KR20130024847A - Adhesive composition containing antistaic agent and adhesive film - Google Patents

Abstract

PURPOSE: An adhesive composition is provided to have excellent antistatic performance, to have excellent adhesion to a glass plate, and to have excellent re-workability to an object. CONSTITUTION: An adhesive composition contains a (meth)acrylic polymer as a main component and comprises an ionic compound indicated in chemical formula 1: Z^+X^-. The ionic compound has an organic cation which contains a hydrolyzable silicon-containing group. In the chemical formula 1, Z^+ is a cation and X^- is an anion. The adhesive composition has a surface resistance of 1.0×10^12 Ω/□ or less.

Description

Adhesive composition and adhesive film containing an antistatic agent {ADHESIVE COMPOSITION CONTAINING ANTISTAIC AGENT AND ADHESIVE FILM}

The present invention relates to an adhesive composition and an adhesive film containing an antistatic agent. More specifically, it relates to the adhesive composition containing an alkoxysilyl group containing ionic compound as an antistatic agent. An adhesive composition having excellent antistatic performance without impairing adhesive performance, containing an alkoxysilyl group, excellent adhesion to a glass plate, and excellent rework to an adherend, and an adhesive film using the same It is about providing.

Background Art Conventionally, in the manufacturing and assembling process of precision parts and members such as electronic device parts, optical device parts, and image display panels, the surfaces of such precision parts and members are temporarily protected, and the particles and gaseous state are removed from the working environment atmosphere. In order to prevent contaminants from adhering to each other or to cause damage and scratches caused by friction, a surface protective film is attached to the surfaces of the precision parts and members.

For example, in the surface protection film used at the process of manufacturing optical members, such as a polarizing plate and retardation plate which are members which comprise a liquid crystal display, an adhesive layer is formed in one surface of the polyethylene terephthalate (PET) resin film which has optical transparency. Although it is, the peeling process release film for protecting the adhesive layer is affixed on the adhesive layer until it adheres to an optical member.

In addition, since optical members, such as a polarizing plate and a retardation plate, perform the product test | inspection which involves optical evaluation, such as display capability, a hue, contrast, and a foreign material mixing, of a liquid crystal display panel in the state with a surface protection film adhered, As a required performance with respect to a surface protection film, it is calculated | required that foam | bubble and a foreign material do not adhere to an adhesive layer.

In addition, in recent years, peeling charging generated due to static electricity generated when peeling off the pressure-sensitive adhesive layer from the adherend when peeling the surface protective film from optical members such as polarizing plates and retardation plates has caused a failure of the electrical control circuit of the liquid crystal display. There is a possibility of adversely affecting, and excellent antistatic performance is required for the pressure-sensitive adhesive layer.

Moreover, the optical member often has the surface which consists of glass (inorganic glass, especially an alkali free glass), and it is calculated | required that it is excellent in adhesiveness with respect to a glass plate.

In addition, when attaching a surface protection film to optical members, such as a polarizing plate and retardation plate, for a variety of reasons, a surface protection film may be peeled off once and a surface protection film may be affixed again, and at this time, from an optical member which is a to-be-adhered body It is required to be easy to peel off (reworkability).

As described above, in recent years, as the performance required for the pressure-sensitive adhesive layer constituting the surface protection film, the adhesion to the glass plate, the excellent antistatic performance, the reworkability to the adherend, etc. It is required from the standpoint of ease of use.

However, even though each of the required performances such as adhesion to such a glass plate, excellent antistatic performance, and reworkability to the adherend, which are required performances for the adhesive layer constituting the surface protective film, can be individually satisfied, the surface It was difficult to simultaneously meet all the required performances required for the pressure-sensitive adhesive layer of the protective film at low production cost.

About the outstanding antistatic performance, the method of penetrating an antistatic agent into a base film as a method for giving antistatic performance to a surface protection film, etc. are shown. Examples of the antistatic agent include (a) various cationic antistatic agents having cationic groups such as quaternary ammonium salts, pyridinium salts, and primary to tertiary amino groups, (b) sulfonate groups, sulfate ester bases, and phosphate esters. Anionic antistatic agents having anionic groups such as bases and phosphonic acid bases, (c) amphoteric antistatic agents such as amino acid-based and amino sulfate esters, and (d) nonionic charging such as amino alcohols, glycerins, and polyethylene glycols. The antistatic agent, (e) The polymeric antistatic agent etc. which made the above antistatic agent high molecular weight are disclosed (patent document 1).

Moreover, in recent years, the method of making it contain, such as an antistatic agent in a base film or directly in an adhesive layer, without apply | coating to the surface of a base film is proposed (patent document 2).

In Patent Literature 2, a polymerizable mixture comprising (1) (a) urethane acrylate, (b) a (meth) acrylate having a polyalkylene oxide chain, and (c) an adhesive force imparting monomer as a main component is a radiation. The adhesive composition which has an antistatic performance containing the copolymer obtained by superposing | polymerizing, and (2) ionic compound, and the adhesive sheet using the same are disclosed.

As a specific manufacturing method of an adhesive composition, it is urethane acrylate like polyester urethane acrylate, (meth) acrylate monomer which has a polyoxyalkylene chain like methoxy polyethyleneglycol acrylate, and hydroxypropyl acrylate. To the polymerizable mixture comprising a monomer having a property of imparting adhesion and a new comonomer, such as isooctyl acrylate, if necessary, an ionic compound such as lithium perchlorate is mixed, and a photopolymerization initiator is added if necessary. After stirring until it melt | dissolves completely, an adhesive composition is obtained by irradiating and hardening an ultraviolet-ray etc ..

However, since lithium perchlorate used as an ionic compound has metal corrosiveness, there exists a problem that the place where it can use the adhesive composition which has the obtained antistatic performance is limited.

Moreover, about the rework to the polarizing plate of a liquid crystal panel, the adhesive composition which mix | blended the hardening | curing agent of an isocyanate type compound and a specific silicate oligomer with 0.0001-10 weight part with respect to 100 weight part of acrylic resin in acrylic resin, for example. This has been proposed (patent document 3).

In patent document 3, acrylic acid alkyl ester whose carbon number of an alkyl group is about 2-12, methacrylic acid alkyl ester whose carbon number is about 4-12 of an alkyl group, etc. are made into a main monomer component, For example, other functional groups, such as a carboxyl group-containing monomer, etc. It is supposed that the containing monomer component can be included. Generally, it is preferable to contain the main monomer at 50% by weight or more. Moreover, content of a functional group containing monomer component is 0.001 to 50 weight%, Preferably it is 0.001 to 25 weight%, More preferably, it is 0.01 to 25 weight%. Such a pressure-sensitive adhesive composition described in Patent Document 3 has reworkability in that the change in cohesion and adhesion over time is small even under high temperature or high temperature and high humidity, and also shows an excellent effect in adhesion to curved surfaces. It is.

In general, when the pressure-sensitive adhesive layer is made soft, the residual of the pressure-sensitive adhesive component tends to be generated, and reworkability tends to decrease. That is, peeling is difficult and reattachment becomes difficult when attached by mistake. For this reason, it is thought that crosslinking monomer which has functional groups, such as a carboxyl group, to a main body and making an adhesive layer constant hardness is necessary in order to provide reworkability.

Japanese Patent Laid-Open No. H11-070629 Japanese Patent Laid-Open No. 2000-129235 Japanese Patent Laid-Open No. H8-199130

It is often required to impart antistatic performance to an adhesive sheet, and various kinds of antistatic agents have been tried. However, especially in the use of an optical film, the antistatic performance can be imparted, but there are disadvantages such as poor transparency, and further, due to the lack of compatibility of the antistatic agent with respect to the pressure-sensitive adhesive, etc., the glass plate as the adherend. There is a problem such as poor adhesion to, or durability does not improve. Moreover, when the bleed out of the antistatic agent and the adhesive sheet were peeled off, there were many defects such as poor reworkability of the adherend. Even if these performances can be satisfied, there are also problems such as high price, and there has been a need for an adhesive containing an antistatic agent that can overcome such defects at low cost.

This invention is made | formed in view of the said situation, The subject is the antistatic agent which is excellent in antistatic performance, excellent adhesiveness with respect to a glass plate, without impairing adhesive performance, and also excellent in reworkability to a to-be-adhered body. It provides the adhesive composition containing and the adhesive film using this.

MEANS TO SOLVE THE PROBLEM In order to solve the said subject, this invention is an adhesive composition containing an antistatic agent, Comprising: (meth) acrylic-type polymer as a main component, The antistatic agent contains the ionic compound represented by following formula (1), The said ionic compound There is provided an adhesive composition characterized by having an organic cation comprising a hydrolyzable silicon-containing group:

Z⁺ X^- (Formula 1)

Wherein Z ⁺ represents a cation and X ⁻ represents an anion.

The cation (Z ⁺ ) of the ionic compound is preferably one or two or more alkoxysilyl group-containing cations represented by the following general formula (2):

(R ¹ O) _n (R ² ) _{3- n} Si-Q ¹ -EQ ² -COO-Q ³ -V ⁺ (Formula 2)

Wherein R ¹ and R ² represent the same or different alkyl groups, n represents an integer of 1 to 3, Q ¹ represents an alkylene group having 1 to 10 carbon atoms, E represents NH or S, and Q ² represents a single bond or an alkylene group having 1 to 10 carbon atoms, Q ³ represents an alkylene group having 1 to 10 carbon atoms, and V ⁺ represents an ammonium group, a pyridinium group, a pyrrolidinium group, an imidazolium group or a guani It represents a monovalent cation group selected from dinium group, isouronium group, thiouronium group, piperidinium group, pyrazolium group, morpholinium group, phosphonium group, sulfonium group, the cation group may be substituted or unsubstituted.

The hydrolyzable silicon-containing group is preferably an alkoxysilyl group selected from trimethoxysilyl group, triethoxysilyl group, methyldimethoxysilyl group, methyldiethoxysilyl group, ethyldimethoxysilyl group and ethyldiethoxysilyl group. Do.

At least 1 of the copolymerizable vinyl monomer in which the said (meth) acrylic-type polymer contains the at least 1 sort (s) of the alkyl (meth) acrylate monomer whose C1-C14 carbon number of (A) alkyl group, and (B) hydroxyl group and / or a carboxyl group. It is a copolymer composition which consists of a species, It is preferable that the said antistatic agent contains 0.1-20 weight part of ionic compounds represented by the said (C) said Formula (1) as an essential component with respect to 100 weight part of said copolymerization compositions.

Copolymerization of the said (meth) acrylic-type polymer consisting of at least 1 sort (s) of the alkyl (meth) acrylate monomer which has C1-C14 carbon number of (A) alkyl group, and at least 1 sort (s) of the copolymerizable vinyl monomer which has a (B ') vinyl group. It is a composition, It is preferable that the said antistatic agent contains 0.1-20 weight part of ionic compounds represented by the said (1) as an essential component with respect to 100 weight part of said copolymerization compositions.

The said (meth) acrylic-type polymer is a copolymer composition which consists of at least 2 or more types of alkyl (meth) acrylate monomers whose C1-C14 carbon number of the (A) alkyl group is the said antistatic agent with respect to 100 weight part of the said copolymer composition. (C) It is preferable to contain 0.1-20 weight part of ionic compounds represented by the said General formula (1) as an essential component.

It is preferable that the surface resistivity of the adhesive layer which consists of the said adhesive composition is 1.0x10 ^{+ 12} ohms / square or less.

The anion (X ⁻ ) of the ionic compound is a hexafluorophosphate anion, bis (fluorosulfonyl) imide anion, tris (pentafluoroethyl) trifluoro phosphate anion, bis (trifluoromethanesulfonyl) It is preferable that it is 1 type, or 2 or more types chosen from the inorganic or organic anion group which consists of an imide anion, a thiocyanate anion, an alkylbenzene sulfonic acid anion, a perchlorate anion salt, and a tetrafluoroborate anion.

Moreover, this invention provides the adhesive film characterized by the said adhesive composition laminated | stacked on one side of the base material.

In addition, the present invention provides a pressure-sensitive adhesive film characterized in that the pressure-sensitive adhesive layer made of the pressure-sensitive adhesive composition is laminated on one side of the substrate.

Moreover, this invention provides the surface protection film in which the said adhesive film was used.

Moreover, this invention provides the surface protection film for polarizing plates in which the said adhesive film was used.

Moreover, this invention provides the surface protection film for optics in which the said adhesive film was used.

Moreover, this invention provides the optical film with an adhesive with which the adhesive layer which consists of said adhesive composition is laminated | stacked on at least one surface of an optical film.

It is preferable that the optical film of the optical film with an adhesive is a polarizing plate.

Moreover, this invention provides the image display apparatus with which the said optical film with an adhesive was stuck through the said adhesive layer.

According to the present invention, by using an adhesive containing an antistatic agent having a hydrolyzable silicon-containing group, particularly an alkoxysilyl group, the adhesiveness to the glass plate is excellent, and the antistatic performance, reworkability to the adherend, etc. It is possible to improve the defect.

EMBODIMENT OF THE INVENTION Hereinafter, this invention is demonstrated based on suitable embodiment.

The adhesive composition of this invention has the adhesive polymer which becomes a main component of an adhesive, and the antistatic agent which provides antistatic performance, and contains as said antistatic agent an ionic compound which has a hydrolyzable silicon-containing group, especially an alkoxysilyl group. It is characterized by.

Thereby, it is excellent in the adhesiveness with respect to a glass plate, and can improve defects, such as antistatic performance and reworkability to a to-be-adhered body.

As an adhesive polymer used for this invention, an acryl-type polymer is preferable and especially the copolymer composition which has at least 1 sort (s) of the alkyl (meth) acrylate monomer whose carbon number of (A) alkyl group is C1-C14 is preferable.

As an alkyl (meth) acrylate monomer whose carbon number of (A) alkyl group is C1-C14, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, isobutyl (Meth) acrylate, pentyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, octyl (meth) acrylate, isooctyl (meth) acrylate, 2-ethyl hexyl (meth) acrylic The rate, nonyl (meth) acrylate, isononyl (meth) acrylate, decyl (meth) acrylate, cyclopentyl (meth) acrylate, cyclohexyl (meth) acrylate, etc. are mentioned. The alkyl group of the alkyl (meth) acrylate monomer may be linear, branched or cyclic.

As an adhesive polymer used for this invention, the copolymer composition which consists of at least 1 sort (s) of the alkyl (meth) acrylate monomer whose carbon number of (A) alkyl group is C1-C14, and at least 1 sort (s) of another copolymerizable monomer can also be used. In this case, as another copolymerizable monomer, the copolymerizable vinyl monomer which has a (B ') vinyl group, and the copolymerizable vinyl monomer containing (B) hydroxyl group and / or a carboxyl group are mentioned.

As a copolymerizable vinyl monomer containing a hydroxyl group, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, and 4-hydroxybutyl (meth ) Hydroxyl-containing (meth) acrylic acid esters such as acrylate, 6-hydroxyhexyl (meth) acrylate and 8-hydroxyoctyl (meth) acrylate, N-hydroxy (meth) acrylamide, and N-hydroxy Hydroxyl group-containing (meth) acrylamides such as methyl (meth) acrylamide and N-hydroxyethyl (meth) acrylamide; and the like, and are preferably at least one or more selected from these compound groups.

Examples of the copolymerizable vinyl monomer containing a carboxyl group include (meth) acrylic acid, itaconic acid, crotonic acid, maleic acid, fumaric acid, carboxyethyl (meth) acrylate, carboxypentyl (meth) acrylate, and the like. It is preferable that it is at least 1 sort (s) or more selected from the group.

As copolymerizable vinyl monomers other than the above, in addition to aromatic group-containing (meth) acrylic acid esters such as benzyl (meth) acrylate and phenoxyethyl (meth) acrylate, styrene, acrylamide, acrylonitrile, methyl vinyl ether, Various vinyl monomers, such as ethyl vinyl ether, vinyl acetate, and a vinyl chloride, are mentioned.

Moreover, as an adhesive polymer used for this invention, the copolymer composition which consists of at least 2 or more types of the alkyl (meth) acrylate monomer whose carbon number of (A) alkyl group is C1-C14 can also be used. In this case, it can be set as a copolymer composition, even if it does not use a copolymerizable vinyl monomer other than the alkyl (meth) acrylate monomer whose carbon number of (A) alkyl group is C1-C14.

The ionic compound used as an antistatic agent in the present invention is represented by the following formula (1), the cation (Z ⁺ ) is an organic cation having a hydrolyzable silicon-containing group, the ionic compound is a room temperature (for example 30 ℃) It may be an ionic liquid which becomes a liquid at, and may be a solid at room temperature:

Z⁺ X^- (Formula 1)

Wherein Z ⁺ represents a cation and X ⁻ represents an anion.

The anion (X ⁻ ) of the ionic compound is a hexafluorophosphate anion, bis (fluorosulfonyl) imide anion, tris (pentafluoroethyl) trifluorophosphate anion, bis (trifluoromethanesulfonyl) It is preferable that it is 1 type, or 2 or more types chosen from the inorganic or organic anion group which consists of an imide anion, a thiocyanate anion, an alkylbenzene sulfonic acid anion, a perchlorate anion salt, and a tetrafluoroborate anion.

The cation (Z ⁺ ) of the ionic compound is pyridinium cation, imidazolium cation, sulfonium cation, phosphonium cation, pyrrolidinium cation, guanidinium cation, ammonium cation, isuroronium cation, thiouronium It is preferable that it is 1 type, or 2 or more types chosen from the cation group which consists of a cation, a piperidinium cation, a pyrazolium cation, a morpholinium cation, etc.

The cation (Z ⁺ ) is an organic cation having a hydrolyzable silicon-containing group.

As the hydrolyzable silicon-containing group, an alkoxysilyl group, alkenyloxysilyl group, acyloxysilyl group, aminosilyl group, aminooxysilyl group, oxime silyl group, amide silyl group and the like can be suitably used. Especially, the alkoxy silyl group represented by following formula (1a) is preferable.

(R ¹ O) _n (R ² ) _{3- n} Si- (Formula 1a)

In Formula 1a, R ¹ and R ² represent the same or different alkyl groups, and n represents an integer of 1 to 3.

As an alkoxy silyl group, the alkoxy dialkyl silyl group (n = 1), the alkyl dialkoxy silyl group (n = 2), and the trialkoxy silyl group (n = 3) are mentioned. An alkyl dialkoxy silyl group (n = 2) or a trialkoxy silyl group (n = 3) is preferable.

Examples of an alkoxy group (R ¹ O), there may be mentioned a methoxy group, an ethoxy group, a propoxy group, isopropoxy group, butoxy group, isobutoxy group, such as Messenger.

Examples of the alkyl group (R ² ) include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group and the like.

Specific examples of the alkoxysilyl group include trimethoxysilyl groups (Formula 1a-1), triethoxysilyl groups (Formula 1a-2), and methyldimethoxysilyl groups represented by the following Formulas 1a-1 to 1a-6 And methyldiethoxysilyl group (formula 1a-4), ethyldimethoxysilyl group (formula 1a-5), ethyldiethoxysilyl group (formula 1a-6), and the like.

(CH ₃ O) ₃ Si- (Formula 1a-1)

(C ₂ H ₅ O) ₃ Si- (Formula 1a-2)

(CH ₃ ) (CH ₃ O) ₂ Si- (Formula 1a-3)

(CH ₃ ) (C ₂ H ₅ O) ₂ Si- (Formula 1a-4)

(C ₂ H ₅ ) (CH ₃ O) ₂ Si- (Formula 1a-5)

(C ₂ H ₅ ) (C ₂ H ₅ O) ₂ Si- (Formula 1a-6)

In the silicon-containing groups of the other hydrolyzable group, an alkoxy group (R ¹ O) as possible instead to use a hydrolyzable group, vinyloxy group, alkenyloxy group such as 1-methyl vinyloxy group, 1-ethylvinyl group; Acyloxy groups such as acetyl oxy group, propanoyloxy group and benzoyloxy group; Amino groups such as dimethylamino group, methylethylamino group and diethylamino group; Amino oxy groups such as dimethylaminooxy group, methylethylaminooxy group and diethylaminooxy group; Oxime groups such as (CH ₃ ) ₂ C = NO- or (C ₂ H ₅ ) ₂ C = NO-; CH ₃ CON (CH ₃₎ - or _{C 2 H 5 CON (CH 3} ) - can be an amide group and the like. These hydrolyzable groups (L) have hydrolyzability when bonded to the Si atom of the silyl group.

The silyl group in the hydrolyzable silicon-containing group may be a siloxane group. Examples of the hydrolyzable silicon-containing group having a siloxane group include those represented by the following general formula (1a ') and those having the above hydrolyzable groups such as alkenyloxy groups instead of alkoxy groups (R ¹ O):

(R ² ) ₃ SiO (R ¹ O) ₂ Si- (Formula 1a ')

The cation (Z ⁺ ) of the ionic compound is preferably one or two or more alkoxysilyl group-containing cations represented by the following general formula (1b):

(R ¹ O) _n (R ² ) _{3- n} Si-QV ⁺ (Formula 1b)

In Formula 1b, R ¹ and R ² represent the same or different alkyl groups, and n represents an integer of 1 to 3.

Q represents an alkylene group having 1 to 20 carbon atoms, and the alkylene group may be linear or branched, and may be substituted or unsubstituted. In addition, an ether bond (-O-), a sulfide bond (-S-), an imino group (-NH-), a carbonyl group (-CO-), an ester bond (-COO- or -OCO- is attached to the main chain of the alkylene group. ), Heteroatoms constituting functional groups such as amide bonds (-CONH- or -NHCO-), carbonate bonds (-OCOO-), urethane bonds (-NHCOO- or -OCONH-), and urea bonds (-NHCONH-) One or two or more atoms of elements other than carbon and hydrogen, such as O, S, and N, may be included.

However, when it has a hetero atom in the principal chain of the said alkylene group (Q), the number of the said hetero atom shall not be included in carbon number of an alkylene group. In the alkylene group (Q), atoms adjacent to Si of the silicon-containing group are carbon atoms, not heteroatoms.

V ⁺ silver, ammonium group, pyridinium group, pyrrolidinium group, imidazolium group, guanidinium group, isouronium group, thiouronium group, piperidinium group, pyrazolium group, morpholinium group, phosphonium group, sulfonium group It represents a monovalent cation group selected from, wherein the cationic group (V ⁺ ) may be substituted or unsubstituted.

As a substituent which can be couple | bonded with the said alkylene group (Q), Alkyl groups, such as a methyl group, an ethyl group, a propyl group, a butyl group; Aryl groups which may have substituents, such as a phenyl group, a naphthyl group, 4-methylphenyl group, and 4-methoxyphenyl group; Alkoxy group which may have substituents such as methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, trifluoromethoxy group and benzyloxy group ; Aryloxy groups which may have substituents such as phenoxy group, 2-methylphenoxy group, 4-methylphenoxy group, 4-methoxyphenoxy group and 3-phenoxyphenoxy group; Halogen atoms, such as a fluorine atom and a chlorine atom, etc. are illustrated. In addition, when the said alkylene group has a substituent, the carbon number of the said substituent shall not be included in the carbon number of an alkylene group.

The alkylene group (Q) may be a linking group connecting a hydrolyzable silicon-containing group (such as an alkoxysilyl group) and a cationic group (V ⁺ ), for example, -C _i H _2i- , -C _i H _2i OC _{j H 2j -, -C i H 2i} SC j H 2j -, -C i H 2i NHC j H 2j -, -C i H 2i COC j H 2j -, -C i H 2i COOC j H 2j -, -C _{i H 2i OCOC j H 2j -} , -C i H 2i NHCOC j H 2j -, -C i H 2i CONHC j H 2j -, -C i H 2i OCOOC j H 2j -, -C i H 2i NHCOOC j H _{2j -, -C i H 2i OCONHC} j H 2j -, -C i H 2i NHCONHC j H 2j -, -C i H 2i OC j H 2j OC k H 2k -, -C i H 2i OC j H 2j COOC _k H _2k- , -C _i H _2i NHC _j H _2j COOC _k H _2k- , -C _i H _2i SC _j H _2j COOC _k H _2k -and the like. Integer).

As an alkylene group represented by said C _i H _2i , C _j H _2j , C _k H _2k , for example, —CH ₂ —, —CH ₂ CH ₂ —, —C (CH ₃ ) —, —CH ₂ CH ₂ CH _And divalent aliphatic hydrocarbon groups having a straight or branched chain, such as _2- , -CH ₂ C (CH ₃ )-, -C (CH ₃ ) CH _2- , -CH ₂ CH ₂ CH ₂ CH ₂ -and the like.

When the linking group (Q) has a hetero atom in the main chain of the alkylene group, it is preferable that these hetero atoms constitute a chemical bond that is difficult to be cleaved by hydrolysis or the like. As a result, the linking group Q can function as a linking group connecting the hydrolyzable silicon-containing group (such as an alkoxysilyl group) and the cationic group (V ⁺ ).

The cation (Z ⁺ ) of the ionic compound is preferably one or two or more alkoxysilyl group-containing cations represented by the following general formula (2):

(R ¹ O) _n (R ² ) _{3- n} Si-Q ¹ -EQ ² -COO-Q ³ -V ⁺ (Formula 2)

In Formula 2, R ¹ and R ² represent the same or different alkyl group, n represents an integer of 1 to 3, Q ¹ represents an alkylene group having 1 to 10 carbon atoms, E is NH or S Q ² represents a single bond or an alkylene group having 1 to 10 carbon atoms, Q ³ represents an alkylene group having 1 to 10 carbon atoms, and V ⁺ represents an ammonium group, a pyridinium group, a pyrrolidinium group, or an imidazole Monovalent cation group selected from lium group, guanidinium group, isuroronium group, thiouronium group, piperidinium group, pyrazolium group, morpholinium group, phosphonium group, sulfonium group, and the cationic group may be substituted or unsubstituted have.

Examples of the ammonium group include trialkylammonium group (-N ⁺ R ₃ ), dialkylammonium group (-N ⁺ HR ₂ ), and the like. Examples of the phosphonium group include trialkylphosphonium groups (-P ⁺ R ₃ ), dialkylphosphonium groups (-P ⁺ HR ₂ ), and the like. As the sulfonium nyumgi there may be mentioned dialkyl sulfonium nyumgi (-S ⁺ R _2). R in these formulas represents the same or different alkyl group.

As a pyridinium group, a pyrrolidinium group, an imidazolium group, a guanidinium group, an isouronium group, a thiouronium group, a piperidinium group, a pyrazolium group, and a morpholinium group, pyridinium, a pyrrolidinium, an imida, respectively In the nitrogen atom or carbon atom contained in solium, guanidinium, isouronium, thiouronium, piperidinium, pyrazolium, morpholinium, or an oxygen atom of isouronium or a sulfur atom of thiouronium, The group which can combine with Q <^{3> is} mentioned.

As a substituent which can be couple | bonded with the said cationic group (V ⁺ ), Alkyl groups, such as a methyl group, an ethyl group, a propyl group, a butyl group; Aryl groups which may have substituents, such as a phenyl group, a naphthyl group, 4-methylphenyl group, and 4-methoxyphenyl group; Alkoxy group which may have substituents such as methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, trifluoromethoxy group and benzyloxy group ; Aryl oxy groups which may have substituents such as phenoxy group, 2-methylphenoxy group, 4-methylphenoxy group, 4-methoxyphenoxy group and 3-phenoxyphenoxy group; Halogen atoms, such as a fluorine atom and a chlorine atom, etc. are illustrated.

Examples of the cation (Z ⁺ ) used in the present invention include trialkyl (alkoxysilylalkyl) ammonium, trialkyl ([({[(alkoxysilyl) alkyl] carbamoyl} oxy) alkyl]) ammonium, trialkyl ( Hydrolyzable, such as [({[(alkoxysilyl) alkyl] amino} acyl) oxy] alkyl}) ammonium, trialkyl ([({[(alkoxysilyl) alkyl] sulfanyl} acyl) oxy] alkyl}) ammonium Ammonium cation having a silicon-containing group of;

1-[(alkoxysilyl) alkyl] pyridinium, 1-[({[(alkoxysilyl) alkyl] carbamoyl} oxy) alkyl] pyridinium, 1-[({[(alkoxysilyl) alkyl] amino} acyl Pyridinium cations having hydrolyzable silicon-containing groups such as) oxy] alkyl} pyridinium and 1-[({[(alkoxysilyl) alkyl] sulfanyl} acyl) oxy] alkyl} pyridinium;

1-alkyl-1-[(alkoxysilyl) alkyl] pyrrolidinium, 1-alkyl-1-[({[(alkoxysilyl) alkyl] carbamoyl} oxy) alkyl] pyrrolidinium, 1-alkyl-1 -[({[(Alkoxysilyl) alkyl] amino} acyl) oxy] alkyl} pyrrolidinium, 1-alkyl-1-[({[(alkoxysilyl) alkyl] sulfanyl} acyl) oxy] alkyl} pyrroli Pyrrolidinium cations having hydrolyzable silicon-containing groups such as dinium;

1-alkyl-3-[(alkoxysilyl) alkyl] imidazolium, 1,2-dialkyl-3-[(alkoxysilyl) alkyl] imidazolium, 1-alkyl-3-[({[(alkoxysilyl ) Alkyl] carbamoyl} oxy) alkyl] imidazolium, 1-alkyl-3-[({[(alkoxysilyl) alkyl] amino} acyl) oxy] alkyl} imidazolium, 1-alkyl-3- [ Imidazolium cations having hydrolyzable silicon-containing groups such as ({[(alkoxysilyl) alkyl] sulfanyl} acyl) oxy] alkyl} imidazolium;

1-[(alkoxysilyl) alkyl] guanidinium, 2-[(alkoxysilyl) alkyl] guanidinium, 1,1,3,3-tetraalkyl-2-[(alkoxysilyl) alkyl] guanidinium, etc. Guanidinium cation having a hydrolyzable silicon-containing group;

2-alkyl-1-[(alkoxysilyl) alkyl] isouronium, 2-[(alkoxysilyl) alkyl] isouronium, 1,1,3,3-tetra alkyl-2-[(alkoxysilyl) alkyl] Isornium cations having hydrolyzable silicon-containing groups such as isuroronium;

2-alkyl-1-[(alkoxysilyl) alkyl] thiouronium, 1-alkyl-2-[(alkoxysilyl) alkyl] thiouronium, 1,1,3,3-tetraalkyl-2-[(alkoxy Thiouronium cations having hydrolyzable silicon-containing groups such as silyl) alkyl] thiouronium;

1-alkyl-1-[(alkoxysilyl) alkyl] piperidinium, 1-alkyl-1-[({[(alkoxysilyl) alkyl] carbamoyl} oxy) alkyl] piperidinium, 1-alkyl-1 -[({[(Alkoxysilyl) alkyl] amino} acyl) oxy] alkyl} piperidinium, 1-alkyl-1-[({[(alkoxysilyl) alkyl] sulfanyl} acyl) oxy] alkyl} piperidi Piperidinium cations having hydrolyzable silicon-containing groups such as nium;

1-alkyl-2-[(alkoxysilyl) alkyl] pyrazolium, 1-alkyl-2-[({[(alkoxysilyl) alkyl] carbamoyl} oxy) alkyl] pyrazolium, 1-alkyl-2- [ ({[(Alkoxysilyl) alkyl] amino} acyl) oxy] alkyl} pyrazolium, 1-alkyl-2-[({[(alkoxysilyl) alkyl] sulfanyl} acyl) oxy] alkyl} pyrazolium, Pyrazolium cations having hydrolyzable silicon-containing groups;

4-alkyl-4-[(alkoxysilyl) alkyl] morpholinium, 4-alkyl-4-[({[(alkoxysilyl) alkyl] carbamoyl} oxy) alkyl] morpholinium, 4-alkyl-4 -[({[(Alkoxysilyl) alkyl] amino} acyl) oxy] alkyl} morpholinium, 4-alkyl-4-[({[(alkoxysilyl) alkyl] sulfanyl} acyl) oxy] alkyl} morpho Morpholinium cations having hydrolyzable silicon-containing groups such as nium;

Trialkyl [(alkoxysilyl) alkyl] phosphonium, trialkyl ([({[(alkoxysilyl) alkyl] carbamoyl} oxy) alkyl]) phosphonium, trialkyl ([({[(alkoxysilyl) alkyl] Phosphonium cations having hydrolyzable silicon-containing groups such as amino} acyl) oxy] alkyl}) phosphonium and trialkyl ([({[(alkoxysilyl) alkyl] sulfanyl} acyl) oxy] alkyl}) phosphonium ;

Dialkyl [(alkoxysilyl) alkyl] sulfonium, dialkyl ([({[(alkoxysilyl) alkyl] carbamoyl} oxy) alkyl]) sulfonium, dialkyl ([({[(alkoxysilyl) alkyl] Sulfonium cations having hydrolyzable silicon-containing groups such as amino} acyl) oxy] alkyl}) sulfonium and dialkyl ([({[(alkoxysilyl) alkyl] sulfanyl} acyl) oxy] alkyl}) sulfonium ; And the like.

As a specific example of the cation (Z ⁺ ) used in the present invention, for example,

Trimethyl ([2-({[3- (trimethoxysilyl) propyl] carbamoyl} oxy) ethyl]) ammonium, trimethyl ([2-({[3- (triethoxysilyl) propyl] carbamoyl } Oxy) ethyl]) ammonium, trimethyl ([2-({[3- (methyldimethoxysilyl) propyl] carbamoyl} oxy) ethyl]) ammonium, trimethyl ([2-({[3- (methyldie Methoxysilyl) propyl] carbamoyl} oxy) ethyl]) ammonium, trimethyl ([2-({[3- (ethyldimethoxysilyl) propyl] carbamoyl} oxy) ethyl]) ammonium, trimethyl ([2- ({[3- (ethyldiethoxysilyl) propyl] carbamoyl} oxy) ethyl]) ammonium,

1- [2-({[3- (trimethoxysilyl) propyl] carbamoyl} oxy) ethyl] pyridinium, 1- [2-({[3- (triethoxysilyl) propyl] carbamoyl } Oxy) ethyl] pyridinium, 1- [2-({[3- (methyldimethoxysilyl) propyl] carbamoyl} oxy) ethyl] pyridinium, 1- [2-({[3- (methyldie Methoxysilyl) propyl] carbamoyl} oxy) ethyl] pyridinium, 1- [2-({[3- (ethyldimethoxysilyl) propyl] carbamoyl} oxy) ethyl] pyridinium, 1- [2- ({[3- (ethyldiethoxysilyl) propyl] carbamoyl} oxy) ethyl] pyridinium,

Trimethyl ({2-[(3-{[3- (trimethoxysilyl) propyl] amino} propanoyl) oxy] ethyl}) ammonium, trimethyl ({2-[(3-{[3- (triethoxy Silyl) propyl] amino} propanoyl) oxy] ethyl}) ammonium, trimethyl ({2-[(3-{[3- (methyldimethoxysilyl) propyl] amino} propaneyl) oxy] ethyl}) ammonium, trimethyl ({2-[(3-{[3- (methyldiethoxysilyl) propyl] amino} propanoyl) oxy] ethyl}) ammonium, trimethyl ({2-[(3-{[3- (ethyldimethoxysilyl ) Propyl] amino} propanoyl) oxy] ethyl}) ammonium, trimethyl ({2-[(3-{[3- (ethyldiethoxysilyl) propyl] amino} propanoyl) oxy] ethyl}) ammonium,

Trimethyl ({2-[(2-methyl-3-{[3- (trimethoxysilyl) propyl] sulfanyl} propanoyl) oxy] ethyl}) ammonium, trimethyl ({2-[(2-methyl-3 -{[3- (triethoxysilyl) propyl] sulfanyl} propanoyl) oxy] ethyl}) ammonium, trimethyl ({2-[(2-methyl-3-{[3- (methyldimethoxysilyl) propyl ] Sulfanyl} propanoyl) oxy] ethyl}) ammonium, trimethyl ({2-[(2-methyl-3-{[3- (methyldiethoxysilyl) propyl] sulfanyl} propaneyl) oxy] ethyl}) Ammonium, trimethyl ({2-[(2-methyl-3-{[3- (ethyldimethoxysilyl) propyl] sulfanyl} propaneyl) oxy] ethyl}) ammonium, trimethyl ({2-[(2-methyl -3-{[3- (ethyldiethoxysilyl) propyl] sulfanyl} propanoyl) oxy] ethyl}) ammonium, and the like.

The compound represented by the said Formula (2) can be synthesize | combined using a well-known synthetic method.

For example, the compound represented by (R ¹ O) _n (R ² ) _{3- n} Si-QV ⁺ is (R ¹ O) _n (R ² ) _{3- n} Si-Q-Hal (wherein Hal is Cl And halogen, such as Br, I, or the like), can be synthesized by reacting with an amine or imidazole.

_{^{Furthermore, (R 1 O) n (}} R 2) 3- n Si-Q 1 -NH-COO-Q ⁺ is a compound represented by -V _{^{3, (R 1 O) n (}} R 2) 3-n Si- represented by Q ¹ -NCO compound, it can also be synthesized by reacting a compound represented by HO-Q ³ -V ^+.

Specific examples of the anion (X ⁻ ) used in the present invention include tetrafluoroborate [BF ₄ ⁻ ], hexafluorophosphate [PF ₆ ⁻ ], tris (pentafluoroethyl) trifluorophosphate [PF ₃ (C ₂ F). _{5) 3} ^-], a bis (alkylsulfonyl fluorophenyl) imide [(FSO _{2) 2} ^N-imide _{[(CF 3 SO 2) 2} N], methanesulfonyl as bis ^{(trifluoromethyl)],} bis ( pentafluoroethane sulfonyl) imide _{[(C 2 F 5 SO 2} ) 2 N -], bis (propane heptafluoropropane sulfonyl) imide _{[(C 3 F 7 SO 2} ) 2 N -], ( tree methanesulfonyl-fluorophenyl) (ethanesulfonyl pentafluorophenyl) imide _{[(CF 3 SO 2) (} C 2 F 5 SO 2) N -], ( methanesulfonyl trifluoromethyl) (propane heptafluoropropane sulfonyl ) imide _{[(CF 3 SO 2) (} C 3 F 7 SO 2) N -], ( methanesulfonyl trifluoromethyl) (butane sulfonyl nonafluorobutyl) imide _{[(CF 3 SO 2) (} C 4 F ₉ SO ₂₎ N ^-], and the like.

BF ₄ of which ^{_{-, PF 6 -, PF 3}} (C 2 F 5) 3 -, (FSO 2) 2 N -, (CF 3 SO 2) 2 N - is preferred.

And combinations of, for example, ionic compounds (Z ⁺ · X ^{- -)} to be used in the present invention Specific examples of preferred cation (Z ⁺⁾ and the preferred anions (X) of the above-described

Trimethyl ([2-({[3- (trimethoxysilyl) propyl] carbamoyl} oxy) ethyl]) ammonium bis (fluorosulfonyl) imide salt, trimethyl ([2-({[3- (tri Methoxysilyl) propyl] carbamoyl} oxy) ethyl]) ammonium hexafluorophosphate, trimethyl ([2-({[3- (trimethoxysilyl) propyl] carbamoyl} oxy) ethyl]) ammonium tetrafluoride Borate, trimethyl ([2-({[3- (trimethoxysilyl) propyl] carbamoyl} oxy) ethyl]) ammonium tris (pentafluoroethyl) trifluorophosphate salt,

Trimethyl ([2-({[3- (triethoxysilyl) propyl] carbamoyl} oxy) ethyl]) ammonium bis (fluorosulfonyl) imide salt, trimethyl ([2-({[3- (tri Ethoxysilyl) propyl] carbamoyl} oxy) ethyl]) ammonium hexafluorophosphate, trimethyl ([2-({[3- (triethoxysilyl) propyl] carbamoyl} oxy) ethyl]) ammonium tetrafluoride Borate, trimethyl ([2-({[3- (triethoxysilyl) propyl] carbamoyl} oxy) ethyl]) ammonium tris (pentafluoroethyl) trifluorophosphate salt,

Trimethyl ([2-({[3- (methyldimethoxysilyl) propyl] carbamoyl} oxy) ethyl]) ammonium bis (fluorosulfonyl) imide salt, trimethyl ([2-({[3- (methyl Dimethoxysilyl) propyl] carbamoyl} oxy) ethyl]) ammonium hexafluorophosphate, trimethyl ([2-({[3- (methyldimethoxysilyl) propyl] carbamoyl} oxy) ethyl]) ammonium tetrafluoride Borate, trimethyl ([2-({[3- (methyldimethoxysilyl) propyl] carbamoyl} oxy) ethyl]) ammonium tris (pentafluoroethyl) trifluorophosphate salt,

Trimethyl ([2-({[3- (methyldiethoxysilyl) propyl] carbamoyl} oxy) ethyl]) ammonium bis (fluorosulfonyl) imide salt, trimethyl ([2-({[3- (methyl Diethoxysilyl) propyl] carbamoyl} oxy) ethyl]) ammonium hexafluorophosphate, trimethyl ([2-({[3- (methyldiethoxysilyl) propyl] carbamoyl} oxy) ethyl]) ammonium tetrafluoride Borate, trimethyl ([2-({[3- (methyldiethoxysilyl) propyl] carbamoyl} oxy) ethyl]) ammonium tris (pentafluoroethyl) trifluorophosphate salt,

Trimethyl ([2-({[3- (ethyldimethoxysilyl) propyl] carbamoyl} oxy) ethyl]) ammonium bis (fluorosulfonyl) imide salt, trimethyl ([2-({[3- (ethyl Dimethoxysilyl) propyl] carbamoyl} oxy) ethyl]) ammonium hexafluorophosphate, trimethyl ([2-({[3- (ethyldimethoxysilyl) propyl] carbamoyl} oxy) ethyl]) ammonium tetrafluoride Borate, trimethyl ([2-({[3- (ethyldimethoxysilyl) propyl] carbamoyl} oxy) ethyl]) ammonium tris (pentafluoroethyl) trifluorophosphate salt,

Trimethyl ([2-({[3- (ethyldiethoxysilyl) propyl] carbamoyl} oxy) ethyl]) ammonium bis (fluorosulfonyl) imide salt, trimethyl ([2-({[3- (ethyl Diethoxysilyl) propyl] carbamoyl} oxy) ethyl]) ammonium hexafluorophosphate, trimethyl ([2-({[3- (ethyldiethoxysilyl) propyl] carbamoyl} oxy) ethyl]) ammonium tetrafluoride Borate, trimethyl ([2-({[3- (ethyldiethoxysilyl) propyl] carbamoyl} oxy) ethyl]) ammonium tris (pentafluoroethyl) trifluorophosphate salt,

1- [2-({[3- (trimethoxysilyl) propyl] carbamoyl} oxy) ethyl] pyridiniumbis (fluorosulfonyl) imide salt, 1- [2-({[3- (tri Methoxysilyl) propyl] carbamoyl} oxy) ethyl] pyridinium hexafluorophosphate, 1- [2-({[3- (trimethoxysilyl) propyl] carbamoyl} oxy) ethyl] pyridinium tetrafluoride Borate, 1- [2-({[3- (trimethoxysilyl) propyl] carbamoyl} oxy) ethyl] pyridinium tris (pentafluoroethyl) trifluorophosphate salt,

1- [2-({[3- (triethoxysilyl) propyl] carbamoyl} oxy) ethyl] pyridiniumbis (fluorosulfonyl) imide salt, 1- [2-({[3- (tri Ethoxysilyl) propyl] carbamoyl} oxy) ethyl] pyridinium hexafluorophosphate, 1- [2-({[3- (triethoxysilyl) propyl] carbamoyl} oxy) ethyl] pyridinium tetrafluoride Borate, 1- [2-({[3- (triethoxysilyl) propyl] carbamoyl} oxy) ethyl] pyridinium tris (pentafluoroethyl) trifluorophosphate salt,

1- [2-({[3- (methyldimethoxysilyl) propyl] carbamoyl} oxy) ethyl] pyridiniumbis (fluorosulfonyl) imide salt, 1- [2-({[3- (methyl Dimethoxysilyl) propyl] carbamoyl} oxy) ethyl] pyridinium hexafluorophosphate, 1- [2-({[3- (methyldimethoxysilyl) propyl] carbamoyl} oxy) ethyl] pyridinium tetrafluoride Borate, 1- [2-({[3- (methyldimethoxysilyl) propyl] carbamoyl} oxy) ethyl] pyridinium tris (pentafluoroethyl) trifluorophosphate salt,

1- [2-({[3- (methyldiethoxysilyl) propyl] carbamoyl} oxy) ethyl] pyridiniumbis (fluorosulfonyl) imide salt, 1- [2-({[3- (methyl Diethoxysilyl) propyl] carbamoyl} oxy) ethyl] pyridinium hexafluorophosphate, 1- [2-({[3- (methyldiethoxysilyl) propyl] carbamoyl} oxy) ethyl] pyridinium tetrafluoride Borate, 1- [2-({[3- (methyldiethoxysilyl) propyl] carbamoyl} oxy) ethyl] pyridinium tris (pentafluoroethyl) trifluorophosphate salt,

1- [2-({[3- (ethyldimethoxysilyl) propyl] carbamoyl} oxy) ethyl] pyridiniumbis (fluorosulfonyl) imide salt, 1- [2-({[3- (ethyl Dimethoxysilyl) propyl] carbamoyl} oxy) ethyl] pyridinium hexafluorophosphate, 1- [2-({[3- (ethyldimethoxysilyl) propyl] carbamoyl} oxy) ethyl] pyridinium tetrafluoride Borate, 1- [2-({[3- (ethyldimethoxysilyl) propyl] carbamoyl} oxy) ethyl] pyridinium tris (pentafluoroethyl) trifluorophosphate salt,

1- [2-({[3- (ethyldiethoxysilyl) propyl] carbamoyl} oxy) ethyl] pyridiniumbis (fluorosulfonyl) imide salt, 1- [2-({[3- (ethyl Diethoxysilyl) propyl] carbamoyl} oxy) ethyl] pyridinium hexafluorophosphate, 1- [2-({[3- (ethyldiethoxysilyl) propyl] carbamoyl} oxy) ethyl] pyridinium tetrafluoride Borate, 1- [2-({[3- (ethyldiethoxysilyl) propyl] carbamoyl} oxy) ethyl] pyridinium tris (pentafluoroethyl) trifluorophosphate salt,

Trimethyl ({2-[(3-{[3- (trimethoxysilyl) propyl] amino} propanoyl) oxy] ethyl}) ammonium bis (fluorosulfonyl) imide salt, trimethyl ({2-[(3 -{[3- (trimethoxysilyl) propyl] amino} propanoyl) oxy] ethyl}) ammonium hexafluorophosphate, trimethyl ({2-[(3-{[3- (trimethoxysilyl) propyl] amino } Propanoyl) oxy] ethyl}) ammonium tetrafluoroborate, trimethyl ({2-[(3-{[3- (trimethoxysilyl) propyl] amino} propaneyl) oxy] ethyl}) ammoniumtris (pentafluor Roethyl) trifluorophosphate salt,

Trimethyl ({2-[(3-{[3- (triethoxysilyl) propyl] amino} propanoyl) oxy] ethyl}) ammonium bis (fluorosulfonyl) imide salt, trimethyl ({2-[(3 -{[3- (triethoxysilyl) propyl] amino} propanoyl) oxy] ethyl}) ammonium hexafluorophosphate, trimethyl ({2-[(3-{[3- (triethoxysilyl) propyl] amino } Propanoyl) oxy] ethyl}) ammonium tetrafluoroborate, trimethyl ({2-[(3-{[3- (triethoxysilyl) propyl] amino} propaneyl) oxy] ethyl}) ammoniumtris (pentafluor Roethyl) trifluorophosphate salt,

Trimethyl ({2-[(3-{[3- (methyldimethoxysilyl) propyl] amino} propanoyl) oxy] ethyl}) ammonium bis (fluorosulfonyl) imide salt, trimethyl ({2-[(3 -{[3- (methyldimethoxysilyl) propyl] amino} propanoyl) oxy] ethyl}) ammonium hexafluorophosphate, trimethyl ({2-[(3-{[3- (methyldimethoxysilyl) propyl] amino } Propane oil) oxy] ethyl}) ammonium tetrafluoroborate,

Trimethyl ({2-[(3-{[3- (methyldimethoxysilyl) propyl] amino} propanoyl) oxy] ethyl}) ammoniumtris (pentafluoroethyl) trifluorophosphate salt, trimethyl ({2- [(3-{[3- (methyldiethoxysilyl) propyl] amino} propanoyl) oxy] ethyl}) ammonium bis (fluorosulfonyl) imide salt, trimethyl ({2-[(3-{[3- (Methyldiethoxysilyl) propyl] amino} propanoyl) oxy] ethyl}) ammonium hexafluorophosphate, trimethyl ({2-[(3-{[3- (methyldiethoxysilyl) propyl] amino} propaneyl) oxy ] Ethyl}) ammonium tetrafluoroborate, trimethyl ({2-[(3-{[3- (methyldiethoxysilyl) propyl] amino} propanoyl) oxy] ethyl}) ammonium tris (pentafluoroethyl) trifluor Lophosphate Salt,

Trimethyl ({2-[(3-{[3- (ethyldimethoxysilyl) propyl] amino} propanoyl) oxy] ethyl}) ammonium bis (fluorosulfonyl) imide salt, trimethyl ({2-[(3 -{[3- (ethyldimethoxysilyl) propyl] amino} propanoyl) oxy] ethyl}) ammonium hexafluorophosphate, trimethyl ({2-[(3-{[3- (ethyldimethoxysilyl) propyl] amino } Propanoyl) oxy] ethyl}) ammonium tetrafluoroborate, trimethyl ({2-[(3-{[3- (ethyldimethoxysilyl) propyl] amino} propaneyl) oxy] ethyl}) ammonium tris (pentafluor Roethyl) trifluorophosphate salt,

Trimethyl ({2-[(3-{[3- (ethyldiethoxysilyl) propyl] amino} propanoyl) oxy] ethyl}) ammonium bis (fluorosulfonyl) imide salt, trimethyl ({2-[(3 -{[3- (ethyldiethoxysilyl) propyl] amino} propanoyl) oxy] ethyl}) ammonium hexafluorophosphate, trimethyl ({2-[(3-{[3- (ethyldiethoxysilyl) propyl] amino } Propanoyl) oxy] ethyl}) ammonium tetrafluoroborate, trimethyl ({2-[(3-{[3- (ethyldiethoxysilyl) propyl] amino} propaneyl) oxy] ethyl}) ammonium tris (pentafluor Roethyl) trifluorophosphate salt,

Trimethyl ({2-[(2-methyl-3-{[3- (trimethoxysilyl) propyl] sulfanyl} propaneyl) oxy] ethyl}) ammonium bis (fluorosulfonyl) imide salt, trimethyl ({ 2-[(2-methyl-3-{[3- (trimethoxysilyl) propyl] sulfanyl} propanoyl) oxy] ethyl}) ammonium hexafluorophosphate, trimethyl ({2-[(2-methyl-3 -{[3- (trimethoxysilyl) propyl] sulfanyl} propanoyl) oxy] ethyl}) ammonium tetrafluoroborate, trimethyl ({2-[(2-methyl-3-{[3- (trimethoxy Silyl) propyl] sulfanyl} propane oil) oxy] ethyl}) ammonium tris (pentafluoroethyl) trifluorophosphate salt,

Trimethyl ({2-[(2-methyl-3-{[3- (triethoxysilyl) propyl] sulfanyl} propaneyl) oxy] ethyl}) ammonium bis (fluorosulfonyl) imide salt, trimethyl ({ 2-[(2-methyl-3-{[3- (triethoxysilyl) propyl] sulfanyl} propanoyl) oxy] ethyl}) ammonium hexafluorophosphate, trimethyl ({2-[(2-methyl-3 -{[3- (triethoxysilyl) propyl] sulfanyl} propanoyl) oxy] ethyl}) ammonium tetrafluoroborate, trimethyl ({2-[(2-methyl-3-{[3- (triethoxy Silyl) propyl] sulfanyl} propane oil) oxy] ethyl}) ammonium tris (pentafluoroethyl) trifluorophosphate salt,

Trimethyl ({2-[(2-methyl-3-{[3- (methyldimethoxysilyl) propyl] sulfanyl} propaneyl) oxy] ethyl}) ammonium bis (fluorosulfonyl) imide salt, trimethyl ({ 2-[(2-methyl-3-{[3- (methyldimethoxysilyl) propyl] sulfanyl} propanoyl) oxy] ethyl}) ammonium hexafluorophosphate, trimethyl ({2-[(2-methyl-3 -{[3- (methyldimethoxysilyl) propyl] sulfanyl} propaneoyl) oxy] ethyl}) ammonium tetrafluoroborate, trimethyl ({2-[(2-methyl-3-{[3- (methyldimethoxy Silyl) propyl] sulfanyl} propane oil) oxy] ethyl}) ammonium tris (pentafluoroethyl) trifluorophosphate salt,

Trimethyl ({2-[(2-methyl-3-{[3- (methyldiethoxysilyl) propyl] sulfanyl} propaneyl) oxy] ethyl}) ammonium bis (fluorosulfonyl) imide salt, trimethyl ({ 2-[(2-methyl-3-{[3- (methyldiethoxysilyl) propyl] sulfanyl} propaneyl) oxy] ethyl}) ammonium hexafluorophosphate, trimethyl ({2-[(2-methyl-3 -{[3- (methyldiethoxysilyl) propyl] sulfanyl} propanoyl) oxy] ethyl}) ammonium tetrafluoroborate, trimethyl ({2-[(2-methyl-3-{[3- (methyldiethoxy Silyl) propyl] sulfanyl} propane oil) oxy] ethyl}) ammonium tris (pentafluoroethyl) trifluorophosphate salt,

Trimethyl ({2-[(2-methyl-3-{[3- (ethyldimethoxysilyl) propyl] sulfanyl} propanoyl) oxy] ethyl}) ammonium bis (fluorosulfonyl) imide salt, trimethyl ({ 2-[(2-methyl-3-{[3- (ethyldimethoxysilyl) propyl] sulfanyl} propaneoyl) oxy] ethyl}) ammonium hexafluorophosphate, trimethyl ({2-[(2-methyl-3 -{[3- (ethyldimethoxysilyl) propyl] sulfanyl} propanoyl) oxy] ethyl}) ammonium tetrafluoroborate, trimethyl ({2-[(2-methyl-3-{[3- (ethyldimethoxy Silyl) propyl] sulfanyl} propane oil) oxy] ethyl}) ammonium tris (pentafluoroethyl) trifluorophosphate salt,

Trimethyl ({2-[(2-methyl-3-{[3- (ethyldiethoxysilyl) propyl] sulfanyl} propaneyl) oxy] ethyl}) ammonium bis (fluorosulfonyl) imide salt, trimethyl ({ 2-[(2-methyl-3-{[3- (ethyldiethoxysilyl) propyl] sulfanyl} propanoyl) oxy] ethyl}) ammonium hexafluorophosphate, trimethyl ({2-[(2-methyl-3 -{[3- (ethyldiethoxysilyl) propyl] sulfanyl} propanoyl) oxy] ethyl}) ammonium tetrafluoroborate, trimethyl ({2-[(2-methyl-3-{[3- (ethyldiethoxy Silyl) propyl] sulfanyl} propane oil) oxy] ethyl}) ammonium tris (pentafluoroethyl) trifluoro phosphate salt, etc. are mentioned.

The antistatic agent contains 0.1 to 20 parts by weight, more preferably 0.1 to 10 parts by weight of the ionic compound represented by the formula (C), based on 100 parts by weight of the copolymer composition of the pressure-sensitive adhesive polymer used in the present invention. It is preferable.

It is preferable that the surface resistivity of the adhesive layer which consists of the said adhesive composition is 1.0x10 ^{+ 12} ohms / square or less. If the surface resistivity is large, the performance of releasing static electricity generated by charging at the time of peeling is inferior. Thus, by sufficiently reducing the surface resistivity, the peeling band voltage caused by the static electricity generated when the adherend is peeled off, reduces the adherend. The influence on the electric control circuit and the like can be suppressed.

It is preferable that the adhesive composition of this invention crosslinks an adhesive polymer, when forming an adhesive layer. In order to perform bridge | crosslinking, an adhesive composition may contain a known crosslinking agent, and may be bridge | crosslinked by optical crosslinking, such as an ultraviolet-ray (UV). As a crosslinking agent, a bifunctional or more isocyanate compound, a bifunctional or more functional epoxy compound, a bifunctional or more functional acrylate compound, a metal chelate compound, etc. are mentioned.

Moreover, as other components, well-known additives, such as a silane coupling agent, antioxidant, surfactant, a hardening accelerator, a plasticizer, a filler, a hardening retardant, a processing aid, and an antioxidant, can be mix | blended suitably. These can be used individually or in combination of 2 or more types.

In the adhesive film of this invention, the adhesive layer which consists of an adhesive composition of this invention is laminated | stacked on one side of a base film. The adhesive film of this invention can be used suitably for a surface protection film, the surface protection film for polarizing plates, the surface protection film for optics, the optical film with adhesive, the polarizing plate with adhesive.

As a base film of an adhesive layer and a peeling film (separator) which protects an adhesive surface, resin films, such as a polyester film, etc. can be used.

The base film may be subjected to an antistatic treatment by applying a silicone antibacterial or fluorine-based release agent or coating agent, silica fine particles or the like, on the surface opposite to the side on which the pressure-sensitive adhesive layer is formed, or by applying an antistatic agent. Can be.

The release film is subjected to a release film by a silicone-based, fluorine-based release agent or the like on the side of the release film that is joined to the adhesive face of the pressure-sensitive adhesive layer.

In the case of surface protection films for optics, such as a surface protection film for polarizing plates, it is preferable that a base film and an adhesive layer have sufficient transparency.

In the optical film with an adhesive, optical films, such as a polarizing plate film, a retardation plate film, a lens film, the polarizing plate film for both retardation plates, and the polarizing plate film for both lens films, can be used as a base film.

The optical film with an adhesive is formed by laminating an adhesive layer on one or both surfaces of the optical film, and can be used for attachment to a glass plate or the like of an image display device. The optical film with these adhesives can be attached to a glass substrate etc. through an adhesive layer, and can be introduce | transduced into an image display apparatus. It is preferable that the adhesive layer used for optical films with adhesives, such as a polarizing plate with an adhesive, has sufficient transparency.

Moreover, the polarizing plate used as a base film generally has the 3-layered structure pinched by the triacetyl cellulose type protective film on both surfaces of a polyvinyl alcohol-type polarizer.

A stretched triacetylcellulose-based film, a stretched polycycloolefin-based film, or a stretched cellulose acetate propio, on the surface of the protective film instead of a polarizing plate coated with a discotic liquid crystal or a triacetylcellulose-based film It has a structure attached by a nate film or the like. Moreover, these polarizing plate films are affixed on the glass substrate which is a surface base material of a liquid crystal display panel via an adhesive layer.

According to the present invention, by using an antistatic agent, an ionic compound represented by the formula (1), in an adhesive, it is possible to impart antistatic performance and to further improve adhesion to a glass plate, and to improve adhesion and durability, and thus, conventional charging Compared with the case where both the inhibitor and the silane coupling agent are used together, the advantages of both can be utilized at low cost, and the above problems can be improved.

Example

Hereinafter, the present invention will be described in detail through examples.

<Production of Acrylic Copolymer>

Example 1

Nitrogen gas was introduce | transduced into the reaction apparatus provided with the stirrer, the thermometer, the reflux cooler, and the nitrogen introduction tube, and the air in the reaction apparatus was replaced with nitrogen gas. Then, 100 parts of solvents (ethyl acetate) were added to the reaction apparatus with 100 weight part of 2-ethylhexyl acrylates, and 1.5 weight part of 6-hydroxyhexyl acrylates. Then, 0.1 weight part of azobisisobutylonitrile was dripped over 2 hours as a polymerization initiator, and it reacted at 65 degreeC for 8 hours, and obtained the acrylic copolymer solution (1) of Example 1 whose weight average molecular weight is 500,000.

[Examples 2 to 7 and Comparative Examples 1 to 2]

The acrylic copolymer solution used in Examples 2-7 and Comparative Examples 1-2 was carried out similarly to the acrylic copolymer solution 1 used in Example 1 except having made the composition of a monomer like the description of Table 1, respectively. Got.

<Manufacture of an adhesive composition, a surface protection film, and a polarizing plate film>

Example 1

1.0 weight part of antistatic agent (C-1, Table 3, and Table 4) with respect to the acrylic copolymer solution (1, 100 weight part of them) prepared as mentioned above, coronate HX (hexamethylene 1.5 weight part of isocyanurate bodies of a diisocyanate (HDI) compound were added, and it stirred and mixed, and obtained the adhesive composition of Example 1. After apply | coating this adhesive composition on the peeling film which consists of a silicone resin coated polyethylene terephthalate (PET) film, the solvent was removed by drying at 90 degreeC, and the adhesive sheet whose thickness of an adhesive layer was 25 micrometers was obtained.

After that, the adhesive sheet was transferred to a surface opposite to the antistatic and antifouling surface of the antistatic and antifouling polyethylene terephthalate (PET) film on one side, and the antistatic and antifouling PET The surface protection film of Example 1 which has a laminated structure of "film / adhesive layer / peeling film (silicon resin coated PET film)."

[Examples 2 to 4 and Comparative Examples 1 to 2]

Except having made the composition of an additive like the description of Table 1, it carried out similarly to the surface protection film of the said Example 1, and obtained the surface protection films of Examples 2-4 and Comparative Examples 1-2.

[Examples 5 to 7]

The laminated structure of "polarizing plate / adhesive layer / peeling film (silicon resin coated PET film)" was carried out similarly to Example 1 except having made the composition of an additive like the base material of Table 1, and using the base material to be transferred as a polarizing plate. The polarizing plate films of Examples 5 to 7 were obtained.

In Table 1, the compounding ratio of each component is the numerical value of the weight part calculated | required as 100 weight part of the sum total of an alkyl acrylate monomer (when using a copolymerizable vinyl monomer). It is shown in parentheses. In addition, the compound name of the abbreviation code | symbol of each component used in Table 1 is shown in Table 2. Moreover, the chemical formula of the antistatic agent used in Table 1 is shown in Table 3.

Coronate HX, HL and L-45 are trade names of Nippon Polyurethane Co., Ltd., and TETRAD X is Mitsubishi Gas Kagaku Co., Ltd. Nate 24A-100 is a trade name of Asahi Kasei Chemicals.

Alkyl
Acrylate
Monomer Copolymerizability
vinyl
Monomer Contains functional group
Monomer Cross-linking agent Antistatic Silane
Coupling agent Example 1 2EHA 100 6HHA (1.5) HX (1.5) C-1 (1.0) Example 2 IOA (100) 4HBA (2.5) HL (3.5) C-2 (1.5) Example 3 BA (80)
MA (20) AAc (3.0) T-X (0.02) C-3 (0.5) Example 4 BA (70)
EA (30) CPA (2.0) L-45 (0.2) C-4 (5.0) Example 5 BA (90) PHEA (10) HEAA (1.5) 24A-200 (2.5) C-5 (0.5)
C-6 (0.5) Example 6 BA (80) PHEA (10)
BZA (10) AAc (1.0) T-X (0.03) C-6 (1.5) Example 7 BA (50)
CHA (50) UV curing C-7 (2.0) Comparative Example 1 2EHA 100 HL (3.5) C-4 (0.05) Comparative Example 2 2EHA (90)
BA (10) HEA (0.05) HX (6.0) C-8 (1.0) D-1 (0.1)

Abbreviation Compound name Alkyl
Acrylate
Monomer 2EHA 2-ethylhexyl acrylate IOA Isooctyl acrylate BA Butyl acrylate MA Methyl acrylate EA Ethyl acrylate CHA Cyclohexyl acrylate Copolymerizability
vinyl
Monomer PHEA Phenoxy ethyl acrylate BZA Benzyl acrylate Functional group
contain
Monomer 6HHA 6-hydroxyhexyl acrylate 4HBA 4-hydroxybutyl acrylate HEA 2-hydroxyethyl acrylate AAc Acrylic acid CEA Carboxyethyl acrylate CPA Carboxypentylacrylate HEAA N-hydroxyethylacrylamide Cross-linking agent HX Coronate HX (HDI isocyanurate) HL Coronate HL (HDI Additive) T-X TETRAD-X (N, N, N ', N'-tetraglycidyl-m-xylenediamine) L-45 Coronate L-45 24A-100 Duranate 24A-100 Daejeon
Inhibitor C-1 Trimethyl ([2-({[3- (trimethoxysilyl) propyl] carbamoyl} oxy) ethyl])
Ammonium Hexafluoride Phosphate C-2 1- [2-({[3- (trimethoxysilyl) propyl] carbamoyl} oxy) ethyl] pyridinium
6-fluorophosphate C-3 Trimethyl ({2-[(3-{[3- (trimethoxysilyl) propyl] amino} propanoyl) oxy]
Ethyl}) ammonium tetrafluoroborate C-4 Trimethyl ({2-[(2-methyl-3-{[3- (trimethoxysilyl) propyl] sulfanyl} propaneyl)
Oxy] ethyl}) ammonium tris (pentafluoroethyl) trifluorophosphate salt C-5 Trimethyl ({2-[(2-methyl-3-{[3- (ethyldiethoxysilyl) propyl] sulfanyl}
Propane oil) oxy] ethyl}) ammonium hexafluorophosphate C-6 1- [2-({[3- (triethoxysilyl) propyl] carbamoyl} oxy) ethyl] pyridinium
Bis (fluorosulfonyl) imide salt C-7 1- [2-({[3- (ethyldimethoxysilyl) propyl] carbamoyl} oxy) ethyl]
Pyridinium tetrafluoroborate C-8 Diallylmethyllaurylammonium tetrafluoroborate Silane coupling agent D-1 3-glycidoxypropyltrimethoxysilane

Abbreviation Chemical formula C-1 _{(CH 3 O) 3 Si-} CH 2 CH 2 CH 2 NHCOOCH 2 CH 2 -N + (CH 3) 3 PF 6 - C-2 _{(CH 3 O) 3 Si-} CH 2 CH 2 CH 2 NHCOOCH 2 CH 2 -N + C 5 H 5 PF 6 - C-3 _{(CH 3 O) 3 Si-} CH 2 CH 2 CH 2 NHCH 2 CH 2 COOCH 2 CH 2 -N + (CH 3) 3 BF 4 - C-4 _{(CH 3 O) 3 Si-} CH 2 CH 2 CH 2 SCH 2 CH (CH 3) COOCH 2 CH 2 -N + (CH 3) 3 PF 3 (C 2 F 5) 3 - C-5 _{(C 2 H 5) (C} 2 H 5 O) 2 Si-CH 2 CH 2 CH 2 SCH 2 CH (CH 3) COOCH 2 CH 2 -N + (CH 3) 3 PF 6 - C-6 _{(C 2 H 5 O) 3} Si-CH 2 CH 2 CH 2 NHCOOCH 2 CH 2 -N + C 5 H 5 (FSO 2) 2 N - C-7 _{(C 2 H 5) (CH} 3 O) 2 Si-CH 2 CH 2 CH 2 NHCOOCH 2 CH 2 -N + C 5 H 5 BF 4 - C-8 _{(CH 2 = CHCH 2) 2} N + (CH 3) (nC 12 H 25) BF 4 - However, -N + C ₅ H ₅ groups are pyridinium, nC ₁₂ H ₂₅ is referred to us represents a group.

<Test method and evaluation>

The surface protective films of Examples 1 to 4 and Comparative Examples 1 and 2 and the polarizing plate films of Examples 5 to 7 were aged at 23 ° C. and 50% RH for 7 days, followed by a release film (silicon resin coated PET film). ) Was peeled off, and the adhesive layer was expressed, and it was set as the measurement sample of surface resistivity.

Furthermore, the surface protection film and the polarizing plate film which expressed the said adhesive layer and the polarizing plate film were affixed on the surface of the alkali free glass plate through the adhesive layer, and left to stand for 1 day, and then autoclave-processed at 50 degreeC, 5 atmospheres, and 20 minutes, and it was made at room temperature. What was left to stand for 12 hours was made into the measurement sample of adhesive force.

In addition, the surface protection film which expressed this adhesive layer and the polarizing plate film were affixed on the surface of the alkali free glass plate through the adhesive layer, and it was set as the measurement sample of durability and reworkability.

<Surface resistivity>

After aging, the adhesive film is peeled off by peeling off the release film (silicon resin coated PET film) before adhering to the alkali-free glass plate, and using a resistivity meter Hiresta UP-HT450 (manufactured by Mitsubishi Kagaku Analytics) The surface resistivity of the adhesive layer was measured.

<Durability>

After leaving the measurement sample of the durability obtained above for 250 hours in 60 degreeC and 90% RH atmosphere, it took out at room temperature and confirmed visually peeling, foaming, etc. from an adherend. Evaluation criteria evaluated the case where "(circle)" and the case where peeling and foaming were confirmed a little "(circle)" and the case where peeling and foaming were confirmed clearly "x" when the peeling and foaming were not confirmed at all.

<Reworkability>

After leaving the measurement sample of reworkability obtained above for 24 hours in 70 degreeC and DRY atmosphere, it is taken out at room temperature, and the residual of the adhesive component on the surface of a to-be-adhered body at the time of peeling off a surface protection film and a polarizing plate film from an alkali free glass plate Visually confirmed. The evaluation criteria evaluated the case where "(circle)" and the case where the residual of an adhesive component were confirmed slightly "(circle)" and the case where the residual of an adhesive component were confirmed clearly "x" when the residual of an adhesive component was not confirmed at all.

<Adhesion to Glass Plate>

The measurement sample of the adhesive force obtained above (with a 25 mm width surface protective film and a polarizing plate film attached to the surface of an alkali free glass plate) was peeled off at a tensile speed of 0.3 m / min in a 180 ° direction using a tensile tester and measured. One peeling strength was made into adhesive force.

Table 4 shows the evaluation results. In addition, surface resistivity was described by the system which makes "m * 10 ^{+ n} " into "mE + n" (m is arbitrary real value and n is a positive integer).

Of adhesive film
Embodiment Surface resistivity
[Ω / □] durability Reworkability adhesiveness
[N / 25mm] Example 1 Protective film 1.50E + 11 ○ ○ 0.1 Example 2 Protective film 6.80E + 09 ○ ○ 0.06 Example 3 Protective film 2.40E + 11 ○ ○ 12.5 Example 4 Protective film 4.50E + 09 ○ ○ 11.3 Example 5 Polarizer film 1.78E + 10 ○ ○ 4.5 Example 6 Polarizer film 1.60E + 10 ○ ○ 8.5 Example 7 Polarizer film 4.70E + 10 ○ ○ 8.8 Comparative Example 1 Protective film 2.65E + 13 △ △ 35 Comparative Example 2 Protective film 2.13E + 12 △ × 3

The surface protection films of Examples 1-4 and the polarizing plate films of Examples 5-7 were 1.0 * 10 ^{+ 12} ohms / square or less, and were equipped with moderate adhesive force. That is, defects such as antistatic performance and reworkability of the adherend could be improved.

The surface protection films of Comparative Examples 1-2 had a surface resistivity ^exceeding 1.0x10 ^{+ 12} ohms / square, and there ^{existed a} problem in antistatic performance. Furthermore, the surface protection films of Comparative Examples 1 and 2 also had problems in durability and reworkability of the adherend.

Claims (15)

An adhesive composition containing an antistatic agent, comprising (meth) acrylic polymer as a main component, and containing an ionic compound represented by the following formula (1) as the antistatic agent, wherein the ionic compound contains a hydrolyzable silicon-containing group The pressure-sensitive adhesive composition having an organic cation
Z⁺ X^- (Formula 1)
In which Z is⁺Represents a cation, X^-Represents an anion. The pressure-sensitive adhesive composition of claim 1, wherein the cation (Z ⁺ ) of the ionic compound is one or two or more alkoxysilyl group-containing cations represented by the following general formula (2):
(R ¹ O) _n (R ² ) _{3- n} Si-Q ¹ -EQ ² -COO-Q ³ -V ⁺ (Formula 2)
In this formula,
R ¹ and R ² each represent the same or different alkyl group,
n represents an integer of 1 to 3,
Q ¹ represents an alkylene group having 1 to 10 carbon atoms,
E represents NH or S,
Q ² represents a single bond or an alkylene group having 1 to 10 carbon atoms,
Q ³ represents an alkylene group having 1 to 10 carbon atoms,
V ⁺ silver, ammonium group, pyridinium group, pyrrolidinium group, imidazolium group, guanidinium group, isouronium group, thiouronium group, piperidinium group, pyrazolium group, morpholinium group, phosphonium group, sulfonium group Monovalent cation groups selected from which may be substituted or unsubstituted. The hydrolyzable silicon-containing group according to claim 1 or 2, wherein the hydrolyzable silicon-containing group is trimethoxysilyl group, triethoxysilyl group, methyldimethoxysilyl group, methyldiethoxysilyl group, ethyldimethoxysilyl group, ethyldie The pressure-sensitive adhesive composition, which is an alkoxysilyl group selected from a oxysilyl group. The said (meth) acrylic-type polymer is an at least 1 sort (s) of the alkyl (meth) acrylate monomer whose carbon number of (A) alkyl group is C1-C14, and (B) hydroxyl group and / or carboxyl group of Claim 1 or 2 It is a copolymer composition which consists of at least 1 sort (s) of the copolymerizable vinyl monomer containing the said antistatic agent with respect to 100 weight part of said copolymerization compositions (C) 0.1-20 weight part of ionic compounds represented by the said General formula (1) an essential component It contains as an adhesive composition. The said (meth) acrylic-type polymer is an air which has at least 1 sort (s) of the alkyl (meth) acrylate monomers whose C1-C14 carbon number of the (A) alkyl group has a (B ') vinyl group, It is a copolymer composition which consists of at least 1 sort (s) of a synthetic vinyl monomer,
The adhesive composition which the said antistatic agent contains 0.1-20 weight part of ionic compounds represented by the said (1) with respect to 100 weight part of said copolymerization compositions as an essential component. The adhesive composition of Claim 1 or 2 whose surface resistivity of the adhesive layer which consists of said adhesive composition is 1.0 * 10 ^{+ 12 (} ohm) / square or less. The anion (X ⁻ ) of the ionic compound is a hexafluorophosphate anion, a bis (fluorosulfonyl) imide anion, or a tris (pentafluoroethyl) tree according to any one of claims 1 to 6. 1 type selected from inorganic or organic anion groups consisting of a fluorophosphate anion, a bis (trifluoromethanesulfonyl) imide anion, a thiocyanate anion, an alkylbenzenesulfonate anion, a perchlorate anion salt, a tetrafluoroborate anion, or 2 or more types of adhesive compositions. The adhesive composition of Claim 7 was laminated | stacked on one side of a base material, The adhesive film characterized by the above-mentioned. The adhesive film which consists of an adhesive composition of Claim 7 laminated | stacked on one side of a base material, The adhesive film characterized by the above-mentioned. The surface protection film in which the adhesive film of Claim 9 was used. The surface protection film for polarizing plates in which the adhesive film of Claim 9 was used. The surface protection film for optics in which the adhesive film of Claim 9 was used. The optical film with an adhesive with which the adhesive layer which consists of an adhesive composition of Claim 7 is laminated | stacked on at least one surface of an optical film. The optical film with an adhesive according to claim 13, wherein said optical film is a polarizing plate. The image display apparatus by which the optical film with an adhesive of Claim 13 adheres through the said adhesive layer.