WO2016122145A1 - Antistatic adhesive composition and antistatic adhesive tape using same - Google Patents

Abstract

The present invention relates to: an antistatic adhesive composition containing an acrylate resin, a reactive acrylate monomer comprising an alkylene oxide unit, and an ionic antistatic agent; and an antistatic adhesive tape using the same.

Description

Antistatic adhesive composition and antistatic adhesive tape using same

The present invention relates to an antistatic adhesive composition and an antistatic adhesive tape using the same.

Adhesive tape is a component that does not change its composition unless it is artificially moved by attaching two or more products having completely different physical properties. In other words, the adhesive tape is a material having viscoelastic properties that can be strongly adhered to a small pressure in a short time.

Typical pressure-sensitive adhesive compositions include rubber, acrylic, and silicone, among which acrylic pressure-sensitive adhesive compositions are most widely used for various application properties, and such pressure-sensitive adhesive compositions include various adhesive tapes for electronic parts, optical pressure tapes, and industrial pressure-sensitive adhesive tapes. It is widely applied in the field.

In particular, in the application of an adhesive tape for electronic components or an adhesive tape for optics, an antistatic function is required for the pressure-sensitive adhesive composition itself in order to block the generation of fundamental static electricity.

The present invention is an acrylate resin; Reactive acrylate monomers comprising alkylene oxide units; And to provide an antistatic adhesive composition comprising an ionic antistatic agent and an antistatic adhesive tape using the same.

However, the technical problem to be achieved by the present invention is not limited to the above-mentioned problem, another task that is not mentioned will be clearly understood by those skilled in the art from the following description.

The present invention is an acrylate resin; Reactive acrylate monomers comprising alkylene oxide units; And it provides an antistatic pressure-sensitive adhesive composition comprising an ionic antistatic agent.

The acrylate resin is a non-functional acrylate monomer; And it may be polymerized from a carboxyl group or a hydroxyl group containing monomer.

The weight ratio of the nonfunctional acrylate monomer and the carboxyl or hydroxy group-containing monomer may be 80:20 to 99: 1.

 The viscosity of the acrylate resin may be 2,000 cP to 20,000 cP at 25 ℃.

The reactive acrylate monomer is from the group consisting of 2- (2-ethoxyethoxy) ethyl acrylate, 2-ethoxyethyl acrylate, 2-methoxyethoxyethyl acrylate and 2-methoxyethyl methacrylate It may be one or more selected.

The ionic antistatic agent may be an organic cation or a metal cation; And anions.

25 parts by weight to 75 parts by weight of the acrylate resin, based on 100 parts by weight of the antistatic pressure-sensitive adhesive composition; 25 parts by weight to 75 parts by weight of the reactive acrylate monomer; And 0.1 parts by weight to 10 parts by weight of the ionic antistatic agent.

With respect to 100 parts by weight of the antistatic pressure-sensitive adhesive composition, it may further comprise 50 parts by weight to 500 parts by weight of the thermally conductive filler.

The thermally conductive filler may be an inorganic filler including one or more selected from the group consisting of metal oxides, metal hydroxides, metal nitrides, metal carbides, metal borides, and combinations thereof.

In one embodiment of the present invention, there is provided an antistatic adhesive tape prepared from the antistatic adhesive composition.

The surface resistance of the antistatic adhesive tape may be 1.0 × 10 ⁶ kV / □ to 1.0 × 10 ⁹ kV / □.

Antistatic pressure-sensitive adhesive composition according to the invention is an acrylate resin; Reactive acrylate monomers comprising alkylene oxide units; And by including an ionic antistatic agent, the reactive acrylate monomer can improve the ionic stability of the ionic antistatic agent.

Therefore, when the antistatic pressure-sensitive adhesive composition is cured and used as an antistatic pressure-sensitive adhesive tape, the surface resistance is very excellent.

In addition, when the antistatic adhesive composition according to the present invention further comprises a thermally conductive filler and cures it to be used as an antistatic adhesive tape, the heat dissipation effect is also excellent in a high temperature operating environment in an electronic device such as an LED due to high thermal conductivity. Do.

Hereinafter, the present invention will be described in detail.

Antistatic Adhesive Composition

The present invention is an acrylate resin; Reactive acrylate monomers comprising alkylene oxide units; And it provides an antistatic pressure-sensitive adhesive composition comprising an ionic antistatic agent.

Antistatic pressure-sensitive adhesive composition according to the invention comprises an acrylate resin, the acrylate resin is a non-functional acrylate monomer; And polymerized from a carboxyl group or a hydroxyl group-containing monomer, but is not limited thereto.

Specifically, the acrylate resin is a non-functional acrylate monomer; Carboxyl group or hydroxyl group-containing monomers; And one or more additives selected from the group consisting of photoinitiators, photocuring agents, ultraviolet stabilizers, thermal initiators, antioxidants, fillers and plasticizers.

The nonfunctional acrylate monomer may be selected from the group consisting of ethyl acrylate, butyl acrylate, ethylmethyl acrylate, propyl acrylate, 2-ethylhexyl acrylate, methyl methacrylate, ethyl methacrylate and butyl methacrylate. It may be one or more selected.

In addition, the carboxyl group-containing monomer is a monomer capable of providing a carboxyl group on the side chain or terminal of the acrylate resin after polymerization with an acrylate resin. Specifically, at least one selected from the group consisting of acrylic acid, (meth) acrylic acid, crotonic acid, maleic acid, maleic anhydride, itaconic acid, fumaric acid, cinnamic acid and acrylamide N-glycolic acid may be used as the carboxyl group-containing monomer. Acrylic acid is preferable in terms of securing a certain level or more of adhesive strength, but is not limited thereto.

The hydroxy group-containing monomer is a monomer capable of providing a hydroxy group on the side chain or terminal of the acrylate resin after polymerizing with an acrylate resin. Specifically, the hydroxy group-containing monomer is 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 4-hydroxybutyl acrylate, 5-hydroxypentyl acrylate, 6-hydroxyhexyl acrylate , At least one selected from the group consisting of 8-hydroxyoctyl acrylate and 10-hydroxydecyl acrylate can be used, and 2-hydroxyethyl acrylate can secure low resistance while having a certain level of adhesion. Preferred in that it is, but not limited to.

In this case, the weight ratio of the non-functional acrylate monomer and the carboxyl or hydroxy group-containing monomer is preferably 80:20 to 99: 1, but is not limited thereto. At this time, when the weight ratio of the non-functional acrylate monomer and the carboxyl group or hydroxy group-containing monomer is less than 80:20, there is a problem that the glass transition temperature (Tg) of the pressure-sensitive adhesive is increased to reduce the wetting at room temperature. When the weight ratio of the non-functional acrylate monomer and the carboxyl or hydroxy group-containing monomer exceeds 99: 1, there is a problem in that the cohesion of the composition worsens and the adhesion decreases.

As above, non-functional acrylate monomers; And the viscosity of the acrylate resin polymerized from the carboxyl group or the hydroxyl group-containing monomer is preferably 2,000 cP to 20,000 cP at 25 ℃, but is not limited thereto. At this time, if the viscosity of the acrylate resin is less than the above range, there is a problem that the coating is difficult to coating at an appropriate thickness because the viscosity is too low, when the viscosity of the acrylate resin exceeds the above range, the viscosity is too high when stirring causes a poor mixing There is a problem.

With respect to 100 parts by weight of the antistatic adhesive composition, the acrylate resin preferably includes 25 parts by weight to 75 parts by weight, but is not limited thereto. In this case, when the acrylate resin is included in less than 25 parts by weight, there is a problem that the appearance defects occur during coating due to failing to secure an appropriate viscosity to the coating, if the acrylate resin contains more than 75 parts by weight, There is a problem that can not secure the surface resistance value.

In addition, the antistatic pressure-sensitive adhesive composition according to the present invention includes a reactive acrylate monomer containing an alkylene oxide unit, the alkylene oxide unit may improve the ionic stability of the ionic antistatic agent.

Specifically, the alkylene oxide unit includes an ether bond, whereby non-covalent electron pairs can stabilize the organic cation or metal cation of the ionic antistatic agent on the oxygen of the ethyr bond.

The reactive acrylate monomer including the alkylene oxide unit is included separately from the acrylate resin in the form of a monomer in the antistatic pressure-sensitive adhesive composition, there is an advantage that can improve the compatibility with the ionic antistatic agent. In this case, the reactive acrylate monomer is very useful as a medium for dispersing the antistatic agent during the compounding process. For example, it is more preferable to dissolve the antistatic agent in the monomer (liquid) state than to dissolve the ionic antistatic agent in the resin (solid state) state.

The reactive acrylate monomer is from the group consisting of 2- (2-ethoxyethoxy) ethyl acrylate, 2-ethoxyethyl acrylate, 2-methoxyethoxyethyl acrylate and 2-methoxyethyl methacrylate It is preferably at least one selected, and more preferably 2- (2-ethoxyethoxy) ethyl acrylate, but is not limited thereto.

With respect to 100 parts by weight of the antistatic pressure-sensitive adhesive composition, the reactive acrylate monomer preferably includes 25 parts by weight to 75 parts by weight, but is not limited thereto. In this case, when the reactive acrylate monomer is included in less than 25 parts by weight, there is a problem that the surface resistance value of the desired level is not secured, and when the reactive acrylate monomer is included in excess of 75 parts by weight, to secure a suitable viscosity for the coating There is a problem that appearance defects occur during coating.

In addition, the antistatic pressure-sensitive adhesive composition according to the invention comprises an ionic antistatic agent, the ionic antistatic agent is an organic cation or a metal cation; And anions. That is, the ionic antistatic agent may include an organic salt or an inorganic salt, and has excellent antistatic properties.

Examples of the organic cation of the ionic antistatic agent include pyridinium cation, piperidinium cation, pyrrolidinium cation, cation having a pyrroline skeleton, cation having a pyrrole skeleton, imidazolium cation, tetrahydropyrimidinium cation, and di Hydropyrimidinium cation, pyrazolium cation, pyrazolinium cation, and a tetraalkylammonium cation, trialkylsulfonium cation, tetraalkylphosphonium cation, and a cation in which some of their alkyl groups are substituted with alkenyl, alkoxyl or epoxy groups Etc. can be mentioned. Among them, tetraalkylammonium cation is preferred in terms of compatibility, but is not limited thereto.

Specific examples of the pyridinium cation include 1-ethylpyridinium, 1-butylpyridinium, 1-hexylpyridinium, 1-butyl-3-methylpyridinium, 1-butyl-4-methylpyridinium, 1- Hexyl-3-methylpyridinium, 1-butyl-3,4-dimethylpyridinium, 1-octyl-4-methylpyridinium cation and the like.

Specific examples of the pyrrolidinium cation include 1,1-dimethylpyrrolidinium, 1-ethyl-1-methylpyrrolidinium, 1-methyl-1-propylpyrrolidinium cation and the like.

Specific examples of the cation having a pyrroline skeleton include 2-methyl-1-pyrroline cation, and specific examples of the cation having the pyrroline skeleton include 1-ethyl-2-phenylindole and 1,2-dimethylindole. And 1-ethylcarbazole cation.

Specific examples of the imidazolium cation include 1,3-dimethylimidazolium, 1,3-diethylimidazolium, 1-ethyl-3-methylimidazolium, 1-butyl-3-methylimidazolium , 1-hexyl-3-methylimidazolium, 1-octyl-3-methylimidazolium, 1-decyl-3-methylimidazolium, 1-dodecyl-3-methylimidazolium, 1-tetradecyl 3-methylimidazolium, 1,2-dimethyl-3-propylimidazolium, 1-ethyl-2,3-dimethylimidazolium, 1-butyl-2,3-dimethylimidazolium, 1-hexyl -2,3-dimethylimidazolium cation etc. are mentioned.

Specific examples of the tetrahydropyrimidinium cation include 1,3-dimethyl-1,4,5,6-tetrahydropyrimidinium, 1,2,3-trimethyl-1,4,5,6-tetrahydro Pyrimidinium, 1,2,3,4-tetramethyl-1,4,5,6-tetrahydropyrimidinium, 1,2,3,5-tetramethyl-1,4,5,6-tetrahydro Pyrimidinium cation etc. are mentioned.

Specific examples of the dihydropyrimidinium cation include 1,3-dimethyl-1,4-dihydropyrimidinium, 1,3-dimethyl-1,6-dihydropyrimidinium, and 1,2,3- Trimethyl-1,4-dihydropyrimidinium, 1,2,3-trimethyl-1,6-dihydropyrimidinium, 1,2,3,4-tetramethyl-1,4-dihydropyrimidinium And 1,2,3,4-tetramethyl-1,6-dihydropyrimidinium cation.

Specific examples of the pyrazolium cation include 1-methylpyrazolium, 3-methylpyrazolium cation, and the like, and specific examples of the pyrazolium cation include 1-ethyl-2-methylpyrazolium cation. .

Specific examples of the tetraalkylammonium cation include tetramethylammonium, tetraethylammonium, tetrapropylammonium, tetrabutylammonium, tetrapentylammonium, tetrahexylammonium, tetraheptylammonium, triethylmethylammonium, tributylethylammonium and trimethyldecyl Ammonium, Trioctylmethylammonium, Tripentylbutylammonium, Trihexylmethylammonium, Trihexylpentylammonium, Triheptylmethylammonium, Tripentylbutylammonium, Triheptylhexylammonium, Dimethyldihexylammonium, Dipropyldihexylammonium, Heptyldimethyl Hexylammonium, N, N-diethyl-N-methyl-N- (2-methoxyethyl) ammonium, glycidyltrimethylammonium, N, N-dimethyl-N-ethyl-N-propylammonium, N, N- Dimethyl-N-ethyl-N-butylammonium, N, N-dimethyl-N-ethyl-N-pentylammonium, N, N-dimethyl-N-ethyl-N-hexylammonium, N, N-dimethyl-N-ethyl -N-heptylammonium, N, N-dimethyl-N-ethyl-N-nonylammonium, N, N-dimethyl-N- Lofil-N-butylammonium, N, N-dimethyl-N-propyl-N-pentylammonium, N, N-dimethyl-N-propyl-N-hexylammonium, N, N-dimethyl-N-propyl-N-heptyl Ammonium, N, N-dimethyl-N-butyl-N-hexylammonium, N, N-dimethyl-N-butyl-N-heptylammonium, N, N-dimethyl-N-pentyl-N-hexylammonium, trimethylheptylammonium , N, N-diethyl-N-methyl-N-propylammonium, N, N-diethyl-N-methyl-N-pentylammonium, N, N-diethyl-N-methyl-N-heptylammonium, N , N-diethyl-N-propyl-N-pentylammonium, triethylmethylammonium, triethylpropylammonium, triethylpentylammonium, triethylheptylammonium, N, N-dipropyl-N-methyl-N-ethylammonium , N, N-dipropyl-N-methyl-N-pentylammonium, N, N-dipropyl-N-butyl-N-hexylammonium, N, N-dibutyl-N-methyl-N-pentylammonium, N , N-dibutyl-N-methyl-N-hexylammonium, trioctylmethylammonium, N-methyl-N-ethyl-N-propyl-N-pentylammonium cation, etc. are mentioned.

Specific examples of the trialkylsulfonium cation include trimethylsulfonium, triethylsulfonium, tributylsulfonium, trihexylsulfonium, diethylmethylsulfonium, dibutylethylsulfonium, and dimethyldecylsulfonium cation. Can be.

Specific examples of the tetraylalkylphosphonium cation include tetramethylphosphonium, tetraethylphosphonium, tetrabutylphosphonium, tetrapentylphosphonium, tetrahexylphosphonium, tetraheptylphosphonium, tetraoctylphosphonium and triethylmethyl Phosphonium, tributylethylphosphonium, trimethyldecylphosphonium cation, and the like.

Examples of the metal cation of the ionic antistatic agent include alkali metals, alkaline earth metals, group 13 elements, group 14 elements, group 15 elements, transition metals, and rare earth elements. Among them, lithium (Li) cation is preferred in terms of compatibility, but is not limited thereto.

Anions of the ionic antistatic agent include bis (trifluoromethanesulfonyl) imide, tetrafluoroborate, hexafluorophosphate, bis (pentafluoroethanesulfonyl) imide, perfluorobutanesulfonate , Heptafluorophosphate, (trifluoromethanesulfonyl) trifluoroacetamide, and the like. Of these, bis (trifluoromethanesulfonyl) imide is preferred in terms of compatibility, but is not limited thereto.

With respect to 100 parts by weight of the antistatic pressure-sensitive adhesive composition, the ionic antistatic agent preferably comprises 0.1 parts by weight to 10 parts by weight, but is not limited thereto. At this time, when the ionic antistatic agent contains less than 0.1 parts by weight, there is a problem that does not obtain sufficient antistatic properties, when the ionic antistatic agent contains more than 10 parts by weight, the adhesive force is lowered, or durability is lowered There is a problem.

In addition, the antistatic adhesive composition according to the present invention may further include 50 parts by weight to 300 parts by weight of the thermally conductive filler. The thermally conductive filler may be an inorganic filler including at least one selected from the group consisting of metal oxides, metal hydroxides, metal nitrides, metal carbides, metal borides, and combinations thereof to reduce thermal deformation (shrinkage or expansion) at high temperatures. Can be. At this time, since the thermally conductive filler maintains the above range, the antistatic adhesive tape prepared from the antistatic adhesive composition may have a high thermal conductivity for realizing a heat dissipation effect, for the electronic component for bonding or processing between electronic components It is useful as an antistatic adhesive tape.

That is, the antistatic adhesive composition may further include a thermally conductive filler to increase thermal conductivity so that heat dissipation may be imparted, and the thermal conductivity of the antistatic adhesive tape prepared from the antistatic adhesive composition is 0.3 to 0.8 W. / mK. For example, the thermal conductivity of the antistatic adhesive tape prepared from the antistatic adhesive composition may be about 0.5 to about 1.0 W / mK. Antistatic adhesive tape implemented to have a thermal conductivity of the above range is also excellent heat dissipation effect in a high temperature operating environment in an electronic device such as LED.

In addition, the thermally conductive filler may impart flame retardancy with high thermal conductivity. In particular, by using an inorganic system such as magnesium hydroxide or aluminum hydroxide among the thermally conductive fillers, an endothermic reaction that absorbs energy during the reaction may generate H ₂ O and CO ₂ , which are incombustible materials, thereby exerting a physical flame retardant effect.

The thermally conductive filler may have an average particle diameter of about 1 μm to about 200 μm, specifically about 10 μm to about 180 μm. Since the average particle diameter of the thermally conductive filler maintains the above range, the antistatic adhesive tape prepared from the antistatic adhesive composition may have a high thermal conductivity for implementing a heat dissipation effect.

The thermally conductive filler may be, for example, an inorganic thermally conductive filler including at least one selected from the group consisting of metal oxides, metal hydroxides, metal nitrides, metal carbides, metal borides, and combinations thereof. Specifically, the inorganic thermal conductive filler may include aluminum oxide, magnesium oxide, zinc oxide, silicon carbide, aluminum nitride, boron nitride, silicon nitride, aluminum hydroxide, magnesium hydroxide, silicon oxide, and the like.

More specifically, in the case of using aluminum hydroxide or magnesium hydroxide as the thermally conductive inorganic filler, the amount of smoke generated during combustion of the antistatic pressure-sensitive adhesive composition is very small, which is advantageous in terms of environment, and excellent flame retardancy can be ensured. The aluminum hydroxide is suitable when the processing temperature of the pressure-sensitive adhesive composition is low because the decomposition temperature is low as about 200 ℃, when the processing temperature is high, the magnesium hydroxide can be used relatively high decomposition temperature of about 320 ℃. Furthermore, the magnesium hydroxide can ensure excellent flame retardancy even when the addition amount is small when using nano-sized particles.

The antistatic pressure sensitive adhesive composition according to the present invention may further include one or more additives selected from the group consisting of photoinitiators, photocuring agents, ultraviolet stabilizers, thermal initiators, antioxidants, fillers and plasticizers. The additive may be appropriately adjusted within a range that does not impair the physical properties of the antistatic pressure-sensitive adhesive composition, it is possible to further include additives such as pigments, ultraviolet stabilizers, dispersants, antifoaming agents, thickeners, plasticizers, brighteners.

Antistatic Adhesive Tape

In addition, the present invention provides an antistatic pressure-sensitive adhesive tape prepared from the antistatic pressure-sensitive adhesive composition.

That is, the antistatic adhesive tape can secure the coating film stability through the curing of the antistatic adhesive composition, wherein the curing of the antistatic adhesive composition, heat, ultraviolet light, visible light, infrared radiation, and electron beam radiation It can be carried out using an energy source selected from the group consisting of.

The antistatic adhesive tape may be used as an adhesive tape for electronic components or an adhesive tape for optics.

The antistatic adhesive tape has a very excellent surface resistance. Specifically, the surface resistance of the antistatic adhesive tape is preferably 1.0 × 10 ⁶ Ω / □ to 1.0 × 10 ⁹ Ω / □, but is not limited thereto. Do not. At this time, if the surface resistance of the antistatic adhesive tape is less than 1.0 × 10 ⁶ Ω / □, it may cause malfunction when applied to display devices such as CRT (Cathod Ray Tube), LCD (Liquid Crystal Display), PDP (Plasma Display Panel), etc. In the case of exceeding 1.0 × 10 ⁹ Ω / □, there is a problem of dust adhesion to the electronic component due to the deterioration of the antistatic performance and the rupture and deterioration of the component due to ESD discharge.

In order to use the antistatic adhesive tape as an adhesive tape for electronic components for bonding or processing between electronic components, the above-mentioned thermally conductive filler is further included in the antistatic adhesive composition. It is desirable to increase the thermal conductivity so that a heat dissipation function can be given. Thus, the thermal conductivity of the antistatic adhesive tape may be 0.3 to 0.8 W / mK, preferably 0.5 to 0.8 W / mK.

The antistatic adhesive tape may be used as an optical adhesive tape. In order to use the antistatic adhesive tape as an optical adhesive tape, transparency must be maintained, and it is preferable not to further include the above-described thermally conductive filler. For example, the antistatic adhesive tape may be formed on one side or both sides of the polarizing film. The polarizing film may be made of a material such as polypropylene resin, polyethylene resin, polyamide resin, polyester resin, polyacrylic resin, polyvinyl chloride resin, polycarbonate resin, polyvinyl chloride resin, polyurethane resin, or the like. It may be formed as, but is not limited thereto.

As described above, the antistatic adhesive composition according to the present invention is an acrylate resin; Reactive acrylate monomers comprising alkylene oxide units; And by including an ionic antistatic agent, the reactive acrylate monomer can improve the ionic stability of the ionic antistatic agent.

Therefore, when the antistatic pressure-sensitive adhesive composition is cured and used as an antistatic pressure-sensitive adhesive tape, the surface resistance is very excellent.

In addition, when the antistatic adhesive composition according to the present invention further comprises a thermally conductive filler and cures it to be used as an antistatic adhesive tape, the heat dissipation effect is also excellent in a high temperature operating environment in an electronic device such as an LED due to high thermal conductivity. Do.

Hereinafter, preferred examples are provided to aid in understanding the present invention. However, the following examples are merely provided to more easily understand the present invention, and the contents of the present invention are not limited by the following examples.

EXAMPLE

Example 1

In 1 L of the glass reactor, 96 parts by weight of 2-ethylhexyl acrylate, 4 parts by weight of acrylic acid and 0.05 parts by weight of Irgacure # 651 as a photoinitiator were photopolymerized to prepare an acrylate resin having a viscosity of 10,000 cP at 25 ° C.

200 parts by weight of 2- (2-ethoxyethoxy) ethyl acrylate, 100 parts by weight of Irgacure # 651 as a photoinitiator and 0.1 part by weight of 1,6-hexanediol diacrylate as a photocrosslinker After addition and sufficient stirring, 2 parts by weight of tributylmethylammonium bis (trifluoromethanesulfonyl) imide was added and sufficiently stirred to prepare an antistatic pressure-sensitive adhesive composition.

After degassing the prepared antistatic pressure-sensitive adhesive composition with a vacuum pump, it was coated with a knife coating on the PET film to a thickness of 150㎛, after laminating a PET film on the coated antistatic pressure-sensitive adhesive composition to block oxygen An antistatic adhesive tape was prepared by curing for 3 minutes using a black fluorescent lamp.

Example 2

An acrylate resin having a viscosity of 10,000 cP at 25 ° C. was prepared by photopolymerizing 80 parts by weight of 2-ethylhexyl acrylate, 20 parts by weight of 2-hydroxyethyl acrylate and 0.05 parts by weight of Irgacure # 651 as a photoinitiator in a 1 L glass reactor.

100 parts by weight of 2- (2-ethoxyethoxy) ethyl acrylate, 100 parts by weight of Irgacure # 651 as a photoinitiator and 0.1 part by weight of 1,6-hexanediol diacrylate as a photocrosslinker After adding and stirring sufficiently, 2.0 parts by weight of tributylmethylammonium bis (trifluoromethanesulfonyl) imide was added and stirred sufficiently to prepare an antistatic pressure-sensitive adhesive composition, in the same manner as in Example 1 An anti-stick tape was prepared.

Example 3

Except that 1.0 parts by weight of lithium bis (trifluoromethanesulfonyl) imide was added instead of 2.0 parts by weight of tributylmethylammonium bis (trifluoromethanesulfonyl) imide and sufficiently stirred to prepare an antistatic pressure-sensitive adhesive composition. , An antistatic adhesive tape was prepared in the same manner as in Example 1.

Example 4

An antistatic adhesive tape was prepared in the same manner as in Example 1, except that 450 parts by weight of aluminum hydroxide powder (H-100, Showa Denko) having an average particle diameter of 100 μm was further added.

Comparative Example 1

It carried out similarly to Example 1 except not adding 200 weight part of 2- (2-ethoxyethoxy) ethyl acrylate.

Comparative Example 2

It carried out similarly to Example 2 except not adding 100 weight part of 2- (2-ethoxyethoxy) ethyl acrylate.

Comparative Example 3

The same procedure as in Comparative Example 1 was performed except that 1.0 part by weight of 1-ethyl-3-methylimidazolium tetrafluoroborate was added instead of 1.0 part by weight of tributylmethylammonium bis (trifluoromethanesulfonyl) imide. .

Comparative Example 4

In the same manner as in Comparative Example 1, except that 1.0 part by weight of tetrabutylphosphonium bis (trifluoromethanesulfonyl) imide was added instead of 1.0 part by weight of tributylmethylammonium bis (trifluoromethanesulfonyl) imide. It was.

Comparative Example 5

The same procedure as in Comparative Example 2 was performed except that 1.0 part by weight of 1-ethyl-3-methylimidazolium tetrafluoroborate was added instead of 2.0 parts by weight of tributylmethylammonium bis (trifluoromethanesulfonyl) imide. .

Comparative Example 6

In the same manner as in Comparative Example 2, except that 1.0 part by weight of tetrabutylphosphonium bis (trifluoromethanesulfonyl) imide was added instead of 2.0 parts by weight of tributylmethylammonium bis (trifluoromethanesulfonyl) imide. It was.

	Acrylate resin (parts by weight)	Reactive acrylate monomer (parts by weight)	Photoinitiator (parts by weight)	Optical crosslinking agent (parts by weight)	Ionic Antistatic Agent (parts by weight)	Thermally conductive filler (parts by weight)
Example 1	2-EHA 96 / AA 4	EOEOEA 200	Irgacure # 651 0.2	HDDA 0.1	TBMA-TFSI 2.0	-
Example 2	2-EHA 80 / HEA 20	EOEOEA 100	Irgacure # 651 0.2	HDDA 0.1	TBMA-TFSI 2.0	-
Example 3	2-EHA 96 / AA 4	EOEOEA 200	Irgacure # 651 0.2	HDDA 0.1	Li-TFSI 1.0	-
Example 4	2-EHA 96 / AA 4	EOEOEA 200	Irgacure # 651 0.2	HDDA 0.1	TBMA-TFSI 2.0	Al (OH) 3 450
Comparative Example 1	2-EHA 96 / AA 4	-	Irgacure # 651 0.2	HDDA 0.1	TBMA-TFSI 1.0	-
Comparative Example 2	2-EHA 80 / HEA 20	-	Irgacure # 651 0.2	HDDA 0.1	TBMA-TFSI 2.0	-
Comparative Example 3	2-EHA 96 / AA 4	-	Irgacure # 651 0.2	HDDA 0.1	EMIM-BF4 1.0	-
Comparative Example 4	2-EHA 96 / AA 4	-	Irgacure # 651 0.2	HDDA 0.1	TBP-TFSI 1.0	-
Comparative Example 5	2-EHA 80 / HEA 20	-	Irgacure # 651 0.2	HDDA 0.1	EMIM-BF4 1.0	-
Comparative Example 6	2-EHA 80 / HEA 20	-	Irgacure # 651 0.2	HDDA 0.1	TBP-TFSI 1.0	-

2-EHA 2-ethylhexyl acrylate

* AA: acrylic acid

2-HEA: 2-hydroxyethyl acrylate

* EOEOEA: 2- (2-ethoxyethoxy) ethyl acrylate

TBMA-TFSI: tributylmethylammonium bis (trifluoromethanesulfonyl) imide

Li-TFSI: lithium bis (trifluoromethanesulfonyl) imide

EMIM-BF4: 1-ethyl-3-methylimidazolium tetrafluoroborate

* TBP-TFSI: tetrabutylphosphonium bis (trifluoromethanesulfonyl) imide

Experimental Example 1: Measurement of Surface Resistance

Surface resistance of the antistatic coating layer according to Examples 1 to 4 and Comparative Examples 1 to 6 after peeling the PET film laminated on the coated antistatic adhesive composition, the surface resistance measuring instrument (MCP-HT450, MITSUBISHI CHEMICAL) and the probe After 10 seconds under the applied voltage of 100 ~ 500V (URS, UR100) was measured 10 times the surface resistance (Ω / □) was repeated 10 times, the average value is shown in Table 2 below.

Experimental Example 2: Measurement of Thermal Conductivity

The thermal conductivity of the antistatic coating layer according to Examples 1 to 4 and Comparative Examples 1 to 6 was cut into antistatic coating layers of 60 mm x 120 mm, respectively, and then using the quick thermal conductivity meter QTM-500 manufactured by Kyoto Electronics Co., Ltd. The measured values are shown in Table 2 below.

	Surface resistance (Ω / □)	Thermal Conductivity (W / mK)
Example 1	6.35 × 10 8	0.31-0.33
Example 2	2.30 × 10 8	0.31-0.33
Example 3	1.85 × 10 8	0.31-0.33
Example 4	9.29 × 10 8	0.54
Comparative Example 1	7.39 × 10 11	0.31-0.33
Comparative Example 2	8.23 × 10 10	0.31-0.33
Comparative Example 3	5.23 × 10 13	0.31-0.33
Comparative Example 4	9.31 × 10 11	0.31-0.33
Comparative Example 5	3.19 × 10 11	0.31-0.33
Comparative Example 6	8.84 × 10 11	0.31-0.33

As shown in Table 2, the antistatic adhesive tape according to Examples 1 to 4 was confirmed to have an excellent surface resistance of 1.85 × 10 ⁸ Ω / □ to 9.29 × 10 ⁸ Ω / □.

In particular, the antistatic adhesive tape according to Example 4 was found to be particularly excellent in thermal conductivity of 0.54 W / mK due to the addition of a thermally conductive filler.

The foregoing description of the present invention is intended for illustration, and it will be understood by those skilled in the art that the present invention may be easily modified in other specific forms without changing the technical spirit or essential features of the present invention. will be. Therefore, it should be understood that the embodiments described above are exemplary in all respects and not restrictive.

Claims (11)

1. Acrylate resins;

   Reactive acrylate monomers comprising alkylene oxide units; And

   Containing ionic antistatic agents

   Antistatic pressure-sensitive adhesive composition.
2. The method of claim 1,

   The acrylate resin is a non-functional acrylate monomer; And polymerized from a carboxyl group or a hydroxyl group-containing monomer.

   Antistatic pressure-sensitive adhesive composition.
3. The method of claim 2,

   The weight ratio of the non-functional acrylate monomer and the carboxyl or hydroxy group-containing monomer is 80:20 to 99: 1

    Antistatic pressure-sensitive adhesive composition.
4. The method of claim 1,

   The viscosity of the acrylate resin is 2,000 cP to 20,000 cP at 25 ℃

   Antistatic pressure-sensitive adhesive composition.
5. The method of claim 1,

   The reactive acrylate monomer is from the group consisting of 2- (2-ethoxyethoxy) ethyl acrylate, 2-ethoxyethyl acrylate, 2-methoxyethoxyethyl acrylate and 2-methoxyethyl methacrylate One or more selected

   Antistatic pressure-sensitive adhesive composition.
6. The method of claim 1,

   The ionic antistatic agent may be an organic cation or a metal cation; And anions

   Antistatic pressure-sensitive adhesive composition.
7. The method of claim 1,

   25 parts by weight to 75 parts by weight of the acrylate resin, based on 100 parts by weight of the antistatic pressure-sensitive adhesive composition; 25 parts by weight to 75 parts by weight of the reactive acrylate monomer; And 0.1 parts by weight to 10 parts by weight of the ionic antistatic agent.

   Antistatic pressure-sensitive adhesive composition.
8. The method of claim 1,

   Based on 100 parts by weight of the antistatic pressure-sensitive adhesive composition, further comprising 50 parts by weight to 500 parts by weight of the thermally conductive filler

   Antistatic pressure-sensitive adhesive composition.
9. The method of claim 8,

   The thermally conductive filler is an inorganic filler including at least one selected from the group consisting of metal oxides, metal hydroxides, metal nitrides, metal carbides, metal borides, and combinations thereof.

   Antistatic pressure-sensitive adhesive composition.
10. An antistatic adhesive tape prepared from the antistatic adhesive composition according to any one of claims 1 to 9.
11. The method of claim 10,

    The surface resistance of the antistatic adhesive tape is 1.0 × 10 ⁶ Ω / □ to 1.0 × 10 ⁹ Ω / □

    Antistatic adhesive tape.