Composition, cured product, and method for producing the cured product

Abstract

To provide a composition having excellent adhesion to metal and metal oxide.SOLUTION: A composition includes an acrylamide compound (A), an ethylenic unsaturated compound (B) having a carboxy group or an alkoxysilyl group, and a radical polymerization initiator (C). Preferably, the acrylamide compound (A) includes a monofunctional acrylamide compound and a polyfunctional acrylamide compound. Also preferably, the acrylamide compound (A) is a water-soluble acrylamide compound that dissolves in water 25°C, with a concentration of 1 mass% or more.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a composition containing an acrylamide compound, an ethylenically unsaturated compound having a carboxy group or an alkoxysilyl group, and a radical polymerization initiator.

Background Art

[0002] Acrylamide compounds are used as water-soluble polymerizable compounds. For example, in Citation 1, an ink composition having good stability over time, curing sensitivity, and landing position accuracy, which contains α-aminoacetophenone having a morpholine structure as a water-soluble initiator and a compound having an acrylamide structure as a water-soluble polymerizable compound, is described.

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0004] The main object of the present invention is to provide a composition having excellent adhesion to metals and metal oxides.

Means for Solving the Problems

[0005] As a result of intensive studies to solve the above problems, the present inventors have found that by using an ethylenically unsaturated compound having a carboxy group or an alkoxysilyl group, a composition having excellent adhesion to metals and metal oxides can be obtained, and thus the present invention has been completed.

[0006] The present invention is a composition containing an acrylamide compound (A), an ethylenically unsaturated compound (B) having a carboxy group or a group represented by the following general formula (I), and a radical polymerization initiator (C).

[0007] [Chemical formula] (In the formula, R 1 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, R 2 represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a heterocyclic group having 2 to 10 carbon atoms, or a group having 3 to 20 carbon atoms containing a heterocyclic ring, X 1 represents a single bond, -O-, -CO-, -COO-, -OCO-, -NR 3 -, -NR 3 CO-, -CONR 3 -, -S-, or -SO2-, X 2 represents a single bond, a hydrocarbon group having 1 to 20 carbon atoms, a heterocyclic group having 2 to 10 carbon atoms, or a group having 3 to 20 carbon atoms containing a heterocyclic ring, R 3 each independently represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a heterocyclic group having 2 to 10 carbon atoms, or a group having 3 to 20 carbon atoms containing a heterocyclic ring, a is a number from 1 to 3. When a is 2 or more, a plurality of R 1 may be the same or different, b is a number from 0 to 2. When b is 2, a plurality of R 2 may be the same or different, a + b = 3, * represents a bond.) [Advantages of the Invention]

[0008] According to the present invention, a composition having good adhesion to metals and metal oxides, particularly copper, can be provided. [Modes for Carrying Out the Invention]

[0009] A. Composition The composition of the present invention contains an acrylamide compound (A), an ethylenically unsaturated compound (B) having a carboxyl group or a group represented by the general formula (I) (hereinafter also referred to as an "alkoxysilyl group"), and a radical polymerization initiator (C).

[0010] 1. Acrylamide compound (A) The acrylamide compound (A) used in the composition of the present invention is a compound having at least one acrylamide group or methacrylamide group in its molecule, and lacking carboxyl groups and alkoxysilyl groups.

[0011] The acrylamide compound (A) may be a monofunctional acrylamide compound having one ethylenically unsaturated bond in its molecule, or a polyfunctional acrylamide compound having two or more ethylenically unsaturated bonds in its molecule. A monofunctional acrylamide compound is a compound having one acrylamide group or a methacrylamide group and no other ethylenically unsaturated bonds. A polyfunctional acrylamide compound is a compound having two or more ethylenically unsaturated bond-containing groups, at least one of which is an acrylamide group or a methacrylamide group.

[0012] Examples of monofunctional acrylamide compounds include acrylamides such as N-hydroxymethylacrylamide, N-(2-hydroxyethyl)acrylamide, N-methylacrylamide, N-ethylacrylamide, N-isopropylacrylamide, N-butylacrylamide, diacetoneacrylamide, N,N-dimethylacrylamide, N,N-diethylacrylamide, N,N-dipropylacrylamide, 4-acryloylmorpholine, Nn-butoxymethylacrylamide, N-isobutoxymethylacrylamide, and N-methoxymethylacrylamide; N Examples of methacrylamides include N-hydroxymethylmethacrylamide, N-(2-hydroxyethyl)methacrylamide, N-methylmethacrylamide, N-ethylmethacrylamide, N-isopropylmethacrylamide, N-butylmethacrylamide, diacetonemethacrylamide, N,N-dimethylmethacrylamide, N,N-diethylmethacrylamide, N,N-dipropylmethacrylamide, 4-methacrylroylmorpholine, Nn-butoxymethylmethacrylamide, N-isobutoxymethylmethacrylamide, and N-methoxymethylmethacrylamide.

[0013] Examples of polyfunctional acrylamide compounds include those represented by the following general formula (II), which are preferred because they exhibit particularly excellent adhesion to metal and metal oxide substrates, as well as excellent patternability.

[0014] [ka] (In the formula, L 11 and L 12 Each of these independently represents a hydrocarbon group having 1 to 20 carbon atoms which may have substituents, a heterocyclic group having 2 to 10 carbon atoms which may have substituents, a group in which one or more methylene groups in the hydrocarbon group are substituted with a group selected from the following <Group A>, a group in which one or more methylene groups in the heterocyclic group are substituted with a group selected from the following <Group A>, or a group having 3 to 20 carbon atoms which contains a heterocycle. Group A consists of -O-, -CO-, -COO-, -OCO-, and -NR 15-, -NR 15 CO-, -CONR 15 -, -S-, X 11 represents a single bond, -O- or -S-, R 11 , R 12 , R 13 and R 14 Each of these independently represents either a hydrogen atom or a methyl group. n1, n2, n3, and n4 each independently represent integers between 0 and 5 (inclusive). If n1 is 2 or greater, there are multiple R 11 They may be the same or different. If n2 is 2 or greater, there are multiple R 12 They may be the same or different. If n3 is 2 or greater, there are multiple R 13 They may be the same or different. If n4 is 2 or greater, there are multiple R 14 They may be the same or different. n1+n3≧1 n1 + n2 + n3 + n4 ≥ 2.

[0015] In this invention, a hydrocarbon group is a group consisting of carbon atoms and hydrogen atoms. Examples of hydrocarbon groups having 1 to 20 carbon atoms in the general formula (II) include aliphatic hydrocarbon groups having 1 to 20 carbon atoms and aromatic hydrocarbon ring-containing groups having 6 to 20 carbon atoms.

[0016] The aliphatic hydrocarbon group having 1 to 20 carbon atoms is a hydrocarbon group that does not contain an aromatic hydrocarbon ring or a heterocyclic ring, and may have substituents. A substituted aliphatic hydrocarbon group is a group in which a hydrogen atom in the aliphatic hydrocarbon group is replaced by a substituent.

[0017] Examples of unsubstituted aliphatic hydrocarbon groups having 1 to 20 carbon atoms include alkyl groups having 1 to 20 carbon atoms, alkenyl groups having 2 to 20 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, and cycloalkylalkyl groups having 4 to 20 carbon atoms. Furthermore, substituted aliphatic hydrocarbon groups having 1 to 20 carbon atoms are groups having 1 to 20 carbon atoms in which a hydrogen atom in an unsubstituted aliphatic hydrocarbon group is replaced by a substituent. Examples of such substituents include halogen atoms, cyano groups, nitro groups, hydroxyl groups, amino groups, methacryloyl groups, acryloyl groups, epoxy groups, vinyl groups, vinyl ether groups, mercapto groups, and isocyanate groups.

[0018] Examples of the halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0019] The alkyl group having 1 to 20 carbon atoms may be linear or branched. Examples of linear alkyl groups include methyl, ethyl, propyl, butyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, and octadecyl. Examples of branched alkyl groups include iso-propyl, sec-butyl, tert-butyl, iso-butyl, iso-pentyl, tert-pentyl, 2-hexyl, 3-hexyl, 2-heptyl, 3-heptyl, iso-heptyl, tert-heptyl, iso-octyl, tert-octyl, 2-ethylhexyl, and isononyl.

[0020] The aforementioned alkenyl group having 2 to 20 carbon atoms may be linear or branched. It may also be a terminal alkenyl group having an unsaturated bond at its end, or an internal alkenyl group having an unsaturated bond inside. Examples of terminal alkenyl groups include vinyl, allyl, 2-methyl-2-propenyl, 3-butenyl, 4-pentenyl, and 5-hexenyl. Examples of internal alkenyl groups include 2-butenyl, 3-pentenyl, 2-hexenyl, 3-hexenyl, 2-heptenyl, 3-heptenyl, 4-heptenyl, 3-octenyl, 3-nonenyl, 4-decenyl, 3-undecenyl, 4-dodecenyl, and 4,8,12-tetradecatrienylenylallyl.

[0021] Examples of cycloalkyl groups having 3 to 20 carbon atoms include saturated monocyclic alkyl groups having 3 to 20 carbon atoms, saturated polycyclic alkyl groups having 3 to 20 carbon atoms, and groups having 4 to 20 carbon atoms in which the hydrogen atoms in the ring of these groups are substituted with alkyl groups. Examples of saturated monocyclic alkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, and cyclodecyl. Examples of saturated polycyclic alkyl groups include adamantyl, decahydronaphthyl, octahydropentalene, and bicyclo[1.1.1]pentanyl. Examples of alkyl groups that substitute the hydrogen atoms in the ring of saturated monocyclic or saturated polycyclic alkyl groups include the groups exemplified as alkyl groups having 1 to 20 carbon atoms. Examples of groups in which the hydrogen atoms in the ring of saturated polycyclic alkyl groups are substituted with alkyl groups include bornyl.

[0022] The aforementioned cycloalkylalkyl group having 4 to 20 carbon atoms is a group having 4 to 20 carbon atoms in which the hydrogen atoms of the alkyl group are substituted with cycloalkyl groups. The cycloalkyl group in the cycloalkylalkyl group may be monocyclic or polycyclic. Examples of monocyclic cycloalkylalkyl groups include cyclopropylmethyl, 2-cyclobutylethyl, 3-cyclopentylpropyl, 4-cyclohexylbutyl, cycloheptylmethyl, cyclooctylmethyl, 2-cyclononylethyl, and 2-cyclodecylethyl. Examples of polycyclic cycloalkylalkyl groups include 3-adamantylpropyl and 3-decahydronaphthylpropyl.

[0023] The aforementioned aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms is a hydrocarbon group that contains an aromatic hydrocarbon ring but does not contain a heterocycle, and may have an aliphatic hydrocarbon group or substituents. A substituent-containing aromatic hydrocarbon ring-containing group is a group in which a hydrogen atom in the aromatic hydrocarbon ring-containing group is substituted with a substituent.

[0024] Examples of unsubstituted aromatic hydrocarbon ring-containing groups having 6 to 20 carbon atoms include aryl groups having 6 to 20 carbon atoms and arylalkyl groups having 7 to 20 carbon atoms. Furthermore, substituted aromatic hydrocarbon ring-containing groups having 6 to 20 carbon atoms are groups having 6 to 20 carbon atoms in which a hydrogen atom in an unsubstituted aromatic hydrocarbon ring-containing group is replaced by a substituent. Examples of such substituents include halogen atoms, cyano groups, nitro groups, hydroxyl groups, amino groups, methacryloyl groups, acryloyl groups, epoxy groups, vinyl groups, vinyl ether groups, mercapto groups, or isocyanate groups.

[0025] The aryl group having 6 to 20 carbon atoms may be a monocyclic structure, a fused ring structure, or a structure in which two aromatic hydrocarbon rings are linked.

[0026] Examples of monocyclic aryl groups include phenyl, tolyl, xylyl, ethylphenyl, and 2,4,6-trimethylphenyl. Examples of fused ring aryl groups include naphthyl, anthracenyl, phenanthryl, pyrenyl, fluorenyl, and indenofluorenyl.

[0027] An aryl group formed by linking two aromatic hydrocarbon rings may be formed by linking two monocyclic aromatic hydrocarbon rings, or by linking a monocyclic aromatic hydrocarbon ring with a fused ring aromatic hydrocarbon ring, or by linking two fused ring aromatic hydrocarbon rings. Examples of linking groups that connect two aromatic hydrocarbon rings include single bonds, sulfide groups (-S-), and carbonyl groups. Examples of aryl groups formed by linking two monocyclic aromatic hydrocarbon rings include biphenyl, diphenyl sulfide, and benzoylphenyl.

[0028] Arylalkyl groups with 7 to 20 carbon atoms are groups in which a hydrogen atom in the alkyl group is replaced by an aryl group. Examples of arylalkyl groups with 7 to 20 carbon atoms include benzyl, fluorenyl, indenyl, 9-fluorenylmethyl, α-methylbenzyl, α,α-dimethylbenzyl, phenylethyl, and naphthylpropyl groups.

[0029] A divalent hydrocarbon group having 1 to 20 carbon atoms is a group obtained by removing one hydrogen atom from the aforementioned hydrocarbon group having 1 to 20 carbon atoms. Examples of divalent aliphatic hydrocarbon groups having 1 to 20 carbon atoms include alkylene groups having 1 to 20 carbon atoms, alkenylene groups having 2 to 20 carbon atoms, cycloalkylene groups having 3 to 20 carbon atoms, and cycloalkylalkylene groups having 4 to 20 carbon atoms. Examples of divalent aromatic hydrocarbon ring-containing groups having 6 to 20 carbon atoms include arylene groups having 6 to 20 carbon atoms and arylalkylene groups having 7 to 20 carbon atoms.

[0030] In the present invention, a heterocyclic group is a group obtained by removing one hydrogen atom from a heterocyclic compound. Examples of heterocyclic groups having 2 to 10 carbon atoms include pyridyl, quinolyl, thiazolyl, tetrahydrofuranil, dioxolanil, tetrahydropyranil, methylthiophenyl, hexylthiophenyl, benzothiophenyl, pyrrolyl, pyrrolidinyl, imidazolyl, imidazolidinyl, imidazolinyl, pyrazolyl, pyrazolidinyl, piperidinyl, piperazinyl, pyrimidinyl, furyl, thienyl, benzoxazol-2-yl, thiazolyl, isothiazoli, oxazolyl, isoxazolyl, and morphoryl.

[0031] The heterocyclic group may have substituents, and examples of such substituents include halogen atoms, cyano groups, nitro groups, hydroxyl groups, amino groups, methacryloyl groups, acryloyl groups, epoxy groups, vinyl groups, vinyl ether groups, mercapto groups, and isocyanate groups.

[0032] In the present invention, a group containing a heterocyclic ring (hereinafter sometimes referred to as a "heterocyclic ring-containing group") is a group having a structure in which a hydrogen atom in a hydrocarbon group is substituted with a heterocyclic ring. Examples of heterocyclic rings in heterocyclic ring-containing groups having 3 to 20 carbon atoms include the groups exemplified as heterocyclic rings having 2 to 10 carbon atoms. Examples of hydrocarbon groups include the hydrocarbon groups having 1 to 20 carbon atoms. The heterocyclic group may have an aromatic hydrocarbon ring, an aliphatic hydrocarbon group, or a substituent. Examples of substituents include halogen atoms, cyano groups, nitro groups, hydroxyl groups, amino groups, methacryloyl groups, acryloyl groups, epoxy groups, vinyl groups, vinyl ether groups, mercapto groups, and isocyanate groups. Furthermore, the "3 to 20 carbon atoms" in the heterocyclic group containing 3 to 20 carbon atoms refers to the total number of carbon atoms in the heterocyclic group.

[0033] In the present invention, a group in which a methylene group is substituted with a specific divalent group means, for example, a group that contains a -CH2O- structure when the divalent group is -O-.

[0034] Groups in which two or more methylene groups in hydrocarbon groups having 1 to 20 carbon atoms and heterocyclic groups having 3 to 20 carbon atoms are substituted with divalent groups selected from the above-mentioned Group A do not have adjacent structures of these divalent groups.

[0035] In this invention, the number of carbon atoms in a group refers to the number of carbon atoms in the group after a substituent has replaced a hydrogen atom in the group. For example, when a hydrogen atom is substituted in an alkyl group having 1 to 20 carbon atoms, the number of carbon atoms, 1 to 20, refers to the number of carbon atoms after the hydrogen atom has been replaced, and not to the number of carbon atoms before the hydrogen atom was replaced. Furthermore, in this invention, the number of carbon atoms in a group in which a methylene group is replaced with a divalent group defines the number of carbon atoms in the substituted group. For example, in the case of a group with 1 to 20 carbon atoms in which a methylene group in an alkyl group is replaced with a divalent group, the number of carbon atoms (1 to 20) refers to the number of carbon atoms in the group after the methylene group in the alkyl group has been replaced with a divalent group, and not to the number of carbon atoms in the group before the substitution.

[0036] X in the above general formula (II) 11 It is preferably -O- or -S-, and particularly preferably -O-. 11 This is because, when the above-mentioned group is present, the resulting composition will have excellent adhesion to metal and metal oxide substrates, as well as excellent patternability.

[0037] In the above general formula (II), R 11 , R 12 , R 13 and R 14 It is preferable that the atom is a hydrogen atom, as this results in a composition that has excellent solubility in water and patternability, and improves the adhesion of the resulting cured product to copper.

[0038] L in the above general formula (II) 11 and L 12Since the resulting composition has excellent adhesion to copper and patternability, it is preferable that each is independently an alkylene group or arylene group having 1 to 15 carbon atoms, or a group having 1 to 15 carbon atoms in which the methylene group in the alkylene group is substituted with -O- or -S-, and it is more preferable that it is an alkylene group or arylene group having 1 to 10 carbon atoms, or a group having 1 to 10 carbon atoms in which the methylene group in the alkylene group is substituted with -O-.

[0039] In the above general formula (II), it is preferable that n2 + n4 ≥ 1, and more preferable that n2 + n4 = 1, so that the resulting composition has excellent adhesion to copper and patternability. Furthermore, it is preferable that n1 + n3 = 1, as this results in a composition with excellent adhesion to copper and patternability.

[0040] In the present invention, the resulting composition has particularly excellent adhesion to copper and patternability, therefore, R in the general formula (II) 11 , R 12 , R 13 and R 14 It is preferable that R is a hydrogen atom, n1+n3≧1, and n2+n4≧1. In particular, R 11 , R 12 , R 13 and R 14 It is preferable that the atom is a hydrogen atom, n1+n3=, and n2+n4=1, that is, that it has one acrylamide group and one acryloyl group.

[0041] Specific examples of compounds represented by the general formula (II) include the following compounds (1-1) to (1-22).

[0042] [ka]

[0043] [ka]

[0044] Other polyfunctional acrylamide compounds include the following compounds (1-23) to (1-33).

[0045] [ka]

[0046] In the present invention, it is preferable that the acrylamide compound (A) contains both a monofunctional acrylamide compound and a polyfunctional acrylamide compound, since a composition with excellent adhesion to metals and metal oxides can be obtained. In this case, it is preferable that the content of the monofunctional acrylamide compound in the acrylamide compound (A) is 50% by mass or more and 95% by mass or less, and more preferably 60% by mass or more and 90% by mass or less, since a composition with even better adhesion to metals and metal oxides can be obtained.

[0047] The acrylamide compound (A) is preferably a water-soluble acrylamide compound that dissolves in water at 25°C in an amount of 1% by mass or more, since this yields a composition with high solubility in water and excellent water-developability.

[0048] The content of the acrylamide compound (A) in the composition of the present invention is preferably 60% to 98% by mass, more preferably 70% to 95% by mass, and preferably 75% to 93% by mass, in the solid content of the composition, in order to obtain a composition with excellent adhesion to metals and metal oxides. The solid content refers to the components of the composition excluding the solvent described later.

[0049] 2. Ethylene-unsaturated compounds having a carboxyl group or an alkoxysilyl group (B) The ethylenically unsaturated compound (B) used in the composition of the present invention is a compound having a group having an ethylenically unsaturated bond in its molecule and a carboxyl group or an alkoxysilyl group. Since ethylenically unsaturated compounds (B) having both a carboxyl group and an alkoxysilyl group have poor storage stability, ethylenically unsaturated compounds (B) having either a carboxyl group or an alkoxysilyl group are preferred.

[0050] In the present invention, since a composition with excellent adhesion to metals and metal oxides can be obtained, it is preferable that the group having an ethylenically unsaturated bond is an acryloyl group, a methacryloyl group, an acrylamide group, or a methacrylamide group.

[0051] (1) Ethylene unsaturated compounds having a carboxyl group (B) A carboxyl-containing ethylenically unsaturated compound (B) is a compound having a group with an ethylenically unsaturated bond and a carboxyl group. Ethylene-unsaturated compounds (B) having a carboxyl group are preferred because they exhibit particularly excellent adhesion to metals and metal oxides, as well as excellent patternability.

[0052] Specific examples of ethylenically unsaturated compounds (B) having a carboxyl group include the following compounds (2-1) to (2-10).

[0053] [ka]

[0054] (2) Ethylene unsaturated compounds having an alkoxysilyl group (B) Ethylene-unsaturated compounds (B) having an alkoxysilyl group are compounds having a group with an ethylenically unsaturated bond and an alkoxysilyl group represented by the following general formula (I) within the molecule.

[0055] [ka] (In the formula, R 1 This represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms. R2 This represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a heterocyclic group having 2 to 10 carbon atoms, or a group having 3 to 20 carbon atoms that contains a heterocyclic ring. X 1 These are single bonds, -O-, -CO-, -COO-, -OCO-, -NR 3 -, -NR 3 CO-, -CONR 3 -, -S- or -SO2- X 2 This represents single bonds, hydrocarbon groups with 1 to 20 carbon atoms, heterocyclic groups with 2 to 10 carbon atoms, and groups containing heterocyclic elements with 3 to 20 carbon atoms. R 3 Each of these independently represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a heterocyclic group having 2 to 10 carbon atoms, or a group having 3 to 20 carbon atoms containing a heterocyclic ring. a is a number between 1 and 3, and if a is 2 or greater, there are multiple R's. 1 They may be the same or different. b is a number between 0 and 2, and if b is 2, there are multiple R values. 2 They may be the same or different. a+b=3, * indicates a bonding operation.

[0056] Examples of hydrocarbon groups having 1 to 20 carbon atoms, heterocyclic groups having 2 to 10 carbon atoms, and groups having 3 to 20 carbon atoms containing a heterocycle in general formula (I) include the same groups as those exemplified as hydrocarbon groups having 1 to 20 carbon atoms, heterocyclic groups having 2 to 10 carbon atoms, and groups having 3 to 20 carbon atoms containing a heterocycle in general formula (II). Furthermore, examples of alkyl groups having 1 to 8 carbon atoms in general formula (I) include alkyl groups having 1 to 8 carbon atoms from among those exemplified as hydrocarbon groups having 1 to 20 carbon atoms in general formula (II).

[0057] In the present invention, since the resulting composition exhibits excellent adhesion to metals and metal oxides, it is preferable that the ethylenically unsaturated compound (B) having an alkoxysilyl group has one ethylenically unsaturated bond in its molecule, and more preferably has one acryloyl group or methacryloyl group in its molecule.

[0058] In the general formula (I), a is preferably 2 or 3, and more preferably 3, because the resulting composition has excellent adhesion to metals and metal oxides. Also, in the general formula (I), b is preferably 0 or 1, and more preferably 0, because the resulting composition has excellent adhesion to metals and metal oxides.

[0059] X in the above general formula (I) 1 Because the resulting composition exhibits excellent adhesion to metals and metal oxides, -O- or -NR 3 - is preferable, and -O- is more preferable.

[0060] X in the above general formula (I) 2 The obtained composition exhibits excellent adhesion to metals and metal oxides, so it is preferably a hydrocarbon group having 1 to 20 carbon atoms, more preferably an alkylene group having 1 to 20 carbon atoms, even more preferably an alkylene group having 1 to 10 carbon atoms, particularly preferably an alkylene group having 1 to 5 carbon atoms, and most preferably a linear alkylene group having 1 to 5 carbon atoms.

[0061] Examples of ethylenically unsaturated compounds (B) having an alkoxysilyl group include vinyltrimethoxysilane, vinyltriethoxysilane, vinylmethyldimethoxysilane, vinylmethyldiethoxysilane, allyltrimethoxysilane, allyltriethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropyltriethoxysilane, 3-acryloxypropyltrimethoxysilane, 3-acryloxypropyltriethoxysilane, p-styryltrimethoxysilane, and p-styryltriethoxysilane.

[0062] As the ethylenically unsaturated compound (B) having an alkoxysilyl group, commercially available products can be used, for example, KBM-502, KBM-503, KBE-502, KBE-503, KBM-1003, KBE-1003, KBM-1403, KBM-5103 and KBM-503 (all manufactured by Shin-Etsu Silicone), Z-2349, Z-6518, Z-6300 and Z-6172 (Dow Corning).

[0063] (3) Ethylene unsaturated compounds having a carboxyl group or an alkoxy group (B) The ethylenically unsaturated compound (B) is preferably an ethylenically unsaturated compound that dissolves in water at 25°C at a concentration of 1% by mass or more (hereinafter also referred to as a water-soluble ethylenically unsaturated compound), as this yields a composition with high solubility in water and excellent water-developability.

[0064] The content of the ethylenically unsaturated compound (B) in the composition of the present invention is preferably 1 to 50 parts by mass, more preferably 5 to 30 parts by mass, and particularly preferably 10 to 20 parts by mass, per 100 parts by mass of the acrylamide compound (A), in order to obtain a composition with excellent adhesion to metals and metal oxides. Furthermore, the content of the ethylenically unsaturated compound (B) is preferably 1% by mass or more and 40% by mass or less, more preferably 3% by mass or more and 30% by mass or less, and preferably 5% by mass or more and 20% by mass or less, in order to obtain a composition with excellent adhesion to metals and metal oxides.

[0065] 3. Radical polymerization initiator (C) The radical polymerization initiator used in the composition of the present invention may be any initiator used for polymerization of compounds having an ethylenically unsaturated bond. Examples include photoradical polymerization initiators that generate radicals upon light irradiation and thermal radical polymerization initiators that generate radicals upon heating. Photoradical polymerization initiators are preferred because they allow for fine patterning.

[0066] Examples of preferred photoradical polymerization initiators include ketone compounds such as acetophenone compounds, benzyl compounds, benzophenone compounds, and thioxanthone compounds, as well as oxime ester compounds.

[0067] Acetophenone compounds include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 4'-isopropyl-2-hydroxy-2-methylpropiophenone, 2-hydroxymethyl-2-methylpropiophenone, 2,2-dimethoxy-1,2-diphenylethane-1-one, p-dimethylaminoacetophenone, p-tert-butyldichloroacetophenone, p-tert-butyltrichloroacetophenone, p-azidobenzalacetophenone, and 1-hydroxy Examples include cyclohexylphenyl ketone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropanone-1, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin n-butyl ether, benzoin isobutyl ether, and 1-[4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propan-1-one.

[0068] Examples of benzyl compounds include benzyl.

[0069] Examples of benzophenone compounds include benzophenone, o-methyl benzoylbenzoate, Michler ketone, 4,4'-bisdiethylaminobenzophenone, 4,4'-dichlorobenzophenone, and 4-benzoyl-4'-methyldiphenyl sulfide.

[0070] Examples of thioxanthone compounds include thioxanthone, 2-methylthioxanthone, 2-ethylthioxanthone, 2-chlorothioxanthone, 2-isopropylthioxanthone, and 2,4-diethylthioxanthone.

[0071] Oxime ester compounds are a general term for compounds containing an oxime ester group, such as 1-phenyl[(propionyloxy)imino]propan-1-one. These oxime ester compounds are superior among polymerization initiators in that they have good sensitivity.

[0072] Examples of commercially available radical polymerization initiators include ADEKA optomer N-1414, N-1717, N-1919, ADEKA Arcules NCI-831, NCI-930 (manufactured by ADEKA); IRGACURE 184, IRGACURE 369, IRGACURE 651, IRGACURE 907, IRGACURE OXE 01, IRGACURE OXE 02, IRGACURE 784 (manufactured by BASF); TR-PBG-304, TR-PBG-305, TR-PBG-309, TR-PBG-314 (manufactured by Tronly); and others.

[0073] In the present invention, since a composition with high solubility in water and excellent water-developability can be obtained, it is preferable that the radical polymerization agent (C) is water-soluble, that is, it is preferable that it is a water-soluble radical polymerization initiator. The water-soluble radical polymerization initiator is preferably soluble in water at 25°C at a concentration of 1% by mass or more.

[0074] Specific examples of water-soluble radical polymerization initiators include the following compounds (4-1) to (4-57).

[0075] [ka]

[0076] [ka]

[0077] [ka]

[0078] The amount of the radical polymerization initiator (C) in the composition of the present invention is preferably 1 to 10 parts by mass, more preferably 2 to 15 parts by mass, and particularly preferably 3 to 10 parts by mass, per 100 parts by mass of the total of the acrylamide compound (A) and the ethylenically unsaturated compound (B), in order to obtain a composition with excellent adhesion to metals and metal oxides.

[0079] 4. Solvent (D) The composition of the present invention may contain a solvent. The solvent only needs to be able to disperse or dissolve the acrylamide compound (A), the ethylenically unsaturated compound (B), and the radical polymerization initiator (C), and is not particularly limited in type. The solvent may be an aqueous solvent containing water (pure water or deionized water) in any proportion, or an organic solvent.

[0080] Aqueous solvents are a general term for solvents containing water and organic solvents that are miscible with water. In other words, an aqueous solvent may be water alone, a water-miscible organic solvent alone, or a mixture of both. A water-miscible organic solvent means an organic solvent that dissolves at least 10 g in 100 g of water at 20°C.

[0081] Compositions using aqueous solvents offer the following advantages: Firstly, the thickness of the coating can be easily controlled. Secondly, they can be used not only on substrates with high resistance to organic solvents but also on substrates with low resistance to organic solvents, thus increasing the freedom in selecting substrate types. Thirdly, when applied to organic materials (e.g., films containing organic compounds), the organic materials are less likely to be damaged. Fourthly, aqueous solvents are environmentally friendly, thus reducing the environmental impact during use.

[0082] Organic solvents miscible with water include methanol, ethanol, 1-propanol, 2-propanol, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, 2-pyrrolidone, N-methyl-2-pyrrolidone, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, 2,2-dimethyl-1,3-propanediol, 2-methyl-1,3-propanediol, and 1,2-pentanediol. 1,5-pentanediol, 2,4-pentanediol, 1,2-hexanediol, 3,5-dimethyl-3-hexyne-2,5-diol, 2,5-hexanediol, hexylene glycol, 1,6-hexanediol, 2-ethyl-1,3-hexanediol, 2,2,4-trimethyl-1,3-pentanediol, 2,5-dimethyl-2,5-hexanediol, sulfolane, 1,4-cyclohexanedimethanol, 2,2-thiodiethanol, 3-pyridylcarbinol, propylene glycol monomethyl ether, dipropylene glycol Examples include methyl ether, tripropylene glycol methyl ether, propylene glycol ethyl ether, propylene glycol n-propyl ether, dipropylene glycol n-propyl ether, tripropylene glycol n-propyl ether, propylene glycol n-butyl ether, dipropylene glycol n-butyl ether, tripropylene glycol n-butyl ether, propylene glycol t-butyl ether, dipropylene glycol t-butyl ether, propylene glycol phenyl ether, ethylene glycol methyl ether, diethylene glycol methyl ether, triethylene glycol methyl ether, ethylene glycol ethyl ether, diethylene glycol ethyl ether, triethylene glycol ethyl ether, ethylene glycol n-propyl ether, ethylene glycol n-butyl ether, diethylene glycol n-butyl ether, triethylene glycol n-butyl ether, ethylene glycol n-hexyl ether, diethylene glycol n-hexyl ether, and ethylene glycol phenyl ether.

[0083] Among these, lower alcohols with 5 or fewer carbon atoms are preferred as organic solvents that can be mixed with water, because their solubility in water is significantly improved.

[0084] Examples of organic solvents include ketones, ether solvents, ester solvents, cellosolve solvents, alcohol solvents (excluding alcohol solvents that fall under the category of aqueous solvents), ether ester solvents, BTX solvents, aliphatic hydrocarbon solvents, terpene hydrocarbon oils, halogenated aliphatic hydrocarbon solvents, and halogenated aromatic hydrocarbon solvents.

[0085] Ketones include, for example, methyl ethyl ketone, acetone, and cyclohexanone. Ether solvents include, for example, dioxane, tetrahydrofuran, and 1,2-dimethoxyethane. Ester solvents include methyl acetate, ethyl acetate, and propyl acetate. Cellosolve solvents include, for example, ethylene glycol monomethyl ether and ethylene glycol monoethyl ether. Alcohol solvents include, for example, 1-butanol and 1-hexanol. Ether ester solvents include, for example, ethylene glycol monomethyl acetate and ethylene glycol monoethyl acetate. BTX solvents include, for example, benzene, toluene, and xylene. Aliphatic hydrocarbon solvents include, for example, hexane, heptane, octane, and cyclohexane. Terpene hydrocarbon oils include, for example, turpentine oil, D-limonene, and pinene. Examples of halogenated aliphatic hydrocarbon solvents include carbon tetrachloride, chloroform, trichloroethylene, methylene chloride, and 1,2-dichloroethane. Examples of halogenated aromatic hydrocarbon solvents include chlorobenzene. Other organic solvents may include, for example, aniline, triethylamine, pyridine, acetic acid, acetonitrile, carbon disulfide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and dimethyl sulfoxide.

[0086] In the present invention, in order to further reduce the environmental burden, the water content in the solvent is preferably 90% by mass or more, 95% by mass or more, or 99% by mass or more, and it is particularly preferable that the solvent is water (pure water or ion-exchanged water) only.

[0087] The solvent content in the composition of the present invention may be adjusted as appropriate from the viewpoint of coating properties and film-forming properties, but the solid content of the composition is preferably 30 to 70% by mass, more preferably 30 to 70% by mass, and particularly preferably 30 to 70% by mass. When the solvent content is within the above range, coating properties and film-forming properties are good.

[0088] 5. Other ingredients The composition of the present invention may contain various additives such as leveling agents and coupling agents (excluding those corresponding to the ethylene unsaturated compound (B) having an alkoxysilyl group).

[0089] The leveling agent is not particularly limited as long as it is a material capable of exhibiting a leveling effect; therefore, known leveling agents can be used. Examples of leveling agents include silicone-based leveling agents and fluorine-based leveling agents.

[0090] Commercially available silicone leveling agents can be used as silicone leveling agents. Specifically, commercially available silicone leveling agents include, for example, the following: BYK-300, BYK-306, BYK-310, BYK-315, BYK-313, BYK-320, BYK-322, BYK-323, BYK-325, BYK-330, BYK-344, BYK-370, BYK-UV3510, BYK-UV3570, BYK-3550, and BYK-SILCLEAN3700 from BIC Chemie Japan Co., Ltd. ACFS180, ACFS360, and AC S20 from Algin Chemie, Inc. Polyflow KL-400X and Polyflow KL-400HF from Kyoeisha Chemical Co., Ltd. These include KP-323, KP-326, KP-341, KP-104, KP-110, and KP-112 manufactured by Shin-Etsu Chemical Co., Ltd., and LP-7001, LP-7002, 8032 ADDITIVE, 57 ADDITIVE, L-7604, FZ-2110, FZ-2105, 67 ADDITIVE, 8618 ADDITIVE, 3 ADDITIVE, and 56 ADDITIVE manufactured by Toray Dow Corning Co., Ltd.

[0091] Examples of commercially available water-based silicone leveling agents include: Disparon LS-009, Disparon LS-430, and Disparon AQ-7120 from Kusumoto Kasei Co., Ltd.; and BYK-301, BYK-302, BYK-307, BYK-331, BYK-333, BYK-337, BYK-341, BYK-345, BYK-346, BYK-347, BYK-348, BYK-349, BYK-375, BYK-377, BYK-378, BYK-UV 3500, and BYK-SILCLEAN 3720 from BYK Chemie Japan Co., Ltd. These include Polyflow WS, Polyflow WS-314, Polyflow KL-100, Polyflow KL-401, Polyflow KL-402, Polyflow KL-403, and Polyflow KL-404 from Kyoeisha Chemical Co., Ltd., and TEGO Flow 425, TEGO Glide100, TEGO Glide110, TEGO Glide410, TEGO Glide440, TEGO Glide450, TEGO Glide482, and TEGO Glide485 from EVONIC.

[0092] Among silicone-based leveling agents, water-based silicone-based leveling agents are preferred because they have excellent compatibility with aqueous solvents.

[0093] Commercially available fluorine-based leveling agents can be used as fluorine-based leveling agents. Specifically, commercially available fluorine-based leveling agents include, for example, the following: Optool DSX and Optool DAC-HP from Daikin Industries, Ltd. Surflon S-420, Surflon S-611 and Surflon S-651 from AGC Seimi Chemical Co., Ltd. BYK-340 from Bic Chemie Japan Co., Ltd. AC110a and AC100a from Algin Chemie. These include the MegaFac EXPTP-2066, MegaFac F-430, MegaFac F-472SF, MegaFac F-477, MegaFac F-552, MegaFac F-554, MegaFac F-555, MegaFac RS-72-K, MegaFac RS-75, MegaFac F-556, MegaFac EXPTF-1367, MegaFac EXPTF-1437, MegaFac F-558, and MegaFac EXPTF-1537, all manufactured by DIC Corporation. FC-4430 and FC-4432, all manufactured by 3M Japan Limited (formerly Sumitomo 3M Limited), and F-Fertgent AK, F-Fertgent 501, F-Fertgent 251, F-Fertgent 222F, F-Fertgent 208G, F-Fertgent 300, and F-Fertgent 310, all manufactured by Neos Corporation. These include PF-136A, PF-156A, PF-151N, PF-636, PF-6320, PF-656, PF-6520, PF-651, PF-652, and PF-3320, all manufactured by Kitamura Chemical Industry Co., Ltd.

[0094] Examples of commercially available water-based fluorine-based leveling agents include: Megafac F-114, Megafac 410, Megafac 444, Megafac 477, Megafac 553, Megafac 556, Megafac 559, Megafac 569, Megafac 574, and Megafac R-94 from DIC Corporation; and Surflon S-211, Surflon S-212, Surflon S-221, Surflon S-231, Surflon S-241, Surflon S-242, Surflon S-243, and Surflon S-386 from AGC Seimi Chemical Co., Ltd. These include the Futtergent 100, Futtergent 100C, Futtergent 110, Futtergent 150, Futtergent 150CH, Futtergent 320, Futtergent 400SW, Futtergent 212M, Futtergent 215M, Futtergent 250, Futtergent 730FL, Futtergent 683, Futtergent 602A, and Futtergent 681, all manufactured by Neos Co., Ltd.

[0095] Among fluorine-based leveling agents, water-based fluorine-based leveling agents are preferred because they have excellent compatibility with aqueous solvents.

[0096] Other coupling agents besides the ethylene unsaturated compound (B) having an alkoxysilyl group include alkyl-functional alkoxysilanes such as dimethyldimethoxysilane, dimethyldiethoxysilane, methylethyldimethoxysilane, methylethyldiethoxysilane, methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, and ethyltrimethoxysilane; epoxy-functional alkoxysilanes such as γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropylmethyldiethoxysilane, and β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane; amino-functional alkoxysilanes such as N-β(aminoethyl)-γ-aminopropyltrimethoxysilane, γ-aminopropyltriethoxysilane, and N-phenyl-γ-aminopropyltrimethoxysilane; and mercapto-functional alkoxysilanes such as γ-mercaptopropyltrimethoxysilane.

[0097] Furthermore, additives such as crosslinking agents, sensitizers, surfactants, colorants, inorganic fillers, organic fillers, and water-soluble preservatives may be added as needed, provided that they do not impair the effects of the present invention.

[0098] The composition of the present invention can be easily prepared by mixing the components described above. There are no particular restrictions on the order of mixing or the mixing method. For example, it can be prepared by adding the acrylamide compound (A), the ethylenically unsaturated compound (B), the radical polymerization initiator (C), and various additives to a solvent such as water, and then stirring and mixing.

[0099] The compositions of the present invention include curable paints, varnishes, curable adhesives, printed circuit boards, color filters for display devices (specifically, color liquid crystal display panels for color televisions, PC monitors, mobile information terminals, and digital cameras), color filters for CCD image sensors, touch panels, black partitions for electroluminescent display devices, plasma display panels, and organic EL display devices, powder coatings, printing inks, printing plates, adhesives, gel coats, photoresists for electronics, electroplating resists, etching resists, solder resists, insulating films, black matrices, resists for forming structures in the manufacturing process of LCDs, compositions for encapsulating electrical and electronic components, solder resists, magnetic recording materials, micro-mechanical parts, waveguides, optical switches, plating masks, etching masks, and glass. It can be used in a variety of applications, such as fiber cable coatings, stencils for screen printing, materials for manufacturing three-dimensional objects by stereolithography, holographic recording materials, image recording materials, microelectronic circuits, decolorizing agents, decolorizing agents for image recording materials, decolorizing agents for image recording materials using microcapsules, photoresist materials for printed circuit boards, photoresist materials for UV and visible laser direct imaging systems, and photoresist materials and protective films used for dielectric layer formation in sequential lamination of printed circuit boards. There are no particular limitations on its applications, but because it has good adhesion to metals and metal oxides, especially copper, and is a patternable composition, it can be suitably used as a patterning material for metal substrates such as etching resists and for metal oxide substrates.

[0100] The compositions of the present invention can be suitably used in a variety of applications, particularly as black partitions for printed circuit boards, touch panels, electroluminescent display devices, plasma display panels, and organic EL display devices; photoresists for electronics, electroplating resists, etching resists, solder resists, insulating films, black matrices; and resists for forming structures in the manufacturing process of LCDs, solder resists, photoresist materials for printed circuit boards, photoresist materials for UV and visible laser direct imaging systems, and photoresist materials and protective films used for forming dielectric layers in sequential lamination of printed circuit boards.

[0101] In particular, it can be used in a variety of applications such as printed circuit boards, photoresists for electronics, electroplating resists, etching resists, solder resists, resists for forming structures in the manufacturing process of LCDs, solder resists, photoresist materials for printed wiring boards, photoresist materials for UV and visible laser direct imaging systems, and photoresist materials used for dielectric layer formation in sequential lamination of printed circuit boards. Because it has good adhesion to metals and metal oxides, especially copper, and is a patternable composition, it can be suitably used as a patterning material for metal substrates such as etching resists and a patterning material for metal oxide substrates.

[0102] Metal substrate patterning materials are water-soluble patterning materials that exhibit good adhesion to metal substrates (substrates) or to substrates such as plastics and ceramics that contain metal parts. Examples of metals include gold, silver, copper, aluminum, iron, platinum, nickel, titanium, solder, chromium, lead, and tin, as well as their alloys. Gold, silver, copper, and aluminum and their alloys are preferred due to their excellent conductivity, and copper and copper alloys are particularly preferred due to their easy availability. Furthermore, water-soluble or water-dispersible patterning materials for metal substrates that do not use organic solvents are preferred because they have a low environmental impact.

[0103] Patterning materials for metal oxide substrates are water-soluble patterning materials that exhibit good adhesion to metal oxide substrates (substrates) or to substrates such as plastics and ceramics containing metal oxide components. Examples of metal oxides include aluminum-doped tin oxide, indium-doped tin oxide, antimond-doped tin oxide (ATO), gallium-doped zinc oxide (GZO), indium-doped zinc oxide (IZO), aluminum-doped zinc oxide particles (AZO), niobium-doped titanium oxide, sodium-doped tungsten oxide, cesium-doped tungsten oxide, thallium-doped tungsten oxide, rubidium-doped tungsten oxide, tin-doped indium oxide (ITO), tin-doped zinc oxide, and silicon-doped zinc oxide. Furthermore, because they have a low environmental impact, water-soluble or water-dispersible patterning materials for metal oxide substrates that do not use organic solvents are preferred.

[0104] B. Cured product The cured product of the present invention is a cured product of the above-described composition. By using the above-described composition, the cured product of the present invention exhibits excellent adhesion to metals and metal oxides.

[0105] C. Method for manufacturing cured products The manufacturing method of the present invention includes a step of curing the above-mentioned composition. Methods for curing the composition include commonly used methods such as irradiating the composition with active energy rays and heating the composition.

[0106] 1. Curing process In the present invention, the composition can be cured by generating radicals from a polymerization initiator. When the polymerization initiator (C) is a photoradical polymerization initiator, the method is preferably a method of irradiating the composition with active energy rays, and when the polymerization initiator is a thermal radical polymerization initiator, the method is preferably a method of heating the composition.

[0107] A method for irradiating the aforementioned composition with active energy rays will be described in detail. When the polymerizable composition contains a photoradical polymerization initiator as a polymerization initiator (C), the polymerization of the acrylamide compound (A) and the ethylenically unsaturated compound (B) can be initiated and cured by irradiation with active energy rays. Examples of light sources used for curing include electromagnetic wave energy with wavelengths from 200 nm to 700 nm obtained from 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, CRT light sources, etc., as well as high-energy rays such as electron beams, X-rays, and radiation. However, ultra-high pressure mercury lamps, mercury vapor arc lamps, carbon arc lamps, xenon arc lamps, etc., which emit light with wavelengths of 300 to 450 nm, are preferred.

[0108] A method for heating the aforementioned composition will be described in detail. If the composition contains a thermal radical polymerization initiator as the polymerization initiator (C), the polymerization of the acrylamide compound (A) and the ethylenically unsaturated compound (B) can be initiated by heating, allowing for curing. Depending on the type of polymerization initiator, the composition can be cured by initiating polymerization at a temperature of approximately 80 to 120°C, for example.

[0109] In the present invention, it is preferable that the curing method is a method of irradiating the composition with active energy rays, that is, that the curing step includes a step of irradiating the composition with active energy rays. This is because the process time can be shortened and patterning using active energy rays becomes possible.

[0110] 2. Other processes Pattern formation using the above composition can be carried out, for example, by (1) forming a coating film of the above composition on a substrate, (2) irradiating the coating film with active energy rays through a mask having a predetermined pattern shape, and (3) developing the exposed film with a developer (especially water). (2) In the step of irradiating the coating film with active energy rays through a mask having a predetermined pattern shape, the method of irradiating with active energy rays may be to irradiate the entire surface of the coating film of the composition, but it is preferable to irradiate with active energy rays through a mask having a predetermined pattern shape. This is because it facilitates the formation of the pattern.

[0111] The aforementioned composition can form a coating on substrates such as soda glass, quartz glass, semiconductor substrates, metals, metal oxides, paper, and plastics by known means such as spin coaters, roll coaters, bar coaters, die coaters, curtain coaters, various printing methods, and immersion. Furthermore, after forming a coating on a substrate such as a film, it can be transferred to another substrate, and there are no limitations on the method. [Examples]

[0112] The present invention will be described in more detail below with reference to examples and comparative examples, but the present invention is not limited to these examples.

[0113] [Examples 1-11 and Comparative Examples 1-8] The components were mixed according to the formulations shown in Table 1 to obtain the compositions for the examples and comparative examples. The obtained compositions were then evaluated for solubility, copper foil adhesion, and patterning properties. The results are shown in Table 1. The values ​​in the table represent the mass portion, and the symbols in the table represent the components listed below. A-1: Compound (1-13) (Polyfunctional water-soluble acrylamide compound represented by general formula (II)) A-2: Compound (1-23) (Polyfunctional water-soluble acrylamide compound) A-3: Compound (1-1) (Polyfunctional water-soluble acrylamide compound represented by general formula (II)) A-4: 4-Acryloylmorpholine (monofunctional water-soluble acrylamide compound) A-5: N-(2-hydroxyethyl)acrylamide (monofunctional water-soluble acrylamide compound) B-1: Compound (2-1) (Water-soluble ethylenically unsaturated compound having a carboxyl group) B-2: Compound (2-3) (Water-soluble ethylenically unsaturated compound having a carboxyl group) B-3: 3-Acryloxypropyltrimethoxysilane (a water-soluble ethylenically unsaturated compound having an alkoxysilyl group) B-4: 3-Methacryloxypropyltrimethoxysilane (a water-soluble ethylenically unsaturated compound having an alkoxysilyl group) C-1: Compound (4-3) (Water-soluble radical polymerization initiator) C-2: Compound (4-57) (Water-soluble radical polymerization initiator) D-1: Solvent (Ion-exchanged water) E-1: Leveling agent (TEGO Glide 440, manufactured by Evonik)

[0114] <Evaluation Method> (Solubility) Each composition was placed in a screw-cap tube at room temperature and stirred with a magnetic stirrer for 30 minutes. Solubility was then visually checked, and those that were clear were designated A, those that were slightly cloudy were designated B, and those that were cloudy or separated were designated C. Compositions rated A or B were preferred because they had excellent storage stability and water-developability.

[0115] (Copper foil adhesion) Each composition was applied to the surface of a copper substrate (ESPANEX, manufactured by Nippon Steel & Sumitomo Metal Chemical Co., Ltd.) using a bar coater, and then a coating film was formed by heat drying (heating temperature: 80°C, heating time: 2 minutes). Subsequently, this coating film was treated with active energy rays (ultraviolet rays, wavelength: 320nm~390nm, irradiation dose: 350mJ / cm²). 2 A coating (cured material) was formed by irradiating it with a light source (irradiation time: 1 second). Next, 100 cuts were made on the surface of the coating using a cutter, and adhesive tape (Sellotape® CT-18 manufactured by Nichiban Co., Ltd.) was applied to it. The adhesive tape was then quickly peeled off. The condition of the coating after the adhesive tape was peeled off was evaluated by visual observation. The copper foil adhesion was categorized as follows: A for adhesion of 90 or more squares, B for adhesion of 50 to 89 squares, C for adhesion of 10 to 49 squares, and D for adhesion of 9 squares or less.

[0116] (Patternability) Each composition was applied to the surface of a copper substrate (ESPANEX, manufactured by Nippon Steel & Sumitomo Metal Chemical Co., Ltd.) using a bar coater, and then a coating film was formed by heat drying (heating temperature: 80°C, heating time: 2 minutes). Subsequently, this coating film was exposed to active energy rays (ultraviolet light, wavelength: 365 nm, irradiation dose: 100 mJ / cm²) through a photomask (three types with mask aperture sizes of 5 μm, 10 μm, and 20 μm) with a gap of 300 μm. 2 , illuminance 20mW / cm 2 The surface was irradiated for 5 seconds. Furthermore, a patterning film was formed by developing the surface for 10 seconds using only water as the developer. For patternability, materials with mask opening sizes of 5 μm, 10 μm, and 15 μm were classified as A if the pattern was formed within ±20% of the mask opening size, and B if all others were B. Materials with pattern formation of A are useful as patterning materials for metal or metal oxide substrates. Materials with a mask opening of 15 μm and a pattern of A are preferably used as patterning materials for metal or metal oxide substrates, materials with mask openings of 15 μm and 10 μm and a pattern of A are more preferable, and materials with mask openings of 5 μm, 10 μm, and 20 μm and a pattern of A are particularly preferable.

[0117] [Table 1]

[0118] As shown in Table 1, the compositions of the present invention have good solubility in water and excellent metal adhesion and patterning properties.

Claims

1. A composition comprising an acrylamide compound (A), an ethylenically unsaturated compound (B) having a carboxyl group or a group represented by the following general formula (I), and a radical polymerization initiator (C), A composition in which the acrylamide compound (A) contains a polyfunctional acrylamide compound represented by the following general formula (II). 【Chemistry 1】 (In the formula, R １ This represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms. R ２ This represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a heterocyclic group having 2 to 10 carbon atoms, or a group having 3 to 20 carbon atoms containing a heterocyclic group. X １ These are single bonds, -O-, -CO-, -COO-, -OCO-, -NR ３ -, -NR ３ CO-, -CONR ３ -, -S- or -SO ２ - represents, X ２ This represents single bonds, hydrocarbon groups with 1 to 20 carbon atoms, heterocyclic groups with 2 to 10 carbon atoms, and groups containing heterocyclic elements with 3 to 20 carbon atoms. R ３ each independently represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a heterocyclic group having 2 to 10 carbon atoms, or a group having 3 to 20 carbon atoms containing a heterocyclic ring. a is a number between 1 and 3, and if a is 2 or greater, there are multiple R １ They may be the same or different. b is a number between 0 and 2, and if b is 2, there are multiple R's. ２ They may be the same or different. a + b = 3, * indicates a coupling. 【Chemistry 2】 (In the formula, L11 and L12 are each independently a hydrocarbon group having 1 to 20 carbon atoms which may have substituents, a heterocyclic group having 2 to 10 carbon atoms which may have substituents, a group in which one or more methylene groups in the hydrocarbon group are substituted with a group selected from the following <Group A>, and in the heterocyclic group This represents a group in which one or more methylene groups are substituted with groups selected from the following <Group A>, or a group containing a heterocycle with 3 to 20 carbon atoms. Group A consists of -O-, -CO-, -COO-, -OCO-, -NR 15-, -NR 15CO-, -CONR 15-, and -S-. X 11 represents a single bond, -O- or -S-, R11, R12, R13, and R14 each independently represent a hydrogen atom or a methyl group. R 15 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms. n1, n2, n3, and n4 each independently represent integers between 0 and 5, If n1 is 2 or more, the multiple R11s may be the same or different. If n2 is 2 or more, the multiple R12s may be the same or different. If n3 is 2 or more, the multiple R13s may be the same or different. If n4 is 2 or more, the multiple R14s may be the same or different. n1 + n3 ≥ 1, n1 + n2 + n3 + n4 ≥ 2.

2. X in the above general formula (I) １ The composition according to claim 1, wherein is -O-.

3. The composition according to claim 1 or 2, wherein in the general formula (II), n² + n₄ ≥ 1.

4. In the above general formula (II), R １１ , R １２ , R １３ and R １４ The composition according to any one of claims 1 to 3, wherein the atom is a hydrogen atom.

5. The composition according to any one of claims 1 to 4, wherein the acrylamide compound (A) is a water-soluble acrylamide compound that dissolves in water at 25°C in an amount of 1% by mass or more.

6. The composition according to any one of claims 1 to 5, wherein the content of the ethylenically unsaturated compound (B) is 1 part by mass or more and 50 parts by mass or less per 100 parts by mass of the acrylamide compound (A).

7. A composition according to any one of claims 1 to 6, which is a patterning material for metal or metal oxide substrates.

8. A cured product of the composition according to any one of claims 1 to 7.

9. A method for producing a cured product, comprising irradiating a composition according to any one of claims 1 to 7 with an active energy ray.

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