Compound, polymer, composition, adhesive, coating agent, cured product, and method for producing the cured product

Abstract

To provide a compound capable of forming a film that is less prone to shrinkage during curing and demonstrates superior heat resistance.SOLUTION: The present invention provides a compound represented by the formula (I). In at least the formula (I), R1 has an ethylenically unsaturated bond group. Preferably, the ethylenically unsaturated bond group should be a vinyl group, an isopropenyl group, an acryloyloxy group or a methacryloyloxy group.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a compound, a polymer, a composition, a cured product using the compound, and a method for producing the cured product. [Background technology]

[0002] Acrylic polymerizable compounds are used in a variety of applications, including inks, paints, adhesives, and coatings, due to their characteristics of transparency and fast curing speed.

[0003] For example, Patent Document 1 proposes isocyanuric acid triacrylate, isocyanuric acid diacrylate, and a curable resin composition containing them as a curable resin composition that has excellent dimensional stability against temperature and humidity and can maintain a stable shape for a long period of time. Also, Patent Document 2 describes that a photocurable resin composition that has high coating hardness, high contamination resistance, and excellent adhesion to substrates can be obtained by dimerizing an isocyanuric acid diacrylate with isophorone diisocyanate and mixing it with an acrylic copolymer compound.

[0004] Patent Documents 3 and 4 describe that by adding dipentaerythritol hexaacrylate to PVC resin, it is possible to suppress the shrinkage rate before and after electron beam irradiation and obtain a condenser tube with excellent heat resistance.

[0005] Patent Document 5 proposes compositions containing various alkoxy(meth)acrylates and photopolymerization initiators as ultraviolet-curable liquid compositions that have a small cure shrinkage rate and an excellent polymerization rate. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] Japanese Patent Application Publication No. 61-208646 [Patent Document 2] Japanese Patent Application Laid-Open No. 2000-273128 [Patent Document 3] Japanese Patent Application Publication No. 1-184120 [Patent Document 4] Japanese Patent Application Publication No. 1-310937 [Patent Document 5] Japanese Patent Application Laid-Open No. 2006-348230 Summary of the Invention [Problem to be solved by the invention]

[0007] However, films formed using curable compositions containing these polymerizable compounds still suffer from large shrinkage upon curing, which can cause problems in terms of adhesion to substrates and dimensional accuracy.

[0008] The problem to be solved by the present invention is to provide a compound capable of forming a film that shrinks little when cured and has excellent heat resistance. [Means for solving the problem]

[0009] The present inventors have conducted extensive research and found that the above-mentioned problems can be solved by introducing an isocyanurate structure into a compound having a urethane bond and an ethylenically unsaturated bond group.

[0010] That is, the present invention relates to the following items. [1] A compound represented by the following general formula (I): [ka] (In the formula, a represents 0 or 1, R 1 represents an unsubstituted or substituted hydrocarbon group having 3 to 20 carbon atoms and having an ethylenically unsaturated bond group at a terminal, or a group in which one or more methylene groups in the hydrocarbon group having an ethylenically unsaturated bond group at a terminal are substituted with a divalent group selected from the following <Group A>, R 2 and R 4each independently represents a hydrogen atom, an unsubstituted or substituted alkyl group having 1 to 3 carbon atoms, or the above alkyl group in which one or more methylene groups are substituted with a divalent group selected from the following <Group A>, When a is 0, R 3 is a hydrogen atom, When a is 1, R 3 represents an unsubstituted or substituted hydrocarbon group having 3 to 20 carbon atoms and having an ethylenically unsaturated bond group at a terminal, an unsubstituted or substituted hydrocarbon group having 6 to 20 carbon atoms and having an aromatic ring, a hydrocarbon group having 3 to 20 carbon atoms and having an aliphatic hydrocarbon ring, or a group in which one or more methylene groups in the above-mentioned hydrocarbon group having an ethylenically unsaturated bond group at a terminal, the above-mentioned hydrocarbon group having an aromatic ring, or the above-mentioned hydrocarbon group having an aliphatic hydrocarbon ring are substituted with a divalent group selected from the following <Group A>, R 5 represents a hydrogen atom, an unsubstituted or substituted hydrocarbon group having 1 to 20 carbon atoms, or the above hydrocarbon group in which one or more methylene groups have been substituted with a divalent group selected from the following <Group A>, X 1 , X 2 and X 3 each independently represents a divalent hydrocarbon group having 1 to 20 carbon atoms, or a group in which one or more methylene groups in the divalent hydrocarbon group are substituted with a divalent group selected from the following <Group A>, <Group A> is -O-, -S-, -CO-, -CO-O- and -SO2-.

[0011] [2] The compound according to [1], wherein in the general formula (I), a is 1.

[0012] [3] In the above general formula (I), R 3is an unsubstituted or substituted hydrocarbon group having 3 to 20 carbon atoms and having an ethylenically unsaturated bond group at a terminal, or a group in which one or more methylene groups in the unsubstituted or substituted hydrocarbon group having 3 to 20 carbon atoms and having an ethylenically unsaturated bond group at a terminal are substituted with a divalent group selected from the above <Group A>.

[0013] [4] A compound represented by the following general formula (II): [ka] (In the formula, n represents 2 to 6, R 6 , R 7 and R 8 each independently represents a hydrogen atom, an unsubstituted or substituted alkyl group having 1 to 3 carbon atoms, or the above alkyl group in which one or more methylene groups are substituted with a divalent group selected from the following <Group B>, R 9 represents an unsubstituted or substituted hydrocarbon group having 3 to 20 carbon atoms and having an ethylenically unsaturated bond group at a terminal, or a group in which one or more methylene groups in the hydrocarbon group having an ethylenically unsaturated bond group at a terminal are substituted with a divalent group selected from the following <Group B>, R 10 represents an unsubstituted or substituted hydrocarbon group having 3 to 20 carbon atoms and having an ethylenically unsaturated bond group at a terminal, an unsubstituted or substituted hydrocarbon group having 6 to 20 carbon atoms and having an aromatic ring, a hydrocarbon group having 3 to 20 carbon atoms and having an aliphatic hydrocarbon ring, or a group in which one or more methylene groups in the hydrocarbon group having an ethylenically unsaturated bond group at a terminal, the hydrocarbon group having an aromatic ring, or the hydrocarbon group having an aliphatic hydrocarbon ring are substituted with a divalent group selected from the following <Group B>, X 4 , X 5 and X 6 each independently represents a divalent hydrocarbon group having 1 to 20 carbon atoms, or a group in which one or more methylene groups in the divalent hydrocarbon group are substituted with a divalent group selected from the following <Group B>, Y 1 represents an unsubstituted or substituted hydrocarbon group having 1 to 20 carbon atoms, a heterocyclic group having 2 to 30 carbon atoms, an unsubstituted or substituted hydrocarbon group having a heterocycle having 2 to 30 carbon atoms, or a group in which one or more methylene groups in the above unsubstituted or substituted hydrocarbon group having 1 to 20 carbon atoms or the above unsubstituted or substituted hydrocarbon group having a heterocycle having 2 to 30 carbon atoms are substituted with a divalent group selected from the following <Group B>, <Group B> is -O-, -S-, -CO-, -CO-O- and -SO2-.

[0014] [5] The compound according to [4], wherein n is 2 or 3 in the general formula (II).

[0015] [6] In the above general formula (II), R 10 is an unsubstituted or substituted hydrocarbon group having 3 to 20 carbon atoms and having an ethylenically unsaturated bond group at a terminal, or a group in which one or more methylene groups in the unsubstituted or substituted hydrocarbon group having 3 to 20 carbon atoms and having an ethylenically unsaturated bond group at a terminal are substituted with a divalent group selected from the above <Group B>.

[0016] [7] Y above 1 represents an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms and from which n-1 hydrogen atoms have been removed, an unsubstituted or substituted hydrocarbon group having 6 to 20 carbon atoms and having an aromatic ring, an unsubstituted or substituted hydrocarbon group having 2 to 30 carbon atoms and having a heterocycle, or a group in which one or more methylene groups in the alkyl group, the hydrocarbon group having an aromatic ring, or the hydrocarbon group having a heterocycle are substituted with a divalent group selected from <Group B>.

[0017] [8] The compound according to any one of [1] to [7], wherein the ethylenically unsaturated bond group is a vinyl group, an isopropenyl group, an acryloyloxy group, or a methacryloyloxy group.

[0018] [9] A polymer having a structural unit derived from the compound according to any one of [1] to [8].

[0019]

[10] A composition containing the compound according to any one of [1] to [8].

[0020]

[11] An adhesive containing the composition according to

[10] .

[0021]

[12] A coating agent containing the composition according to

[10] .

[0022]

[13] A cured product of the composition described in

[10] .

[0023]

[14] A method for producing a cured product, comprising a step of curing the composition according to

[10] .

[0024]

[15] The method for producing a cured product according to

[14] , wherein the curing step is a step of irradiating the composition with light. [Effects of the Invention]

[0025] According to the present invention, it is possible to provide a compound capable of forming a film that shrinks little when cured and has excellent heat resistance. DETAILED DESCRIPTION OF THE INVENTION

[0026] The present invention relates to a compound, a polymer, a composition, an adhesive, a coating agent, a cured product, and a method for producing the cured product. The present invention will be described in detail below.

[0027] A. Compound A First, the compound of the present invention will be described. The compound of the present disclosure is a compound represented by the following general formula (I) (hereinafter, sometimes referred to as Compound 1), or a compound represented by the following general formula (II) (hereinafter, sometimes referred to as Compound 2). Hereinafter, Compound 1 and Compound 2 may be collectively referred to as Compound A.

[0028] According to the present invention, the compound A can form a film with small cure shrinkage and excellent heat resistance. Furthermore, the film can also have excellent handleability. The reason for the excellent cure shrinkage and heat resistance is unclear, but is presumed to be as follows. The action of hydrogen bonds in the urethane bond portion in the above general formula reduces shrinkage during hardening compared to a structure without hydrogen bonds. Similarly, the action of hydrogen bonds and R 1 or R 3 The structure of (R 3 The thermal resistance is improved by hydrogen bonding when a=0 and by a specific group when a=1, resulting in excellent heat resistance.

[0029] The compound A can be used as a radical polymerizable compound. The compound A can be polymerized by a commonly used method, for example, by irradiating the compound A with light, by heating the compound A, or the like. The polymerization can be carried out by adding a polymerization initiator and generating radicals from the polymerization initiator. If the polymerization initiator is a photoradical polymerization initiator, radicals are generated by irradiation with light, and if the polymerization initiator is a thermal radical polymerization initiator, radicals are generated by heat treatment, and the generated radicals can easily promote the polymerization reaction. Examples of light sources used for light irradiation include ultra-high pressure mercury lamps, high pressure mercury lamps, medium pressure mercury lamps, low pressure mercury lamps, mercury vapor arc lamps, xenon arc lamps, carbon arc lamps, metal halide lamps, fluorescent lamps, tungsten lamps, excimer lamps, germicidal lamps, light emitting diodes, and CRT light sources. Preferably, ultra-high pressure mercury lamps, mercury vapor arc lamps, carbon arc lamps, xenon arc lamps, and the like that emit light with a wavelength of 300 to 450 nm are used. The exposure dose of the light source is not particularly limited and can be appropriately determined depending on the application of the compound A, etc. The heating temperature in the heat treatment can be appropriately determined depending on the application of the compound A, etc.

[0030] The compound A can be used as a monomer material for a polymer or composition. The applications of the polymer or composition containing the compound A include adhesives, coating agents, and cured products, which will be described later. Hereinafter, such compound A will be explained separately as compound 1 and compound 2.

[0031] 1. Compound 1 The compound 1 is a compound represented by the following general formula (I). [ka] (In the formula, a represents 0 or 1, R 1 represents an unsubstituted or substituted hydrocarbon group having 3 to 20 carbon atoms and having an ethylenically unsaturated bond group at a terminal, or a group in which one or more methylene groups in the hydrocarbon group having an ethylenically unsaturated bond group at a terminal are substituted with a divalent group selected from the following <Group A>, R 2 and R 4 each independently represents a hydrogen atom, an unsubstituted or substituted alkyl group having 1 to 3 carbon atoms, or the above alkyl group in which one or more methylene groups are substituted with a divalent group selected from the following <Group A>, When a is 0, R 3 is a hydrogen atom, When a is 1, R 3 represents an unsubstituted or substituted hydrocarbon group having 3 to 20 carbon atoms and having an ethylenically unsaturated bond group at a terminal, an unsubstituted or substituted hydrocarbon group having 6 to 20 carbon atoms and having an aromatic ring, a hydrocarbon group having 3 to 20 carbon atoms and having an aliphatic hydrocarbon ring, or a group in which one or more methylene groups in the above-mentioned hydrocarbon group having an ethylenically unsaturated bond group at a terminal, the above-mentioned hydrocarbon group having an aromatic ring, or the above-mentioned hydrocarbon group having an aliphatic hydrocarbon ring are substituted with a divalent group selected from the following <Group A>, R 5represents a hydrogen atom, an unsubstituted or substituted hydrocarbon group having 1 to 20 carbon atoms, or the above hydrocarbon group in which one or more methylene groups have been substituted with a divalent group selected from the following <Group A>, X 1 , X 2 and X 3 each independently represents a divalent hydrocarbon group having 1 to 20 carbon atoms, or a group in which one or more methylene groups in the divalent hydrocarbon group are substituted with a divalent group selected from the following <Group A>, <Group A> is -O-, -S-, -CO-, -CO-O- and -SO2-.

[0032] In the above general formula (I), R 5 The hydrocarbon group having 1 to 20 carbon atoms used in the above may or may not have a substituent, but a hydrocarbon group having a substituent is a group having a structure in which one or more hydrogen atoms in the hydrocarbon group are substituted with a substituent. Examples of the substituent include a halogen atom, a halogenated alkyl group having 1 to 3 carbon atoms, a cyano group, a nitro group, a hydroxyl group, an amino group, a carboxy group, an epoxy group, a mercapto group, and an isocyanate group. Examples of the unsubstituted hydrocarbon group include an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an alkenyl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a cycloalkylalkyl group having 4 to 20 carbon atoms, and an arylalkyl group having 7 to 20 carbon atoms.

[0033] In the present invention, when a hydrogen atom in a group is substituted with a substituent, the number of carbon atoms in the group refers to the number of carbon atoms in the group after the substitution. For example, the term "1 to 20 carbon atoms" in "a hydrocarbon group having a substituent having 1 to 20 carbon atoms" refers to the total number of carbon atoms in the group after the hydrogen atoms have been substituted, and does not refer to the number of carbon atoms in the hydrocarbon group before the hydrogen atoms are substituted. In the present invention, the number of carbon atoms in a group in which a methylene group in a group having a predetermined number of carbon atoms is substituted with a divalent group selected from the above <Group A> defines the number of carbon atoms in the group after substitution. For example, in this specification, the number of carbon atoms in a group in which one methylene group (-CH2-) in an alkyl group having 20 carbon atoms is substituted with the divalent group "-O-" is 19. Furthermore, a hydrocarbon group in which one or more methylene groups have been substituted with a divalent group selected from the above <Group A> does not have a structure in which multiple divalent groups are adjacent to each other. The multiple divalent groups may be the same or different. Furthermore, in a hydrocarbon group having an ethylenically unsaturated bond group at its terminal, the ethylenically unsaturated bond group and the group substituted with a divalent group selected from the above <Group A> do not have a structure in which they are adjacent to each other.

[0034] The alkyl group having 1 to 20 carbon atoms may be linear or branched. Examples of linear alkyl groups include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, and octadecyl. Examples of branched alkyl groups include isopropyl, sec-butyl, tert-butyl, isobutyl, isopentyl, tert-pentyl, 2-hexyl, 3-hexyl, 2-heptyl, 3-heptyl, isoheptyl, tert-heptyl, isooctyl, tert-octyl, 2-ethylhexyl, nonyl, isononyl, decyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, and octadecyl.

[0035] Examples of the cycloalkyl group having 3 to 20 carbon atoms include saturated monocyclic alkyl groups, saturated polycyclic alkyl groups, and groups in which one or more hydrogen atoms in the ring of these groups are substituted with alkyl groups. Examples of the saturated monocyclic alkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, and cyclodecyl. Examples of the saturated polycyclic alkyl groups include adamantyl, decahydronaphthyl, octahydropentalene, and bicyclo[1.1.1]pentanyl. Examples of the alkyl groups substituting hydrogen atoms in the ring of saturated monocyclic or saturated polycyclic alkyl groups include the groups exemplified above as alkyl groups. Examples of the saturated polycyclic alkyl group in which one or more hydrogen atoms in the ring are substituted with alkyl groups include bornyl.

[0036] The alkenyl group having 3 to 20 carbon atoms is an internal alkenyl group having an internal unsaturated bond. It may be linear or branched. Examples of the internal alkenyl group include 2-butenyl, 3-pentenyl, 2-hexenyl, 3-hexenyl, 2-heptenyl, 3-heptenyl, 4-heptenyl, 3-octenyl, 3-nonenyl, 4-decenyl, 3-undecenyl, 4-dodecenyl, and 4,8,12-tetradecatrienylallyl.

[0037] The aryl group having 6 to 20 carbon atoms may have a monocyclic structure, a fused ring structure, or a structure in which two aromatic hydrocarbon rings are linked together. The aryl group in which two aromatic hydrocarbon rings are linked may be one in which two aromatic hydrocarbon rings of a monocyclic structure are linked, one in which an aromatic hydrocarbon ring of a monocyclic structure is linked to an aromatic hydrocarbon ring of a fused ring structure, or one in which two aromatic hydrocarbon rings of a fused ring structure are linked. Examples of the linking group linking the two aromatic hydrocarbon rings include a single bond and a carbonyl group. Examples of aryl groups having a single ring structure include phenyl, tolyl, xylyl, ethylphenyl, 2,4,6-trimethylphenyl, etc. Examples of aryl groups having a fused ring structure include naphthyl, anthracenyl, phenanthryl, pyrenyl, etc. Examples of aryl groups having two linked aromatic hydrocarbon rings include biphenyl, benzoylphenyl, etc.

[0038] The cycloalkylalkyl group having 4 to 20 carbon atoms refers to a group in which a hydrogen atom of an alkyl group is substituted with a cycloalkyl group. The cycloalkyl group in the cycloalkylalkyl group may be monocyclic or polycyclic. Examples of cycloalkylalkyl groups in which the cycloalkyl group is monocyclic include cyclopropylmethyl, 2-cyclobutylethyl, 3-cyclopentylpropyl, 4-cyclohexylbutyl, cycloheptylmethyl, cyclooctylmethyl, 2-cyclononylethyl, and 2-cyclodecylethyl. Examples of cycloalkylalkyl groups in which the cycloalkyl group is polycyclic include 3-3-adamantylpropyl and decahydronaphthylpropyl.

[0039] The arylalkyl group having 7 to 20 carbon atoms refers to a group in which one or more hydrogen atoms in an alkyl group are substituted with an aryl group. Examples of the arylalkyl group include benzyl, fluorenyl, indenyl, 9-fluorenylmethyl, α-methylbenzyl, phenylethyl, and naphthylpropyl groups.

[0040] In the above general formula (I), R 2 and R 4 The alkyl group having 1 to 3 carbon atoms may or may not have a substituent. The alkyl group having a substituent is a group in which one or more hydrogen atoms in the alkyl group are substituted with a substituent. Examples of the substituent include R 5 The substituents for substituting hydrogen atoms in the hydrocarbon groups used in the above can be any of those listed above.

[0041] The unsubstituted alkyl group having 1 to 3 carbon atoms includes R5 Among the alkyl groups listed above, those having a predetermined number of carbon atoms can be used.

[0042] R 1 and R 3 The hydrocarbon group having an ethylenically unsaturated bond group at its terminal, as used above, refers to a group in which one or more hydrogen atoms in the hydrocarbon group have been substituted with an ethylenically unsaturated bond group. For example, when the hydrocarbon group has a linear or branched chain structure having one or more methylene groups, the phrase "having an ethylenically unsaturated bond group at its terminal" means that the ethylenically unsaturated bond group is bonded to at least one of the methylene groups in the chain structure. The ethylenically unsaturated bond group is a group having a carbon-carbon double bond, and examples thereof include a vinyl group, a vinyloxy group, an allyl group, an allyloxy group, an allylamino group, an isopropenyl group, an isopropenyloxy group, an isopropenylamino group, an acryloyloxy group, an acrylamide group, a methacryloyloxy group, and a methacrylamide group. 1 (and possibly) R 3 may have only one ethylenically unsaturated bond group, or may have two or more ethylenically unsaturated bond groups. The hydrocarbon group having an ethylenically unsaturated bond group at the terminal may or may not have a substituent, but a hydrocarbon group having a substituted ethylenically unsaturated bond group is a group having a structure in which one or more remaining hydrogen atoms in a hydrocarbon group substituted with an ethylenically unsaturated bond group are substituted with a substituent. On the other hand, a hydrocarbon group having an unsubstituted ethylenically unsaturated bond group is a group having a structure in which one or more remaining hydrogen atoms in a hydrocarbon group substituted with an ethylenically unsaturated bond group are not substituted with a substituent. Examples of the substituent include R 5 The substituents for substituting hydrogen atoms in the hydrocarbon groups used in the above can be any of those listed above. Examples of the hydrocarbon group in which a hydrogen atom is substituted with an ethylenically unsaturated bond group include an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a cycloalkylalkyl group, and an arylalkyl group. The number of carbon atoms in the "unsubstituted or substituted hydrocarbon group having an ethylenically unsaturated bond group at a terminal" is intended to include the carbon atoms of the ethylenically unsaturated bond group, as defined for the number of carbon atoms in a group having a substituent. Therefore, the hydrocarbon group used in the hydrocarbon group having an ethylenically unsaturated bond group at its terminal is selected so that the total number of carbon atoms in the group after hydrogen atoms are substituted with ethylenically unsaturated bond groups satisfies the number of carbon atoms of 3 to 20. Examples of the alkyl group, cycloalkyl group, alkenyl group, aryl group, cycloalkylalkyl group and arylalkyl group used as such hydrocarbon group include R 5 Among the groups listed as usable in the above, those satisfying the specified number of carbon atoms can be used.

[0043] R 3 The hydrocarbon group having an aromatic ring and 6 to 20 carbon atoms used in the above may or may not have a substituent, but a hydrocarbon group having a substituent is a group in which one or more hydrogen atoms in the hydrocarbon group are substituted with a substituent. 5 The substituents for substituting hydrogen atoms in the hydrocarbon groups used in the above can be the same as those listed above. Examples of hydrocarbon groups containing an unsubstituted aromatic ring include aryl groups having 6 to 20 carbon atoms and arylalkyl groups having 7 to 20 carbon atoms.

[0044] Such aryl groups and arylalkyl groups include R 5 The same groups as those used in the above can be used.

[0045] R 3 The hydrocarbon group having an aliphatic hydrocarbon ring with 3 to 20 carbon atoms used in the above may or may not have a substituent, but a hydrocarbon group having a substituent is a group having a structure in which one or more hydrogen atoms in the hydrocarbon group are substituted with a substituent. 5The substituents for substituting hydrogen atoms in the hydrocarbon groups used in the above can be the same as those listed above. Examples of hydrocarbon groups containing an unsubstituted aliphatic hydrocarbon ring include cycloalkyl groups having 3 to 20 carbon atoms and cycloalkylalkyl groups having 4 to 20 carbon atoms.

[0046] Such cycloalkyl groups and cycloalkylalkyl groups include R 5 The same groups as those used in the above can be used.

[0047] In the above general formula (I), X 1 , X 2 and X 3 Examples of the unsubstituted divalent hydrocarbon group having 1 to 20 carbon atoms used in 5 A group in which one hydrogen atom has been removed from the groups listed as hydrocarbon groups usable in the above can be used. Specific examples of such divalent hydrocarbon groups include alkylene groups having 1 to 20 carbon atoms, cycloalkylene groups having 3 to 20 carbon atoms, alkenylene groups having 3 to 20 carbon atoms, arylene groups having 6 to 20 carbon atoms, cycloalkylalkylene groups having 4 to 20 carbon atoms, and arylalkylene groups having 7 to 20 carbon atoms.

[0048] The alkylene group having 1 to 20 carbon atoms may be linear or branched. Examples of such alkylene groups include R 5It is possible to use a group in which one hydrogen atom has been removed from the groups listed as the alkyl groups used in 1. Specifically, it may be linear or branched, and examples of linear alkyl groups include methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, and octadecylene. Examples of branched chains include iso-propylene, sec-butylene, tert-butylene, iso-butylene, iso-pentylene, tert-pentylene, 2-hexylene, 3-hexylene, 2-heptylene, 3-heptylene, iso-heptylene, tert-heptylene, iso-octylene, tert-octylene, 2-ethylhexylene, nonylene, isononylene, decylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, and octadecylene.

[0049] The cycloalkylene group having 3 to 20 carbon atoms is R 5 A group in which one hydrogen atom has been removed from the groups listed as the cycloalkyl groups used in the above can be used.

[0050] The alkenylene group having 3 to 20 carbon atoms is an internal alkenylene group having an internal unsaturated bond. It may be linear or branched. The internal alkenylene group includes R 5 The alkenyl groups used in the above may be groups in which one hydrogen atom has been removed.

[0051] The arylene group having 6 to 20 carbon atoms is R 5 A group in which one hydrogen atom has been removed from the groups listed as the aryl group used in (1) can be used.

[0052] The cycloalkylalkylene group having 4 to 20 carbon atoms includes R 5 A group in which one hydrogen atom has been removed from the group exemplified as the cycloalkylalkyl group used in the above can be used.

[0053] The aryl alkylene group having 7 to 20 carbon atoms includes R 5 The arylalkyl groups mentioned above may have one hydrogen atom removed.

[0054] In the present invention, R 2 and R 4 are each independently preferably a hydrogen atom or an unsubstituted or substituted alkyl group having 1 to 3 carbon atoms, and are preferably a hydrogen atom or a methyl group, and are particularly preferably a hydrogen atom. This is because Compound 1 has the above structure, which strengthens the intermolecular hydrogen bonding, and as a result, a film can be formed that shrinks less during curing and has excellent heat resistance and handleability.

[0055] In the present invention, R 1 is an unsubstituted or substituted hydrocarbon group having 3 to 20 carbon atoms and having an ethylenically unsaturated bond group at its terminal (hereinafter, this may be referred to as unsaturated bond-containing group A), or the above-mentioned unsubstituted or substituted hydrocarbon group having 3 to 20 carbon atoms and having an ethylenically unsaturated bond group at its terminal, in which one or more methylene groups have been substituted with a divalent group selected from the above <Group A> (hereinafter, this may be referred to as unsaturated bond-containing group B), and it is preferable that it is unsaturated bond-containing group A. This is because it is possible to form a film that shrinks less during curing and has better heat resistance and handleability.

[0056] In the present invention, R 1 The unsaturated bond-containing group A used in is preferably an unsubstituted hydrocarbon group having 3 to 20 carbon atoms and having an ethylenically unsaturated bond group at its terminal. This is because compound 1 has the above structure, which allows it to form a film that shrinks less when cured and is excellent in heat resistance and handleability.

[0057] In the present invention, R 1The unsaturated bond-containing group A used in the above has 3 to 20 carbon atoms, preferably 3 to 18 carbon atoms, more preferably 3 to 15 carbon atoms, even more preferably 3 to 12 carbon atoms, still more preferably 3 to 10 carbon atoms, particularly preferably 4 to 8 carbon atoms, and especially preferably 5 to 6 carbon atoms. This is because compound 1 has the above structure, which allows it to form a film that shrinks less when cured and has excellent heat resistance and handleability. In addition, R 1 When the group used in is the unsaturated bond-containing group B, the preferred range of the number of carbon atoms therein can also be the same as the preferred ranges given above for the unsaturated bond-containing group A.

[0058] In the present invention, R 1 The type of hydrocarbon group in which the hydrogen atom is substituted by the ethylenically unsaturated bond group in the unsaturated bond-containing group A used in the above is preferably an alkyl group, and in particular, a straight-chain alkyl group. This is because a film can be formed that shrinks less when cured and has better heat resistance and handling properties. Similarly, R 1 The type of hydrocarbon group that substitutes the methylene group in the unsaturated bond-containing group B used in is preferably an alkyl group.

[0059] In the present invention, R 1 The unsaturated bond-containing group A used in may have only one ethylenically unsaturated bond group or may have two or more ethylenically unsaturated bond groups, but preferably has three or less ethylenically unsaturated bond groups, more preferably has two or less ethylenically unsaturated bond groups, and most preferably has one ethylenically unsaturated bond group. This is because compound 1 has the above structure, which allows it to form a film that shrinks less during curing and is more excellent in heat resistance and handleability. In addition, R 1 When the group used in is the unsaturated bond-containing group B, the preferred ranges thereof are the same as those given for the unsaturated bond-containing group A.

[0060] In the present invention, R 1 The ethylenically unsaturated bond group of the unsaturated bond-containing group A used in is preferably a vinyl group, an isopropenyl group, an acryloyloxy group, or a methacryloyloxy group, and among these, an acryloyloxy group or a methacryloyloxy group is preferred. This is because, due to the above structure, Compound 1 is easy to obtain raw materials for, is easy to synthesize, and can form a film that shrinks less during curing and is excellent in heat resistance and handleability. In addition, R 1 When the group used in is the unsaturated bond-containing group B, the preferred ranges thereof are the same as those given above for the unsaturated bond-containing group A.

[0061] In the present invention, when a=1, R 3 is an unsaturated bond-containing group A, an unsaturated bond-containing group B, an unsubstituted or substituted hydrocarbon group having 6 to 20 carbon atoms and an aromatic ring (hereinafter sometimes referred to as aromatic ring-containing group C), an unsubstituted or substituted hydrocarbon group having 3 to 20 carbon atoms and an aliphatic hydrocarbon ring (hereinafter sometimes referred to as aliphatic ring-containing group D), or a group in which one or more methylene groups in the above hydrocarbon group having an aromatic ring or the above hydrocarbon group having an aliphatic hydrocarbon ring are substituted with a divalent group selected from the above <Group A>, but is preferably the unsaturated bond-containing group A, the unsaturated bond-containing group B, or the aromatic ring-containing group C, and of these, the unsaturated bond-containing group A or the unsaturated bond-containing group B is more preferred, and of these, the unsaturated bond-containing group A is particularly preferred. This is because compound 1 has the above structure and can form a film that shrinks less when cured and has excellent heat resistance and handleability.

[0062] In the present invention, R 3 Preferable structures of the unsaturated bond-containing group A and the unsaturated bond-containing group B used in R 1 The unsaturated bond-containing group A and the unsaturated bond-containing group B preferably used in the above formula (1) can be the same as the unsaturated bond-containing group A and the unsaturated bond-containing group B preferably used in the above formula (1).

[0063] In the present invention, R 3 The aromatic-containing group C used in the above is preferably an unsubstituted hydrocarbon group having 6 to 20 carbon atoms and having an aromatic ring, because this allows the formation of a film that shrinks less during curing and has excellent heat resistance and handling properties.

[0064] In the present invention, R 3 The aromatic-containing group C used in the above has 6 to 20 carbon atoms, more preferably 6 to 18 carbon atoms, and even more preferably 6 to 15 carbon atoms, and among these, it is preferable that it has 6 to 12 carbon atoms, and particularly preferably 6 to 10 carbon atoms, and among these, it is particularly preferable that it has 6 to 8 carbon atoms. This is because compound 1 has the above structure, which allows it to form a film that shrinks less when cured and has excellent heat resistance and handleability.

[0065] In the present invention, R 3 The aromatic-containing group C used in is preferably a hydrocarbon group that is unsubstituted or substituted and has phenyl, biphenyl, benzyl, or phenylethyl. This is because Compound 1 has the above structure, and can form a film that shrinks less during curing and has excellent heat resistance and handleability.

[0066] In the present invention, R 3 The aliphatic ring-containing group D used in the above is preferably an unsubstituted hydrocarbon group having 3 to 20 carbon atoms and having an aliphatic hydrocarbon ring. In the present invention, R 3 The aliphatic ring-containing group D used in the above has 3 to 20 carbon atoms, preferably 4 to 18 carbon atoms, more preferably 5 to 15 carbon atoms, and even more preferably 6 to 12 carbon atoms. This is because compound 1 has the above structure, which allows it to form a film that shrinks less when cured and has excellent heat resistance and handleability.

[0067] In the present invention, R 3The aliphatic ring-containing group D used in is preferably a hydrocarbon group that is unsubstituted or substituted and has a cyclohexyl or adamantyl group, because the compound 1 has the above structure and can form a film that shrinks less during curing and has excellent heat resistance and handleability.

[0068] In the present invention, R 5 is a hydrogen atom, an unsubstituted or substituted hydrocarbon group having 1 to 20 carbon atoms, or the above hydrocarbon group in which one or more methylene groups have been substituted with a divalent group selected from <Group A> below, preferably a hydrogen atom or an unsubstituted or substituted hydrocarbon group having 1 to 20 carbon atoms, more preferably a hydrogen atom or an unsubstituted or substituted hydrocarbon group having 1 to 15 carbon atoms, even more preferably a hydrogen atom or an unsubstituted or substituted hydrocarbon group having 1 to 10 carbon atoms, still more preferably a hydrogen atom or an unsubstituted or substituted hydrocarbon group having 1 to 6 carbon atoms, of which a hydrogen atom or an unsubstituted or substituted hydrocarbon group having 1 to 3 carbon atoms is preferred, and a hydrogen atom is particularly preferred. This is because Compound 1 has the above structure, which allows it to form a film that shrinks less when cured and has better heat resistance and handleability.

[0069] In the present invention, X 1 , X 2 and X 3 are each independently a divalent hydrocarbon group having 1 to 20 carbon atoms, or a divalent hydrocarbon group in which one or more methylene groups have been substituted with a divalent group selected from the following <Group A>, and are preferably a divalent hydrocarbon group having 1 to 20 carbon atoms. This is because Compound 1 has the above structure, making it easy to obtain raw materials and easy to synthesize, and also enabling the formation of a film that shrinks less when cured and is more excellent in heat resistance and handleability.

[0070] X 1 , X2 and X 3 The divalent hydrocarbon group having 1 to 20 carbon atoms used in the above is more preferably an alkylene group having 1 to 20 carbon atoms, even more preferably an alkylene group having 1 to 15 carbon atoms, and among these, an alkylene group having 1 to 10 carbon atoms is preferred, and particularly preferably an alkylene group having 1 to 6 carbon atoms, and among these, an alkylene group having 1 to 3 carbon atoms is particularly preferred. This is because Compound 1 has the above structure, making it easy to obtain raw materials and easy to synthesize, and also enabling the formation of a film that shrinks less when cured and has excellent heat resistance and handleability.

[0071] Specific examples of Compound 1 of the present invention include compounds represented by the following formulae (1) to (16), although the present invention is not limited to these examples.

[0072] [ka] [ka] [ka] [ka]

[0073] The method for producing the compound 1 may be any method that can yield a compound of the desired structure, and can be synthesized by applying well-known chemical reactions. One such example is a method in which an isocyanuric acid derivative is reacted with an isocyanate. For example, in the following scheme (A), the target compound is obtained by reacting an isocyanuric acid derivative having two or more hydroxy groups, such as tris(2-hydroethyl)isocyanate, which is known and commercially available, with an isocyanate. By adjusting the reaction amount and carrying out a stepwise reaction, the target compound can be obtained when a is 1 and R 1 and R 3Compounds where a is different from each other can also be obtained. In addition, compounds where a is 0 can also be obtained by the same scheme. Also, by changing the type of isocyanuric acid derivative, X 1 , X 2 , X 3 There are no particular limitations on the reaction conditions in the production method, such as the reaction temperature, reaction time, and amount of raw materials used, and known conditions may be used.

[0074] [ka] (wherein X is X in formula (I) 1 The two Rs may be the same or different, and the Rs in formula (I) are the same as 1 or R 3 is the group corresponding to

[0075] 2. Compound 2 The compound 2 is a compound represented by the following general formula (II).

[0076] [ka] (In the formula, n represents 2 to 6, R 6 , R 7 and R 8 each independently represents a hydrogen atom, an unsubstituted or substituted alkyl group having 1 to 3 carbon atoms, or the above alkyl group in which one or more methylene groups are substituted with a divalent group selected from the following <Group B>, R 9 represents an unsubstituted or substituted hydrocarbon group having 3 to 20 carbon atoms and having an ethylenically unsaturated bond group at a terminal, or a group in which one or more methylene groups in the hydrocarbon group having an ethylenically unsaturated bond group at a terminal are substituted with a divalent group selected from the following <Group B>, R 10represents an unsubstituted or substituted hydrocarbon group having 3 to 20 carbon atoms and having an ethylenically unsaturated bond group at a terminal, an unsubstituted or substituted hydrocarbon group having 6 to 20 carbon atoms and having an aromatic ring, a hydrocarbon group having 3 to 20 carbon atoms and having an aliphatic hydrocarbon ring, or a group in which one or more methylene groups in the hydrocarbon group having an ethylenically unsaturated bond group at a terminal, the hydrocarbon group having an aromatic ring, or the hydrocarbon group having an aliphatic hydrocarbon ring are substituted with a divalent group selected from the following <Group B>, X 4 , X 5 and X 6 each independently represents a divalent hydrocarbon group having 1 to 20 carbon atoms, or a group in which one or more methylene groups in the divalent hydrocarbon group are substituted with a divalent group selected from the following <Group B>, Y 1 represents an unsubstituted or substituted hydrocarbon group having 1 to 20 carbon atoms, a heterocyclic group having 2 to 30 carbon atoms, an unsubstituted or substituted hydrocarbon group having a heterocycle having 2 to 30 carbon atoms, or a group in which one or more methylene groups in the above unsubstituted or substituted hydrocarbon group having 1 to 20 carbon atoms or the above unsubstituted or substituted hydrocarbon group having a heterocycle having 2 to 30 carbon atoms are substituted with a divalent group selected from the following <Group B>, <Group B> is -O-, -S-, -CO-, -CO-O- and -SO2-.

[0077] According to the present disclosure, compound 2 has a structure derived from compound 1. By linking compound 1 via a spacer to form compound 2, various functions can be imparted. For example, when compound 2 is polymerized to form a cured film, it becomes easy to adjust the glass transition temperature of the cured film to a desired range, facilitating the formation of a film with excellent handleability.

[0078] In the above general formula (II), R 6 , R 7 and R 8The alkyl group having 1 to 3 carbon atoms used in the formula (I) may or may not have a substituent. The alkyl group having a substituent is a group in which one or more hydrogen atoms in the alkyl group are substituted with a substituent. The substituent includes, for example, the alkyl group having 1 to 3 carbon atoms in the formula (I) above, R 5 The substituents for substituting hydrogen atoms in the hydrocarbon groups used in the above can be any of those listed above.

[0079] The unsubstituted alkyl group having 1 to 3 carbon atoms includes the above-mentioned R 5 Among the alkyl groups listed above, those having a predetermined number of carbon atoms can be used.

[0080] The number of carbon atoms in the group in Compound 2 is the same as that in Compound 1 of general formula (I). Furthermore, the definition of the number of carbon atoms in a group in which a methylene group in a group having a predetermined number of carbon atoms is substituted with a divalent group selected from the above <Group B> is the same as that for the group in the above general formula (I) substituted with a divalent group selected from the above <Group A>.

[0081] R 9 and R 10 The hydrocarbon group having an ethylenically unsaturated bond group at its terminal, as used herein, refers to a group in which one or more hydrogen atoms in the hydrocarbon group have been substituted with an ethylenically unsaturated bond group. For example, when the hydrocarbon group has a linear or branched chain structure having one or more methylene groups, the phrase "having an ethylenically unsaturated bond group at its terminal" means that the ethylenically unsaturated bond group is bonded to at least one of the methylene groups in the chain structure. The ethylenically unsaturated bond group is a group having a carbon-carbon double bond, and examples thereof include a vinyl group, a vinyloxy group, an allyl group, an allyloxy group, an allylamino group, an isopropenyl group, an isopropenyloxy group, an isopropenylamino group, an acryloyloxy group, an acrylamide group, a methacryloyloxy group, and a methacrylamide group. R 9 , (and possibly) R 10may each have only one ethylenically unsaturated bond group, or may each have two or more ethylenically unsaturated bond groups. The hydrocarbon group having an ethylenically unsaturated bond group at the terminal may or may not have a substituent, but a hydrocarbon group having an ethylenically unsaturated bond group with a substituent is a group having a structure in which one or more remaining hydrogen atoms in a hydrocarbon group substituted with an ethylenically unsaturated bond group are substituted with a substituent. On the other hand, a hydrocarbon group having an unsubstituted ethylenically unsaturated bond group is a group having a structure in which one or more remaining hydrogen atoms in a hydrocarbon group substituted with an ethylenically unsaturated bond group are not substituted with a substituent. The substituents include the above R 5 The substituents for substituting hydrogen atoms in the hydrocarbon groups used in the above can be any of those listed above. Examples of the hydrocarbon group in which a hydrogen atom is substituted with an ethylenically unsaturated bond group include an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a cycloalkylalkyl group, and an arylalkyl group. The number of carbon atoms in the "unsubstituted or substituted hydrocarbon group having an ethylenically unsaturated bond group at a terminal" is intended to include the carbon atoms of the ethylenically unsaturated bond group, as defined for the number of carbon atoms in a group having a substituent. Therefore, the hydrocarbon group used in the hydrocarbon group having an ethylenically unsaturated bond group at its terminal is selected so that the total number of carbon atoms in the group after hydrogen atoms are substituted with ethylenically unsaturated bond groups satisfies the number of carbon atoms of 3 to 20. Examples of the alkyl group, cycloalkyl group, alkenyl group, aryl group, cycloalkylalkyl group and arylalkyl group used as such hydrocarbon group include the above-mentioned R 5 Among the groups listed as usable in the above, those satisfying the specified number of carbon atoms can be used.

[0082] R 10The hydrocarbon group having an aromatic ring and 6 to 20 carbon atoms used in the formula (1) may or may not have a substituent, but a hydrocarbon group having a substituent is a group in which one or more hydrogen atoms in the hydrocarbon group are substituted with a substituent. 5 The substituents for substituting hydrogen atoms in the hydrocarbon groups used in the above can be the same as those listed above. The hydrocarbon group containing an unsubstituted aromatic ring includes R 3 The same can be used.

[0083] In the above general formula (II), X 4 , X 5 and X 6 The divalent hydrocarbon group having 1 to 20 carbon atoms used in the above formula (I) is, for example, X 1 , X 2 and X 3 The same can be used.

[0084] Y 1 The hydrocarbon group having 1 to 20 carbon atoms used in may or may not have a substituent, but a hydrocarbon group having a substituent is a group in which one or more hydrogen atoms in the hydrocarbon group are substituted with a substituent. 5 The substituents for substituting hydrogen atoms in the hydrocarbon groups used in the above can be the same as those listed above. Y 1 The hydrocarbon group having 1 to 20 carbon atoms used in the formula (1) is an n-valent group, and a group obtained by removing n-1 hydrogen atoms from a monovalent hydrocarbon group having 1 to 20 carbon atoms can be used.

[0085] The monovalent hydrocarbon group having 1 to 20 carbon atoms may be a group that does not contain a heterocycle, and examples thereof include aliphatic hydrocarbon groups having 1 to 20 carbon atoms and hydrocarbon groups having 6 to 20 carbon atoms that contain an aromatic ring.

[0086] The monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms can be a group that does not contain an aromatic ring, and examples thereof include alkyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, alkenyl groups having 2 to 20 carbon atoms, and cycloalkylalkyl groups having 3 to 20 carbon atoms.

[0087] The alkyl group having 1 to 20 carbon atoms includes the above-mentioned R 5 Among the alkyl groups listed above, those having the specified number of carbon atoms can be used.

[0088] The cycloalkyl group having 3 to 20 carbon atoms includes the above-mentioned R 5 Among the groups listed as cycloalkyl groups used in 1, those having the specified number of carbon atoms can be used.

[0089] The alkenyl group having 2 to 20 carbon atoms includes the above-mentioned R 5 Among the alkenyl groups listed above, those having the specified number of carbon atoms can be used.

[0090] The cycloalkylalkyl group having 3 to 20 carbon atoms includes the above-mentioned R 5 Among the cycloalkylalkyl groups listed above, those having the specified number of carbon atoms can be used.

[0091] Examples of monovalent hydrocarbon groups containing an aromatic ring having 6 to 20 carbon atoms include aryl groups having 6 to 20 carbon atoms, arylalkyl groups having 7 to 20 carbon atoms, and polyaromatic ring groups having 13 to 20 carbon atoms.

[0092] The aryl group having 6 to 20 carbon atoms includes the above-mentioned R 5 Among the groups listed as aryl groups used in (1), groups having the specified number of carbon atoms can be used.

[0093] The arylalkyl group having 7 to 20 carbon atoms includes the above-mentioned R 5Among the groups listed as arylalkyl groups used in 1, those having the specified number of carbon atoms can be used.

[0094] The polyaromatic ring group having 13 to 20 carbon atoms is a group having a structure in which hydrocarbon groups containing two or more aromatic rings are bonded together. Examples of such a monovalent polyaromatic ring group include a group in which an aryl group and an arylalkyl group are bonded together, and a group in which two arylalkyl groups are bonded together.

[0095] The aryl group and arylalkyl group used in the polyaromatic ring group are the same as those in the above R 5 Among the aryl groups and arylalkyl groups used in the above, those which satisfy the predetermined number of carbon atoms when bonded can be used. For example, 1-benzyl-4-methylbenzene having 13 carbon atoms, which is a combination of a phenyl group as the aryl group and a benzyl group as the arylalkyl group, can be mentioned.

[0096] More specifically, examples of the monovalent polyaromatic ring group include compounds represented by the following formulae (p1) to (p5). However, the present invention is not limited to the following examples. When n is 2 or more, Y 1 When is a polyaromatic ring group, the bonds are preferably on different aromatic rings.

[0097] [ka] (In the formula, * indicates a bond.)

[0098] Y 1 The hydrocarbon group having a heterocyclic ring with 2 to 30 carbon atoms used in may or may not have a substituent, but a hydrocarbon group having a substituent is a group having a structure in which one or more hydrogen atoms in the hydrocarbon group are substituted with a substituent. 5 The substituents for substituting hydrogen atoms in the hydrocarbon groups used in the above can be the same as those listed above.

[0099] The hydrocarbon group having a heterocyclic ring with 2 to 30 carbon atoms is an n-valent hydrocarbon group in which one or more carbon atoms are substituted with a heterocyclic group having a valence of divalent or higher. The number of carbon atoms in the "hydrocarbon group having a heterocyclic ring with 2 to 30 carbon atoms" is intended to include the carbon atoms in the heterocyclic group, as defined for the number of carbon atoms in a group having a substituent. Therefore, the hydrocarbon group used in the hydrocarbon group having a heterocycle with 2 to 30 carbon atoms is selected so that the total number of carbon atoms in the group after the carbon atoms are substituted with the heterocyclic group satisfies 2 to 30 carbon atoms. The heterocyclic group having a valence of 2 or more and substituting a carbon atom in the hydrocarbon group may be a heterocyclic ring obtained by removing the same number of hydrogen atoms as the valence of the heterocyclic group. The hydrocarbon group in which one or more carbon atoms are substituted with a divalent or higher heterocyclic group can be a monovalent hydrocarbon group from which n-1 hydrogen atoms have been removed, and specific examples thereof include an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a cycloalkylalkyl group, and an arylalkyl group. 5 The groups mentioned above as groups used in the above can be used. In a hydrocarbon group in which one or more carbon atoms are substituted with a heterocyclic group having a valence of at least two, the number of hydrocarbon groups is not limited to one and may be two or more. Furthermore, the n bonds in the n-valent group may be present in either the heterocyclic group or the hydrocarbon group. For example, in Compound 2-4 described below, n hydrocarbon groups are substituted with one n-valent heterocyclic group, and a bond is present in each of the n hydrocarbon groups.

[0100] The heterocycle may be a monocyclic ring or a fused ring. The heterocycle having a fused ring structure is a structure in which a heterocycle is fused with a heterocycle or a hydrocarbon ring, and examples thereof include heterocycle-containing fused rings. Specific examples of the heterocycle include saturated monocyclic heterocycles such as a pyrrolidine ring, a piperidine ring, a piperazine ring, a morpholine ring, a thiomorpholine ring, a homopiperidine ring, a homopiperazine ring, a tetrahydropyridine ring, a tetrahydrofuran ring, a tetrahydropyran ring, a caprolactam ring, an isocyanuric ring, and a hydantoin ring, and saturated polycyclic hydrocarbon rings such as a tetrahydroquinoline ring, a tetrahydroisoquinoline ring, a dihydrobenzofuran ring, and a tetrahydrocarbazole ring.

[0101] Y 1 As the heterocyclic group having 2 to 30 carbon atoms represented by the formula (I), n-valent heterocyclic rings listed above as examples of the heterocyclic ring contained in the hydrocarbon group having a heterocyclic ring having 2 to 30 carbon atoms can be used.

[0102] In the present invention, R 6 , R 7 and R 8 are each independently preferably a hydrogen atom or an unsubstituted or substituted alkyl group having 1 to 3 carbon atoms, and are preferably a hydrogen atom or a methyl group, and are particularly preferably a hydrogen atom. This is because compound 2 has the above structure, which strengthens the intermolecular hydrogen bonding, and as a result, a film can be formed that shrinks less during curing and has excellent heat resistance and handleability.

[0103] In the present invention, R 9 is a hydrocarbon group having an ethylenically unsaturated bond group (hereinafter may be referred to as unsaturated bond-containing group A'), or a group in which one or more methylene groups of the unsaturated bond-containing group A' have been substituted with a divalent group selected from the above <Group B> (hereinafter may be referred to as unsaturated bond-containing group B'), and is preferably the unsaturated bond-containing group A'. This is because a film can be formed that shrinks less when cured and has better heat resistance and handling properties.

[0104] In the present invention, R 9The unsaturated bond-containing group A' used in is preferably an unsubstituted hydrocarbon group having 3 to 20 carbon atoms and having an ethylenically unsaturated bond group at its terminal. This is because compound 2 having the above structure can form a film that shrinks less when cured and has excellent heat resistance and handleability.

[0105] In the present invention, R 9 The unsaturated bond-containing group A' used in the above has 3 to 20 carbon atoms, preferably 3 to 18 carbon atoms, more preferably 3 to 15 carbon atoms, and even more preferably 3 to 12 carbon atoms, and among these, it is preferable that it has 3 to 10 carbon atoms, and particularly preferably 4 to 8 carbon atoms, and among these, it is particularly preferable that it has 5 to 6 carbon atoms. This is because a film can be formed that shrinks less when cured and has better heat resistance and handling properties. In addition, R 9 When the group used in is the unsaturated bond-containing group B', the preferred range of the number of carbon atoms therein can also be any of the preferred ranges given above for the unsaturated bond-containing group A'.

[0106] In the present invention, R 9 The type of hydrocarbon group in which a hydrogen atom is substituted with an ethylenically unsaturated bond group in the unsaturated bond-containing group A' used in is preferably an alkyl group, and particularly preferably a straight-chain alkyl group. This is because compound 2 has the above structure and can form a film that shrinks less during curing and is excellent in heat resistance and handleability. Similarly, R 9 The hydrocarbon group that substitutes the methylene group in the unsaturated bond-containing group B' used in is preferably an alkyl group.

[0107] In the present invention, R 9The ethylenically unsaturated bond group of the unsaturated bond-containing group A' used in is preferably a vinyl group, an isopropenyl group, an acryloyloxy group, or a methacryloyloxy group, and among these, an acryloyloxy group or a methacryloyloxy group is preferred. This is because, due to the above structure, compound 2 is easy to obtain as raw materials, is easy to synthesize, and can form a film that shrinks less during curing and is excellent in heat resistance and handleability. In addition, R 9 When the group used in is the unsaturated bond-containing group B', the preferred range can also be the same as the preferred range given above for the unsaturated bond-containing group A'.

[0108] In the present invention, R 9 The unsaturated bond-containing group A' used in may have only one ethylenically unsaturated bond group or may have two or more ethylenically unsaturated bond groups, but preferably has three or less ethylenically unsaturated bond groups, more preferably has two or less ethylenically unsaturated bond groups, and most preferably has one ethylenically unsaturated bond group. This is because compound 1 has the above structure, which allows it to form a film that shrinks less during curing and has excellent heat resistance and handleability. In addition, R 9 When the group used in is the unsaturated bond-containing group B', the preferred range can also be the same as the preferred range given above for the unsaturated bond-containing group A'.

[0109] In the present invention, R 10is an unsaturated bond-containing group A', an unsaturated bond-containing group B', an unsubstituted or substituted hydrocarbon group having 6 to 20 carbon atoms and an aromatic ring (hereinafter sometimes referred to as aromatic ring-containing group C'), an unsubstituted or substituted hydrocarbon group having 3 to 20 carbon atoms and an aliphatic hydrocarbon ring (hereinafter sometimes referred to as aliphatic ring-containing group D'), or a group in which one or more methylene groups in the above hydrocarbon group having an aromatic ring or the above hydrocarbon group having an aliphatic hydrocarbon ring are substituted with a divalent group selected from the above <Group B>, but is preferably unsaturated bond-containing group A', unsaturated bond-containing group B', or aromatic ring-containing group C', and particularly preferably unsaturated bond-containing group A' or unsaturated bond-containing group B', with unsaturated bond-containing group A' being particularly preferred. This is because compound 2 has the above structure and can form a film that shrinks less when cured and has excellent heat resistance and handleability.

[0110] In the present invention, R 10 Preferred structures of the unsaturated bond-containing group A′ and the unsaturated bond-containing group B′ used in R 9 The unsaturated bond-containing group A' and the unsaturated bond-containing group B' can be the same as those preferably used in the above formula (1).

[0111] In the present invention, R 10 The aromatic-containing group C′ used in the above is preferably an unsubstituted hydrocarbon group having 6 to 20 carbon atoms and having an aromatic ring, because this allows the formation of a film that shrinks less during curing and has excellent heat resistance and handling properties.

[0112] In the present invention, R 10The aromatic-containing group C' used in the formula (1) has 6 to 20 carbon atoms, more preferably 6 to 18 carbon atoms, and even more preferably 6 to 15 carbon atoms, and among these, it is preferable that it has 6 to 12 carbon atoms, and particularly preferably 6 to 10 carbon atoms, and among these, it is particularly preferable that it has 6 to 8 carbon atoms. This is because compound 2 has the above structure, which allows it to form a film that shrinks less when cured and has excellent heat resistance and handleability.

[0113] In the present invention, R 10 The aromatic-containing group C′ used in is preferably a hydrocarbon group that is unsubstituted or substituted and has phenyl, biphenyl, benzyl, or phenylethyl. This is because compound 2 having the above structure can form a film that shrinks less during curing and has excellent heat resistance and handleability.

[0114] In the present invention, R 10 The aliphatic ring-containing group D' used in is preferably an unsubstituted hydrocarbon group having 3 to 20 carbon atoms and having an aliphatic hydrocarbon ring. In the present invention, R 10 The aliphatic ring-containing group D' used in the above has 3 to 20 carbon atoms, preferably 4 to 18 carbon atoms, more preferably 5 to 15 carbon atoms, and even more preferably 6 to 12 carbon atoms. This is because compound 1 has the above structure, which allows it to form a film that shrinks less during curing and has excellent heat resistance and handleability.

[0115] In the present invention, R 10 The aliphatic ring-containing group D' used in is preferably a hydrocarbon group that is unsubstituted or substituted and has a cyclohexyl or adamantyl group, because the compound 1 has the above structure and can form a film that shrinks less during curing and has excellent heat resistance and handleability.

[0116] In the present invention, X 4 , X5 and X 6 are each independently a divalent hydrocarbon group having 1 to 20 carbon atoms, or a divalent hydrocarbon group in which one or more methylene groups have been substituted with a divalent group selected from the above <Group B>, and are preferably a divalent hydrocarbon group having 1 to 20 carbon atoms. This is because Compound 2 has the above structure, which allows it to form a film that shrinks less when cured and has excellent heat resistance and handleability.

[0117] X 4 , X 5 and X 6 The number of carbon atoms in the divalent hydrocarbon group having 1 to 20 carbon atoms used in the above is preferably 1 to 20, more preferably 1 to 15, more preferably 1 to 10, particularly preferably 1 to 6, and most preferably 1 to 3. This is because compound 2 has the above structure, making it easy to obtain raw materials and easy to synthesize, and also enabling the formation of a film that shrinks less during curing and is more excellent in heat resistance and handleability.

[0118] In the present invention, Y 1 The n-valent group used in is preferably an alkyl group from which n-1 hydrogen atoms have been removed, a hydrocarbon group having an aromatic ring, or a hydrocarbon group having a heterocyclic ring, or a group in which a methylene group in these groups has been substituted with a group of <Group B>, and among these, Y 1 The n-valent group used in is preferably an alkyl group from which n-1 hydrogen atoms have been removed, a hydrocarbon group having an aromatic ring, or a hydrocarbon group having a heterocycle, particularly preferably an alkyl group from which n-1 hydrogen atoms have been removed, or a hydrocarbon group having an aromatic ring, and among these, a hydrocarbon group having an aromatic ring is particularly preferred. This is because Compound 2 having the above structure can form a film that shrinks less when cured and is excellent in heat resistance and handleability.

[0119] In the present invention, Y 1The hydrocarbon group used in is preferably unsubstituted. This is because, with the above structure, Compound 2 is easy to obtain raw materials for, is easy to synthesize, and can form a film that shrinks less during curing and is excellent in heat resistance and handleability.

[0120] In the present invention, Y 1 The aliphatic hydrocarbon group used in the above has 2 to 15 carbon atoms. It is preferable that the number of carbon atoms in the compound 2 is 3 to 10, and more preferably 5 to 8. This is because compound 2 has the above structure, and raw materials thereof are readily available, the compound 2 is easy to synthesize, and a film can be formed which shrinks less when cured and has excellent heat resistance and handleability.

[0121] In the present invention, Y 1 The number of carbon atoms in the hydrocarbon group having an aromatic ring used in is preferably 6 to 18, more preferably 7 to 16, and particularly preferably 8 to 14. This is because compound 2 has the above structure, making it easy to obtain raw materials and easy to synthesize, and also enabling the formation of a film that shrinks less during curing and is more excellent in heat resistance and handleability.

[0122] In the present invention, Y 1 The number of carbon atoms in the hydrocarbon group having a heterocycle used in the above is preferably 5 to 28, more preferably 10 to 25, and particularly preferably 15 to 23. This is because compound 2 has the above structure, making it easy to obtain raw materials and easy to synthesize, and also enabling the formation of a film that shrinks less during curing and is more excellent in heat resistance and handleability.

[0123] In the present invention, Y 1 The hydrocarbon group in which one or more carbon atoms are substituted with a heterocyclic group used in is preferably an alkyl group. This is because, with the above structure, Compound 2 is easy to obtain raw materials for, is easy to synthesize, and can form a film that shrinks less during curing and is excellent in heat resistance and handleability.

[0124] In the present invention, Y 1 The heterocyclic group used in is preferably an isocyanuric ring group, because the compound 2 has the above structure, raw materials are readily available, the compound 2 is easy to synthesize, and a film can be formed that shrinks less during curing and has excellent heat resistance and handleability.

[0125] In the present invention, n is preferably 2 or 3. This is because compound 2 has the above structure, and the raw materials are readily available, the compound is easy to synthesize, and a film can be formed which shrinks less during curing and has excellent heat resistance and handleability.

[0126] Specific examples of compound 2 of the present invention include compounds represented by the following formulae (101) to (142). However, the present invention is not limited to the following examples. In the formulae, m is a number of 0 to 9.

[0127] [ka] [ka] [ka] [ka] [ka] [ka]

[0128] The method for producing the compound 2 may be any method that can produce a compound of the desired structure, and can be synthesized by applying well-known chemical reactions. For example, the method shown in the following scheme can be mentioned. Specifically, after synthesizing the compound 1, the compound 1 is further reacted with an isocyanate to obtain compound 2, which is a polymer of compound 1. The following illustrates an example in which compound 1 produced by scheme (A) is used. There are no particular limitations on the reaction conditions in the production method, such as the reaction temperature, reaction time, and amount of raw materials used, and well-known conditions may be used.

[0129] [ka] (X is X in formula (I) 1 The two Rs may be the same or different, and each R 1 and R 3 is the group corresponding to [ka] (X is X 1 , X 4 The plural Xs may be the same or different. Y is Y in formula (II). 1 and Y-(NCO)n is an isocyanate that reacts with compound 1 to give compound 2.

[0130] B. Polymer The polymer of the present invention (hereinafter, sometimes referred to as polymer B) has structural units derived from compound A above. According to the present invention, by having a structural unit derived from compound A, polymer B can form a film that shrinks little during curing and has excellent heat resistance and handleability.

[0131] 1. Building block derived from compound A Polymer B of the present invention has a structural unit derived from compound A (hereinafter, may be referred to as structural unit A). Here, the compound A constituting the structural unit A can be the same as those described in the above section "A. Compound," and therefore, further explanation will be omitted here.

[0132] The content of the structural unit A is preferably 50 parts by mass or more, more preferably 70 parts by mass or more, particularly preferably 80 parts by mass or more, and particularly preferably 90 parts by mass or more, per 100 parts by mass of polymer B. This is because the polymer B shrinks less when cured at this content.

[0133] 2. Constituent units other than constituent unit A The polymer B has the structural unit A, but may also have other structural units as necessary. Examples of such other structural units include structural units (hereinafter sometimes referred to as structural unit X) derived from a radically polymerizable compound other than compound A (hereinafter sometimes referred to as radically polymerizable compound X). The polymer B may be a homopolymer of the compound A, or a copolymer of the compound A and the radical polymerizable compound X.

[0134] The radical polymerizable compound X may be any compound other than the compound A, for example, a compound having a radical polymerizable reactive group and an ethylenically unsaturated bond group. is preferred, and among these, acrylate or methacrylate is more preferred, because the radical polymerizable compound X has high reactivity and it is easy to adjust the ratio of the structural unit A to the structural unit X in the polymer. The radical polymerizable compound X may be used alone or in combination of two or more. In this specification, "(meth)acrylate" means acrylate or methacrylate, and "(meth)acrylic" means acrylic or methacrylic.

[0135] Examples of monofunctional (meth)acrylates include isoamyl (meth)acrylate, stearyl (meth)acrylate, lauryl (meth)acrylate, octyl (meth)acrylate, decyl (meth)acrylate, isomylstyryl (meth)acrylate, isostearyl (meth)acrylate, 2-ethylhexyl-diglycol (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 2-(meth)acryloyloxyethyl hexahydrophthalate, butoxyethyl (meth)acrylate, ethoxydiethylene glycol (meth)acrylate, methoxydiethylene glycol (meth)acrylate, and methoxypolyethylene. Examples of the acrylates include propylene glycol (meth)acrylate, methoxypropylene glycol (meth)acrylate, phenoxyethyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, isobornyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, 2-(meth)acryloyloxyethyl succinate, 2-(meth)acryloyloxyethyl phthalate, 2-(meth)acryloyloxyethyl-2-hydroxyethyl phthalate, and t-butylcyclohexyl (meth)acrylate.

[0136] Examples of polyfunctional (meth)acrylates include triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, tricyclodecane dimethanol di(meth)acrylate, bisphenol A PO adduct di(meth)acrylate, and neopentyl glycol hydroxypivalate. Examples of the acrylates include difunctional (meth)acrylates such as diethyl acrylate, polytetramethylene glycol di(meth)acrylate, polyethylene glycol diacrylate, and tripropylene glycol diacrylate, and trifunctional or higher (meth)acrylates such as trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol hexa(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, glycerin propoxy tri(meth)acrylate, and pentaerythritol ethoxy tetra(meth)acrylate.

[0137] When polymer B is a copolymer of compound A and radically polymerizable compound X, the content of structural unit X is preferably 50 parts by mass or less, more preferably 30 parts by mass or less, particularly preferably 20 parts by mass or less, and particularly preferably 10 parts by mass or less, per 100 parts by mass of polymer B. This is because the shrinkage of polymer B during curing is reduced by the content in the above range.

[0138] 3.Other The method for producing polymer B may be any method that can contain structural unit A in the desired blending amount. The polymerization method is not particularly limited, and may be solution polymerization using a solvent, or bulk polymerization when the polymerizable compound containing compound A is in a liquid state.

[0139] C. Composition The composition of the present invention (hereinafter, sometimes referred to as composition C) is characterized by containing compound A. According to the present invention, it is possible to form a film that has little shrinkage upon curing and is excellent in heat resistance and handling properties.

[0140] 1. Compound A As for compound A, the same compounds as those described above in "A. Compound" can be used, and therefore a description thereof will be omitted here.

[0141] The content of compound A is preferably 0.1 parts by mass or more, more preferably 30 parts by mass or more, more preferably 50 parts by mass or more, and more preferably 60 parts by mass or more, and of these, preferably 70 parts by mass or more, particularly preferably 80 parts by mass or more, and of these, particularly preferably 90 parts by mass or more, based on 100 parts by mass of the solid content of composition C. This is because the shrinkage of composition C during curing is reduced by using the above content. Furthermore, the upper limit is preferably 99.9 parts by mass or less. This is because the content is such that composition C can contain other components such as a polymerization initiator. The above solid content refers to the components of composition C excluding the solvent.

[0142] The content of Compound A is preferably 1 to 99 parts by mass, more preferably 5 to 80 parts by mass, even more preferably 8 to 70 parts by mass, particularly preferably 10 to 60 parts by mass, even more preferably 15 to 50 parts by mass, in 100 parts by mass of Composition C. With the content in the above range, composition C can form a film that shrinks less when cured and has excellent heat resistance and handling properties.

[0143] 2. Other ingredients 2-1. Radical polymerizable compound Y other than compound A 1 Composition C contains a radical polymerizable compound other than compound A (hereinafter referred to as radical polymerizable compound Y 1 The radical polymerizable compound Y may be contained. 1 Regarding the radical polymerizable compound X, the same compounds as those described above in the section "B. Polymer" can be used, and therefore the description here will be omitted.

[0144] Composition C comprises compound A and radical polymerizable compound Y 1 When both of the radical polymerizable compound Y 1 The content of compound A and radical polymerizable compound Y 1 The content is preferably 50 parts by mass or less, more preferably 30 parts by mass or less, particularly preferably 20 parts by mass or less, and particularly preferably 10 parts by mass or less, based on a total of 100 parts by mass of the components. This is because, with the content in the above range, composition C can form a film that shrinks less when cured and has excellent heat resistance and handleability.

[0145] 2-2. Polymerization initiator Composition C preferably contains a polymerization initiator as needed, because this provides better curability.

[0146] The polymerization initiator may be any radical polymerization initiator used for polymerizing a compound having an ethylenically unsaturated bond, and any conventionally known compound may be used. The radical polymerization initiator may be either a photoradical polymerization initiator or a thermal radical polymerization initiator. In the present invention, it is particularly preferred that the polymerization initiator is a photoradical polymerization initiator, since composition C exhibits little cure shrinkage and can easily form a film having excellent heat resistance.

[0147] Examples of the photoradical polymerization initiator include benzoins such as benzoin, benzoin methyl ether, benzoin propyl ether, and benzoin butyl ether; benzil ketals such as benzil dimethyl ketal; acetophenone, 2,2-dimethoxy-2-phenylacetophenone, 2,2-diethoxy-2-phenylacetophenone, 1-benzyl-1-dimethylamino-1-(4'-morpholinobenzoyl)propane, 2-morpholyl-2-(4'-methylmercapto)benzoylpropane, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholino-propan-1-one, 1-hydroxycyclohexyl phenyl ketone, 1-hydroxy-1-benzoylcyclohexane, 2-hydroxy-2-benzoylpropane, 2-hydroxy-2-(4'-isopropyl)benzoylpropane, N,N-dimethylaminoacetophenone, 1,1-dichloroacetophenone, 4-butylbenzoyltrichloromethane, and 4-phenoxybenzyl. Acetophenones such as dichloromethane; anthraquinones such as 2-methylanthraquinone, 1-chloroanthraquinone, and 2-amylanthraquinone; thioxanthones such as 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone, and 2,4-diisopropylthioxanthone; ketals such as acetophenone dimethyl ketal and benzyl dimethyl ketal; benzophenone, methylbenzophenone, and 4,4'-dichlorobenzophenone Benzophenones such as 4,4'-bisdiethylaminobenzophenone, Michler's ketone, and 4-benzoyl-4'-methyldiphenyl sulfide; oxides such as 2,4,6-trimethylbenzoyldiphenylphosphine oxide and bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide; carbazoles such as 3-(2-methyl-2-morpholinopropionyl)-9-methylcarbazole; α-dicarbonyls such as benzyl and methyl benzoylformate;Oxygen compounds such as those described in JP 2000-80068 A, JP 2001-233842 A, JP 2005-97141 A, JP 2006-516246 A, Japanese Patent No. 3860170 A, Japanese Patent No. 3798008 A, WO2006 / 018973 A, JP 2011-132215 A, and WO2015 / 152153 A p-Methoxyphenyl-2,4-bis(trichloromethyl)-s-triazine, 2-methyl-4,6-bis(trichloromethyl)-s-triazine, 2-phenyl-4,6-bis(trichloromethyl)-s-triazine, 2-naphthyl-4,6-bis(trichloromethyl)-s-triazine, 2-(p-butoxystyryl)-s-triazine Triazines such as triazine; benzoyl peroxide, 2,2'-azobisisobutyronitrile, ethyl anthraquinone, 1,7-bis(9'-acridinyl)heptane, thioxanthone, 1-chloro-4-propoxythioxanthone, isopropylthioxanthone, diethylthioxanthone, benzophenone, phenyl biphenyl ketone, 4-benzoyl-4'-methyldiphenyl sulfide, 2-(p-butoxystyryl)-5-trichloromethyl-1,3,4-oxadiazole, 9-phenylacridine, 9,10-dimethylbenzphenazine, benzophenone / Michler's ketone, hexaarylbiimidazole / mercaptobenzimidazole, thioxanthone / amine, etc.;

[0148] Examples of the thermal radical polymerization initiator include azo compounds and organic peroxides. Examples of azo compounds include 2,2'-azobis(isobutyronitrile), 2,2'-azobis(2,4-dimethylvaleronitrile), 2,2'-azobis(2-methylbutyronitrile), 4,4'-azobis(4-cyanovaleric acid), 2,2'-azobis(2-methyl)dihydrochloride, 1,1'-azobis(1-acetoxy-1-phenylethane), 1,1'-azobis(cyclohexane-1-carboxamide), 1,1'-azobis(1-methyl-2-methylpropional ... Examples of suitable azo compounds include 2,2'-azobis(isobutyrate), 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile), 2,2'-azobis(2-methylpropionitrile), 2,2'-azobis(2-methylbutyronitrile), 1-[(1-cyano-1-methylethyl)azo]formamide, 2-phenylazo-4-methoxy-2,4-dimethylvaleronitrile, dimethyl 2,2'-azobis(2-methylpropionate), and 2,2'-azobis(N-butyl-2-methylpropionamide). Among these, azo compounds such as 2,2'-azobis(2-methylbutyronitrile) are preferred due to their high yield.

[0149] Examples of the organic peroxide include benzoyl peroxide, tert-butyl hydroperoxide, cumene hydroperoxide, di-tert-butyl peroxide, methyl ethyl ketone peroxide, 1,1-di(t-hexylperoxy)cyclohexane, 2,2-di(t-butylperoxy)butane, n-butyl 4,4-di(t-butylperoxy)valerate, 2,2-di(4,4-di(t-butylperoxy)cyclohexyl)propane, and p-menthane hydroperoxide.

[0150] Commercially available thermal radical polymerization initiators include, for example, "AIBN" (2,2'-azobis(isobutyronitrile)), "V-40" (1,1'-azobis(cyclohexane-1-carbonitrile), "VAm-110" (2,2'-azobis(N-butyl-2-methylpropionamide), and "V-601" (dimethyl 2,2'-azobis(isobutyrate)), all manufactured by Wako Pure Chemical Industries, Ltd.; and "OTAZO-15" (1,1'-azobis(1-acetoxy-1-phenylethane) and "MAIB" (dimethyl 2,2'-azobisisobutyrate), all manufactured by Otsuka Chemical Co., Ltd.

[0151] The thermal radical polymerization initiator used preferably has a 10-hour half-life temperature of 40°C to 80°C, more preferably 50°C to 70°C, from the viewpoints of reaction efficiency and safety.

[0152] The content of the polymerization initiator is preferably 0.1 to 10 parts by mass, more preferably 0.5 to 8 parts by mass, and particularly preferably 1 to 6 parts by mass, relative to 100 parts by mass of compound A, because this provides better curability. The content of the polymerization initiator is preferably 0.1 to 10 parts by mass, more preferably 0.5 to 8 parts by mass, and particularly preferably 1 to 6 parts by mass, relative to 100 parts by mass of the total of compound A and radically polymerizable compound X. This is because the curability is superior.

[0153] 2-3. Polymer B The composition C may contain a polymer B in addition to the compound A. As for such polymer B, the same polymers as those described in the above section "B. Polymer" can be used, and therefore the description here will be omitted.

[0154] 2-4.Solvent Composition C may contain a solvent. The solvent is a compound that is liquid at 25° C. and 1 atmosphere, and is a compound other than the compound A, the polymer B, the radical polymerizable compound X, and the polymerization initiator. The solvent may be any solvent capable of dissolving or dispersing each component of composition C (compound A, etc.), and examples thereof include ketone-based solvents such as methyl ethyl ketone, methyl amyl ketone, diethyl ketone, acetone, methyl isopropyl ketone, methyl isobutyl ketone, cyclohexanone, and 2-heptanone; ether-based solvents such as ethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, and dipropylene glycol dimethyl ether; ester-based solvents such as methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, 3-methoxybutyl acetate, cyclohexyl acetate, ethyl lactate, dimethyl succinate, and Texanol; cellosolve-based solvents such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; alcohol-based solvents such as methanol, ethanol, iso- or n-propanol, iso- or n-butanol, and amyl alcohol; ethylene glycol monomethyl acetate, ethylene glycol monoethyl acetate, propylene glycol monomethyl ether ... Ether ester solvents such as ethylene glycol monomethyl ether acetate, dipropylene glycol monomethyl ether acetate, 3-methoxybutyl acetate, and ethoxyethyl propionate; BTX solvents such as benzene, toluene, and xylene; aliphatic hydrocarbon solvents such as hexane, heptane, octane, and cyclohexane; terpene hydrocarbon oils such as turpentine oil, D-limonene, and pinene; mineral spirits, Swazol #310 (all manufactured by Cosmo Matsuyama Oil); and Solvesso #100 (all manufactured by Exxon Chemical). halogenated aliphatic hydrocarbon solvents such as carbon tetrachloride, chloroform, trichloroethylene, methylene chloride, and 1,2-dichloroethane; halogenated aromatic hydrocarbon solvents such as chlorobenzene; carbitol solvents, aniline, triethylamine, pyridine, acetic acid, acetonitrile, carbon disulfide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, and water, and these solvents can be used alone or in combination.Ether solvents and polar solvents are preferred because of their good yield, and 1,4-dioxane and dimethylformamide are particularly preferred.

[0155] The content of the solvent is preferably 1 to 99 parts by mass, more preferably 10 to 95 parts by mass, particularly preferably 30 to 90 parts by mass, and particularly preferably 50 to 85 parts by mass, relative to 100 parts by mass of Composition C. This is because the content within the above range makes the composition easier to handle.

[0156] 2-5. Other additives Composition C may contain an ultraviolet absorber. Examples of the ultraviolet absorber include benzotriazole-based ultraviolet absorbers, triazine-based ultraviolet absorbers, benzophenone-based ultraviolet absorbers, cyanoacrylate-based ultraviolet absorbers, and inorganic fine particles that absorb ultraviolet light, such as titanium oxide fine particles. These ultraviolet absorbents may be used alone or in combination of two or more.

[0157] Composition C may contain various components depending on the purpose. For example, it may contain a hindered amine light stabilizer (HALS) to improve weather resistance, an antioxidant to improve heat resistance and weather resistance, or a radical polymerization inhibitor to improve storage stability.

[0158] The content of the other components can be 50 parts by mass or less in 100 parts by mass of Composition C.

[0159] 3.Other The method for producing the composition C may be any method that can contain the compound A and the polymer B in the desired amounts. When the composition C contains the compound A, the polymer B, and other components, a method using a known mixing means can be used.

[0160] D. Adhesive The adhesive of the present invention (hereinafter, sometimes referred to as adhesive D) contains composition C described above. According to the present invention, by containing the composition C, shrinkage during curing is small, heat resistance is excellent, and both adhesion and durability are high.

[0161] 1. Composition C Adhesive D contains composition C described above. The contents of such a composition can be the same as those described in the above section "C. Composition," and therefore, a description thereof will be omitted.

[0162] 2. Other ingredients 2-1. Solvent The adhesive D may contain a solvent. As the solvent, the same solvents as those described in the above section "C. Composition" can be used, and therefore a description thereof will be omitted here.

[0163] 2-2. Other additives Furthermore, various resin additives such as coupling agents, sensitizers, surfactants, crosslinking agents, inorganic fillers, organic fillers, antifoaming agents, thickeners, leveling agents, organometallic coupling agents, thixotropic agents, colorants, carbon compounds, metal fine particles, flame retardants, plasticizers, light stabilizers, heat stabilizers, antioxidants, elastomer particles, chain transfer agents, polymerization inhibitors, ultraviolet absorbers, antioxidants, antistatic agents, release agents, flow adjusters, adhesion promoters, water-soluble preservatives, conductive substances, and unsaturated monomers may be added to adhesive D as needed, as long as the effects of the present invention are not impaired.

[0164] Adhesive D may contain a liquid photopolymerizable acrylic monomer or liquid photopolymerizable monovinyl monomer as a reactive diluent to reduce viscosity or improve application. Liquid photopolymerizable acrylic monomers are commercially available or can be prepared by known methods. Examples of liquid photopolymerizable monovinyl monomers include vinyl esters such as vinyl acetate; monoacrylic esters such as alkyl acrylates, alkyl methacrylates, hydroxyalkyl methacrylates, isobornyl acrylate, isobornyl methacrylate, dicyclopentenyl acrylate, and dicyclopentenyl methacrylate; esters of acrylic acid or methacrylic acid with polyhydric alcohols; and polyhydric alcohols such as glycerol, 1,1,1-trimethylolpropane, trihydroxyethyl isocyanurate, erythritol, and pentaerythritol.

[0165] 3.Other The adhesive of the present invention can be applied to a substrate such as glass, metal, paper, plastic, etc. by known means such as a spin coater, a bar coater, a roll coater, a curtain coater, various printing methods, dipping, etc. Alternatively, once the adhesive is applied to a substrate such as a film, it can be transferred to another substrate, and there are no limitations on the application method.

[0166] Specific applications of the adhesive of the present invention include optical materials such as eyeglasses and imaging lenses, antistatic films, optical films, conductive films, protective films, heat-shielding materials, transfer foils, printing plates, insulating varnishes, insulating sheets, laminates, printed circuit boards, substrates for flexible displays, substrates for touch panels, printing masks, molding materials, automobile parts, in-vehicle equipment, putty, building materials, siding, bookbinding, packaging, fibers, IC cards, substrates for IC tags, substrates for electronic paper, glass fiber impregnation agents, sealants, passivation films for semiconductors, solar cells, etc., interlayer insulating films, protective films, lens portions of lens sheets such as prism lens sheets used in the backlights of liquid crystal display devices, Fresnel lens sheets used in screens of projection televisions, etc., and lenticular lens sheets, and the like, as well as the use of such sheets. Examples of suitable adhesives include backlights using adhesives, protective films and spacers for liquid crystal color filters, DNA separation chips, microreactors, nanobiodevices, hard disk recording materials, solid-state imaging devices, solar cell panels, light-emitting diodes, organic light-emitting devices, electrode protective materials, luminescent films, fluorescent films, MEMS devices, actuators, holograms, plasmonic devices, polarizing plates, polarizing films, alignment films, optical lenses such as microlenses, optical elements, optical connectors, optical waveguides, optical molding agents, fluidic devices, inkjet nozzles, precision-machined parts, food and beverage containers, food packaging materials, dental materials, sanitary ware, and household equipment such as bathtubs. Substrates suitable for use as adhesives include metal, wood, rubber, plastic, glass, ceramic products, cloth, and paper. Specific examples of adhesives suitable for use in fixing camera lenses and CD image sensors are preferred. This is because they exhibit minimal shrinkage upon curing, excellent heat resistance, and excellent positioning accuracy.

[0167] E. Coating agent The coating agent of the present invention (hereinafter, sometimes referred to as coating agent E) contains composition C described above. According to the present invention, by containing the composition C, shrinkage during curing is small, heat resistance is excellent, and both adhesion and durability are high.

[0168] 1. Composition C Coating agent E contains composition C described above. The contents of such a composition can be the same as those described in the above section "C. Composition," and therefore, a description thereof will be omitted.

[0169] 2. Other ingredients 2-1. Solvent Coating agent E may contain a solvent. As the solvent, the same solvents as those described in the above section "C. Composition" can be used, and therefore a description thereof will be omitted here.

[0170] 2-2. Other additives Furthermore, various resin additives such as coupling agents, sensitizers, surfactants, crosslinking agents, inorganic fillers, organic fillers, antifoaming agents, thickeners, leveling agents, organometallic coupling agents, thixotropic agents, colorants, carbon compounds, metal fine particles, flame retardants, plasticizers, light stabilizers, heat stabilizers, antioxidants, elastomer particles, chain transfer agents, polymerization inhibitors, ultraviolet absorbers, antioxidants, antistatic agents, release agents, flow adjusters, adhesion promoters, water-soluble preservatives, conductive substances, and unsaturated monomers may be added to Coating Agent E as needed, as long as the effects of the present invention are not impaired.

[0171] 3.Other The coating agent of the present invention can be applied to a substrate such as glass, metal, paper, plastic, etc. by known means such as a spin coater, a bar coater, a roll coater, a curtain coater, various printing methods, dipping, etc. Alternatively, once applied to a substrate such as a film, it can be transferred to another substrate, and there is no limitation on the application method.

[0172] Specific applications of the coating agent of the present invention include optical materials such as eyeglasses and imaging lenses, antistatic films, optical films, conductive films, protective films, heat-shielding materials, transfer foils, printing plates, insulating varnishes, insulating sheets, laminates, printed circuit boards, substrates for flexible displays, substrates for touch panels, printing masks, molding materials, automobile parts, in-vehicle equipment, putty, building materials, siding, bookbinding, packaging, fibers, IC cards, substrates for IC tags, substrates for electronic paper, glass fiber impregnation agents, sealants, passivation films for semiconductors, solar cells, etc., interlayer insulating films, protective films, lens portions of lens sheets such as prism lens sheets used in backlights of liquid crystal display devices, Fresnel lens sheets used in screens of projection televisions, etc., and lenticular lens sheets, and the like. Examples of applications include backlights using the sheet, protective films and spacers for liquid crystal color filters, DNA separation chips, microreactors, nanobiodevices, hard disk recording materials, solid-state imaging devices, solar cell panels, light-emitting diodes, organic light-emitting devices, electrode protective materials, luminescent films, fluorescent films, MEMS devices, actuators, holograms, plasmon devices, polarizing plates, polarizing films, alignment films, optical lenses such as microlenses, optical elements, optical connectors, optical waveguides, optical molding agents, fluidic devices, inkjet nozzles, precision-machined parts, food and beverage containers, food packaging materials, dental materials, sanitary ware, and household equipment such as bathtubs. Substrates that can be used as adhesives include metal, wood, rubber, plastic, glass, ceramic products, cloth, and paper. A more specific example of a surface coating for touch panel devices is its use. This is because it exhibits low shrinkage upon curing, excellent heat resistance, and is an excellent coating agent with high adhesion and durability.

[0173] F. Cured product The cured product of the present invention (hereinafter sometimes referred to as cured product F) is a cured product of composition C above. According to the present invention, the use of the composition C results in little shrinkage during curing, and excellent heat resistance and handling properties.

[0174] 1. Composition C Cured product F was obtained using composition C described above. The contents of such a composition can be the same as those described in the above section "C. Composition," and therefore, a description thereof will be omitted.

[0175] 2. Other ingredients Furthermore, various resin additives such as coupling agents, sensitizers, surfactants, crosslinking agents, inorganic fillers, organic fillers, antifoaming agents, thickeners, leveling agents, organometallic coupling agents, thixotropic agents, colorants, carbon compounds, metal fine particles, flame retardants, plasticizers, light stabilizers, heat stabilizers, antioxidants, elastomer particles, chain transfer agents, polymerization inhibitors, ultraviolet absorbers, antioxidants, antistatic agents, release agents, flow adjusters, adhesion promoters, water-soluble preservatives, conductive substances, and unsaturated monomers may be added to the cured product F as needed, as long as the effects of the present invention are not impaired.

[0176] 3.Other The method for producing the cured product F is not particularly limited as long as it is a method that can cure the composition C. As a method for producing such a cured product F, the method described later in the section "G. Method for producing a cured product" can be used.

[0177] The cured product of the present invention has a small change in volume before and after curing, and is therefore suitable for use in a variety of applications, including curable paints, varnishes, curable adhesives, printed circuit boards, display devices (color filters in color display liquid crystal display panels for color televisions, PC monitors, personal digital assistants, digital cameras, etc., color filters for various display applications, color filters for CCD image sensors, touch panels, electroluminescent display devices, plasma display panels, and black partition walls for organic EL), powder coatings, printing inks, printing plates, adhesives, gel coats, photoresists for electronics, electroplating resists, etching resists, solder resists, insulating films, black matrices, and resists for forming structures in the manufacturing process of LCDs, electrical and and compositions for encapsulating electronic components, solder resists, magnetic recording materials, micromechanical components, waveguides, optical switches, plating masks, etching masks, color test systems, glass fiber cable coatings, screen printing stencils, materials for producing three-dimensional objects by stereolithography, holographic recording materials, image recording materials, fine electronic circuits, bleaching materials, bleaching materials for image recording materials, bleaching materials for image recording materials using microcapsules, photoresist materials for printed wiring boards, photoresist materials for UV and visible laser direct imaging systems, photoresist materials and protective films used to form dielectric layers in the sequential lamination of printed circuit boards, and the like.

[0178] G. Manufacturing method of cured product The method for producing the cured product of the present invention will now be described. The method for producing a cured product of the present invention is characterized by comprising a step of curing the above-described composition.

[0179] 1. Hardening process In the curing step of the present invention, the method for curing the composition can be a commonly used method, such as a method of irradiating the composition C with light or a method of heating the composition C. In the present invention, when composition C contains a polymerization initiator together with compound A, the polymerization can be carried out by a method in which radicals are generated from the polymerization initiator. When the polymerization initiator is a photoradical polymerization initiator, the method is preferably a method of irradiating the composition C with light, and when the polymerization initiator is a thermal radical polymerization initiator, the method is preferably a method of heating the composition C. In the present invention, the curing method is preferably a method of irradiating the composition C with light, i.e., the curing step is preferably a step of irradiating the composition C with light, because this makes it easy to form a film with little cure shrinkage and excellent heat resistance. Specific examples of the light irradiation method, heating method, etc. include the same methods as those exemplified as the polymerization method described in the section "A. Compound" above.

[0180] 2. Other processes The method for producing a cured product of the present invention may include other steps in addition to the curing step, if necessary. Examples of the other steps include a developing step in which unpolymerized portions in the coating film of the composition are removed after the curing step to obtain a patterned cured product; a post-baking step in which the cured product is heat-treated after the curing step; a pre-baking step in which the composition is heat-treated to remove the solvent in the composition before the curing step; and a step in which a coating film of the composition is formed before the curing step. When a crosslinking agent, a coupling agent, or the like is contained, a reaction step with each agent may be included in addition to the above steps. The curing conditions may be appropriately set depending on the components used.

[0181] 3.Cured product The cured product produced by the method for producing a cured product according to the present disclosure can be similar to the content described in the above section "F. Cured product," and therefore a description thereof will be omitted here.

[0182] The present invention is not limited to the above-described embodiments. The above-described embodiments are merely examples, and any configuration that is substantially identical to the technical idea described in the claims of the present invention and that provides similar effects is included within the technical scope of the present invention. [Example]

[0183] EXAMPLES The present invention will be specifically explained below by showing examples and comparative examples, but the present invention is not limited to the following examples in any way.

[0184] [Example 1] (Synthesis of Compound 1-1) Tris(2-hydroethyl)isocyanate (1.0 eq.), dibutyltin dilaurate (0.04 eq.), and tetrahydrofuran were added to a 100 mL recovery flask and the atmosphere was replaced with nitrogen. 2-Isocyanatoethyl acrylate (2.2 eq.) was slowly added to the white suspension using a syringe in an ice bath, and the reaction was allowed to proceed at room temperature for 16 hours. The reaction solution was concentrated under reduced pressure to remove the solvent, and the resulting reaction residue was fractionated by silica gel column chromatography to obtain compound 1-1, represented by the following formula. Compound 1-1 corresponds to compound 1 in Compound A above.

[0185] [ka]

[0186] [Table 1]

[0187] [Comparative Example 1] (Comparative Compound 1) As comparative compound 1, Aronix M-215 (isocyanuric acid ethylene oxide modified diacrylate, manufactured by Toagosei Co., Ltd.) represented by the following formula was used.

[0188] [ka]

[0189] [Comparative Example 2] (Comparative Compound 2) Tris(2-hydroethyl)isocyanate (1.0 eq.), dibutyltin dilaurate (0.04 eq.), and tetrahydrofuran were added to a 100 mL recovery flask and the atmosphere was replaced with nitrogen. 2-Isocyanatoethyl acrylate (2.2 eq.) was slowly added to the white suspension using a syringe in an ice bath, and the reaction was allowed to proceed at room temperature for 16 hours. The reaction solution was concentrated under reduced pressure to remove the solvent, and the resulting reaction residue was fractionated by silica gel column chromatography to obtain comparative compound 2, which is represented by the following formula:

[0190] [ka]

[0191] Comparative Example 3 (Synthesis of Comparative Compound 3) In a 50 mL recovery flask, diol 1 (1.0 eq.) represented by the formula below and dibutyltin dilaurate (0.06 eq.) were dissolved in THF and the atmosphere was purged with nitrogen. A THF solution of hexyl isocyanate (2.04 eq.) was slowly added to this solution via syringe, and the reaction solution was allowed to react at 60°C for 4 hours. Next, a 1 M THF solution of tetrabutylammonium fluoride (1.1 eq.) was added to this reaction solution, and the reaction was allowed to proceed at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure to remove the solvent, and the resulting reaction residue was fractionated by silica gel column chromatography to obtain intermediate 3 represented by the formula below.

[0192] [ka]

[0193] [ka]

[0194] [Table 2]

[0195] [Table 3]

[0196] [Table 4]

[0197] In a 30 mL recovery flask, the above intermediate 3 (1.0 eq.) and dibutyltin dilaurate (0.02 eq.) were dissolved in THF, and the atmosphere was purged with nitrogen. 2-Isocyanatoethyl acrylate (2.9 eq.) was added to this solution via syringe, and the reaction was carried out at 60°C for 2 hours. The reaction solution was concentrated under reduced pressure to remove the solvent, and the resulting reaction residue was fractionated by silica gel column chromatography to obtain comparative compound 3 represented by the following formula.

[0198] [ka]

[0199] [Table 5]

[0200] [Table 6]

[0201] [Table 7]

[0202] [Comparative Example 4] (Comparative Compound 4) As comparative compound 4, DPHA (dipentaerythritol hexaacrylate, manufactured by Tokyo Chemical Industry Co., Ltd.) represented by the following formula was used.

[0203] [ka]

[0204] [evaluation] <Production of polymers> According to the formulations in Table 8, the compounds obtained in the Examples and Comparative Examples, N-1919 (product name, photoradical polymerization initiator, manufactured by ADEKA Corporation), and solvent were placed in a recovery flask and irradiated with light at 365 nm and an illuminance of 2000 mW while stirring at room temperature. The resulting polymer was reprecipitated or washed with methanol or a mixed solvent of methanol and water, and the resulting solid was recovered by suction filtration and dried by heating under conditions of 100°C and 0.10 MPa, yielding each polymer.

[0205] [Table 8]

[0206] <Volume change rate> The volume change rates of the compounds obtained in the Examples and Comparative Examples and the polymers obtained by the above-mentioned methods were measured as follows. The results are shown in Table 9. The densities of the compounds and polymers were measured under a helium atmosphere using a SHIMADZU AccuPyc 1330, and the volume change was calculated using the following formula: - volume change value indicates volume contraction, and + volume change value indicates volume expansion. [(density of compound - density of polymer) / density of compound] x 100 A smaller volume change rate is preferable because the shrinkage rate during curing is smaller.

[0207] <Glass transition temperature (Tg)> The polymers obtained in the examples and comparative examples were subjected to DSC chart measurement using a Seiko Instruments Inc. DSC-6200R differential scanning calorimeter at a heating rate of 10°C / min over a scanning temperature range of 0 to 200°C. After measurement, the samples were cooled to -20°C with liquid nitrogen, and a second measurement was performed at a heating rate of 10°C / min over a scanning temperature range of -20 to 200°C. The inflection point of the second heat capacity measurement was taken as the glass transition point. The results are shown in Table 9. The glass transition point is preferably 80 to 200° C., and more preferably 100 to 160° C. If the glass transition point is too low, heat resistance will be poor, and if it is too high, handling will be poor during polymerization and processing, necessitating work at high temperatures, which will lead to deterioration of the substrate, etc.

[0208] [Table 9]

[0209] As shown in Table 9, it was confirmed that Compound 1 of the present invention can form a polymer with a small volume change rate and little cure shrinkage. It was also confirmed that the glass transition point was neither too low nor too high, and the polymer had excellent heat resistance and handleability.

[0210] Next, using the above compound 1-1 which gave good results, the following compound corresponding to the above compound 2 was synthesized and comparatively evaluated.

[0211] [Example 2] (Synthesis of Compound 2-1) Compound 1-1 (1.00 eq.) from Example 1 above, dibutyltin dilaurate (0.008 eq.), hexamethylene diisocyanate (0.41 eq.), and dichloromethane were added to a 10 mL recovery flask and purged with nitrogen. The reaction solution was reacted at 40°C for 2 hours and concentrated under reduced pressure. The resulting reaction residue was added to 1-propanol for reprecipitation. After stirring for 2 hours, the supernatant was decanted to obtain compound 2-1 represented by the following formula. Compound 2-1 corresponds to compound 2 in compound A above.

[0212] [ka]

[0213] [Table 10]

[0214] [Table 11]

[0215] [Table 12]

[0216] [Example 3] (Synthesis of Compound 2-2) Compound 1-1 (1.00 eq.) from Example 1 above, dibutyltin dilaurate (0.011 eq.), m-xylene diisocyanate (0.38 eq.), and dichloromethane were added to a 10 mL recovery flask and purged with nitrogen. The reaction solution was reacted at 40°C for 2 hours and concentrated under reduced pressure. The resulting reaction residue was added to 1-propanol for reprecipitation. After stirring for 2 hours, the supernatant was decanted to obtain compound 2-2 represented by the following formula. Compound 2-2 corresponds to compound 2 in compound A above.

[0217] [ka]

[0218] [Table 13]

[0219] [Table 14]

[0220] [Table 15]

[0221] [Example 4] (Synthesis of Compound 2-3) Compound 1-1 (1.00 eq.) from Example 1 above, dibutyltin dilaurate (0.009 eq.), methylenediphenyl diisocyanate (0.43 eq.), and dichloromethane were added to a 10 mL recovery flask and purged with nitrogen. The reaction solution was reacted at 40°C for 2 hours and concentrated under reduced pressure. The resulting reaction residue was added to 1-propanol for reprecipitation. After stirring for 2 hours, the supernatant was decanted to obtain compound 2-3 represented by the following formula. Compound 2-3 corresponds to compound 2 in compound A above.

[0222] [ka]

[0223] [Table 16]

[0224] [Table 17]

[0225] [Table 18]

[0226] [Example 5] (Synthesis of Compound 2-4) Compound 1-1 (1.00 eq.) from Example 1 above, dibutyltin dilaurate (0.014 eq.), Sumidur N3300 (0.31 eq., product name, manufactured by Sumika Covestro Urethane Co., Ltd., hexamethylene diisocyanate nurate), and dichloromethane were added to a 10 mL recovery flask and purged with nitrogen. The reaction solution was reacted at 40°C for 4 hours and concentrated under reduced pressure. The resulting reaction residue was added to 1-propanol for reprecipitation. After stirring for 2 hours, the supernatant was decanted to obtain compound 2-4 represented by the following formula. Compound 2-4 corresponds to compound 2 in compound A above.

[0227] [ka]

[0228] [Table 19]

[0229] [Table 20]

[0230] [Table 21]

[0231] [Comparative Example 5] (Comparative Compound 5) The above-mentioned Aronix M-215 (1.00 eq., product name, Toagosei Co., Ltd., isocyanuric acid ethylene oxide-modified diacrylate), dibutyltin dilaurate (0.007 eq.), toluene diisocyanate (0.43 eq.), and dichloromethane were added to a 10 mL recovery flask and purged with nitrogen. The reaction solution was reacted at 40°C for 2 hours and concentrated under reduced pressure. The resulting reaction residue was added to 1-propanol for reprecipitation. After stirring for 2 hours, the supernatant was decanted to obtain comparative compound 5 represented by the following formula.

[0232] [ka]

[0233] [Table 22]

[0234] [Table 23]

[0235] [Comparative Example 6] (Comparative Compound 6) In a 10 mL recovery flask, the above-mentioned Aronix M-215 (1.00 eq.), dibutyltin dilaurate (0.006 eq.), Stabio D-370N (0.43 eq., product name, manufactured by Mitsui Chemicals, Inc., pentamethylene diisocyanate nurate), and dichloromethane were added and purged with nitrogen. The reaction solution was reacted at 40°C for 2 hours, concentrated under reduced pressure, and the resulting reaction residue was added to 1-propanol for reprecipitation. After stirring for 2 hours, the supernatant was decanted to obtain comparative compound 6 represented by the following formula.

[0236] [ka]

[0237] [Table 24]

[0238] [Table 25]

[0239] A polymer was synthesized according to the formulation in Table 26 in the same manner as in Example 1 (compound 1-1), and the volume change rate and glass transition temperature were evaluated. The evaluation results are shown in Table 27.

[0240] [Table 26]

[0241] [Table 27]

[0242] As shown in Table 27, it was confirmed that Compound 2 synthesized from Compound 1 also has a smaller volume change rate and can form a polymer with less cure shrinkage than the comparative compound. It was also confirmed that the glass transition point is neither too low nor too high, and that Compound 2 has excellent heat resistance and handleability. Furthermore, the Y 1 It was also confirmed that the glass transition temperature of the polymer can be changed by the structure of the polymer.

Claims

1. A compound represented by the following general formula (I): 【Chemistry 1】 (wherein a represents 0 or 1, R １ represents an unsubstituted or substituted hydrocarbon group having 3 to 20 carbon atoms and having an ethylenically unsaturated bond group at a terminal, or a group in which one or more methylene groups in the hydrocarbon group having an ethylenically unsaturated bond group at a terminal are substituted with a divalent group selected from the following <Group A>, R ２ and R ４ each independently represents a hydrogen atom, an unsubstituted or substituted alkyl group having 1 to 3 carbon atoms, or an alkyl group in which one or more methylene groups are substituted with a divalent group selected from the following <Group A>, When a is 0, R ３ is a hydrogen atom, When a is 1, R ３ represents an unsubstituted or substituted hydrocarbon group having 3 to 20 carbon atoms and having an ethylenically unsaturated bond group at a terminal, an unsubstituted or substituted hydrocarbon group having 6 to 20 carbon atoms and having an aromatic ring, or an unsubstituted or substituted hydrocarbon group having 3 to 20 carbon atoms and having an aliphatic hydrocarbon ring, or a group in which one or more methylene groups in the hydrocarbon group having an ethylenically unsaturated bond group at a terminal, the hydrocarbon group having an aromatic ring, or the hydrocarbon group having an aliphatic hydrocarbon ring are substituted with a divalent group selected from the following <Group A>, R ５ represents a hydrogen atom, an unsubstituted or substituted hydrocarbon group having 1 to 20 carbon atoms, or a group in which one or more methylene groups in the hydrocarbon group are substituted with a divalent group selected from the following <Group A>, and the substituent in the hydrocarbon group having 1 to 20 carbon atoms and a group in which one or more methylene groups in the hydrocarbon group are substituted with a divalent group selected from the following <Group A> used for R 5 is one or more selected from a cyano group, a nitro group, a hydroxyl group, an amino group, a carboxy group, an epoxy group, a mercapto group, and an isocyanate group, X １ , X ２ and X ３ each independently represents an unsubstituted divalent hydrocarbon group having 1 to 20 carbon atoms, or a divalent hydrocarbon group in which one or more methylene groups are substituted with a divalent group selected from the following <Group A>: <Group A> is —O—, —S—, —CO—, —CO—O— and —SO ２ - is.)

2. The compound according to claim 1, wherein a is 1 in the general formula (I).

3. In the above general formula (I), R ３ is an unsubstituted or substituted hydrocarbon group having 3 to 20 carbon atoms and having an ethylenically unsaturated bond group at a terminal, or a group in which one or more methylene groups in the unsubstituted or substituted hydrocarbon group having 3 to 20 carbon atoms and having an ethylenically unsaturated bond group at a terminal are substituted with a divalent group selected from <Group A> above.

4. A compound represented by the following general formula (II): 【Chemistry 2】 (wherein n represents 2 to 6, R ６ , R ７ and R ８ each independently represents a hydrogen atom, an unsubstituted or substituted alkyl group having 1 to 3 carbon atoms, or an alkyl group in which one or more methylene groups are substituted with a divalent group selected from the following <Group B>, R ９ represents an unsubstituted or substituted hydrocarbon group having 3 to 20 carbon atoms and having an ethylenically unsaturated bond group at a terminal, or a group in which one or more methylene groups in the hydrocarbon group having an ethylenically unsaturated bond group at a terminal are substituted with a divalent group selected from the following <Group B>, R １０ represents an unsubstituted or substituted hydrocarbon group having 3 to 20 carbon atoms and having an ethylenically unsaturated bond group at a terminal, an unsubstituted or substituted hydrocarbon group having 6 to 20 carbon atoms and having an aromatic ring, or an unsubstituted or substituted hydrocarbon group having 3 to 20 carbon atoms and having an aliphatic hydrocarbon ring, or a group in which one or more methylene groups in the hydrocarbon group having an ethylenically unsaturated bond group at a terminal, the hydrocarbon group having an aromatic ring, or the hydrocarbon group having an aliphatic hydrocarbon ring are substituted with a divalent group selected from the following <Group B>, X ４ , X ５ and X ６ each independently represents a divalent hydrocarbon group having 1 to 20 carbon atoms, or a group in which one or more methylene groups in the divalent hydrocarbon group have been substituted with a divalent group selected from the following <Group B>, Y １ represents an unsubstituted or substituted hydrocarbon group having 1 to 20 carbon atoms, a heterocyclic group having 2 to 30 carbon atoms, an unsubstituted or substituted hydrocarbon group having a heterocycle having 2 to 30 carbon atoms, or a group in which one or more methylene groups in the unsubstituted or substituted hydrocarbon group having 1 to 20 carbon atoms or the unsubstituted or substituted hydrocarbon group having 2 to 30 carbon atoms and a heterocycle are substituted with a divalent group selected from the following <Group B>, <Group B> is —O—, —S—, —CO—, —CO—O— and —SO ２ - is.)

5. The compound according to claim 4, wherein n is 2 or 3 in the general formula (II).

6. In the above general formula (II), R １０ is an unsubstituted or substituted hydrocarbon group having 3 to 20 carbon atoms and having an ethylenically unsaturated bond group at a terminal, or a group in which one or more methylene groups in the unsubstituted or substituted hydrocarbon group having 3 to 20 carbon atoms and having an ethylenically unsaturated bond group at a terminal are substituted with a divalent group selected from <Group B>.

7. Above Y １ represents an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms and from which n-1 hydrogen atoms have been removed, an unsubstituted or substituted hydrocarbon group having 6 to 20 carbon atoms and having an aromatic ring, an unsubstituted or substituted hydrocarbon group having 2 to 30 carbon atoms and having a heterocycle, or a group in which one or more methylene groups in the alkyl group, the hydrocarbon group having an aromatic ring, or the hydrocarbon group having a heterocycle are substituted with a divalent group selected from <Group B>.

8. 8. The compound according to any one of claims 1 to 7, wherein the ethylenically unsaturated bond group is a vinyl group, an isopropenyl group, an acryloyloxy group, or a methacryloyloxy group.

9. A polymer having a structural unit derived from the compound according to any one of claims 1 to 8.

10. A composition comprising the compound according to any one of claims 1 to 8.

11. An adhesive comprising the composition of claim 10.

12. A coating agent comprising the composition according to claim 10.

13. A cured product of the composition according to claim 10.

14. A method for producing a cured product, comprising the step of curing the composition according to claim 10.

15. The method for producing a cured product according to claim 14 , wherein the curing step is a step of irradiating the composition with light.

Images