Wettability improver and resin composition containing the same, and hydrophilic coating agent

Abstract

To provide means that can maintain high hydrophilicity even after cleaning in a hydrophilic coating layer.SOLUTION: A wettability improver contains an ion-bonding salt represented by the formula (1) or a polymer thereof, and a silicate represented by the formula (A) or a condensate thereof. In the formula (1) and the formula (A), each symbol is defined as in the specifications.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a wettability enhancer, a resin composition containing the same, and a hydrophilic coating agent comprising the same. [Background technology]

[0002] High contamination resistance is required for components used in baths, toilets, wallpaper, window glass, building exterior walls, optical films, etc., and one method for achieving this is to subject the surface of the component to hydrophilic treatment. By carrying out such treatment, a uniform water film is formed on the surface of the component, so even if dirt adheres to the surface, the dirt can be easily removed by washing it off with water. Inorganic compounds with photocatalytic properties such as titanium oxide are generally used for hydrophilic treatment, but they have low transparency and do not exhibit high hydrophilicity unless exposed to light (such as ultraviolet light), so there are problems in that sufficient contamination resistance cannot be obtained in the actual usage environment and the treatment process is complicated.

[0003] Here, as a conventional wettability improver that shows excellent hydrophilicity-imparting effect even when added in a small amount, Patent Document 1 proposes one that contains an ion-bonding salt composed of an anion consisting of a polyoxyalkylene alkyl ether sulfate ion containing at least two kinds of oxyalkylene groups and a cation consisting of a monovalent or divalent metal ion or a nitrogen-containing compound ion. The wettability improver described in Patent Document 1 is said to form a hydrophilic coating film with a very small contact angle with water by, for example, being mixed with a resin and coated and then cured. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] JP 2017-66401 A Summary of the Invention [Problem to be solved by the invention]

[0005] However, according to the investigations of the present inventors, when the wettability enhancer described in Patent Document 1 is used, although the coating film exhibits high hydrophilicity immediately after it is formed by coating, the hydrophilicity decreases after washing, which is a problem.

[0006] Therefore, an object of the present invention is to provide a means for maintaining high hydrophilicity in a hydrophilic coating film even after washing. [Means for solving the problem]

[0007] As a result of intensive research by the inventors to solve the above problems, they found that the above problems can be solved by using an ionically-bonding salt having a specific structure or a polymer thereof in combination with a silicate having a specific structure and / or a condensate thereof to form a wettability improver, and thus completed the present invention.

[0008] That is, one aspect of the present invention is a compound represented by the following chemical formula (1):

[0009] [ka]

[0010] In chemical formula (1), Q n+ represents a monovalent metal ion, a divalent metal ion, or a nitrogen-containing compound ion, T - represents an alkyl sulfate ion, a polyoxyalkylene alkyl ether sulfate ion, a polyoxyalkylene alkyl phenyl ether sulfate ion, an alkyl sulfonate ion, an alkylbenzene sulfonate ion, an alkyl phosphate ion, a polyoxyalkylene alkyl ether phosphate ion, or a polyoxyalkylene alkyl phenyl ether phosphate ion, n is Q n+ The valence of is 1 or 2. An ionic salt represented by the formula: The following chemical formula (A):

[0011] [ka]

[0012] In chemical formula (A), R are the same or different and each represents a hydrogen atom or an optionally substituted monovalent hydrocarbon group having 1 to 10 carbon atoms; and / or a condensate thereof, A wettability enhancer comprising: Effect of the Invention

[0013] The wettability enhancer according to the present invention can maintain high hydrophilicity even after cleaning. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0014] Hereinafter, embodiments of the present invention will be described in detail. Note that the present invention is not limited to the following embodiments.

[0015] In this specification, the term "the coating film (or molded article) surface is highly hydrophilic" is synonymous with the term "the coating film (or molded article) surface is highly wettable by water" and means that the contact angle of the coating film (or molded article) surface with water is 90° or less, preferably 40° or less, more preferably 20° or less, and even more preferably 10° or less, and in particular 10° or less is referred to as "superhydrophilic."

[0016] In this specification, the range "X to Y" means "X or more and Y or less." Unless otherwise specified, the operations and measurements of physical properties are performed under the conditions of room temperature (20 to 25°C) and relative humidity of 40 to 50% RH.

[0017] <Wettability improver> [Ionic salt or its polymer] A wettability enhancer according to one embodiment of the present invention essentially contains the following ion-bonding salt or a polymer thereof.

[0018] (Structure of ionic salt) The ionically bonded salt contained in the wettability enhancer according to the present embodiment is represented by the following chemical formula (1).

[0019] [ka]

[0020] In the above chemical formula (1), T - represents an alkyl sulfate ion, a polyoxyalkylene alkyl ether sulfate ion, a polyoxyalkylene alkyl phenyl ether sulfate ion, an alkyl sulfonate ion, an alkyl benzene sulfonate ion, an alkyl phosphate ion, a polyoxyalkylene alkyl ether phosphate ion, or a polyoxyalkylene alkyl phenyl ether phosphate ion. - is preferably an alkyl sulfate ion, a polyoxyalkylene alkyl ether sulfate ion, or a polyoxyalkylene alkyl phenyl ether sulfate ion, more preferably a polyoxyalkylene alkyl ether sulfate ion, or a polyoxyalkylene alkyl phenyl ether sulfate ion, and even more preferably a polyoxyalkylene alkyl ether sulfate ion. - ) n is particularly preferably a polyoxyalkylene alkyl ether sulfate ion represented by the following chemical formula (2).

[0021] [ka]

[0022] In the above chemical formula (2), R' is a linear or branched alkyl group having 12 to 14 carbon atoms which may be substituted, i.e., a linear or branched dodecyl group, tridecyl group, or tetradecyl group, with the tridecyl group being preferred from the viewpoint of availability. When R' is substituted, examples of such a substituent include a halogen atom such as fluorine, chlorine, bromine, or iodine; an aryl group such as a phenyl group, a p-tolyl group, a xylyl group, a cumenyl group, a naphthyl group, an anthryl group, or a phenanthryl group; an alkoxy group such as a methoxy group, an ethoxy group, or a tert-butoxy group; an aryloxy group such as a phenoxy group or a p-tolyloxy group; an alkoxycarbonyl group such as a methoxycarbonyl group, a butoxycarbonyl group, a 2-ethylhexyloxycarbonyl group, or a phenoxycarbonyl group; an acyloxy group such as an acetoxy group, a propionyloxy group, or a benzoyloxy group; an acetyl group, a benzoyl group, an isobutyryl group, an acryloyl group, a methacryloyl group, a methoxalyl group, or a methyl group; Examples of the alkyl group include acyl groups such as a methylsulfanyl group, alkylsulfanyl groups such as a methylsulfanyl group and a tert-butylsulfanyl group, arylsulfanyl groups such as a phenylsulfanyl group and a p-tolylsulfanyl group, alkylamino groups such as a methylamino group and a cyclohexylamino group, dialkylamino groups such as a dimethylamino group, a diethylamino group, a morpholino group and a piperidino group, and arylamino groups such as a phenylamino group and a p-tolylamino group, as well as a hydroxy group, a carboxy group, a formyl group, a mercapto group, a sulfo group, a mesyl group, a p-toluenesulfonyl group, an amino group, a nitro group, a cyano group, a trifluoromethyl group, a trichloromethyl group, a trimethylsilyl group, a phosphinico group, and a phosphono group.

[0023] In the above chemical formula (2), A is a linear or branched alkylene group having 2 to 4 carbon atoms, and examples thereof include an ethylene group, a trimethylene group, a propylene group (-CH2-CH(CH3)-), an n-butylene group, a 1-methylpropylene group (-CH2-CH2-CH(CH3)-), a 2-methylpropylene group (-CH2-CH(CH3)-CH2-), a dimethylethylene group (-CH2-C(CH3)2-), and an ethylethylene group (-CH2-CH(CH2CH3)-). When A is an alkylene group having 3 to 4 carbon atoms, it is preferably a branched alkylene group. In addition, when A is (AO) m The number of carbon atoms constituting the main chain of is preferably 2 or less. That is, A preferably has at least one type selected from the group consisting of an ethylene group, a propylene group, and an ethylethylene group, and more preferably has at least two types. By having such a group, it is possible to form a coating film or a molded article that has both water resistance and surface hydrophilicity.

[0024] In the above chemical formula (2), m is the average number of moles of AO added, and is an integer of 2 to 50. From the viewpoints of improving workability by reducing viscosity and improving wettability, m is preferably 2 to 30, and more preferably 2 to 20.

[0025] In the above chemical formula (2), (AO) m represents polyoxyalkylene and contains at least two types of oxyalkylene groups. By using such a polyoxyalkylene structure, it is possible to form a coating film or molded product that has both water resistance and surface hydrophilicity. (AO) m Preferably, the AO group contains at least two groups selected from the group consisting of an oxyethylene group (-C2H4O-, hereinafter also referred to as EO), an oxypropylene group (-C3H6O-, hereinafter also referred to as PO), and an oxybutylene group (-C4H8O-, hereinafter also referred to as BO). mMore preferably, it contains an oxyethylene group and an oxybutylene group. The oxypropylene group and the oxybutylene group can have a linear or branched alkylene group, but preferably have a branched alkylene group. Furthermore, the oxypropylene group and the oxybutylene group are preferably (AO) m The number of carbon atoms constituting the main chain is preferably 2 or less. That is, the oxypropylene group preferably has at least one of the groups represented by the following chemical formula (P1) or (P2), and the oxybutylene group preferably has at least one of the groups represented by the following chemical formula (B1) or (B2). By having such a group, it is possible to form a coating film or molded article that has both water resistance and surface hydrophilicity.

[0026] [ka]

[0027] Also, (AO) m In the above, the proportion of oxybutylene groups is preferably 3 to 90 mol %, more preferably 10 to 80 mol %. When the oxybutylene group has two or more types of structures, the proportion of the oxybutylene group represents the total proportion (mol %) of each structure. The arrangement of the at least two types of oxyalkylene groups may be either a random type or a block type, but from the viewpoint of effectively exerting hydrophilicity and simplifying the synthesis process, a block type is preferable. In the case of a block type, the order of the arrangement does not matter. That is, for example, (AO) m When the copolymer is an ethylene oxide / butylene oxide block copolymer, the sulfonic acid group may be linked to a polyoxyethylene chain or a polyoxybutylene chain.

[0028] (AO) mis an alkylene oxide adduct having 2 to 4 carbon atoms, and the structure of such an alkylene oxide adduct is a structure formed by one or more alkylene oxides such as ethylene oxide, propylene oxide, 1,2-butylene oxide, 2,3-butylene oxide, isobutylene oxide, etc. Among them, a structure formed by an alkylene oxide including ethylene oxide and 1,2-butylene oxide is preferable. Note that (AO) m When is formed by two or more of the above compounds, it may be formed by either random addition or block addition.

[0029] According to this specification, (AO) m Also provided is an alkylene oxide adduct having a structure different from the above. In this embodiment, specifically, the alkylene oxide adduct (AO) m However, instead of or in addition to the alkylene oxide having 2 to 4 carbon atoms, it may have an AO structure derived from a monofunctional epoxy compound. Examples of such monofunctional epoxy compounds include compounds obtained by epoxidizing alcohol or phenol with epichlorohydrin. In this case, examples of the alcohol include saturated or unsaturated, linear, branched or cyclic alcohols having 1 to 24 carbon atoms.

[0030] In the above chemical formula (1), n ​​is Q n+ represents the valence of the atom, which is 1 or 2. That is, Q n+ is a monovalent cation (Q + ), then n is 1 and Q n+ is a divalent cation (Q 2+ ), then n is 2.

[0031] In the above chemical formula (1), Q n+ represents a monovalent metal ion, a divalent metal ion, or a nitrogen-containing compound ion.

[0032] Examples of monovalent metal ions include sodium ions, potassium ions, and lithium ions.

[0033] Examples of divalent metal ions include calcium ions and magnesium ions.

[0034] The nitrogen-containing compound ion may be at least one selected from the group consisting of ammonium ion, imidazolium ion, pyridinium ion, pyrrolidinium ion, pyrrolinium ion, piperidinium ion, pyrazinium ion, pyrimidinium ion, triazolium ion, triazinium ion, quinolinium ion, isoquinolinium ion, indolinium ion, quinoxalinium ion, piperazinium ion, oxazolinium ion, thiazolinium ion and morpholinium ion. Each of the above ions may have an ethylenically unsaturated bond such as a (meth)acryloyl group or a vinyl group.

[0035] Specific examples of ammonium ions include the following ions: dimethylammonium ion, trimethylammonium ion, tetramethylammonium ion, diethylammonium ion, triethylammonium ion, tetraethylammonium ion, monopropylammonium ion, dipropylammonium ion, tripropylammonium ion, tetrapropylammonium ion, monobutylammonium ion, dibutylammonium ion, tributylammonium ion, tetrabutylammonium ion, monopentylammonium ion, dipentylammonium ion, tripentylammonium ion, tetrapentylammonium ion, monohexylammonium ion, dihexylammonium ion, monoheptylammonium ion, diheptylammonium ion, monooctylammonium ion, dioctylammonium ion, monononylammonium ion, monodecylammonium ion, monoundecylammonium ion, monododecylammonium ion, monotridecylammonium ion, monotetradecylammonium ion, monopentadecyl ...adecylammonium ion, monopentadecylammonium ion, monopentadecylammonium ion, monopentadecylammonium ion, monopentadecylammonium ion, monopentadecylammonium ion, monopentadecylammonium ion, monopentadecylammonium ion, monopentadecylammonium ion, monopentadecylammonium ion, monopentadecylammonium ion, monopentadecylammonium ion, monopentadecylammonium ion, monopentadecylammonium ion, monopentadecylammonium ion, monopentadecylammonium ion, monopentadecyl ammonium ion, monohexadecylammonium ion, monoheptadecylammonium ion, monooctadecylammonium ion, monononadecylammonium ion, monoicosylammonium ion, monohenicosylammonium ion, monodocosylammonium ion, monotricosylammonium ion, methyl(ethyl)ammonium ion, methyl(propyl)ammonium ion, methyl(butyl)ammonium ion, methyl(pentyl)ammonium ion, methyl(hexyl)ammonium ion, methyl(heptyl)ammonium ion, methyl(octyl)ammonium ion, methyl(nonyl)ammonium ion, methyl(decyl)ammonium ion, methyl(undecyl)ammonium ion, methyl(dodecyl)ammonium ion, methyl(tridecyl)ammonium ion, methyl(tetradecyl)ammonium ion, methyl(pentadecyl)ammonium ion, methyl(hexadecyl)ammonium ion, methyl(heptadecyl)ammonium ion, methyl(octadecyl)ammonium ion,Methyl(nonadecyl)ammonium ion, methyl(icosyl)ammonium ion, methyl(henicosyl)ammonium ion, methyl(tricosyl)ammonium ion, ethyl(propyl)ammonium ion, ethyl(butyl)ammonium ion, ethyl(pentyl)ammonium ion, ethyl(hexyl)ammonium ion, ethyl(heptyl)ammonium ion, ethyl(octyl)ammonium ion, ethyl(nonyl)ammonium ion, ethyl(decyl)ammonium ion, ethyl(undecyl)ammonium ion, ethyl(dodecyl)ammonium ion, ethyl(tridecyl)ammonium ion, ethyl(tetradecyl)ammonium ion, ethyl(pentadecyl)ammonium ion, ethyl(hexadecyl)ammonium ion, ethyl(heptadecyl)ammonium ion, ethyl(octadecyl)ammonium ion, ethyl(nonadecyl)ammonium ion, ethyl(icosyl)ammonium ion, ethyl(henicosyl)ammonium ion, ethyl(tricosyl)ammonium ion, dimethyl(ethyl)ammonium ion, diethyl Methyl(propyl)ammonium ion, dimethyl(butyl)ammonium ion, dimethyl(pentyl)ammonium ion, dimethyl(hexyl)ammonium ion, dimethyl(heptyl)ammonium ion, dimethyl(octyl)ammonium ion, dimethyl(nonyl)ammonium ion, dimethyl(decyl)ammonium ion, dimethyl(undecyl)ammonium ion, dimethyl(dodecyl)ammonium ion, dimethyl(tridecyl)ammonium ion, dimethyl(tetradecyl)ammonium ion, dimethyl(pentadecyl)ammonium ion, dimethyl(hexadecyl)ammonium ion, dimethyl(heptadecyl)ammonium ion, dimethyl(octadecyl)ammonium ion, dimethyl(nonadecyl)ammonium ion, dimethyl(icosyl)ammonium ion, dimethyl(henicosyl)ammonium ion, dimethyl(tricosyl)ammonium ion, trimethyl(ethyl)ammonium ion, trimethyl(propyl)ammonium ion, trimethyl(butyl)ammonium ion, trimethyl(pentyl)ammonium ion,Alkyl ammonium ions such as trimethyl(hexyl)ammonium ion, trimethyl(heptyl)ammonium ion, trimethyl(octyl)ammonium ion, trimethyl(nonyl)ammonium ion, trimethyl(decyl)ammonium ion, trimethyl(undecyl)ammonium ion, trimethyl(dodecyl)ammonium ion, trimethyl(tridecyl)ammonium ion, trimethyl(tetradecyl)ammonium ion, trimethyl(pentadecyl)ammonium ion, trimethyl(hexadecyl)ammonium ion, trimethyl(heptadecyl)ammonium ion, trimethyl(octadecyl)ammonium ion, trimethyl(nonadecyl)ammonium ion, trimethyl(icosyl)ammonium ion, trimethyl(henicosyl)ammonium ion, and trimethyl(tricosyl)ammonium ion.

[0036] Monovinyl ammonium ion, divinyl ammonium ion, trivinyl ammonium ion, monopropenyl ammonium ion, dipropenyl ammonium ion, tripropenyl ammonium ion, monobutenyl ammonium ion, dibutenyl ammonium ion, tributenyl ammonium ion, monopentenyl ammonium ion, dipentenyl ammonium ion, tripentenyl ammonium ion, monohexenyl ammonium ion, dihexenyl ammonium ion, monoheptenyl ammonium ion, diheptenyl ammonium ion, monooctenyl ammonium ion, dioctenyl ammonium ion alkenyl ammonium ions such as monononenyl ammonium ion, monodecenyl ammonium ion, monoundecenyl ammonium ion, monododecenyl ammonium ion, monotridecenyl ammonium ion, monotetradecenyl ammonium ion, monopentadecenyl ammonium ion, monohexadecenyl ammonium ion, monoheptadecenyl ammonium ion, monooctadecenyl ammonium ion, monononadecenyl ammonium ion, monoicosenyl ammonium ion, monohenicosenyl ammonium ion, monodocosenyl ammonium ion, and monotricosenyl ammonium ion.

[0037] Dimethyl(vinyl)ammonium ion, dimethyl(propenyl)ammonium ion, dimethyl(butenyl)ammonium ion, dimethyl(pentenyl)ammonium ion, dimethyl(hexenyl)ammonium ion, dimethyl(heptenyl)ammonium ion, dimethyl(octenyl)ammonium ion, dimethyl(nonenyl)ammonium ion, dimethyl(decenyl)ammonium ion, dimethyl(undecenyl)ammonium ion, dimethyl(dodecenyl)ammonium ion, dimethyl(tridecenyl)ammonium ion, dimethyl(tetradecenyl)ammonium ion, dimethyl(penta Monoammonium ions having alkyl and alkenyl groups, such as dimethyl(hexadecenyl)ammonium ion, dimethyl(heptadecenyl)ammonium ion, dimethyl(octadecenyl)ammonium ion, dimethyl(nonadecenyl)ammonium ion, dimethyl(icosenyl)ammonium ion, dimethyl(henicosenyl)ammonium ion, dimethyl(tricosenyl)ammonium ion, bis(2-methoxyethyl)monoethylammonium ion, trimethyl(vinyl)ammonium ion, and bis(2-methoxyethyl)monomethylammonium ion.

[0038] Aromatic substituted alkyl ammonium ions such as monobenzyl ammonium ion, (1-phenethyl) ammonium ion, (2-phenethyl) ammonium ion (also known as monophenethyl ammonium ion), dibenzyl ammonium ion, bis(1-phenethyl) ammonium ion, and bis(2-phenethyl) ammonium ion (also known as diphenethyl ammonium ion); cycloalkyl ammonium ions having 5 to 16 carbon atoms such as monocyclopentyl ammonium ion, dicyclopentyl ammonium ion, tricyclopentyl ammonium ion, monocyclohexyl ammonium ion, dicyclohexyl ammonium ion, monocycloheptyl ammonium ion, and dicycloheptyl ammonium ion; monoammonium ions having alkyl groups and cycloalkyl groups such as dimethyl(cyclopentyl) ammonium ion, dimethyl(cyclohexyl) ammonium ion, and dimethyl(cycloheptyl) ammonium ion; (methylcyclopentyl) ammonium ion, bis(methylcyclopentyl) ammonium ion, and (dimethylcyclopentyl) ammonium ion. alkylcycloalkylammonium ions such as ammonium ions, bis(dimethylcyclopentyl)ammonium ions, (ethylcyclopentyl)ammonium ions, bis(ethylcyclopentyl)ammonium ions, (methylethylcyclopentyl)ammonium ions, bis(methylethylcyclopentyl)ammonium ions, (diethylcyclopentyl)ammonium ions, (methylcyclohexyl)ammonium ions, bis(methylcyclohexyl)ammonium ions, (dimethylcyclohexyl)ammonium ions, bis(dimethylcyclohexyl)ammonium ions, (ethylcyclohexyl)ammonium ions, bis(ethylcyclohexyl)ammonium ions, (methylethylcyclohexyl)ammonium ions, (diethylcyclohexyl)ammonium ions, (methylcycloheptyl)ammonium ions, bis(methylcycloheptyl)ammonium ions, (dimethylcycloheptyl)ammonium ions, (ethylcycloheptyl)ammonium ions, (methylethylcycloheptyl)ammonium ions, and (diethylcycloheptyl)ammonium ions.

[0039] Monomethanol ammonium ion, dimethanol ammonium ion, trimethanol ammonium ion, monoethanol ammonium ion, diethanol ammonium ion, triethanol ammonium ion, mono(n-propanol)ammonium ion, di(n-propanol)ammonium ion, tri(n-propanol)ammonium ion, monoisopropanol ammonium ion, diisopropanol ammonium ion, triisopropanol ammonium ion, monobutanol ammonium ion, dibutanol ammonium ion, tribetanol ammonium ion, monopentanol ammonium ion, dipentanol ammonium ion, tripentanol ammonium ion, monohexanol ammonium ion, dihexanol ammonium ion, monoheptanol ammonium ion, diheptanol ammonium ion, monooctanol ammonium ion, monononanol ammonium ion, monodecanol ammonium ion, monoundecanol ammonium ion, monododecanol ammonium ion, monotridecanol Ammonium ion, monotetradecanol ammonium ion, monopentadecanol ammonium ion, monohexadecanol ammonium ion, monomethyl monoethanol ammonium ion, monoethyl monoethanol ammonium ion, monoethyl monopropanol ammonium ion, monoethyl monobutanol ammonium ion, monoethyl monopentanol ammonium ion, monopropyl monoethanol ammonium ion, monopropyl monopropanol ammonium ion, monopropyl monobutanol ammonium ion, monopropyl monopentanol ammonium ion, monobutyl monoethanol ammonium ion, monobutyl monopropanol ammonium ion, monobutyl monobutanol ammonium ion, monobutyl monopentanol ammonium ion, dimethyl monoethanol ammonium ion, diethyl monoethanol ammonium ion, diethyl monopropanol ammonium ion, diethyl monobutanol ammonium ion, diethyl monopentanol ammonium ion, dipropyl monoethanol ammonium ion,Dipropyl monopropanol ammonium ion, dipropyl monobutanol ammonium ion, dipropyl monopentanol ammonium ion, dibutyl monoethanol ammonium ion, dibutyl monopropanol ammonium ion, dibutyl monobutanol ammonium ion, dibutyl monopentanol ammonium ion, monomethyl diethanol ammonium ion, monomethyl dipropanol ammonium ion, monomethyl dibutanol ammonium ion, monomethyl dipentanol ammonium ion, monoethyl diethanol ammonium ion, monoethyl dipropanol ammonium ion, monoethyl dibutanol ammonium ion, monoethyl dipentanol ammonium ion, monopropyl diethanol ammonium ion, monopropyl dipropanol ammonium ion, monopropyl dibutanol ammonium ion, monopropyl dipentanol ammonium ion, monobutyl diethanol ammonium ion, monobutyl dipropanol ammonium ion, monobutyl dibutanol ammonium ion, Dipentanol ammonium ion, monocyclohexyl monoethanol ammonium ion, monocyclohexyl diethanol ammonium ion, monocyclohexyl monopropanol ammonium ion, monocyclohexyl dipropanol ammonium ion, mono(β-aminoethyl) monoethanol ammonium ion, mono tert-butyl monoethanol ammonium ion, mono tert-butyl diethanol ammonium ion, mono(β-aminoethyl) isopropanol ammonium ion, diethyl monoisopropanol ammonium ion, trimethyl monoethanol ammonium ion, triethyl monoethanol ammonium ion, triethyl monopropanol ammonium ion, triethyl monobutanol ammonium ion, triethyl monopentanol ammonium ion, tripropyl monoethanol ammonium ion, tripropyl monopropanol ammonium ion, tripropyl monobutanol ammonium ion, tripropyl monopentanol ammonium ion, diethyl monomethylethanol ammonium ion,Alkanol ammonium ions such as bis(2-methoxyethyl)monoethyl monomethyl ammonium ion, monoethyl monomethyl diethanol ammonium ion, and diethyl monomethyl monoethanol ammonium ion. From the viewpoint of availability, monoethyl monoethanol ammonium ion, diethyl monoethanol ammonium ion, diethyl monomethyl ethanol ammonium ion, bis(2-methoxyethyl)monoethyl ammonium ion, bis(2-methoxyethyl)monoethyl monomethyl ammonium ion, monoethyl diethanol ammonium ion, and monoethyl monomethyl diethanol ammonium ion are preferred, and monoethyl monoethanol ammonium ion, diethyl monoethanol ammonium ion, and diethyl monomethyl monoethanol ammonium ion are particularly preferred.

[0040] Dimethyl ethyl monoacrylate ammonium ion, dimethyl ethyl monomethacrylate ammonium ion, diethyl ethyl monoacrylate ammonium ion, diethyl ethyl monomethacrylate ammonium ion, diethyl mono(2-isocyanoethyl)ammonium ion, diethyl mono(2-cyanopropyl)ammonium ion, diethyl mono(1,2-epoxypropane)ammonium ion.

[0041] In the above ammonium ions, descriptions such as "N-" and "N,N-" indicating a substituent on N are omitted.

[0042] Specific examples of the imidazolium ion include an imidazolium ion, an N-isobutylimidazolium ion, a 2-methylimidazolium ion, a 2-ethylimidazolium ion, a 2-n-propylimidazolium ion, a 2-isopropylimidazolium ion, a 2-n-butylimidazolium ion, a 2-phenylimidazolium ion, a 4-methylimidazolium ion, a 4-ethylimidazolium ion, a 4-nitroimidazolium ion, and a 4-phenylimidazolium ion. Examples of the imidazolium ion include 2-methyl-4-phenylimidazolium ion, 4,5-dimethylimidazolium ion, 1-isobutyl-2-methylimidazolium ion, 1-isobutyl-2,3-methylimidazolium ion, 2,4,5-trimethylimidazolium ion, 2,4,5-triphenylimidazolium ion, benzimidazolium ion, 2-methylbenzimidazolium ion, 2-phenylbenzimidazolium ion, etc. From the viewpoint of availability, 1-isobutyl-2-methylimidazolium ion and 1-isobutyl-2,3-methylimidazolium ion are particularly preferred.

[0043] Specific examples of pyridinium ions include pyridinium ion, 2-isobutylpyridinium ion, 3-isobutylpyridinium ion, 3-methylpyridinium ion, 4-methylpyridinium ion, 2-ethylpyridinium ion, 3-ethylpyridinium ion, 4-ethylpyridinium ion, 4-propylpyridinium ion, 2-n-hexylpyridinium ion, 3-n-hexylpyridinium ion, 3,5-dimethylpyridinium ion, 3,5-diethylpyridinium ion, 2,6-di-tert-butylpyridinium ion, 2-benzylpyridinium ion, 4-benzylpyridinium ion, 2-phenylpyridinium ion, 3-phenylpyridinium ion, 4-phenylpyridinium ion, 2,6-diphenylpyridinium ion, 2-( ... phenylpropyl)pyridinium ion, 4-(3-phenylpropyl)pyridinium ion, 2-benzoylpyridinium ion, 3-benzoylpyridinium ion, 4-benzoylpyridinium ion, 2-methoxypyridinium ion, 2-n-butoxypyridinium ion, 2,6-dimethoxypyridinium ion, 2-methoxy-6-methylpyridinium ion, 4-methoxy-3-nitropyridinium ion, 3-ethoxy-2-nitropyridinium ion, 2-methoxy-3-nitropyridinium ion, 4-(4-nitrobenzyl)pyridinium ion, 2-vinylpyridinium ion, 4-vinylpyridinium ion, 2-hydroxypyridinium ion, 3-hydroxypyridinium ion, 4-hydroxypyridinium ion, 2,4-dihydroxypyridinium ion, 2,6-dihydroxypyridinium ion, 3-hydroxymethylpyridinium ion, 4-hydroxymethylpyridinium ion, 2-(2-hydroxyethyl)pyridinium ion, 2-hydroxy-6-methylpyridinium ion, 3-hydroxy-2-methylpyridinium ion, 5-hydroxy-2-methylpyridinium ion, 2-hydroxy-3-nitropyridinium ion, 2-hydroxy-5-nitropyridinium ion, 4-hydroxy-3-nitropyridinium ion, 3-hydroxy-2-nitropyridinium ion, 2-hydroxy-6-methyl-5-nitropyridinium ion, 2-ethenylpyridinium ion, 2-ethynylpyridinium ion, 2-methyl-5-ethylpyridinium ion, 4-ethyl-2-methylpyridinium ion, 5-butyl-2-methylpyridinium ion, 2-ethyl-6-isopropylpyridinium ion, 3-ethyl-4-methylpyridinium ion, 2-methyl phenyl-5-vinylpyridinium ion, 4-(phenylpropyl)pyridinium ion, 4-(1-piperidyl)pyridinium ion, 4-pyrrolidinopyridinium ion, 2-pyrrolidin-2-ylpyridinium ion, 4-phenoxypyridinium ion, 2-methyl-3-ethylpyridinium ion, 2-methyl-5-(iso)propylpyridinium ion, 2-acetylpyridinium ion, 3-acetylpyridinium ion, 4-acetylpyridinium ion, 2-methyl-5-acetylpyridinium ion, 2,6-diacetylpyridinium ion, 2-phenoxy-5-acetylpyridinium ion, 2,6-bis(hydroxymethyl)pyridinium ion, 2,2'-bipyridinium ion, 2,6-bis(p-tolyl)pyridinium ion, N-Boc-3-hydroxy-1,2,3,6-tetrahydropyridinium ion, and N-Boc-1,2,3,6-tetrahydropyridinium ion. ,

[0044] Specific examples of pyrrolidinium ions include, for example, pyrrolidinium ion, N-methylpyrrolidinium ion, N-ethylpyrrolidinium ion, N-propylpyrrolidinium ion, N-butylpyrrolidinium ion, N-phenylpyrrolidinium ion, N-nitrosopyrrolidinium ion, 2-methylpyrrolidinium ion, 2-phenylpyrrolidinium ion, 3-phenylpyrrolidinium ion, 3-hydroxy-1-methylpyrrolidinium ion, 3-(4-methylphenyl)pyrrolidinium ion, 3-(pyrrolidinium-1-ylmethyl)piperidine, and 2-pyrrolidinium-2-ylpyridine.

[0045] Specific examples of the pyrrolinium ion include pyrrolinium ion, N-methylpyrrolinium ion, 2-acetyl-5-methylpyrrolinium ion, pyrrolinium-1-methyl carboxylate, 2-acetylpyrrolinium ion, 3-acetylpyrrolinium ion, 2,5-dimethyl-1-(4-nitrophenyl)-1H-pyrrolinium ion, 1-furfurylpyrrolinium ion, 1-(2-nitrophenyl)pyrrolinium ion, 1,2,5-trimethylpyrrolinium ion, 2,4-dimethylpyrrolinium-3,5-dicarboxylate, ethyl, 4-methylpyrrolinium-3-carboxylate, 4-phenylpyrrolinium-3-carboxylate, 3,4,5-trimethylpyrrolinium-2-carboxylate, 2,5-dimethylpyrrolinium-3-carboxylate, 1,2,5-trimethyl-1H-pyrrolinium-3-carboxylate, N-trimethoxysilylpyrrolinium ion, N-triethoxysilylpyrrolinium ion, N-(3-trimethoxysilylpropyl)pyrrolinium ion, and N-(3-triethoxysilylpropyl)pyrrolinium ion.

[0046] Specific examples of the piperidinium ion include, for example, a 2,6-dimethylpiperidinium ion, a 1,3-dimethyl-4-piperidinium ion, a 2,2,6,6-tetramethylpiperidinium ion, a 2,2,6,6-tetramethyl-4-hydroxypiperidinium ion, a 2,2-6-6-tetramethyl-4-acetoxypiperidinium ion, a 2,2,6,6-tetramethyl-4-acetamidopiperidinium ion, a 2,2,6,6-tetramethyl-4-oxopiperidinium ion, and a 2,2,6,6-tetramethyl-4-methoxypiperidinium ion. ion, 2,2,6,6-tetramethyl-4-propoxypiperidinium ion, 2,2,6,6-tetramethyl-4-(2-hydroxy-4-oxapentoxy)piperidinium ion, 2,2,6,6-tetramethyl-4-methacrylate piperidinium ion, 1,2,2,6,6-pentamethyl-4-methacrylate piperidinium ion, 1,2,2,6,6-pentamethyl-4-oxycarbonyl-2-propene piperidinium ion, 1,3-dimethyl-4-[2-cyclopentyl-2-phenylpropanoyl]oxypiperidinium ion, 1,3-dimethyl-4-(2-cyclopropyl-2-phenylpropanoyl)oxypiperidinium ion, 1,3-dimethyl-4-(2-cyclopentyl-2-pyridin-3-ylpropanoyl)oxypiperidinium ion, 1,3-dimethyl-4-[2-cyclopentyl-2-(4-hydroxyphenyl)propanoyl]oxypiperidinium ion, 1,3-dimethyl-4-(2-cyclobutyl-2-phenylpropanoyl)oxypiperidinium ion, 1,3-dimethyl-4-[2-cyclopentyl-2-(4-methoxyphenyl)propanoyl]oxypiperidinium ion, 1,3-dimethyl-4-[2-cyclopentyl-2-(2-thienyl)propanoyl]oxypiperidinium ion, 1,3-dimethyl-4-[2-cyclopentyl-2-(5-methyl-2-thienyl)propanoyl]oxypiperidinium ion, 1,3-dimethyl-4-[2-(3-bromophenyl)-2-cyclopentylpropanoyl]oxypiperidinium ion, 1,3-dimethyl-4-[2-(4-bromophenyl)-2-cyclopentylpropanoyl]oxypiperidinium ion, 1,3-Dimethyl-4-[2-(4-cyanophenyl)-2-cyclopentylpropanoyl]oxypiperidinium ion, 1,3-Dimethyl-4-[2-(3-cyanophenyl)-2-cyclopentylpropanoyl]oxypiperidinium ion, 1,3-Dimethyl-4-[2-(3-methylthiophenyl)-2-cyclopentylpropanoyl]oxypiperidinium ion, 1,3-Dimethyl-4-[2-(4-methylthiophenyl)-2-cyclopentylpropanoyl]oxypiperidinium ion, 1,3-Dimethyl-4-[2-(4-methylsulfonylphenyl)-2-cyclopentylpropanoyl]oxypiperidinium ion, 1,3-Dimethyl-4-[2-(4-methylsulfonylphenyl)-2-cyclopentylpropanoyl]oxypiperidinium ion, 1,3-dimethyl-4-[2-(3-methylsulfonylphenyl)-2-cyclopentylpropanoyl]oxypiperidinium ion, 1,3-dimethyl-4-[2-(4-fluorophenyl)-2-cyclopentylpropanoyl]oxypiperidinium ion, 1,3-dimethyl-4-[2-(4-chlorophenyl)-2-cyclopentylpropanoyl]oxypiperidinium ion, 1,3-dimethyl-4-[2-(3-fluorophenyl)-2-cyclopentylpropanoyl]oxypiperidinium ion, and 1,3-dimethyl-4-[2-(5-chloro-2-thienyl)-2-cyclobutylpropanoyl]oxypiperidinium ion.

[0047] Specific examples of the pyrazinium ion include, for example, a pyrazinium ion, a methyl pyrazinium carboxylate, a pyrazinium-2-carbonitrile, a pyrazinium carboxamide, a 2-acetyl-3-ethylpyrazinium ion, a 2-acetyl-3-methylpyrazinium ion, a 2-acetylpyrazinium ion, a 2-(aminomethyl)-5-methylpyrazinium ion, a 2-amino-3-(phenylmethyl)pyrazinium ion, a 2,3-bis(2'-pyridyl)-5,6-dihydropyrazinium ion, a 2-cyanopyrazinium ion, a 2,3-diethylpyrazinium ion, a 2-methyl ... 1-methylpyrazinium ion, 2,3-diethylpyrazinium ion, 6,7-dihydro-5-methyl-5H-cyclopentapyrazinium ion, 3,5-dimethyl-2-ethylpyrazinium ion, 2,3-dimethyl-5-isopropylpyrazinium ion, 2,3-dimethylpyrazinium ion, 2,5-dimethylpyrazinium ion, 2,6-dimethylpyrazinium ion, 2,3-diphenylpyrazinium ion, 2-ethoxy-3-ethylpyrazinium ion, 2-ethoxy-3-methylpyrazinium ion, 2-ethoxypyrazinium ion, 5-ethyl-2,3-dimethylpyrazinium ion, 2-ethyl-3-methoxypyrazinium ion, 2-ethyl-3-methylpyrazinium ion, ethylpyrazinium ion, 2-furfurylthiopyrazinium ion, 5-isobutyl-2,3-dimethylpyrazinium ion, 2-isobutyl-3-methoxypyrazinium ion, 2-isopropylpyrazinium ion, 2-(2-mercaptoethyl)pyrazinium ion, 2-methoxy-3-ethylpyrazinium ion, 2-methoxy-3-(1-methylpropyl)pyrazinium ion, 2- Methoxypyrazinium ion, 5-methyl-6,7-dihydrocyclopentapyrazinium ion, 2-methylmercapto-3-methylpyrazinium ion, 2-methyl-3-(methylthio)pyrazinium ion, 2-methyl-3-n-propylpyrazinium ion, 2-methylpyrazinium ion, 2-(methylthio)-3-ethylpyrazinium ion, 2-(methylthio)pyrazinium ion, 2-propylpyrazinium ion, 2-(1H-pyrazol-4-yl)pyrazinium ion, 2,3,5,6-tetramethylpyrazinium ion, 2,3,Examples include 5-trimethylpyrazinium ion and 2-vinylpyrazinium ion.

[0048] Specific examples of pyrimidinium ions include, for example, pyrimidinium ion, 4-methylpyrimidinium ion, 4-hydroxypyrimidinium ion, 4,6-dimethylpyrimidinium ion, 4,6-dihydroxypyrimidinium ion, 2,4,5-trihydroxypyrimidinium ion, 4,6-dihydroxy-2-methylpyrimidinium ion, 4,6-dihydroxy-5-nitropyrimidinium ion, 2,4-dimethyl-6-hydroxypyrimidinium ion, 4,6-dimethyl-2-hydroxypyrimidinium ion, 2-[4-n-(hexyloxy)phenyl]-5-n-octylpyrimidinium ion, 4-hydroxypyrazolo[3,4-d]-pyrimidinium ion, and 4,6-dihydroxypyrazolo[3,4-d]pyrimidinium ion.

[0049] Specific examples of triazolium ions include 1,2,3-triazolium ion, 1,2,4-triazolium ion, 3-mercapto-1,2,4-triazolium ion, 3-hydroxy-1,2,4-triazolium ion, 3-methyl-1,2,4-triazolium ion, 1-methyl-1,2,4-triazolium ion, 1-methyl-3-mercapto-1,2,4-triazolium ion, 4-methyl-1,2,3-triazolium ion, benzotriazolium ion, tolyltriazolium ion, 1-hydroxybenzotriazolium ion, 4,5,6 ,7-tetrahydrotriazolium ion, 3-amino-1,2,4-triazolium ion, 3-amino-5-methyl-1,2,4-triazolium ion, carboxybenzotriazolium ion, 2-(2'-hydroxy-5'-methylphenyl)benzotriazolium ion, 2-(2'-hydroxy-5'-tert-butylphenyl)benzotriazolium ion, 2-(2'-hydroxy-3',5'-di-tert-butylphenyl)benzotriazolium ion, and 2-(2'-hydroxy-4-octoxyphenyl)benzotriazolium ion.

[0050] Specific examples of the triazinium ion include, for example, a 1,2,3-triazinium ion, a 1,2,4-triazinium ion, a 1,3,5-triazinium ion, a 3,4-dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazinium ion, a 3-(2-pyridyl)-5,6-diphenyl-1,2,4-triazinium ion, a 5,6-diphenyl-1,2,4-triazinium ion, a hexahydro-1,3,5-triethyl-s-triazinium ion, a hexahydro-1,3,5-triphenyl-1,3,5-triazinium ion, a 2-(4-pyridinyl)-1,3,5-triazinium ion, a 1,3,5-triethyl-s-triazinium ion, a 2-(4-pyridinyl)-1,3,5 ... Examples of the acryloylhexahydro-1,3,5-triazinium ion include 2,4,6-triphenyl-s-triazinium ion, 2,4,6-tri(2-pyridyl)-s-triazinium ion, 2,4,6-tris(allyloxy)-1,3,5-triazinium ion, 1,3,5-tris(4-pyridyl)-2,4,6-triazinium ion, 2,4,6-tris(2-pyridyl)-1,3,5-triazinium ion, 1-(1,3,5-triazinium-2-yl)piperazine, 2,4,6-tripyridyl-s-triazinium ion, and 2,4,6-tris(allyloxy)-1,3,5-triazinium ion.

[0051] Specific examples of quinolinium ions include, for example, a quinolinium ion, a 2-methylquinolinium ion, a 3-methylquinolinium ion, a 4-methylquinolinium ion, an 8-methylquinolinium ion, a 2,8-dimethylquinolinium ion, a 3,8-dimethylquinolinium ion, a 4,8-dimethylquinolinium ion, a 7-methylquinolinium ion, a 2,7-dimethylquinolinium ion, a 3,7-dimethylquinolinium ion, a 4,7-dimethylquinolinium ion, a 6-methylquinolinium ion, a 2,6-dimethylquinolinium ion, a 3,6-dimethylquinolinium ion, a 4,6-dimethylquinolinium ion, an 8-ethylquinolinium ion, a 2-methyl-8-ethylquinolinium ion, a 4-methyl-8-ethylquinolinium ion, a 7-isopropyl-2-methylquinolinium ion, and a 6-tert-butyl-4-methylquinolinium ion.

[0052] Specific examples of the isoquinolinium ion include an isoquinolinium ion, a 3-methylisoquinolinium ion, a 4-methylisoquinolinium ion, a 5-methylisoquinolinium ion, a 6-methylisoquinolinium ion, a 7-methylisoquinolinium ion, an 8-methylisoquinolinium ion, a 1,3-dimethylisoquinolinium ion, a 5,8-dimethylisoquinolinium ion, a 5,6,7,8-tetramethylisoquinolinium ion, a 3-tert-butylisoquinolinium ion, a 4-tert-butylisoquinolinium ion, a 6-tert-butylisoquinolinium ion, and a 7-tert-butylisoquinolinium ion.

[0053] Specific examples of indolinium ions include, for example, an indolinium ion, a 3-methylindolinium ion, a 2-methylindolinium ion, a 1-methyl-3-methylindolinium ion, a 2,3-dimethylindolinium ion, a 3-ethylindolinium ion, a 2-phenylindolinium ion, a 3-phenylindolinium ion, a 2,3-phenylindolinium ion, a 2,3-dimethyl-7-nitroindolinium ion, a 2,3-dimethyl-7-chloroindolinium ion, a 3-ethyl-7-methylindolinium ion, a 2,3-dimethyl-7-methoxymethylindolinium ion, and a 7-methoxymethyl-3-methylindolinium ion. indolinium ion, 3-(pyridin-2-yl)indolinium ion, 3-(pyridin-2-yl)-2-methylindolinium ion, 3-(4,6-dimethoxypyrimidin-2-yl)-2-methylindolinium ion, 3-(4,6-dimethoxypyrimidin-2-yl)-7-ethyl-2-methylindolinium ion, 3-(4,6-dimethoxypyrimidin-2-yl)-7-methoxymethyl-2-methylindolinium ion, 3-(4,6-dimethoxypyrimidin-2-yl)-2-butoxymethylindolinium ion, 3-(4,6-diethoxypyrimidin-2-yl)-7-methoxymethylindolinium ion, and the like.

[0054] Specific examples of the quinoxalinium ion include a quinoxalinium ion, a 2-methylquinoxalinium ion, and a 2,3-dimethylquinoxalinium ion.

[0055] Specific examples of piperazinium ions include piperazinium ion, N-methylpiperazinium ion, N-ethylpiperazinium ion, N-(iso)propylpiperazinium ion, N-butylpiperazinium ion, N-phenylpiperazinium ion, 2-methylpiperazinium ion, 2,5-dimethylpiperazinium ion, 2,6-dimethylpiperazinium ion, 1,4-diphenylpiperazinium ion, 1-acetylpiperazinium ion, 1-allylpiperazinium ion, 1-(2-methylallyl)piperazinium ion, 1-(1-methylbutyl)piperazinium ion, 1-benzoyl rupiperazinium ion, 1-cyclopentylpiperazinium ion, 1-formylpiperazinium ion, 1-phenethylpiperazinium ion, 1-(4-pyridyl)piperazinium ion, 1-(2-pyrrolidinoethyl)piperazinium ion, 1-(o-tolyl)piperazinium ion, 1,4-diethylpiperazinium ion, 1,4-diformylpiperazinium ion, 1-(1,3-dimethylbutyl)piperazinium ion, 1-(2,3-dimethylphenyl)piperazinium ion, 1-(2,6-dimethylphenyl)piperazinium ion, 1-(3,4-dimethylphenyl)piperazinium ion, N,N'-dimethylpiperazinium ion, 1-(2-ethoxyethyl)piperazinium ion, 1-(2-ethoxyphenyl)piperazinium ion, 1-(2-methoxyethyl)piperazinium ion, 1-(2-methoxyphenyl)piperazinium ion, 1-(3-methoxyphenyl)piperazinium ion, 1-(4-methoxybenzyl)piperazinium ion, 1-(4-methoxybenzoyl)piperazinium ion, 1-[2-(phenoxy)ethyl]piperazinium ion, N-(2-hydroxyethyl)piperazinium ion, N-(4-hydroxyphenyl)piperazinium ion, 1- (2-hydroxyethyl)-4-isopropylpiperazinium ion, N-4-benzyl-2-phenylpiperazinium ion, 1-benzyl-4-(piperidin-3-ylmethyl)piperazinium ion, 1-(3-biphenylyl)piperazinium ion, 1-(4-biphenylyl)piperazinium ion, 1-cyclohexyl-4-(piperidin-3-ylmethyl)piperazinium ion, 1-(2,3-dimethylphenyl)-4-(piperidin-3-ylmethyl)piperazinium ion, 1-(2,4-dimethylphenyl)-4-(piperidin-3-ylmethyl)piperazinium ion, 1-(2,5-dimethylphenyl)-4-(piperidin-3-ylmethyl)piperazinium ion, 1-ethyl-4-(piperidin-3-ylmethyl)piperazinium ion, 1-(1-ethylpropyl)piperazinium ion, 1-(2-methoxyphenyl)-4-(piperidin-3-ylmethyl)piperazinium ion, 1-(2-methoxyphenyl)-4-(piperidin-4-ylmethyl)piperazinium ion, 1-(3-methoxyphenyl)-4-(piperidin-3-ylmethyl)piperazinium ion, 1-(3-methoxyphenyl)-4-(piperidin-4-ylmethyl)piperazinium ion, 2-methyl-1-(3-methylphenyl) 1-(3-methylphenyl)-4-(piperidin-3-ylmethyl)piperazinium ion, 2-methyl-1-(3-methylphenyl)-4-(piperidin-4-ylmethyl)piperazinium ion, 1-[(1-methylpiperidin-3-yl)methyl]piperazinium ion, 1-methyl-4-(piperidin-3-ylmethyl)piperazinium ion, 1-(3-methylpyridin-2-yl)piperazinium ion, 1-(piperidin-3-ylmethyl)-4-propylpiperazinium ion, 1-(piperidin-4-ylmethyl)-4-propylpiperazinium ion, 1-acetyl-4-(4-hydroxyphenyl)piperazinium ion, and the like.

[0056] Specific examples of the oxazolinium ion include, for example, an oxazolinium ion, a 4-methyloxazolinium ion, a 5-methyloxazolinium ion, a 4-phenyloxazolinium ion, a 4,5-diphenyloxazolinium ion, a 4-ethyloxazolinium ion, a 4,5-dimethyloxazolinium ion, a 5-phenyloxazolinium ion, a benzoxazolinium ion, a 5-chlorobenzoxazolinium ion, a 5-methylbenzoxazolinium ion, a 5-phenylbenzoxazolinium ion, a 6-methylbenzoxazolinium ion, and a 5-chlorobenzoxazolinium ion. Examples of the oxazolinium ion include sazolinium ion, 5,6-dimethylbenzoxazolinium ion, 4,6-dimethylbenzoxazolinium ion, 6-methoxybenzoxazolinium ion, 5-methoxybenzoxazolinium ion, 4-ethoxybenzoxazolinium ion, 5-chlorobenzoxazolinium ion, 6-methoxybenzoxazolinium ion, 5-hydroxybenzoxazolinium ion, 6-hydroxybenzoxazolinium ion, naphtho[1,2]oxazolinium ion, and naphtho[2,1]oxazolinium ion.

[0057] Specific examples of thiazolinium ions include, for example, thiazolinium ion, 2-aminothiazolinium ion, 2-methylthiazolinium ion, 2-methoxythiazolinium ion, 2-ethoxythiazolinium ion, 2-isobutylthiazolinium ion, 2-trimethylsilylthiazolinium ion, 5-trimethylsilylthiazolinium ion, 4-methylthiazolinium ion, 4,5-dimethylthiazolinium ion, 2-ethylthiazolinium ion, 2,4-dimethylthiazolinium ion, 2-amino-5-methylthiazolinium ion, 2-amino-4-methylthiazolinium ion, 2,4,5-trimethylthiazolinium ion, benzothiazolinium ion, 2-methylbenzothiazolinium ion, and 2,5-dimethylbenzothiazolinium ion.

[0058] Specific examples of the morpholinium ion include, for example, a morpholinium ion, an N-methylmorpholinium ion, an N-ethylmorpholinium ion, an N-(iso)propylmorpholinium ion, an N-(iso)butylmorpholinium ion, an N-acetylmorpholinium ion, an N-(2-nitrobutyl)morpholinium ion, an N-phenylmorpholinium ion, 4-morpholinoacetophenone, an N-(meth)acrylmorpholinium ion, an N-(meth)acryloylmorpholinium ion, and a bis(2 -morpholinium ethyl) ether, 4-morpholinium nitrobenzene, dimorpholinium methane, acetoacetomorpholide, 4-tert-butyl-2-(phenoxymethyl)morpholinium ion, 2,6-dimethylmorpholinium ion, 4-(2,3-epoxypropyl)morpholinium ion, N-formylmorpholinium ion, N-(2-hydroxyethyl)morpholinium ion, N-(4-nitrophenyl)morpholinium ion, N-nonanoylmorpholinium ion, etc. From the viewpoint of availability, N-methylmorpholinium ion and N-ethylmorpholinium ion are particularly preferred.

[0059] In the present invention, Q n+ is preferably an ammonium ion having an ethylenically unsaturated bond. n+ is more preferably an N,N-dimethyl ethyl ammonium monoacrylate ion, an N,N-dimethyl ethyl ammonium monomethacrylate ion, an N,N-diethyl ethyl ammonium monoacrylate ion, an N,N-diethyl ethyl ammonium monomethacrylate ion, an N,N-diethyl mono(2-isocyanoethyl)ammonium ion, an N,N-diethyl mono(2-cyanopropyl)ammonium ion, or an N,N-diethyl mono(1,2-epoxypropane)ammonium ion. n+ is even more preferably an N,N-dimethyl ethyl ammonium monoacrylate ion, an N,N-dimethyl ethyl ammonium monomethacrylate ion, an N,N-diethyl ethyl ammonium monoacrylate ion, or an N,N-diethyl ethyl ammonium monomethacrylate ion. n+is particularly preferably an N,N-dimethylmonoacrylate ethylammonium ion.

[0060] Q n+ has an ethylenically unsaturated bond, the number of ethylenically unsaturated bonds contained in the ionically bondable salt according to the present invention is not particularly limited and can be arbitrarily selected depending on the application, but is preferably one.

[0061] More preferred compounds of the ionic salt represented by the chemical formula (1) include ionic salts represented by the following chemical formulas (3) to (6). In the following chemical formulas (3) to (6), the oxybutylene group (-C4H8O-) is not particularly limited, but preferably has a branched butylene group, and more preferably has an ethylethylene group (-CH2-CH(CH2CH3)-). That is, the oxybutylene group preferably has a group represented by the above chemical formula (B1) or / and (B2). Such a compound can form a coating film or a molded product that has both water resistance and surface hydrophilicity. In the wettability improver according to this embodiment, only one type of ionic salt may be used alone, or two or more types may be used in combination. In addition, an ionic salt and a polymer thereof may be used in combination.

[0062] [ka]

[0063] (Method for producing ionic salt) The method for producing the ionically bonded salt having the reactive group is not particularly limited, and examples thereof include anion exchange method, neutralization method, acid ester method, etc. Also preferably used is a deammonification method in which an ionically bonded salt having a reactive group is obtained by reacting an ammonium salt of a sulfate ester or an ammonium salt of a sulfonate ester with a nitrogen-containing compound and distilling off ammonia.

[0064] The wettability enhancer according to one embodiment of the present invention is Q n+ has an ethylenically unsaturated bond (preferably, Qn+ is an ammonium ion having an ethylenically unsaturated bond). The polymer may be either a homopolymer of the ion-binding salt or a copolymer of the ion-binding salt and other monomers.

[0065] Here, the other monomer is not particularly limited as long as it is a monomer copolymerizable with the above-mentioned ion-bonding salt, but a monofunctional (meth)acrylic monomer is preferable, a (meth)acrylic acid alkyl ester having a substituted or unsubstituted C1-C20 alkyl group is more preferable, a (meth)acrylic acid alkyl ester having a substituted or unsubstituted C1-C8 alkyl group is even more preferable, a (meth)acrylic acid alkyl ester having a substituted or unsubstituted C1-C4 alkyl group is particularly preferable, and a (meth)acrylic acid alkyl ester having a substituted or unsubstituted C1-C2 alkyl group is most preferable.

[0066] Examples of the C1 to C20 alkyl group include a methyl group, an ethyl group, an n-propyl group, an isobutyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an n-hexyl group, and a 2-ethylhexyl group.

[0067] Substituents that may be contained in the other monomers include a hydroxyl group, an epoxy group, an amino group, a carboxyl group, and the like.

[0068] Specific examples of other monomers include (meth)acrylic acid, methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, t-butyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, methoxypolyethylene glycol (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, glycidyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, monoesters of (meth)acrylic acid and polyethylene glycol, 2-aminoethyl (meth)acrylate and its salts, caprolactone-modified (meth)acrylic acid, and (meth)acrylic acid. (Meth)acrylic acid esters such as 2,2,6,6-tetramethylpiperidine and (meth)acrylic acid-1,2,2,6,6-pentamethylpiperidine; (meth)acrylic acid salts such as sodium (meth)acrylate, potassium (meth)acrylate and ammonium (meth)acrylate; unsaturated nitriles such as acrylonitrile and methacrylonitrile; unsaturated amides such as (meth)acrylamide, N-methylol (meth)acrylamide and N-(2-hydroxyethyl) (meth)acrylamide; vinyl esters such as vinyl acetate and vinyl propionate; vinyl ethers such as methyl vinyl ether and ethyl vinyl ether; α-olefins such as ethylene and propylene; halogen-containing α,β-unsaturated aliphatic hydrocarbons such as vinyl chloride, vinylidene chloride and vinyl fluoride;Examples of the (meth)acrylic monomers include α,β-unsaturated aromatic hydrocarbons such as styrene, divinylbenzene, α-methylstyrene, and sodium styrenesulfonate, allyl (meth)acrylate, vinyl (meth)acrylate, epoxy acrylate, polyester (meth)acrylate, polyether (meth)acrylate, urethane (meth)acrylate, hexanediol di(meth)acrylate, butanediol di(meth)acrylate, (poly)ethylene glycol di(meth)acrylate, (poly)propylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, pentaerythritol di(meth)acrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol hexa(meth)acrylate, trimethylolpropane tri(meth)acrylate, and tetramethylolmethane tri(meth)acrylate. These may be used alone or in combination of two or more, but it is preferable to use two or more.;

[0069] When the polymer is a copolymer, the content of the structural unit derived from the ion-bonding salt is preferably 0.1 to 99% by mass, more preferably 0.5 to 95% by mass, 1.0 to 90% by mass, or 1.5 to 85% by mass, based on 100% by mass of the total amount of all structural units constituting the polymer. As in Example 7 described below, by preparing a polymer with a high content and adding a small amount of the polymer to a resin, the hydrophilicity of the resin surface can be increased without impairing the properties of the resin itself. The content is substantially equal to the ratio of the mass of the ion-bonding salt to the total mass of all monomers when producing the polymer.

[0070] The weight-average molecular weight of the polymer is not particularly limited, but is preferably 500 to 1,000,000, and more preferably 1,000 to 500,000. The weight-average molecular weight is a value measured using gel filtration chromatography (standard substance: polystyrene).

[0071] (Polymer manufacturing method) The polymer can be obtained by mixing an ion-bonding salt and, if necessary, other monomers, a solvent, additives, etc., and polymerizing the mixture by heating or irradiating light (such as ultraviolet light), etc. The polymerization method is not particularly limited, and known methods such as high-pressure radical polymerization, medium-low pressure polymerization, solution polymerization, slurry polymerization, bulk polymerization, emulsion polymerization, and gas phase polymerization can be used.

[0072] In the polymerization, it is preferable to use a polymerization initiator such as a thermal polymerization initiator or a photopolymerization initiator, or a polymerization catalyst such as a Ziegler-Natta catalyst or a metallocene catalyst, which may be used alone or in combination of two or more. The amount of the polymerization initiator added is preferably 0.1 to 5 parts by mass relative to 100 parts by mass of the total amount of all monomers.

[0073] Examples of the thermal polymerization initiator include methyl ethyl ketone peroxide, cyclohexanone peroxide, methylcyclohexanone peroxide, methylacetoacetate peroxide, acetylacetate peroxide, 1,1-bis(t-hexylperoxy)-3,3,5-trimethylcyclohexane, 1,1-bis(t-hexylperoxy)-cyclohexane, 1,1-bis(t-butylperoxy)-3,3,5-trimethylcyclohexane, 1,1-bis(t-butylperoxy)-2-methylcyclohexane, 1,1-bis(t -butylperoxy)-cyclohexane, 1,1-bis(t-butylperoxy)cyclododecane, 1,1-bis(t-butylperoxy)butane, 2,2-bis(4,4-di-t-butylperoxycyclohexyl)propane, p-menthane hydroperoxide, diisopropylbenzene hydroperoxide, 1,1,3,3-tetramethylbutyl hydroperoxide, cumene hydroperoxide, t-hexyl hydroperoxide, t-butyl hydroperoxide, α,α'-bis(t-butylperoxy)diisopropyl Pyrbenzene, dicumyl peroxide, 2,5-dimethyl-2,5-bis(t-butylperoxy)hexane, t-butylcumyl peroxide, di-t-butyl peroxide, 2,5-dimethyl-2,5-bis(t-butylperoxy)hexyne-3, isobutyryl peroxide, 3,5,5-trimethylhexanoyl peroxide, octanoyl peroxide, lauroyl peroxide, stearoyl peroxide, succinic acid peroxide, m-toluoylbenzoyl peroxide, benzoyl peroxide, di-n-propanol propyl peroxydicarbonate, diisopropyl peroxydicarbonate, bis(4-t-butylcyclohexyl) peroxydicarbonate, di-2-ethoxyethyl peroxydicarbonate, di-2-ethoxyhexyl peroxydicarbonate, di-3-methoxybutyl peroxydicarbonate, di-s-butyl peroxydicarbonate, di(3-methyl-3-methoxybutyl) peroxydicarbonate, α,α'-bis(neodecanoylperoxy)diisopropylbenzene, cumyl peroxyneodecanoate, 1,1,3,3-Tetramethylbutylperoxyneodecanoate, 1-cyclohexyl-1-methylethylperoxyneodecanoate, t-hexylperoxyneodecanoate, t-butylperoxyneodecanoate, t-hexylperoxypivalate, t-butylperoxypivalate, 1,1,3,3-tetramethylbutylperoxy-2-ethylhexanoate, 2,5-dimethyl-2,5-bis(2-ethylhexanoylperoxy)hexanoate, 1-cyclohexyl-1-methylethylperoxy-2-ethylhexanoate , t-hexylperoxy-2-ethylhexanoate, t-butylperoxy-2-ethylhexanoate, t-hexylperoxyisopropyl monocarbonate, t-butylperoxyisobutyrate, t-butylperoxymalate, t-butylperoxy-3,5,5-trimethylhexanoate, t-butylperoxylaurate, t-butylperoxyisopropyl monocarbonate, t-butylperoxy-2-ethylhexyl monocarbonate, t-butylperoxyacetate, t-butylperoxy-m-toluylbe organic peroxide initiators such as benzoate, t-butyl peroxybenzoate, bis(t-butylperoxy)isophthalate, 2,5-dimethyl-2,5-bis(m-toluylperoxy)hexane, t-hexyl peroxybenzoate, 2,5-dimethyl-2,5-bis(benzoylperoxy)hexane, t-butylperoxyallyl monocarbonate, t-butyltrimethylsilyl peroxide, 3,3',4,4'-tetra(t-butylperoxycarbonyl)benzophenone, and 2,3-dimethyl-2,3-diphenylbutane; 2-Phenylazo-4-methoxy-2,4-dimethylvaleronitrile, 1-[(1-cyano-1-methylethyl)azo]formamide, 1,1'-azobis(cyclohexane-1-carbonitrile), 2,2'-azobis(2-methylbutyronitrile), 2,2'-azobisisobutyronitrile (AIBN), 2,2'-azobis(2,4-dimethylvaleronitrile), 2,2'-azobis(2-methylpropionamidine) dihydrochloride, 2,2'-azobis(2-methyl-N-phenylpropionamidine) dihydrochloride, 2,2'-Azobis[N-(4-chlorophenyl)-2-methylpropionamidine]dihydridochloride, 2,2'-Azobis[N-(4-hydrophenyl)-2-methylpropionamidine]dihydrochloride, 2,2'-Azobis[2-methyl-N-(phenylmethyl)propionamidine]dihydrochloride, 2,2'-Azobis[2-methyl-N-(2-propenyl)propionamidine]dihydrochloride, 2,2'-Azobis[N-(2-hydroxyethyl)-2-methylpropionamidine] dihydrochloride, 2,2'-azobis[2-(5-methyl-2-imidazolin-2-yl)propane]dihydrochloride, 2,2'-azobis[2-(2-imidazolin-2-yl)propane]dihydrochloride, 2,2'-azobis[2-(4,5,6,7-tetrahydro-1H-1,3-diazepin-2-yl)propane]dihydrochloride, 2,2'-azobis[2-(3,4,5,6-tetrahydropyrimidin-2-yl)propane]dihydrochloride, 2,2'-azobis[2-(5- 2,2'-Azobis[2-[1-(2-hydroxyethyl)-2-imidazolin-2-yl]propane]dihydrochloride, 2,2'-Azobis[2-(2-imidazolin-2-yl)propane], 2,2'-Azobis[2-methyl-N-[1,1-bis(hydroxymethyl)-2-hydroxyethyl]propionamide], 2,2'-Azobis[2-methyl-N-[1,1-bis(hydroxymethyl)-2-hydroxyethyl]propionamide] )ethyl]propionamide], 2,2'-azobis[2-methyl-N-(2-hydroxyethyl)propionamide], 2,2'-azobis(2-methylpropionamide), 2,2'-azobis(2,4,4-trimethylpentane), 2,2'-azobis(2-methylpropane), dimethyl-2,2-azobis(2-methylpropionate), 4,4'-azobis(4-cyanopentanoic acid), 2,2'-azobis[2-(hydroxymethyl)propionitrile], and the like. These thermal polymerization initiators may be used alone or in combination of two or more.

[0074] Examples of photopolymerization initiators include 2-hydroxy-1-{4-[4-(2-hydroxy-2-methyl-propionyl)-benzyl]phenyl}-2-methyl-propan-1-one, diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyl dimethyl ketal, 4-(2-hydroxyethoxy)phenyl-(2-hydroxy-2-propyl)ketone, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-2-morpholino(4-thiomethylphenyl)propan-1-one, 2-benzyl dimethyl ketone ... acetophenones such as 2-hydroxy-2-methyl-1-[4-(1-methylvinyl)phenyl]propanone oligomer; benzoins such as benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone, o-benzoyl methyl benzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyl-diphenyl sulfide, 3,3',4,4'-tetrabenzoyl benzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyl-diphenyl sulfide, 3,3',4,4'-tetrabenzoyl benzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyl-diphenyl sulfide, 3,3',4,4'-tetrabenzoyl benzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyl-diphenyl sulfide, 3,3',4,4'-tetrabenzoyl benzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyl-diphenyl sulfide, 3,3',4,4'-tetrabenzoyl benzoate, 4-phenylbenzophenone, 4-phenyl ... benzophenones such as tetra(t-butylperoxycarbonyl)benzophenone, 2,4,6-trimethylbenzophenone, 4-benzoyl-N,N-dimethyl-N-[2-(1-oxo-2-propenyloxy)ethyl]benzenemethanaminium bromide, and (4-benzoylbenzyl)trimethylammonium chloride; 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4-propoxythioxanthone, 2-(3-dimethylthioxanthone, 4-methylthioxanthone, 1 ... thioxanthones such as bis(2,6-dimethoxybenzoyl)-2,4,4-trimethyl-pentylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, and the like; oxime esters; cationic photopolymerization initiators; intramolecular hydrogen abstraction photopolymerization initiators; and the like. These photopolymerization initiators may be used alone or in combination of two or more.

[0075] In addition, the method of obtaining the above polymer by emulsion polymerization of other monomers in an aqueous solvent in the presence of a polymerization initiator using the ion-bonding salt according to the present invention as an emulsifier, or the method of obtaining the above polymer by solution polymerization or ultraviolet polymerization of the ion-bonding salt according to the present invention and other monomers in an organic solvent in the presence of a polymerization initiator, are also preferably used because they have excellent productivity. In this case, other surfactants such as anionic surfactants and nonionic surfactants can be used as emulsifiers together with the above ion-bonding salt.

[0076] Examples of the solvent used in the solution polymerization method include ethyl acetate, butyl acetate, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, tetrahydrofuran, dioxane, N,N-dimethylformamide, N,N-dimethylacetamide, benzene, toluene, xylene, acetonitrile, methylene chloride, chloroform, dichloroethane, methanol, ethanol, n-propanol, isopropanol, n-butanol, propylene glycol monomethyl ether, etc. These may be used alone or in combination of two or more, or may be used as a mixed solvent with water.

[0077] The polymerization conditions in the solution polymerization method are not particularly limited, and for example, the polymerization temperature can be appropriately set depending on the type of catalyst used, but is preferably 50 to 120° C. The polymerization time is also not particularly limited, but is preferably 1 to 10 hours. The polymerization method is also not particularly limited, and examples thereof include polymerization by batch charging of monomers, polymerization by dropping, and power feed polymerization.

[0078] When polymerization is performed by irradiation with ultraviolet light, a mercury lamp (e.g., a high-pressure mercury lamp or a low-pressure mercury lamp), a metal halide lamp, etc. can be used as the irradiation light source. The conditions for the ultraviolet light irradiation are not particularly limited, but the cumulative light amount is preferably 100 mJ / cm. 2 More than 200 mJ / cm is preferable. 2 The above is more preferable.

[0079] [Silicate or its condensate] The wettability enhancer according to the present embodiment essentially contains the following silicate or a condensate thereof in addition to the above-mentioned ion-bonding salt or a polymer thereof.

[0080] (Silicate structure) The silicate contained in the wettability enhancer according to the present embodiment is represented by the following chemical formula (A).

[0081] [ka]

[0082] In the above chemical formula (A), R may be the same or different and represent a hydrogen atom or an optionally substituted monovalent hydrocarbon group having 1 to 10 carbon atoms. Preferably, at least one of R's, more preferably at least two, even more preferably at least three, and particularly preferably all four of R's are the above hydrocarbon group.

[0083] The monovalent hydrocarbon group may be linear, branched, or cyclic, and may be saturated or unsaturated. Examples of the monovalent hydrocarbon group include an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a cycloalkenyl group, a cycloalkynyl group, and an aryl group.

[0084] Examples of the alkyl group include alkyl groups having 1 to 10 carbon atoms, such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a tert-pentyl group, a neopentyl group, a 1,2-dimethylpropyl group, an n-hexyl group, an isohexyl group, a 1,3-dimethylbutyl group, a 1-isopropylpropyl group, a 1,2-dimethylbutyl group, an n-heptyl group, a 1,4-dimethylpentyl group, a 3-ethylpentyl group, a 2-methyl-1-isopropylpropyl group, a 1-ethyl-3-methylbutyl group, an n-octyl group, a 2-ethylhexyl group, a 3-methyl-1-isopropylbutyl group, a 2-methyl-1-isopropyl group, a 1-t-butyl-2-methylpropyl group, an n-nonyl group, a 3,5,5-trimethylhexyl group, an n-decyl group, and an isodecyl group.

[0085] Examples of the alkenyl group include alkenyl groups having 2 to 10 carbon atoms, such as a vinyl group, an allyl group, a 2-butenyl group, a 3-pentenyl group, a hexenyl group, a heptenyl group, an octenyl group, a nonenyl group, and a decenyl group.

[0086] Examples of the alkynyl group include alkynyl groups having 2 to 10 carbon atoms, such as a 2-butynyl group, a 3-pentynyl group, a hexynyl group, a heptynyl group, an octynyl group, and a decynyl group.

[0087] Examples of the cycloalkyl group include cycloalkyl groups having 3 to 10 carbon atoms, such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and a cyclodecyl group.

[0088] Examples of the cycloalkenyl group include cycloalkenyl groups having 3 to 10 carbon atoms, such as a cyclopropenyl group, a cyclobutenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a cyclooctenyl group, and a cyclodecenyl group.

[0089] Examples of the cycloalkynyl group include cycloalkynyl groups having 3 to 10 carbon atoms, such as a cyclobutynyl group, a cyclopentynyl group, a cyclohexynyl group, a cycloheptynyl group, a cyclooctynyl group, and a cyclodecynyl group.

[0090] Examples of the aryl group include aryl groups having 6 to 10 carbon atoms, such as a phenyl group and a naphthyl group, of which the phenyl group is preferred.

[0091] The substituent that can be introduced into the monovalent hydrocarbon group as R is not particularly limited, and examples thereof include a cyano group, a halogen atom, an alkyl group, an alkoxy group, a cycloalkyl group, a cycloalkoxy group, an aryl group, an aryloxy group, an aralkyl group, an alkylamino group, and an arylamino group. However, the form in which the substituted structure is the same as the group before the substitution is excluded. Therefore, for example, when R is an alkyl group, the alkyl group is not further substituted with an alkyl group.

[0092] From the viewpoint of further improving the effects of the present invention, R is preferably an optionally substituted alkyl group having 1 to 10 carbon atoms or an optionally substituted aryl group having 6 to 10 carbon atoms, and from the viewpoint of further improving the water resistance of the coating film to be formed, it is more preferably an optionally substituted alkyl group having 1 to 10 carbon atoms. Furthermore, the number of carbon atoms in the alkyl group represented by R is preferably 8 or less, more preferably 6 or less, even more preferably 4 or less, particularly preferably 3 or less, and most preferably 2 or less.

[0093] Among silicates, specific examples of compounds in which all four R are hydrocarbon groups include tetramethoxysilane, tetraethoxysilane, tetra-n-propoxysilane, tetra-i-propoxysilane, tetra-n-butoxysilane, tetra-i-butoxysilane, and tetra-t-butoxysilane.

[0094] In the wettability improver according to the present embodiment, only one type of silicate may be used alone, or two or more types may be used in combination. Also, silicate and its condensate may be used in combination. Furthermore, organosilicates containing different alkoxysilyl groups in the same molecule may be used. For example, methyl ethyl silicate, methyl propyl silicate, methyl butyl silicate, ethyl propyl silicate, propyl butyl silicate, etc. may be used. The ratio of each of these substituents can be changed arbitrarily between 0% and 100%.

[0095] In addition, in the wettability improver according to the present embodiment, the partial hydrolysis / condensation product of the above-mentioned silicate (also simply referred to as "condensation product" in this specification) may be used. Here, the molar number of the silicate constituting the condensation product is not particularly limited, but a dimer to octamer of the silicate is preferable, a trimer to octamer is more preferable, and a tetramer to octamer is particularly preferable.

[0096] The content of the silicate or condensate thereof in the wettability improver according to the present invention is preferably 50 to 250 mass%, more preferably 65 to 200 mass%, and even more preferably 80 to 150 mass%, relative to 100 mass% of the content of the ionically bondable salt or polymer thereof.

[0097] The wettability improver according to the present embodiment may contain components other than the ion-bonding salt or its polymer, and the silicate or its condensate. Examples of such components include compounds in which one or more of the four OR groups in the chemical formula (A) are substituted with an R group (having a Si-R bond). In such compounds, it is preferable that one to three OR groups out of the four OR groups in the chemical formula (A) are substituted with an R group, more preferable that one to two OR groups are substituted with an R group, and particularly preferable that one OR group is substituted with an R group. Examples of compounds in which one OR group out of the four OR groups in the chemical formula (A) is substituted with an R group include so-called silane coupling agents. In silane coupling agents, various reactive functional groups such as (meth)acrylic groups, vinyl groups, amino groups, glycidyl groups, and mercapto groups are usually present at the end of the R group that has substituted the OR group. Specific examples of the silane coupling agent include (meth)acrylic group-containing silane coupling agents such as γ-methacryloxypropyltrimethoxysilane; vinyl group-containing silane coupling agents such as vinyltris(β-methoxyethoxy)silane, vinyltriethoxysilane, and vinyltrimethoxysilane; amino group-containing silane coupling agents such as 3-(2-aminoethylamino)propyltrimethoxysilane (N-β-(aminoethyl)-γ-aminopropyltrimethoxysilane), γ-aminopropyltriethoxysilane, and N-phenyl-γ-aminopropyltrimethoxysilane. coupling agents; glycidyl group-containing silane coupling agents such as 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, glycidylpropyltrimethoxysilane (3-glycidoxypropyltrimethoxysilane), and 3-glycidoxypropylmethyldiethoxysilane; γ-mercaptopropyltrimethoxysilane, γ-chloropropyltrimethoxysilane, styrylsilane, ureidosilane, sulfidosilane, and isocyanate silane.Among these, the silane coupling agent is preferably a (meth)acrylic group-containing silane coupling agent, a vinyl group-containing silane coupling agent, or an amino group-containing silane coupling agent, more preferably a (meth)acrylic group-containing silane coupling agent or a vinyl group-containing silane coupling agent, and particularly preferably a (meth)acrylic group-containing silane coupling agent. The present invention also provides a wettability improver using a silane coupling agent instead of the above-mentioned silicate or its condensate. That is, according to the present invention, a wettability improver is also provided, which includes an ion-bonding salt represented by the above chemical formula (1) or a polymer thereof and a silane coupling agent. Such a wettability improver can also solve the above-mentioned problems.

[0098] The content of the "compound in which one or more of the four OR groups in chemical formula (A) are substituted with R groups (having a Si-R bond)" (preferably a silane coupling agent) in the wettability improver of the present invention is preferably 0 to 30 mass%, more preferably 0 to 20 mass%, and even more preferably 0 to 15 mass%, relative to 100 mass% of the content of the ionically bondable salt or its polymer.

[0099] In addition to the above, the wettability improver according to the present embodiment may contain solvents, inorganic or organic fillers, various surfactants, reactive compounds such as polyisocyanate compounds, epoxy compounds, and organometallic compounds, antioxidants, processing aids, ultraviolet absorbers, fluorescent brightening agents, antislip agents, antiblocking agents, antistatic agents, light stabilizers, lubricants, softeners, colored dyes, and other stabilizers.

[0100] <Resin composition> The present invention also provides a resin composition containing the above-mentioned wettability improver and a resin. The resin is preferably a thermoplastic resin or / and a thermosetting resin, more preferably a thermoplastic resin. Each resin will be described below. In this specification, the concept of "resin" includes monomers, oligomers, prepolymers, and polymers.

[0101] [Thermoplastic resin] The thermoplastic resin used in the present invention is not particularly limited, but examples thereof include (meth)acrylic resin, styrene resin, olefin resin (including cyclic olefin resin), polyester resin, polycarbonate resin, polyamide resin, polyphenylene ether resin, polyphenylene sulfide resin, halogen-containing resin (polyvinyl chloride, polyvinylidene chloride, fluororesin, etc.), polysulfone resin (polyethersulfone, polysulfone, etc.), cellulose derivatives (cellulose esters, cellulose carbamates, cellulose ethers, etc.), silicone resins (polydimethylsiloxane, polymethylphenylsiloxane, etc.), polyvinyl ester resins such as polyvinyl acetate, polyvinyl alcohol resins and their derivative resins, rubber or elastomer (diene rubbers such as polybutadiene and polyisoprene, styrene-butadiene copolymers, acrylonitrile-butadiene copolymers, acrylic rubbers, urethane rubbers, silicone rubbers, etc.). The above thermoplastic resins can be used alone or in combination of two or more.

[0102] Specific examples of the (meth)acrylic resin include monofunctional (meth)acrylic monomers and homopolymers or copolymers thereof, polyfunctional (meth)acrylic monomers and homopolymers or copolymers thereof, and copolymers of monofunctional or polyfunctional (meth)acrylic monomers and other monomers.

[0103] Specific examples of monofunctional (meth)acrylic monomers include (meth)acrylic acid, (meth)acrylic acid esters having 1 to 10 carbon atoms, such as methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, n-butyl (meth)acrylate, and 2-ethylhexyl (meth)acrylate, hydroxyalkyl (meth)acrylates, such as hydroxyethyl (meth)acrylate, glycidyl (meth)acrylate, and (meth)acrylonitrile.

[0104] Specific examples of polyfunctional (meth)acrylic monomers include polyethylene glycol diacrylate, decanediol diacrylate, nonanediol diacrylate, hexanediol diacrylate, tricyclodecane dimethanol diacrylate, trimethylolpropane triacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, dipentaerythritol pentaacrylate, and dipentaerythritol hexaacrylate.

[0105] Specific examples of the homopolymer or copolymer of the (meth)acrylic monomer include poly(meth)acrylic acid ester, acrylic acid ester-methacrylic acid ester copolymer, polyacrylonitrile, etc. Specific examples of the copolymer of the (meth)acrylic monomer and another monomer include (meth)acrylic acid-styrene copolymer, (meth)acrylic acid ester-styrene copolymer, (meth)acrylic acid ester-(meth)acrylic acid-styrene copolymer, acrylonitrile-butadiene-styrene copolymer, acrylonitrile-styrene copolymer, acrylonitrile-styrene-(meth)acrylic acid ester copolymer, acrylonitrile-acrylic acid ester-styrene copolymer (AAS resin), methyl methacrylate-butadiene-styrene copolymer (MBS resin), etc.

[0106] Specific examples of styrene resins include polystyrene, poly-α-methylstyrene, α-methylstyrene-acrylonitrile copolymer, styrene-N-phenylmaleimide copolymer, styrene-N-phenylmaleimide-acrylonitrile copolymer, and rubber-reinforced polystyrene resin (HIPS resin).

[0107] The olefin resin includes homopolymers of olefin monomers, copolymers of olefin monomers, and copolymers of olefin monomers and other copolymerizable monomers. Specific examples of olefin monomers include linear olefins [α-olefins having 2 to 20 carbon atoms, such as ethylene, propylene, 1-butene, isobutene, 1-pentene, 4-methyl-1-pentene, 1-hexene, 1-octene, and 1-decene], and cyclic olefins [cycloalkenes having 4 to 10 carbon atoms, such as cyclopentene; cycloalkadienes having 4 to 10 carbon atoms, such as cyclopentene; bicycloalkenes having 7 to 20 carbon atoms or bicycloalkadienes having 7 to 20 carbon atoms, such as norbornene and norbornadiene; tricycloalkenes having 10 to 25 carbon atoms, such as dihydrodicyclopentadiene and dicyclopentadiene]. These olefin monomers can be used alone or in combination of two or more. Among the above olefin monomers, chain olefins such as α-olefins having 2 to 4 carbon atoms, such as ethylene, propylene, and 1-butene, are preferred.

[0108] Specific examples of other copolymerizable monomers that can be copolymerized with the olefin monomer include fatty acid vinyl esters such as vinyl acetate and vinyl propionate; (meth)acrylic monomers such as (meth)acrylic acid, alkyl (meth)acrylate, and glycidyl (meth)acrylate; unsaturated dicarboxylic acids or anhydrides thereof such as maleic acid, fumaric acid, and maleic anhydride; vinyl esters of carboxylic acids (e.g., vinyl acetate, vinyl propionate, etc.); cyclic olefins such as norbornene and cyclopentadiene; and dienes such as butadiene and isoprene. These copolymerizable monomers can be used alone or in combination of two or more.

[0109] More specific examples of the olefin resin include polyethylene (low density polyethylene, medium density polyethylene, high density polyethylene, linear low density polyethylene, etc.), polypropylene (homopolypropylene, block polypropylene, random polypropylene, etc.), ethylene-propylene copolymer, ethylene-propylene-butene terpolymer, and other linear olefin (particularly, C2-4 α-olefin) (co)polymers. Specific examples of copolymers of olefin monomers and other copolymerizable monomers include, for example, copolymers of linear olefins (particularly, C2-4 α-olefins such as ethylene and propylene) and fatty acid vinyl ester monomers (for example, ethylene-vinyl acetate copolymer, ethylene-vinyl propionate copolymer, etc.); copolymers of linear olefins and (meth)acrylic monomers [copolymers of linear olefins (particularly, C2-4 α-olefins) and (meth)acrylic acid (for example, ethylene-(meth)acrylic acid copolymer, propylene-(meth)acrylic acid copolymer, ionomer, etc.); copolymers of linear olefins (particularly, C2-4 α-olefins) and alkyl ( copolymers of linear olefins (particularly α-olefins having 2 to 4 carbon atoms) and dienes (for example, ethylene-butadiene copolymers); modified polyolefins such as epoxy-modified polyolefins (for example, ethylene-glycidyl (meth)acrylate copolymers), carboxy-modified polyolefins (for example, ethylene-maleic anhydride copolymers), and epoxy and carboxy-modified polyolefins (for example, ethylene-maleic anhydride-glycidyl (meth)acrylate copolymers); olefin elastomers (ethylene-propylene rubber, etc.).

[0110] Specific examples of polyester resins include polymers or copolymers obtained by polycondensation of at least one selected from the group consisting of (a) dicarboxylic acids or derivatives thereof and diols or derivatives thereof, (b) hydroxycarboxylic acids or derivatives thereof, and (c) lactones.

[0111] Examples of the dicarboxylic acid or a derivative thereof include aromatic dicarboxylic acids such as terephthalic acid, isophthalic acid, phthalic acid, 2,6-naphthalenedicarboxylic acid, 1,5-naphthalenedicarboxylic acid, bis(p-carboxyphenyl)methane, anthracenedicarboxylic acid, 4,4'-diphenyletherdicarboxylic acid, 5-tetrabutylphosphoniumisophthalic acid, and 5-sodiumsulfoisophthalic acid; aliphatic dicarboxylic acids such as oxalic acid, succinic acid, adipic acid, sebacic acid, azelaic acid, dodecanedioic acid, malonic acid, glutaric acid, and dimer acid; 1,3-cyclohexanedicarboxylic acid, and 1,4-cyclohexanedicarboxylic acid. Examples of the diol or derivative include aliphatic glycols having 2 to 20 carbon atoms, i.e., ethylene glycol, propylene glycol, 1,4-butanediol, neopentyl glycol, 1,5-pentanediol, 1,6-hexanediol, decamethylene glycol, cyclohexanedimethanol, cyclohexanediol, dimer diol, etc., long-chain glycols having a molecular weight of 200 to 100,000, i.e., polyethylene glycol, poly-1,3-propylene glycol, polytetramethylene glycol, etc., aromatic dioxy compounds, i.e., 4,4'-dihydroxybiphenyl, hydroquinone, t-butylhydroquinone, bisphenol A, bisphenol S, bisphenol F, etc., and derivatives thereof. Examples of the hydroxycarboxylic acid include glycolic acid, lactic acid, hydroxypropionic acid, hydroxybutyric acid, hydroxyvaleric acid, hydroxycaproic acid, hydroxybenzoic acid, p-hydroxybenzoic acid, 6-hydroxy-2-naphthoic acid, and derivatives thereof. Examples of the lactone include caprolactone, valerolactone, propiolactone, undecalactone, 1,5-oxepan-2-one, etc. The polyester resin also includes polyester elastomers.

[0112] Specific examples of polycarbonate resins include thermoplastic resins obtained by reacting a divalent or higher phenol compound with a carbonate diester compound such as phosgene or diphenyl carbonate.

[0113] Examples of the divalent or higher phenolic compound include 2,2-bis(4-hydroxyphenyl)propane (commonly known as bisphenol A), bis(4-hydroxyphenyl)methane, bis(4-hydroxyphenyl)phenylmethane, bis(4-hydroxyphenyl)naphthylmethane, bis(4-hydroxyphenyl)-(4-isopropylphenyl)methane, bis(3,5-dichloro-4-hydroxyphenyl)methane, bis(3,5-dimethyl-4-hydroxyphenyl)methane, 1,1-bis(4-hydroxyphenyl)ethane, 1,2-bis(4-hydroxyphenyl)ethane, 1,3-bis(4-hydroxyphenyl)ethane, 1,4-bis(4-hydroxyphenyl)ethane, 1,5-bis(4-hydroxyphenyl)ethane, 1,6-bis(4-hydroxyphenyl)ethane, 1,7-bis(4-hydroxyphenyl)ethane, 1,8-bis(4-hydroxyphenyl)ethane, 1,9-bis(4-hydroxyphenyl) ... -Naphthyl-1,1-bis(4-hydroxyphenyl)ethane, 1-phenyl-1,1-bis(4-hydroxyphenyl)ethane, 1,2-bis(4-hydroxyphenyl)ethane, 2-methyl-1,1-bis(4-hydroxyphenyl)propane, 2,2-bis(3,5-dimethyl-4-hydroxyphenyl)propane, 1-ethyl-1,1-bis(4-hydroxyphenyl)propane, 2,2-bis(3,5-dichloro-4-hydroxyphenyl)propane, 2,2-bis(3,5-dibromo-4-hydroxyphenyl)propane , 2,2-bis(3-chloro-4-hydroxyphenyl)propane, 2,2-bis(3-methyl-4-hydroxyphenyl)propane, 2,2-bis(3-fluoro-4-hydroxyphenyl)propane, 1,1-bis(4-hydroxyphenyl)butane, 2,2-bis(4-hydroxyphenyl)butane, 1,4-bis(4-hydroxyphenyl)butane, 2,2-bis(4-hydroxyphenyl)pentane, 4-methyl-2,2-bis(4-hydroxyphenyl)pentane, 2,2-bis(4-hydroxyphenyl)hexane , 4,4-bis(4-hydroxyphenyl)heptane, 2,2-bis(4-hydroxyphenyl)nonane, 1,10-bis(4-hydroxyphenyl)decane, 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane, 2,2-bis(4-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropane and other dihydroxydiarylalkanes, 1,1-bis(4-hydroxyphenyl)cyclohexane, 1,1-bis(3,5-dichloro-4-hydroxyphenyl)cyclohexane, 1,Dihydroxydiarylcycloalkanes such as 1-bis(4-hydroxyphenyl)cyclodecane, dihydroxydiarylsulfones such as bis(4-hydroxyphenyl)sulfone, bis(3,5-dimethyl-4-hydroxyphenyl)sulfone, and bis(3-chloro-4-hydroxyphenyl)sulfone, dihydroxyaryl ethers such as bis(4-hydroxyphenyl)ether and bis(3,5-dimethyl-4-hydroxyphenyl)ether, 4,4'-dihydroxybenzophenone, 3,3',5,5'-tetramethyl-4,4'-dihydro Examples of the dihydric phenol compound include dihydroxydiaryl ketones such as 4-hydroxybenzophenone, dihydroxydiaryl sulfides such as bis(4-hydroxyphenyl)sulfide, bis(3-methyl-4-hydroxyphenyl)sulfide, and bis(3,5-dimethyl-4-hydroxyphenyl)sulfide, dihydroxydiaryl sulfoxides such as bis(4-hydroxyphenyl)sulfoxide, dihydroxydiphenyls such as 4,4'-dihydroxydiphenyl, and dihydroxyarylfluorenes such as 9,9-bis(4-hydroxyphenyl)fluorene. In addition to the above dihydric phenol compounds, dihydroxybenzenes such as hydroquinone, resorcinol, and methylhydroquinone, and dihydroxynaphthalenes such as 1,5-dihydroxynaphthalene and 2,6-dihydroxynaphthalene can be used as the dihydric phenol compound.

[0114] These divalent or higher phenolic compounds may be used alone or in combination of two or more. In addition, linear aliphatic divalent carboxylic acids such as adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, and decanedicarboxylic acid may be used as copolymerization components.

[0115] Specific examples of polyamide resins include aliphatic polyamides such as polyamide 46, polyamide 5, polyamide 6, polyamide 66, polyamide 610, polyamide 612, polyamide 11, polyamide 12, polyamide 6 / 66, and polyamide 6 / 11; alicyclic polyamides such as poly-1,4-norbornene terephthalamide, poly-1,4-cyclohexane terephthalamide, and poly-1,4-cyclohexane-1,4-cyclohexanamide; aromatic polyamides such as polyamide 6T, polyamide 9T, and polyamide MXD; and copolyamides formed from at least two different polyamide forming components among these polyamides. The polyamide resins also include polyamide elastomers.

[0116] Specific examples of polyphenylene ether resins include homopolymers such as poly(2,5-dimethyl-1,4-phenylene ether), poly(2,6-dimethyl-1,4-phenylene ether), poly(2-methyl-6-ethyl-1,4-phenylene ether), poly(2,6-di-n-propyl-1,4-phenylene ether), and poly(2-methyl-6-chloroethyl-1,4-phenylene ether); modified polyphenylene ether copolymers based on these homopolymers; and modified graft copolymers in which a styrene polymer is grafted onto a polyphenylene ether homopolymer or its copolymer.

[0117] Specific examples of the polyphenylene sulfide resin include polyphenylene sulfide, polyphenylene sulfide ketone, polybiphenylene sulfide, and polyphenylene sulfide sulfone.

[0118] The thermoplastic resin may be a synthetic product or a commercially available product. In the case of a synthetic product, a resin (resin polymer) may be synthesized using a known method such as high pressure radical polymerization, medium and low pressure polymerization, solution polymerization, slurry polymerization, bulk polymerization, emulsion polymerization, or gas phase polymerization, and may be applied to the resin composition. In this case, the above-mentioned thermal polymerization initiator or photopolymerization initiator may be used.

[0119] When the thermoplastic resin is a copolymer, the copolymer may be in the form of a block copolymer, a random copolymer, a graft copolymer or an alternating copolymer.

[0120] The thermoplastic resin preferably includes at least one selected from the group consisting of a (meth)acrylic resin, a styrene resin, an olefin resin, and a polyester resin, and more preferably includes a (meth)acrylic resin.

[0121] [Thermosetting resin] The thermosetting resin used in the present invention is not particularly limited, and examples thereof include phenol resin, urea resin, melamine resin, epoxy resin, unsaturated polyester resin, silicone resin, polyurethane resin, polyimide resin, diallyl phthalate resin, etc. As the thermosetting resin, a synthetic product or a commercially available product may be used.

[0122] In the resin composition of the present invention, the content of the ion-bonding salt represented by chemical formula (1) or the constituent unit derived from the ion-bonding salt is preferably 0.1 to 40 parts by mass, more preferably 0.1 to 20 parts by mass, more preferably 0.1 to 10 parts by mass, and particularly preferably 0.1 parts by mass or more and less than 5 parts by mass, relative to 100 parts by mass of the resin. By being in such a content range, the surface of the coating film formed from the resin composition can exhibit good hydrophilicity and stain resistance without impairing the inherent properties of the resin.

[0123] The resin composition of the present invention can be appropriately blended with other additives such as polymerization initiators, antioxidants, fillers, lubricants, dyes, organic pigments, inorganic pigments, plasticizers, processing aids, ultraviolet absorbers, light stabilizers, foaming agents, waxes, crystal nucleating agents, release agents, hydrolysis inhibitors, antiblocking agents, antistatic agents, radical scavengers, antifogging agents, antifogging agents, ion trapping agents, flame retardants, flame retardant assistants, and surfactants, within the scope of the present invention. For example, when a resin composition containing a resin monomer is applied to an object and cured, it is preferable to blend a polymerization initiator into the resin composition in order to promote curing. Examples of the polymerization initiator include the thermal polymerization initiator and photopolymerization initiator described above.

[0124] The form of the resin composition of the present invention is not particularly limited and may be, for example, any form such as a solid, emulsion, translucent solution, or transparent solution. From the viewpoint of reducing the environmental load, however, an emulsion is preferable.

[0125] The resin composition of the present invention can be produced by mixing the wettability improver containing the ion-bonding salt or its polymer, the silicate or its condensate, the resin, and, if necessary, the above-mentioned additives, by stirring or melt-kneading, etc. The melt-kneading method is not particularly limited, and for example, a method using an apparatus such as a single-screw extruder, a twin-screw extruder, a heat roll, a Banbury mixer, a Henschel mixer, a tumbler mixer, or various kneaders can be adopted.

[0126] <Uses of the wettability improver and the resin composition containing the same> The wettability improver according to the present invention and the resin composition containing the same can be suitably used as a hydrophilic coating agent. Specifically, the hydrophilic coating agent consisting of the wettability improver or the resin composition according to the present invention is applied to the surface of a molded article and dried or cured to form a hydrophilic coating film on the surface of the molded article. The surface of the obtained hydrophilic coating film has excellent hydrophilicity, for example, a contact angle with water of 90° or less, preferably 40° or less, more preferably 20° or less, and even more preferably less than 10°. Therefore, the molded article having the hydrophilic coating film disposed on the surface thereof has excellent hydrophilicity and therefore excellent contamination resistance.

[0127] The molded article to be improved in hydrophilicity is not particularly limited, but examples thereof include films, plastics, glass, fibers, sheets, tapes, etc., and preferably films, plastics, and glass.

[0128] As the coating method, a known coating method can be appropriately used, for example, spin coating, roll coating, gravure coating, reverse coating, spray coating, air knife coating, curtain coating, roll brush, impregnation, coating with a bar coater, etc.

[0129] The drying conditions can be appropriately adjusted depending on the heat resistance of the molded product, the boiling point of the solvent contained in the hydrophilic coating agent, etc. The drying temperature is not particularly limited, but is, for example, 50 to 180°C, 80 to 150°C, or 110 to 130°C. The drying time is also not particularly limited, but is, for example, 0.5 to 120 minutes, 1 to 60 minutes, or 1 to 10 minutes. The drying atmosphere is also not particularly limited, but is, for example, air, inert gas (e.g., nitrogen), or vacuum.

[0130] The curing method may be either photocuring or heat curing, but photocuring is preferred from the viewpoint of short-time curing and reducing damage to the molded product. That is, in the hydrophilic coating agent according to a preferred embodiment of the present invention, the resin composition contains a photocurable resin. As the photocurable resin, the (meth)acrylic resin described in the section [Thermoplastic resin] is preferred, and a polyfunctional (meth)acrylic monomer is more preferred.

[0131] In the case of photocuring, it is preferable to use a light source that generates ultraviolet rays, and a mercury lamp (e.g., a high-pressure mercury lamp or a low-pressure mercury lamp), a metal halide lamp, etc. can be used. The irradiation conditions of the ultraviolet rays are not particularly limited, but the cumulative light amount is 100 to 1000 mJ / cm. 2 is preferable, and 200 to 500 mJ / cm 2 In the case of heat curing, it may be carried out under the same conditions as the drying described above. That is, drying and heat curing may proceed simultaneously.

[0132] In forming the hydrophilic coating film, both drying and curing may be performed. For example, the solvent contained in the hydrophilic coating agent may be removed by pre-drying, and then photo-curing may be performed.

[0133] The thickness of the hydrophilic coating film formed is preferably 1 to 50 μm, more preferably 5 to 20 μm, and even more preferably 10 to 15 μm, in terms of dry thickness. Within such ranges, the hydrophilicity of the surface of the molded article is excellent, and the surface hardness is well maintained before and after the coating film formation.

[0134] In the hydrophilic coating film, the content of the constitutional unit derived from the ion-bonding salt is preferably 0.1 to 800 mass%, more preferably 0.5 to 400 mass%, based on 100 mass% of the resin. Within such a range, the hydrophilicity of the surface of the molded article can be improved without impairing the inherent properties of the molded article. The content is substantially equal to the ratio of the mass of the ion-bonding salt to the total mass of the resin (e.g., resin monomer).

[0135] Another use of the wettability enhancer according to the present invention is, for example, mixing with the raw materials for manufacturing a molded product to be hydrophilic. The molded product is not particularly limited, but examples thereof include films, plastics, glass, fibers, sheets, tapes, etc., and preferably films, plastics, and glass.

[0136] Other uses of the resin composition of the present invention include, for example, paints, adhesives, pressure sensitive adhesives, textile auxiliaries, building material films, protective films such as hard coats, housings for home appliances, papermaking applications (surface coating agents, etc.), civil engineering applications (concrete admixtures, etc.), etc. Molded articles made of the resin composition of the present invention may be produced and applied to these applications. The surface of the molded article has excellent hydrophilicity, and for example, the contact angle with water may be 90° or less, preferably 40° or less, more preferably 20° or less, and even more preferably less than 10°.

[0137] The molded article can be produced by a known method such as injection molding, extrusion molding, transfer molding, inflation molding, compression molding, etc. These methods can be appropriately selected depending on the shape of the molded article to be obtained. EXAMPLES

[0138] The effects of the present invention will be described using the following examples and comparative examples. However, the technical scope of the present invention is not limited to the following examples. In the following examples, unless otherwise specified, the operations were performed at 25°C. Furthermore, unless otherwise specified, "%" and "parts" mean "% by mass" and "parts by mass", respectively.

[0139] (Synthesis Example 1: Synthesis of [2M-AA] [130305-S]) 2 parts by mass of potassium hydroxide was added to 200.4 parts by mass of tridecanol, and the mixture was heated to 170°C, after which 216.3 parts by mass of 1,2-butylene oxide was added under pressure at 1.0 MPa or less and reacted for 10 hours. Thereafter, 220.3 parts by mass of ethylene oxide was added under pressure at 1.0 MPa or less and reacted for 10 hours to obtain 639 parts by mass of polyoxybutylene / polyoxyethylene tridecyl ether. 637 parts by mass of the obtained polyoxybutylene / polyoxyethylene tridecyl ether was heated to 110°C, and 97.1 parts by mass of sulfamic acid was added and reacted for 3 hours. After the reaction, unreacted sulfamic acid was filtered off, and polyoxybutylene / polyoxyethylene tridecyl ether sulfate ammonium salt ([C 13 H27 -O-(BO)3-(EO)5-SO3 - ][NH4 + ]) 734.1 parts by mass were obtained.

[0140] 734.1 parts by mass of the polyoxybutylene / polyoxyethylene tridecyl ether sulfate ammonium salt (abbreviation: 130305-SF) synthesized above was added to 143.2 parts by mass of N,N-dimethylaminoethyl acrylate (abbreviation: 2M-AA), and the mixture was allowed to react for 1 hour at 50° C. After the reaction, 860.1 parts by mass of the target ionic salt (abbreviation: [2M-AA] [130305-S], a compound represented by the above chemical formula (2)) was obtained.

[0141] (Synthesis Example 2: Synthesis of [2M-AA][707-S]) 920.1 parts by mass of polyoxyethylene polycyclic phenyl ether sulfate ammonium salt (abbreviation: 707-SF) obtained by distilling water under reduced pressure from a 30% aqueous solution of polyoxyethylene polycyclic phenyl ether sulfate ammonium salt (manufactured by Nippon Nyukazai Co., Ltd., product name: Newcol 707-SF, abbreviation: N-707-SF) was added to 157.2 parts by mass of N,N-dimethylaminoethyl acrylate (abbreviation: 2M-AA), and the mixture was allowed to react for 1 hour. After the reaction, 1060.3 parts by mass of the target ionic salt (abbreviation: [2M-AA] [707-S]) was obtained. This ionic salt has the following chemical structure.

[0142] [ka]

[0143] (Examples 1 to 5 and Comparative Examples 1 to 8) A mixed solution having the composition (mass ratio) shown in Tables 1 and 2 below was applied to a polyethylene terephthalate (PET) plate using a bar coater so that the wet film thickness was 15 μm. Then, an ultraviolet irradiation device (manufactured by iGraphics Co., Ltd., ECS-4011GX, mercury lamp) was used as the irradiation light source, and the accumulated light amount was 300 mJ / cm. 2The test pieces thus obtained were aged for 48 hours and then subjected to the following evaluations.

[0144] The details of each component listed in Tables 1 and 2 are as follows: UV-7550B: urethane acrylate resin, manufactured by Mitsubishi Chemical Corporation, product name Shikou UV-7550B; A-200: polyethylene glycol diacrylate (average number of moles of oxyethylene groups added: 4), manufactured by Shin-Nakamura Chemical Co., Ltd., trade name NK Ester A-200; Irgacure 184: Photopolymerization initiator (1-hydroxycyclohexyl phenyl ketone) MMA: methyl methacrylate; [2M-AA][130305-S]: the ionic salt represented by chemical formula (1) obtained in Synthesis Example 1 above (the cation has an ethylenically unsaturated bond); [2M-AA][707-S]: an ionic salt represented by chemical formula (1) obtained in Synthesis Example 2 above (the cation has an ethylenically unsaturated bond); Silicate MS51: hydrolysis and condensation product of tetramethoxysilane (average heptamer to nonamer, molecular weight 800 to 1,000), manufactured by Mitsubishi Chemical Corporation, trade name Methyl Silicate MS51; KBM-503: Silane coupling agent (3-methacryloxypropyltrimethoxysilane), manufactured by Shin-Etsu Chemical Co., Ltd., trade name Shin-Etsu Silicone KBM-503.

[0145] (Evaluation of hydrophilicity) The contact angle of water (25°C) was measured for the test pieces obtained in the above examples and comparative examples. Specifically, a contact angle meter (manufactured by Kyowa Interface Science Co., Ltd., model number: CA-XP) was used to create a droplet of about 2 μL using pure water as the liquid at a dry state (25°C / 50% RH) on the tip of a needle, which was then brought into contact with the surface of the test piece to create a droplet on the surface of the test piece. The angle formed by the tangent to the liquid surface and the test piece surface at the point where the test piece and the liquid come into contact was measured as the contact angle, and the angle on the side containing the liquid was measured. The values ​​of the contact angles measured for each example and comparative example are shown in Tables 1 and 2 below.

[0146] (Washing resistance test) A sponge was moistened with tap water, and the test piece was rubbed 10 times with the sponge, rinsed with tap water, and wiped off the water droplets. This operation was repeated twice, and the contact angle (25°C) was measured after each cleaning operation using the same method as above. The contact angle values ​​measured for each Example and Comparative Example are shown in Tables 1 and 2 below.

[0147] [Table 1]

[0148] [Table 2]

[0149] As is clear from Tables 1 and 2, the coating films (Examples 1 to 5) prepared using [2M-AA] [130305-S] as the ion-bonding salt and a specified silicate condensate maintained low water contact angle values ​​after rinsing with water, compared to the coating films (Comparative Examples 1 to 5) prepared without using the specified silicate condensate.

[0150] Moreover, the coating films of Examples 1 to 5 were able to maintain the water contact angle after washing at an extremely low value, even when compared with the coating films (Comparative Examples 6 to 8) prepared using a specific silicate condensate but without using the specific ion-bonding salt of the present application. Such a remarkable effect can be said to be a synergistic effect that could not be predicted by combining the results of Comparative Examples 1 to 5 with those of Comparative Examples 6 to 8. The mechanism by which such a remarkable effect is obtained is considered to be that the silicate forms a highly hydrophilic layer on the surface, which acts to retain the highly hydrophilic specific ion-bonding salt (or its polymer) on the coating film, thereby maintaining high hydrophilicity even after washing with water as described above.

[0151] From the above, it has been demonstrated that the wettability improver according to the present invention can maintain high hydrophilicity in a hydrophilic coating film even after washing.

Claims

1. The following chemical formula (1): 【Chemical 1】 In chemical formula (1), Q ｎ＋ represents a monovalent metal ion, a divalent metal ion, or a nitrogen-containing compound ion, T － represents an alkyl sulfate ion, a polyoxyalkylene alkyl ether sulfate ion, a polyoxyalkylene alkyl phenyl ether sulfate ion, an alkyl sulfonate ion, an alkylbenzene sulfonate ion, an alkyl phosphate ester ion, a polyoxyalkylene alkyl ether phosphate ester ion, or a polyoxyalkylene alkyl phenyl ether phosphate ester ion, n is Q ｎ＋ is 1 or 2 in valence; an ion-binding salt represented by the formula (I) or a polymer thereof; The following chemical formula (A): 【Chemistry 2】 In chemical formula (A), R are the same or different and each represent a hydrogen atom or an optionally substituted monovalent hydrocarbon group having 1 to 10 carbon atoms; a silicate represented by the formula (I) or a condensate thereof; A wetting enhancer comprising:

2. Q ｎ＋ is at least one selected from the group consisting of an ammonium ion, an imidazolium ion, a pyridinium ion, a pyrrolidinium ion, a pyrrolinium ion, a piperidinium ion, a pyrazinium ion, a pyrimidinium ion, a triazolium ion, a triazinium ion, a quinolinium ion, an isoquinolinium ion, an indolinium ion, a quinoxalinium ion, a piperazinium ion, an oxazolinium ion, a thiazolinium ion, and a morpholinium ion.

3. Q ｎ＋ The wettability improver according to claim 2 , wherein

4. Q ｎ＋ The wettability improver according to claim 3 , wherein is an ammonium ion having an ethylenically unsaturated bond.

5. In the compound (1), T － The wettability improver according to claim 1 or 3, wherein is an alkyl sulfate ion, a polyoxyalkylene alkyl ether sulfate ion, or a polyoxyalkylene alkyl phenyl ether sulfate ion.

6. In the compound (1), (T － ) ｎ is represented by the following chemical formula (2): 【Chemistry 3】 In chemical formula (2), R' is an optionally substituted linear or branched alkyl group having 12 to 14 carbon atoms, A is a linear or branched alkylene group having 2 to 4 carbon atoms; m is the average number of moles of AO added and is an integer of 2 to 50; (AO) ｍ contains at least two kinds of oxyalkylene groups, the arrangement of which may be random or block, n is Q ｎ＋ is 1 or 2 in valence; The wettability improver according to claim 5, which is a polyoxyalkylene alkyl ether sulfate ion represented by the formula:

7. (AO) ｍ The wettability enhancer of claim 6 , wherein: comprises an oxyethylene group and an oxybutylene group.

8. (AO) ｍ 8. The wettability improver according to claim 7, wherein the proportion of oxybutylene groups is 3 to 90 mol %.

9. A wettability enhancer comprising a polymer having structural units derived from the ionically bondable salt according to claim 3 .

10. 4. The wettability improver according to claim 1, comprising one or more condensates of 4 to 10 monomers of the silicate in which R is a methyl group or an ethyl group.

11. A resin composition comprising the wettability improver according to claim 1 or 9 and a resin.

12. The resin composition according to claim 11, wherein the ion-bonding salt or a structural unit derived from the ion-bonding salt is contained in an amount of 0.1 parts by mass or more and less than 5 parts by mass per 100 parts by mass of the resin.

13. A hydrophilic coating agent comprising the wettability improver according to claim 9.

14. A hydrophilic coating agent comprising the resin composition according to claim 11.

15. The hydrophilic coating agent according to claim 14, wherein the resin composition comprises a photocurable resin.

16. A hydrophilic coating film obtained by drying or curing the hydrophilizing coating agent according to claim 13.

17. The hydrophilic coating film according to claim 16, wherein the contact angle (25°C) of the surface with water is 20° or less.

18. A molded article having a hydrophilic surface, comprising: a molded article; and the hydrophilic coating film according to claim 16 disposed on the surface of the molded article.

19. A method for producing a molded article having a hydrophilic surface, comprising the step of applying the hydrophilizing coating agent according to claim 13 to the surface of the molded article and drying or curing the coating agent to form a hydrophilic coating film on the surface of the molded article.

20. The method for producing a molded article according to claim 19, wherein the hydrophilic coating film has a contact angle (25°C) with water of 20° or less.

21. A molded article made from the resin composition according to claim 11.

22. 22. The molded article according to claim 21, wherein the contact angle of the surface of the molded article with water is 20° or less.

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