KR20120060695A - Manufacturing Method of Acrylic Pressure Sensitive Adhesive Composition Comprising Vinyl Group on Polymer Side Chain - Google Patents

Abstract

PURPOSE: A manufacturing method of an adhesive composition is provided to provide to have simple manufacturing process, to provide adhesive composition having excellent wettability, low releasing force after ultraviolet irradiation, and excellent curing stability, and not remaining residues to an object. CONSTITUTION: A manufacturing method of an adhesive composition comprises: a step of polymerization by mixing a (meth)acrylate based monomer containing a C1-14 alkyl group, a (meth)acrylate based monomer containing a hydroxy group, a carboxy group, or a glycidiyl group, or a mixture thereof, and an initiator; and a step of addition polymerization by putting a photocurable monomer with carbon-carbon double bond having a carbon-carbon double bond, a catalyst, and polymerization inhibitor into the side chain of the polymer.

Description

Manufacturing Method of Acrylic Pressure Sensitive Adhesive Composition Comprising Vinyl Group on Polymer Side Chain

The present invention relates to a method for producing an acrylic pressure-sensitive adhesive composition containing a vinyl group through the addition reaction to the polymer side chain, more specifically, the pressure-sensitive adhesive composition excellent in adhesion and stability over time and easily peeled off from an ultra-thin wafer, leaving no adhesive residue; It relates to a manufacturing method thereof.

In the semiconductor manufacturing process, circuit-designed wafers are separated into small chips through dicing in a size having a large diameter, and each separated chip is subjected to a step-by-step process of bonding to a supporting member such as a PCB substrate or a lead frame substrate by bonding. have. In general, the bonding / debonding tape has a structure including an adhesive layer on the base film and a release film on the adhesive layer. In the semiconductor process using an ultra-thin wafer, after peeling the release film, the adhesive layer is laminated on the ultra-thin wafer chip, and the chip is cut to the size of the designed circuit. The cutting process is called a dicing process. Generally, dicing is carried out to a depth of a lower base film under the adhesive layer, and the ultraviolet ray is applied from the lower part of the film to pick up the individualized chip and attach it to the support member. Reduces the peel force between the layer and the wafer chip interface. The individualized chip having the adhesive layer attached thereto is picked up with a constant force by using a pickup called a collet and attached to a supporting member such as a PCB substrate or a lead frame.

The main purpose of the dicing tape is to adhere to the backside of the wafer to prevent the film from scattering or flowing during dicing to prevent cracking of the wafer and to easily peel off from the ultra-thin wafer after irradiation with radiation and ultraviolet rays. If the dicing tape is not used, the film is scattered or flows due to the blade rotating at a high speed, and the chip is damaged. It was easily peeled off later to facilitate the individualization process.

Existing dicing tape has applied (Poly vinyl chloride, PVC) based film as a base film, but PVC film film has high modulus and low elongation, so it has good expanding effect, but plasticizer and additive for softening PVC film These plasticizers and additives were migrated to the coating adhesive layer by adding so that it could not solve the fundamental problems of PVC film use such as the fatal problem of the durability of the product over time and the environmental problem of polyvinyl chloride. .

Therefore, the development of the tape for (Bonding / Debonding) using the composition and the PO (polyolefin) series film which are optimal for pick-up property is given priority.

In addition, according to the Republic of Korea Patent No. 2002-0001270, 2002-0001271 isocyanate type after preparing a terpolymer using butyl acrylate, ethyl acrylate, glycidyl methacrylate, 2-hydroxy methacrylate After adding a curing agent of the urethane acrylate or epoxy acrylate as an oligomer and irradiating ultraviolet rays, the method of reducing the adhesive strength without leaving an adhesive on the adherend is used. Japanese Patent Laid-Open No. 61-2433878 discloses a first intermediate layer made of ethylene copolymer containing anionic surfactant and a second intermediate layer made of polyethylene between a tape base layer made of a plastic film and an adhesive layer made of ethylene-vinyl acetate copolymer. The technique of the dicing tape which consists of such a structure which can reduce an adhesive strength by heat processing after a cutting operation and can extract a chip easily is proposed.

However, in the case of the acrylic pressure-sensitive adhesives used in the above methods, there is a problem that photopolymerization does not proceed effectively during ultraviolet irradiation, or an intermediate layer between the tape base material and the adhesive layer is essentially constituted, and thus the manufacturing process is complicated. An adhesive composition capable of doing is required.

The present invention is to solve the above problems, excellent wettability, the adhesive strength is maintained at the time of initial attachment, the change over time even after the time of adhesion is small, the residue on the adherend according to the optical crosslinking integrated with the polymer It is an object of the present invention to provide a method for producing an acrylic pressure-sensitive adhesive composition containing a vinyl group having excellent adhesion and re-peelability without remaining. In addition, an object of the present invention is to provide an addition reaction pressure-sensitive adhesive composition prepared from the production method.

The present invention has sufficient adhesive strength and stability over time before radiation and ultraviolet irradiation, and has an effective peeling force on an ultra-thin wafer according to photocrosslinking integrated with a polymer after radiation and ultraviolet radiation, and includes a catalyst and a high conversion rate. It provides a method for producing the composition and the pressure-sensitive adhesive composition prepared therefrom.

In another aspect, the present invention is to provide a pressure-sensitive adhesive composition that hardly remains an adhesive residue on the ultra-thin wafer, and provides a bonding / debonding pressure-sensitive adhesive tape to which the addition-reactive acrylic pressure-sensitive adhesive composition is applied.

Method for producing a pressure-sensitive adhesive composition of the present invention

a) (meth) acrylate type monomer which has C1-C14 alkyl group; (Meth) acrylate monomers having a hydroxy group, a carboxyl group or a glycidyl group or mixtures thereof; And polymerizing by mixing an initiator; And

b) adding and polymerizing a photocurable monomer having a carbon-carbon double bond, a catalyst, and a polymerization inhibitor into the side chain of the polymer;

It includes.

In addition, c) characterized in that it further comprises the step of mixing a crosslinking agent and a photoinitiator to the addition polymer.

Hereinafter, the present invention will be described in detail.

The (meth) acrylate-based monomer having an alkyl group of C1 to C14 of the present invention is a monomer that provides adhesion, and has a glass transition temperature of -70 to 130 ° C, more preferably using an alkyl group of C4 to C14. If the carbon number is out of the above range, the glass transition temperature is high or the adhesion is difficult to control.

Examples of the (meth) acrylate monomer having an alkyl group of C1 to C14 include methyl acrylate, ethyl acrylate, butyl acrylate, 2-ethyl butyl acrylate, 2-ethylhexyl (meth) acrylate and hexyl acryl. Latex, heptyl acrylate, octyl acrylate, n-pentyl acrylate, vinyl acrylate, lauryl acrylate, methyl methacrylate, ethyl methacrylate, butyl methacrylate, 2-ethylbutyl methacrylate, 2- At least one selected from ethylhexyl methacrylate and lauryl methacrylate is used.

The (meth) acrylate monomer having a hydroxy group, a carboxyl group or a glycidyl group of the present invention or a mixture thereof is included as a functional group and a crosslinkable monomer to effectively give an addition polymerization monomer for photocurability.

The (meth) acrylate monomer having a hydroxy group, a carboxyl group or a glycidyl group or a mixture thereof is 2-hydroxyethyl acrylate, 2-hydroxymethyl acrylate, 2-hydroxypropyl acrylate, 2-hydroxy Butyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxymethyl methacrylate, 2-hydroxypropyl methacrylate, 2-hydroxy butyl methacrylate, glycidyl (meth) acrylate At least one selected from (meth) acrylic acid, hydroxy (meth) acrylic acid, hydroxyglycidyl (meth) acrylate, amine (meth) acrylic acid and amineglycidyl (meth) acrylate, and more preferably. Preferably, (meth) acrylic acid or glycidyl (meth) acrylate is used. In particular, the (meth) acrylic acid has a high polarity and is easy to control adhesiveness and physical properties through interaction with the adherend, and excellent reactivity when addition reactions with other heterogeneous monomers and materials and chemical bonding with various functional groups.

The (meth) acrylate monomer having a hydroxy group, a carboxyl group or a glycidyl group or a mixture thereof is preferably used in an amount of 10 to 30 parts by weight based on 100 parts by weight of the (meth) acrylate monomer having an alkyl group of C1 to C14. Do. The content of the photocuring monomer, which is an addition polymerization monomer, is determined according to the content, and affects photocuring density, cohesion and peeling force. When the range is less than 10 parts by weight, the cohesion force is low, and the re-peelability is lowered. When the range is more than 30 parts by weight, the polarity is increased, the change over time and the degree of crosslinking are increased.

In addition, the initiator used in the polymerization of step a) of the present invention may be a photopolymerization initiator of 4- (2-hydroxyethoxyphenyl); Azo polymerization initiators, such as 2,2'- azobisisobutyronitrile, 2,2'- azobis (2-methylbutyronitrile), and 1,1'- azobis (cyclohexane-1-carbonitrile) ; There is a thermal polymerization initiator of organic peroxides such as tert-butyl hydroperoxide, benzoyl peroxide, cumene hydroperoxide, inorganic peroxides such as potassium persulfate and hydrogen peroxide, but is not necessarily limited thereto.

The polymerization of step a) uses photopolymerization and copolymerization, and the copolymerization includes solution polymerization, photopolymerization, bulk polymerization, suspension polymerization or emulsion polymerization, and solution polymerization is most preferred. At this time, the polymerization is preferably carried out by reacting for 6 to 12 hours at 50 to 140 ℃ in a nitrogen atmosphere, it is preferable to add the initiator after mixing the monomers uniformly.

The copolymer resin prepared by the copolymerization of step a) uses a weight average molecular weight of 100,000 to 1,000,000, more preferably 400,000 to 700,000. When the molecular weight is 400,000 or less, the cohesive force of the polymer is low, so that the resistance to heat is low. When the molecular weight is 1,000,000 or more, the adhesion to the substrate is low, which may cause transfer in the film. In addition, in order to obtain appropriate initial adhesive strength after heat curing, the glass transition temperature is preferably -70 to -20 ° C, more preferably -60 to -30 ° C. When the glass transition temperature is about −10 ° C., when the initial adhesive strength is low, the adhesion force to the ring frame may be low due to dicing, or the chip may be scattered because the adhesion force to the wafer is low.

In the addition polymerization step of the present invention, a photocurable monomer having a carbon-carbon double bond capable of photocuring with a functional group of a resin produced by copolymerization may be integrated with a copolymerized resin, and a photocurable resin is prepared through an addition reaction including a catalyst. .

The photocurable monomer of the present invention is a monomer having a carbon-carbon double bond, which is used to cause photopolymerization by reaction of photoinitiators due to radiation and ultraviolet rays, and is a monomer that is additionally polymerized to functional groups and crosslinkable monomers. Examples of the photocuring monomers include (meth) acrylic acid or glycidyl (meth) acrylate, and more specifically glycidyl (meth) acrylate, (meth) acrylic acid, hydroxy (meth) acrylic acid, At least one selected from hydroxyglycidyl (meth) acrylate, amine (meth) acrylic acid and amine glycidyl (meth) acrylate is used.

The photocuring monomer is preferably 0.5 to 1.0 mol (mol) relative to 1.0 mol (mol) of a (meth) acrylate monomer having a hydroxy group, a carboxyl group or a glycidyl group or a mixture thereof. If the range is 0.5 mole or less, the photocuring density is low, the cohesive force and the peeling force is lowered, and the residue remains. If it is 1.0 mole or more, crosslinking is difficult, so that it is difficult to prepare a pressure-sensitive adhesive of uniform quality including cohesion of the polymer. In other words, the amount of the photocuring monomer added is very important.

The catalyst used in the addition polymerization of step b) of the present invention is used to shorten the reaction time and increase the conversion rate in the synthesis process, and includes an imidazole compound, triphenylphosphine (TPP), paratoluenesulperic acid (PTSA), and 3 One or more selected from the tertiary amines are used, but not limited thereto. Specific examples of the imidazole compound include 2-methylimidazole (2MZ), 2-ethyl-4-methylimidazole (2E4MZ), 2-phenylimidazole (2PZ), 1-cyanoethyl-2- Pettylimidazole (2PZ-CN), 2-Undecylimidazole (C11Z), 2-heptadecylimidazole (C17Z) and 1-cyanoethyl-2phenylimidazole trimetalate (2PZ-CNS ) Is selected from, and more preferably 2-methylimidazole (2MZ).

The catalyst is used in an amount of 0.001 to 10 parts by weight based on 100 parts by weight of the photocuring monomer, and more preferably 0.01 to 5 parts by weight. If the content is less than 0.001 part by weight, the reaction rate of the addition polymerization of the photocuring monomer is low, so the conversion tends to be low, so that unreacted monomers are present, affecting physical properties. Is lowered.

In addition, the pressure-sensitive adhesive composition of the present invention may further include, for example, butylated hydroxy toluene as a polymerization inhibitor, but is not limited thereto.

The polymerization of step b) is prepared by using an addition polymerization method to produce a photocurable resin, the addition polymerization is preferably carried out by reacting for 6 to 12 hours at 50 to 140 ℃ in a nitrogen atmosphere.

The crosslinking agent of step c) of the present invention is one or more selected from isocyanate compounds, epoxy compounds, aziridine compounds and metal chelate compounds, more preferably epoxy compounds. Examples of the epoxy compound include ethylene glycol diglycidyl ether, triglycidyl ether, trimethol propane triglycidyl ether, N, N, N ', N'-tetraglycidyl ethylenediamine or glycerin diglycidyl ether. Etc., but is not necessarily limited thereto.

The crosslinking agent is used 0.1 to 5 parts by weight based on 100 parts by weight of the photocurable resin. When the content of the crosslinking agent is less than 0.1 part by weight, the crosslinking reaction may not proceed smoothly, and the cohesive force of the pressure sensitive adhesive may be lowered. When the content of the crosslinking agent is more than 5 parts by weight, the crosslinking reaction may be excessively progressed and durability may be lowered.

In addition, when the addition-responsive pressure-sensitive adhesive of the present invention is cured by radiation and ultraviolet rays, a photoinitiator (photopolymerization initiator) may be further added. The photoinitiator is α-ketol compound, acetophenone compound, ketal compound, aromatic sulfonyl chloride compound, photoactive oxime compound, benzophenone compound, thioxanthone compound, camphorquinone compound, halogenated ketone compound, At least one selected from acyl phosphoxide compound and acyl phosphonate compound is used.

More specifically, for example, 4- (2-hydroxyethoxy) phenyl (2-hydroxy-2-propyl) ketone, α-hydroxy-α, α'-dimethylacetophenone, 2-methyl-2- Α-ketol compounds such as hydroxypropiophenone and 1-hydroxycyclohexylphenyl ketone; Methoxyacetophenone, 2,2-dimethoxy-2-phenylacetophenone, 2,2-diethoxyacetophenone, 2-methyl-1- [4- (methylthio) -phenyl] -2-morpholinopropane Acetophenone compounds such as -1; Benzoin ether compounds such as benzoin ethyl ether, benzoin isopropyl ether and anisoin methyl ether; Ketal compounds such as benzyl dimethyl ketal; Aromatic sulfonyl chloride-based compounds such as 2-naphthalenesulfonyl chloride; Photoactive oxime compounds such as 1-phenone-1,1-propanedione-2- (o-ethoxycarbonyl) oxime; Benzophenone compounds such as benzophenone, benzoylbenzoic acid and 3,3'-dimethyl-4-methoxybenzophenone; Thioxanthone, 2-chloro thioxanthone, 2-methyl thioxanthone, 2,4-dimethyl thioxanthone, isopropyl thioxanthone, 2,4-dichloro thioxanthone, 2,4-diethyl thioxide Thioxanthone type compounds, such as a santon and 2, 4- diisopropyl thioxanthone; Camphorquinone; Halogenated ketones; Acylphosphinoxide; Acyl phosphonate etc. are mentioned.

The photoinitiator is activated by the radiation or ultraviolet rays to activate a carbon-carbon double bond in the adhesive layer to generate a radical reaction. The photoinitiator uses 0.05 to 10 parts by weight based on 100 parts by weight of the photocurable acrylic adhesive resin through the addition reaction according to step b). More preferably, 2 to 7 parts by weight is used. When the content of the photopolymerization initiator is less than 0.05 parts by weight, the degree of photocurability is reduced and the stickiness of the sticky film after UV curing is insignificant. If it is 10 parts by weight or more, the unreacted initiator acts as an impurity in addition to the irritating odor in the initiator portion which does not participate in the reaction during UV curing, thereby affecting the physical properties.

In addition, UV stabilizers, antioxidants, pigments, dyes, reinforcing agents, fillers and the like may be appropriately added and used in the pressure-sensitive adhesive composition according to the general purpose within a range that does not affect the effect of the invention.

The pressure-sensitive adhesive composition of the present invention provides a pressure-sensitive adhesive film having a uniform pressure-sensitive adhesive layer of 5 ~ 30 ㎛ after drying by coating on one surface of a polyolefin-based, polyethylene terephthalate, polyethylene or polypropylene film.

The acrylic pressure-sensitive adhesive composition containing a vinyl group by addition reaction to the polymer side chain of the present invention is added with (meth) acrylic acid or glycidyl methacrylate having a low boiling point together with the solvent in the dicing or dicing die-bonding film coating process. By blowing away, the content of unreacted monomer in the coating can be minimized.

The unreacted glycidyl acrylate which was a problem of the polymer completed by introducing a conventional method (meth) acrylic acid or glycidyl methacrylate into the polymer structure and then polymerizing glycidyl acrylate or (meth) acrylic acid. Alternatively, the change in the temporal change of the adhesive film caused by the residual of (meth) acrylic acid is improved in the reaction including the catalyst and the reaction inhibiting agent in the addition reaction step, and thus the temporal change and the stability of the adhesive film generated due to the remaining of the unreacted material I was able to improve considerably.

In addition, it has the advantage that the addition reaction can be performed smoothly at a lower temperature than the condensation addition reaction, and by using a low-cost (meth) acrylic acid or glycidyl methacrylate, it is more expensive than the introduction of a substance having an isocyanate group and a vinyl group It has advantageous advantages.

The pressure-sensitive adhesive composition prepared by the manufacturing method according to the present invention is an acrylic pressure-sensitive adhesive containing carbon-carbon double bonds through the addition reaction of the polymer side chain, and has excellent wettability, thereby maintaining a constant adhesive force at the time of initial attachment, The initial adhesive strength is kept constant even though it has passed, and the adhesive strength is stable. The cohesion and peeling force are high, and thus the yield can be increased in the semiconductor manufacturing process using the ultra-thin wafer, and the catalyst is used to shorten the reaction time and increase the conversion rate. The resin manufacturing process is also simple, and is excellent in productivity and economy, and is suitable for application to semiconductor processes.

Hereinafter, the present invention will be described in more detail with reference to Examples. However, the present invention is not intended to limit the scope of the present invention.

Production Example 1-2 Preparation of Pressure-Sensitive Adhesive Composition

Nitrogen gas is filled, and a thermometer and a cooling device are installed inside and outside to facilitate temperature control, and the (meth) acrylate monomer in the composition of Table 1 in a 2 L reactor that can control the reaction rate and heat generation of the reactants. , (Meth) acrylate monomers having a hydroxy group, a carboxyl group or a glycidyl group were added thereto.

To 100 parts by weight of the mixture composed of the monomers shown in Table 1, 30 parts by weight of toluene and 70 parts by weight of ethylacetate (ethylacetate, EAc) were added.

Then, after purging nitrogen gas for 20 minutes to remove oxygen, the monomer mixture was uniformly stirred, and then 0.06 parts by weight of azobisisobutyronitrile (AIBN) was added as a reaction initiator. The temperature of the reactor was maintained at 90 ° C. and a small amount of the reactant was added dropwise to react for 10 hours to prepare a copolymerizable resin. To the copolymerization resin was added a photocuring monomer having a carbon-carbon double bond, 2-methylimidazole, and butylate hydroxy toluene in the composition of Table 1, followed by addition polymerization at 80 ° C. for 10 hours to prepare an addition polymerization resin. .

[Comparative Production Example 1]

Preparation was carried out in the same manner as in Example except that glycidyl methacrylate (GMA), 2-methylimidazole (2MZ) and butylate hydroxy toluene (BHT) were not added.

[Comparative Production Example 2 ~ 3]

Preparation was carried out in the same manner as in Example, except that 2-methylimidazole (2MZ) and butyrate hydroxy toluene (BHT) were not added.

[Table 1]

week)

* BA: Butyl acrylate

2-EHA 2-ethylhexyl acrylate

* 2-EHMA: 2-ethylhexyl methacrylate

* AA, MA: acrylic acid, methacrylic acid

* GMA: glycidyl methacrylate (glycidyl metaacrylate) (molar ratio compared to AA, MA >>)

* 2MZ: 2-methyl imidazole (% of GMA >>)

* BHT: Butyl hydroxy toluene (% of GMA >>)

* AIBN: 2,2'-Azobis Isobutyronitrile

α-Hydroxyketone: alpha-hydroxy ketone

[Examples 1 and 2] Preparation of Adhesive Film

2.0 parts by weight of a crosslinking agent (trade name Tetra-DX: manufactured by Japan) and 5.0 parts by weight of a photoinitiator (α-Hydroxyketone) were added to the prepared Preparation Examples 1 to 2, followed by uniform mixing, followed by biaxially stretched polyolefin and polyethylene having a thickness of 80 μm. After coating and drying one surface of a terephthalate film (SKC Hass) to prepare an adhesive film having a uniform adhesive layer of 20㎛ and evaluated the physical properties as shown in Table 2 below.

Comparative Example 1 to 3 Preparation of Adhesive Film

Except for using Comparative Preparation Examples 1-3 were prepared in the same manner as in Example.

(1) adhesion test

The release film was laminated to the prepared pressure-sensitive adhesive film, and stored at a temperature of 43 ° C. for 3 days to mature, and then attached to glass to test adhesion. The film was attached to the glass surface with a roller of 2 kg according to JIS Z 0.27, and then stored at 25 ° C. and 50% relative humidity for 24 hours, followed by 180 ° angle and 300 mm / min peeling. Rate was measured using a tensile tester Texture Analyzer (manufacturer: Stable Micro Systems).

(2) wetting properties

The prepared pressure-sensitive adhesive film was cut into silicon wafers in a size of 2.54 cm and 10 cm, respectively, to prepare a sample, and after peeling off the protective film, measuring the time when the protective film completely wets the glass surface without applying external pressure. And evaluated according to the following criteria. (○: less than 10 seconds, Δ: 10 seconds or more, less than 30 seconds, ×: 30 seconds or more)

(3) increased adhesion with time

In order to measure the adhesive strength over time, after the adhesive film is adhered to the glass surface, the adhesive strength of 20 minutes was measured, and after 24 minutes, the adhesive strength after 24 hours and the adhesive strength after 7 days were measured. The rate of increase was expressed in%.

(4) Residue of appearance after peeling (adhesive, ie residue on wafer surface)

After the adhesion test, the degree of contamination, appearance, peel strength, and the like of the silicon surface on which the film was peeled off were comprehensively evaluated.

(Good: easily peelable, no residue of adhesive on glass substrate, poor: adhesive residue on glass substrate)

TABLE 2

As shown in Table 2, Examples 1 to 2 exhibited stable physical properties with little change over time even after attachment while maintaining the initial adhesive force, and Comparative Examples 2 to 3 showed a change over time compared to the initial adhesive force, leaving residues on the adherend. The remaining results were shown.

In the case of not using a catalyst, glycidyl methacrylate may not be sufficiently reacted and remains as an unreacted substance, and thus sufficient peeling force may not be obtained after UV irradiation, leaving a residue.

On the other hand, in the case of Comparative Example 1 without the photocurable monomer there is no carbon-carbon double bond that can not react even after photocuring, it does not react after UV irradiation, it can be seen that the stability over time and poor peeling force, It was confirmed that the adhesive strength was relatively high and the re-peelability was relatively low, and the surface contamination was severe during peeling.

Claims (12)

a) (meth) acrylate type monomer which has C1-C14 alkyl group; (Meth) acrylate monomers having a hydroxy group, a carboxyl group or a glycidyl group or mixtures thereof; And polymerizing by mixing an initiator; And
b) adding and polymerizing a photocurable monomer having a carbon-carbon double bond, a catalyst, and a polymerization inhibitor into the side chain of the polymer;
Method of producing a pressure-sensitive adhesive composition comprising a. The method of claim 1,
c) A method for producing a pressure-sensitive adhesive composition further comprises a crosslinking agent and a photoinitiator in the addition polymer. The method of claim 1,
The (meth) acrylate monomer having an alkyl group of C1 to C14 is methyl acrylate, ethyl acrylate, butyl acrylate, 2-ethyl butyl acrylate, 2-ethylhexyl (meth) acrylate, hexyl acrylate, heptyl Acrylate, octyl acrylate, n-pentyl acrylate, vinyl acrylate, lauryl acrylate, methyl methacrylate, ethyl methacrylate, butyl methacrylate, 2-ethylbutyl methacrylate, 2-ethylhexyl meth Method for producing a pressure-sensitive adhesive composition selected from at least one of acrylate and lauryl methacrylate. The method of claim 1,
The (meth) acrylate monomer having a hydroxy group, a carboxyl group or a glycidyl group or a mixture thereof is 2-hydroxyethyl acrylate, 2-hydroxymethyl acrylate, 2-hydroxypropyl acrylate, 2-hydroxy Butyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxymethyl methacrylate, 2-hydroxypropyl methacrylate, 2-hydroxy butyl methacrylate, glycidyl (meth) acrylate , (Meth) acrylic acid, hydroxy (meth) acrylic acid, hydroxyglycidyl (meth) acrylate, amine (meth) acrylic acid and amine glycidyl (meth) acrylate . The method of claim 1,
The photocuring monomer is glycidyl (meth) acrylate, (meth) acrylic acid, hydroxy (meth) acrylic acid, hydroxyglycidyl (meth) acrylate, amine (meth) acrylic acid and amine glycidyl (meth). Method for producing a pressure-sensitive adhesive composition selected from the group of acrylates. The method of claim 1,
The catalyst is a method for producing a pressure-sensitive adhesive composition is at least one selected from imidazole compound, triphenylphosphine (TPP), paratoluenesulperic acid (PTSA) and tertiary amine. The method of claim 2,
The crosslinking agent is at least one selected from isocyanate compound, epoxy compound, aziridine compound and metal chelate compound, and the photoinitiator is α-ketol compound, acetophenone compound, ketal compound, aromatic sulfonyl chloride compound Preparation of pressure-sensitive adhesive composition selected from the group consisting of photoactive oxime compounds, benzophenone compounds, thioxanthone compounds, camphorquinone compounds, halogenated ketone compounds, acylphosphinoxide compounds and acylphosphonate compounds Way. The method of claim 4, wherein
The pressure-sensitive adhesive composition using 10 to 30 parts by weight based on 100 parts by weight of the (meth) acrylate monomer having a hydroxy group, a carboxyl group or a glycidyl group, or a mixture thereof, based on an alkyl group of C1 to C14. Manufacturing method. 6. The method of claim 5,
The photocurable monomer is a (meth) acrylate monomer having a hydroxyl group, a carboxyl group or a glycidyl group or 0.5 to 1.0 mol (mol) relative to 1.0 mol (mol) of a mixture thereof. . The method of claim 1,
The polymerization of step a) and step b) is carried out by reacting for 6 to 12 hours at 50 to 140 ℃ in a nitrogen atmosphere, respectively. An addition reaction pressure-sensitive adhesive composition prepared by using the method for preparing a pressure-sensitive adhesive composition of any one of claims 1 to 10. 12. The method of claim 11,
Pressure-sensitive adhesive film prepared by coating the addition reaction pressure-sensitive adhesive composition on a film.