of the (B12) urethane prepolymer with the di-n-butylamine. Next, the di-n-butylamine that was not consumed (did not participate in the reaction) is titrated with acid to determine the amount of consumed di-n-butylamine. Since the amount of consumed di-n-butylamine is equal to the amount of isocyanate groups and / or isothiocyanate groups in the (B12) urethane prepolymer, the isocyanate equivalent can be determined. Furthermore, since the (B12) urethane prepolymer is a linear urethane prepolymer with isocyanate groups and / or isothiocyanate groups at both ends, the number-average molecular weight of the (B12) urethane prepolymer is twice the isocyanate equivalent. The molecular weight of this (B12) urethane prepolymer tends to match the value measured by gel permeation chromatography (GPC). Note that, for example, when using the (B12) urethane prepolymer in combination with the (B13) bifunctional isocyanate compound, the mixture of both can be measured according to the method described above.

[0070] The (B12) urethane prepolymer is not particularly limited, but it is preferably an iso(thio)cyanate equivalent of 300 to 5000, more preferably 350 to 3000, and most preferably 350 to 2000. The reason for this is not particularly clear, but it is thought to be as follows: When a (B12) urethane prepolymer having a certain molecular weight reacts with the active hydrogen group of a cyclic molecule having an active hydrogen group-containing side chain, the movable site of the molecule, including the side chain, becomes larger, increasing the movement of the molecule itself, and as a result, it is thought to recover from deformation (elastic recovery; low hystericity) more easily. Furthermore, it is thought that by using the (B12) urethane prepolymer, the crosslinking points in the resin become more dispersed and exist randomly and uniformly, resulting in stable performance. In addition, the resin obtained using the (B12) urethane prepolymer is easier to control during manufacturing. For example, it is thought that it can be suitably used when the curable composition of the present invention is used as an abrasive pad. These effects are thought to occur even when the average iso(thio)cyanate equivalent of the polyiso(thio)cyanate compound is 300 to 5000, when (B12) urethane prepolymer and (B13) bifunctional iso(thio)cyanate compound are used in combination. However, these effects are thought to be more pronounced when (B12) urethane prepolymer is used alone.

[0071] The method for producing the (B12) urethane prepolymer used in the present invention involves reacting a (C12) bifunctional active hydrogen-containing compound having two active hydrogen-containing groups in its molecule, such as a hydroxyl group, an amino group, or a thiol group, with a (B13) bifunctional iso(thio)cyanate compound to produce a (B12) urethane prepolymer having an isocyanate group or an isothiocyanate group at the end of the molecule. There are no limitations as long as a prepolymer having an isocyanate group or an isothiocyanate group at the end can be obtained.

[0072] As mentioned above, the preferred amounts of the (C12) bifunctional active hydrogen-containing compound and the (B13) bifunctional iso(thio)cyanate compound for obtaining the (B12) urethane prepolymer are as follows. Specifically, it is preferable to manufacture the product in a range where the number of moles of isocyanate groups or isothiocyanate groups in the (B13) component (n5) and the number of moles of active hydrogen in the (C12) bifunctional active hydrogen-containing compound (n6) are within the range of 1 < (n5) / (n6) ≤ 2.3.

[0073] Furthermore, the reaction for the production of urethane prepolymers can be carried out by adding heating or a urethane catalyst as needed.

[0074] The most preferred examples of the (B1) component used in the present invention are, from the viewpoint of controlling the strength and reactivity of the formed resin, isophorone diisocyanate, 1,3-bis(isocyanate methyl)cyclohexane, dicyclohexylmethane-4,4'-diisocyanate, alicyclic isocyanate of (bicyclo[2.2.1]heptane-2,5(2,6)-diyl)bismethylene diisocyanate, 2,4-tolylene diisocyanate, and 2,6-tolylene diisocyanate. Examples include aromatic isocyanates such as annetes, 4,4'-diphenylmethane diisocyanate, xylylene diisocyanate (o-, m-, p-), polyfunctional isocyanates with burette, uretdione, and isocyanurate structures, which are mainly derived from diisocyanates such as hexamethylene diisocyanate and tolylene diisocyanate, polyfunctional isocyanates as adducts with trifunctional or more polyols, or (B12) urethane prepolymers.

[0075] Among these, (B12) urethane prepolymer is particularly preferred. By using (B12) urethane prepolymer, it is possible to obtain desirable resin properties. Particularly preferred is a urethane prepolymer in which (B12) urethane prepolymer consists of an aromatic isocyanate, and most preferably a urethane prepolymer consisting of 2,4-tolylene diisocyanate or 2,6-tolylene diisocyanate.

[0076] <(B2) Epoxy group-containing monomer; (B2) component> Epoxy group-containing monomers are those that have an epoxy group within their molecule as a polymerizable functional group.

[0077] Such epoxy compounds can be broadly classified into aliphatic epoxy compounds, alicyclic epoxy monomers, and aromatic epoxy monomers. Suitable specific examples include those described in International Publication No. 2015 / 068798.

[0078] The content of component (B) in the curable composition is not particularly limited, but is preferably 100 to 1000 parts by mass, and more preferably 300 to 800 parts by mass, per 100 parts by mass of component (A).

[0079] <(C1)(thiol) compounds; (C1) components> (C1)(thiol) compounds can be used without restriction as long as they have at least two groups selected from the group consisting of hydroxyl groups and thiol groups in one molecule. Of course, compounds having both a hydroxyl group and a thiol group are also selected.

[0080] The aforementioned (C1) component can be broadly classified into aliphatic alcohols, alicyclic alcohols, aromatic alcohols, polyester polyols, polyether polyols, polycaprolactone polyols, polycarbonate polyols, polyacrylic polyols, castor oil-based polyols, thiols, monomers containing OH / SH type polymerizable groups, and polyrotaxanes having hydroxyl and / or thiol groups that can be polymerized with isocyanate groups. Specific examples include the following:

[0081] Aliphatic alcohol; (C1) component Difunctional polyols such as ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, butylene glycol, 1,5-dihydroxypentane, 1,6-dihydroxyhexane, 1,7-dihydroxyheptane, 1,8-dihydroxyoctane, 1,9-dihydroxynonane, 1,10-dihydroxydecane, 1,11-dihydroxyundecane, 1,12-dihydroxydodecane, neopentyl glycol, glyceryl monooleate, monoelidine, polyethylene glycol, 3-methyl-1,5-dihydroxypentane, dihydroxyneopentyl, 2-ethyl-1,2-dihydroxyhexane, and 2-methyl-1,3-dihydroxypropane (corresponding to the (C12) difunctional active hydrogen-containing compounds that constitute the urethane prepolymer (B12)).

[0082] Polyfunctional polyols such as glycerin, trimethylolethane, trimethylolpropane, ditrimethylolpropane, trimethylolpropane tripolyoxyethylene ether (e.g., TMP-30, TMP-60, TMP-90 from Nippon Emulsifier Co., Ltd.), butanetriol, 1,2-methylglucoside, pentaerythritol, dipentaerythritol, tripentaerythritol, sorbitol, erythritol, slayitol, ribitol, arabinitol, xylitol, alitol, mannitol, dolucitol, iditol, glycol, inositol, hexanetriol, triglycerol, diglycerol, and triethylene glycol.

[0083] Alicyclic alcohol; (C1) component Hydrogenated bisphenol A, cyclobutanediol, cyclopentanediol, cyclohexanediol, cycloheptanediol, cyclooctanediol, cyclohexanedimethanol, hydroxypropylcyclohexanol, tricyclo[5,2,1,0 2,6 ] Decane-dimethanol, bicyclo[4,3,0]-nonanediol, dicyclohexanediol, tricyclo[5,3,1,13,9]dodecanediol, bicyclo[4,3,0]nonanedimethanol, tricyclo[5,3,1,13,9 ] Dodecane-diethanol, hydroxypropyl tricyclo[5,3,1,1 3,9 ]Dodecanol, spiro[3,4]octanediol, butylcyclohexanediol, 1,1'-bicyclohexylidenediol, 1,4-cyclohexanedimethanol, 1,3-cyclohexanedimethanol, 1,2-cyclohexanedimethanol, and difunctional polyols such as o-dihydroxyxylylene (corresponding to the (C12) difunctional active hydrogen-containing compounds that constitute the (B12) urethane prepolymer).

[0084] Polyfunctional polyols such as tris(2-hydroxyethyl) isocyanurate, cyclohexanetriol, sucrose, maltitol, and lactitol.

[0085] Aromatic alcohol; (C1) component Dihydroxynaphthalene, dihydroxybenzene, bisphenol A, bisphenol F, xylylene glycol, tetrabrombisphenol A, bis(4-hydroxyphenyl)methane, 1,1-bis(4-hydroxyphenyl)ethane, 1,2-bis(4-hydroxyphenyl)ethane, bis(4-hydroxyphenyl)phenylmethane, bis(4-hydroxyphenyl)diphenylmethane, bis(4-hydroxyphenyl)-1-naphthylmethane, 1,1-bis(4-hydroxyphenyl)-1-phenylethane, 2-(4-hydroxyphenyl 2,2-(3-hydroxyphenyl)propane, 2,2-bis(4-hydroxyphenyl)butane, 1,1-bis(4-hydroxyphenyl)butane, 2,2-bis(4-hydroxyphenyl)-3-methylbutane, 2,2-bis(4-hydroxyphenyl)pentane, 3,3-bis(4-hydroxyphenyl)pentane, 2,2-bis(4-hydroxyphenyl)hexane, 2,2-bis(4-hydroxyphenyl)octane, 2,2-bis(4-hydroxyphenyl)-4-methylpentane, 2,2-bis(4-hydroxyphenyl) Butane, 4,4-bis(4-hydroxyphenyl)heptane, 2,2-bis(4-hydroxyphenyl)tridecane, 2,2-bis(4-hydroxyphenyl)octane, 2,2-bis(3-methyl-4-hydroxyphenyl)propane, 2,2-bis(3-ethyl-4-hydroxyphenyl)propane, 2,2-bis(3-n-propyl-4-hydroxyphenyl)propane, 2,2-bis(3-isopropyl-4-hydroxyphenyl)propane, 2,2-bis(3-sec-butyl-4-hydroxyphenyl)propane, 2,2-bis(3- tert-butyl-4-hydroxyphenyl)propane, 2,2-bis(3-cyclohexyl-4-hydroxyphenyl)propane, 2,2-bis(3-allyl-4'-hydroxyphenyl)propane, 2,2-bis(3-methoxy-4-hydroxyphenyl)propane, 2,2-bis(3,5-dimethyl-4-hydroxyphenyl)propane, 2,2-bis(2,3,5,6-tetramethyl-4-hydroxyphenyl)propane, bis(4-hydroxyphenyl)cyanomethane, 1-cyano-3,3-bis(4-hydroxyphenyl)butane, 2,2-bis(4-hydroxyphenyl)hexafluoropropane, 1,1-bis(4-hydroxyphenyl)cyclopentane, 1,1-bis(4-hydroxyphenyl)cyclohexane, 1,1-bis(4-hydroxyphenyl)cycloheptane, 1,1-bis(3-methyl-4-hydroxyphenyl)cyclohexane, 1,1-bis(3,5-dimethyl-4-hydroxyphenyl)cyclohexane, 1,1-bis(3,5-dichloro-4-hydroxyphenyl)cyclohexane, 1,1-bis(3-methyl-4-hydroxyphenyl)-4-methylcyclohexane, 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane, 2,2-bis(4-hydroxyphenyl)norbornane, 2,2-bis(4-hydroxyphenyl)adamantane, 4,4'-dihydroxydiphenyl ether, 4,4'-dihydroxy-3,3'-dimethyldiphenyl ether, ethylene glycol bis(4-hydroxyphenyl) ether, 4,4'- Dihydroxydiphenyl sulfide, 3,3'-dimethyl-4,4'-dihydroxydiphenyl sulfide, 3,3'-dicyclohexyl-4,4'-dihydroxydiphenyl sulfide, 3,3'-diphenyl-4,4'-dihydroxydiphenyl sulfide, 4,4'-dihydroxydiphenyl sulfoxide, 3,3'-dimethyl-4,4'-dihydroxydiphenyl sulfoxide, 4,4'-dihydroxydiphenyl sulfone, 4,4'-dihydroxy-3,3'-dimethyldiphenyl sulfone, bis(4-hydroxyphenyl) ketone, bis(4-hydroxy-3-methylphenyl) ketone, 7,7' -Dihydroxy-3,3',4,4'-tetrahydro-4,4,4',4'-tetramethyl-2,2'-spirobi(2H-1-benzopyran), trans-2,3-bis(4-hydroxyphenyl)-2-butene, 9,9-bis(4-hydroxyphenyl)fluorene, 3,3-bis(4-hydroxyphenyl)-2-butanone, 1,6-bis(4-hydroxyphenyl)-1,6-hexanedione, 4,4'-dihydroxybiphenyl, m-dihydroxyxylylene, p-dihydroxyxylylene, 1,4-bis(2-hydroxyethyl)benzene, 1,4-bis(3-hydroxypropyl)benzene, 1,4-bis(4-hydroxybutyl)benzene, 1,4-bis(5-hydroxypentyl)benzene, 1,4-bis(6-hydroxyhexyl)benzene, 2,2-bis[4-(2"-hydroxyethyloxy)phenyl]propane, and difunctional polyols such as hydroquinone and resorcin (corresponding to the (C12) difunctional active hydrogen-containing compounds constituting the (B12) urethane prepolymer).

[0086] Polyfunctional polyols such as trihydroxynaphthalene, tetrahydroxynaphthalene, benzenetriol, biphenyltetraol, pyrogallol, (hydroxynaphthyl)pyrogallol, and trihydroxyphenanthrene.

[0087] Polyester polyol; (C1) component Examples include compounds obtained by the condensation reaction of polyols and polybasic acids. Among these, a number-average molecular weight of 400 to 2000 is preferred, more preferably 500 to 1500, and most preferably 600 to 1200. Compounds having hydroxyl groups only at both ends of the molecule (two within the molecule) correspond to the (C12) bifunctional active hydrogen-containing compounds that constitute the (B12) urethane prepolymer. Examples of polyols include ethylene glycol, 1,2-propanediol, 1,3-butanediol, 1,4-butanediol, 3-methyl-1,5-pentanediol, 1,6-hexanediol, 3,3'-dimethylolheptane, 1,4-cyclohexanedimethanol, neopentyl glycol, 3,3-bis(hydroxymethyl)heptane, diethylene glycol, dipropylene glycol, glycerin, and trimethylolpropane. These may be used individually or in combination of two or more. Examples of polybasic acids include succinic acid, adipic acid, azelaic acid, sebacic acid, dodecanedicarboxylic acid, cyclopentanedicarboxylic acid, cyclohexanedicarboxylic acid, orthophthalic acid, isophthalic acid, terephthalic acid, and naphthalenedicarboxylic acid. These may be used individually or in combination of two or more. These polyester polyols are available as reagents or industrially. Examples of commercially available products include the "Polylight®" series from DIC Corporation, the "Nipporan®" series from Nippon Polyurethane Industry Co., Ltd., the "Maximol®" series from Kawasaki Chemical Industries, Ltd., and the "Kuraray Polyol®" series from Kuraray Co., Ltd.

[0088] Polyether polyol; (C1) component Examples include compounds obtained by ring-opening polymerization of alkylene oxides, or by the reaction of an alkylene oxide with a compound having two or more active hydrogen-containing groups in its molecule, and their modified forms. Among these, a number-average molecular weight of 400 to 2000 is preferred, more preferably 500 to 1500, and most preferably 600 to 1200. Compounds having hydroxyl groups only at both ends of the molecule (two in the molecule) correspond to the (C12) bifunctional active hydrogen-containing compounds that constitute the (B12) urethane prepolymer. Here, examples of polyether polyols include polymer polyols, urethane-modified polyether polyols, and polyether ester copolymer polyols. Examples of compounds having two or more active hydrogen-containing groups in their molecules include water, ethylene glycol, propylene glycol, butanediol, glycerin, trimethylolpropane, hexanetriol, triethanolamine, diglycerin, pentaerythritol, trimethylolpropane, hexanetriol, and polyol compounds such as glycols and glycerin that have one or more hydroxyl groups in their molecules. These may be used individually or in mixtures of two or more. Furthermore, examples of alkylene oxides include cyclic ether compounds such as ethylene oxide, propylene oxide, and tetrahydrofuran, which may be used individually or in combination of two or more. Such polyether polyols are available as reagents or industrially. Examples of commercially available products include the "Exenol®" series and "Emulstar®" from Asahi Glass Co., Ltd., and the "ADEKA Polyether" series from ADEKA Corporation.

[0089] Polycaprolactone polyol; (C1) component Examples include compounds obtained by ring-opening polymerization of ε-caprolactone. Among these, a number-average molecular weight of 400 to 2000 is preferred, more preferably 500 to 1500, and most preferably 600 to 1200. Compounds having hydroxyl groups only at both ends of the molecule (two within the molecule) correspond to the (C12) bifunctional active hydrogen-containing compounds that constitute the (B12) urethane prepolymer. These polycaprolactone polyols are available as reagents or industrially, and commercially available examples include the "Praxel®" series manufactured by Daicel Chemical Industries, Ltd.

[0090] Polycarbonate polyol; (C1) component Examples include compounds obtained by phosgenating one or more low molecular weight polyols, or compounds obtained by transesterification using ethylene carbonate, diethyl carbonate, diphenyl carbonate, etc. Among these, the number average molecular weight is preferably 400 to 2000, more preferably 500 to 1500, and most preferably 600 to 1200. Compounds having hydroxyl groups only at both ends of the molecule (two within the molecule) correspond to the (C12) bifunctional active hydrogen-containing compounds that constitute the (B12) urethane prepolymer. Examples of low molecular weight polyols include ethylene glycol, 1,2-propanediol, 1,3-propanediol, 2-methyl-1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, 3-methyl-1,5-pentanediol, 2-ethyl-4-butyl-1,3-propanediol, diethylene glycol, dipropylene glycol, neopentyl glycol, cyclohexane-1,4-diol, cyclohexane-1,4-dimethanol, dimer acid diol, ethylene oxide and propylene oxide adducts of bisphenol A, bis(β-hydroxyethyl)benzene, xylylene glycol, glycerin, trimethylolpropane, pentaerythritol, and other low molecular weight polyols.

[0091] Polyacrylic polyol; (C1) component Examples include polyol compounds obtained by polymerizing (meth)acrylate esters and vinyl monomers. Those having hydroxyl groups only at both ends of the molecule (two within the molecule) correspond to the (C12) bifunctional active hydrogen-containing compounds that constitute the (B12) urethane prepolymer.

[0092] Castor oil-based polyol; (C1) component Examples of castor oil-based polyols include polyol compounds that use castor oil, a natural oil, as a starting material. Those having hydroxyl groups only at both ends of the molecule (two groups within the molecule) correspond to the (C12) component that makes up the (B12) urethane prepolymer. These castor oil polyols are available as reagents or industrially, and commercially available examples include the "URIC®" series manufactured by Ito Oil Co., Ltd.

[0093] Thiol; (C1) component Suitable examples of thiols can be found in the International Publication No. 2015 / 068798 brochure. Among these, particularly suitable examples include the following:

[0094] Tetraethylene glycol bis(3-mercaptopropionate), 1,4-butanediol bis(3-mercaptopropionate), 1,6-hexanediol bis(3-mercaptopropionate), 1,4-bis(mercaptopropylthiomethyl)benzene (corresponding to the (C12) bifunctional active hydrogen-containing compound constituting the (B12) urethane prepolymer).

[0095] Trimethylolpropanetris(3-mercaptopropionate), pentaerythritoltetrakis(3-mercaptopropionate), dipentaerythritolhexakis(3-mercaptopropionate), 1,2-bis[(2-mercaptoethyl)thio]-3-mercaptopropane, 2,2-bis(mercaptomethyl)-1,4-butanedithiol, 2,5-bis(mercaptomethyl)-1,4-dithiane, 4- Thiols such as mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 1,1,1,1-tetrakis(mercaptomethyl)methane, 1,1,3,3-tetrakis(mercaptomethylthio)propane, 1,1,2,2-tetrakis(mercaptomethylthio)ethane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, and tris-{(3-mercaptopropionyloxy)ethyl}isocyanurate.

[0096] OH / SH type polymerizable group-containing monomer; (C1) component 2-mercaptoethanol, 1-hydroxy-4-mercaptocyclohexane, 2-mercaptohydroquinone, 4-mercaptophenol, 1-hydroxyethylthio-3-mercaptoethylthiobenzene, 4-hydroxy-4'-mercaptodiphenylsulfone, 2-(2-mercaptoethylthio)ethanol, dihydroxyethyl sulfide mono(3-mercaptopropionate), dimercaptoethane mono(saltylate) (corresponding to the (C12) bifunctional active hydrogen-containing compound constituting the (B12) urethane prepolymer).

[0097] Polyfunctional OH / SH type polymerizable group-containing monomers such as 3-mercapto-1,2-propanediol, glycerin di(mercaptoacetate), 2,4-dimercaptophenol, 1,3-dimercapto-2-propanol, 2,3-dimercapto-1-propanol, 1,2-dimercapto-1,3-butanediol, pentaerythritol tris(3-mercaptopropionate), pentaerythritol mono(3-mercaptopropionate), pentaerythritol bis(3-mercaptopropionate), pentaerythritol tris(thioglycolate), pentaerythritol pentakis(3-mercaptopropionate), hydroxymethyl-tris(mercaptoethylthiomethyl)methane, and hydroxyethylthiomethyltris(mercaptoethylthio)methane.

[0098] Polyrotaxane having isocyanate groups and polymerizable hydroxyl and / or thiol groups; (C1) component A polyrotaxane is a molecular complex in which a chain-like axial molecule penetrates the rings of multiple cyclic molecules, and bulky groups are bonded to both ends of the axial molecule, preventing the cyclic molecules from detaching from the axial molecule due to steric hindrance. It is also called a supramolecule. The polyrotaxane that can be used in component (C1) of the present invention is a polyrotaxane having an isocyanate group and polymerizable hydroxyl and / or thiol groups. The polyrotaxane having hydroxyl and / or thiol groups used in component (C1) of the present invention is not particularly limited, but examples include the polyrotaxane described in International Application No. 2018 / 092826.

[0099] <(C2) Amino group-containing monomer; (C2) component> The (C2) amino group-containing monomers used in the present invention are not limited to any monomer having two or more groups selected from primary and secondary amino groups in one molecule. The amino group-containing monomers can be broadly classified into aliphatic amines, alicyclic amines, aromatic amines, and polyrotaxanes having amino groups that can be polymerized with isocyanate groups.

[0100] (C2)Specific examples of monomers containing an amino group include the following:

[0101] Aliphatic amines; (C2) components Difunctional amines such as ethylenediamine, hexamethylenediamine, nonamethylenediamine, undecanemethylenediamine, dodecamethylenediamine, metaxylenediamine, 1,3-propanediamine, and putrescine (corresponding to the (C12) difunctional active hydrogen-containing compounds that constitute the (B12) urethane prepolymer). Polyfunctional amines such as diethylenetriamine and other polyamines.

[0102] Alicyclic amines; (C2) components Difunctional amines such as isophorone diamine and cyclohexyl diamine (corresponding to the (C12) difunctional active hydrogen-containing compounds that constitute the (B12) urethane prepolymer).

[0103] Aromatic amine; (C2) component 4,4'-Methylenebis(o-chloroaniline)(MOCA), 2,6-Dichloro-p-phenylenediamine, 4,4'-Methylenebis(2,3-Dichloroaniline), 4,4'-Methylenebis(2-Ethyl-6-methylaniline), 3,5-Bis(methylthio)-2,4-Toluenediamine, 3,5-Bis(methylthio)-2,6-Toluenediamine, 3,5-Diethyltoluene-2,4-Diamine, 3,5-Diethyltoluene-2,6 -Diamine, trimethylene glycol-di-p-aminobenzoate, polytetramethylene glycol-di-p-aminobenzoate, 4,4'-diamino-3,3',5,5'-tetraethyldiphenylmethane, 4,4'-diamino-3,3'-diisopropyl-5,5'-dimethyldiphenylmethane, 4,4'-diamino-3,3',5,5'-tetraisopropyldiphenylmethane, 1,2-bis(2-aminophenylthio)ethane , 4,4'-diamino-3,3'-diethyl-5,5'-dimethyldiphenylmethane, N,N'-di-sec-butyl-4,4'-diaminodiphenylmethane, 3,3'-diethyl-4,4'-diaminodiphenylmethane, m-xylylenediamine, N,N'-di-sec-butyl-p-phenylenediamine, m-phenylenediamine, p-xylylenediamine, p-phenylenediamine, 3,3'-methylenebis(methyl-6-amino Difunctional amines such as (B12) di-active hydrogen-containing compounds (C12) that constitute the (B12) urethane prepolymer, including (B12) di-active hydrogen-containing compounds (C Polyfunctional amines such as 1,3,5-benzenetriamine and melamine.

[0104] Polyrotaxane having an isocyanate group and a polymerizable amino group; (C2) component The polyrotaxane that can be used in component (C2) of the present invention is a polyrotaxane having an isocyanate group and a polymerizable amino group. The polyrotaxane having an amino group used in component (C2) of the present invention is not particularly limited, but examples include the polyrotaxane described in International Application No. 2018 / 092826.

[0105] In the present invention, when a curable composition containing component (A) and component (B), and optionally component (C), is used to produce a cured product of the present invention, the curable composition containing component (A), component (B1), component (B2), component (C1), and component (C2) is preferably formulated as follows.

[0106] Specifically, it is preferable that the total amount of components (B1), (B2), (C1), and (C2) (hereinafter also referred to as "amounts of components (B) and (C)") plus component (A) be in the range of 2 to 70 parts by mass, and the amounts of components (B) and (C) be in the range of 30 to 98 parts by mass. By including component (A) in this ratio, the resulting cured body can exhibit excellent mechanical properties. Furthermore, a preferred range can be adjusted depending on the application. For example, when used in polishing pad applications, it is preferable that the cured body be a urethane resin. Note that if the cured body is a urethane resin, component (B1) is essential. When used in polishing pad applications, it is more preferable that the cured body contains 5 to 70 parts by mass of component (A) and the amounts of components (B) and (C) be in the range of 30 to 95 parts by mass, and even more preferably that the cured body contains 8 to 50 parts by mass of component (A) and the amounts of components (B) and (C) be in the range of 50 to 92 parts by mass. By including it within this range, it becomes possible to achieve excellent wear resistance and polishing properties.

[0107] Furthermore, when used for polishing pad applications, when the amounts of components (B) and (C) are set to 100% by mass, it is preferable to have (B1) at 20-100% by mass, (B2) at 0-100% by mass, (C1) at 0-80% by mass, and (C2) at 0-30% by mass, in order to exhibit excellent mechanical properties. To further enhance this effect, it is even more preferable to have (B1) at 20-95% by mass, (B2) at 0-20% by mass, (C1) at 0-70% by mass, and (C2) at 0-25% by mass, and most preferably (B1) at 40-95% by mass, (B2) at 0-5% by mass, (C1) at 0-35% by mass, and (C2) at 0-20% by mass.

[0108] Among the above, in order for the final cured product to exhibit particularly excellent properties, it is preferable to use (B12) urethane prepolymer as at least component (B1). In that case, when used for polishing pad applications, when the amounts of components (B) and (C) are set to 100% by mass, it is preferable that the amounts of components other than (B12) be 0-10% by mass for (B1) component, 50-90% by mass for (B12) component, 0-5% by mass for (B2) component, 0-20% by mass for (C1) component, and 0-20% by mass for (C2) component.

[0109] <Regarding suitable curable compositions> The curable composition containing component (A) and component (B) above, and optionally component (C), is not particularly limited in composition and can be used.

[0110] In particular, for use in preferred polishing pad materials, the curable composition preferably has an active hydrogen group of component (A) selected from hydroxyl groups and amino groups, and component (B) preferably contains an iso(thio)cyanate compound (B1). By selecting from these, the cured product becomes a cured product made of urethane resin.

[0111] Among these, it is preferable that component (B1) be selected from the (B12) urethane prepolymer. This makes it easier to adjust for excellent mechanical properties and polishing properties. In particular, it is preferable that the active hydrogen group of component (A) contains at least a hydroxyl group or an amino group, and that the (B1) iso(thio)cyanate compound contained in component (B) contains component (B12).

[0112] The aforementioned component (B) preferably comprises (B1) an iso(thio)cyanate compound and further (C1) a (thio)ol compound and / or (C2) an amino group-containing monomer. In this case as well, it is even more preferable that the above component (B1) is component (B12). In the present invention, urethane resin refers to a resin in which the cured product has any of the following bonds: urethane bond, urea bond, thiourethane bond, thiourea bond, or a mixture thereof.

[0113] <Other ingredients included in the curable composition> In the curable composition of the present invention, various (D) polymerization curing accelerators (hereinafter also referred to as (D) component) can be used to rapidly promote curing, depending on the type of component (A) and (B) described above.

[0114] For example, if component (B) contains an iso(thio)cyanate compound (B1), then component (D) may be a reaction catalyst for urethane or urea or a condensing agent (D2).

[0115] Furthermore, if component (B) contains (B2) an epoxy group-containing monomer, then component (D) may be (D3) an epoxy curing agent or (D4) a cationic polymerization catalyst for ring-opening polymerization of the epoxy group.

[0116] As specific examples of polymerization accelerators (D1) to (D4) that can be suitably used in the present invention, those described in International Publication No. WO2015 / 068798 can be used.

[0117] Each of these various (D) components can be used individually or in combination of two or more, but the amount used should be in the so-called catalytic amount, for example, 0.001 to 10 parts by mass, particularly 0.01 to 5 parts by mass, per 100 parts by mass of the total of components (A), (B), and (C) as needed.

[0118] The curable composition of the present invention may also contain various known compounding agents, as long as they do not impair the effects of the present invention. For example, abrasive grains, antioxidants, ultraviolet absorbers, infrared absorbers, color inhibitors, fluorescent dyes, dyes, photochromic compounds, pigments, fragrances, surfactants, flame retardants, plasticizers, fillers, antistatic agents, foam stabilizers, solvents, leveling agents, and other additives may be added. These additives may be used individually or in combination of two or more. These additives can be incorporated into the curable composition and then incorporated into the cured product of the present invention by curing the curable composition.

[0119] The method for producing the curable composition of the present invention is not particularly limited and can be produced by mixing the above-mentioned components by known methods. In particular, it is preferable to store the reacting components (for example, component (A) and component (B)) separately before curing and mix them immediately before curing to form the curable composition. Known methods can be used for curing in the present invention. In the case of sequential addition reactions, the conditions described in International Publication Nos. 2015 / 068798, 2016 / 143910, and 2018 / 092826 can be used. Specifically, dry methods such as the one-pot method and the prepolymer method, and wet methods using solvents can be used. Among these, dry methods are preferably used. In the case of chain polymerization, the conditions described in International Publication Nos. 2014 / 136804 and 2015 / 068798 are preferably used.

[0120] In the present invention, the cured body obtained by curing the curable composition can also be a foamed cured body obtained by foaming the cured body. Whether to make a foamed cured body or a non-foamed cured body can be selected depending on the desired application and hardness, but in the present invention, a foamed cured body is more preferable when used as an abrasive pad. Such a foamed cured body can be obtained by foaming methods known to the public, for example, by blending a foaming agent or fine particles into the curable composition, or by blowing gas into the curable composition and then curing it. Examples of specific methods for foaming the cured body include foaming methods using volatile foaming agents such as low-boiling hydrocarbons or by adding water, methods for dispersing and curing fine hollow particles (microballoons), methods for mixing thermally expandable fine particles and then heating to foam the fine particles, or mechanical floss foaming methods in which an inert gas such as air or nitrogen is blown in during mixing. Among these, fine hollow particles are preferable as they can be suitably used when the resulting cured body is a foam.

[0121] The following describes minute hollow particles. <(E) Microscopic hollow particles> The aforementioned (E) fine hollow particles (hereinafter also referred to as "component (E)") can be any known material without limitation. For example, particles forming the outer shell can be made from vinylidene chloride resin, (meth)acrylate resin, acrylonitrile-vinylidene chloride copolymer, epoxy resin, phenolic resin, melamine resin, urethane resin, etc. Among these, component (E) is preferably a hollow particle composed of an outer shell made of urethane resin and melamine resin, and a hollow portion surrounded by the outer shell. In this invention, the urethane resin is a resin having urethane bonds and / or urea bonds. The melamine resin is a resin produced by polycondensation of melamine and formaldehyde. Using these hollow particles allows for the efficient and easy production of a uniform foam. Furthermore, using these hollow particles reduces the likelihood of defects such as scratches, and also reduces hysteresis loss.

[0122] (E) component's average particle size is not particularly limited, but is preferably in the following range. Specifically, it is preferably 1 μm to 500 μm, more preferably 5 μm to 200 μm, and most preferably 10 μm to 100 μm.

[0123] Also, the density of the (E) component is not particularly limited, but is preferably in the following range. Specifically, it is preferably 0.01 g / cm 3 ~0.5 g / cm 3 and more preferably 0.02 g / cm 3 ~0.3 g / cm 3 Here, the density is the density of the (E) component when expanded. In the stage of mixing with the curable composition of the present invention, as long as it is an unexpanded type particle and the (E) component expands by the heat during curing, it is preferable that the density when expanded is the above density.

[0124] (E) component's blending amount may be appropriately determined according to the intended use. Among them, when the obtained cured body is used as a polishing pad, it is preferably the following blending amount. Specifically, per 100 parts by mass of the total of the (A) component, the (B) component, and the (C) component contained as necessary, the (E) component is preferably 0.1 to 20 parts by mass, more preferably 0.2 to 10 parts by mass, and even more preferably 0.5 to 8 parts by mass.

[0125] The density of the cured body when foamed is preferably 0.40 to 0.95 g / cm 3 and when using a curable composition containing an iso(thio)cyanate compound as the (B) component, in the foaming agent foaming method of adding water, after water and the iso(thio)cyanate group react, carbon dioxide and an amino group are formed, and carbon dioxide is used as the foaming gas, while the amino group further reacts with the iso(thio)cyanate group to form a urea bond and / or a thiourea bond.

[0126] When a cured body obtained from the curable composition of the present invention is used as an abrasive pad, the cured body can have any suitable hardness. The hardness can be measured according to the Shore hardness test, for example, according to JIS standard (hardness test) K6253. In the present invention, when the cured body is used as an abrasive pad, the Shore hardness of the cured body is preferably 30A to 70D, and more preferably 40A to 60D (where "A" indicates hardness on the Shore "A" scale and "D" indicates hardness on the Shore "D" scale). The hardness can be any desired hardness by changing the compound composition and the amount of compounding as needed. When a cured body obtained from the curable composition of the present invention is used as a polishing pad, the hysteresis loss of the cured body is preferably 60% or less, more preferably 50% or less, and even more preferably 40% or less. The hysteresis loss can be measured, for example, by a method conforming to JIS K 6251. Specifically, a dumbbell-shaped test piece is stretched to 100% and then returned to its original shape to measure the hysteresis loss (area of ​​elongation and stress when stretched and returned to its original shape / area of ​​elongation and stress when stretched × 100). It is presumed that a lower hysteresis loss allows the kinetic energy of the abrasive grains to be uniformly utilized for polishing the workpiece when used as a polishing pad, thus enabling excellent flatness and a high polishing rate. Furthermore, it is believed that a lower hysteresis loss enables an excellent polishing rate even with a soft pad. In the measurement of hysteresis loss described above, the "area of ​​elongation and stress when stretched and then returned to its original state" is expressed as "area of ​​stress-strain curve during stretching - area of ​​stress-strain curve during contraction," and the "area of ​​elongation and stress when stretched" described above means "area of ​​stress-strain curve during stretching."

[0127] When a cured body obtained from the curable composition of the present invention is used as a polishing pad, the wear resistance of the cured body is preferably 60 mg or less in the Taber abrasion test, and more preferably 50 mg or less. By reducing the amount of Taber abrasion, it becomes possible to exhibit excellent wear resistance when used as a polishing pad. The detailed method for conducting the Taber abrasion test can be the method described in the examples below.

[0128] Furthermore, when a cured body obtained from the curable composition of the present invention is used as a polishing pad member, it is preferable that the cured body has a compressibility within a certain range in order to achieve flatness of the workpiece. The compressibility can be measured by a method in accordance with JIS L 1096. The compressibility of the cured body is preferably 0.5% to 50%. Being within this range makes it possible to achieve excellent flatness of the workpiece.

[0129] Furthermore, when a polishing pad is constructed from multiple layers, the hardened material described above can be used as a component of the polishing pad in at least one of the layers. For example, when a polishing pad is constructed from two layers, it consists of a first layer having a polishing surface that contacts the workpiece during polishing, and a second layer that contacts the first layer on the surface opposite the polishing surface of the first layer. In this case, the properties of the polishing pad can be adjusted by giving the second layer and the first layer different hardnesses and moduli. In the present invention, it is sufficient to construct at least one of the first or second layer with the hardened material described above.

[0130] Furthermore, when the hardened body is used as a polishing pad, it can also be made into a fixed abrasive hardened body by incorporating abrasive grains into the hardened composition and hardening it. Examples of the abrasive grains include particles made of materials selected from cerium oxide, silicon oxide, alumina, silicon carbide, zirconia, iron oxide, manganese dioxide, titanium oxide, and diamond, or two or more particles made of these materials. The method of incorporating these abrasive grains is not particularly limited, but for example, they can be incorporated into the hardened body by dispersing these abrasive grains in the hardened composition and then hardening the hardened composition.

[0131] In the present invention, the shape of the polishing pad is not particularly limited, and a groove structure can be formed on its surface. In particular, it is preferable that the groove structure be shaped to hold and refresh the slurry when polishing the workpiece. Specifically, examples include X (stripe) grooves, XY grid grooves, concentric grooves, through holes, non-through holes, polygonal prisms, cylinders, spiral grooves, eccentric grooves, radial grooves, and combinations thereof.

[0132] The method for manufacturing the groove structure described above is not particularly limited. Examples include mechanical cutting using a jig such as a cutting tool of a predetermined size, manufacturing by pouring resin into a mold having a predetermined surface shape and allowing it to harden, manufacturing by pressing resin with a press plate having a predetermined surface shape, manufacturing using photolithography, manufacturing using printing techniques, and manufacturing using laser light such as a carbon dioxide laser.

[0133] In the present invention, the curable composition can also be applied to or impregnated onto a nonwoven fabric, for example, and then cured to form a nonwoven polishing pad.

[0134] Furthermore, the cured product of the present invention may be a photochromic curable composition by incorporating a photochromic compound. A photochromic cured product can be obtained by curing such a photochromic curable composition. This photochromic cured product can be suitably used for photochromic eyeglass lenses and the like.

[0135] In addition to polishing pads and photochromic cured materials, the cured bodies of the present invention can also be used as cushioning materials, vibration damping materials, sound absorbing materials, and the like. Furthermore, in the present invention, the nonwoven fabric-like cured body obtained by coating or impregnating a nonwoven fabric with the curable composition and then curing it can be applied not only to the aforementioned nonwoven fabric-like polishing pads, but also to cushioning materials, vibration damping materials, and sound absorbing materials. [Examples]

[0136] Next, the present invention will be described in detail using examples and comparative examples, but the present invention is not limited to these examples. In the following examples and comparative examples, the evaluation methods, etc., are as follows.

[0137] [Measurement method] (Molecular weight measurement; Gel permeation chromatography (GPC measurement)) GPC measurements were performed using a liquid chromatograph (Waters Ltd.). Depending on the molecular weight of the sample being analyzed, Showa Denko Corporation's Shodex GPC KF-802 (exclusion limit molecular weight: 5000) and KF802.5 (exclusion limit molecular weight: 20000) columns were used as appropriate. Dimethylformamide (DMF) was used as the developing solvent, and measurements were performed at a flow rate of 1 ml / min and a temperature of 40°C. Polyethylene oxide was used as the standard sample, and the weight-average molecular weight of component (A) was determined by comparative conversion. A differential refractometer was used as the detector.

[0138] (viscosity measurement) Viscosity was measured using a Brookfield rotational viscometer (BROOKFIELD RST-CPS Rheometer, manufactured by Eiko Seiki Co., Ltd.) at 60°C under a shear stress of 100 Pa.

[0139] (Measurement of residual tin; ICP emission) For ICP emission measurement, the sample was dissolved at 1000 ppm in a mixture of methyl isobutyl ketone and isopropyl alcohol, and the amount of metal contained in the extract was calculated using an ICP emission spectrometer (i CAP 6500 DUO, Thermo Fisher Scientific Co., Ltd.).

[0140] (Measurement of water content in reaction system; Karl Fischer method) To measure the moisture content, 4 g of the solution was withdrawn from the reaction system, dissolved in 8 g of anhydrous DMF with a known moisture content, and the moisture content of the solution was measured by volumetric method using a Karl Fischer moisture meter, model KF-31 series (manufactured by Nitto Seikou Analytech Co., Ltd.). The dehydrating solvent used was GEX (manufactured by Mitsubishi Chemical Corporation), and the titrator used was SS-Z (manufactured by Mitsubishi Chemical Corporation).

[0141] [Evaluation Method] (1) Density: Density (g / cm³) measured using Toyo Seiki's (DSG-1) 3 ) was measured.

[0142] (2) D hardness: Shore D hardness was measured using a durometer manufactured by Polymer Instruments in accordance with JIS standard (hardness test) K6253. The samples were stacked to a thickness of 6 mm for measurement. Samples with relatively low hardness were measured using Shore A hardness, and samples with relatively high hardness were measured using Shore D hardness.

[0143] (3) Wear resistance: The Taber wear test was measured using a Taber 5130 type apparatus. The Taber wear test was performed with a load of 1 kg, a rotation speed of 60 rpm, and 1000 rotations per minute, using an H-18 wear wheel, and the amount of wear was measured.

[0144] (4) Hysteresis loss: A resin die-cast torso 8, with a thickness of 2 mm, was stretched 20 mm at 10 mm / min using a Shimadzu AG-SX autograph. The hysteresis loss was then measured when the die was returned to its original state until the stress was zero.

[0145] (5) Polishing rate: The polishing rate was measured when polishing was performed under the following conditions. The polishing rate is the average value for 10 2-inch sapphire wafers. CMP polishing pad: A pad with concentric grooves formed on its surface, measuring 500mm in diameter and 1mm thick. Slurry: FUJIMI Conpol 80 Concentrate Pressure: 4 psi Rotation speed: 45 rpm Time: 1 hour

[0146] (6) Surface roughness (Ra): The surface roughness (Ra) of 10 2-inch sapphire wafers polished under the conditions described in (5) above was measured using a nanosearch microscope SFT-4500 (manufactured by Shimadzu Corporation). The surface roughness is the average value of 10 2-inch sapphire wafers.

[0147] (7) Edge rounding: Edge rounding of 2-inch sapphire wafers was confirmed when polished under the same conditions as those described in (5) Polishing Rate. The evaluation was conducted according to the following criteria. 1: The edge of the wafer is measured using a laser microscope, and the edge sag is 30 μm or less. 2: The edge of the wafer is measured using a laser microscope, and the edge sag is greater than 30 μm but less than 50 μm. 3. The edge of the wafer is measured using a laser microscope, and the edge sag is greater than 50 μm but less than 70 μm. 4. When measuring the edge of the wafer with a laser microscope, if the edge sag exceeds 70 μm.

[0148] <Example 1>: (Manufacturing of A-1) 10 g of hydroxypropylated β-cyclodextrin (manufactured by Cyclochem Co., Ltd.) and 32.0 g of ε-caprolactone were stirred while heating to 130°C with a flow of dry nitrogen to form a homogeneous solution. Dehydration was then carried out under reduced pressure of 20 kPa for 5 hours, and the water content in the reaction system was confirmed to be 80 ppm. Subsequently, 0.04 g of tin(II) 2-ethylhexanoate was added and reacted for 16 hours to obtain A-1, a cyclic molecule with an active hydrogen group-containing side chain. The physical properties of A-1 were as follows. In addition, in GPC measurement, in addition to the single peak of the main product, a small peak considered to be an impurity due to the polymerizable cyclic compound was observed in the low molecular weight region. The purity was calculated from the ratio of the single peak of the main product to the total peaks. Weight average molecular weight Mw (GPC): 4800 Dispersion degree (GPC): 1.05 Purity (GPC): 99.8% Impurity content due to polymerizable cyclic compounds: 0.2% by mass Side chain modification degree: 0.43 (expressed as 43%) Molecular weight of side chain: approximately 560 on average Viscosity: 3,800mPa·s Residual tin content: 300 ppm

[0149] <Example 2>: (Manufacturing of A-2) A-2 was produced in the same manner as A-1, except that dehydration was carried out under reduced pressure of 20 kPa for 2 hours and the water content in the reaction system was confirmed to be 700 ppm. The physical properties of A-2 were as follows. Weight average molecular weight Mw (GPC): 4800 Dispersion degree (GPC): 1.05 Purity (GPC): 99.2% Impurity content due to polymerizable cyclic compounds: 0.8% by mass Side chain modification degree: 0.43 (expressed as 43%) Molecular weight of side chain: approximately 550 on average Viscosity: 3,800mPa·s Residual tin content: 300 ppm

[0150] <Example 3>: (Manufacturing of A-3) A-3 was produced in the same manner as A-1, except that dehydration was carried out under reduced pressure of 20 kPa for 1 hour, and the water content in the reaction system was confirmed to be 1800 ppm. The physical properties of A-3 were as follows. Weight average molecular weight Mw (GPC): 4800 Dispersion degree (GPC): 1.05 Purity (GPC): 98.5% Impurity content due to polymerizable cyclic compounds: 1.5% by mass Side chain modification degree: 0.42 (expressed as 42%) Molecular weight of side chain: approximately 550 on average Viscosity: 3,800mPa·s Residual tin content: 300 ppm

[0151] <Example 4>: (Manufacturing of A-4) A-4 was produced in the same manner as A-1, except that dehydration was carried out under reduced pressure of 30 kPa for 1 hour and the water content in the reaction system was confirmed to be 5000 ppm. The physical properties of A-4 were as follows. Weight average molecular weight Mw (GPC): 4800 Dispersion degree (GPC): 1.05 Purity (GPC): 97.2% Impurity content due to polymerizable cyclic compounds: 2.8% by mass Side chain modification degree: 0.42 (43% when expressed as a percentage) Molecular weight of side chain: approximately 540 on average Viscosity: 3,800mPa·s Residual tin content: 300 ppm

[0152] <Example 5>: (Manufacturing of A-5) A-5 was produced in the same manner as A-1, except that dehydration was carried out under reduced pressure of 30 kPa for 0.5 hours and the water content in the reaction system was confirmed to be 10,000 ppm. The physical properties of A-5 were as follows. Weight average molecular weight Mw (GPC): 4800 Dispersion degree (GPC): 1.05 Purity (GPC): 94.5% Impurity content due to polymerizable cyclic compounds: 5.5% by mass Side chain modification degree: 0.42 (expressed as 42%) Side chain molecular weight: approximately 530 on average Viscosity: 3,800mPa·s Residual tin content: 300 ppm <Example 6>: (Manufacturing of A-6) A-6 was prepared in the same manner as A-1, except that 0.007 g of tin(II) 2-ethylhexanoate was added. The physical properties of A-6 were as follows. Dispersity (GPC): 1.23 Purity (GPC): 99.8% Impurity content due to polymerizable cyclic compounds: 0.2% by mass Side chain modification degree: 0.43 (expressed as 43%) Molecular weight of side chain: approximately 560 on average Viscosity: 4,200mPa·s Residual tin content: 50 ppm

[0153] <Comparative Example 1>: (Manufacturing of M-1) M-1 was obtained by the same procedure as A-1, except that the water content in the reaction system was confirmed to be 15,000 ppm without performing a dehydration step. The physical properties of M-1 were as follows. Weight average molecular weight Mw (GPC): 4800 Dispersion degree (GPC): 1.05 Purity (GPC): 89.5% Impurity content due to polymerizable cyclic compounds: 10.5% by mass Side chain modification degree: 0.41 (expressed as 41%) Molecular weight of side chain: approximately 510 on average Viscosity: 3,900mPa·s Residual tin content: 300 ppm

[0154] <(B) Polymerizable monomers> (B12) Component: Urethane prepolymer Pre-1: Terminal isocyanate urethane prepolymer with an isocyanate equivalent of 840. In a flask equipped with a nitrogen inlet tube, thermometer, and stirrer, 348 g of 2,4-tolylene diisocyanate and 650 g of polyoxytetramethylene glycol (number average molecular weight: 650) were reacted at 80°C for 3 hours under a nitrogen atmosphere. Then, 40 g of diethylene glycol was reacted at 80°C for 3 hours to obtain a terminal isocyanate urethane prepolymer (Pre-1) with an isocyanate equivalent of 840.

[0155] (C2) Component: Amino group-containing monomer MOCA: 4,4'-methylenebis(o-chloroaniline)

[0156] <(E) Hollow particles (micro hollow particles)> Hollow particle 1: Microcapsule 920-40 (manufactured by Nippon Philite Co., Ltd.) with a hollow particle size of 40 μm and a density of 0.03 g / cm³.

[0157] <Example 7> Component (A), A-1:13 parts by mass, and component (C2), 4,4'-methylenebis(o-chloroaniline) (MOCA):6 parts by mass, were mixed at 120°C to form a homogeneous solution, which was then thoroughly degassed to prepare solution A. Separately, Component (B), Pre-1:81 parts by mass of the above-mentioned product, which was heated to 70°C, was mixed with 1:0.8 parts by mass of hollow particles of component (E), and stirred with a rotary-orbiting stirrer to prepare a homogeneous solution, solution B. Solution A was added to the solution B prepared above and mixed uniformly to form a curable composition. The curable composition was poured into a mold and cured at 100°C for 15 hours. After curing was complete, it was removed from the mold to obtain a cured body. The respective component amounts are shown in Table 1.

[0158] Next, the obtained hardened material was sliced ​​to create hardened materials with thicknesses of 2 mm and 1 mm. The 2 mm thick hardened material obtained by slicing was used to perform the various evaluations described above. As a result, the density of the obtained hardened material was 0.8 g / cm³. 3 The Shore D hardness was 27D, the abrasion resistance was 19mg, and the hysteresis loss was 25%.

[0159] Furthermore, by forming spiral grooves on the surface of a 1mm thick hardened body obtained by slicing, and attaching double-sided tape to the back surface, a polishing pad consisting of a hardened body with a diameter of 500mm and a thickness of 1mm was created.

[0160] The polishing rate of the polishing pad made from the hardened material obtained above was 3.3 μm / hr, the surface roughness of the wafer after polishing was 0.25 nm, and the edge sag was 1. The results are also shown in Table 1.

[0161] <Examples 8-12, Comparative Example 2> Except for using the compositions shown in Table 1, a cured body and a polishing pad were prepared and evaluated in the same manner as in Example 6. The results are shown in Table 1.

[0162] [Table 1]

Claims

1. A method for producing a side-chain-containing cyclic molecule, comprising: a reaction system containing a cyclic lactone and a cyclodextrin, wherein the water content is 10,000 ppm or less, and the cyclic lactone is subjected to ring-opening polymerization to introduce a side chain containing an active hydrogen group into the cyclodextrin.

2. A method for producing a side-chain-containing cyclic molecule according to claim 1, comprising mixing a catalyst selected from the group consisting of organotitanium compounds, organotin compounds, stannous halide compounds, metal acetylacetonate compounds, and metal salts of organocarboxylates with the reaction system to produce the ring-opening polymerization.

3. The method for producing a side-chain-containing cyclic molecule according to claim 1 or 2, wherein the number-average molecular weight of the side chain is 300 or more.

4. A method for producing a curable composition, comprising mixing the side-chain-containing cyclic molecule obtained by the method according to any one of claims 1 to 3 with a polymerizable monomer having a polymerizable functional group that can polymerize with the active hydrogen group.

5. A method for producing a curable composition according to claim 4, comprising further mixing in fine hollow particles.

6. A method for producing a cured product, comprising curing a curable composition obtained by the method described in claim 4 or 5.

7. A method for producing an abrasive pad, comprising curing a curable composition obtained by the method described in claim 4 or 5.

Images