Zinc Complex

Abstract

[Problem] The present invention addresses the problem of providing a technology that increases the solubility of a zinc compound having an alkenyloxycarbonyl group, such as a zinc di(meth)acrylate or a derivative thereof, in various solvents and monomers. [Solution] A zinc complex represented by general formula (I). In the formula, L each independently is a ligand that is a nitrogen-containing organic compound and R each independently is a C2-10 alkenyl group in which the α-position of the double bond may be substituted by a methyl group.

Description

[Technical field]

[0001] The present invention relates to zinc complexes. [Background technology]

[0002] It is already known that a transparent methacrylic resin can be produced by dissolving zinc diacrylate and / or zinc dimethacrylate (hereinafter also referred to as zinc di(meth)acrylate) in methyl methacrylate and copolymerizing the resulting mixture.

[0003] However, zinc di(meth)acrylate has low solubility in methyl methacrylate, and in order to produce a methacrylic resin while maintaining performance such as transparency, it is necessary to keep the amount of zinc di(meth)acrylate used extremely small, which has the problem that the obtained methacrylic resin cannot be fully imparted with properties derived from zinc di(meth)acrylate, such as heat resistance and mechanical strength.

[0004] As a measure to solve such problems, attempts have been made to improve the solubility of zinc di(meth)acrylate by adding water to methyl methacrylate, and to obtain a resin composition by copolymerization that has improved heat resistance without impairing the inherent transparency and mechanical properties of methacrylic resins (Patent Document 1).

[0005] Furthermore, zinc di(meth)acrylate is known to be blended with rubber compositions to improve vulcanizability, or to be used as a modifier for synthetic resins (Patent Documents 2 to 5). [Prior art documents] [Patent documents]

[0006] [Patent Document 1] Japanese Patent Application Publication No. 6-145255 [Patent Document 2] Japanese Patent Application Publication No. 52-154436 [Patent Document 3] Japanese Patent Application Publication No. 53-83834 [Patent Document 4] Japanese Patent Application Publication No. 60-94434 [Patent Document 5] Japanese Patent Application Publication No. 2-218639 Summary of the Invention

[0007] The present inventors have noticed that the applications of zinc di(meth)acrylate are generally limited to the above-mentioned applications. They have found that the reason behind this is that zinc di(meth)acrylate can only be dissolved in limited solvents such as water. They therefore thought that if zinc di(meth)acrylate could be dissolved in various solvents and monomers other than water, the versatility of zinc di(meth)acrylate would be significantly improved.

[0008] Therefore, an object of the present invention is to provide a technique for increasing the solubility of zinc compounds having an alkenyloxycarbonyl group, such as zinc di(meth)acrylate or a derivative thereof, in various solvents and monomers.

[0009] One aspect of the present invention is a compound represented by the following general formula (I):

[0010] [ka]

[0011] In the formula, each L is independently a ligand which is a nitrogen-containing organic compound, and each R is independently an alkenyl group having 2 to 10 carbon atoms which may be substituted with a methyl group at the α-position of the double bond.

[0012] One aspect of the present invention is a compound represented by the following general formula (II): Zn(OCOR a )2···(II) In the formula, R aand each independently represent an alkenyl group having 2 to 10 carbon atoms which may be substituted with a methyl group at the α-position of the double bond; and a nitrogen-containing organic compound in an amount of 2 or more molar equivalents relative to the zinc atom of the zinc carboxylate. [Brief description of the drawings]

[0013] [Figure 1] Figure 1 shows the results of single crystal X-ray structure analysis. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0014] In this specification, "X to Y" indicating a range means "X or more and Y or less". When "X to Y" are described multiple times, for example, when "X1 to Y1 or X2 to Y2" is described, the disclosure of each numerical value as the upper limit, the disclosure of each numerical value as the lower limit, and the combination of the upper and lower limits are all disclosed (i.e., the basis for the amendment is lawful). Specifically, the amendment with X1 or more, the amendment with Y2 or less, the amendment with X1 or less, the amendment with Y2 or more, the amendment with X1 to X2, and the amendment with X1 to Y2 must all be considered lawful. In addition, unless otherwise specified, the operation and measurement of physical properties are performed under the conditions of room temperature (20 to 25°C) / relative humidity 50±5%RH.

[0015] <Zinc complex> One aspect of the present invention is a compound represented by the following general formula (I):

[0016] [ka]

[0017] In the formula, L is a ligand which is a nitrogen-containing organic compound, and R is an alkenyl group having 2 to 10 carbon atoms which may be substituted with a methyl group at the α-position of the double bond. Such a complex is soluble in various organic solvents and monomers other than water. In this specification, the organic solvent and / or (other) monomer may be referred to as a solvent. According to one aspect of the present invention, a technology can be provided for increasing the solubility of a zinc compound having an alkenyloxycarbonyl group, such as zinc di(meth)acrylate or a derivative thereof, in various solvents and monomers.

[0018] In one embodiment of the present invention, the alkenyl group having 2 to 10 carbon atoms and optionally substituted with a methyl group at the α-position of the double bond in R may have a substituent. In one embodiment of the present invention, R is an alkenyl group having 2 to 9, 2 to 8, 2 to 7, 2 to 6, 2 to 5, or 2 to 4 carbon atoms and optionally substituted with a methyl group at the α-position of the double bond. In one embodiment of the present invention, the alkenyl group having 2 to 10 carbon atoms which may be substituted with a methyl group at the α-position of the double bond is a vinyl group, a 1-propenyl group, a 2-propenyl group (allyl group), an isopropenyl group, a 1-butenyl group, a 1-methyl-1-butenyl group, a 2-butenyl group, a 2-methyl-2-butenyl group, a 3-butenyl group, a 3-methyl-3-butenyl group, a 1-pentenyl group, a 1-methyl-1-pentenyl group, a 2-pentenyl group, a 2-methyl-2-pentenyl group, a 3-pentenyl group, a 3-methyl-3-pentenyl group, a 4-pentenyl group, a 5-pentenyl group, a 6-pentenyl group, a 7-pentenyl group, a 8-pentenyl group, a 9-pentenyl group, a 10-pentenyl group, a 11-pentenyl group, a 12-pentenyl group, a 13-pentenyl group, a 14-pentenyl group, a 15-pentenyl group, a 16-pentenyl group, a 17-pentenyl group, a 18-pentenyl group, a 21-pentenyl group, a 22-pentenyl group, a 23-pentenyl group, a 24-pentenyl group, a 25-pentenyl group, a 26-pentenyl group, a 27-pentenyl group, a 28-pentenyl group, a 29-pentenyl group, a 30-pentenyl group, a 31-pentenyl group, a 32-pentenyl group, a 33-pentenyl group, a 34-pentenyl group, a 35-pentenyl group, a 36-pentenyl Examples of such an alkyl group include a 4-methyl-4-pentenyl group, a 1-hexenyl group, a 1-methyl-1-hexenyl group, a 2-hexenyl group, a 2-methyl-2-hexenyl group, a 3-hexenyl group, a 3-methyl-3-hexenyl group, a 4-hexenyl group, a 4-methyl-4-hexenyl group, a 5-hexenyl group, a 5-methyl-5-hexenyl group, a 6-heptenyl group, a 6-methyl-heptenyl group, a 7-octenyl group, a 7-methyl-7-octenyl group, an 8-nonyl group, an 8-methyl-8-nonyl group, a 9-decenyl group, and a 9-methyl-9-decenyl group.

[0019] In one embodiment of the present invention, the nitrogen-containing organic compound may be an organic compound containing one or more nitrogen atoms in the molecule. In one embodiment of the present invention, the nitrogen-containing organic compound may be a tertiary amine or a nitrogen-containing heterocyclic compound. In one embodiment of the present invention, the nitrogen-containing organic compound includes those that do not have a polymerizable group such as an ethylenically unsaturated group.

[0020] (Tertiary amine) In one embodiment of the invention, the tertiary amine is N(R 1 )(R 2 )(R 3 ), where R 1 , R 2 and R 3 are each independently an alkyl group having 1 to 10 carbon atoms, which may be substituted by a substituent. Examples of the alkyl group having 1 to 10 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, a c-propyl group, an n-butyl group, an i-butyl group, a s-butyl group, a t-butyl group, a c-butyl group, an n-pentyl group, a c-pentyl group, an n-hexyl group, a c-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, and an n-decyl group. In one embodiment of the present invention, R 1 , R 2 and R 3 may each independently be an alkyl group having 1 to 8, 1 to 6, 1 to 4, 1 to 3, or 1 or 2 carbon atoms, which may be substituted.

[0021] In one embodiment of the present invention, R 1 , R 2 and R 3 The substituents substituted on the alkyl group having 1 to 10 carbon atoms in b (However, R b may each independently be an alkenyl group having 2 to 10 carbon atoms, the α-position of the double bond of which may be substituted with a methyl group. In one embodiment of the present invention, R bThe alkenyl group having 2 to 10 carbon atoms and in which the α-position of the double bond may be substituted with a methyl group is an alkenyl group having 2 to 9, 2 to 8, 2 to 7, 2 to 6, 2 to 5, or 2 to 4 carbon atoms and in which the α-position of the double bond may be substituted with a methyl group. b In the above, the alkenyl group having 2 to 10 carbon atoms and which may be substituted with a methyl group at the α-position of the double bond is a vinyl group, a 1-propenyl group, a 2-propenyl group (allyl group), an isopropenyl group, a 1-butenyl group, a 1-methyl-1-butenyl group, a 2-butenyl group, a 2-methyl-2-butenyl group, a 3-butenyl group, a 3-methyl-3-butenyl group, a 1-pentenyl group, a 1-methyl-1-pentenyl group, a 2-pentenyl group, a 2-methyl-2-pentenyl group, a 3-pentenyl group, a 3-methyl-3-pentenyl group, a 4-pentenyl group, a 4-methyl- Examples of such alkyl groups include ethyl-4-pentenyl group, 1-hexenyl group, 1-methyl-1-hexenyl group, 2-hexenyl group, 2-methyl-2-hexenyl group, 3-hexenyl group, 3-methyl-3-hexenyl group, 4-hexenyl group, 4-methyl-4-hexenyl group, 5-hexenyl group, 5-methyl-5-hexenyl group, 6-heptenyl group, 6-methyl-heptenyl group, 7-octenyl group, 7-methyl-7-octenyl group, 8-nonyl group, 8-methyl-8-nonyl group, 9-decenyl group, and 9-methyl-9-decenyl group.

[0022] In one embodiment of the present invention, R 1 , R 2 and R 3 The number of substituents substituted with each of is 1, 2 or 3.

[0023] In one embodiment of the present invention, R 1 , R 2 and R 3 are respectively an unsubstituted alkyl group having 1 to 10 carbon atoms, an unsubstituted alkyl group having 1 to 10 carbon atoms, and -OCOR b is an alkyl group having 1 to 10 carbon atoms substituted with

[0024] In one embodiment of the present invention, R 1 , R 2 and R3 are each independently an unsubstituted alkyl group having 1 to 10 carbon atoms.

[0025] (Nitrogen-containing heterocyclic compound) In one embodiment of the present invention, the heterocycle in the nitrogen-containing heterocyclic compound may be a five-membered ring or may be a six-membered ring. In one embodiment of the present invention, the heteroatom other than the nitrogen atom in the nitrogen-containing heterocyclic compound may be at least one of an oxygen atom and a sulfur atom. In one embodiment of the present invention, the nitrogen-containing heterocyclic compound may have at least one of an aromatic ring and an alicyclic ring. In one embodiment of the present invention, the nitrogen-containing heterocyclic compound may be a single ring or a condensed ring. In one embodiment of the present invention, the nitrogen-containing heterocyclic compound may have one, two or three heteroatoms.

[0026] In one embodiment of the present invention, specific examples of the nitrogen-containing heterocyclic compound include pyridine, N-methylpyrrolidone, quinoline, piperazine, piperidine, morpholine, carbazole, triazine, etc. When pyridine is used as the nitrogen-containing heterocyclic compound, the stability of the zinc complex as a crystal can be improved.

[0027] In one embodiment of the present invention, the nitrogen-containing heterocyclic compounds may be used alone or in combination of two or more.

[0028] In one embodiment of the present invention, the zinc complex represented by general formula (I) is represented by the following general formula (II): Zn(OCOR a )2···(II) In the formula, R a and each independently represent an alkenyl group having 2 to 10 carbon atoms, the α-position of the double bond of which may be substituted with a methyl group, and a nitrogen-containing organic compound in an amount of 2 or more molar equivalents relative to the zinc atom of the zinc carboxylate. If the molar equivalent of the nitrogen-containing organic compound relative to the zinc atom of the zinc carboxylate is less than 2 molar equivalents, it is difficult to obtain a dicoordinated complex.

[0029] Thus, in another aspect of the present invention, one embodiment of the present invention is a compound represented by the following general formula (II): Zn(OCOR a )2···(II) In the formula, R a and each independently represent an alkenyl group having 2 to 10 carbon atoms, the α-position of which may be substituted with a methyl group, and a nitrogen-containing organic compound in an amount of 2 or more molar equivalents relative to the zinc atom of the zinc carboxylate.

[0030] In one embodiment of the present invention, the above R a In the above formula, the alkenyl group having 2 to 10 carbon atoms and in which the α-position of the double bond may be substituted with a methyl group may have a substituent. a The alkenyl group having 2 to 10 carbon atoms and in which the α-position of the double bond may be substituted with a methyl group is an alkenyl group having 2 to 9, 2 to 8, 2 to 7, 2 to 6, 2 to 5, or 2 to 4 carbon atoms and in which the α-position of the double bond may be substituted with a methyl group. a In the above, the alkenyl group having 2 to 10 carbon atoms and which may be substituted with a methyl group at the α-position of the double bond is a vinyl group, a 1-propenyl group, a 2-propenyl group (allyl group), an isopropenyl group, a 1-butenyl group, a 1-methyl-1-butenyl group, a 2-butenyl group, a 2-methyl-2-butenyl group, a 3-butenyl group, a 3-methyl-3-butenyl group, a 1-pentenyl group, a 1-methyl-1-pentenyl group, a 2-pentenyl group, a 2-methyl-2-pentenyl group, a 3-pentenyl group, a 3-methyl-3-pentenyl group, a 4-pentenyl group, a 4-methyl- Examples of such alkyl groups include ethyl-4-pentenyl group, 1-hexenyl group, 1-methyl-1-hexenyl group, 2-hexenyl group, 2-methyl-2-hexenyl group, 3-hexenyl group, 3-methyl-3-hexenyl group, 4-hexenyl group, 4-methyl-4-hexenyl group, 5-hexenyl group, 5-methyl-5-hexenyl group, 6-heptenyl group, 6-methyl-heptenyl group, 7-octenyl group, 7-methyl-7-octenyl group, 8-nonyl group, 8-methyl-8-nonyl group, 9-decenyl group, and 9-methyl-9-decenyl group.

[0031] In one embodiment of the present invention, the nitrogen-containing organic compound mixed with the zinc carboxylate may be the same as that described above for the nitrogen-containing heterocyclic compound.

[0032] In one embodiment of the present invention, the molar equivalent of the nitrogen-containing organic compound relative to the zinc atom of the zinc carboxylate is 30 molar equivalents or less, 25 molar equivalents or less, 10 molar equivalents or less, 8 molar equivalents or less, 6 molar equivalents or less, 4.5 molar equivalents or less, 4 molar equivalents or less, 3.5 molar equivalents or less, 3 molar equivalents or less, or 2.5 molar equivalents or less.

[0033] As described above, the compound represented by the following general formula (II): Zn(OCOR a )2···(II) In the formula, R a are each independently an alkenyl group having 2 to 10 carbon atoms, the α-position of which may be substituted with a methyl group, and zinc carboxylates (e.g., zinc diacrylate) are generally poorly soluble in water and organic solvents / monomers other than methanol (or alcohol). Therefore, they are difficult to use in liquid phase polymerization, and have mostly been used as rubber modifiers in solid phase polymerization.

[0034] According to one embodiment of the present invention, as described above, a nitrogen-containing organic compound is used, and the solubility of the zinc carboxylate (e.g., zinc diacrylate) in an organic solvent / monomer can be dramatically improved. This is believed to be because the nitrogen-containing organic compound is coordinated / complexed to the zinc carboxylate (e.g., zinc diacrylate) (e.g., 2 to 4 molecules), resulting in improved solubility.

[0035] In one embodiment of the present invention, the zinc complex may exhibit a tetrahedral structure.

[0036] In one embodiment of the present invention, the zinc complex is soluble in various organic solvents and monomers and polymerizable.

[0037] In one embodiment of the present invention, the method of mixing the zinc carboxylate with the nitrogen-containing organic compound is not particularly limited. The nitrogen-containing organic compound may be added to the zinc carboxylate, or the zinc carboxylate may be added to the nitrogen-containing organic compound. In one embodiment of the present invention, the zinc carboxylate and the nitrogen-containing organic compound may be mixed together with various solvents and / or various monomers, and the order of addition is not particularly limited.

[0038] <Solubility of zinc complexes> The zinc complex according to one embodiment of the present invention has excellent solubility in various monomers and organic solvents. In one embodiment of the present invention, the indicator of solubility is transmittance. This transmittance can be calculated by the measurement method described in the Examples. More specifically, it can mean the transmittance at a wavelength of 660 nm using a spectrophotometer of a monomer / organic solvent (composition temperature: 25° C.) containing a zinc complex (zinc carboxylate) at a concentration of 2.5% by mass calculated as zinc salt.

[0039] In one embodiment of the present invention, the compound represented by the following general formula (I):

[0040] [ka]

[0041] In the formula, L is independently a ligand which is a nitrogen-containing organic compound, and R is independently an alkenyl group having 2 to 10 carbon atoms, the α-position of which may be substituted with a methyl group, has a zinc complex concentration of 2.5 mass% calculated as a zinc salt, and the transmittance in at least one of another monomer having an ethylenically unsaturated bond group and an organic solvent is 90% or more. The reason why it is described as "another monomer having an ethylenically unsaturated bond" is to distinguish it from R, which also has an ethylenically unsaturated bond.

[0042] In one embodiment of the present invention, the compound represented by the following general formula (II): Zn(OCOR a )2···(II) In the formula, R aare each independently an alkenyl group having 2 to 10 carbon atoms at the α-position of a double bond which may be substituted with a methyl group; and a nitrogen-containing organic compound in an amount of 2 molar equivalents or more relative to the zinc atom of the zinc carboxylate. The zinc complex obtained by mixing the zinc carboxylate has a concentration of 2.5 mass % calculated as the zinc salt and has a transmittance of 90% or more in at least one of another monomer having an ethylenically unsaturated bond group and an organic solvent.

[0043] In addition, the following general formula (II): Zn(OCOR a )2···(II) In the formula, R a are each independently an alkenyl group having 2 to 10 carbon atoms, the α-position of which may be substituted with a methyl group, and the zinc carboxylate shown has excellent solubility in methanol even when not complexed. In that sense, the organic solvent does not need to be methanol. In one embodiment of the present invention, the organic solvent does not contain alcohol. In one embodiment of the present invention, the organic solvent does not contain methanol.

[0044] In one embodiment of the present invention, the transmittance may be, for example, 91% or more, 92% or more, 93% or more, 94% or more, 95% or more, 96% or more, 97% or more, or 98% or more.

[0045] (Other monomers having ethylenically unsaturated bond groups) In one embodiment of the present invention, the other monomer having an ethylenically unsaturated bond group is a zinc complex and / or a monomer represented by the following general formula (II): Zn(OCOR a )2···(II) In the formula, R aare each independently an alkenyl group having 2 to 10 carbon atoms, the α-position of the double bond of which may be substituted with a methyl group. There are no particular limitations on the type of copolymerizable with the zinc salt of a carboxylate shown, and examples of such copolymerizable groups include (meth)acrylic acid ester compounds ((meth)acrylic acid alkyl) such as methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, butyl (meth)acrylate, pentyl (meth)acrylate, hexyl (meth)acrylate, octyl (meth)acrylate, dodecyl (meth)acrylate, and octadecyl (meth)acrylate; olefinic hydrocarbons such as ethylene, propylene, and vinyl chloride, or halogen-substituted derivatives thereof; aromatic vinyl compounds such as styrene and methylstyrene; vinyl acetate, vinyl propionate, and other vinyl compounds of monovalent carboxylic acids. Examples of the monomers include ester compounds, unsaturated alcohol compounds such as (meth)allyl alcohol and crotonic alcohol, α,β-ethylenically unsaturated carboxylic acid compounds such as (meth)acrylic acid, crotonic acid and cinnamic acid, unsaturated dibasic carboxylic acids such as maleic acid, fumaric acid and itaconic acid, monoester compounds of monohydric alcohols and unsaturated dibasic carboxylic acids such as maleic acid monomethyl ester and maleic acid monoallyl ester, and polyvinyl compounds such as divinylbenzene, ethylene glycol diacrylate, ethylene glycol dimethacrylate, trimethylolpropane triacrylate, trimethylolpropane trimethacrylate and diallyl maleate. These other monomers having a vinyl group can be used alone or in combination of two or more kinds. In one embodiment of the present invention, the number of carbon atoms of the alkyl in the (meth)acrylic acid is 1 to 18, 1 to 15, 1 to 10, 1 to 7, or 1 to 4. In one embodiment of the present invention, the alkyl in the (meth)acrylic acid may be substituted with a hydroxyl group. In one embodiment of the present invention, the alkyl in the alkyl (meth)acrylate may be substituted with an alkoxy group. In one embodiment of the present invention, the alkoxy group may have 1 to 5 carbon atoms, or 1 to 3 carbon atoms. In one embodiment of the present invention, the alkyl (meth)acrylate may be substituted with an alkenyloxy group. In one embodiment of the present invention, the alkyl (meth)acrylate may have an alkenyloxy group and an ether bond.In one embodiment of the present invention, the alkenyloxy group may have 1 to 3 carbon atoms.

[0046] In this specification, when another monomer having an ethylenically unsaturated bond group also corresponds to a nitrogen-containing organic compound, it is classified as a nitrogen-containing organic compound. Therefore, the other monomer having an ethylenically unsaturated bond group in this specification is not a nitrogen-containing organic compound.

[0047] In one embodiment of the present invention, the other monomer may be an oligomer. Here, an oligomer means a monomer having two or more repeating units, and may also be recognized as a polymer. In this embodiment, when the other monomer is an oligomer (polymer), it may be less than 5% by mass, 4% by mass or less, 3% by mass or less, 2% by mass or less, 1% by mass or less, 0.5% by mass or less, or 0% by mass of the total mass of the monomers.

[0048] (Organic solvent) The organic solvent may be an organic compound that is liquid at room temperature and normal pressure (25°C, 1 atm). When the organic solvent is also a nitrogen-containing organic compound, it is classified as a nitrogen-containing organic compound. Thus, the organic solvent in this specification is not a nitrogen-containing organic compound. In one embodiment of the present invention, the organic solvent includes an organic solvent that does not have a polymerizable group such as an ethylenically unsaturated group. This embodiment can more effectively impart properties derived from zinc di(meth)acrylate, such as heat resistance.

[0049] In one embodiment of the present invention, the organic solvent is not particularly limited, but examples thereof include alcohols such as methanol, ethanol, propanol, butanol, methoxybutanol, glycol ethers (for example, glycol ethers such as ethylene glycol monobutyl ether (butyl cellosolve), propylene glycol monomethyl ether, and propylene glycol monomethyl ether acetate), and polyfunctional alcohols (for example, ethylene glycol, propylene glycol, and trimethylolpropane); esters such as methyl acetate, ethyl acetate, butyl acetate, ethyl lactate, methyl lactate, and butyl lactate; hydrocarbons such as toluene and xylene, ketones such as acetone and methyl ethyl ketone; and ethers (diethyl ether, diphenyl ether, ethylene glycol diethyl ether, and tetrahydrofuran). These organic solvents may be used alone or in combination of two or more.

[0050] <Zinc Complex Composition> In one embodiment of the present invention, there is provided a composition comprising the above zinc complex and a solvent, the solvent being substantially composed of other monomers having an ethylenically unsaturated bond group and / or an organic solvent. Zn(OCOR a )2···(II) In the formula, R ais an alkenyl group having 2 to 10 carbon atoms at the α-position of the double bond, which may be substituted with a methyl group; a nitrogen-containing organic compound; and a solvent, wherein the solvent is substantially composed of other monomers having an ethylenically unsaturated bond group and / or an organic solvent. Here, "substantially composed of" means that the solvent does not contain any medium other than the monomer having an ethylenically unsaturated bond group and the organic solvent, or if it does contain any medium, the amount of such medium in the solvent is, for example, 5% by mass or less, 1% by mass or less, 0.1% by mass or less, 0.05% by mass or less, 0.01% by mass or less, 0.005% by mass or less, or 0.001% by mass or less. In one embodiment of the present invention, the solvent is substantially free of water. Here, "substantially free of water" not only encompasses cases where the solvent does not contain any water at all, but also conceptually encompasses cases where the solvent unavoidably contains moisture from the air, or cases where the solvent contains a very small amount of water, for example, 5% by mass or less, 1% by mass or less, 0.1% by mass or less, 0.05% by mass or less, 0.01% by mass or less, 0.005% by mass or less, or 0.001% by mass or less.

[0051] In one embodiment of the present invention, the explanation given in <Solubility of zinc complex> may be applied to the type of other monomer having an ethylenically unsaturated bond group and the organic solvent. As described above, zinc carboxylate has excellent solubility in methanol even if it is not complexed. In that sense, the organic solvent does not need to be methanol. Zinc carboxylate may have excellent solubility in alcohol. Therefore, in one embodiment of the present invention, the organic solvent does not need to be alcohol. In one embodiment of the present invention, the organic solvent does not include alcohol. In one embodiment of the present invention, the organic solvent does not include methanol.

[0052] In one embodiment of the present invention, the ratio of the other monomer having an ethylenically unsaturated bond group in the composition may be 70% by weight or more, 75% by weight or more, 80% by weight or more, 85% by weight or more, 90% by weight or more, or 95% by weight or more. In one embodiment of the present invention, the ratio of the other monomer having an ethylenically unsaturated bond group in the composition may be 99.5% by weight or less, 97.5% by weight or less, 96% by weight or less, 94% by weight or less, 92% by weight or less, 90% by weight or less, 88% by weight or less, 86% by weight or less, or 84% by weight or less.

[0053] In one embodiment of the present invention, a compound represented by the following general formula (II): Zn(OCOR a )2···(II) In the formula, R a are each independently an alkenyl group having 2 to 10 carbon atoms, the α-position of which may be substituted with a methyl group, and the proportion of the zinc carboxylate may be 0.01 to 40 parts by mass, 0.01 to 30 parts by mass, 0.01 to 20 parts by mass, or 0.01 to 10 parts by mass.

[0054] In one embodiment of the present invention, the proportion of the organic solvent in the composition may be 60% by weight or more, 70% by weight or more, 75% by weight or more, 80% by weight or more, 85% by weight or more, 90% by weight or more, or 95% by weight or more. In one embodiment of the present invention, the proportion of the organic solvent in the composition may be 97.5% by weight or less, 96% by weight or less, 94% by weight or less, 92% by weight or less, 90% by weight or less, 88% by weight or less, 86% by weight or less, 84% by weight or less, 80% by weight or less, 75% by weight or less, 70% by weight or less, or 65% by weight or less.

[0055] In one embodiment of the present invention, the proportion of the zinc complex in the composition may be 0.5% by weight or more, 0.7% by weight or more, 1% by weight or more, 1.2% by weight or more, 1.5% by weight or more, 1.7% by weight or more, 2% by weight or more, 2.2% by weight or more, 2.4% by weight or more, 2.6% by weight or more, 2.8% by weight or more, 3% by weight or more, 3.5% by weight or more, 4% by weight or more, 4.5% by weight or more, 5% by weight or more, 5.5% by weight or more, 6% by weight or more, 6.5% by weight or more, 7% by weight or more, 10% by weight or more, 15% by weight or more, 20% by weight or more, 25% by weight or more, or 30% by weight or more. In one embodiment of the present invention, the proportion of the zinc complex in the composition may be 55% by weight or less, 50% by weight or less, or 45% by weight or less.

[0056] In one embodiment of the present invention, the proportion of the zinc carboxylate in the composition may be 0.1% by weight or more, 0.3% by weight or more, 0.5% by weight or more, 0.7% by weight or more, 1% by weight or more, 1.2% by weight or more, 1.5% by weight or more, 1.7% by weight or more, 2% by weight or more, 2.2% by weight or more, 2.4% by weight or more, 2.6% by weight or more, 2.8% by weight or more, 3% by weight or more, 4% by weight or more, 5% by weight or more, 6% by weight or more, 7% by weight or more, 8% by weight or more, or 9% by weight or more. In one embodiment of the present invention, the proportion of the zinc carboxylate in the composition may be 40% by weight or less, 30% by weight or less, or 25% by weight or less.

[0057] In one embodiment of the present invention, the molar ratio of the nitrogen-containing organic compound to the zinc atom of the zinc carboxylate is at least 2. In one embodiment of the present invention, the molar equivalent of the nitrogen-containing organic compound to the zinc atom of the zinc carboxylate is 30 molar equivalents or less, 20 molar equivalents or less, 10 molar equivalents or less, 8 molar equivalents or less, 6 molar equivalents or less, 4.5 molar equivalents or less, 4 molar equivalents or less, 3.5 molar equivalents or less, 3 molar equivalents or less, or 2.5 molar equivalents or less.

[0058] In one embodiment of the present invention, the composition containing the zinc complex and a solvent may further contain a polymerization initiator. Zn(OCOR a )2···(II) In the formula, R a and each independently represent an alkenyl group having 2 to 10 carbon atoms, the α-position of which may be substituted with a methyl group, a nitrogen-containing organic compound, and a solvent, the composition may further contain a polymerization initiator.

[0059] (Polymerization initiator) In one embodiment of the present invention, the polymerization initiator may be a photopolymerization initiator or a thermal polymerization initiator. The photopolymerization initiator is not particularly limited, but may be benzoin, benzoin methyl ether, benzoin ethyl ether, or other benzoin and its alkyl ethers; acetophenone, 2,2-dimethoxy-2-phenylacetophenone, 1,1-dichloroacetophenone, 4-(1-t-butyldioxy-1-methylethyl)acetophenone, or other acetophenones; 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, or other alkylphenones; 2-methylanthraquinone, 2-amyl anthraquinone, 2-t-butyl anthraquinone, 1-chloro anthraquinone, or other anthraquinones; 2,4-dimethylthioxanthone, 2,4-diisopropylthioxanthone, 2-chlorothioxanthone, or other thioxanthones; acetophenone dimethyl ketal, benzyl dimethyl ketal, or other ketals. benzophenone, 4-(1-t-butyldioxy-1-methylethyl)benzophenone, 3,3',4,4'-tetrakis(t-butyldioxycarbonyl)benzophenone and the like benzophenones; 1,2-octanedione, 1-[4-(phenylthio)-2-(O-benzoyloxime)], ethanone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl], 1-(0-acetyloxime) and the like oxime esters; 2-methyl-1-[4-(methylthio)phenyl]-2-morpholino-propan-1-one; 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butanone-1; 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide and the like acylphosphine oxides; xanthones and the like. These may be used alone or in combination of two or more.

[0060] In one embodiment of the present invention, the proportion of the photopolymerization initiator in the composition may be 0.01% by weight or more, 0.05% by weight or more, 0.1% by weight or more, 0.2% by weight or more, 0.3% by weight or more, or 0.4% by weight or more. In one embodiment of the present invention, the proportion of the photopolymerization initiator in the composition may be 20% by weight or less, 10% by weight or less, or 5% by weight or less.

[0061] In one embodiment of the present invention, the composition containing the zinc complex and a solvent may further contain known additives such as plasticizers, inorganic fillers, colorants, reinforcing agents, modifiers, stabilizers, extenders, release agents, and dispersants. These may be used alone or in combination of two or more. In one embodiment of the present invention, the composition may be represented by the following general formula (II): Zn(OCOR a )2···(II) In the formula, R a and each independently represent an alkenyl group having 2 to 10 carbon atoms at the α-position of the double bond which may be substituted with a methyl group, a nitrogen-containing organic compound, and a solvent, the composition may further contain known additives such as a plasticizer, an inorganic filler, a colorant, a reinforcing agent, a modifier, a stabilizer, an extender, a release agent, a dispersant, etc. These may be used alone or in combination of two or more kinds.

[0062] In one embodiment of the present invention, in producing the composition, the method of mixing the zinc complex with the solvent is not particularly limited. The solvent may be added to the zinc complex, or the zinc complex may be added to the solvent. In addition, in one embodiment of the present invention, in producing the composition, a compound represented by the following general formula (II): Zn(OCOR a )2···(II) In the formula, R a are each independently an alkenyl group having 2 to 10 carbon atoms, the α-position of which may be substituted with a methyl group, and the method of mixing the zinc carboxylate, the nitrogen-containing organic compound, and the solvent is also not particularly limited. They may be added in any order.

[0063] In one embodiment of the present invention, when a polymerization initiator or an additive is further added to produce the composition, the method of mixing these is similarly not particularly limited. They may be added in any order.

[0064] <Ionomer and its manufacturing method> In one embodiment of the present invention, there is provided a method for producing an ionomer containing zinc atoms comprising polymerizing the above composition.

[0065] In one embodiment of the present invention, the polymerization of the composition may be thermal polymerization or photopolymerization. The light source used for exposure to light in the photopolymerization in one embodiment of the present invention is not particularly limited, but a low pressure mercury lamp, a medium pressure mercury lamp, a high pressure mercury lamp, a xenon lamp, a metal halide lamp, an ultraviolet LED, etc. can be used. In addition, the exposure dose (ultraviolet illuminance) in the photopolymerization in one embodiment of the present invention is not particularly limited, but is 0.1 to 600 mW / cm. 2 , 1~400mW / cm 2 Or 5 to 200 mW / cm 2 Examples of the time period are 0.1 seconds to 60 minutes, 1 second to 45 minutes, or 5 seconds to 30 minutes.

[0066] By polymerizing the above composition, Zn(OCOR a )2···(II) In the formula, R a and a structural unit derived from a monomer having an ethylenically unsaturated bond group other than the structural unit derived from the zinc carboxylate, wherein each of the structural units derived from the zinc carboxylate is independently an alkenyl group having 2 to 10 carbon atoms, the α-position of the double bond of which may be substituted with a methyl group.

[0067] After polymerization, nitrogen-containing organic compounds such as triethylamine can be removed by drying under reduced pressure, etc. In this way, liquid phase polymerization, which was previously difficult, is now possible, and this is expected to lead to a wide range of applications.

[0068] Although the embodiments of the present invention have been described in detail, it is apparent that the same are illustrative and exemplary, not restrictive, and the scope of the present invention should be interpreted by the appended claims.

[0069] The present invention may include the following aspects and configurations.

[0070] 1. The following general formula (I):

[0071] [ka]

[0072] In the formula, each L is independently a ligand which is a nitrogen-containing organic compound, and each R is independently an alkenyl group having 2 to 10 carbon atoms, the α-position of which may be substituted with a methyl group.

[0073] 2. The following general formula (II): Zn(OCOR a )2···(II) In the formula, R a and each independently represent an alkenyl group having 2 to 10 carbon atoms, the α-position of which may be substituted with a methyl group, at the double bond thereof; and a nitrogen-containing organic compound in an amount of 2 or more molar equivalents relative to the zinc atom of the zinc carboxylate.

[0074] 3. The zinc complex according to 2., wherein the molar equivalents are 4 molar equivalents or less.

[0075] 4.R a are each independently an alkenyl group which may be substituted with a methyl group at the α-position of the double bond having 2 to 4 carbon atoms.

[0076] 5. The zinc complex according to any one of 1. to 4., wherein the nitrogen-containing organic compound is a tertiary amine or a nitrogen-containing heterocyclic compound.

[0077] 6. The tertiary amine is N(R 1 )(R 2 )(R 3 ), where R 1 , R 2 and R 3 are each independently an alkyl group having 1 to 10 carbon atoms which may be substituted with a substituent, and the substituent is represented by: b (However, R b and each independently represent an alkenyl group having 2 to 10 carbon atoms, the α-position of which may be substituted with a methyl group.

[0078] 7. The zinc complex according to 5., wherein the nitrogen-containing heterocyclic compound is pyridine.

[0079] 8. The zinc complex according to any one of 1. to 7., which has a transmittance of 90% or more in another monomer having an ethylenically unsaturated bond group, containing the zinc complex at a concentration of 2.5% by mass calculated as a zinc salt.

[0080] 9. The zinc complex according to any one of 1. to 7., which has a transmittance of 90% or more in an organic solvent containing the zinc complex at a concentration of 2.5% by mass calculated as a zinc salt.

[0081] 10. A composition comprising the zinc complex according to any one of 1. to 9. and a solvent, wherein the solvent consists essentially of another monomer having an ethylenically unsaturated bond group and / or an organic solvent.

[0082] 11. The following general formula (II): Zn(OCOR a )2···(II) In the formula, R a and each independently represent an alkenyl group having 2 to 10 carbon atoms, the α-position of which may be substituted with a methyl group, a nitrogen-containing organic compound, and a solvent, wherein the solvent consists essentially of other monomers having an ethylenically unsaturated bond group and / or an organic solvent.

[0083] 12. The composition described in 11, wherein the proportion of the zinc carboxylate in the composition is 0.1 mass% or more, and the molar ratio of the nitrogen-containing organic compound to the zinc atoms of the zinc carboxylate is 2 moles or more.

[0084] 13. A method for producing an ionomer containing zinc atoms, comprising polymerizing the composition according to any one of 10. to 12.

[0085] 14. A compound represented by the following general formula (II): Zn(OCOR a )2···(II) In the formula, R a each independently represents an alkenyl group having 2 to 10 carbon atoms at the α-position of a double bond which may be substituted with a methyl group; and a structural unit derived from a monomer having an ethylenically unsaturated bond group other than the structural unit derived from the zinc carboxylate. EXAMPLES

[0086] The present invention will be described in more detail below with reference to examples and comparative examples, but the present invention should not be interpreted as being limited to these examples and comparative examples, and examples obtained by appropriately combining the technical means disclosed in each example are also included in the scope of the present invention. Unless otherwise noted, measurements were taken at room temperature (20 to 25°C) and at a relative humidity of 50±5% RH.

[0087] <Confirmation of solubility> (Visual results) Mixtures (75° C.) of zinc diacrylate (ZN-DA), toluene, and various dissolution aids having the compositions shown in the table below were prepared, and the solubility of zinc diacrylate was visually confirmed.

[0088] [Table 1]

[0089] As described above, it is clear that zinc diacrylate can be dissolved in toluene containing various dissolution aids, but zinc diacrylate cannot be dissolved in toluene not containing any dissolution aids.

[0090] <Identification of zinc diacrylate / 2-pyridine ligand> ( 1 H-NMR) A mixture of zinc diacrylate, toluene, and pyridine as a dissolution aid, as shown in Table 1, was concentrated (dried under reduced pressure) to obtain a powder.

[0091] 40 mg of the above powder was taken, dissolved in 2,000 mg of deuterated toluene, and analyzed using a JNM-ECZ600R (manufactured by JEOL Ltd.). 1 H-NMR was measured and the results are shown in the table below.

[0092] [Table 2]

[0093] (thermal mass measurement) The thermal mass of the powder was measured using a Hitachi STA7200 TG / DTA. Specifically, the mass loss rate at the time of constant weight when held at 100°C under a nitrogen stream was considered as the amount of free ligands and compared with the theoretical value. The results are shown in the table below.

[0094] [Table 3]

[0095] (Bromine number measurement) The bromine number of the powder was measured according to JIS K 2605:1996 and compared with the theoretical value. The results are shown in the table below.

[0096] [Table 4]

[0097] (Elemental analysis) The elemental analysis of the above powder was performed using a vario EL cube manufactured by elementar, and the results were compared with theoretical values.

[0098] [Table 5]

[0099] (Single crystal X-ray structure analysis) The single crystal X-ray structure analysis of the above powder was performed on a Rigaku Saturn724+ diffractometer using MoKα radiation (λ=0.71075Å) monochromated by a graphite monochromator. Data were collected using CrystalClear-SM 1.4.0 SP1 and processed with CrysAlisPro 171.41.105a 64 bit. The results are shown in Figure 1.

[0100] <Confirmation of solubility> (Solubility Measurement) Next, the solubility of zinc diacrylate in various solvents and various monomers was evaluated by the following method. That is, in a comparative example (without triethylamine (TEA)), 1 g of zinc diacrylate was prepared in a sealed container. Various solvents and various monomers (25°C) were gradually added thereto while stirring, and complete dissolution was confirmed by visual inspection, and the solubility (mass%) was calculated from the mass of the solution (25°C) at that time. In an example (with triethylamine (TEA)), 1 g of zinc diacrylate was further added with 2 g of triethylamine (4.1 equivalents / zinc diacrylate) and prepared in a sealed container, and the solubility (mass%) of zinc diacrylate in various solvents and various monomers was measured in the same manner as in the comparative example.

[0101] (Transmittance measurement) As an index showing the effect of the solubilizing agent, the transmittance was measured at 2.5 mass% of the solubilizing agent (TEA) in various solvents and monomers.

[0102] More specifically, samples (25° C.) having the following mass ratio were prepared, and the transmittance (%) at a wavelength of 660 nm was measured using a spectrophotometer (manufactured by JASCO Corporation, model number: V-650).

[0103] In the comparative example (without TEA), the ratio of various solvents and monomers to zinc diacrylate was 97.5:2.5. In the examples (TEA added), the ratio of various solvents / various monomers: zinc diacrylate: triethylamine was 92.5:2.5:5.0.

[0104] [Table 6]

[0105] [Table 7]

[0106] As described above, the use of a dissolution aid dramatically improved the solubility of zinc diacrylate in various solvents and various monomers. In addition, the presence or absence of a dissolution aid resulted in a significant difference in the transmittance in various solvents and various monomers. In one embodiment of the present invention, the indicator of "solubility" is a transmittance of 90% or more.

[0107] <Photopolymerization test results> (glass transition temperature) A mixture was prepared by mixing the monomers, polymerization initiator, zinc diacrylate, and dissolution aid shown in the following table. The order of mixing these is not particularly limited.

[0108] Then, a structure was created in which a gap of about 2 mm was provided between two transparent glass plates using double-sided tape as a spacer, and each mixture (2 g) was poured into the gap, and UV intensity: 170 mW / cm was applied using HLR100T-2 manufactured by Sen Special Light Sources Co., Ltd. 2 The polymer was then peeled off from the glass plate to obtain a polymer. The glass transition temperature of each polymer was measured by differential thermal analysis (DTA).

[0109] [Table 8]

[0110] (mass reduction rate) The polymers obtained in Comparative Example 1 and Examples 1-1 to 1-3 were heated and the temperatures at which the mass reduction rates reached 5 mass %, 10 mass %, and 50 mass % were measured.

[0111] In addition, in the measurement of the glass transition temperature and the mass loss rate of Examples 2-1 to 2-3, in order to suppress the influence of the volatile matter (mainly triethylamine) remaining in the obtained polymer, a drying treatment was performed under conditions of 70°C, 0.004 MPa, and 1 hour before the measurement of the glass transition temperature and the mass loss rate.

[0112] [Table 9]

[0113] As shown in Examples 1-1 to 1-3 and Examples 2-1 to 2-3, the glass transition temperature of the polymer obtained by polymerizing methyl methacrylate and butyl acrylate in the presence of a dissolution aid and zinc diacrylate is higher than the glass transition temperature of the polymer of methyl methacrylate and butyl acrylate in Comparative Example 1. This shows that the addition of the dissolution aid and zinc diacrylate has an effect of improving heat resistance.

[0114] It is particularly noteworthy that, in comparison between Examples 1-1 to 1-3, in which a polymerizable dissolution aid A (2-dimethylaminoethyl acrylate) was used, and Examples 2-1 to 2-3, in which a non-polymerizable dissolution aid B (triethylamine) was used, the latter is able to more effectively impart the properties (heat resistance) derived from zinc di(meth)acrylate.

[0115] This application is based on Japanese Patent Application No. 2022-200007 filed on December 15, 2022, the disclosure of which is incorporated by reference in its entirety.

Claims

1. The following general formula (II): Zn(OCOR ａ ) ２ ・・・(II) In the formula, R ａ each independently represents an alkenyl group having 2 to 10 carbon atoms, the α-position of the double bond of which may be substituted with a methyl group; a nitrogen-containing organic compound in an amount of 2 or more molar equivalents relative to the zinc atom of the zinc carboxylate; and the nitrogen-containing organic compound is a nitrogen-containing heterocyclic compound or a tertiary amine, the nitrogen-containing heterocyclic compound is N-methylpyrrolidone, quinoline, piperazine, piperidine, morpholine, carbazole, or triazine; A zinc complex in which the tertiary amine is represented by N(R 1 )(R 2 )(R 3 ), where R 1 , R 2 and R 3 are each independently an alkyl group having 1 to 10 carbon atoms which may be substituted with a substituent, and when substituted with a substituent, the substituent is each independently -OCOR b (wherein each R b is independently an alkenyl group having 2 to 10 carbon atoms which may be substituted with a methyl group at the α-position of the double bond), with the proviso that when the tertiary amine is dimethylaminoethyl methacrylate, the α-position of R a is not substituted with a methyl group, and the nitrogen-containing organic compound is not triethylamine.

2. 2. The zinc complex of claim 1, wherein the molar equivalents are 30 molar equivalents or less.

3. 2. The zinc complex according to claim 1, which has a transmittance of 90% or more in another monomer having an ethylenically unsaturated bond group containing the zinc complex at a concentration of 2.5% by mass calculated as a zinc salt.

4. 2. The zinc complex according to claim 1, which has a transmittance of 90% or more in an organic solvent containing the zinc complex at a concentration of 2.5% by mass in terms of a zinc salt.

5. A zinc complex; A solvent; A composition comprising: The zinc complex is represented by the following general formula (I): 【Chemistry 1】 In the formula, each L is independently a ligand which is a nitrogen-containing organic compound which is a nitrogen-containing heterocyclic compound or a tertiary amine, and each R is independently an alkenyl group having 2 to 10 carbon atoms and which may be substituted with a methyl group at the α-position of the double bond. or The following general formula (II): Zn(OCOR ａ ) ２ ・・・(II) In the formula, R ａ each independently represents an alkenyl group having 2 to 10 carbon atoms at the α-position of the double bond which may be substituted with a methyl group; and a nitrogen-containing organic compound which is a nitrogen-containing heterocyclic compound or a tertiary amine, in an amount of 2 or more molar equivalents relative to the zinc atom of the zinc carboxylate, wherein the nitrogen-containing heterocyclic compound is pyridine, N-methylpyrrolidone, quinoline, piperazine, piperidine, morpholine, carbazole, or triazine, the tertiary amine is represented by N(R 1 )(R 2 )(R 3 ), where R 1 , R 2 and R 3 are each independently an alkyl group having 1 to 10 carbon atoms which may be substituted with a substituent, and when substituted with a substituent, the substituent is each independently -OCOR b (wherein each R b is independently an alkenyl group having 2 to 10 carbon atoms which may be substituted with a methyl group at the α-position of the double bond); A composition, wherein the solvent consists essentially of other monomers having ethylenically unsaturated bond groups and / or an organic solvent, with the proviso that the organic solvent does not contain alcohol.

6. The composition described in claim 5, having a transmittance of 90% or more when containing the zinc complex at a concentration of 2.5 mass% in terms of zinc salt.

7. The following general formula (II): Zn(OCOR ａ ) ２ ・・・(II) In the formula, R ａ each independently represents an alkenyl group having 2 to 10 carbon atoms, the α-position of the double bond of which may be substituted with a methyl group; a nitrogen-containing organic compound which is a nitrogen-containing heterocyclic compound or a tertiary amine; A solvent; Including, a composition in which the nitrogen-containing heterocyclic compound is pyridine, N-methylpyrrolidone, quinoline, piperazine, piperidine, morpholine, carbazole, or triazine, the tertiary amine is represented by N(R 1 )(R 2 )(R 3 ), where R 1 , R 2 , and R 3 are each independently an alkyl group having 1 to 10 carbon atoms which may be substituted with a substituent, and when substituted with a substituent, the substituent is each independently -OCOR b (wherein each R b is independently an alkenyl group having 2 to 10 carbon atoms which may be substituted with a methyl group at the α-position of the double bond); A composition, wherein the solvent consists essentially of other monomers having ethylenically unsaturated bond groups and / or an organic solvent, with the proviso that the organic solvent does not contain alcohol.

8. The composition according to claim 7, wherein the proportion of the zinc carboxylate in the composition is 0.1 mass% or more, and the molar ratio of the nitrogen-containing organic compound to zinc atoms of the zinc carboxylate is 2 moles or more.

9. The composition described in claim 7, having a transmittance of 90% or more when containing the zinc carboxylate at a concentration of 2.5 mass%.

10. 1. A method for producing an ionomer containing zinc atoms, comprising polymerizing a composition comprising a zinc complex and a solvent, comprising: The zinc complex is represented by the following general formula (I): 【Chemistry 2】 In the formula, each L is independently a ligand which is a nitrogen-containing organic compound, and each R is independently an alkenyl group having 2 to 10 carbon atoms and which may be substituted with a methyl group at the α-position of the double bond, or The following general formula (II): Zn(OCOR ａ ) ２ ・・・(II) In the formula, R ａ each independently represents an alkenyl group having 2 to 10 carbon atoms at the α-position of the double bond which may be substituted with a methyl group; and a nitrogen-containing organic compound in an amount of 2 or more molar equivalents relative to the zinc atom of the zinc carboxylate, the nitrogen-containing organic compound is a nitrogen-containing heterocyclic compound or a tertiary amine, the nitrogen-containing heterocyclic compound is pyridine, N-methylpyrrolidone, quinoline, piperazine, piperidine, morpholine, carbazole, or triazine, the tertiary amine is represented by N(R 1 )(R 2 )(R 3 ), where R 1 , R 2 , and R 3 are each independently an alkyl group having 1 to 10 carbon atoms which may be substituted with a substituent, and when substituted with a substituent, the substituent is each independently -OCOR b (wherein each R b is independently an alkenyl group having 2 to 10 carbon atoms which may be substituted with a methyl group at the α-position of the double bond); The method according to claim 1, wherein the solvent consists essentially of other monomers having ethylenically unsaturated bond groups and / or an organic solvent, with the proviso that the organic solvent does not contain an alcohol.

11. The following general formula (II): Zn(OCOR ａ ) ２ ・・・(II) In the formula, R ａ each independently represents an alkenyl group having 2 to 10 carbon atoms, the α-position of the double bond of which may be substituted with a methyl group; a nitrogen-containing organic compound; and a solvent; the nitrogen-containing organic compound is a nitrogen-containing heterocyclic compound or a tertiary amine, the nitrogen-containing heterocyclic compound is pyridine, N-methylpyrrolidone, quinoline, piperazine, piperidine, morpholine, carbazole, or triazine, the tertiary amine is represented by N(R 1 )(R 2 )(R 3 ), where R 1 , R 2 , and R 3 are each independently an alkyl group having 1 to 10 carbon atoms which may be substituted with a substituent, and when substituted with a substituent, the substituent is each independently -OCOR b (wherein each R b is independently an alkenyl group having 2 to 10 carbon atoms which may be substituted with a methyl group at the α-position of the double bond); A method for producing an ionomer containing zinc atoms, comprising polymerizing a composition, wherein the solvent consists essentially of other monomers having ethylenically unsaturated bond groups and / or an organic solvent, with the proviso that the organic solvent does not contain alcohol.

12. The following general formula (II): Zn(OCOR ａ ) ２ ・・・(II) In the formula, each Ra is independently an alkenyl group having 2 to 10 carbon atoms, the α-position of the double bond of which may be substituted with a methyl group; a nitrogen-containing organic compound in an amount of 2 or more molar equivalents relative to the zinc atom of the zinc carboxylate; and the nitrogen-containing organic compound is a nitrogen-containing heterocyclic compound or a tertiary amine, A zinc complex, wherein when the nitrogen-containing organic compound is a nitrogen-containing heterocyclic compound, the nitrogen-containing heterocyclic compound does not have a pyridine skeleton, when the nitrogen-containing organic compound is a tertiary amine, the tertiary amine is not substituted with an amide, when the tertiary amine is dimethylaminoethyl methacrylate, the α-position is not substituted with a methyl group, and the nitrogen-containing organic compound is not triethylamine; A zinc complex having a transmittance of 90% or more in another monomer having an ethylenically unsaturated bond group containing the zinc complex at a concentration of 2.5% by mass, calculated as a zinc salt, or a zinc complex having a transmittance of 90% or more in an organic solvent containing the zinc complex at a concentration of 2.5% by mass, calculated as a zinc salt.

13. A zinc complex; A solvent; A composition comprising: The zinc complex is represented by the following general formula (I): 【Chemistry 3】 In the formula, each L is independently a ligand which is a nitrogen-containing organic compound which is a nitrogen-containing heterocyclic compound or a tertiary amine, and each R is independently an alkenyl group having 2 to 10 carbon atoms and which may be substituted with a methyl group at the α-position of the double bond. or The following general formula (II): Zn(OCOR ａ ) ２ ・・・(II) In the formula, R ａ each independently represents an alkenyl group having 2 to 10 carbon atoms at the α-position of the double bond which may be substituted with a methyl group; and a nitrogen-containing organic compound which is a nitrogen-containing heterocyclic compound or a tertiary amine, in an amount of 2 or more molar equivalents relative to the zinc atom of the zinc carboxylate, The composition, wherein the solvent is substantially composed of another monomer having an ethylenically unsaturated bond group and / or an organic solvent, provided that the organic solvent does not contain alcohol, and when the zinc complex is contained in a concentration of 2.5 mass% in terms of a zinc salt, the composition has a transmittance of 90% or more.

14. The following general formula (II): Zn(OCOR ａ ) ２ ・・・(II) In the formula, R ａ each independently represents an alkenyl group having 2 to 10 carbon atoms, the α-position of the double bond of which may be substituted with a methyl group; a nitrogen-containing organic compound which is a nitrogen-containing heterocyclic compound or a tertiary amine; A solvent; A composition comprising: The composition has a transmittance of 90% or more when the solvent is substantially composed of another monomer having an ethylenically unsaturated bond group and / or an organic solvent, provided that the organic solvent does not contain alcohol and contains the zinc carboxylate at a concentration of 2.5 mass%.

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