JP5142076B2 - Silicone adhesive - Google Patents

Description

  The present invention relates to a silicone adhesive comprising a polyorganosiloxane composition that gives an elastomeric cured product (silicone rubber cured product).

Conventional addition-curable silicone adhesives need to be heated to 100 ° C. or higher when cured (for example, Patent Document 1). Under these conditions, it is necessary to introduce and maintain a device that manages the temperature conditions. Energy is also required to keep the temperature constant.
JP 2000-265067 A

  An object of the present invention is to provide an addition-curable silicone adhesive that can exhibit adhesion even when cured at room temperature. Furthermore, an object of the present invention is to provide an addition-curable silicone adhesive capable of developing adhesion in a shorter time.

The object of the present invention is to provide the following components (A) to (E):
(A) Diorganopolysiloxane containing at least two alkenyl groups in one molecule other than the following component (E): 100 parts by mass (B) At least two hydrogen atoms bonded to silicon atoms in one molecule Organohydrogenpolysiloxane other than the following component (C) to be contained: The number of hydrogen atoms bonded to silicon atoms contained in one molecule of this component is one alkenyl group of the organopolysiloxane of component (A). 0 to 5.0 (C) Organosilicon compound represented by the following general formula (1):

（１）

(1)

(In the formula, n is an integer of 0 to 10, and R is a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms.): 0.01 to 5 parts by mass (D) Hydrosilylation reaction catalyst An effective amount of the catalyst, and (E) an adhesion assistant comprising an alkenyl group in one molecule and further comprising at least one group selected from the group consisting of an alkoxy group, a carbonyl group, an epoxy group and an alkoxysilyl group. Agent: (C) An amount of 0.01 to 10 moles per mole of component,
(However, when R in general formula (1) of component (C) contains a phenyl group, each component of (A) and (B) does not contain a phenyl group)
It is achieved by an addition-curable silicone adhesive containing
Alternatively, in place of the components (C) and (E), a product (component (C ′)) obtained by subjecting the components (C) and (E) to an addition reaction in advance may be used.

  When the addition curable silicone adhesive of the present invention is used, adhesiveness is exhibited in a short time of about 12 hours even at room temperature.

Below, each component of the silicone adhesive of this invention is explained in full detail.
[(A) Alkenyl group-containing diorganopolysiloxane]
The (A) component diorganopolysiloxane is the main component of the present composition, and contains an average of two or more alkenyl groups in one molecule. The alkenyl group is preferably bonded to a silicon atom. (A) As an alkenyl group of a component, a C2-C10 alkenyl group, for example, a vinyl group, an allyl group, a butenyl group, a pentenyl group, a hexenyl group, a heptenyl group is mentioned, Especially, it is a vinyl group. Is preferred. Examples of the bonding position of the alkenyl group of component (A) include molecular chain terminals and / or molecular chain side chains. (A) As an organic group couple | bonded with silicon atoms other than the alkenyl group of a component, C1-C10, such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, etc., for example. Alkyl group; aryl group such as phenyl group, tolyl group, xylyl group and naphthyl group; aralkyl group such as benzyl group and phenethyl group; chloromethyl group, 3-chloropropyl group, 3,3,3-trifluoropropyl group and the like And an unsubstituted or substituted monovalent hydrocarbon group containing 1 to 10 carbon atoms and not containing an aliphatic unsaturated bond, and particularly preferably a methyl group or a phenyl group. . Examples of the molecular structure of the component (A) include linear, partially branched linear, cyclic, and branched. The viscosity of component (A) at 25 ° C. is within the range of 100 to 500,000 mPa · s because the physical properties of the resulting silicone rubber are good and the workability of the resulting composition is good. It is preferable that it is within a range of 300 to 100,000 mPa · s.

Examples of the organopolysiloxane of the component (A) include, for example, a trimethylsiloxy group-capped dimethylsiloxane / methylvinylsiloxane copolymer, a molecular chain both-ends trimethylsiloxy group-capped methylvinylpolysiloxane, and both molecular chains. Terminal trimethylsiloxy group-blocked dimethylsiloxane / methylvinylsiloxane / methylphenylsiloxane copolymer, molecular chain both ends dimethylvinylsiloxy group-blocked dimethylpolysiloxane, molecular chain both ends dimethylvinylsiloxy group-blocked methylvinylpolysiloxane, molecular chain both ends Dimethylvinylsiloxy-blocked dimethylsiloxane / methylvinylsiloxane copolymer, dimethylvinylsiloxy-blocked dimethylsiloxane / methylvinylsiloxane / methylphenylsiloxane copolymer Both molecular chain terminals by trimethylsiloxy blocked with dimethylvinylsiloxy groups, wherein: the siloxane units of the formula R ¹ ₃ SiO _0.5: siloxane units represented by the formula R ^{1 ₂} R ₂ SiO _0.5: represented by R ¹ ₂ SiO Unit and a small amount of a formula: an organopolysiloxane copolymer composed of a siloxane unit represented by SiO ₂ , a siloxane unit represented by a formula: R ¹ ₃ SiO _0.5 and a siloxane unit represented by a formula: R ¹ ₂ R ² SiO _0.5 And an organopolysiloxane copolymer comprising a siloxane unit represented by SiO ₂ , a siloxane unit represented by formula: R ¹ ₂ R ² SiO _0.5 and a siloxane unit represented by formula: R ¹ ₂ SiO and a small amount of formula: Organopolysiloxane copolymer comprising siloxane units represented by SiO ₂ , siloxane units represented by formula: R ¹ R ² SiO and a small amount of siloxane units represented by formula: R ¹ SiO _1.5 or formula: R ² SiO _1.5 Shiroki indicated Examples thereof include organopolysiloxane copolymers composed of sun units and mixtures composed of two or more of these organopolysiloxanes. R ¹ in the above formula is an unsubstituted or substituted monovalent hydrocarbon group containing no aliphatic unsaturated bond, for example, methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, etc. Alkyl groups; phenyl groups, tolyl groups, xylyl groups, naphthyl groups and other aryl groups; benzyl groups, phenethyl groups and other aralkyl groups; chloromethyl groups, 3-chloropropyl groups, 3,3,3-trifluoropropyl groups And halogenated alkyl groups such as R ² in the above formula is an alkenyl group, and examples thereof include a vinyl group, an allyl group, a butenyl group, a pentenyl group, a hexenyl group, and a heptenyl group, and a vinyl group is preferable.
However, when R in the general formula (1) of the component (C) includes a phenyl group, the component (A) does not include a phenyl group.

[(B) Organohydrogenpolysiloxane]
The organohydrogenpolysiloxane used as the component (B) in the composition of the present invention contains at least 2, preferably 3 or more, hydrogen atoms bonded to silicon atoms (that is, SiH groups) in one molecule. , Other than the component (C), any of a linear, branched, cyclic, or three-dimensional network resinous material may be used. Representative examples of such organohydrogenpolysiloxanes include, for example, the following average composition formula (2):
H _a R ³ _b SiO _{(4-ab) / 2} (2)
(Wherein R ³ is an unsubstituted or substituted monovalent hydrocarbon group that does not independently contain an aliphatic unsaturated bond, and a and b are 0 <a <2, 0.8 ≦ b ≦ 2, and 0.8 <a + b ≦ 3, preferably 0.05 ≦ a ≦ 1, 1.5 ≦ b ≦ 2, and 1.8 ≦ a + b ≦ 2.7.).

In the above formula (2), the unsubstituted or substituted monovalent hydrocarbon group not containing the aliphatic unsaturated bond of R ³ is the same as those exemplified as R ^{1 in} the formula of the component (A). A typical example is an unsubstituted or substituted monovalent hydrocarbon group having 1 to 10 carbon atoms, particularly 1 to 7 carbon atoms, preferably 1 to 3 carbon atoms such as a methyl group. Lower alkyl group, phenyl group, and 3,3,3-trifluoropropyl group.
Examples of the organohydrogenpolysiloxane of the average composition formula (2) include 1,1,3,3-tetramethyldisiloxane, 1,3,5,7-tetramethyltetracyclosiloxane, 1,3, Siloxane oligomers such as 5,7,8-pentamethylpentacyclosiloxane; molecular hydrogen trimethylsiloxy group-blocked methylhydrogen polysiloxane, molecular chain trimethylsiloxy group-blocked dimethylsiloxane / methylhydrogensiloxane copolymer, molecule Silanol group-blocked methylhydrogenpolysiloxane with both ends of chain chain, Silanol group-blocked dimethylsiloxane / methylhydrogensiloxane copolymer with chain end, dimethylhydrogensiloxy group-blocked dimethylpolysiloxane with molecular chain ends, and dimethylhydrosiloxane with molecular chain ends Gensiloxy group-blocked methyl high Roger down polysiloxane with both molecular chain terminals blocked with dimethylhydrogensiloxy groups dimethylsiloxane-methylhydrogensiloxane copolymers; consists R ³ ₂ (H) SiO _1/2 units and SiO _4/2 units, optionally R ³ ₃ SiO _1/2 unit, R ³ ₂ SiO _2/2 unit, R ³ (H) SiO _2/2 unit, (R ³ is unsubstituted or substituted without the aliphatic unsaturated bond exemplified as R ¹ above) The same as the substituted monovalent hydrocarbon group), and the following formula:
(H4), M ^H -Dn-M ^H , or M-Dn-D ^H mM
And the like. Here, (H4) is a cyclic body composed of four ^DH units, ^MH is an M unit (R ³ ₂ (H) SiO _1/2 ) containing a hydrogen atom bonded to a silicon atom, and D is a D unit. (R ³ ₂ SiO _2/2 ), D ^H is a D unit containing a hydrogen atom bonded to a silicon atom (R ³ (H) SiO _2/2 ) (R ³ is exemplified as R ¹ in the component (A). The same as an unsubstituted or substituted monovalent hydrocarbon group not containing an aliphatic unsaturated bond), n is an integer of 0 to 200, and m is an integer of 1 to 200. However, when a phenyl group is contained in R of (C) component, it is preferable that a phenyl group is not contained in (B) component.

The organohydrogenpolysiloxane used as the component (B) of the composition of the present invention can be obtained by a known method. For example, the general formula: R ³ SiHCl ₂ and R ³ ₂ SiHCl (wherein R ² is the above-mentioned formula) Co-hydrolyzing at least one chlorosilane selected from the formula (2), or the chlorosilane and the general formulas: R ³ ₃ SiCl and R ³ ₂ SiCl ₂ (wherein R ³ is It can be obtained by cohydrolyzing by combining at least one chlorosilane selected from (as defined in the average composition formula (2)). In addition, the organohydrogenpolysiloxane may be one obtained by equilibrating the polysiloxane obtained by cohydrolysis.

  Component (B) is used in an amount of hydrogen atoms bonded to silicon atoms in the organohydrogenpolysiloxane of component (B) per mole of alkenyl groups in the alkenyl group-containing diorganopolysiloxane of component (A) (that is, , SiH group) is usually in an amount of 0 to 5 mol, preferably 0.1 to 2.0 mol.

[(C) Organosilicon compound represented by general formula (1)]
(C) is an organosilicon compound represented by the following general formula (1):

（１）

(1)

(Wherein n is an integer of 0 to 10, preferably 0 to 2, and R is a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms).

R as a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms does not contain an aliphatic unsaturated bond similar to that exemplified as R ^{1 in} the formula of the component (A). Examples thereof include an unsubstituted or substituted monovalent hydrocarbon group, a group similar to the alkenyl group exemplified in the component (A), and other aliphatic unsaturated monovalent hydrocarbon groups such as a phenyl group and a cyclohexyl group.

By adding the component (C) and the component (E), which will be described in detail later, to the silicone composition, the adhesion at room temperature is improved, and in the past, adhesion requires 24 hours at room temperature within 12 hours. It became possible to shorten.
Examples of specific structures of the organosilicon compound represented by the general formula (1) are shown below.

  However, when the component (C) contains a phenyl group, the component (A) and the component (B) do not contain a phenyl group.

  (C) 0.01-5 mass parts is preferable with respect to 100 mass parts of (A) component, and, as for the compounding quantity of (C) component, 0.1-2 mass parts is more preferable.

[(D) Platinum group metal catalyst]
The platinum group metal catalyst used as the component (D) in the present invention includes the alkenyl groups of the components (A) and (E) and the hydrogen atoms bonded to the silicon atoms of the components (B) and (C). As a catalyst for promoting the addition reaction, a known catalyst can be used as a catalyst used in the hydrosilylation reaction. Specific examples thereof include platinum group metals such as platinum (including platinum black), rhodium and palladium; H ₂ PtCl ₄ · nH ₂ O, H ₂ PtCl ₆ · nH ₂ O, NaHPtCl ₆ · nH ₂ O , KHPtCl ₆ · nH ₂ O, Na ₂ PtCl ₆ · nH ₂ O, K ₂ PtCl ₄ · nH ₂ O, PtCl ₄ · nH ₂ O, PtCl ₂ , Na ₂ HPtCl ₄ · nH ₂ O Wherein n is an integer of 0 to 6, preferably 0 or 6, and chloroplatinic acid and chloroplatinate; alcohol-modified chloroplatinic acid (US Pat. No. 3,220,972) A complex of chloroplatinic acid and an olefin (see US Pat. Nos. 3,159,601, 3,159,662, and 3,775,452); platinum Black, palladium, etc. A platinum group metal supported on a carrier such as alumina, silica or carbon; rhodium-olefin complex; chlorotris (triphenylphosphine) rhodium (Wilkinson catalyst); platinum chloride, chloroplatinic acid or chloroplatinate and vinyl group And a complex with a containing siloxane, particularly a vinyl group-containing cyclic siloxane.

  The amount of the component (D) used may be a so-called effective catalyst amount, and is usually about 0.1 to 500 ppm, particularly about 0.5 to 200 ppm in terms of the mass of the platinum group metal relative to the total amount of the components (A) and (B). .

[(E) Adhesive auxiliary component]
The adhesion assistant component used as the component (E) in the composition of the present invention has an alkenyl group in one molecule, and at least one selected from the group consisting of an alkoxy group, a carbonyl group, an epoxy group, and an alkoxysilyl group. A compound containing a species.

Specific examples of the component (E) are as follows.
KBM1003 (trade name, vinyltrimethoxysilane, manufactured by Shin-Etsu Chemical Co., Ltd.)
KBE1003 (trade name, vinyltriethoxysilane, manufactured by Shin-Etsu Chemical Co., Ltd.)
Allyl glycidyl ether vinyl cyclohexene monooxide
3, 4-epoxycyclohexylmethyl methacrylate
KBM503 (trade name, γ- (methacryloxypropyl) trimethoxysilane, manufactured by Shin-Etsu Chemical Co., Ltd.)
Hydrolyzate of KBM502 (trade name, γ- (methacryloxypropyl) dimethoxymethylsilane, manufactured by Shin-Etsu Chemical Co., Ltd.) Allyl phenoxyacetate 2-allylmalonic acid diethylisophthalate allyl acetate vinyl benzoate vinyl acrylate phenylphenyl acetate allyl

  (E) As for the compounding quantity of a component, 0.01-10 mass parts is preferable with respect to 100 mass parts of (A) component, and 0.1-2 mass parts is more preferable. Moreover, it is preferable to mix | blend in the ratio of 0.01-10 mol with respect to 1 mol of (C) component, especially about 1 mol.

  The aforementioned component (C) and component (E) may be added to the silicone composition as they are, or a compound obtained by subjecting the component (C) and component (E) to an addition reaction in advance by some method is added. Also good. The ratio of these components to be reacted is not particularly limited, but the ratio of the component (C) and the component (E) is preferably 1: 1 to 3 in terms of molar ratio.

[Other ingredients]
As other components, it is recommended that fine powdery silica with reinforcing properties be blended. This fine powder silica is used to reinforce the mechanical strength of the cured product, and may be a known one conventionally used for silicone rubber, such as fumed silica, precipitated silica, calcined silica, quartz powder, diatomaceous earth, etc. is there. You may use these 1 type individually or in combination of 2 or more types. These silica particles specific surface area of ^{50 m} 2 / g or more usually by the BET method, in particular 50~500m general of about ² / g. Such fine powder silica may be used as it is, but in order to give good fluidity to the composition of the present invention, it was treated with an organosilicon compound such as methylchlorosilanes, dimethylpolysiloxane and hexamethyldisilazane. It is preferable to use one.

  In addition, in order to further improve the adhesiveness, those that improve the adhesiveness, such as organic silicon compounds containing an epoxy group or an alkoxy group generally used as an adhesion-imparting component, and compounds in which an ester group is bonded to the benzene ring If it is, you may add in the quantity to 10 mass% of the whole silicone composition.

  In addition to the components (A), (B), (C), (D), and (E), the composition of the present invention may contain, for example, fine fumed titanium dioxide. Reinforcing inorganic fillers other than powdered silica; reinforcing silicone resins; non-reinforcing inorganic fillers such as calcium silicate, titanium dioxide, ferric oxide, and carbon black can be added. The amount of the reinforcing and non-reinforcing inorganic fillers including the reinforcing fine powder silica is usually 0 to 200 parts by mass per 100 parts by mass of the total amount of the components (A) to (E). It is.

  The composition according to the present invention may be prepared as a one-part mold, or may be prepared as a mold comprising two or more parts used by mixing just before use.

  The silicone adhesive of the present invention can be used for bonding metal, glass, organic resin, particularly aluminum, SUS, glass, PBT, PPS, PPA and the like.

Hereinafter, the present invention will be described more specifically with reference to Examples and Comparative Examples.
A silicone composition was prepared using the following raw materials and examined.
-Raw material of silicone composition (A) 100 parts by mass of diorganopolysiloxane represented by the following formula and containing two vinyl groups in one molecule
Vi (Me) ₂ Si- (OSiMe ₂ ) n-OSi (Me) ₂ Vi
(In the formula, Me is methyl, Vi is a vinyl group, and n is a number such that the viscosity of the siloxane at 25 ° C. is 10,000 mPa · s).
(B) Organohydrogenpolysiloxane represented by the following formula and containing at least two hydrogen atoms bonded to silicon atoms in one molecule:
MD ^H ₂₀ -D ₁₈ -M
(In the formula, M represents Me ₃ SiO _1/2 , ^DH represents MeHSiO, and D represents Me ₂ SiO.)
(C) The following organosilicon compound (C-1) and / or (C-2):
(C-1) Organosilicon compound represented by the following formula

(C-2) 次の式で表される有機ケイ素化合物

(C-2) Organosilicon compound represented by the following formula

(D) The following hydrosilylation reaction catalyst:
Platinum-divinyltetramethyldisiloxane complex / toluene solution Platinum element content 0.5% by mass
(E) Adhesion aid component of any of the following (E-1) to (E-5):
(E-1) Allyl glycidyl ether represented by the following formula

(E-2) Vinyltrimethoxysilane represented by the following formula
_{CH 2 = CH-Si (OCH} 3) 3
(E-3) 1,2-epoxy-4-vinylcyclohexene represented by the following formula

(E-4)下式で示される3、4-エポキシシクロヘキシルメチルメタアクリレート：

(E-4) 3,4-epoxycyclohexylmethyl methacrylate represented by the following formula:

(E-5)下式で示されるγ-メタクリロイルオキシプロピルトリメトキシシラン：

(E-5) γ-methacryloyloxypropyltrimethoxysilane represented by the following formula:

(F) The following fillers:
Fumed silica manufactured by Shin-Etsu Chemical Co., Ltd. (dry silica, specific surface area 200 m ² / g)
(G) The following reinforcing resin:
Reinforcing resin made by Shin-Etsu Chemical Co., Ltd. (vinyl group-containing methylpolysiloxane resin (vinyl group content 2.3 wt%) consisting of Vi (Me) ₂ SiO _1/2 units and SiO _4/2 units))
(H) Other adhesion assistant components of (H-1) and (H-2) below:
(H-1) Compound having the following structural formula

(H-2)下記構造式の化合物（和光純薬工業（株）製、商品名：TRIAM805）

(H-2) Compound having the following structural formula (trade name: TRIAM805, manufactured by Wako Pure Chemical Industries, Ltd.)

Experimental Method The silicone composition is prepared by mixing (A), (D), (F) and (G) in advance, and (B), (C), (E), (H) and (I). (The component (I) was used in place of the components (C) and (E) in Examples 8 to 11), and after sufficient stirring, a defoaming step was added.
As shown in FIG. 1, two plates 1 and 2 made of PBT (polybutylene isophthalate) having a width of 25 cm, a length of 10 cm, and a thickness of 2 mm have a bonding area of 25 mm × 10 mm, and the thickness of the adhesive layer 3 is 2 mm. Glued together. The curing temperature was 23 ± 2 ° C. and the curing time was 12 hours. Pull the ends 5 and 6 of the test piece 4 using a tester (Shimadzu AG-IS) and pull it in the opposite direction at a speed of 500 mm / min, measure the shear adhesive force, and check the state of adhesive failure. Examined. The failure state of the adhesive layer can be divided into three types: CF (cohesive failure), TCF (thin layer cohesive failure), and AF (interfacial debonding). The destruction state is CF best, then TCF, and AF is inferior. The numerical value after each destruction state indicates the ratio of the area indicating the destruction state, and is 100 in total.

Comparative Examples 1-5
The above raw materials were used in the proportions shown in Table 1 below, and the silicone adhesives of Comparative Examples 1 to 5 were prepared according to the above experimental method, the shear adhesive force was measured, and the fracture state of the adhesive was confirmed. The results are shown in Table 1. In addition, the numerical value of each component is a mass part.

剪断接着力の単位：MPa

Units of the shear bond strength: MPa

  As can be seen from the above results, it can be seen that when any of the component (C) and the component (E) is not included, no improvement in adhesion is observed in a short time of 12 hours after the application of the adhesive.

Examples 1-7
Using the raw materials described above in the proportions in Table 2 below and following the experimental method, the silicone adhesives of Examples 1-7 were prepared, the shear adhesion was measured, and the fracture state of the adhesive was confirmed. The results are shown in Table 2. In addition, the numerical value of each component is a mass part.

剪断接着力の単位：MPa

Shear adhesion unit: MPa

  From the results in Table 2, it was confirmed that the adhesion at room temperature was improved by adding both the component (C) and the component (E).

Examples 8-11
(C-1) Prepare 1 mol (E-1), (E-2) or (E-5) 1 mol of the following compounds (I-1) to (I-3) obtained by addition reaction, This was used in place of the component (C) and the component (E), and the others were prepared using the above raw materials in the proportions shown in Table 3 below to prepare a silicone adhesive.
(I-1): Addition reaction product of (C-1) and (E-1):

(I-2)：(C-1)と(E-2)の付加反応生成物：

(I-2): Addition product of (C-1) and (E-2):

(I-3)：(C-1)と(E-5)の付加反応生成物：

(I-3): (C-1) and (E-5) addition reaction product:

  According to the above experimental method, the shear adhesive strength was measured for the silicone adhesives of Examples 8 to 11, and the fracture state of the adhesive was confirmed. The results are shown in Table 3. In addition, the numerical value of each component is a mass part.

剪断接着力の単位：MPa

Shear adhesion unit: MPa

  From the above results, it can be seen that the component (C) and the component (E) may be pre-added and used.

It is the schematic which shows the test of the shearing adhesive force of the test piece using the adhesive agent of this invention.

Explanation of symbols

1, 2: Plate 3: Adhesive layer 3
4: Test piece 5, 6: End of test piece

Claims (10)

The following (A) to (E) components:
(A) Diorganopolysiloxane containing at least two alkenyl groups in one molecule, other than the following component (E): 100 parts by weight
(B) Organohydrogenpolysiloxane other than the following component (C), which contains at least two hydrogen atoms bonded to silicon atoms in one molecule: Hydrogen atoms bonded to silicon atoms contained in one molecule of this component Is an amount of 0 to 5.0 per alkenyl group of the organopolysiloxane of component (A),
(C) Organosilicon compound represented by the following general formula (1):

(1)
(Wherein n is an integer of 0 to 10, R is a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms): 0.01 to 5 parts by mass,
(D) Hydrosilylation reaction catalyst: effective amount, and (E) an alkenyl group in one molecule, and at least one group selected from the group consisting of an alkoxy group, a carbonyl group, an epoxy group, and an alkoxysilyl group. Adhesion aid comprising a compound comprising: (C) an amount of 0.01 to 10 mol per mol of component,
(However, when R in general formula (1) of component (C) contains a phenyl group, each component of (A) and (B) does not contain a phenyl group)
An addition-curable silicone adhesive comprising: (B) component is the following average composition formula (2):
    H _a  R ³ _b  SiO _{(4-a-b) / 2}           (2)
(Wherein R ³ Is an unsubstituted monovalent hydrocarbon group independently containing no aliphatic unsaturated bond, and a and b are numbers satisfying 0 <a <2, 0.8 ≦ b ≦ 2, and 0.8 <a + b ≦ 3. The addition-curable silicone adhesive according to claim 1, which is an organohydrogenpolysiloxane represented by the formula: The addition according to claim 1 or 2 , wherein R in the general formula (1) of the component (C) is a phenyl group, and each component of (A) and (B) does not contain a phenyl group. Curing type silicone adhesive. The addition-curable silicone adhesive according to any one of claims 1 to 3, which exhibits adhesion at room temperature. The addition-curable silicone adhesive according to any one of claims 1 to 4 , which is used for adhesion of metal, glass, or organic resin. The following (A), (B), (C ′) and (D) components:
(A) Diorganopolysiloxane containing at least two alkenyl groups in one molecule other than the following component (E): 100 parts by weight (B) At least two hydrogen atoms bonded to silicon atoms in one molecule Containing organohydrogenpolysiloxane other than the following component (C): The number of hydrogen atoms bonded to silicon atoms contained in one molecule of this component is one alkenyl group possessed by the organopolysiloxane of component (A) An amount of 0 to 5.0 per unit (C ′) (C) Organosilicon compound represented by the following general formula (1):

(1)
(Wherein n is an integer of 0 to 10, R is a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms);
(E) an addition reaction product with an adhesion assistant having an alkenyl group in one molecule and further containing at least one group selected from the group consisting of an alkoxy group, a carbonyl group, an epoxy group and an alkoxysilyl group; (D) Hydrosilylation reaction catalyst: effective amount,
(However, when R in general formula (1) of component (C) contains a phenyl group, each component of (A) and (B) does not contain a phenyl group)
An addition-curable silicone adhesive comprising: (B) component is the following average composition formula (2):
    H _a  R ³ _b  SiO _{(4-a-b) / 2}           (2)
(Wherein R ³ Is an unsubstituted monovalent hydrocarbon group independently containing no aliphatic unsaturated bond, and a and b are numbers satisfying 0 <a <2, 0.8 ≦ b ≦ 2, and 0.8 <a + b ≦ 3. The addition-curable silicone adhesive according to claim 6, which is an organohydrogenpolysiloxane represented by the formula: (C ') wherein R is a phenyl group in the general formula of component (1), the components (A) and (B) is characterized by containing no phenyl group, according to claim 6 or 7 Addition-curing silicone adhesive. The addition-curable silicone adhesive according to any one of claims 6 to 8, which exhibits adhesion at room temperature. The addition-curable silicone adhesive according to any one of claims 6 to 9 , which is used for bonding a metal, glass, or organic resin.

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