KR20110064979A - Acrylate-adhesive resin composition, photocurable removable adhesive composition comprising the same and adhesive tape comprising the same - Google Patents

Abstract

PURPOSE: An acrylate-adhesive resin composition is provided to obtain a photocurable removable adhesive composition with high initial adhesive property, no foreign substances or residues, and low releasability. CONSTITUTION: An acrylate-adhesive resin composition comprises, based on 100.0 parts by weight of an adhesive acrylic binder resin, 1-30 parts by weight of (meth)acrylic acids and 1-30 parts by weight of dicarboxylic anhydrides. The adhesive acrylic binder resin includes 70-98 parts by weight of (meth)acrylic acid ester monomers having a C1-14 alkyl group and 2-30 parts by weight of (meth)acrylic acid monomers having a glycidyl functional group. The photocurable removable adhesive composition comprises the acrylate-adhesive resin composition, hardener and photoinitiator.

Description

Acrylate-Adhesive Resin Composition, Photocurable Removable Adhesive Composition Comprising the Same and Adhesive Tape Comprising the Same}

Embodiments of the present invention relate to an acrylic adhesive resin composition, a photocurable re-peelable adhesive resin composition comprising the same, and an adhesive tape including the same.

In the semiconductor manufacturing process, a dicing process is a process of individually shearing wafers using a blade to separate the semiconductor chips, which are individual devices, at a wafer level having a constant diameter.

A semiconductor wafer of silicon or gallium arsenide is manufactured in a disk shape having a certain diameter, and the wafer is cut / diced into small chips and then mounted in a lead frame. In this process, the semiconductor wafer is cut, washed, dried, picked up and adhered to the adhesive tape and transferred to the mounting process. The adhesive tape is a tape attached to the back side of the wafer to prevent the semiconductor chip from protruding or shaking in the process of cutting the semiconductor. The adhesive tape includes an adhesive composition, and the adhesive composition is an adhesive component exhibiting adhesive force.

The adhesive tape including the adhesive composition has a constant adhesive force to prevent chip shaking and scattering during wafer cutting, and when picking up the cut chips, each chip is easily reduced due to a rapid decrease in adhesive force due to ultraviolet irradiation. Functional tape to separate from the adhesive tape.

Therefore, the adhesive tape should have a constant adhesive force before the ultraviolet irradiation, and after the ultraviolet irradiation, the adhesive force is reduced to peel off the chip while leaving no adhesive on the chip. Therefore, in the case of the adhesive composition used for the dicing tape, it is important to satisfy the above requirements.

Therefore, there has been a need to develop a photocurable repeelable pressure-sensitive adhesive composition and a photocurable repeelable pressure-sensitive adhesive tape including the same, which have superior re-peelability and high adhesion due to excellent photocuring properties when photocuring.

Embodiments of the present invention have a high initial adhesive force and a photocurable re-peelable adhesive resin composition comprising an acrylic adhesive resin composition having a low peeling force when there is no foreign matter or residue when photocuring to solve the above problems and the adhesive comprising the same Provide a tape.

Embodiments of the present invention 100 weight of the adhesive acrylic binder resin containing 70 to 98 parts by weight of (meth) acrylic acid ester monomer having an alkyl group of 1 to 14 carbon atoms, 2 to 30 parts by weight of (meth) acrylic acid monomer having a glycidyl functional group About wealth,

 It provides an acrylic adhesive resin composition comprising 1 to 30 parts by weight of (meth) acrylic acid and 1 to 30 parts by weight of dicarboxylic acid anhydride.

In addition, an embodiment of the present invention provides a photo-curable re-peelable adhesive resin composition comprising the acrylic adhesive resin composition, comprising a curing agent and a photoinitiator.

In addition, embodiments of the present invention provides a pressure-sensitive adhesive tape comprising a photocurable re-peelable pressure-sensitive adhesive composition.

According to embodiments of the present invention, a photocurable re-peelable adhesive resin composition comprising an acrylic adhesive resin composition having a high initial adhesive strength and no foreign matter or residue upon photocuring and a low peeling force is obtained, and an adhesive tape including the same. .

Embodiments of the present invention 100 weight of the adhesive acrylic binder resin containing 70 to 98 parts by weight of (meth) acrylic acid ester monomer having an alkyl group of 1 to 14 carbon atoms, 2 to 30 parts by weight of (meth) acrylic acid monomer having a glycidyl functional group About wealth,

 It provides an acrylic adhesive resin composition comprising 1 to 30 parts by weight of (meth) acrylic acid and 1 to 30 parts by weight of dicarboxylic acid anhydride.

The (meth) acrylic acid and dicarboxylic acid anhydride are those polymerized by addition to the glycidyl functional group of the adhesive acrylic binder resin.

The adhesive resin composition in which (meth) acrylic acid is added and reacted with a conventional acrylic adhesive resin has a chemical reaction of two functional groups when copolymerizing (meth) acrylate including a glycidyl functional group and an acrylate including a carboxyl functional group simultaneously. Although it is difficult to give a carboxyl functional group which has a great influence on the adhesive force because it is formed, it is difficult to obtain an adhesive resin composition having a high adhesive strength, but the carboxyl functional group is imparted in the adhesive resin composition by sequentially reacting (meth) acrylic acid and dicarboxylic anhydride. It is possible to obtain a high pressure-sensitive adhesive composition as a result.

The acrylic adhesive resin composition has a weight average molecular weight of 300,000 to 1,500,000, an acid value of 2 to 100, (meth) acryloyl functional equivalent 400 to 6000g / eq. Or 1000 to 2000 g / eq. to be.

If the molecular weight is less than 300,000, the retention force of the adhesive resin is low, the transition occurs in the base film, if it is more than 1,500,000 it is difficult to obtain the desired level of adhesion. Functional equivalent 400 g / eq. In order to achieve the objective, when glycidyl (meth) acrylate is excessively used during polymerization, it is difficult to function as an adhesive resin, and it is 6000 g / eq. If it is above, the hardening density at the time of photocuring will be low, and peeling force will become high. The glass transition temperature is -80 ℃ to -10 ℃ or -60 ℃ to -40 ℃, if the glass transition temperature is -10 ℃ or more, the initial adhesive strength is low and the adhesion to the adhesive is poor, the defect occurs, below -80 ℃ Is difficult to achieve with the above material conditions.

The (meth) acrylic acid ester monomer has an alkyl group having 1 to 14 carbon atoms, but is not limited thereto. Examples thereof include 2-ethylhexyl (meth) acrylate, butyl (meth) acrylate, lauryl (meth) acrylate, and t-. Butyl (meth) acrylate, n-octyl (meth) acrylate, ethyl (meth) acrylate, methyl (meth) acrylate, n-propyl (meth) acrylate, iso-butyl (meth) acrylate and iso- It contains at least one selected from the group consisting of propyl (meth) acrylate, it is preferred to use 2-ethylhexyl (meth) acrylate and butyl (meth) acrylate.

This serves to maintain the adhesion by controlling the glass transition temperature of the acrylic adhesive resin composition. 70 to 98 parts by weight, 75 to 95 parts by weight or 80 to 90 parts by weight is appropriate, and when the amount is more than 98 parts by weight, the amount of functional groups to be introduced in the addition polymerization reaction process becomes smaller, and re-peeling becomes difficult, and 70 parts by weight. If less than, it is difficult to control the glass transition temperature, it is difficult to obtain a high adhesion.

A (meth) acrylic acid monomer having a glycidyl functional group is a raw material used to introduce a carboxyl functional group and an acryloyl functional group in an addition polymerization reaction process, in the group consisting of glycidyl acrylate and glycidyl methacrylate. Any one or more selected may be used. Its amount is 2 to 30 parts by weight, 5 to 25 parts by weight or 10 to 20 parts by weight is appropriate, if the glass transition temperature of the acrylic adhesive resin composition is too high to obtain a high adhesive strength, less than 2 parts by weight of addition polymerization Introduced amount of acryloyl and carboxyl functional groups in the reaction step is small, it is difficult to obtain the desired adhesion and photocurable re-peeling properties.

The addition polymerization reaction in the process for obtaining the acrylic adhesive resin composition according to an embodiment of the present invention adds 1 to 30 parts by weight of (meth) acrylic acid and 1 to 30 parts by weight of dicarboxylic anhydride based on 100 parts by weight of the adhesive acrylic binder resin. To react.

In this case, any conventional addition polymerization method may be used without limitation, but a copolymer of 70 to 98 parts by weight of a (meth) acrylic acid ester monomer having an alkyl group having 1 to 14 carbon atoms and 2 to 30 parts by weight of a (meth) acrylic acid monomer having a glycidyl functional group In the group consisting of 4-tert-butylpyrocatechol, 4-tert-butylpyrocatechol, hydroquinone, methoxy hydroquinone, and butyl hydrotoluene, but not limited thereto. 0.01 to 0.5 parts by weight of any one or more selected from the group consisting of triphenylphosphite, triethylamine and dimethylaminopyridine, but not limited to 0.01 to 0.5 parts by weight of an addition reaction catalyst 8 to 24 hours, 12 to 18 hours at 80 to 150 ° C or 90 to 120 ° C You can use the method of reacting.

The (meth) acrylic acid added to the glycidyl functional group of the adhesive acrylic binder resin cures the acrylic adhesive resin during photocuring, thereby imparting photocurable re-peeling properties, and the amount used is 100 parts by weight of the adhesive acrylic binder resin. 1 to 30 parts by weight, 5 to 20 parts by weight or 8 to 15 parts by weight can be used. If it exceeds 30 parts by weight, the amount of dicarboxylic acid to be introduced is relatively low, the adhesion is lowered, if less than 1 part by weight may leave a residue after photocuring.

In addition, the dicarboxylic anhydride added to the glycidyl functional group of the adhesive acrylic binder resin serves to increase the adhesive force by imparting a carboxylic acid functional group to the adhesive acrylic binder resin. As the dicarboxylic anhydride, one or more selected from the group consisting of maleic anhydride, itaconic anhydride, amber anhydride, phthalic anhydride, phthalic anhydride, and tetrahydrophthalic anhydride may be used, and the amount of the dicarboxylic anhydride may be used as the adhesive acrylic binder resin. 1 to 30 parts by weight, 5 to 20 parts by weight or 8 to 15 parts by weight relative to 100 parts by weight may be used. When the amount exceeds 30 parts by weight, the amount of acryloyl functional group to be introduced is relatively reduced, so that the residue is easily left after photocuring, and the viscosity is excessively increased, and when less than 1 part by weight, high adhesion is difficult to obtain.

In addition, an embodiment of the present invention provides a photocurable re-peelable adhesive resin composition comprising the acrylic adhesive resin composition and comprising a curing agent and a photoinitiator.

The photocurable re-peelable adhesive composition refers to an adhesive resin composition which can be re-peeled only by photocuring, compared to an existing re-peelable adhesive resin composition, which is an adhesive resin composition capable of always re-peeling.

The curing agent may use any one or more selected from the group consisting of 1 to 20 parts by weight of the photocurable urethane acrylic oligomer curing agent and 1 to 5 parts by weight of the thermosetting isocyanate curing agent relative to 100 parts by weight of the acrylic adhesive resin composition.

As the photocurable urethane acrylic oligomer curing agent, a urethane acrylate oligomer including a tetrafunctional or higher acryloyl functional group may be used. Examples include, but are not limited to, UA-306H, UV-306I, UV-306T, and UV of Japanese public corporations. One or more selected from the group consisting of -510H and SK Cytec's EB1290, EB8405, EB220, and the like can be used. The amount used is 1 to 20 parts by weight based on 100 parts by weight of the acrylic adhesive resin composition, but when used less than 1 part by weight, the curing strength is low due to the low curing density during photocuring, and contamination of the adherend occurs, and 20 parts by weight or more. In the case of use, the adhesive strength becomes low.

Thermosetting isocyanate curing agents include, but are not limited to, isophorone diisocyanate, hexamethylene diisocyanate, toluene diisocyanate, methylene diphenyl diisocyanate, hydrogenated toluene diisocyanate, xylene diisocyanate, 1,3-bisisocyanate methylcyclo Monomer types, such as hexane, tetramethyl xylene diisocyanate, 1, 5- naphthalene diisocyanate, 2, 2, 4- trimethyl hexamethylene diisocyanate, 2, 4, 4- trimethyl hexamethylene diisocyanate, the said isocyanate hardener group etc. 3,5-dimethylpyrazole (3,5-dimethyl) according to trimethylolpropane duct type, biuret type such as the isocyanate curing agent group, tolonate type such as the isocyanate curing agent group and each isocyanate curing agent group type pyrazole, DMP) block type, diethyl As may be used to carbonate (diethyl Malonate, DDM) block type, methyl ethyl Kane oxime (methylethyl keoxime, MEKO) block type, caproic raktan (caprolactan, ε-CAP) at least one selected from the group consisting of a block type and the like. The amount used is 0.1 to 5 parts by weight based on 100 parts by weight of the acrylic adhesive resin composition, but when used less than 0.1 parts by weight, the adhesive strength is lowered when using less than 0.1 parts by weight, and when using 5 parts by weight or more.

The photoinitiator preferably has a pyrolysis temperature of 120 ° C. or higher, and examples thereof include, but are not limited to, alpha-hydroxy ketone type compounds, benzyl ketal type compounds, alpha-amino ketone type compounds, acrylic phosphine type compounds, and metallocene types. Any one or more selected from the group consisting of compounds may be used. The amount used is 1 to 10 parts by weight based on 100 parts by weight of the acrylic adhesive resin composition, but when used less than 1 part by weight, the curing density is lowered and the peeling force is increased after the photocuring, and when it is 10 parts by weight or more, the unreacted residual initiator during the photocuring is used. Causes irritating odors and pollutes the working environment.

In addition, one embodiment of the present invention provides a pressure-sensitive adhesive tape comprising a photocurable re-peelable pressure-sensitive adhesive composition.

The adhesive tape may be prepared by a conventional method and is prepared by applying and curing the photocurable re-peelable adhesive resin composition on one or both sides of the substrate.

The substrate may be a film of rayon, acetate, vinyl chloride, polyester, acrylic, polyethylene, polypropylene, and the like, and the coating thickness is preferably in the range of 5 to 30 μm in consideration of adhesive strength, but is not limited thereto.

The adhesive tape is suitable for use in processes requiring higher adhesive strength than conventional dicing or dicing die-bonding processes because of its high adhesive strength and low peeling force after photocuring. It can be usefully used in a process requiring strong backgrinding such as for optical glass processing.

Hereinafter, examples will be described in detail to help understand the present invention. However, the following examples are merely to illustrate the content of the present invention is not limited to the scope of the present invention. The embodiments of the present invention are provided to more completely explain the present invention to those skilled in the art.

< Experimental Example >

The following experimental examples are intended to provide experimental examples that are commonly applied to each embodiment according to the present invention.

Investigation of adhesion before UV curing

The 180 ° peel force (mN / 25mm) was measured using each pressure-sensitive adhesive film prepared from the photocurable re-peelable pressure-sensitive adhesive composition obtained in Examples or Comparative Examples.

In an atmosphere of 23 ° C. and 65% relative humidity, a test piece was prepared by reciprocally compressing an adhesive tape having a width of 25 mm and a length of 250 mm on a SUS # 304 stainless steel plate (50 mm width 300 mm thickness 3 mm) once with a 2 kg load rubber roller. It was. After leaving for 30 minutes, using a universal tensile tester (trade name: VersaTest, manufactured by Mecmesin) in accordance with Clause 8 of KS-A-01107 (Testing Method of Adhesive Tape and Adhesive Sheet) at a peel rate of 300 mm / min. , The peeling force of the pressure-sensitive adhesive sheet was measured.

After ultraviolet irradiation Peel force  Research

Ultraviolet irradiation apparatus (trade name: LZ-UHF 402RCH, manufactured by Ridzen Co., Ltd.) : 300 mW / cm <2>, light quantity: 700 mJ / cm <2>, Air state), and the ultraviolet-ray was irradiated from the base material side. The treated test piece was measured for 180 ° peel force (mN / 25mm) under the above conditions.

Change over time

Immediately after preparation of the test piece prepared by the ultraviolet pre-cured adhesion test method and left for 10 days at 2 kg load, and after peeling off after irradiation with ultraviolet light, the contamination state of the adherend was observed by optical microscope to determine the presence of residue.

< Example  1>

1. Acrylic Adhesive resin  Composition manufacturing

300 g of propylene glycol monomethyl ether acetate, 236 g of 2-ethylhexyl acrylate and 64 g of glycidyl methacrylate were first introduced into a 2 L four-necked reactor, a reflux condenser was installed, and the temperature inside the reactor was raised to 60 ° C. Nitrogen bubbling was then performed. After nitrogen bubbling was maintained for 30 minutes, a mixture of 0.08 g of azobisisobutyronitrile and 1 g of propylene glycol monomethyl ether acetate was added thereto, and the solid content was maintained for 15 hours while maintaining the temperature inside the reactor within ± 10 ° C. The end point of the reaction was when the conversion rate was 90% or more based on the change. After the addition of 400 g of propylene glycol monomethyl ether acetate and 0.3 g of hydroquinone, the reaction was stopped to obtain an adhesive acrylic binder resin intermediate having a weight average molecular weight of 1 million and a solid content of 28% conversion of 94%. Again, the temperature inside the reactor was increased to 100 ° C., followed by blowing air, adding 16.2 g of acrylic acid and 0.06 g of dimethylaminopyridine, and maintaining the mixture for 8 hours. The residual acid value of the reactants was measured and the temperature inside the reactor was lowered to 90 ° C. at an acid value of 2.5 or less. Then, 0.06 g of dimethylaminopyridine, 22.1 g of maleic anhydride, and 300 g of propylene glycol monomethyl ether acetate were added thereto and maintained for 4 hours. The reaction was terminated to obtain an acrylic adhesive resin composition having a viscosity of 12000 cps, a solid content of 27% and an acid value of 36.

2. Photocuring Re-peelable Adhesive resin  Composition of the composition

100 g of the acrylic adhesive resin composition prepared above was a photocurable urethane acryl-based oligomer curing agent 5g UV-306T of the Japanese public company, a trimethylolpropane toluene diisocyanate adduct with a thermosetting isocyanate-based curing agent (Japan Polyurethane Co., Coronate LS) 1g, heat DBTDL (Dibutyltin dilaurate) 0.03g as a curing catalyst, Irgacure 184 1g of Ciba Special Co., Ltd., Irgacure 907 1g as a photoinitiator was mixed to prepare a photocurable re-peelable adhesive resin composition.

3. Photocuring Re-peelable  Adhesive tape manufacturers

The photocurable re-peelable pressure-sensitive adhesive composition was applied to a 100 μm polyethylene terephthalate film so that the final pressure-sensitive adhesive film had a coating thickness of 25 μm to prepare a photocurable re-peelable pressure-sensitive adhesive tape, and then adhesive strength was measured. The measured results are shown in Table 1 below.

< Example  2>

1. Acrylic Adhesive resin  Composition manufacturing

Except for using 33.3 g of phthalic anhydride instead of 22.1 g of maleic anhydride, it was used in the same manner as in Experiment 1. The weight average molecular weight of the adhesive acrylic binder resin intermediate was 970,000, and the viscosity of the final acrylic adhesive resin composition was 13000 cps, and the solid content was 27.5%. , The mountain was 35.5.

2. Photocuring Re-peelable Adhesive resin  Composition of the composition

Photocurable re-peelable adhesive resin composition was prepared in the same manner as in Example 1.

3. Photocuring Re-peelable  Adhesive tape manufacturers

Photocurable re-peelable pressure-sensitive adhesive tape was prepared using the same method as in Example 1, and then adhesive strength was measured. The measured results are shown in Table 1 below.

< Example  3>

1. Acrylic Adhesive resin  Composition manufacturing

The same acrylic adhesive resin composition prepared in Example 1 was used.

2. Photocuring Re-peelable Adhesive resin  Composition of the composition

Except for the photocurable urethane acrylic oligomer curing agent, a photocurable re-peelable pressure-sensitive adhesive composition was prepared in the same manner as in Example 1.

3. Photocuring Re-peelable  Adhesive tape manufacturers

Photocurable re-peelable pressure-sensitive adhesive tape was prepared using the same method as in Example 1, and then adhesive strength was measured. The measured results are shown in Table 1 below.

< Example  4>

1. Acrylic Adhesive resin  Composition manufacturing

The same acrylic adhesive resin composition prepared in Example 1 was used.

2. Photocuring Re-peelable Adhesive resin  Composition of the composition

Photocurable re-peelable pressure-sensitive adhesive composition was prepared in the same manner as in Example 1 except for the thermosetting isocyanate curing agent.

3. Photocuring Re-peelable  Adhesive tape manufacturers

Photocurable re-peelable pressure-sensitive adhesive tape was prepared using the same method as in Example 1, and then adhesive strength was measured. The measured results are shown in Table 1 below.

< Comparative example  1>

1. Acrylic Adhesive resin  Composition manufacturing

200 g of ethyl acetate, 187 g of 2-ethylhexyl acrylate, and 13 g of acrylic acid were first introduced into a 1 L four-neck reactor, a reflux condenser was installed, and the temperature inside the reactor was raised to 60 ° C., followed by nitrogen bubbling. Nitrogen bubbling was maintained for 30 minutes, and then a mixed solution of azobisisobutyronitrile 0.05g and 1g of ethyl acetate was added, and then maintained for 15 hours while maintaining the temperature inside the reactor within ± 10 ° C. The reaction end point was 90% or more. Thereafter, 100 g of ethyl acetate and 0.2 g of hydroquinone were added, and the reaction was stopped to obtain an acrylic adhesive resin having a weight average molecular weight of 1.2 million and a solid content of 38% conversion of 95%.

2. Photocuring Re-peelable Adhesive resin  Composition of the composition

100 g of the acrylic adhesive resin composition prepared above, a photocurable urethane acryl-based oligomer curing agent UV-306T 15g of the Japanese public company, a trimethylolpropane toluene diisocyanate adduct (Japanese Polyurethane Co., Coronate LS) 1g, heat with a thermosetting isocyanate curing agent DBTDL (Dibutyltin dilaurate) 0.03g as a curing catalyst, Irgacure 184 1.2g, Irgacure 907 1.2g of Ciba Special Inc. as a photoinitiator was blended to prepare a photocurable re-peelable adhesive resin composition.

3. Photocuring Re-peelable  Adhesive tape manufacturers

Photocurable re-peelable pressure-sensitive adhesive tape was prepared using the same method as in Example 1, and then adhesive strength was measured. The measured results are shown in Table 1 below.

< Comparative example  2>

1. Acrylic Adhesive resin  Composition manufacturing

130 g of toluene and 260 g of ethyl acetate were added to a 2-L four-necked reactor, and the temperature was raised to 80 ° C., followed by 260 g of 2-ethylhexyl acrylate, 104 g of butyl acrylate, 123.5 of methyl methacrylate, and 32.5 g of 2-hydroxyethyl methacrylate. 130 g glycidyl methacrylate and 4.6 g mixed solution of benzoyl peroxide were added dropwise for 150 minutes and maintained for three hours. After adding 65 g of toluene and 1.3 g of azobisisobutyronitrile for 10 minutes, the mixture was maintained for 4 hours, and 162.5 g of methyl ethyl ketone 162.5 g of ethyl acetate and 195 g of toluene were added to terminate the reaction. The weight average molecular weight of the reaction product was 220,000, solid content 38%, and viscosity 1400 cps. The reactor was again heated to 100 ° C. while blowing air, adding 65 g of acrylic acid, 5000 ppm of hydroquinone, 1000 ppm of triphenylphosphite, and 2000 ppm of quaternary ammonium salt and maintaining the mixture for 8 hours. The acid value was 2.5.

2. Photocuring Re-peelable Adhesive resin  Composition of the composition

To 100 g of the acrylic adhesive resin composition prepared above, 3.7 g of trimethylolpropane toluene diisocyanate adduct as a thermosetting isocyanate-based curing agent (Coronate LS, Nippon Polyurethane Co., Ltd.), 0.12 g of DBTDL (Dibutyltin dilaurate) as a thermosetting catalyst, Ciba as a photoinitiator Irgacure 184 1.2 g and Irgacure 907 1.2 g of special company were blended to prepare a photocurable re-peelable adhesive resin composition.

3. Photocuring Re-peelable  Adhesive tape manufacturers

Photocurable re-peelable pressure-sensitive adhesive tape was prepared using the same method as in Example 1, and then adhesive strength was measured. The measured results are shown in Table 1 below.

[Table 1] Comparison of adhesive force of photocurable re-peelable tape

division Example 1 Example 2 Example 3 Example 4 Comparative Example 1 Comparative Example 2 Adhesive force before UV irradiation [gf] 2400 2000 2200 2500 2200 900 Adhesive force after UV irradiation [gf] 20 30 60 40 30 20 depreciation
change 1 day left radish radish radish U U radish After 10 days radish radish U U U radish

According to the results measured and compared in the table, Comparative Example 2, which did not introduce a carboxyl functional group in the acrylic adhesive resin, showed the lowest adhesive force, and the photocurable urethane acrylic oligomer curing agent was not added (Example 3), or the thermosetting agent was When not added (Example 4), or even if the addition of the acryloyl functional group in the acrylic adhesive resin (Comparative Example 1) can improve the adhesion, but it will result in contaminating the adherend in the time-dependent change test Able to know.

In addition, when maleic anhydride is used as in Example 1, it is possible to simultaneously introduce carboxylic acid and acryloyl functional groups at the same time, thereby controlling the adhesion more weakly after UV irradiation.

Putting together the results of evaluation of the physical property test, the embodiments of the present invention have acryloyl functional group in the acrylic adhesive resin, but newly introduce a carboxyl functional group, but the adhesive strength is high after the photocuring, but the adhesive strength after photocuring re-peeling type adhesive It can be seen that the tape is provided.

Having described the specific parts of the present invention in detail, it will be apparent to those skilled in the art that such specific descriptions are merely preferred embodiments, and thus the scope of the present invention is not limited thereto. will be. Thus, the substantial scope of the present invention will be defined by the appended claims and their equivalents.

Claims (12)

70 to 98 parts by weight of a (meth) acrylic acid ester monomer having an alkyl group having 1 to 14 carbon atoms and 2 to 30 parts by weight of a (meth) acrylic acid monomer having a glycidyl functional group.  Acrylic adhesive resin composition comprising 1 to 30 parts by weight of (meth) acrylic acid and 1 to 30 parts by weight of dicarboxylic anhydride. The acrylic adhesive resin composition according to claim 1, wherein the (meth) acrylic acid and dicarboxylic acid anhydride are added to the glycidyl functional group of the adhesive acrylic binder resin. The (meth) acrylic acid ester monomer according to claim 1, wherein the (meth) acrylic acid ester monomer is 2-ethylhexyl (meth) acrylate, butyl (meth) acrylate, lauryl (meth) acrylate, t-butyl (meth) acrylate, n-octyl In the group consisting of (meth) acrylate, ethyl (meth) acrylate, methyl (meth) acrylate, n-propyl (meth) acrylate, iso-butyl (meth) acrylate and iso-propyl (meth) acrylate Acrylic adhesive resin composition is any one or more selected. The acrylic adhesive resin composition of claim 1, wherein the (meth) acrylic acid monomer having a glycidyl functional group is any one or more selected from the group consisting of glycidyl acrylate and glycidyl methacrylate. The acrylic adhesive resin composition of claim 1, wherein the acrylic adhesive resin composition has a weight average molecular weight of 300,000 to 1,500,000. The acrylic adhesive resin composition of claim 1, wherein the glass transition temperature of the acrylic adhesive resin composition is -80 ° C to -10 ° C. A photocurable re-peelable pressure-sensitive adhesive composition comprising an acrylic pressure-sensitive adhesive composition according to any one of claims 1 to 6, a curing agent and a photoinitiator. The photocurable re-peeling according to claim 7, wherein the curing agent is any one or more selected from the group consisting of 1 to 20 parts by weight of a photocurable urethane acrylic oligomer curing agent and 1 to 5 parts by weight of a thermosetting isocyanate curing agent relative to 100 parts by weight of the acrylic adhesive resin composition. Type adhesive resin composition. The photocuring agent according to claim 7, wherein the photoinitiator is at least one selected from the group consisting of an alpha-hydroxy ketone type compound, a benzyl ketal type compound, an alpha-amino ketone type compound, an acrylic phosphine type compound, and a metallocene type compound. Re-peelable adhesive resin composition. The photocurable re-peelable pressure-sensitive adhesive composition of claim 7, wherein the amount of the photoinitiator is 1 part by weight to 10 parts by weight with respect to 100 parts by weight of the acrylic adhesive resin composition. An adhesive tape comprising the photocurable re-peelable adhesive resin composition according to claim 7. The adhesive tape according to claim 11, wherein the adhesive tape is for wafer processing or optical glass processing.