Compound, composition, cured product, method for producing cured product, and polymer
The composition, featuring a compound with cyclic ether and unsaturated bond groups, addresses the limitations of curability and durability in existing compounds, achieving enhanced adhesiveness and long-term performance in cured products for various applications.
Patent Information
- Application Number
- PCT/JP2024/023223
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2023-07-19
- Filing Date
- 2024-06-26
- Publication Date
- 2025-01-23
AI Technical Summary
Existing compounds with cyclic ether groups and unsaturated bonds lack sufficient curability, adhesiveness, and durability in cured products, limiting their applications in adhesives, paints, and construction materials.
A composition comprising a compound with a structure represented by specific general formulas, containing two or more cyclic ether groups and an unsaturated bond-containing group, along with a polymerization initiator, such as a cationic or radical initiator, to enhance curability and adhesiveness during curing.
The composition achieves high curability, adhesiveness, and durability of the cured product, suitable for applications in adhesives, paints, and construction materials, with reduced curing shrinkage and improved long-term performance.
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Figure JP2024023223_23012025_PF_FP_ABST
Abstract
Description
Compound, composition, cured product, method for producing cured product, and polymer
[0001] The present invention relates to a compound having a cyclic ether group and an unsaturated bond-containing group, as well as a composition using the compound, a cured product, a method for producing the cured product, and a polymer.
[0002] Compounds having a cyclic ether group exhibit excellent properties in a wide range of applications, such as adhesives, paints, electrical insulating materials, and civil engineering and construction materials.
[0003] For example, in Patent Document 1, a dioxetane compound is used as a component of a photocurable adhesive composition, and in Patent Document 2, a compound having one oxetane ring and one ethylenically unsaturated bond in the molecule is used as a component of a photocurable inkjet ink composition.
[0004] US2020 / 0291279A1 JP2010-132787A
[0005] However, the above compounds may still lack curability, and the adhesiveness and durability of the cured product may be insufficient.
[0006] An object of the present invention is to provide a composition that is excellent in curability, adhesiveness, and / or durability of the cured product. Another object of the present invention is to provide a compound that is highly curable.
[0007] The present inventors have investigated compounds having a cyclic ether group and an unsaturated bond-containing group and have found a configuration that can solve the above-mentioned problems.
[0008] The present invention relates to the following items: [1] A composition comprising a compound having a structure represented by the following general formula (I), a structure represented by the following general formula (II), and an unsaturated bond-containing group, and a polymerization initiator, wherein the compound has two or more structures represented by the following general formula (I): (wherein R represents a hydrogen atom, a halogen atom, a cyano group, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 30 carbon atoms and in which a hydrogen atom may be substituted by a substituent, or a group having 1 to 30 carbon atoms in which one or more methylene groups in the hydrocarbon group are substituted by a group selected from <Group A> below and in which a hydrogen atom in the group may be substituted by a substituent, a represents an integer of 0 to 5, b represents an integer of 0 to 5, a+b represents an integer of 1 or more, *, **, and *** represent bonding sites, D and J each independently represent a direct bond, a hydrocarbon group having 1 to 30 carbon atoms and in which a hydrogen atom may be substituted by a substituent, or a group having 1 to 30 carbon atoms in which one or more methylene groups in the hydrocarbon group are substituted by a group selected from <Group A> below and in which a hydrogen atom in the group may be substituted by a substituent, G and L each independently represent a direct bond or a group selected from the following <Group A>, where <Group A> represents —O—, —S—, —NR 101 -, -CO-, -CO-O-, -O-CO-, CO-NR 101 -, -NR 101 -CO-, -CO-S- or -S-CO-, R 101 is a hydrogen atom, a halogen atom, a cyano group, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 10 carbon atoms, or a heterocyclic ring-containing group having 2 to 10 carbon atoms.
[0009] [2] A composition comprising the compound according to [1], which has a structure represented by the following general formula (III): (In the formula, D 1 and J 1 are each independently a direct bond, a hydrocarbon group having 1 to 30 carbon atoms in which a hydrogen atom may be substituted by a substituent, or a hydrocarbon group having 1 to 30 carbon atoms in which one or more methylene groups are substituted by a group selected from the following <Group A>, in which a hydrogen atom may be substituted by a substituent; 1 and L 1 are each independently a direct bond or a group selected from the following <Group A>, 1is a hydrogen atom, a halogen atom, a cyano group, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 30 carbon atoms in which a hydrogen atom may be substituted by a substituent, or a hydrocarbon group having 1 to 30 carbon atoms in which one or more methylene groups are substituted by a group selected from the following <Group A> in which a hydrogen atom may be substituted by a substituent; Z 1 and Z 2 are each independently a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, or a group represented by the following formula (III-1), a1 is an integer of 0 to 5, b1 is an integer of 0 to 5, a1+b1 is an integer of 1 or more, <Group A> is -O-, -S-, -NR 101 -, -CO-, -CO-O-, -O-CO-, CO-NR 101 -, -NR 101 -CO-, -CO-S- or -S-CO-, R 101 is a hydrogen atom, a halogen atom, a cyano group, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 10 carbon atoms, or a heterocyclic ring-containing group having 2 to 10 carbon atoms. (In the formula, D 1 , G 1 , J 1 , L 1 , R 1 , a1 and b1 are the same as those in formula (III), and L 2 is a direct bond or a hydrocarbon group having 1 to 10 carbon atoms. * indicates the bonding point.)
[0010] [3] The composition according to [1] or [2], wherein the polymerization initiator is a cationic polymerization initiator.
[0011] [4] The composition according to [3], further comprising a radical polymerization initiator.
[0012] [5] The composition according to [3] or [4], wherein the cationic polymerization initiator is an aromatic sulfonium salt.
[0013] [6] A cured product of the composition according to any one of [1] to [5].
[0014] [7] A method for producing a cured product, comprising a step of curing the composition according to any one of [1] to [5] by irradiating it with light.
[0015] [8] A compound having a structure represented by the following general formula (III): (In the formula, D 1 and J 1 are each independently a direct bond, a hydrocarbon group having 1 to 30 carbon atoms in which a hydrogen atom may be substituted by a substituent, or a hydrocarbon group having 1 to 30 carbon atoms in which one or more methylene groups are substituted by a group selected from the following <Group A>, in which a hydrogen atom may be substituted by a substituent; 1 and L 1 are each independently a direct bond or a group selected from the following <Group A>, 1 is a hydrogen atom, a halogen atom, a cyano group, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 30 carbon atoms in which a hydrogen atom may be substituted by a substituent, or a hydrocarbon group having 1 to 30 carbon atoms in which one or more methylene groups are substituted by a group selected from the following <Group A> in which a hydrogen atom may be substituted by a substituent; Z 1 and Z 2 are each independently a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, or a group represented by the following formula (III-1), a1 is an integer of 0 to 5, b1 is an integer of 0 to 5, a1+b1 is an integer of 1 or more, <Group A> is -O-, -S-, -NR 101 -, -CO-, -CO-O-, -O-CO-, CO-NR 101 -, -NR 101 -CO-, -CO-S- or -S-CO-, R 101 is a hydrogen atom, a halogen atom, a cyano group, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 10 carbon atoms, or a heterocyclic ring-containing group having 2 to 10 carbon atoms. (In the formula, D 1 , G 1 , J 1 , L 1 , R 1, a1 and b1 are the same as those in formula (III), and L 2 is a direct bond or a hydrocarbon group having 1 to 10 carbon atoms. * indicates the bonding point.)
[0016] [9] The D 1 is a hydrocarbon group having 1 to 10 carbon atoms in which a hydrogen atom may be substituted by a substituent, or a hydrocarbon group having 1 to 10 carbon atoms in which one or more methylene groups are substituted by a group selected from the above <Group A>, in which a hydrogen atom may be substituted by a substituent, 1 is —O—, —S—, —CO—, —CO—O— or —O—CO—, and 1 is a hydrocarbon group having 1 to 10 carbon atoms in which a hydrogen atom may be substituted by a substituent, or a hydrocarbon group having 1 to 10 carbon atoms in which one or more methylene groups are substituted by a group selected from the above <Group A> in which a hydrogen atom may be substituted by a substituent, 1 is —CO—O— or —O—CO—, and 1 is a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms in which a hydrogen atom may be substituted with a substituent, or a group having 1 to 10 carbon atoms in which one or more methylene groups in the hydrocarbon group are substituted with a group selected from <Group A>, in which a hydrogen atom may be substituted with a substituent, a1 is 1, and b1 is 1.
[0017]
[10] The D 1 is a hydrocarbon group having 1 to 6 carbon atoms in which a hydrogen atom may be substituted with a substituent, 1 is —O—, —CO—O— or —O—CO—, and 1 is a hydrocarbon group having 1 to 10 carbon atoms in which a hydrogen atom may be substituted with a substituent, 1 is a hydrocarbon group having 1 to 10 carbon atoms, in which a hydrogen atom may be substituted with a substituent.
[0018]
[11] A polymer obtained by polymerizing the compound according to any one of [8] to
[10] as a monomer.
[0019] According to the present invention, it is possible to provide a composition that is excellent in curability, adhesiveness, and / or durability of the cured product. Furthermore, the present invention can provide a compound that is highly curable and suitable for obtaining the composition.
[0020] The compound, composition, polymer and cured product of the present invention will be described below.
[0021] A. Compound First, the compound of the present invention (hereinafter, sometimes referred to as "Compound A") will be described. The compound of the present disclosure is a compound having a structure represented by the following general formula (I), a structure represented by the following general formula (II), and an unsaturated bond-containing group, and is a compound having two or more structures represented by the following general formula (I).
[0022] In the general formula, R represents a hydrogen atom, a halogen atom, a cyano group, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 30 carbon atoms in which a hydrogen atom may be substituted with a substituent, or a hydrocarbon group having 1 to 30 carbon atoms in which one or more methylene groups are substituted with a group selected from <Group A> below, and in which a hydrogen atom may be substituted with a substituent. Hereinafter, "a hydrocarbon group in which one or more methylene groups are substituted with a group selected from <Group A> below" will also be referred to as "methylene-substituted hydrocarbon group".
[0023] a is an integer of 0 to 5, b is an integer of 0 to 5, a+b is an integer of 1 or more, *, ** and *** are bonding points,
[0024] D and J each independently represent a direct bond, a hydrocarbon group having 1 to 30 carbon atoms in which a hydrogen atom may be substituted by a substituent, or a methylene-substituted hydrocarbon group having 1 to 30 carbon atoms in which a hydrogen atom may be substituted by a substituent; G and L each independently represent a direct bond or a group selected from the following <Group A>, <Group A> being -O-, -S-, -NR 101-, -CO-, -CO-O-, -O-CO-, CO-NR 101 -, -NR 101 -CO-, -CO-S- or -S-CO-, R 101 is a hydrogen atom, a halogen atom, a cyano group, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 10 carbon atoms, or a heterocyclic group having 2 to 10 carbon atoms. When there are multiple R, D, G, J, and L in one molecule, they may be the same or different. Here, "same" includes symmetrical relationships. An example of mutual symmetry is the relationship between -COO- and -OCO-.
[0025] Compound A of the present disclosure is highly curable due to its structure, and can achieve high curability in compositions such as curable resin compositions. Furthermore, when compound A is used in compositions such as curable resin compositions, it can also achieve high adhesion upon curing. Furthermore, compound A and compositions using the same can achieve low cure shrinkage because compound A also functions as a crosslinking agent, and the durability of the cured product is also excellent. Hereinafter, the durability of the cured product will also be simply referred to as "durability." By achieving the effects described above, compound A of the present disclosure can be suitably used for curable adhesives and coatings.
[0026] Compound A of the present disclosure will be described in detail below. As described above, the compound of the present disclosure is a compound having a structure represented by the following general formula (I), a structure represented by the following general formula (II), and an unsaturated bond-containing group, and is a compound having two or more structures represented by the following general formula (I). Here, having the structure represented by the general formula (I) (hereinafter sometimes referred to as Structure I), the structure represented by the general formula (II) (hereinafter sometimes referred to as Structure II), and an unsaturated bond-containing group means that Structure I, Structure II, and the unsaturated bond-containing group are contained in the same molecule. Similarly, having two or more structures represented by the general formula (I) means that two or more Structures I are contained in the same molecule. Furthermore, Structure I, Structure II, and the unsaturated bond-containing group may be directly covalently bonded at *, **, and *** in Structure I and Structure II, or may be covalently bonded via a linking group.
[0027] The combination of bonds between the Structure I, the Structure II, and the unsaturated bond-containing group may include any combination of a bond between Structure I and Structure II, a bond between Structure I and the unsaturated bond-containing group, a bond between Structure II and the unsaturated bond-containing group, a bond between Structures I, a bond between Structures II, and a bond between unsaturated bond-containing groups. The compound of the present disclosure contains at least two Structures I, at least one Structure II, and at least one unsaturated bond-containing group, which are covalently bonded directly or via a linking group in any of the above combinations. Preferably, the compound includes a bond between Structure I and Structure II and / or a bond between Structure II and the unsaturated bond-containing group.
[0028] The unsaturated bond-containing group is an unsaturated bond group, that is, a group containing a carbon-carbon double bond. A carbon-carbon double bond is sometimes called an aliphatic double bond. Specific examples of the unsaturated bond-containing group include groups in which a carbon-carbon single bond in a hydrocarbon group and a total of two hydrogen atoms bonded to the carbon atom are substituted with a carbon-carbon double bond. The unsaturated bond-containing group may have multiple carbon-carbon double bonds, but the double bonds are not adjacent to each other, for example, as in -C=C=C-. As the hydrocarbon group substituted with a carbon-carbon double bond, a divalent group in which one hydrogen atom has been removed can be used from among the monovalent groups listed as hydrocarbon groups used for R in the structure I described below.
[0029] Examples of divalent groups obtained by removing one hydrogen atom from a monovalent hydrocarbon group include alkylene groups, which are groups obtained by removing one hydrogen atom from an alkyl group. Examples of alkylene groups include linear and branched groups such as methylene, 1,2-ethylene, 1,2-propylene, 1,3-propylene, 1,4-butylene, 1,6-hexylene, 2-methyltrimethylene, 2-methyltetramethylene, and 2-methylpentamethylene.
[0030] When a divalent group obtained by removing one hydrogen atom from an aryl group or an arylalkyl group is used as the unsaturated bond-containing group, it is necessary that the group have an aliphatic carbon-carbon double bond in addition to the aromatic carbon-carbon double bond constituting the aromatic ring. Furthermore, when a group obtained by replacing the carbon-carbon single bond in a divalent group obtained by removing one hydrogen atom from a cycloalkyl group or a cycloalkylalkyl group with a carbon-carbon double bond is used as the unsaturated bond-containing group, the unsaturated bond-containing group does not include groups having only aromatic carbon-carbon double bonds constituting the aromatic ring.
[0031] In the present disclosure, the number of carbon atoms in the unsaturated bond-containing group is preferably 2 to 15, more preferably 2 to 10, particularly preferably 2 to 5, particularly preferably 2 or 3, and most preferably 2. Having the above structure, Compound A and compositions using the same have higher curability, and the durability and adhesiveness of the cured product can be improved.
[0032] Furthermore, the monovalent hydrocarbon group substituted with a carbon-carbon double bond before removing one hydrogen atom is preferably an alkyl group, a cycloalkyl group, a cycloalkylalkyl group, an aryl group, or an arylalkyl group, and among these, an alkyl group, a cycloalkyl group, or a cycloalkylalkyl group is preferred, with an alkyl group being particularly preferred. Having this structure makes compound A and compositions using it more highly curable, and can also improve the durability and adhesiveness of the cured product.
[0033] The hydrocarbon group substituted with a carbon-carbon double bond may have one or more hydrogen atoms in the group substituted with a substituent, or one or more methylene groups in the group substituted with a group selected from Group A above, but is preferably unsubstituted or one or more methylene groups in the group substituted with -O-, -CO-, -CO-O-, or -O-CO-, and is preferably unsubstituted. Having the above structure, Compound A and compositions using it have higher curability and can improve the durability and adhesion of the cured product.
[0034] The bonding mode of formula (I) and / or formula (II) to the carbon-carbon double bond in the unsaturated bond-containing group may be either a cis or trans isomer, but the trans isomer is preferred because it has higher reactivity. The bonding of formula (I) and / or formula (II) to the carbon-carbon double bond is direct or via a linking group.
[0035] In the above-mentioned Structure I, Structure II, and unsaturated bond-containing group (hereinafter also referred to as "Structure I, etc."), one or more hydrogen atoms in the structure may be substituted with a substituent. Examples of the substituent substituting the hydrogen atom include a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, -COOH, and -SO. 3 Examples of the substituent include H, an isocyanate group, a hydrocarbon group having 1 to 10 carbon atoms, a hydrocarbon group having 1 to 10 carbon atoms in which one or more methylene groups have been substituted with a group selected from the above <Group A>, a heterocycle-containing group having 2 to 10 carbon atoms, and a heterocycle-containing group having 2 to 10 carbon atoms in which one or more methylene groups have been substituted with a group selected from the above <Group A>, and combinations thereof. Examples of the combinations include a hydrocarbon group having 1 to 10 carbon atoms or a methylene-substituted hydrocarbon group, or a heterocycle-containing group having 2 to 10 carbon atoms I or II (described below) as a substituent, which further contains a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, -COOH, -SO 3 Examples include the case where a hydrogen atom in the group is substituted with an H or isocyanate group.
[0036] As mentioned above, in this specification, "a group in which one or more methylene groups in a hydrocarbon group are substituted with a group selected from the above <Group A>" is also referred to as a "methylene-substituted hydrocarbon group." Furthermore, the heterocyclic group I described below, heterocyclic group II in which one or more hydrogen atoms of heterocyclic group I are substituted with hydrocarbon groups, and groups in which hydrogen atoms in these groups are substituted with substituents are referred to as heterocycle-containing groups I, and "a group in which a methylene group in a hydrocarbon group in heterocycle-containing group I is substituted with a group selected from the above <Group A>" is also referred to as a "heterocycle-containing group II." Unless otherwise specified, the term "heterocycle-containing group" can refer to both heterocycle-containing groups I and II.
[0037] In the present disclosure, the number of carbon atoms in a group defines the number of carbon atoms in the group after substitution of a hydrogen atom in the group with a substituent. For example, "1 to 30 carbon atoms" in "a hydrocarbon group having a substituent of 1 to 30 carbon atoms" refers to the number of carbon atoms in the entire 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 addition, in the present disclosure, the number of carbon atoms in a group in which a methylene group in a group with a predetermined number of carbon atoms has been substituted with a group selected from the above <Group A> defines the number of carbon atoms in the group after substitution. For example, in this specification, examples of hydrocarbon groups in a predetermined (e.g., 1 to 30 carbon atoms) methylene-substituted hydrocarbon group are the same as the examples of a predetermined (e.g., 1 to 30 carbon atoms) hydrocarbon group, but a methylene group (-CH 2 The number of carbon atoms in a group in which one of the methylene groups in a hydrocarbon group is substituted with a divalent group "-O-" is 19. Furthermore, a group in which one or more methylene groups in a hydrocarbon group are substituted with a divalent group selected from <Group A> does not have a structure in which multiple divalent groups are adjacent to each other. Nor does it have a structure in which all hydrocarbon groups are substituted with divalent groups selected from <Group A>. For example, -CO- is not a group in which a hydrocarbon group having one carbon atom (methylene group) is substituted with a group selected from <Group A>, but is the group selected from <Group A> itself. The multiple groups selected from <Group A> may be the same or different.
[0038] As the hydrocarbon group having 1 to 10 carbon atoms used as a substituent that may substitute a hydrogen atom in the structure I etc., any monovalent group having a predetermined number of carbon atoms can be used among the hydrocarbon groups used for R in the structure I described below.
[0039] The heterocyclic ring-containing group I having 2 to 10 carbon atoms, which is used as a substituent that may replace a hydrogen atom in the structure I or the like, may have 2 to 10 carbon atoms, and may include a group in which one hydrogen atom has been removed from an unsubstituted heterocyclic compound (hereinafter, a "group in which one hydrogen atom has been removed from an unsubstituted heterocyclic compound" may be referred to as a "heterocyclic group I"); a group in which one or more hydrogen atoms in the heterocyclic group I have been substituted with a hydrocarbon group (hereinafter, this may be referred to as a "heterocyclic group II"); or a group having a structure in which one or more hydrogen atoms in the unsubstituted heterocyclic group I or heterocyclic group II have been substituted with a substituent. The heterocyclic ring-containing group II is as described above. Examples of the substituent that may replace a hydrogen atom in the unsubstituted heterocyclic group I or heterocyclic group II include a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, -COOH, -SO 3 H and an isocyanate group. As the hydrocarbon group used as a substituent that may substitute a hydrogen atom in the heterocyclic group I, a hydrocarbon group selected from the monovalent groups listed as the hydrocarbon group used as R in structure I described below, so as to satisfy the predetermined number of carbon atoms as a heterocycle-containing group, can be used. When a hydrogen atom in the heterocyclic group II is substituted with a substituent, the substituent may be bonded to either the heterocyclic group I or the hydrocarbon group.
[0040] The heterocyclic compound (hereinafter sometimes referred to as a heterocycle) may have a monocyclic structure or a fused ring structure. The heterocycle having a fused ring structure is a structure in which a heterocycle and a heterocycle or a hydrocarbon ring are fused together, and examples thereof include a heterocycle-containing fused ring. Specific examples of the heterocycle include saturated or unsaturated monocyclic heterocycles such as a thiophene ring, a furan ring, a pyrrole ring, a pyrrolidine ring, a pyridine 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 or unsaturated polycyclic hydrocarbon rings such as a tetrahydroquinoline ring, a tetrahydroisoquinoline ring, a dihydrobenzofuran ring, a tetrahydrocarbazole ring, a benzothiazole ring, a benzoxazole ring, a benzimidazole ring, an indole ring, and an indene ring.
[0041] When the respective structures are covalently bonded via a linking group, examples of the linking group include a group selected from Group A, -N, a hydrocarbon group having 1 to 20 carbon atoms in which a hydrogen atom may be substituted with a substituent, a methylene-substituted hydrocarbon group having 1 to 20 carbon atoms in which a hydrogen atom may be substituted with a substituent, a heterocycle-containing group I having 2 to 20 carbon atoms in which a hydrogen atom may be substituted with a substituent, or a heterocycle-containing group II having 2 to 20 carbon atoms in which a hydrogen atom may be substituted with a substituent. Examples of the group substituting the hydrogen atom in the hydrocarbon group and heterocycle-containing group include a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, -COOH, -SO 3 H, an isocyanate group, or an alkyl group having 1 to 6 carbon atoms. As the alkyl group having 1 to 6 carbon atoms, any monovalent group having a predetermined number of carbon atoms can be used, among the alkyl groups used for R in Structure I described below.
[0042] As the hydrocarbon group having 1 to 20 carbon atoms used in the linking group, a divalent or higher valent group obtained by removing one or more hydrogen atoms from a monovalent group exemplified as the hydrocarbon group used for R in Structure I described below can be used.
[0043] As the heterocycle-containing group having 2 to 20 carbon atoms used in the linking group, a divalent or higher group in which one or more hydrogen atoms have been removed from the groups exemplified as heterocycle-containing groups used as substituents that may substitute hydrogen atoms in the structure I or the like, or groups similar thereto, can be used.
[0044] Examples of the unsubstituted hydrocarbon group having 1 to 30 carbon atoms used for R in Structure I include an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a cycloalkylalkyl group having 4 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, and an arylalkyl group having 7 to 30 carbon atoms.
[0045] The alkyl group having 1 to 30 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.
[0046] Examples of the cycloalkyl group having 3 to 30 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 group substituting a hydrogen atom in the ring of a saturated monocyclic or saturated polycyclic alkyl group include the groups exemplified above as the alkyl group. Examples of the group in which one or more hydrogen atoms in the ring of a saturated polycyclic alkyl group are substituted with alkyl groups include bornyl.
[0047] The cycloalkylalkyl group having 4 to 30 carbon atoms refers to a group in which one or more hydrogen atoms of an alkyl group are 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.
[0048] The alkenyl group having 2 to 30 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 vinyl, 1-propenyl, 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-tetradecatrienyl allyl.
[0049] The aryl group having 6 to 30 carbon atoms may have a monocyclic structure, a fused ring structure, or two linked aromatic hydrocarbon rings. The aryl group having two linked aromatic hydrocarbon rings may be two linked aromatic hydrocarbon rings having a monocyclic structure, a linked aromatic hydrocarbon ring having a monocyclic structure and a linked aromatic hydrocarbon ring having a fused ring structure, or a linked aromatic hydrocarbon ring having two fused ring structures. Examples of the linking group connecting the two aromatic hydrocarbon rings include a single bond and a carbonyl group. Examples of aryl groups having a monocyclic structure include phenyl, tolyl, xylyl, ethylphenyl, and 2,4,6-trimethylphenyl. Examples of aryl groups having a fused ring structure include naphthyl, anthracenyl, phenanthryl, and pyrenyl. Examples of aryl groups having two linked aromatic hydrocarbon rings include biphenyl and benzoylphenyl.
[0050] The arylalkyl group having 7 to 30 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, A-methylbenzyl, phenylethyl, and naphthylpropyl groups.
[0051] The groups used for R to substitute hydrogen atoms in hydrocarbon groups and methylene-substituted hydrocarbon groups include halogen atoms, cyano groups, nitro groups, hydroxyl groups, thiol groups, -COOH, -SO 3 H and an isocyanate group. 1 The same groups can also be used as the substituents for the hydrocarbon group and methylene-substituted hydrocarbon group in the formula (I).
[0052] As the unsubstituted hydrocarbon group having 1 to 30 carbon atoms used for D and J, a divalent group obtained by removing one hydrogen atom from the monovalent groups listed as the hydrocarbon group used for R in Structure I can be used.
[0053] The groups that substitute hydrogen atoms in the hydrocarbon group and methylene-substituted hydrocarbon group used for D and J include halogen atoms, cyano groups, nitro groups, hydroxyl groups, thiol groups, -COOH, -SO 3 H, an isocyanate group, an epoxy group, and an oxetanyl group. 1 and J 1 The same groups can also be used as the substituents for the hydrocarbon group and methylene-substituted hydrocarbon group in the formula (I).
[0054] The R 101 As the hydrocarbon group having 1 to 10 carbon atoms used in R, any of the monovalent groups listed as hydrocarbon groups used in R in the structure I above, which satisfy the specified number of carbon atoms, can be used.
[0055] The R 101 As the heterocyclic ring-containing group having 2 to 10 carbon atoms used in the above, any monovalent group having a predetermined number of carbon atoms can be used, from among the heterocyclic ring-containing groups exemplified as the heterocyclic ring-containing group used as a substituent that may substitute a hydrogen atom in the above structure I, etc.
[0056] In the present disclosure, Compound A preferably has a structure in which Structure I and Structure II are bonded directly or via a linking group, and has a structure in which Structure II and an unsaturated bond-containing group are bonded directly or via a linking group, and particularly preferably has a structure in which Structure I and Structure II are bonded directly, and has a structure in which Structure II and an unsaturated bond-containing group are bonded directly. Also preferably, two Structures I are bonded to two different Structures II, respectively, directly or via a linking group, and each of the two Structures II is bonded to the same single unsaturated bond-containing group. Compound A and compositions using the same have higher curability and can improve the durability and adhesiveness of the cured product.
[0057] In compound A, the number of structures I may be 2 or more and 10 or less, or may be 2 or more and 6 or less, or may be 2 or more and 4 or less, or may be 2. The number of structures II may be 1 or more and 5 or less, or may be 1 or more and 4 or less, or may be 1 or more and 3 or less, or may be 2. The number of unsaturated bond-containing groups may be 1 or more and 6 or less, or may be 1 or more and 4 or less, or may be 1 or more and 2 or less.
[0058] In compound A, R is preferably a hydrogen atom, a halogen atom, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 30 carbon atoms in which a hydrogen atom in the group may be substituted with a substituent, or a methylene-substituted hydrocarbon group having 1 to 30 carbon atoms in which a hydrogen atom in the group may be substituted with a substituent, and particularly preferably a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 15 carbon atoms in which a hydrogen atom in the group may be substituted with a substituent, or a methylene-substituted hydrocarbon group having 1 to 15 carbon atoms in which a hydrogen atom in the group may be substituted with a substituent. Preferably, the hydrocarbon group is a methylene-substituted hydrocarbon group which may be substituted by a group, and more preferably, it is a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms in which a hydrogen atom in the group may be substituted by a substituent, or a methylene-substituted hydrocarbon group having 1 to 10 carbon atoms in which a hydrogen atom in the group may be substituted by a substituent, and more preferably, it is a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms in which a hydrogen atom in the group may be substituted by a substituent, or a hydrocarbon group in which one or more methylene groups in the hydrocarbon group are -O-, -COO-, -OCO-, -S- or -NR 101 Preferably, it is a group having 1 to 10 carbon atoms substituted with -, in which a hydrogen atom in the group may be substituted with a substituent, particularly preferably a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms in which a hydrogen atom in the group may be substituted with a substituent, more preferably a hydrogen atom or an unsubstituted hydrocarbon group having 1 to 6 carbon atoms, and most preferably an unsubstituted alkyl group having 1 to 3 carbon atoms. Compound A and compositions using it have higher curability and can improve the durability and adhesiveness of the cured product.
[0059] In Compound A, a is preferably 0 or more and 3 or less, more preferably 1 or more and 2 or less, and particularly preferably 1. Compound A and compositions using the same have higher curability, and the durability and adhesiveness of the cured product can be improved.
[0060] In Compound A, b is preferably 0 or more and 3 or less, more preferably 0 or more and 1 or less, and particularly preferably 1. Compound A and compositions using the same have higher curability, and the durability and adhesiveness of the cured product can be improved.
[0061] In Compound A, a+b is preferably 1 or more and 2 or less, and particularly preferably 2. Compound A and compositions using the same have higher curability, and the durability and adhesiveness of the cured product can be improved.
[0062] In compound A, D is preferably a direct bond, a hydrocarbon group having 1 to 20 carbon atoms in which a hydrogen atom in the group may be substituted with a substituent, or a methylene-substituted hydrocarbon group having 1 to 20 carbon atoms in which a hydrogen atom in the group may be substituted with a substituent, and among these, a direct bond, a hydrocarbon group having 1 to 10 carbon atoms in which a hydrogen atom in the group may be substituted with a substituent, or a methylene-substituted hydrocarbon group having 1 to 10 carbon atoms in which a hydrogen atom in the group may be substituted with a substituent, is particularly preferred, and a direct bond, a hydrocarbon group having 1 to 10 carbon atoms in which a hydrogen atom in the group may be substituted with a substituent, or a hydrocarbon group in which one or more methylene groups in the hydrocarbon group are -O-, -COO-, -OCO-, -S-, or -NR 101Preferably, it is a group having 1 to 10 carbon atoms substituted with -, in which a hydrogen atom in the group may be substituted with a substituent, and particularly preferably a direct bond or a hydrocarbon group having 1 to 6 carbon atoms in which a hydrogen atom in the group may be substituted with a substituent, more preferably a direct bond or an unsubstituted hydrocarbon group having 1 to 6 carbon atoms, and most preferably an unsubstituted alkylene group having 1 to 3 carbon atoms. Compound A and compositions using it have higher curability and can improve the durability and adhesion of the cured product.
[0063] In Compound A, G is a direct bond, —O—, —S—, or —NR 101 -, -CO-, -CO-O-, -O-CO-, -CO-S- or -S-CO- is preferred, and among these, a direct bond, -O-, -S-, -NR 101 Compound A and compositions using the same are highly curable, and can improve the durability and adhesiveness of the cured product.
[0064] In compound A, J is preferably a direct bond, a hydrocarbon group having 1 to 20 carbon atoms in which a hydrogen atom in the group may be substituted with a substituent, or a methylene-substituted hydrocarbon group having 1 to 20 carbon atoms in which a hydrogen atom in the group may be substituted with a substituent, and among these, a direct bond, a hydrocarbon group having 1 to 10 carbon atoms in which a hydrogen atom in the group may be substituted with a substituent, or a methylene-substituted hydrocarbon group having 1 to 10 carbon atoms in which a hydrogen atom in the group may be substituted with a substituent, is particularly preferred, and a direct bond, a hydrocarbon group having 1 to 10 carbon atoms in which a hydrogen atom in the group may be substituted with a substituent, or one or more of the methylene groups in the hydrocarbon group is -O-, -COO-, -OCO-, -S-, or -NR 101Preferably, it is a group of 1 to 10 carbon atoms substituted with -, in which a hydrogen atom in the group may be substituted with a substituent, and particularly preferably a direct bond or a hydrocarbon group of 1 to 10 carbon atoms in which a hydrogen atom in the group may be substituted with a substituent, more preferably a direct bond or a hydrocarbon group of 1 to 6 carbon atoms in which a hydrogen atom in the group may be substituted with a substituent, more preferably an unsubstituted hydrocarbon group of 1 to 6 carbon atoms, and most preferably an unsubstituted alkylene group of 1 to 6 carbon atoms. Compound A and compositions using it have higher curability and can improve the durability and adhesion of the cured product.
[0065] In Compound A, L is a direct bond, —O—, —S—, or —NR 101 -, -CO-, -CO-O-, -O-CO-, -CO-S- or -S-CO- is preferred, and among these, a direct bond, -O-, -S-, -NR 101 Compound A and compositions using the same are more highly curable, and the durability and adhesiveness of the cured product can be improved.
[0066] In compound A, R 101is preferably a hydrogen atom, a halogen atom, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 10 carbon atoms, or a heterocyclic group having 2 to 10 carbon atoms, among which a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 10 carbon atoms, or a heterocyclic group having 2 to 10 carbon atoms is preferred, and a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, or a heterocyclic group having 2 to 10 carbon atoms is particularly preferred, and a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms is particularly preferred, and a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a cycloalkylalkyl group having 4 to 10 carbon atoms, an aryl group having 6 carbon atoms, or an arylalkyl group having 7 to 10 carbon atoms is more preferred, and a hydrogen atom or an alkyl group having 1 to 6 carbon atoms is most preferred. Compound A and compositions using it have higher curability and can improve the durability and adhesion of the cured product.
[0067] Specific examples of the structure of Compound A include Compounds No. 1 to No. 36 shown below.
[0068]
[0069]
[0070]
[0071]
[0072]
[0073]
[0074]
[0075]
[0076] In the present disclosure, the compound A is preferably a compound represented by the following general formula (III): Compound A and a composition using the same have higher curability, and the resulting cured product can have improved durability, cure shrinkage, and adhesion.
[0077] (In the formula, D 1 and J 1 are each independently a direct bond, a hydrocarbon group having 1 to 30 carbon atoms in which a hydrogen atom may be substituted with a substituent, or a methylene-substituted hydrocarbon group having 1 to 30 carbon atoms in which a hydrogen atom may be substituted with a substituent, 1 and L 1 are each independently a direct bond or a group selected from the following <Group A>, 1 is a hydrogen atom, a halogen atom, a cyano group, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 30 carbon atoms in which a hydrogen atom may be substituted with a substituent, or a methylene-substituted hydrocarbon group having 1 to 30 carbon atoms in which a hydrogen atom may be substituted with a substituent, and Z 1 and Z 2 are each independently a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, or a group represented by the following formula (III-1), a1 is an integer of 0 to 5, b1 is an integer of 0 to 5, a1+b1 is an integer of 1 or more, <Group A> is -O-, -S-, -NR 101 -, -CO-, -CO-O-, -O-CO-, CO-NR 101 -, -NR 101 -CO-, -CO-S- or -S-CO-, R 101 is a hydrogen atom, a halogen atom, a cyano group, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 10 carbon atoms, or a heterocyclic ring-containing group having 2 to 10 carbon atoms. (In the formula, D 1 , G 1 , J 1 , L 1 , R 1 , a1 and b1 are the same as those in formula (III), and L 2is a direct bond or a hydrocarbon group having 1 to 10 carbon atoms. * indicates the bonding point.)
[0078] The R 1 As the hydrocarbon group having 1 to 30 carbon atoms used for R, any of the monovalent hydrocarbon groups used for R that satisfy the specified number of carbon atoms can be used.
[0079] The above D 1 and J 1 As the hydrocarbon group having 1 to 30 carbon atoms used for D, any of the divalent hydrocarbon groups used for D and J above that satisfy the predetermined number of carbon atoms can be used.
[0080] Z 1 , Z 2 As the hydrocarbon group having 1 to 10 carbon atoms used for R, any of the monovalent hydrocarbon groups used for R that satisfy the specified number of carbon atoms can be used.
[0081] L 2 As the hydrocarbon group having 1 to 10 carbon atoms used for D, any of the divalent hydrocarbon groups used for D and J that satisfy the predetermined number of carbon atoms can be used.
[0082] In compound A, R 1is preferably a hydrogen atom, a halogen atom, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 30 carbon atoms in which a hydrogen atom may be substituted with a substituent, or a methylene-substituted hydrocarbon group having 1 to 30 carbon atoms in which a hydrogen atom may be substituted with a substituent, and among these, a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 15 carbon atoms in which a hydrogen atom may be substituted with a substituent, or a methylene-substituted hydrocarbon group having 1 to 15 carbon atoms in which a hydrogen atom may be substituted with a substituent, and particularly preferably a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms in which a hydrogen atom may be substituted with a substituent, or a methylene-substituted hydrocarbon group having 1 to 10 carbon atoms in which a hydrogen atom may be substituted with a substituent, and among these, a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms in which a hydrogen atom may be substituted with a substituent, or a methylene-substituted hydrocarbon group having 1 to 10 carbon atoms in which a hydrogen atom may be substituted with a substituent, or 101 Preferably, it is a group having 1 to 10 carbon atoms substituted with -, in which a hydrogen atom in the group may be substituted with a substituent, and particularly preferably a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms in which a hydrogen atom in the group may be substituted with a substituent, more preferably a hydrogen atom or an unsubstituted hydrocarbon group having 1 to 6 carbon atoms, and most preferably an unsubstituted alkyl having 1 to 3 carbon atoms. Compound A and compositions using it have higher curability and can improve the durability and adhesiveness of the cured product.
[0083] In Compound A, a1 is preferably 0 or more and 3 or less, more preferably 1 or more and 2 or less, and particularly preferably 1. This is because Compound A and a composition using the same have higher curability and can improve the durability and adhesiveness of the cured product.
[0084] In Compound A, b1 is preferably 0 or more and 3 or less, more preferably 0 or more and 1 or less, and particularly preferably 1. Compound A and compositions using the same have higher curability, and the durability and adhesiveness of the cured product can be improved.
[0085] In Compound A, a1+b1 is preferably 1 or more and 2 or less, and particularly preferably 2. Compound A and compositions using the same have higher curability, and the durability and adhesiveness of the cured product can be improved.
[0086] In compound A, D 1 is preferably a direct bond, a hydrocarbon group having 1 to 20 carbon atoms in which a hydrogen atom in the group may be substituted with a substituent, or a methylene-substituted hydrocarbon group having 1 to 20 carbon atoms in which a hydrogen atom in the group may be substituted with a substituent, and among these, a direct bond, a hydrocarbon group having 1 to 10 carbon atoms in which a hydrogen atom in the group may be substituted with a substituent, or a methylene-substituted hydrocarbon group having 1 to 10 carbon atoms in which a hydrogen atom in the group may be substituted with a substituent, is particularly preferably a direct bond, a hydrocarbon group having 1 to 10 carbon atoms in which a hydrogen atom in the group may be substituted with a substituent, or a group in which one or more methylene groups in the hydrocarbon group are -O-, -COO-, -OCO-, -S-, or -NR 101 Preferably, it is a group having 1 to 10 carbon atoms substituted with -, in which a hydrogen atom in the group may be substituted with a substituent, and particularly preferably a direct bond or a hydrocarbon group having 1 to 6 carbon atoms in which a hydrogen atom in the group may be substituted with a substituent, more preferably a direct bond or an unsubstituted hydrocarbon group having 1 to 6 carbon atoms, and most preferably an unsubstituted alkylene group having 1 to 3 carbon atoms. Compound A and compositions using it have higher curability and can improve the durability and adhesion of the cured product.
[0087] In compound A, G 1 represents a direct bond, —O—, —S—, or —NR 101-, -CO-, -CO-O-, -O-CO-, -CO-S- or -S-CO- is preferred, and among these, a direct bond, -O-, -S-, -NR 101 Compound A and compositions using the same are highly curable, and can improve the durability and adhesiveness of the cured product.
[0088] In compound A, J 1 is preferably a direct bond, a hydrocarbon group having 1 to 20 carbon atoms in which a hydrogen atom in the group may be substituted with a substituent, or a methylene-substituted hydrocarbon group having 1 to 20 carbon atoms in which a hydrogen atom in the group may be substituted with a substituent, and among these, a direct bond, a hydrocarbon group having 1 to 10 carbon atoms in which a hydrogen atom in the group may be substituted with a substituent, or a methylene-substituted hydrocarbon group having 1 to 10 carbon atoms in which a hydrogen atom in the group may be substituted with a substituent, is particularly preferably a direct bond, a hydrocarbon group having 1 to 10 carbon atoms in which a hydrogen atom in the group may be substituted with a substituent, or a hydrocarbon group in which one or more methylene groups in the hydrocarbon group are -O-, -COO-, -OCO-, -S-, or -NR 101 Preferably, it is a group having 1 to 10 carbon atoms substituted with -, in which a hydrogen atom in the group may be substituted with a substituent, and particularly preferably a direct bond or a hydrocarbon group having 1 to 10 carbon atoms in which a hydrogen atom in the group may be substituted with a substituent, more preferably a direct bond or a hydrocarbon group having 1 to 6 carbon atoms in which a hydrogen atom in the group may be substituted with a substituent, more preferably an unsubstituted hydrocarbon group having 1 to 6 carbon atoms, and most preferably an unsubstituted alkylene group having 1 to 6 carbon atoms. Compound A and compositions using it have higher curability and can improve the durability and adhesion of the cured product.
[0089] In compound A, L1 represents a direct bond, —O—, —S—, or —NR 101 -, -CO-, -CO-O-, -O-CO-, -CO-S- or -S-CO- is preferred, and among these, a direct bond, -O-, -S-, -NR 101 Compound A and compositions using the same are more highly curable, and the durability and adhesiveness of the cured product can be improved.
[0090] In compound A, Z 1 and Z 2 Preferably, at least one of Z is a hydrogen atom, and particularly preferably, both are hydrogen atoms. Compound A and compositions using the same have higher curability, and the resulting cured product can have improved durability and adhesiveness. 1 and Z 2 Among these, the group that is not a hydrogen atom is preferably a group represented by formula (III-1). Compound A and compositions using the same have higher curability, and the durability and adhesiveness of the cured product can be improved.
[0091] In compound A, L 2 is more preferably a direct bond or a hydrocarbon group having 1 to 6 carbon atoms, and most preferably an alkylene group having 1 to 3 carbon atoms. Compound A and compositions using the same have higher curability, and the durability and adhesiveness of the cured product can be improved.
[0092] The method for producing Compound A may be any method that can yield a compound of the desired structure, and can be synthesized by applying a known chemical reaction. For example, Compound A can be synthesized by any of the methods represented by the following schemes 1 to 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.
[0093] (D, G, J, and R are the same as D, G, J, and R in formulae (I) and (II). R' is a direct bond, a hydrocarbon group, or a group in which a methylene group in a hydrocarbon group is substituted with a group selected from the above <Group A>. As these groups, those used for D and J can be used.)
[0094] (D, G, J, and R are the same as D, G, J, and R in formulae (I) and (II). R' is a direct bond, a hydrocarbon group, or a group in which a methylene group in a hydrocarbon group is substituted with a group selected from the above <Group A>. As these groups, those used for D and J can be used.)
[0095] (D, G, J, and R are the same as D, G, J, and R in formulae (I) and (II). R' is a direct bond, a hydrocarbon group, or a group in which a methylene group in a hydrocarbon group is substituted with a group selected from the above <Group A>. As these groups, those used for D and J can be used.)
[0096] The compound A is a polyfunctional compound having multiple cyclic ether groups and unsaturated bond-containing groups, and is capable of two types of polymerization (crosslinking and curing) reactions. In addition to the multiple terminal cyclic ether groups, the unsaturated bond-containing groups in the group also function as a crosslinking agent, so that the compound A and compositions using the same have higher curability and can improve the durability, cure shrinkage, and adhesion of the cured product.
[0097] The compound A can be used as a polymerizable compound. A commonly used method can be used as a method for polymerizing the compound A, and examples thereof include a method of irradiating the compound A with light and a method of heating the compound A. The polymerization can be carried out by adding a polymerization initiator and generating radicals or ions (acids or bases) from the polymerization initiator. When the polymerization initiator is a photopolymerization initiator, radicals or ions (acids or bases) are generated by irradiation with light, and when the polymerization initiator is a thermal polymerization initiator, radicals or ions (acids or bases) are generated by heat treatment, and the generated radicals or ions (acids or bases) 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 determined appropriately depending on the application of compound A and other factors. The heating temperature in the heat treatment can be determined appropriately depending on the application of compound A and other factors.
[0098] The use of the compound A can include a monomer material and a polymer of the composition.The use of the composition and the polymer containing the compound A is not particularly limited as long as it is an use that requires a balance of curability, adhesiveness, and durability, and can include, for example, adhesives, resist materials for printed wiring boards, resist inks, pigment resist inks for car filters, semiconductor sealants, inks, plastic paints, paper printing, film coatings, glass coatings, shatterproof paints, various coating fields such as furniture paints, FRP, linings, display media such as insulating varnishes, insulating sheets, laminates, plasma display panels, and display elements in the electronics field, optical anisotropics such as retardation plates, polarizing plates, light polarizing prisms, and various optical filters, adhesives, insulating materials, structural materials, and optical waveguide clads.
[0099] B. Composition The composition of the present invention (hereinafter, sometimes referred to as composition B) is characterized by containing compound A and a polymerization initiator. According to the present invention, a composition excellent in curability, adhesiveness, and / or durability can be provided.
[0100] The use of the composition B can be the same as that described in the section "A. Compounds."
[0101] 1. Compound A As for Compound A, the same compounds as those described above in "A. Compound" can be used, and therefore further explanation will be omitted here.
[0102] The content of the compound A is preferably 5 parts by mass or more, more preferably 10 parts by mass or more, particularly preferably 15 parts by mass or more, and particularly preferably 20 parts by mass or more, per 100 parts by mass of the solid content of the composition B. This content makes it easy for the composition B to form a polymer and a film that are excellent in curability and superior in adhesion and durability. The solid content is the total amount of components other than the solvent in the composition B.
[0103] The content of the compound A is preferably 2 parts by mass or more, more preferably 5 parts by mass or more, particularly preferably 7 parts by mass or more, and particularly preferably 10 parts by mass or more, in 100 parts by mass of the composition B. This is because the composition B has excellent curability and can easily form a polymer and a film having excellent adhesion and durability.
[0104] 2. Polymerization Initiator The polymerization initiator contained in the composition of the present disclosure will be described in detail. The polymerization initiator may be used alone or in combination of two or more types. The polymerization initiator may be a cationic polymerization initiator used in the polymerization of a compound having a cyclic ether group or a radical polymerization initiator used in the polymerization of a compound having an ethylenically unsaturated bond, and any conventionally known compound may be used. The polymerization initiator may be either a photopolymerization initiator or a thermal polymerization initiator. In the present invention, it is particularly preferable that the polymerization initiator is a photopolymerization initiator. This is because Composition B has excellent curability and facilitates the formation of a polymer and a film that are superior in adhesion and durability.
[0105] 2-1. Cationic Polymerization Initiator The cationic polymerization initiator may be either a photocationic polymerization initiator or a thermal cationic polymerization initiator. In the present invention, the polymerization initiator is preferably a photocationic polymerization initiator. This is because composition B has excellent curability and facilitates the formation of a polymer and a film that are more excellent in adhesiveness and durability.
[0106] The cationic photopolymerization initiator, also called a photoacid generator, generates an acid capable of initiating cationic polymerization upon irradiation with energy rays such as ultraviolet rays. Specific examples of the cationic photopolymerization initiator include those in which the cationic moiety is an aromatic sulfonium ion, aromatic iodonium ion, aromatic diazonium ion, aromatic ammonium ion, thianthrhenium ion, thioxanthonium ion, or (2,4-cyclopentadien-1-yl)[(1-methylethylbenzene]-Fe cation and the anionic moiety is BF 4 - , P.F. 6 - , SbF 6 - , [BX 4 ] - (wherein X is a phenyl group substituted with at least two fluorine atoms or trifluoromethyl groups) may be used alone or in combination of two or more kinds.
[0107] Specific examples of the aromatic sulfonium salt include bis[4-(diphenylsulfonio)phenyl]sulfide bishexafluorophosphate, bis[4-(diphenylsulfonio)phenyl]sulfide bishexafluoroantimonate, bis[4-(diphenylsulfonio)phenyl]sulfide bistetrafluoroborate, bis[4-(diphenylsulfonio)phenyl]sulfide tetrakis(pentafluorophenyl)borate, diphenyl-4-(phenylthio)phenylsulfonium hexafluorophosphate, diphenyl-4-(phenylthio)phenylsulfonium hexafluoroantimonate, diphenyl-4-(phenylthio)phenylsulfonium tetrafluoroborate, and diphenyl-4-(phenylthio)phenylsulfonium tetrakis(pentafluorophenyl)borate. bis[4-(di(4-(2-hydroxyethoxy))phenylsulfonio)phenyl]sulfide bishexafluorophosphate, triphenylsulfonium hexafluoroantimonate, triphenylsulfonium tetrafluoroborate, triphenylsulfonium tetrakis(pentafluorophenyl)borate, bis[4-(di(4-(2-hydroxyethoxy))phenylsulfonio)phenyl]sulfide bishexafluorophosphate, bis[4-(di(4-(2-hydroxyethoxy))phenylsulfonio)phenyl]sulfide bishexafluoroantimonate, bis[4-(di(4-(2-hydroxyethoxy))phenylsulfonio)phenyl]sulfide bistetrafluoroborate, bis[4-(di(4-(2-hydroxyethoxy))phenylsulfonio)phenyl]sulfide tetrakis(pentafluorophenyl)borate, and the like.
[0108] Specific examples of the aromatic iodonium salts include diphenyliodonium hexafluorophosphate, diphenyliodonium hexafluoroantimonate, diphenyliodonium tetrafluoroborate, diphenyliodonium tetrakis(pentafluorophenyl)borate, bis(dodecylphenyl)iodonium hexafluorophosphate, bis(dodecylphenyl)iodonium hexafluoroantimonate, bis(dodecylphenyl)iodonium tetrafluoroborate, bis(dodecylphenyl)iodonium tetrakis(pentafluorophenyl)borate, 4-methylphenyl-4-(1-methylethyl)phenyliodonium hexafluorophosphate, 4-methylphenyl-4-(1-methylethyl)phenyliodonium hexafluoroantimonate, 4-methylphenyl-4-(1-methylethyl)phenyliodonium tetrafluoroborate, and 4-methylphenyl-4-(1-methylethyl)phenyliodonium tetrakis(pentafluorophenyl)borate.
[0109] Specific examples of the aromatic diazonium salt include phenyldiazonium hexafluorophosphate, phenyldiazonium hexafluoroantimonate, phenyldiazonium tetrafluoroborate, and phenyldiazonium tetrakis(pentafluorophenyl)borate.
[0110] Specific examples of the aromatic ammonium salt include 1-benzyl-2-cyanopyridinium hexafluorophosphate, 1-benzyl-2-cyanopyridinium hexafluoroantimonate, 1-benzyl-2-cyanopyridinium tetrafluoroborate, 1-benzyl-2-cyanopyridinium tetrakis(pentafluorophenyl)borate, 1-(naphthylmethyl)-2-cyanopyridinium hexafluorophosphate, 1-(naphthylmethyl)-2-cyanopyridinium hexafluoroantimonate, 1-(naphthylmethyl)-2-cyanopyridinium tetrafluoroborate, and 1-(naphthylmethyl)-2-cyanopyridinium tetrakis(pentafluorophenyl)borate.
[0111] Specific examples of the thianthrhenium salt include 5-methylthianthrhenium hexafluorophosphate, 5-methyl-10-oxothianthrhenium tetrafluoroborate, and 5-methyl-10,10-dioxothianthrhenium hexafluorophosphate.
[0112] Specific examples of the thioxanthonium salt include S-biphenyl 2-isopropyl thioxanthonium hexafluorophosphate.
[0113] Furthermore, other cationic moieties include, for example, (2,4-cyclopentadien-1-yl)[(1-methylethyl)benzene]-Fe salts such as (2,4-cyclopentadien-1-yl)[(1-methylethylbenzene]-Fe(II) hexafluorophosphate, (2,4-cyclopentadien-1-yl)[(1-methylethylbenzene]-Fe(II) hexafluoroantimonate, (2,4-cyclopentadien-1-yl)[(1-methylethylbenzene]-Fe(II) tetrafluoroborate, and (2,4-cyclopentadien-1-yl)[(1-methylethylbenzene]-Fe(II) tetrakis(pentafluorophenyl)borate.
[0114] Commercially available products of the photocationic polymerization initiator include, for example, CPI(R)-100P, CPI(R)-110P, CPI(R)-101A, CPI(R)-200K, and CPI(R)-210S (all manufactured by San-Apro Co., Ltd.); Cyracure(R) photocuring initiator UVI-6990, Cyracure(R) photocuring initiator UVI-6992, and Cyracure(R) photocuring initiator UVI-6976 (all manufactured by Dow Chemical Japan Co., Ltd.); Adeka Arcles SP-150, Adeka Arcles SP-151, Adeka Arcles SP-152, Adeka Arcles SP-170, Adeka Arcles SP-172, and Adeka Arcles SP-300 (all manufactured by Dow Chemical Japan Co., Ltd.). , manufactured by ADEKA Corporation); CI-5102, CI-2855 (all manufactured by Nippon Soda Co., Ltd.); San-Aid® SI-60L, San-Aid® SI-80L, San-Aid® SI-100L, San-Aid® SI-110L, San-Aid® SI-180L, San-Aid® SI-110, San-Aid® SI-180 (all manufactured by Sanshin Chemical Industry Co., Ltd.); Esacure® 1064, Esacure® 1187 (all manufactured by Lamberti Co., Ltd.); Omnicat 550, Omnicat 250 (manufactured by IGM Resins Co., Ltd.); Rhodesil Photoinitiator 2074 (manufactured by Rhodia Japan Co., Ltd.), and the like.
[0115] A thermal cationic polymerization initiator, which is also called a thermal acid generator, functions as a polymerization initiator that promotes thermal curing by exciting a compound containing a cationic species upon heating and undergoing a thermal decomposition reaction. Examples of the thermal cationic polymerization initiator include phonate, triphenylsulfonium tetrafluoroborate, tri-p-tolylsulfonium hexafluorophosphate, tri-p-tolylsulfonium trifluoromethanesulfonate, bis(cyclohexylsulfonyl)diazomethane, bis(tert-butylsulfonyl)diazomethane, bis(p-toluenesulfonyl)diazomethane, triphenylsulfonium trifluoromethanesulfonate, diphenyl-4-methylphenylsulfonium trifluoromethanesulfonate, diphenyl-2,4,6-trimethylphenylsulfonium-p-toluenesulfonate, and diphenyl-p-phenylthiophenylsulfonium hexafluorophosphate.
[0116]
[0033] Examples of commercially available thermal cationic polymerization initiators include the AMERICURE series (manufactured by American Scan) which is a diazonium salt-based compound; the UVE series (manufactured by General Electric Co.) which is an iodonium salt-based compound; the FC series (manufactured by 3M); UV9310C (manufactured by GE Toshiba Silicones Co., Ltd.); the WPI series and WPAG series (manufactured by Fujifilm Wako Pure Chemical Industries Co., Ltd.); the CYRACURE series (manufactured by Union Carbide Corporation) which is a sulfonium salt-based compound; the UVI series (manufactured by General Electric Co.); the CD series (manufactured by Sartomer); the Optomer SP series and Optomer CP series (manufactured by ADEKA Corporation); the SAN-AID SI series (manufactured by Sanshin Chemical Industry Co., Ltd.); the CI series (manufactured by Nippon Soda Co., Ltd.); and the CPI series (manufactured by San-Apro Ltd.).
[0117] The thermal cationic polymerization initiator used preferably has a 10-hour half-life temperature of 80°C to 180°C, more preferably 100°C to 150°C, from the viewpoint of reaction efficiency and safety.
[0118] The content of the photo- and thermal cationic polymerization initiator is preferably 0.1 to 30 parts by mass, more preferably 0.5 to 20 parts by mass, and particularly preferably 1 to 15 parts by mass, relative to 100 parts by mass of Compound A. This is because Composition B has excellent curability and facilitates the formation of a polymer and a film having even more excellent adhesion and durability. The content of the cationic polymerization initiator is preferably 0.1 to 30 parts by mass, more preferably 0.5 to 20 parts by mass, and particularly preferably 1 to 15 parts by mass, relative to 100 parts by mass of the total of Compound A and the cationically polymerizable compound X2 described below. This is because Composition B has excellent curability and facilitates the formation of a polymer and a film having even more excellent adhesion and durability.
[0119] 2-2. Radical Polymerization Initiator The polymerization initiator may be any radical polymerization initiator used for polymerizing a compound having an ethylenically unsaturated bond group, 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, the polymerization initiator is preferably a photoradical polymerization initiator. This is because composition B has excellent curability and facilitates the formation of a polymer and a film that are superior in adhesion and durability.
[0120] 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-phenoxybenzoyl 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, 4,4'-dichlorobenzophenone, 4,4 benzophenones such as 4-benzoyl-4'-methyldiphenyl sulfide, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, and the like; carbazoles such as 3-(2-methyl-2-morpholinopropionyl)-9-methylcarbazole, and the like; α-dicarbonyls such as benzyl and methyl benzoylformate, and the like;Oxygen compounds such as those described in JP-A-2000-80068, JP-A-2001-233842, JP-A-2005-97141, JP-T-2006-516246, Japanese Patent No. 3860170, Japanese Patent No. 3798008, WO2006 / 018973, JP-A-2011-132215, and WO2015 / 152153 esters; 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, and the like;
[0121] 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-carbonitrile), dimethyl 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 Examples include 2,2-azobis(2-methylpropionate) and 2,2'-azobis(N-butyl-2-methylpropionamide), and azo compounds such as 2,2'-azobis(2-methylbutyronitrile) are preferred because of their high yield.
[0122] 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.
[0123] 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.
[0124] The thermal radical polymerization initiator used preferably has a 10-hour half-life temperature of 80°C to 180°C, more preferably 100°C to 150°C, from the viewpoint of reaction efficiency and safety.
[0125] The content of the photo- and thermal-radical polymerization initiator is preferably 0.1 to 30 parts by mass, more preferably 0.5 to 20 parts by mass, and particularly preferably 1 to 15 parts by mass, relative to 100 parts by mass of Compound A. This is because Composition B has excellent curability and facilitates the formation of a polymer and a film that are more excellent in adhesion and durability. The content of the radical polymerization initiator is preferably 0.1 to 30 parts by mass, more preferably 0.5 to 20 parts by mass, and particularly preferably 1 to 15 parts by mass, relative to 100 parts by mass of the total of Compound A and radically polymerizable Compound X1. This is because Composition B has excellent curability and facilitates the formation of a polymer and a film that are more excellent in adhesion and durability.
[0126] Composition B of the present disclosure preferably contains a cationic polymerization initiator, and more preferably contains both a cationic polymerization initiator and a radical polymerization initiator, because this allows the polymerization (crosslinking / curing) reaction of both the cyclic ether group and the unsaturated bond-containing group in Compound A to proceed.
[0127] Composition B of the present disclosure preferably contains both a photocationic polymerization initiator and a photoradical polymerization initiator. When a photocationic polymerization initiator and a photoradical polymerization initiator are used in combination, the mass ratio of the photocationic polymerization initiator to the photoradical polymerization initiator is preferably 100:30 to 300, more preferably 100:50 to 200, and particularly preferably 100:75 to 150. This is because composition B has excellent curability and facilitates the formation of a polymer and a film that are more excellent in adhesion and durability.
[0128] As the photocationic polymerization initiator, aromatic sulfonium salt-based and aromatic iodonium salt-based cationic polymerization initiators are preferred, and aromatic sulfonium salt-based cationic polymerization initiators are particularly preferred, because composition B has excellent curability and facilitates the formation of a polymer and a film having excellent adhesion and durability.
[0129] As the photoradical polymerization initiator, benzil ketals, hydroxyacetophenones, aminoacetophenones, phosphine oxides, carbazoles, and oxime esters are preferred, and among these, aminoacetophenones, phosphine oxides, carbazoles, and oxime esters are preferred, and phosphine oxides are particularly preferred, because composition B has excellent curability and can easily form a polymer and a film having excellent adhesion and durability.
[0130] In Composition B of the present disclosure, the photoradical polymerization initiator preferably has absorption in the long wavelength region of 300 nm or more. This is because Composition B has excellent curability and facilitates the formation of a polymer and a film that are superior in adhesion and durability. The absorption wavelength is confirmed by dissolving each polymerization initiator in a solvent such as acetonitrile to a concentration of 0.05% by mass, placing the solution in a 10 mm square quartz cell, and measuring the absorbance using a V-760 ultraviolet-visible-near-infrared spectrophotometer manufactured by JASCO Corporation.
[0131] In Composition B of the present disclosure, the photoradical polymerization initiator preferably has an absorption wavelength peak at 300 nm or more, more preferably at 330 nm or more, and particularly preferably at 360 nm or more. This is because Composition B has excellent curability and facilitates the formation of a polymer and a film with superior adhesion and durability. The absorption wavelength is confirmed by dissolving each polymerization initiator in a solvent such as acetonitrile to a concentration of 0.1% by mass, placing the solution in a 10 mm square quartz cell, and measuring the absorbance using a UV-Vis-NIR spectrophotometer V-760 manufactured by JASCO Corporation.
[0132] 3. Other Components 3-1. Polymerizable Compound X The composition B may contain a polymerizable compound other than compound A (hereinafter, sometimes referred to as polymerizable compound X). The polymerizable compound X may be any compound other than compound A, as long as it has a polymerizable reactive group. Examples of the polymerizable compound X include radical polymerizable compounds such as unsaturated carboxylic acids, unsaturated acid anhydrides, aromatic vinyl compounds, N-substituted maleimides, conjugated dienes, vinyl ethers, N-vinyl compounds, and unsaturated isocyanates, and cationically polymerizable compounds such as epoxy compounds and oxetane compounds. The composition of the present invention may contain, in addition to compound A, either a radical polymerizable compound (hereinafter, also referred to as "radical polymerizable compound X1") or a cationically polymerizable compound (hereinafter, also referred to as "cationically polymerizable compound X2"), or may contain both radical polymerizable compound X1 and cationically polymerizable compound X2.
[0133] In the composition of the present invention, the total amount of compound A and radical polymerizable compound X1 is preferably 30 parts by mass or more and 99.9 parts by mass or less, more preferably 40 parts by mass or more and 99.8 parts by mass or less, and particularly preferably 50 parts by mass or more and 99.5 parts by mass or less, per 100 parts by mass of the solids content of composition B. This content makes it easy for composition B to form a polymer and a film that are excellent in curability and superior in adhesion and durability. In the composition of the present invention, the total amount of compound A and radical polymerizable compound X1 is preferably 15 parts by mass or more and 99.9 parts by mass or less, more preferably 20 parts by mass or more and 99.8 parts by mass or less, and particularly preferably 25 parts by mass or more and 99.5 parts by mass or less, per 100 parts by mass of composition B. This content makes it easy for composition B to form a polymer and a film that are excellent in curability and superior in adhesion and durability.
[0134] In the composition of the present invention, the total amount of compound A and cationically polymerizable compound X2 is preferably 30 parts by mass or more and 99.9 parts by mass or less, more preferably 40 parts by mass or more and 99.8 parts by mass or less, and particularly preferably 50 parts by mass or more and 99.5 parts by mass or less, per 100 parts by mass of the solid content of composition B. This content allows composition B to easily form a polymer and a film having excellent curability, adhesion, and durability. In the composition of the present invention, the total amount of compound A and cationically polymerizable compound X2 is preferably 15 parts by mass or more and 99.9 parts by mass or less, more preferably 20 parts by mass or more and 99.8 parts by mass or less, and particularly preferably 25 parts by mass or more and 99.5 parts by mass or less, per 100 parts by mass of composition B. This content allows composition B to easily form a polymer and a film having excellent curability, adhesion, and durability.
[0135] Specific examples of the unsaturated carboxylic acids include crotonic acid, cinnamic acid, vinylbenzoic acid, maleic acid, fumaric acid, itaconic acid, citraconic acid, and mesaconic acid. Also included are various acrylates and methacrylates. These unsaturated carboxylic acids 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.
[0136] 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 glycol. Examples of the acrylates include ethylene 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.
[0137] 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 hydroxypivalic acid neopentyl glycol di(meth)acrylate. and difunctional (meth)acrylates including 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.
[0138] Specific examples of the unsaturated acid anhydride include maleic anhydride, phthalic anhydride, itaconic anhydride, etc. These unsaturated acid anhydrides may be used alone or in combination of two or more.
[0139] Specific examples of the aromatic vinyl compounds include styrene, α-methylstyrene, vinyltoluene, methoxystyrene, etc. These aromatic vinyl compounds may be used alone or in combination of two or more.
[0140] Specific examples of the N-substituted maleimide include methylmaleimide, ethylmaleimide, isopropylmaleimide, cyclohexylmaleimide, phenylmaleimide, benzylmaleimide, naphthylmaleimide, etc. These N-substituted maleimides may be used alone or in combination of two or more.
[0141] Specific examples of the conjugated diene include 1,3-butadiene, isoprene, chloroprene, etc. These conjugated dienes may be used alone or in combination of two or more.
[0142] Specific examples of the vinyl ether include methyl vinyl ether, ethyl vinyl ether, propyl vinyl ether, butyl vinyl ether, 2-ethylhexyl vinyl ether, n-nonyl vinyl ether, lauryl vinyl ether, cyclohexyl vinyl ether, methoxyethyl vinyl ether, ethoxyethyl vinyl ether, methoxyethoxyethyl vinyl ether, methoxypolyethylene glycol vinyl ether, 2-hydroxyethyl vinyl ether, 4-hydroxybutyl vinyl ether, etc. These vinyl ethers may be used alone or in combination of two or more.
[0143] Specific examples of the N-vinyl compound include N-vinylpyrrolidone, N-vinylcaprolactam, N-vinylimidazole, N-vinylmorpholine, N-vinylacetamide, etc. These N-vinyl compounds may be used alone or in combination of two or more.
[0144] Specific examples of the unsaturated isocyanate include isocyanatoethyl (meth)acrylate, allyl isocyanate, etc. These unsaturated isocyanates may be used alone or in combination of two or more kinds.
[0145] The epoxy compound and the oxetane compound are compounds having a three-membered or four-membered ring ether and can be used without any particular limitation as long as they are compounds that have been used in conventional curable compositions. The epoxy compound and the oxetane compound may be used alone or in combination of two or more types.
[0146] 3-2. Sensitizer Composition B of the present invention may contain a sensitizer in addition to the polymerization initiator to improve the sensitivity and curability of the composition. Examples of sensitizers include dye compounds, dialkylaminobenzene compounds, and mercaptan hydrogen donors. Examples of dye compounds include xanthene dyes, coumarin dyes, 3-ketocoumarin compounds, and pyrromethene dyes. Examples of dialkylaminobenzene compounds include ethyl 4-dimethylaminobenzoate and 2-ethylhexyl 4-dimethylaminobenzoate. Examples of mercaptan hydrogen donors include 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, and 2-mercaptobenzimidazole. These sensitizers may be used alone or in combination.
[0147] 3-3. Solvent The composition B may contain a solvent. The solvent is capable of dissolving or dispersing each component in the composition. Therefore, even if the composition B is in a liquid state at room temperature (25°C) and atmospheric pressure, the compound A, polymerizable compound X, and polymerization initiator are not included in the solvent. Either water or an organic solvent can be used as the solvent. In the present invention, the solvent is preferably an organic solvent, as this makes it easier to dissolve or disperse compound A.
[0148] Examples of the organic solvent include carbonates such as propylene carbonate and diethyl carbonate; ketones such as acetone and 2-heptanone; polyhydric alcohols and derivatives thereof such as ethylene glycol, propylene glycol, propylene glycol monoacetate, dipropylene glycol, and monomethyl ether or monophenyl ether of dipropylene glycol monoacetate; cyclic ethers such as dioxane; esters such as ethyl formate and 3-methyl-3-methoxybutyl acetate; aromatic hydrocarbons such as toluene and xylene; and lactones such as γ-caprolactone and δ-caprolactone.
[0149] The content of the solvent in composition B of the present invention is appropriately set depending on the use of composition B, and can be, for example, 1 part by mass or more and 99 parts by mass or less per 100 parts by mass of the composition.
[0150] 3-4. Other Components Composition B may contain other components as needed. Such other components may be selected depending on the intended use of the composition, and include, for example, binder resins (non-reactive oligomers or polymers); other polymerization initiators; benzotriazole-, triazine-, or benzoate-based ultraviolet absorbers; phenol-, phosphorus-, or sulfur-based antioxidants; antistatic agents such as cationic surfactants, anionic surfactants, nonionic surfactants, and amphoteric surfactants; flame retardants such as halogen-based compounds, phosphate ester compounds, phosphoric acid amide compounds, melamine-based compounds, fluororesins or metal oxides, (poly)melamine phosphate, and (poly)piperazine phosphate; Examples of other components include hydrocarbon-based, fatty acid-based, aliphatic alcohol-based, aliphatic ester-based, aliphatic amide-based, and metal soap-based lubricants; colorants such as dyes, pigments, and carbon black; silicic acid-based inorganic additives such as fumed silica, fine particle silica, silica stone, diatomaceous earth, clay, kaolin, diatomaceous earth, silica gel, calcium silicate, sericite, kaolinite, flint, feldspar powder, vermiculite, attapulgite, talc, mica, minesotite, pyrophyllite, and silica; fillers such as glass fiber and calcium carbonate; crystallization agents such as nucleating agents and crystallization accelerators; silane coupling agents, and agents imparting rubber elasticity such as flexible polymers. The content of these other components in Composition B of the present invention can be 50 parts by mass or less per 100 parts by mass of Composition B.
[0151] The method for producing the composition B may be any known method as long as it can mix the components in the desired amounts. For example, a method may be used in which the compound A is dissolved or dispersed in a solvent or the like, and then the resin component is added to the solvent. Examples of the mixer that can be used include a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, and a three-roll mill.
[0152] C. Polymer The polymer of the present invention (hereinafter may be referred to as polymer C) has structural units derived from compound A. According to the present invention, polymer C has structural units derived from compound A, which makes it easier to form a polymer having superior adhesiveness and durability.
[0153] The use of the polymer C can be the same as that described in the section "A. Compounds."
[0154] 1. Structural Unit Derived from Compound A Polymer C of the present invention has a structural unit derived from compound A (hereinafter, may be referred to as structural unit A). Here, as compound A constituting structural unit A, the same compounds as those described in the above section "A. Compound" can be used, and therefore further explanation here will be omitted.
[0155] The content of the structural unit A is preferably 5% by mass or more, more preferably 10% by mass or more, particularly preferably 20% by mass or more, and particularly preferably 25% by mass or more, relative to the polymer C. This is because the above content makes it easier to form a polymer C having superior adhesiveness and durability.
[0156] 2. Components Other Than Compound A Polymer C has structural unit A, but may also have other structural units as necessary. Examples of such other structural units include structural units derived from polymerizable compounds X other than compound A (hereinafter, sometimes referred to as structural unit X). Here, the polymerizable compounds X constituting structural unit X can be the same as those described in the section "B. Composition" above, and therefore further explanation will be omitted here. Polymer C may be a homopolymer of compound A, or a copolymer of compound A and polymerizable compound X.
[0157] When polymer C is a copolymer of compound A and polymerizable compound X, the content of structural unit X is preferably 90 parts by mass or less, more preferably 80 parts by mass or less, and particularly preferably 70 parts by mass or less, per 100 parts by mass of polymer C. This is because such a content makes it easier to form polymer C having superior adhesiveness and durability.
[0158] 3. Others The method for producing polymer C may be any method capable of polymerizing compound A, from which structural unit A is derived. While the polymerization method is not particularly limited, a method of polymerization using a polymerization initiator is preferred. When the polymerization initiator is a photopolymerization initiator, the method is preferably a method of irradiating composition B with light. When the polymerization initiator is a thermal polymerization initiator, the method is preferably a method of heating composition B. Furthermore, it is preferred to contain a cationic polymerization initiator, and it is particularly preferred to contain both a cationic polymerization initiator and a radical polymerization initiator. It is particularly preferred to contain both a photocationic polymerization initiator and a photoradical polymerization initiator. This is because it facilitates the formation of a polymer with superior adhesion and durability.
[0159] D. Cured Product The cured product of the present invention (hereinafter, sometimes referred to as cured product D) is a cured product of composition B.
[0160] According to the present invention, by using composition B, it becomes easy to form a cured product having excellent adhesiveness and durability.
[0161] The uses of the cured product D can be the same as those described in the section "A. Compounds."
[0162] 1. Composition B As for composition B, the same as that described above in "B. Composition" can be used, and therefore a description thereof will be omitted here.
[0163] The method for producing the cured product D is not particularly limited as long as it is a method that can form a desired shape into a cured product of the composition B. As such a production method, for example, the production methods described in the section "E. Production method of cured product" below can be used.
[0164] E. Method for Producing the Cured Product The method for producing the cured product D of the present invention will be described. One of the features of the method for producing the cured product D of the present invention is that it includes a curing step of curing the composition B.
[0165] 1. Curing Step In the curing step of the present invention, a commonly used method can be used to cure the composition, such as irradiating composition B with light or heating composition B. In the present invention, composition B preferably contains a polymerization initiator together with compound A, and more preferably contains a cationic polymerization initiator, and particularly preferably contains both a cationic polymerization initiator and a radical polymerization initiator. This is because a cured product with excellent adhesion and durability can be provided. When the polymerization initiator is a photopolymerization initiator, the method is preferably a method of irradiating composition B with light. When the polymerization initiator is a thermal polymerization initiator, the method is preferably a method of heating composition B. In the present invention, the curing method is preferably a method of irradiating composition B with light, i.e., the curing step is preferably a step of irradiating composition B with light. This is because a cured product with excellent adhesion and durability can be provided. Specific light irradiation methods, heating methods, etc. can be the same as those listed as the polymerization methods described in the section "A. Compound" above.
[0166] 2. Other Steps The method for producing a cured product of the present invention may include other steps as necessary in addition to the curing step. Examples of the other steps include a development 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-bake step in which the cured product is heat-treated after the curing step, a pre-bake step in which the composition is heat-treated to remove 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 included, a reaction step with each agent may be included in addition to the above steps. The curing conditions may be set appropriately depending on the components used.
[0167] 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.
[0168] The present disclosure will be described in more detail below with reference to examples, but the present disclosure is not limited to these examples.
[0169] Synthesis Example 1 Compound A1 163 mL of methylene chloride, 76.86 g (408 mmol) of 3-ethyl-3-(4-hydroxybutyloxymethyl)oxetane, and 41.25 g (408 mmol) of triethylamine were added to a flask and stirred under ice cooling. A solution of 25.0 g (163 mmol) of fumarolic acid dichloride and 25 g of methylene chloride was added dropwise, and the mixture was reacted at 10°C for 3 hours. After completion of the reaction, 100 mL of 5 wt % diluted hydrochloric acid was added, and the oil layer was removed and washed four times with distilled water. The oil layer was dried over magnesium sulfate and the solvent was removed. The resulting brown oil was purified by silica gel column chromatography to obtain 29.7 g of a colorless, transparent oil (yield: 40.0%). 1 The results of H-NMR measurement are shown in Table 1.
[0170]
[0171] [Synthesis Example 2] Compound A2 A flask was charged with 64.0 g of dichloromethane, 18.8 g (155 mmol) of dimethylaniline, and 38.0 g (310 mmol) of 3-ethyl-3-hydroxymethyloxetane and cooled. A solution of 10.0 g (62 mmol) of fumarolic acid dichloride and 18.6 g of dichloromethane was added dropwise, and the mixture was allowed to react at 0°C for 1 hour. After the reaction was completed, 80 g of distilled water was added and the mixture was stirred for 30 minutes. The oil layer was removed and washed three times with distilled water. The oil layer was dried over sodium sulfate and the solvent was removed. The resulting crude crystals were purified by silica gel column chromatography to obtain 9.4 g of white crystals (yield: 48.2%). 1 The results of H-NMR measurement are shown in Table 1.
[0172]
[0173] [Synthesis Example 3] Compound A3 A flask was charged with 30 mL of dichloromethane, 15.1 g (125 mmol) of dimethylaniline, and 18.7 g (252 mmol) of glycidol and cooled to 0°C. 7.59 g (49.6 mmol) of fumarolic acid dichloride was added dropwise, and the mixture was allowed to react at 0°C for 1 hour. After the reaction was completed, 80 g of distilled water was added and the mixture was stirred for 30 minutes. The oil layer was removed and washed three times with distilled water. The oil layer was dried over sodium sulfate and the solvent was removed. The obtained crude crystals were purified by silica gel column chromatography to obtain 9.78 g of white crystals (yield 86.0%). 1 The results of H-NMR measurement are shown in Table 1.
[0174]
[0175]
[0176] A1': 4-HBAGE (manufactured by Mitsubishi Chemical) A2': OXE-10 (manufactured by Osaka Organic) A3': OXT-221 (manufactured by Toagosei) A4': The following compound
[0177] [Cationic polymerizable compound] EP-4100E (manufactured by ADEKA) Glycidyl phenyl ether: GPE (manufactured by Tokyo Chemical Industry Co., Ltd.) [Radical polymerizable compound] A-HD-N (manufactured by Shin-Nakamura Chemical Co., Ltd.) Viscoat #540 (manufactured by Osaka Organic Chemical Industry Co., Ltd.) [Cationic polymerization initiator] SP-151 (manufactured by ADEKA) SP-172 (manufactured by ADEKA) [Radical polymerization initiator] Omnirad 819 (manufactured by IGM ResinS, hereinafter also referred to as "Irg819") Omnirad 184 (manufactured by IGM ResinS, hereinafter also referred to as "Irg184")
[0178] [Evaluation 1] 1. Preparation of Composition 3 g of Compound A1, 4 g of GPE, 1 g of EP-4100E, and 2 g of Viscoat #540 were added and stirred until uniform. After stirring, 0.3 g of SP-151 as a photocationic polymerization initiator and 0.3 g of Irg819 as a photoradical polymerization initiator were added and stirred until uniform, thereby obtaining a composition (Example 1). Each composition was prepared using the blending amounts shown in Tables 2, 3, and 4, and the compositions of Examples 2 to 5 and Comparative Examples 1 to 12 were obtained.
[0179] 2. Evaluation of adhesive strength Approximately 0.2 mL of the composition was applied to a glass plate, sandwiched between SUS substrates, and exposed to light from the glass surface (exposure dose 3000 mJ / cm 2 ), and a sample for adhesion test was prepared. The shear stress of the sample was measured using a universal testing machine (Shimadzu Corporation). The peeled area after peeling was also measured using a micrometer. The adhesive strength was calculated by dividing the shear stress by the peeled area. Adhesion strength (MPa) = [shear stress] / [peel area] <Evaluation criteria> Adhesion strength of 30 MPa or more: A 20 MPa or more but less than 30 MPa: B 10 MPa or more but less than 20 MPa: C Less than 10 MPa: D
[0180] 3. Evaluation of Tg and tan δ of the cured product Polyimide tape was attached to a glass plate whose surface had been subjected to a release treatment, and the composition was uniformly spread and then exposed (exposure amount: 3000 mJ / cm 2 , one side 1500mJ / cm 2 (Double-sided exposure at 100°C). After exposure, the film was heated in an oven at 100°C for 1 hour to obtain a cured film measuring 2.0 cm long x 0.5 cm wide x 50 μm thick. The Tg and tan δ of the cured film were measured using a dynamic viscoelasticity measuring device (HITACHI DMS7100). The higher the Tg, the higher the curability, and the lower the tan δ, the higher the crosslinking density, which can be said to be excellent in durability. <Evaluation criteria: Tg> 100°C or higher: A 50°C or higher but less than 100°C: B Less than 50°C: C <Evaluation criteria: tan δ> Less than 0.3: A 0.3 or higher but less than 0.6: B 0.6 or higher: C
[0181] 4. Evaluation of Curing Speed The composition was applied to a glass plate with a bar coater to a thickness of 30 μm. The exposure dose was 200 mJ / cm. 2 The film was exposed to light (exposure device: Eye Graphics curing conveyor system, mercury lamp) at 200 mJ / cm until the tackiness disappeared. 2 The exposure was carried out step by step, and the exposure dose at which tack disappeared (200 mJ / cm 2 × number of exposures) was defined as the exposure amount for hardening. The evaluation results are shown in Tables 2 to 4.
[0182]
[0183]
[0184]
[0185] [Evaluation 2] 1. Preparation of Compositions Compositions were prepared in the amounts listed in Table 5, to obtain the compositions of Examples 6 and 7 and Comparative Examples 13 to 14.
[0186] 2. Evaluation of Curing Speed The composition was applied to a glass plate with a bar coater to a thickness of 30 μm. The exposure dose was 200 mJ / cm. 2 The film was exposed to light (exposure device: Eye Graphics curing conveyor system, mercury lamp) at 200 mJ / cm until the tackiness disappeared. 2 The exposure was carried out step by step, and the exposure dose at which tack disappeared (200 mJ / cm 2 × number of exposures) was defined as the curing exposure amount. 2 Less than: A 3000 mJ / cm 2 More than 5000mJ / cm 2 Less than: B 5000 mJ / cm 2 More than 7000mJ / cm 2 Less than: C 7000 mJ / cm 2 Above: D
[0187] 3. Evaluation of Tg of Cured Product Polyimide tape was attached to a glass plate whose surface had been subjected to a release treatment, and the composition was uniformly spread on the surface and then exposed to light (exposure device: EYE GRAPHIC curing conveyor system, mercury lamp). 2 After exposure, the film was heated in an oven at 100°C for 1 hour to obtain a cured film measuring 2.0 cm long x 0.5 cm wide x 50 μm thick. The Tg of the cured film was measured using a dynamic viscoelasticity measuring device (HITACHI DMS7100). <Evaluation criteria> 70°C or higher: A 50°C or higher but lower than 70°C: B 30°C or higher but lower than 50°C: C Less than 30°C: D
[0188] The evaluation results are shown in Table 5.
[0189]
[0190] As shown in Table 5, it can be seen that Compound A of the present invention can achieve excellent curing speed and curability (Tg).
Claims
1. A composition comprising a compound having a structure represented by the following general formula (I), a structure represented by the following general formula (II), and an unsaturated bond-containing group, and a polymerization initiator, wherein the compound has two or more structures represented by the following general formula (I): (wherein R is a hydrogen atom, a halogen atom, a cyano group, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 30 carbon atoms in which a hydrogen atom may be substituted by a substituent, or a group having 1 to 30 carbon atoms in which one or more methylene groups in the hydrocarbon group are substituted by a group selected from the following <Group A> in which a hydrogen atom in the group may be substituted by a substituent; a is an integer of 0 to 5, b is an integer of 0 to 5, a+b is an integer of 1 or more, *, **, and *** are bonding sites; D and J each independently represent a direct bond, a hydrocarbon group having 1 to 30 carbon atoms in which a hydrogen atom may be substituted by a substituent, or a group having 1 to 30 carbon atoms in which one or more methylene groups in the hydrocarbon group are substituted by a group selected from the following <Group A> in which a hydrogen atom in the group may be substituted by a substituent; G and L each independently represent a direct bond or a group selected from the following <Group A>, <Group A> being -O-, -S-, -NR 101 -, -CO-, -CO-O-, -O-CO-, CO-NR 101 --, --NR 101 -CO-, -CO-S- or -S-CO-; R 101 is a hydrogen atom, a halogen atom, a cyano group, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 10 carbon atoms, or a heterocyclic ring-containing group having 2 to 10 carbon atoms.
2. The composition of claim 1, wherein the compound has a structure represented by the following general formula (III): (In the formula, D 1 and J. 1 each independently represents a direct bond, a hydrocarbon group having 1 to 30 carbon atoms in which a hydrogen atom may be substituted by a substituent, or a group having 1 to 30 carbon atoms in which one or more methylene groups in the hydrocarbon group are substituted by a group selected from the following <Group A> in which a hydrogen atom may be substituted by a substituent; 1 and L 1 are each independently a direct bond or a group selected from the following <Group A>, 1 is a hydrogen atom, a halogen atom, a cyano group, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 30 carbon atoms in which a hydrogen atom may be substituted by a substituent, or a hydrocarbon group having 1 to 30 carbon atoms in which one or more methylene groups are substituted by a group selected from the following <Group A> in which a hydrogen atom may be substituted by a substituent; Z 1 and Z 2 are each independently a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, or a group represented by the following formula (III-1), a1 is an integer of 0 to 5, b1 is an integer of 0 to 5, and a1+b1 is an integer of 1 or more, <Group A> is -O-, -S-, -NR 101 -, -CO-, -CO-O-, -O-CO-, CO-NR 101 --, --NR 101 -CO-, -CO-S- or -S-CO-; R 101 is a hydrogen atom, a halogen atom, a cyano group, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 10 carbon atoms, or a heterocyclic ring-containing group having 2 to 10 carbon atoms. (In the formula, D 1 , G 1 , J 1 , L 1 , R 1 , a1 and b1 are the same as those in formula (III); L 2 is a direct bond or a hydrocarbon group having 1 to 10 carbon atoms. * indicates the bonding site.) 3. The composition according to claim 1 or 2, which contains a cationic polymerization initiator as the polymerization initiator.
4. The composition according to claim 3, further comprising a radical polymerization initiator.
5. The composition according to claim 3, wherein said cationic polymerization initiator is an aromatic sulfonium salt.
6. A cured product of the composition according to claim 1 or 2.
7. A method for producing a cured product, comprising the step of curing the composition according to claim 3 by irradiating it with light.
8. A compound having a structure represented by the following general formula (III): (In the formula, D 1 and J. 1 each independently represents a direct bond, a hydrocarbon group having 1 to 30 carbon atoms in which a hydrogen atom may be substituted by a substituent, or a group having 1 to 30 carbon atoms in which one or more methylene groups in the hydrocarbon group are substituted by a group selected from the following <Group A> in which a hydrogen atom may be substituted by a substituent; 1 and L 1 are each independently a direct bond or a group selected from the following <Group A>, 1 is a hydrogen atom, a halogen atom, a cyano group, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 30 carbon atoms in which a hydrogen atom may be substituted by a substituent, or a hydrocarbon group having 1 to 30 carbon atoms in which one or more methylene groups are substituted by a group selected from the following <Group A> in which a hydrogen atom may be substituted by a substituent; Z 1 and Z 2 are each independently a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, or a group represented by the following formula (III-1), a1 is an integer of 0 to 5, b1 is an integer of 0 to 5, and a1+b1 is an integer of 1 or more, <Group A> is -O-, -S-, -NR 101 -, -CO-, -CO-O-, -O-CO-, CO-NR 101 --, --NR 101 -CO-, -CO-S- or -S-CO-; R 101 is a hydrogen atom, a halogen atom, a cyano group, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 10 carbon atoms, or a heterocyclic ring-containing group having 2 to 10 carbon atoms. (In the formula, D 1 , G 1 , J 1 , L 1 , R 1 , a1 and b1 are the same as those in formula (III); L 2 is a direct bond or a hydrocarbon group having 1 to 10 carbon atoms. * indicates the bonding site.) 9. D above 1 is a hydrocarbon group having 1 to 10 carbon atoms in which a hydrogen atom may be substituted by a substituent, or a hydrocarbon group having 1 to 10 carbon atoms in which one or more methylene groups are substituted by a group selected from the above <Group A> in which a hydrogen atom may be substituted by a substituent, 1 is -O-, -S-, -CO-, -CO-O- or -O-CO-, 1 is a hydrocarbon group having 1 to 10 carbon atoms in which a hydrogen atom may be substituted by a substituent, or a hydrocarbon group having 1 to 10 carbon atoms in which one or more methylene groups are substituted by a group selected from the above <Group A>, and a hydrogen atom in the group may be substituted by a substituent, 1 is -CO-O- or -O-CO-, 1 is a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms in which a hydrogen atom may be substituted by a substituent, or a group having 1 to 10 carbon atoms in which one or more methylene groups in the hydrocarbon group are substituted by a group selected from the following <Group A> in which a hydrogen atom may be substituted by a substituent, a1 is 1, and b1 is 1.
10. D above 1 is a hydrocarbon group having 1 to 6 carbon atoms, the hydrogen atoms of which may be substituted with a substituent, 1 is -O-, -CO-O- or -O-CO-, 1 is a hydrocarbon group having 1 to 10 carbon atoms, the hydrogen atoms of which may be substituted with a substituent, 1 The compound according to claim 9, wherein is a hydrocarbon group having 1 to 10 carbon atoms in which a hydrogen atom may be substituted by a substituent.
11. A polymer obtained by polymerizing the compound according to any one of claims 8 to 10 as a monomer.
Citation Information
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