JP6450353B2 - Wetting property improving agent, resin composition containing the same, and hydrophilic coating agent - Google Patents

Description

  The present invention relates to a wettability improving agent, a resin composition containing the same, and a hydrophilic coating agent comprising the same.

  High contamination resistance is required for members used in baths, toilets, wallpaper, window glass, building outer walls, optical films, etc. As one of the methods for achieving this, the surface of the members is hydrophilized. The method of doing is mentioned. By performing such a treatment, a uniform water film is formed on the surface of the member. Even if dirt adheres to the surface of the member, the dirt can be easily removed by washing with water. As the hydrophilization treatment, an inorganic compound having photocatalytic performance such as titanium oxide is generally used. However, since it has low transparency, it does not exhibit high hydrophilicity unless it is irradiated with light (such as ultraviolet light). There was a problem that sufficient contamination resistance could not be obtained in the use environment and the treatment process was complicated. Therefore, Patent Document 1 proposes an organic wettability improver that is excellent in transparency and can exhibit high hydrophilicity without performing treatment such as light irradiation.

Japanese Patent No. 576632

  However, the wettability improving agent described in Patent Document 1 has a problem that the effect of imparting hydrophilicity is insufficient when the addition amount is small.

  Therefore, the present invention has been made in view of the above problems, and an object thereof is to provide a wettability improver having an excellent hydrophilicity imparting effect even when added in a small amount. Another object of the present invention is to provide a wettability improver capable of forming a hydrophilic coating film having a surface having a contact angle with water of 20 ° or less.

  As a result of intensive studies to solve the above problems, the present inventors have found that the above problems can be solved by a wettability improver having a specific structure, and have completed the present invention.

  That is, the present invention is a wettability improver containing an ion-binding salt represented by the following chemical formula (1).

In the chemical formula (1), R is an optionally substituted linear alkyl group having 12 to 14 carbon atoms, and A is a linear or branched alkylene group having 2 to 4 carbon atoms. M is an average added mole number of AO and is an integer of 2 to 50, (AO) _m contains at least two oxyalkylene groups, and the arrangement thereof may be either random type or block type, and n is Q ⁺ 1 or 2 in valence, Q ⁺ is a monovalent metal ion, a bivalent metal ion or a nitrogen-containing compound ions.

  The wettability improver of the present invention has an excellent hydrophilicity imparting effect even when added in a small amount. Moreover, the coating film formed using the wettability improver of the present invention has good hydrophilicity, for example, the contact angle of water on the surface is 20 ° or less (particularly preferably 5 ° or less).

  Hereinafter, embodiments of the present invention will be described in detail. In addition, this invention is not limited only to the following embodiment.

  In the present specification, the phrase “the coating film (or molded article) surface has high hydrophilicity” is synonymous with the phrase “the coating film (or molded article) surface has high wettability to water”. The contact angle of water on the surface of the coating film (or molded product) is 90 ° or less, preferably 40 ° or less, more preferably 20 ° or less, even more preferably 10 ° or less, and particularly preferably 5 ° or less. Good, especially 5 degrees or less is called super hydrophilicity.

  In this specification, “X to Y” indicating a range means “X or more and Y or less”. Unless otherwise specified, measurement of operation and physical properties is performed under conditions of room temperature (20 to 25 ° C.) / Relative humidity 40 to 50% RH.

<Wettability improver>
The wettability improver of the present invention contains the following ion-binding salt or polymer thereof.

[Ion-binding salt]
(Structure of ion-binding salt)
The ion-binding salt contained in the wettability improver of the present invention is represented by the following chemical formula (1).

  In the chemical formula (1), R is an optionally substituted linear alkyl group having 12 to 14 carbon atoms, that is, an n-dodecyl group, an n-tridecyl group, or an n-tetradecyl group. However, an n-tridecyl group is preferable from the viewpoint of availability. When R is substituted, examples of such substituent include halogen atoms such as fluorine, chlorine, bromine and iodine, phenyl group, p-tolyl group, xylyl group, cumenyl group, naphthyl group, anthryl group, Aryl groups such as phenanthryl group, alkoxy groups such as methoxy group, ethoxy group, tert-butoxy group, aryloxy groups such as phenoxy group, p-tolyloxy group, methoxycarbonyl group, butoxycarbonyl group, 2-ethylhexyloxycarbonyl group, Alkoxycarbonyl groups such as phenoxycarbonyl group, acyloxy groups such as acetoxy group, propionyloxy group and benzoyloxy group, acyl groups such as acetyl group, benzoyl group, isobutyryl group, acryloyl group, methacryloyl group and methoxalyl group, methylsulfanyl Alkylsulfanyl groups such as tert-butylsulfanyl group, arylsulfanyl groups such as phenylsulfanyl group and p-tolylsulfanyl group, alkylamino groups such as methylamino group and cyclohexylamino group, dimethylamino group, diethylamino group, morpholino group, In addition to dialkylamino groups such as piperidino group, arylamino groups such as phenylamino group and p-tolylamino group, hydroxy group, carboxy group, formyl group, mercapto group, sulfo group, mesyl group, p-toluenesulfonyl group, amino group Group, nitro group, cyano group, trifluoromethyl group, trichloromethyl group, trimethylsilyl group, phosphinico group, phosphono group and the like.

In the chemical formula (1), A is a linear or branched alkylene group having 2 to 4 carbon atoms, an ethylene group, a trimethylene group, a propylene group (—CH ₂ —CH (CH ₃ ) —), n-butylene group, 1-methylpropylene group (—CH ₂ —CH ₂ —CH (CH ₃ ) —), 2-methylpropylene group (—CH ₂ —CH (CH ₃ ) —CH ₂ —), dimethylethylene group _{(-CH 2 -C (CH 3)} 2 -), ethyl ethylene group _{(-CH 2 -CH (CH 2 CH} 3) -), and the like. In addition, when A is a C3-C4 alkylene group, it is preferable that it is a branched alkylene group. Further, in A, the number of carbon atoms in the portion constituting the main chain of (AO) _m is preferably 2 or less. That is, A preferably has at least one 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 having both water resistance and surface hydrophilicity.

  In the chemical formula (1), m is an average added mole number of AO and is an integer of 2 to 50. m is preferably 2 to 30 and more preferably 2 to 20 from the viewpoints of workability improvement and wettability due to viscosity reduction.

In the chemical formula (1), (AO) _m represents polyoxyalkylene and includes at least two oxyalkylene groups. By setting it as such a polyoxyalkylene structure, the coating film or molded article which can make water resistance and surface hydrophilicity compatible can be formed. (AO) _m is preferably an oxyethylene group (—C ₂ H ₄ O—, hereinafter also referred to as EO), an oxypropylene group (—C ₃ H ₆ O—, hereinafter also referred to as PO) and an oxybutylene group (— C ₄ H ₈ O—, hereinafter also referred to as BO). (AO) _m more preferably includes an oxyethylene group and an oxybutylene group. The oxypropylene group and 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 preferably have 2 or less carbon atoms in the portion constituting the main chain of (AO) _m . 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 is at least one of the groups represented by the following chemical formula (B1) or (B2). It is preferable to have. By having such a group, it is possible to form a coating film or a molded article having both water resistance and surface hydrophilicity.

In (AO) _m , the proportion of the oxybutylene group is preferably 3 to 90 mol%, more preferably 10 to 80 mol%. In addition, when an oxybutylene group has 2 or more types of structures, the ratio of the said oxybutylene group represents the sum total of the ratio (mol%) of each structure. The arrangement of at least two kinds of oxyalkylene groups may be either a random type or a block type, but is preferably a block type from the viewpoint of effectively exhibiting hydrophilicity and simplicity of the synthesis process. In the case of a block type, the order of arrangement is not limited. That is, for example, when (AO) _m is a block copolymer of ethylene oxide / butylene oxide, a polyoxyethylene chain may be linked to the sulfonic acid group, or a polyoxybutylene chain may be linked.

(AO) _m is an alkylene oxide adduct having 2 to 4 carbon atoms, and the structure of such an alkylene oxide adduct is ethylene oxide, propylene oxide, 1,2-butylene oxide, 2,3-butylene oxide, isobutylene. It is a structure formed by one or more of alkylene oxides such as oxides. Among these, a structure formed by alkylene oxide including ethylene oxide and 1,2-butylene oxide is preferable. In addition, when (AO) _m is formed of two or more kinds of the above compounds, it may be formed by random addition or block addition.

In addition, according to this specification, the form that (AO) _m is an alkylene oxide adduct containing the structure different from the above is also provided. In this embodiment, specifically, the alkylene oxide adduct (AO) _m is an AO structure derived from a monofunctional epoxy compound in place of or in addition to the above-described alkylene oxide having 2 to 4 carbon atoms. It may have. 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.

In the chemical formula (1), n represents a valence of Q ⁺ and is 1 or 2. That is, if the Q ⁺ is a monovalent cation n is 1, if Q ⁺ is a divalent cation and n is 2.

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

  Examples of monovalent metal ions include sodium ions, potassium ions, lithium ions and the like.

  Examples of divalent metal ions include calcium ions and magnesium ions.

  Nitrogen-containing compound ions include ammonium ion, imidazolium ion, pyridinium ion, pyrrolidinium ion, pyrrolium ion, piperidinium ion, pyrazinium ion, pyrimidinium ion, triazolium ion, triazinium ion, quinolinium ion And at least one selected from the group consisting of 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.

  Specific examples of ammonium ions include the following ions. For example, dimethyl ammonium ion, trimethyl ammonium ion, tetramethyl ammonium ion, diethyl ammonium ion, triethyl ammonium ion, tetraethyl ammonium ion, monopropyl ammonium ion, dipropyl ammonium ion, tripropyl ammonium ion, tetrapropyl ammonium ion, monobutyl ammonium Ion, dibutylammonium ion, tributylammonium ion, tetrabutylammonium ion, monopentylammonium ion, dipentylammonium ion, tripentylammonium ion, tetrapentylammonium ion, monohexylammonium ion, dihexylammonium ion, monoheptylammonium ion, diheptyl Ammonium ion, monooctyl ammonium ion, dioctyl ammonium ion, monononyl ammonium ion, monodecyl ammonium ion, monoundecyl ammonium ion, monododecyl ammonium ion, monotridecyl ammonium ion, monotetradecyl ammonium ion, monopentadecyl ammonium ion , Monohexadecyl ammonium ion, monoheptadecyl ammonium ion, monooctadecyl ammonium ion, monononadecyl ammonium ion, monoicosyl ammonium ion, monohenicosyl ammonium ion, monodocosyl ammonium ion, monotricosyl ammonium ion, methyl (Ethyl) ammonium ion, methyl (propyl) ammonium ion, Til (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, Chill (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, Ru (octadecyl) ammonium ion, ethyl (nonadecyl) ammonium ion, ethyl (icosyl) ammonium ion, ethyl (henicosyl) ammonium ion, ethyl (tricosyl) ammonium ion, dimethyl (ethyl) ammonium ion, dimethyl (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, 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, trimethyl (tricosyl) ammonium ion Alkyl ammonium ions such as.

  Monovinylammonium ion, divinylammonium ion, trivinylammonium ion, monopropenylammonium ion, dipropenylammonium ion, tripropenylammonium ion, monobutenylammonium ion, dibutenylammonium ion, tributenylammonium ion, monopentenylammonium ion, di Pentenyl ammonium ion, tripentenyl ammonium ion, monohexenyl ammonium ion, dihexenyl ammonium ion, monoheptenyl ammonium ion, diheptenyl ammonium ion, monooctenyl ammonium ion, dioctenyl ammonium ion, monononenyl ammonium ion, mono Decenyl ammonium ion, monoundecenyl ammonium Ion, monododecenyl ammonium ion, monotridecenyl ammonium ion, monotetradecenyl ammonium ion, monopentadecenyl ammonium ion, monohexadecenyl ammonium ion, monoheptadecenyl ammonium ion, mono Alkenylammonium ions such as octadecenylammonium ion, monononadecenylammonium ion, monoicocenylammonium ion, monohenicocenylammonium ion, monodocosenylammonium ion, and monotricocenylammonium ion.

  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 (pentadecenyl) ammonium ion, dimethyl ( Hexadecenyl) ammonium ion, dimethyl (heptadecenyl) an Nium ion, dimethyl (octadecenyl) ammonium ion, dimethyl (nonadecenyl) ammonium ion, dimethyl (icosenyl) ammonium ion, dimethyl (henicosenyl) ammonium ion, dimethyl (tricocenyl) ammonium ion, bis (2-methoxyethyl) monoethylammonium ion, Monoammonium ions having an alkyl group and an alkenyl group, such as trimethyl (vinyl) ammonium ion and bis (2-methoxyethyl) monomethylammonium ion;

  Monobenzylammonium ion, (1-phenethyl) ammonium ion, (2-phenethyl) ammonium ion (also known as monophenethylammonium ion), dibenzylammonium ion, bis (1-phenethyl) ammonium ion, bis (2-phenethyl) ammonium Aromatic substituted alkyl ammonium ions such as ions (also known as diphenethyl ammonium ions); monocyclopentyl ammonium ions, dicyclopentyl ammonium ions, tricyclopentyl ammonium ions, monocyclohexyl ammonium ions, dicyclohexyl ammonium ions, monocycloheptyl ammonium ions, dicyclo C5-C16 cycloalkyl ammonium ion such as heptyl ammonium ion; dimethyl (Cyclopentyl) ammonium ion, dimethyl (cyclohexyl) ammonium ion, monoammonium ion having an alkyl group and a cycloalkyl group such as dimethyl (cycloheptyl) ammonium ion; (methylcyclopentyl) ammonium ion, bis (methylcyclopentyl) ammonium ion, ( Dimethylcyclopentyl) ammonium ion, bis (dimethylcyclopentyl) ammonium ion, (ethylcyclopentyl) ammonium ion, bis (ethylcyclopentyl) ammonium ion, (methylethylcyclopentyl) ammonium ion, bis (methylethylcyclopentyl) ammonium ion, (diethylcyclopentyl) Ammonium ion, (methylcyclohexyl) ammonium ion Bis (methylcyclohexyl) ammonium ion, (dimethylcyclohexyl) ammonium ion, bis (dimethylcyclohexyl) ammonium ion, (ethylcyclohexyl) ammonium ion, bis (ethylcyclohexyl) ammonium ion, (methylethylcyclohexyl) ammonium ion, (diethyl) (Cyclohexyl) ammonium ion, (methylcycloheptyl) ammonium ion, bis (methylcycloheptyl) ammonium ion, (dimethylcycloheptyl) ammonium ion, (ethylcycloheptyl) ammonium ion, (methylethylcycloheptyl) ammonium ion, (diethylcyclo Heptyl) alkylcycloalkyl ammonium ions such as ammonium ions.

  Monomethanolammonium ion, dimethanolammonium ion, trimethanolammonium ion, monoethanolammonium ion, diethanolammonium ion, triethanolammonium ion, mono (n-propanol) ammonium ion, di (n-propanol) ammonium ion, tri (n -Propanol) ammonium ion, monoisopropanolammonium ion, diisopropanolammonium ion, triisopropanolammonium ion, monobutanolammonium ion, dibutanolammonium ion, tributanolammonium ion, monopentanolammonium ion, dipentanolammonium ion, tripen Tanol ammonium ion, monohexano Ruammonium 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, mono Ethyl monobutanol ammonium ion, monoethyl monopentano 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, di Propyl monopropa Nolamammonium ion, Dipropylmonobutanolammonium ion, Dipropylmonopentanolammonium ion, Dibutylmonoethanolammonium ion, Dibutylmonopropanolammonium ion, Dibutylmonobutanolammonium ion, Dibutylmonopentanolammonium ion, Monomethyldiethanolammonium ion, Monomethyl Dipropanolammonium ion, monomethyldibutanolammonium ion, monomethyldipentanolammonium ion, monoethyldiethanolammonium ion, monoethyldipropanolammonium ion, monoethyldibutanolammonium ion, monoethyldipentanolammonium ion, monopropyldiethanolammonium Ion, monopropyldipropanolammonium ion, monopropyldibutanolammonium ion, monopropyldipentanolammonium ion, monobutyldiethanolammonium ion, monobutyldipropanolammonium ion, monobutyldibutanolammonium ion, monobutyldipentanolammonium Ion, monocyclohexyl monoethanolammonium ion, monocyclohexyldiethanolammonium ion, monocyclohexylmonopropanolammonium ion, monocyclohexyldipropanolammonium ion, mono (β-aminoethyl) monoethanolammonium ion, mono tert-butylmonoethanolammonium ion, Mono tert-butyldiethano Ruammonium ion, mono (β-aminoethyl) isopropanolammonium ion diethylmonoisopropanolammonium ion, trimethylmonoethanolammonium ion, triethylmonoethanolammonium ion, triethylmonopropanolammonium ion, triethylmonobutanolammonium ion, triethylmonopentanolammonium ion , Tripropylmonoethanolammonium ion, tripropylmonopropanolammonium ion, tripropylmonobutanolammonium ion, tripropylmonopentanolammonium ion, diethylmonomethylethanolammonium ion, bis (2-methoxyethyl) monoethylmonomethylammonium ion, monoethylmolybdenum Methyl diethanol ammonium ions, alkanol ammonium ions such as diethyl monomethyl monoethanol ammonium ion. From the viewpoint of availability, monoethylmonoethanolammonium ion, diethylmonoethanolammonium ion, diethylmonomethylethanolammonium ion, bis (2-methoxyethyl) monoethylammonium ion, bis (2-methoxyethyl) monoethylmonomethylammonium ion Monoethyldiethanolammonium ion and monoethylmonomethyldiethanolammonium ion are preferable, and monoethylmonoethanolammonium ion, diethylmonoethanolammonium ion and diethylmonomethylmonoethanolammonium ion are particularly preferable.

  Dimethyl monoacrylate ethylammonium ion, dimethylmonoethyl ammonium methacrylate ion, diethylmonoethyl acrylate ethylammonium ion, diethylmonoethyl methacrylate ethylammonium ion, diethylmono (2-isocyanoethyl) ammonium ion, diethylmono (2-cyanopropyl) ) Ammonium ion, diethyl mono (1,2-epoxypropane) ammonium ion.

  In the above ammonium ion, descriptions such as “N—” and “N, N—” indicating a substituent on N are omitted.

  Specific examples of the imidazolium ion include, for example, imidazolium ion, N-isobutylimidazolium ion, 2-methylimidazolium ion, 2-ethylimidazolium ion, 2-n-propylimidazolium ion, and 2-isopropyl. Imidazolium ion, 2-n-Butylimidazolium ion, 2-Phenylimidazolium ion, 4-Methylimidazolium ion, 4-Ethylimidazolium ion, 4-Nitroimidazolium ion, 4-Phenylimidazolium ion, 2- Methyl-4-phenylimidazolium ion, 4,5-dimethylimidazolium ion, 1-isobutyl-2-methylimidazolium ion, 1-isobutyl-2,3-methylimidazolium ion, 2,4,5-trimethylimidazole Riu Ions, 2,4,5 triphenyl imidazolium ions, benzimidazolium ion, 2-methyl benzimidazolium ion, such as 2-phenylbenzimidazole imidazolium ion. From the viewpoint of availability, 1-isobutyl-2-methylimidazolium ion and 1-isobutyl-2,3-methylimidazolium ion are particularly preferable.

  Specific examples of the pyridinium ion include, for example, pyridinium ion, 2-isobutylpyridinium ion, 3-isobutylpyridinium ion, 3-methylpyridinium ion, 4-methylpyridinium ion, 2-ethylpyridinium ion, and 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- (3-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- Droxypyridinium 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 Ion, 4-hydroxy-3-nitropyridinium ion, 3-hydroxy-2-nitropyridinium ion, 2-hydroxy-6-methyl-5-nitropyridinium ion, 2-ethenylpyri Dinium 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-5-vinylpyridinium ion, 4- (phenylpropyl) pyridinium ion, 4- (1-piperidyl) pyridinium ion, 4-pyrrolidinopyridinium ion, 2-pyrrolidine-2 -Ylpyridinium ion, 4-phenoxypyridinium ion, 2-methyl-3-ethylpyridinium ion, 2-methyl-5- (iso) propylpyridinium ion, 2-acetylpyridinium ion, 3-acetylpyridinium ion, 4- Cetylpyridinium 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, N-Boc-1,2,3,6-tetrahydropyridinium ion Etc.

  Specific examples of the pyrrolidinium ion include, for example, pyrrolidinium ion, N-methylpyrrolidinium ion, N-ethylpyrrolidinium ion, N-propylpyrrolidinium ion, N-butylpyrrolidinium ion, N-phenylpyrrolidinium ion. Ion, N-nitrosopyrrolidinium ion, 2-methylpyrrolidinium ion, 2-phenylpyrrolidinium ion, 3-phenylpyrrolidinium ion, 3-hydroxy-1-methylpyrrolidinium ion, 3- (4-methylphenyl) pyrrole Examples include dinium ion, 3- (pyrrolidinium-1-ylmethyl) piperidine, and 2-pyrrolidinium-2-ylpyridine.

  Specific examples of the pyrrolinium ion include, for example, pyrrolinium ion, N-methylpyrrolinium ion, 2-acetyl-5-methylpyrrolium ion, pyrrolium-1-carboxylate methyl, 2-acetylpyrrolium ion, 3-acetylpyrrolium ion, 2,5-dimethyl-1- (4-nitrophenyl) -1H-pyrrolium ion, 1-furfurylpyrrolium ion, 1- (2-nitrophenyl) pyrrolium ion, 1, 2,5-trimethylpyrrolinium ion, diethyl 2,4-dimethylpyrrolium-3,5-dicarboxylate, ethyl 4-methylpyrrolium-3-carboxylate, ethyl 4-phenylpyrrolium-3-carboxylate, 3 , 4,5-Trimethylpyrrolinium-2-carboxylate, 2,5-dimethylpi Methyl linium-3-carboxylate, methyl 1,2,5-trimethyl-1H-pyrrolium-3-carboxylate, N-trimethoxysilylpyrrolium ion, N-triethoxysilylpyrrolium ion, N- (3-tri And methoxysilylpropyl) pyrrolinium ion and N- (3-triethoxysilylpropyl) pyrrolinium ion.

  Specific examples of piperidinium ions include, for example, 2,6-dimethylpiperidinium ion, 1,3-dimethyl-4-piperidinium ion, 2,2,6,6-tetramethylpiperidinium ion, 2 , 2,6,6-tetramethyl-4-hydroxypiperidinium ion, 2,2-6-6-tetramethyl-4-acetoxypiperidinium ion, 2,2,6,6-tetramethyl-4-acetamidopipe Lizinium ion, 2,2,6,6-tetramethyl-4-oxopiperidinium ion, 2,2,6,6-tetramethyl-4-methoxypiperidinium 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-propenepiperidinium 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-bromo Phenyl) -2-cyclopentylpropanoyl] oxypiperidinium ion, 1,3-dimethyl -4- [2- (4-Cyanophenyl) -2-cyclopentylpropanoyl] oxypiperidinium ion, 1,3-dimethyl-4- [2- (3-cyanophenyl) -2-cyclopentylpropanoyl] oxypipe Lidinium 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- (3-Methylsulfonylphenyl) -2-cyclopentylpropanoyl] oxypipe Dinium 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 and the like.

  Specific examples of the pyrazinium ion include, for example, pyrazinium ion, methyl pyrazinium carboxylate, pyrazinium-2-carbonitrile, pyrazinium carboxamide, 2-acetyl-3-ethylpyrazinium ion, 2-acetyl -3-methylpyrazinium ion, 2-acetylpyrazinium ion, 2- (aminomethyl) -5-methylpyrazinium ion, 2-amino-3- (phenylmethyl) pyrazinium ion, 2,3-bis (2 '-Pyridyl) -5,6-dihydropyrazinium ion, 2-cyanopyrazinium ion, 2,3-diethyl-5-methylpyrazinium ion, 2,3-diethylpyrazinium ion, 6,7-dihydro-5 -Methyl-5H-cyclopentapyrazinium ion, 3,5-dimethyl-2-ethylpi Dinium 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-methoxypi Radinium 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) pyrazini Ions, 2,3,5,6-tetramethylpyrazinium ions, 2,3,5-tri Examples thereof include methyl pyrazinium ion and 2-vinyl pyrazinium ion.

  Specific examples of the pyrimidinium ion include, for example, pyrimidinium ion, 4-methylpyrimidinium ion, 4-hydroxypyrimidinium ion, 4,6-dimethylpyrimidinium ion, and 4,6-dihydroxy. Pyrimidinium 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, 4,6-dihydroxypyrazolo [3,4-d Such as pyrimidinium ion.

  Specific examples of the triazolium ion include, for example, 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-tetrahydrotriazoli 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, 2- (2'-hydroxy-4-octoxyphenyl) benzotriazolium ion, and the like.

  Specific examples of the triazinium ion include, for example, 1,2,3-triazinium ion, 1,2,4-triazinium ion, 1,3,5-triazinium ion, and 3,4-dihydro-3. -Hydroxy-4-oxo-1,2,3-benzotriazinium ion, 3- (2-pyridyl) -5,6-diphenyl-1,2,4-triazinium ion, 5,6-diphenyl-1, 2,4-triazinium ion, hexahydro-1,3,5-triethyl-s-triazinium ion, hexahydro-1,3,5-triphenyl-1,3,5-triazinium ion, 2- (4- Pyridinyl) -1,3,5-triazinium ion, 1,3,5-triacryloylhexahydro-1,3,5-triazinium ion, 2,4,6-triphenyl- -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, 2,4,6-tris (allyloxy) -1,3,5-triazinium ion, and the like.

  Specific examples of quinolinium ions include, for example, quinolinium ions, 2-methylquinolinium ions, 3-methylquinolinium ions, 4-methylquinolinium ions, and 8-methylquinolinium ions. 2,8-dimethylquinolinium ion, 3,8-dimethylquinolinium ion, 4,8-dimethylquinolinium ion, 7-methylquinolinium ion, 2,7-dimethylquinolinium ion, 3 , 7-dimethylquinolinium ion, 4,7-dimethylquinolinium ion, 6-methylquinolinium ion, 2,6-dimethylquinolinium ion, 3,6-dimethylquinolinium ion, 4,6 -Dimethylquinolinium ion, 8-ethylquinolinium ion, 2-methyl-8-ethylquinolinium ion, 4-methyl-8-ethyl Glue ions, 7-isopropyl-2-methyl quinolinium ion, and the like 6-tert-butyl-4-methyl quinolinium ion.

  Specific examples of isoquinolinium ions include, for example, isoquinolinium ions, 3-methylisoquinolinium ions, 4-methylisoquinolinium ions, 5-methylisoquinolinium ions, 6- Methylisoquinolinium ion, 7-methylisoquinolinium ion, 8-methylisoquinolinium ion, 1,3-dimethylisoquinolinium ion, 5,8-dimethylisoquinolinium ion, 5,6 , 7,8-tetramethylisoquinolinium ion, 3-tert-butylisoquinolinium ion, 4-tert-butylisoquinolinium ion, 6-tert-butylisoquinolinium ion, 7-tert- A butyl isoquinolinium ion etc. are mentioned.

  Specific examples of indolinium ions include, for example, indolinium ions, 3-methylindolinium ions, 2-methylindolinium ions, 1-methyl-3-methylindolinium ions, and 2,3-dimethylindolinium ions. 3-ethylindolinium ion, 2-phenylindolinium ion, 3-phenylindolinium ion, 2,3-phenylindolinium ion, 2,3-dimethyl-7-nitroindolinium ion, 2,3-dimethyl- 7-chloroindolinium ion, 3-ethyl-7-methylindolinium ion, 2,3-dimethyl-7-methoxymethylindolinium ion, 7-methoxymethyl-3-methylindolinium ion, 3- (pyridine-2 -Ill) Indolium ion, 3- (pi Gin-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-dimethoxypyrimidine-2 -Yl) -2-butoxymethylindolinium ion, 3- (4,6-diethoxypyrimidin-2-yl) -7-methoxymethylindolinium ion, and the like.

  Specific examples of quinoxalinium ions include quinoxalinium ions, 2-methylquinoxalinium ions, and 2,3-dimethylquinoxalinium ions.

  Specific examples of the piperazinium ion include, for example, 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-allylpipe Radiumium ion, 1- (2-methylallyl) piperazinium ion, 1- (1-methylbutyl) piperazinium ion, 1-benzoylpiperazinium ion, 1-cyclopentylpiperazinium ion, 1-formylpiperazinium ion, 1-fur Netylpiperazinium 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) piperazini 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) piperazini 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, -(3-methoxyphenyl) -4- (piperidin-4-ylmethyl) piperazinium ion, 2-methyl-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- (piperidine) -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) piperazi Ion and the like.

  Specific examples of the oxazolinium ion include, for example, oxazolinium ion, 4-methyloxazolinium ion, 5-methyloxazolinium ion, 4-phenyloxazolinium ion, and 4,5-diphenyloxazolyl. Nium ion, 4-ethyloxazolinium ion, 4,5-dimethyloxazolinium ion, 5-phenyloxazolinium ion, benzoxazolinium ion, 5-chlorobenzoxazolinium ion, 5-methylbenzoxazolyl Nium ion, 5-phenylbenzoxazolinium ion, 6-methylbenzoxazolinium ion, 5,6-dimethylbenzoxazolinium ion, 4,6-dimethylbenzoxazolinium ion, 6-methoxybenzoxazolinium ion Ion, 5-meth Cibenzoxazolinium ion, 4-ethoxybenzoxazolinium ion, 5-chlorobenzoxazolinium ion, 6-methoxybenzoxazolinium ion, 5-hydroxybenzoxazolinium ion, 6-hydroxybenzoxazolinium ion Ions, naphtho [1,2] oxazolinium ions, naphtho [2,1] oxazolinium ions, and the like.

  Specific examples of thiazolinium ions include, for example, thiazolinium ions, 2-aminothiazolinium ions, 2-methylthiazolinium ions, 2-methoxythiazolinium ions, and 2-ethoxythiazolinium ions. , 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, benzothiazoli ion Nium ion, 2-methylbenzothiazolinium ion, 2, - dimethyl-benzothiazolyl ion.

  Specific examples of the morpholinium ion include, for example, morpholinium ion, N-methylmorpholinium ion, N-ethylmorpholinium ion, N- (iso) propylmorpholinium ion, N- (iso ) Butylmorpholinium ion, N-acetylmorpholinium ion, N- (2-nitrobutyl) morpholinium ion, N-phenylmorpholinium ion, 4-morpholinoacetophenone, N- (meth) acrylmorpholinium ion N- (meth) acryloylmorpholinium ion, bis (2-morpholinium ethyl) ether, 4-morpholinium nitrobenzene, dimorpholinium methane, acetoacetomorpholide, 4-tert-butyl-2- (Phenoxymethyl) morpholinium ion, 2,6-dimethylmorpholine Umum ion, 4- (2,3-epoxypropyl) morpholinium ion, N-formylmorpholinium ion, N- (2-hydroxyethyl) morpholinium ion, N- (4-nitrophenyl) morpholinium ion And N-nonanoylmorpholinium ion. From the viewpoint of availability, N-methylmorpholinium ion and N-ethylmorpholinium ion are particularly preferable.

In the present invention, Q ⁺ is preferably an ammonium ion having an ethylenically unsaturated bond. Q ⁺ is more preferably N, N-dimethylmonoacrylate ethylammonium ion, N, N-dimethylmonoethylmethacrylate ion, N, N-diethylmonoacrylate ethylammonium ion, N, N-diethylmono Ethylammonium methacrylate ion, N, N-diethylmono (2-isocyanoethyl) ammonium ion, N, N-diethylmono (2-cyanopropyl) ammonium ion, N, N-diethylmono (1,2-epoxypropane) Ammonium ion. Q ⁺ is still more preferably N, N-dimethylmonoethyl acrylate, ammonium ammonium, N, N-dimethylmonoethyl methacrylate, ammonium ammonium N, N-diethyl monoacrylate, N, N-diethyl. It is monoethyl methacrylate ethylammonium ion. Q ⁺ is particularly preferably an ethylammonium ion of N, N-dimethylmonoacrylate.

When Q ⁺ has an ethylenically unsaturated bond, the number of ethylenically unsaturated bonds that the ionic bond salt of the present invention has is not particularly limited and can be arbitrarily selected depending on the use, but is preferably one.

More preferable compounds of the ion binding salt represented by the chemical formula (1) include ion binding salts represented by the following chemical formulas (2) to (5). In the following chemical formulas (2) to (5), the oxybutylene group (—C ₄ H ₈ O—) is not particularly limited, but preferably has a branched butylene group, and preferably has an ethylethylene group (—CH ₂ — More preferably, it has CH (CH ₂ CH ₃ )-). That is, the oxybutylene group preferably has a group represented by the chemical formula (B1) or / and (B2). With such a compound, it is possible to form a coating film or a molded article having both water resistance and surface hydrophilicity.

(Method for producing ion-binding salt)
The production method of the ion-binding salt having a reactive group is not particularly limited, and examples thereof include an anion exchange method, a neutralization method, and an acid ester method. In addition, a deammonia method in which an ammonium salt of a sulfate ester or an ammonium salt of a sulfonic acid ester is reacted with a nitrogen-containing compound to distill off ammonia to obtain an ion-binding salt having a reactive group is also preferably used.

Wettability enhancer according to an embodiment of the present invention, Q ⁺ has an ethylenically unsaturated bond (preferably, Q ⁺ is an ammonium ion having an ethylenically unsaturated bond) derived from the ion-binding salt A polymer having a structural unit is included. The polymer may be either a homopolymer of an ion-binding salt or a copolymer of an ion-binding salt and other monomers.

  Here, the other monomer is not particularly limited as long as it is a monomer copolymerizable with the ion-binding salt, but is preferably a monofunctional (meth) acrylic monomer and has a substituted or unsubstituted C1-C20 alkyl group. (Meth) acrylic acid alkyl ester is more preferred, (meth) acrylic acid alkyl ester having a substituted or unsubstituted C1-C8 alkyl group is even more preferred, and having a substituted or unsubstituted C1-C4 alkyl group (meth) Particularly preferred are alkyl acrylates.

  Examples of C1-C20 alkyl groups include methyl, ethyl, n-propyl, isobutyl, n-butyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, 2 -An ethylhexyl group etc. are mentioned.

  Examples of the substituent that can be contained in other monomers include a hydroxyl group, an epoxy group, an amino group, and a carboxyl group.

  Specific examples of other monomers include (meth) acrylic acid, methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, (meth) acrylic acid. t-butyl, cyclohexyl (meth) acrylate, (2-ethylhexyl) (meth) acrylate, methoxypolyethylene glycol (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, glycidyl (meth) acrylate, (Meth) acrylic acid-2-hydroxyethyl, (meth) acrylic acid-2-hydroxypropyl, monoesterified product of (meth) acrylic acid and polyethylene glycol, (meth) acrylic acid-2-aminoethyl and salts thereof, (Meth) acrylic acid caprolactone modified product, (meth) acrylic (Meth) acrylic acid esters such as acid-2,2,6,6-tetramethylpiperidine, (meth) acrylic acid-1,2,2,6,6-pentamethylpiperidine; sodium (meth) acrylate, ( (Meth) acrylic acid salts such as potassium (meth) acrylate and ammonium (meth) acrylate; unsaturated nitriles such as acrylonitrile and methacrylonitrile; (meth) acrylamide, N-methylol (meth) acrylamide, N- (2- Hydroxyethyl) Unsaturated amides such as (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; Vinyl chloride, vinylidene chloride, fluoride Halogen-containing α, β-unsaturated aliphatic such as vinyl Hydrogen; styrene, divinylbenzene, alpha-methylstyrene, such as sodium styrene sulfonate alpha, beta-unsaturated aromatic hydrocarbons, and the like. These may be used individually by 1 type, and may use 2 or more types together, but it is preferable to use 2 or more types together.

  When the polymer is a copolymer, the content of the constituent unit derived from the ion-binding salt is preferably 0.1 to 99 with respect to 100% by mass of the total amount of all the constituent units constituting the polymer. It is mass%, More preferably, it is 0.5-95 mass%, 1.0-90 mass%, and 1.5-85 mass%. By preparing a polymer having a high content and adding a small amount to the resin as in Example 7 to be described later, the hydrophilicity of the resin surface can be enhanced without impairing the properties of the resin body. In addition, the said content is substantially equivalent to the ratio of the mass of the ion binding salt with respect to the total mass of all the monomers at the time of manufacturing a polymer.

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

(Method for producing polymer)
The polymer can be obtained by mixing an ion-binding salt and, if necessary, other monomers, solvents, additives and the like, and polymerizing them by heating or irradiation with light (such as ultraviolet rays). The polymerization method is not particularly limited, and known methods such as a high-pressure radical polymerization method, a medium-low pressure polymerization method, a solution polymerization method, a slurry polymerization method, a bulk polymerization method, an emulsion polymerization method, and a gas phase polymerization method can be used.

  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. These may be used alone or in combination of two or more. You may use together. The addition amount of the polymerization initiator is preferably 0.1 to 5 parts by mass with respect to 100 parts by mass of the total amount of all monomers.

  Examples of thermal polymerization initiators include methyl ethyl ketone peroxide, cyclohexanone peroxide, methylcyclohexanone peroxide, methyl acetoacetate peroxide, acetyl acetate 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-butylper Oxy) butane, 2,2-bis (4,4-di-t-butylper Xylcyclohexyl) propane, p-menthane hydroperoxide, diisopropylbenzene hydroperoxide, 1,1,3,3-tetramethylbutyl hydroperoxide, cumene hydroperoxide, t-hexyl hydroperoxide, t-butyl hydroper Oxide, α, α′-bis (t-butylperoxy) diisopropylbenzene, 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 Oxide, Lauroyl -Oxide, stearoyl peroxide, succinic acid peroxide, m-toluoylbenzoyl peroxide, benzoyl peroxide, di-n-propyl peroxydicarbonate, diisopropyl peroxydicarbonate, bis (4-t-butylcyclohexyl) peroxy Dicarbonate, 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, cumylperoxyneodecanoate, 1,1,3,3-tetramethylbutylpero Cineodecanoate, 1-cyclohexyl-1-methylethylperoxyneodecanoate, t-hexylperoxyneodecanoate, t-butylperoxyneodecanoate, t-hexylperoxypivalate, t- Butyl peroxypivalate, 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-hexylperoxyisopropylmono Carbonate, t-butylperoxyisobutyrate, t-butylperoxy Rate, t-butylperoxy-3,5,5-trimethylhexanoate, t-butylperoxylaurate, t-butylperoxyisopropylmonocarbonate, t-butylperoxy-2-ethylhexylmonocarbonate, t -Butylperoxyacetate, t-butylperoxy-m-toluylbenzoate, t-butylperoxybenzoate, bis (t-butylperoxy) isophthalate, 2,5-dimethyl-2,5-bis (m-toluyl) Peroxy) hexane, t-hexylperoxybenzoate, 2,5-dimethyl-2,5-bis (benzoylperoxy) hexane, t-butylperoxyallyl monocarbonate, t-butyltrimethylsilyl peroxide, 3,3 ′ , 4,4'-Tetra (t-butylperoxy Organic peroxide initiators such as carbonyl) 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-phenylpropylene) Onamidine) dihydrochloride, 2,2′-azobis [N- (4-chlorophenyl) -2-methylpropionamidine] dihydride 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] Hydrochloride, 2,2′-azobis [2- (3,4,5,6-tetrahydropyrimidin-2-yl) propane] dihydrochloride, 2,2′-azobis [2- (5-hydroxy-3,4) , 5,6-tetrahydropyrimidin-2-yl) propane] dihydrochloride, 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] propion Amido], 2,2′-azobis [2-methyl-N- [1,1-bis (hydroxymethyl) 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. In addition, these thermal polymerization initiators may be used independently and may use 2 or more types together.

  Examples of photopolymerization initiators include 2-hydroxy-1- {4- [4- (2-hydroxy-2-methyl-propionyl) -benzyl] phenyl} -2-methyl-propan-1-one, diethoxy Acetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyldimethyl 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-2-dimethylamino-1- (4-morpholinophenyl) butanone, 2-hydroxy-2-methyl-1- Acetophenones such as [4- (1-methylvinyl) phenyl] propanone oligomer; benzoin, ben Benzoins such as inmethyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether; benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4′-methyl-diphenyl sulfide, 3,3 ′ , 4,4'-tetra (t-butylperoxycarbonyl) benzophenone, 2,4,6-trimethylbenzophenone, 4-benzoyl-N, N-dimethyl-N- [2- (1-oxo-2-propenyloxy) ) Ethyl] benzenemethananium bromide, benzophenones such as (4-benzoylbenzyl) trimethylammonium chloride; 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2, Thioxanthones such as dichlorothioxanthone, 1-chloro-4-propoxythioxanthone, 2- (3-dimethylamino-2-hydroxy) -3,4-dimethyl-9H-thioxanthone-9-one mesochloride; 6-trimethylbenzoyl-diphenylphosphine oxide, bis (2,6-dimethoxybenzoyl) -2,4,4-trimethyl-pentylphosphine oxide, bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide, etc. And oxime esters; cationic photopolymerization initiators; intramolecular hydrogen abstraction photopolymerization initiators; and the like. In addition, these photoinitiators may be used independently and may use 2 or more types together.

  In addition, the ion-binding salt of the present invention is used as an emulsifier, and in the presence of a polymerization initiator, other monomers are emulsion-polymerized in an aqueous solvent to obtain the above polymer, or the ion-binding of the present invention in an organic solvent. A method of obtaining the above polymer by solution polymerization or ultraviolet polymerization of an organic salt and other monomers in the presence of a polymerization initiator is also preferably used since it has excellent productivity. In this case, as the emulsifier, other surfactants such as anionic surfactants and nonionic surfactants can be used together with the ion-binding salt.

  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, and xylene. , Acetonitrile, methylene chloride, chloroform, dichloroethane, methanol, ethanol, n-propanol, isopropanol, n-butanol, propylene glycol monomethyl ether and the like. These may be used alone or in combination of two or more, or may be used as a mixed solvent with water.

  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 not particularly limited, but is preferably 1 to 10 hours. The polymerization method is not particularly limited, and examples thereof include polymerization by batch charging of monomers, polymerization by dropping, and power feed polymerization.

In the case of polymerization by irradiating with ultraviolet rays, a mercury lamp (for example, a high-pressure mercury lamp or a low-pressure mercury lamp), a metal halide lamp, or the like can be used as the irradiation light source. Although the ultraviolet irradiation conditions are not particularly limited, the integrated light amount is preferably 100 mJ / cm ² or more, and more preferably 200 mJ / cm ² or more.

  The wettability improver may contain components other than the above-mentioned ion-binding salt or polymer thereof, for example, solvents, inorganic or organic fillers, various surfactants, polyvalent isocyanate compounds, epoxy compounds. , Reactive compounds such as organometallic compounds, antioxidants, processing aids, UV absorbers, fluorescent brighteners, anti-slip agents, anti-blocking agents, antistatic agents, light stabilizers, lubricants, softeners, colored dyes And other stabilizers.

<Resin composition>
The present invention also provides a resin composition containing the above-described wettability improver and a resin. The resin is preferably a thermoplastic resin and / or a thermosetting resin, and more preferably a thermoplastic resin. Hereinafter, each resin will be described. In the present specification, the term “resin” includes monomers, oligomers, prepolymers and polymers.

[Thermoplastic resin]
The thermoplastic resin used in the present invention is not particularly limited. For example, (meth) acrylic resin, styrene resin, olefin resin (including cyclic olefin resin), polyester resin, polycarbonate resin, polyamide resin, polyphenylene ether resin, polyphenylene Sulfide resins, halogen-containing resins (polyvinyl chloride, polyvinylidene chloride, fluorine resins, etc.), polysulfone resins (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 elastomers Tomah (polybutadiene, diene rubbers such as polyisoprene, styrene - butadiene copolymer, acrylonitrile - butadiene copolymer, acrylic rubber, urethane rubber, silicone rubber, etc.) and the like. The above thermoplastic resins can be used alone or in combination of two or more.

  Specific examples of (meth) acrylic resins include monofunctional (meth) acrylic monomers and their homopolymers or copolymers, polyfunctional (meth) acrylic monomers and their homopolymers or copolymers, monofunctional or polyfunctional Copolymers of (meth) acrylic monomers and other monomers are exemplified.

  Specific examples of monofunctional (meth) acrylic monomers include (meth) acrylic acid, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n-butyl (meth) acrylate, ( C1-C10 (meth) acrylic acid esters such as 2-ethylhexyl methacrylate, hydroxyalkyl (meth) acrylates such as hydroxyethyl (meth) acrylate, glycidyl (meth) acrylate, (meth) acrylonitrile Etc.

  Specific examples of the polyfunctional (meth) acrylic monomer include polyethylene glycol diacrylate, decanediol diacrylate, nonanediol diacrylate, hexanediol diacrylate, tricyclodecane dimethanol diacrylate, trimethylolpropane triacrylate, and pentaerythritol triacrylate. Examples include acrylate, pentaerythritol tetraacrylate, dipentaerythritol pentaacrylate, and dipentaerythritol hexaacrylate.

  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 and the like. Specific examples of the copolymer of the (meth) acrylic monomer and another monomer include, for example, (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) and the like can be mentioned.

  Specific examples of the styrene resin include, for example, polystyrene, poly-α-methylstyrene, α-methylstyrene-acrylonitrile copolymer, styrene-N-phenylmaleimide copolymer, and styrene-N-phenylmaleimide-acrylonitrile copolymer. And rubber reinforced polystyrene resin (HIPS resin).

  Examples of the olefin resin include a homopolymer of an olefin monomer, a copolymer of an olefin monomer, and a copolymer of an olefin monomer and another copolymerizable monomer. Specific examples of the olefin monomer include, for example, a chain olefin [carbon such as ethylene, propylene, 1-butene, isobutene, 1-pentene, 4-methyl-1-pentene, 1-hexene, 1-octene, 1-decene and the like. C2-C10 cycloalkene such as cyclopentadiene; C4-C10 cycloalkadiene such as cyclopentadiene; C7 such as norbornene and norbornadiene -20 bicycloalkene or C7-20 bicycloalkadiene; dihydrodicyclopentadiene, dicyclopentadiene, etc. C10-25 tricycloalkene or tricycloalkadiene, etc.]. These olefin monomers can be used alone or in combination of two or more. Of the olefin monomers, chain olefins such as α-olefins having 2 to 4 carbon atoms such as ethylene, propylene, and 1-butene are preferable.

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

  More specific examples of the olefin resin include, for example, polyethylene (low density polyethylene, medium density polyethylene, high density polyethylene, linear low density polyethylene, etc.), polypropylene (homopolypropylene, block polypropylene, random polypropylene, etc.), Examples include (co) polymers of chain olefins (particularly α-olefins having 2 to 4 carbon atoms) such as ethylene-propylene copolymers and ethylene-propylene-butene terpolymers. Specific examples of copolymers of olefin monomers and other copolymerizable monomers include, for example, chain olefins (particularly α-olefins having 2 to 4 carbon atoms such as ethylene and propylene) and fatty acid vinyl ester monomers. Copolymer (for example, ethylene-vinyl acetate copolymer, ethylene-vinyl propionate copolymer, etc.); copolymer of chain olefin and (meth) acryl monomer [chain olefin (especially 2 carbon atoms) (Α-olefin of ˜4) and (meth) acrylic acid (for example, ethylene- (meth) acrylic acid copolymer, propylene- (meth) acrylic acid copolymer, ionomer, etc.); chain olefin Copolymers (for example, ethylene-alkyl (meth) acrylates) (especially α-olefins having 2 to 4 carbon atoms) and alkyl (meth) acrylates. A copolymer of a chain olefin (particularly an α-olefin having 2 to 4 carbon atoms) and a diene (for example, ethylene-butadiene copolymer); an epoxy-modified polyolefin (for example, Ethylene-glycidyl (meth) acrylate copolymer), carboxy-modified polyolefin (eg, ethylene-maleic anhydride copolymer), epoxy and carboxy-modified polyolefin (eg, ethylene-maleic anhydride-glycidyl (meth) acrylate copolymer) Modified polyolefins such as olefin; and olefin elastomers (ethylene-propylene rubber, etc.).

  Specific examples of the polyester resin include, for example, (a) at least one selected from the group consisting of a dicarboxylic acid or a derivative thereof and a diol or a derivative thereof, (b) a hydroxycarboxylic acid or a derivative thereof, and (c) a lactone. Examples thereof include a polymer or copolymer obtained by polycondensation.

  Examples of the dicarboxylic acid or derivatives thereof include terephthalic acid, isophthalic acid, phthalic acid, 2,6-naphthalenedicarboxylic acid, 1,5-naphthalenedicarboxylic acid, bis (p-carboxyphenyl) methane, anthracene dicarboxylic acid, 4 , 4'-diphenyl ether dicarboxylic acid, 5-tetrabutylphosphonium isophthalic acid, 5-sodium sulfoisophthalic acid and other aromatic dicarboxylic acids, oxalic acid, succinic acid, adipic acid, sebacic acid, azelaic acid, dodecanedioic acid, malonic acid And aliphatic dicarboxylic acids such as glutaric acid and dimer acid, 1,3-cyclohexanedicarboxylic acid, 1,4-cyclohexanedicarboxylic acid and the like. Examples of the diol or derivative include aliphatic glycols having 2 to 20 carbon atoms, that is, ethylene glycol, propylene glycol, 1,4-butanediol, neopentyl glycol, 1,5-pentanediol, and 1,6-hexanediol. , Decamethylene glycol, cyclohexanedimethanol, cyclohexanediol, dimer diol, or the like, or long chain glycols having a molecular weight of 200 to 100,000, that is, polyethylene glycol, poly-1,3-propylene glycol, polytetramethylene glycol, and the like, aromatic dioxy compounds, That is, 4,4′-dihydroxybiphenyl, hydroquinone, t-butylhydroquinone, bisphenol A, bisphenol S, bisphenol F, and derivatives thereof And the like. 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 these. Derivatives and the like. Examples of the lactone include caprolactone, valerolactone, propiolactone, undecalactone, 1,5-oxepan-2-one and the like. The polyester resin also includes a polyester elastomer.

  Specific examples of the polycarbonate resin include a thermoplastic resin obtained by reacting a divalent or higher valent phenol compound with a carbonic acid diester compound such as phosgene or diphenyl carbonate.

  Examples of the divalent or higher phenol compound include 2,2-bis (4-hydroxyphenyl) propane (commonly called bisphenol A), bis (4-hydroxyphenyl) methane, bis (4-hydroxyphenyl) phenylmethane, and 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-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- Til-2,2-bis (4-hydroxyphenyl) pentane, 2,2-bis (4-hydroxyphenyl) hexane, 4,4-bis (4-hydroxyphenyl) heptane, 2,2-bis (4-hydroxy) Phenyl) nonane, 1,10-bis (4-hydroxyphenyl) decane, 1,1-bis (4-hydroxyphenyl) -3,3,5-trimethylcyclohexane, 2,2-bis (4-hydroxyphenyl)- Dihydroxydiarylalkanes such as 1,1,1,3,3,3-hexafluoropropane, 1,1-bis (4-hydroxyphenyl) cyclohexane, 1,1-bis (3,5-dichloro-4-hydroxy Dihydroxydiarylcycloalkanes such as phenyl) cyclohexane, 1,1-bis (4-hydroxyphenyl) cyclodecane Dihydroxydiaryl sulfones such as bis (4-hydroxyphenyl) sulfone, bis (3,5-dimethyl-4-hydroxyphenyl) sulfone, bis (3-chloro-4-hydroxyphenyl) sulfone, bis (4-hydroxy Phenyl) ether, dihydroxyaryl ethers such as bis (3,5-dimethyl-4-hydroxyphenyl) ether, 4,4′-dihydroxybenzophenone, 3,3 ′, 5,5′-tetramethyl-4,4 ′ -Dihydroxydiaryl ketones such as dihydroxybenzophenone, dihydroxydiaryls such as bis (4-hydroxyphenyl) sulfide, bis (3-methyl-4-hydroxyphenyl) sulfide, bis (3,5-dimethyl-4-hydroxyphenyl) sulfide Sulfides Examples include dihydroxydiaryl sulfoxides such as bis (4-hydroxyphenyl) sulfoxide, dihydroxydiphenyls such as 4,4′-dihydroxydiphenyl, and dihydroxyaryl fluorenes such as 9,9-bis (4-hydroxyphenyl) fluorene. . In addition to the above divalent 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 divalent phenol compound. .

  These divalent or higher valent phenol compounds may be used alone or in combination of two or more. Moreover, you may use linear aliphatic divalent carboxylic acid, such as adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, decanedicarboxylic acid, as a copolymerization component.

  Specific examples of the polyamide resin include aliphatic polyamides such as polyamide 46, polyamide 5, polyamide 6, polyamide 66, polyamide 610, polyamide 612, polyamide 11, polyamide 12, polyamide 6/66, polyamide 6/11; -1,4-norbornene terephthalamide, poly-1,4-cyclohexane terephthalamide poly-1,4-cyclohexane-1,4-cyclohexaneamide and other alicyclic polyamides; polyamide 6T, polyamide 9T, polyamide MXD and other fragrances Group polyamides; copolyamides formed by at least two different polyamide-forming components among these polyamides. The polyamide resin includes a polyamide elastomer.

  Specific examples of the polyphenylene ether resin include poly (2,5-dimethyl-1,4-phenylene ether), poly (2,6-dimethyl-1,4-phenylene ether), and poly (2-methyl-6). -Ethyl-1,4-phenylene ether), poly (2,6-di-n-propyl-1,4-phenylene ether), poly (2-methyl-6-chloroethyl-1,4-phenylene ether), etc. Examples include homopolymers, modified polyphenylene ether copolymers based on these homopolymers, polyphenylene ether homopolymers or modified graft copolymers in which a styrene polymer is grafted on the copolymer. .

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

  As the thermoplastic resin, a synthetic product or a commercially available product may be used. In the case of synthetic products, resins (resin polymers) are synthesized using known methods such as high-pressure radical polymerization, medium-low pressure polymerization, solution polymerization, slurry polymerization, bulk polymerization, emulsion polymerization, and gas phase polymerization. However, it may be applied to a resin composition. At that time, the above-mentioned thermal polymerization initiator or photopolymerization initiator may be used.

  The form of the copolymer when the thermoplastic resin is a copolymer may be a block copolymer, a random copolymer, a graft copolymer, or an alternating copolymer.

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

[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 and the like. It is done. As the thermosetting resin, a synthetic product or a commercially available product may be used.

  In the resin composition of the present invention, the content of the ionic bond salt represented by the chemical formula (1) or the structural unit derived from the ionic bond salt is 0.1 to 400 parts by mass with respect to 100 parts by mass of the resin. It is preferably 0.1 to 20 parts by mass, more preferably 0.1 to 10 parts by mass, and particularly preferably 0.1 to 5 parts by mass. By being in such a content range, the surface of the coating film formed from the resin composition can express good hydrophilicity and stain resistance without impairing the original properties of the resin.

  The resin composition of the present invention is a polymerization initiator, an antioxidant, a filler, a lubricant, a dye, an organic pigment, an inorganic pigment, a plasticizer, a processing aid, an ultraviolet absorber, as long as the object of the present invention is not impaired. Light stabilizer, foaming agent, wax, crystal nucleating agent, mold release agent, hydrolysis inhibitor, antiblocking agent, antistatic agent, radical scavenger, antifogging agent, antifungal agent, ion trapping agent, flame retardant, difficult Other additive components such as a fuel auxiliary agent and a surfactant can be appropriately blended. For example, when a resin composition containing a resin monomer is applied to an object and cured, the resin composition preferably contains a polymerization initiator in order to accelerate curing. Examples of the polymerization initiator include the thermal polymerization initiator and the photopolymerization initiator as described above.

  The form of the resin composition of the present invention is not particularly limited, and may be any form such as a solid form, an emulsion, a translucent solution, and a transparent solution, but an emulsion is preferable from the viewpoint of reducing environmental burden.

  The resin composition of the present invention can be produced by mixing an ion-binding salt or a wettability improver containing a polymer thereof, a resin, and, if necessary, the above additives by stirring or melt-kneading. it can. The melt kneading method is not particularly limited, and for example, a method using a device 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 employed. .

<Use of wettability improver and resin composition containing the same>
The wettability improver of the present invention and the resin composition containing the same can be suitably used as a hydrophilic coating agent. Specifically, a hydrophilic coating film is formed on the surface of the molded article by applying the hydrophilic coating agent comprising the wettability improver or the resin composition of the present invention to the surface of the molded article and drying or curing it. . The surface of the obtained hydrophilic coating film is excellent in hydrophilicity, for example, the contact angle with water is preferably 20 ° or less, more preferably 10 ° or less, even more preferably 5 ° or less, and particularly preferably less than 5 °. It is. Therefore, the molded article in which the hydrophilic coating film is disposed on the surface is excellent in hydrophilicity and thus stain resistance.

  Although it does not restrict | limit especially as a molded article used as the object which improves hydrophilicity, For example, a film, a plastics, glass, a fiber, a sheet | seat, a tape, etc. are mentioned, Preferably a film, a plastics, glass is mentioned.

  As a 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 brushing, impregnation, and coating by a bar coater. Such a method can be used.

  The drying conditions can be adjusted as appropriate according to the heat resistance of the molded product and the boiling point of the solvent contained in the hydrophilic coating agent. The drying temperature is not particularly limited, and is, for example, 50 to 180 ° C, 80 to 150 ° C, or 110 to 130 ° C. The drying time is not particularly limited, and is, for example, 0.5 to 120 minutes, 1 to 60 minutes, or 1 to 10 minutes. The drying atmosphere is not particularly limited, and is, for example, air, inert gas (for example, nitrogen), or vacuum.

  The curing method may be either photocuring or heat curing, but photocuring is preferable from the viewpoint of short-time curing and reduced 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, a (meth) acrylic resin as described in the section of [Thermoplastic resin] is preferable, and a polyfunctional (meth) acrylic monomer is more preferable.

In the case of photocuring, a light source that generates ultraviolet rays is preferably used, and a mercury lamp (for example, a high-pressure mercury lamp or a low-pressure mercury lamp), a metal halide lamp, or the like can be used. The irradiation conditions of the ultraviolet ray is not particularly limited, the integrated light quantity is preferably 100~1000mJ / cm ^2, more preferably 200~500mJ / cm ^2. In the case of thermosetting, it may be performed under the same conditions as the above-mentioned drying. That is, drying and heat curing may proceed simultaneously.

  In forming the hydrophilic coating film, both drying and curing may be performed. For example, photocuring may be performed after removing the solvent contained in the hydrophilic coating agent by preliminary drying.

  The film thickness of the hydrophilic coating film to be formed is preferably 1 to 50 μm, more preferably 5 to 20 μm, and even more preferably 10 to 15 μm as a dry film thickness. If it is such a range, it will be excellent in the hydrophilicity of the surface of a molded article, and surface hardness will be maintained favorable before and after coating-film formation.

  In the hydrophilic coating film, the content of the structural unit derived from the ion-binding salt is preferably 0.1 to 800% by mass, more preferably 0.5 to 400% by mass with respect to 100% by mass of the resin. is there. Within such a range, the hydrophilicity of the surface of the molded product can be improved without impairing the original properties of the molded product. In addition, the said content is substantially equivalent to the ratio of the mass of ion binding salt with respect to the total mass of resin (for example, resin monomer).

  As another use of the wettability improver of the present invention, for example, it can be mixed with a raw material for producing a molded article having hydrophilicity. Although it does not restrict | limit especially as a molded article, For example, a film, a plastics, glass, a fiber, a sheet | seat, or a tape etc. are mentioned, Preferably a film, a plastics, glass is mentioned.

  Other uses of the resin composition of the present invention include, for example, paints, adhesives, pressure-sensitive adhesives, fiber 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.). You may produce the molded article which consists of a resin composition of this invention, and may apply the said molded article to these uses. The surface of the molded article is excellent in hydrophilicity, for example, the contact angle with water is preferably 20 ° or less, more preferably 10 ° or less, even more preferably 5 ° or less, and particularly preferably less than 5 °. .

  The molded product can be produced by a known method such as injection molding, extrusion molding, transfer molding, inflation method, compression molding or the like. These methods can be appropriately selected according to the shape of the obtained molded product.

  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 only to the following examples. In the following examples, the operation was performed at 25 ° C. unless otherwise specified. Unless otherwise specified, “%” and “part” mean “% by mass” and “part by mass”, respectively.

(Synthesis Example 1: Synthesis of [2M-AA] [130305-S])
After adding 2 parts by mass of potassium hydroxide to 200.4 parts by mass of tridecanol and raising the temperature to 170 ° C., 216.3 parts by mass of 1,2-butylene oxide was injected under conditions of 1.0 MPa or less. Reacted for hours. Thereafter, 220.3 parts by mass of ethylene oxide was further injected under a condition of 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., 97.1 parts by mass of sulfamic acid was added, and the reaction was performed for 3 hours. After the reaction, unreacted sulfamic acid was filtered off and polyoxybutylene / polyoxyethylene tridecyl ether sulfate ammonium salt ([C ₁₃ H ₂₇ —O— (BO) ₃ — (EO) ₅ —SO ₃ ⁻ ]]. [NH ₄ ⁺ ]) 734.1 parts by mass were obtained.

N, N-dimethylaminoethyl A acrylate (abbreviation: 2M-AA) to 143.2 parts by mass, the above-synthesized polyoxybutylene / polyoxyethylene tridecyl ether sulfate ammonium salt (abbreviation: 130305-SF) 734 After adding 1 part by mass, the mixture was reacted at 50 ° C. for 1 hour. After the reaction, 860.1 parts by mass of the target ion-binding salt (abbreviation: [2M-AA] [130305-S], a compound represented by the chemical formula (2)) was obtained.

  (Synthesis Example 2: Synthesis of [2M-AA] [1305-S]) Polyoxyethylene tridecyl ether sulfate ester salt (abbreviation: 1305-SF) synthesized by a conventionally known method instead of 130305-S 517. The target ion-binding salt (abbreviation: [2M-AA] [1305-S], Japanese Patent No. 5763832 (Patent Document 1)) is the same as Synthesis Example 1 except that 4 parts by mass is used. The compound represented by the chemical formula (7) was obtained in an amount of 643.6 parts by mass.

Example 1
In a Kolben equipped with a cooling pipe, a nitrogen introduction pipe, a thermometer, and a Teflon (registered trademark) half moon stirring blade, 100 parts by mass of toluene, 65 parts by mass of methyl methacrylate, 35 parts by mass of n-butyl acrylate, 2 parts by weight of the synthesized [2M-AA] [130305-S] was charged, 1 part by weight of 2,2′-azobisisobutyronitrile was added as a polymerization initiator, and solution polymerization was performed at 90 ° C. for 3 hours. . The obtained polymer solution was applied on a glass plate with a bar coater so as to have a wet film thickness of 75 μm, and dried for 10 minutes with a dryer at 110 ° C. to obtain a test piece having a coating film with a dry film thickness of 15 μm.

(Comparative Example 1)
In the same manner as in Example 1 except that 2 parts by mass of [2M-AA] [1305-S] synthesized in Synthesis Example 2 was used instead of [2M-AA] [130305-S], A test piece having a coating film with a dry film thickness of 15 μm was obtained.

(Example 2)
100 parts by mass of dipentaerythritol hexaacrylate (manufactured by Shin-Nakamura Chemical Co., Ltd., NK ester A-DPH), 2 parts by mass of [2M-AA] [130305-S] synthesized in Synthesis Example 1 above, 100 of propylene glycol monomethyl ether A part by mass was charged, and 3 parts by mass of Irgacure 127 (manufactured by BASF Japan Ltd.) was added as a polymerization initiator. The obtained solution was applied onto a PET plate with a bar coater so as to have a wet film thickness of 75 μm, dried for 1 minute with a dryer at 70 ° C., and then irradiated with an ultraviolet irradiation device (ECS, manufactured by Eye Graphics Co., Ltd.). −4011GX, mercury lamp) was used for polymerization with an integrated light quantity of 500 mJ / cm ² to obtain a test piece having a coating film with a dry film thickness of 15 μm.

(Comparative Example 2)
Instead of [2M-AA] [130305-S], in the same manner as in Example 2 except that 2 parts by mass of [2M-AA] [1305-S] synthesized in Synthesis Example 2 was used, A test piece having a coating film with a dry film thickness of 15 μm was obtained.

Example 3
20 parts by mass of dipentaerythritol hexaacrylate (manufactured by Shin-Nakamura Chemical Co., Ltd., NK ester A-DPH), 80 parts by mass of [2M-AA] [130305-S] synthesized in Synthesis Example 1 above, 100 propylene glycol monomethyl ether A part by mass was charged, and 3 parts by mass of Irgacure 127 (manufactured by BASF Japan Ltd.) was added as a polymerization initiator. The obtained solution was applied onto a PET plate with a bar coater so as to have a wet film thickness of 75 μm, dried for 1 minute with a dryer at 70 ° C., and then irradiated with an ultraviolet irradiation device (ECS, manufactured by Eye Graphics Co., Ltd.). −4011GX, mercury lamp) was used for polymerization with an integrated light quantity of 500 mJ / cm ² to obtain a test piece having a coating film with a dry film thickness of 15 μm.

(Example 4)
A four-necked flask equipped with a cooling tube, a nitrogen introducing tube, a thermometer, and a Teflon (registered trademark) half moon stirring blade was charged with 100 parts by mass of propylene glycol monomethyl ether, heated to 70 ° C. in a nitrogen atmosphere, Under reflux, 5 parts by weight of methyl methacrylate, 15 parts by weight of glycidyl methacrylate, 80 parts by weight of [2M-AA] [130305-S] synthesized in Synthesis Example 1, and 2,2′-azobisbutyroyl as a polymerization initiator A mixture of 1 part by mass of nitrile (AIBN) was added dropwise over 180 minutes using a dropping pump. Thereafter, 0.5 part by mass of AIBN was added and aged at 70 ° C. for 60 minutes. The obtained polymer solution was applied on a glass plate with a bar coater so as to have a wet film thickness of 75 μm, and dried for 10 minutes with a dryer at 130 ° C. to obtain a test piece having a coating film with a dry film thickness of 15 μm.

(Example 5)
In Example 4 above, dry conditions were changed in the same manner as in Example 4 except that methyl methacrylate was changed to 35 parts by mass, glycidyl methacrylate 15 parts by mass, and [2M-AA] [130305-SF] 50 parts by mass. A test piece having a coating film with a thickness of 15 μm was obtained.

(Example 6)
In Example 4 above, except that methyl methacrylate 65 parts by mass, glycidyl methacrylate 15 parts by mass, and [2M-AA] [130305-SF] 20 parts by mass were changed, A test piece having a coating film with a thickness of 15 μm was obtained.

(Example 7)
<Preparation of test (meth) acrylic resin>
A four-necked flask equipped with a cooling tube, a nitrogen introduction tube, a thermometer, and a Teflon (registered trademark) half moon stirring blade was charged with 100 parts by mass of toluene, 35 parts by mass of n-butyl acrylate, and 65 parts by mass of methyl methacrylate, and polymerization catalyst 1 part by weight of AIBN was added and polymerization was carried out at 90 ° C. for 3 hours to obtain a (meth) acrylic resin toluene solution having a solid content of 50% by mass. 5 parts by mass of the polymer solution synthesized in Example 4 (solid content: 50% by mass propylene glycol monomethyl ether solution) was mixed with 100 parts by mass of the prepared (meth) acrylic resin solution. The obtained mixed solution was applied onto a glass plate with a bar coater so as to have a wet film thickness of 75 μm, and dried for 10 minutes with a dryer at 130 ° C. to obtain a test piece having a coating film with a dry film thickness of 15 μm.

<Evaluation of contact angle>
The contact angle of water was measured for the coating films of the test pieces obtained in the above Examples and Comparative Examples. Specifically, using a contact angle meter (manufactured by Kyowa Interface Science Co., Ltd., model number: CA-XP), in a dry state (25 ° C./50% RH), about 1 μL droplet using pure water as a liquid. Was made on the needle tip and brought into contact with the surface of the resin composition to form droplets on the coating film. The angle between the tangent to the liquid surface and the surface of the coating film at the point where the resin composition and the liquid are in contact with each other and the angle on the side containing the liquid was defined as the contact angle.

  Table 1 shows the evaluation results of the contact angles of the examples and comparative examples.

  As is clear from Table 1, the coating films (Examples 1 to 7) prepared using [2M-AA] [130305-S] as the ion-binding salt had [2M-AA] as the ion-binding salt. Compared to the coating films prepared using [1305-S] (Comparative Examples 1 and 2), the surface contact angle with water was low, and the hydrophilicity was very good. The affinity between the hydrophobic part of the oxybutylene group of [2M-AA] [130305-S] and the hydrophobic part of the resin (MMA, BA, DPHA) is higher, and it is coated than [2M-AA] [1305-S]. Since it is dispersed locally, not locally, in the film, the hydrophilic part of [2M-AA] [130305-S] is efficiently oriented on the coating film surface, so that it is more efficiently made hydrophilic. Conceivable.

  From the above, it has been confirmed that the ion-binding salt according to the present invention has the effect of improving the hydrophilicity of the coating film surface even when added in a small amount. Moreover, it was found that the coating film formed using the ion-binding salt according to the present invention has a contact angle with water of less than 5 ° and is extremely hydrophilic (superhydrophilic).

Claims (19)

Wettability improver containing an ion-binding salt represented by the following chemical formula (1):

In the chemical formula (1),
R is a linear alkyl group having 12 to 14 carbon atoms which may be substituted;
A is a linear or branched alkylene group having 2 to 4 carbon atoms,
m is an average added mole number of AO and is an integer of 2 to 50;
(AO) _m includes an oxyethylene group and an oxybutylene group , and the arrangement thereof may be either a random type or a block type.
n is 1 or 2 with a valence of Q ⁺ ,
Q ⁺ is a nitrogen-containing compound ion having an ethylenically unsaturated bond . 2. The wettability improver according to claim 1, wherein in (AO) _m , the proportion of oxybutylene groups is 3 to 90 mol%. The nitrogen-containing compound ions are ammonium ion, imidazolium ion, pyridinium ion, pyrrolidinium ion, pyrrolium ion, piperidinium ion, pyrazinium ion, pyrimidinium ion, triazolium ion, triazinium ion, quinolinium ion. And at least one selected from the group consisting of isoquinolinium ion, indolinium ion, quinoxalinium ion, piperazinium ion, oxazolinium ion, thiazolinium ion, and morpholinium ion. The wettability improver according to 1 or 2 . The wettability improver according to any one of claims 1 to 3 , wherein the Q ⁺ is an ammonium ion having an ethylenically unsaturated bond. The wettability improver according to any one of claims 1 to 4, wherein R is an optionally substituted linear alkyl group having 13 carbon atoms. Q ⁺ N, N-dimethylmonoethyl acrylate ammonium ion, N, N-dimethylmonoethyl methacrylate ion ammonium ion, N, N-diethyl monoacrylate ethylammonium ion or N, N-diethylmonoethyl methacrylate ammonium ion The wettability improving agent according to any one of claims 1 to 5. The wettability improvement agent containing the polymer which has a structural unit derived from the ion binding salt of any one of Claims 1-6 .   A resin composition comprising the wettability improver according to claim 1 and a resin.   The resin composition according to claim 8, wherein the constituent unit derived from the ion-binding salt or the ion-binding salt is contained in an amount of 0.1 part by mass or more and less than 5 parts by mass with respect to 100 parts by mass of the resin.   A hydrophilic coating agent comprising the wettability improver according to claim 7.   A hydrophilic coating agent comprising the resin composition according to claim 8 or 9.   The hydrophilic coating agent according to claim 11, wherein the resin composition contains a photocurable resin.   The hydrophilic coating film which dried or hardened the hydrophilization coating agent of any one of Claims 10-12.   The hydrophilic coating film of Claim 13 whose contact angle with respect to the water of the surface is 20 degrees or less.   The molded article which has a hydrophilic surface which has a molded article and the hydrophilic coating film of Claim 13 or 14 arrange | positioned on the surface of the said molded article.   A step of forming a hydrophilic coating film on the surface of the molded article by applying the hydrophilic coating agent according to any one of claims 10 to 12 to the surface of the molded article and drying or curing the coating agent. A method for producing a molded article having a hydrophilic surface.   The manufacturing method of the molded article of Claim 16 whose contact angle with respect to the water of the said hydrophilic coating film is 20 degrees or less.   A molded article comprising the resin composition according to claim 8 or 9.   The molded product according to claim 18, wherein a contact angle with respect to water of the molded product surface is 20 ° or less.