KR102546544B1 - Antistatic additive composition, adhesive composition and protective film comprising the same - Google Patents

Abstract

The present application can provide an additive composition having excellent compatibility with silicone adhesive resins, being transparent, and having excellent antistatic properties. In addition, the present application can provide a pressure-sensitive adhesive composition having excellent adhesiveness, transparency, heat resistance, etc., excellent antistatic property, and no steaming during peeling, by including the additive composition.

Description

Antistatic additive composition, adhesive composition, and protective film comprising the same {Antistatic additive composition, adhesive composition and protective film comprising the same}

The present invention relates to an antistatic additive composition, an adhesive composition, and a protective film containing the same.

A protective film is used to protect a polarizer when manufacturing and/or packaging displays such as organic light-emitting diodes (OLEDs). At this time, static electricity is often generated in the process of peeling the protective film from the polarizing plate or the like. Since the static electricity generated in this way affects the alignment of liquid crystals inside the display panel and causes defects such as malfunction, it is important to control the generation of static electricity.

Recently, as a pressure-sensitive adhesive applied to displays, the use of silicone pressure-sensitive adhesives having excellent heat resistance, cold resistance, re-peelability, electrical insulation, and excellent adhesion to various adherends is increasing. However, in the case of silicone adhesives, it is not easy to prevent static electricity due to the excellent insulating properties of silicone.

In order to solve this problem, a method of performing corona treatment on the protective film, etc. has been considered, but there are disadvantages such as poor fairness and economic feasibility due to unsatisfactory static electricity prevention and the need to perform an additional process.

One object of the present application is to provide an additive composition having excellent compatibility with silicone adhesive resins, being transparent, and having excellent antistatic properties.

Another object of the present application is to provide a pressure-sensitive adhesive composition having excellent adhesiveness, transparency, heat resistance, and the like, excellent antistatic properties, and no steaming during peeling, by including the additive composition.

Among the physical properties mentioned in this specification, the physical properties in which the measurement temperature and/or the measurement pressure affect the results are the results measured at room temperature and/or normal pressure, unless otherwise specified.

The term room temperature is a natural temperature that is not heated or cooled, and means, for example, any temperature within the range of 10 ° C to 30 ° C, about 23 ° C or about 25 ° C. In addition, the unit of temperature in this specification is °C unless otherwise specified.

The term normal pressure is a natural pressure that is not pressurized or reduced, and usually means about 1 atmosphere of atmospheric pressure level.

In the present specification, in the case of physical properties in which measured humidity affects the result, unless otherwise specified, the corresponding physical property is a physical property measured at natural humidity that is not particularly controlled at room temperature and / or normal pressure.

In this application, the term hydrocarbon group may mean a substituted and/or unsubstituted hydrocarbon group, and examples thereof include an alkyl group, an alkenyl group, an alkynyl group, or an aryl group.

In this application, the term alkyl group, alkylene group or alkoxy group, unless otherwise specified, is a linear or branched chain alkyl group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms, or 1 to 4 carbon atoms, It may mean an alkylene group or an alkoxy group, or a cyclic alkyl group having 3 to 20 carbon atoms, 3 to 16 carbon atoms, 3 to 12 carbon atoms, 3 to 8 carbon atoms, or 3 to 6 carbon atoms, an alkylene group, or an alkoxy group.

In this application, the term alkenyl group or alkynyl group, unless otherwise specified, is a linear or branched alkenyl group having 2 to 20 carbon atoms, 2 to 16 carbon atoms, 2 to 12 carbon atoms, 2 to 8 carbon atoms, or 2 to 4 carbon atoms. Alternatively, it may mean an alkynyl group, or a cyclic alkenyl group or alkynyl group having 3 to 20 carbon atoms, 3 to 16 carbon atoms, 3 to 12 carbon atoms, 3 to 8 carbon atoms, or 3 to 6 carbon atoms.

In this application, the term aryl group or arylene group, unless otherwise specified, may mean an aryl group or arylene group having 6 to 24 carbon atoms, 6 to 18 carbon atoms, or 6 to 12 carbon atoms, for example, a phenyl group or It may be a perylene group or the like.

This application may relate, for example, to an additive composition. The additive composition may include, for example, a polysiloxane component represented by Chemical Formula 1 below.

[Formula 1]

(R ¹ ₃ SiO) - (R ² ₂ SiO) _n - (SiR ³ ₃ )

In Formula 1, R ¹ to R ³ may each independently be a hydrogen atom, a hydrocarbon group, or a compound represented by the following Formula 2, and when a plurality of R ¹ to R ³ are present, each may be the same as or different from each other, , At least one of R ¹ to R ³ may be a compound represented by Formula 2 below, and n may be a number within the range of 100 to 50000:

[Formula 2]

P-L-Q

In Formula 2, P to Q may each independently be a hydrogen atom or a hydrocarbon group, and L may be a single bond, an oxygen atom, a sulfur atom, an alkylene group, an alkenylene group, or an alkynylene group.

In this application, the term hydrocarbon group may mean a substituted and/or unsubstituted hydrocarbon group. The substituted hydrocarbon group is composed of, for example, carbon and hydrogen, and the hydrogen may be substituted with one or more functional groups. The substituted hydrocarbon group may be, for example, an alkyl group, an alkenyl group, an alkynyl group or an aryl group.

In the present application, at least one of the plurality of R ¹ of Formula 1 may be a compound represented by Formula 2. In the present application, at least one of P and Q in Chemical Formula 2 may be a hydrocarbon group. In the present application, Q in Formula 2 may be, for example, a hydrocarbon group substituted with at least one functional group. In this case, the functional group may be a hydroxyl group, a carboxyl group, an aldehyde group, an amine group, a carbonyl group or an isocyanate group, but is not limited thereto. In the present application, the term hydroxyl group, carboxyl group, aldehyde group, amine group, carbonyl group, or isocyanate group may include, for example, those in which an alkyl group or the like is substituted with the hydroxyl group, carboxyl group, aldehyde group, amine group, carbonyl group, or isocyanate group. there is. In the present application, the L may preferably be a single bond, an oxygen atom or a sulfur atom, and may be more preferably an oxygen atom in view of surface resistance characteristics of the protective film including the additive composition of the present application.

In Formula 1 of the present application, in another example, n is 200 or more, 300 or more, 400 or more, 500 or more, 600 or more, 700 or more, 800 or more, 900 or more, 1000 or more, 1100 or more, 1200 or more, 1300 or more, 1400 1500 or more, 1600 or more, 1700 or more, 1800 or more, 1900 or more, 2000 or more, 2100 or more, 2200 or more, 2300 or more, 2400 or more, 2500 or more, 2600 or more, 2700 or more, 2800 or more, 2900 or more, or 3000 or more; 45000 or less, 40000 or less, 35000 or less, 30000 or less, 25000 or less, 20000 or less, 15000 or less, 10000 or less, 9000 or less, 8000 or less, or 7000 or less, but is not limited thereto.

The additive composition of the present application includes a polysiloxane component having the above structure, thereby providing an additive composition having excellent compatibility with silicone adhesive resins, being transparent, and having excellent antistatic properties.

The weight average molecular weight (Mw, Weight Average Molecular Weight) of the polysiloxane component represented by Formula 1 may be, for example, within the range of 5000 to 50000 g/mol. The weight average molecular weight may be a standard polystyrene conversion value measured by so-called GPC (Gel Permeation Chromatography), and its unit may be g/mol. In another example, the weight average molecular weight (Mw) of the polysiloxane component is 6000 g/mol or more, 7000 g/mol or more, 8000 g/mol or more, 9000 g/mol or more, 10000 g/mol or more, 11000 g/mol or more, 12000 g/mol or more, 13000 g/mol or more, or 14000 g/mol or more, or 45000 g/mol or less, 40000 g/mol or less, 35000 g/mol or less, 30000 g/mol or less, 25000 g/mol or less, or 20000 g / mol or less, but is not limited thereto.

The polysiloxane component represented by Formula 1 may also have a molecular weight distribution (PDI, Mw/Mn), that is, a ratio of weight average molecular weight (Mw) to number average molecular weight (Mn) in the range of 1.2 to 5.2. In another example, the molecular weight distribution is 1.3 or more, 1.4 or more, 1.5 or more, 1.6 or more, 1.7 or more, 1.8 or more, 1.9 or more, 2.0 or more, or 2.1 or more, or 5 or less, 4.8 or less, 4.6 or less, 4.4 or less, 4.2 or less, 4.0 or less, 3.8 or less, 3.6 or less, 3.4 or less, 3.2 or less, 3.0 or less, 2.8 or less, 2.6 or less, 2.4 or less, or 2.2 or less.

In the present application, the weight average molecular weight (Mw) and/or molecular weight distribution (Mw/Mn) may be measured according to the following evaluation examples.

The additive composition of the present application has compatibility with the silicone adhesive resin described later by controlling the weight average molecular weight (Mw) and/or molecular weight distribution (Mw/Mn) of the polysiloxane component represented by Formula 1 within the range described below. can be better

The additive composition of the present application may further include, for example, an ionic liquid. By further including an ionic liquid having the characteristics described below, it is possible to provide an additive composition having excellent compatibility with silicone adhesive resins, being transparent and having excellent antistatic properties.

The ionic liquids of the present application may include, for example, organic cations and inorganic anions. The organic cation and/or the inorganic anion may be appropriately selected in consideration of desired effects.

The ionic liquids of the present application include, for example, ammonium, imidazolium, oxazolium, piperidinium, pyrazinium, pyrazolium, pyriakinium, pyridinium, pyrimidium, pyrrolidinium, pyrrolinium and tria It may include a cation selected from the group consisting of zolium, but is not limited thereto. The ionic liquid of the present application is more preferably, for example, triethylmethylammonium, ethyltrimethylammonium, tripropylmethylammonium, tributylmethylammonium, N-ethyl-N-methylpyrrolidinium and N,N-di It may contain a cation selected from the group consisting of methylenepyrrolidinium. The ionic liquid of the present application may most preferably contain tributylmethylammonium as a cation in consideration of, for example, compatibility with anions, chemical stability, heat resistance, and/or antistatic properties, which will be described later.

The ionic liquids of the present application are, for example, F ^- , Cl ^- , B ^r -, I ^- , NO ₃ ^- , N(CN) ₂ ^- , BF ₄ ^- , ClO ₄ ^- , PF ₆ ^- , (CF ₃ ) ₂ PF ₄ ^- , (CF ₃ ) ₃ PF ₃ ^- , (CF ₃ ) ₄ PF ₂ ^- , (CF ₃ ) ₅ PF-, (CF ₃ ) ₆ P-, (CF ₃ SO ₃ ^- ) ₂ , (CF ₂ CF ₂ SO ₃ ^- ) ₂ , (CF ₃ SO ₃ ) ₂ N ^- , CF ₃ CF ₂ (CF ₃ ) ₂ CO ^- , (CF ₃ SO ₂ ) ₂ CH ^- , (SF ₅ ) ₃ C ^- , (CF ₃ SO ₂ ) ₃ C ^- , (CF ₃ SO ₂ ) ₂ N ^- , CF ₃ (CF ₂ ) ₇ SO ₃ ^- , CF ₃ CO ₂ ^- and CH ₃ CO ₂ ^- It may include, but is not limited to.

The ionic liquid of the present application may preferably include (CF ₃ SO ₂ ) ₂ N ^- as an anion in consideration of, for example, prevention of denaturation at high temperatures and/or fairness.

The additive composition of the present application includes the polysiloxane component represented by Formula 1 and/or the ionic liquid having the above characteristics, so that it has excellent compatibility with silicone adhesive resin, is transparent, and has excellent antistatic properties. can This object can be achieved more effectively by controlling the weight ratio of the polysiloxane component and the ionic liquid within a predetermined range.

The additive composition of the present application may include, for example, the ionic liquid in an amount within the range of 100 to 10,000 parts by weight based on 100 parts by weight of the polysiloxane component represented by Formula 1. In the present application, the ionic liquid is 200 parts by weight or more, 300 parts by weight or more, 400 parts by weight or more, 500 parts by weight or more, 600 parts by weight or more, 700 parts by weight or more, based on 100 parts by weight of the polysiloxane component represented by Formula 1. 800 parts by weight or more or 900 parts by weight or more, 9000 parts by weight or less, 8000 parts by weight or less, 7000 parts by weight or less, 6000 parts by weight or less, 5000 parts by weight or less, 4000 parts by weight or less, 3000 parts by weight or less, or 2000 parts by weight The following may be included, but are not limited thereto.

The ionic liquid of the present application may also further include, for example, lithium ions and the like. The lithium ion and the like may be included within a range of 5000 ppm or less. In another example, the lithium ion may be included in the ionic liquid within a range of 4000 ppm or less, 3000 ppm or less, 2000 ppm or less, or 1000 ppm or less.

The present application may provide an additive composition having excellent compatibility with a silicone adhesive resin, being transparent, and having excellent antistatic properties through a combination of the polysiloxane component and/or the ionic liquid.

This application may also relate to an adhesive composition.

The pressure-sensitive adhesive composition of the present application may include, for example, a silicone pressure-sensitive adhesive resin and the additive composition. In this case, the contents of the additive composition may be equally applied to the above-described additive composition.

In the present application, the silicone adhesive resin may be, for example, DC 7460 from Dow Corning, DC 7647 from Dow Corning, DC 7652 from Dow Corning, DC 7651 from Dow Corning, or DC 7659 from Dow Corning, but are not limited thereto. A silicone adhesive resin may be used.

Through the combination of the additive composition and the silicone adhesive resin of the present application, it is possible to provide a pressure-sensitive adhesive composition having excellent adhesiveness, transparency, and/or heat resistance, excellent antistatic properties, and no steaming during peeling.

The pressure-sensitive adhesive composition of the present application may include, for example, the additive composition in the range of 5 to 30 parts by weight based on 100 parts by weight of the silicone pressure-sensitive adhesive resin. In another example, the pressure-sensitive adhesive composition of the present application may contain 6 parts by weight or more, 7 parts by weight or more, 8 parts by weight or more, 9 parts by weight or more, 10 parts by weight or more, 11 parts by weight or more, 12 parts by weight or more, 13 parts by weight or more, 14 parts by weight or more, 15 parts by weight or more, 16 parts by weight or more, or 17 parts by weight or more, or 29 parts by weight or less, 28 parts by weight or less, 27 parts by weight or less, 26 parts by weight or less, 25 parts by weight or less, 24 parts by weight or less, 23 parts by weight or less, 22 parts by weight or less, 21 parts by weight or less, 20 parts by weight or less, 19 parts by weight or less, or 18 parts by weight or less, but is not limited thereto.

This application may also relate to a protective film.

The protective film of the present application may include, for example, a base film and/or a pressure-sensitive adhesive layer including a pressure-sensitive adhesive composition formed on the base film. In this application, the meaning that the pressure-sensitive adhesive layer is formed on the base film may mean, for example, that the pressure-sensitive adhesive layer is directly contacted and formed on the base film, and a separate layer is formed between the base film and the pressure-sensitive adhesive layer. It could mean that it exists. In this case, the contents of the pressure-sensitive adhesive composition may be equally applied to the contents of the above-described pressure-sensitive adhesive composition. The separate layer may not be limited as long as the function of the protective film is not impaired.

The base film of the present application may have, for example, a thickness in the range of 10 μm to 500 μm. In another example, the thickness of the base film is 15 μm or more, 20 μm or more, 25 μm or more, 30 μm or more, 35 μm or more, 40 μm or more, 45 μm or more, 50 μm or more, 55 μm or more, 60 μm or more, It may be 65 μm or more or 70 μm or more, 450 μm or less, 400 μm or less, 350 μm or less, 300 μm or less, 250 μm or less, 200 μm or less, 150 μm or less, or 100 μm or less.

The pressure-sensitive adhesive layer may have, for example, a thickness in the range of 0.1 μm to 10 μm. In another example, the pressure-sensitive adhesive layer has a thickness of 0.5 μm or more, 1 μm or more, 1.5 μm or more, 2 μm or more, or 2.5 μm or more, or 9 μm or less, 8 μm or less, 7 μm or less, 6 μm or less, 5 μm or less, or It may be 4 μm or less.

The protective film of the present application may have excellent properties such as antistatic properties, bonding strength, surface resistance, haze characteristics and/or appearance by including the above-described additive composition and/or pressure-sensitive adhesive composition.

In one example, the protective film of the present application may have excellent antistatic properties. In the present application, excellent antistatic property may mean, for example, that the stripping electrification voltage is within a range of 10000 V or less. In another example, the protective film of the present application has a peeling electrification voltage of 9500 V or less, 9000 V or less, 8500 V or less, 8000 V or less, 7500 V or less, 7000 V or less, 6500 V or less, 6000 V or less, 5500 V or less, 5000 V or less, 4500 V or less, 4000 V or less, 3500 V or less, 3000 V or less, 2500 V or less, 2000 V or less, 1500 V or less, or 1000 V or less. The lower limit of the peeling electrification voltage is not particularly limited, but is, for example, 10 V or more, 20 V or more, 30 V or more, 40 V or more, 50 V or more, 60 V or more, 70 V or more, 80 V or more, 90 V or more. It may be on the order of more than 100 V or more. The peel electrification voltage may be measured according to an evaluation example to be described later.

In another example, the protective film of the present application may have excellent bonding strength. In the present application, excellent bonding strength may mean that steaming of the pressure-sensitive adhesive layer of the protective film is appropriately controlled. In the present application, the proper control of the steaming means that, for example, in the process of attaching and/or detaching a separate layer on the pressure-sensitive adhesive layer of the protective film, all and/or some of the components of the pressure-sensitive adhesive layer are attached to the separate layer. It may mean that the phenomenon does not occur, or even if the phenomenon occurs, the degree is insignificant, so that there is no problem in exhibiting the function of the protective film.

The protective film of the present application may also have excellent surface properties, for example. In the present application, excellent surface properties may mean, for example, that no wavy patterns or irregularities are observed during visual observation. In the present application, excellent surface properties may mean, in another example, that the thickness uniformity of the protective film is excellent. In one example, the surface properties of the protective film may be evaluated according to a surface condition evaluation method described later.

The protective film of the present application may also have excellent surface resistance characteristics. In the present application, excellent surface resistance characteristics of the protective film may mean, for example, that the protective film has a surface resistance of less than E+13 Ω/ㅁ. In another example, the protective film of the present application has a surface resistance of less than E + 12Ω / ㅁ, less than E + 11 Ω / ㅁ, or less than E + 10 Ω / ㅁ, E + 5 Ω / ㅁ or more, E + 6 It may have a surface resistance of Ω/ㅁ or more, E+7 Ω/ㅁ or more, E+8 Ω/ㅁ or more, or E+9 Ω/ㅁ or more.

The protective film of the present application may have excellent transparency. In the present application, excellent transparency of the protective film may mean, for example, excellent haze characteristics. The protective film of the present application may have, for example, a measured haze value of 2% or less. The haze characteristics may be measured according to evaluation examples described later. In another example, the protective film of the present application may mean that the haze measurement value is 1.9% or less, 1.8% or less, 1.7% or less, 1.6% or less, 1.5% or less, or 1.4% or less. The lower limit of the haze measurement value is not particularly limited, but in one example, it may be 0.1% or more, 0.2% or more, 0.3% or more, 0.4% or more, 0.5% or more, 0.6% or more, 0.7% or more, or 0.8% or more.

The protective film of the present application may be applied, for example, to protect a polarizer during manufacture and/or packaging of a display such as OLED (Organic Light-Emitting Diodes). The protective film of the present application includes the additive composition and/or the pressure-sensitive adhesive composition having the above-described characteristics, so that the desired antistatic property can be realized without a separate post-treatment process, and other physical properties, such as adhesion, transparency and/or Heat resistance and the like may be excellent.

The present application can provide an additive composition having excellent compatibility with silicone adhesive resins, being transparent, and having excellent antistatic properties. In addition, the present application can provide a pressure-sensitive adhesive composition having excellent adhesiveness, transparency, heat resistance, etc., excellent antistatic property, and no steaming during peeling, by including the additive composition.

Evaluation Example 1. Evaluation of surface resistance

After the protective film prepared in Examples and Comparative Examples was prepared as a sample of 30 cm in width X 30 cm in length, surface resistance was measured using a surface resistance meter (PRS-801, PROSTAT (USA)). At this time, the surface resistance is measured for 8 seconds at a voltage of 100V for the top, middle, and bottom 3 points of the sample (upper, middle, and mean each point within a straight line divided into thirds horizontally or vertically) did The average values of the measurement results are shown in Table 1 below.

Evaluation Example 2. Evaluation of binding force

The protective film prepared in Examples and Comparative Examples was prepared as a sample of 30 cm in width X 30 cm in length. Subsequently, a tape (Scotch tape, 3M) measuring 2 cm in width X 5 cm in length was horizontally attached to the pressure-sensitive adhesive layer surface of the sample, and then attached and detached once. After the attachment and detachment, the tape was visually observed, and the results are shown in Table 1 below.

<Evaluation Criteria>

O: As a result of bonding force evaluation, the material smeared on the tape was not visually observed.

△: As a result of bonding force evaluation, a very small amount of foreign matter on the tape was observed (as a result of cross-cutting and observing a random 1 cm x 1 cm area of the sample in units of 1 mm x 1 mm, 3 out of 100 unit areas) levels at which foreign bodies are observed in less than 10).

X: As a result of bonding force evaluation, foreign matter on the tape was visually observed.

Evaluation Example 3. Peeling electrification voltage evaluation

의 온도 및 50%R.H.의 환경 하에서 측정하였다. After attaching the release film (product name, manufacturer) on the adhesive layer of the protective film prepared in Examples and Comparative Examples, it was prepared as a sample of 30 cm in width X 30 cm in length. Then, the sample was left for 1 day in an environment of a temperature of 23° C. and 50% R.H. Subsequently, the peeling electrification voltage when the protective film was peeled from the release film was measured using a static meter (SPE-100, MISUMI, Korea). At this time, a voltage of 10 kV was applied to the sample, and 23

of temperature and 50%R.H.

Evaluation Example 4. Cotton condition evaluation

After scratching the protective film prepared in Examples and Comparative Examples three times with a bar quarterer (RDS, RDS/USA), the surface of the protective film was visually observed.

<Evaluation Criteria>

O: When observing the surface of the protective film with the naked eye, the surface is smooth.

△: When observing the surface of the protective film with the naked eye, some minor irregularities are present.

X: When the surface of the protective film is observed with the naked eye, irregularities are present.

Evaluation Example 5. Haze Evaluation

The haze of the protective film was measured using a measuring instrument (HM-150, MCRL). The measurement was performed according to the JIS K 7136 standard in a transmission mode by allowing light to be incident on the concave-convex surface of the protective film.

Evaluation Example 6. GPC (Gel Permeation Chromatography)

Number average molecular weight (Mn) and molecular weight distribution were measured using GPC (Gel permeation chromatography). Put the analyte in a 5 mL vial, and dilute in THF (tetrahydro furan) to a concentration of about 1 mg/mL. After that, the standard sample for calibration and the sample to be analyzed were filtered through a syringe filter (pore size: 0.45 μm) and then measured. The analysis program used ChemStation from Agilent Technologies, and the elution time of the sample was compared with the calibration curve to obtain the weight average molecular weight (Mw) and number average molecular weight (Mn), and the molecular weight distribution (PDI) was determined by the ratio (Mw/Mn) was calculated. The measurement conditions of GPC are as follows.

<GPC measurement conditions>

Device: 1200 series by Agilent technologies

Column: Use 2 PLgel mixed B from Polymer laboratories

Solvent: THF

Column temperature: 35 ℃

Sample concentration: 1 mg/mL, 200 μL injection

Standard samples: Polystyrene (Mp: 3900000, 723000, 316500, 52200, 31400, 7200, 3940, 485)

Preparation Example 1. Preparation of Additive Composition A

의 온도에서 rpm 30의 조건으로 20분 간 믹싱(mixing)하였다. 상기 -부틸-w-[[3-[2,2-비스(히드록시메틸)부토리]프로필]폴리디메틸 실록산의 중량평균분자량(Mw)은 15000 g/mol 이었고, 분자량 분포(Mw/Mn)는 약 2.14 정도였다. 이후 상기 조성물을 상온이 될 때까지 냉각시켜 첨가제 조성물을 완성하였다. After adding tributylmethylammonium bis(trifluoromethylsulfonyl)imide (FC4400, 3M) to a double jacketed cylinder, mixing was performed at a temperature of about 50°C and an rpm of 100 for 10 minutes. Then, based on 100 parts by weight of the tributylmethylammonium bis (trifluoromethylsulfonyl) imide, -butyl-w-[[3-[2,2-bis(hydroxymethyl)butyric]propyl]polydimethylsiloxane (Silaplane, JNC) after adding 10 parts by weight, about 60

At a temperature of 20 minutes under the condition of rpm 30 (mixing) was. The weight average molecular weight (Mw) of the -butyl-w-[[3-[2,2-bis(hydroxymethyl)butory]propyl]polydimethylsiloxane was 15000 g/mol, and the molecular weight distribution (Mw/Mn) was about 2.14. Thereafter, the composition was cooled to room temperature to complete an additive composition.

Example 1.

An adhesive composition was prepared by adding about 17.65 parts by weight of the additive composition A of Preparation Example 1 to 100 parts by weight of a silicone adhesive resin (DC 7460, Dow Corning). At this time, the preparation of the pressure-sensitive adhesive composition was performed in a mixer (MARK-2, Hansol) with one impeller. Subsequently, the prepared pressure-sensitive adhesive composition was coated on a PET film (SKC) having a thickness of about 75 μm using a micro gravure method. As a result, a protective film having a pressure-sensitive adhesive layer having a thickness of about 3 μm was prepared.

Example 2.

A protective film was prepared in the same manner as in Example, except that about 11.11 parts by weight of additive composition A was added to 100 parts by weight of silicone adhesive resin (DC 7460, Dow Corning).

Example 3.

A protective film was prepared in the same manner as in Example, except that about 25 parts by weight of additive composition A was added to 100 parts by weight of silicone adhesive resin (DC 7460, Dow Corning).

Comparative Example 1.

A protective film was prepared in the same manner as in Example, except that the additive composition A was not introduced.

Comparative Example 2.

A protective film was prepared in the same manner as in Example, except that 5 parts by weight of an additive composition (fluorine-based ionic liquid, HAIHANG) was added to 100 parts by weight of a silicone adhesive resin (DC7460, Dow Corning).

[Table 1]

Claims (11)

Including a polysiloxane component and an ionic liquid represented by Formula 1 below,
The ionic liquid is an additive composition included in parts by weight within the range of 100 to 10000 based on 100 parts by weight of the polysiloxane component represented by Formula 1:
[Formula 1]
(R ¹ ₃ SiO) - (R ² ₂ SiO) _n - (SiR ³ ₃ )
In Formula 1, R ¹ to R ³ are each independently a hydrogen atom, a hydrocarbon group, or a compound represented by the following Formula 2, and when a plurality of R ¹ to R ³ are present, they are the same as or different from each other, and R ¹ to R 3 At least one of R ³ is a compound represented by Formula 2, n is a number within the range of 300 to 50000, and the weight average molecular weight (Mw) of the polysiloxane component represented by Formula 1 is within the range of 5000 to 50000 g/mol. am:
[Formula 2]
PLQ
In Formula 2, P to Q are each independently a hydrogen atom or a hydrocarbon group, L is an oxygen atom or a sulfur atom, and at least one of Q is a hydroxyl group, a carboxyl group, an aldehyde group, a carbonyl group, or an isocyanate group.
delete delete delete 2. The method of claim 1, wherein the ionic liquid is selected from ammonium, imidazolium, oxazolium, piperidinium, pyrazinium, pyrazolium, pyriakinium, pyridinium, pyrimidium, pyrrolidinium, pyrrolinium and triazolium. A cation selected from the group consisting of F ^- , Cl ^- , B ^r -, I ^- , NO ₃ ^- , N(CN) ₂ ^- , BF ₄ ^- , ClO ₄ ^- , PF ₆ ^- , (CF ₃ ) ₂ PF ₄ ^- , (CF ₃ ) ₃ PF ₃ ^- , (CF ₃ ) ₄ PF ₂ ^- , (CF ₃ ) ₅ PF-, (CF ₃ ) ₆ P-, (CF ₃ SO ₃ ^- ) ₂ , (CF ₂ CF ₂ SO ₃ ^- ) ₂ , (CF ₃ SO ₃ ) ₂ N ^- , CF ₃ CF ₂ (CF ₃ ) ₂ CO ^- , (CF ₃ SO ₂ ) ₂ CH ^- , (SF ₅ ) ₃ C ^- , (CF ₃ SO ₂ ) An additive composition comprising an anion selected from the group consisting of ₃ C ^- , (CF ₃ SO ₂ ) ₂ N ^- , CF ₃ (CF ₂ ) ₇ SO ₃ ^- , CF ₃ CO ₂ ^- and CH ₃ CO ₂ ^- .
delete The additive composition according to claim 1, wherein the molecular weight distribution (Mw/Mn) of the polysiloxane component represented by Formula 1 is in the range of 1.2 to 5.2.
The additive composition of claim 1 , wherein the ionic liquid further comprises lithium ions.
silicone adhesive resin; And a pressure-sensitive adhesive composition comprising the additive composition of claim 1.
10. The pressure-sensitive adhesive composition according to claim 9, wherein the additive composition is included in the range of 5 to 30 parts by weight based on 100 parts by weight of the silicone pressure-sensitive adhesive resin.
base film; and a pressure-sensitive adhesive layer comprising the pressure-sensitive adhesive composition of claim 9 formed on the base film.