KR20240045116A - Antistatic aid - Google Patents

Abstract

(식 중, R¹ 은 산소 원자를 함유하는 탄화수소기, 하이드록시기, 또는 카르복시기를 나타내고,
R² 는 산소 원자를 함유하고 있어도 되는 탄화수소기, 하이드록시기, 카르복시기, 혹은 수소 원자를 나타낸다.)
로 나타내는 화합물을 함유하는, 대전 방지 보조제를 제공하는 것이다.The present invention has the following formula (I)

(Wherein, R ¹ represents a hydrocarbon group containing an oxygen atom, a hydroxy group, or a carboxyl group,
R ² represents a hydrocarbon group, hydroxy group, carboxyl group, or hydrogen atom that may contain an oxygen atom.)
To provide an antistatic auxiliary agent containing a compound represented by .

Description

Antistatic auxiliary {ANTISTATIC AID}

The present invention relates to antistatic auxiliaries. Additionally, the present invention relates to a composition containing an antistatic auxiliary agent, an adhesive composition, an adhesive layer, an adhesive sheet, a surface protection film, and an optical film with an adhesive.

The adhesive layer used when bonding a polarizer used in a liquid crystal display, etc., or a touch panel substrate, contains ionic compounds such as inorganic salts or organic salts as an antistatic agent in order to prevent static electricity by lowering the surface resistance of the adhesive layer. There are cases where it is added as . If static electricity stays on the surface of the adhesive layer, it becomes easy for fine particles to adhere to the surface, and that static electricity is transferred to the polarizer or touch panel substrate to be bonded in the next step, causing malfunction. This prevents static electricity on the surface of the adhesive layer. has become increasingly important recently.

Therefore, in order to further demonstrate the function of these antistatic agents, it is known to add ethylene carbonate or propylene carbonate to the adhesive as an auxiliary agent for the antistatic agent (Patent Documents 1 to 3).

However, because ethylene carbonate has a melting point around 35°C, it is difficult to handle industrially both as a solid and as a liquid, and even if it is actually added to the adhesive together with an antistatic agent, the effect of lowering the surface resistance may be small (described later). (see Comparative Example 2).

In addition, when propylene carbonate was used, even though low surface resistance was obtained immediately after forming the adhesive layer, there was a problem in that the surface resistance increased over time and the antistatic performance was not stable (comparison described later). see example 3).

In this regard, there is a demand for an antistatic auxiliary that can provide low antistatic properties when added to an adhesive together with an antistatic agent and also has stability over time.

Japanese Patent Publication 2019-156916 WO2007/111200A1 Japanese Patent Publication No. 2010-265388

The object of the present invention is to provide an antistatic auxiliary agent that achieves low surface resistance and stable surface resistance over time compared to conventional auxiliary carbonate compounds for antistatic agents.

The present inventors have carefully studied an antistatic auxiliary agent that achieves low surface resistance and stable surface resistance over time compared to carbonate compounds, which are conventional auxiliary agents for antistatic agents, and completed the present invention. It has arrived.

That is, the present invention provides the following [1] to [12].

〔One〕

Equation (I)

(Wherein, R ¹ represents a hydrocarbon group containing an oxygen atom, a hydroxy group, or a carboxyl group,

R ² represents a hydrocarbon group, hydroxy group, carboxyl group, or hydrogen atom that may contain an oxygen atom.)

An antistatic auxiliary containing the compound represented by .

〔2〕

The antistatic auxiliary agent according to [1], wherein R ¹ represents a hydrocarbon group having an ether bond.

〔3〕

R ¹ is the following formula (II)

-R ³ -OR ⁴ (II)

(In the formula, R ³ represents a divalent aliphatic hydrocarbon group, and R ⁴ represents a hydrocarbon group.)

The antistatic auxiliary agent described in [1].

〔4〕

The antistatic auxiliary agent according to [1], wherein R ² represents a hydrogen atom.

〔5〕

A composition containing an antistatic agent and an antistatic auxiliary agent according to [1].

〔6〕

The composition according to [5], wherein the antistatic agent is a salt consisting of a cation and an anion, and one or both of the cation and anion are organic ions.

〔7〕

An adhesive composition containing an acrylic adhesive, an antistatic agent, and an antistatic auxiliary agent according to [1].

〔8〕

An adhesive layer containing an acrylic adhesive, an antistatic agent, and an antistatic auxiliary agent according to [1].

〔9〕

An adhesive sheet formed by forming a base layer and an adhesive layer as described in [8].

〔10〕

A surface protection film comprising a base material layer and an adhesive layer according to [8].

〔11〕

An optical film with an adhesive comprising an optical film and an adhesive layer according to [8].

〔12〕

For preparing an antistatic auxiliary, the following formula (I)

(Wherein, R ¹ represents a hydrocarbon group containing an oxygen atom, a hydroxy group, or a carboxyl group,

R ² represents a hydrocarbon group, hydroxy group, carboxyl group, or hydrogen atom that may contain an oxygen atom.)

Use of compounds represented by .

The present invention provides an antistatic auxiliary agent that produces a low-resistance surface and has excellent stability over time.

Figure 1 shows the IR measurement results of auxiliary agent 1.
Figure 2 shows the IR measurement results of adjuvant 2.
Figure 3 shows the IR measurement results of auxiliary agent 3.

The antistatic auxiliary of the present invention has the following formula (I)

(Wherein, R ¹ represents a hydrocarbon group containing an oxygen atom, a hydroxy group, or a carboxyl group,

R ² represents a hydrocarbon group, hydroxy group, carboxyl group, or hydrogen atom that may contain an oxygen atom.)

Contains the compound represented by .

In the hydrocarbon group containing an oxygen atom, the oxygen atom consists of a hydroxy group, ether (-O-), ester (-O-CO- or -CO-O-), and carbonyl (-CO-). It is contained as at least one type of group selected from the group. The hydrocarbon group containing an oxygen atom is preferably a hydrocarbon group having at least one type of ether (-O-) bond.

The number of oxygen atoms in the hydrocarbon group containing oxygen atoms is preferably 1 to 5, more preferably 1 to 3, and still more preferably 1 to 2.

In the hydrocarbon group of a hydrocarbon group containing an oxygen atom or a hydrocarbon group that may contain an oxygen atom, one preferred embodiment includes a hydrocarbon group having 1 to 20 carbon atoms, more preferably a hydrocarbon group having 1 to 12 carbon atoms. .

Preferred R ¹ is represented by the following formula (II)

-R ³ -OR ⁴ (II)

(In the formula, R ³ represents a divalent aliphatic hydrocarbon group, and R ⁴ represents a hydrocarbon group.)

It is a group represented by .

The divalent aliphatic hydrocarbon group represented by R ³ is preferably a divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms, for example -(CH ₂ ) _n1 - (n1 represents an integer of 1 to 8), -CH( CH ₃ )-(CH ₂ ) _n2 - (n2 represents an integer from 1 to 6), -C(CH ₃ ) ₂ -(CH ₂ ) _n3 - (n3 represents an integer from 1 to 5), etc. can be, and -(CH ₂ )- is preferable.

The hydrocarbon group represented by R ⁴ includes a saturated straight-chain hydrocarbon group, a saturated branched-chain hydrocarbon group, a saturated cyclic hydrocarbon group, an unsaturated straight-chain hydrocarbon group, an unsaturated branched-chain hydrocarbon group, an aromatic hydrocarbon group, and an aromatic aliphatic hydrocarbon group. I can hear it. In one embodiment, the hydrocarbon group represented by R ⁴ is preferably a hydrocarbon group having 1 to 10 carbon atoms.

Examples of the saturated linear hydrocarbon group include linear alkyl groups having 1 to 10 carbon atoms, such as methyl group, ethyl group, and n-propyl group.

Examples of the saturated branched hydrocarbon group include branched alkyl groups having 3 to 10 carbon atoms, such as isopropyl group, sec-butyl group, isobutyl group, tert-butyl group, and 2-ethylhexyl group.

Examples of the saturated cyclic hydrocarbon group include cycloalkyl groups such as cyclopropyl group, cyclopentyl group, cyclohexyl group, norbornyl group, and adamantyl group, methylcyclohexyl group, and ethylcyclohexyl group.

Examples of the unsaturated linear hydrocarbon group include vinyl group, vinylidene group, allyl group, butenyl group, and linear alkenyl group of 2 to 10 carbon atoms having a CH ₂ =C structure.

Examples of the unsaturated branched hydrocarbon group include branched alkenyl groups having 3 to 10 carbon atoms such as propen-2-yl group, buten-2-yl group and buten-3-yl group, and branched alkenyl groups having 4 to 10 carbon atoms such as butyn-3-yl group. 10 branched chain alkynyl groups, etc.

Examples of the aromatic hydrocarbon group include aromatic hydrocarbon groups having 6 to 10 carbon atoms, such as phenyl group, tolyl group, xylyl group, and naphthyl group.

The aromatic aliphatic hydrocarbon group includes benzyl group, methylbenzyl group, β-phenylethyl group (phenethyl group), 1-phenylethyl group, 1-methyl-1-phenylethyl group, p-methylbenzyl group, styryl group, cinnamyl group, etc. An aromatic hydrocarbon group having 7 to 10 carbon atoms is included.

Hydrocarbon groups containing oxygen atoms include methoxymethyl group, ethoxymethyl group, n-propyloxymethyl group, isopropyloxymethyl group, n-butyloxymethyl group, isobutyloxymethyl group, tert-butyloxymethyl group, (2-ethylhexyl) )Oxymethyl group, allyloxymethyl group, (2-propenyloxy)methyl, 2-methoxyethyl group, 3-methoxypropyl group, 4-methoxybutyl group, 5-methoxypentyl group, 6-methoxyhexyl group , 7-methoxyheptyl group, 8-methoxyoctyl group, 9-methoxynonyl group, 10-methoxydecyl group, 2-ethoxyethyl group, 3-ethoxypropyl group, 4-ethoxybutyl group, 2- (2'-methoxyethoxy)ethyl group, 2-(2'-ethoxyethoxy)ethyl group, 2-(2'-n-propyloxyethoxy)ethyl group, 2-(2'-isopropyloxyethoxy) ) Ethyl group, 2-(2'-n-butyloxyethoxy)ethyl group, 2-(2'-isobutyloxyethoxy)ethyl group, 2-(2'-tert-butyloxyethoxy)ethyl group, 2-( 2'-n-pentyloxyethoxy)ethyl group, 2-[2'-(2"-ethylbutyloxy)ethoxy]ethyl group, 2-(2'-n-hexyloxyethoxy)ethyl group, 2-[2 '-(3"-ethylpentyloxy)ethoxy]ethyl group, 2-(2'-n-heptyloxyethoxy)ethyl group, 2-(2'-n-octyloxyethoxy)ethyl group, etc.

Hydrocarbon groups containing oxygen atoms include methoxymethyl group, ethoxymethyl group, n-propyloxymethyl group, isopropyloxymethyl group, n-butyloxymethyl group, isobutyloxymethyl group, tert-butyloxymethyl group, (2-ethylhexyl) ) Oxymethyl group, allyloxymethyl group, 2-(2'-methoxyethoxy)ethyl group, 2-(2'-ethoxyethoxy)ethyl group, 2-(2'-n-propyloxyethoxy)ethyl group, 2 -(2'-isopropyloxyethoxy)ethyl group, 2-(2'-n-butyloxyethoxy)ethyl group, 2-(2'-isobutyloxyethoxy)ethyl group, 2-(2'-tert- Butyloxyethoxy)ethyl group and the like are preferred.

When the antistatic auxiliary of the present invention is used together with an antistatic agent in an adhesive or other resin product, it is preferable that it is a liquid at 10°C or higher from the viewpoint of handling, etc. Additionally, it is desirable to have good compatibility with the resin of the adhesive or other resin products or with the antistatic agent used together.

As the antistatic agent in the present invention, known antistatic agents can be widely used and are not particularly limited, but examples include Q ⁺ · A ^- (Q ⁺ is an organic ammonium ion, an organic phosphonium ion, and an organic sulfonium ion. , represents an imidazolium ion or a pyridinium ion. A ^- represents an organic or inorganic anion.) Examples include antistatic agents of onium salts represented by . Such antistatic agents are, for example, Japanese Patent Publication No. 2019-147771, Japanese Patent Publication No. 2019-108414, Japanese Patent Publication No. 2019-85570, Japanese Patent Publication No. 2019-65173, Japanese Patent Publication No. 2018-150257, Japan. Antistatic agents disclosed in Unexamined Patent Publication 2017-218465, Japanese Unexamined Patent Publication 2017-48149, Japanese Unexamined Patent Publication 2016-188315, etc. can be mentioned. When using an antistatic agent for the adhesive resin, it is preferable to use one that has good compatibility with the adhesive resin.

Preferred examples of Q ⁺ include cations of the following formulas (2b) to (5e).

(R ^1b to R ^3b are an alkyl group having 1 to 20 carbon atoms which may contain an oxygen atom, an alkenyl group having 1 to 20 carbon atoms which may contain an oxygen atom, or an aryl group having 6 to 20 carbon atoms which may contain an oxygen atom , or an aralkyl group of 7 to 20 carbon atoms which may contain an oxygen atom, and R ^4b is a hydrogen atom, an alkyl group of 1 to 20 carbon atoms which may contain an oxygen atom, or an aralkyl group of 1 to 20 carbon atoms which may contain an oxygen atom. It is an alkenyl group, an aryl group with 6 to 20 carbon atoms which may contain an oxygen atom, or an aralkyl group with 7 to 20 carbon atoms which may contain an oxygen atom. R ^1b and R ^2b are bonded to each other at the terminals and have a substituent. It may form a pyrrolidine ring, a piperidine ring which may have a substituent, or a pyridine ring which may have a substituent. However, when R ^1b and R ^2b are bonded to each other at the terminals to form a pyridine ring, R ^3b does not exist.)

(R ^1c to R ^3c are an alkyl group of 1 to 20 carbon atoms which may contain an oxygen atom, an alkenyl group of 1 to 20 carbon atoms which may contain an oxygen atom, an aryl group of 6 to 20 carbon atoms which may contain an oxygen atom, or an aralkyl group of 7 to 20 carbon atoms which may contain an oxygen atom, and R ^4c is a hydrogen atom, an alkyl group of 1 to 20 carbon atoms which may contain an oxygen atom, or an alkyl group of 1 to 20 carbon atoms which may contain an oxygen atom. It is a nyl group, an aryl group having 6 to 20 carbon atoms which may contain an oxygen atom, or an aralkyl group having 7 to 20 carbon atoms which may contain an oxygen atom, and R ^1c and R ^2c are bonded to each other at the terminals and may have a substituent. It may form a phosphorane ring, a phosphorinane ring that may have a substituent, or a phosphorine ring that may have a substituent. However, when R ^1c and R ^2c are bonded to each other at the terminals to form a phosphorine ring, R ^3c does not exist.)

(R ^1d and R ^5d are an alkyl group with 1 to 20 carbon atoms which may contain an oxygen atom, an alkenyl group with 1 to 20 carbon atoms which may contain an oxygen atom, an aryl group with 6 to 20 carbon atoms which may contain an oxygen atom, or an aralkyl group having 7 to 20 carbon atoms which may contain an oxygen atom, and R ^2d to R ^4d are a hydrogen atom, an alkyl group with 1 to 20 carbon atoms, an alkenyl group with 1 to 20 carbon atoms, an aryl group with 6 to 20 carbon atoms, or a carbon number. An aralkyl group with 7 to 20 carbon atoms, an alkoxy group with 1 to 20 carbon atoms, an alkenyloxy group with 1 to 20 carbon atoms, an aryloxy group with 6 to 20 carbon atoms, or an aralkyloxy group with 7 to 20 carbon atoms.)

(R ^1e is an alkyl group with 1 to 20 carbon atoms which may contain an oxygen atom, an alkenyl group with 1 to 20 carbon atoms which may contain an oxygen atom, an aryl group with 6 to 20 carbon atoms which may contain an oxygen atom, or is an aralkyl group having 7 to 20 carbon atoms which may contain an oxygen atom, and R ^2e and R ^3e are each independently a hydrogen atom, a fluorine atom, a trifluoromethyl group, an alkyl group having 1 to 20 carbon atoms which may contain an oxygen atom, It represents an alkoxy group with 1 to 20 carbon atoms.)

R ^1e and R ^2e may be bonded to each other at the ends to form a ring, and when R ^1e and R ^2e are bonded to each other to form a ring, for example, a piperidine ring, pyrrolidine ring, morpholine ring, etc. may be formed.

Here, R ^1b to R ^3b and R ^4b represented by the formula (2b), R ^1c to R ^3c and R 4c represented by the formula (3c), ^{and R 1d ,} R ^5d and R represented by the formula (4d). The alkyl groups having 1 to 20 carbon atoms for R ^1e to R ^3e represented by ^2d to R ^4d and formula (5e) may be linear, branched, or cyclic. Alkyl groups having 1 to 20 carbon atoms include methyl group, ethyl group, propyl group, butyl group, hexyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, icosyl group, 2-ethylhexyl group, cyclopropyl group, Cyclobutyl group, cyclohexyl group, etc. are mentioned, and methyl group, ethyl group, propyl group, butyl group, octyl group, decyl group, and dodecyl group are preferable.

R ^1b to R ^3b and R ^4b represented by formula (2b), R ^1c to R ^3c and R ^4c represented by formula (3c), and R ^1d , R ^5d , and R ^2d to R ^4d represented by formula (4d). , Alkenyl groups having 1 to 20 carbon atoms for R ^1e shown in formula (5e) include vinyl group, allyl group, 1-propenyl group, isopropenyl group, butenyl group, 1,3-butadienyl group, pentenyl group, Hexenyl group, heptenyl group, octenyl group, nonenyl group, decenyl group, undecenyl group, dodecenyl group, cyclobutenyl group, cyclopentenyl group, cyclohexenyl group, etc., preferably vinyl group and allyl group. It's awesome.

R ^1b to R ^3b and R ^4b represented by formula (2b), R ^1c to R ^3c and R ^4c represented by formula (3c), and R ^1d , R ^5d , and R ^2d to R ^4d represented by formula (4d). , Examples of the aryl group having 6 to 20 carbon atoms for R ^1e represented by formula (5e) include phenyl group, naphthyl group, and anthracene group, and phenyl group is preferred.

R ^1b to R ^3b and R ^4b represented by formula (2b), R ^1c to R ^3c and R ^4c represented by formula (3c), and R ^1d , R ^5d , and R ^2d to R ^4d represented by formula (4d). , The aralkyl group having 7 to 20 carbon atoms for R ^1e shown in formula (5e) includes benzyl group, methylbenzyl group, β-phenylethyl group (phenethyl group), 1-phenylethyl group, and 1-methyl-1-phenylethyl group. , p-methylbenzyl group, styryl group, cinnamyl group, etc., and benzyl group is preferred.

R ^1b to R ^3b and R ^4b represented by formula (2b), R ^1c to R ^3c and R ^4c represented by formula (3c), and R ^1d , R ^5d , and R ^2d to R ^4d represented by formula (4d). , R ^1e shown in formula (5e) is an alkyl group having 1 to 20 carbon atoms containing an oxygen atom, an alkenyl group having 1 to 20 carbon atoms containing an oxygen atom, an aryl group having 6 to 20 carbon atoms containing an oxygen atom, or oxygen. In the case of an aralkyl group containing 7 to 20 carbon atoms, the oxygen atom is a hydroxy group, ether (-O-), ester (-O-CO- or -CO-O-), and carbonyl (- It contains at least one type of group selected from the group consisting of CO-), and is preferably a group containing at least one type of ether (-O-) bond.

When it contains oxygen atoms, the number of oxygen atoms is preferably 1 to 5, more preferably 1 to 3, and even more preferably 1 to 2.

R ^1b to R ^3b and R ^4b represented by formula (2b), R ^1c to R ^3c and R ^4c represented by formula (3c), and R ^1d , R ^5d , and R ^2d to R ^4d represented by formula (4d). , an alkyl group of 1 to 20 carbon atoms containing an oxygen atom for R ^1e represented by formula (5e), an alkenyl group of 1 to 20 carbon atoms containing an oxygen atom, an aryl group of 6 to 20 carbon atoms or oxygen containing an oxygen atom. Examples of aralkyl groups containing 7 to 20 carbon atoms include methoxymethyl group, ethoxymethyl group, n-propyloxymethyl group, isopropyloxymethyl group, n-butyloxymethyl group, isobutyloxymethyl group, and tert-butyloxymethyl group. , (2-ethylhexyl)oxymethyl group, 2-(2'-methoxyethoxy)ethyl group, 2-(2'-ethoxyethoxy)ethyl group, 2-(2'-n-propyloxyethoxy)ethyl group , 2-(2'-isopropyloxyethoxy)ethyl group, 2-(2'-n-butyloxyethoxy)ethyl group, 2-(2'-isobutyloxyethoxy)ethyl group, 2-(2'- tert-butyloxyethoxy)ethyl group, 2-(2'-n-pentyloxyethoxy)ethyl group, 2-[2'-(2"-ethylbutyloxy)ethoxy]ethyl group, allyloxymethyl group, allyloxyethyl group , 1-propenyloxymethyl group, 1-propenyloxyethyl group, isopropenyloxymethyl group, isopropenyloxyethyl group, butenyloxymethyl group, butenyloxyethyl group, 4-methoxyphenyl group, 4-methoxybenzyl group, Examples include phenyloxymethyl group, phenyloxyethyl group, naphthyloxymethyl group, naphthyloxyethyl group, etc., preferably methoxymethyl group, ethoxymethyl group, isopropyloxymethyl group, (2-ethylhexyl)oxymethyl group, 2- (2'-methoxyethoxy)ethyl group, 2-(2'-ethoxyethoxy)ethyl group, 2-(2'-n-propyloxyethoxy)ethyl group, 2-(2'-isopropyloxyethoxy) ) An ethyl group can be mentioned.

R ^2d to R ^4d represented by formula (4d), R ^1e represented by formula (5e), an alkoxy group having 1 to 20 carbon atoms, an alkenyloxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, or Examples of aralkyloxy groups having 7 to 20 carbon atoms include methoxy group, ethoxy group, n-propyloxy group, isopropyloxy group, n-butyloxymethyl group, isobutyloxy group, tert-butyloxy group, (2- Ethylhexyl)oxy group, 2-methoxyethoxy group, 2-(n-propyloxy)ethoxy group, 2-(isopropyloxy)ethoxy group, 2-(n-butyloxy)ethoxy group, 2-(iso Butyloxy) ethoxy group, 2-(tert-butyloxy) ethoxy group, 2-(n-pentyloxy) ethoxy group, 2-(2'-ethylbutyloxy) ethoxy group, allyloxy group, 1-propenyl oxide group, isopropenyloxy group, butenyloxy group, 4-methoxyphenyl group, phenoxy group, naphthyloxy group, etc.

A ^- is trifluoromethanesulfonate anion, nonafluorobutanesulfonate anion, bis(fluorosulfonyl)imide anion, bis(trifluoromethanesulfonyl)imide anion, bis(pentafluor Bis(perfluoroalkylsulfonyl)imide anion such as loethanesulfonyl)imide anion, tetrafluoroborate anion, hexafluorophosphate anion, fluoride ion, chloride ion, bromide ion, thio Cyanate ion, iodide ion, acetate ion, methoxyacetate ion, ethoxyacetate ion, propoxyacetate ion, (2-methoxyethoxy)acetate ion, (2-ethoxyethoxy)acetate ion, trifluoride Carboxylic acid ions such as loacetate ion, pentafluoropropionate ion, heptafluorobutanoate ion, pentadecafluorooctanoate ion, benzoate ion, methanesulfonate ion, ethanesulfonate ion, trifluoromethanesulfonate ion, penta Sulfonic acid ions such as fluoroethanesulfonate ion, p-toluenesulfonate ion, and p-dodecylbenzenesulfonate ion, methyl phosphate monoester ion, ethyl phosphate monoester ion, propyl phosphate monoester ion, methyl phosphate diester ion, and ethyl phosphorus. Phosphate ions such as acid diester ions, and anions represented by formula (III) can be mentioned.

(In the formula, R ^IIIa to R ^IIId each independently represent a fluorine atom or a hydrocarbon group that may have a substituent.)

Examples of the hydrocarbon group include an aliphatic hydrocarbon group and an aromatic hydrocarbon group, and it is preferable that at least one of R ^IIIa to R ^IIId is an aromatic hydrocarbon group that may have a substituent. In R ^IIIa to R ^IIId , the number of carbon atoms of the hydrocarbon group is preferably 1 to 20, more preferably 1 to 14, and still more preferably 1 to 6.

Aliphatic hydrocarbon groups include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, ethenyl, propenyl, butenyl, and pentenyl. , hexenyl group, ethynyl group, propynyl group, pentynyl group, hexynyl group, cyclopentyl group, cyclohexyl group, etc. Examples of aromatic hydrocarbon groups include phenyl group, biphenyl group, biphenylenyl group, azulenyl group, terphenyl group, naphthyl group, anthryl group, naphthacenyl group, phenanthryl group, and fluorenyl group, and are preferred. It is a phenyl group.

For R ^IIIa to R ^IIId , when the hydrocarbon group has a substituent, the substituent includes, for example, a halogen group such as a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methoxy group, an ethoxy group, and a tert-butoxy group. Alkoxy groups such as phenoxy groups, aryloxy groups such as p-tolyloxy groups, aralkyloxy groups such as benzyloxy groups, alkyl groups such as methyl groups, ethyl groups, tert-butyl groups, and dodecyl groups, phenyl groups, and p-tolyl groups. In addition to aryl groups such as aryl group, xylyl group, cumenyl group, naphthyl group, and phenanthryl group, and aralkyl groups such as benzyl group, hydroxyl group, amino group, etc. can be mentioned. Preferably, halogen groups such as fluorine atom, chlorine atom, bromine atom, and iodine atom, alkoxy groups such as methoxy group, ethoxy group, and tert-butoxy group, aryloxy groups such as phenoxy group and p-tolyloxy group, and benzyl. It is an aralkyloxy group such as an oxy group, and a fluorine atom is particularly preferable. The number of substituents is preferably 1 to 9, more preferably 1 to 7, and still more preferably 1 to 5.

Anions represented by formula (III) include, for example, tetraphenylborate anion, tetrakis(4-chlorophenyl)borate anion, tetrakis(4-fluorophenyl)borate anion, tetrakis(4) -methylphenyl)borate anion, tetrakis[4-(trifluoromethyl)]phenylborate anion, tetrakis(4-methoxyphenyl)borate anion, tetrakis(pentafluorophenyl)borate anion, etc. I can hear it.

The antistatic auxiliary of the present invention can be used by mixing it with an antistatic agent in an adhesive, hard coat agent, paint, or other resin.

At this time, the antistatic agent and the antistatic auxiliary are mixed to form a composition containing the antistatic agent and the antistatic auxiliary of the present invention, and the composition can be used by adding it to an adhesive, hard coat agent, paint, or other resin.

Here, by selecting an antistatic auxiliary that can dissolve the antistatic agent used as an antistatic auxiliary, when the composition is used by adding it to an adhesive, hard coat agent, paint, or other resin, a solvent for dissolving the antistatic agent is used. The use of can also be omitted.

In addition, generally, antistatic agents and antistatic auxiliaries are separately supplied from the manufacturer to the maker who applies the adhesive, and are mixed with the adhesive resin solution or dilution solvent at the coating manufacturer, but the antistatic agent of the present invention is By using a liquid composition dissolved in an antistatic auxiliary agent, the preparation work of the adhesive in the coating maker can be omitted.

The composition of the present invention containing an antistatic agent and an antistatic auxiliary agent may be a composition consisting of an antistatic agent and an antistatic auxiliary agent, or a composition diluted with a solvent.

The composition comprising an antistatic agent and an antistatic auxiliary is preferably a composition in which an antistatic agent is dissolved in 0.1 to 30% by mass of an antistatic auxiliary, preferably a composition in which an antistatic agent is dissolved in 0.5 to 20% by mass of an antistatic auxiliary, more preferably is a composition in which an antistatic agent is dissolved in 1.0 to 10% by mass of an antistatic auxiliary agent.

In addition, the composition consisting of an antistatic agent, an antistatic auxiliary, and a solvent is a composition containing 0.1 to 20% by mass of an antistatic agent, 30 to 80% by mass of an antistatic auxiliary, and the remainder is a solvent, preferably 0.1 to 0.1% by mass of an antistatic agent. It is a composition containing 10% by mass, 40 to 70% by mass of an antistatic auxiliary, and the remainder as a solvent.

The solvent in this case is preferably one that can dissolve all of the antistatic agent, antistatic auxiliary agent, and adhesive resin composition. As a solvent, for example, ethyl acetate, methanol, toluene, methyl ethyl ketone, acetone, etc. are preferable, and ethyl acetate is more preferable.

The composition of the present invention containing an antistatic agent and an antistatic auxiliary may further contain various additives depending on the intended use. These additives include crosslinking agents, tackifiers, plasticizers, antioxidants, flame retardants, clarifying agents, etc.

The adhesive composition of the present invention contains an antistatic agent, an antistatic auxiliary agent, and an adhesive, and may further contain a solvent. After the adhesive composition is applied to the surface of an arbitrary substrate such as a resin molded body, an antistatic adhesive layer can be formed on the substrate surface by removing the solvent as necessary.

As the adhesive, known adhesives can be widely used and are not particularly limited, but examples include acrylic adhesives, rubber adhesives, vinyl alkyl ether adhesives, silicone adhesives, polyester adhesives, polyamide adhesives, urethane adhesives, and epoxy. These include adhesives and the like, and acrylic adhesives are preferred. The adhesive may be of any type. For example, it can be used in the form of an active energy ray-curable adhesive, a solvent-type (solution-type) adhesive, an emulsion-type adhesive, or a heat-melting adhesive (hot melt-type adhesive). there is.

Acrylic adhesives are preferably used in optical member applications for reasons such as their high transparency. In this regard, the antistatic auxiliary of the present invention, which shows little change in color over time, is particularly preferably used in acrylic adhesives. An acrylic adhesive is an adhesive composition containing an acrylic polymer as an essential ingredient. In addition to the acrylic polymer, the acrylic adhesive may contain other components (additives) such as a solvent as needed.

The acrylic polymer is preferably an acrylic polymer composed of an alkyl (meth)acrylate ester having a straight-chain or branched alkyl group as an essential monomer component (monomer component). In addition, in this specification, unless otherwise specified, “(meth)acryl” refers to “acrylic” and/or “methacryl.”

The adhesive composition of the present invention preferably contains 0.01 to 10 parts by mass of an antistatic agent and 0.01 to 30 parts by mass of an antistatic auxiliary, based on 100 parts by mass of resin for adhesive, and more preferably contains 0.1 to 30 parts by mass of an antistatic agent. It contains 5.0 parts by mass and 0.1 to 15.0 parts by mass of an antistatic auxiliary agent. If the amount of the antistatic auxiliary is less than 0.01 parts by mass, it is difficult to fully exert the effect of the antistatic auxiliary, and if it is more than 30 parts by mass, the adhesive strength of the adhesive may decrease, so the above range is preferable.

If the amount of the antistatic agent used is less than 0.01 parts by mass, it is difficult to fully exert the effect of the antistatic agent, and if it is more than 10 parts by mass, the adhesive strength of the adhesive may decrease, so the above range is preferable.

In the adhesive composition of the present invention, various additives can be used together depending on the intended use. These additives include crosslinking agents, tackifiers, plasticizers, antioxidants, flame retardants, clarifying agents, etc.

As a crosslinking agent, for example, when the acrylic polymer has an active hydrogen-containing functional group such as a hydroxyl group or a carboxyl group, an isocyanate-based crosslinking agent can be used.

In addition to this, crosslinking agents such as epoxy-based crosslinking agents, melamine-based resins, aziridine derivatives, and metal chelate compounds may be used. These crosslinking agents may be used individually or in combination.

The isocyanate-based crosslinking agent includes aliphatic polyisocyanates such as trimethylene diisocyanate, butylene diisocyanate, hexamethylene diisocyanate (HDI), and dimer acid diisocyanate, cyclopentylene diisocyanate, cyclohexylene diisocyanate, and isophorone diisocyanate ( IPDI), alicyclic isocyanates such as 1,3-bis(isocyanatomethyl)cyclohexane, 2,4-tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate, xylylene diisocyanate (XDI), etc. aromatic isocyanates, the isocyanate compound is modified by an allophanate bond, biuret bond, isocyanurate bond, urethione bond, urea bond, carbodiimide bond, uretonimine bond, oxadiazinetrione bond, etc. and polyisocinate modified products. For example, commercial products include Takenate 300S, Takenate 500, Takenate 600, Takenate D165N, Takenate D178N, Takenate D170N (manufactured by Mitsui Chemicals Co., Ltd.), Sumidur T80, Sumidur L, and Desmo. Dur N3400 (above, manufactured by Sumika Kobe Strourethane Co., Ltd.), Millionate MR, Millionate MT, Coronate L, Coronate HL, Coronate HX (above, manufactured by Tosoh Corporation), etc. These isocyanate compounds may be used individually or in mixture of two or more types, and it is also possible to use a bifunctional isocyanate compound and a trifunctional or higher isocyanate compound in combination. By using a crosslinking agent in combination, it becomes possible to achieve both adhesion and repellency resistance (adhesion to curved surfaces), and when a pressure-sensitive adhesive sheet is produced using the pressure-sensitive adhesive composition, a pressure-sensitive adhesive sheet with more excellent adhesive reliability can be obtained.

The adhesive composition of the present invention may further contain a curing catalyst.

When using an isocyanate-based crosslinking agent as a crosslinking agent, known urethane catalysts such as tin catalysts and amine catalysts can be used as the curing catalyst, for example. By using the catalyst in combination, high crosslinking properties (crosslinking degree and curability) are obtained, surface migration occurs due to appropriate phase separation of the adhesive layer with a high crosslinking density and the antistatic agent, and high antistatic properties are obtained, which is a desirable aspect. .

Examples of the tin catalyst include dibutyltin dichloride, dibutyltin oxide, dibutyltin dibromide, dibutyltin maleate, dibutyltin dilaurate, dibutyltin diacetate, and dibutyltin alcohol. Pide, tributyltin methoxide, tributyltin acetate, triethyltin ethoxide, tributyltin ethoxide, dioctyltin oxide, dioctyltin dilaurate, tributyltin chloride, tributyltin trichloroacetate , tin 2-ethylhexanoate, etc. These catalysts may be used individually or in combination.

The substrate for coating the adhesive composition of the present invention is not particularly limited as various substrates can be used regardless of whether they are inorganic or organic, and include, for example, polyethylene terephthalate (PET), polybutylene terephthalate, and polyethylene terephthalate. Phthalate, polyethylene, polypropylene, cellophane, diacetylcellulose, triacetylcellulose, acetylcellulose butyrate, polyvinyl chloride, polyvinylidene chloride, polyvinyl alcohol, ethylene-vinyl acetate copolymer, polystyrene, polycarbonate, polymethylpentene, Resins such as polysulfone, polyetheretherketone, polyethersulfone, polyetherimide, polyimide, fluororesin, nylon, acrylic resin, glass, etc. may be mentioned, and all known ones can be used. The base material may be sheet-shaped, film-shaped, plate-shaped, etc. depending on the intended use.

The adhesive layer of the present invention can be obtained by applying a coating solution containing an adhesive composition to a substrate and drying it as necessary, thereby obtaining a coating having an adhesive layer on at least a portion of the surface and/or the back surface of the substrate. The application method is not particularly limited, and examples include gravure coating, bar coating, knife coating, roll coating, blade coating, die coating, spray coating, brush coating, dipping, and curtain coating. Methods, spin coat methods, etc. are known, and various methods can be appropriately selected. The film thickness of the adhesive layer is 1 to 200 μm, preferably 1 to 50 μm, and more preferably 5 to 20 μm as the film thickness after drying.

When curing the adhesive with ultraviolet rays, light sources such as a high-pressure mercury lamp, low-pressure mercury lamp, ultra-high pressure mercury lamp, metal halide lamp, carbon arc, or xenon arc can be used.

Articles having an adhesive layer of the present invention include adhesive sheets, adhesive tapes, and adhesive plates.

The adhesive sheet of the present invention is one in which an adhesive layer made of the adhesive composition of the present invention is laminated on one side of a base material. In addition to the adhesive layer, a release sheet (separator) may be laminated. The release sheet may be subjected to a mold release treatment with a silicone-based or fluorine-based mold release agent or the like on the side that joins the adhesive side of the pressure-sensitive adhesive layer.

The adhesive sheet of the present invention can be suitably used as a surface protection film for a polarizing plate or other optical film.

The optical film having an adhesive layer of the present invention is not particularly limited, but examples include a polarizing plate film for a display, a retardation film, a lens film, an optical compensation film, a light diffusion film, and an electromagnetic wave shield film.

As a specific example of the optical film with an adhesive of the present invention, an adhesive layer of the present invention is formed on one side of a PET film as a substrate by applying the adhesive of the present invention by a roll coater method, a bar coat method, etc., and a polarizing plate is formed through the adhesive layer. There is a laminated film in which a pressure-sensitive adhesive layer of the present invention is equally applied to both sides of a laminated polarizing plate film or a PET film as a substrate, and a polarizing plate is bonded to one side and a light diffusion film to one side. Further examples include image display devices and members in which these optical films, glass substrates, color filter substrates, touch panel substrates, etc. are bonded together with the adhesive of the present invention.

[Example]

Next, the present invention will be specifically explained based on examples, but the present invention is not limited to these at all.

・Measurement of surface resistance value

Measurement was made using a resistivity meter (Hirester UP manufactured by Mitsubishi Chemical Corporation).

Manufacturing Example 1

25.0 g of allyl glycidyl ether (reagent manufactured by Tokyo Chemical Industry Co., Ltd.), 25.0 g of ethyl acetate (reagent manufactured by Tokyo Chemical Industry Co., Ltd.), and 4.0 g of sodium iodide (reagent manufactured by Kanto Chemical Co., Ltd.) were placed in a 180 ml autoclave and sealed. , the temperature inside the container was heated to 100°C using a heater installed on the outer periphery of the container. Carbon dioxide gas was supplied there until the pressure inside the container reached 0.5 MPa, and the mixture was stirred for 3 hours while maintaining the pressure, thereby obtaining a reaction solution in which the glycidyl group was carbonated. Thereafter, the reaction solution was dissolved in the same volume of ethyl acetate, and then passed through a spherical silica column (Biotage sfar sillica HD C_High Capasity Duo 20 um, manufactured by Biotage Japan) to support the reaction solution and sodium iodide in the silica column. Afterwards, sodium iodide was removed by eluting the carbonation reaction product by passing a mixed solvent of ethyl acetate and hexane. Afterwards, unnecessary ethyl acetate was removed by drying under reduced pressure using an evaporator to obtain auxiliary agent 1 (1,3-dioxolane, 4-[(2-propenyloxy)methyl]).

＜Identification data＞

The obtained auxiliary agent 1, along with allyl glycidyl ether as a raw material, was subjected to comparative measurement using ATR-FTIR (total reflection Fourier transform infrared spectrophotometer (FT/IR-6600 manufactured by Nippon Spectrophotometer Co., Ltd.)) using a diamond prism, and the result was 1750 Production of the reactant was confirmed by detection of the C=O bond of the cyclic carbonate group detected in the vicinity of ~1800 cm ^-1 (see Figure 1).

Production example 2

Auxiliary agent 2 (1,3-dioxolane, 4-[[( 2-ethylhexyl)oxy]methyl]) was obtained.

＜Identification data＞

The obtained auxiliary agent 2 was confirmed as a reaction product by detection of a C=O bond by ATR-FTIR measurement using a diamond prism in the same manner as in Production Example 1 (see Fig. 2).

Production example 3

Auxiliary agent 3 (1,3-dioxolane, 4-ethoxymethyl) was prepared in the same reaction except that the allyl glycidyl ether in Preparation Example 1 was replaced with ethyl glycidyl ether (reagent manufactured by Tokyo Chemical Industry Co., Ltd.). got it

＜Identification data＞

The obtained auxiliary agent 3 was confirmed as a reaction product by detection of a C=O bond by ATR-FTIR measurement using a diamond prism in the same manner as in Production Example 1 (see Fig. 3).

Preparation Example 4: Antistatic agent 1

(4-1) Synthesis of 1-decylpyridinium tetrakis(pentafluorophenyl)borate

In a 1 L 4-neck flask, 432.6 g of ammonium tetrakis (pentafluorophenyl) borate aqueous solution (ammonium tetrakis (pentafluorophenyl) borate net content of 1.64 mol), 151.3 g of toluene, and 140.1 g of 1-decylpyridinium bromide aqueous solution. (1-Decylpyridinium bromide pure content: 139.1 mmol) was added and reacted at 60°C for 2 hours. After the reaction, it was left to stand and cooled to room temperature. Ion-exchanged water was added to the cooled reaction solution, and the washing operation was performed three times. The obtained organic layer was concentrated under reduced pressure to obtain 127.6 g of 1-decylpyridinium-tetrakis(pentafluorophenyl)borate. Additionally, the 1-decylpyridinium bromide aqueous solution can be prepared according to the description of Example 2 of Japanese Patent Application Laid-Open No. 2015-78131.

(4-2) Preparation of antistatic agent 1

1-Decylpyridiniumtetrakis(pentafluorophenyl)borate was dissolved by adding ethyl acetate, and an ethyl acetate solution of 1-decylpyridiniumtetrakis(pentafluorophenyl)borate with a concentration of 5 mass% was prepared ( It was used as antistatic agent 1).

Preparation Example 5: Antistatic Agent 2

(5-1) Synthesis of methyltrioctylammonium·dodecylbenzenesulfonate

In a 5 L flask, 620.9 g of methyltrioctylammonium chloride aqueous solution (methyltrioctylammonium chloride net content: 1.25 mol), 894.6 g of ion-exchanged water, and 979.4 g of toluene were added, and 422.9 g of dodecylbenzenesulfonic acid was added dropwise over 4 hours. . After dropwise addition, it was allowed to react for 3 hours. After completion of the reaction, the reaction solution was allowed to stand, the liquid was separated, and the aqueous layer was removed. The operation of adding ion-exchanged water to the obtained organic layer and washing it was performed twice. The organic layer after washing was concentrated under reduced pressure, and the concentrated liquid was filtered to obtain 814.7 g of methyltrioctylammonium dodecylbenzenesulfonate.

(5-2) Preparation of antistatic agent 2

Ethyl acetate was added and dissolved in methyltrioctylammonium dodecylbenzenesulfonate to obtain an ethyl acetate solution (antistatic agent 2) of methyltrioctylammonium dodecylbenzenesulfonate with a concentration of 5% by mass.

Preparation Example 6: Antistatic Agent 3

(6-1) Synthesis of tributyldodecylphosphonium trifluoromethanesulfonate

729.2 g (4.67 mol) of lithium trifluoromethane sulfonate, 2317 g of ion-exchanged water, and 2756.0 g of tributyldodecylphosphonium bromide were added to the flask and allowed to react for 3 hours. After the reaction, the liquid was separated and the aqueous layer was removed. The operation of adding ion-exchanged water and washing the obtained organic layer was performed three times. The organic layer after washing was concentrated under reduced pressure to obtain 2167.5 g of tributyldodecylphosphonium trifluoromethane sulfonate.

(6-2) Preparation of antistatic agent 3

Ethyl acetate was added and dissolved in tributyldodecylphosphonium trifluoromethane sulfonate to obtain an ethyl acetate solution of tributyldodecylphosphonium trifluoromethane sulfonate with a concentration of 5 mass% (antistatic agent 3). .

Preparation Example 7: Antistatic agent 4

(7-1) Synthesis of 1-ethyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide

In a 3 L flask, 763.8 g of 1-ethyl-3-methylimidazolium chloride aqueous solution (1-ethyl-3-methylimidazolium chloride net content: 2.87 mol) and 497.6 g of ion-exchanged water were added, and lithium bis (trifluoride) was added thereto. 1153.0 g of lomethanesulfonyl)imide aqueous solution (lithium bis(trifluoromethanesulfonyl)imide net content of 3.01 mol) was added dropwise and allowed to react for 3 hours. After the reaction, the reaction liquid was separated and the aqueous layer was removed. The operation of adding ion-exchanged water to the obtained organic layer and washing it was performed twice. The organic layer after washing was concentrated under reduced pressure, and the concentrated liquid was filtered to obtain 1051.1 g of 1-ethyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide.

(7-2) Preparation of antistatic agent 4

1-ethyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide was dissolved by adding ethyl acetate, and 1-ethyl-3-methylimidazolium bis(trifluoroethylene)imide was dissolved at a concentration of 5% by mass. It was used as an ethyl acetate solution of lomethanesulfonyl)imide (antistatic agent 4).

Preparation Example 8: Method for adjusting adhesive composition

＜Synthesis of adhesive base material＞

150 g of 2-ethylhexyl acrylate monomer (reagent manufactured by Tokyo Chemical Industry Co., Ltd.), 4-hydroxybutylacrylate (reagent manufactured by Tokyo Chemical Industry Co., Ltd.) 7.5 g, azobisisobutyronitrile (reagent manufactured by Tokyo Chemical Industry Co., Ltd.) 0.3 g and 236 g of ethyl acetate (reagent manufactured by Tokyo Chemical Industry Co., Ltd.) were added to a 1 L separable flask, and the inside of the flask was purged with nitrogen while nitrogen bubbling was performed. After that, the temperature was raised while stirring, and the reaction was performed at 60°C for 5 hours, and the temperature was further raised to react at 70°C for 2 hours to obtain base material A for an adhesive containing 40% by mass of acrylic resin.

Assessment Methods

(Measurement of surface resistance 1)

The adhesive obtained with the composition shown in Table 1 was coated on a polyethylene terephthalate (PET) film (Lumire Film T60 manufactured by Toray Industries, Inc.) with a bar coater (No. 50) to a thickness of 20 um, and then coated at 120°C. It was dried in an oven for 3 minutes. After that, the surface of the coated film was laminated with a PET separator (release film manufactured by Nippa Co., Ltd.) as a protective film, and then left overnight in a room controlled at a temperature of 25°C and a humidity of 50%Rh.

After that, the surface resistance value (Ω/□) of the surface of the adhesive layer after peeling off the PET separator was measured in an environment with a temperature of 25°C and a humidity of 50%Rh.

(Measurement of surface resistance 2)

The laminated adhesive layer film with a surface resistance of 1 left overnight was left in an oven at 60°C for 3 days, after which the PET separator was peeled off and its surface resistance (Ω/□) was measured in an environment of 25°C and 50%Rh. .

(Measurement of surface resistance 3)

The laminated adhesive layer film after being left overnight with a surface resistance of 1 was left for one week in a room controlled at 25°C 50%Rh, and then the PET separator was peeled off and the surface resistance (Ω/□) was measured at 25°C 50%. Measurements were made under a %Rh environment.

Example 1

59.3 g of adhesive base material, antistatic agent 1 (ethyl acetate solution containing 5% by mass of 1-decylpyridinium tetrakis(pentafluorophenyl)borate) 4.8 g, auxiliary agent 1 (1.9 g, 1.2 mmol) , 4.8 g of an ethyl acetate solution containing 20 mass% of Takenate D-170N (manufactured by Mitsui Chemicals Co., Ltd.) as a crosslinking agent A, and 4.8 g of an ethyl acetate solution containing 0.05 mass% of dibutyltin dilaurate as a curing catalyst B. , and 24.3 g of ethyl acetate as a solvent were mixed to obtain 100 g of an adhesive composition. The obtained adhesive composition was evaluated. The results are shown in Table 2.

Example 2

An adhesive composition was obtained in the same manner as in Example 1, except that the auxiliary agent 1 was replaced with auxiliary agent 2 (2.7 g, 1.2 mmol) and ethyl acetate as the solvent was changed to 23.4 g. The obtained adhesive composition was evaluated. The results are shown in Table 2.

Example 3

An adhesive composition was obtained in the same manner as in Example 1, except that the auxiliary agent 1 was replaced with auxiliary agent 3 (1.7 g, 1.2 mmol) and ethyl acetate as the solvent was changed to 24.4 g. The obtained adhesive composition was evaluated. The results are shown in Table 2.

Comparative Example 1

An adhesive composition was obtained in the same manner as in Example 1, except that the auxiliary agent 1 was not used and ethyl acetate as the solvent was changed to 26.1 g. The obtained adhesive composition was evaluated. The results are shown in Table 2.

Comparative Example 2

An adhesive composition was obtained in the same manner as in Example 1, except that the auxiliary agent 1 was replaced with auxiliary agent 4 (1.0 g, 1.2 mmol) and ethyl acetate as the solvent was changed to 25.0 g. The obtained adhesive composition was evaluated. The results are shown in Table 2.

Comparative Example 3

An adhesive composition was obtained in the same manner as in Example 1, except that the auxiliary agent 1 was replaced with auxiliary agent 5 (1.2 g, 1.2 mmol) and ethyl acetate as the solvent was changed to 25.0 g. The obtained adhesive composition was evaluated. The results are shown in Table 2.

Examples 4, 5 and Comparative Examples 4 to 7

Base A for adhesive, ethyl acetate solution containing 5% by mass of the ionic liquid shown below as antistatic agents 2 and 3, compounds shown in Table 1 as auxiliary agents 1, 2, and 5, crosslinking agent A, and catalyst B for curing as shown in Table 1. The solution shown and ethyl acetate as a solvent were mixed in the formulation (unit: g) shown in Table 3 to obtain an adhesive composition. The obtained adhesive composition was evaluated. The results are shown in Table 3. In Table 3, all numerical units other than surface resistance values are "g".

Example 6

Base A for adhesive, ethyl acetate solution containing 5% by mass of the ionic liquid shown below as antistatic agents 1, 2, and 3, compounds shown in Table 1 as auxiliary agents 1, 2, and 5, crosslinking agent A, and catalyst B for curing. The solution shown in 1 and ethyl acetate as a solvent were mixed in the formulation (unit: g) shown in Table 4 to obtain an adhesive composition. The obtained adhesive composition was evaluated. The results are shown in Table 4. In Table 4, all numerical units other than surface resistance values are "g".

Claims (12)

Equation (I)

(Wherein, R ¹ represents a hydrocarbon group containing an oxygen atom, a hydroxy group, or a carboxyl group,
R ² represents a hydrocarbon group, hydroxy group, carboxyl group, or hydrogen atom that may contain an oxygen atom.)
An antistatic auxiliary containing the compound represented by . According to claim 1,
An antistatic auxiliary agent, wherein R ¹ represents a hydrocarbon group having an ether bond. According to claim 1,
R ¹ is the following formula (II)
-R ³ -OR ⁴ (II)
(In the formula, R ³ represents a divalent aliphatic hydrocarbon group, and R ⁴ represents a hydrocarbon group.)
Represented by gin, anti-static adjuvant. According to claim 1,
An antistatic auxiliary agent in which R ² represents a hydrogen atom. A composition containing an antistatic agent and an antistatic auxiliary agent according to claim 1. According to claim 5,
A composition in which the antistatic agent is a salt consisting of a cation and an anion, and either or both of the cation and anion are organic ions. An adhesive composition containing an acrylic adhesive, an antistatic agent, and the antistatic auxiliary agent according to claim 1. An adhesive layer containing an acrylic adhesive, an antistatic agent, and the antistatic auxiliary agent according to claim 1. An adhesive sheet formed by forming a base layer and an adhesive layer according to claim 8. A surface protection film comprising a base material layer and the adhesive layer according to claim 8. An optical film with an adhesive comprising an optical film and the adhesive layer according to claim 8. For preparing an antistatic auxiliary, the following formula (I)

(Wherein, R ¹ represents a hydrocarbon group containing an oxygen atom, a hydroxy group, or a carboxyl group,
R ² represents a hydrocarbon group, hydroxy group, carboxyl group, or hydrogen atom that may contain an oxygen atom.)
Use of compounds represented by .