JPH11166122A - Organopolysiloxane composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a silicone composition having excellent stability by including a specified organopolysiloxane, a specified liquid organohydrogenpolysiloxane, an addition reaction inhibitor comprising an acetylene alcohol having a specified structure and a silylated acetylene alcohol having a specified structure, and a platinum metal catalyst. SOLUTION: This composition comprises 100 pts.wt. organopolysiloxane having at least two unsaturations in the molecule, 0.1-30 pts.wt. liquid organohydrogenpolysiloxane having at least two hydrogen atoms directly bonded to a silicon atom (SiH bond) in the molecule, 0.1-6.0 pts.wt, addition reaction inhibitor being a mixture of an acetylene alcohol (a) of formula I with a silylated acetylene alcohol (b) of formula II, and a platinum metal catalyst. The weight ratio (a)/(b) should be above 5 to 100. R<1> to R<4> are each H, an alky, or an aryl; and R<5> is an alkyl or an aryl.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organopolysiloxane composition, and more particularly to an organopolysiloxane composition which is suitable for forming a cured release film and has excellent stability.

[0002]

2. Description of the Related Art Conventionally, release agents utilizing organopolysiloxanes are classified according to the type of curing reaction at the time of curing. Among them, alkenyl group-containing organopolysiloxanes, organohydrogenpolysiloxanes and platinum-based release agents are particularly preferred. So-called addition-reaction-type organopolysiloxane compositions comprising a catalyst are widely used, and are used as release agents for adhesive labels and adhesive tapes.

In this case, in order to utilize the addition reaction for release paper silicone, the reaction of the platinum catalyst is suppressed at room temperature, and the addition reaction of the alkenyl group-containing siloxane and the hydrogen siloxane proceeds rapidly at a high temperature. Control agents are required. Various such control agents have already been proposed, and it is disclosed that acetylene alcohols are particularly useful (Japanese Patent Publication No. Sho 44-3).
1476, JP-A-6-329917, and JP-A-9
143371 publications).

On the other hand, in recent years, there has been a demand for high-speed and low-temperature curing of silicone from the viewpoint of improving productivity, and therefore, in order to cope with the demand, the amount of catalyst used is often increased. However, increasing the amount of catalyst improves the initial curability,
There is a drawback that the gelation proceeds with the aging of the treatment bath. Further, even if the catalyst is not particularly increased, if the silicone treatment bath after the addition of the platinum catalyst is exposed to a high temperature for a long time, the same gelation phenomenon as in the case of increasing the catalyst occurs.

Therefore, when the amount of the addition reaction controlling agent is increased to prevent the gelation, the pot life is prolonged, but there is a disadvantage that the initial curability is lowered. Also,
When long-chain α-acetylene alcohols as described in JP-A-6-329917 are used as an addition reaction controlling agent, the pot life is prolonged even if the amount is small, but the initial curability is lowered.

On the other hand, as a control agent which does not decrease the curability of the silicone composition even if the amount of the control agent is increased in order to obtain a sufficient control action, a control agent in which a hydroxyl group of acetylene alcohol is silylated is known. (Japanese Patent Laid-Open No. 61
-261 publication). However, when this control agent is used in a large amount, although the initial curability does not change, there is a disadvantage that the curability may decrease with the aging of the treatment bath.

Further, Japanese Patent Application Laid-Open No. Hei 9-143371 discloses that the use of two kinds of control agents having different boiling points can extend the time until gelation in a thin film. Even with the method, it has been difficult to maintain a sufficient pot life without deteriorating curability under severe conditions such as when the amount of catalyst is increased or the treatment bath is left at a high temperature. Therefore, there has been a strong demand for a control agent capable of achieving both pot life and curability even when the amount of the catalyst is increased or the treatment bath is at a high temperature.

Accordingly, the present inventors have further studied the control action of conventional acetylene alcohols and silylated products thereof. As a result, it has been found that these compounds behave as follows in a silicone treatment bath. did. First, when acetylene alcohols are used as a control agent,
Immediately after the preparation of the treatment bath, the acetylene alcohols strongly coordinate with the platinum group catalyst to lower the activity of the catalyst in the treatment bath.
As a result, the activity of the catalyst to which the acetylene alcohol is coordinated is reduced, but the addition reaction cannot be completely stopped, and the catalyst tends to advance the catalytic cycle of the addition reaction.

However, in the treatment bath, since the triple bond of acetylene alcohol causes the addition reaction earlier than the alkenyl group in the siloxane causes the addition reaction, the amount of acetylene alcohol decreases with time and the control action becomes insufficient. As a result, the treatment bath gels. In addition, it was found that when the amount of acetylene alcohol used was increased, the time until gelation could be extended, but the control action was too strong and the initial curability was reduced.

On the other hand, when a silylated product of acetylene alcohol is used as a control agent, these are coordinated to a platinum group metal-based catalyst to reduce the activity of the catalyst, as in the case of acetylene alcohols. Since the coercive force is weaker than that of acetylene alcohol and the ability to suppress the addition reaction is small, the triple bond of the silylated product causes the addition reaction in the treatment bath. For this reason, even if a large amount of the silylated compound is used, the initial curability does not change much. However, since the triple bond of the silylated compound is present in a large amount in the system, the Si bond is not easily removed over time in the treatment bath.
H is consumed, and the curability after the aging of the treatment bath decreases.

Therefore, the present inventors presume that if both these control agents are used in combination, it is possible to achieve both pot life and curability, and as a result of various studies, a small amount of acetylene alcohol and a large amount of By combining silylated products, it was found that a composition with good initial curability, and with a treatment bath with an increased amount of catalyst, the curability did not decrease even with the lapse of time, and a change in peeling properties was small, was found. The invention has been reached.

[0012]

SUMMARY OF THE INVENTION Accordingly, an object of the present invention is to provide an addition-curable silicone composition which cures and exhibits releasability, when the amount of catalyst is increased, or when the treatment bath is at a high temperature. Another object of the present invention is to provide a silicone composition having excellent stability, in which the peeling property and the curability hardly change over time.

The object of the present invention is to provide (1) 100 parts by weight of an organopolysiloxane having at least two unsaturated groups per molecule, and (2) hydrogen base paper directly bonded to silicon base paper in one molecule. Liquid organohydrogenpolysiloxane having at least two (≡SiH bonds) 0.1 to 0.1
30 parts by weight, (3) as an addition reaction control agent, which will be described later,
(A) acetylene alcohol having a specific structure, and
(B) 0.1 to 6.0 parts by weight of a mixture of silylated acetylene alcohols having a specific structure, and
(4) It consists of a catalytic amount of a platinum group metal-based catalyst, and the ratio (b) / (a) of (a) and (b) in the component (3).
Has been achieved by an organopolysiloxane composition characterized in that the weight ratio is greater than 5 and less than or equal to 100.

[0014] Component constituting the silicone composition of the present invention (1), as the organopolysiloxane having at least two alkenyl groups in one molecule, R ⁶ _a R ⁷ _b
SiO _{(4-ab) / 2} (wherein, R ⁶ is the same or different, substituted or unsubstituted hydrocarbon group, and R ⁷ is —C _n H _2n
CH = CH ₂ (n is 0-6) is an alkenyl group represented by, a is 0 to 3, b is a positive number other than 0 in 3 below, a + b
Is 1-3. ) Is used.

In this organopolysiloxane, an alkenyl group R ⁷ directly bonded to a silicon atom in one molecule is contained in an amount of 0.05 to 5.0 mol%, preferably 0.2 to 5.0 mol%, based on all the substituents R ⁶ + R ⁷ . It is preferable to contain it at a ratio of 10 mol%.
If the amount of the alkenyl group is less than 0.05 mol%, a substantial curing rate may not be obtained, and if it exceeds 50 mol%, the peeling property is deteriorated.

R ⁶ other than the alkenyl group bonded to the silicon atom includes, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, octyl, decyl, dodecyl, tetradecyl, Alkyl groups such as hexadecyl group and octadecyl group; cycloalkyl groups such as cyclohexyl group; phenyl group, naphthyl group,
An aryl group such as a tolyl group; or a chloromethyl group or a 3,3,3-trifluoro group in which part or all of the hydrogen atoms bonded to carbon atoms of these groups have been substituted with a halogen atom, a cyano group, a hydroxyl group, or the like. Propyl group, cyanopropyl group, phenol group, hindered phenol group, etc.
Examples thereof include the same or different unsubstituted or substituted monovalent hydrocarbon groups having 1 to 30 carbon atoms. In the present invention, a methyl group, a phenyl group and an alkyl group having 2 to 8 carbon atoms are particularly preferable. In particular, it is preferable that at least 50 mol% of all the substituents other than the alkenyl group bonded to the silicon atom be a methyl group.

The organopolysiloxane may be linear or branched, and its terminal may be any organic group such as a methyl group, a hydroxyl group, an alkenyl group, a phenyl group and an acryloxyalkyl group. Good, but preferably an alkenyl group. The viscosity of the organopolysiloxane may be 50 cs or more at 25 ° C.

The organohydrogenpolysiloxane of the component (2) constituting the organopolysiloxane composition of the present invention is an addition-reactive silicone composition as long as it has at least two hydrogen atoms bonded to silicon atoms in one molecule. It can be appropriately selected from known ones used for products. In the present invention, those in which 90 mol% or more of the organic groups are methyl groups are particularly preferred. These organohydrogenpolysiloxanes are linear, branched,
Any of cyclic structures may be used.
Shown in the

[0019]

Embedded image

And a co-hydrolysis condensate having an average composition formula represented by the following formula (where c and h are integers of 2 or more,
d, f and g are 0 or positive integers, e, i, j, k and l are positive integers, and h + i = 3 to 10). In this case, c is an integer of 2-200, and d is 0-200.
An integer of 100, e is an integer of 1 to 200, f is 0 to 200
G is an integer of 0 to 100, h is an integer of 2 to 10,
And i is preferably an integer of 1 to 8.

Embedded image

The viscosity of these organohydrogenpolysiloxanes ranges from several cs to several hundred thousand cs at 25 ° C.
A wide range of good. The amount of component (2) used is
Although it slightly varies depending on the purpose and use of the composition of the present invention, it may generally be in the range of 0.1 to 30 parts by weight based on 100 parts by weight of the organopolysiloxane of the above-mentioned component (1). , 20 parts by weight or less.

The component (3) used in the present invention is the most important component in the present invention, and the component (a) is an acetylene alcohol having a basic skeleton represented by the following formula (5). In addition, R ¹ and R ² in Chemical Formula 5 are hydrogen atoms; linear or branched alkyl groups such as methyl group, ethyl group, propyl group, isopropyl group, and butyl group; aryl groups such as phenyl group and tolyl group. Group.

Embedded image

The carbon atoms at the α-position to the triple bond with the groups R ¹ and R ² can form a ring, and the total number of carbon atoms of R ¹ and R ² is 8 or less, especially It is preferable that the number is 5 or less. When the total number of carbon atoms of R ¹ and R ² exceeds 8, the initial curability is significantly reduced. The amount of the component (a) depends on the amounts of the components (1), (2) and (4), but is basically from 0.01 to 1 to 100 parts by weight of the component (1). It may be in the range of 0 parts by weight. If the amount of the component (a) is less than 0.01, controlled curability cannot be obtained, and if it is more than 1.0, the initial curability decreases.

Component (a) that can be used in the present invention
As a specific example of, for example, 3-methyl-1-butyne-
3-ol (boiling point 104 ° C), 3-methyl-1-pentyn-3-ol (boiling point 121 ° C), 3,5-dimethylhexyn-3-en-1-yne (boiling point 103 ° C), 3,5
-Dimethyl-1-hexyn-3-ol (boiling point 150
C), 1-ethynyl-1-cyclohexanol (boiling point 1
80 ° C.).

As the component (b), a silylated acetylene alcohol having a basic skeleton represented by the following formula 6 is used.

Embedded image R ³ and R ^{4 in} Chemical Formula 6 are hydrogen atoms; linear or branched alkyl groups such as methyl group, ethyl group, propyl group, isopropyl group, and butyl group; aryl groups such as phenyl group and tolyl group. Yes, the groups R ³ and R ⁴ and the carbon atom α-position to the triple bond can form a ring.

The total number of carbon atoms of R ³ and R ⁴ is 8 or less, and it is particularly preferable that the total number of carbon atoms is 5 or less. When the total number of carbon atoms of R ³ and R ⁴ exceeds 8, the initial curability decreases. R ⁵ is selected from a linear or branched alkyl group such as a methyl group, an ethyl group, a propyl group, an isopropyl group, and a butyl group; and an aryl group such as a phenyl group and a tolyl group.

Component (b) that can be used in the present invention
As a specific example of, for example, tolmethyl (3-methyl-
1-butyne-3-oxy) silane (boiling point 115 ° C.), tetramethyltetravinylsiloxane cyclic (boiling point 200
° C or more), methyl tris (3-methyl-1-butyne-3)
-Oxy) silane (boiling point 200 ° C. or higher), dimethylbis (3-methyl-1-butyne-3-oxy) silane (boiling point 195 ° C.), methylvinylbis (3-methyl-1-butyne-3-oxy) silane (Boiling point 200 ° C. or more).

The amount of the component (3) depends on the amounts of the components (1), (2) and (4), but is basically based on 100 parts by weight of the component (1) in the composition. 0.1 to 6.0 parts by weight. If the amount of the component (3) is less than 0.1 part by weight, a sufficient pot life cannot be obtained, and if it is more than 6.0 parts by weight, the curability after treatment bath aging decreases. Further, (a)
It is necessary that the usage ratio between (b) and (b) is in the range of 5 <(b) / (a) ≦ 100. When this ratio is smaller than 5, the initial curability tends to decrease when the total amount of (a) and (b) is large, and sufficient pot life is obtained when the total amount of (a) and (b) is small. Is difficult to obtain. When this ratio is larger than 100, the curability is reduced over time in the treatment bath. Both (a) and (b) preferably have a boiling point in the range of 130 ° C. to 170 ° C., and when one of (a) and (b) has a boiling point of 130 ° C. or less, Preferably, one boiling point is 170 ° C. or higher.

The mechanism of action of the control system according to the present invention using these two compounds in combination is considered as follows. First, a small amount of acetylene alcohol, which is the component (a), strongly coordinates with the catalyst after adjusting the treatment bath to lower the catalytic activity.
On the other hand, the silylated acetylene alcohol which is a component (b), which is present in excess as a substrate for the addition reaction which proceeds slightly, acts to suppress the reduction of the non-silylated acetylene alcohol.

That is, since the silylated acetylene alcohol acts as a substrate for the addition reaction, the consumption of the acetylene alcohol (addition reaction) is suppressed. On the other hand, since the consumption of acetylene alcohol is suppressed in the system, the state of low catalytic activity continues for a long time, and the consumption of SiH is suppressed. By the above mechanism, a composition having a sufficiently long pot life can be obtained without using acetylene alcohol that reduces the initial curability.

In the present invention, a platinum group catalyst conventionally known as this kind of addition catalyst is used as the component (4) in order to effectively advance the addition curing reaction. Examples of such platinum group catalysts include, for example, platinum-based, palladium-based, and rhodium-based catalysts. Platinum-based catalysts are particularly preferred.Specifically, chloroplatinic acid, alcohol solutions of chloroplatinic acid and aldehyde Solutions, complexes of chloroplatinic acid with various olefins, vinyl siloxane, and the like. The addition amount of the platinum-based catalyst may be a catalyst amount, but from the viewpoint of obtaining a good cured film and being economical, the amount of the platinum group metal relative to the components (1) and (2) is from 1 to 1,000 p.
pm.

[0032] In addition to the above components, optional components can be further added to the silicone composition of the present invention. For example, for the purpose of adjusting the peeling force, an organopolysiloxane having no hydrogen atom bonded to a vinyl group or a silicon atom or the like can be added as needed. In addition, the addition amount of the optional component can be appropriately determined as long as the effect of the present invention is not hindered.

The silicone composition of the present invention can be obtained by blending the aforementioned components (1) to (4) and a predetermined amount of an optional component. In this case, each component except the component (4) is used. It is preferable to add the component (4) after previously mixing uniformly. Further, if necessary, it may be used by dissolving it in an organic solvent such as toluene, xylene or n-hexane. The silicone composition prepared as described above is applied to a substrate such as paper or plastic film and then heat-cured by an ordinary method. The substrate on which the cured film of the composition of the present invention is formed in this manner is used as a release paper.

[0034]

EFFECTS OF THE INVENTION The silicone composition of the present invention comprises a small amount of an acetylene alcohol-based addition control agent which strongly coordinates with a catalyst to reduce the catalytic activity, and a silylated acetylene which acts as a substrate for a slightly progressing addition reaction. Since an excess amount of alcohol is contained at the same time, there is an advantage that the pot life is long and the peeling characteristics and the curing performance do not change even if the treatment bath is aged.

[0035]

Next, the present invention will be further described with reference to Examples and Comparative Examples.
The present invention is limited by these
is not. Parts in the examples represent parts by weight, and
The physical property values mean values measured by the following test methods.Treatment bath viscosity  Immediately after preparation of the organopolysiloxane composition of the present invention,
The initial viscosity is the viscosity at 30 ° C. in this composition.
The viscosity after storage at 30 ° C. for 24 hours was defined as the viscosity over time.

[0036]Curability  The initial curability depends on the organopolysiloxane composition of the present invention.
0.6g / m on polyethylene laminated paper immediately after product preparation
²In a hot air dryer at 100 ° C.
The cured film formed by heating for a fixed time was rubbed several times with a finger
Visually assess the presence or absence of cloudiness and shedding at
The curability was indicated using the time required for the formation. Also, over time
The curability of the organopolysiloxane of the present invention
After storing the composition at 30 ° C. for 24 hours, proceed as above.
And the curability was measured.

[0037]Peeling force  The initial release force is determined by the organopolysiloxane composition of the present invention.
Immediately after preparation of the product,
Cured at 100 ° C for 30 seconds,
Attach sa-7475 tape (manufactured by BDF).
C. for 2 hours, using a tensile tester for 18 hours.
Pull the tape at an angle of 0 ° at a peeling speed of 0.3 m / min.
Measure the force (g / 2.5cm) required for peeling
This value was used as the initial peel force. Also, the peeling force over time
Is to prepare the organopolysiloxane composition of the present invention at 30 ° C.
After storing for 24 hours, peel force is measured in the same manner as above.
This value was defined as the time-dependent peeling force.

[0038]Residual adhesion rate  The initial residual adhesion rate is the same as for the peel force.
A cured film of the nopolysiloxane composition is formed,
Polyester tape Nitto 31B (Nitto Denko)
20g / cm²Load
And heat-treat at 70 ° C for 20 hours, then remove the tape
Then, it was attached to a stainless steel plate. Next, this processing
The force required to peel off the loop and peel off the stainless steel plate
(G / 2.5 cm) and peel off the untreated standard tape
The percentage of the force required to release is defined as the initial residual adhesion rate.
did.

The untreated standard tape is a polyester tape knit-31B (trade name, manufactured by Nitto Denko Corporation) bonded to a Teflon sheet, a load of 20 g / cm ² is applied, and the tape is treated at 70 ° C. for 20 hours. The tape is peeled off after heat treatment and then attached to a stainless steel plate. As described above, the force (g / 2.5 cm) required to peel the tape from the stainless steel plate was measured, and this was defined as the force required to peel the untreated standard tape. The residual adhesion rate after aging was measured in the same manner as described above after storing the organopolysiloxane composition of the present invention at 30 ° C. for 24 hours, and this value was defined as the aging residual adhesion rate.

Embodiment 1 As component (1), the vinylation is 0.0075 mol / 100 g, and the viscosity when diluted to 30% by weight with toluene is 10,000 cp.
30 parts of a vinyl group-containing organopolysiloxane represented by the following average composition formula were dissolved in 570 parts of toluene.

Embedded image

Next, as component (2), a viscosity of 250 c
p and the SiH value is 1.0 ml / 100 g.
0.65 parts of methyl hydrogen polysiloxane represented by an average composition formula of

Embedded image 3.5-dimethyl-1 as component (a) of component (3)
-Hexin-3-ol (boiling point 150 ° C) 0.1 part and 1-dimethylpropynyloxytrimethylsilane (boiling point 115 ° C) 0.8 part as the component (b) were added and mixed well.

To this mixture, a complex of platinum and vinyl siloxane was added as component (4) to the above polysiloxane in an amount of 200 ppm in terms of platinum, followed by stirring to obtain a silicone composition 1. Table 1 shows the results of measuring the pot life, curability, peeling force, and residual adhesion of the obtained composition, together with the type of control agent used, the amount of catalyst, and the viscosity of the composition.

[0043]

[Table 1]

Embodiment 2 FIG. In Example 1, component (3)
A silicone composition 2 was obtained in exactly the same manner as in Example 1 except that the addition amount of 1-dimethylpropynyloxytrimethylsilane used as the component (b) was 1.2 parts. The results of examining the properties of the obtained composition 2 are as shown in Table 1.

Embodiment 3 FIG. Except that the addition amount of 3,5-dimethyl-hexyn-3-ol used as the component (a) of the component (3) in Example 1 was 0.05 part,
A silicone composition 3 was obtained in exactly the same manner as in Example 1.
The results of examining the properties of the obtained composition 3 are as shown in Table 1.

Embodiment 4 FIG. 3-Methyl-1-butyne-3 used as component (a) of component (3) in Example 1
A silicone composition 4 was obtained in exactly the same manner as in Example 1 except that 0.07 parts of -ol (boiling point: 104 ° C.) was added.

Embodiment 5 FIG. A silicone composition was prepared in exactly the same manner as in Example 1 except that 0.1 part of 1-ethynyl-1-cyclohexanol (boiling point: 192 ° C.) used as the component (a) of the component (3) in Example 1 was added. The product 5 was obtained, and the characteristics were examined. The results are shown in Table 1.

Embodiment 6 FIG. Component (4) used in Example 1
Except that the amount of added was 400 ppm in terms of platinum.
A silicone composition 6 was obtained in exactly the same manner as in Example 1, and the characteristics were examined. The results are shown in Table 2 together with the type of control agent used, the amount of the catalyst, and the viscosity of the composition.

[0049]

[Table 2]

Embodiment 7 FIG. Component (4) used in Example 2
A silicone composition 7 was obtained in exactly the same manner as in Example 2 except that the addition amount of was set to 400 ppm. The results of examining its properties are shown in Table 2.

Embodiment 8 FIG. Component (4) used in Example 3
Was obtained in exactly the same manner as in Example 3 except that the amount of added was 400 ppm. The results of examining the properties of the silicone composition 8 are shown in Table 2.

Embodiment 9 FIG. Ingredient (4) used in Example 4
A silicone composition 9 was obtained in exactly the same manner as in Example 4 except that the amount of was added was 400 ppm. The results of examining the properties of the silicone composition 9 are shown in Table 2.

Embodiment 10 FIG. A silicone composition 10 was obtained in exactly the same manner as in Example 5 except that the addition amount of the component (4) used in Example 5 was 400 ppm, and the characteristics were examined. Table 2 shows the results.

Comparative Example 1 Component (3) used in Example 1
Was used, and a silicone composition 11 was obtained in exactly the same manner as in Example 1 except that 0.1 part of 3.5-dimethyl-1-hexyn-3-ol was used alone. Table 1 shows the results of measuring the pot life, curability, peeling force, and residual adhesiveness of the obtained composition.

Comparative Example 2 A silicone composition 12 was obtained in exactly the same manner as in Comparative Example 1, except that the amount of the control agent used in Comparative Example 1 was changed to 0.2 part. Table 1 shows the results of measuring the pot life, curability, peeling force, and residual adhesiveness of the obtained composition.

Comparative Example 3 A silicone composition 12 was obtained in exactly the same manner as in Comparative Example 1, except that the control agent used in Comparative Example 1 and the amount added were 0.8 parts of 1-dimethylpropynyloxytrimethylsilane. Table 1 shows the results of measuring the pot life, curability, peeling force, and residual adhesiveness of the obtained composition.

Comparative Example 4 Component (4) used in Comparative Example 1
Except that the amount of added was 400 ppm in terms of platinum.
A silicone composition 14 was obtained in exactly the same manner as in Comparative Example 1. Table 2 shows the results of measuring the pot life, the curability, the peeling force, and the residual adhesiveness of the obtained composition.

Comparative Example 5 A silicone composition 15 was obtained in exactly the same manner as in Comparative Example 2, except that the amount of the component (4) in Comparative Example 2 was changed to 400 ppm. The obtained composition was measured for pot life, curability, peeling strength, and residual adhesiveness. The results are shown in Table 2.

Comparative Example 6 A silicone composition 16 was obtained in exactly the same manner as in Comparative Example 3, except that the amount of the component (4) in Comparative Example 3 was changed to 400 ppm. Table 2 shows the results of measuring the pot life, the curability, the peeling force, and the residual adhesiveness of the obtained composition.

[Procedure amendment]

[Submission date] September 9, 1998

[Procedure amendment 1]

[Document name to be amended] Statement

[Correction target item name] 0013

[Correction method] Change

[Correction contents]

The object of the present invention is to provide (1) 100 parts by weight of an organopolysiloxane having at least two unsaturated groups in one molecule, (2) a hydrogen atom directly bonded to a silicon atom in one molecule ( Liquid organohydrogenpolysiloxane having at least two (≡SiH bonds) 0.1 to 0.1
30 parts by weight, (3) as an addition reaction control agent, which will be described later,
(A) acetylene alcohol having a specific structure, and
(B) 0.1 to 6.0 parts by weight of a mixture of silylated acetylene alcohols having a specific structure, and
(4) It consists of a catalytic amount of a platinum group metal-based catalyst, and the ratio (b) / (a) of (a) and (b) in the component (3).
Has been achieved by an organopolysiloxane composition characterized in that the weight ratio is greater than 5 and less than or equal to 100.

 ──────────────────────────────────────────────────続 き Continued on the front page (72) Inventor Kenichi Isobe 1-10 Hitomi, Matsuida-cho, Usui-gun, Gunma Prefecture Shin-Etsu Chemical Co., Ltd. Silicone Electronic Materials Technology Laboratory

Claims (1)

[Claims] (1) 100 parts by weight of an organopolysiloxane having at least two unsaturated groups per molecule,
(2) 0.1 to 30 parts by weight of a liquid organohydrogenpolysiloxane having at least two hydrogen atoms (≡SiH bonds) directly bonded to silicon atoms in one molecule;
(3) As an addition reaction controlling agent, (a) acetylene alcohol having a structure of the following formula 1 (However, R ¹ and R ² in Chemical Formula ¹ are a hydrogen atom or a group selected from an alkyl group and an aryl group.) And (b) a silylated compound having the following chemical structure Acetylene alcohol (However, R ³ and R ⁴ in Chemical Formula 2 are a hydrogen atom or a group selected from an alkyl group and an aryl group, and R ⁵ is a group selected from an alkyl group and an aryl group.) 0.1 to 6.0 parts by weight, and (4) a catalytic amount of a platinum group metal-based catalyst, and the ratio (b) / (a) of (a) and (b) in the component (3). Is 5% by weight
An organopolysiloxane composition having a molecular weight of more than 100 and not more than 100.