WO2017069382A1 - Silicone adhesive composition - Google Patents

Abstract

The present invention relates to a silicone adhesive composition containing: an organopolysiloxane comprising a vinyl silane group; an organopolysiloxane comprising a hydrosilyl group; a compound containing, within one molecule, a vinyl group and one or more selected from the group consisting of an epoxy group, an isocyanate group, a hydroxyl group and an amino group; and an addition reaction catalyst, and the silicone adhesive composition of the present invention has a low modulus of elasticity and excellent adhesive strength.

Description

Silicone adhesive composition

The present invention relates to a silicone pressure-sensitive adhesive composition, more specifically organopolysiloxane comprising a vinylsilane group; Organopolysiloxanes including hydrosilyl groups; A compound comprising at least one member selected from the group consisting of a vinyl group and an epoxy group, an isocyanate group, a hydroxy group and an amino group in one molecule; It relates to a silicone pressure-sensitive adhesive composition comprising; and an addition reaction catalyst.

An adhesive is one kind of adhesive, and is often used in the form of an adhesive tape, an adhesive label, etc. which apply | coated an adhesive to the base material, and is a typical thing of the article using the adhesive which we usually see. These articles are used for various purposes, such as used for labels for identifying articles, for packing bags, or for connecting a plurality of things together.

There are several kinds of base materials for constituting the pressure-sensitive adhesive, and largely divided into rubber, acrylic, silicone, and the like.

Rubber-based pressure-sensitive adhesives are a general-purpose base material that has been used for a long time, and are used for products such as general-purpose tapes with low cost.

The acrylic pressure sensitive adhesive uses polyacrylate as a base, and can be applied to pressure sensitive adhesive products having a higher function than rubber in that chemical properties and the like are superior to rubber.

The silicone pressure sensitive adhesive includes high viscosity silicone raw rubber (gum) and silicone resin, and has various excellent characteristics in that the main chain has a plurality of siloxane bonds, and specifically, heat resistance, cold resistance, weather resistance, chemical resistance, electrical insulation, etc. Can be mentioned.

The silicone pressure-sensitive adhesive is used for high-performance tapes for industrial use such as heat-resistant tapes, process masking tapes, and mica tapes having flame retardancy by utilizing the excellent properties as described above. It is used.

However, in recent years, the demand of silicone adhesives is rapidly expanding, and the cause thereof is the expansion of the product market employing a touch panel mounted on a smartphone, a tablet terminal, or the like. In most cases, the touch panel is bonded to a screen protection film in order to prevent contamination or scratches of the display since it is directly operated by a human finger. Most of the silicone pressure sensitive adhesives used in the pressure-sensitive adhesive layer of the screen protective film are made of the characteristics of wettability and rework property of the excellent adherend of the silicone pressure sensitive adhesive.

The base material used for a screen protection film is a plastic film, and many polyester films, such as PET, which have transparency are used. However, the plastic film is considered to be inferior to adhesiveness with an adhesive compared with a paper base material. This is considered to be because the plastic film has a flat surface and a weak anchoring effect in which the adhesive penetrates into the substrate as compared with paper having a large unevenness. When adhesiveness is bad, a problem may arise that an adhesive layer transfers to a to-be-adhered body when peeling after a time passes by adhering to a back surface or adhering to a to-be-adhered body when winding up with a roll.

In order to improve this adhesiveness, various measures have been taken before, and there exist methods, such as using a base material with good adhesiveness, or corona-treating a base material. Moreover, the primer process is also widely performed, and development is progressing also about the primer composition for silicone pressure sensitive adhesives. Although primer treatment is very effective, one increase in the number of coating processes is a major drawback, and cost and productivity are a problem. As an effective countermeasure, the method of adding the component which improves adhesiveness to a silicone adhesive and ensuring adhesiveness by one coating is considered. Although such additives exist, the improvement of adhesiveness is calculated | required further. In addition, Japanese Patent No. 3324166 describes an additive that selectively adheres to an organic resin, but the object is a silicone rubber composition, and no silicone adhesive is mentioned.

Conventional silicone pressure-sensitive adhesive composition improved the cohesive force by using the MQ resin, thereby improving the cohesive force. However, when the cohesive force is improved, the elastic modulus is increased to harden the silicone pressure-sensitive adhesive composition, and thus, when the substrate to which the silicone pressure-sensitive adhesive composition is applied is bent, cracks may occur.

Therefore, an object of the present invention is to provide a silicone pressure-sensitive adhesive composition excellent in adhesive strength by improving the softness and adhesion while low elastic modulus to solve the above problems.

Moreover, an object of this invention is to provide the silicone adhesive composition excellent in peeling resistance.

In order to achieve the above object,

The present invention is an organopolysiloxane comprising a vinylsilane group; Organopolysiloxanes including hydrosilyl groups; A compound comprising at least one member selected from the group consisting of a vinyl group and an epoxy group, an isocyanate group, a hydroxy group and an amino group in one molecule; It provides a silicone pressure-sensitive adhesive composition comprising; and an addition reaction catalyst.

In addition, the present invention provides a silicone pressure-sensitive adhesive prepared from the silicone pressure-sensitive adhesive composition of the present invention.

In addition, the present invention provides a film coated with the silicone pressure-sensitive adhesive.

The silicone pressure-sensitive adhesive composition of the present invention has a low elastic modulus and excellent adhesive force.

Therefore, when the silicone pressure-sensitive adhesive composition of the present invention is applied to a substrate and the substrate is bent, cracks do not occur, and the peeling resistance is excellent.

In addition, the silicone pressure-sensitive adhesive composition of the present invention has an effect of excellent adhesion to the substrate.

1 is a view showing a mechanism in which the silicone pressure-sensitive adhesive composition of the present invention is bonded to a substrate.

2 is a view showing a folding characteristic evaluation method of a substrate on which a silicone pressure-sensitive adhesive composition is applied.

Hereinafter, the present invention will be described in more detail.

The present invention is an organopolysiloxane comprising a vinylsilane group; Organopolysiloxanes including hydrosilyl groups; A compound comprising at least one member selected from the group consisting of a vinyl group and an epoxy group, an isocyanate group, a hydroxy group and an amino group in one molecule; It relates to a silicone pressure-sensitive adhesive composition comprising; and an addition reaction catalyst.

Increasing the modulus of elasticity increases cohesion, thereby increasing the cohesion.

Conventional silicone pressure-sensitive adhesive composition has increased the adhesive strength with the substrate by increasing the elastic modulus, and in order to increase the elastic modulus, MQ resin is added to the silicone pressure-sensitive adhesive composition or a technique of improving the crosslinking density is used.

However, when the elastic modulus is high, the composition is hardened, so that a crack occurs when the silicone pressure-sensitive adhesive composition is applied to the substrate and the substrate is bent.

Therefore, the present invention was to provide a silicone adhesive composition having a low elastic modulus and excellent adhesion to solve the above problems, for this purpose, without adding a MQ resin or using a technique for increasing the crosslinking density, while suppressing the increase in the elastic modulus Adhesion enhancers were used to enhance adhesion.

In the present invention, the adhesion promoter is a compound containing at least one selected from the group consisting of a vinyl group, an epoxy group, an isocyanate group, a hydroxyl group and an amino group in one molecule.

The board | substrate to which the silicone adhesive composition of this invention is apply | coated is a board | substrate containing a carboxyl group or a hydroxyl group on the surface.

Preferably, a cycloolefin polymer (CycloOlefinPolymer, COP) having a carboxyl group introduced on the surface by corona treatment or triacetate cellulose (TAC) having a hydroxyl group on the surface may be used as a substrate.

The organopolysiloxane including the vinylsilane group serves as a main body of the silicone pressure sensitive adhesive composition, and the organopolysiloxane including the hydrosilyl group serves as a crosslinking agent of the silicone pressure sensitive adhesive composition.

Due to the addition reaction catalyst, addition reaction of the organopolysiloxane including the hydrosilyl group and the organopolysiloxane including the vinylsilane group occurs.

In addition, the vinyl group of the organopolysiloxane including the hydrosilyl group and the adhesion enhancer of the low modulus of elasticity may be cross-linked to form an adhesive layer of the silicone pressure-sensitive adhesive composition.

In addition, at least one member selected from the group consisting of an epoxy group, an isocyanate group, a hydroxyl group and an amino group of the adhesion modifier of the low elastic modulus is connected by reacting with a carboxyl group or a hydroxyl group of the substrate (FIG. 1), so that the elastic modulus is low and the adhesion force with the substrate is low. This very excellent silicone adhesive composition can be provided.

Hereinafter, the silicone pressure-sensitive adhesive composition of the present invention will be described in detail for each component.

(A) organopolysiloxane containing vinylsilane group

The organopolysiloxane including the vinylsilane group which is one component of the silicone pressure sensitive adhesive composition of the present invention is a component that serves as a main component of the silicone pressure sensitive adhesive composition.

The vinylsilane group (CH ₂ = CH-Si) may be included in the terminal or molecule of the organopolysiloxane, and the position of the vinylsilane group and the type of organopolysiloxane including the vinylsilane group are not particularly limited.

However, the organopolysiloxane including the vinylsilane group may preferably include one or more selected from the group consisting of the following Chemical Formulas 1 to 3.

[Formula 1]

[Formula 2]

[Formula 3]

N, m, p, q and r are each independently an integer of 1 to 1000,

The ratio of the p unit and m unit is 100: 1 to 10: 1,

The ratio of the q unit and the r unit is 100: 1 to 10: 1.

When the ratio of m unit in the ratio of p unit and m unit exceeds the above range, the glass transition temperature (Tg) of the polymer increases, the elastic modulus of the adhesive layer becomes excessively high, resulting in a problem of insufficient crack suppression of the substrate. do.

In addition, when the ratio of the r unit in the ratio of the q unit and the r unit exceeds the above range, the degree of crosslinking increases, the elastic modulus of the pressure-sensitive adhesive layer becomes too high, resulting in a problem that the crack suppressibility of the substrate is insufficient.

The vinylsilane group of the organopolysiloxane including the vinylsilane group may cause an addition reaction with the organopolysiloxane (B) including the hydrosilyl group due to the addition reaction catalyst (D) described later to connect the two compounds.

In addition, the organopolysiloxane including the vinylsilane group is included in 50 to 90% by weight, preferably 60 to 80% by weight based on the total weight of the silicone pressure-sensitive adhesive composition of the present invention.

When the organopolysiloxane including the vinylsilane group is included in the range of 50 to 90% by weight, low elastic modulus and high adhesion may be expressed.

(B) organopolysiloxane containing a hydrosilyl group

The organopolysiloxane including a hydrosilyl group as one component of the silicone pressure sensitive adhesive composition of the present invention is a component that serves as a crosslinking agent of the silicone pressure sensitive adhesive composition.

In the present invention, the type of organopolysiloxane including the hydrosilyl group (Si-H) is not particularly limited, but may preferably include one or more selected from the group consisting of the following Chemical Formulas 4 to 7.

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

X, a, b, c, d, e and f are each independently an integer of 1 to 1000,

The ratio of the a unit and b unit is 100: 1 to 10: 1,

The ratio of the c unit and d unit is 100: 1 to 10: 1,

The ratio of the e unit and f unit is 100: 1 to 10: 1.

If the ratio of the a unit, the c unit and the e unit in the ratio of the a unit and the b unit, the ratio of the c unit and the d unit and the ratio of the e unit and the f unit is less than 10, the crosslinking degree is excessively increased to increase the elastic modulus. This makes it difficult to secure folding characteristics. In addition, when the ratio of a unit, c unit, and e unit exceeds 100, the hydrosilyl group has a small farm, and it is difficult to fix the adhesion enhancer, and thus it is difficult to expect the effect of improving adhesion.

The organopolysiloxane including the hydrosilyl group may be reacted with the organopolysiloxane (A) including the vinylsilane group described above due to the addition reaction catalyst (D) described below to connect the two compounds.

In addition, a vinyl group and a vinyl group of a compound (C) containing at least one member selected from the group consisting of an epoxy group, an isocyanate group, a hydroxy group and an amino group in a molecule to be described later, which is a low elastic modulus adhesion promoter, react with the compound. Can be connected.

That is, the organopolysiloxane including the hydrosilyl group includes at least one member selected from the group consisting of a vinyl group and an epoxy group, an isocyanate group, a hydroxy group and an amino group in one molecule of the organopolysiloxane (A) including a vinylsilane group. It may be linked with compound (C).

In addition, the organopolysiloxane including the hydrosilyl group is included in 5 to 40% by weight, preferably 15 to 25% by weight based on the total weight of the silicone pressure-sensitive adhesive composition of the present invention.

When the organopolysiloxane including the hydrosilyl group is included in the range of 5 to 40% by weight, the elastic modulus is low and the adhesive force is easily expressed.

In addition, when included in less than 5% by weight, the effect of improving the adhesive force is insufficient due to the decrease in the concentration of the hydrosilyl group, when the content exceeds 40% by weight may cause a problem that the release peel force is increased.

(C) A compound containing at least one member selected from the group consisting of a vinyl group and an epoxy group, an isocyanate group, a hydroxyl group and an amino group in one molecule

Compounds containing at least one member selected from the group consisting of a vinyl group, an epoxy group, an isocyanate group, a hydroxy group, and an amino group in one molecule of the silicone adhesive composition of the present invention serve as a low modulus adhesion enhancer of the silicone adhesive composition. Ingredient.

That is, by using the compound, it is possible to provide a silicone pressure-sensitive adhesive composition having a low elastic modulus and excellent adhesion.

The vinyl group of the compound is connected by reaction with an organopolysiloxane including the hydrosilyl group, and at least one selected from the group consisting of an epoxy group, an isocyanate group, a hydroxyl group and an amino group of the compound reacts with a carboxyl group or a hydroxy group on the substrate surface. Connected.

By connecting with the hydroxyl group or carboxyl group of a board | substrate, the silicone adhesive composition excellent in the adhesive force can be obtained.

The compound containing at least one member selected from the group consisting of a vinyl group, an epoxy group, an isocyanate group, a hydroxy group and an amino group in the molecule is not particularly limited, but preferably from the group consisting of the following Chemical Formulas 8 to 14 It includes one or more selected.

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

[Formula 13]

[Formula 14]

The compound containing at least one selected from the group consisting of a vinyl group, an epoxy group, an isocyanate group, a hydroxy group and an amino group in the molecule is included in an amount of 1 to 15% by weight, based on the total weight of the silicone pressure-sensitive adhesive composition of the present invention. Preferably 5 to 10% by weight.

When the compound is included in the range of 1 to 15% by weight, the elastic modulus is low, and the adhesive force is easily expressed.

If the compound is contained in less than 1% by weight, the hydrogen bonding or covalent bonds with the substrate lacks the ability to improve the adhesion, if included in more than 15% by weight, the lowering of the adhesion by dissolution of the uncured additive This may be a concern.

(D) addition reaction catalyst

The addition reaction catalyst which is one component of the silicone pressure-sensitive adhesive composition of the present invention is a catalyst causing the addition reaction of the organopolysiloxane (A) including the vinylsilane group and the organopolysiloxane (B) including the hydrosilyl group.

The addition reaction catalyst is a platinum group metal catalyst, and is selected from the group consisting of platinum (Pt), palladium (Pd), iridium (Ir), rhodium (Rh), osmium (Os), and ruthenium (Ru) as a central metal. It contains the above, Preferably it contains platinum (Pt).

The addition reaction catalyst is included in 0.01 to 1% by weight, preferably 0.05 to 0.5% by weight based on the total weight of the silicone pressure-sensitive adhesive composition of the present invention.

When the compound is contained in less than 0.01% by weight, there is a fear that the degree of curing of the adhesive layer is lowered, or the curing temperature is excessively increased, and when the compound is included in an amount of more than 1% by weight, the time-dependent change of the composition is large, resulting in a gel (gel) during the coating process. There is a risk of becoming).

In addition, the silicone pressure-sensitive adhesive composition of the present invention may further include a solvent, and the silicone pressure-sensitive adhesive composition may be dissolved in the solvent, the solution may be applied to a substrate, heated and dried to form a silicone pressure-sensitive adhesive layer.

An aromatic hydrocarbon type, an aliphatic hydrocarbon type, a ketone type solvent, etc. can be used for the said solvent, Preferably, toluene is used also in an aromatic hydrocarbon type.

In addition, the present invention provides a silicone pressure-sensitive adhesive prepared from the silicone pressure-sensitive adhesive composition of the present invention.

Since the silicone pressure-sensitive adhesive composition of the present invention has a low elastic modulus and excellent adhesion, it can be said that the silicone pressure-sensitive adhesive of the present invention has the same characteristics as described above.

In addition, the silicone pressure-sensitive adhesive of the present invention is applied to a substrate containing a carboxyl group or a hydroxyl group on the surface, and a vinyl group, an epoxy group, an isocyanate group, a hydroxyl group and an amino group in one molecule which is one of the components of the silicone pressure-sensitive adhesive composition of the present invention. At least one selected from the group consisting of an epoxy group, an isocyanate group, a hydroxyl group, and an amino group of a compound including at least one member selected from the group consisting of reacts with a carboxyl group or a hydroxyl group on the surface of the substrate and has excellent adhesion to the substrate, thereby providing excellent adhesion. Silicone adhesives can be provided.

In addition, the present invention may provide a film to which the silicone pressure-sensitive adhesive of the present invention is applied, and the film has an effect of not causing cracks when bent.

Hereinafter, the present invention will be described in detail with reference to Examples. However, embodiments according to the present invention can be modified in many different forms, and the scope of the present invention should not be construed as being limited to the embodiments described below. The embodiments of the present invention are provided to more completely explain the present invention to those skilled in the art.

<Silicone Adhesive Composition Preparation>

Example  1 to 12 and Comparative example  1 to 6.

By stirring for 1 hour to the composition of Table 1, to prepare a silicone pressure-sensitive adhesive composition of Examples 1 to 12 and Comparative Examples 1 to 6.

(Unit: g)

division	Organopolysiloxanes containing vinylsilane groups		Organopolysiloxanes containing hydrosilyl groups		Adhesion Enhancer		Addition reaction catalyst	toluene	Organopolysiloxanes containing silanol groups
	Kinds	content	Kinds	content	Kinds	content	content	content	Kinds	content
Example 1	Formula 1	100	Formula 4	30	Formula 8	10	0.5	200	-	-
Example 2	Formula 2	100	Formula 4	30	Formula 8	10	0.5	200	-	-
Example 3	Formula 3	100	Formula 4	30	Formula 8	10	0.5	200	-	-
Example 4	Formula 1	100	Formula 4	30	Formula 10	10	0.5	200	-	-
Example 5	Formula 1	100	Formula 4	30	Formula 11	10	0.5	200	-	-
Example 6	Formula 2	100	Formula 4	30	Formula 11	10	0.5	200	-	-
Example 7	Formula 3	100	Formula 4	30	Formula 11	10	0.5	200	-	-
Example 8	Formula 1	100	Formula 4	30	Formula 13	10	0.5	200	-	-
Example 9	Formula 1	100	Formula 5	30	Formula 8	10	0.5	200	-	-
Example 10	Formula 1	100	Formula 7	30	Formula 8	10	0.5	200	-	-
Example 11	Formula 1	100	Formula 5	30	Formula 11	10	0.5	200	-	-
Example 12	Formula 1	100	Formula 7	30	Formula 11	10	0.5	200	-	-
Comparative Example 1	Formula 1	100	Formula 4	30	-	-	0.5	200	-	-
Comparative Example 2	Formula 2	100	Formula 4	30	-	-	0.5	200	-	-
Comparative Example 3	Formula 3	100	Formula 4	30	-	-	0.5	200	-	-
Comparative Example 4	Formula 1	100	Formula 5	30	-	-	0.5	200	-	-
Comparative Example 5	Formula 1	100	Formula 7	30	-	-	0.5	200	-	-
Comparative Example 6	-	-	-	-	Formula 8	10	-	200	Formula 15	130

Formula 1 (manufactured by gelist, DMS-V05)

Formula 2 (manufactured by gelist, PDV-0331)

Formula 3 (manufactured by gelist, VDT-131)

Organopolysiloxanes containing hydrosilyl groups:

[Formula 4] (manufactured by gelist, HMS-H11)

[Formula 5] (manufactured by gelist, HMS-031)

[Formula 7] (HDP-111 manufactured by gelist)

Adhesion Enhancer:

[Formula 8]

[Formula 10]

[Formula 11]

[Formula 13]

Addition Catalyst: PLATINUM-DIVINYLTETRAMETHYLDISILOXANE COMPLEX (SIP6830.3)

Organopolysiloxanes containing silanol groups:

[Formula 15] (manufactured by gelist, DMS-S15)

Experimental Example  One. Peel force  Measure

On the polyimide (PI) substrate having a thickness of 50 μm, the silicone adhesive compositions of Examples 1 to 12 and Comparative Examples 1 to 6 were coated (optically clear adhesive, OCA), and dried at 120 ° C. for 3 minutes to adhere the silicone. A layer was formed.

Bonding the fluorine-based release film on the silicon adhesive layer, and left for 24 hours at room temperature.

After cutting the sample to 25 mm width, the release film was removed. Using a double-sided pressure-sensitive adhesive on the top of the release film was bonded a saponified TAC (TriAcetyl Cellulose) film fixed on the glass.

The bonded sample (TAC / OCA / PI) was left at room temperature for 24 hours, and then peeled at 180 ° using an autograph to measure the peel force, and the results are shown in Table 2 below.

Experimental Example  2. Folding (folding) properties

By folding the sample prepared in Experimental Example 1 (TAC / OCA / PI) at an angle of 0 ° and 180 ° in the direction of the TAC film (FIG. 2), cracks and adhesives of PI every 10,000 times Peeling was observed under a microscope.

Each, cracking and peeling were measured by measuring the number of folding occurs, and crack resistance and peeling resistance were evaluated, and the results are shown in Table 2 below.

	adhesiveness	Crack	Peeling occurrence
Example 1	9N	Not Occurred	Not Occurred
Example 2	13N	150,000 times	Not Occurred
Example 3	11N	Not Occurred	Not Occurred
Example 4	5N	Not Occurred	180,000 times
Example 5	5N	Not Occurred	150,000 times
Example 6	8N	150,000 times	200,000 times
Example 7	6N	Not Occurred	170,000 times
Example 8	4N	Not Occurred	130,000 times
Example 9	11N	Not Occurred	Not Occurred
Example 10	13N	180,000 times	Not Occurred
Example 11	9N	Not Occurred	Not Occurred
Example 12	11N	Not Occurred	Not Occurred
Comparative Example 1	1.5N	Not Occurred	10,000 times
Comparative Example 2	2.7 N	130,000 times	30,000 times
Comparative Example 3	2.3N	Not Occurred	20,000 times
Comparative Example 4	2.9N	Not Occurred	40,000 times
Comparative Example 5	3.1N	Not Occurred	50,000 times
Comparative Example 6	1.8N	Not Occurred	10,000 times

In the results of Table 2, Examples 1 to 12 of the silicone pressure-sensitive adhesive composition of the present invention, when compared with Comparative Examples 1 to 6, showed a very excellent adhesive force.

In addition, no crack was generated except that cracks were generated in Examples 2, 6, and 10, and peeling was also satisfactory.

On the other hand, the silicone pressure-sensitive adhesive composition of Comparative Examples 1 to 6 was relatively excellent in the occurrence of cracks, the adhesion was very weak, it was confirmed that the peeling easily occurs.

Therefore, the silicone pressure-sensitive adhesive composition of the present invention is very excellent in adhesion, thereby exhibiting excellent peeling resistance, has a low elastic modulus has the effect of preventing the occurrence of cracking of the substrate.

Claims (10)

1. Organopolysiloxane comprising a vinylsilane group; Organopolysiloxanes including hydrosilyl groups; A compound comprising at least one member selected from the group consisting of a vinyl group and an epoxy group, an isocyanate group, a hydroxy group and an amino group in one molecule; And an addition reaction catalyst.
2. The silicone pressure-sensitive adhesive composition of claim 1, wherein the organopolysiloxane including the vinylsilane group includes at least one member selected from the group consisting of the following Chemical Formulas 1 to 3.

   [Formula 1]

   

   [Formula 2]

   

   [Formula 3]

   

   N, m, p, q and r are each independently an integer of 1 to 1000,

   The ratio of the p unit and m unit is 100: 1 to 10: 1,

   The ratio of the q unit and the r unit is 100: 1 to 10: 1.
3. The silicone pressure-sensitive adhesive composition of claim 1, wherein the organopolysiloxane including the hydrosilyl group comprises at least one member selected from the group consisting of Formulas 4 to 7.

   [Formula 4]

   

   [Formula 5]

   

   [Formula 6]

   

   [Formula 7]

   

   X, a, b, c, d, e and f are each independently an integer of 1 to 1000,

   The ratio of the a unit and b unit is 100: 1 to 10: 1,

   The ratio of the c unit and d unit is 100: 1 to 10: 1,

   The ratio of the e unit and f unit is 100: 1 to 10: 1.
4. The compound according to claim 1, wherein the compound including at least one selected from the group consisting of a vinyl group, an epoxy group, an isocyanate group, a hydroxy group, and an amino group in one molecule thereof is selected from the group consisting of the following Chemical Formulas 8 to 14 Silicone pressure-sensitive adhesive composition comprising a.

   [Formula 8]

   

   [Formula 9]

   

   [Formula 10]

   

   [Formula 11]

   

   [Formula 12]

   

   [Formula 13]

   

   [Formula 14]

   
5. The silicone pressure-sensitive adhesive composition of claim 1, wherein the addition reaction catalyst is a platinum group metal catalyst, and includes at least one selected from the group consisting of platinum, palladium, iridium, rhodium, osmium, and ruthenium as a center metal.
6. The method according to claim 1, 50 to 90% by weight of the organopolysiloxane including a vinylsilane group, 5 to 40% by weight of the organopolysiloxane including a hydrosilyl group, vinyl group and epoxy group in one molecule , 1 to 15% by weight of a compound comprising at least one selected from the group consisting of an isocyanate group, a hydroxyl group and an amino group and 0.01 to 1% by weight of an addition reaction catalyst.
7. The silicone pressure sensitive adhesive composition of claim 1, wherein the silicone pressure sensitive adhesive composition is applied to a substrate including a carboxyl group or a hydroxyl group on a surface thereof.
8. Silicone pressure-sensitive adhesive prepared by the silicone pressure-sensitive adhesive composition of claim 1.
9. The silicone pressure sensitive adhesive of claim 8, wherein the silicone pressure sensitive adhesive is applied to a substrate including a carboxyl group or a hydroxyl group on a surface thereof.
10. The film to which the silicone adhesive of Claim 8 was apply | coated.

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