Silicone adhesive composition, adhesive tape, and adhesive film

Abstract

[Problem] The purpose of the present invention is to provide a silicone adhesive composition giving an adhesive layer having strong adhesive force to silicone rubber and capable of maintaining a high storage elastic modulus G' even at room temperature or high temperature, and to provide an adhesive tape and an adhesive film having an adhesive layer composed of a cured product of the adhesive composition. [Solution] This silicone adhesive composition comprises (I) at least one linear organopolysiloxane and at least one organopolysiloxane resin having a R3 3SiO1 / 2 unit and a SiO4 / 2 unit; or (II) a condensation reaction product of at least one linear organopolysiloxane and at least one organopolysiloxane resin having a R3 3SiO1 / 2 unit and a SiO4 / 2 unit. The linear organopolysiloxane in (I) and (II) contains (A) a linear organopolysiloxane having one or more alkenyl groups in one molecule, having an alkenyl group content of 0.0001-0.03 mol / 100 g and optionally having a hydroxyl group or a C1-6 alkoxy group linked to a silicon atom, and optionally contains (A') a linear organopolysiloxane that does not have an alkenyl group or a hydrogen atom linked to a silicon atom. The organopolysiloxane resin in (I) and (II) contains (B) an organopolysiloxane resin having a R3 3SiO1 / 2 unit and a SiO4 / 2 unit, having a hydroxyl group and / or a C1-6 alkoxy group linked to a silicon atom, and having a molar ratio represented by (R3 3SiO1 / 2 unit) / (SiO4 / 2 unit) of 0.5-1.5 (wherein R3 groups are independently a substituted or unsubstituted monovalent hydrocarbon group having 1-10 carbon atoms, a hydroxyl group, or an alkoxy group having 1-6 carbon atoms), the organopolysiloxane resin not containing an alkenyl group or containing an alkenyl group at an amount resulting in the total content of alkenyl group in the organopolysiloxane resin of less than 0.005 mol / 100 g, and having a weight average molecular weight of 5,000 or more as measured by gel permeation chromatography in terms of the standard polystyrene. The silicone adhesive composition further comprises (C) an organohydrogenpolysiloxane having three or more hydrogen atoms linked to silicon atoms in one molecule at an amount that results in the ratio of the total number of SiH groups in the component (C) to the total number of alkenyl groups in the alkenyl group-containing organopolysiloxane contained in the silicone adhesive composition of 0.1-30.0, and (D) a catalytic amount of a platinum group metal catalyst, and the ratio of the total mass of the linear organopolysiloxane to the total mass of the organopolysiloxane resin is 25 / 75-70 / 30.

Description

Silicone pressure-sensitive adhesive composition, pressure-sensitive adhesive tape, and pressure-sensitive adhesive film

[0001] The present invention relates to a silicone pressure-sensitive adhesive composition, and more specifically to a silicone pressure-sensitive adhesive composition that provides an adhesive layer that has strong adhesion to silicone rubber and a high storage modulus G' at room temperature and at high temperatures, and to a pressure-sensitive adhesive tape and pressure-sensitive adhesive film that include an adhesive layer made of a cured product of the pressure-sensitive adhesive composition.

[0002] The polysiloxane that makes up the silicone pressure-sensitive adhesive has excellent heat resistance, cold resistance, weather resistance, electrical insulation, and chemical resistance, and is therefore used in harsh environments such as heat-resistant pressure-sensitive adhesive tapes, electrical insulating pressure-sensitive adhesive tapes, masking tapes for manufacturing processes, temporary fixing tapes, heat-sealing tapes, and flame-retardant mica tapes.

[0003] Silicone pressure-sensitive adhesives also exhibit excellent wettability with a variety of adherends, and are adhesive to silicone resins, polyolefins, fluororesins, silicone rubber, silicone release paper, etc., which are difficult to adhere to with organic resin pressure-sensitive adhesives such as acrylic pressure-sensitive adhesives, rubber pressure-sensitive adhesives, and urethane pressure-sensitive adhesives. For this reason, silicone pressure-sensitive adhesives are considered suitable for adhesive tapes used, for example, when bonding or fixing a silicone rubber member to another member.

[0004] Furthermore, in recent years, there has been an increase in the use of adhesive tape to fix silicone rubber parts used in electronic devices, such as conductive silicone rubber, heat-dissipating silicone rubber, vibration-proof silicone rubber, selective adhesive LIMS, and electromagnetic wave blocking silicone rubber, and there has been an increase in demand for adhesives that can stably adhere to silicone rubber.

[0005] Conventional adhesive tapes using silicone adhesives for silicone rubber typically use peroxide-curable silicone adhesive compositions. However, peroxide-curable silicone adhesive compositions have a high curing temperature, making them unsuitable for use on substrates with low heat distortion temperatures and in terms of energy costs. Another problem is the residual benzoic acid, a decomposition product of peroxide. On the other hand, silicone adhesives for silicone rubber using addition-reaction-curable silicone adhesive compositions provide stable adhesion to various metals and tape substrates, but have low adhesion to silicone rubber. Furthermore, when exposed to high temperatures, the edges of the adhesive tape may peel and lift, or the adhesive tape may peel and cause parts to fall off. This is because the storage modulus G' of the silicone adhesive layer decreases when heated, resulting in a corresponding decrease in the adhesive strength of the adhesive layer.

[0006] As improvements to silicone rubber pressure-sensitive adhesives based on addition reaction curing silicone pressure-sensitive adhesive compositions, the following are known: a silicone pressure-sensitive adhesive composition containing an organosilicon compound having a B-O-Si bond (Patent Document 1), a silicone pressure-sensitive adhesive composition using a mixture of an alkenyl group-containing diorganopolysiloxane and an alkenyl group-free diorganopolysiloxane (Patent Document 2), a silicone pressure-sensitive adhesive composition containing a metal compound (Patent Document 3), and a silicone pressure-sensitive adhesive composition containing a specific organopolysiloxane containing T units and D units (Patent Document 4).However, all of these compositions have insufficient adhesive strength to silicone rubber, and there is no mention of the storage modulus G' at high temperatures. Instead of the storage modulus G' at high temperatures, the holding strength at high temperatures was measured, but the results were low.

[0007] Furthermore, in a silicone pressure-sensitive adhesive composition (Patent Document 5) in which the molar ratio of SiH groups in the organohydrogenpolysiloxane to the alkenyl groups in the linear diorganopolysiloxane is 50 to 2,000, the adhesive strength to silicone rubber is improved, but the storage modulus G' at high temperatures is insufficient. Furthermore, because of the large number of SiH groups, there is a problem in that when the adhesive thickness of the adhesive layer is increased, air bubbles remain in the adhesive layer due to a dehydrogenation reaction.

[0008] Japanese Patent Laid-Open No. 7-11228 Japanese Patent Laid-Open No. 2008-24777 Japanese Patent Laid-Open No. 2010-13632 Japanese Patent Laid-Open No. 2011-1448 Japanese Patent Laid-Open No. 2017-222819

[0009] As described above, there are no silicone pressure-sensitive adhesives that have strong adhesive strength to silicone rubber and can maintain a high storage modulus G' at room temperature or in a high temperature environment.

[0010] The present invention has been made in view of the above circumstances, and aims to provide a silicone pressure-sensitive adhesive composition that provides an adhesive layer that has strong adhesion to silicone rubber and can maintain a high storage modulus G' even at room temperature or at high temperatures, and an adhesive tape and adhesive film that have an adhesive layer made of a cured product of the pressure-sensitive adhesive composition.

[0011] As a result of extensive research conducted by the present inventors to achieve the above object, it was discovered that an addition reaction curable silicone pressure sensitive adhesive composition contains (A) a linear organopolysiloxane containing a specific amount of alkenyl groups, (B) R ３ ３ SiO １／２ Units and SiO ４／２ The present inventors have found that the above object can be achieved by blending specific amounts of an organopolysiloxane resin having a specific weight-average molecular weight and a specific ratio of units, and an organohydrogenpolysiloxane (C), respectively, and have completed the present invention.

[0012] That is, the present invention provides a method for producing a polysiloxane comprising the steps of: [1] (I) at least one linear organopolysiloxane and R ３ ３ SiO １／２ Units and SiO ４／２ or (II) at least one linear organopolysiloxane and at least one organopolysiloxane resin having a unit R ３ ３ SiO １／２ Units and SiO ４／２a silicone pressure-sensitive adhesive composition comprising a condensation reaction product with at least one organopolysiloxane resin having a unit, wherein the linear organopolysiloxane in (I) and (II) comprises: (A) a linear organopolysiloxane having one or more alkenyl groups per molecule, with an alkenyl group content of 0.0001 to 0.03 mol / 100 g, and optionally having a silicon-bonded hydroxyl group or a C alkoxy group; and optionally (A') a linear organopolysiloxane having no alkenyl groups and no silicon-bonded hydrogen atoms; and the organopolysiloxane resin in (I) and (II) comprises: (B) R ３ ３ SiO １／２ Units and SiO ４／２ units, and has a hydroxyl group and / or an alkoxy group having 1 to 6 carbon atoms bonded to a silicon atom, (R ３ ３ SiO １／２ Unit) / (SiO ４／２ The organopolysiloxane resin (wherein R ３and (b) a platinum group metal catalyst in a catalytic amount such that the ratio of the total number of alkenyl groups in the alkenyl-containing organopolysiloxane contained in the silicone pressure-sensitive adhesive composition is 0.1 to 30.0, and (c) a catalytic amount of a platinum group metal catalyst in a catalytic amount such that the ratio of the total number of SiH groups in the alkenyl-containing organopolysiloxane contained in the silicone pressure-sensitive adhesive composition is 0.1 to 30.0, and (d) a catalytic amount of a platinum group metal catalyst in a catalytic amount such that the ratio of the total number of SiH groups in the alkenyl-containing organopolysiloxane contained in the silicone pressure-sensitive adhesive composition is 0.1 to 30.0, and (e) a catalytic amount of a platinum group metal catalyst in a catalytic amount such that the ratio of the total number of SiH groups in the alkenyl-containing organopolysiloxane contained in the silicone pressure-sensitive adhesive composition is 0.1 to 30.0, and (f) a catalytic amount of a platinum group metal catalyst in a catalytic amount such that the ratio of the total number of SiH groups in the alkenyl-containing organopolysiloxane contained in the silicone pressure-sensitive adhesive composition is 0.1 to 30.0, and (g) a catalytic amount of a platinum group metal catalyst in a catalytic amount such that the ratio of the total number of SiH groups in the alkenyl-containing organopolysiloxane contained in the silicone pressure-sensitive adhesive composition is 0.1 to 30.0, and (h) a catalytic amount of a platinum group metal catalyst in a catalytic amount such that the ratio of the total number of SiH groups in the alkenyl-containing organopolysiloxane contained in the silicone pressure-sensitive adhesive composition is 0.1 to 30.0, and (g) a catalytic amount of a platinum group metal catalyst in a catalytic amount such that the ratio of the total number of SiH groups in the alkenyl-containing organopolysiloxane contained in the silicone pressure-sensitive adhesive composition is 0.1 to 30.0. The silicone pressure-sensitive adhesive composition is provided, wherein the ratio of the total mass of the linear organopolysiloxane to the total mass of the organopolysiloxane resin is 25 / 75 to 70 / 30.

[0013] The present invention further provides the silicone pressure-sensitive adhesive composition, further comprising at least one of the following structures [2] to

[13] : [2] The silicone pressure-sensitive adhesive composition, in which the amount of the component (A) is 0.1 to 70 mass%, the amount of the component (B) is 0.01 to 70 mass%, and the amount of the component (A') is 0 to 50 mass%, relative to the total mass of the silicone pressure-sensitive adhesive composition. [3] (F)R ３ ３ SiO １／２ Units and SiO ４／２ units, (R ３ ３ SiO １／２ Unit) / (SiO ４／２ units) is 0.5 to 1.5, has one or more alkenyl groups in one molecule, the alkenyl group content is 0.005 to 0.5 mol / 100 g, and optionally has silicon-bonded hydroxyl groups and / or silicon-bonded alkoxy groups having 1 to 6 carbon atoms (wherein R ３are each independently a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, a hydroxyl group, or an alkoxy group having 1 to 6 carbon atoms), in an amount of 0.01 to 45 mass% relative to the total mass of the silicone pressure-sensitive adhesive composition. [4] The silicone pressure-sensitive adhesive composition comprising a condensation reaction product of the component (A), optionally the component (A'), the component (B), and the component (F). [5] The silicone pressure-sensitive adhesive composition comprising a condensation reaction product of the component (A), optionally the component (A'), and the component (B), and further comprising the component (F). [6] (E)R ３ ３ SiO １／２ Units and SiO ４／２ units, and has a hydroxyl group and / or an alkoxy group having 1 to 6 carbon atoms bonded to a silicon atom, (R ３ ３ SiO １／２ Unit) / (SiO ４／２ The organopolysiloxane resin (wherein R ３ and (E) are each independently a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, a hydroxyl group, or an alkoxy group having 1 to 6 carbon atoms), and the organopolysiloxane resin does not contain alkenyl groups or contains alkenyl groups in such an amount that the total amount of alkenyl groups in the organopolysiloxane resin is less than 0.005 mol / 100 g, and the organopolysiloxane resin has a weight average molecular weight (Mw) of less than 5,000 as measured by gel permeation chromatography (GPC) relative to standard polystyrene. [7] The silicone pressure-sensitive adhesive composition comprising a condensation reaction product of the component (A), optionally the component (A'), the component (B), the component (E), and the component (F). [8] (E)R ３ ３ SiO １／２ Units and SiO ４／２ units, and has a hydroxyl group and / or an alkoxy group having 1 to 6 carbon atoms bonded to a silicon atom, (R ３ ３ SiO１／２ Unit) / (SiO ４／２ The organopolysiloxane resin (wherein R ３ and (b) are each independently a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, a hydroxyl group, or an alkoxy group having 1 to 6 carbon atoms), and the organopolysiloxane resin does not contain alkenyl groups or contains alkenyl groups in such an amount that the total amount of alkenyl groups in the organopolysiloxane resin is less than 0.005 mol / 100 g, and the organopolysiloxane resin has a weight average molecular weight (Mw) of less than 5,000 as measured by gel permeation chromatography (GPC) relative to standard polystyrene standards, in an amount of 0.01 to 35 mass %, relative to the total mass of the silicone pressure-sensitive adhesive composition. [9] The silicone pressure-sensitive adhesive composition comprising a condensation reaction product of component (A), and optionally component (A'), component (B), component (E), and component (F).

[10] The silicone pressure-sensitive adhesive composition, comprising a condensation reaction product of the component (A), optionally the component (A'), the component (B), and the component (E), and further comprising the component (F).

[11] The silicone pressure-sensitive adhesive composition, wherein the component (A) is represented by the following formula (1): (In the formula, R １ are each independently a hydroxyl group, an alkoxy group having 1 to 6 carbon atoms, or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, provided that R １ at least one of R is an alkenyl-containing organic group having 2 to 10 carbon atoms; １ the ratio of the number of hydroxyl groups to the total number of R is 10% or less, the alkenyl group content in the organopolysiloxane is 0.0001 to 0.03 mol / 100 g, and a is a positive number such that a solution of the organopolysiloxane in toluene to a concentration of 30% by mass has a viscosity of 1,000 to 200,000 mPa s at 25°C.

[12] The component (F) further comprises R ５ R ６ SiO ２／２ units (wherein R ５ is the above R other than an alkenyl group. ３ and R６ is an alkenyl group having 2 to 10 carbon atoms), (R ５ R ６ SiO ２／２ Unit) / (SiO ４／２

[13] Any of the above silicone pressure-sensitive adhesive compositions, wherein the adhesive strength of a 40 μm-thick cured layer formed by curing the silicone pressure-sensitive adhesive composition to a silicone rubber sheet is 3.0 N / 25 mm or more, as measured at a tensile speed of 300 mm / min using a 180° peel test method.

[0014] The present invention further provides a cured product obtained by curing the above-mentioned silicone pressure-sensitive adhesive composition.The present invention further provides the above-mentioned cured product, in which the adhesive layer formed from the cured product obtained by curing the above-mentioned silicone pressure-sensitive adhesive composition has a storage modulus G' at 25°C of 1.00 MPa or more.The present invention further provides the above-mentioned cured product, in which the adhesive layer formed from the cured product obtained by curing the above-mentioned silicone pressure-sensitive adhesive composition has a storage modulus G' at 80°C of 0.10 MPa or more.The present invention further provides a pressure-sensitive adhesive tape comprising a substrate and an adhesive layer formed on at least one surface of the substrate, wherein the adhesive layer is a cured product obtained by curing the above-mentioned silicone pressure-sensitive adhesive composition.The present invention further provides a pressure-sensitive adhesive film comprising a substrate and an adhesive layer formed on at least one surface of the substrate, wherein the adhesive layer is a cured product obtained by curing the above-mentioned silicone pressure-sensitive adhesive composition.

[0015] An adhesive tape or film having an adhesive layer formed by curing the silicone adhesive composition of the present invention has strong adhesive strength to silicone rubber and can maintain a high storage modulus G' even at high temperatures. Therefore, this adhesive tape or film can be suitably used for adhering and bonding silicone materials, as masking tape or temporary fixing tape in the manufacturing process of electronic components or semiconductor components, or as a member for electronic materials or display devices.

[0016] The silicone pressure-sensitive adhesive composition of the present invention will now be described in more detail.

[0017] The present invention provides a composition comprising (I) at least one linear organopolysiloxane and R ３ ３ SiO １／２ units (so-called M units) and SiO ４／２ or (II) at least one organopolysiloxane resin having a linear organopolysiloxane and an organopolysiloxane having a linear organopolysiloxane group (a so-called MQ resin) having a unit (a so-called Q unit). ３ ３ SiO １／２ units (so-called M units) and SiO ４／２ The silicone pressure-sensitive adhesive composition contains a condensation reaction product of at least one organopolysiloxane resin (so-called MQ resin) having units (so-called Q units). The silicone pressure-sensitive adhesive composition containing (I) above may further contain a condensation reaction product shown in (II) above.

[0018] The linear organopolysiloxane in (I) and (II) above includes (A) a linear organopolysiloxane having one or more alkenyl groups per molecule, an alkenyl group content of 0.0001 to 0.03 mol / 100 g, and optionally having a silicon-bonded hydroxyl group or a C alkoxy group. The linear organopolysiloxane may further include, optionally, (A') a linear organopolysiloxane having no alkenyl groups and no silicon-bonded hydrogen atoms.

[0019] The organopolysiloxane resin (MQ resin) in (I) and (II) above is (B)R ３ ３ SiO １／２ Units and SiO ４／２ units and has hydroxyl groups and / or alkoxy groups having 1 to 6 carbon atoms bonded to silicon atoms, (R ３ ３ SiO １／２ Unit) / (SiO ４／２ The organopolysiloxane resin (wherein R ３are each independently a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, a hydroxyl group, or an alkoxy group having 1 to 6 carbon atoms), wherein the organopolysiloxane resin contains no alkenyl groups or contains alkenyl groups in an amount such that the total amount of alkenyl groups in the organopolysiloxane resin is less than 0.005 mol / 100 g, and has a weight average molecular weight (Mw) of 5,000 or more as measured by gel permeation chromatography (GPC) relative to standard polystyrene.

[0020] The organopolysiloxane resin (MQ resin) may further preferably contain (F) an MQ resin having one or more alkenyl groups per molecule, with the alkenyl group content being 0.005 to 0.5 mol / 100 g, in an amount of 0.01 to 45% by mass relative to the total mass of the silicone pressure-sensitive adhesive composition. ３ ３ SiO １／２ Units and SiO ４／２ is an organopolysiloxane resin having units (R ３ ３ SiO １／２ Unit) / (SiO ４／２ The molar ratio of R to C is 0.5 to 1.5, and optionally has hydroxyl groups bonded to silicon atoms and / or alkoxy groups having 1 to 6 carbon atoms bonded to silicon atoms. ３ are each independently a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, a hydroxyl group, or an alkoxy group having 1 to 6 carbon atoms.

[0021] The organopolysiloxane resin (MQ resin) may preferably further contain (E) an MQ resin having a weight average molecular weight (Mw) of less than 5,000 as measured by gel permeation chromatography (GPC) relative to standard polystyrene standards, and having a total amount of alkenyl groups of less than 0.005 mol / 100 g, in an amount of 0.01 to 35% by mass relative to the total mass of the silicone pressure-sensitive adhesive composition. ３ ３ SiO １／２ Units and SiO ４／２units and has hydroxyl groups and / or alkoxy groups having 1 to 6 carbon atoms bonded to silicon atoms, (R ３ ３ SiO １／２ Unit) / (SiO ４／２ The molar ratio represented by R is 0.5 to 1.5. ３ are each independently a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, a hydroxyl group, or an alkoxy group having 1 to 6 carbon atoms. The MQ resin (E) does not contain any alkenyl groups, or contains alkenyl groups in such an amount that the total amount of alkenyl groups in the organopolysiloxane resin is less than 0.005 mol / 100 g.

[0022] Preferably, the organopolysiloxane resin (MQ resin) comprises the component (B) and, optionally, at least one MQ resin selected from the components (E) and (F). More preferably, the organopolysiloxane resin comprises the components (B) and (F), and, optionally, the component (E).

[0023] A preferred embodiment of the silicone pressure-sensitive adhesive composition (II) is a silicone pressure-sensitive adhesive composition comprising a condensation reaction product of the component (A), optionally the component (A'), and the component (B), more preferably a condensation reaction product of the component (A), optionally the component (A'), the component (B), and optionally at least one MQ resin selected from the components (E) and (F).

[0024] Another preferred embodiment of the present invention is a silicone pressure-sensitive adhesive composition comprising a condensation reaction product of the component (A), optionally the component (A'), the component (B), and the component (F). Another preferred embodiment of the present invention is a silicone pressure-sensitive adhesive composition comprising a condensation reaction product of the component (A), optionally the component (A'), and the component (B), and the component (F). Another preferred embodiment of the present invention is a silicone pressure-sensitive adhesive composition comprising a condensation reaction product of the component (A), optionally the component (A'), the component (B), and the component (E). Another more preferred embodiment of the present invention is a silicone pressure-sensitive adhesive composition comprising a condensation reaction product of the component (A), optionally the component (A'), the component (B), the component (E), and the component (F). Another more preferred embodiment of the present invention is a silicone pressure-sensitive adhesive composition comprising the component (A), optionally the component (A'), the component (B), and a condensation reaction product of the component (E), and the component (F).

[0025] Each component will be described in more detail below.

[0026] [Component (A)] Component (A) is a linear organopolysiloxane having one or more alkenyl groups per molecule. Component (A) may be any linear organopolysiloxane having one or more alkenyl groups per molecule, and may be used alone or in combination of two or more types.

[0027] Component (A) may be any oil- or gum-like organopolysiloxane, preferably a gum-like organopolysiloxane. For oil-like organopolysiloxanes, the viscosity at 25°C is preferably 1,000 mPa·s or higher, more preferably 10,000 mPa·s or higher, and particularly preferably 50,000 mPa·s or higher. For gum-like organopolysiloxanes, the viscosity of a 30% by mass solution in toluene is preferably 1,000 to 200,000 mPa·s, more preferably 5,000 to 150,000 mPa·s, even more preferably 10,000 to 120,000 mPa·s, and particularly preferably 15,000 to 100,000 mPa·s. Viscosities below the lower limit may make uniform coating difficult or may result in reduced adhesive strength and storage modulus G' of the resulting adhesive layer. If the viscosity exceeds the upper limit, the viscosity of the composition becomes very high, which may result in poor workability, such as difficulty in stirring and mixing. In this specification, viscosity (mPa s) is a value measured at 25°C using a B-type rotational viscometer in accordance with JIS K 7117-1 (the same applies hereinafter).

[0028] The amount of alkenyl groups contained in component (A) is preferably 0.0001 to 0.03 mol per 100 g of organopolysiloxane, more preferably 0.0002 to 0.02 mol / 100 g, more preferably 0.0003 to 0.01 mol / 100 g, and even more preferably 0.0005 to 0.005 mol / 100 g. If the amount is less than the lower limit, the curing properties may be reduced, and the storage modulus G' and adhesive strength of the resulting adhesive layer may be reduced. If the amount is greater than the upper limit, the crosslink density of the resulting adhesive layer may be increased, and adhesive strength may be reduced. This amount of alkenyl groups is determined by the amount of the deuterated chloroform solution. １ H-NMR and ２９ This can be determined by a known structural analysis method using Si-NMR (the same applies hereinafter).

[0029] Component (A) optionally contains silicon-bonded hydroxyl groups or alkoxy groups having 1 to 6 carbon atoms. When component (A) contains hydroxyl groups, the ratio of the number of hydroxyl groups and alkoxy groups to the total number of silicon-bonded groups in the organopolysiloxane is preferably 10% or less, more preferably 0.001 to 5%, and even more preferably 0.002 to 1%. That is, the amount of hydroxyl groups and alkoxy groups in component (A) is preferably 0.00002 to 0.15 mol / 100 g, and particularly preferably 0.00005 to 0.03 mol / 100 g. The presence of hydroxyl groups or alkoxy groups enables component (A) to undergo a condensation reaction with component (B) and optional components (E) and (F), which will be described later. The amount of SiOH groups is determined by the concentration of the hydroxyl groups in a deuterated chloroform solution. １ H-NMR and ２９ This can be determined by a known structural analysis method using Si-NMR (the same applies hereinafter). The alkoxy group is preferably an alkoxy group having 1 to 6 carbon atoms, and examples thereof include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, and a phenoxy group.

[0030] The organopolysiloxane (A) is preferably represented by the following formula (1): In the formula, R １ are each independently a hydroxyl group, an alkoxy group having 1 to 6 carbon atoms, or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, provided that R １ at least one of the groups is an alkenyl-containing organic group having 2 to 10 carbon atoms, and a is a positive number such that a solution of the organopolysiloxane in toluene to a concentration of 30% by mass has a viscosity of 1,000 to 200,000 mPa s at 25°C.

[0031] In formula (1), R １ are each independently a hydroxyl group, an alkoxy group having 1 to 6 carbon atoms, or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms; R １At least one of the alkenyl-containing organic groups has 2 to 10 carbon atoms. The alkenyl-containing organic group has 2 to 10 carbon atoms, preferably 2 to 8 carbon atoms, and may contain an oxygen atom. Examples include alkenyl groups such as vinyl, allyl, hexenyl, and octenyl, and cycloalkenylalkyl groups such as cyclohexenylethyl. Examples of the alkenyl-containing monovalent hydrocarbon group that may contain an oxygen atom include acryloylalkyl groups and methacryloylalkyl groups such as acryloylpropyl, acryloylmethyl, methacryloylpropyl, and methacryloylmethyl. The methylene chain may also contain an ether bond, for example, -(CH ２ ) ２ -O-CH ２ -CH=CH ２ , or -(CH ２ ) ３ -O-CH ２ -CH=CH ２ Examples include:

[0032] The monovalent hydrocarbon group other than the alkenyl group-containing organic group is a monovalent hydrocarbon group having 1 to 10 carbon atoms and no aliphatic unsaturated bond. Examples include alkyl groups preferably having 1 to 6 carbon atoms, such as methyl, ethyl, propyl, and butyl, cycloalkyl groups preferably having 5 to 8 carbon atoms, such as cyclohexyl, aryl groups preferably having 6 to 10 carbon atoms, such as phenyl and tolyl, aralkyl groups preferably having 7 to 10 carbon atoms, such as benzyl, and monovalent hydrocarbon groups having 1 to 10 carbon atoms in which some or all of the hydrogen atoms bonded to carbon atoms have been substituted with hydroxy groups, cyano groups, halogen atoms, alkoxy groups, alkoxysilyl groups, polyoxyalkylene groups, epoxy groups, carboxyl groups, or the like, such as hydroxypropyl, cyanoethyl, 3-chloropropyl, 3,3,3-trifluoropropyl, 3,3,4,4,5,5,6,6,6-nonafluorohexyl, methoxypropyl, ethoxypropyl, and γ-glycidoxypropyl groups. Among these, a methyl group or a phenyl group is preferred, and a methyl group is particularly preferred. １ It is particularly preferred that the ratio of the number of methyl groups to the total number of R is 70% or more, preferably 80% or more, and more preferably 90% or more.１ When R １ The ratio of the total number of aryl groups and aralkyl groups to the total number of groups) is preferably 0.1 to 30%, and more preferably 0.5 to 15%. When an aryl group or an aralkyl group is contained, the adhesive strength and storage modulus G' of the resulting adhesive layer may be improved.

[0033] When the above formula (1) has a hydroxyl group or an alkoxy group, R １ The ratio of the number of hydroxyl groups and alkoxy groups to the total number of groups is preferably 10% or less, more preferably 0.001 to 5%, and even more preferably 0.002 to 1%. That is, the amount of hydroxyl groups and alkoxy groups in component (A) is preferably 0.00002 to 0.15 mol / 100g, and particularly preferably 0.00005 to 0.03 mol / 100g. By having hydroxyl groups or alkoxy groups, component (A) can undergo a condensation reaction with component (B) and optional components (E) and (F), which will be described later. The amount of SiOH groups is determined by the concentration of the hydroxyl groups and alkoxy groups in the deuterated chloroform solution. １ H-NMR and ２９ This can be determined by a known structural analysis method using Si-NMR (the same applies hereinafter).

[0034] In formula (1), a is preferably 100 to 20,000, more preferably 500 to 15,000, more preferably 1,000 to 13,500, and even more preferably 2,000 to 12,000. If a is less than the above lower limit, uniform coating may be difficult, and the adhesive strength and storage modulus G' of the resulting adhesive layer may decrease. If a exceeds the above upper limit, the viscosity of the composition may become very high, making it difficult to stir and mix, and other workability problems may result.

[0035] Component (A) is preferably a crude rubber-like organopolysiloxane represented by the following formula (2). In the formula, R ２ are each independently a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms that does not have a hydroxyl group or an aliphatic unsaturated bond, and R ２where X′ is an alkyl group having 1 to 6 carbon atoms, X is an alkenyl-containing organic group having 2 to 10 carbon atoms, b is a number from 1 to 3, c is a number from 1 to 3, d is a number from 0 to 2, e is a number from 0 to 2, f is a number from 0 to 2, g is a number from 0 to 2, d+e+f+g=2, h is a number of 0 or greater, c×f+h≧1, i is a number of 100 or greater, and h+i is a positive number such that the organopolysiloxane has the above-mentioned viscosity. More preferably, 100≦h+i≦20,000.

[0036] In formula (2), R ２ are each independently a hydroxyl group or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms that does not have an aliphatic unsaturated bond. For example, R １ Examples of monovalent hydrocarbon groups other than the alkenyl-containing organic groups exemplified by R include those mentioned above. Among these, a methyl group or a phenyl group is preferred, and a methyl group is particularly preferred. ２ When R contains a hydroxyl group, ２ The ratio of the number of hydroxyl groups to the total number of groups is preferably 10% or less, more preferably 0.001 to 5%, and even more preferably 0.002 to 1%.

[0037] X is an alkenyl-containing monovalent organic group having 2 to 10 carbon atoms, preferably 2 to 8 carbon atoms, and may contain an oxygen atom. １ Examples of the alkenyl group-containing organic group include those mentioned above. Among them, a vinyl group is preferred.

[0038] In formula (2), b is a number from 1 to 3, preferably 1. c is a number from 1 to 3, preferably 1. d is a number from 0 to 2, preferably 0 to 1.5, and more preferably 0 to 1.0. e is a number from 0 to 2, preferably 0 to 1, more preferably 0 to 0.5, and even more preferably 0. f is a number from 0 to 2, preferably 0.5 to 2, and more preferably 1.0 to 2. g is a number from 0 to 2, preferably 0 to 1.5, more preferably 0 to 1.0, and even more preferably 0. h is a number of 0 or more, preferably 0 to 500, more preferably 0 to 100, and even more preferably 0 to 50. i is a number of 100 or more, preferably 500 to 15,000, more preferably 1,000 to 13,500, and even more preferably 2,000 to 12,000. c×f+h is 2 or more, preferably 2 to 500, more preferably 2 to 100, and even more preferably 2 to 50. h+i is 100 to 20,000, preferably 500 to 15,000, more preferably 1,000 to 13,500, and even more preferably 2,000 to 12,000.

[0039] Examples of component (A) include, but are not limited to, the following: In the following formulas, Me, Vi, and Ph represent a methyl group, a vinyl group, and a phenyl group, respectively. The bonding order of each siloxane unit shown in parentheses is not limited to the following: In each of the following formulas, the total number of siloxane repeating units is an average value. (z1 + z2 + z3 + z4 + z5 = 2, and z6, z7, and z8 are numbers at which the organopolysiloxane has the above-mentioned viscosity. Preferably, 100≦z6 + z7 + z8 ≦20,000.) (z6 is the number at which the organopolysiloxane has the above-mentioned viscosity. Preferably, 100≦z6≦20,000.) (z6 and z7 are numbers at which the organopolysiloxane has the above-mentioned viscosity. Preferably, 100≦z6+z7≦20,000.) (z6 is the number at which the organopolysiloxane has the above-mentioned viscosity. Preferably, 100≦z6≦20,000.) (z6 and z7 are numbers at which the organopolysiloxane has the above-mentioned viscosity. Preferably, 100≦z6+z7≦20,000.) (z8≧1, z6 and z8 are numbers at which the organopolysiloxane has the above-mentioned viscosity. Preferably, 100≦z6+z8≦20,000.) (z8≧1, z6, z7, and z8 are numbers at which the organopolysiloxane has the above-mentioned viscosity. Preferably, 100≦z6+z7+z8≦20,000.) (z1 + z5 = 2, z8 ≥ 1, z6 and z8 are numbers that allow the organopolysiloxane to have the above-mentioned viscosity. Preferably, 100 ≤ z6 + z8 ≤ 20,000.) (z1 + z5 = 2, z8 ≥ 1, z6, z7, and z8 are numbers that allow the organopolysiloxane to have the above-mentioned viscosity. Preferably, 100 ≤ z6 + z7 + z8 ≤ 20,000.) (z1 + z3 = 2, z3 + z8 ≥ 1, z6 and z8 are numbers that allow the organopolysiloxane to have the above-mentioned viscosity. Preferably, 100 ≤ z6 + z8 ≤ 20,000.) (z1 + z3 = 2, z3 + z8 ≥ 1, z6, z7, and z8 are numbers that allow the organopolysiloxane to have the above-mentioned viscosity. Preferably, 100 ≤ z6 + z7 + z8 ≤ 20,000.) (z1 + z4 = 2, z4 × 3 + z8 ≥ 1, z6 and z8 are numbers that allow the organopolysiloxane to have the above-mentioned viscosity. Preferably, 100 ≤ z6 + z8 ≤ 20,000.) (z1 + z4 = 2, z4 × 3 + z8 ≥ 1, z6, z7, and z8 are numbers that allow the organopolysiloxane to have the above-mentioned viscosity. Preferably, 100 ≤ z6 + z7 + z8 ≤ 20,000.) (z1 + z2 = 2, z8 ≥ 1, z6 and z8 are numbers that allow the organopolysiloxane to have the above-mentioned viscosity. Preferably, 100 ≤ z6 + z8 ≤ 20,000.) (z1 + z2 = 2, z8 ≥ 1, z6, z7, and z8 are numbers that allow the organopolysiloxane to have the above-mentioned viscosity. Preferably, 100 ≤ z6 + z7 + z8 ≤ 20,000.)

[0040] The silicone composition of the present invention may further contain, as the linear organopolysiloxane, a linear organopolysiloxane (A') that does not have an alkenyl group or an SiH group. When the organopolysiloxane (A') has a SiOH group or an alkoxysilyl group, it can undergo a condensation reaction with the later-described component (B) and optional components (E) and (F). The content of component (A') is preferably 70% by mass or less, more preferably 50% by mass or less, and even more preferably 40% by mass or less, based on the total mass of components (A) and (A'). Within the above range, the adhesive strength and storage modulus G' of the resulting adhesive layer may be improved. The lower limit of the content of component (A') relative to the total mass of components (A) and (A') is not particularly limited, and may be 0% by mass or more. For example, it may be 0.1% by mass or more, or 1% by mass or more.

[0041] The component (A') is represented, for example, by the following formula (1'). (In the formula, R １ ' are each independently a hydroxyl group, an alkoxy group having 1 to 6 carbon atoms, or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, provided that R １ a' is not an alkenyl group-containing organic group, and a' is a positive number of 1 or more.

[0042] Component (A') may be an oily or crude rubber organopolysiloxane. If it is an oily organopolysiloxane, its viscosity at 25°C is preferably 1,000 mPa·s or more, more preferably 10,000 mPa·s or more, and particularly preferably 50,000 mPa·s or more. If it is a crude rubber-like organopolysiloxane, the viscosity of a 30% by mass solution in toluene is preferably 1,000 to 200,000 mPa·s, more preferably 5,000 to 150,000 mPa·s, even more preferably 10,000 to 120,000 mPa·s, and particularly preferably 15,000 to 100,000 mPa·s.

[0043] In formula (1'), a' is a positive number of 1 or greater, and may have any value that allows the organopolysiloxane to have the above-mentioned viscosity. Preferably, a' is 100 to 20,000, more preferably 500 to 15,000, more preferably 1,000 to 13,500, and even more preferably 2,000 to 12,000. R １ ' is, for example, R １ Examples of monovalent hydrocarbon groups other than the alkenyl-containing organic groups exemplified by R include those mentioned above. Among these, a methyl group or a phenyl group is preferred, and a methyl group is particularly preferred. １ When R ′ contains a hydroxyl group or an alkoxy group, １ The ratio of the number of hydroxyl groups and alkoxy groups to the total number of ' is preferably 10% or less, more preferably 0.001 to 5%, and even more preferably 0.002 to 1%.

[0044] [Component (B)] Component (B) is R ３ ３ SiO １／２ Units and SiO ４／２ units, R ３ ３ SiO １／２ Units / SiO ４／２ The organopolysiloxane resin has a molar ratio of units of 0.5 to 1.5, preferably 0.55 to 1.3, and more preferably 0.6 to 1.0. If the molar ratio is less than the lower limit or exceeds the upper limit, the adhesive strength and storage modulus G' of the resulting adhesive layer may decrease. ３ ３ SiO １／２ Units / SiO ４／２ The molar ratio of the unit is that of a deuterated chloroform solution. １ H-NMR and ２９ This can be determined by a known structural analysis method such as Si-NMR (the same applies hereinafter). The component (B) may be used alone or in combination of two or more.

[0045] The organopolysiloxane resin (B) can undergo a condensation reaction with the component (A) and, optionally, the components (A'), (E), and (F).

[0046] R ３are each independently a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, a hydroxyl group, or an alkoxy group having 1 to 6 carbon atoms. Examples include alkyl groups preferably having 1 to 6 carbon atoms, such as methyl, ethyl, propyl, and butyl; cycloalkyl groups preferably having 5 to 8 carbon atoms, such as cyclohexyl; aryl groups preferably having 6 to 10 carbon atoms, such as phenyl and tolyl; aralkyl groups preferably having 7 to 10 carbon atoms, such as benzyl; alkenyl groups preferably having 2 to 8 carbon atoms, such as vinyl, allyl, and hexenyl; and monovalent hydrocarbon groups having 1 to 10 carbon atoms in which some or all of the hydrogen atoms bonded to carbon atoms of the hydrocarbon groups have been substituted with hydroxy groups, cyano groups, halogen atoms, alkoxy groups, alkoxysilyl groups, polyoxyalkylene groups, epoxy groups, carboxyl groups, or the like, such as hydroxypropyl, cyanoethyl, 3-chloropropyl, 3,3,3-trifluoropropyl, 3,3,4,4,5,5,6,6,6-nonafluorohexyl, methoxypropyl, ethoxypropyl, and γ-glycidoxypropyl groups. Of these, methyl and phenyl groups are preferred, with methyl being particularly preferred.

[0047] Component (B) may contain or not contain alkenyl groups, but the total amount of alkenyl groups contained in the resin is less than 0.005 mol / 100 g, more preferably less than 0.004 mol / 100 g, and even more preferably less than 0.003 mol / 100 g. Component (B) most preferably does not contain alkenyl groups. If the alkenyl group content in component (B) exceeds the above upper limit, the adhesive strength and storage modulus G' of the resulting adhesive layer may decrease.

[0048] The component (B) is R ３ ３ SiO １／２ Units and SiO ４／２ Although the organopolysiloxane resin essentially contains the R unit, it may contain the R unit within a range that does not impair the properties of the present invention. ３ ２ SiO ２／２ Units and R ３ SiO ３／２ Unit (R ３is as described above). More preferably, the above R ３ ３ SiO １／２ Units and the above SiO ４／２ It is an organopolysiloxane resin consisting of units.

[0049] Component (B) may contain either or both of siloxane units having a hydroxyl group bonded to a silicon atom (silanol group-containing units) and siloxane units having an alkoxy group having 1 to 6 carbon atoms bonded to a silicon atom (alkoxy group-containing units). The amount of silanol group-containing units is preferably such that the hydroxyl group content of component (B) is 0.005 to 0.3 mol / 100g, more preferably 0.008 to 0.25 mol / 100g, and even more preferably 0.01 to 0.2 mol / 100g. If the hydroxyl group content exceeds 0.3 mol / 100g, the adhesive strength and storage modulus G' of the resulting adhesive layer may decrease, or curability may decrease. Furthermore, the amount of alkoxy group-containing units is preferably such that the alkoxy group content of component (B) is 0.3 mol / 100g or less, more preferably 0.2 mol / 100g or less, and even more preferably 0.1 mol / 100g or less. If the alkoxy group content exceeds 0.3 mol / 100 g, the adhesive strength and storage modulus G' of the resulting adhesive layer may decrease, and curing properties may also decrease. There is no lower limit, but it can be, for example, 0.003 mol / 100 g or more. The SiOH group content and alkoxy group content are determined by the concentration of the alkoxy group in the deuterated chloroform solution. １ H-NMR and ２９ This can be determined by a known structural analysis method using Si-NMR (the same applies hereinafter).

[0050] Furthermore, the total amount of the silanol group-containing units and alkoxy group-containing units, as the sum of the hydroxyl group content and alkoxy group content, in component (B) is preferably 0.008 to 0.3 mol / 100 g, more preferably 0.01 to 0.25 mol / 100 g, and particularly preferably 0.02 to 0.2 mol / 100 g. The presence of such hydroxyl groups or alkoxy groups enables condensation reactions with component (A), optional component (A'), component (E), and component (F).

[0051] Examples of the alkoxy group having 1 to 6 carbon atoms include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, and a phenoxy group. ３ ２ (OH)SiO １／２ Unit, R ３ (OH) ２ SiO １／２ Unit, R ３ (OH)SiO ２／２ Units: (OH)SiO ３／２ The alkoxy group-containing unit is, for example, a unit represented by R ３ ２ (OR')SiO １／２ Unit, R ３ (OR') ２ SiO １／２ Unit, R ３ (OR')SiO ２／２ Units, (OR')SiO ３／２ (OR' are each independently an alkoxy group having 1 to 6 carbon atoms, as exemplified above). ３ ３ SiO １／２ Units and SiO ４／２ When the unit is SiO ４／２ It can be bonded to a silicon atom from the unit.

[0052] Component (B) is an organopolysiloxane resin having a weight-average molecular weight of 5,000 or more. The weight-average molecular weight is more preferably 5,300 to 15,000, more preferably 5,600 to 12,000, even more preferably 6,000 to 10,000, and most preferably 6,500 to 10,000. If the weight-average molecular weight is below the lower limit or exceeds the upper limit, the adhesive strength and storage modulus G' of the resulting adhesive layer may decrease. The weight-average molecular weight can be determined as the polystyrene-equivalent weight-average molecular weight by gel permeation chromatography (GPC) analysis using toluene as the developing solvent.

[0053] In the present invention, the weight average molecular weight (Mw) is a value determined by GPC (gel permeation chromatography) analysis using polystyrene as a standard substance under the following conditions. (Measurement conditions) GPC measurement device: HLC-8320 (manufactured by Tosoh Corporation) Detector: differential refractive index detector (RI) Measurement solvent: toluene Flow rate: 0.35 mL / min GPC columns: (passed in the following order) TSKgel Guardcolumn SuperHZ-L (4.6 mm I.D. × 2 cm × 1) TSKgel SuperHZ4000 (4.6 mm I.D. × 15 cm × 1) TSKgel SuperHZ3000 (4.6 mm I.D. × 15 cm × 1) TSKgel SuperHZ2000 (4.6 mm I.D. × 15 cm × 2) (all manufactured by Tosoh Corporation) Measurement temperature: 40°C Sample injection amount: 10 μL (toluene solution with a silicone concentration of 0.5 wt%)

[0054] [Component (C)] Component (C) is an organohydrogenpolysiloxane having three or more silicon-bonded hydrogen atoms (SiH groups) per molecule. This organohydrogenpolysiloxane (C) may be used alone or in combination of two or more different types.

[0055] The average degree of polymerization of the siloxane in component (C) is preferably 100 or less, more preferably 3 to 80, more preferably 4 to 70, more preferably 5 to 50, and even more preferably 6 to 30.

[0056] The SiH groups in component (C) undergo an addition reaction with the alkenyl groups in component (A) and component (F), described below, to cure and form an adhesive layer. The amount of component (C) added is such that the ratio of the total number of SiH groups in component (C) to the total number of alkenyl groups in the alkenyl group-containing organopolysiloxane contained in the silicone adhesive composition is 0.1 to 30.0, preferably 0.2 to 20.0, more preferably 0.3 to 15.0, more preferably 0.3 to 10.0, even more preferably 0.4 to 5.0, and even more preferably 0.5 to 2.0. An especially preferred lower limit is 0.75 or greater. That is, the ratio of the total number of SiH groups in component (C) to the total number of alkenyl groups in component (A) and optional component (F) is 0.1 to 30.0, preferably 0.2 to 20.0, more preferably 0.3 to 15.0, more preferably 0.3 to 10.0, even more preferably 0.4 to 5.0, and even more preferably 0.5 to 2.0. An especially preferred lower limit is 0.75 or greater. The amount of component (C) is preferably 0.01 to 10.0 parts by mass, preferably 0.05 to 7.0 parts by mass, and even more preferably 0.10 to 5.0 parts by mass, per 100 parts by mass of the total of components (A), (B), and optional components (A'), (E), and (F).

[0057] The blending amount of component (C) is preferably 0.00005 to 10 mass%, more preferably 0.00010 to 7.0 mass%, and even more preferably 0.00050 to 5.0 mass%, based on the total amount of the silicone pressure-sensitive adhesive composition including the optional components described below. If the blending amount or number ratio is less than the above lower limit, the adhesive strength and storage modulus G' of the resulting adhesive layer may decrease. If the blending amount or number ratio exceeds the above upper limit, the adhesive strength of the resulting adhesive layer may decrease, or the usable time of the treatment bath may be shortened.

[0058] The component (C) may be linear, branched, or cyclic, or may be a mixture thereof. Examples of the component (C) include R ４ ２ HSiO １／２ Unit, R ４ HSiO ２／２ Units, and HSiO ３／２and optionally further comprises at least one R ４ ３ SiO １／２ Unit, R ４ ２ SiO ２／２ Unit, R ４ SiO ３／２ units, and SiO ４／２ Examples include polymers or copolymers comprising at least one of the units ４ are each independently a hydroxyl group, an alkoxy group having 1 to 6 carbon atoms, or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms and no aliphatic unsaturated bonds). ４ ２ HSiO １／２ Unit or R ４ HSiO ２／２ It is preferable that the total number of units in one molecule is 3 to 100, preferably 4 to 70, more preferably 5 to 50, and even more preferably 6 to 30. If the number of SiH groups is less than the above lower limit or exceeds the above upper limit, the curability may decrease, and the adhesive strength and storage modulus G' of the resulting adhesive layer may decrease.

[0059] The above R ４are each independently a hydroxyl group, an alkoxy group having 1 to 6 carbon atoms, or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms and no aliphatic unsaturated bond. Examples of the monovalent hydrocarbon group include alkyl groups preferably having 1 to 6 carbon atoms, such as methyl, ethyl, propyl, and butyl groups; cycloalkyl groups preferably having 5 to 8 carbon atoms, such as cyclohexyl groups; aryl groups preferably having 6 to 10 carbon atoms, such as phenyl and tolyl groups; aralkyl groups preferably having 7 to 10 carbon atoms, such as benzyl groups; and monovalent hydrocarbon groups having 1 to 10 carbon atoms in which some or all of the hydrogen atoms bonded to carbon atoms have been substituted with hydroxy groups, cyano groups, halogen atoms, alkoxy groups, alkoxysilyl groups, polyoxyalkylene groups, epoxy groups, carboxyl groups, or the like, such as hydroxypropyl groups, cyanoethyl groups, 3-chloropropyl groups, 3,3,3-trifluoropropyl groups, 3,3,4,4,5,5,6,6,6-nonafluorohexyl groups, methoxypropyl groups, ethoxypropyl groups, and γ-glycidoxypropyl groups. Among these, R ４ is preferably an alkyl group or an aryl group, and more preferably a methyl group, an ethyl group, a propyl group or a phenyl group. ４ may be a hydroxyl group, but R ４ The ratio of the number of hydroxyl groups to the total number of (a) and (b) is preferably 10% or less, more preferably 5% or less, and even more preferably 1% or less. There is no lower limit, but the fewer the amount of hydroxyl groups in component (C), the better, and component (C) may not contain hydroxyl groups.

[0060] The component (C) has a viscosity of 1 to 2,000 mPa·s, and preferably 2 to 1,000 mPa·s at 25° C. If the viscosity is less than the above lower limit or exceeds the above upper limit, the curability may decrease, and the adhesive strength and storage modulus G′ of the resulting adhesive layer may decrease.

[0061] Component (C) is preferably a linear organohydrogenpolysiloxane represented by the following formula (4). (In the formula, R ４are each independently a hydroxyl group, an alkoxy group having 1 to 6 carbon atoms, or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms and no aliphatic unsaturated bonds; j is 0 to 1; k and m are numbers such that 1≦k≦98 and 0≦m≦60; 3≦2j+k≦100; and 3≦k+m+2≦100.

[0062] In the above formula (4), R ４ are each independently a hydroxyl group, an alkoxy group having 1 to 6 carbon atoms, or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms and no aliphatic unsaturated bond, as defined above. ４ is preferably an alkyl group or an aryl group, and more preferably a methyl group, an ethyl group, a propyl group or a phenyl group. ４ may be a hydroxyl group, but R ６ The ratio of the number of hydroxyl groups to the total number of groups is preferably 10% or less, more preferably 5% or less, and even more preferably 1% or less. There is no lower limit, but the smaller the amount of hydroxyl groups, the better, and it is also possible for the polymer to contain no hydroxyl groups.

[0063] With regard to j, k, and m, k is a number from 1 to 98, preferably from 3 to 80, more preferably from 4 to 70, more preferably from 5 to 50, and even more preferably from 6 to 30. m is a number from 0 to 60, preferably from 0 to 30, more preferably from 0 to 20, and even more preferably from 0 to 10. j is 0 or 1, and 2j + k is 3 to 100, preferably from 4 to 70, more preferably from 5 to 50, and even more preferably from 6 to 30. k + m + 2 is 3 to 100, preferably from 4 to 70, more preferably from 5 to 50, and even more preferably from 6 to 30.

[0064] In addition, the hydrogen atom bonded to the silicon atom and the group R bonded to the silicon atom ４The ratio of the total number of hydrogen atoms bonded to silicon atoms to the total number of hydrogen atoms bonded to silicon atoms (hereinafter referred to as the ratio of SiH groups) is preferably 20 to 50%, more preferably 25 to 49%, and even more preferably 30 to 48%. If the ratio of SiH groups is less than the above lower limit or exceeds the above upper limit, the curability may decrease, and the adhesive strength and storage modulus G' of the resulting adhesive layer may decrease.

[0065] Examples of component (C) include, but are not limited to, the following: In the following formulas, Me and Ph represent a methyl group and a phenyl group, respectively. The bonding order of each siloxane unit shown in parentheses is not limited to the following: In each of the following formulas, the total number of siloxane repeating units is an average value. (5≦z9+2≦100) (3≦z10+2≦100) (3≦z11≦97, 1≦z12≦60, 6≦z11+z12+2≦100, and the ratio of SiH groups is 20% to 50%.) (These numbers satisfy the conditions of 1≦z13≦97, 1≦z14≦60, and 4≦z13+z14+2≦100, and the proportion of SiH groups is 20% to 50%.) (These numbers satisfy the conditions of 0≦z15, 0≦z16, 0≦z17, 3≦z18, and 1≦z19, the proportion of SiH groups is 20% to 50%, and the average degree of polymerization of siloxane is 100 or less.) (These numbers satisfy the conditions of 0≦z20, 0≦z21, 0≦z22, 3≦z23, and 1≦z24, the proportion of SiH groups is 20% to 50%, and the average degree of polymerization of siloxane is 100 or less.) (These numbers satisfy the conditions of 0≦z25, 0≦z26, 0≦z27, 3≦z28, 1≦z29, and 1≦z30, the proportion of SiH groups is 20% to 50%, and the average degree of polymerization of siloxane is 100 or less.) (3≦z31≦97, 1≦z32≦60, 6≦z31+z32+2≦100, and the ratio of SiH groups is 20% to 50%.) (These numbers satisfy the conditions of 1≦z33≦97, 1≦z34≦60, and 4≦z33+z34+2≦100, and the proportion of SiH groups is 20% to 50%.) (3≦z35≦97, 1≦z36≦60, 6≦z35+z36+2≦100, and the ratio of SiH groups is 20% to 50%.) (3≦z37≦96, 1≦z38≦60, 1≦z39≦60, 7≦z37+z38+z39+2≦100, and the ratio of SiH groups is 20% to 50%.) (These numbers satisfy the conditions of 1≦z40≦96, 1≦z41≦60, 1≦z42≦60, and 5≦z40+z41+z42+2≦100, and the proportion of SiH groups is 20% to 50%.)

[0066] [Component (D)] Component (D) is a catalyst for promoting the addition reaction between component (A) and optional component (F) described below with component (C). Any catalyst that promotes the so-called hydrosilylation reaction can be used, and known platinum group metal catalysts can be used. Examples of platinum group metal catalysts include platinum, palladium, rhodium, ruthenium, and iridium catalysts, with platinum catalysts being particularly preferred. Examples of platinum catalysts include chloroplatinic acid, alcohol solutions or aldehyde solutions of chloroplatinic acid, reaction products of chloroplatinic acid with alcohols, and complexes of chloroplatinic acid or platinum with various olefins or vinylsiloxanes. Component (D) may be used alone or in combination of two or more.

[0067] The amount of component (D) to be blended may be a catalytic amount. The catalytic amount is an amount effective for promoting the addition reaction with component (A), optional component (F), and component (C). To obtain a good adhesive layer, the amount is 1 to 5,000 ppm, preferably 5 to 500 ppm, and particularly preferably 10 to 200 ppm, calculated as platinum group metal mass relative to the total mass of components (A), (B), (C), and optional components (A'), (E), and (F). If the amount is less than 1 ppm, the curability may be reduced, or the crosslink density of the resulting adhesive layer may be low, resulting in reduced adhesive strength and storage modulus G'. If the amount exceeds 5,000 ppm, the usable time of the treatment bath may be shortened.

[0068] [Component (E)] The silicone pressure-sensitive adhesive composition of the present invention comprises the component (E)R ３ ３ SiO１／２ Units and SiO ４／２ units and has hydroxyl groups and / or alkoxy groups having 1 to 6 carbon atoms bonded to silicon atoms, (R ３ ３ SiO １／２ Unit) / (SiO ４／２ The silicone pressure-sensitive adhesive composition may further contain an organopolysiloxane resin having a molar ratio, expressed as a molar ratio (R / R units), of 0.5 to 1.5 and a weight average molecular weight (Mw) of less than 5,000 as measured by gel permeation chromatography (GPC) relative to standard polystyrene standards, in an amount of 0.01 to 35% by mass relative to the total mass of the silicone pressure-sensitive adhesive composition. ３ are each independently a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, a hydroxyl group, or an alkoxy group having 1 to 6 carbon atoms. The organopolysiloxane resin does not contain alkenyl groups, or contains alkenyl groups in such an amount that the total amount of alkenyl groups in the organopolysiloxane resin is less than 0.005 mol / 100 g.

[0069] The component (E) is R ３ ３ SiO １／２ Units and SiO ４／２ units, R ３ ３ SiO １／２ Units / SiO ４／２ The organopolysiloxane resin has a molar ratio of units of 0.5 to 1.5, preferably 0.55 to 1.3, and preferably 0.6 to 1.0. If the molar ratio is less than the above lower limit or exceeds the above upper limit, the adhesive strength and storage modulus G' of the resulting adhesive layer may decrease. The component (E) may be used alone or in combination of two or more types.

[0070] The organopolysiloxane resin (E) can undergo a condensation reaction with components (A), (B), and optionally components (A') and (F).

[0071] R ３ are each independently a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, a hydroxyl group, or an alkoxy group having 1 to 6 carbon atoms. １Among them, a methyl group and a phenyl group are preferred, and a methyl group is particularly preferred.

[0072] Component (E) may contain or not contain alkenyl groups, but the total amount of alkenyl groups contained in the resin is less than 0.005 mol / 100 g, more preferably less than 0.004 mol / 100 g, and even more preferably less than 0.003 mol / 100 g. Component (E) most preferably does not contain alkenyl groups. If the amount exceeds the upper limit, the adhesive strength and storage modulus G' of the resulting adhesive layer may decrease.

[0073] The component (E) is R ３ ３ SiO １／２ Units and SiO ４／２ Although the organopolysiloxane resin essentially contains the R unit, it may contain the R unit within a range that does not impair the properties of the present invention. ３ ２ SiO ２／２ Units and R ３ SiO ３／２ Unit (R ３ is as described above).

[0074] Component (E) may contain siloxane units (silanol group-containing units) having a hydroxyl group bonded to a silicon atom, or siloxane units (alkoxy group-containing units) having an alkoxy group having 1 to 6 carbon atoms bonded to a silicon atom. The amount of silanol group-containing units is preferably such that the hydroxyl group content of component (E) is 0.005 to 0.3 mol / 100g, more preferably 0.008 to 0.25 mol / 100g, and even more preferably 0.01 to 0.2 mol / 100g. If the hydroxyl group content exceeds 0.3 mol / 100g, the adhesive strength and storage modulus G' of the resulting adhesive layer may decrease, or curability may decrease. Furthermore, the amount of alkoxy group-containing units is preferably such that the alkoxy group content of component (E) is 0.3 mol / 100g or less, more preferably 0.2 mol / 100g or less, and even more preferably 0.1 mol / 100g or less. If the alkoxy group content exceeds 0.3 mol / 100 g, the adhesive strength and storage modulus G' of the resulting adhesive layer may decrease, or the curing properties may decrease. There is no lower limit, but the alkoxy group content can be set to, for example, 0.003 mol / 100 g or more.

[0075] Furthermore, the total amount of the silanol group-containing units and alkoxy group-containing units, as the sum of the hydroxyl group content and alkoxy group content, in component (E) is preferably 0.008 to 0.3 mol / 100 g, more preferably 0.01 to 0.25 mol / 100 g, and particularly preferably 0.02 to 0.2 mol / 100 g. By having hydroxyl groups or alkoxy groups in such amounts, the component (E) can undergo a condensation reaction with component (A), component (B), or optional component (A') and component (F).

[0076] Examples of the alkoxy group having 1 to 6 carbon atoms include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, and a phenoxy group. ３ ２ (OH)SiO １／２ Unit, R ３ (OH) ２ SiO １／２ Unit, R ３ (OH)SiO ２／２ Units: (OH)SiO ３／２The alkoxy group-containing unit is, for example, a unit represented by R ３ ２ (OR')SiO １／２ Unit, R ３ (OR') ２ SiO １／２ Unit, R ３ (OR')SiO ２／２ Units, (OR')SiO ３／２ (OR' are each independently an alkoxy group having 1 to 6 carbon atoms, as exemplified above), etc. ３ ３ SiO １／２ Units and SiO ４／２ When the unit is SiO ４／２ It can be bonded to a silicon atom from the unit.

[0077] Component (E) has a weight-average molecular weight of less than 5,000. The weight-average molecular weight is preferably 500 to 4,750, and more preferably 1,000 to 4,500. The weight-average molecular weight (Mw) is a value determined by GPC (gel permeation chromatography) analysis using polystyrene as a standard substance under the conditions described above.

[0078] [Component (F)] The silicone pressure-sensitive adhesive composition of the present invention comprises (F) a compound having one or more alkenyl groups per molecule, the alkenyl group content being 0.005 to 0.5 mol / 100 g, and R ３ ３ SiO １／２ Units and SiO ４／２ is an organopolysiloxane resin having units (R ３ ３ SiO １／２ Unit) / (SiO ４／２ The organopolysiloxane resin may be contained in an amount of 0.01 to 45% by mass relative to the total mass of the silicone pressure-sensitive adhesive composition, and the organopolysiloxane resin may have a molar ratio, expressed as a molar ratio of 0.5 to 1.5, represented by the formula (R), and optionally have silicon-bonded hydroxyl groups and / or silicon-bonded alkoxy groups having 1 to 6 carbon atoms. ３are each independently a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, a hydroxyl group, or an alkoxy group having 1 to 6 carbon atoms.

[0079] Component (F) has one or more alkenyl groups in one molecule, and R ３ ３ SiO １／２ Units and SiO ４／２ units, R ３ ３ SiO １／２ Units / SiO ４／２ The organopolysiloxane resin has a molar ratio of the unit of 0.5 to 1.5, preferably 0.55 to 1.3, and more preferably 0.6 to 1.0. If the molar ratio is less than the above lower limit or exceeds the above upper limit, the adhesive strength and storage modulus G' of the resulting adhesive layer may decrease. The component (F) may be used alone or in combination of two or more types.

[0080] The organopolysiloxane resin (F) can undergo a condensation reaction with components (A), (B), and optionally components (A') and (E).

[0081] R ３ are each independently a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, a hydroxyl group, or an alkoxy group having 1 to 6 carbon atoms. １ Among them, methyl group, phenyl group and vinyl group are preferred, and methyl group and vinyl group are particularly preferred.

[0082] Component (F) has 0.005 to 0.5 mol of alkenyl groups per 100 g of organopolysiloxane. The amount of alkenyl groups is preferably 0.01 to 0.3 mol / 100 g, more preferably 0.02 to 0.2 mol / 100 g, and even more preferably 0.05 to 0.16 mol / 100 g. If the amount is less than the above lower limit or exceeds the above upper limit, the adhesive strength and storage modulus G' of the resulting adhesive layer may decrease.

[0083] The component (F) is R ３ ３ SiO １／２ Units and SiO ４／２Although the organopolysiloxane resin essentially contains the R unit, it may contain the R unit within a range that does not impair the properties of the present invention. ３ ２ SiO ２／２ Units and R ３ SiO ３／２ Unit (R ３ is as defined above). Preferably, R ３ ２ SiO ２／２ units, (R ３ ２ SiO ２／２ ) / (SiO ４／２ The molar ratio represented by the unit (unit) is preferably 0.01 to 0.5, more preferably 0.02 to 0.4, even more preferably 0.03 to 0.3, and even more preferably 0.05 to 0.25.

[0084] More preferably, R ５ ３ SiO １／２ Unit, R ５ ２ R ６ SiO １／２ units, and SiO ４／２ an organopolysiloxane resin consisting of units, or R ５ ３ SiO １／２ Unit, R ５ R ６ SiO ２／２ units, and SiO ４／２ An organopolysiloxane resin consisting of R units is preferred. ５ is the above R other than an alkenyl group. ３ and R ６ is an alkenyl group having 2 to 10 carbon atoms. ５ is the above R other than an alkenyl group. ３ In particular, a methyl group and a phenyl group are preferred. ６ is an alkenyl group having 2 to 10 carbon atoms, and a vinyl group is particularly preferred.

[0085] R ５ ３ SiO １／２ Unit, R ５ ２ R ６SiO １／２ units, and SiO ４／２ In the organopolysiloxane resin consisting of units, the molar ratio of each unit is SiO ４／２ R for unit (hereinafter referred to as Q unit) ５ ３ SiO １／２ Units and R ５ ２ R ６ SiO １／２ It is sufficient that the molar ratio of M units / Q units (hereinafter collectively referred to as M units) is 0.5 to 1.5, preferably 0.55 to 1.3, and more preferably 0.6 to 1.0.

[0086] R ５ ３ SiO １／２ Unit (hereinafter referred to as M unit), R ５ R ６ SiO ２／２ units (hereinafter referred to as D units), and SiO ４／２ In an organopolysiloxane resin composed of units (hereinafter referred to as Q units), the molar ratios of the respective units, that is, the molar ratio of M units / Q units and the molar ratio of D units / Q units, may both be within the above-mentioned ranges. That is, the ratio of M units / Q units is 0.5 to 1.5, preferably 0.55 to 1.3, and preferably 0.6 to 1.0, and the ratio of D units / Q units is 0.01 to 0.5, more preferably 0.02 to 0.4, more preferably 0.03 to 0.3, and even more preferably 0.05 to 0.25. The molar ratios of M units / Q units and D units / Q units are determined by the concentration of the molar ratios of the deuterated chloroform solution. １ H-NMR and ２９ This can be determined by a known structural analysis method using Si-NMR (the same applies hereinafter).

[0087] Component (F) may contain siloxane units (silanol group-containing units) having a hydroxyl group bonded to a silicon atom, or siloxane units (alkoxy group-containing units) having an alkoxy group having 1 to 6 carbon atoms bonded to a silicon atom. The amount of silanol group-containing units is preferably such that the hydroxyl group content of component (F) is 0.005 to 0.3 mol / 100g, more preferably 0.008 to 0.2 mol / 100g, and even more preferably 0.01 to 0.1 mol / 100g. If the hydroxyl group content exceeds 0.3 mol / 100g, the adhesive strength and storage modulus G' of the resulting adhesive layer may decrease, or curability may decrease. Furthermore, the amount of alkoxy group-containing units is preferably such that the alkoxy group content of component (F) is 0.3 mol / 100g or less, more preferably 0.2 mol / 100g or less, and even more preferably 0.1 mol / 100g or less. If the alkoxy group content exceeds 0.3 mol / 100g, the adhesive strength or storage modulus G' of the resulting adhesive layer may decrease, or curing properties may be impaired. There is no lower limit, but it can be, for example, 0.003 mol / 100g or more. Furthermore, the total amount of the silanol group-containing units and alkoxy group-containing units, as the sum of the hydroxyl group content and alkoxy group content, in component (F) is preferably 0.008 to 0.3 mol / 100g, more preferably 0.01 to 0.2 mol / 100g, and particularly preferably 0.015 to 0.1 mol / 100g. The presence of such hydroxyl or alkoxy groups allows for condensation reactions with the hydroxyl group-containing components (A) and (B) and optional components (A') and (E).

[0088] Examples of the alkoxy group having 1 to 6 carbon atoms include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, and a phenoxy group. ３ ２ (OH)SiO １／２ Unit, R ３ (OH) ２ SiO １／２ Unit, R ３ (OH)SiO ２／２ Units: (OH)SiO ３／２ The alkoxy group-containing unit is, for example, a unit represented by R３ ２ (OR')SiO １／２ Unit, R ３ (OR') ２ SiO １／２ Unit, R ３ (OR')SiO ２／２ Units, (OR')SiO ３／２ (OR' are each independently an alkoxy group having 1 to 6 carbon atoms, as exemplified above), etc. ３ ３ SiO １／２ Units, SiO ４／２ units, and optionally R ３ ２ SiO ２／２ When the hydroxyl group or alkoxyl group is SiO ４／２ It can be bonded to a silicon atom from the unit.

[0089] The component (F) preferably has a weight average molecular weight of 1,000 to 10,000, more preferably 1,200 to 8,000, even more preferably 1,400 to 6,000, and even more preferably 1,600 to 4,000. If the weight average molecular weight is less than the above lower limit or exceeds the above upper limit, the adhesive strength and storage modulus G' of the resulting adhesive layer may decrease.

[0090] In the silicone pressure-sensitive adhesive composition of the present invention, the blending ratio of the above-mentioned components (A), (B), and optional components (A'), (E), and (F) is preferably 25 to 70 mass%, more preferably 30 to 60 mass%, even more preferably 33 to 55 mass%, and most preferably 35 to 50 mass%, relative to the total mass of components (A), (B), (A'), (E), and (F). The blending ratio of component (B) is preferably 5 to 70 mass%, more preferably 6 to 55 mass%, even more preferably 8 to 50 mass%, and most preferably 10 to 45 mass%, relative to the total mass of components (A), (B), (A'), (E), and (F). The blending ratio of component (A') is preferably 0 to 50 mass%, more preferably 0 to 40 mass%, and most preferably 0 to 30 mass%, relative to the total mass of components (A), (B), (A'), (E), and (F). The blending ratio of component (E) is preferably 0 to 35 mass%, more preferably 0 to 30 mass%, and even more preferably 0 to 25 mass%, relative to the total mass of components (A), (B), (A'), (E), and (F). When component (E) is contained, the lower limit is preferably 0.01 mass% or more. The blending ratio of component (F) is preferably 0 to 45 mass%, more preferably 0 to 40 mass%, even more preferably 0 to 35 mass%, and most preferably 0 to 30 mass%, relative to the total mass of components (A), (B), (A'), (E), and (F). When component (F) is contained, the lower limit thereof is preferably 0.01 mass % or more.

[0091] The amount of each component relative to the total mass of the entire silicone pressure-sensitive adhesive composition, including the optional components described below, is preferably 0.1 to 70 mass%, more preferably 0.3 to 60 mass%, and even more preferably 0.5 to 55 mass% for component (A). Component (B) is preferably 0.01 to 70 mass%, more preferably 0.05 to 55 mass%, and even more preferably 0.10 to 50 mass% for component (A'). Component (E) is preferably 0 to 35 mass%, more preferably 0 to 30 mass%, and even more preferably 0 to 25 mass% for component (E). When component (E) is included, the lower limit is preferably 0.01 mass% or greater. Component (F) is preferably 0 to 45 mass%, more preferably 0 to 40 mass%, even more preferably 0 to 35 mass%, and most preferably 0 to 30 mass%. When component (E) is contained, the lower limit thereof is preferably 0.01 mass % or more.

[0092] In the silicone pressure-sensitive adhesive composition of the present invention, the ratio of the total mass of the linear organopolysiloxane component to the total mass of the organopolysiloxane resin component is 25 / 75 to 70 / 30, more preferably 30 / 70 to 60 / 40, more preferably 33 / 67 to 55 / 45, more preferably 35 / 65 to 50 / 50, and even more preferably 40 / 60 to 48 / 52. That is, the ratio of (total mass of component (A) and optional component (A')) / (total mass of component (B) and optional component (E) and / or component (F)) is 25 / 75 to 70 / 30, more preferably 30 / 70 to 60 / 40, more preferably 33 / 67 to 55 / 45, more preferably 35 / 65 to 50 / 50, and even more preferably 40 / 60 to 48 / 52. If the content is less than the lower limit or exceeds the upper limit, the adhesive strength and storage modulus G' of the resulting adhesive layer may decrease.

[0093] Another preferred embodiment of the present invention is a silicone pressure-sensitive adhesive composition comprising a condensation reaction product of the above-mentioned component (A), the optional component (A'), the component (B), and the optional components (F) and / or (E). That is, some or all of the components (A), (B), and the optional components (A'), (E), and (F) may be subjected to a condensation reaction in advance. Specifically, the alkoxy groups or hydroxyl groups of the component (A) and the optional component (A') and the alkoxy groups or hydroxyl groups of the component (B) and the optional components (E) and (F) may be subjected to a hydrolysis-condensation reaction or condensation reaction to obtain a condensation reaction product, which may then be mixed with the other components. Alternatively, the alkoxy groups or hydroxyl groups of the optional component (A') and the alkoxy groups or hydroxyl groups of the component (B) and the optional components (E) and (F) may be subjected to a hydrolysis-condensation reaction or condensation reaction to obtain a condensation reaction product, which may then be mixed with the other components. Alternatively, the alkoxy groups or hydroxyl groups of component (A) and any component (A') and the alkoxy groups or hydroxyl groups of component (B) and any component (E) and component (F) may be subjected to a hydrolysis condensation reaction or a condensation reaction to obtain a condensation reaction product, which may then be mixed with the other components.

[0094] To carry out the condensation reaction, a mixture of component (A) and / or (A') dissolved in a solvent such as toluene and component (B) and / or component (E) and / or component (F) is reacted at room temperature (25°C) or under heat using one or more condensation catalysts such as acids, bases, and organic acid metal salts, and neutralized as necessary. In this case, the reaction is preferably carried out so that the total amount of hydroxyl groups and alkoxy groups in the SiOH groups (silanol groups) in the condensation reaction product is 0.3 mol / 100g or less, particularly 0.25 mol / 100g or less. The lower limit is not particularly limited, and is, for example, 0.001 mol / 100g or more. Therefore, the silicone pressure-sensitive adhesive composition of the present invention can be a composition containing the product obtained by the condensation reaction of component (A) and / or (A') with component (B) and / or component (E) and / or component (F), as well as the aforementioned component (C) and component (D). By carrying out a condensation reaction in advance, the adhesive strength, storage modulus G', holding power, tack, etc. of the resulting cured product may be improved, and migration of the silicone component to the adherend may be suppressed.

[0095] Examples of the basic condensation catalyst used in the reaction include metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide; carbonates such as sodium carbonate and potassium carbonate; bicarbonates such as sodium bicarbonate and potassium bicarbonate; metal alkoxides such as sodium methoxide and potassium butoxide; organic metals such as butyllithium; potassium silanolate; ammonia gas, aqueous ammonia, methylamine, ethylamine, propylamine, hexylamine, butanolamine, butylamine, dimethylamine, diethylamine, diethanolamine, dipropylamine, dibutylamine, dihexylamine, ethylamylamine, imidazole, propylhexylamine, trimethylamine, triethylamine, tripropylamine, tripropanolamine, pyridine, N-methylimidazole, methylpropylhexylamine, dodecylamine phosphate, tetramethylguanidine, and nitrogen compounds and salts thereof such as diazabicyclononane. Among these, ammonia gas or aqueous ammonia is preferred.

[0096] The temperature for the condensation reaction can be 10 to 150° C., but is usually from room temperature (25° C.) to the reflux temperature of the organic solvent. The reaction time is not particularly limited, but may be from 0.5 to 20 hours, preferably from 1 to 16 hours.

[0097] Furthermore, after the reaction is completed, a neutralizing agent may be added to neutralize the basic catalyst, if necessary. Examples of the neutralizing agent include acidic gases such as hydrogen chloride and carbon dioxide; organic acids such as acetic acid, octylic acid, and citric acid; and mineral acids such as hydrochloric acid, sulfuric acid, and phosphoric acid. When ammonia gas, aqueous ammonia, or a low-boiling amine compound is used as the alkaline catalyst, the neutralizing agent may be distilled off by passing an inert gas such as nitrogen through the system.

[0098] [Component (G)] Component (G) is an addition reaction inhibitor and is an optional component. It can be added before heat curing, for example, when preparing the silicone pressure-sensitive adhesive composition or when applying the pressure-sensitive adhesive composition to a substrate, to prevent thickening or gelation of the treatment liquid containing the pressure-sensitive adhesive composition. Examples of the component (G) include various organic nitrogen compounds, organic phosphorus compounds, organic silicon compounds, acetylene compounds, unsaturated carboxylic acid esters, and oxime compounds.

[0099] More specifically, examples of the acetylene-based compounds include acetylene alcohols such as 3-methyl-1-butyn-3-ol, 3,5-dimethyl-1-hexyn-3-ol, 3-methyl-1-pentyn-3-ol, 2-phenyl-3-butyn-2-ol, and 1-ethynylcyclohexanol; acetylene compounds such as 3-methyl-3-penten-1-yne and 3,5-dimethyl-3-hexen-1-yne; 3-methyl-3-trimethylsiloxy-1-butyne, 3-methyl-3-trimethylsiloxy-1-pentyne, 3,5-dimethyl-3-trimethylsiloxy-1-hexyne, and 1-ethynyl-1-trimethylsiloxysilane; Examples of the component (G) include reaction products of acetylene compounds such as cyclohexane and bis(2,2-dimethyl-3-butynoxy)dimethylsilane with chlorosilanes, alkoxysilanes, siloxanes, or hydrogensilanes, vinylsiloxanes such as 1,3,5,7-tetramethyl-1,3,5,7-tetravinylcyclotetrasiloxane and 1,1,3,3-tetramethyl-1,3-divinyldisiloxane, unsaturated carboxylic acid esters such as diallyl maleate, dimethyl maleate, diallyl fumarate, and diethyl fumarate, organic nitrogen compounds such as benzotriazole, other organic phosphorus compounds, and oxime compounds. Component (G) may be used alone or in combination of two or more types.

[0100] The amount of component (G) blended is in the range of 0 to 8.0 parts by mass per 100 parts by mass of the total of components (A), (B), (C), and optional components (A'), (E), and (F). When blended, the amount is preferably in the range of 0.01 to 8.0 parts by mass, and more preferably in the range of 0.05 to 5.0 parts by mass. If the blended amount exceeds the upper limit, the curability of the resulting composition may decrease. If the blended amount is equal to or greater than the lower limit, the reaction control effect is fully exerted.

[0101] [Other Optional Components] In addition to the above-mentioned components, other components can be optionally added to the silicone pressure-sensitive adhesive composition of the present invention. The amount of other components may be in accordance with that of conventionally known silicone pressure-sensitive adhesives, and may be appropriately adjusted within a range that does not impair the effects of the present invention. For example, non-reactive organopolysiloxanes such as polydimethylsiloxane and polydimethyldiphenylsiloxane; antioxidants such as phenols, quinones, amines, phosphorus, phosphite, sulfur, and thioethers; light stabilizers such as triazoles and benzophenones; flame retardants such as phosphate esters, halogens, phosphorus, and antimony; antistatic agents such as cationic surfactants, anionic surfactants, and nonionic surfactants; dyes; pigments; antifoaming agents; fillers; leveling agents; adhesion improvers such as silane coupling agents; thickeners; photopolymerization initiators; reactive diluents, and solvents for reducing viscosity during coating.

[0102] Examples of the solvent include aromatic hydrocarbon solvents such as toluene and xylene, aliphatic hydrocarbon solvents such as hexane, heptane, octane, isooctane, decane, cyclohexane, methylcyclohexane, and isoparaffin, hydrocarbon solvents such as industrial gasoline, petroleum benzine, and solvent naphtha, ketone solvents such as acetone, methyl ethyl ketone, 2-pentanone, 3-pentanone, 2-hexanone, 2-heptanone, 4-heptanone, methyl isobutyl ketone, diisobutyl ketone, acetonylacetone, and cyclohexanone, ester solvents such as ethyl acetate, propyl acetate, isopropyl acetate, butyl acetate, and isobutyl acetate, and diethyl Examples of solvents that can be used include ether solvents such as diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, 1,2-dimethoxyethane, and 1,4-dioxane, solvents having an ester and an ether moiety such as 2-methoxyethyl acetate, 2-ethoxyethyl acetate, propylene glycol monomethyl ether acetate, and 2-butoxyethyl acetate, and siloxane solvents such as hexamethyldisiloxane, octamethyltrisiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, tris(trimethylsiloxy)methylsilane, and tetrakis(trimethylsiloxy)silane. These can be used alone or in appropriate combinations of two or more. When a solvent is added, the amount thereof is preferably 10 to 20,000 parts by mass, more preferably 25 to 10,000 parts by mass, and even more preferably 50 to 1,000 parts by mass, per 100 parts by mass of the total of components (A), (B), and (C), and optional components (A'), (E), and (F). The silicone pressure-sensitive adhesive composition of the present invention can also be a solvent-free type.

[0103] [Method for Producing Silicone Pressure-Sensitive Adhesive Compositions] (I) A silicone pressure-sensitive adhesive composition containing a linear organopolysiloxane and the organopolysiloxane resin can be prepared by mixing and dissolving the above-mentioned components. From the standpoint of pot life, it is desirable to premix components (A), (B), and (C), optional components (A'), (E), and (F), optionally component (G), and other optional components, and then add component (D) immediately before use. (II) A method for producing a silicone pressure-sensitive adhesive composition containing a condensation reaction product of at least one linear organopolysiloxane with at least one other linear organopolysiloxane can be achieved by, as described above, precondensing component (A) and / or optional component (A') and component (B) and / or optional component (E), and / or optional component (F).

[0104] The silicone pressure-sensitive adhesive composition of the present invention can be applied to various substrates and cured under specified conditions to obtain a silicone adhesive layer. The silicone pressure-sensitive adhesive composition of the present invention can be suitably used, for example, as an adhesive tape, adhesive sheet, or adhesive film having a substrate and an adhesive layer made of a cured product of the composition laminated on at least one side of the substrate.

[0105] [Substrate] The substrate may be selected from paper, plastic film made of plastic, glass, metal, cloth, etc. Examples of paper include fine paper, coated paper, art paper, glassine paper, polyethylene-laminated paper, kraft paper, Japanese paper, synthetic paper, etc. Examples of plastic films include polyethylene film, polypropylene film, polyester film, polyimide film, polyamide film, polyvinyl chloride film, polyvinylidene chloride film, polyvinyl alcohol film, polycarbonate film, polytetrafluoroethylene film, polystyrene film, ethylene-vinyl acetate copolymer film, ethylene-vinyl alcohol copolymer film, triacetyl cellulose film, polyether ether ketone film, polyphenylene sulfide film, etc. There are no particular limitations on the thickness or type of glass, and it may be chemically strengthened. Glass fiber can also be used, and it may be used alone or in combination with other resins. Examples of cloth include natural fiber cloth, synthetic fiber cloth, and artificial leather, and examples of metal include aluminum foil, copper foil, gold foil, silver foil, and nickel foil.

[0106] To further improve the adhesion between these substrates and the silicone adhesive layer, the substrates may be subjected to a primer treatment, corona treatment, etching treatment, sandblasting treatment, or plasma treatment.

[0107] The surface of the substrate opposite to the adhesive layer surface may be surface-treated to prevent scratches, stains, fingerprints, glare, reflection, static electricity, etc. The adhesive layer may be applied to the substrate before the surface treatment, or the adhesive layer may be applied after the surface treatment.

[0108] Examples of the scratch prevention treatment (hard coating treatment) include treatment with an acrylate-based, silicone-based, oxetane-based, inorganic-based, or organic-inorganic hybrid hard coating agent.

[0109] Examples of the antifouling treatment include treatment with an antifouling agent such as a fluorine-based, silicone-based, ceramic-based, or photocatalytic-based agent.

[0110] Examples of antireflection treatments include wet treatments using a fluorine-based, silicone-based, or other antireflection agent, and dry treatments using vapor deposition or sputtering. Examples of antistatic treatments include treatments using surfactant-based, silicone-based, organoboron-based, conductive polymer-based, metal oxide-based, or vapor-deposited metal-based antistatic agents.

[0111] [Method for producing adhesive tape and adhesive film] The coating method may be performed using a known coating method, such as a comma coater, lip coater, roll coater, die coater, knife coater, blade coater, rod coater, bar coater, kiss coater, gravure coater, screen coating, dip coating, or cast coating.

[0112] The coating amount is determined appropriately depending on the application, but typically it is an amount that results in a silicone adhesive layer having a thickness of 1 to 2,000 μm, preferably 2 to 1,000 μm, and especially 3 to 500 μm after curing.

[0113] The curing conditions for the silicone pressure-sensitive adhesive composition are preferably, but not limited to, 70 to 250° C. for 10 seconds to 10 minutes.

[0114] The pressure-sensitive adhesive tape or pressure-sensitive adhesive film of the present invention may be produced by directly applying the silicone pressure-sensitive adhesive composition of the present invention to a substrate as described above and curing the composition to form a silicone adhesive layer, or by a transfer method in which the composition is applied to a release-coated release film or release paper and cured to form a silicone adhesive layer, and then the silicone adhesive layer is laminated to the above-mentioned substrate.

[0115] [Range of Adhesion and Adhesion Strength] The silicone pressure-sensitive adhesive composition of the present invention is characterized in that the cured layer obtained by curing the composition via a hydrosilylation reaction is adhesive. The pressure-sensitive adhesive layer of the present invention has the above-mentioned configuration and exhibits sufficient adhesion strength for practical use, so it can be used in place of known silicone pressure-sensitive adhesives as desired.

[0116] More specifically, for a pressure-sensitive adhesive tape having a 40 μm thick adhesive layer obtained by curing the silicone pressure-sensitive adhesive composition of the present invention laminated onto a 25 μm thick polyimide film, the pressure-sensitive adhesive layer can be designed to have an adhesive strength of 3.0 N / 25 mm or more when measured at a tensile speed of 300 mm / min using a 180° peel test method against a 2 mm thick silicone rubber sheet (cured KE951U manufactured by Shin-Etsu Chemical Co., Ltd.) More preferably, the adhesive strength is in the range of 3.5 to 15.0 N / 25 mm, more preferably in the range of 4.0 to 13.0 N / 25 mm, even more preferably in the range of 4.5 to 12.0 N / 25 mm, and even more preferably in the range of 5.0 to 10.0 N / 25 mm. It should be noted that the thickness of the cured layer (40 μm) mentioned above is the thickness of the cured layer itself, which serves as a standard for objectively defining the adhesive strength of the cured layer according to the present invention, and it goes without saying that the silicone pressure-sensitive adhesive composition of the present invention is not limited to a thickness of 40 μm and can be used as a cured layer or adhesive layer of any thickness.

[0117] [Storage Modulus and Other Viscoelastic Properties] The adhesive layer obtained by curing the silicone pressure-sensitive adhesive composition of the present invention has a storage modulus G' at 25°C of 1.00 MPa or more, preferably 1.20 to 20.0 MPa, more preferably 1.50 to 18.0 MPa, even more preferably 2.00 to 15.0 MPa, even more preferably 2.50 to 13.0 MPa, and even more preferably 3.00 to 10.0 MPa. Furthermore, the adhesive layer obtained by curing the silicone pressure-sensitive adhesive composition of the present invention has a storage modulus G' at 80°C of 0.10 MPa or more, preferably 0.12 to 10.0 MPa, even more preferably 0.15 to 8.00 MPa, even more preferably 0.17 to 6.00 MPa, even more preferably 0.19 to 4.0 MPa, and even more preferably 0.20 to 2.0 MPa. Because the silicone pressure-sensitive adhesive composition of the present invention has such a storage modulus G' at room temperature and at high temperatures, it is suitable for use in the formation of elastic pressure-sensitive adhesive members, as components for electronic devices and electrical equipment such as speakers and transducers, as well as for application in the fields of advanced electronics materials and display elements for smart devices and the like.

[0118] The storage modulus G' of the pressure-sensitive adhesive layer according to the present invention can be measured by a known measurement method. For example, it can be measured using a viscoelasticity measuring device DHR-2 (TA Instruments Inc.), using a disk-shaped sample having a diameter of 8 mm and a thickness of about 0.5 to 1.5 mm, with Φ8 mm parallel plates, a frequency of 1 Hz, a strain of 0.1%, a heating rate of 3°C / min, and values ​​at 25°C and 80°C in the operating temperature range of -55°C to 100°C.

[0119] [Uses of Adhesive Tapes and Adhesive Films] There are no particular limitations on the types of adherends that can be bonded or fixed with an adhesive tape produced using the silicone adhesive composition of the present invention, but examples include silicone materials such as silicone rubber, silicone sealant, silicone potting material, silicone LIM material, and silicone varnish; silicone-coated release paper or release film; metal, plastic, wood, cloth, or paper coated with a silicone coating material, a silicone release agent, a silicone water repellent, or a paint containing silicone; and composites formed by combining two or more of these. Thus, the silicone adhesive composition of the present invention can be suitably used for adhesion and bonding of silicone materials, particularly for adhesion and bonding of silicone rubber.

[0120] Furthermore, the cured product obtained by curing the silicone pressure-sensitive adhesive composition of the present invention is useful as an elastic pressure-sensitive adhesive member for various electronic devices or electrical equipment, and is particularly useful as an electronic material, a member for a display device, or a member for a transducer (including for sensors, speakers, actuators, and generators).

[0121] Furthermore, the tape is also useful for applications in high-temperature environments. Examples include heat-resistant tape, electrical insulating tape, heat-sealing tape, plating masking tape, and heat treatment masking tape. Examples of applications include protection, masking, temporary fixation, fixation during transport, and splicing of adherends in the manufacturing process of electronic components and semiconductor components. Examples of adherends include, but are not limited to, metals such as stainless steel, copper, and iron, and these metals whose surfaces have been plated or rust-proofed; glass, tempered or stain-proofed glass, and ceramics such as porcelain; resins such as polytetrafluoroethylene, polyimide, epoxy resin, novolac resin, and polarizing plates; and composites formed by combining two or more of these materials.

[0122] The present invention will be described in more detail below with reference to examples and comparative examples, but the present invention is not limited to the following examples. In the following, parts represent parts by mass, and characteristic values ​​represent values ​​measured by the following test methods.

[0123] [Viscosity] The viscosity (mPa·s) is a value measured using a B-type rotational viscometer in accordance with JIS K7117-1.

[0124] [Weight Average Molecular Weight (Mw)] In the present invention, the weight average molecular weight (Mw) is a value determined by GPC (gel permeation chromatography) analysis using polystyrene as a standard substance under the following conditions. (Measurement conditions) GPC measurement device: HLC-8320 (manufactured by Tosoh Corporation) Detector: differential refractive index detector (RI) Measurement solvent: toluene Flow rate: 0.35 mL / min GPC columns: (passed in the following order) TSKgel Guardcolumn SuperHZ-L (4.6 mm I.D. × 2 cm × 1) TSKgel SuperHZ4000 (4.6 mm I.D. × 15 cm × 1) TSKgel SuperHZ3000 (4.6 mm I.D. × 15 cm × 1) TSKgel SuperHZ2000 (4.6 mm I.D. × 15 cm × 2) (all manufactured by Tosoh Corporation) Measurement temperature: 40°C Sample injection amount: 10 μL (toluene solution with a silicone concentration of 0.5 wt%)

[0125] [Adhesion to Silicone Rubber] Each silicone pressure-sensitive adhesive composition was applied to a 25 μm thick, 25 mm wide polyimide film using an applicator so that the thickness of the adhesive layer after curing was 40 μm, and then heated and cured at 150°C for 3 minutes to produce an adhesive tape. This adhesive tape was attached to a 2 mm thick silicone rubber sheet (cured KE951U (trade name) manufactured by Shin-Etsu Chemical Co., Ltd.) and pressure-bonded by moving a 2 kg rubber-coated roller back and forth once. After leaving it at room temperature for about 24 hours, one end of the adhesive tape was peeled off at 25°C, and the force (N / 25 mm) required to peel it from the silicone rubber sheet at a pulling rate of 300 mm / min and an angle of 180° was measured using a tensile tester (DSC-500 model manufactured by Shimadzu Corporation).

[0126] [Dynamic Viscoelasticity (Storage Modulus G')] Each silicone pressure-sensitive adhesive composition was coated onto a release liner coated with a fluorosilicone release coating so that the thickness after curing was approximately 40 μm, and then cured at 150°C for 3 minutes. The process of overlapping the pressure-sensitive adhesive layers and peeling off the release liners was repeated to overlap 16 pressure-sensitive adhesive layers, obtaining a film sample with a thickness of 600 μm or more and sandwiched between release liners on both sides. After storing the film at 70°C for 7 days, an 8 mm diameter circle was cut out, the release liners on both sides were peeled off, and the film was attached to the parallel plate probe of a dynamic viscoelasticity apparatus to measure the storage modulus G'. (Measurement Conditions) Measuring Instrument: DHR-2 (TA Instruments Inc.) Adhesion Jig (Geometry): Φ8 mm Parallel Plate Measurement Temperature: -55°C to 100°C Heating Rate: 3°C / min Frequency: 1 Hz Strain: 0.1%

[0127] The following raw materials were used in the examples and comparative examples. In the following formulas, Me represents a methyl group, Vi represents a vinyl group, and Ph represents a phenyl group. The bonding order of each siloxane unit shown in parentheses is not limited to the following. In each formula below, the total number of siloxane repeating units is an average value.

[0128] (A-1) An organopolysiloxane represented by the following formula, which has a viscosity of 58,000 mPa·s at 25°C when dissolved in toluene to a concentration of 30% by mass and has an alkenyl group content of 0.0008 mol / 100 g: (z51 and z52 are numbers that satisfy the above viscosity and vinyl group amount, and the ratio of the number of hydroxyl groups to the total number of groups bonded to silicon atoms is 0.007%).

[0129] (A-2) An organopolysiloxane represented by the following formula, which has a viscosity of 25,000 mPa·s at 25°C when dissolved in toluene to a concentration of 30% by mass, has an alkenyl group content of 0.0015 mol / 100 g, and has a ratio of the total number of phenyl groups to the total number of groups bonded to silicon atoms of 1.0%: (z53, z54, and z55 are numbers that satisfy the above-mentioned viscosity, vinyl group content, and phenyl group content, and the ratio of the number of hydroxyl groups to the total number of groups bonded to silicon atoms is 0.006%).

[0130] (A'-1) An organopolysiloxane represented by the following formula, which has a viscosity of 70,000 mPa·s at 25°C when dissolved in toluene to a concentration of 30% by mass, is capped at both molecular chain terminals with SiOH groups, and contains no alkenyl groups: (z58 is a number that satisfies the above viscosity, and the ratio of the number of hydroxyl groups to the total number of groups bonded to silicon atoms is 0.017%).

[0131] (B-1) Me ３ SiO １／２ Units and SiO ４／２ Organopolysiloxane (Me) consisting of units, having hydroxyl groups bonded to silicon atoms, and having no alkenyl groups. ３ SiO １／２ Units / SiO ４／２ Unit (molar ratio) = 0.70 / 1.0, weight average molecular weight 7,120, silicon atom-bonded hydroxyl group content 0.026 mol / 100 g, hydroxyl group is SiO ４／２ bonded to silicon atoms derived from units)

[0132] (B-2) Me ３ SiO １／２ Units and SiO ４／２ Organopolysiloxane (Me) consisting of units, having hydroxyl groups bonded to silicon atoms, and having no alkenyl groups. ３ SiO １／２ Units / SiO ４／２ Unit (molar ratio) = 0.68 / 1.0, weight average molecular weight 6,910, silicon atom-bonded hydroxyl group content 0.033 mol / 100 g, hydroxyl group is SiO ４／２ bonded to silicon atoms derived from units)

[0133] (B-3) Me ３ SiO １／２ Units and SiO ４／２ Organopolysiloxane (Me) consisting of units, having hydroxyl groups bonded to silicon atoms, and having no alkenyl groups. ３ SiO１／２ Units / SiO ４／２ Unit (molar ratio) = 0.72 / 1.0, weight average molecular weight 9,010, silicon atom-bonded hydroxyl group content 0.031 mol / 100 g, hydroxyl group is SiO ４／２ bonded to silicon atoms derived from units)

[0134] (C-1) Organohydrogenpolysiloxane represented by the following formula: Ratio of SiH groups: 46.5%, Amount of hydrogen atoms bonded to silicon atoms: 1.558 mol / 100 g

[0135] (C-2) Organohydrogenpolysiloxane represented by the following formula: Ratio of SiH groups: 41.7%, Amount of hydrogen atoms bonded to silicon atoms: 1.409 mol / 100 g

[0136] (D-1) Platinum catalyst: CAT-PL-50T (manufactured by Shin-Etsu Chemical Co., Ltd.)

[0137] (E-1) Me ３ SiO １／２ Units and SiO ４／２ Organopolysiloxane (Me) consisting of units, having hydroxyl groups bonded to silicon atoms, and having no alkenyl groups. ３ SiO １／２ Units / SiO ４／２ Unit (molar ratio) = 0.83 / 1.0, weight average molecular weight 3,450, silicon atom-bonded hydroxyl group content 0.078 mol / 100 g, hydroxyl group is SiO ４／２ bonded to silicon atoms derived from units)

[0138] (E-2) Me ３ SiO １／２ Units and SiO ４／２ Organopolysiloxane (Me) consisting of units, having hydroxyl groups bonded to silicon atoms, and having no alkenyl groups. ３ SiO １／２ Units / SiO ４／２ Unit (molar ratio) = 0.84 / 1.0, weight average molecular weight 2,190, silicon atom-bonded hydroxyl group content 0.108 mol / 100 g, hydroxyl group is SiO ４／２ bonded to silicon atoms derived from units)

[0139] (E-3) Me ３ SiO １／２ Units and SiO ４／２ Organopolysiloxane (Me) consisting of units, having hydroxyl groups bonded to silicon atoms, and having no alkenyl groups. ３ SiO １／２ Units / SiO ４／２ Unit (molar ratio) = 0.68 / 1.0, weight average molecular weight 2,690, silicon atom-bonded hydroxyl group content 0.110 mol / 100 g, hydroxyl group is SiO ４／２ bonded to silicon atoms derived from units)

[0140] (E-4) Me ３ SiO １／２ Units and SiO ４／２ Organopolysiloxane (Me) consisting of units, having hydroxyl groups bonded to silicon atoms, and having no alkenyl groups. ３ SiO １／２ Units / SiO ４／２ Unit (molar ratio) = 0.76 / 1.0, weight average molecular weight 4,320, silicon atom-bonded hydroxyl group content 0.051 mol / 100 g, hydroxyl group is SiO ４／２ bonded to silicon atoms derived from units)

[0141] (F-1) Me ３ SiO １／２ Units, MeViSiO ２／２ units, and SiO ４／２ Organopolysiloxane (Me ３ SiO １／２ Unit / MeViSiO ２／２ Units / SiO ４／２ Units (molar ratio) = 0.79 / 0.13 / 1.0, weight average molecular weight 2,380, alkenyl group content 0.123 mol / 100 g, silicon atom-bonded hydroxyl group content 0.031 mol / 100 g, hydroxyl groups are SiO ４／２ bonded to silicon atoms derived from units)

[0142] (F-2) Me ３ SiO １／２ Units, Me ２ ViSiO １／２ units, and SiO ４／２Organopolysiloxane (Me ３ SiO １／２ Unit / Me ２ ViSiO １／２ / SiO ４／２ Units (molar ratio) = 0.73 / 0.12 / 1.0, weight average molecular weight 2,950, alkenyl group content 0.089 mol / 100 g, silicon atom-bonded hydroxyl group content 0.026 mol / 100 g, hydroxyl groups are SiO ４／２ bonded to silicon atoms derived from units)

[0143] (G-1) Ethynylcyclohexanol

[0144] [Additives for Comparative Examples] (H-1) Organic peroxide curing agent: benzoyl peroxide (trade name: Nyper (registered trademark) BMT-K40, manufactured by NOF Corporation)

[0145] [Preparation of Silicone Pressure-Sensitive Adhesive Base Composition] <Preparation Example 1> The linear organopolysiloxane (A-1) (43 parts by mass), a 50% by mass toluene solution of the organopolysiloxane resin (B-1) (114 parts by mass), and the ethynylcyclohexanol (G-1) (0.2 parts by mass) were mixed, and toluene (71.5 parts by mass) was added to obtain a silicone pressure-sensitive adhesive base composition (1) containing approximately 50% by mass of the active ingredient.

[0146] Preparation Example 2 The linear organopolysiloxane (A-1) (40 parts by mass), a 50% by mass toluene solution of the organopolysiloxane resin (B-2) (100 parts by mass), a 50% by mass toluene solution of the organopolysiloxane resin (E-1) (20 parts by mass), and the ethynylcyclohexanol (G-1) (0.2 parts by mass) were mixed, and toluene (70 parts by mass) was added to obtain a silicone pressure-sensitive adhesive base composition (2) containing approximately 50% by mass of the active ingredient.

[0147] Preparation Example 3 The linear organopolysiloxane (A-1) (40 parts by mass), a 50% by mass toluene solution of the organopolysiloxane resin (B-1) (90 parts by mass), a 50% by mass toluene solution of the organopolysiloxane resin (F-1) (30 parts by mass), and the ethynylcyclohexanol (G-1) (0.2 parts by mass) were mixed, and toluene (70 parts by mass) was added to obtain a silicone pressure-sensitive adhesive base composition (3) containing approximately 50% by mass of the active ingredient.

[0148] Preparation Example 4 A solution consisting of the linear organopolysiloxane (A-1) (41 parts by mass), a 50% by mass toluene solution of the organopolysiloxane resin (B-1) (118 parts by mass), toluene (70.5 parts by mass), and aqueous ammonia (0.5 parts by mass) was stirred at room temperature (25°C) for 12 hours to cause a condensation reaction. The mixture was then heated under reflux at approximately 110 to 125°C for 6 hours to distill off the ammonia and water. The resulting reaction product was allowed to cool, and then the ethynylcyclohexanol (G-1) (0.2 parts by mass) was added thereto, followed by addition of toluene so that the solids content was approximately 50% by mass, yielding a silicone pressure-sensitive adhesive base composition (4).

[0149] Preparation Example 5 A solution consisting of the linear organopolysiloxane (A-1) (43 parts by mass), a 50% by mass toluene solution of the organopolysiloxane resin (B-1) (84 parts by mass), toluene (71.5 parts by mass), and aqueous ammonia (0.5 parts by mass) was stirred at room temperature (25°C) for 12 hours to cause a condensation reaction. The mixture was then heated under reflux at approximately 110 to 125°C for 6 hours to distill off the ammonia and water. The resulting reaction product was allowed to cool, and then a 50% by mass toluene solution of the organopolysiloxane resin (F-1) (30 parts by mass) and the ethynylcyclohexanol (G-1) (0.2 parts by mass) were added thereto, followed by addition of toluene to adjust the solids content to approximately 50% by mass, yielding a silicone pressure-sensitive adhesive base composition (5).

[0150] Preparation Example 6 A solution consisting of the linear organopolysiloxane (A-1) (42 parts by mass), a 50% by mass toluene solution of the organopolysiloxane resin (B-1) (68 parts by mass), a 50% by mass toluene solution of the organopolysiloxane resin (F-1) (48 parts by mass), toluene (71 parts by mass), and aqueous ammonia (0.5 parts by mass) was stirred at room temperature (25°C) for 12 hours to cause a condensation reaction. The solution was then heated under reflux at approximately 110 to 125°C for 6 hours, and the ammonia and water were distilled off. The resulting reaction product was allowed to cool, and then the ethynylcyclohexanol (G-1) (0.2 parts by mass) was added thereto, and toluene was added and mixed so that the solids content was approximately 50% by mass, yielding a silicone pressure-sensitive adhesive base composition (6).

[0151] Preparation Example 7 A solution consisting of the linear organopolysiloxane (A-1) (40 parts by mass), a 50% by mass toluene solution of the organopolysiloxane resin (B-2) (80 parts by mass), a 50% by mass toluene solution of the organopolysiloxane resin (F-1) (40 parts by mass), toluene (70 parts by mass), and aqueous ammonia (0.5 parts by mass) was stirred at room temperature (25°C) for 12 hours to cause a condensation reaction. The solution was then heated under reflux at approximately 110 to 125°C for 6 hours, and the ammonia and water were distilled off. The resulting reaction product was allowed to cool, and then the ethynylcyclohexanol (G-1) (0.2 parts by mass) was added thereto, and toluene was added and mixed so that the solids content was approximately 50% by mass, yielding a silicone pressure-sensitive adhesive base composition (7).

[0152] Preparation Example 8 A solution consisting of the linear organopolysiloxane (A-1) (45 parts by mass), a 50% by mass toluene solution of the organopolysiloxane resin (B-2) (70 parts by mass), a 50% by mass toluene solution of the organopolysiloxane resin (F-2) (40 parts by mass), toluene (72.5 parts by mass), and aqueous ammonia (0.5 parts by mass) was stirred at room temperature (25°C) for 12 hours to cause a condensation reaction. The solution was then heated under reflux at approximately 110 to 125°C for 6 hours, and the ammonia and water were distilled off. The resulting reaction product was allowed to cool, and then the ethynylcyclohexanol (G-1) (0.2 parts by mass) was added thereto, and toluene was added and mixed so that the solids content was approximately 50% by mass, yielding a silicone pressure-sensitive adhesive base composition (8).

[0153] Preparation Example 9 A solution consisting of the linear organopolysiloxane (A-1) (38 parts by mass), a 50% by mass toluene solution of the organopolysiloxane resin (B-3) (20 parts by mass), a 50% by mass toluene solution of the organopolysiloxane resin (E-3) (44 parts by mass), a 50% by mass toluene solution of the organopolysiloxane resin (F-1) (60 parts by mass), toluene (69 parts by mass), and aqueous ammonia (0.5 parts by mass) was stirred at room temperature (25°C) for 12 hours to cause a condensation reaction. The solution was then heated under reflux at approximately 110 to 125°C for 6 hours, and the ammonia and water were distilled off. The resulting reaction product was allowed to cool, and then the ethynylcyclohexanol (G-1) (0.2 parts by mass) was added thereto, and toluene was added and mixed so that the solids content was approximately 50% by mass, yielding a silicone pressure-sensitive adhesive base composition (9).

[0154] Preparation Example 10 A solution consisting of the linear organopolysiloxane (A-2) (42 parts by mass), a 50% by mass toluene solution of the organopolysiloxane resin (B-2) (76 parts by mass), a 50% by mass toluene solution of the organopolysiloxane resin (F-1) (40 parts by mass), toluene (71 parts by mass), and aqueous ammonia (0.5 parts by mass) was stirred at room temperature (25°C) for 12 hours to cause a condensation reaction. The solution was then heated under reflux at approximately 110 to 125°C for 6 hours, and the ammonia and water were distilled off. The resulting reaction product was allowed to cool, and then the ethynylcyclohexanol (G-1) (0.2 parts by mass) was added thereto, and toluene was added and mixed so that the solids content was approximately 50% by mass, yielding a silicone pressure-sensitive adhesive base composition (10).

[0155] Preparation Example 11 A solution consisting of the linear organopolysiloxane (A-1) (35 parts by mass), the linear organopolysiloxane (A'-1) (5 parts by mass), a 50% by mass toluene solution of the organopolysiloxane resin (B-2) (70 parts by mass), a 50% by mass toluene solution of the organopolysiloxane resin (E-3) (10 parts by mass), a 50% by mass toluene solution of the organopolysiloxane resin (F-1) (40 parts by mass), toluene (70 parts by mass), and aqueous ammonia (0.5 parts by mass) was stirred at room temperature (25°C) for 12 hours to cause a condensation reaction. The solution was then heated under reflux at about 110 to 125°C for 6 hours, and the ammonia and water were distilled off. The resulting reaction product was allowed to cool, and then the above-mentioned (G-1) ethynylcyclohexanol (0.2 parts by mass) was added thereto, and toluene was added thereto so that the solids content was approximately 50% by mass, and the mixture was mixed to obtain a silicone pressure-sensitive adhesive base composition (11).

[0156] Preparation Example 12 The linear organopolysiloxane (A-1) (37 parts by mass), a 50% by mass toluene solution of the organopolysiloxane resin (E-1) (126 parts by mass), and the ethynylcyclohexanol (G-1) (0.2 parts by mass) were mixed, and toluene (68.5 parts by mass) was added to obtain a silicone pressure-sensitive adhesive base composition (12) containing approximately 50% by mass of the active ingredient.

[0157] Preparation Example 13 The linear organopolysiloxane (A-1) (43 parts by mass), a 50% by mass toluene solution of the organopolysiloxane resin (E-4) (114 parts by mass), and the ethynylcyclohexanol (G-1) (0.2 parts by mass) were mixed, and toluene (71.5 parts by mass) was added to obtain a silicone pressure-sensitive adhesive base composition (13) containing approximately 50% by mass of the active ingredient.

[0158] Preparation Example 14 A solution consisting of the linear organopolysiloxane (A-1) (40 parts by mass), a 50% by mass toluene solution of the organopolysiloxane resin (E-2) (120 parts by mass), toluene (70 parts by mass), and aqueous ammonia (0.5 parts by mass) was stirred at room temperature (25°C) for 12 hours to cause a condensation reaction. The mixture was then heated under reflux at approximately 110 to 125°C for 6 hours to distill off the ammonia and water. The resulting reaction product was allowed to cool, and then the ethynylcyclohexanol (G-1) (0.2 parts by mass) was added thereto, followed by addition of toluene so that the solids content was approximately 50% by mass, yielding a silicone pressure-sensitive adhesive base composition (14).

[0159] Preparation Example 15 A solution consisting of the linear organopolysiloxane (A-1) (45 parts by mass), a 50% by mass toluene solution of the organopolysiloxane resin (E-3) (110 parts by mass), toluene (72.5 parts by mass), and aqueous ammonia (0.5 parts by mass) was stirred at room temperature (25°C) for 12 hours to cause a condensation reaction. The mixture was then heated under reflux at approximately 110 to 125°C for 6 hours to distill off the ammonia and water. The resulting reaction product was allowed to cool, and then the ethynylcyclohexanol (G-1) (0.2 parts by mass) was added thereto, followed by addition of toluene so that the solids content was approximately 50% by mass, yielding a silicone pressure-sensitive adhesive base composition (15).

[0160] Preparation Example 16 A solution consisting of the linear organopolysiloxane (A-1) (42 parts by mass), a 50% by mass toluene solution of the organopolysiloxane resin (F-1) (116 parts by mass), toluene (71 parts by mass), and aqueous ammonia (0.5 parts by mass) was stirred at room temperature (25°C) for 12 hours to cause a condensation reaction. The mixture was then heated under reflux at approximately 110 to 125°C for 6 hours to distill off the ammonia and water. The resulting reaction product was allowed to cool, and then (G-1) ethynylcyclohexanol (0.2 parts by mass) was added thereto, followed by addition of toluene and mixing so that the solids content was approximately 50% by mass, yielding a silicone pressure-sensitive adhesive base composition (16).

[0161] Preparation Example 17 A solution consisting of the linear organopolysiloxane (A-1) (45 parts by mass), a 50% by mass toluene solution of the organopolysiloxane resin (E-2) (70 parts by mass), a 50% by mass toluene solution of the organopolysiloxane resin (F-1) (40 parts by mass), toluene (72.5 parts by mass), and aqueous ammonia (0.5 parts by mass) was stirred at room temperature (25°C) for 12 hours to cause a condensation reaction. The solution was then heated under reflux at approximately 110 to 125°C for 6 hours, and the ammonia and water were distilled off. The resulting reaction product was allowed to cool, and then the ethynylcyclohexanol (G-1) (0.2 parts by mass) was added thereto, and toluene was added and mixed so that the solids content was approximately 50% by mass, yielding a silicone pressure-sensitive adhesive base composition (17).

[0162] Preparation Example 18 A solution consisting of the linear organopolysiloxane (A'-1) (45 parts by mass), a 50% by mass toluene solution of the organopolysiloxane resin (E-3) (110 parts by mass), toluene (72.5 parts by mass), and aqueous ammonia (0.5 parts by mass) was stirred at room temperature (25°C) for 12 hours to cause a condensation reaction. The solution was then heated under reflux at approximately 110 to 125°C for 6 hours, and the ammonia and water were distilled off. The resulting reaction product was allowed to cool, and then toluene was added and mixed to give a solids content of approximately 50% by mass, yielding a silicone pressure-sensitive adhesive base composition (18).

[0163] [Preparation and Property Evaluation of Silicone Pressure-Sensitive Adhesive Compositions] <Examples 1 to 11, Comparative Examples 1 to 8> The above-described silicone pressure-sensitive adhesive base composition and the above-described (C) organohydrogenpolysiloxane were placed in a flask according to the blending amounts shown in Tables 1 to 4, and 50 parts by mass of toluene was added and stirred to dissolve. To the resulting solution, the above-described (D-1) platinum-based catalyst was added in an amount equivalent to 50 ppm platinum by mass relative to the total mass of components (A), (A'), (B), (C), (E), and (F), and the mixture was stirred and mixed to prepare a silicone pressure-sensitive adhesive composition. The resulting silicone pressure-sensitive adhesive composition was cured using the method described above. The adhesion to silicone rubber and dynamic viscoelasticity (storage modulus G') were measured using the methods described above, and the evaluation results are shown in Tables 1 to 4.

[0164] Comparative Example 9 The silicone pressure-sensitive adhesive base composition (18) shown above was placed in a flask according to the blending amounts in Table 4, and 50 parts by mass of toluene was added and stirred to dissolve. 3.0 parts by mass of the organic peroxide curing agent (H-1) above was added to the resulting solution, and the mixture was stirred and mixed to prepare a silicone pressure-sensitive adhesive composition. The resulting silicone pressure-sensitive adhesive composition was cured by the method described above. The adhesive strength to silicone rubber and dynamic viscoelasticity (storage modulus G') were measured by the methods described above, and the evaluation results are shown in Table 4.

[0165]

[0166]

[0167]

[0168]

[0169] As shown in Tables 3 and 4 above, the silicone rubber compositions of Comparative Examples 1 to 4, and 6, which used an (E) component with a weight-average molecular weight of less than 5,000 instead of the (B) component, exhibited low adhesion to silicone rubber and low storage modulus G' at both room temperature and 80°C. The silicone rubber composition of Comparative Example 5, in which the SiH / Vi number ratio was set to 300, exhibited improved adhesion to silicone rubber, but only a slight improvement in storage modulus G'. The silicone rubber composition of Comparative Example 7, which used an (F) component having an alkenyl group instead of the (B) component, and the silicone rubber composition of Comparative Example 8, which did not contain the (B) component but contained the (E) and (F) components, also exhibited low adhesion and storage modulus G' of the silicone rubber. Furthermore, the silicone rubber composition of Comparative Example 9, which used benzoyl peroxide as an organic peroxide curing agent, exhibited high adhesion to silicone rubber but a low storage modulus G'.

[0170] In contrast, as shown in Tables 1 and 2, pressure-sensitive adhesive tapes made from the silicone pressure-sensitive adhesive composition of the present invention exhibited high adhesive strength to silicone rubber, and also had high storage moduli G' at 25° C. and 80° C. This is thought to be because the organopolysiloxane resin component (B) having a weight-average molecular weight of 5,000 or greater maintains its crystallinity even in high-temperature environments.

[0171] As described above, a pressure-sensitive adhesive tape or film having an adhesive layer formed by curing the silicone pressure-sensitive adhesive composition of the present invention has strong adhesive strength to silicone rubber and can maintain a high storage modulus G' even at high temperatures. Therefore, the silicone pressure-sensitive adhesive composition of the present invention is useful for pressure-sensitive adhesive tapes or films for adhering or bonding silicone materials, masking tapes, temporary fixing tapes, heat-sealing tapes in the manufacturing processes of electronic components and semiconductor components, and components for electronic materials or display devices.

Claims

1. (I) at least one linear organopolysiloxane and R ３ ３ SiO １／２ Units and SiO ４／２ or (II) at least one linear organopolysiloxane and at least one organopolysiloxane resin having a unit R ３ ３ SiO １／２ Units and SiO ４／２ a silicone pressure-sensitive adhesive composition comprising a condensation reaction product with at least one organopolysiloxane resin having a unit, wherein the linear organopolysiloxane in (I) and (II) comprises: (A) a linear organopolysiloxane having one or more alkenyl groups per molecule, with an alkenyl group content of 0.0001 to 0.03 mol / 100 g, and optionally having a silicon-bonded hydroxyl group or a C alkoxy group; and optionally (A') a linear organopolysiloxane having no alkenyl groups and no silicon-bonded hydrogen atoms; and the organopolysiloxane resin in (I) and (II) comprises: (B) R ３ ３ SiO １／２ Units and SiO ４／２ units, and has a hydroxyl group and / or an alkoxy group having 1 to 6 carbon atoms bonded to a silicon atom, (R ３ ３ SiO １／２ Unit) / (SiO ４／２ The organopolysiloxane resin (wherein R ３ are each independently a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, a hydroxyl group, or an alkoxy group having 1 to 6 carbon atoms), wherein the organopolysiloxane resin does not contain alkenyl groups or contains alkenyl groups in an amount such that the total amount of alkenyl groups in the organopolysiloxane resin is less than 0.005 mol / 100 g, and the organopolysiloxane resin has a weight average molecular weight of 5,000 or more as measured using standard polystyrene standards by gel permeation chromatography; the silicone pressure-sensitive adhesive composition further contains: (C) an organohydrogenpolysiloxane having three or more silicon-bonded hydrogen atoms per molecule, in an amount such that the ratio of the total number of SiH groups in component (C) to the total number of alkenyl groups in the alkenyl-group-containing organopolysiloxane contained in the silicone pressure-sensitive adhesive composition is 0.1 to 30.0; and (D) a catalytic amount of a platinum group metal catalyst; the silicone pressure-sensitive adhesive composition, wherein the ratio of the total mass of the linear organopolysiloxane to the total mass of the organopolysiloxane resin is 25 / 75 to 70 / 30; 2. The silicone pressure-sensitive adhesive composition according to claim 1, wherein the amount of said component (A) is 0.1 to 70 mass %, the amount of said component (B) is 0.01 to 70 mass %, and the amount of said component (A') is 0 to 50 mass %, relative to the total mass of said silicone pressure-sensitive adhesive composition.

3. (F)R ３ ３ SiO １／２ Units and SiO ４／２ units, (R ３ ３ SiO １／２ Unit) / (SiO ４／２ units) is 0.5 to 1.5, has one or more alkenyl groups in one molecule, the alkenyl group content is 0.005 to 0.5 mol / 100 g, and optionally has silicon-bonded hydroxyl groups and / or silicon-bonded alkoxy groups having 1 to 6 carbon atoms (wherein R ３ and each independently represent a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, a hydroxyl group, or an alkoxy group having 1 to 6 carbon atoms) in an amount of 0.01 to 45 mass % relative to the total mass of the silicone pressure-sensitive adhesive composition.

4. The silicone pressure-sensitive adhesive composition according to claim 3, comprising a condensation reaction product of said component (A), optionally said component (A'), said component (B), and said component (F).

5. The silicone pressure-sensitive adhesive composition according to claim 3, comprising a condensation reaction product of said component (A), optionally said component (A'), and said component (B), and further comprising said component (F).

6. (E)R ３ ３ SiO １／２ Units and SiO ４／２ units, and has a hydroxyl group and / or an alkoxy group having 1 to 6 carbon atoms bonded to a silicon atom, (R ３ ３ SiO １／２ Unit) / (SiO ４／２ The organopolysiloxane resin (wherein R ３ and each independently represent a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, a hydroxyl group, or an alkoxy group having 1 to 6 carbon atoms), and the organopolysiloxane resin contains no alkenyl groups or contains alkenyl groups in such an amount that the total amount of alkenyl groups in the organopolysiloxane resin is less than 0.005 mol / 100 g, and has a weight average molecular weight of less than 5,000 as measured by gel permeation chromatography relative to standard polystyrene standards, in an amount of 0.01 to 35 mass %, based on the total mass of the silicone pressure-sensitive adhesive composition.

7. The silicone pressure-sensitive adhesive composition according to claim 6, comprising a condensation reaction product of said component (A), optional component (A'), said component (B), and said component (E).

8. (E)R ３ ３ SiO １／２ Units and SiO ４／２ units, and has a hydroxyl group and / or an alkoxy group having 1 to 6 carbon atoms bonded to a silicon atom, (R ３ ３ SiO １／２ Unit) / (SiO ４／２ The organopolysiloxane resin (wherein R ３ and each independently represent a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, a hydroxyl group, or an alkoxy group having 1 to 6 carbon atoms), wherein the organopolysiloxane resin does not contain alkenyl groups or contains alkenyl groups in such an amount that the total amount of alkenyl groups in the organopolysiloxane resin is less than 0.005 mol / 100 g, and wherein the organopolysiloxane resin has a weight average molecular weight of less than 5,000 as measured by gel permeation chromatography relative to standard polystyrene standards, in an amount of 0.01 to 35 mass %, relative to the total mass of the silicone pressure-sensitive adhesive composition.

9. The silicone pressure-sensitive adhesive composition according to claim 8, comprising a condensation reaction product of said component (A), optionally said component (A'), said component (B), said component (E), and said component (F).

10. The silicone pressure-sensitive adhesive composition according to claim 8, comprising a condensation reaction product of said component (A), optionally said component (A'), said component (B), and said component (E), and further comprising said component (F).

11. The silicone pressure-sensitive adhesive composition according to claim 1, wherein component (A) is represented by the following formula (1): (In the formula, R １ are each independently a hydroxyl group, an alkoxy group having 1 to 6 carbon atoms, or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, provided that R １ at least one of R is an alkenyl-containing organic group having 2 to 10 carbon atoms; １ the ratio of the number of hydroxyl groups to the total number of groups is 10% or less, the alkenyl group content in the organopolysiloxane is 0.0001 to 0.03 mol / 100 g, and a is a positive number such that a solution of the organopolysiloxane in toluene to a concentration of 30% by mass has a viscosity at 25°C of 1,000 to 200,000 mPa s.

12. The component (F) further contains R ５ R ６ SiO ２／２ units (wherein R ５ is the above R other than an alkenyl group. ３ and R ６ is an alkenyl group having 2 to 10 carbon atoms), (R ５ R ６ SiO ２／２ Unit) / (SiO ４／２ 4. The silicone pressure-sensitive adhesive composition according to claim 3, wherein the organopolysiloxane resin has a molar ratio, expressed as ##STR1## of 0.01 to 0.

5.

13. The component (F) further contains R ５ R ６ SiO ２／２ units (wherein R ５ is the above R other than an alkenyl group. ３ and R ６ is an alkenyl group having 2 to 10 carbon atoms), (R ５ R ６ SiO ２／２ Unit) / (SiO ４／２ 9. The silicone pressure-sensitive adhesive composition according to claim 8, wherein the organopolysiloxane resin has a molar ratio, expressed as ##STR1## of 0.01 to 0.

5.

14. The silicone pressure-sensitive adhesive composition according to any one of claims 1 to 13, wherein the adhesive strength of a 40 μm-thick cured layer formed by curing the silicone pressure-sensitive adhesive composition to a silicone rubber sheet is 3.0 N / 25 mm or more, as measured using a 180° peel test method at a tensile speed of 300 mm / min.

15. A cured product obtained by curing the silicone pressure-sensitive adhesive composition according to any one of claims 1 to 13.

16. The cured product according to claim 15, wherein the adhesive layer made of the cured product has a storage modulus G' at 25°C of 1.00 MPa or more.

17. The cured product according to claim 15, wherein the adhesive layer made of the cured product has a storage modulus G' at 80°C of 0.10 MPa or more.

18. An adhesive tape comprising a substrate and an adhesive layer formed on at least one surface of the substrate, the adhesive layer being the cured product according to claim 15.

19. An adhesive film comprising a substrate and an adhesive layer formed on at least one surface of the substrate, the adhesive layer being the cured product according to claim 15.

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